cytellin and gamma-sitosterol

cytellin has been researched along with gamma-sitosterol* in 1626 studies

Reviews

62 review(s) available for cytellin and gamma-sitosterol

ArticleYear
β-Sitosterol as a Promising Anticancer Agent for Chemoprevention and Chemotherapy: Mechanisms of Action and Future Prospects.
    Advances in nutrition (Bethesda, Md.), 2023, Volume: 14, Issue:5

    Cancer is one of the primary causes of death worldwide, and its incidence continues to increase yearly. Despite significant advances in research, the search for effective and nontoxic preventive and therapeutic agents remains greatly important. Cancer is a multimodal disease, where various mechanisms play significant roles in its occurrence and progression. This highlights the need for multitargeted approaches that are not only safe and inexpensive but also provide effective alternatives for current therapeutic regimens. β-Sitosterol (SIT), the most abundant phytosterol found in various plant foods, represents such an option. Preclinical evidence over the past few decades has overwhelmingly shown that SIT exhibits multiple anticancer activities against varied cancers, such as liver, cervical, colon, stomach, breast, lung, pancreatic, and prostate cancers, in addition to leukemia, multiple myeloma, melanoma, and fibrosarcoma. In this article, we present the latest advances and perspectives on SIT-systematically summarizing its antitumor mechanisms of action into 7 main sections and combining current challenges and prospects-for its use as a promising agent for cancer prevention and treatment. In particular, SIT plays a role in cancer prevention and treatment mainly by enhancing apoptosis, inducing cell cycle arrest, bidirectionally regulating oxidative stress, improving metabolic reprogramming, inhibiting invasion and metastasis, modulating immunity and inflammation, and combating drug resistance. Although SIT holds such great promise, the poor aqueous solubility and bioavailability coupled with low targeting efficacy limit its therapeutic efficacy and clinical application. Further research on novel drug delivery systems may improve these deficiencies. Overall, through complex and pleiotropic mechanisms, SIT has good potential for tumor chemoprevention and chemotherapy. However, no clinical trials have yet proven this potential. This review provides theoretical basis and rationality for the further design and conduct of clinical trials to confirm the anticancer activity of SIT.

    Topics: Antineoplastic Agents; Chemoprevention; Humans; Male; Prostatic Neoplasms; Sitosterols

2023
Multifunctional roles and pharmacological potential of β-sitosterol: Emerging evidence toward clinical applications.
    Chemico-biological interactions, 2022, Sep-25, Volume: 365

    Currently, available therapeutic medications are both costly as well as not entirely promising in terms of potency. So, new candidates from natural resources are of research interest to find new alternative therapeutics. A well-known combination is a β-sitosterol, a plant-derived nutrient with anticancer properties against breast, prostate, colon, lung, stomach, and leukemia. Studies have shown that β-sitosterol interferes with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis, anti-inflammatory, anticancer, hepatoprotective, antioxidant, cardioprotective, and antidiabetic effects have been discovered during pharmacological screening without significant toxicity. The pharmacokinetic profile of β-sitosterol has also been extensively investigated. However, a comprehensive review of the pharmacology, phytochemistry and analytical methods of β-sitosterol is desired. Because β-sitosterol is a significant component of most plant materials, humans use it for various reasons, and numerous β-sitosterol-containing products have been commercialized. To offset the low efficacy of β-sitosterol, designing β-sitosterol delivery for "cancer cell-specific" therapy holds great potential. Delivery of β-sitosterol via liposomes is a demonstration that has shown great promise. But further research has not progressed on the drug delivery of β-sitosterol or how it can enhance β-sitosterol mediated anti-inflammatory activity, thus making β-sitosterol an orphan nutraceutical. Therefore, extensive research on β-sitosterol as an anticancer nutraceutical is recommended.

    Topics: Apoptosis; Cell Cycle; Humans; Male; Neoplasms; Plant Extracts; Sitosterols

2022
Phytosterols: Potential Metabolic Modulators in Neurodegenerative Diseases.
    International journal of molecular sciences, 2021, Nov-12, Volume: 22, Issue:22

    Phytosterols constitute a class of natural products that are an important component of diet and have vast applications in foods, cosmetics, and herbal medicines. With many and diverse isolated structures in nature, they exhibit a broad range of biological and pharmacological activities. Among over 200 types of phytosterols, stigmasterol and β-sitosterol were ubiquitous in many plant species, exhibiting important aspects of activities related to neurodegenerative diseases. Hence, this mini-review presented an overview of the reported studies on selected phytosterols related to neurodegenerative diseases. It covered the major phytosterols based on biosynthetic considerations, including other phytosterols with significant in vitro and in vivo biological activities.

    Topics: Brain; Humans; Molecular Structure; Neurodegenerative Diseases; Neuroprotective Agents; Phytosterols; Phytotherapy; Plants, Medicinal; Sitosterols; Stigmasterol

2021
An update on β-sitosterol: A potential herbal nutraceutical for diabetic management.
    Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 2020, Volume: 131

    Phytosterols are bioactive compounds that are naturally present in plant cell membranes with chemical structure similar to the mammalian cell- derived cholesterol. They are highly present in lipid-rich plant foods such as nuts, seed, legumes and olive oil. Among various phytosterols, β-sitosterol (SIT) is the major compound, found plentiful in plants. It has been evidenced in many in-vitro and in-vivo studies that SIT possesses various biological actions such as anxiolytic & sedative effects, analgesic, immunomodulatory, antimicrobial, anticancer, anti - inflammatory, lipid lowering effect, hepatoprotective, protective effect against NAFLD and respiratory diseases, wound healing effect, antioxidant and anti-diabetic activities. In this review, in order to compile the sources, characterization, biosynthesis, pharmacokinetics, antioxidant and anti-diabetic activities of SIT, classical and online-literature were studied which includes the electronic search (Sci Finder, Pubmed, Google Scholar, Scopus, and Web of Science etc) and books on photochemistry. The experimental studies on SIT gives a clear evidence that the potential phytosterol can be used as supplements to fight against life threatening diseases. High potential of this compound, classifies it as the notable drug of the future. Therefore, immense researches regarding its action at molecular level on life threatening diseases in humans are highly endorsed.

    Topics: Animals; Antioxidants; Diabetes Mellitus; Dietary Supplements; Humans; Sitosterols

2020
Microalgal carotenoids and phytosterols regulate biochemical mechanisms involved in human health and disease prevention.
    Biochimie, 2019, Volume: 167

    Microalgae are photosynthetic microorganisms that produce numerous bioactive molecules that can be used as food supplement to prevent chronic disease installation. Indeed, they produce phycobiliproteins, polysaccharides, lipids, carotenoids and sterolic compounds. The use of microalgae in human nutrition provide a mixture of these molecules with synergistic effect. The aim of this review is to present the specific roles played by the xanthophylls, and specifically astaxanthin and fucoxanthin, two high added value carotenoids, and by microalgal phytosterols such as β-sitosterol, campesterol and stigmasterol on several cell mechanisms involved in the prevention of cardiometabolic diseases and cancers. This review explains how these microalgal molecules modulate cell signaling pathways involved in carbohydrate and lipid metabolisms, inflammation, apoptosis, invasion and metastasis. Xanthophylls and phytosterols are involved in the reduction of inflammatory markers in relation with the regulation of the c-Jun N-terminal kinases and nuclear factor-kappa B signaling pathways, and suppression of production of pro-inflammatory mediators. Xanthophylls act on glucose and lipid metabolisms via both the upregulation of peroxisome proliferator-activated receptors (PPARs) and glucose transporters and its effects on the expression of enzymes involved in fatty acid synthesis and cholesterol metabolism. Their anti-cancer effects are related to the induction of intrinsic apoptosis due to down-regulation of key regulatory kinases. The anti-angiogenesis, anti-proliferative and anti-invasive effects are correlated with decreased production of endothelial growth factors and of matrix metalloproteinases. Phytosterols have a major role on cholesterol absorption via modification of the activities of Niemann-Pick C1 like 1 and ATP-binding cassette transporters and on cholesterol esterification. Their action are also related with the modulation of PPARs and sterol regulatory element-binding protein-1 activities.

    Topics: Apoptosis; Carbohydrate Metabolism; Cardiovascular Diseases; Cholesterol; Dietary Supplements; Humans; Lipid Metabolism; Metabolic Diseases; Microalgae; Neoplasms; Phytosterols; Signal Transduction; Sitosterols; Xanthophylls

2019
Non-Cholesterol Sterol Concentrations as Biomarkers for Cholesterol Absorption and Synthesis in Different Metabolic Disorders: A Systematic Review.
    Nutrients, 2019, Jan-09, Volume: 11, Issue:1

    Non-cholesterol sterols are validated biomarkers for intestinal cholesterol absorption and endogenous cholesterol synthesis. However, their use in metabolic disturbances has not been systematically explored. Therefore, we conducted a systematic review to provide an overview of non-cholesterol sterols as markers for cholesterol metabolism in different metabolic disorders. Potentially relevant studies were retrieved by a systematic search of three databases in July 2018 and ninety-four human studies were included. Cholesterol-standardized levels of campesterol, sitosterol and cholestanol were collected to reflect cholesterol absorption and those of lathosterol and desmosterol to reflect cholesterol synthesis. Their use as biomarkers was examined in the following metabolic disorders: overweight/obesity (

    Topics: Biomarkers; Cardiovascular Diseases; Cholesterol; Desmosterol; Diabetes Mellitus; Humans; Intestinal Absorption; Intestinal Diseases; Kidney Diseases; Liver Diseases; Metabolic Diseases; Obesity; Overweight; Phytosterols; Sitosterols; Sterols

2019
The biochemical and genetic diagnosis of lipid disorders.
    Current opinion in lipidology, 2019, Volume: 30, Issue:2

    To examine recent advances in our knowledge on the diagnosis of lipid disorders.. Fasting values above the 99th percentile for direct LDL-cholesterol (LDL-C), lipoprotein(a), and triglycerides are greater than 225 mg/dl, greater than 160 mg/dl, and greater than 500 mg/dl (>5.82, >394, and >5.65 mmol/l), respectively, whereas such values for plasma lathosterol, β-sitosterol, and cholestanol are greater than 8.0, 8.0, and 5.0 mg/l (>0.021, 0.019, and 0.013 mmol/l), respectively. Values below the first percentile for LDL-C are less than 40 mg/dl (<1.03 mmol/l) and for HDL-cholesterol (HDL-C) less than 25 mg/dl (<0.65 mmol/l) in men and less than 30 mg/dl (<0.78 mmol/l) in women, respectively. The above values can predispose to premature CVD, pancreatitis, neurologic disease, and kidney failure, and may be associated with monogenic lipid disorders. In the absence of secondary causes including diabetes or kidney, liver, or thyroid disease, consideration should be given to sequencing the following genes: ABCA1, ABCG5, ABCG8, APOA1, APOA5, APOB, APOC2, APOE, CETP, CYP27A1, GPIHBP1, LCAT, LDLR, LDLRAP1, LIPA, LIPC, LMF1, LPL, MTTP, PCSK9, SCARB1, and STAP1.. Recent data indicate that secondary causes and a wider range of conditions need to be considered in identifying the underlying causes of hypercholesterolemia, hypertriglyceridemia, hyperalphalipoproteinemia, hypobetalipoproteinemia, and HDL deficiency. Identifying such disorders allows for a more precise assessment of prognosis and the formulation of optimal therapy.

    Topics: Apolipoproteins; Biomarkers; Cardiovascular Diseases; Cholestanol; Cholesterol; Cholesterol, LDL; Fasting; Gene Expression; Genetic Predisposition to Disease; High-Throughput Nucleotide Sequencing; Humans; Lipid Metabolism Disorders; Lipoprotein(a); Mutation; Pancreatitis; Receptors, Lipoprotein; Sitosterols; Triglycerides

2019
Diurnal Variation of Markers for Cholesterol Synthesis, Cholesterol Absorption, and Bile Acid Synthesis: A Systematic Review and the Bispebjerg Study of Diurnal Variations.
    Nutrients, 2019, Jun-26, Volume: 11, Issue:7

    Human studies have shown diurnal rhythms of cholesterol and bile acid synthesis, but a better understanding of the role of the circadian system in cholesterol homeostasis is needed for the development of targeted interventions to improve metabolic health. Therefore, we performed a systematic literature search on the diurnal rhythms of cholesterol synthesis and absorption markers and of bile acid synthesis markers. We also examined the diurnal rhythms of the cholesterol synthesis markers lathosterol and desmosterol, and of the cholesterol absorption markers cholestanol, campesterol, and sitosterol in serum samples from the Bispebjerg study. These samples were collected every three hours over a 24-hour period in healthy males (

    Topics: Adolescent; Adult; Bile Acids and Salts; Biomarkers; Cholestanol; Cholesterol; Circadian Rhythm; Desmosterol; Female; Humans; Intestinal Absorption; Male; Middle Aged; Phytosterols; Sitosterols; Time Factors; Young Adult

2019
Sitosterolemia, Hypercholesterolemia, and Coronary Artery Disease.
    Journal of atherosclerosis and thrombosis, 2018, Sep-01, Volume: 25, Issue:9

    Sitosterolemia is a rare inherited disease characterized by increased levels of plant sterols, such as sitosterol. The cause of this disease is ATP-binding cassette (ABC) subfamily G member 5 or member 8 (ABCG5 or ABCG8, respectively) gene mutations. Recent advances in genetics have revealed that the prevalence of subjects with deleterious mutations in ABCG5 and/or ABCG8 genes could be more than 1 in ~200,000 individuals among the general population. Furthermore, accumulated evidence, including infantile cases exhibiting progression/regression of systemic xanthomas associated with LDL cholesterol levels, have shown that the elevation of LDL cholesterol seems to be the major cause of development of atherosclerosis and not the elevation of sitosterol. Regarding therapies, LDL apheresis, as well as proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitors, could be useful for sitosterolemia, in addition to ezetimibe and/or colestimide. In this study, we provide the current understanding and future perspectives of sitosterolemia, which is currently considered an extremely rare disorder but is expected to be much more prevalent in clinical settings.

    Topics: ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; Coronary Artery Disease; Heterozygote; Humans; Hypercholesterolemia; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Lipoproteins; Mutation; Phenotype; Phytosterols; Polymorphism, Genetic; Proprotein Convertase 9; Sitosterols

2018
Two novel variants of the ABCG5 gene cause xanthelasmas and macrothrombocytopenia: a brief review of hematologic abnormalities of sitosterolemia.
    Journal of thrombosis and haemostasis : JTH, 2017, Volume: 15, Issue:9

    Essentials Diagnosis of sitosterolemia, a rare recessive or syndromic disorder, is usually delayed. Peripheral blood smear is extremely useful for establishing the suspicion of sitosterolemia. High-throughput sequencing technology enables the molecular diagnosis of inherited thrombocytopenias. Accurate characterization of sitosterolemia helps us determine appropriate management.. Background Sitosterolemia (STSL) is a recessive inherited disorder caused by pathogenic variants in the ABCG5 and ABCG8 genes. Increased levels of plasma plant sterols (PSs) usually result in xanthomas and premature coronary atherosclerosis, although hematologic abnormalities may occasionally be present. This clinical picture is unfamiliar to many physicians, and patients may be at high risk of misdiagnosis. Objectives To report two novel ABCG5 variants causing STSL in a Spanish patient, and review the clinical and mutational landscape of STSL. Patient/Methods A 46-year-old female was referred to us with lifelong macrothrombocytopenia. She showed familial hypercholesterolemia-related xanthomas. Molecular analysis was performed with high-throughput sequencing. Plasma PS levels were evaluated with gas-liquid chromatography. The STSL landscape was reviewed with respect to specific online databases and all reports published since 1974. Results A blood smear revealed giant platelets and stomatocytes. Novel compound heterozygous variants were detected in exons 7 (c.914C>G) and 13 (c.1890delT) of ABCG5. The patient showed an increased plasma level of sitosterol. These findings support the diagnosis of STSL. In our review, we identified only 25 unrelated STLS patients who presented with hematologic abnormalities including macrothrombocytopenia. It remains unknown why only some patients develop hematologic abnormalities. Conclusions This is the first Spanish STSL patient to be reported and molecularly characterized. The early diagnosis of STLS is strongly supported by the presence of stomatocytes in blood smears. The definitive diagnosis of STSL by measurement of serum PS levels and molecular analyses prompted the use of ezetimibe therapy.

    Topics: Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 5; DNA Mutational Analysis; Ezetimibe; Female; Genetic Predisposition to Disease; High-Throughput Nucleotide Sequencing; Humans; Hypercholesterolemia; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Lipoproteins; Middle Aged; Mutation; Phenotype; Phytosterols; Sitosterols; Spain; Thrombocytopenia; Xanthomatosis

2017
Oxysterols formation: A review of a multifactorial process.
    The Journal of steroid biochemistry and molecular biology, 2017, Volume: 169

    Dietary sterols are nutritionally interesting compounds which can suffer oxidation reactions. In the case of plant sterols, they are being widely used for food enrichment due to their hypocholesterolemic properties. Besides, cholesterol and plant sterols oxidation products are associated with the development of cardiovascular and neurodegenerative diseases, among others. Therefore, the evaluation of the particular factors affecting sterol degradation and oxysterols formation in foods is of major importance. The present work summarizes the main results obtained in experiments which aimed to study four aspects in this context: the effect of the heating treatment, the unsaturation degree of the surrounding lipids, the presence of antioxidants on sterols degradation, and at last, oxides formation. The use of model systems allowed the isolation of some of these effects resulting in more accurate data. Thus, these results could be applied in real conditions.

    Topics: Animals; Antioxidants; Cholesterol; Hot Temperature; Humans; Kinetics; Models, Theoretical; Oxygen; Oxysterols; Phytosterols; Sitosterols; Stigmasterol

2017
Approaches to intravenous clinical pharmacokinetics: Recent developments with isotopic microtracers.
    Journal of clinical pharmacology, 2016, Volume: 56, Issue:1

    Obtaining pharmacokinetic data from the intravenous route for drugs intended for oral administration has traditionally been expensive and time consuming because of the toxicology requirements and challenges in intravenous formulations. Such studies are necessary, however, particularly when regulator agencies request absolute bioavailability data. A method has emerged whereby the drug administered intravenously is isotopically labeled and dosed at a maximum of 100 µg concomitantly with an oral administration given at a therapeutically relevant level. The intravenous administration has been termed a microtracer and obviates intravenous toxicology requirements as well as simplifying formulations. The study design also essentially removes issues of nonlinear pharmacokinetics that may occur when oral and intravenous doses are administered separately. This review examines the methodology and the literature to date, including those studies intended for regulatory submission. The method has been extended to the study of prodrug-to-active drug kinetics and to obtaining clearance, volume of distribution, and absolute bioavailability at steady-state conditions.

    Topics: Administration, Intravenous; Amino Acids; Anilides; Animals; Benzhydryl Compounds; Bridged Bicyclo Compounds, Heterocyclic; Cyclic S-Oxides; Glucosides; Healthy Volunteers; Humans; Isotope Labeling; Pharmaceutical Preparations; Pharmacokinetics; Pyridines; Sitosterols

2016
An Evidence-Based Systematic Review of Beta-Sitosterol, Sitosterol (22,23- dihydrostigmasterol, 24-ethylcholesterol) by the Natural Standard Research Collaboration.
    Journal of dietary supplements, 2016, Volume: 13, Issue:1

    An evidence-based systematic review of beta-sitosterol, sitosterol (22,23-dihydrostigmasterol, 24-ethylcholesterol) by the Natural Standard Research Collaboration consolidates the safety and efficacy data available in the scientific literature using a validated, reproducible grading rationale. This article includes written and statistical analysis of clinical trials, plus a compilation of expert opinion, folkloric precedent, history, pharmacology, kinetics/dynamics, interactions, adverse effects, toxicology, and dosing.

    Topics: Evidence-Based Medicine; Humans; Phytotherapy; Plant Extracts; Sitosterols; Stigmasterol

2016
Current Knowledge about Oxysterols: A Review.
    Journal of food science, 2016, Volume: 81, Issue:10

    For years food consumers have been warned that a cholesterol-rich diet may result in atherosclerosis. It is also well known that consumption of large amounts of phytosterols decreases concentration of low-density lipoproteins (LDLs) in blood (LDLs are regarded a key risk factor in development of cardiovascular diseases). However, no scientific evidence has unambiguously proved any direct connection between amount of consumed cholesterol and LDL level in blood. On the other hand, concentration of cholesterol oxidation products, oxysterols, seems to be indeed relevant; for example, they significantly impact appearance of atherosclerotic lesions (plaques). Phytosterols (like sitosterol or campasterol) decrease LDL level in blood, but on the other hand products of their oxidation are toxic. Therefore, it is worth to know influence of phytosterols on living organisms, processes which lead to their formation, and their levels in popular foodstuffs. This paper is an attempt to review literature data on the above aspects, as well as on impact on living organisms of oxidation products of popular sterols.

    Topics: Animals; Atherosclerosis; Cardiovascular Diseases; Cholesterol; Cholesterol, Dietary; Humans; Lipoproteins, LDL; Mice; Oxidation-Reduction; Oxysterols; Phytosterols; Risk Factors; Sitosterols

2016
Bioactivity of Phytosterols and Their Production in Plant in Vitro Cultures.
    Journal of agricultural and food chemistry, 2016, Sep-28, Volume: 64, Issue:38

    Phytosterols are a kind of plant metabolite belonging to the triterpene family. These compounds are essential biomolecules for human health, and so they must be taken from foods. β-Sitosterol, campesterol, and stigmasterol are the main phytosterols found in plants. Phytosterols have beneficial effects on human health since they are able to reduce plasma cholesterol levels and have antiinflammatory, antidiabetic, and anticancer activities. However, there are many difficulties in obtaining them, since the levels of these compounds produced from plant raw materials are low and their chemical synthesis is not economically profitable for commercial exploitation. A biotechnological alternative for their production is the use of plant cell and hairy root cultures. This review is focused on the biosynthesis of phytosterols and their function in both plants and humans as well as the different biotechnological strategies to increase phytosterol biosynthesis. Special attention is given to describing new methodologies based on the use of recombinant DNA technology to increase the levels of phytosterols.

    Topics: Anti-Inflammatory Agents; Antineoplastic Agents; Biological Availability; Biotechnology; Cholesterol; Empirical Research; Humans; Hypoglycemic Agents; Phytosterols; Plant Cells; Plants; Sitosterols; Stigmasterol

2016
Factors affecting intestinal absorption of cholesterol and plant sterols and stanols.
    Journal of oleo science, 2015, Volume: 64, Issue:1

    Various factors affect intestinal absorption of cholesterol and plant sterols and stanols. Plant sterols and stanols are generally less absorptive than cholesterol. Differential absorption rates among various plant sterols and stanols have been also reported. Although it was suggested that differential absorption among cholesterol and various plant sterols was determined by difference in excretion rates of sterols and stanols through ATP-binding cassette transporter (ABC) G5/ABCG8 of intestinal cells, our study suggests that affinity for and solubility in bile salt micelles can be important determinants for differential absorption of plant sterols and stanols. It was also suggested that plant sterols were transiently incorporated into intestinal cells and then excreted to intestinal lumen through ABCG5/ABCG8. However, in a rat study, transient incorporation of sitosterol into intestinal cells was not observed, suggesting that sitosterol is differentiated from cholesterol at the incorporation site of intestinal cells. It is well established that plant sterols inhibit intestinal absorption of cholesterol and exert a hypocholesterolemic activity. Plant sterols are solubilized in bile salt micelles as cholesterol. Our study clearly showed that because the sterol-solubilizing capacity of bile salt micelles was limited, plant sterols solubilized in micelles reduced the solubility of cholesterol. This can be the major cause of inhibition of cholesterol absorption by plant sterols. Pancreatic cholesterol esterase accelerates intestinal absorption of unesterified cholesterol. Although it was suggested that cholesterol esterase accelerated esterification of cholesterol incorporated into intestinal cells and acted as a transporter at the surface of intestinal cells, our research revealed that the accelerated cholesterol absorption was caused by hydrolysis of phosphatidylcholine in bile salt micelles. It is thought that hydrolysis of phosphatidylcholine reduces the affinity of cholesterol for the micelles and accelerates the incorporation of cholesterol released from the micelles into intestinal cells.

    Topics: Animals; Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile Acids and Salts; Cholesterol; Esterification; Humans; Hydrolysis; Intestinal Absorption; Intestinal Mucosa; Intestines; Lipoproteins; Micelles; Phosphatidylcholines; Phytosterols; Rats; Sitosterols; Solubility; Sterol Esterase

2015
Beta-Sitosterol: A Promising but Orphan Nutraceutical to Fight Against Cancer.
    Nutrition and cancer, 2015, Volume: 67, Issue:8

    All the currently available cancer therapeutic options are expensive but none of them are safe. However, traditional plant-derived medicines or compounds are relatively safe. One widely known such compound is beta-sitosterol (BS), a plant derived nutrient with anticancer properties against breast cancer, prostate cancer, colon cancer, lung cancer, stomach cancer, ovarian cancer, and leukemia. Studies have shown that BS interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation. Most of the studies are incomplete partly due to the fact that BS is relatively less potent. But the fact that it is generally considered as nontoxic, the opposite of all currently available cancer chemo-therapeutics, is missed by almost all research communities. To offset the lower efficacy of BS, designing BS delivery for "cancer cell specific" therapy hold huge potential. Delivery of BS through liposome is one of such demonstrations that has shown to be highly promising. But further research did not progress neither in the field of drug delivery of BS nor in the field on how BS mediated anticancer activities could be improved, thus making BS an orphan nutraceutical. Therefore, extensive research with BS as potent anticancer nutraceutical is highly recommended.

    Topics: Apoptosis; Breast Neoplasms; Cell Cycle; Colonic Neoplasms; Dietary Supplements; Drug Delivery Systems; Female; Humans; Leukemia; Liposomes; Lung Neoplasms; Male; Neoplasms; Orphan Drug Production; Phytoestrogens; Prostatic Neoplasms; Signal Transduction; Sitosterols

2015
Plant polyisoprenoids and control of cholesterol level.
    Archivum immunologiae et therapiae experimentalis, 2014, Volume: 62, Issue:1

    The ability of plant polyisoprenoids (polyprenols and polyprenyl phosphates) to diminish the levels of serum cholesterol affecting its biosynthetic pathway are highlighted here. Possible mechanism of such process is discussed. It is also noted that polyisoprenoids can prevent toxic injuries of the liver and restore disturbed hepatic functions. The possibility of polyprenyl phosphates to reveal at the same time anti-inflammatory action suppressing lipoxygenase activity and lowering the levels of proinflammatory cytokines will be illustrated. Attention will be focused on the potential usefulness of plant polyisoprenoids in the course of prevention and treatment of hypercholesterolemia. High efficiency for combined use of polyprenyl phosphate and β-sitosterol, which leads to substantial enhancement of the ability to overcome hypercholesterolemia versus the individual constituents will be demonstrated.

    Topics: Animals; Anti-Inflammatory Agents; Antineoplastic Combined Chemotherapy Protocols; Chemical and Drug Induced Liver Injury; Cholesterol; Humans; Hypercholesterolemia; Lipoxygenase; Phytotherapy; Plants; Sitosterols; Terpenes

2014
Plant sterols as anticancer nutrients: evidence for their role in breast cancer.
    Nutrients, 2013, Jan-31, Volume: 5, Issue:2

    While many factors are involved in the etiology of cancer, it has been clearly established that diet significantly impacts one's risk for this disease. More recently, specific food components have been identified which are uniquely beneficial in mitigating the risk of specific cancer subtypes. Plant sterols are well known for their effects on blood cholesterol levels, however research into their potential role in mitigating cancer risk remains in its infancy. As outlined in this review, the cholesterol modulating actions of plant sterols may overlap with their anti-cancer actions. Breast cancer is the most common malignancy affecting women and there remains a need for effective adjuvant therapies for this disease, for which plant sterols may play a distinctive role.

    Topics: Anticholesteremic Agents; Antineoplastic Agents; Apoptosis; Breast Neoplasms; Cell Membrane; Cholesterol; Estrogens; Female; Glucose; Humans; Immunity; Inflammation; Liver X Receptors; Orphan Nuclear Receptors; Oxidative Stress; Phytosterols; Receptors, Estrogen; Risk Factors; Signal Transduction; Sitosterols

2013
Ocimum sanctum L (Holy Basil or Tulsi) and its phytochemicals in the prevention and treatment of cancer.
    Nutrition and cancer, 2013, Volume: 65 Suppl 1

    Ocimum sanctum L. or Ocimum tenuiflorum L, commonly known as the Holy Basil in English or Tulsi in the various Indian languages, is a important medicinal plant in the various traditional and folk systems of medicine in Southeast Asia. Scientific studies have shown it to possess antiinflammatory, analgesic, antipyretic, antidiabetic, hepatoprotective, hypolipidemic, antistress, and immunomodulatory activities. Preclinical studies have also shown that Tulsi and some of its phytochemicals eugenol, rosmarinic acid, apigenin, myretenal, luteolin, β-sitosterol, and carnosic acid prevented chemical-induced skin, liver, oral, and lung cancers and to mediate these effects by increasing the antioxidant activity, altering the gene expressions, inducing apoptosis, and inhibiting angiogenesis and metastasis. The aqueous extract of Tulsi and its flavanoids, orintin, and vicenin are shown to protect mice against γ-radiation-induced sickness and mortality and to selectively protect the normal tissues against the tumoricidal effects of radiation. The other important phytochemicals like eugenol, rosmarinic acid, apigenin, and carnosic acid are also shown to prevent radiation-induced DNA damage. This review summarizes the results related to the chemopreventive and radioprotective properties of Tulsi and also emphasizes aspects that warrant future research to establish its activity and utility in cancer prevention and treatment.

    Topics: Abietanes; Animals; Apigenin; Cinnamates; Depsides; Disease Models, Animal; Drug Evaluation, Preclinical; Eugenol; Humans; Luteolin; Neoplasms; Ocimum; Phytochemicals; Plant Extracts; Plants, Medicinal; Rosmarinic Acid; Sitosterols

2013
Perioperative statin therapy for improving outcomes during and after noncardiac vascular surgery.
    The Cochrane database of systematic reviews, 2013, Jul-03, Issue:7

    Patients undergoing vascular surgery are a high-risk population with widespread atherosclerosis, an adverse cardiovascular risk profile and often multiple co-morbidities. Postoperative cardiovascular complications, including myocardial infarct (MI), are common. Statins are the medical treatment of choice to reduce high cholesterol levels. Evidence is accumulating that patients taking statins at the time of surgery are protected against a range of perioperative complications, but the specific benefits for patients undergoing noncardiac vascular surgery are not clear.. We examined whether short-term statin therapy, commenced before or on the day of noncardiac vascular surgery and continuing for at least 48 hours afterwards, improves patient outcomes including the risk of complications, pain, quality of life and length of hospital stay. We also examined whether the effect of statin therapy on these outcomes changes depending on the dose of statin received.. We searched the Cochrane Central Register of Controlled Trials (CENTRAL) (The Cochrane Library 2012, Issue 7), MEDLINE via Ovid SP (1966 to August 2012), EMBASE via Ovid SP (1966 to August 2012), CINAHL via EBSCO host (1966 to August 2012) and ISI Web of Science (1946 to July 2012) without any language restriction. We used a combination of free text search and controlled vocabulary search. The results were limited to randomized controlled clinical trials (RCTs). We conducted forwards and backwards citation of key articles and searched two clinical trial Websites for ongoing trials (www.clinicaltrials.gov and http://www.controlled-trials.com).. We included RCTs that had compared short-term statin therapy, either commenced de novo or with existing users randomly assigned to different dosages, in adult participants undergoing elective and emergency noncardiac arterial surgery, including both open and endovascular procedures. We defined short-term as commencing before or on the day of surgery and continuing for at least 48 hours afterwards.. Two authors independently assessed trial quality and extracted data, including information on adverse events. We contacted study authors for additional information. We performed separate analyses for the comparisons of statin with placebo/no treatment and between different doses of statin. We presented results as pooled risk ratios (RRs) with 95% confidence intervals (CIs) based on random-effects models (inverse variance method). We employed the Chi(2) test and calculated the I(2) statistic to investigate study heterogeneity.. We identified six eligible studies in total. The six Included studies were generally of high quality, but the largest eligible study was excluded because of concerns about its validity. Study populations were statin naive, which led to a considerable loss of eligible participants.Five RCTs compared statin use with placebo or standard care. We pooled results from three studies, with a total of 178 participants, for mortality and non-fatal event outcomes. In the statin group, 7/105 (6.7%) participants died within 30 days of surgery, as did 10/73 (13.7%) participants in the control group. Only one death in each group was from cardiovascular causes, with an incidence of 0.95% in statin participants and 1.4% in control participants, respectively. All deaths occurred in a single study population, and so effect estimates were derived from one study only. The risk ratio (RR) of all-cause mortality in statin users showed a non-significant decrease in risk (RR 0.73, 95% CI 0.31 to 1.75). For cardiovascular death, the risk ratio was 1.05 (95% CI 0.07 to 16.20). Non-fatal MI within 30 days of surgery was reported in three studies and occurred in 4/105 (3.8%) participants in the statin group and 8/73 (11.0%) participants receiving placebo, for a non-significant decrease in risk (RR 0.47, 95% CI 0.15 to 1.52). Several studies reported muscle enzyme levels as safety measures, but only three (with a total of 188 participants) reported explicitly on clinical muscle syndromes, with seven events reported and no significant difference found between statin users and controls (RR 0.94, 95% CI 0.24 to 3.63). The only participant-reported outcome was nausea in one small study,with no significant difference in risk between groups.Two studies compared different doses of atorvastatin, with a total of 145 participants, but reported data were not sufficient to allow us to determine the effect of higher doses on any outcome.. Evidence was insufficient to allow review authors to conclude that statin use resulted in either a reduction or an increase in any of the outcomes examined. The existing body of evidence leaves questions about the benefits of perioperative use of statins for vascular surgery unanswered. Widespread use of statins in the target population means that it may now be difficult for researchers to undertake the large RCTs needed to demonstrate any effect on the incidence of postoperative cardiovascular events. However, participant-reported outcomes have been neglected and warrant further study.

    Topics: Adult; Angioplasty; Atherosclerosis; Atorvastatin; Cardiovascular Diseases; Cause of Death; Cholestyramine Resin; Heptanoic Acids; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Lovastatin; Perioperative Care; Postoperative Complications; Pyrroles; Randomized Controlled Trials as Topic; Sitosterols; Vascular Surgical Procedures

2013
Consumption of plant sterol-enriched foods and effects on plasma plant sterol concentrations--a meta-analysis of randomized controlled studies.
    Atherosclerosis, 2013, Volume: 230, Issue:2

    Intake of plant sterol (PS)-enriched foods effectively lowers plasma total- and LDL-cholesterol concentrations while increasing plasma PS concentrations. The magnitude of this increase has not been systematically assessed. This study aimed to investigate the effect of PS-enriched foods on plasma PS concentrations by performing a meta-analysis of randomized controlled studies.. Published PS intervention studies reporting plasma PS concentrations were searched through June 2012. Studies were selected that fulfilled pre-defined in- and exclusion criteria. Data were extracted, particularly on campesterol, sitosterol, total- and LDL-cholesterol. Random-effects models were used to calculate net effects while weighing each study by the inverse of its variance. Potential sources of heterogeneity were investigated.. The meta-analysis included data from 41 studies (55 strata) with in total 2084 subjects. The average dose of PS from enriched foods was 1.6 g/d (range: 0.3-3.2 g/d). Plasma sitosterol and campesterol concentrations were increased by on average 2.24 μmol/L (31%) and 5.00 μmol/L (37%), respectively, compared to control. Total- and LDL-cholesterol were reduced by on average 0.36 mmol/L (5.9%) and 0.33 mmol/L (8.5%), respectively. The increase in sitosterol and campesterol was impacted by the dose of PS, the baseline PS concentration and the PS composition of the test products. In the highest PS dose category (2.0-3.2 g/d), increases in sitosterol and campesterol were on average 3.56 and 7.64 μmol/L, respectively.. Intake of PS-enriched foods increases plasma sitosterol and campesterol concentrations. However, total PS remain below 1% of total sterols circulating in the blood.

    Topics: Cholesterol; Cholesterol, LDL; Diet; Food, Fortified; Humans; Phytosterols; Randomized Controlled Trials as Topic; Risk Factors; Sitosterols

2013
Dietary phosphilipids and sterols protective against peptic ulceration.
    Phytotherapy research : PTR, 2013, Volume: 27, Issue:9

    The prevalence of duodenal ulceration in regions of developing countries with a stable diet is related to the staple food(s) in that diet. A higher prevalence occurs in areas where the diet is principally milled rice, refined wheat or maize, yams, cassava, sweet potato or green bananas, and a lower prevalence in areas where the staple diet is based on unrefined wheat or maize, soya, certain millets or certain pulses. Experiments using animal peptic ulcer models showed that the lipid fraction in foods from the staple diets of low prevalence areas gave protection against both gastric and duodenal ulceration, including ulceration due to non-steroidal anti-inflammatory drugs (NSAIDs), and also promoted healing of ulceration. The protective activity was found to lie in the phospholipid, sterol and sterol ester fractions of the lipid. Amongst individual phospholipids present in the phospholipid fraction, phosphatidyl ethanolamine (cephalin) and phosphatidyl choline (Lecithin) predominated. The sterol fraction showing activity contained β-sitosterol, stigmasterol and an unidentified isomer of β-sitosterol. The evidence shows that dietary phytosterols and phospholipids, both individually and in combination, have a protective effect on gastroduodenal mucosa. These findings may prove to be important in the prevention and management of duodenal and gastric ulceration including ulceration due to NSAIDs.

    Topics: Animals; Diet; Disease Models, Animal; Duodenal Ulcer; Humans; Phospholipids; Phytosterols; Sitosterols

2013
Plant sterols and atherosclerosis.
    Current opinion in lipidology, 2013, Volume: 24, Issue:1

    Plant sterols as ingredients to functional foods are recommended for lowering LDL cholesterol. However, there is an ongoing discussion whether the use of plant sterols is safe.. Genetic analyses showed that common variants of the ATP binding cassette transporter G8 (ABCG8) and ABO genes are associated with elevated circulating plant sterols and higher risk for cardiovascular disease. However, these data do not prove a causal role for plant sterols in atherosclerosis because the risk alleles in ABCG8 and ABO are also related to elevated total and LDL cholesterol levels. The ABO locus exhibits still further pleiotropy. Moreover, analyses in the general population indicated that moderately elevated circulating plant sterols are not correlated with present or future vascular disease. In agreement, novel studies using food frequency questionnaires, studies in experimental animals, and dietary intervention studies support that ingestion of plant sterols may be beneficial to cardiovascular health.. Taken together, current evidence supports the recommendations for the use of plant sterols as LDL cholesterol-lowering agents. Nevertheless, a prospective, randomized, controlled, double-blinded, intervention trial conclusively showing that plant sterol supplementation will prevent hard cardiovascular endpoints is not available to date.

    Topics: Alleles; Animals; Anticholesteremic Agents; Atherosclerosis; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Azetidines; Cholesterol, LDL; Ezetimibe; Genetic Loci; Humans; Lipoproteins; Phytosterols; Phytotherapy; Randomized Controlled Trials as Topic; Risk Factors; Sitosterols

2013
Nutrition and benign prostatic hyperplasia.
    Current opinion in urology, 2013, Volume: 23, Issue:1

    Nutrition seems to modify the pathogenesis of benign prostatic hyperplasia (BPH) effect symptomology in men suffering from lower urinary tract symptoms (LUTS). Although there are numerous pharmaceuticals and procedures for these conditions, nutrition may improve outcomes as a primary approach or in tandem with BPH medications or procedures. The purpose of this review is to highlight the benefits of nutrition and dietary supplements in men with BPH and LUTS.. Dietary factors have an impact on metabolic disorders that lead to diabetes and obesity - both of which inversely effect BPH and LUTS. Dietary patterns associated with increased risks include starches and red meats, whereas moderate alcohol intake and polyunsaturated fat and vegetable consumption decrease risks. Dietary supplements of zinc, saw palmetto, and beta-sitosterol in relieving BPH symptoms have had mixed results. Randomized clinical trials of nutritional practices and other lifestyle alterations such as exercise for the prevention or treatment of BPH and LUTS have yet to be performed.. Nutritional practices may provide for the prevention and treatment of BPH and LUTS while positively affecting other systemic parameters. Whereas there are a few clinical randomized trials for the prevention and treatment of BPH and LUTS, nutritional modifications may have a healthy lifestyle alternative with minimal to no adverse effects.

    Topics: Dietary Supplements; Humans; Life Style; Lower Urinary Tract Symptoms; Male; Nutrition Therapy; Plant Extracts; Prostatic Hyperplasia; Secale; Sitosterols

2013
Plant sterols and cardiovascular disease: a systematic review and meta-analysis.
    European heart journal, 2012, Volume: 33, Issue:4

    The impact of increased serum concentrations of plant sterols on cardiovascular risk is unclear. We conducted a systematic review and meta-analysis aimed to investigate whether there is an association between serum concentrations of two common plant sterols (sitosterol, campesterol) and cardiovascular disease (CVD). We systematically searched the databases MEDLINE, EMBASE, and COCHRANE for studies published between January 1950 and April 2010 that reported either risk ratios (RR) of CVD in relation to serum sterol concentrations (either absolute or expressed as ratios relative to total cholesterol) or serum sterol concentrations in CVD cases and controls separately. We conducted two meta-analyses, one based on RR of CVD contrasting the upper vs. the lower third of the sterol distribution, and another based on standardized mean differences between CVD cases and controls. Summary estimates were derived by fixed and random effects meta-analysis techniques. We identified 17 studies using different designs (four case-control, five nested case-control, three cohort, five cross-sectional) involving 11 182 participants. Eight studies reported RR of CVD and 15 studies reported serum concentrations in CVD cases and controls. Funnel plots showed evidence for publication bias indicating small unpublished studies with non-significant findings. Neither of our meta-analyses suggested any relationship between serum concentrations of sitosterol and campesterol (both absolute concentrations and ratios to cholesterol) and risk of CVD. Our systematic review and meta-analysis did not reveal any evidence of an association between serum concentrations of plant sterols and risk of CVD.

    Topics: Cardiovascular Diseases; Cholesterol; Diet; Epidemiologic Methods; Humans; Phytosterols; Publication Bias; Risk Factors; Sitosterols

2012
Dietary supplements for benign prostatic hyperplasia: an overview of systematic reviews.
    Maturitas, 2012, Volume: 73, Issue:3

    Benign prostatic hyperplasia (BPH) is a common chronic condition in older men. The aim of this overview of systematic reviews (SRs) is to summarise the current evidence on the efficacy and adverse effects of dietary supplements for treating BPH with lower urinary tract symptoms. We searched 5 electronic databases and relevant overviews without limitations on language or publication status. Six SRs of 195 articles were included in this overview. Serenoa repens was reviewed in 3 studies and no specific effect on BPH symptoms and urinary flow measures was observed. However, β-sitosterol, Pygeum africannum and Cernilton were reviewed in one study each, and significant improvement was observed for all three. All the included compounds have mild and infrequent adverse effects. SRs on β-sitosterol, Pygeum africannum and Cernilton have not been updated since 2000, thus an update of reviews on these compounds will be necessary in the future.

    Topics: Dietary Supplements; Humans; Male; Phytotherapy; Plant Extracts; Prostatic Hyperplasia; Prunus africana; Secale; Serenoa; Sitosterols; Treatment Outcome; Urologic Diseases

2012
Patterns of cholesterol metabolism: pathophysiological and therapeutic implications for dyslipidemias and the metabolic syndrome.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2011, Volume: 21, Issue:9

    Investigating cholesterol metabolism, which derives from balancing cholesterol synthesis and absorption, opens new perspectives in the pathogenesis of dyslipidemias and the metabolic syndrome (MS). Cholesterol metabolism is studied by measuring plasma levels of campesterol, sitosterol and cholestanol, that is, plant sterols which are recognised as surrogate cholesterol-absorption markers and lathosterol or squalene, that is, cholesterol precursors, which are considered surrogate cholesterol-synthesis markers. This article presents current knowledge on cholesterol synthesis and absorption, as evaluated by means of cholesterol precursors and plant sterols, and discusses patterns of cholesterol balance in the main forms of primary hyperlipidaemia and MS. Understanding the mechanism(s) underlying these patterns of cholesterol synthesis and absorption will help to predict the response to hypolipidemic treatment, which can then be tailored to ensure the maximum clinical benefit for patients.

    Topics: Biomarkers; Cholestanol; Cholesterol; Dyslipidemias; Humans; Lipid Metabolism; Metabolic Syndrome; Phytosterols; Sitosterols

2011
Current pharmacological and phytochemical studies of the plant Alpinia galanga.
    Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine, 2011, Volume: 9, Issue:10

    Traditional medicine systems consist of large numbers of plants with medicinal and pharmacological importance and hence represent an invaluable reservoir of new bioactive molecules. Alpinia galanga (family Zingiberaceae) is commonly known as galangal and has been used for its emmenagogue, aphrodisiac, abortifacient, carminative, antipyretic and anti-inflammatory qualities and used in the treatment of various diseases such as bronchitis, heart diseases, chronic enteritis, renal calculus, diabetes, rheumatism and kidney disorders. It was reported to contain, among other components, essential oils, tannins, phenol, glycosides, monoterpenes and carbohydrates. In the last few years, new compounds such as gallic acid glycoside, galangoisoflavonoid,β-sitosterol, galangin, alpinin, zerumbone and kampferide have been isolated from various parts of A. galanga. Therefore, the present review is aimed to summarize the information regarding A. galanga concerning the new phytoconstituents and pharmacological uses that have appeared in recent years.

    Topics: Alpinia; Flavonoids; Plant Extracts; Rhizome; Sitosterols

2011
Current therapy for patients with sitosterolemia--effect of ezetimibe on plant sterol metabolism.
    Journal of atherosclerosis and thrombosis, 2010, Sep-30, Volume: 17, Issue:9

    Sitosterolemia is a rare, autosomal recessive inherited sterol storage disease associated with high tissue and serum plant sterol concentrations, caused by mutations in the adenosine triphosphate-bind-ing cassette (ABC) transporter ABCG5 or ABCG8 genes. Markedly increased serum concentration of plant sterols. such as sitosterol and campesterol, cause premature atherosclerosis and massive xanthomas. Hitherto known treatments for sitosterolemia, including a low-sterol diet, bile-salt binding resins, ileal bypass surgery and low density lipoprotein (LDL) apheresis have not yielded sufficient reduction of serum plant sterol levels and many patients show a sustained elevation of plant sterol levels, subsequently developing premature atherosclerotic cardiovascular diseases. Ezetimibe, an inhibitor of intestinal cholesterol absorption through its binding to Niemann-Pick C1-like 1 (NPC1L1), has been widely used for decreasing serum LDL-cholesterol levels in patients with hypercholesterolemia. Ezetimibe also reduces the gastrointestinal absorption of plant sterols, thereby also lowering the serum concentrations of plant sterols. This pharmacological property of ezetimibe shows its potential as a novel effective therapy for sitosterolemia. In the current review, we discuss the current therapy for patients with sitosterolemia and present two Japanese adolescent patients with this disease, one of whom underwent percutaneous coronary intervention for accelerated coronary atherosclerosis. Ezetimibe administration in addition to conventional drug therapy successfully reduced serum sitosterol levels by 51.3% and 48.9%, respectively, in the two patients, demonstrating ezetimibe as a novel and potent treatment agent for sitosterolemia that could work additively with conventional drug therapy.

    Topics: Adolescent; Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Azetidines; Bile Acids and Salts; Cardiovascular Diseases; Ezetimibe; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Ileum; Ion Exchange Resins; Lipid Metabolism, Inborn Errors; Lipoproteins; Male; Models, Biological; Mutation, Missense; Phytosterols; Sitosterols; Young Adult

2010
Steroidal triterpenes: design of substrate-based inhibitors of ergosterol and sitosterol synthesis.
    Molecules (Basel, Switzerland), 2009, Nov-18, Volume: 14, Issue:11

    This article reviews the design and study, in our own laboratory and others, of new steroidal triterpenes with a modified lanosterol or cycloartenol frame. These compounds, along with a number of known analogs with the cholestane skeleton, have been evaluated as reversible or irreversible inhibitors of sterol C24-methyltransferase (SMT) from plants, fungi and protozoa. The SMT catalyzes the C24-methylation reaction involved with the introduction of the C24-methyl group of ergosterol and the C24-ethyl group of sitosterol, cholesterol surrogates that function as essential membrane inserts in many photosynthetic and non-photosynthetic eukaryotic organisms. Sterol side chains constructed with a nitrogen, sulfur, bromine or fluorine atom, altered to possess a methylene cyclopropane group, or elongated to include terminal double or triple bonds are shown to exhibit different in vitro activities toward the SMT which are mirrored in the inhibition potencies detected in the growth response of treated cultured human and plant cells or microbes. Several of the substrate-based analogs surveyed here appear to be taxaspecific compounds acting as mechanism-based inactivators of the SMT, a crucial enzyme not synthesized by animals. Possible mechanisms for the inactivation process and generation of novel products catalyzed by the variant SMTs are discussed.

    Topics: Enzyme Activation; Ergosterol; Methyltransferases; Molecular Structure; Sitosterols; Triterpenes

2009
Effects of yoghurt enriched with free plant sterols on the levels of serum lipids and plant sterols in moderately hypercholesterolaemic subjects on a high-fat diet.
    International journal of food sciences and nutrition, 2008, Volume: 59, Issue:5

    This study examined the effect of plant sterols added, together with an emulsifying agent, to a low-fat yoghurt on the serum lipid and plant sterol values in moderately hypercholesterolaemic volunteers. Study I was a randomized double-blind, cross-over trial. For 4 weeks, 15 volunteers consumed yoghurt containing 1 g plant sterols or a placebo yoghurt. Study II was a randomized, double-blind, parallel-group study. For 8 weeks, the sterol group (n = 12) ingested daily two yoghurts (2 g/day plant sterols) and the placebo group (n = 14) ingested two yoghurts without plant sterols. Study I: compared with the placebo, the sterol yoghurt reduced serum total cholesterol by 0.15 mmol/l (2.2%, P=0.235) and low-density lipoprotein (LDL) cholesterol by 0.19 mmol/l (4.3%, P=0.082), and increased serum campesterol by 0.26 mg/100 ml (P=0.006) and sitosterol by 0.11 mg/100 ml (P=0.015). Study II: compared with the placebo, the sterol yoghurt reduced serum total cholesterol by 0.41 mmol/l (6.3%, P=0.167) and LDL cholesterol by 0.28 mmol/l (6.4%, P=0.306), and increased serum campesterol by 0.28 mg/100 ml (P=0.016) and sitosterol by 0.40 mg/100 ml (P=0.206). Meta-analysis: the pooled treatment difference was -0.34 mmol/l (5.2%, P=0.173) in total cholesterol and was -0.26 mmol/l (-5.8%, P=0.261) in LDL cholesterol, when the sterol yoghurt was compared with the placebo. A low-fat yoghurt enriched with 1-2 g/day plant sterols reduced serum cholesterol levels in moderately hypercholesterolaemic subjects. Campesterol and sitosterol serum levels increased, but their concentration remained in the range of normal values.

    Topics: Adult; Analysis of Variance; Anticholesteremic Agents; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Double-Blind Method; Female; Humans; Hypercholesterolemia; Lipids; Male; Middle Aged; Phytosterols; Sitosterols; Yogurt

2008
Sterolins ABCG5 and ABCG8: regulators of whole body dietary sterols.
    Pflugers Archiv : European journal of physiology, 2007, Volume: 453, Issue:5

    ABCG5 and ABCG8 are two ATP-binding cassette half-transporters that belong to the G family members. They were identified as proteins that are mutated in a rare human disorder, sitosterolemia, and their identification led to the completion of the physiological pathways by which dietary cholesterol, as well as noncholesterol sterols, traffics in the mammalian body. These proteins are likely to function as heterodimers, and current evidence suggests that these proteins are responsible for the majority of sterol secretions into bile, thus may define the long sought-after biliary sterol transporters. This review will focus on some of the backgrounds of this physiology, the genetics and regulation of these genes, as well as our current understanding of their functions. This review will also highlight the current limitations in our knowledge gap.

    Topics: Amino Acid Sequence; Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Cholesterol, Dietary; Gene Expression Regulation; Humans; Lipoproteins; Molecular Sequence Data; Phytosterols; Sequence Alignment; Sitosterols

2007
ATP-binding cassette, subfamily G (ABCG family).
    Pflugers Archiv : European journal of physiology, 2007, Volume: 453, Issue:5

    This review summarizes the characteristics of the ATP-binding cassette, subfamily G (ABCG family), which has five members: ABCG1, ABCG2, ABCG4, ABCG5, and ABCG8. The members consist of a single ABC cassette in the amino terminal followed by six putative transmembrane domains, and to become functionally active, they form homo- or obligate heterodimers. Except for ABCG2, the members of the ABCG family play an important role in efflux transport of cholesterol. Mutations causing a loss of function of ABCG5 or ABCG8 are associated with sitosterolemia characterized by accumulation of phyto- and shellfish sterols. Unlike other members, ABCG2 is not involved in cholesterol efflux, but it exhibits broad substrate specificity to xenobiotic compounds. ABCG2 confers cancer cells resistance to anticancer drugs and plays a critical role in the pharmacokinetics of drugs in the clearance organs and tissue barriers. ABCG2 is also associated with a subpopulation phenotype of stem cells. Genetic polymorphisms of ABCG2 have been suggested to account for the interindividual differences in the pharmacokinetics of drugs.

    Topics: Animals; ATP Binding Cassette Transporter, Subfamily G; ATP Binding Cassette Transporter, Subfamily G, Member 1; ATP Binding Cassette Transporter, Subfamily G, Member 2; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Cholesterol; Gene Expression Regulation; Humans; Lipoproteins; Mice; Neoplasm Proteins; Phylogeny; Sitosterols

2007
[Change in the cholesterol metabolism associated with the combined inhibition of synthesis and absorption].
    Orvosi hetilap, 2007, Apr-08, Volume: 148, Issue:14

    Lowering lipid levels in the cardiovascular prevention we confine ourselves to measure the cholesterol level and care less for the background effects. Namely blood cholesterol level beyond the amount consumed with the diet highly depends on balance of intestinal absorption/secretion and synthesis. Studying the rate of absorption and synthesis has come only recently into the foreground of interest. Many observations proved that using even the strongest cholesterol lowering drug - beyond reducing the synthesis in the liver - may be associated with an up to 50 percent increase of the intestinal cholesterol absorption. When studying the effectiveness of statins in everyday practice we measure only the decrease of serum cholesterol level as the final result, and do not examine the changes in the synthesis and absorption. The amount of cholesterol synthesized or absorbed can be determined in an indirect way by measuring that of the non-cholesterol sterols (phytosterols). The absorption markers are campesterol, sitosterol, avenasterol as well as cholestanol. The biosynthesis of cholesterol correlates with the level of lathosterol, cholestanol, desmostenol. In practice the concentration of lathosterol or lathosterol/cholesterol can be considered the marker of synthesis and the campesterol or campesterol/cholesterol ratio the marker of absorption. So recent study results show that while inhibiting the cholesterol synthesis with statin the cholesterol absorption increases and the absorption inhibitor ezetimibe is associated with boost of synthesis. The increase in absorption caused by statins can be reduced or prevented by combining with ezetimibe. These data confirm that combination of statin and ezetimibe, inhibiting simultaneously both the synthesis and absorption provides the most effective cholesterol-level lowering with the least side-effects.

    Topics: Anticholesteremic Agents; Azetidines; Biomarkers; Cholestanol; Cholesterol; Cholesterol, Dietary; Ezetimibe; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Intestinal Absorption; Phytosterols; Sitosterols

2007
Efficacy and safety of sitosterol in the management of blood cholesterol levels.
    Cardiovascular drug reviews, 2005,Spring, Volume: 23, Issue:1

    Elevated levels of plasma LDL cholesterol (LDL-C) represent a major risk factor for cardiovascular disease. Treatments aimed at reducing levels of circulating LDL are regarded, therefore, as cardioprotective. The cholesterol lowering properties of plant sterols have been known for some time and many clinical studies have confirmed the efficacy of sitosterol in lowering plasma LDL-C concentrations. Animal studies have also shown reductions in LDL by sitosterol. The use of animal models has been useful in facilitating the elucidation of specific mechanisms by which this sterol exerts its hypocholesterolemic action. It is well known that plant sterols compete with cholesterol for space within bile salt micelles in the intestinal lumen thereby reducing cholesterol absorption. The understanding of the function of plant sterols in impeding cholesterol absorption has been clarified with the discovery of the adenosine binding cassette transporters, ABCG5/8, involved in the regulation of sterol absorption and secretion into the enterocyte and hepatocyte. Compared to cholesterol and other sterols, sitosterol is preferentially pumped out to the intestinal lumen by the ABCG5/8 transporters. This selective binding of sitosterol to the transporters ultimately results in significant lowering of plasma cholesterol. However, some findings support the hypothesis that plant sterols might be an additional risk factor for coronary heart disease. From the review of these studies, it is apparent that sitosterol is a useful dietary supplement for the lowering of plasma cholesterol. Nevertheless, this plant sterol should be used with caution in certain individuals who have a higher absorption rate of sitosterol.

    Topics: Animals; Cholesterol, LDL; Contraindications; Dietary Supplements; Humans; Sitosterols

2005
Taraxasterol and beta-sitosterol: new naturally compounds with chemoprotective/chemopreventive effects.
    Neoplasma, 2004, Volume: 51, Issue:6

    Substantial attention has been given to primary cancer prevention in daily life. Dietary factors are through to contribute to as much as one-third of the factors influencing the development of cancer. Ones of the components of a plant-based diet are beta-sitosterol and taraxasterol, compounds attracting our specific attention. This review summarizes the biological activities of presented phytosterols (anti-inflammatory, cholesterol-lowering, anti-microbial, anti-bacterial, anti-fungal effects). Our interest has been focussed especially on their anti-tumor and chemopreventive activity. They have been shown experimentally to inhibit colon and breast cancer development. They act at various stages of tumor development, including inhibition of tumorigenesis, inhibition of tumor promotion, and induction of cell differentiation. They effectively inhibit invasion of tumor cells and metastasis. With regard to toxicity, no obvious side effects of phytosterols have been observed in studies to date, with the exception of individuals with phytosterolemia. The exact mechanism by which dietary phytosterols act is not fully understood. However, some mechanisms have been offered. Therefore, they have a bright future in clinical application. Further investigation to explore their potential in tumor treatment may prove to be worthwhile.

    Topics: Animals; Anti-Inflammatory Agents; Anticarcinogenic Agents; Antineoplastic Agents; Antioxidants; Breast Neoplasms; Colonic Neoplasms; Diet; Drugs, Chinese Herbal; Female; Humans; Phytosterols; Sitosterols; Sterols; Triterpenes

2004
Benign prostatic hyperplasia.
    Clinical evidence, 2004, Issue:11

    Topics: 5-alpha Reductase Inhibitors; Adrenergic alpha-Antagonists; Humans; Lolium; Male; Phytotherapy; Plant Extracts; Pollen; Prostatic Hyperplasia; Serenoa; Sitosterols; Transurethral Resection of Prostate

2004
The role of sterols in plant growth and development.
    Progress in lipid research, 2003, Volume: 42, Issue:3

    Sterols found in all eukaryotic organisms are membrane components which regulate the fluidity and the permeability of phospholipid bilayers. Certain sterols in minute amounts, such as campesterol in Arabidopsis thaliana, are precursors of oxidized steroids acting as growth hormones collectively named brassinosteroids. The crucial importance of brassinosteroids upon growth and development has been established through the study of a set of dwarf mutants affected in brassinosteroid synthesis or perception. Some of these dwarfs are, in fact, deficient in the final steps of sterol biosynthesis and their developmental phenotypes are primarily caused by a depletion in the sterol precursor for brassinosteroids. Recently, the characterization of genes encoding sterol biosynthetic enzymes and the isolation of novel plant lines affected in the expression of those genes, either by insertional or classical mutagenesis, overexpression or cosuppression, have shed new light on the involvement of sterols in biological processes such as embryonic development, cell and plant growth, and fertility, which will be presented and discussed in this review article.

    Topics: Arabidopsis; Cholesterol; Mutation; Phytosterols; Plant Development; Sitosterols

2003
Monogenic hypercholesterolemia: new insights in pathogenesis and treatment.
    The Journal of clinical investigation, 2003, Volume: 111, Issue:12

    Topics: Apolipoprotein B-100; Apolipoproteins B; Coronary Artery Disease; Genes, Dominant; Genes, Recessive; History, 20th Century; Humans; Hyperlipoproteinemia Type II; Lipoproteins, LDL; Sitosterols

2003
Benign prostatic hyperplasia.
    Clinical evidence, 2003, Issue:10

    Topics: 5-alpha Reductase Inhibitors; Adrenergic alpha-Antagonists; Adult; Humans; Lolium; Male; Phytotherapy; Plant Extracts; Pollen; Prostatic Hyperplasia; Serenoa; Sitosterols; Transurethral Resection of Prostate

2003
Phytotherapy for benign prostatic hyperplasia.
    Current urology reports, 2002, Volume: 3, Issue:4

    Phytotherapy has become a more popular treatment option among American men with benign prostatic hyperplasia (BPH). The most popular herbal agent is saw palmetto (Serenoa repens), which is derived from the berry of the American dwarf palm tree. Pygeum africanum and beta-sitosterol are also used by many patients with BPH, either alone or in combination with saw palmetto. A significant limiting factor to our understanding of the use and effectiveness of phytotherapy is the lack of standardization of these products. Despite this lack of standardization and the variation in results that may be seen with herbal products, there is growing evidence from well-conducted clinical trials that phytotherapeutic agents may lead to subjective and objective symptom improvement beyond a placebo effect in men with BPH. In addition, histologic evidence has been presented demonstrating that saw palmetto causes atrophy and epithelial contraction within the prostate gland. Overall, it is likely that herbal therapy will continue to be used by a growing number of Americans to treat a variety of ailments. Physicians should attempt to remain open-minded regarding alternative approaches and educate themselves so that they may counsel patients in an informed and credible fashion.

    Topics: Androgen Antagonists; Humans; Male; Phytotherapy; Plant Extracts; Pollen; Prostate; Prostatic Hyperplasia; Prunus; Serenoa; Sitosterols; Urodynamics

2002
Arabidopsis mutants reveal multiple roles for sterols in plant development.
    The Plant cell, 2002, Volume: 14, Issue:9

    Topics: Arabidopsis; Brassinosteroids; Cell Membrane; Cell Wall; Cholestanols; Cholesterol; Mutation; Phytosterols; Signal Transduction; Sitosterols; Steroids, Heterocyclic

2002
Genetic defenses against hypercholesterolemia.
    Cold Spring Harbor symposia on quantitative biology, 2002, Volume: 67

    Topics: Adaptor Proteins, Signal Transducing; Adaptor Proteins, Vesicular Transport; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile; Chromosomes, Human, Pair 1; Endocytosis; Genes, Recessive; Humans; Hyperlipoproteinemia Type II; Lipoproteins; Mutation; Receptors, LDL; Sitosterols; Sterols

2002
[A review of the study on Schefflera plants: chemical constituents and physiological activities].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2002, Volume: 25, Issue:5

    Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Anticonvulsants; Antihypertensive Agents; Araliaceae; Oleanolic Acid; Plants, Medicinal; Sitosterols

2002
Choosing the best pulse sequences, acquisition parameters, postacquisition processing strategies, and probes for natural product structure elucidation by NMR spectroscopy.
    Journal of natural products, 2002, Volume: 65, Issue:2

    The relative merits of different pairs of two-dimensional NMR pulse sequences (COSY-90 vs COSY-45, NOESY vs T-ROESY, HSQC vs HMQC, HMBC vs CIGAR, etc.) are compared and recommendations are made for the preferred choice of sequences for natural product structure elucidation. Similar comparisons are made between different selective 1D sequences and the corresponding 2D sequences. Many users of 2D NMR use longer than necessary relaxation delays and neglect to use forward linear prediction processing. It is shown that using shorter relaxation delays in combination with forward linear prediction allows one to get better resolved spectra in less time. The relative merits of different probes and likely future probe developments are also discussed.

    Topics: Biological Factors; Diterpenes; Epoxy Compounds; Furans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Sesquiterpenes; Sitosterols; Time Factors

2002
Cerebrotendinous xanthomatosis: a rare disease with diverse manifestations.
    Archives of neurology, 2002, Volume: 59, Issue:4

    This mini-review deals with a new appraisal of cerebrotendinous xanthomatosis. In addition to neurologic symptoms, patients with cerebrotendinous xanthomatosis develop cataracts, diarrhea, Achilles tendon xanthoma, atherosclerotic vascular disease, and many other abnormalities. Although the pathophysiology of the disease is not completely understood, excess production and consequent accumulation of cholestanol in tissues may play a crucial role. Chenodeoxycholic acid is the most effective therapy. The causative role and detrimental effects (at a low plasma level) of cholestanol merit further investigation.

    Topics: Brain Diseases; Chenodeoxycholic Acid; Cholestanol; Diagnosis, Differential; Humans; Hyperlipoproteinemia Type II; Musculoskeletal Diseases; Sitosterols; Tendons; Xanthomatosis

2002
Plant sterol margarines. Nutraceuticals for lowering cholesterol.
    Advance for nurse practitioners, 2001, Volume: 9, Issue:1

    Topics: Cholesterol, LDL; Humans; Hypercholesterolemia; Hypolipidemic Agents; Margarine; Sitosterols

2001
[Plants sterols and stanols: new prospects in prevention of ischemic heart disease (based on data published in the European Heart Journal, 1999, vol. 1 (Suppl S))].
    Terapevticheskii arkhiv, 2001, Volume: 73, Issue:1

    Topics: Anticholesteremic Agents; Cholesterol; Cholesterol, LDL; Clinical Trials as Topic; Esters; Humans; Hypolipidemic Agents; Myocardial Ischemia; Phytosterols; Sitosterols

2001
Genetic basis of sitosterolemia.
    Current opinion in lipidology, 2001, Volume: 12, Issue:2

    The molecular mechanisms regulating the amount of dietary cholesterol retained by the body, as well as the body's ability to exclude other dietary sterols selectively, are poorly understood. An average Western diet will contain approximately 250-500 mg of dietary cholesterol and approximately 200-400 mg of non-cholesterol sterols, of which plant sterols are the major constituents. Approximately 50-60% of dietary cholesterol is absorbed and retained by the normal human body, but less than 1% of the non-cholesterol sterols are retained. There thus exists a subtle mechanism that allows the body to distinguish between cholesterol and non-cholesterol sterols. In sitosterolemia, a rare autosomal recessive disorder, affected individuals hyperabsorb and retain not only cholesterol but also all other sterols, including plant and shellfish sterols from the intestine. Consequently, patients with this disease have very high levels of plant sterols in the plasma, and develop tendon and tuberous xanthomas, accelerated atherosclerosis, and premature coronary artery disease. The STSL locus has been mapped to human chromosome 2p21. Mutations in two tandem ABC genes, ABCG5 and ABCG8, encoding sterolin-1 and -2, respectively, are now known to be mutant in sitosterolemia. The identification of these genes should now lead to a better understanding of the molecular mechanism(s) governing the highly selective absorption and retention of cholesterol by the body. Indeed, it is the very existence of this disease that has given credence to the hypothesis that there is a molecular pathway that regulates dietary cholesterol absorption and sterol excretion by the body.

    Topics: ATP-Binding Cassette Transporters; Cholesterol; Chromosomes, Human, Pair 2; Female; Homozygote; Humans; Lipid Metabolism, Inborn Errors; Male; Mutation; Pedigree; Sitosterols

2001
[Sitosterolemia].
    Nihon rinsho. Japanese journal of clinical medicine, 2001, Volume: 59 Suppl 3

    Topics: Arteriosclerosis; Cholestyramine Resin; Contraindications; Diagnosis, Differential; Genes, Recessive; Humans; Ion Exchange Resins; Lipid Metabolism, Inborn Errors; Phytosterols; Prognosis; Sitosterols; Xanthomatosis

2001
Dietary cholesterol absorption; more than just bile.
    Trends in endocrinology and metabolism: TEM, 2001, Volume: 12, Issue:7

    Absorption of dietary cholesterol from the intestine is an important part of cholesterol homeostasis and represents the first step that allows dietary cholesterol to exert its metabolic effects. Although the role of bile salts in the initial absorption of dietary cholesterol, by the formation of emulsions, is readily appreciated, the recognition that other molecular mechanisms might govern this process is only recently gaining momentum. Not only does the intestine regulate the amount of dietary cholesterol that enters the body; it is very selective with regard to the sterols that are allowed in. The human intestine is responsible for absorbing a significant amount of cholesterol each day. In addition to approximately 0.5 g d(-1) of dietary cholesterol, many other sterols are also present in almost equal abundance in the normal diet. Approximately 0.4 g of plant sterols, such as sitosterol, brassicasterol and avanesterol, are also present. However, the human body seems to allow only cholesterol to enter and remain in the body, with almost negligible amounts of plant sterols being retained. That specific molecular mechanisms are responsible for this behavior is supported by the identification of the genetic defect(s) in a rare disorder, beta-sitosterolemia (MIM 210250), where this process is disrupted. Such studies are now beginning to throw light on sterol absorption and excretion and elucidate the molecular mechanisms that govern these processes.

    Topics: Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Bile; Bile Acids and Salts; Cholesterol, Dietary; Humans; Intestinal Absorption; Lipoproteins; Metabolism, Inborn Errors; Mutation; Phytosterols; Sitosterols

2001
Beta-sitosterols for benign prostatic hyperplasia.
    The Cochrane database of systematic reviews, 2000, Issue:2

    This systematic review aimed to assess the effects of beta-sitosterols (B-sitosterol) on urinary symptoms and flow measures in men with of benign prostatic hyperplasia (BPH).. Trials were searched in computerized general and specialized databases (MEDLINE, EMBASE, Cochrane Library, Phytodok), by checking bibliographies, and by contacting manufacturers and researchers.. Trials were eligible for inclusion provided they (1) randomized men with BPH to receive B-sitosterol preparations in comparison to placebo or other BPH medications, and (2) included clinical outcomes such as urologic symptom scales, symptoms, or urodynamic measurements.. Information on patients, interventions, and outcomes was extracted by at least two independent reviewers using a standard form. Main outcome measure for comparing the effectiveness of B-sitosterols with placebo and standard BPH medications was the change in urologic symptom scale scores. Secondary outcomes included changes in nocturia as well as urodynamic measures (peak and mean urine flow, residual volume, prostate size). Main outcome measure for side effects was the number of men reporting side effects.. 519 men from 4 randomized, placebo-controlled, double-blind trials, (lasting 4 to 26 weeks) were assessed. 3 trials used non-glucosidic B-sitosterols and one utilized a preparation that contained 100% B-sitosteryl-B-D-glucoside. B-Sitosterols improved urinary symptom scores and flow measures. The weighted mean difference (WMD) for the IPSS was -4.9 IPSS points (95%CI = -6.3 to -3.5, n = 2 studies). The WMD for peak urine flow was 3.91 ml/sec (95%CI = 0.91 to 6.90, n = 4 studies) and the WMD for residual volume was -28.62 ml (95%CI = -41. 42 to -15.83, n = 4 studies). The trial using 100% B-sitosteryl-B-D-glucoside (WA184) show improvement in urinary flow measures. B-sitosterols did not reduce prostate size. Withdrawal rates for men assigned to B-sitosterol and placebo were 7.8% and 8. 0%, respectively.. The evidence suggests non-glucosidic B-sitosterols improve urinary symptoms and flow measures. Their long term effectiveness, safety and ability to prevent BPH complications are not known.

    Topics: Humans; Male; Phytotherapy; Prostatic Hyperplasia; Sitosterols; Urodynamics

2000
beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review.
    BJU international, 1999, Volume: 83, Issue:9

    To conduct a systematic review of the evidence for the efficacy of beta-sitosterol in men with symptomatic benign prostatic hyperplasia (BPH).. Studies were identified through Medlinetrade mark (1966-98), EMBASEtrade mark, Phytodok, the Cochrane Library, bibliographies of identified trials and review articles, and contact with study authors and pharmaceutical companies. Randomized trials were included if: men had symptomatic BPH; plant extract preparations contained beta-sitosterols; a control group received placebo or a pharmacological therapy; and treatment duration was >/=30 days. Study characteristics, demographic information, enrolment criteria and outcomes were extracted.. Four trials comprising a total of 519 men met the inclusion criteria. All were double-blind and lasted 4-26 weeks. Three studies used nonglucosidic beta-sitosterols and one used a preparation that contained only beta-sitosterol-beta-d-glucoside. Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures. For the two studies reporting the International Prostate Symptom Score (IPSS), the weighted mean difference (WMD) against placebo was -4.9 IPSS points (95% confidence interval, CI,-6.3 to-3.5). The WMD for peak urinary flow rate was 3.91 mL/s (95% CI 0.91 to 6.90, four studies) and for residual volume the WMD was -28.62 mL (95% CI-41.42 to-15.83, four studies). beta-sitosterol did not reduce prostate size. The trial using pure beta-sitosterol-beta-d-glucoside (WA184) showed no improvement in urinary flow measures. Withdrawal rates for men assigned to beta-sitosterol and placebo were 7.8% and 8.0% (not significant), respectively.. beta-sitosterol improves urological symptoms and flow measures. However, the existing studies are limited by short treatment duration and lack of standardized beta-sitosterol preparations. Their long-term effectiveness, safety and ability to prevent the complications of BPH are unknown.

    Topics: Adult; Aged; Aged, 80 and over; Humans; Male; Middle Aged; Prostatic Hyperplasia; Randomized Controlled Trials as Topic; Sitosterols; Treatment Outcome; Urination; Urination Disorders

1999
Plant sterols and sterolins: a review of their immune-modulating properties.
    Alternative medicine review : a journal of clinical therapeutic, 1999, Volume: 4, Issue:3

    Beta-sitosterol (BSS) and its glycoside (BSSG) are sterol molecules which are synthesized by plants. When humans eat plant foods phytosterols are ingested, and are found in the serum and tissues of healthy individuals, but at concentrations orders of magnitude lower than endogenous cholesterol. Epidemiological studies have correlated a reduced risk of numerous diseases with a diet high in fruits and vegetables, and have concluded that specific molecules, including b-carotene, tocopherols, vitamin C, and flavonoids, confer some of this protective benefit. However, these epidemiologic studies have not examined the potential effect that phytosterols ingested with fruits and vegetables might have on disease risk reduction. In animals, BSS and BSSG have been shown to exhibit anti-inflammatory, anti-neoplastic, anti-pyretic, and immune-modulating activity. A proprietary BSS:BSSG mixture has demonstrated promising results in a number of studies, including in vitro studies, animal models, and human clinical trials. This phytosterol complex seems to target specific T-helper lymphocytes, the Th1 and Th2 cells, helping normalize their functioning and resulting in improved T-lymphocyte and natural killer cell activity. A dampening effect on overactive antibody responses has also been seen, as well as normalization of the DHEA:cortisol ratio. The re-establishment of these immune parameters may be of help in numerous disease processes relating to chronic immune-mediated abnormalities, including chronic viral infections, tuberculosis, rheumatoid arthritis, allergies, cancer, and auto-immune diseases.

    Topics: Adjuvants, Immunologic; Animals; Cats; HIV Infections; Humans; Immune Tolerance; Sitosterols; Tuberculosis, Pulmonary

1999
Effects of dietary phytosterols on cholesterol metabolism and atherosclerosis: clinical and experimental evidence.
    The American journal of medicine, 1999, Volume: 107, Issue:6

    Although plant sterols (phytosterols) and cholesterol have similar chemical structures, they differ markedly in their synthesis, intestinal absorption, and metabolic fate. Phytosterols inhibit intestinal cholesterol absorption, thereby lowering plasma total and low-density lipoprotein (LDL) cholesterol levels. In 16 recently published human studies that used phytosterols to reduce plasma cholesterol levels in a total of 590 subjects, phytosterol therapy was accompanied by an average 10% reduction in total cholesterol and 13% reduction in LDL cholesterol levels. Phytosterols may also affect other aspects of cholesterol metabolism that contribute to their antiatherogenic properties, and may interfere with steroid hormone synthesis. The clinical and biochemical features of hereditary sitosterolemia, as well as its treatment, are reviewed, and the effects of cholestyramine treatment in 12 sitosterolemic subjects are summarized. Finally, new ideas for future research into the role of phytosterols in health and disease are discussed.

    Topics: Anticholesteremic Agents; Arteriosclerosis; Cholesterol; Cholestyramine Resin; Humans; Intestinal Absorption; Phytosterols; Sitosterols

1999
[When statins alone are insufficient for lowering lipid levels. Efficacy and risks of lipid lowering combination therapies, in particular, that of statin-fibrate combination].
    Der Internist, 1999, Volume: 40, Issue:12

    Topics: Coronary Disease; Drug Therapy, Combination; Humans; Hyperlipoproteinemias; Hypolipidemic Agents; Niacin; Sitosterols

1999
Sitosterolemia.
    Sub-cellular biochemistry, 1997, Volume: 28

    Topics: Bile Acids and Salts; Cholesterol; Genes, Recessive; Humans; Hydroxymethylglutaryl CoA Reductases; Lipid Metabolism, Inborn Errors; Lipoproteins; Liver; Mevalonic Acid; Sitosterols; Sterols

1997
Relationship between absorption of cholesterol and serum plant sterols.
    Nutrition reviews, 1987, Volume: 45, Issue:6

    Topics: Cholesterol; Humans; Intestinal Absorption; Phytosterols; Sitosterols

1987
Adenomas: preneoplastic events, growth and development in man and experimental systems.
    Pathology annual, 1983, Volume: 18 Pt 1

    Adenoma formation in the colon has been shown to be initiated by an alteration in the genetic make-up which controls the repopulation of the mucosa. This defect is recognized primarily by an upward displacement of the major zone of DNA synthesis within one or a few crypts. Progression to a microadenoma involves an elevation of cell proliferation within these glands and may be hastened by mucosal responses to environmental and dietary factors which enhance cell turnover. The high proliferative activity of epithelial cells within these select crypts allows the unmasking of the neoplastic genotype and the expansion of these cells with a proliferative advantage. Continued rapid cell proliferation within the adenoma either indigenous to the excrescence or fueled additionally by luminal conditions may contribute to the evolution of a malignant genotype, the establishment of a severely dysplastic clone and ultimately to the production of invasive colon cancer.

    Topics: Adult; Animals; Antioxidants; Colon; Colonic Neoplasms; Humans; Intestinal Polyps; Mice; Middle Aged; Neoplasms, Experimental; Precancerous Conditions; Rats; Sitosterols

1983
Therapy of hyperlipidemic states.
    Annual review of medicine, 1982, Volume: 33

    Topics: Cholesterol, Dietary; Cholestyramine Resin; Clofibrate; Colestipol; Dietary Fats; Drug Therapy, Combination; Humans; Hyperlipidemias; Hyperlipoproteinemia Type II; Hyperlipoproteinemia Type IV; Lipoproteins, LDL; Lipoproteins, VLDL; Niacin; Nicotinic Acids; Sitosterols

1982
HYPOCHOLESTEREMIC EFFECT OF SITOSTEROL.
    Nutrition reviews, 1964, Volume: 22

    Topics: Diet; Diet Therapy; Dietary Fats; Humans; Hypercholesterolemia; Sitosterols; Sterols

1964

Trials

91 trial(s) available for cytellin and gamma-sitosterol

ArticleYear
A double blind, placebo-controlled randomized comparative study on the efficacy of phytosterol-enriched and conventional saw palmetto oil in mitigating benign prostate hyperplasia and androgen deficiency.
    BMC urology, 2020, Jul-03, Volume: 20, Issue:1

    The present clinical trial was conducted to evaluate the efficacy and tolerability of a standardized saw palmetto oil containing 3% β-sitosterol in the treatment of benign prostate hyperplasia (BPH) and androgen deficiency.. Subjects aged 40-65 years with symptomatic BPH were randomized to 12-week double-blind treatment with 500 mg doses of β-sitosterol enriched saw palmetto oil, conventional saw palmetto oil and placebo orally in the form of capsules (n = 33 in each group). BPH severity was determined using the International Prostate Symptom Score (IPSS), uroflowmetry, serum measurement of prostate specific antigen (PSA), testosterone and 5α-reductase. During the trial, the androgen deficiency was evaluated using Aging Male Symptoms (AMS) scale, the Androgen Deficiency in the Aging Male (ADAM) questionnaire, serum levels of free testosterone.. Subjects treated with β-sitosterol enriched saw palmetto oil showed significant decrease in IPSS, AMS and ADAM scores along with reduced postvoiding residual volume (p < 0.001), PSA (p < 0.01) and 5α-reductase from baseline to end of 12-week treatment as compared to placebo. There was also a significant increment in the maximum and average urine flow rate (p < 0.001), and serum free testosterone level of subjects treated with enriched saw palmetto oil as compared to placebo.. This study demonstrates the efficacy of β-sitosterol enriched saw palmetto oil superior to conventional oil thus extending the scope of effective BPH and androgen deficiency treatment with improved quality of life through the intake of functional ingredients.. CTRI/2018/12/016724 dated 19/12/2018 prospectively registered. URL: http://ctri.nic.in/Clinicaltrials/advsearch.php.

    Topics: Adult; Aged; Androgens; Double-Blind Method; Humans; Male; Middle Aged; Phytosterols; Phytotherapy; Plant Extracts; Plant Oils; Prostatic Hyperplasia; Serenoa; Sitosterols; Treatment Outcome; Urological Agents

2020
Differences in lipid metabolism between anagliptin and sitagliptin in patients with type 2 diabetes on statin therapy: a secondary analysis of the REASON trial.
    Cardiovascular diabetology, 2019, 11-16, Volume: 18, Issue:1

    Anagliptin, a dipeptidyl peptidase-4 inhibitor, is reported to reduce the level of low-density lipoprotein cholesterol (LDL-C). The underlying mechanism of this effect and effect on lipid metabolism however remains uncertain.. We therefore evaluate the effects of anagliptin on lipid metabolism-related markers compared with those of sitagliptin. The study was a secondary analysis using data obtained from the Randomized Evaluation of Anagliptin versus Sitagliptin On low-density lipoproteiN cholesterol in diabetes (REASON) trial. This trial in patients with type 2 diabetes at a high risk of cardiovascular events and on statin therapy showed that anagliptin reduced LDL-C levels to a greater extent than sitagliptin. Cholesterol absorption (campesterol and sitosterol) and synthesis (lathosterol) markers were measured at baseline and 52 weeks in the study cohort (n = 353).. There was no significant difference in the changes of campesterol or sitosterol between the two treatment groups (p = 0.85 and 0.55, respectively). Lathosterol concentration was increased significantly at 52 weeks with sitagliptin treatment (baseline, 1.2 ± 0.7 μg/mL vs. 52 weeks, 1.4 ± 1.0 μg/mL, p = 0.02), whereas it did not change in the anagliptin group (baseline, 1.3 ± 0.8 μg/mL vs. 52 weeks, 1.3 ± 0.7 μg/mL, p = 0.99). The difference in absolute change between the two groups showed a borderline significance (p = 0.06).. These findings suggest that anagliptin reduces LDL-C level by suppressing excess cholesterol synthesis, even in combination with statin therapy. Trial registration ClinicalTrials.gov number NCT02330406. https://clinicaltrials.gov/ct2/show/NCT02330406; registered January 5, 2015.

    Topics: Aged; Biomarkers; Cholesterol; Cholesterol, LDL; Diabetes Mellitus, Type 2; Dipeptidyl-Peptidase IV Inhibitors; Dyslipidemias; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Japan; Male; Middle Aged; Phytosterols; Pyrimidines; Sitagliptin Phosphate; Sitosterols; Time Factors; Treatment Outcome

2019
Sitosterol prevents obesity-related chronic inflammation.
    Biochimica et biophysica acta. Molecular and cell biology of lipids, 2018, Volume: 1863, Issue:2

    The physiological roles of phytosterols in chronic inflammation, which are believed to be involved in the underlying mechanisms for metabolic diseases, have yet to be elucidated. Therefore, in the present study, we aimed to elucidate the physiological roles of phytosterols in both clinical studies and animal experiments. We observed the existence of rather specific negative correlations between the serum sitosterol level and the serum IL-6 and the TNF-α levels in both diabetic subjects (n=46) and non-diabetic subjects (n=178). Multiple regression analyses also revealed that the serum IL-6 and TNF-α levels exhibited strong negative correlations with the serum sitosterol levels. When ABCG5/8 KO mice with markedly elevated plasma sitosterol levels and ABCG5/8 hetero mice were fed a high-fat diet, we observed that the increase in body weight, the fatty liver changes, and the expansion of perigonadal adipose tissues were suppressed in ABCG5/8 KO mice without any modulation of food intake. We also observed that the plasma IL-6 and TNF-α levels, the expressions of TNF-α and PAI-1 in the liver and the expressions of the IL-6, TNF-α, and MCP-1 levels in the adipose tissue were lower in ABCG5/8 KO mice. These results suggest that sitosterol might suppress obesity-related chronic inflammation and might be applicable to the treatment of metabolic diseases.

    Topics: Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; Chronic Disease; Female; Humans; Inflammation; Interleukin-6; Lipoproteins; Male; Mice; Mice, Knockout; Middle Aged; Obesity; Sitosterols; Tumor Necrosis Factor-alpha

2018
Plant sterol ester diet supplementation increases serum plant sterols and markers of cholesterol synthesis, but has no effect on total cholesterol levels.
    The Journal of steroid biochemistry and molecular biology, 2017, Volume: 169

    This double-blind, randomized, placebo-controlled, cross-over intervention-study was conducted in healthy volunteers to evaluate the effects of plant sterol ester supplemented margarine on cholesterol, non-cholesterol sterols and oxidative stress in serum and monocytes. Sixteen volunteers, average age 34 years, with no or mild hypercholesterolemia were subjected to a 4 week period of daily intake of 3g plant sterols per day supplied via a supplemented margarine on top of regular eating habits. After a wash-out period of one week, volunteers switched groups. Compared to placebo, a diet supplementation with plant sterols increased serum levels of plant sterols such as campesterol (+0.16±0.19mg/dL, p=0.005) and sitosterol (+0.27±0.18mg/dL, p<0.001) and increased markers of cholesterol synthesis such as desmosterol (+0.05±0.07mg/dL, p=0.006) as well as lathosterol (+0.11±0.16mg/dL, p=0.012). Cholesterol serum levels, however, were not changed significantly (+18.68±32.6mg/dL, p=0.052). These findings could not be verified in isolated circulating monocytes. Moreover, there was no effect on monocyte activation and no differences with regard to redox state after plant sterol supplemented diet. Therefore, in a population of healthy volunteers with no or mild hypercholesterolemia, consumption of plant sterol ester supplemented margarine results in increased concentrations of plant sterols and cholesterol synthesis markers without affecting total cholesterol in the serum, activation of circulating monocytes or redox state.

    Topics: Adult; Biomarkers; Cell Separation; Cholesterol; Cross-Over Studies; Diet; Double-Blind Method; Female; Flow Cytometry; Gas Chromatography-Mass Spectrometry; Humans; Male; Margarine; Monocytes; Oxidation-Reduction; Oxidative Stress; Oxygen; Phytosterols; Reactive Oxygen Species; Sitosterols; Young Adult

2017
Increases in plasma plant sterols stabilize within four weeks of plant sterol intake and are independent of cholesterol metabolism.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2016, Volume: 26, Issue:4

    Plant sterols (PS) lower plasma LDL-cholesterol through partial inhibition of intestinal cholesterol absorption. Although PS themselves are poorly absorbed, increased intakes of PS result in elevated plasma concentrations. In this paper, we report time curves of changes in plasma PS during 12 weeks of PS intake. Furthermore, the impact of cholesterol synthesis and absorption on changes in plasma PS is explored.. The study was a double-blind, randomized, placebo-controlled, parallel-group study with the main aim to investigate the effects of PS on vascular function (clinicaltrials.gov: NCT01803178). Hypercholesterolemic but otherwise healthy men and women (n = 240) consumed low-fat spreads without or with added PS (3 g/d) for 12 weeks after a 4-week run-in period. Blood sampling was performed at week 0, 4, 8 and 12. Basal cholesterol-standardized concentrations of lathosterol and sitosterol + campesterol were used as markers of cholesterol synthesis and absorption, respectively. In the PS group, plasma sitosterol and campesterol concentrations increased within the first 4 weeks of intervention by 69% (95%CI: 58; 82) starting at 7.2 μmol/L and by 28% (95%CI: 19; 39) starting at 11.4 μmol/L, respectively, and remained stable during the following 8 weeks. Placebo-corrected increases in plasma PS were not significantly different between high and low cholesterol synthesizers (P-values >0.05). Between high and low cholesterol absorbers, no significant differences were observed, except for the cholesterol-standardized sum of four major plasma PS (sitosterol, campesterol, brassicasterol and stigmasterol) showing larger increases in low absorbers (78.3% (95%CI: 51.7; 109.5)) compared to high absorbers (40.8% (95%CI: 19.9; 65.5)).. Increases in plasma PS stabilize within 4 weeks of PS intake and do not seem impacted by basal cholesterol synthesis or absorption efficiency. This study was registered at clinicaltrials.gov (NCT01803178).

    Topics: Adult; Aged; Cholestadienols; Cholesterol; Cholesterol, LDL; Double-Blind Method; Female; Humans; Hypercholesterolemia; Intestinal Absorption; Lipid Metabolism; Male; Middle Aged; Phytosterols; Prospective Studies; Sitosterols; Stigmasterol

2016
Triterpene alcohols and sterols from rice bran reduce postprandial hyperglycemia in rodents and humans.
    Molecular nutrition & food research, 2016, Volume: 60, Issue:7

    Hyperglycemia is a major public health problem worldwide and there is increasing demand for prevention of postprandial hyperglycemia in diabetic, prediabetic, and healthy humans.. We investigated whether rice bran and triterpene alcohol and sterol preparation (TASP) lowered hyperglycemia in mice and humans. Brown rice and white rice supplemented with TASP lowered the postprandial hyperglycemia in humans. TASP and its components (cycloartenol [CA], 24-methylene cycloartanol, β-sitosterol, and campesterol) decreased postprandial hyperglycemia in C57BL/6J mice. Glucose transport into everted rat intestinal sacs and human HuTu80 cells transfected with sodium-glucose cotransporter-1 (SGLT1) was significantly reduced by the addition of CA. Intracellular localization analysis suggested that SGLT1 translocation to the apical plasma membrane was inhibited when the cells were treated with CA.. We demonstrated for the first time that TASP from rice bran lowered postprandial hyperglycemia in mice and humans. The smaller increase in blood glucose following TASP consumption may be due to the CA-induced decrease in glucose absorption from the intestine, which may be related to decreased membrane translocation of SGLT1.

    Topics: Adult; Animals; Blood Glucose; Body Mass Index; Body Weight; Cell Line, Tumor; Cholesterol; Dietary Fiber; Humans; Hyperglycemia; Insulin; Male; Mice; Mice, Inbred C57BL; Oryza; Phytosterols; Rats; Rats, Wistar; Single-Blind Method; Sitosterols; Sodium-Glucose Transporter 1; Sterols; Triterpenes

2016
A randomized trial of efficacy of beta-sitosterol and its glucoside as adjuvant to cryotherapy in the treatment of anogenital warts.
    The Journal of dermatological treatment, 2015, Volume: 26, Issue:2

    All available treatments for anogenital warts have substantial failure rates. An immunomodulating treatment that enhances the patient's own immunity could be valuable as an adjuvant to conventional methods.. About 123 patients were enrolled in this study and were randomized either to undergo only cryotherapy every 3 weeks (n = 60 patients) or to undergo cryotherapy and to receive a mixture containing 20 mg sterol and 0.2 mg sterolin (BSS-BSSG mixture), known for its immunomodulating properties (n = 63).. A complete response after 3 months was demonstrated by 18.3% of the patients in the first group and 30.2% of the second group, while 61.7% of the first group and 79.4% of the second group were lesion free at the end of the 6-month follow-up period. Cox regression analysis of the time until response showed a significant advantage to the mixture treatment group (hazard ratio 2.76, 95% confidence interval 1.61-5.67).. The study was not placebo controlled.. The BSS-BSSG mixture gave promising results as an adjuvant to cryotherapy and may be used in patients with refractory warts.

    Topics: Adult; Combined Modality Therapy; Condylomata Acuminata; Cryotherapy; Female; Glucosides; Humans; Male; Middle Aged; Sitosterols; Young Adult

2015
Dietary plant stanols or sterols neither accumulate in stenotic aortic valves nor influence their structure or inflammatory status.
    Clinical nutrition (Edinburgh, Scotland), 2015, Volume: 34, Issue:6

    Consumption of plant stanols and plant sterols decreases LDL cholesterol level and increases serum concentrations of plant stanols/sterols, but it is practically unexplored whether also their tissue concentrations increase. Thus, the aim of this study was to assess whether consuming plant stanols/sterols increases their concentrations in stenotic aortic valves and affect the valvular structure (collagen and elastin) or inflammation (macrophages and mast cells).. In a randomized, double-blind controlled intervention patients with severe aortic stenosis consumed margarine without (n = 11) or with 2 g of plant stanols (n = 12) or sterols (n = 13) until valve replacement surgery (2.6 months, on average). The effects of sitostanol and sitosterol on the expression and secretion of proinflammatory cytokines by cultured aortic valve myofibroblasts were also assessed.. Control-related LDL-cholesterol was diminished by 16% (p < 0.05) by plant stanol and by 11% (NS) by plant sterol consumption, respectively. In the resected valves, cholesterol, plant stanol and sterol levels were similar in all groups. Consumed plant stanols or sterols had no effect on valvular structure or mast cell or macrophage numbers in valves. Incubation of cultured myofibroblasts derived from stenotic valves with sitostanol or sitosterol decreased mRNA expression of the monocyte chemotactic protein-1 (p < 0.05) and interleukin-1 beta (p < 0.05).. In this study, plant stanol/sterol consumption did not affect cholesterol, plant stanol or sterol levels in stenotic aortic valves; neither did they influence the structure or the inflammatory status of the valves. However, these findings need to be confirmed in a larger-scale intervention. ClinicalTrials.govRegister #NCT00738933.

    Topics: Aged; Aged, 80 and over; Aortic Valve; Chemokine CCL2; Cholesterol, LDL; Diet; Double-Blind Method; Female; Heart Valve Prosthesis Implantation; Humans; Interleukin-1beta; Male; Margarine; Middle Aged; Myofibroblasts; Phytosterols; RNA, Messenger; Sitosterols

2015
Postprandial plasma oxyphytosterol concentrations after consumption of plant sterol or stanol enriched mixed meals in healthy subjects.
    Steroids, 2015, Volume: 99, Issue:Pt B

    Epidemiological studies have reported inconsistent results on the relationship between increased plant sterol concentrations with cardiovascular risk, which might be related to the formation of oxyphytosterols (plant sterol oxidation products) from plant sterols. However, determinants of oxyphytosterol formation and metabolism are largely unknown. It is known, however, that serum plant sterol concentrations increase after daily consumption of plant sterol enriched products, while concentrations decrease after plant stanol consumption. Still, we have earlier reported that fasting oxyphytosterol concentrations did not increase after consuming a plant sterol- or a plant stanol enriched margarine (3.0g/d of plant sterols or stanols) for 4weeks. Since humans are in a non-fasting state for most part of the day, we have now investigated effects on oxyphytosterol concentrations during the postprandial state. For this, subjects consumed a shake (50g of fat, 12g of protein, 67g of carbohydrates), containing no, or 3.0g of plant sterols or plant stanols. Blood samples were taken up to 8h and after 4h subjects received a second shake (without plant sterols or plant stanols). Serum oxyphytosterol concentrations were determined in BHT-enriched EDTA plasma via GC-MS/MS. 7β-OH-campesterol and 7β-OH-sitosterol concentrations were significantly higher after consumption of a mixed meal enriched with plant sterol esters compared to the control and plant stanol ester meal. These increases were seen only after consumption of the second shake, illustrative for a second meal effect. Non-oxidized campesterol and sitosterol concentrations also increased after plant sterol consumption, in parallel with 7β-OH concentrations and again only after the second meal. Apparently, plant sterols and oxyphytosterols follow the same second meal effect as described for dietary cholesterol. However, the question remains whether the increase in oxyphytosterols in the postprandial phase is due to absorption or endogenous formation.

    Topics: Adult; Cholesterol; Fasting; Feeding Behavior; Female; Healthy Volunteers; Humans; Male; Meals; Oxidation-Reduction; Phytosterols; Postprandial Period; Sitosterols

2015
The effect of a low-fat spread with added plant sterols on vascular function markers: results of the Investigating Vascular Function Effects of Plant Sterols (INVEST) study.
    The American journal of clinical nutrition, 2015, Volume: 101, Issue:4

    Plant sterols (PSs) lower LDL cholesterol, an established risk factor for coronary artery disease (CAD). No direct evidence is available supporting a reduced risk of CAD for foods with added PSs. Endothelial dysfunction is seen as an early indicator of atherosclerotic damage.. This study was primarily designed to investigate the effect of a low-fat spread with added PSs on brachial artery endothelial function as measured by flow-mediated dilation (FMD). Second, effects on arterial stiffness, blood pressure, serum lipids, and plasma PS concentrations were investigated. We hypothesized that PSs would not worsen FMD but would rather modestly improve FMD.. This study had a double-blind, randomized, placebo-controlled, parallel design. After a 4-wk run-in period, 240 hypercholesterolemic but otherwise healthy men and women consumed 20 g/d of low-fat spread without (control) or with added PSs (3 g/d) during 12 wk. Pre- and postintervention, vascular function measurements and blood sampling were performed.. In total, 232 participants completed the study period. For the primary endpoint FMD, 199 participants were included in the statistical analysis. PS intake did not affect FMD (+0.01 percentage points; 95% CI: -0.73, 0.75) compared with control. Measures of arterial stiffness (pulse wave velocity and augmentation index) and blood pressure were also not significantly changed compared with control. After PS intervention, LDL cholesterol significantly decreased on average by 0.26 mmol/L (95% CI: -0.40, -0.12) or 6.7% compared with control. Plasma sitosterol and campesterol concentrations significantly increased in the PS group up to on average 11.5 μmol/L and 13.9 μmol/L (expressed as geometric means), respectively.. The intake of a low-fat spread with added PSs neither improved nor worsened FMD or other vascular function markers in hypercholesterolemic men and women. As expected, serum LDL cholesterol decreased, whereas plasma PSs increased after PS intake. This study was registered at clinicaltrials.gov as NCT01803178.

    Topics: Biomarkers; Brachial Artery; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dietary Carbohydrates; Dietary Fats; Dietary Proteins; Double-Blind Method; Endpoint Determination; Energy Intake; Female; Humans; Hypercholesterolemia; Life Style; Male; Middle Aged; Phytosterols; Pulse Wave Analysis; Sitosterols; Triglycerides

2015
Potential role of milk fat globule membrane in modulating plasma lipoproteins, gene expression, and cholesterol metabolism in humans: a randomized study.
    The American journal of clinical nutrition, 2015, Volume: 102, Issue:1

    Butter is rich in saturated fat [saturated fatty acids (SFAs)] and can increase plasma low density lipoprotein (LDL) cholesterol, which is a major risk factor for cardiovascular disease. However, compared with other dairy foods, butter is low in milk fat globule membrane (MFGM) content, which encloses the fat. We hypothesized that different dairy foods may have distinct effects on plasma lipids because of a varying content of MFGM.. We aimed to investigate whether the effects of milk fat on plasma lipids and cardiometabolic risk markers are modulated by the MFGM content.. The study was an 8-wk, single-blind, randomized, controlled isocaloric trial with 2 parallel groups including overweight men and women (n = 57 randomly assigned). For the intervention, subjects consumed 40 g milk fat/d as either whipping cream (MFGM diet) or butter oil (control diet). Intervention foods were matched for total fat, protein, carbohydrates, and calcium. Subjects were discouraged from consuming any other dairy products during the study. Plasma markers of cholesterol absorption and hepatic cholesterol metabolism were assessed together with global gene-expression analyses in peripheral blood mononuclear cells.. As expected, the control diet increased plasma lipids, whereas the MFGM diet did not [total cholesterol (±SD): +0.30 ± 0.49 compared with -0.04 ± 0.49 mmol/L, respectively (P = 0.024); LDL cholesterol: +0.36 ± 0.50 compared with +0.04 ± 0.36 mmol/L, respectively (P = 0.024); apolipoprotein B:apolipoprotein A-I ratio: +0.03 ± 0.09 compared with -0.05 ± 0.10 mmol/L, respectively (P = 0.007); and non-HDL cholesterol: +0.24 ± 0.49 compared with -0.14 ± 0.51 mmol/L, respectively (P = 0.013)]. HDL-cholesterol, triglyceride, sitosterol, lathosterol, campesterol, and proprotein convertase subtilisin/kexin type 9 plasma concentrations and fatty acid compositions did not differ between groups. Nineteen genes were differentially regulated between groups, and these genes were mostly correlated with lipid changes.. In contrast to milk fat without MFGM, milk fat enclosed by MFGM does not impair the lipoprotein profile. The mechanism is not clear although suppressed gene expression by MFGM correlated inversely with plasma lipids. The food matrix should be considered when evaluating cardiovascular aspects of different dairy foods. This trial was registered at clinicaltrials.gov as NCT01767077.

    Topics: Adult; Aged; Apolipoprotein A-I; Apolipoproteins B; Body Mass Index; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dairy Products; Energy Intake; Fatty Acids; Feeding Behavior; Female; Gene Expression; Glycolipids; Glycoproteins; Healthy Volunteers; Homeostasis; Humans; Leukocytes, Mononuclear; Lipid Droplets; Male; Middle Aged; Nutrition Assessment; Phytosterols; Proprotein Convertase 9; Proprotein Convertases; Serine Endopeptidases; Single-Blind Method; Sitosterols; Triglycerides; Young Adult

2015
Anagliptin decreases serum lathosterol level in patients with type 2 diabetes: a pilot study.
    Expert opinion on pharmacotherapy, 2015, Volume: 16, Issue:12

    The mechanism responsible for the lipid-lowering effect of dipeptidyl peptidase-4 (DPP-4) inhibitors remains unknown in humans. We evaluated the effect of anagliptin on serum lipid profiles, including cholesterol synthesis and absorption markers, in Japanese patients with type 2 diabetes.. Thirty patients with type 2 diabetes (20 - 70 years old, low-density lipoprotein cholesterol (LDL-C) level over 120 mg/dl, and no history of treatment with antidiabetic or antihyperlipidemic drugs) were enrolled. One hundred milligrams of anagliptin were administered twice a day for a month.. After treatment of anagliptin, the LDL-C and total cholesterol (TC) levels did not decrease overall, but the TC level decreased significantly in 28 patients whose HbA1c levels decreased. Lathosterol decreased significantly, whereas no changes in campesterol, sitosterol or cholestanol were observed.. These results of our study show no significant change in LDL-C, a tendency of decrease in TC and non-high-density lipoprotein cholesterol (non-HDL-C) after treatment of anagliptin for 1 month. Anagliptin therapy decreased the cholesterol synthesis marker lathosterol without changing cholesterol absorption markers.

    Topics: Adult; Aged; Biomarkers; Cholestanol; Cholesterol; Cholesterol, LDL; Diabetes Mellitus, Type 2; Dipeptidyl-Peptidase IV Inhibitors; Female; Humans; Hypoglycemic Agents; Hypolipidemic Agents; Lipids; Lipoproteins, HDL; Male; Middle Aged; Phytosterols; Pilot Projects; Pyrimidines; Sitosterols; Young Adult

2015
Efficacy, safety and effect on biomarkers related to cholesterol and lipoprotein metabolism of rosuvastatin 10 or 20 mg plus ezetimibe 10 mg vs. simvastatin 40 or 80 mg plus ezetimibe 10 mg in high-risk patients: Results of the GRAVITY randomized study.
    Atherosclerosis, 2014, Volume: 232, Issue:1

    Combination therapy may help high-risk patients achieve low-density lipoprotein cholesterol (LDL-C) goals. Impact of rosuvastatin 10 or 20 mg plus ezetimibe 10 mg (RSV10/EZE10 and RSV20/EZE10) has not been fully characterized previously. GRAVITY (NCT00525824) compared efficacy, safety and effect on biomarkers of RSV10/EZE10 and RSV20/EZE10 vs. simvastatin 40 mg and 80 mg plus EZE10 (SIM40/EZE10 and SIM80/EZE10) in patients with coronary heart disease (CHD) or CHD risk equivalent.. Adult patients (n = 833) were randomized to RSV10/EZE10, RSV20/EZE10, SIM40/EZE10 or SIM80/EZE10. Following a 6-week dietary lead-in, patients received 6 weeks' statin monotherapy followed by same statin dose plus ezetimibe for 6 more weeks. Primary endpoint was LDL-C change from baseline to 12 weeks.. Significantly greater (p < 0.05) reductions in LDL-C and other atherogenic lipids were observed with RSV20/EZE10 vs. SIM40/EZE10 and SIM80/EZE10 and with RSV10/EZE10 vs. SIM40/EZE10. A significantly greater proportion of patients achieved LDL-C goals of <100 mg/dl and <70 mg/dl with RSV20/EZE10 vs. SIM40/EZE10 and SIM80/EZE10 and with RSV10/EZE10 vs. SIM40/EZE10. LDL-C was reduced ∼10-14% further with combination therapy vs. monotherapy. Statin monotherapy reduced cholesterol and bile acid synthesis biomarkers, ezetimibe reduced β-sitosterol (sterol absorption marker), and combination therapy achieved additive reductions in lipoprotein-associated phospholipase A2 mass and activity, free cholesterol and 7-ketocholesterol. Safety profiles of rosuvastatin/ezetimibe and simvastatin/ezetimibe combinations were comparable.. Co-administration of rosuvastatin 10 or 20 mg plus ezetimibe achieved significant improvements in lipid profiles in high-risk patients vs. simvastatin 40 or 80 mg plus ezetimibe.

    Topics: Absorption; Adult; Atherosclerosis; Azetidines; Biomarkers; Cholesterol, LDL; Coronary Disease; Drug Administration Schedule; Ezetimibe; Female; Fluorobenzenes; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Lipids; Lipoproteins; Male; Pyrimidines; Risk; Rosuvastatin Calcium; Simvastatin; Sitosterols; Sulfonamides; Treatment Outcome

2014
Effect of β-cryptoxanthin plus phytosterols on cardiovascular risk and bone turnover markers in post-menopausal women: a randomized crossover trial.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2014, Volume: 24, Issue:10

    Post-menopausal women are at higher risk of cardiovascular disease and bone demineralization. Phytosterols (PS) may be used for hypercholesterolemia in some groups and β-cryptoxanthin (β-Cx) displays a unique anabolic effect on bone. Our aim was to assess the changes in cardiovascular and bone turnover markers from the oral intake of β-Cx and PS in post-menopausal women.. A randomized, double-blind, crossover study with β-Cx (0.75 mg/day) and PS (1.5 g/day), single and combined, was performed in 38 postmenopausal women. Diet was supplemented with 1 × 250 mL milk-based fruit drink/day for 4 weeks with a wash-out period of 4-weeks in between. Serum β-Cx and PS were determined by UPLC and CG-FID respectively. Outcome variables included markers of bone turnover and cardiovascular risk. Biological effect was assessed by paired t test and generalized estimating equations analysis that included the previous treatment, the order of intervention and the interactions. The intake of beverages containing β-Cx and PS brought about a significant increase in serum levels of β-Cx, β-sitosterol and campesterol. Intervention caused changes in almost all the markers while the order, previous treatment and the interaction did not reach statistical significance. Only the intake of the beverage containing β-Cx plus PS brought about significant decreases in total cholesterol, c-HDL, c-LDL and bone turnover markers.. β-Cx improves the cholesterol-lowering effect of PS when supplied simultaneously and this combination may also be beneficial in reducing risk of osteoporosis.. ClinicalTrials.gov number NCT01074723.

    Topics: Administration, Oral; Aged; Bone and Bones; Cardiovascular Diseases; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Cross-Over Studies; Cryptoxanthins; Dietary Supplements; Dose-Response Relationship, Drug; Double-Blind Method; Female; Healthy Volunteers; Humans; Hypercholesterolemia; Middle Aged; Phytosterols; Postmenopause; Risk Factors; Sitosterols; Treatment Outcome; Triglycerides

2014
A moderate-fat diet containing pistachios improves emerging markers of cardiometabolic syndrome in healthy adults with elevated LDL levels.
    The British journal of nutrition, 2014, Sep-14, Volume: 112, Issue:5

    A randomised, cross-over, controlled-feeding study was conducted to evaluate the cholesterol-lowering effects of diets containing pistachios as a strategy for increasing total fat (TF) levels v. a control (step I) lower-fat diet. Ex vivo techniques were used to evaluate the effects of pistachio consumption on lipoprotein subclasses and functionality in individuals (n 28) with elevated LDL levels ( ≥ 2·86 mmol/l). The following test diets (SFA approximately 8 % and cholesterol < 300 mg/d) were used: a control diet (25 % TF); a diet comprising one serving of pistachios per d (1PD; 30 % TF); a diet comprising two servings of pistachios per d (2PD; 34 % TF). A significant decrease in small and dense LDL (sdLDL) levels was observed following the 2PD dietary treatment v. the 1PD dietary treatment (P= 0·03) and following the 2PD dietary treatment v. the control treatment (P= 0·001). Furthermore, reductions in sdLDL levels were correlated with reductions in TAG levels (r 0·424, P= 0·025) following the 2PD dietary treatment v. the control treatment. In addition, inclusion of pistachios increased the levels of functional α-1 (P= 0·073) and α-2 (P= 0·056) HDL particles. However, ATP-binding cassette transporter A1-mediated serum cholesterol efflux capacity (P= 0·016) and global serum cholesterol efflux capacity (P= 0·076) were only improved following the 2PD dietary treatment v. the 1PD dietary treatment when baseline C-reactive protein status was low ( < 103μg/l). Moreover, a significant decrease in the TAG:HDL ratio was observed following the 2PD dietary treatment v. the control treatment (P= 0·036). There was a significant increase in β-sitosterol levels (P< 0·0001) with the inclusion of pistachios, confirming adherence to the study protocol. In conclusion, the inclusion of pistachios in a moderate-fat diet favourably affects the cardiometabolic profile in individuals with an increased risk of CVD.

    Topics: Anticholesteremic Agents; Biomarkers; C-Reactive Protein; Cardiovascular Diseases; Cholesterol; Cross-Over Studies; Dietary Fats; Female; Humans; Insulin Resistance; Lipoproteins; Lipoproteins, LDL; Male; Metabolic Syndrome; Middle Aged; Nuts; Phytosterols; Phytotherapy; Pistacia; Sitosterols; Triglycerides

2014
Elevated serum squalene and cholesterol synthesis markers in pregnant obese women with gestational diabetes mellitus.
    Journal of lipid research, 2014, Volume: 55, Issue:12

    We examined serum cholesterol synthesis and absorption markers and their association with neonatal birth weight in obese pregnancies affected by gestational diabetes mellitus (GDM). Pregnant women at risk for GDM (BMI >30 kg/m²) were enrolled from maternity clinics in Finland. GDM was determined from the results of an oral glucose tolerance test. Serum samples were collected at six time-points, one in each trimester of pregnancy, and at 6 weeks, 6 months, and 12 months postpartum. Analysis of serum squalene and noncholesterol sterols by gas-liquid chromatography revealed that in subjects with GDM (n = 22), the serum Δ8-cholestenol concentration and lathosterol/sitosterol ratio were higher (P < 0.05) than in the controls (n = 30) in the first trimester, reflecting increased cholesterol synthesis. Also, subjects with GDM had an increased ratio of squalene to cholesterol (100 × μmol/mmol of cholesterol) in the second (11.5 ± 0.5 vs. 9.1 ± 0.5, P < 0.01) and third (12.1 ± 0.8 vs. 10.0 ± 0.7, P < 0.05) trimester. In GDM, the second trimester maternal serum squalene concentration correlated with neonatal birth weight (r = 0.70, P < 0.001). In conclusion, in obesity, GDM associated with elevated serum markers of cholesterol synthesis. Correlation of maternal serum squalene with neonatal birth weight suggests a potential contribution of maternal cholesterol synthesis to newborn weight in GDM.

    Topics: Adult; Biomarkers; Birth Weight; Body Mass Index; Cholesterol; Diabetes, Gestational; Female; Fetal Macrosomia; Finland; Follow-Up Studies; Humans; Infant, Newborn; Male; Maternal Nutritional Physiological Phenomena; Obesity; Phytosterols; Postpartum Period; Pregnancy; Risk; Sitosterols; Squalene

2014
Consumption of a dietary portfolio of cholesterol lowering foods improves blood lipids without affecting concentrations of fat soluble compounds.
    Nutrition journal, 2014, Oct-18, Volume: 13

    Consumption of a cholesterol lowering dietary portfolio including plant sterols (PS), viscous fibre, soy proteins and nuts for 6 months improves blood lipid profile. Plant sterols reduce blood cholesterol by inhibiting intestinal cholesterol absorption and concerns have been raised whether PS consumption reduces fat soluble vitamin absorption.. The objective was to determine effects of consumption of a cholesterol lowering dietary portfolio on circulating concentrations of PS and fat soluble vitamins.. Using a parallel design study, 351 hyperlipidemic participants from 4 centres across Canada were randomized to 1 of 3 groups. Participants followed dietary advice with control or portfolio diet. Participants on routine and intensive portfolio involved 2 and 7 clinic visits, respectively, over 6 months.. No changes in plasma concentrations of α and γ tocopherol, lutein, lycopene and retinol, but decreased β-carotene concentrations were observed with intensive (week 12: p = 0.045; week 24: p = 0.039) and routine (week 12: p = 0.031; week 24: p = 0.078) portfolio groups compared to control. However, cholesterol adjusted β-carotene and fat soluble compound concentrations were not different compared to control. Plasma PS concentrations were increased with intensive (campesterol:p = 0.012; β-sitosterol:p = 0.035) and routine (campesterol: p = 0.034; β-sitosterol: p = 0.080) portfolio groups compared to control. Plasma cholesterol-adjusted campesterol and β-sitosterol concentrations were negatively correlated (p < 0.001) with total and LDL-C levels.. Results demonstrate that consuming a portfolio diet reduces serum total and LDL-C levels while increasing PS values, without altering fat soluble compounds concentrations. The extent of increments of PS with the current study are not deleterious and also maintaining optimum levels of fat soluble vitamins are of paramount necessity to maintain overall metabolism and health. Results indicate portfolio diet as one of the best options for CVD risk reduction.. clinicaltrials.gov Identifier: NCT00438425.

    Topics: Adult; beta Carotene; Canada; Carotenoids; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Diet; Dietary Fiber; Feeding Behavior; Female; Follow-Up Studies; Humans; Hyperlipidemias; Lutein; Lycopene; Male; Middle Aged; Nuts; Phytosterols; Single-Blind Method; Sitosterols; Tocopherols; Triglycerides; Vitamin A; Vitamins

2014
Effects of ezetimibe on markers of synthesis and absorption of cholesterol in high-risk patients with elevated C-reactive protein.
    Life sciences, 2013, May-02, Volume: 92, Issue:14-16

    High-risk subjects with elevated C-reactive protein (CRP) are at high risk for cardiovascular events and frequently require potent statins or combined lipid-lowering therapy to achieve lipid targets and decrease inflammation. Our study aimed at evaluating the effects of three lipid-modifying therapies on LDL-cholesterol, CRP levels and markers of cholesterol absorption and synthesis.. A prospective intervention study was performed in high cardiovascular risk individuals receiving atorvastatin 10mg daily for four weeks. Those with CRP≥2.0mg/L were randomized to another four-week treatment period with atorvastatin 40mg, ezetimibe 10mg or the combination of atorvastatin 40mg / ezetimibe 10mg. Lipids, markers of cholesterol absorption (campesterol and β-sitosterol), and synthesis (desmosterol), as well as CRP were quantified at baseline and end of study.. One hundred and twenty two individuals were included. Atorvastatin alone or combined with ezetimibe reduced both LDL-cholesterol and CRP (P<0.002 vs. baseline; Wilcoxon); ezetimibe did not modify CRP. Ezetimibe-based therapies reduced absorption markers and their ratios to cholesterol (P<0.0001 vs. baseline, for all; Wilcoxon), whereas atorvastatin alone increased campesterol/cholesterol and β-sitosterol/cholesterol ratios (P<0.05 vs. baseline; Wilcoxon). In addition, ezetimibe also increased desmosterol and desmosterol/cholesterol ratio (P<0.0001 vs. baseline; Wilcoxon).. These results contribute to understanding the link between cellular cholesterol homeostasis, inflammation and lipid-modifying therapies. Our findings highlight the broader benefit of combined therapy with a potent statin and ezetimibe decreasing inflammation, and preventing increase in cholesterol biosynthesis, an effect not observed with ezetimibe alone.

    Topics: Aged; Anticholesteremic Agents; Atorvastatin; Azetidines; C-Reactive Protein; Cardiovascular Diseases; Cholesterol; Desmosterol; Ezetimibe; Female; Heptanoic Acids; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Inflammation; Male; Middle Aged; Phytosterols; Prospective Studies; Pyrroles; Risk Factors; Sitosterols; Statistics, Nonparametric

2013
The effect of 5 intravenous lipid emulsions on plasma phytosterols in preterm infants receiving parenteral nutrition: a randomized clinical trial.
    The American journal of clinical nutrition, 2013, Volume: 98, Issue:2

    Elevated plasma phytosterol concentrations are an untoward effect of parenteral nutrition (PN) with vegetable oil-based lipid emulsions (LEs). Phytosterols are elevated in neonatal cholestasis, but the relation remains controversial.. The objective was to study the effect of 5 LEs on plasma phytosterols in preterm infants.. One hundred forty-four consecutive admitted preterm infants (birth weight: 500-1249 g) were studied. Patients were randomly assigned to receive 1 of 5 different LEs: S [100% soybean oil (SO)], MS [50% medium-chain triglycerides (MCTs) and 50% SO], MSF (50% MCTs, 40% SO, and 10% fish oil (FO)], OS (80% olive oil and 20% SO), or MOSF (30% MCTs, 25% olive oil, 30% SO, and 15% FO). Phytosterols in the LEs and in plasma (on postnatal day 7 and day 14) were measured by gas chromatography-mass spectrometry.. Patients in the S group had significantly higher total phytosterol intakes than did the other study groups. On PN days 7 and 14, plasma phytosterol concentrations were highest in the S group and lowest in the MOSF group. Despite similar β-sitosterol intakes between the MS and MSF groups, plasma concentrations were significantly lower in the MSF than in the MS group. Only 3 patients (2.1%) developed cholestasis: 1 in the MS, 1 in the MSF, and 1 in the MOSF group. No cases of cholestasis were observed in the S and OS groups.. In uncomplicated preterm infants receiving routine PN, we found a correlation between phytosterol intake and plasma phytosterol concentrations; however, cholestasis was rare and no difference in liver function at 6 wk was observed.

    Topics: Birth Weight; Cholestasis; Emulsions; Fat Emulsions, Intravenous; Female; Fish Oils; Gas Chromatography-Mass Spectrometry; Humans; Infant, Newborn; Infant, Premature; Infant, Premature, Diseases; Liver; Male; Olive Oil; Parenteral Nutrition; Phytosterols; Plant Oils; Sitosterols; Soybean Oil; Triglycerides

2013
Cholesterol metabolism differs after statin therapy according to the type of hyperlipemia.
    Life sciences, 2012, Jun-06, Volume: 90, Issue:21-22

    Non-cholesterol sterols reflect cholesterol metabolism. Statins reduce cholesterol synthesis usually with a rise in cholesterol absorption. Common hyperlipemias have shown different patterns of cholesterol metabolism. We evaluated whether cholesterol absorption and synthesis may differ after statin therapy in primary hyperlipemias.. We determined lipid profile, apoprotein B and serum sterols (lathosterol, sitosterol, campesterol by gas chromatography/mass spectrometry) before and after statins in 80 untreated hyperlipemic patients, 40 with polygenic hypercholesterolemia (PH) and 40 with familial combined hyperlipemia (FCH).. At baseline in FCH lathosterol was significantly higher while campesterol and sitosterol were significantly lower than in PH. After statins, the reduction in LDL-C did not significantly differ between the two groups; in PH there was a significant decrease of lathosterol from 96.1 to 52.6 102 μmol/mmol cholesterol (p=0.0001) with no significant modifications in campesterol and sitosterol; on the opposite, in FCH lathosterol decreased from 117 to 43 102 μmol/mmol cholesterol (p=0.0001) and campesterol and sitosterol significantly increased from 38 to 48 102 μmol/mmol cholesterol (p=0.0001), and from 75 to 86 102 μmol/mmol cholesterol, (p=0.022), respectively. After statin therapy only in FCH Δ-LDL-C showed a significant inverse correlation with Δ-sitosterol and with Δ-campesterol.. Primary hyperlipemias show different patterns of response to statins: in PH LDL reduction appears completely "synthesis inhibition" dependent, while in FCH LDL decrease appears to be synthesis dependent, partially limited by absorption increase. Studying cholesterol metabolism before and after hypolipemic therapy might be useful in identifying the best tailored treatment.

    Topics: Adult; Aged; Atorvastatin; Cholesterol; Cholesterol, LDL; Female; Gas Chromatography-Mass Spectrometry; Heptanoic Acids; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Hyperlipidemia, Familial Combined; Hyperlipidemias; Lipids; Male; Middle Aged; Phytosterols; Pyrroles; Simvastatin; Sitosterols

2012
Absolute oral bioavailability and metabolic turnover of β-sitosterol in healthy subjects.
    Drug metabolism and disposition: the biological fate of chemicals, 2012, Volume: 40, Issue:10

    The metabolic turnover, absolute oral bioavailability, clearance, and volume of distribution for β-sitosterol were measured in healthy subjects. [(14)C]β-Sitosterol was used as an isotopic tracer to distinguish pulse doses from dietary sources and was administered by both oral and intravenous routes. The administered doses of [(14)C]β-sitosterol were in the region of 3 to 4 μg, sufficiently low as not to perturb the kinetics of β-sitosterol derived from the diet. Because the plasma concentrations of [(14)C]β-sitosterol arising from such low doses were anticipated to be very low, the ultrasensitive isotope ratio analytical method of accelerator mass spectrometry was used. The limit of quantification for [(14)C]β-sitosterol was approximately 0.1 pg/ml, the oral absolute bioavailability was just 0.41%, clearance was 85 ml/h, volume of distribution was 46 L, and the turnover was 5.8 mg/day. Given the steady-state concentrations of β-sitosterol (2.83 μg/ml), then the dietary load was calculated to be approximately 1400 mg/day.

    Topics: Administration, Oral; Adolescent; Adult; Area Under Curve; Biological Availability; Biotransformation; Carbon Radioisotopes; Diet; Half-Life; Humans; Hypolipidemic Agents; Injections, Intravenous; Male; Mass Spectrometry; Metabolic Clearance Rate; Middle Aged; Models, Biological; Sitosterols; Young Adult

2012
Cholesterol lowering and inhibition of sterol absorption by Lactobacillus reuteri NCIMB 30242: a randomized controlled trial.
    European journal of clinical nutrition, 2012, Volume: 66, Issue:11

    The percentage of hypercholesterolemic individuals not reaching their LDL-cholesterol (LDL-C) goal remains high and additional therapeutic strategies should be evaluated. The objective of this study was to evaluate the cholesterol-lowering efficacy and mechanism of action of bile salt hydrolase-active Lactobacillus reuteri NCIMB 30242 capsules in hypercholesterolemic adults.. A total of 127 subjects completed a randomized, double-blind, placebo-controlled, parallel-arm, multicenter study. Subjects were randomized to consume L. reuteri NCIMB 30242 capsules or placebo capsules over a 9-week intervention period. The primary outcome was LDL-C relative to placebo at the study end point.. L. reuteri NCIMB 30242 capsules reduced LDL-C by 11.64% (P<0.001), total cholesterol by 9.14%, (P<0.001), non-HDL-cholesterol (non-HDL-C) by 11.30% (P < 0.001) and apoB-100 by 8.41% (P = 0.002) relative to placebo. The ratios of LDL-C/HDL-cholesterol (HDL-C) and apoB-100/apoA-1 were reduced by 13.39% (P = 0.006) and 9.00% (P = 0.026), respectively, relative to placebo. Triglycerides and HDL-C were unchanged. High-sensitivity C-reactive protein and fibrinogen were reduced by 1.05 mg/l (P = 0.005) and 14.25% (P = 0.004) relative to placebo, respectively. Mean plasma deconjugated bile acids were increased by 1.00 nmol/l (P=0.025) relative to placebo, whereas plasma campesterol, sitosterol and stigmasterol were decreased by 41.5%, 34.2% and 40.7%, respectively.. The present results suggest that the deconjugation of intraluminal bile acids results in reduced absorption of non-cholesterol sterols and indicate that L. reuteri NCIMB 30242 capsules may be useful as an adjunctive therapy for treating hypercholesterolemia.

    Topics: Adult; Apolipoprotein A-I; Apolipoprotein B-100; Bile Acids and Salts; C-Reactive Protein; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Double-Blind Method; Female; Fibrinogen; Humans; Hypercholesterolemia; Intestinal Absorption; Limosilactobacillus reuteri; Male; Middle Aged; Phytosterols; Sitosterols; Stigmasterol

2012
Effects of ezetimibe added to statin therapy on markers of cholesterol absorption and synthesis and LDL-C lowering in hyperlipidemic patients.
    Atherosclerosis, 2012, Volume: 225, Issue:2

    Statins inhibit cholesterol synthesis but can upregulate cholesterol absorption, with higher doses producing larger effects. Ezetimibe inhibits cholesterol absorption but also upregulates synthesis. We tested whether ezetimibe added to on-going statin therapy would be most effective in lowering LDL-cholesterol (LDL-C) in subjects on high-potency statins and whether these effects would be related to alterations in cholesterol absorption (β-sitosterol) and synthesis (lathosterol) markers.. Hypercholesterolemic subjects (n = 874) on statins received ezetimibe 10 mg/day. Plasma lipids, lathosterol, and β-sitosterol were measured at baseline and on treatment. Subjects were divided into low- (n = 133), medium- (n = 582), and high- (n = 159) statin potency groups defined by predicted LDL-C-lowering effects of each ongoing statin type and dose (reductions of ~20-30%, ~31-45%, or ~46-55%, respectively).. The high-potency group had significantly lower baseline lathosterol (1.93 vs. 2.58 vs. 3.17 μmol/l; p < 0.001) and higher baseline β-sitosterol values (6.21 vs. 4.58 vs. 4.51 μmol/l, p < 0.001) than medium-/low-potency groups. Ezetimibe treatment in the high-potency group produced significantly greater reductions from baseline in LDL-C than medium-/low-potency groups (-29.1% vs. -25.0% vs. -22.7%; p < 0.001) when evaluating unadjusted data. These effects and group differences were significantly (p < 0.05) related to greater β-sitosterol reductions and smaller lathosterol increases. However, LDL-C reduction differences between groups were no longer significant after controlling for placebo effects, due mainly to modest LDL-C lowering by placebo in the high-potency group.. Patients on high-potency statins have the lowest levels of cholesterol synthesis markers and the highest levels of cholesterol absorption markers at baseline, and the greatest reduction in absorption markers and the smallest increases in synthesis markers with ezetimibe addition. Therefore, such patients may be good candidates for ezetimibe therapy if additional LDL-C lowering is needed.

    Topics: Aged; Anticholesteremic Agents; Apolipoproteins; Azetidines; Biomarkers; C-Reactive Protein; Cholesterol; Cholesterol, LDL; Double-Blind Method; Drug Therapy, Combination; Ezetimibe; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Intestinal Absorption; Male; Middle Aged; Multivariate Analysis; Sitosterols; Time Factors; Treatment Outcome; United States

2012
Non-cholesterol sterols in serum and endarterectomized carotid arteries after a short-term plant stanol and sterol ester challenge.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2011, Volume: 21, Issue:3

    It is not known whether dietary intake of plant stanols or sterols changes the composition of arterial sterols. Therefore, we compared serum and carotid artery cholesterol and non-cholesterol sterols after plant stanol (staest) or sterol (steest) ester feeding in endarterectomized patients.. Elderly statin-treated asymptomatic patients undergoing carotid endarterectomy were randomized double-blind to consume staest (n=11) or steest (n=11) spread (2 g of stanol or sterol/day) for four weeks preoperatively. Non-cholesterol sterols from serum and carotid artery tissue were analysed with gas-liquid chromatography. Staest spread lowered serum total (17.2%), VLDL, and LDL cholesterol and serum triglycerides, while steest spread lowered serum total (13.8%) and LDL cholesterol levels from baseline (p<0.05 for all). Serum cholestanol and avenasterol were decreased in both groups, but campesterol and sitosterol were decreased by staest and increased by steest from baseline (p<0.05 from baseline and between the groups). Serum sitostanol to cholesterol ratio was increased by staest, but in arterial tissue this ratio was similar in both groups. On staest, lathosterol, campesterol, and sitosterol, and on steest sitosterol and avenasterol correlated significantly between serum and arterial tissue. Cholesterol metabolism, eg. lathosterol/campesterol, suggested that plant sterols were reduced in serum and in arterial tissue during staest.. The novel observations were that plant stanol ester consumption, in contrast to plant sterols, tended to reduce carotid artery plant sterols in statin-treated patients. Furthermore, despite increased serum sitostanol contents during plant stanol ester consumption, their arterial levels were unchanged suggesting that sitostanol is not taken up into the arterial wall.

    Topics: Aged; Carotid Stenosis; Cholesterol; Condiments; Double-Blind Method; Endarterectomy, Carotid; Esters; Female; Humans; Male; Phytosterols; Plaque, Atherosclerotic; Preoperative Care; Sitosterols; Sterols

2011
Effects of long term plant sterol and -stanol consumption on the retinal vasculature: a randomized controlled trial in statin users.
    Atherosclerosis, 2011, Volume: 214, Issue:1

    As sitosterolemic patients have an increased cardiovascular risk, there is concern that reducing serum LDL-cholesterol concentrations by plant sterols enriched functional foods might adversely affect vascular function. Whether increased concentrations of plant sterols truly affect vascular function and whether these effects are exclusive to the larger vessels remains unknown. We compared the effects of long-term plant sterol and -stanol consumption on changes in retinal vessels diameter which reflex alterations in the microcirculation. Three randomized groups were studied at baseline and after 85-weeks. Group one (N=11) consumed plant sterol enriched margarine (2.5g/day), the second (N=8) plant stanol enriched margarine (2.5g/day), and the control group (N=11) non-enriched margarine (2.5g/day). Serum cholesterol-standardized campesterol and sitosterol concentrations increased by 354.84±168.22·102μmol/mmol and 84.36±48.26·102μmol/mmol (p<0.001), respectively in the sterol group, while decreasing non-significantly in the plant stanol group. Serum LDL-cholesterol concentrations decreased significantly in both the plant sterol (-0.33±0.33mmol/L, p=0.016) and -stanol groups (-0.38±0.34mmol/L, p=0.018) compared to the increase in the controls (0.29±0.34mmol/L). The mean change in venular diameters for the plant sterol group (2.3±3.1μm), plant stanol groups (-0.8±3.4μm) and control group (-0.8±5.1μm) did not reach significance but the change in cholesterol-standardized campesterol concentrations correlated positively with the change in venular diameter independent of changes in serum LDL-cholesterol concentrations (r=0.39, N=30, p=0.033). Increased serum campesterol concentration correlated positively with increased retinal venular diameter, independent from changes in serum LDL-cholesterol concentrations. This may constitute an explanation for the suggested effects of plant sterols on vascular function. However, this novel finding needs confirmation and further study.

    Topics: Adolescent; Adult; Aged; Arterioles; Cholesterol; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Male; Middle Aged; Phytosterols; Plant Extracts; Retinal Vessels; Sitosterols; Sterols; Venules

2011
Low intestinal cholesterol absorption is associated with a reduced efficacy of phytosterol esters as hypolipemic agents in patients with metabolic syndrome.
    Clinical nutrition (Edinburgh, Scotland), 2011, Volume: 30, Issue:5

    Phytosterols (PS) lower LDLc, but their effect on metabolic syndrome (MetS) remains unknown. We evaluated whether low-fat milk enriched with PS improves cardiovascular risk factors in these patients.. A randomised parallel trial employing 24 moderate-hypercholesterolaemic MetS patients and consisting of two 3-month intervention phases. After a 3-month healthy diet, patients were divided into two intervention groups: diet (n = 10) and diet + PS (n = 14) (2 g/day). A control group of 24 moderate-hypercholesterolaemic patients without MetS (matched in age and BMI) underwent the same procedure.. Neither dietary intervention nor enrichment of PS induced any improvement in the serum lipoprotein profile of MetS patients. By contrast, in the non-MetS population, a healthy diet effectively reduced TC, LDLc, non-HDLc and Apo B-100, with further decreases in TC (6.9%), LDLc (10.5%), non-HDLc (10.3%), Apo B-100 (6.2%) and Apo B-100/ApoA-I ratio (11.6%) being observed when PS were administered. No differences in LDL diameter, hsCRP or homocysteine were detected in any of the groups after consuming PS. This supplementation produced a significant increase in PS levels only in the non-MetS population.. PS therapy appears to be of little value to MetS patients, likely due to its reduced intestinal cholesterol absorption. The efficacy of PS as hypocholesterolaemic agents is thus limited.

    Topics: Adult; Anticholesteremic Agents; Cardiovascular Diseases; Cholesterol; Cholesterol, Dietary; Dietary Supplements; Female; Humans; Hypercholesterolemia; Hypolipidemic Agents; Intestinal Absorption; Lipoproteins; Male; Metabolic Syndrome; Middle Aged; Phytosterols; Risk Factors; Severity of Illness Index; Sitosterols; Spain

2011
Comparison of the impact of trans fatty acids from ruminant and industrial sources on surrogate markers of cholesterol homeostasis in healthy men.
    Molecular nutrition & food research, 2011, Volume: 55 Suppl 2

    Mechanisms by which trans fatty acids (TFA) from industrial (iTFA) and ruminant (rTFA) sources alter cholesterol homeostasis are virtually unknown. We compared the impact of dietary iTFA and rTFA on surrogate markers of cholesterol absorption (β-sitosterol and campesterol) and synthesis (lathosterol) in healthy men.. In a randomized, controlled double-blind crossover study, 38 healthy men consumed three experimental isoenergetic diets for 4 wk each. The three diets were (i) high in iTFA (10.2 g/2500 kcal), (ii) high in rTFA (10.2 g/2500 kcal) and (iii) control diet low in TFA from any source (2.2 g/2500 kcal). The sum of plasma β-sitosterol and campesterol concentrations was significantly reduced after the iTFA diet compared with the control diet (-12%, p=0.050). The reduction in combined β-sitosterol and campesterol levels was larger in magnitude after the rTFA diet (-29% versus the control diet and -20% versus the iTFA diet, p<0.0001). The TFA-rich diets had no impact on plasma lathosterol concentrations.. Very high intakes of rTFA and iTFA decrease cholesterol absorption but have no impact on cholesterol synthesis. Consumption of rTFA reduces cholesterol absorption to a greater extent than iTFA, but this difference does not ultimately affect plasma cholesterol concentrations.

    Topics: Adolescent; Adult; Aged; Animals; Biomarkers; Cholesterol; Double-Blind Method; Homeostasis; Humans; Male; Middle Aged; Phytosterols; Ruminants; Sitosterols; Trans Fatty Acids; Young Adult

2011
Action of plant sterol intervention on sterol kinetics in hypercholesterolemic men with high versus low basal circulatory plant sterol concentrations.
    Journal of the American College of Nutrition, 2011, Volume: 30, Issue:2

    The relationship between plant sterol (PS) absorption and circulatory concentrations with cholesterol absorption and biosynthesis during PS consumption has yet to be clearly elucidated in humans. It is therefore essential to examine campesterol, β-sitosterol, and cholesterol absorption and cholesterol fractional synthesis rate (FSR) following PS consumption in individuals with high versus low basal circulatory PS concentrations.. A randomized, crossover trial was conducted in 82 hypercholesterolemic men consuming spreads with or without 2 g/d of PS for two 4-week periods, each separated by a 4-week washout. Endpoint tracer enrichments after ingestion of (2)H-labeled campesterol or β-sitosterol and (13)C-labeled cholesterol were determined by isotope ratio mass spectrometry.. For both phases of dietary intervention, the endpoint cholesterol absorption index was positively correlated with campesterol (r = 0.5864, p < 0.0001) and β-sitosterol (r = 0.4676, p < 0.0001) absorption indices; inversely, endpoint cholesterol FSR correlated negatively with the absorption indices of campesterol (r = -0.5004, p < 0.0009), β-sitosterol (r = -0.4154, p < 0.05), and cholesterol (r = -0.4056, p < 0.0001). PS intervention reduced absorption indices of campesterol, β-sitosterol, and cholesterol by 36.5% ± 2.7%, 39.3% ± 2.9%, and 34.3% ± 1.9%, respectively, but increased cholesterol FSR by 33.0% ± 3.3% relative to control. Endpoint circulatory PS levels (cholesterol adjusted) were positively associated with endpoint absorption indices of campesterol (r = 0.5586, p < 0.0001, for placebo; r = 0.6530, p < 0.0001, for PS intake) and cholesterol (r = 0.3683, p < 0.001 for placebo; r = 0.3469, p < 0.002, for PS intake) and were negatively associated with cholesterol FSR (r = -0.3551, p < 0.002, for placebo; r = -0.3643, p < 0.001, for PS intake). The cholesterol-lowering effect of PS was most pronounced among individuals falling within the 50th-75th percentiles of basal PS concentrations.. These data suggest that basal PS concentrations indicate not only sterol absorption efficiency but also the extent of PS-induced cholesterol reduction and thus might be clinically useful to predict the extent of cholesterol response to PS intervention within a given individual.

    Topics: Adult; Aged; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Cross-Over Studies; Endpoint Determination; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Sitosterols; Triglycerides

2011
The role of soluble fiber intake in patients under highly effective lipid-lowering therapy.
    Nutrition journal, 2011, Aug-02, Volume: 10

    It has been demonstrated that statins can increase intestinal sterol absorption. Augments in phytosterolemia seems related to cardiovascular disease.. We examined the role of soluble fiber intake in endogenous cholesterol synthesis and in sterol absorption among subjects under highly effective lipid-lowering therapy.. In an open label, randomized, parallel-design study with blinded endpoints, subjects with primary hypercholesterolemia (n = 116) were assigned to receive during 12 weeks, a daily dose of 25 g of fiber (corresponding to 6 g of soluble fibers) plus rosuvastatin 40 mg (n = 28), rosuvastatin 40 mg alone (n = 30), sinvastatin 40 mg plus ezetimibe 10 mg plus 25 g of fiber (n = 28), or sinvastatin 40 mg plus ezetimibe 10 mg (n = 30) alone.. The four assigned therapies produced similar changes in total cholesterol, LDL-cholesterol, and triglycerides (p < 0.001 vs. baseline) and did not change HDL-cholesterol. Fiber intake decreased plasma campesterol (p < 0.001 vs. baseline), particularly among those patients receiving ezetimibe (p < 0.05 vs. other groups), and β-sitosterol (p = 0.03 vs. baseline), with a trend for lower levels in the group receiving fiber plus ezetimibe (p = 0.07). Treatment with rosuvastatin alone or combined with soluble fiber was associated with decreased levels of desmosterol (p = 0.003 vs. other groups). Compared to non-fiber supplemented individuals, those treated with fibers had weight loss (p = 0.04), reduced body mass index (p = 0.002) and blood glucose (p = 0.047).. Among subjects treated with highly effective lipid-lowering therapy, the intake of 25 g of fibers added favorable effects, mainly by reducing phytosterolemia. Additional benefits include improvement in blood glucose and anthropometric parameters.

    Topics: Azetidines; Blood Glucose; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dietary Fiber; Ezetimibe; Female; Fluorobenzenes; Humans; Hypercholesterolemia; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Male; Middle Aged; Phytosterols; Pyrimidines; Rosuvastatin Calcium; Sitosterols; Sulfonamides; Triglycerides

2011
Effect of dalcetrapib, a CETP modulator, on non-cholesterol sterol markers of cholesterol homeostasis in healthy subjects.
    Atherosclerosis, 2011, Volume: 219, Issue:2

    Subjects with high HDL-C show elevated plasma markers of cholesterol absorption and reduced markers of cholesterol synthesis. We evaluated the effect of dalcetrapib, a cholesteryl ester transfer protein modulator, on markers of cholesterol homeostasis in healthy subjects.. Dalcetrapib was administered daily with or without ezetimibe in a randomized, open-label, crossover study in 22 healthy subjects over three 7-day periods: dalcetrapib 900 mg, ezetimibe 10mg, dalcetrapib 900 mg plus ezetimibe 10mg. Plasma non-cholesterol sterols lathosterol and desmosterol (cholesterol synthesis markers) and campesterol, β-sitosterol and cholestanol (intestinal cholesterol absorption markers) were measured. A hamster model was used to compare the effect of dalcetrapib and torcetrapib with or without ezetimibe on these markers and determine the effect of dalcetrapib on cholesterol absorption.. Dalcetrapib increased campesterol, β-sitosterol, and cholestanol by 27% (p = 0.001), 32% (p < 0.001), and 12% (p = 0.03), respectively, in man (non-cholesterol sterol/cholesterol ratio). Dalcetrapib+ezetimibe reduced campesterol by 11% (p = 0.02); β-sitosterol and cholestanol were unaffected. Lathosterol and desmosterol were unchanged with dalcetrapib, but both increased with ezetimibe alone (56-148%, p < 0.001) and with dalcetrapib + ezetimibe (32-38%, p < 0.001). In hamsters, dalcetrapib and torcetrapib increased HDL-C by 49% (p = 0.04) and 72% (p = 0.003), respectively. Unlike torcetrapib, dalcetrapib altered cholesterol homeostasis towards increased markers of cholesterol absorption; cholesterol synthesis markers were unaffected by either treatment. Dalcetrapib did not change plasma (3)H-cholesterol level but increased (3)H-cholesterol in plasma HDL vs non-HDL, after oral dosing of labeled cholesterol.. Dalcetrapib specifically increased markers of cholesterol absorption, most likely reflecting nascent HDL lipidation by intestinal ABCA1, without affecting markers of synthesis.

    Topics: Amides; Animals; Anticholesteremic Agents; Azetidines; Biomarkers; Cholestanol; Cholesterol; Cholesterol Ester Transfer Proteins; Cholesterol, HDL; Cricetinae; Cross-Over Studies; Desmosterol; Esters; Ezetimibe; Homeostasis; Humans; Intestinal Absorption; Lipid Metabolism; Male; Mesocricetus; Models, Animal; Phytosterols; Quinolines; Sitosterols; Sulfhydryl Compounds; Switzerland

2011
Cholesterol absorption and synthesis markers in individuals with and without a CHD event during pravastatin therapy: insights from the PROSPER trial.
    Journal of lipid research, 2010, Volume: 51, Issue:1

    Cholesterol homeostasis, defined as the balance between absorption and synthesis, influences circulating cholesterol concentrations and subsequent coronary heart disease (CHD) risk. Statin therapy targets the rate-limiting enzyme in cholesterol biosynthesis and is efficacious in lowering CHD events and mortality. Nonetheless, CHD events still occur in some treated patients. To address differences in outcome during pravastatin therapy (40 mg/day), plasma markers of cholesterol synthesis (desmosterol, lathosterol) and fractional cholesterol absorption (campesterol, sitosterol) were measured, baseline and on treatment, in the Prospective Study of Pravastatin in the Elderly at Risk trial participants with (cases, n = 223) and without (controls, n = 257) a CHD event. Pravastatin therapy decreased plasma LDL-cholesterol and triglycerides and increased HDL-cholesterol concentrations to a similar extent in cases and controls. Decreased concentrations of the cholesterol synthesis markers desmosterol (-12% and -11%) and lathosterol (-50% and -56%) and increased concentrations of the cholesterol absorption markers campesterol (48% and 51%) and sitosterol (25% and 26%) were observed on treatment, but the magnitude of change was similar between cases and controls. These data suggest that decreases in cholesterol synthesis in response to pravastatin treatment were accompanied by modest compensatory increases in fractional cholesterol absorption. The magnitude of these alterations were similar between cases and controls and do not explain differences in outcomes with pravastatin treatment.

    Topics: Aged; Aged, 80 and over; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Coronary Disease; Desmosterol; Female; Homeostasis; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Male; Phytosterols; Pravastatin; Sitosterols; Triglycerides

2010
Baseline cholesterol absorption and the response to ezetimibe/simvastatin therapy: a post-hoc analysis of the ENHANCE trial.
    Journal of lipid research, 2010, Volume: 51, Issue:4

    Subjects with increased cholesterol absorption might benefit more from statin therapy combined with a cholesterol absorption inhibitor. We assessed whether baseline cholesterol absorption markers were associated with response to ezetimibe/simvastatin therapy, in terms of LDL-cholesterol (LDL-C) lowering and cholesterol absorption inhibition, in patients with familial hypercholesterolemia (FH). In a posthoc analysis of the two-year ENHANCE trial, we assessed baseline cholesterol-adjusted campesterol (campesterol/TC) and sitosterol/TC ratios in 591 FH patients. Associations with LDL-C changes and changes in cholesterol absorption markers were evaluated by multiple regression analysis. No association was observed between baseline markers of cholesterol absorption and the extent of LDL-C response to ezetimibe/simvastatin therapy (beta = 0.020, P = 0.587 for campesterol/TC and beta<0.001, P = 0.992 for sitosterol/TC). Ezetimibe/simvastatin treatment reduced campesterol levels by 68% and sitosterol levels by 62%; reductions were most pronounced in subjects with the highest cholesterol absorption markers at baseline, the so-called high absorbers (P < 0.001). Baseline cholesterol absorption status does not determine LDL-C lowering response to ezetimibe/simvastatin therapy in FH, despite more pronounced cholesterol absorption inhibition in high absorbers. Hence, these data do not support the use of baseline absorption markers as a tool to determine optimal cholesterol lowering strategy in FH patients. However, due to the exploratory nature of any posthoc analysis, these results warrant further prospective evaluation in different populations.

    Topics: Adult; Aged; Anticholesteremic Agents; Azetidines; Biomarkers; Cholesterol; Cholesterol, LDL; Double-Blind Method; Drug Therapy, Combination; Ezetimibe; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hyperlipoproteinemia Type II; Intestinal Absorption; Male; Middle Aged; Phytosterols; Simvastatin; Sitosterols; Statistics as Topic

2010
Atorvastatin reduces macrophage accumulation in atherosclerotic plaques: a comparison of a nonstatin-based regimen in patients undergoing carotid endarterectomy.
    Stroke, 2010, Volume: 41, Issue:6

    The object of our study was to compare the effect of high-dose vs low-dose atorvastatin vs nonstatin-based treatment (cholestyramine plus sitosterol) on cell composition of carotid plaque.. We recruited 60 hypercholesterolemic patients (total cholesterol, 5.83-7.64 mmol/L) eligible for carotid endarterectomy. Three months before surgery, patients were randomized into 3 groups (n=20) receiving atorvastatin 10 mg/day (AT-10) or atorvastatin 80 mg/day (AT-80) or cholestyramine 8 g/day plus sitosterol 2.5 g/day. Analysis of cell composition was performed on endarterectomy specimens.. The 3 treatments resulted in a significant reduction of total cholesterol and low-density lipoprotein cholesterol (LDL-C), although the decrease in total cholesterol and LDL-C was of smaller magnitude in the cholestyramine plus sitosterol group. The 3 regimens did not influence the levels of inflammatory markers (including high-sensitivity C-reactive protein). Macrophage content was significantly lower in the AT-10 group plaques compared to the cholestyramine plus sitosterol group. It was further reduced in the AT-80 group plaques. These differences were no longer significant after adjustment for changes in LDL-C. No difference in lymphocyte number was observed among treatments, whereas the content of smooth muscle cells was higher in the AT- 80 group. An inverse association was observed between LDL-C changes in the 3 groups and macrophage content in the plaques.. Short-term treatment with high-dose statin is superior to a nonstatin lipid-lowering regimen in reducing the macrophage cell content within atherosclerotic lesions, but this effect was determined by the degree of LDL-C-lowering.

    Topics: Aged; Aged, 80 and over; Anticholesteremic Agents; Atherosclerosis; Atorvastatin; Biomarkers; C-Reactive Protein; Cholesterol, LDL; Cholestyramine Resin; Endarterectomy, Carotid; Female; Heptanoic Acids; Humans; Hypercholesterolemia; Lymphocyte Count; Macrophages; Male; Pyrroles; Sitosterols

2010
Lipid-lowering effects of ezetimibe for hypercholesterolemic patients with and without type 2 diabetes mellitus.
    Endocrine journal, 2010, Volume: 57, Issue:10

    To date, there are very few clinical reports that have compared the effects of ezetimibe on lipid parameters between hypercholesterolemic patients with and without type 2 diabetes mellitus (T2DM). In this study, we recruited patients for hypercholesterolemic groups with T2DM (n = 42; men/women = 24/18; HbA1c = 6.7 ± 5.4%) and without T2DM (n = 21; men/women = 7/14; HbA1c = 5.3 ± 0.4%). Patients were prescribed ezetimibe at a dose of 10 mg/daily for the course of the 12-week study. At baseline and after 12 weeks of treatment, several lipid parameters, including serum low-density-lipoprotein cholesterol (LDL-C), non-high-density-lipoprotein cholesterol (non-HDL-C), high-sensitivity C-reactive protein (hs-CRP), and cholesterol synthesis/absorption-related markers, were measured. Compared with those at the baseline, the levels of LDL-C, non-HDL-C, campesterol, and sitosterol were significantly reduced after 12 weeks of ezetimibe treatment in both groups. After adjusting for confounding factors, such as age, gender, smoking, and BMI, the levels of LDL-C and non-HDL-C displayed significantly greater reductions in the patients with T2DM (-25.1 ± 13.6% in LDL-C, -20.5 ± 11.2% in non-HDL-C) than those without T2DM (-20.5 ± 7.8% in LDL-C, P < 0.05; -17.4 ± 7.6% in non-HDL-C, P < 0.05). The reduction of the level of cholestanol was significantly and positively correlated with those of LDL-C and non-HDL-C in the patients with T2DM. Taken together, these findings indicate that ezetimibe could reduce the levels of atherogenic lipoproteins to a greater extent in hypercholesterolemic patients with T2DM than in those without T2DM.

    Topics: Aged; Azetidines; Biomarkers; Body Mass Index; C-Reactive Protein; Cardiovascular Diseases; Cholestanol; Cholesterol; Cholesterol, LDL; Diabetes Mellitus, Type 2; Ezetimibe; Female; Humans; Hypercholesterolemia; Hypolipidemic Agents; Lipids; Male; Middle Aged; Phytosterols; Sitosterols

2010
Baseline plasma plant sterol concentrations do not predict changes in serum lipids, C-reactive protein (CRP) and plasma plant sterols following intake of a plant sterol-enriched food.
    European journal of clinical nutrition, 2009, Volume: 63, Issue:4

    Plant sterol (PS) consumption lowers serum cholesterol levels, while modestly increasing plasma PS concentrations. Plasma PS concentrations may reflect sterol absorption, thus individuals with high plasma plant sterol (HPS) concentrations may show greater changes in circulating cholesterol and PS than individuals with low plasma plant sterol (LPS) concentrations. The objective of this study was to examine whether HPS and LPS concentrations are related to subsequent changes in plasma PS, serum lipid and C-reactive protein (CRP) concentrations, following dietary PS intake in otherwise healthy hypercholesterolemic men.. This single-blinded, randomized, diet-controlled study consisted of two 4-week phases, separated by a 4-week washout, where a diet with a placebo or the 2.0 g per day PS-enriched spread was consumed during the phases.. At baseline, men with HPS possessed higher (P<0.01) mean serum cholesterol concentration, while those with LPS had higher (P<0.05) body mass index. Following PS intake, plasma sum of campesterol plus sitosterol concentrations were elevated from 34.6+/-4.2 to 46.2+/-3.3 micromol l(-1) (mean+/-SE) and 16.5+/-0.9 to 20.8+/-1.2 micromol l(-1) after PS intake in men with HPS and LPS, respectively. Changes in plasma PS concentrations, however, were not different between individuals with either HPS or LPS baseline concentrations. Total cholesterol and low-density lipoprotein cholesterol levels were decreased (P<0.0001) by 6.3 and 7.8%, respectively, with PS consumption for all individuals. Changes in lipid parameters were not different between individuals with HPS or LPS baseline concentrations. No changes in CRP were apparent subsequent to PS intervention.. Baseline plasma PS concentrations are not associated or predictive of changes in serum cholesterol or plasma PS concentrations after PS intervention. Thus, individuals with HPS show similar increases in PS concentrations as individuals with LPS following PS supplementation. Plasma PS remained in the range of previously reported concentrations.

    Topics: Body Mass Index; C-Reactive Protein; Cholesterol; Cholesterol, LDL; Food, Fortified; Humans; Lipids; Male; Middle Aged; Phytosterols; Single-Blind Method; Sitosterols

2009
Safety assessment of common foods enriched with natural nonesterified plant sterols.
    European journal of clinical nutrition, 2009, Volume: 63, Issue:5

    To assess safety during a diet based on low-fat foods enriched with nonesterified wood-derived plant sterols and mineral nutrients related to serum phytosterol, sex hormone and fat-soluble vitamin metabolism.. Seventy-one study participants (52 women, 19 men) with mild-to-moderate hypercholesterolemia completed the double-blind, placebo-controlled feeding trial lasting for 15 weeks. The subjects were randomly allocated to the sterol group receiving food items enriched with mineral nutrients as well as with a total of 1.25, 2.5 and 5.0 g per day of plant sterols during the first, second and third 5-week periods, respectively, or to the placebo group receiving similar food items without plant sterols. This outpatient clinical trial with free-living subjects was carried out at two hospital clinics.. Two significant findings were observed. Serum sitosterol concentrations increased from 2.84 to 5.35 mg l(-1) (P<0.004 vs placebo) but those of serum total plant sterols did not because of compensatory changes in other phytosterols. The highest plant sterol levels did not exceed 0.6% of total serum sterols. Serum alpha-tocopherol concentrations decreased in the sterol group by 10% (P<0.0002), but the between-group difference disappeared after adjusting for the change in the carrier (LDL cholesterol).. Fifteen-week consumption of natural nonesterified plant sterol-enriched food does not cause any serious adverse effects during such a period. However, serum alpha-tocopherol levels were somewhat reduced in the sterol group suggesting that long-term effects of plant sterols on serum fat-soluble vitamin concentrations should be further explored, especially in relation to very low-fat diets.

    Topics: Adult; Aged; alpha-Tocopherol; Cholesterol, LDL; Diet; Double-Blind Method; Female; Finland; Food, Fortified; Gonadal Steroid Hormones; Humans; Hypercholesterolemia; Hypolipidemic Agents; Male; Middle Aged; Phytosterols; Sitosterols; Vitamins

2009
Long-term efficacy and safety of ezetimibe 10 mg in patients with homozygous sitosterolemia: a 2-year, open-label extension study.
    International journal of clinical practice, 2008, Volume: 62, Issue:10

    To assess the long-term efficacy and safety profile of ezetimibe 10 mg/day in patients with homozygous sitosterolemia.. This was an extension of a multi-centre, randomised, double-blind, placebo-controlled base study in which patients with homozygous sitosterolemia and plasma sitosterol concentrations > 5 mg/dl were randomised 4 : 1 to ezetimibe 10 mg/day (n = 30) or placebo (n = 7) for 8 weeks. Patients who successfully completed the base study with > 80% compliance to study medication were eligible to enter two, successive, 1-year extension studies in which ezetimibe 10 mg/day was administered in an open-label manner. Patients remained on their current treatment regimen (e.g. bile salt-binding resins, statins and low-sterol diet) during the base and extension studies. Patients had to be off ezetimibe therapy for > or = 4 weeks prior to entering the first extension. Efficacy and safety/tolerability parameters were evaluated every 12 and 26 weeks in the first and second years respectively. The primary efficacy end-point was mean percentage change in plasma sitosterol from baseline to study end for the cohort of patients (n = 21) who successfully completed the second extension study.. Treatment with ezetimibe 10 mg/day led to significant mean percentage reductions from baseline in plasma concentrations of sitosterol (-43.9%; p < 0.001), campesterol (-50.8%; p < 0.001), low-density lipoprotein (LDL) sterols (-13.1%; p < 0.050), total sterols (-10.3%; p < 0.050) and apolipoprotein (apo) B (-10.1%; p < 0.050). No significant changes from baseline were observed for lathosterol, high-density lipoprotein sterol, triglycerides or apo A-1. Maximal reductions in sitosterol and campesterol occurred within the first 52 weeks of treatment and were sustained for the duration of the study. For LDL sterol, total sterols and apo B, maximal reductions were achieved early (by weeks 4 or 16) and waned slightly through the remainder of the study. Overall ezetimibe 10 mg was well tolerated.. In patients with homozygous sitoserolemia, long-term treatment with ezetimibe 10 mg/day for 2 years was effective in reducing plasma plant sterol concentrations with an overall favourable safety and tolerability profile.

    Topics: Achilles Tendon; Adolescent; Adult; Aged; Anticholesteremic Agents; Azetidines; Child; Double-Blind Method; Ezetimibe; Female; Homozygote; Humans; Hypercholesterolemia; Male; Middle Aged; Sitosterols; Treatment Outcome; Young Adult

2008
Effects of long-term plant sterol or stanol ester consumption on lipid and lipoprotein metabolism in subjects on statin treatment.
    The British journal of nutrition, 2008, Volume: 100, Issue:5

    Consumption of plant sterol- or stanol-enriched margarines by statin users results in an additional LDL-cholesterol reduction of approximately 10 %, which may be larger than the average decrease of 3-7 % achieved by doubling the statin dose. However, whether this effect persists in the long term is not known. Therefore, we examined in patients already on stable statin treatment the effects of 85 weeks of plant sterol and stanol ester consumption on the serum lipoprotein profile, cholesterol metabolism, and bile acid synthesis. For this, a double-blind randomised trial was designed in which fifty-four patients consumed a control margarine with no added plant sterols or stanols for 5 weeks (run-in period). For the next 85 weeks, seventeen subjects continued with the control margarine and the other two groups with either a plant sterol (n 18) or plant stanol (n 19) (2.5 g/d each) ester-enriched margarine. Blood was sampled at the end of the run-in period and every 20 weeks during the intervention period. Compared with the control group, plant sterol and stanol ester consumption reduced LDL-cholesterol by 0.28 mmol/l (or 8.7 %; P = 0.08) and 0.42 mmol/l (13.1 %; P = 0.006) respectively after 85 weeks. No effects were found on plasma concentrations of oxysterols or 7 alpha-hydroxy-4-cholesten-3-one, a bile acid synthesis marker. We conclude that long-term consumption of both plant sterol and stanol esters effectively lowered LDL-cholesterol concentrations in statin users.

    Topics: Analysis of Variance; Anticholesteremic Agents; Biomarkers; Cholestenones; Cholesterol; Cholesterol, LDL; Double-Blind Method; Esters; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Lipid Metabolism; Lipoproteins; Male; Margarine; Middle Aged; Phytosterols; Sitosterols; Stigmasterol

2008
Effects of yoghurt enriched with free plant sterols on the levels of serum lipids and plant sterols in moderately hypercholesterolaemic subjects on a high-fat diet.
    International journal of food sciences and nutrition, 2008, Volume: 59, Issue:5

    This study examined the effect of plant sterols added, together with an emulsifying agent, to a low-fat yoghurt on the serum lipid and plant sterol values in moderately hypercholesterolaemic volunteers. Study I was a randomized double-blind, cross-over trial. For 4 weeks, 15 volunteers consumed yoghurt containing 1 g plant sterols or a placebo yoghurt. Study II was a randomized, double-blind, parallel-group study. For 8 weeks, the sterol group (n = 12) ingested daily two yoghurts (2 g/day plant sterols) and the placebo group (n = 14) ingested two yoghurts without plant sterols. Study I: compared with the placebo, the sterol yoghurt reduced serum total cholesterol by 0.15 mmol/l (2.2%, P=0.235) and low-density lipoprotein (LDL) cholesterol by 0.19 mmol/l (4.3%, P=0.082), and increased serum campesterol by 0.26 mg/100 ml (P=0.006) and sitosterol by 0.11 mg/100 ml (P=0.015). Study II: compared with the placebo, the sterol yoghurt reduced serum total cholesterol by 0.41 mmol/l (6.3%, P=0.167) and LDL cholesterol by 0.28 mmol/l (6.4%, P=0.306), and increased serum campesterol by 0.28 mg/100 ml (P=0.016) and sitosterol by 0.40 mg/100 ml (P=0.206). Meta-analysis: the pooled treatment difference was -0.34 mmol/l (5.2%, P=0.173) in total cholesterol and was -0.26 mmol/l (-5.8%, P=0.261) in LDL cholesterol, when the sterol yoghurt was compared with the placebo. A low-fat yoghurt enriched with 1-2 g/day plant sterols reduced serum cholesterol levels in moderately hypercholesterolaemic subjects. Campesterol and sitosterol serum levels increased, but their concentration remained in the range of normal values.

    Topics: Adult; Analysis of Variance; Anticholesteremic Agents; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Double-Blind Method; Female; Humans; Hypercholesterolemia; Lipids; Male; Middle Aged; Phytosterols; Sitosterols; Yogurt

2008
Basal plasma concentrations of plant sterols can predict LDL-C response to sitosterol in patients with familial hypercholesterolemia.
    European journal of clinical nutrition, 2008, Volume: 62, Issue:4

    Familial hypercholesterolemia (FH) is associated with a high risk of coronary heart disease. Pharmacological treatment and diet are both essential for the management of FH. Foods rich in plant sterols (PS) may play an important role in the treatment of patients with these disorders.. To test the effect of the intake of PS on low-density lipoprotein (LDL) concentration, endothelial function (EF) and LDL particle size in 30 patients with FH.. Randomized and crossover dietary intervention study.. Tertiary outpatient care.. Thirty-eight were recruited, but only 30 were subjected to four low-fat dietary intervention periods, each of 4 weeks.. Each intervention had a different content of cholesterol (<150 or 300 mg/day) and sitosterol (<1 or 2 g/day). Lipid response, EF and LDL particle size were analysed after the intervention.. Plasma sitosterol/cholesterol ratio was higher during both plant sterol-rich periods than during the low plant sterols periods. Basal sitosterol concentrations predicted the LDL-cholesterol response during the intake of plant sterol-enriched diets. The change in LDL-cholesterol was significantly greater in subjects in the upper and intermediate tertiles of basal plasma sitosterol concentrations (-21+/-8 mg/dl, P=0.03; -19+/-7 mg/dl, P=0.04, respectively) than in subjects in the lower tertile (8+/-5 mg/dl) when they changed from a low cholesterol diet to a low cholesterol plus plant sterol diet.. Our study demonstrates that basal sitosterol values can predict hypolipidemic response in patients with FH.

    Topics: Adult; Cholesterol, LDL; Combined Modality Therapy; Cross-Over Studies; Diet, Fat-Restricted; Endothelium, Vascular; Female; Humans; Hyperlipoproteinemia Type II; Hypolipidemic Agents; Male; Particle Size; Phytosterols; Predictive Value of Tests; Sitosterols; Treatment Outcome

2008
Effects of ezetimibe, simvastatin, atorvastatin, and ezetimibe-statin therapies on non-cholesterol sterols in patients with primary hypercholesterolemia.
    Current medical research and opinion, 2008, Volume: 24, Issue:1

    Levels of cholesterol are regulated by its synthesis, absorption, and elimination. Plasma levels of phytosterols (e.g., sitosterol, campesterol) and ratios of these sterols to total cholesterol (TC) are reported to correlate with efficiency of intestinal cholesterol absorption, whereas levels of certain cholesterol precursor sterols (e.g., desmosterol, lathosterol) and their ratios to TC correlate with cholesterol biosynthesis. However, there is a paucity of published data concerning the effects of combined treatment using HMG-CoA reductase inhibitors (statins) and a cholesterol absorption inhibitor (ezetimibe) on these parameters.. To characterize the effects of ezetimibe co-administered with statins, compared with each treatment alone, on cholesterol precursor sterols and plasma phytosterol levels.. A post-hoc analysis was performed to determine the effects of treatment with ezetimibe 10 mg, simvastatin (10-80 mg), and atorvastatin (10-80 mg), alone or in combination, on these non-cholesterol sterols using plasma samples from two randomized controlled trials involving patients with primary hypercholesterolemia (low-density lipo protein [LDL-C] = 145-250 mg/dL; triglycerides < or = 350 mg/dL; N = 975) but without a recent (< or = 6-month) history of coronary heart disease (CHD) or either uncontrolled or newly diagnosed diabetes mellitus.. Ezetimibe monotherapy significantly reduced plasma sitosterol and campesterol concentrations from baseline compared with placebo (both p < 0.001), whereas statins significantly lowered desmo sterol and lathosterol levels (p < 0.001 vs. placebo). Co-administration of ezetimibe and statins significantly decreased plasma levels of all of these sterols (p < 0.001).. The observed effects of co-administration of ezetimibe and statins on non-cholesterol sterols are consistent with net inhibition of sterol absorption (driven by ezetimibe) in conjunction with net inhibition of cholesterol synthesis (driven by statins). The potential influence of treatment-induced changes in phytosterols on cardiovascular risk warrants further investigation in long-term, prospective, randomized controlled trials. This post-hoc study was by nature exploratory, and, because data from such analyses are not customarily adjusted for multiple comparisons, some associations may have emerged as statistically significant by chance. Future prospective randomized controlled studies may help to confirm our findings and address other research issues, such as the generalizability of our findings to patients with CHD or diabetes mellitus and possible dose:response relationships between escalating statin (or ezetimibe-statin) doses and circulating non-cholesterol levels.

    Topics: Aged; Anticholesteremic Agents; Azetidines; Cholesterol; Double-Blind Method; Drug Therapy, Combination; Ezetimibe; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Placebos; Simvastatin; Sitosterols; Sterols

2008
Efficacy and safety of ezetimibe 40 mg vs. ezetimibe 10 mg in the treatment of patients with homozygous sitosterolaemia.
    International journal of clinical practice, 2008, Volume: 62, Issue:7

    To assess the effect of ezetimibe (EZE) 40 mg/day on non-cholesterol sterol plasma concentrations in patients with homozygous sitosterolaemia (HoS).. This was a multi-centre, randomised, double-blind, placebo-controlled parallel group study. Twenty-seven patients (> or = 18 years) with HoS and plasma sitosterol levels > 5 mg/dl who had been taking EZE 10 mg/day for > or = 6 months prior to enrolment received open-label EZE 10 mg/day for the duration of the study and were randomised 1 : 1 to blinded EZE 30 mg/day (4 x EZE 10 mg tablets; n = 13) or placebo (1 x EZE 10 mg tablet and 3 x matching placebo tablets; n = 14) for 26 weeks. Patients were permitted to remain on other ongoing treatments (e.g. bile salt-binding resin, statin and/or low sterol diet). End-points included median per cent between-group changes from baseline in plasma sitosterol, campesterol, lathosterol, low-density lipoprotein (LDL) sterols, LDL cholesterol (LDL-C) measured by gas-liquid chromatography, and Achilles tendon thickness size measured radiographically.. Ezetimibe 40 mg/day resulted in median per cent changes from baseline in plasma sitosterol levels of 3.3% vs. -10% in the EZE 10 mg/day group, in plasma campesterol of -0.5% vs. -9.7% in the EZE 10 mg/day group, and in plasma lathosterol of 0.8% vs. 1.1% in the EZE 10 mg/day group (p = ns for all between-group differences). Median per cent changes in the EZE 40 mg/day and EZE 10 mg/day groups, respectively, were 1.3% and 0% for LDL sterols and 2.5% and 4.4% for LDL-C (p = ns for both between-group differences). At study end-point, Achilles tendon thickness remained unchanged in the EZE 40 mg/day group and increased slightly in the EZE 10 mg/day group (2.2%), yielding a non-significant between-group difference of -2.2%. EZE 40 mg/day was generally well tolerated.. In patients with HoS, treatment with EZE 40 mg/day for 26 weeks was no more effective at reducing plasma plant sterol concentrations vs. EZE 10 mg/day. EZE 40 mg/day had a safety and tolerability profile similar to EZE 10 mg/day.

    Topics: Adolescent; Adult; Aged; Anticholesteremic Agents; Azetidines; Dose-Response Relationship, Drug; Double-Blind Method; Ezetimibe; Female; Humans; Lipid Metabolism, Inborn Errors; Male; Middle Aged; Sitosterols; Treatment Outcome; Young Adult

2008
Effect of low-fat, fermented milk enriched with plant sterols on serum lipid profile and oxidative stress in moderate hypercholesterolemia.
    The American journal of clinical nutrition, 2007, Volume: 86, Issue:3

    Plant sterol (PS)-enriched foods have been shown to reduce plasma LDL-cholesterol concentrations. In most studies, however, PSs were incorporated into food products of high fat content.. We examined the effect of daily consumption of PS-supplemented low-fat fermented milk (FM) on the plasma lipid profile and on systemic oxidative stress in hypercholesterolemic subjects.. Hypercholesterolemic subjects (LDL-cholesterol concentrations >or=130 and

    Topics: Animals; C-Reactive Protein; Carotenoids; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Double-Blind Method; Female; Fermentation; Humans; Hypercholesterolemia; Lipids; Male; Middle Aged; Milk; Oxidative Stress; Patient Compliance; Phytosterols; Sitosterols; Treatment Outcome; Triglycerides

2007
Serum noncholesterol sterols in children with heterozygous familial hypercholesterolemia undergoing pravastatin therapy.
    The Journal of pediatrics, 2006, Volume: 148, Issue:2

    To assess causes for insufficient cholesterol-lowering response to pravastatin and plant stanol esters in children with heterozygous familial hypercholesterolemia (HeFH).. Nine of 16 children with HeFH who had not reached normocholesterolemia (< or =194 mg/dL [< or =5 mmol/L]) by 1 year after treatment (40 mg pravastatin and plant stanol ester) were called nonresponders. The 7 remaining children were responders. Serum noncholesterol sterol ratios (10(2) x mmol/mol of cholesterol), surrogate estimates of cholesterol absorption (cholestanol, campesterol, sitosterol) and synthesis (desmosterol and lathosterol), were studied at study baseline (on plant stanol esters) and during combination therapy with pravastatin and plant stanol esters.. Pravastatin decreased the serum levels of cholesterol and cholesterol synthesis markers, and increased the ratios of cholesterol absorption markers. Compared with the responders, the nonresponders had higher study baseline (on plant stanol esters) serum cholesterol concentrations (299 +/- 39 vs 251 +/- 35 mg/dL [7.7 +/- 1.0 vs 6.5 +/- 0.9 mmol/L]; P <.001) and higher respective ratios of campesterol (371 +/- 99 vs 277 +/- 67 10(2) x mmol/mol of cholesterol; P = .049) and sitosterol (176 +/- 37 vs 126 +/- 24 10(2) x mmol/mol of cholesterol; P = .008). The higher the ratio of cholestanol at study baseline, the smaller the 1-year percent reduction in cholesterol (r = .556; P = .025).. Pravastatin treatment increases the markers of cholesterol absorption and decreases those of cholesterol synthesis in HeFH during simultaneous inhibition of cholesterol absorption. Combined inhibition of cholesterol absorption and synthesis may not normalize serum lipids in those patients with the highest cholesterol levels, especially if signs of enhanced cholesterol absorption are detectable.

    Topics: Adolescent; Anticholesteremic Agents; Child; Cholestanol; Cholesterol; Desmosterol; Female; Heterozygote; Humans; Hyperlipoproteinemia Type II; Male; Phytosterols; Pravastatin; Sitosterols; Triglycerides

2006
Beta-glucan incorporated into a fruit drink effectively lowers serum LDL-cholesterol concentrations.
    The American journal of clinical nutrition, 2006, Volume: 83, Issue:3

    beta-Glucan can reduce serum concentrations of total and LDL cholesterol. The mechanism of this action is not clear, however, and it is difficult to predict the cholesterol-lowering effect of a food product enriched with beta-glucan.. We examined the effects of a beta-glucan-enriched fruit juice on serum lipids and lipoproteins and on markers of cholesterol absorption (serum concentrations of plant sterols) and synthesis (serum concentrations of lathosterol). In addition, we measured effects on lipid-soluble antioxidants.. After a 3-wk run-in period, healthy subjects consumed daily a fruit drink providing 5 g rice starch [placebo (control) group; n = 22] or beta-glucan from oats (n = 25) for 5 wk (parallel design). At the end of the run-in period and at the end of the intervention, blood samples were taken for analysis of lipids and lipoproteins, noncholesterol sterols, and fat-soluble antioxidants. Changes between the end of the run-in period and the end of the intervention were calculated for each subject. Differences in changes between the groups were analyzed statistically.. The differences between the control and beta-glucan groups in the change in serum concentrations of total and LDL cholesterol, respectively, were -4.8% (P = 0.012) and -7.7% (P = 0.005). The differences between the groups in the change in serum concentrations of lathosterol and sitosterol were -13% (P = 0.023) and -11% (P = 0.030), respectively. No significant effects were found on fat-soluble antioxidants.. Beta-glucan lowers serum concentrations of total and LDL cholesterol when incorporated into a fruit drink. A reduced cholesterol absorption contributes to the cholesterol-lowering effect of beta-glucan without affecting plasma concentrations of lipid-soluble antioxidants.

    Topics: Adolescent; Adult; Aged; Antioxidants; beta-Glucans; Beverages; Cholesterol; Cholesterol, Dietary; Cholesterol, LDL; Dietary Fiber; Double-Blind Method; Female; Fruit; Humans; Intestinal Absorption; Male; Middle Aged; Sitosterols

2006
Disposition and sterol-lowering effect of ezetimibe are influenced by single-dose coadministration of rifampin, an inhibitor of multidrug transport proteins.
    Clinical pharmacology and therapeutics, 2006, Volume: 80, Issue:5

    The disposition and sterol-lowering effect of ezetimibe are associated with long-lasting enterosystemic circulation, which is initiated by secretion of ezetimibe and its glucuronide via intestinal P-glycoprotein (P-gp) (ABCB1) and the multidrug resistance-associated protein 2 (MRP2) (ABCC2) into gut lumen. Hepatic uptake and secretion may contribute to recycling. To obtain deeper insight into the intestinal and hepatic processes, the disposition of ezetimibe was studied in the presence of rifampin (INN, rifampicin), a modulator of P-gp, MRP2, and hepatic organic anion (uptake) transporting polypeptides (OATPs) (SLCOs).. The disposition of ezetimibe (20 mg orally) alone and after coadministration of rifampin (600 mg orally) was measured in a crossover study of 8 healthy subjects with the SLCO1B1 *1a/*1a genotype. Concentrations of ezetimibe and its glucuronide in serum, urine, and feces, as well as cholesterol, lathosterol, and the plant sterols campesterol and sitosterol in serum, were quantified by use of liquid chromatography and gas chromatography with mass spectrometric detection.. After rifampin administration, the maximum serum concentrations of ezetimibe and its glucuronide were significantly elevated (12.0+/-4.20 ng/mL versus 4.67+/-2.72 ng/mL, P=.017, and 282+/-73.8 ng/mL versus 107+/-35.3 ng/mL, P=.012, respectively). The area under the curve of ezetimibe was not affected (102+/-37.6 ng.h/mL versus 140+/-86.3 ng.h/mL, P=not significant), whereas that of the glucuronide was markedly increased (2150+/-687 ng.h/mL versus 1030+/-373 ng.h/mL, P=.012). Renal clearance remained unchanged. Fecal excretion of ezetimibe was markedly decreased (7.6+/-2.2 mg versus 10.4+/-1.8 mg, P=.036), whereas renal excretion of the glucuronide was strongly elevated (4.8+/-1.9 mg versus 2.0+/-1.2 mg, P=.049) after coadministration. The onset of a significant sterol-lowering effect of ezetimibe was significantly shortened by rifampin coadministration.. Coadministration of rifampin increases the maximum serum concentrations of ezetimibe but reduces its enterosystemic recycling, most likely by inhibition of the secretion of ezetimibe and its glucuronide via P-gp and MRP2.

    Topics: Administration, Oral; Adult; Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily B; ATP-Binding Cassette Sub-Family B Member 4; Azetidines; Cholesterol; Chromatography, Gas; Chromatography, Liquid; Cross-Over Studies; Enzyme Inhibitors; Ezetimibe; Feces; Female; Genotype; Glucuronides; Humans; Intestinal Absorption; Intestinal Mucosa; Intestines; Liver-Specific Organic Anion Transporter 1; Male; Multidrug Resistance-Associated Protein 2; Organic Anion Transporters; Phytosterols; Rifampin; Sitosterols; Time Factors

2006
Plant sterol-fortified orange juice effectively lowers cholesterol levels in mildly hypercholesterolemic healthy individuals.
    Arteriosclerosis, thrombosis, and vascular biology, 2004, Volume: 24, Issue:3

    Hypercholesterolemia is a major risk factor for coronary artery disease. Therapeutic lifestyle changes include dietary modifications such as inclusion of phytosterols, which effectively lowers low-density lipoprotein (LDL) cholesterol in margarines and other fats. Their effectiveness in nonfat moieties is not yet established. The aim of this study was to examine if phytosterols alter the plasma lipoprotein profile when incorporated into nonfat orange juice.. After a 2-week run-in phase with orange juice, 72 mildly hypercholesterolemic healthy subjects were randomized to receive either placebo orange juice (placebo OJ) or plant sterol-fortified orange juice (sterol OJ) (2g/d) for 8 weeks. Fasting blood was obtained at baseline, after 2 weeks of OJ, and after 8 weeks of placebo/sterol-OJ supplementation. Sterol OJ supplementation significantly decreased total (7.2%), LDL (12.4%), and non-high-density lipoprotein (HDL) cholesterol (7.8%) compared with baseline and compared with placebo OJ (P<0.01). Apolipoprotein B levels were significantly decreased (9.5%) with sterol OJ. There were no significant changes in HDL cholesterol or triglycerides with the sterol OJ. While folate and B12 levels significantly increased, homocysteine levels were unchanged.. Orange juice fortified with plant sterols are effective in reducing LDL cholesterol and could easily be incorporated into the therapeutic lifestyle changes dietary regimen.

    Topics: Adult; Aged; Apolipoproteins B; Beverages; Cholesterol; Cholesterol, LDL; Citrus; Double-Blind Method; Female; Folic Acid; Food, Fortified; Homocysteine; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Sitosterols; Stigmasterol; Treatment Outcome; Vitamin B 12

2004
Long-term compliance and changes in plasma lipids, plant sterols and carotenoids in children and parents with FH consuming plant sterol ester-enriched spread.
    European journal of clinical nutrition, 2004, Volume: 58, Issue:12

    To study the compliance and changes in plasma lipids, plant sterols, fat-soluble vitamins and carotenoids in children and parents with familial hypercholesterolemia (FH) consuming a plant sterol ester-enriched (PSE) spread.. A 26-week open-label follow-up of children who had previously been studied in a controlled cross-over design. The parents were also included in the open-label arm of the study.. Outpatient clinic for treatment of hyperlipidemia.. A total of 37 children (7-13 y) and 20 parents (32-51 y) diagnosed with 'definite' or 'possible' heterozygous FH. In all, 19 of the parents, but no children, used statins. All were patients at the Lipid Clinic, National Hospital in Oslo.. Subjects were recommended to eat 20 g/day of PSE spread as part of their lipid-lowering diet.. The mean intake of PSE spread was 13.7 and 16.5 g/days in the children and parents, respectively, corresponding to 1.2 and 1.5 g of plant sterols. Plasma total cholesterol decreased by 9.1% in both children (P<0.001) and parents (P=0.002). The corresponding decreases in LDL cholesterol were 11.4% (P<0.001) and 11.0% (P=0.012). Increases in serum lathosterol, campesterol and sitosterol, adjusted for total cholesterol, were observed in the children (31, 96, 48%, respectively, P<0.001) at the end of the controlled cross-over period. In the parents, serum campesterol and sitosterol, adjusted for total cholesterol, increased by 92 and 39%, respectively (P< 0.001). Lipid-adjusted serum alpha- and beta-carotene decreased by 17.4% (P=0.008) and 10.9% (P=0.018), respectively, in the children at the end of the controlled PSE period, but increased again during the follow-up. In the parents, serum alpha- and beta-carotene concentrations were unchanged, while serum lutein and lycopene decreased by 7.3% (P=0.037) and 14.6% (P=0.044), respectively.. Sustained efficacy of cholesterol reduction and long-term compliance of PSE intake were demonstrated in this study.

    Topics: Adolescent; Adult; Carotenoids; Child; Cholesterol; Cross-Over Studies; Female; Humans; Hyperlipoproteinemia Type II; Lipids; Male; Margarine; Middle Aged; Patient Compliance; Phytosterols; Sitosterols; Treatment Outcome

2004
Effects of a new low dose soy protein/beta-sitosterol association on plasma lipid levels and oxidation.
    European journal of nutrition, 2004, Volume: 43, Issue:5

    High doses of soy protein are able to decrease plasma cholesterolemia significantly, but they unbalance daily protein intake and strongly modify nutritional habits in patients.. To evaluate the antihypercholesterolemic efficacy of a low dose soy protein product with added beta-sitosterol (rapport = 4:1) in 36 moderately hypercholesterolemic subjects.. The study was divided into 3 separate periods of 40 days each: a stabilization diet period, followed by a treatment period during which all subjects took 10 g of the test product once daily and, finally, a wash out period. The following parameters were monitored: weight, dietary habits, plasma lipid levels, glycemia, uric acid, fibrinogenemia and antibodies against oxidized LDL (ox-LDL Ab).. From the end of the stabilization diet period to the end of the supplementation with the soy protein product with added beta-sitosterol we observed a 19.64 +/- 20.32 mg/dL, 8.47 +/- 54.61 mg/dL, 1.69 +/- 10.92 mg/dL, and 7.06 +/- 16.66 mg/dL mean +/- SD decrease respectively in LDL-C (p < 0.001), TG (p = 0.358), VLDLs (p = 0.358) and apoB (p = 0.016) levels, associated with a 1.31 +/- 8.08 mg/dL and 1.03 +/- 19.09 mg/dL mean increase respectively in HDLC (p = 0.251) and apoAI (p = 0.749) plasma concentrations. The dietary supplementation did not influence Lp(a) (p = 0.984) and ox-LDL Ab (p = 0.953) plasma levels. A statistically significant correlation was observed for LDL-C plasma levels, between the end of the stabilization diet period and the end of the period of supplementation with soy proteins with added beta-sitosterols (p < 0.001).. Although further long-term clinical studies are necessary before claims can be made regarding the therapeutic effects of the tested formulation, the preliminary findings regarding its efficacy and safety as an antihypercholesterolemic agent are encouraging.

    Topics: Anticholesteremic Agents; Body Weight; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dose-Response Relationship, Drug; Feeding Behavior; Female; Humans; Hypercholesterolemia; Lipid Peroxidation; Male; Middle Aged; Sitosterols; Soybean Proteins; Treatment Outcome; Triglycerides

2004
Impact of simvastatin, niacin, and/or antioxidants on cholesterol metabolism in CAD patients with low HDL.
    Journal of lipid research, 2003, Volume: 44, Issue:4

    The HDL Atherosclerosis Treatment Study (HATS) demonstrated a clinical benefit in coronary artery disease patients with low HDL cholesterol (HDL-C) levels treated with simvastatin and niacin (S-N) or S-N plus antioxidants (S-N+A) compared with antioxidants alone or placebo. Angiographically documented stenosis regressed in the S-N group but progressed in all other groups. To assess the mechanism(s) responsible for these observations, surrogate markers of cholesterol absorption and synthesis were measured in a subset of 123 HATS participants at 24 months (on treatment) and at 38 months (off treatment). Treatment with S-N reduced desmosterol and lathosterol levels (cholesterol synthesis indicators) 46% and 36% (P < 0.05), respectively, and elevated campesterol and beta-sitosterol levels (cholesterol absorption indicators) 70% and 59% (P < 0.05), respectively, relative to placebo and antioxidant but not S-N+A. Treatment with antioxidants alone had no significant effect. Combining S-N with antioxidants reduced desmosterol and lathosterol by 37% and 31%, and elevated campesterol and beta-sitosterol levels by 54% and 46%, but differences did not attain significance. Mean change in percent stenosis was positively associated with a percent change in lathosterol (r = 0.26, P < 0.005) and negatively associated with a percent change in beta-sitosterol (r = -0.21, P < 0.01). These data suggest that changes in stenosis were attributable, in part, to changes in cholesterol metabolism.

    Topics: Antioxidants; Cholesterol; Constriction, Pathologic; Coronary Artery Disease; Desmosterol; Drug Therapy, Combination; Female; Humans; Hypolipidemic Agents; Lipoproteins, HDL; Male; Middle Aged; Niacin; Simvastatin; Sitosterols

2003
Serum noncholesterol sterols during inhibition of cholesterol synthesis by statins.
    The Journal of laboratory and clinical medicine, 2003, Volume: 141, Issue:2

    We studied changes in serum cholestanol and plant sterols (indexes of cholesterol absorption) and cholesterol precursors (indexes of cholesterol synthesis) in response to cholesterol reduction by way of 1 year's treatment with atorvastatin (n = 102) and simvastatin (n = 105) treatments in patients with coronary heart disease. Serum cholesterol levels and ratios of the precursor sterols to cholesterol after 1 year of treatment were reduced in proportion to the pretreatment values (33% +/- 1% by simvastatin and 36% +/- 1% by atorvastatin; P <.01 for difference between groups) for cholesterol; the respective reductions in the precursor sterol:cholesterol ratios were also higher with atorvastatin (50% +/- 2% for lathosterol) than with simvastatin (42% +/- 1%; P <.01 between groups), but the ratio of squalene to cholesterol was increased (17% +/- 5%, P <.001) by atorvastatin. Plant sterol concentrations were gradually increased by atorvastatin but decreased initially by simvastatin. However, their ratios with respect to cholesterol were increased by as much as 82% with atorvastatin and by as much as 39% with simvastatin. In conclusion, effective inhibition of cholesterol synthesis and subsequent reduction in serum cholesterol levels by statins lead to increases in serum plant-sterol levels, probably as a result of reduced biliary secretion and enhanced absorption of these sterols. Because serum plant sterols have been claimed to be involved in the early development of atherosclerosis, the question arises whether continuously increasing serum plant sterols during long-term statin treatment should be prevented by cholesterol malabsorption (eg, by plant stanol ester consumption), especially in subjects with high baseline plant sterol values and effective sterol absorption.

    Topics: Anticholesteremic Agents; Atorvastatin; Cholestanol; Cholesterol; Coronary Disease; Female; Heptanoic Acids; Humans; Male; Middle Aged; Phytosterols; Pyrroles; Simvastatin; Sitosterols; Squalene; Sterols

2003
Red cell and plasma plant sterols are related during consumption of plant stanol and sterol ester spreads in children with hypercholesterolemia.
    The Journal of pediatrics, 2003, Volume: 142, Issue:5

    To show whether the ratios of squalene and cholesterol precursor sterols to cholesterol and cholestanol and plant sterols to cholesterol change differently in plasma and especially in the red cells of hypercholesterolemic children during consumption of plant stanol and sterol ester spreads.. In a randomized, double-blind, crossover study, hypercholesterolemic children (n = 23) consumed low-fat plant stanol and sterol ester spreads for 5-week periods separated by a 5-week washout period. Plasma and red cell lipids, squalene, and noncholesterol sterols were measured before and at the end of each period.. The plant stanol and sterol ester spreads lowered plasma total (-9% and -6%, respectively) and low-density lipoprotein (-12% and -9%) cholesterol but had no effect on red cell cholesterol, high-density lipoprotein cholesterol, or plasma triglycerides. The ratios of plasma and red cell sitosterol and campesterol to cholesterol decreased by 32% to 36% (P <.001) with the plant stanol ester and increased by 40% to 52% (P <.001) with the sterol ester spread.. Consumption of plant sterols increases and consumption of plant stanols decreases the ratios of plant sterols to cholesterol in red cells of hypercholesterolemic children proportionately to the respective changes in plasma.

    Topics: Child; Child, Preschool; Cholesterol, HDL; Cholesterol, LDL; Cross-Over Studies; Double-Blind Method; Erythrocytes; Female; Humans; Hypercholesterolemia; Male; Margarine; Phytosterols; Sitosterols; Time Factors; Triglycerides

2003
Safety of long-term consumption of plant sterol esters-enriched spread.
    European journal of clinical nutrition, 2003, Volume: 57, Issue:5

    To evaluate both efficacy and safety in humans of long-term consumption of spreads containing plant sterol esters.. Randomized double-blind placebo-controlled parallel trial.. : Hundred and eighty-five healthy volunteers (35-64 y).. Volunteers daily consumed 20 g spread enriched with 1.6 g plant sterols as fatty acid esters or a control spread for 1 y. They continued their habitual diet and lifestyle. Outcome measures included efficacy markers such as total and LDL-cholesterol, a large range of safety parameters, and reporting of adverse events.. Consumption of the plant sterol ester-enriched spread consistently lowered total and LDL cholesterol during the 1 y period on average by 4 and 6%, respectively (0.01 < P < 0.05). Plant sterols intake did on average not result in a lower carotenoid concentration (when expressed per LDL-cholesterol) after 52 weeks (P>0.05). However, carotenoid concentrations changed over time. Plant sterols intake reduced lipid adjusted alpha- and beta-carotene-concentrations by only 15-25% after 1 y, relative to control. Lipid-adjusted fat-soluble vitamin concentrations remained unchanged. Plant sterol concentrations in serum were increased from 2.76 to 5.31 ( micro mol/mmol total cholesterol) for campesterol (P<0.0001) and from 1.86 to 2.47 ( micro mol/mmol total cholesterol) for beta-sitosterol (P<0.0001). The increase in total plant sterol concentration in red blood cells (5.29-9.62 micro g/g) did not affect red blood cell deformability. Hormone levels in males (free and total testosterone) and females (luteinizing hormone, follicle stimulating hormone, beta-estradiol and progesterone) as well as all clinical chemical and hematological parameters measured were unaffected. Adverse events reported were not different between subjects consuming control spread and subjects consuming plant sterol esters-enriched spread.. Consumption of a plant sterol esters-enriched spread is an effective way to consistently lower blood cholesterol concentrations and is safe to use over a long period of time.

    Topics: Adult; beta Carotene; Carotenoids; Cholesterol; Cholesterol, LDL; Diet; Dietary Fats; Double-Blind Method; Esters; Female; Humans; Male; Margarine; Middle Aged; Phytosterols; Placebos; Sitosterols

2003
A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women.
    The Journal of nutrition, 2003, Volume: 133, Issue:12

    Plant sterols or phytosterols are common components of plant foods, especially plant oils, seeds and nuts, cereals and legumes. The most common phytosterols are campesterol, beta-sitosterol and stigmasterol. Phytosterols have anticarcinogenic properties. Previous studies have suggested that populations with low breast cancer incidence often consume diets high in phytosterols. The present study evaluated whether consumption of a plant food-based diet, low in animal fat, may increase serum phytosterol levels in postmenopausal women. One hundred and four women volunteers were randomized to dietary intervention or control groups. The dietary intervention included intensive dietary counseling to replace animal products with plant-based foods. Subjects in the dietary intervention group participated twice a week for 18 wk in workshops about the preparation and consumption of a plant food-based diet. The absolute change in serum total phytosterol concentration was greater in the dietary intervention group than in the control group. The percent change tended to differ between groups (P = 0.06). However, only for beta-sitosterol did the absolute and percent changes within a group differ significantly between groups (P = 0.0017). The decrease in serum total cholesterol in the dietary intervention group (-14%) was greater than that in the control group (-4%; P = 0.0005). The results of this study show that circulating levels of phytosterols can be affected by dietary modification. These findings indicate that phytosterols, in particular beta-sitosterol, can be used as biomarkers of exposure in observational studies or as compliance indicators in dietary intervention studies of cancer prevention.

    Topics: Cholesterol; Cohort Studies; Diet; Female; Humans; Hyperandrogenism; Middle Aged; Osmolar Concentration; Phytosterols; Plants, Edible; Postmenopause; Randomized Controlled Trials as Topic; Sitosterols

2003
Consumption of tall oil-derived phytosterols in a chocolate matrix significantly decreases plasma total and low-density lipoprotein-cholesterol levels.
    The British journal of nutrition, 2002, Volume: 88, Issue:5

    In a randomized, double-blind, placebo-controlled trial we evaluated the effect of dietary chocolates enriched with a wood-based phytosterol-phytostanol mixture, containing 18 % (w/w) sitostanol, compared with placebo dietary chocolates in seventy subjects with primary hypercholesterolaemia (total cholesterol levels below 8 mmol/l). For 4 weeks, participants consumed three servings of the phytosterol-enriched chocolate/d that provided 1.8 g unesterified phytosterols/d or a placebo chocolate in conjunction with a low-fat, low-cholesterol diet. Plasma total and LDL-cholesterol levels were statistically significantly reduced by 6.4 % (-0.44 mmol/l) and 10.3 % (-0.49 mmol/l), respectively, after 4 weeks of phytosterol-enriched-chocolate treatment. Plasma HDL-cholesterol and triacylglycerol levels were not affected. Consumption of phytosterol-enriched chocolates significantly increased plasma lathosterol concentration (+20.7 %), reflecting an increased endogenous cholesterol synthesis in response to phytosterol-induced decreased intestinal cholesterol absorption. Furthermore, the chocolates enriched with phytosterols significantly increased both plasma sitosterol (+95.8 %) and campesterol (+64.1 %) levels, compared with the placebo chocolate group. However, the absolute values of plasma sitosterol and campesterol remained within the normal range, that is, below 10 mg/l. The chocolates with phytosterols were palatable and induced no clinical or biochemical side effects. These findings indicate that dietary chocolate enriched with tall oil-derived phytosterols (1.8 g/d) is effective in lowering blood total and LDL-cholesterol levels in subjects with mild hypercholesterolaemia and thus may be helpful in reducing the risk of CHD in these individuals.

    Topics: Adult; Apolipoproteins B; Cacao; Chi-Square Distribution; Cholesterol; Cholesterol, LDL; Double-Blind Method; Female; Humans; Hypercholesterolemia; Lipids; Male; Middle Aged; Phytosterols; Plant Oils; Sitosterols; Statistics, Nonparametric

2002
Comparison of the hepatic clearances of campesterol, sitosterol, and cholesterol in healthy subjects suggests that efflux transporters controlling intestinal sterol absorption also regulate biliary secretion.
    Gut, 2002, Volume: 51, Issue:6

    Recently identified ABCG5/8 transporters are responsible in part for the different absorption rates of campesterol, sitosterol, and cholesterol. These transporters are also expressed in the liver and might regulate biliary sterol secretion.. This study was therefore conducted to determine the biliary secretion rates and hepatic clearances of campesterol, sitosterol, and cholesterol.. Six healthy, male volunteers.. Deuterium labelled sitosterol and campesterol, and unlabelled sitostanol were constantly infused together with a liquid formula using a duodenal perfusion technique. Biliary secretion and hepatic clearance rates were calculated from hourly bile and plasma samples.. Plasma concentrations of cholesterol, campesterol, and sitosterol averaged 167.5 (50) mg/dl (SD), 0.50 (0.22) mg/dl, and 0.30 (0.10) mg/dl, respectively. Sitosterol showed a significantly higher biliary secretion rate (1.23 (0.87) mg/h) than campesterol (0.76 (0.54) mg/h, p=0.0321), but both plant sterols had significantly lower biliary secretion rates compared with cholesterol (47.7 (17.5) mg/h; p=0.001 for both). Hepatic clearance of cholesterol (0.31 (0.18) dl/h) was significantly lower compared with campesterol (2.11 (2.51) dl/h) and sitosterol (4.97 (4.70) dl/h; p=0.028 for both), and the clearance of campesterol was significant lower compared with sitosterol (p=0.028).. The observed inverse relation between hepatic clearance and known intestinal absorption of cholesterol, campesterol, and sitosterol supports the hypothesis that the ABCG5/8 transporters regulating intestinal sterol absorption might also be involved in biliary sterol excretion.

    Topics: Adult; Bile; Cholesterol; Deuterium; Duodenum; Humans; Liver; Male; Metabolic Clearance Rate; Perfusion; Phytosterols; Sitosterols; Statistics, Nonparametric; Sterols

2002
Unesterified plant sterols and stanols lower LDL-cholesterol concentrations equivalently in hypercholesterolemic persons.
    The American journal of clinical nutrition, 2002, Volume: 76, Issue:6

    Plant sterols, in various forms, have been shown to reduce total and LDL-cholesterol concentrations. Particularly controversial at present is the effect of the degree of hydrogenation of the plant sterols on cholesterol-lowering efficacy and the responsible mechanisms.. Our goal was to examine the effect of supplementation with unesterified plant sterols and stanols on plasma lipid and phytosterol concentrations and cholesterol absorption, synthesis, and turnover.. Fifteen otherwise healthy hypercholesterolemic subjects consumed each of 4 dietary treatments in a randomized crossover design. Unesterified sterols and stanols were blended into the butter component of the diet at a dosage of 1.8 g/d. The diets contained plant sterols (NS), plant stanols (SS), a 50:50 mixture of sterols and stanols (NSS), or cornstarch (control).. Plasma total cholesterol concentrations were 7.8%, 11.9%, and 13.1% lower (P < 0.01) in the NS, SS, and NSS groups, respectively, than in the control group. LDL-cholesterol concentrations were 11.3%, 13.4%, and 16.0% lower (P < 0.03) in the NS, SS, and NSS groups, respectively, than in the control group. Plasma triacylglycerols and HDL-cholesterol concentrations did not differ significantly across diets. Cholesterol absorption efficiency was 56.0%, 34.4%, and 48.9% lower (P < 0.001) in the NS, SS, and NSS groups, respectively, than in the control group. The fractional synthesis rate was higher by 45.5% (P < 0.003) in the NSS group than in the control group. Plasma campesterol and sitosterol concentrations were higher (P < 0.01) in the NS group and sitosterol concentrations were lower (P < 0.01) in the SS group than in the control group.. These data indicate that, in their free unesterified form, sterols and stanols lower plasma LDL cholesterol equivalently in hypercholesterolemic persons by suppressing cholesterol absorption.

    Topics: Adult; Butter; Cholesterol; Cholesterol, LDL; Cross-Over Studies; Diet; Double-Blind Method; Female; Humans; Hypercholesterolemia; Kinetics; Lipids; Male; Middle Aged; Phytosterols; Phytotherapy; Sitosterols

2002
Effects of a new soy/beta-sitosterol supplement on plasma lipids in moderately hypercholesterolemic subjects.
    Journal of the American Dietetic Association, 2002, Volume: 102, Issue:12

    Our aim was to test the hypocholesterolemic effect of a low-dose formulation of soy proteins supplemented with isolated b-sitosterol in a ratio of 4:1 in 20 moderately hypercholesterolemic subjects. The study has been divided in three different periods of forty days each: a stabilization diet period, then a treatment period during which all subjects assumed 10 g one time a day of the tested product and, finally, a wash out period. From the end of the stabilization diet period to the end of the soy protein added in b-sitosterol supplementation we observed a 0.45 +/- 0.30 mmol/L, 0.09 +/- 0.31 mmol/L and 0.17 +/- 0.22 mmol/L mean +/- SE decrease in respectively LDL-C, TG and apoB levels, associated with a 0.12 +/- 0.25 and 0.03 +/- 0.51 mg/dL mean increase respectively in HDL-C and apoA plasma concentrations. According to this recommends, low doses of soy protein added in b-sitosterol seems to be a practical and safe alternative for patients seeking modest reductions in LDL-C (< 15%).

    Topics: Apolipoproteins A; Body Weight; Cholesterol, LDL; Female; Humans; Hypercholesterolemia; Hypolipidemic Agents; Linear Models; Male; Middle Aged; Sitosterols; Soybean Proteins

2002
Effects of plant stanol esters supplied in low-fat yoghurt on serum lipids and lipoproteins, non-cholesterol sterols and fat soluble antioxidant concentrations.
    Atherosclerosis, 2002, Volume: 160, Issue:1

    Oil-based products enriched with plant stanol esters can lower low-density lipoprotein (LDL) cholesterol concentrations by 10-14%. Effectiveness of low-fat products, however, has never been evaluated, although such products fit into a healthy diet. We therefore examined the effects of plant stanol esters emulsified into low-fat yoghurt (0.7% fat) on fasting concentrations of plasma lipids and lipid-soluble antioxidants, which may also change by plant stanol consumption. Sixty non-hypercholesterolemic subjects first consumed daily three cups (3 x 150 ml) of placebo yoghurt for 3 weeks. For the next 4 weeks, 30 subjects continued with the placebo yoghurt, while the other 30 subjects received three cups of experimental yoghurt. Each cup provided 1 g of plant stanols (0.71 g sitostanol plus 0.29 g campestanol) as its fatty acid ester. LDL cholesterol (mean+/-S.D.) increased by 0.06+/-0.21 mmol/l in the placebo group, but decreased by -0.34+/-0.30 mmol/l in the experimental group. The difference in changes between the two groups of 0.40 mmol or 13.7% was highly significant (P<0.001; 95% confidence interval for the difference, (-)0.26 -(-)0.53 mmol/l). Effects were already maximal after 1 week. HDL cholesterol and triacylglycerol concentrations did not change. Total tocopherol levels increased by 1.43 micromol/mmol LDL cholesterol (14.0%, P=0.015). beta-carotene levels, however, decreased by -0.02 micromol/mmol LDL cholesterol (-14.4%, P=0.038). Decreases in absolute beta-carotene concentrations were found in all apoB-containing lipoproteins. LDL-cholesterol standardised phytofluene levels decreased by 21.4+/-25.7% (P<0.001), while other plasma carotenoid (lutein/zeaxanthin, beta-cryptoxanthin, lycopene and alpha-carotene) levels did not change significantly. We conclude that low-fat yoghurt enriched with plant stanol esters lowers within 1 week LDL cholesterol to the same extent as oil-based products. LDL-cholesterol standardised concentrations of tocopherol increased. The observed decrease in beta-carotene levels, as found in many other studies, appears not to be limited to the LDL fraction.

    Topics: Adolescent; Adult; Aged; Antioxidants; Body Weight; Cholesterol; Diet, Fat-Restricted; Double-Blind Method; Female; Humans; Intestinal Mucosa; Lipids; Lipoproteins; Male; Middle Aged; Netherlands; Phytosterols; Plants; Sitosterols; Solubility; Stigmasterol; Yogurt

2002
Carbamazepine increases atherogenic lipoproteins: mechanism of action in male adults.
    American journal of physiology. Heart and circulatory physiology, 2002, Volume: 282, Issue:2

    Treatment with carbamazepine (CBZ) affects cholesterol concentrations, but little is known about the precise nature and underlying mechanisms of changes in lipoprotein metabolism. We investigated prospectively the effects of CBZ on lipid metabolism in normolipemic adults. In 21 healthy males, lipoprotein and noncholesterol sterol concentrations were measured before and during treatment with CBZ for 70 +/- 18 days. Thirteen subjects underwent kinetic studies of apolipoprotein-B (ApoB) metabolism with the use of endogenous stable isotope labeling. Lipoprotein kinetic parameters were calculated by multicompartmental modeling. Significant increases in total cholesterol, in ApoB-containing lipoproteins [very-low-density lipoprotein (VLDL), intermediate density lipoprotein (IDL), and low-density lipoprotein (LDL)], and in triglycerides, but not in high-density lipoprotein (HDL), were observed. Lipoprotein particle composition remained unchanged. Mean fractional catabolic and production rates of ApoB-containing lipoproteins were not significantly different, although mean production rates of VLDL and IDL were substantially increased (+46 +/- 139% and +30 +/- 97%, respectively), whereas mean production of LDL remained unchanged (+2.1 +/- 45.6%). Cholestanol in serum increased significantly but not the concentrations of plant sterols (campesterol, sitosterol) and the cholesterol precursors (lathosterol, mevalonic acid). There was a significant correlation between the decrease in free thyroxine and the increase in IDL cholesterol. Treatment with CBZ increases mainly ApoB-containing lipoproteins. CBZ seems not to influence endogenous cholesterol synthesis or intestinal absorption directly. The increase is neither related to increased ApoB production nor to decreased catabolism but is rather due to changes in the conversion cascade of IDL particles, most likely as an indirect effect through a decrease in thyroid hormones.

    Topics: Adult; Anticonvulsants; Arteriosclerosis; Body Composition; Body Weight; Carbamazepine; Cholestanol; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Cholesterol, VLDL; Diet; Humans; Hydrocortisone; Intestinal Absorption; Lipoproteins; Male; Mevalonic Acid; Phytosterols; Sitosterols

2002
Gastrointestinal absorption and plasma kinetics of soy Delta(5)-phytosterols and phytostanols in humans.
    American journal of physiology. Endocrinology and metabolism, 2002, Volume: 282, Issue:4

    Our objective was to measure the systemic absorption of lecithin-emulsified Delta(5)-phytosterols and phytostanols during test meals by use of dual stable isotopic tracers. Ten healthy subjects underwent two single-meal absorption tests in random order 2 wk apart, one with intravenous dideuterated Delta(5)-phytosterols and oral pentadeuterated Delta(5)-phytosterols and the other with the corresponding labeled stanols. The oral-to-intravenous tracer ratio in plasma, a reflection of absorption, was measured by a sensitive negative ion mass spectroscopic technique and became constant after 2 days. Absorption from 600 mg of Delta(5)-soy sterols given with a standard test breakfast was 0.512 +/- 0.038% for sitosterol and 1.89 +/- 0.27% for campesterol. The absorption from 600 mg of soy stanols was 0.0441 +/- 0.004% for sitostanol and 0.155 +/- 0.017% for campestanol. Reduction of the double bond at position 5 decreased absorption by 90%. Plasma t(1/2) for stanols was significantly shorter than that for Delta(5)-sterols. We conclude that the efficiency of phytosterol absorption is lower than what was reported previously and is critically dependent on the structure of both sterol nucleus and side chain.

    Topics: Adult; Cholesterol; Cross-Over Studies; Deuterium; Female; Glycine max; Half-Life; Humans; Intestinal Absorption; Kinetics; Male; Middle Aged; Phytosterols; Sitosterols

2002
A randomized, double-blind, placebo-controlled trial to determine the effectiveness of botanically derived inhibitors of 5-alpha-reductase in the treatment of androgenetic alopecia.
    Journal of alternative and complementary medicine (New York, N.Y.), 2002, Volume: 8, Issue:2

    Androgenetic alopecia (AGA) is characterized by the structural miniaturization of androgen-sensitive hair follicles in susceptible individuals and is anatomically defined within a given pattern of the scalp. Biochemically, one contributing factor of this disorder is the conversion of testosterone (T) to dihydrotestosterone (DHT) via the enzyme 5-alpha reductase (5AR). This metabolism is also key to the onset and progression of benign prostatic hyperplasia (BPH). Furthermore, AGA has also been shown to be responsive to drugs and agents used to treat BPH. Of note, certain botanical compounds have previously demonstrated efficacy against BPH. Here, we report the first example of a placebo-controlled, double-blind study undertaken in order to examine the benefit of these botanical substances in the treatment of AGA.. The goal of this study was to test botanically derived 5AR inhibitors, specifically the liposterolic extract of Serenoa repens (LSESr) and beta-sitosterol, in the treatment of AGA.. Included in this study were males between the ages of 23 and 64 years of age, in good health, with mild to moderate AGA.. The results of this pilot study showed a highly positive response to treatment. The blinded investigative staff assessment report showed that 60% of (6/10) study subjects dosed with the active study formulation were rated as improved at the final visit.. This study establishes the effectiveness of naturally occurring 5AR inhibitors against AGA for the first time, and justifies the expansion to larger trials.

    Topics: Adult; Alopecia; Cholestenone 5 alpha-Reductase; Double-Blind Method; Enzyme Inhibitors; Humans; Male; Middle Aged; Oxidoreductases; Phytotherapy; Pilot Projects; Plant Extracts; Serenoa; Sitosterols; Treatment Outcome

2002
Micellar distribution of cholesterol and phytosterols after duodenal plant stanol ester infusion.
    American journal of physiology. Gastrointestinal and liver physiology, 2002, Volume: 282, Issue:6

    Properties of the intestinal digestion of the dietary phytosterols, cholesterol and cholestanol, and the mechanisms by which phytosterols inhibit the intestinal absorption of cholesterol in healthy human subjects are poorly known. We have studied the hydrolysis of dietary plant sterol and stanol esters and their subsequent micellar solubilization by determining their concentrations in micellar and oil phases of the jejunal contents. Two liquid formulas with low (formula 1) and high (formula 2) plant stanol concentrations were infused via a nasogastric tube to the descending duodenum of 8 healthy human subjects, and intestinal contents were sampled for gas-liquid chromatographic sterol analysis 60 cm more distally. During the duodenal transit, phytosterol esters were hydrolyzed. This was especially profound for sitostanol, as its esterified fraction per milligram of sitosterol decreased 80% (P < 0.001) in formula 1 and 61% (P < 0.001) in formula 2. Contrary to that, esterified fraction of cholesterol per milligram of sitosterol was increased fourfold (P < 0.001) in formula 1 and almost sixfold (P < 0.001) in formula 2, whereas that of cholestanol remained unchanged. Percentages of esterified sterols and stanols in total intestinal fluid samples were higher after the administration of formula 2 than of formula 1. Esterified cholesterol and stanols accumulated in the oil phase, and free stanols replaced cholesterol in the micellar phase. At high intestinal plant stanol concentrations, cholesterol looses its micellar solubility possibly by replacement of its free fraction in the micellar phase by hydrolyzed plant stanols, which leads to a decreased intestinal absorption of cholesterol.

    Topics: Cholesterol; Cholesterol, Dietary; Esters; Female; Humans; Hydrolysis; Hypolipidemic Agents; Intestinal Absorption; Jejunum; Male; Micelles; Phytosterols; Sitosterols

2002
A single daily dose of soybean phytosterols in ground beef decreases serum total cholesterol and LDL cholesterol in young, mildly hypercholesterolemic men.
    The American journal of clinical nutrition, 2002, Volume: 76, Issue:1

    Consumption of phytosterol-supplemented margarine lowers total plasma cholesterol (TC) and LDL-cholesterol concentrations in older middle-aged hypercholesterolemic individuals. The effects of incorporating phytosterols into lower-fat foods on the plasma lipids of young men at increased risk of developing cardiovascular disease have not been studied.. We tested the hypothesis that a single daily dose of soybean phytosterols added to ground beef will lower plasma TC and LDL-cholesterol concentrations in mildly hypercholesterolemic young men.. In a triple-blind, 4-wk study, 34 male college students with elevated plasma TC (5.85 +/- 0.70 mmol/L), LDL cholesterol (4.02 +/- 0.60 mmol/L), and TC:HDL cholesterol (5.5 +/- 1.2) were randomly assigned to the control (ground beef alone) or treatment (ground beef with 2.7 g of phytosterols) group. The phytosterol mixture was two-thirds esterified and one-third nonesterified and consisted of beta-sitosterol (48%), campesterol (27%), and stigmasterol (21%).. Consumption of phytosterol-supplemented ground beef lowered plasma TC and LDL-cholesterol concentrations and TC:HDL cholesterol from baseline by 9.3%, 14.6%, and 9.1%, respectively (P < 0.001). The LDL particle size did not change, suggesting that the decrease was primarily of particle number. The decreases were similar in subjects with (n = 8) and without (n = 9) a family history of premature cardiovascular disease. No significant changes were found in the control group.. Phytosterol-supplemented ground beef effectively lowers plasma TC and LDL cholesterol and has the potential to become a functional food to help reduce the risk of cardiovascular disease.

    Topics: Adult; Animals; Cattle; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Food, Fortified; Glycine max; Humans; Hypercholesterolemia; Male; Meat Products; Phytosterols; Sitosterols; Stigmasterol

2002
Serum plant sterols and biliary cholesterol secretion in humans: studies with ursodeoxycholic acid.
    Journal of lipid research, 2002, Volume: 43, Issue:7

    Ratios of cholestanol, campesterol, and sitosterol to cholesterol in serum are known to reflect cholesterol absorption efficiency. Here, a possible link between these ratios and biliary secretion rates of cholesterol was investigated. Biliary lipid secretion rates and serum sterols were determined in 13 patients with gallstones. Seven were treated with ursodeoxycholic acid (UDCA) (1,000 mg/d). Serum cholesterol and non-cholesterol sterols were also measured in a cross over study in 20 healthy volunteers, who received either placebo or UDCA (750 mg/d). Biliary cholesterol secretion was significantly lower, whereas the non-cholesterol sterols and their ratio to cholesterol were higher in patients with gallstones treated with UDCA. A highly significant negative linear correlation between the ratios of non-cholesterol sterols to cholesterol and biliary cholesterol secretion was observed. In volunteers, administration of UDCA for 4 weeks was followed by a significant increase in non-cholesterol sterols and their ratios. Even 4 weeks after discontinuing UDCA administration, campesterol and sitosterol were still significantly higher than pretreatment levels, which was also true for the campesterol-cholesterol ratio after 8 weeks. The results suggest that the ratios of cholestanol, campesterol, and sitosterol to cholesterol can be used as indicators of changes in biliary cholesterol secretion rates.

    Topics: Adult; Bile; Cholagogues and Choleretics; Cholesterol; Female; Humans; Male; Middle Aged; Phytosterols; Sitosterols; Ursodeoxycholic Acid

2002
Split-thickness skin graft donor site dressing: preliminary results of a controlled, clinical comparative study of MEBO and Sofra-Tulle.
    Annals of plastic surgery, 2001, Volume: 46, Issue:1

    Topics: Bandages; Framycetin; Humans; Postoperative Care; Sitosterols; Skin Transplantation; Tissue and Organ Harvesting; Wound Healing

2001
Divergent changes in serum sterols during a strict uncooked vegan diet in patients with rheumatoid arthritis.
    The British journal of nutrition, 2001, Volume: 85, Issue:2

    The effects of a strict uncooked vegan diet on serum lipid and sterol concentrations were studied in patients with rheumatoid arthritis. The subjects were randomized into a vegan diet group (n 16), who consumed a vegan diet for 2-3 months, or into a control group (n 13), who continued their usual omnivorous diets. Serum total and LDL-cholesterol and -phospholipid concentrations were significantly decreased by the vegan diet. The levels of serum cholestanol and lathosterol also decreased, but serum cholestanol:total cholesterol and lathosterol:total cholesterol did not change. The effect of a vegan diet on serum plant sterols was divergent as the concentration of campesterol decreased while that of sitosterol increased. This effect resulted in a significantly greater sitosterol:campesterol value in the vegan diet group than in the control group (1.48 (SD 0.39) v. 0.72 (SD 0.14); P < 0.001). A higher concentration of campesterol compared with sitosterol is normal in omnivorous subjects and can be explained by lower absorption and esterification rates of sitosterol. Our results suggest that a strict uncooked vegan diet changes the relative absorption rates of these sterols and/or their biliary clearance.

    Topics: Arthritis, Rheumatoid; Cholestanol; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Diet, Vegetarian; Female; Humans; Middle Aged; Phospholipids; Phytosterols; Sitosterols; Statistics, Nonparametric; Sterols

2001
Dietary plant sterols alter the serum plant sterol concentration but not the cholesterol precursor sterol concentrations in young children (the STRIP Study). Special Turku Coronary Risk Factor Intervention Project.
    The Journal of nutrition, 2001, Volume: 131, Issue:7

    Plant sterol supplementation reduces serum cholesterol concentration but may increase serum plant sterol concentrations, especially in children. We determined whether natural dietary plant sterols derived mainly from vegetable oil or margarine in early childhood affect serum concentrations of plant sterols (campesterol and sitosterol) and cholesterol precursor sterols (Delta-8 cholestenol, desmosterol, and lathosterol), reflecting endogenous cholesterol synthesis. We measured the serum sterol concentrations using gas liquid chromatography in 20 healthy 13-mo-old intervention children in a randomized, prospective study designed to decrease exposure of the children to known environmental atherosclerosis risk factors and in 20 control children. The diet of the intervention children was rich in plant sterols due to replacement of milk fat with vegetable fat, whereas the diet of the control children contained only small amounts of plant sterols. The intervention children consumed twice as much plant sterols as the control children (P < 0.001). Their serum concentrations of campesterol and sitosterol were 75% and 44% higher, respectively, than those in the control children (P < 0.001 for both), but serum cholesterol precursor sterol concentrations did not differ between the two groups. We conclude that doubling dietary plant sterol intake almost doubles serum plant sterol concentrations in 13-mo-old children, but has no effect on endogenous cholesterol synthesis. Relative intestinal absorption of natural plant sterols from the diet in early childhood is similar to that in adults.

    Topics: Arteriosclerosis; Case-Control Studies; Cholesterol; Chromatography, Gas; Desmosterol; Diet Records; Female; Humans; Hypolipidemic Agents; Infant; Intestinal Absorption; Male; Margarine; Phytosterols; Plant Oils; Prospective Studies; Risk Factors; Sitosterols

2001
Solubilization of phytosterols in diacylglycerol versus triacylglycerol improves the serum cholesterol-lowering effect.
    European journal of clinical nutrition, 2001, Volume: 55, Issue:7

    This study was performed to investigate the difference in the serum-cholesterol- and triglyceride-lowering activities between phytosterols dissolved in diacylglycerol (PS/DG) and dispersed in triacylglycerol (PS/TG). The effects of the solvent on the concentrations of serum beta-sitosterol and campesterol were examined.. The study had a randomised crossover design.. Twelve healthy normocholesterolemic or moderately hypercholesterolemic men aged 29-50 y participated in this study.. For 2 weeks before the test period (designated as the control period), all subjects consumed control mayonnaise (PS free) daily with supper and were randomly assigned to two groups for the 2 week test period; one group was given mayonnaise containing PS (500 mg/day) dissolved in DG (10 g/day), and the other mayonnaise containing PS (500 mg/day) dispersed in TG (10 g/day). After a wash out period consuming control PS-free mayonnaise for 4 weeks, the groups were reversed for 2 weeks.. PS/TG feeding had no effect on the serum cholesterol level. In contrast, PS/DG feeding significantly reduced the total and LDL cholesterol levels from the initial value of 5.57 to 5.31 mmol/l (4.7%; P<0.05) and from 3.69 to 3.39 mmol/l (7.6%; P<0.05), respectively. Moreover, the degree of total cholesterol reduction induced by PS/DG feeding in the test period was significantly greater than that induced by PS/TG feeding (P<0.05). In addition, the serum beta-sitosterol and campesterol concentrations did not change during the PS/TG or PS/DG feeding periods.. Dissolution of PS in DG had a better serum cholesterol lowering effect than dissolution in TG.. Kao Corporation.

    Topics: Adult; Cholesterol; Cholesterol, LDL; Cross-Over Studies; Diglycerides; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Sitosterols; Solubility; Triglycerides

2001
Evaluating the role of alternative therapy in burn wound management: randomized trial comparing moist exposed burn ointment with conventional methods in the management of patients with second-degree burns.
    MedGenMed : Medscape general medicine, 2001, Mar-06, Volume: 3, Issue:2

    Moist exposed burn ointment (MEBO), from China, has been said to revolutionize burn management.. Our study was conducted to compare MEBO with conventional management (C) with respect to the rate of wound healing, antibacterial and analgesic effect, and hospital costs.. This is a prospective, randomized, controlled clinical trial conducted between 1 March 1997 and 24 October 1998.. The trial was conducted in a specialized burn facility located in a tertiary referral hospital in a developed and industrialized island-state in Southeast Asia.. We randomly assigned 115 consecutive patients between the ages of 12 and 80 who had partial-thickness thermal burns covering less than 40% of body surface area (BSA) to receive either MEBO or C. Fifty-seven patients were assigned to MEBO and 58 patients to C. The latter group received twice-daily dressing changes; MEBO patients received MEBO every 4 hours.. Patients were hospitalized until 75% BSA had healed. BSA was determined by visual inspection and charted on Lund and Browder charts regularly. Wound healing rate, bacterial infection rate, pain score, and hospitalization costs were recorded.. The median time to 75% healing was 17.0 and 20.0 days with MEBO and C, respectively (HR = 0.67, 95% CI = 0.41-1.11, P =.11), suggesting similar efficacy between the 2 modalities. Bacterial infection rates were similar between the 2 groups (HR = 1.10, 95% CI = 0.59-2.03, P =.76). MEBO imparted a greater analgesic effect in the first 5 days of therapy and reduced hospital costs by 8%.. MEBO is as effective as conventional management but is not the panacea for all burn wounds. The use of MEBO eases the management of face and neck burns and facilitates early institution of occupational therapy in hand burns. It confers better pain relief such that fewer opiates are used during the first 5 days after burn injury.

    Topics: Adult; Aged; Anti-Infective Agents; Anti-Inflammatory Agents, Non-Steroidal; Bandages; Berberine; Burns; Complementary Therapies; Drugs, Chinese Herbal; Health Care Costs; Hospitalization; Humans; Middle Aged; Ointments; Pain Measurement; Plant Extracts; Prospective Studies; Sesame Oil; Singapore; Sitosterols; Treatment Outcome; Wound Healing

2001
Randomized trial of a combination of natural products (cernitin, saw palmetto, B-sitosterol, vitamin E) on symptoms of benign prostatic hyperplasia (BPH).
    International urology and nephrology, 2001, Volume: 33, Issue:2

    Because benign prostatic hyperplasia (BPH) is relatively common, it is important to discover safe and effective means to treat this often debilitating perturbation. Accordingly, we examined the effectiveness of a combination of natural products (cernitin, saw palmetto, B-sitosterol, vitamin E) in treating symptoms of BPH. We undertook a randomized, placebo-controlled, double-blind study. Patients were enrolled from 3 urological practices in the USA. 144 subjects were randomized for study. 17 subjects eventually withdrew, leaving 70 patients in the test group and 57 in the placebo group to complete the study. Inclusion criteria consisted of a diagnosis of BPH, no evidence of cancer, and a maximal urinary flow rate between 5 and 15 ml/second. Patients received either placebo or the combined natural products for 3 months. Evaluations were performed via the American Urological Association (AUA) Symptom Index score, urinary flow rate, PSA measurement, and residual bladder volume. Nocturia showed a markedly significant decrease in severity in patients receiving the combined natural products compared to those taking placebo (p < 0.001). Daytime frequency was also lessened significantly (p < 0.04). When the average individual total AUA Symptom Index score in the test group was compared to that in the placebo group at the end of the study, the difference proved highly significant (p < 0.014). PSA measurements, maximal and average urinary flow rates, and residual volumes showed no statistically significant differences. When taken for 3 months, a combination of natural products (cernitin, saw palmetto, B-sitosterol, vitamin E) compared to placebo can significantly lessen nocturia and frequency and diminish overall symptomatology of BPH as indicated by an improvement in the total AUA Symptom Index score. The combination of natural products caused no significant adverse side effects.

    Topics: Androgen Antagonists; Biological Products; Double-Blind Method; Humans; Male; Plant Extracts; Prostatic Hyperplasia; Secale; Serenoa; Sitosterols; Urodynamics; Vitamin E

2001
Treatment of symptomatic benign prostatic hyperplasia with beta-sitosterol: an 18-month follow-up.
    BJU international, 2000, Volume: 85, Issue:7

    To determine the long-term effects of phytotherapy with beta-sitosterol (the trade name for beta-sitosterol used in this study is Harzol(R)) for symptomatic benign prostatic hyperplasia (BPH). Patient and methods At 18 months after enrolment in a 6-month multicentre double-blind placebo-controlled clinical trial with beta-sitosterol (reported previously), patients were re-evaluated using the modified Boyarsky score, the International Prostate Symptom Score and quality-of-life index, the maximum urinary flow rate (Qmax) and postvoid residual urine volume (PVR). In this open extension of the original trial (after 6 months of treatment or placebo), patients were free to chose their further treatment for BPH.. In all, 117 patients (59%) were eligible for analysis during the follow-up. Of the formerbeta-sitosterol group, 38 patients who continued beta-sitosterol treatment had stable values for all outcome variables between the end of the double-blind study and after 18 months of follow-up. The 41 patients choosing no further therapy had slightly worse symptom scores and PVR, but no changes in Qmax. Of the former placebo group, 27 patients who started beta-sitosterol after the double-blind trial improved to the same extent as the treated group for all outcome variables. The 18 patients choosing no further therapy showed no signs of improvement.. The beneficial effects of beta-sitosterol treatment recorded in the 6-month double-blind trial were maintained for 18 months. Further clinical trials should be conducted to confirm these results before concluding that phytotherapy with beta-sitosterol is effective.

    Topics: Double-Blind Method; Follow-Up Studies; Humans; Male; Prostatic Hyperplasia; Quality of Life; Sitosterols; Treatment Outcome

2000
Noncholesterol sterols and cholesterol lowering by long-term simvastatin treatment in coronary patients: relation to basal serum cholestanol.
    Arteriosclerosis, thrombosis, and vascular biology, 2000, Volume: 20, Issue:5

    Coronary patients with low baseline ratios of serum cholestanol and plant sterols to cholesterol (indicating low cholesterol absorption) but not those with high ratios (high absorption) experienced reduced recurrences of coronary events during simvastatin treatment in the Scandinavian Simvastatin Survival Study. Thus, in the present study, serum cholesterol, its precursor sterols (reflecting cholesterol synthesis), plant sterols (campesterol and sitosterol), and cholestanol were measured before and during a 5-year period of placebo treatment (n=433) and simvastatin treatment (n=434) in patients from a subgroup of the Scandinavian Simvastatin Survival Study to determine whether changes in cholesterol synthesis and serum levels were related to cholesterol absorption. Serum cholesterol level was unchanged, the ratios of cholesterol precursor sterols to cholesterol were decreased, and the ratios of plant sterols to cholesterol were increased in relation to increasing baseline ratios of cholestanol quartiles. The latter predicted 5-year ratios and simvastatin-induced reductions of the precursor sterols, with the lowering of the ratios (cholesterol synthesis reduction) being almost twice higher in the lowest versus the highest quartile. The ratios of plant sterols, especially campesterol, to cholesterol were markedly increased during simvastatin treatment, mostly in subjects with the highest baseline cholestanol quartiles. Simvastatin reduced serum cholesterol more (P=0.003) in the lowest versus the highest cholestanol quartile during the 5-year treatment period. The results show for the first time that baseline cholesterol metabolism, measured by serum noncholesterol sterols, predicts the effectiveness of simvastatin in reducing cholesterol synthesis and serum levels of cholesterol. The drug suppresses the synthesis of cholesterol markedly more effectively in subjects with high than with low baseline synthesis but reduces respective serum cholesterol levels less markedly than synthesis. Subjects with high cholesterol absorption and low synthesis may need a combination therapy to lower more effectively their serum cholesterol levels and prevent an increase in the levels of plant sterols.

    Topics: Anticholesteremic Agents; Body Weight; Cholestanol; Cholesterol; Coronary Disease; Desmosterol; Humans; Phytosterols; Placebos; Simvastatin; Sitosterols; Sterols

2000
The rebound of lipoproteins after LDL-apheresis. Kinetics and estimation of mean lipoprotein levels.
    Atherosclerosis, 2000, Volume: 152, Issue:2

    We studied the rebound of lipoproteins in 20 hypercholesterolemic men [mean total cholesterol (TC) levels 9.6+/-1.8 mmol/l] after LDL-apheresis (LA) to determine the rate of recovery and the change in cholesterol synthesis, and to find a uniform estimation for time-averaged levels. After 10-20 months on biweekly LA using dextran sulfate cellulose columns and concomitant simvastatin administration, time-averaged levels (+/-SD) measured by integration of the area under the curve were as follows: TC 4.4+/-1.0 mmol/l, LDL cholesterol (LDL-C) 2.5+/-1.0 mmol/l, apolipoprotein B (apo B) 1. 3+/-0.3 g/l, triglycerides (TG) 1.7+/-0.7 mmol/l, HDL-C 1.1+/-0.2 mmol/l, and lipoprotein(a) [Lp(a)] 53.7+/-49.4 mg/dl. Mean acute reductions in TC, LDL-C, apo B, Lp(a), and TG were 61, 77, 75, 76, and 62%, respectively. HDL-C levels were not influenced. Median recovery half times for TC, LDL-C, apo B, and Lp(a) were 3.0, 4.0, 2. 3, and 3.5 days, respectively. The rebound of Lp(a) was identical to LDL-C, in 12 and 13 days post-treatment, respectively, whereas apo B and TC returned to pre-treatment levels in 7.5 and 10 days, respectively, due to the fast rebound of VLDL particles. Notwithstanding these differences, time-averaged levels (C(AVG)) could be estimated uniformly for the four latter parameters with the formula: C(AVG)=C(MIN)+0.73(C(MAX)-C(MIN)), where C(MAX) and C(MIN) are the immediate pre- and post-treatment levels. During long-term treatment the whole-body cholesterol synthesis was increased as measured by the ratio lathosterol to cholesterol of 3.24+/-1.49 mmol/mmol, whereas no further transient increase in the recovery period after LA was found. In conclusion, long-term LA and simvastatin therapy induced acute and chronic changes in lipids and lipoproteins showing the feasibility of biweekly treatment. It was shown that time-averaged levels, as a measure for the effective plasma levels, can be accurately estimated from pre- and post-treatment levels only.

    Topics: Adult; Aged; Anticholesteremic Agents; Apolipoproteins B; Blood Component Removal; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Lipoprotein(a); Lipoproteins, LDL; Male; Middle Aged; Simvastatin; Sitosterols; Triglycerides

2000
The effects of B-sitosterol (BSS) and B-sitosterol glucoside (BSSG) mixture on selected immune parameters of marathon runners: inhibition of post marathon immune suppression and inflammation.
    International journal of sports medicine, 1999, Volume: 20, Issue:4

    A pilot study was undertaken to investigate the effects of the intake of capsules containing the plant sterols and sterolins (BSS:BSSG mixture) on selected immune parameters of volunteers participating in an ultra-marathon in Cape Town, South Africa. Those runners having received active capsules (n=9) showed less neutrophilia, lymphopenia and leukocytosis when compared to their counterparts having received placebo capsules (n=8): the placebo treated individuals showed significant increases in their total white blood cell numbers as well as in their neutrophils (p=0.03 and 0.03 respectively). Furthermore, statistically significant increases within lymphocyte subsets were observed in the runners having received the active capsules: CD3+ cells increased (p=0.02) as did CD4+ cells (p=0.03). In parallel, the BSS:BSSG capsules decreased the plasma level of IL6 in the runners using the active capsules (p=0.08) and significantly decreased the cortisol: DHEAs ratio (p=0.03), suggesting that these volunteers had less of an inflammatory response and were less immune suppressed during the post-marathon recovery period. These findings justify further investigations into the use of the phytosterols to prevent the subtle immunosuppression associated with excessive physical stress.

    Topics: Adult; Blood Cell Count; Dietary Supplements; Exercise; Female; Humans; Immunosuppression Therapy; Inflammation; Leukocytosis; Lymphocyte Subsets; Lymphopenia; Male; Middle Aged; Neutrophils; Phytosterols; Sitosterols

1999
Cholesterol-lowering effect of stanol ester in a US population of mildly hypercholesterolemic men and women: a randomized controlled trial.
    Mayo Clinic proceedings, 1999, Volume: 74, Issue:12

    To determine the efficacy of stanol esters in lowering cholesterol in a US population.. After a run-in phase, 318 subjects were randomized to receive one of the following margarine-like spreads containing stanol ester or placebo for 8 weeks: EU 3 G: 1 g of stanol (ester form) per 8-g serving of a European formula 3 times a day; US 3 G: 1 g of stanol (ester form) per 8-g serving of a US reformulation 3 times a day; US 2 G: 0.67 g of stanol (ester form) per 8-g serving of a US reformulation 3 times a day; or placebo spread.. Mean +/- SD baseline total cholesterol (TC) and low-density lipoprotein cholesterol (LDL-C) levels were 233+/-20 and 153+21 mg+/-dL, respectively. In the US 3 G group, 3 g daily of stanol esters lowered TC and LDL-C levels by 6.4% and 10.1%, respectively. There was a dose-dependent response compared with 2 g daily (US 2 G). Triglyceride and high-density lipoprotein cholesterol levels were unchanged. The incidence of adverse effects was not different from placebo. Serum vitamin A and 25-hydroxyvitamin D levels were not affected.. Stanol esters lowered TC and LDL-C levels in a mildly hypercholesterolemic US population without evidence of adverse effects. It may be a useful dietary adjunct to lower cholesterol.

    Topics: Adult; Anticholesteremic Agents; beta Carotene; Cholestanols; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dietary Fats; Dose-Response Relationship, Drug; Double-Blind Method; Esters; Female; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Sitosterols; Treatment Outcome; Triglycerides; United States; Vitamin A; Vitamin D

1999
Plant sterol-enriched margarines and reduction of plasma total- and LDL-cholesterol concentrations in normocholesterolaemic and mildly hypercholesterolaemic subjects.
    European journal of clinical nutrition, 1998, Volume: 52, Issue:5

    To compare effects on plasma total-, LDL-, and HDL-cholesterol concentrations of margarines enriched with different vegetable oil sterols or sitostanol-ester.. A randomized double-blind placebo-controlled balanced incomplete Latin square design with five treatments and four periods of 3.5 weeks. Margarines enriched with sterols from soybean, sheanut or ricebran oil or with sitostanol-ester were compared to a non-enriched control margarine. Sterol intake was between 1.5-3.3 g/d. Two thirds of the soybean oil sterols were esterified to fatty acids.. Unilever Research Laboratory, Vlaardingen, The Netherlands.. One hundred healthy non-obese normocholesterolaemic and mildly hypercholesterolaemic volunteers aged 45+/-12.8 y, with plasma total cholesterol levels below 8 mmol/L at entry.. Plasma lipid, carotenoid and sterol concentrations, blood clinical chemistry and haematology, fatty acid composition of plasma cholesterylesters and food intake.. Ninety-five volunteers completed the study. None of the margarines induced adverse changes in blood clinical chemistry, serum total bile acids or haematology. Plasma total- and LDL-cholesterol concentrations were significantly reduced by 8-13% (0.37-0.44 mmol/L) compared to control for margarines enriched in soybean oil sterol-esters or sitostanol-ester. No effect on HDL-cholesterol concentrations occurred. The LDL- to HDL-cholesterol ratio was reduced by 0.37 and 0.33 units for these margarines, respectively. Effects on blood lipids did not differ between normocholesterolaemic and mildly hypercholesterolaemic subjects. Plasma sitosterol and campesterol levels were significantly higher for the soybean oil sterol margarine and significantly lower for the sitostanol-ester margarine compared to control. Dietary intake was very similar across treatments. The fatty acid composition of plasma cholesterylesters confirmed the good compliance to the treatment. All sterol enriched margarines reduced lipid-standardized plasma alpha- plus beta-carotene levels. Plasma lycopene levels were also reduced but this effect was not significant for all products.. A margarine with sterol-esters from soybean oil, mainly esters from sitosterol, campesterol and stigmasterol, is as effective as a margarine with sitostanol-ester in lowering blood total- and LDL-cholesterol levels without affecting HDL-cholesterol concentrations. Incorporation in edible fat containing products of such substances may substantially reduce the risk of cardiovascular disease in the population.

    Topics: Adult; Carotenoids; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dietary Fats, Unsaturated; Double-Blind Method; Humans; Hypercholesterolemia; Margarine; Middle Aged; Phytosterols; Placebos; Plant Oils; Sitosterols; Soybean Oil

1998
Oral guar gum treatment of intrahepatic cholestasis and pruritus in pregnant women: effects on serum cholestanol and other non-cholesterol sterols.
    European journal of clinical investigation, 1998, Volume: 28, Issue:5

    Our aim was to investigate whether intestinal binding of bile acids by guar gum, a dietary fibre, relieves cholestasis and pruritus in intrahepatic cholestasis of pregnancy.. Forty-eight pregnant women with cholestasis and pruritus were randomized double-blind to guar gum and placebo until the time of delivery, and 20 healthy pregnant women were used as control subjects. The pruritus score and serum bile acids, lipids and non-cholesterol sterols were measured at baseline, at least 2 weeks after treatment, just before delivery and up to 4 weeks after delivery.. The increase in serum bile acids and worsening of pruritus were prevented by guar gum in relation to placebo (P < 0.05). Serum cholesterol was unchanged, but increased cholesterol precursor sterol values suggested that cholesterol synthesis was increased by guar gum. Serum cholestanol proportion, an indicator of cholestasis, was related to pruritus but was unaffected by guar gum.. We conclude that in intrahepatic cholestasis of pregnancy and pruritus, guar gum treatment is beneficial in relieving pruritus, even although indicators of cholestasis are only partially reduced.

    Topics: Administration, Oral; Adult; Cholestanol; Cholestasis, Intrahepatic; Cholesterol; Desmosterol; Dietary Fiber; Double-Blind Method; Female; Galactans; Humans; Mannans; Phytosterols; Plant Gums; Pregnancy; Pregnancy Complications; Pruritus; Random Allocation; Sitosterols

1998
Serum 27-hydroxycholesterol in patients with primary biliary cirrhosis suggests alteration of cholesterol catabolism to bile acids via the acidic pathway.
    Journal of lipid research, 1998, Volume: 39, Issue:12

    Reduced cholesterol synthesis has been reported in patients with primary biliary cirrhosis but no data are available on changes in cholesterol catabolism induced by the disease. Serum levels of 7alpha-hydroxycholesterol and 27-hydroxycholesterol have been measured in 25 patients (either normocholesterolemic or hypercholesterolemic) with primary biliary cirrhosis and in control subjects. To evaluate cholesterol synthesis, serum levels of lathosterol were measured, and campesterol and sitosterol were considered to reflect intestinal absorption and biliary elimination of sterols. In normocholesterolemic patients with primary biliary cirrhosis, lathosterol was significantly lower than in normocholesterolemic controls (P < 0.05) whereas no difference was found between hypercholesterolemic patients and hypercholesterolemic controls. Serum concentrations of sitosterol were significantly higher in both normocholesterolemic and hypercholesterolemic patients with primary biliary cirrhosis as compared with the respective controls (P < 0.01). In patients with primary biliary cirrhosis, serum 7alpha-hydroxycholesterol was slightly higher than in controls. 27-Hydroxycholesterol was significantly higher in hypercholesterolemic compared to normocholesterolemic controls (P < 0.05) and a significant linear correlation (r = 0.771; P < 0.001) was found between 27-hydroxycholesterol and cholesterol. In contrast, in patients with primary biliary cirrhosis, high cholesterol concentrations were not associated with increased serum levels of 27-hydroxycholesterol. Our data confirm that in patients with primary biliary cirrhosis, cholesterol synthesis and biliary elimination of sterols are impaired and also suggest that both the feedback regulation of retained bile acids on cholesterol 7alpha-hydroxylase and the scavenger effect on elevated serum cholesterol by cholesterol 27-hydroxylase are deficient in these patients. acids via the acidic pathway.

    Topics: Aged; Bile Acids and Salts; Cholesterol; Female; Humans; Hydroxycholesterols; Intestinal Absorption; Liver Cirrhosis, Biliary; Male; Middle Aged; Phytosterols; Sitosterols

1998
Lathosterol and other non-cholesterol sterols during treatment of hypercholesterolaemia with beta-glucan-rich oat bran.
    European journal of clinical nutrition, 1997, Volume: 51, Issue:9

    Dietary fibre has been suggested to interfere with endogenous cholesterol synthesis in the liver. Therefore the effects of oat bran on the proportions of cholesterol synthesis precursors (squalene, delta(8-) cholesterol, desmosterol and lathosterol), cholestanol and plant sterols (campesterol and beta-sitosterol) to cholesterol were analysed in serum of 36 hypercholesterolaemic subjects.. A randomized study of eight weeks duration when beta-glucan-rich oat bran (n = 20, subjects) or wheat bran (n = 16) was used as a part of a cholesterol lowering diet. Plant sterols and cholesterol synthesis precursors were analysed from frozen samples afterward.. In the oat-bran group, but not in the wheat bran group, serum total cholesterol declined transiently. The proportions of plant sterols and cholesterol in serum, which reflect cholesterol absorption efficiency were unchanged. However, the proportions of squalene appeared to be transiently increased during the study. Subjects with apolipoprotein E 4 allele had higher serum campesterol and sitosterol levels (suggestive of efficient cholesterol absorption) than those with homozygous apolipoprotein E 3 allele.. Since the cholesterol precursors in serum reflecting endogenous cholesterol synthesis remained almost unchanged the reduction in the serum cholesterol level by oat bran treatment can not be ascribed to an inhibition of the endogenous cholesterol synthesis.

    Topics: Adult; Alleles; Apolipoprotein E4; Apolipoproteins E; Avena; Cholesterol; Dietary Fiber; Female; Glucans; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Sitosterols; Squalene

1997
A randomised placebo-controlled trial of the efficacy of beta-sitosterol and its glucoside as adjuvants in the treatment of pulmonary tuberculosis.
    The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, 1997, Volume: 1, Issue:6

    To evaluate the adjuvant effect of beta-sitosterol and its glucoside in the treatment of culture proven pulmonary tuberculosis (PTB).. A blinded randomised placebo-controlled trial in culture proven drug sensitive PTB. Patients were hospitalised for the duration of treatment and evaluated at monthly intervals with regard to sputum culture positivity, chest radiography, weight gain, Mantoux test response, routine haematology and liver functions. STATISTICAL EVALUATION: General linear models for repeated measures (SAS GLM package) compared the interaction effects, group effects and time effects of findings in 19 patients receiving sitosterols with those in 18 patients receiving a placebo (talcum powder). Absolute values and change from baseline values were evaluated, although only the latter are reported.. Weight gain was significantly greater in the sitosterol group (mean weight gain 8.9 kg) than the placebo group (mean gain 6.1 kg) (P = 0.0023 group effects; P = 0.0001 for time effects). Speed of achieving culture negativity, radiological improvement and induration on Mantoux testing was similar in the two groups. Change in lymphocyte counts from baseline was significantly higher in the sitosterol group (P = 0.0001 and P = 0.0001 for group and time effects) as was the increase in eosinophil counts (P = 0.0001 and P = 0.0137 for group and time effects).. The study has shown significantly improved weight gain and higher lymphocyte and eosinophil counts in PTB patients receiving sitosterols in addition to an efficacious antituberculosis regimen. Sitosterols and their possible mode of action should now be evaluated in larger numbers of tuberculosis patients and in diseases with a similar immunopathogenesis.

    Topics: Adjuvants, Immunologic; Adult; Antitubercular Agents; Humans; Leukocyte Count; Male; Sitosterols; Tuberculosis, Pulmonary; Weight Gain

1997
Anti-inflammatory efficacy of Melothria madraspatana in active rheumatoid arthritis.
    Clinical rheumatology, 1996, Volume: 15, Issue:2

    Topics: Administration, Oral; Adult; Arthritis, Rheumatoid; Female; Humans; India; Male; Medicine, Traditional; Plant Extracts; Plants, Medicinal; Prospective Studies; Sitosterols

1996
[The effectiveness of beta-sitosterol in treatment of benign prostatic hyperplasia].
    Der Urologe. Ausg. A, 1995, Volume: 34, Issue:2

    Topics: Administration, Oral; Aged; Dose-Response Relationship, Drug; Double-Blind Method; Humans; Male; Middle Aged; Prostatic Hyperplasia; Sitosterols; Treatment Outcome; Urinary Bladder Neck Obstruction; Urodynamics

1995
Randomised, placebo-controlled, double-blind clinical trial of beta-sitosterol in patients with benign prostatic hyperplasia. Beta-sitosterol Study Group.
    Lancet (London, England), 1995, Jun-17, Volume: 345, Issue:8964

    Medical treatments have become available for benign hypertrophy of the prostate, including alpha-receptor blocking agents and 5-alpha-reductase inhibitors. Drugs derived from plants, for which no precise mechanism of action has been described, are widely used for this purpose in Europe. In a randomised, double-blind, placebo-controlled multicentre study, 200 patients (recruited between April and October 1993) with symptomatic benign prostatic hyperplasia were treated with either 20 mg beta-sitosterol (which contains a mixture of phytosterols) three times per day or placebo. Primary end-point was a difference of modified Boyarsky score between treatment groups after 6 months; secondary end-points were changes in International Prostate Symptom Score (IPSS), urine flow, and prostate volume. Modified Boyarsky score decreased significantly with a mean of -6.7 (SD 4.0) points in the beta-sitosterol-treated group versus -2.1 (3.2) points in the placebo group p < 0.01. There was a decrease in IPSS (-7.4 [3.8] points in the beta-sitosterol-treated group vs -2.1 [3.8] points in the placebo group) and changes in urine flow parameters: beta-sitosterol treatment resulted in increasing peak flow (15.2 [5.7] mL/s from 9.9 [2.5] mL/s), and decrease of mean residual urinary volume (30.4 [39.9] mL from 65.8 [20.8] mL). These parameters did not change in the placebo group (p < 0.01). No relevant reduction of prostatic volume was observed in either group. Significant improvement in symptoms and urinary flow parameters show the effectiveness of beta-sitosterol in the treatment of benign prostatic hyperplasia.

    Topics: Aged; Double-Blind Method; Drug Administration Schedule; Follow-Up Studies; Humans; Male; Placebos; Prostate; Prostatic Hyperplasia; Quality of Life; Sitosterols; Treatment Outcome; Urinary Retention; Urodynamics

1995
Dietary sitostanol related to absorption, synthesis and serum level of cholesterol in different apolipoprotein E phenotypes.
    Atherosclerosis, 1994, Volume: 105, Issue:2

    Effects of small amounts of sitosterol, sitostanol and sitostanol esters (< 1 g/day of free sterols) dissolved in rapeseed oil (RSO) were studied on serum lipids and cholesterol metabolism in patients with primary hypercholesterolemia and different apolipoprotein E phenotypes on an RSO diet. One of the four groups was an RSO-fed control. Serum total and LDL cholesterol reductions were small in different plant sterol-fed groups, tended to be highest in the sitostanol ester group (-7%), but were significantly reduced by about 5% in the combined plant sterol groups. The reductions were -8% in the subjects with epsilon 4 allele and insignificant in those with apo E3/3 phenotype. Cholesterol precursor sterols in serum, markers of cholesterol synthesis, were increased only in the subjects with epsilon 4 allele. Cholesterol absorption was reduced by 7%, being 31% in the subjects with epsilon 4 allele, and fecal elimination of cholesterol was increased, a finding also indicating increased cholesterol synthesis. The changes in cholesterol absorption were related to those in fecal plant sterols (change in dietary intake) and serum total and LDL cholesterol (P = 0.04, 0.01 and 0.05, respectively). Thus, small amounts of dietary plant sterols (< 1 g/day), especially sitostanol esters dissolved in dietary fats, decrease serum total and LDL cholesterol by a proportional decrease in cholesterol absorption which, in turn, is associated with a compensatory increase in cholesterol synthesis. The effects are most consistent in subjects with epsilon 4 allele, but for effective hypocholesterolemic treatment dietary amount of sitostanol ester should exceed 1 g/day.

    Topics: Absorption; Adult; Apolipoproteins E; Brassica; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Double-Blind Method; Fatty Acids, Monounsaturated; Female; Humans; Hypercholesterolemia; Male; Middle Aged; Phenotype; Plant Oils; Rapeseed Oil; Sitosterols; Triglycerides

1994
Mechanisms of action of plant sterols on inhibition of cholesterol absorption. Comparison of sitosterol and sitostanol.
    European journal of clinical pharmacology, 1991, Volume: 40 Suppl 1

    The effects of two different plant sterols on intestinal cholesterol absorption were compared in normal volunteers by an intestinal perfusion study during a control period followed by high dose infusion of sitosterol or sitostanol (3.6 mumol/min), to which subjects were allocated in a randomized manner. Cholesterol absorption during the control period was similar in the two groups, averaging 0.88 +/- 0.48 mumol/min (32 +/- 11%) for group I (sitosterol) and 0.68 +/- 0.33 mumol/min (29 +/- 9%) for group II (sitostanol). The infusion of a high dose of sitosterol resulted in a significant reduction of cholesterol absorption to 0.47 mumol/min (16%). Following the same dose of sitostanol, cholesterol absorption diminished significantly to 0.15 +/- 0.11 mumol/min (5.1 +/- 2.9%). Overall cholesterol absorption declined during sitosterol infusion by almost 50%, whereas sitostanol infusion caused a reduction of cholesterol absorption by almost 85%. These findings of a more effective inhibition of cholesterol absorption by sitostanol might confirm the observation recorded by others that an increase in hydrophobicity of a plant sterol results in a higher affinity but lower capacity to mixed micells. This may cause an effective displacement of cholesterol from micellar binding and therefore diminished cholesterol absorption.

    Topics: Cholesterol; Cholesterol, Dietary; Humans; Intestinal Absorption; Male; Sitosterols

1991
Bile acids, neutral steroids, and bacteria in feces as affected by a mixed, a lacto-ovovegetarian, and a vegan diet.
    The American journal of clinical nutrition, 1987, Volume: 46, Issue:6

    In a metabolic ward 12 healthy male subjects consumed mixed Western (M), lacto-ovovegetarian (L), and vegan (V) diets in a randomized order for 20 d each. The concentrations of deoxycholic acid, isolithocholic acid, and total bile acids in 4-d composites of feces on the L and V diets were significantly lower than on the M diet. The chenodeoxycholic-to-isolithocholic plus lithocholic acid ratio was significantly higher on the V diet. The concentrations of coprostanol and of coprostanol plus cholesterol were highest on M diet and lowest on V diet. The number of fecal lactobacilli and enterococci on the V diet was significantly lower than on the M or the L diets. This study showed a decrease in the concentration of fecal (secondary) bile acids by the L and the V diets and an alteration of the fecal flora composition by the V diet.

    Topics: Adult; Animals; Bacteria; Bile Acids and Salts; Cholestanol; Cholesterol; Deoxycholic Acid; Diet, Vegetarian; Eggs; Feces; Humans; Lithocholic Acid; Male; Milk; Sitosterols; Steroids

1987
Effect of plant sterols on serum lipids and atherosclerosis.
    Pharmacology & therapeutics, 1985, Volume: 31, Issue:3

    Topics: Absorption; Animals; Arteriosclerosis; Cholesterol; Cholesterol, Dietary; Cholestyramine Resin; Clinical Trials as Topic; Food; Humans; Hypercholesterolemia; Phytosterols; Risk; Sitosterols

1985
Primary hypercholesterolemia: effect of treatment on serum lipids, lipoprotein fractions, cholesterol absorption, sterol balance, and platelet aggregation.
    Mayo Clinic proceedings, 1984, Volume: 59, Issue:4

    The nonabsorbable bile acid sequestrant resin, colestipol, was administered to 16 patients with primary hypercholesterolemia, and its effect on serum lipids, lipoprotein fractions, and circulating platelet aggregate ratio and platelet aggregation in response to adenosine diphosphate (ADP) was compared with that of sitosterol. Cholesterol absorption and sterol balance studies were done in four of the subjects during the following treatment periods: diet alone, colestipol, and sitosterol. Total serum cholesterol was significantly reduced by colestipol but only slightly decreased by sitosterol. Combination treatment with colestipol and sitosterol was associated with a smaller decrease in serum cholesterol than was demonstrated with colestipol alone. Serum triglycerides tended to increase during colestipol therapy (this increase was not clinically significant) but showed a minimal nonsignificant decrease with sitosterol treatment. Colestipol decreased cholesterol absorption, whereas sitosterol slightly increased it. Fecal sterol excretion was increased with colestipol treatment but was minimally affected by administration of sitosterol. Low-density lipoprotein and high-density lipoprotein cholesterol significantly decreased with colestipol treatment. The circulating platelet aggregate ratio was significantly lower in the group of patients with hypercholesterolemia who received colestipol initially than in control subjects, but platelet aggregation in response to ADP was not significantly different between these two groups. No significant change in platelet aggregation was noted during colestipol or sitosterol treatment despite a significant decrease in total serum cholesterol with colestipol therapy, a suggestion that the platelet and lipid abnormalities are not interrelated.

    Topics: Adenosine Diphosphate; Adult; Aged; Cholesterol; Colestipol; Female; Humans; Hyperlipoproteinemia Type II; Lipids; Lipoproteins; Male; Middle Aged; Platelet Aggregation; Polyamines; Sitosterols; Sterols

1984
[Changes in the echostructure of prostatic adenomas during drug therapy].
    Medizinische Klinik (Praxis-Ausg.), 1982, Aug-27, Volume: 77, Issue:18

    Within the scope of a controlled double-blind study to demonstrate the effect of conservative therapy of benign prostatic hyperplasia with Harzol, ultrasonographic examination of the prostate adenoma was carried out on 23 patients before and after therapy with the trial preparation or placebo. Within a two-month treatment with Harzol, there was a significant change in the echo structure of the prostate adenoma, and this is interpreted as a reduction in the interstitial formation of oedema.

    Topics: Clinical Trials as Topic; Double-Blind Method; Humans; Male; Prostatic Hyperplasia; Sitosterols; Ultrasonography

1982
Optimizing the effect of plant sterols on cholesterol absorption in man.
    The American journal of clinical nutrition, 1982, Volume: 35, Issue:4

    During three experimental periods, nine adults were hospitalized on a metabolic ward and fed a meal containing 500 mg of cholesterol as a component of scrambled eggs. In addition, the meal contained: 1) no additive, 2) 1 g beta-sitosterol, or 3) 2 g beta-sitosteryl oleate. Stools for the succeeding 5 days were analyzed to determine the percentage of the cholesterol in the test meal that was absorbed. The addition of beta-sitosterol resulted in a 42% decrease in cholesterol absorption; the beta-sitosteryl oleate caused a 33% reduction. These results indicate that the judicious addition of beta-sitosterol or beta-sitosteryl oleate to meals containing cholesterol-rich foods will result in a significant decrease in cholesterol absorption, with a consequent decrease in plasma cholesterol.

    Topics: Absorption; Adult; Cholesterol, Dietary; Eggs; Feces; Humans; Sitosterols; Structure-Activity Relationship

1982

Other Studies

1474 other study(ies) available for cytellin and gamma-sitosterol

ArticleYear
β-sitosterol targets glucocorticoid receptor to reduce airway inflammation and remodeling in allergic asthma.
    Pulmonary pharmacology & therapeutics, 2023, Volume: 78

    In most asthma patients, symptoms are controlled by treatment with glucocorticoid, but long-term or high-dose use can produce adverse effects. Therefore, it is crucial to find new therapeutic strategies. β-sitosterol could suppress type Ⅱ inflammation in ovalbumin (OVA)-induced mice, but its mechanisms have remained unclear.. A binding activity of β-sitosterol with glucocorticoid receptor (GR) was analyzed by molecular docking. Human bronchial epithelial cells (BEAS-2B) and human bronchial smooth muscle cells (HBSMC) were treated with different concentrations (0, 1, 5, 10, 20, and 50 μg/mL) of β-sitosterol for suitable concentration selection. In transforming growth factor (TGF)-β1 treated BEAS-2B and HBSMC, cells were treated with 20 μg/mL β-sitosterol or dexamethasone (Dex) to analyze its possible mechanism. In OVA-induced mice, 2.5 mg/kg β-sitosterol or Dex administration was performed to analyze the therapeutic mechanism of β-sitosterol. A GR antagonist RU486 was used to confirm the mechanism of β-sitosterol in the treatment of asthma.. A good binding of β-sitosterol to GR (score = -8.2 kcal/mol) was found, and the GR expression was upregulated with β-sitosterol dose increase in BEAS-2B and HBSMC. Interleukin (IL)-25 and IL-33 secretion was significantly decreased by β-sitosterol in the TGF-β1-induced BEAS-2B, and the levels of collagen 1A and α-smooth muscle actin (SMA) were reduced in the TGF-β1-induced HBSMC. In the OVA-challenged mice, β-sitosterol treatment improved airway inflammation and remodeling through suppressing type Ⅱ immune response and collagen deposition. The therapeutic effects of β-sitosterol were similar to Dex treatment in vitro and in vivo. RU486 treatment clearly hampered the therapeutic effects of β-sitosterol in the TGF-β1-induced cells and OVA-induced mice.. This study identified that β-sitosterol binds GR to perform its functions in asthma treatment. β-sitosterol represent a potential therapeutic drug for allergic asthma.

    Topics: Airway Remodeling; Animals; Asthma; Collagen; Disease Models, Animal; Humans; Inflammation; Lung; Mice; Mice, Inbred BALB C; Mifepristone; Molecular Docking Simulation; Ovalbumin; Receptors, Glucocorticoid; Sitosterols; Transforming Growth Factor beta1

2023
β-Sitosterol mitigates hepatocyte apoptosis by inhibiting endoplasmic reticulum stress in thioacetamide-induced hepatic injury in γ-irradiated rats.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2023, Volume: 172

    The endoplasmic reticulum (ER) controls many biological functions besides maintaining the function of liver cells. Various studies reported the role of the ER stress and UPR signaling pathway in various liver diseases via triggering hepatocytes apoptosis. This study aims to investigate the suppressive effect of β-sitosterol (βS) on apoptosis associated with liver injury and ER stress.. Liver damage in rats was induced by TAA (150 mg/kg I.P twice a week/3 weeks) and γ-irradiation (single dose 3.5 Gy) and treated with βS (20 mg/kg daily for 30 days). Serum aminotransferase activity, lipid profile and lipid metabolic factors were measured beside liver oxidative stress and inflammatory markers. Moreover, the hepatic expression of ER stress markers (inositol-requiring enzyme 1 alpha (IRE1α), X-box-binding protein 1 (XBP1) and CCAAT/enhancer binding protein homologous protein (CHOP) and apoptotic markers were detected together with histopathological examination.. βS diminished the aminotransferase activity, the oxidative stress markers as well as the inflammatory mediators. Furthermore, βS lowered the circulating TG and TC and the hepatic lipotoxicity via the suppression of lipogenesis (Srebp-1c) and improved the β-oxidation (Pparα and Cpt1a) together with the mitochondrial biogenesis (Pgc-1 α). Moreover, the upregulated levels of ER stress markers were reduced upon treatment with βS, which consequently attenuated hepatic apoptosis.. βS relieves hepatic injury, ameliorates mitochondrial biogenesis, and reduces lipotoxicity and apoptosis via inhibition of CHOP and ER stress response.

    Topics: Animals; Apoptosis; Chemical and Drug Induced Liver Injury; Endoplasmic Reticulum Stress; Endoribonucleases; Hepatocytes; Liver; Protein Serine-Threonine Kinases; Rats; Sitosterols; Thioacetamide; Transaminases

2023
Solubilization of free β-sitosterol in milk sphingomyelin and polar lipid vesicles as carriers: Structural characterization of the membranes and sphingosome morphology.
    Food research international (Ottawa, Ont.), 2023, Volume: 165

    High consumption of plant sterols reduces the risk of cardiovascular diseases in humans and provides health benefits. Increasing the amount of plant sterols in the diet is therefore necessary to reach the recommended daily dietary intake. However, food supplementation with free plant sterols is challenging because of their low solubility in fats and water. The objectives of this study were to investigate the capacity of milk-sphingomyelin (milk-SM) and milk polar lipids to solubilise β-sitosterol molecules in bilayer membranes organised as vesicles called sphingosomes. The thermal and structural properties of milk-SM containing bilayers composed of various amounts of β-sitosterol were examined by differential scanning calorimetry (DSC) and temperature-controlled X-ray diffraction (XRD), the molecular interactions were studied using the Langmuir film technique, the morphologies of sphingosomes and β-sitosterol crystals were observed by microscopy. We showed that the milk-SM bilayers devoid of β-sitosterol exhibited a gel to fluid L

    Topics: Animals; Humans; Milk; Phytosterols; Sitosterols; Sphingomyelins

2023
Controlled volatile release from β-sitosterol-based oleogels based on different self-assembly mechanisms.
    Food chemistry, 2023, Nov-01, Volume: 425

    This study examined how the self-assembly mechanisms of β-sitosterol-based oleogels influenced the release of volatile compounds. Microscopy, X-ray diffraction (XRD) and small-angle X-ray scattering (SAXS) measurements showed that the three β-sitosterol-based oleogels (β-sitosterol + γ-oryzanol oleogels (SO), β-sitosterol + lecithin oleogels (SL) and β-sitosterol + monostearate oleogels (SM)) had significant differences in their microstructures, which were formed via different self-assembly mechanisms. SO exhibited the highest oil binding capacity (OBC), complex modulus (G*) and apparent viscosity. Dynamic and static headspace analyses suggested that network structure of β-sitosterol-based oleogels affected the release of volatile components. SO showed the strongest retention effect, followed by SL and SM. The release of volatile compounds mainly related to structural strength and compositions of oleogels. These results indicated that β-sitosterol-based oleogels formed with different self-assembly mechanisms have the potential to serve as effective delivery systems for controlling the release of volatile compounds.

    Topics: Scattering, Small Angle; Sitosterols; X-Ray Diffraction

2023
Countenance and implication of Β-sitosterol, Β-amyrin and epiafzelechin in nickel exposed Rat: in-silico and in-vivo approach.
    Scientific reports, 2023, Dec-04, Volume: 13, Issue:1

    The detrimental impact of reactive oxygen species on D.N.A. repair processes is one of the contributing factors to colon cancer. The idea that oxidative stress may be a significant etiological element for carcinogenesis is currently receiving more and more support. The goal of the current study is to evaluate the anti-inflammatory and anticancer activity of three powerful phytocompounds-sitosterol, amyrin, and epiafzelechin-alone and in various therapeutic combinations against colon cancer to identify the critical mechanisms that mitigate nickel's carcinogenic effect. To evaluate the ligand-protein interaction of four selected components against Vascular endothelial growth factor (VEGF), Matrix metalloproteinase-9 (MMP9) inhibitor and Interleukin-10 (IL-10) molecular docking approach was applied using PyRx bioinformatics tool. For in vivo analysis, hundred albino rats were included, divided into ten groups, each containing ten rats of weight 160-200 g. All the groups were injected with 1 ml/kg nickel intraperitoneally per week for three months, excluding the negative control group. Three of the ten groups were treated with β-sitosterol (100 mg/kg b wt), β-amyrin (100 mg/kg b wt), and epiafzelechin (200 mg/kg b wt), respectively, for one month. The later four groups were fed with combinatorial treatments of the three phyto compounds for one month. The last group was administered with commercial drug Nalgin (500 mg/kg b wt). The biochemical parameters Creatinine, Protein carbonyl, 8-hydroxydeoxyguanosine (8-OHdG), VEGF, MMP-9 Inhibitor, and IL-10 were estimated using ELISA kits and Glutathione (G.S.H.), Superoxide dismutase (S.O.D.), Catalase (C.A.T.) and Nitric Oxide (NO) were analyzed manually. The correlation was analyzed through Pearson's correlation matrix. All the parameters were significantly raised in the positive control group, indicating significant inflammation. At the same time, the levels of the foresaid biomarkers were decreased in the serum in all the other groups treated with the three phytocompounds in different dose patterns. However, the best recovery was observed in the group where the three active compounds were administered concomitantly. The correlation matrix indicated a significant positive correlation of IL-10 vs VEGF (r = 0.749**, p = 0.009), MMP-9 inhibitor vs SOD (r = 0.748**, p = 0.0 21). The study concluded that the three phytocompounds β-sitosterol, β-amyrin, and epiafzelechin are important anticancer agents which can target

    Topics: Animals; Biomarkers; Colonic Neoplasms; Interleukin-10; Matrix Metalloproteinase 9; Molecular Docking Simulation; Nickel; Rats; Sitosterols; Vascular Endothelial Growth Factor A

2023
Evaluation of Anti-Hepatocellular-Cancer Properties of β-Sitosterol and β-Sitosterol-Glucoside from Indigofera zollingeriana Miq.
    Methods in molecular biology (Clifton, N.J.), 2022, Volume: 2343

    Liver cancer is the most frequent cancer, making it the leading cause of cancer death globally. Traditional medicinal plants with anticancer properties can be used as drugs or dietary adjuvants to existing therapies. This chapter presents a protocol for the preparation of β-sitosterol and β-sitosterol-glucoside from Indigofera zollingeriana Miq (I. zollingeriana) and the evaluation of these for anticancer activity in hepatocellular cells.

    Topics: Carcinoma, Hepatocellular; Glucosides; Humans; Indigofera; Liver Neoplasms; Plant Extracts; Sitosterols

2022
Plasma oxyphytosterols most likely originate from hepatic oxidation and subsequent spill-over in the circulation.
    The Journal of steroid biochemistry and molecular biology, 2022, Volume: 216

    We evaluated oxyphytosterol (OPS) concentrations in plasma and various tissues of two genetically modified mouse models with either increased cholesterol (apoE KO mice) or increased cholesterol and plant sterol (PS) concentrations (apoExABCG8 dKO mice). Sixteen female apoE KO and 16 dKO mice followed the same standard, low OPS-chow diet. Animals were euthanized at 36 weeks to measure PS and OPS concentrations in plasma, brain, liver and aortic tissue. Cholesterol and oxysterol (OS) concentrations were analyzed as reference for sterol oxidation in general. Plasma campesterol (24.1 ± 4.3 vs. 11.8 ± 3.0 mg/dL) and sitosterol (67.4 ± 12.7 vs. 4.9 ± 1.1 mg/dL) concentrations were severely elevated in the dKO compared to the apoE KO mice (p < 0.001). Also, in aortic and brain tissue, PS levels were significantly elevated in dKO. However, plasma, aortic and brain OPS concentrations were comparable or even lower in the dKO mice. In contrast, in liver tissue, both PS and OPS concentrations were severely elevated in the dKO compared to apoE KO mice (sum OPS: 7.4 ± 1.6 vs. 4.1 ± 0.8 ng/mg, p < 0.001). OS concentrations followed cholesterol concentrations in plasma and all tissues suggesting ubiquitous oxidation. Despite severely elevated PS concentrations, OPS concentrations were only elevated in liver tissue, suggesting that OPS are primarily formed in the liver and plasma concentrations originate from hepatic spill-over into the circulation.

    Topics: Animals; Apolipoproteins E; ATP Binding Cassette Transporter, Subfamily G, Member 8; Cholesterol; Female; Lipid Metabolism; Lipoproteins; Liver; Mice; Mice, Knockout; Oxidation-Reduction; Oxysterols; Phytosterols; Sitosterols

2022
In Vitro Insecticidal Effect of Commercial Fatty Acids, β-Sitosterol, and Rutin against the Sugarcane Aphid, Melanaphis sacchari Zehntner (Hemiptera: Aphididae).
    Journal of food protection, 2022, 04-01, Volume: 85, Issue:4

    The sugarcane aphid, Melanaphis sacchari Zehntner (Hemiptera: Aphididae), is the main pest of sorghum, Sorghum bicolor L. Moench (Poaceae), in Mexico. To control this insect, farmers currently use synthetic chemical insecticides, which are toxic to humans and biodiversity. However, natural products are a promising potential source of safer alternative means to control different agricultural pests. The main objective of this study was to evaluate the insecticidal effect of contact by fumigation of pure molecules of four commercial fatty acids (palmitic, stearic, pentadecanoic, and linoleic acids), the phytosterol β-sitosterol, and the flavonoid rutin. The results showed that fatty acids were the most effective against M. sacchari; the highest mortality rate (85%) was produced by linoleic acid and the mean lethal concentration was 1,181 ppm, followed by stearic and palmitic acids with 74 and 63% mortality, respectively, at a concentration of 2,500 ppm at 72 h. The positive control, imidacloprid, had 100% mortality in 24 h and the Tween 20, negative control, exhibited 4% mortality in 72 h. Our results show that commercial fatty acids are effective against adults of M. sacchari and can be considered an environmentally friendly alternative to the frequent use of synthetic chemical insecticides.

    Topics: Animals; Aphids; Fatty Acids; Humans; Insecticides; Rutin; Saccharum; Sitosterols; Sorghum

2022
Virtual Screening and Molecular Docking to Study the Mechanism of Chinese Medicines in the Treatment of Coronavirus Infection.
    Medical science monitor : international medical journal of experimental and clinical research, 2022, Jan-25, Volume: 28

    BACKGROUND Heat-clearing and detoxifying herbs (HDHs) play an important role in the prevention and treatment of coronavirus infection. However, their mechanism of action needs further study. This study aimed to explore the anti-coronavirus basis and mechanism of HDHs. MATERIAL AND METHODS Database mining was performed on 7 HDHs. Core ingredients and targets were screened according to ADME rules combined with Neighborhood, Co-occurrence, Co-expression, and other algorithms. GO enrichment and KEGG pathway analyses were performed using the R language. Finally, high-throughput molecular docking was used for verification. RESULTS HDHs mainly acts on NOS3, EGFR, IL-6, MAPK8, PTGS2, MAPK14, NFKB1, and CASP3 through quercetin, luteolin, wogonin, indirubin alkaloids, ß-sitosterol, and isolariciresinol. These targets are mainly involved in the regulation of biological processes such as inflammation, activation of MAPK activity, and positive regulation of NF-kappaB transcription factor activity. Pathway analysis further revealed that the pathways regulated by these targets mainly include: signaling pathways related to viral and bacterial infections such as tuberculosis, influenza A, Ras signaling pathways; inflammation-related pathways such as the TLR, TNF, MAPK, and HIF-1 signaling pathways; and immune-related pathways such as NOD receptor signaling pathways. These pathways play a synergistic role in inhibiting lung inflammation and regulating immunity and antiviral activity. CONCLUSIONS HDHs play a role in the treatment of coronavirus infection by regulating the body's immunity, fighting inflammation, and antiviral activities, suggesting a molecular basis and new strategies for the treatment of COVID-19 and a foundation for the screening of new antiviral drugs.

    Topics: Alkaloids; Caspase 3; Coronavirus; Coronavirus Infections; COVID-19 Drug Treatment; Cyclooxygenase 2; Databases, Pharmaceutical; Drugs, Chinese Herbal; Flavanones; Humans; Indoles; Interleukin-6; Lignin; Luteolin; Mitogen-Activated Protein Kinase 14; Mitogen-Activated Protein Kinase 8; Molecular Docking Simulation; Naphthols; NF-kappa B p50 Subunit; Nitric Oxide Synthase Type III; Protein Interaction Maps; Quercetin; SARS-CoV-2; Signal Transduction; Sitosterols; Transcriptome

2022
Piperine, Reserpine and β-Sitosterol Attenuate Stem Rot (Sclerotium rolfsii Sacc.) of Groundnut by Inducing the Secretion of defense Enzymes and Phenolic Acids.
    Chemistry & biodiversity, 2022, Volume: 19, Issue:4

    Groundnut stem rot caused by Sclerotium rolfsii is a major constraint as it affects the productivity. Although managing this disease using synthetic fungicides is a more feasible method, environmental pollution and side effects caused by them demand some safe fungicides. Seven phytochemicals piperine, quercetin, reserpine, atropine sulfate, β-sitosterol, ethyl protocatechuate and salicylic acid were initially tested against S. rolfsii under in vitro methods. All the compounds exhibited significant effects on mycelial inhibition (except atropine sulfate), sclerotial development, ooze formation, maturity, sclerotial number and germination of S. rolfsii. The more active compounds, piperine, reserpine and β-sitosterol were then evaluated under glasshouse condition by adopting various application methods (seed treatment, foliar application and micro-injection at 2000 μg/mL) on groundnut plants challenged with and without S. rolfsii. All the treatments effectively reduced the plant mortality when tested every 15 days of infection with S. rolfsii. However, the magnitude of reduction varied among the treatments, with the mortality ranging between 9.37 % and 29.68 % compared to the control (40.68 %). The piperine-microinjected plants recorded minimum mortality (3.12 %). The defense enzymes (PAL and PPO) and key end products such as phenolics (total and individual) were determined in the leaf samples collected after 24, 48 and 72 h of infection with S. rolfsii to understand the systemic resistance induction effect. An increase in PAL and PPO activity was observed in all the samples. While microinjection of β-sitosterol caused a maximum PAL induction, piperine caused a maximum PPO activity. Further, samples of piperine treated group showed higher induction of phenolic acids (86.46 μg g

    Topics: Alkaloids; Atropine; Basidiomycota; Benzodioxoles; Fungicides, Industrial; Piperidines; Plant Diseases; Polyunsaturated Alkamides; Reserpine; Sitosterols

2022
Anti-adipogenic β-sitosterol and lupeol from Moringa oleifera suppress adipocyte differentiation through regulation of cell cycle progression.
    Journal of food biochemistry, 2022, Volume: 46, Issue:8

    Topics: Adipocytes; Adipogenesis; Cell Cycle; Glucose; Moringa oleifera; Pentacyclic Triterpenes; Sitosterols; Triterpenes

2022
Protective Role of β-Sitosterol in Glucocorticoid-Induced Osteoporosis in Rats Via the RANKL/OPG Pathway.
    Alternative therapies in health and medicine, 2022, Volume: 28, Issue:7

    Osteoporosis affects approximately 10% of the population worldwide. β-sitosterol (BSS), a major phytosterol in plants, has been claimed for centuries to have numerous medical benefits, including bone strengthening. This study aimed to find the benefit of BSS in treating osteoporosis according to traditional methods and to investigate the protective effect of BSS on glucocorticoid-induced osteoporosis in rats.. Wistar rats were randomly assigned to one of four groups: the control group, the dexamethasone (DEX) group and one of two BSS-treated osteoporosis groups (100 and 200 mg/kg). Blood samples and femur bones were collected for histopathology, immunohistochemistry, biochemical and mRNA expression analysis.. The results indicated that BSS (100 and 200 mg/kg) increased bone length, bone weight and bone mineral density (BMD) and suppressed DEX-induced reduction in body weight, dose-dependently. Mechanistically, BSS (100 and 200 mg/kg) treatment alleviated the increase of bone resorption markers and the decline of osteogenic markers, which might be partially mediated by regulation of nuclear factor kappa-β ligand/osteoprotegerin (RANKL/OPG) and RunX2 pathways. The immunohistochemical inducible nitric oxide synthase (iNOS) results of the rats' distal femur were negative in all groups. However, except in the DEX group, the endothelial nitric oxide synthase (eNOS) color reaction in osteoblasts was strongly positive in the other 3 groups. These results suggest that BSS showed promising effects in protection against glucocorticoid-induced osteoporosis by protecting osteoblasts and suppressing osteoclastogenesis.

    Topics: Animals; Bone Density; Core Binding Factor Alpha 1 Subunit; Dexamethasone; Glucocorticoids; Ligands; Nitric Oxide Synthase Type II; Nitric Oxide Synthase Type III; Osteoporosis; Osteoprotegerin; RANK Ligand; Rats; Rats, Wistar; RNA, Messenger; Sitosterols

2022
Beta-Sitosterol Modulates the Migration of Vascular Smooth Muscle Cells via the PPARG/AMPK/mTOR Pathway.
    Pharmacology, 2022, Volume: 107, Issue:9-10

    The increased migration of vascular smooth muscle cells (VSMCs) is an essential pathological factor in the early development of atherosclerosis. Beta-sitosterol (BS), a natural phytosterol abundant in plant seeds, exhibits various bioactivities, including cardioprotective effects. However, its effects on VSMC migration and underlying mechanisms remain to be explored.. BS inhibited the proliferation and migration of angiotensin II-induced A7r5 cells and reduced intracellular oxidative stress. Targets related to VSMC migration and the targets of BS were screened, cross-referenced, and analyzed by network pharmacology combined with molecular docking technology. The identified targets were verified at the protein and gene levels using Western blotting and quantitative PCR, respectively. BS was observed to activate peroxisome proliferator-activated receptor-γ (PPARG) and adenosine 5'-monophosphate-activated protein kinase (AMPK) and negatively regulate mammalian target of rapamycin (mTOR) expression. Furthermore, a PPARG inhibitor reversed the BS-induced activation of AMPK and mTOR.. This study indicated that regulation of the PPARG/AMPK/mTOR signaling pathway could potentially contribute to the inhibitory effects of BS on angiotensin II-induced VSMC migration.

    Topics: AMP-Activated Protein Kinases; Angiotensin II; Cell Movement; Cell Proliferation; Molecular Docking Simulation; Muscle, Smooth, Vascular; Myocytes, Smooth Muscle; PPAR gamma; Sitosterols; TOR Serine-Threonine Kinases

2022
Building blocks of β-sitosterol-γ-oryzanol gels revealed by small-angle neutron scattering and real space modelling.
    Food & function, 2022, Jul-04, Volume: 13, Issue:13

    Mixtures of β-sitosterol and γ-oryzanol form gels in a range of organic solvents. Despite being widely studied, particularly as potential oleogels for food application, details of the intrinsic gel-forming building blocks remain unclear. Small-angle neutron scattering (SANS) combined with solvent contrast variation has been used to evaluate potential structural models. While evidence exists that the building blocks are hollow cylinders (tubules), the simultaneous fitting of twelve contrast-varied SANS data sets indicates that the previously proposed model of double walled tubules is incorrect. Predicted scattering based on real space models provides compelling evidence that the origin of the gelling behaviour is the limited assembly of adjacent tubules to form a space-filling network of fibrils.

    Topics: Gels; Phenylpropionates; Scattering, Small Angle; Sitosterols; Solvents

2022
4-Hydroxybenzoic Acid and
    Journal of medicinal food, 2022, Volume: 25, Issue:6

    Insulin secretion and GLUT4 expression are two critical events in glucose regulation. The receptors G-protein-coupled receptor 40 (GPR40) and peroxisome proliferator-activated receptor-gamma (PPAR

    Topics: Animals; Cucurbita; Diabetes Mellitus, Experimental; Hypoglycemic Agents; Insulin; Liver Glycogen; Parabens; Plant Extracts; PPAR gamma; RNA, Messenger; Secretagogues; Sitosterols

2022
Verification of the folkloric and anecdotal antidiabetic effects of Hypoxis hemerocallidea (Fisch., C.A. Mey. & Avé-Lall) and isolated, β-sitosterol using early-stage type II spontaneous diabetic mutant BKS-Lepr
    BMC complementary medicine and therapies, 2022, Jun-20, Volume: 22, Issue:1

    Previous studies in our laboratory in ex vivo assays have demonstrated H. hemerocallidea extract as potential antidiabetic agent through increased insulin release from pancreatic beta cells. Thus, for this study the early stage type II spontaneous diabetic mutant mice model was used to evaluate and determine the degree of the antidiabetic efficacy of H. hemerocallidea.. Eight-weeks-old type II spontaneous pre-diabetic mutant BKS-Leprdb mice were fed with feed supplemented with either H. hemerocallidea extract, isolated compound (β-sitosterol) or chlorpropamide (positive control) for 4 weeks. The haematological parameters, clinical chemistry, glucose tolerance, feed intake, faecal output and body weights were measured.. The blood glucose concentrations of all the animals treated with plant extract, β-sitosterol compound and non-treated pre-diabetic animals did not return to baseline levels. Only the β-sitosterol treatment and positive control groups resulted in a respective small decrease of 5.8 and 5.2% in the mouse weights over the study period, with no significant changes (p > 0.05) in food intake. However, there was a general trend for decrease in faecal output for all the groups. Albumin, triglycerides, and total cholesterol levels in β-sitosterol and chlorpropamide-treated animals were lower, relative to untreated-animals. Animals fed with plant extract showed large amounts of internal fat. There were no significant changes (p > 0.05) in total serum protein, globulin, alanine aminotransferase, alkaline phosphatase, urea nitrogen and creatinine attributed to administration of treatments. In all groups, some animals showed lesions associated with cardiac puncture. Few animals except animals treated with plant extract, showed presence of a left-ventricular hypertrophic cardiomyopathy. The liver and kidneys for all groups appeared macroscopically normal and the thymuses were small (±2 mg). There were pathological signs in some of the animals particularly in myocardial fibres, renal tubular, glomerular, hepatocyte granularity and pancreas islets. However, there was no significance trend between the groups.. Based on the results, none of the treatments could be considered highly effective for the management of type II pre-diabetes as sole therapeutic intervention.

    Topics: Animals; Chlorpropamide; Diabetes Mellitus, Type 2; Hypoglycemic Agents; Hypoxis; Mice; Plant Extracts; Prediabetic State; Sitosterols

2022
Synthesis, Physical Properties, and In Vitro-Simulated Gastrointestinal Digestion of Hydrophilic β-Sitosterol Sugar Esters.
    Journal of agricultural and food chemistry, 2022, Jul-13, Volume: 70, Issue:27

    Hydrophilic β-sitosterol sugar esters were synthesized by a two-step biocatalytic approach using β-sitosterol vinyl adipate as an intermediate. The maximum conversion (above 90%) of β-sitosterol vinyl adipate was achieved using the saccharides glucose, sucrose, and raffinose. The chemical structure of the synthesized esters was confirmed by various techniques. The investigation of physical properties revealed that β-sitosterol sugar esters had enhanced water solubility (3.0-8.0 mM at 35 °C), reduced crystallinity, and high wettability. Their lyotropic liquid crystal properties were observed by polarized light microscopy. Furthermore, β-sitosterol sugar esters could be hydrolyzed into β-sitosterol adipate under simulated intestinal conditions at a low rate (2.83-18.14%). Most β-sitosterol sugar esters probably entered into intestinal bile salt micelles with ester bonds intact and showed up to 10-fold higher in vitro bioaccessibility than free β-sitosterol in non-fat systems. The excellent physical and functional characteristics of β-sitosterol sugar esters suggested their great potential application in the food industry.

    Topics: Adipates; Cholesterol; Digestion; Esters; Sitosterols; Sugars

2022
In vivo comparative study of the efficacy of β-sitosterol, ketoconazole 2% and mupirocin for the treatment cutaneous leishmaniosis.
    Annals of parasitology, 2022, Volume: 68, Issue:2

    Cutaneous leishmaniosis (CL) is an important parasitic disease characterized by specific skin lesion, includes the vector that cause the CL and treatment in general. The study aimed to identify the effect of three different drugs which are β-sitosterol, ketoconazole 2% and mupirocin in the treatment of cutaneous leishmaniosis. The study was conducted at Dermatological Unit of Al Hussein Teaching Hospital/Thi-Qar/Iraq from October to November 2021. The patients presented with a lesion will be involved in this study and its involved isolation of parasites from the lesion of patients and the parasite was replicated in (NNN) media then the inoculum was concentered. A total of 40 male of mice (Mus musculus) of BALB/c strain injected by parasite suspension, after the appearance of lesion, β-sitosterol, ketoconazole 2% and mupirocin was applied on a lesions daily for 2 weeks, the statistical analysis was done by SPSS program. In the current study, the β-sitosterol was most effective in the treatment of skin leishmanial lesion than the other drugs with mean is (11.9±1.449 mm) in compared with the other drugs under P-value < 0.046 with the complete recovery. β-sitosterol was highly effect on the L. tropica infections with complete recovery and no scar appearance than ketoconazole and mupirocin and can be used for treatment of the disease lesion.

    Topics: Animals; Ketoconazole; Leishmania tropica; Leishmaniasis, Cutaneous; Male; Mice; Mupirocin; Sitosterols

2022
    Immunopharmacology and immunotoxicology, 2022, Volume: 44, Issue:6

    To investigate the effects of β-sitosterol (B-SIT) and the underlying mechanisms of action in an ovalbumin-induced rat model of asthma.. The pathological and morphological changes in lung and tracheal tissues were observed by H&E, PAS, and Masson's staining. The levels of IgE, TNF-. B-SIT improved the injury in OVA-induced pathology, decreased the levels of inflammatory factors of IgE, TNF-. B-SIT improved symptoms in a rat model of asthma likely

    Topics: Animals; Asthma; Dendritic Cells; Interleukin-10; Interleukin-13; Interleukin-5; Interleukin-6; Ovalbumin; Rats; Sitosterols; Transforming Growth Factor beta1; Tumor Necrosis Factor-alpha

2022
β-Sitosterol Attenuates Dexamethasone-Induced Muscle Atrophy via Regulating FoxO1-Dependent Signaling in C2C12 Cell and Mice Model.
    Nutrients, 2022, Jul-14, Volume: 14, Issue:14

    Sarcopenia refers to a decline in muscle mass and strength with age, causing significant impairment in the ability to carry out normal daily functions and increased risk of falls and fractures, eventually leading to loss of independence. Maintaining protein homeostasis is an important factor in preventing muscle loss, and the decrease in muscle mass is caused by an imbalance between anabolism and catabolism of muscle proteins. Although β-sitosterol has various effects such as anti-inflammatory, protective effect against nonalcoholic fatty liver disease (NAFLD), antioxidant, and antidiabetic activity, the mechanism of β-sitosterol effect on the catabolic pathway was not well known. β-sitosterol was assessed in vitro and in vivo using a dexamethasone-induced muscle atrophy mice model and C2C12 myoblasts. β-sitosterol protected mice from dexamethasone-induced muscle mass loss. The thickness of gastrocnemius muscle myofibers was increased in dexamethasone with the β-sitosterol treatment group (DS). Grip strength and creatine kinase (CK) activity were also recovered when β-sitosterol was treated. The muscle loss inhibitory efficacy of β-sitosterol in dexamethasone-induced muscle atrophy in C2C12 myotube was also verified in C2C12 myoblast. β-sitosterol also recovered the width of myotubes. The protein expression of muscle atrophy F-box (MAFbx) was increased in dexamethasone-treated animal models and C2C12 myoblast, but it was reduced when β-sitosterol was treated. MuRF1 also showed similar results to MAFbx in the mRNA level of C2C12 myotubes. In addition, in the gastrocnemius and tibialis anterior muscles of mouse models, Forkhead Box O1 (FoxO1) protein was increased in the dexamethasone-treated group (Dexa) compared with the control group and reduced in the DS group. Therefore, β-sitosterol would be a potential treatment agent for aging sarcopenia.

    Topics: Animals; Dexamethasone; Disease Models, Animal; Forkhead Box Protein O1; Forkhead Transcription Factors; Mice; Muscle Fibers, Skeletal; Muscle, Skeletal; Muscular Atrophy; Sarcopenia; Sitosterols; Ubiquitin-Protein Ligases

2022
Antimicrobial Activity of β-Sitosterol Isolated from
    Pakistan journal of biological sciences : PJBS, 2022, Volume: 25, Issue:7

    <b>Background and Objective:</b> <i>Kalanchoe tomentosa</i> is identified and their different characteristics regarding the antibacterial and antioxidant properties have a vast effect. Fresh <i>K. tomentosa</i> leaves obtained from Bandung, Indonesia was extracted using n-hexane followed by serial dichloromethane maceration. <b>Materials and Methods:</b> N-hexane and ethyl acetate were used to separate the dichloromethane extract using vacuum liquid chromatography and the isolated compounds were recrystallized with n-hexane. <b>Results:</b> About 37 mg of dichloromethane extract was obtained from the extraction process. Recrystallized compound isolates were identified as stigmast-5-en-3-ol or β-sitosterol. Both dichloromethane extract and β-sitosterol isolated compounds showed strong bacteriostatic activity against <i>S. aureus</i> with MIC = 15.63 and 7.81 μg mL<sup></sup><sup>1</sup> and<i> K. pneumonia</i> with MIC = 7.81 and 31.25 μg mL<sup></sup><sup>1</sup>, respectively. However, only dichloromethane extract exhibited a bactericidal effect (7.81 μg mL<sup></sup><sup>1</sup>). <b>Conclusion:</b> The pure β-sitosterol compound was isolated from<i> K. tomentosa</i> dichloromethane extract. Both the dichloromethane extract and the isolated β-sitosterol compound had antibacterial effects against <i>S. aureus</i> and <i>K. pneumonia.</i>.

    Topics: Anti-Bacterial Agents; Kalanchoe; Klebsiella; Methylene Chloride; Plant Extracts; Plant Leaves; Pneumonia; Sitosterols; Staphylococcus aureus

2022
First Discovery of Beta-Sitosterol as a Novel Antiviral Agent against White Spot Syndrome Virus.
    International journal of molecular sciences, 2022, Sep-09, Volume: 23, Issue:18

    The outbreak of white spot syndrome (WSS) is a looming challenge, due to dramatic losses to the crustacean aquaculture industry. However, at present, there are no prophylactic or therapeutic means to control this infectious viral disease. Here, we screened fifteen medicinal plants for their inhibitory activity on the white spot syndrome virus (WSSV), using red swamp crayfish (Procambarus clarkii) as a model species. The results showed that the crude extracts of Pinellia ternata (Thunb.) Breit. had the highest inhibitory effect (91.59%, 100 mg/kg) on WSSV proliferation, and its main component, beta-sitosterol, showed a much higher activity (95.79%, 50 mg/kg). Further, beta-sitosterol potently reduced (p < 0.01) viral loads and viral gene transcription levels in a concentration-dependent fashion, and significantly promoted the survival rate of WSSV-challenged crayfish (57.14%, 50 mg/kg). The co-incubation assay indicated that beta-sitosterol did not influence the infectivity of WSSV particles. Both pre- and post-treatment of beta-sitosterol exerted a significant inhibitory effect (p < 0.01) on the viral load in vivo. Mechanistically, beta-sitosterol not only interfered with the expression of viral genes (immediate early gene 1, ie1; DNA polymerase, DNApol) that are important in initiating WSSV transcription, but it also attenuated the hijacking of innate immune signaling pathways (Toll, IMD, and JAK/STAT pathways) by viral genes to block WSSV replication. Moreover, the expression of several antiviral immune, antioxidant, pro-inflammatory, and apoptosis-related genes changed significantly in beta-sitosterol-treated crayfish. Beta-sitosterol is a potent WSSV inhibitor and has the potential to be developed as an effective anti-WSSV agent against a WSS outbreak in crustacean aquaculture.

    Topics: Animals; Antioxidants; Antiviral Agents; Astacoidea; Complex Mixtures; Sitosterols; White spot syndrome virus 1

2022
The effect of ethylene on squalene and β-sitosterol biosynthesis and its key gene network analysis in Torreya grandis nuts during post-ripening process.
    Food chemistry, 2022, Jan-30, Volume: 368

    Squalene and β-sitosterol are health-benefit compounds due to their nutritional and medicinal properties. It has been reported that the content of these bioactive compounds is relatively high in Torreya grandis nuts. However, it is not yet known what changes in squalene and β-sitosterol accumulation occur during the special post-ripening process of T. grandis nuts and the effect of the well-known ripening hormone ethylene on the regulatory mechanism of their biosynthetic pathways. Thus, we performed transcriptome and metabolite analyses. The results showed that ethylene not only promoted the post-ripening process but also enhanced the accumulation of squalene by inducing gene expression in the mevalonate pathway. At the same time, ethylene treatment also promoted the accumulation of other sterols but inhibited gene expression in the β-sitosterol biosynthesis pathway. In addition, co-expression and correlation analysis suggested a framework for the transcriptional regulation of squalene and β-sitosterol biosynthesis genes under ethylene treatment.

    Topics: Ethylenes; Fruit; Gene Expression Profiling; Gene Expression Regulation, Plant; Gene Regulatory Networks; Nuts; Sitosterols; Squalene; Taxaceae

2022
DHA loaded nanoliposomes stabilized by β-sitosterol: Preparation, characterization and release in vitro and vivo.
    Food chemistry, 2022, Jan-30, Volume: 368

    DHA loaded nanoliposomes, stabilized by β-sitosterol, were prepared by thin film hydration-sonication method. The characteristics and membranes properties of DHA-NLs with different β-sitosterol content were measured. The samples with the same formulation were used to measure the resistance of environment stress and controlled release & absorption of DHA in vitro and in vivo. The results showed that the maximal encapsulation efficiency of DHA-NLs was (86.95 ± 0.95)%, when the ratio of soybean lecithin to β-sitosterol was 5:1. The particle size of all samples was within 200 nm and relative retention rate was more than 60% after 3 weeks storage. The area under the curve of DHA concentration of DHA-NLs and DHA-emulsion groups was 1.32 and 1.08, respectively. In summary, the nanoliposomes were promising to improve the absorption of DHA in form of ethyl ester.

    Topics: Emulsions; Lecithins; Liposomes; Particle Size; Sitosterols

2022
Research on the Mechanism of Guizhi to Treat Nephrotic Syndrome Based on Network Pharmacology and Molecular Docking Technology.
    BioMed research international, 2021, Volume: 2021

    Nephrotic syndrome (NS) is a common glomerular disease caused by a variety of causes and is the second most common kidney disease. Guizhi is the key drug of Wulingsan in the treatment of NS. However, the action mechanism remains unclear. In this study, network pharmacology and molecular docking were used to explore the underlying molecular mechanism of Guizhi in treating NS.. The active components and targets of Guizhi were screened by the Traditional Chinese Medicine Systems Pharmacology Database and Analysis Platform (TCMSP), Hitpick, SEA, and Swiss Target Prediction database. The targets related to NS were obtained from the DisGeNET, GeneCards, and OMIM database, and the intersected targets were obtained by Venny2.1.0. Then, active component-target network was constructed using Cytoscape software. And the protein-protein interaction (PPI) network was drawn through the String database and Cytoscape software. Next, Gene Ontology (GO) and pathway enrichment analyses of Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analyses were performed by DAVID database. And overall network was constructed through Cytoscape. Finally, molecular docking was conducted using Autodock Vina.. According to the screening criteria, a total of 8 active compounds and 317 potential targets of Guizhi were chosen. Through the online database, 2125 NS-related targets were identified, and 93 overlapping targets were obtained. In active component-target network, beta-sitosterol, sitosterol, cinnamaldehyde, and peroxyergosterol were the important active components. In PPI network, VEGFA, MAPK3, SRC, PTGS2, and MAPK8 were the core targets. GO and KEGG analyses showed that the main pathways of Guizhi in treating NS involved VEGF, Toll-like receptor, and MAPK signaling pathway. In molecular docking, the active compounds of Guizhi had good affinity with the core targets.. In this study, we preliminarily predicted the main active components, targets, and signaling pathways of Guizhi to treat NS, which could provide new ideas for further research on the protective mechanism and clinical application of Guizhi against NS.

    Topics: Acrolein; Drugs, Chinese Herbal; Gene Ontology; Humans; Medicine, Chinese Traditional; Molecular Docking Simulation; Nephrotic Syndrome; Network Pharmacology; Protein Interaction Maps; Signal Transduction; Sitosterols; Software; Technology

2021
Plant Sterol-Poor Diet Is Associated with Pro-Inflammatory Lipid Mediators in the Murine Brain.
    International journal of molecular sciences, 2021, Dec-08, Volume: 22, Issue:24

    Plant sterols (PSs) cannot be synthesized in mammals and are exclusively diet-derived. PSs cross the blood-brain barrier and may have anti-neuroinflammatory effects. Obesity is linked to lower intestinal uptake and blood levels of PSs, but its effects in terms of neuroinflammation-if any-remain unknown. We investigated the effect of high-fat diet-induced obesity on PSs in the brain and the effects of the PSs campesterol and β-sitosterol on in vitro microglia activation. Sterols (cholesterol, precursors, PSs) and polyunsaturated fatty acid-derived lipid mediators were measured in the food, blood, liver and brain of C57BL/6J mice. Under a PSs-poor high-fat diet, PSs levels decreased in the blood, liver and brain (>50%). This effect was reversible after 2 weeks upon changing back to a chow diet. Inflammatory thromboxane B2 and prostaglandin D2 were inversely correlated to campesterol and β-sitosterol levels in all brain regions. PSs content was determined post mortem in human cortex samples as well. In vitro, PSs accumulate in lipid rafts isolated from SIM-A9 microglia cell membranes. In summary, PSs levels in the blood, liver and brain were associated directly with PSs food content and inversely with BMI. PSs dampen pro-inflammatory lipid mediators in the brain. The identification of PSs in the human cortex in comparable concentration ranges implies the relevance of our findings for humans.

    Topics: Animal Feed; Animals; Cells, Cultured; Cholesterol; Chromatography, Liquid; Diet, High-Fat; Disease Models, Animal; Fatty Acids, Unsaturated; Humans; Lipidomics; Liver; Male; Mice; Mice, Inbred C57BL; Microglia; Neuroinflammatory Diseases; Obesity; Phytosterols; Sitosterols; Tandem Mass Spectrometry

2021
New
    Natural product research, 2021, Volume: 35, Issue:8

    A new steroidal ester bearing

    Topics: Anacardium; Animals; Carbon-13 Magnetic Resonance Spectroscopy; Cell Line, Tumor; Humans; Inhibitory Concentration 50; Plant Bark; Plant Extracts; Plant Stems; Proton Magnetic Resonance Spectroscopy; Rats; Sitosterols

2021
Inhibitors of BRD4 protein from the roots of
    Natural product research, 2021, Volume: 35, Issue:12

    A new monoterpene (

    Topics: A549 Cells; Benzofurans; Cell Cycle Proteins; Drug Screening Assays, Antitumor; HeLa Cells; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Roots; Saxifragaceae; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Stigmasterol; Transcription Factors; Triterpenes

2021
Characterization of β-Sitosterol for Potential Selective GR Modulation.
    Protein and peptide letters, 2021, Volume: 28, Issue:3

    Although glucocorticoids (GCs) are characterized as powerful agents to treat inflammatory afflictions, they are accompanied by metabolic side effects which limit their usage. β-Sitosterol, as a minor component found in extraction of vegetable oil, was reported to have anti-inflammatory effects in RAW 264.7 cells.. To test whether β-sitosterol has an effect to dissociate transrepression from transactivation as a selective novel GR binder, this work evaluated the dissociated characteristics of β-sitosterol.. The probable binding interaction between β-sitosterol and GR was explored by molecular docking. The GR transcriptional activity of β-sitosterol was assessed in the reporter gene assay. The ability of β-sitosterol to modulate the transactivation and transrepression of GR was evaluated by real-time quantitative PCR analysis.. In the present study, β-sitosterol treatment cannot induce GR-mediated transactivation. β-Sitosterol exerted a potential to inhibited the expression of GR target transrepressed gene without activating the expression of GR transactivation dependent gene. Molecular docking demonstrated that β-Sitosterol was able to bind the ligand binding domain of GR but unable to induce GR activation.. This work offers evidence that β-sitosterol may serve as a selective GR modulator.

    Topics: Animals; HeLa Cells; Hep G2 Cells; Humans; Mice; Molecular Docking Simulation; RAW 264.7 Cells; Receptors, Glucocorticoid; Sitosterols

2021
Assessments of
    Journal of liposome research, 2021, Volume: 31, Issue:3

    β-sitosterol (BS), a phytosterol, exhibits ameliorative effects on hepatocellular carcinoma (HCC) due to its antioxidant activities. However, its poor aqueous solubility and negotiated bioavailability and short elimination half-life is a huge limitation for its therapeutic applications. To overcome these two shortcomings, BS-loaded niosomes were made to

    Topics: Animals; Antineoplastic Agents; Carcinoma, Hepatocellular; Drug Carriers; Liposomes; Liver Neoplasms; Polyethylene Glycols; Rats; Sitosterols

2021
Characterization of seven sterols in five different types of cattle feedstuffs.
    Food chemistry, 2021, Mar-15, Volume: 340

    This paper provides a method for the quantification of sterols in different types of calf feedstuffs based on soy, sunflower, hay, calf feed and a mixture of all of them. The free fraction and the total sterolic fraction, after saponification and acidic hydrolysis of the samples, are extracted by solvent and the sterols are identified/quantified by reversed phase HPLC coupled to tandem mass spectrometry by atmospheric pressure chemical ionization. After the recovery evaluation, the method is validated in terms of linearity (coefficient of determination R

    Topics: Animal Feed; Animals; Atmospheric Pressure; Cattle; Cholesterol; Chromatography, High Pressure Liquid; Ergosterol; Glycine max; Helianthus; Phytosterols; Sitosterols; Stigmasterol; Tandem Mass Spectrometry

2021
The targets of β-sitosterol as a novel therapeutic against cardio-renal complications in acute renal ischemia/reperfusion damage.
    Naunyn-Schmiedeberg's archives of pharmacology, 2021, Volume: 394, Issue:3

    This research is the first to use β-sitosterol on myocardial and renal tissues in renal ischemia/reperfusion (IR) damage. Female Wistar rats were randomly divided into three groups: control (sham), renal IR (50 min ischemia - 3 h reperfusion), and renal IR + 150 mg/kg/p.o. β-sitosterol (the rats were treated with β-sitosterol orally once 1 h before the IR procedure). β-Sitosterol pretreatment caused an increase in superoxide dismutase and glutathione activities and a decrease in malondialdehyde levels in the kidney and heart. Moreover, it alleviated histopathological changes and downregulated the levels of tumor necrosis factor-alpha and interleukin-6 and upregulated the levels of endothelial nitric oxide synthase. As conclusion, the potential of β-sitosterol for renal and cardiac necrosis and apoptosis appears to act by limiting inflammatory response and oxidative stress. Thus, the potential of this compound is noteworthy and may serve as a potential therapeutic in the treatment of acute organ damages due to renal IR.

    Topics: Animals; Anti-Inflammatory Agents; Apoptosis; Female; Glutathione; Hypolipidemic Agents; Interleukin-6; Ischemia; Kidney; Kidney Diseases; Malondialdehyde; Myocardium; Nitric Oxide Synthase Type III; Protective Agents; Rats, Wistar; Reperfusion Injury; Sitosterols; Superoxide Dismutase; Tumor Necrosis Factor-alpha

2021
Strobilanthes crispus bioactive subfraction inhibits tumor progression and improves hematological and morphological parameters in mouse mammary carcinoma model.
    Journal of ethnopharmacology, 2021, Mar-01, Volume: 267

    Locally known as 'pecah batu', 'bayam karang', 'keci beling' or 'batu jin', the Malaysian medicinal herb, Strobilanthes crispus (S. crispus), is traditionally used by the local communities as alternative or adjuvant remedy for cancer and other ailments and to boost the immune system. S. crispus has demonstrated multiple anticancer therapeutic potential in vitro and in vivo. A pharmacologically active fraction of S. crispus has been identified and termed as F3. Major constituents profiled in F3 include lutein and β-sitosterol.. In this study, the effects of F3, lutein and β-sitosterol on tumor development and metastasis were investigated in 4T1-induced mouse mammary carcinoma model.. Tumor-bearing mice were fed with F3 (100 mg/kg/day), lutein (50 mg/kg/day) and β-sitosterol (50 mg/kg/day) for 30 days (n = 5 each group). Tumor physical growth parameters, animal body weight and development of secondary tumors were investigated. The safety profile of F3 was assessed using hematological and histomorphological changes on the major organs in normal control mice (NM).. Our findings revealed significant reduction of physical tumor growth parameters in all tumor-bearing mice treated with F3 (TM-F3), lutein (TM-L) or β-sitosterol (TM-β) as compared with the untreated group (TM). Statistically significant reduction in body weight was observed in TM compared to the NM or treated (TM-F3, TM-L and TM-β) groups. Histomorphological examination of tissue sections from the F3-treated group showed normal features of the vital organs (i.e., liver, kidneys, lungs and spleen) which were similar to those of NM. Administration of F3 to NM mice (NM-F3) did not cause significant changes in full blood count values.. F3 significantly reduced the total tumor burden and prevented secondary tumor development in metastatic breast cancer without significant toxicities in 4T1-induced mouse mammary carcinoma model. The current study provides further support for therapeutic development of F3 with further pharmacokinetics studies.

    Topics: Acanthaceae; Animals; Antineoplastic Agents, Phytogenic; Breast Neoplasms; Cell Line, Tumor; Female; Kidney Neoplasms; Liver Neoplasms; Lung Neoplasms; Lutein; Mice, Inbred BALB C; Plant Extracts; Sitosterols; Splenic Neoplasms; Tumor Burden

2021
A preliminary investigation into the unsaponifiable fraction of donkey milk: Sterols of animal origin, phytosterols, and tocopherols.
    Journal of dairy science, 2021, Volume: 104, Issue:2

    We investigated the main sterols, phytosterols, and the α- and γ-tocopherol content in donkey milk during the first 2 mo of lactation. Cholesterol was the main sterol in milk (mean ± standard deviation = 0.97 ± 0.443 g/100 g of fat). Lanosterol was the main minor sterol of animal origin, followed by desmosterol (0.003 ± 0.001 and 0.001 ± 0.001 g/100 g of fat, respectively). Of the phytosterols, β-sitosterol was the main sterol of vegetal origin in donkey milk (0.005 ± 0.002 g/100 g of fat), but lower levels of campesterol, brassicasterol, and stigmasterol were also recorded. Mean levels of α- and γ-tocopherol were 0.01 ± 0.007 and 0.003 ± 0.001 g/100 g of fat, respectively. We observed no significant changes in sterol or tocopherol content during the first 2 mo of lactation. The presence of lanosterol in donkey milk is of particular interest, because lanosterol is a potential drug and has important physiological effects. The presence of phytosterols, which are considered nutraceutical molecules, enhances the nutritional quality of donkey milk fat for consumers.

    Topics: Animals; Cholestadienols; Cholesterol; Desmosterol; Equidae; Female; Lactation; Lanosterol; Milk; Nutritive Value; Phytosterols; Saponins; Sitosterols; Sterols; Tocopherols

2021
Supercritical CO
    Molecules (Basel, Switzerland), 2021, Jan-23, Volume: 26, Issue:3

    Topics: Antioxidants; Carbon Dioxide; Carotenoids; Chlorophyll; Drug Compounding; Olea; Olive Oil; Plant Extracts; Polyphenols; Sitosterols; Tocopherols

2021
Network pharmacology integrated molecular docking reveals the bioactive components and potential targets of Morinda officinalis-Lycium barbarum coupled-herbs against oligoasthenozoospermia.
    Scientific reports, 2021, 01-26, Volume: 11, Issue:1

    Oligoasthenozoospermia (OA) is one of the most common types of male infertility affecting sperm count and sperm motility. Unfortunately, it is difficult for existing drugs to fundamentally improve the sperm quality of OA patients, because the pathological mechanism of OA has not been fully elucidated yet. Morinda officinalis-Lycium barbarum coupled-herbs (MOLBCH), as traditional Chinese Medicines, has been widely used for treating OA over thousands of years, but its molecular mechanism is still unclear. For this purpose, we adopted a comprehensive approach integrated network pharmacology and molecular docking to reveal the bioactive components and potential targets of MOLBCH against OA. The results showed that MOLBCH alleviated apoptosis, promoted male reproductive function, and reduced oxidant stress in the treatment of OA. Ohioensin-A, quercetin, beta-sitosterol and sitosterol were the key bioactive components. Androgen receptor (AR), Estrogen receptor (ESR1), Mitogen-activated protein kinase 3 (MAPK3), RAC-alpha serine/threonine-protein kinase (AKT1), Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) were the core potential targets. PI3K/Akt signaling pathway, prostate cancer, AGE-RAGE signaling pathway in diabetic complications were the most representative pathways. Moreover, molecular docking was performed to validate the strong binding interactions between the obtained core components and targets. These observations provide deeper insight into the pathogenesis of OA and can be used to design new drugs and develop new therapeutic instructions to treat OA.

    Topics: Humans; Lycium; Male; Male Urogenital Diseases; Molecular Docking Simulation; Molecular Structure; Morinda; Oligospermia; Quercetin; Signal Transduction; Sitosterols

2021
Fabrication and characterization of stable oleofoam based on medium-long chain diacylglycerol and β-sitosterol.
    Food chemistry, 2021, Jul-15, Volume: 350

    Oleofoams have emerged as attractive low-calorie aeration systems, but saturated lipids or large amount of surfactants are commonly required. Herein, an innovative strategy was proposed to create oleofoams using medium-long chain diacylglycerol (MLCD) and β-sitosterol (St). The oleofoams prepared using MLCD and St in ratios of 15:5 and 12:8 exhibited smaller bubble size and much higher stability. MLCD crystals formed rigid Pickering shell, whereby air bubbles acted as "active fillers" leading to enhanced rigidity. Both Pickering and network stabilization for the MLCD-St oleofoam provided a steric hindrance against coalescence. The gelators interacted via hydrogen bonding, causing a condensing effect in improving the gel elasticity. The oleofoams and foam-based emulsions exhibited a favorable capacity in controlling volatile release where the maximum headspace concentrations and partition coefficients showed a significantly decrease. Overall, the oleofoams have shown great potential for development of low-calorie foods and delivery systems with enhanced textural and nutritional features.

    Topics: Diglycerides; Hydrogen Bonding; Sitosterols; Surface-Active Agents

2021
Simultaneous Quantification of Betulinic Acid, Lupeol, and β-Sitosterol in Madhuca longifolia Methanolic Extract of Bark by Liquid Chromatography-Tandem Mass Spectrometric Method.
    Journal of AOAC International, 2021, May-21, Volume: 104, Issue:2

    Liquid chromatography with tandem mass spectrometry is used widely used for the quantitative analysis of phytoconstituents present in medicinal plants to assess the quality of extract used for different investigations.. A sensitive, precise, and accurate liquid chromatographic method with tandem mass spectrometric detection was developed for simultaneous quantification of lupeol, betulinic acid, and β-sitosterol in the methanolic extract of Madhuca longifolia bark.. The three compounds were eluted with a stationary phase Gemini C18 column (50 × 2.0 mm, 3 μm id) and the temperature of the column was maintained by a column oven at 40 ± 0.3°C; mobile phase A (water and 0.1% formic acid) and mobile phase B [acetonitrile-methanol (50+50, v/v) and 0.1% formic acid] were used in a gradient mode and the flow rate was 0.4 mL/min.. With these conditions, the retention time for betulinic acid, lupeol, and β-sitosterol was found to be 1.25, 3.08, and 3.53 minutes, respectively. The total run time was 5.0 min. Detection and quantitation of all three phytoconstituents were carried out by the mass spectrometer, a triple quadrupole equipped with atmospheric pressure chemical ionization, and multiple reaction monitoring using the predominantly positive ion mode and obtained much higher and more stable response nebulizer gas flow at 3.0 L/min. Linear responses were exhibited for all three phytoconstituents with a dynamic linear range of 10-100 μg/mL with the values of the regression coefficient more than 0.995 for betulinic acid, lupeol, and β-sitosterol. The values of percentage RSD for intraday and interday precision were found to be within the accepted limits for analytical methods (<15%). Selectivity, linearity, LOD, LOQ, accuracy, and precision were evaluated for all three phytoconstituents as per International Conference on Harmonization guidelines.. The proposed method is accurate and sensitive and can be used for the routine quantification of betulinic acid, lupeol, and β-sitosterol from the herbal extract and its poly-herbal formulations.

    Topics: Betulinic Acid; Chromatography, High Pressure Liquid; Chromatography, Liquid; Madhuca; Methanol; Pentacyclic Triterpenes; Plant Bark; Plant Extracts; Reproducibility of Results; Sitosterols

2021
Severe Genotype, Pancreatic Insufficiency and Low Dose of Pancreatic Enzymes Associate with Abnormal Serum Sterol Profile in Cystic Fibrosis.
    Biomolecules, 2021, 02-19, Volume: 11, Issue:2

    Several factors could lead to lipid disturbances observed in cystic fibrosis (CF). This study aimed to assess sterol homeostasis in CF and define potential exogenous and endogenous determinants of lipid dysregulation.. The study involved 55 CF patients and 45 healthy subjects (HS). Sterol concentrations (μg/dL) were measured by gas chromatography/mass spectrometry. CF was characterised by lung function, pancreatic status, liver disease and diabetes coexistence,. Independent determinants of lipid status suggest that malabsorption and pancreatic enzyme supplementation play a significant role in sterol abnormalities. The measurement of campesterol and β-sitosterol concentrations in CF patients may serve for the assessment of the effectiveness of pancreatic enzyme replacement therapy and/or compliance, but further research is required.

    Topics: Adolescent; Adult; Anthropometry; Cholesterol; Cystic Fibrosis; Enzyme Replacement Therapy; Exocrine Pancreatic Insufficiency; Female; Gas Chromatography-Mass Spectrometry; Genotype; Homeostasis; Humans; Lipids; Male; Middle Aged; Pancreas; Phytosterols; Sitosterols; Sterols; Young Adult

2021
Supercritical Fluid Extract of
    Molecules (Basel, Switzerland), 2021, Feb-15, Volume: 26, Issue:4

    Putrajeevak (

    Topics: Animals; Chromatography, Supercritical Fluid; Disease Models, Animal; Euphorbiaceae; Fatty Acids; Female; Fertility; Inflammation; Male; Ovary; Ovum; Pelvis; Plant Oils; Seeds; Sitosterols; Testis; Zebrafish

2021
Associations between Circulating Markers of Cholesterol Homeostasis and Macrovascular Events among Patients Undergoing Hemodialysis.
    Nutrients, 2021, Mar-21, Volume: 13, Issue:3

    Current strategies targeting serum cholesterol bring limited benefits to mortality and macrovascular events prevention among hemodialysis patients. Direct measurements and analysis on circulating markers of cholesterol homeostasis could be promising solutions to this bottleneck. We prospectively enrolled 90 maintenance hemodialysis patients and 9 healthy controls in 2019 for 1 year. We measured circulating desmosterol and lathosterol as markers for cholesterol synthesis and campesterol and sitosterol for cholesterol absorption. At baseline, hemodialysis patients showed higher levels of campesterol (

    Topics: Aged; Biomarkers; Cholesterol; Female; Homeostasis; Humans; Logistic Models; Male; Middle Aged; Odds Ratio; Regression Analysis; Renal Dialysis; Sitosterols; Triglycerides

2021
Phenolic acids and phytosterols in rice grains and wheat flours consumed in five regions of China.
    Journal of food science, 2021, Volume: 86, Issue:5

    Phenolic acids and phytosterols, the main functional compounds in cereals, could promote wellbeing and reduce the risks of diet-related diseases. This study aimed to demonstrate phenolic acid and phytosterol profiles in rice grains and wheat flours, and estimate their intakes in five geographical regions and among different age groups. Phenolic acids and phytosterols mainly existed in bound form, and the whole rice grain had high amount of 161.39 to 368.74 µg/g and 37.50 to 93.31 mg/ 100 g, respectively. In total, nine phenolic acids and six phytosterols were detected with ferulic and p-coumaric acid, and β-sitosterol the most abundant. The dietary intakes of phenolic acids and phytosterols were calculated combined with the dietary foods intake data of Chinese people. The intakes of total phenolic acids and phytosterols from rice grains and wheat flours varied across different regions with Beijing the highest among the five regions. At the age of 2 to 70 years, the average intakes of phenolic acids and phytosterols from rice and wheat flours were 7.74 to 17.52 and 58.02 to 135.61 mg/sp/day, respectively. If 3-ounce of polished rice was replaced by black rice grain, the predicted intakes of total phenolic acids and phytosterols from rice grains and wheat flours would increase by at least 196% and 68%, respectively, especially for free phenolic acids and phytosterols. PRACTICAL APPLICATION: This study would help the consumers know how much phenolic acids and phytosterols they would get from 3 ounces of black rice in a reasonable intake of staple food but shift away other kinds of foods. It could also provide inspirations for food industries to explore the functional cereal foods that are rich in phenolic acids and phytosterols for different regions and different age groups.

    Topics: Adolescent; Adult; Aged; Beijing; Child; Child, Preschool; China; Coumaric Acids; Diet; Edible Grain; Flour; Humans; Hydroxybenzoates; Middle Aged; Oryza; Phytosterols; Sitosterols; Triticum; Whole Grains

2021
β-Sitosterol Circumvents Obesity Induced Inflammation and Insulin Resistance by down-Regulating IKKβ/NF-κB and JNK Signaling Pathway in Adipocytes of Type 2 Diabetic Rats.
    Molecules (Basel, Switzerland), 2021, Apr-06, Volume: 26, Issue:7

    β-sitosterol (SIT), the most abundant bioactive component of vegetable oil and other plants, is a highly potent antidiabetic drug. Our previous studies show that SIT controls hyperglycemia and insulin resistance by activating insulin receptor and glucose transporter 4 (GLUT-4) in the adipocytes of obesity induced type 2 diabetic rats. The current research was undertaken to investigate if SIT could also exert its antidiabetic effects by circumventing adipocyte induced inflammation, a key driving factor for insulin resistance in obese individuals. Effective dose of SIT (20 mg/kg b.wt) was administered orally for 30 days to high fat diet and sucrose induced type-2 diabetic rats. Metformin, the conventionally used antidiabetic drug was used as a positive control. Interestingly, SIT treatment restores the elevated serum levels of proinflammatory cytokines including leptin, resistin, tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) to normalcy and increases anti-inflammatory adipocytokines including adiponectin in type 2 diabetic rats. Furthermore, SIT decreases sterol regulatory element binding protein-1c (SREBP-1c) and enhances Peroxisome Proliferator-activated receptor-γ (PPAR-γ) gene expression in adipocytes of diabetic rats. The gene and protein expression of c-Jun-N-terminal kinase-1 (JNK1), inhibitor of nuclear factor kappa-B kinase subunit beta (IKKβ) and nuclear factor kappa B (NF-κB) were also significantly attenuated in SIT treated groups. More importantly, SIT acts very effectively as metformin to circumvent inflammation and insulin resistance in diabetic rats. Our results clearly show that SIT inhibits obesity induced insulin resistance by ameliorating the inflammatory events in the adipose tissue through the downregulation of IKKβ/NF-κB and c-Jun-N-terminal kinase (JNK) signaling pathway.

    Topics: Adipocytes; Adipokines; Adipose Tissue; Animals; Body Weight; Cytokines; Diabetes Mellitus, Type 2; Diet, High-Fat; Down-Regulation; Feeding Behavior; I-kappa B Kinase; Inflammation; Inflammation Mediators; Insulin Resistance; Male; MAP Kinase Signaling System; Molecular Docking Simulation; NF-kappa B; Obesity; PPAR gamma; Rats; RNA, Messenger; Sitosterols; Sterol Regulatory Element Binding Protein 1; Sucrose; Up-Regulation

2021
Anti-inflammatory β-sitosterols from the Asiatic loop-root mangrove Rhizophora mucronata attenuate 5-lipoxygenase and cyclooxygenase-2 enzymes.
    Steroids, 2021, Volume: 172

    Topics: Anti-Inflammatory Agents; Antioxidants; Arachidonate 5-Lipoxygenase; Cyclooxygenase 2; Cyclooxygenase 2 Inhibitors; Lipoxygenase Inhibitors; Plant Extracts; Plant Roots; Rhizophoraceae; Sitosterols

2021
β-Sitosterol-D-Glucopyranoside Mimics Estrogenic Properties and Stimulates Glucose Utilization in Skeletal Muscle Cells.
    Molecules (Basel, Switzerland), 2021, May-24, Volume: 26, Issue:11

    Topics: Glucose; Glucose Transporter Type 4; HEK293 Cells; Humans; Magnetic Resonance Spectroscopy; Mass Spectrometry; MCF-7 Cells; Molecular Mimicry; Muscle, Skeletal; Phosphatidylinositol 3-Kinases; Phytoestrogens; Proto-Oncogene Proteins c-akt; Signal Transduction; Sitosterols

2021
Importance of Cholesterol Side Chain in the Membrane Stability of Human Erythrocytes.
    Biological & pharmaceutical bulletin, 2021, Volume: 44, Issue:6

    Cholesterol suppresses the hemolysis and the detachment of cytoskeletal proteins from bilayer in the human erythrocyte membrane under stress conditions. However, there is little information on how cholesterol functions. So, examining the role of a short side chain of cholesterol, we used the plant sterols such as β-sitosterol and stigmasterol. Incorporation of sterols into the membrane using a sterol/methyl-β-cyclodextrin complex was confirmed by the mass spectrometry. Hemolysis of human erythrocytes under high hydrostatic pressure (200 MPa) or hypotonic conditions was suppressed by cholesterol, but not by β-sitosterol and stigmasterol. Moreover, the bilayer-cytoskeleton interaction was also strengthened by cholesterol, but not by β-sitosterol and stigmasterol. Taken together, we suggest that the short side chain of cholesterol plays an important role in the membrane stability of human erythrocytes.

    Topics: beta-Cyclodextrins; Cell Membrane; Cells, Cultured; Cholesterol; Cytoskeletal Proteins; Cytoskeleton; Erythrocytes; Hemolysis; Humans; Sitosterols; Stigmasterol

2021
β-sitosterol reduces anxiety and synergizes with established anxiolytic drugs in mice.
    Cell reports. Medicine, 2021, 05-18, Volume: 2, Issue:5

    Anxiety and stress-related conditions represent a significant health burden in modern society. Unfortunately, most anxiolytic drugs are prone to side effects, limiting their long-term usage. Here, we employ a bioinformatics screen to identify drugs for repurposing as anxiolytics. Comparison of drug-induced gene-expression profiles with the hippocampal transcriptome of an importin α5 mutant mouse model with reduced anxiety identifies the hypocholesterolemic agent β-sitosterol as a promising candidate. β-sitosterol activity is validated by both intraperitoneal and oral application in mice, revealing it as the only clear anxiolytic from five closely related phytosterols. β-sitosterol injection reduces the effects of restraint stress, contextual fear memory, and c-Fos activation in the prefrontal cortex and dentate gyrus. Moreover, synergistic anxiolysis is observed when combining sub-efficacious doses of β-sitosterol with the SSRI fluoxetine. These preclinical findings support further development of β-sitosterol, either as a standalone anxiolytic or in combination with low-dose SSRIs.

    Topics: Animals; Anti-Anxiety Agents; Anxiety; Anxiety Disorders; Fear; Fluoxetine; Mice, Inbred C57BL; Motor Activity; Pharmaceutical Preparations; Prefrontal Cortex; Proto-Oncogene Proteins c-fos; Selective Serotonin Reuptake Inhibitors; Sitosterols; Tranquilizing Agents

2021
Improving the nutritional profile of culinary products: oleogel-based bouillon cubes.
    Food & function, 2021, Aug-21, Volume: 12, Issue:16

    Structured fat phases are the basis of many consumer relevant properties of fat-containing foods. To realise a nutritional improvement - less saturated, more unsaturated fatty acids - edible oleogels could be remedy. The feasibility of traditional fat phases structured by oleogel in culinary products has been evaluated in this study. In this contribution the oleogel application in bouillon cubes as model system for culinary products is discussed. Three different gelators (sunflower wax (SFW), a mixture of β-Sitosterol and γ-Oryzanol (SO) and ethylcellulose (EC)), at two concentration levels (5% and 10% (w/w)) each, were evaluated with respect to their physical properties, in the food matrix and application. The application of pure and structured canola oil (CO) was benchmarked against the reference, palm fat (PO). The assessment of the prototypes covered attempts to correlate the physicochemical analyses and sensory data. Organoleptic and analytical studies covered storage stability (up to 6 months) monitoring texture, color and fat oxidation. The results indicate that the substitution of palm fat by oleogel is essentially possible. The characteristics of the bouillon cubes are tuneable by gelator choice and inclusion level. Most importantly, the data show that the anticipated risk of intolerable effects of oxidation during shelf life is limited if antioxidants are used.

    Topics: Cellulose; Chemical Phenomena; Fat Substitutes; Food Handling; Food Quality; Helianthus; Humans; Nutritive Value; Organic Chemicals; Phenylpropionates; Rapeseed Oil; Sitosterols; Taste; Waxes

2021
Antibacterial activity of β-sitosterol isolated from the leaves of Odontonema strictum (Acanthaceae).
    Bioorganic & medicinal chemistry letters, 2021, 09-15, Volume: 48

    Topics: Acanthaceae; Anti-Bacterial Agents; Dose-Response Relationship, Drug; Microbial Sensitivity Tests; Molecular Structure; Plant Leaves; Sitosterols; Staphylococcus aureus; Structure-Activity Relationship

2021
Activity guided isolation and mechanistic approach towards analgesic potential of Chenopodium mediated through opioidergic pathway.
    Pakistan journal of pharmaceutical sciences, 2021, Volume: 34, Issue:1(Suppleme

    The current study is focused towards screening for its phytochemicals, phenolic and flavonoid contents of different species of Chenopodium. The plants were also screened for corroborating the traditional use of medicinal plants locally used for pain by determining the extract and their fractions for the in-vivo analgesic activity by using the modern scientific system. Among chloroform fractions, a high level of total phenolic contents was found in chloroform fraction of Chenopodium ambrosioides (ChAm-Chf) with 57.12±1.02 followed by Chenopodium botrys (ChBt-Chf) with 56.79±0.71. High content of flavonoids was found in chloroform fraction of Chenopodium botrys (ChBt-Chf) extract with 78.35±0.84 followed by Chenopodium ambrosioides (ChAm-Chf) with 75.20±0.81. The crude extract Chenopodium album, Chenopodium botrys and Chenopodium ambrosioides (ChAl-Crd, ChBt-Crd and ChAm-Crd) at 100 and 200 mg/kg, chloroform and ethylacetate fractions (ChAl-Chf, ChBt-Chf, ChAm-Chf, ChAl-Et, ChBt-Et and ChAm-Et) at 75 mg/kg caused significant inhibition (P<0.05, P<0.01, P<0.001, n=8) of the analgesic response induced by acetic acid, formalin and hotplate method. Mechanistically, the naloxone overturns completely the analgesic effects of beta-sitosterol (SN2) while partial reversal was observed by ursolic acid (SN1) indicating other possible mechanisms in association with opioid receptors.

    Topics: Analgesics; Animals; Behavior, Animal; Chenopodium; Chenopodium album; Chenopodium ambrosioides; Drug Discovery; Flavonoids; Mice; Naloxone; Narcotic Antagonists; Phenols; Phytochemicals; Phytotherapy; Plant Extracts; Sitosterols; Triterpenes; Ursolic Acid

2021
A fully reversible 25-hydroxy steroid kinase involved in oxygen-independent cholesterol side-chain oxidation.
    The Journal of biological chemistry, 2021, Volume: 297, Issue:4

    The degradation of cholesterol and related steroids by microbes follows fundamentally different strategies in aerobic and anaerobic environments. In anaerobic bacteria, the primary C26 of the isoprenoid side chain is hydroxylated without oxygen via a three-step cascade: (i) water-dependent hydroxylation at the tertiary C25, (ii) ATP-dependent dehydration to form a subterminal alkene, and (iii) water-dependent hydroxylation at the primary C26 to form an allylic alcohol. However, the enzymes involved in the ATP-dependent dehydration have remained unknown. Here, we isolated an ATP-dependent 25-hydroxy-steroid kinase (25-HSK) from the anaerobic bacterium Sterolibacterium denitrificans. This highly active enzyme preferentially phosphorylated the tertiary C25 of steroid alcohols, including metabolites of cholesterol and sitosterol degradation or 25-OH-vitamin D

    Topics: Bacterial Proteins; Betaproteobacteria; Cholesterol; Oxidation-Reduction; Phosphotransferases; Sitosterols

2021
Yield, Characterization, and Possible Exploitation of
    Molecules (Basel, Switzerland), 2021, Aug-12, Volume: 26, Issue:16

    Topics: Cannabis; Cholesterol; Hydroponics; Oleanolic Acid; Phytosterols; Plant Extracts; Plant Roots; Sitosterols; Stigmasterol; Triterpenes

2021
Reference Intervals of Serum Non-Cholesterol Sterols by Gender in Healthy Japanese Individuals.
    Journal of atherosclerosis and thrombosis, 2020, May-01, Volume: 27, Issue:5

    The present study was conducted to establish a practical method for measuring non-cholesterol sterols and reference intervals of serum levels.. Healthy subjects (109 men and 151 women), four patients with sitosterolemia, and 10 heterozygous mutation carriers of ABCG5/ABCG8 genes were investigated. Then, three non-cholesterol sterols (sitosterol, campesterol, and lathosterol) of fasting serum samples were measured via a practical and highly sensitive gas chromatography (GC) method with 0.2 µg/mL as the lower limit of quantification. The coefficient of variation (CV) values for within-run reproducibility were 3.06%, 1.89%, and 1.77% for lathosterol, campesterol, and sitosterol, respectively. The CV values for between-run reproducibility were 2.81%, 2.06%, and 2.10% for lathosterol, campesterol, and sitosterol, respectively.. The serum levels of sitosterol and campesterol were significantly higher in women than in men, whereas the serum levels of lathosterol were significantly higher in men than in women. Because of these gender difference, the determination of reference intervals of the three sterol values was performed by considering gender. The reference intervals of sitosterol, campesterol, and lathosterol were 0.99-3.88, 2.14-7.43, and 0.77-3.60 µg/mL in men and 1.03-4.45, 2.19-8.34, and 0.64-2.78 µg/mL in women, respectively. The serum levels of sitosterol and campesterol were higher in patients with sitosterolemia (94.3±47.3 and 66.3±36.6 µg/mL, respectively) than in healthy subjects.. These results demonstrate a practical and highly sensitive GC method to measure non-cholesterol sterol levels and gender-segregated reference intervals of sitosterol, campesterol, and lathosterol in Japanese healthy subjects.

    Topics: ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; Cholesterol; Cholesterol, Dietary; Chromatography, Gas; Female; Humans; Hypercholesterolemia; Intestinal Diseases; Japan; Lipid Metabolism, Inborn Errors; Lipoproteins; Male; Middle Aged; Phytosterols; Reference Values; Reproducibility of Results; Sex Factors; Sitosterols

2020
An ultra high performance liquid chromatography with tandem mass spectrometry method for simultaneous determination of thirteen components extracted from Radix Puerariae in rat plasma and tissues: Application to pharmacokinetic and tissue distribution stu
    Journal of separation science, 2020, Volume: 43, Issue:2

    Topics: Administration, Oral; Animals; Apigenin; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Genistein; Isoflavones; Molecular Structure; Pueraria; Rats; Rats, Sprague-Dawley; Sitosterols; Tandem Mass Spectrometry; Tissue Distribution

2020
Efficient solid phase extraction of α-tocopherol and β-sitosterol from sunflower oil waste by improving the mesoporosity of the zeolitic adsorbent.
    Food chemistry, 2020, May-01, Volume: 311

    The recovery of α-tocopherol and β-sitosterol from the deodorizer distillate of sunflower oil using solid phase extraction is reported. Performance of the silicon-rich and inexpensive zeolite, ZSM-5, and its modified versions were compared as adsorbents. Modifications of the zeolite frame were performed under both acidic and basic conditions to desilicate and dealuminate the parent ZSM-5. Base treatment resulted in hierarchical porosity and increased mesoporosity in the structure, which made the desilicated material as the best adsorbent of the study. Optimization of the solid phase extraction conditions was also studied and high recoveries of α-tocopherol and β-sitosterol, up to 99.20% and 97.32%, respectively, were achieved. The preparation and characterisation of the reported sorbents, as high-performance adsorbents, were not only proved to be economically promising, due to recycling of nutritious products, but also improves the ecological credentials of the process through reduction in waste.

    Topics: Adsorption; alpha-Tocopherol; Chromatography, High Pressure Liquid; Porosity; Sitosterols; Solid Phase Extraction; Sunflower Oil; Zeolites

2020
Chemoprotective and antiobesity effects of tocols from seed oil of Maqui-berry: Their antioxidative and digestive enzyme inhibition potential.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2020, Volume: 136

    Maqui-berry (Aristotelia chilensis) is the emerging Chilean superfruit with high nutraceutical value. Until now, the research on this commodity was focused on the formulations enriched with polyphenols from the pulp. Herein, contents of tocols were compared in the seed oil of Maqui-berry obtained through three different extraction methods followed by determining their antioxidative and enzyme inhibitions in-vitro. Firstly, oilseed was extracted with n-hexane (Soxhlet method), chloroform/methanol/water (Bligh and Dyer method) and pressing (industrial). These samples were used to access their effects against DPPH, HORAC, ORAC, FRAP, Lipid-peroxidation (TBARS), α-amylase, α-glucosidase, and pancreatic lipase. All the isomers of tocopherol and tocotrienol were identified, and β-sitosterol was the only sterol found in higher amounts than other vegetable oils. The Bligh and Dyer method could lead to the highest antioxidative capacity compared to Soxhlet and press methods likely because the latter have a higher amount of tocopherols. Further, seed oil from Maqui berry and their tocols (α, β, γ, δ-tocopherols, tocotrienols, and β-sitosterol) warrant clinical investigation for their antioxidative and antiobesity potential. Taken together, these findings provide relevant and suitable conditions for the industrial processing of Maqui-berry.

    Topics: Animals; Anti-Obesity Agents; Antioxidants; Enzyme Inhibitors; Lipase; Magnoliopsida; Male; Rats, Wistar; Seeds; Sitosterols; Tocopherols; Tocotrienols

2020
β-Sitosterol Contributes in the Resistance to Invasion and Survival of
    Journal of microbiology and biotechnology, 2020, Apr-28, Volume: 30, Issue:4

    We previously identified β-sitosterol (BS) as one of the most abundant compounds found in Korean red ginseng oil. BS is a widely prevalent vegetable-derived phytosterol with many known health benefits. Here, we investigated the efficacy of BS against

    Topics: Animals; Brucella abortus; Brucellosis; Cell Survival; Cytokines; Female; Macrophages; MAP Kinase Signaling System; Mice; Mice, Inbred BALB C; Microbial Viability; Nitrates; RAW 264.7 Cells; Sitosterols

2020
Effect of different oleogelators on lipolysis and curcuminoid bioaccessibility upon in vitro digestion of sunflower oil oleogels.
    Food chemistry, 2020, Jun-01, Volume: 314

    Sunflower oil enriched with curcuminoid compounds (CUs) was gelled by adding 5% (w/w) saturated monoglycerides (MG), rice bran waxes (RW) or a mixture of β-sitosterol and γ-oryzanol (PS). The resulting oleogels differed for rheological properties and firmness due to the difference in gel network structure. PS oleogel was the firmest sample followed by RW and MG ones. Upon in vitro digestion, fatty acid release as a function of digestion time was greatly affected by oleogel structure: the extent of lipolysis decreased as oleogel strength increased (PS < RW < MG). On the other hand, the nature of the oleogelator affected CUs bioaccessibility, which was lower in oleogels containing crystalline particles (MG and RW). These findings appear interesting in the attempt to develop oleogels able to control lipid digestion as well as to deliver bioactive molecules in food systems.

    Topics: Biological Availability; Diarylheptanoids; Digestion; Fatty Acids; Humans; Lipolysis; Monoglycerides; Organic Chemicals; Particle Size; Phenylpropionates; Rheology; Sitosterols; Sunflower Oil

2020
Phytosterols extraction from hickory (Carya cathayensis Sarg.) husk with a green direct citric acid hydrolysis extraction method.
    Food chemistry, 2020, Jun-15, Volume: 315

    This study investigated the direct citric acid hydrolysis extraction method to optimize phytosterols extraction from hickory husk. Single factor experiments followed by a three-level three-factor Box-Behnken experiments were performed. The optimal extraction parameters were determined as: pH of 2.0, liquid-to-solid ratio of 17.12: 1 mL/g, and temperature of 55.81 °C. Practical experiments were carried out in triplicate, and subsequently yielded phytosterols of 912.452 ± 17.452 μg/g DW, in good consistence with the predicted extraction yield of 902.874 μg/g DW. The conductivity of the extract was also found to play effective role under direct citric acid hydrolysis and recorded 36.30 ± 1.08 μs/cm at optimum extraction condition. β-Sitosterol stigmasterol, campsterol, ergosterol and lupeol were detected as main PSs and triterpenoids in hickory husk using UPLC-Triple-TOF/MS. Finally, the comparison between direct hydrolysis extraction and traditional solvent extraction showed that this new method was more effective and eco-friendlier to extract both free and conjugated phytosterols.

    Topics: Carya; Citric Acid; Ergosterol; Hydrogen-Ion Concentration; Hydrolysis; Models, Theoretical; Pentacyclic Triterpenes; Phytosterols; Sitosterols; Stigmasterol; Triterpenes

2020
Beta-sitosterol attenuates insulin resistance in adipose tissue via IRS-1/Akt mediated insulin signaling in high fat diet and sucrose induced type-2 diabetic rats.
    European journal of pharmacology, 2020, Apr-15, Volume: 873

    In our previous study, we have shown that β-sitosterol (SIT) enhances glycemic control by increasing the activation of insulin receptor (IR) and glucose transporter 4 (GLUT4) proteins in adipose tissue. However, the possible role of SIT on the regulation of post-receptor insulin signal transduction is not known. Hence, the study was aimed to assess the effects of SIT on IRS-1/Akt mediated insulin signaling molecules in high-fat diet and sucrose induced type-2 diabetic rats. An oral effective dose of SIT (20 mg/kg b.wt) was given for 30 days to high fat-fed type-2 diabetic rats to find out whether SIT regulates IRS-1/Akt pathway of insulin signaling. The results showed that SIT attenuated the insulin receptor substrate-1 serine phosphorylation (p-IRS-1

    Topics: Adipose Tissue; Animals; beta-Arrestin 2; Computer Simulation; Diabetes Mellitus, Type 2; Diet, High-Fat; Insulin; Insulin Receptor Substrate Proteins; Insulin Resistance; Male; Models, Molecular; Molecular Dynamics Simulation; Proto-Oncogene Proteins c-akt; Rats; Rats, Wistar; Signal Transduction; Sitosterols; src-Family Kinases; Sucrose

2020
Two new phenolic glycosides from the leaves of Garcinia epunctata Stapf.
    Zeitschrift fur Naturforschung. C, Journal of biosciences, 2020, Jan-28, Volume: 75, Issue:1-2

    The leaves of Garcinia epunctata Stapf have furnished two new phenolic glucosides, epunctosides A and B, along with 13 known secondary metabolites identified as lanceoloside A, betulinic acid, lupeol, stigmasterol, β-sitosterol, β-sitosterol-3-O-β-d-glucopyranoside, stigmasterol-3-O-β-d-glucopyranoside, luteolin-7-O-glucoside, quercitin-7-O-glucoside, amentoflavone, robustaflavone, 4'-O-methyl-amentoflavone and 4'-O-methyl-robustaflavone. All structures were established from chemical and spectroscopic evidence including 1D and 2D NMR data as well as by comparing the obtained spectroscopic data with literature. This is the first report of the presence of phenolic glucosides in the genus Garcinia.

    Topics: Betulinic Acid; Biflavonoids; Garcinia; Glycosides; Pentacyclic Triterpenes; Phenols; Plant Leaves; Secondary Metabolism; Sitosterols; Stigmasterol; Triterpenes

2020
The simultaneous quantification of phytosterols and tocopherols in liposomal formulations using validated atmospheric pressure chemical ionization- liquid chromatography -tandem mass spectrometry.
    Journal of pharmaceutical and biomedical analysis, 2020, May-10, Volume: 183

    A novel liquid chromatography tandem mass spectrometry (LC-MS/MS) method was developed and validated to simultaneously quantify phytosterols (brassicasterol, campesterol, stigmasterol and β-sitosterol) and tocopherols (alpha, beta, gamma and delta) entrapped in the lipid bilayer of a liposomal formulation. Apart from liposomes (a pharmaceutical product), the developed method was able to quantify target analytes in agricultural products, thus showing wide applications. Atmospheric pressure chemical ionization (APCI) was employed due to the enhanced ionization of phytosterols and tocopherols in comparison to electrospray ionization. Unlike published work, the chromatographic conditions were modified to simplify the analytical approach. For the first time, a simple isocratic elution (acetonitrile:methanol 99:1 v/v) was utilized for the separation of four phytosterols and four tocopherols in a single run. A substantially better baseline separation of phytosterols were obtained in comparison to reported methods by using poroshell C18 column. The method has a total run time of 7 min, which is the shortest run time among all reported quantitative methods for the simultaneous determination of four phytosterols and four tocopherols. Calibration curves for all phytosterols were linear in the range of 0.05-10 μg/mL. In the case of tocopherols, alpha tocopherol showed linear response in the range of 0.25-10 μg/mL. However, gamma and delta tocopherols exhibited quadratic relationship in the same concentration range (0.25-10 μg/mL). Validation parameters met the International Conference on Harmonization (ICH) guidelines in terms of selectivity, accuracy, precision, repeatability, sensitivity, matrix effects, dilution integrity and stability. The method was, for the first time, successfully applied for the quantifying phytosterols and tocopherols entrapped inside liposomes. An interesting chromatographic phenomenon was observed during sample analysis. Alpha tocopherol (entrapped in the liposomal lipid bilayer) was found to elute at two retention times, 2.53 min and 3.60 min. Such dual separation was not observed in calibration standards and quality controls. It was concluded that the chiral recognition ability of liposomes made up of phosphatidylcholine separated the enantiomers of alpha tocopherol, giving rise to two peaks at two different retention time. To sum, the reported novel LC-MS/MS method addresses three major analytical shortcomings, namely i)longer run time,

    Topics: Atmospheric Pressure; Calibration; Cholestadienols; Cholesterol; Chromatography, High Pressure Liquid; Chromatography, Liquid; Liposomes; Phytosterols; Reproducibility of Results; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Stigmasterol; Tandem Mass Spectrometry; Tocopherols

2020
A Phytosterolemic Mixture of Sterols Inhibits Cholesterol Synthesis, Esterification, and Low-Density Lipoprotein Receptor mRNA Abundance in HepG2 Cells.
    Lipids, 2020, Volume: 55, Issue:2

    HepG2 cells were incubated with a 16.5:1.7:1 ratio of cholesterol:sitosterol:campesterol (CSC), a ratio of the major sterols observed in the plasma of phytosterolemia patients, or with cholesterol alone in combination with [

    Topics: Carbon Radioisotopes; Cholesterol; Cholesterol Esters; Down-Regulation; Gene Expression Profiling; Gene Expression Regulation; Hep G2 Cells; Humans; Hypercholesterolemia; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Models, Biological; Phytosterols; Receptors, LDL; Sitosterols

2020
β-Sitosterol regulated microRNAs in endothelial cells against an oxidized low-density lipoprotein.
    Food & function, 2020, Feb-26, Volume: 11, Issue:2

    β-Sitosterol is a natural compound widely found in many vegetable oils, nuts, and plant medicines; it lowers the cholesterol levels, enhances the production of plasminogen activators, and exhibits anticancer and antiatherogenic effects. However, the direct endothelial protection of β-sitosterol against an oxidized low-density lipoprotein (ox-LDL) is not well understood. In the present study, β-sitosterol significantly inhibited cell apoptosis (P < 0.01), increased cell migration (P < 0.01), improved energy metabolism (P < 0.05) and improved morphology after ox-LDL (50 μg ml-1) exposure following β-sitosterol (2 μg mL-1) treatment in human aortic endothelial cells (HAECs ). A total of 691 differentially expressed (DE) mRNAs were identified (579 were upregulated and 112 were downregulated, fold change ≥2.0, P < 0.05) after 24 h of β-sitosterol administration in transcriptome sequencing (β-sitosterol vs. ox-LDL), which suggested that β-sitosterol reversed 62.32% change in mRNAs induced by ox-LDL. DE mRNAs are enriched mainly in focal adhesion, ribosomes, eukaryotic translation elongation, etc. Considering that one of the enrichment is 3'-UTR-mediated translational regulation, we explored DE microRNA (miRNA). The miRNA-seq data proposed 87 up-regulated and 58 down-regulated miRNAs (fold change ≥2.0, P < 0.05) in miRNA-seq (β-sitosterol vs. ox-LDL), suggesting that β-sitosterol reversed 76.67% change in miRNAs induced by ox-LDL. The DE miRNA-DE mRNA coexpression network focused on ribosomes, cell cycle, oxidative phosphorylation, PI3K-Akt signaling pathway, TNF signaling pathway, ErbB signaling pathway, and mTOR signaling pathway. Consequently, miRNAs might be the targets of β-sitosterol and play vital roles in transcriptional regulation in endothelial protective and antiatherogenic effects against ox-LDL.

    Topics: Aorta; Apoptosis; Cell Movement; Cells, Cultured; Endothelial Cells; Humans; Lipoproteins, LDL; MicroRNAs; Protective Agents; Signal Transduction; Sitosterols; Transcriptome

2020
Naturally-occurring cholesterol analogues in lipid nanoparticles induce polymorphic shape and enhance intracellular delivery of mRNA.
    Nature communications, 2020, 02-20, Volume: 11, Issue:1

    Endosomal sequestration of lipid-based nanoparticles (LNPs) remains a formidable barrier to delivery. Herein, structure-activity analysis of cholesterol analogues reveals that incorporation of C-24 alkyl phytosterols into LNPs (eLNPs) enhances gene transfection and the length of alkyl tail, flexibility of sterol ring and polarity due to -OH group is required to maintain high transfection. Cryo-TEM displays a polyhedral shape for eLNPs compared to spherical LNPs, while x-ray scattering shows little disparity in internal structure. eLNPs exhibit higher cellular uptake and retention, potentially leading to a steady release from the endosomes over time. 3D single-particle tracking shows enhanced intracellular diffusivity of eLNPs relative to LNPs, suggesting eLNP traffic to productive pathways for escape. Our findings show the importance of cholesterol in subcellular transport of LNPs carrying mRNA and emphasize the need for greater insights into surface composition and structural properties of nanoparticles, and their subcellular interactions which enable designs to improve endosomal escape.

    Topics: Animals; Biological Transport, Active; Cell Line; Cholesterol; Cryoelectron Microscopy; Endosomes; HEK293 Cells; HeLa Cells; Humans; Lipids; Mice; Nanoparticles; RAW 264.7 Cells; RNA, Messenger; Sitosterols; Transfection; X-Ray Diffraction

2020
Dietary β-sitosterol regulates serum lipid level and improves immune function, antioxidant status, and intestinal morphology in broilers.
    Poultry science, 2020, Volume: 99, Issue:3

    This research investigated effects of dietary β-sitosterol addition at different levels on serum lipid levels, immune function, oxidative status, and intestinal morphology in broilers. One-day-old broiler chicks were allocated to 5 groups of 6 replicates. Chickens in the 5 groups were fed a basal diet supplemented with 0 (control group), 40, 60, 80, and 100 mg/kg of β-sitosterol for 42 D, respectively. β-Sitosterol linearly decreased (P < 0.05) concentrations of serum total cholesterol, jejunal tumor necrosis factor α (TNF-α), and ileal interleukin 1β (IL-1β) and mRNA relative expressions levels of jejunal TLR4 and ileal MyD88, whereas it linearly increased (P < 0.05) contents of jejunal immunoglobulin G (IgG), ileal secreted IgA and glutathione, jejunal catalase activity and Nrf2 mRNA relative expression level, villus height (VH), and VH-to-crypt depth (CD) ratio (VH:CD) in the jejunum and ileum. Linear and quadratic increases (P < 0.05) in absolute and relative spleen weight were observed by dietary β-sitosterol, whereas malondialdehyde (MDA) concentration in the jejunum and ileum followed the opposite trend (P < 0.05). Compared with the control group, dietary β-sitosterol at higher than or equal to 60 mg/kg level decreased (P < 0.05) contents of serum total cholesterol, ileal MDA, and jejunal TLR4 mRNA relative expression level, whereas it increased (P < 0.05) absolute spleen weight and ileal glutathione content. Higher than or equal to 80 mg/kg level of β-sitosterol enhanced (P < 0.05) jejunal IgG concentration, VH, catalase activity, and Nrf2 relative expression level and ileal secreted IgA content, but reduced (P < 0.05) ileal IL-1β content and MyD88 mRNA relative expression level. β-Sitosterol addition at 60 and 80 mg/kg levels increased (P < 0.05) relative spleen weight, whereas it decreased (P < 0.05) jejunal MDA accumulation. Moreover, 100 mg/kg level of β-sitosterol reduced (P < 0.05) jejunal TNF-α level, but it increased (P < 0.05) VH in the jejunum and VH:CD in the jejunum and ileum. Accordingly, dietary β-sitosterol supplementation could regulate serum cholesterol level, promote immune function, and improve intestinal oxidative status and morphology in broilers.

    Topics: Animal Feed; Animals; Chickens; Diet; Dietary Supplements; Dose-Response Relationship, Drug; Immunity, Innate; Intestines; Lipids; Oxidative Stress; Random Allocation; Sitosterols

2020
    Journal of helminthology, 2020, Mar-04, Volume: 94

    Haemonchus contortus is a haematophagous gastrointestinal nematode (GIN) that causes severe anaemia and even death in small ruminants, negatively impacting the economic viability of farms. Traditionally, this parasite has been controlled with chemical compounds; however, inadequate use of these types of products has favoured the emergence of anthelmintic resistance. Therefore, it is necessary to search for alternatives for GIN control. Previous studies have reported the anthelmintic activity of edible mushroom extracts against H. contortus. A recent study reported that a fraction constituted of different fatty acids and β-sitosterol isolated from the basidiomata of the edible mushroom Pleurotus djamor ECS-123 has ovicidal and larvicidal activity against H. contortus. Thus, this study aimed to assess the anthelmintic activity of the pure molecules: pentadecanoic acid, palmitic acid, β-sitosterol, stearic acid and linoleic acid. For this purpose, an egg-hatching inhibition test was carried out in which the compounds were evaluated individually and in combination at a final concentration of 20 mg mL-1. Furthermore, larval mortality was assessed using a combination of the five commercial compounds previously mentioned at different concentrations (1.25-20 mg mL-1). Palmitic acid and stearic acid, in some combinations, inhibited H. contortus egg hatching by 100%. On the other hand, in the larval mortality test, the combination of the five compounds showed dose-dependent behaviour, and 100% mortality was obtained 24 h post-incubation. Pure molecules and their combinations have anthelmintic-like activity against the eggs and larvae of H. contortus.

    Topics: Agaricales; Animals; Antinematodal Agents; Biological Assay; Fatty Acids; Gastrointestinal Tract; Haemonchus; Larva; Male; Plant Extracts; Sheep; Sitosterols

2020
Physical properties and cookie-making performance of oleogels prepared with crude and refined soybean oil: a comparative study.
    Food & function, 2020, Mar-01, Volume: 11, Issue:3

    The objective of this research was to fabricate crude soybean oil oleogels (CSO) using β-sitosterol (BS) and/or monoacylglycerol (MAG) and compare their role with that of refined soybean oil oleogels (RSO) in cookie making. Both crude and refined soybean oil oleogels were formed with BS or MAG, or the combination of both (1 : 1) at a fixed concentration of 10 wt%. The thermal behavior of the oleogels was measured using differential scanning calorimetry (DSC). The crystal structure and morphology of the oleogels were characterized using X-ray diffraction (XRD) and polarized light microscopy (PLM). The hardness of the oleogel and commercial vegetable shortening was compared using a texture analyzer. The characteristics of cookies made with the oleogels were compared with those of cookies made with commercial vegetable shortening. Overall, the incorporation of BS and/or MAG into crude and refined soybean oil can produce oleogels with solid-like properties. Refined soybean oil formed stronger and firmer oleogels as compared to crude soybean oil. RSO structured by BS presented branched fiber-like, elongated plate-like, and needle-like crystals while the same oil gelled by MAG contained spherulite crystals. RSO made with the combination of BS and MAG displayed crystal morphologies from both BS and MAG. The same crystal morphologies were observed in CSO with lower quantities. Comparing the quality of cookies made with the oleogels and commercial vegetable shortening, equal or better performance of both RSO and CSO in terms of weight, thickness, width, spread ratio, and hardness of cookies than that of commercial vegetable shortening was observed. By combining the results of the physical characterization and cookie making performance, it can be concluded that both crude and refined soybean oleogels could resemble commercial shortening, which offers the possibility of using oleogels to replace shortening in the baking industry.

    Topics: Cooking; Monoglycerides; Organic Chemicals; Sitosterols; Soybean Oil

2020
One-step rapid extraction of phytosterols from vegetable oils.
    Food research international (Ottawa, Ont.), 2020, Volume: 130

    Topics: Cholesterol; Chromatography, Gas; Food Handling; Phytosterols; Plant Oils; Sitosterols; Stigmasterol; Temperature; Time Factors

2020
β-Sitosterol Reverses Multidrug Resistance via BCRP Suppression by Inhibiting the p53-MDM2 Interaction in Colorectal Cancer.
    Journal of agricultural and food chemistry, 2020, Mar-25, Volume: 68, Issue:12

    Phytosterols are widely present in vegetable oils, nuts, cereal products, fruits, and berries. Phytosterol-induced treatment sensitivity has recently shed light on alleviating multidrug resistance in cancer therapy. Here, we demonstrated that β-sitosterol, the most common dietary phytosterol, recovers oxaliplatin (OXA) sensitivity in drug-resistant colorectal cancer (CRC) cells by inhibiting breast cancer resistance protein (BCRP) expression. We further showed evidence that β-sitosterol could activate p53 by disrupting the p53-MDM2 interaction, leading to an increase in p53 translocation to the nucleus and silencing the nuclear factor-κB (NF-κB) pathway, which is necessary for BCRP expression. Finally, we suggested that the combination of OXA and β-sitosterol has a synergistic tumor suppression effect in vivo using a xenograft mouse model. These results revealed that β-sitosterol is able to mediate the p53/NF-κB/BCRP signaling axis to regulate the response of CRC to chemotherapy. The combined application of β-sitosterol and OXA can be a potential way to improve CRC treatment.

    Topics: Animals; Antineoplastic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 2; Colorectal Neoplasms; Down-Regulation; Drug Resistance, Neoplasm; Gene Expression Regulation, Neoplastic; HCT116 Cells; Humans; Mice, Inbred BALB C; Neoplasm Proteins; Oxaliplatin; Protein Interaction Maps; Proto-Oncogene Proteins c-mdm2; Sitosterols; Tumor Suppressor Protein p53

2020
Biosorption of sterols from tobacco waste extract using living and dead of newly isolated fungus
    Bioscience, biotechnology, and biochemistry, 2020, Volume: 84, Issue:7

    Sterols are verified to be able to produce polycyclic aromatic hydrocarbons during its pyrolysis. In this study, a kind of

    Topics: Absorption, Physiological; Aspergillus fumigatus; Biodegradation, Environmental; Biomass; Cholesterol; Ergosterol; Hydrogen-Ion Concentration; Microscopy, Electron, Scanning; Nicotiana; Phytosterols; Plant Extracts; Plant Leaves; Sitosterols; Spectroscopy, Fourier Transform Infrared; Stigmasterol; Water Pollutants, Chemical

2020
Depletion of β-sitosterol and enrichment of quercetin and rutin in Cissus quadrangularis Linn fraction enhanced osteogenic but reduced osteoclastogenic marker expression.
    BMC complementary medicine and therapies, 2020, Apr-03, Volume: 20, Issue:1

    Cissus quadrangularis Linn. (CQ) has been used in Indian and Thai traditional medicine for healing bone fractures because of numerous active ingredients in CQ. It is still unclear which compounds are the active ingredients for bone formation.. The molecular docking technique, the ethanolic extraction along with hexane fractionation, and an in vitro experiment with a human osteoblast cell line (MG-63) were used to narrow down the active compounds, to prepare the CQ extract, and to test biological activities, respectively.. The molecular docking technique revealed that quercetin and β-sitosterol had highest and lowest potential to bind to estrogen receptors, respectively. Compared to the crude ethanol extract (P1), the ethanolic fraction (P2) was enriched with rutin and quercetin at 65.36 ± 0.75 and 1.06 ± 0.12 mg/g, respectively. Alkaline phosphatase (ALP) activity was significantly enhanced in osteoblasts exposed to the P2 in both tested concentrations. The amount of hydroxyproline was slightly increased in the P1 treatment, while osteocalcin was inhibited. Moreover, the P2 significantly activated osteoprotegerin (OPG) and inhibited receptor activator of nuclear factor κ ligand (RANKL) expression.. Taken together, the enriched rutin and quercetin fraction of CQ triggered the molecules involved in bone formation and the molecules inhibiting bone resorption.

    Topics: Bone Resorption; Cell Line; Cissus; Humans; Molecular Docking Simulation; Molecular Structure; Osteogenesis; Plant Extracts; Quercetin; Rutin; Sitosterols

2020
β-Sitosterol-assisted silver nanoparticles activates Nrf2 and triggers mitochondrial apoptosis via oxidative stress in human hepatocellular cancer cell line.
    Journal of biomedical materials research. Part A, 2020, Volume: 108, Issue:9

    Cancer nanomedicine is an emerging field of cancer therapeutics. Incidence of hepatocellular carcinoma (HCC) is increasing worldwide, and currently, it is the second leading cause of cancer-related deaths. This study investigates the cytotoxic potential of β-sitosterol-assisted silver nanoparticles (BSS-SNPs) in HepG2 cells. The silver nanoparticles were synthesized using β-sitosterol as a reducing and stabilizing agent. The characterization of BSS-SNPs was done by UV-visible spectrophotometry and transmission electron microscope (TEM) analysis. HepG2 cells were treated with different concentrations of BSS-SNPs for 24 hr, and cytotoxicity was evaluated by MTT assay. Intracellular ROS was investigated by 2',7'-dichlorofluorescin diacetate staining. The nuclear factor erythroid 2-related factor 2 (Nrf-2) protein expression was investigated by immunofluorescence staining. Morphology-related to apoptotic changes were analyzed by annexin V staining. Intrinsic apoptosis pathwayrelated molecular markers were investigated by western blotting and PCR analysis. Spectrophotometry analysis confirmed a strong absorption peak at 420 nm, which showed the successful synthesis of BSS-SNPs. The TEM analysis indicated the spherical-, rod-, and hexagonal BSS-SNPs with the size ranges from 5 to 55 nm. BSS-SNPs significantly inhibited the proliferation and induced ROS and Nrf-2 expression in HepG2 cells. BSS-SNPs treatment caused apoptosis-related morphological changes and upregulated the pro-apoptotic markers such as bax, p53, cytochrome c, and caspases-9, -3 and downregulated bcl-2 expressions. Our findings suggest that BSS-SNPs might serve as potential drug candidates for HCC.

    Topics: Antineoplastic Agents; Apoptosis; Carcinoma, Hepatocellular; Hep G2 Cells; Humans; Liver Neoplasms; Mitochondria; Nanoparticles; NF-E2-Related Factor 2; Oxidative Stress; Silver; Sitosterols

2020
Prophylactic Intra-Uterine β-Cyclodextrin Administration during Intra-Uterine
    Nutrients, 2020, May-05, Volume: 12, Issue:5

    Chorioamnionitis can lead to inflammation and injury of the liver and gut, thereby predisposing patients to adverse outcomes such as necrotizing enterocolitis (NEC). In addition, intestinal bile acids (BAs) accumulation is causally linked to NEC development. Plant sterols are a promising intervention to prevent NEC development, considering their anti-inflammatory properties in the liver. Therefore, we investigated whether an intra-amniotic (IA)

    Topics: Animals; beta-Cyclodextrins; Cholesterol; Chorioamnionitis; Disease Models, Animal; Drug Carriers; Enterocolitis, Necrotizing; Enterohepatic Circulation; Female; Fetus; Inflammation; Injections, Intralesional; Liver; Phytosterols; Phytotherapy; Post-Exposure Prophylaxis; Pregnancy; Sheep; Sitosterols; Ureaplasma; Ureaplasma Infections

2020
Imperatorin and β-sitosterol have synergistic activities in alleviating collagen-induced arthritis.
    Journal of leukocyte biology, 2020, Volume: 108, Issue:2

    Rheumatoid arthritis (RA) is a chronic disease with complex molecular network of pathophysiology, single drug is usually not full satisfactory because it is almost impossible to target the whole molecular network of the disease. Drug combinations that act synergistically with each another is an effective strategy in RA therapy. In this study, we aimed to establish a new strategy to search effective synergized compounds from Chinese herbal medicine (CHM) used in RA. Based on multi-information integrative approaches, imperatorin (IMP) and β-sitosterol (STO) were predicted as the most effective pair for RA therapy. Further animal experiments demonstrated that IMP+STO treatment ameliorated arthritis severity of collagen-induced arthritis (CIA) rats in a synergistic manner, whereas IMP or STO administration separately had no such effect. RNA sequencing and IPA analysis revealed that the synergistic mechanism of IMP+STO treatment was related to its regulatory effect on 5 canonical signaling pathways, which were not found when IMP or STO used alone. Moreover, LTA, CD83, and SREBF1 were 3 important targets for synergistic mechanism of IMP+STO treatment. The levels of these 3 genes were significantly up-regulated in IMP+STO group compared to model group, whereas IMP or STO administration separately had no effect on them. In conclusion, this study found that IMP and STO were 2 synergistic compounds from the CHM in RA therapy, whose synergistic mechanism was closely related to regulate the levels of LTA, CD83, and SREBF1.

    Topics: Animals; Arthritis, Experimental; Arthritis, Rheumatoid; CD4-Positive T-Lymphocytes; Computational Biology; Disease Models, Animal; Drug Synergism; Drugs, Chinese Herbal; Furocoumarins; Male; Phytotherapy; Rats; Severity of Illness Index; Signal Transduction; Sitosterols

2020
Uncovering the active compounds and effective mechanisms of the dried mature sarcocarp of Cornus officinalis Sieb. Et Zucc. For the treatment of Alzheimer's disease through a network pharmacology approach.
    BMC complementary medicine and therapies, 2020, May-25, Volume: 20, Issue:1

    Shanzhuyu (the dried mature sarcocarp of Cornus officinalis Sieb. et Zucc., DMSCO) is a Chinese herb that can be used for the treatment of Alzheimer's disease (AD), but its mechanism remains unknown. The present study aimed to investigate the active ingredients and effective mechanisms of DMSCO for the treatment of AD based on a network pharmacology approach.. The active components of DMSCO were collected from the TCMSP and ETCM databases and the target proteins of these compounds were predicted using TCMSP, SwissTargetPrediction and the STITCH database. The AD-related target proteins were identified from the OMIM, DisGeNet, GEO and GeneCards databases. The network interaction model of the compound-target-disease was established and was used to obtain the key targets of DMSCO on AD through network topology analysis. Subsequently, gene enrichment in Gene Ontology (GO) and KEGG pathways were conducted using the David 6.8 online tool.. A total of 30 DMSCO effective compounds and 209 effective drug targets were obtained. A total of 172 AD-related genes and 37 shared targets of DMSCO and AD were identified. A total of 43 key targets for the treatment of AD were obtained from the topological analysis of the DMSCO-AD target network. These key targets were involved in a variety of biological processes, including amyloid deposition, apoptosis, autophagy, inflammatory response and oxidative stress and pathways, such as the PI3K-AKT, MAPK and TNF pathways. Three key compounds, namely ursolic acid, anethole and β-sitosterol were obtained from the analysis of the key targets.. Ursolic acid, anethole and β-sitosterol may be the main active components of DMSCO in the treatment of AD. DMSCO can treat AD by regulating amyloid deposition, apoptosis, autophagy, inflammatory response and oxidative stress via the PI3K-AKT, MAPK and other signaling pathways.

    Topics: Allylbenzene Derivatives; Alzheimer Disease; Anisoles; Cornus; Drugs, Chinese Herbal; Humans; Protein Interaction Maps; Signal Transduction; Sitosterols; Triterpenes; Ursolic Acid

2020
Phytosterol, Lipid and Phenolic Composition, and Biological Activities of Guava Seed Oil.
    Molecules (Basel, Switzerland), 2020, May-27, Volume: 25, Issue:11

    Plant seeds have been found to contain bioactive compounds that have potential nutraceutical benefits. Guava seeds (

    Topics: Animals; Antioxidants; Carcinoma, Hepatocellular; Cholesterol; Female; Hexanes; Liver Neoplasms; Male; Oxidative Stress; Phenols; Phytosterols; Plant Extracts; Plant Oils; Psidium; Rats; Seeds; Sitosterols; Triglycerides

2020
β-sitosterol ameliorates influenza A virus-induced proinflammatory response and acute lung injury in mice by disrupting the cross-talk between RIG-I and IFN/STAT signaling.
    Acta pharmacologica Sinica, 2020, Volume: 41, Issue:9

    β-Sitosterol (24-ethyl-5-cholestene-3-ol) is a common phytosterol Chinese medical plants that has been shown to possess antioxidant and anti-inflammatory activity. In this study we investigated the effects of β-sitosterol on influenza virus-induced inflammation and acute lung injury and the molecular mechanisms. We demonstrate that β-sitosterol (150-450 μg/mL) dose-dependently suppresses inflammatory response through NF-κB and p38 mitogen-activated protein kinase (MAPK) signaling in influenza A virus (IAV)-infected cells, which was accompanied by decreased induction of interferons (IFNs) (including Type I and III IFN). Furthermore, we revealed that the anti-inflammatory effect of β-sitosterol resulted from its inhibitory effect on retinoic acid-inducible gene I (RIG-I) signaling, led to decreased STAT1 signaling, thus affecting the transcriptional activity of ISGF3 (interferon-stimulated gene factor 3) complexes and resulting in abrogation of the IAV-induced proinflammatory amplification effect in IFN-sensitized cells. Moreover, β-sitosterol treatment attenuated RIG-I-mediated apoptotic injury of alveolar epithelial cells (AEC) via downregulation of pro-apoptotic factors. In a mouse model of influenza, pre-administration of β-sitosterol (50, 200 mg·kg

    Topics: A549 Cells; Acute Lung Injury; Animals; Antiviral Agents; Apoptosis; DEAD Box Protein 58; Dogs; Female; HEK293 Cells; Humans; Inflammation; Influenza A Virus, H1N1 Subtype; Interferon Lambda; Interferon Type I; Interferons; Lung; Madin Darby Canine Kidney Cells; Mice, Inbred BALB C; Plants; Signal Transduction; Sitosterols; STAT1 Transcription Factor

2020
The coronary artery calcium score is linked to plasma cholesterol synthesis and absorption markers: Brazilian Longitudinal Study of Adult Health.
    Bioscience reports, 2020, 07-31, Volume: 40, Issue:7

    It is controversial whether atherosclerosis is linked to increased intestinal cholesterol absorption or synthesis in humans. The aim of the present study was to relate atherosclerosis to the measurements of plasma markers of cholesterol synthesis (desmosterol, lathosterol) and absorption (campesterol, sitosterol). In healthy male (n=344), non-obese, non-diabetics, belonging to the city of São Paulo branch of the Brazilian Longitudinal Study of Adult Health (ELSA-Brasil), we measured in plasma these non-cholesterol sterol markers, together with their anthropometric, dietary parameters, traditional atherosclerotic risk factors, and blood chemistry, coronary arterial calcium score (CAC), and ultrasonographically measured common carotid artery intima-media thickness (CCA-IMT). Cases with CAC>zero had the following parameters higher than cases with CAC = zero: age, waist circumference (WC), plasma total cholesterol (TC), low-density lipoprotein-cholesterol (LDL-C), and non-high density lipoprotein-cholesterol (non HDL-C). Plasma desmosterol and campesterol, duly corrected for TC, age, body mass index (BMI), waist circumference (WC), hypertension, smoking, and the homeostasis model assessment-insulin resistance (HOMA-IR) correlated with CAC, but not with CCA-IMT. The latter related to increased age, BMI, waist circumference (WC), and systolic blood pressure (SBP). Plasma HDL-C concentrations did not define CAC or CCA-IMT degrees, although in relation to the lower tertile of HDL-C in plasma the higher tertile of HDL-C had lower HOMA-IR and concentration of a cholesterol synthesis marker (desmosterol). Present work indicated that increased cholesterol synthesis and absorption represent primary causes of CAD, but not of the common carotid artery atherosclerosis.

    Topics: Adult; Aged; Atherosclerosis; Biomarkers; Body Mass Index; Brazil; Calcium; Carotid Artery, Common; Carotid Intima-Media Thickness; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Coronary Vessels; Cross-Sectional Studies; Desmosterol; Female; Humans; Intestinal Absorption; Intestinal Mucosa; Longitudinal Studies; Male; Middle Aged; Phytosterols; Prospective Studies; Sitosterols; Tomography, X-Ray Computed; Ultrasonography

2020
Characterization of oxyphytosterols generated by β-sitosterol ozonization.
    Archives of biochemistry and biophysics, 2020, 08-15, Volume: 689

    β-Sitosterol (βSito) is the most abundant phytosterol found in elevated concentrations in vegetable oils, nuts, seeds, cereals, fruits, and in many phytosterol-enriched foods. Although the benefits, there is a concern in terms of food quality and health due to the increasing consumption of phytosterols and the possible adverse side effects of their oxidation products, oxyphytosterols. βSito has a similar structure to cholesterol, with an unsaturated double bond at C5-C6, which is susceptible to oxidation by reactive oxygen species like ozone, generating oxyphytosterols. In this work we propose a mechanism of formation of three oxyphytosterols 2-[(7aR)-5-[(1R,4S)-4-hydroxy-1-methyl-2-oxocyclohexyl]-1,7a-dimethyl-1,2,3,3a,4,5,6,7- octahydroinden-4-yl] acetaldehyde (βSec), (2-[(7aR)-5-[(2R,5S)-5-hydroxy-2-methyl-7-oxo-oxepan- 2-yl]-1,7a-dimethyl-1,2,3,3a,4,5,6,7-octahydroinden-4- yl] acetaldehyde (βLac) and 2-((7aR)-5-((1R,4S)-4-hydroxy-1-methyl-2- oxocyclohexyl)-1,7a-dimethyloctahydro-1Hinden-4-yl) acetic acid (βCOOH) generated by ozonization of βSito, through their synthesis and molecular characterization. The cytotoxic effect of βSito and its main oxyphytosterol βSec was evaluated and both reduced the HepG2 cell viability.

    Topics: Cell Survival; Hep G2 Cells; Humans; Oxidation-Reduction; Ozone; Phytosterols; Reactive Oxygen Species; Sitosterols

2020
A case of ezetimibe-effective hypercholesterolemia with a novel heterozygous variant in ABCG5.
    Endocrine journal, 2020, Nov-28, Volume: 67, Issue:11

    Sitosterolemia is caused by homozygous or compound heterozygous gene mutations in either ATP-binding cassette subfamily G member 5 (ABCG5) or 8 (ABCG8). Since ABCG5 and ABCG8 play pivotal roles in the excretion of neutral sterols into feces and bile, patients with sitosterolemia present elevated levels of serum plant sterols and in some cases also hypercholesterolemia. A 48-year-old woman was referred to our hospital for hypercholesterolemia. She had been misdiagnosed with familial hypercholesterolemia at the age of 20 and her serum low-density lipoprotein cholesterol (LDL-C) levels had remained about 200-300 mg/dL at the former clinic. Although the treatment of hydroxymethylglutaryl-CoA (HMG-CoA) reductase inhibitors was ineffective, her serum LDL-C levels were normalized by ezetimibe, a cholesterol transporter inhibitor. We noticed that her serum sitosterol and campesterol levels were relatively high. Targeted analysis sequencing identified a novel heterozygous ABCG5 variant (c.203A>T; p.Ile68Asn) in the patient, whereas no mutations were found in low-density lipoprotein receptor (LDLR), proprotein convertase subtilisin/kexin type 9 (PCSK9), or Niemann-Pick C1-like intracellular cholesterol transporter 1 (NPC1L1). While sitosterolemia is a rare disease, a recent study has reported that the incidence of loss-of-function mutation in the ABCG5 or ABCG8 gene is higher than we thought at 1 in 220 individuals. The present case suggests that serum plant sterol levels should be examined and ezetimibe treatment should be considered in patients with hypercholesterolemia who are resistant to HMG-CoA reductase inhibitors.

    Topics: Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 5; Cholesterol; Cholesterol, LDL; Diagnostic Errors; Ezetimibe; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Hyperlipoproteinemia Type II; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Lipoproteins; Loss of Function Mutation; Middle Aged; Phytosterols; Sitosterols; Treatment Failure

2020
Markers of cholesterol synthesis are elevated in adolescents and young adults with type 2 diabetes.
    Pediatric diabetes, 2020, Volume: 21, Issue:7

    Changes in cholesterol absorption and cholesterol synthesis may promote dyslipidemia and cardiovascular disease in individuals with type 2 diabetes mellitus (T2DM).. To assess cholesterol synthesis and absorption in lean individuals, obese individuals, and individuals with T2DM.. We measured lathosterol and lanosterol (markers of cholesterol synthesis) as well as campesterol and β-sitosterol (markers of cholesterol absorption) in the serum of 15 to 26 years old individuals with T2DM (n = 95), as well as their lean (n = 98) and obese (n = 92) controls.. Individuals with T2DM showed a 51% increase in lathosterol and a 65% increase in lanosterol compared to lean controls. Similarly, obese individuals showed a 31% increase in lathosterol compared to lean controls. Lathosterol and lanosterol were positively correlated with body mass index, fasting insulin and glucose, serum triglycerides, and C-reactive protein, and negatively correlated with HDL-cholesterol. In contrast, campesterol and β-sitosterol were not altered in individuals with T2DM. Moreover, campesterol and β-sitosterol were negatively correlated with body mass index, fasting insulin, and C-reactive protein and were positively correlated with HDL-cholesterol.. Adolescents and young adults with T2DM show evidence of increased cholesterol synthesis compared to non-diabetic lean controls. These findings suggest that T2DM may promote cardiovascular disease by increasing cholesterol synthesis, and provide additional rationale for the use of cholesterol synthesis inhibitors in this group.

    Topics: Adolescent; Adult; Biomarkers; Body Mass Index; Case-Control Studies; Cholesterol; Diabetes Mellitus, Type 2; Humans; Obesity; Phytosterols; Sitosterols; Young Adult

2020
Integrated System Pharmacology and
    CNS & neurological disorders drug targets, 2020, Volume: 19, Issue:7

    Withania somnifera (WS), also referred to as Medhya Rasayana (nootropic or rejuvenating), has traditionally been prescribed for various neurological ailments, including dementia. Despite substantial evidence, pharmacological roles of WS, neither as nootropic nor as an antidementia agent, are well-understood at the cellular and molecular levels.. We aimed at elucidating the pharmacological action mechanisms of WS root constituents against Alzheimer's Disease (AD) pathology.. Various bioinformatics tools and resources, including DAVID, Cytoscape, NetworkAnalyst and KEGG pathway database were employed to analyze the interaction of WS root bioactive molecules with the protein targets of AD-associated cellular processes. We also used a molecular simulation approach to validate the interaction of compounds with selected protein targets.. Network analysis revealed that β-sitosterol, withaferin A, stigmasterol, withanolide A, and withanolide D are the major constituents of WS root that primarily target the cellular pathways such as PI3K/Akt signaling, neurotrophin signaling and toll-like receptor signaling and proteins such as Tropomyosin receptor Kinase B (TrkB), Glycogen Synthase Kinase-3β (GSK-3β), Toll-Like Receptor 2/4 (TLR2/4), and β-secretase (BACE-1). Also, the in silico analysis further validated the interaction patterns and binding affinity of the major WS compounds, particularly stigmasterol, withanolide A, withanolide D and β-sitosterol with TrkB, GSK-3β, TLR2/4, and BACE-1.. The present findings demonstrate that stigmasterol, withanolide A, withanolide D and β-sitosterol are the major metabolites that are responsible for the neuropharmacological action of WS root against AD-associated pathobiology, and TrkB, GSK-3β, TLR2/4, and BACE-1 could be the potential druggable targets.

    Topics: Alzheimer Disease; Computer Simulation; Glycogen Synthase Kinase 3 beta; Humans; Phosphatidylinositol 3-Kinases; Plant Extracts; Sitosterols; Withania; Withanolides

2020
β-Sitosterol-loaded solid lipid nanoparticles ameliorate complete Freund's adjuvant-induced arthritis in rats: involvement of NF-кB and HO-1/Nrf-2 pathway.
    Drug delivery, 2020, Volume: 27, Issue:1

    Topics: Animals; Arthritis, Rheumatoid; Dose-Response Relationship, Drug; Drug Carriers; Freund's Adjuvant; Heme Oxygenase (Decyclizing); Hypolipidemic Agents; Male; Nanoparticles; NF-E2-Related Factor 2; NF-kappa B; Rats; Rats, Wistar; Signal Transduction; Sitosterols

2020
    Food & function, 2020, Nov-18, Volume: 11, Issue:11

    The objective of this study was to investigate the influence of self-assembled microstructure on lipid digestibility in phytosterol (γ-oryzanol and β-sitosterol) oleogels. Different molar ratios of γ-oryzanol and β-sitosterol yielded a variety of crystal morphologies; the resulting gels were tested for their lipid emulsification efficiency, release rate of free fatty acids (FFAs) during lipolysis, and their effect on lipase behavior. Results indicated that oleogels were harder to emulsify when compared to oil samples. The emulsification efficiencly was affected by both the gel strength and crystal morphology of the self-assembled structures within phytosterol oleogels. In oil emulsions, intestinal digestion resulted in more extensive lipid droplet coalescence with increased particle size when compared to oleogel emulsions. The FFA release rate suggested that the extent of lipid digestion was correlated to the emulsification efficiency. The interfacial binding of lipase indicated that the amount of lipase adsorption was positively correlated to the interface area created during the emulsification process. Finally, isothermal titration calorimetry results indicated that self-assembled structures within these oleogels physically obstructed the interaction between lipase and lipid. Ultimately, this led to lower reaction rate during gastrointestinal digestion. Collectively, these results may have important implications in designing oleogel systems with controlled lipid digestibility as well as controlling the bioavailability of delivered lipid-soluble bioactive compounds.

    Topics: Digestion; Emulsions; Humans; Lipase; Organic Chemicals; Phenylpropionates; Phytosterols; Sitosterols; Structure-Activity Relationship

2020
A network-based pharmacology study of active compounds and targets of Fritillaria thunbergii against influenza.
    Computational biology and chemistry, 2020, Volume: 89

    Seasonal and pandemic influenza infections are serious threats to public health and the global economy. Since antigenic drift reduces the effectiveness of conventional therapies against the virus, herbal medicine has been proposed as an alternative. Fritillaria thunbergii (FT) have been traditionally used to treat airway inflammatory diseases such as coughs, bronchitis, pneumonia, and fever-based illnesses. Herein, we used a network pharmacology-based strategy to predict potential compounds from Fritillaria thunbergii (FT), target genes, and cellular pathways to better combat influenza and influenza-associated diseases. We identified five compounds, and 47 target genes using a compound-target network (C-T). Two compounds (beta-sitosterol and pelargonidin) and nine target genes (BCL2, CASP3, HSP90AA1, ICAM1, JUN, NOS2, PPARG, PTGS1, PTGS2) were identified using a compound-influenza disease target network (C-D). Protein-protein interaction (PPI) network was constructed and we identified eight proteins from nine target genes formed a network. The compound-disease-pathway network (C-D-P) revealed three classes of pathways linked to influenza: cancer, viral diseases, and inflammation. Taken together, our systems biology data from C-T, C-D, PPI and C-D-P networks predicted potent compounds from FT and new therapeutic targets and pathways involved in influenza.

    Topics: Anthocyanins; Antiviral Agents; Databases, Chemical; Databases, Genetic; Fritillaria; Humans; Orthomyxoviridae; Pharmacology; Protein Interaction Maps; Sitosterols; Systems Biology

2020
Application of a 2D Molybdenum Telluride in SERS Detection of Biorelevant Molecules.
    ACS applied materials & interfaces, 2020, Oct-21, Volume: 12, Issue:42

    Two-dimensional (2D) transition-metal dichalcogenides have become promising candidates for surface-enhanced Raman spectroscopy (SERS), but currently very few examples of detection of relevant molecules are available. Herein, we show the detection of the lipophilic disease marker β-sitosterol on few-layered MoTe

    Topics: Density Functional Theory; Molybdenum; Particle Size; Sitosterols; Spectrum Analysis, Raman; Surface Properties; Tellurium

2020
Nutritional Component and Chemical Characterization of Chinese Highland Barley Bran Oil.
    Journal of oleo science, 2020, Nov-01, Volume: 69, Issue:11

    The nutritional composition and chemical properties of the Chinese highland barley bran oil were characterized in this study. The barley bran oil extracted with solvent possessed relatively high acid value and peroxide value, indicating that the oil should be further refined before using. The fatty acid composition of the oil showed that the content of unsaturated fatty acids was 80.12 g/100 g, in which the content of polyunsaturated fatty acids was as high as 60.41 g/100 g. The overall triacylglycerol profile showed that the oil contained 27 TAGs including 21 regioisomers. Major TAGs included LLL (21.08 g/100 g), PLL (19.27 g/100 g), LLO (12.24 g/100 g), and LLLn (12.17 g/100 g). The total unsaponifiable matter of the oil reached up to 10.74 g/100 g oil. The total phytosterol content reached 7.90 g/100 g oil, in which β-sitosterol was the most predominant, with the content of 5.69 g/100 g oil. Other important sterols included campesterol (1.32 g/100 g oil), lanosterol (0.70 g/100 g oil) and stigmasterol (0.19 g/100 g oil).

    Topics: China; Cholesterol; Fatty Acids, Unsaturated; Hordeum; Lanosterol; Nutrients; Phytosterols; Plant Oils; Sitosterols; Stigmasterol; Triglycerides

2020
Neurite Outgrowth-Promoting Activity of Compounds in PC12 Cells from Sunflower Seeds.
    Molecules (Basel, Switzerland), 2020, Oct-16, Volume: 25, Issue:20

    In the current super-aging society, the establishment of methods for prevention and treatment of Alzheimer's disease (AD) is an urgent task. One of the causes of AD is thought to be a decrease in the revel of nerve growth factor (NGF) in the brain. Compounds showing NGF-mimicking activity and NGF-enhancing activity have been examined as possible agents for improving symptoms. In the present study, sunflower seed extract was found to have neurite outgrowth-promoting activity, which is an NGF-enhancing activity, in PC12 cells. To investigate neurite outgrowth-promoting compounds from sunflower seed extract, bioassay-guided purification was carried out. The purified active fraction was obtained by liquid-liquid partition followed by some column chromatographies. Proton nuclear magnetic resonance and gas chromatography-mass spectrometry analyses of the purified active fraction indicated that the fraction was a mixture of β-sitosterol, stigmasterol and campesterol, with β-sitosterol being the main component. Neurite outgrowth-promoting activities of β-sitosterol, stigmasterol, campesterol and cholesterol were evaluated in PC12 cells. β-Sitosterol and stigmasterol showed the strongest activity of the four sterol compounds (β-sitosterol ≈ stigmasterol > campesterol > cholesterol), and cholesterol did not show any activity. The results indicated that β-sitosterol was the major component responsible for the neurite outgrowth-promoting activity of sunflower seeds. Results of immunostaining also showed that promotion by β-sitosterol of neurite formation induced by NGF was accompanied by neurofilament expression. β-Sitosterol, which showed NGF-enhancing activity, might be a candidate ingredient in food for prevention of AD.

    Topics: Alzheimer Disease; Animals; Brain; Cholesterol; Gene Expression Regulation; Helianthus; Humans; Nerve Growth Factor; Neurites; Neuronal Outgrowth; PC12 Cells; Phytosterols; Plant Extracts; Rats; Seeds; Sitosterols; Stigmasterol

2020
LC-MS/MS and GC-MS profiling as well as the antimicrobial effect of leaves of selected Yucca species introduced to Egypt.
    Scientific reports, 2020, 10-20, Volume: 10, Issue:1

    Few studies thoroughly investigated different Yucca species introduced to Egypt. As a part of our ongoing investigation of the Yucca species; Yucca aloifolia and its variety Yucca aloifolia variegata, Yucca filamentosa, and Yucca elephantipes (Asparagaceae) were extensively subjected to phytochemical and antimicrobial investigation. Yucca species cultivated in Egypt showed no antimicrobial effect. GC/MS of the lipoid contents of Y. aloifolia variegata was carried out. Twenty-six fatty acids were identified. Saturated fatty acids established almost twice the unsaturated ones and constituted 64.64% of which palmitic acid and palmitoleic acid signifying 58.28% and 30.98%, respectively. Hydrocarbons were 21 constituting 39.64% of the unsaponifiable fraction. Only three sterols 42.36% were detected, major was γ-sitosterol. LC-MS/MS comparison of the 4 plant extracts imply that Y.aloifolia variegata L extract was the richest, which was apparent through its superior biological activity. LC-MS/MS analysis of the total alcoholic extract (Alc) of the leaves of Y.aloifolia variegata L. was performed using MS-techniques at different voltages; equal to 35 and 135 eV. Negative and positive-ion modes analyses at low fragmentation energy allowed the tentative identification of 41 and 34 compounds, respectively. The LC-ESI-MS/MS analysis in the positive mode proved to be better in the identification of saponins.

    Topics: Anti-Infective Agents; Chromatography, Liquid; Egypt; Fatty Acids; Gas Chromatography-Mass Spectrometry; Hydrocarbons; Plant Extracts; Plant Leaves; Saponins; Sitosterols; Yucca

2020
Biological effects of an oxyphytosterol generated by β-Sitosterol ozonization.
    Archives of biochemistry and biophysics, 2020, 12-15, Volume: 696

    Topics: Acetylcysteine; Cell Nucleus; Cell Survival; G1 Phase Cell Cycle Checkpoints; Hep G2 Cells; Humans; Microtubules; Mitotic Index; Oxidative Stress; Ozone; Sitosterols

2020
β-Sitosterol attenuates liver injury in a rat model of chronic alcohol intake.
    Archives of pharmacal research, 2020, Volume: 43, Issue:11

    Liver disease associated with long-term drinking is one of the leading causes of death. There is an urgent need for more effective drugs to reduce alcoholic liver damage. Yin Chen Hao, a traditional Chinese herbal medicine, is widely used for liver diseases. Here, we aimed to explore the protective effect of β-sitosterol (the active ingredient of Artemisia spp.) on alcoholic liver injuries. We treated the rats with alcohol and different dosages of β-sitosterol to detect the expression levels of liver function indicators in serum. The functions of β-sitosterol were evaluated based on variations in histology, liver function indicators and DNA oxidative damages. The underlying mechanism was investigated by measuring lipid peroxidation, the antioxidant, the expression of cytochrome P450 2E1 and the expression of apoptosis related genes. The results showed that β-sitosterol could improve liver histology and suppress biochemical indicators caused by alcohol in serum. In addition, β-sitosterol alleviates alcohol-induced oxidative stress, such as restoring erythrocyte membrane fluidity, reducing glutathione depletion, restoring antioxidant enzyme activity and reducing malondialdehyde overproduction. Furthermore, β-sitosterol downregulated the expression of apoptosis-related genes through the PI3K/Akt pathway. In conclusion, β-sitosterol has a protective effect on chronic alcoholism and has broad clinical application prospects in the treatment of alcohol-induced liver damage.

    Topics: Alcohol Drinking; Animals; Antioxidants; Apoptosis; Apoptosis Regulatory Proteins; Disease Models, Animal; DNA Damage; Lipid Peroxidation; Liver; Liver Diseases, Alcoholic; Male; Oxidative Stress; Phosphatidylinositol 3-Kinase; Proto-Oncogene Proteins c-akt; Rats, Wistar; Sitosterols

2020
Bioassay-based Corchorus capsularis L. leaf-derived β-sitosterol exerts antileishmanial effects against Leishmania donovani by targeting trypanothione reductase.
    Scientific reports, 2020, 11-24, Volume: 10, Issue:1

    Leishmaniasis, a major neglected tropical disease, affects millions of individuals worldwide. Among the various clinical forms, visceral leishmaniasis (VL) is the deadliest. Current antileishmanial drugs exhibit toxicity- and resistance-related issues. Therefore, advanced chemotherapeutic alternatives are in demand, and currently, plant sources are considered preferable choices. Our previous report has shown that the chloroform extract of Corchorus capsularis L. leaves exhibits a significant effect against Leishmania donovani promastigotes. In the current study, bioassay-guided fractionation results for Corchorus capsularis L. leaf-derived β-sitosterol (β-sitosterol

    Topics: Antiprotozoal Agents; Binding Sites; Chemical Fractionation; Corchorus; Leishmania donovani; Mitochondrial Membranes; Models, Molecular; Molecular Docking Simulation; NADH, NADPH Oxidoreductases; Plant Extracts; Plant Leaves; Protein Conformation; Protozoan Proteins; Reactive Oxygen Species; Sitosterols

2020
A Network Pharmacology-Based Strategy for Unveiling the Mechanisms of Tripterygium Wilfordii Hook F against Diabetic Kidney Disease.
    Journal of diabetes research, 2020, Volume: 2020

    Diabetic kidney disease (DKD) poses a major public-health burden globally. Tripterygium wilfordii Hook F (TwHF) is a widely employed herbal medicine in decreasing albuminuria among diabetic patients. However, a holistic network pharmacology strategy to investigate the active components and therapeutic mechanism underlying DKD is still unavailable.. We collected TwHF ingredients and their targets by traditional Chinese Medicine databases (TCMSP). Then, we obtained DKD targets from GeneCards and OMIM and collected and analyzed TwHF-DKD common targets using the STRING database. Protein-protein interaction (PPI) network was established by Cytoscape and analyzed by MCODE plugin to get clusters. In addition, the cytoHubba software was used to identify hub genes. Finally, all the targets of clusters were subjected for Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment analyses via DAVID.. A total of 51 active ingredients in TwHF were identified and hit by 88 potential targets related to DKD. Compounds correspond to more targets include kaempferol, beta-sitosterol, stigmasterol, and Triptoditerpenic acid B, which appeared to be high-potential compounds. Genes with higher degree including VEGFA, PTGS2, JUN, MAPK8, and HSP90AA1 are hub genes of TwHF against DKD, which are involved in inflammation, insulin resistance, and lipid homeostasis. Kaempferol and VEGFA were represented as the uppermost active ingredient and core gene of TwHF in treating DKD, respectively. DAVID results indicated that TwHF may play a role in treating DKD through AGE-RAGE signaling pathway, IL-17 signaling pathway, TNF signaling pathway, insulin resistance, and calcium signaling pathway (. Kaempferol and VEGFA were represented as the uppermost active ingredient and core gene of TwHF in treating DKD, respectively. The key mechanisms of TwHF against DKD might be involved in the reduction of renal inflammation by downregulating VEGFA.

    Topics: Cyclooxygenase 2; Databases, Genetic; Databases, Pharmaceutical; Diabetic Nephropathies; Diterpenes; Drugs, Chinese Herbal; Gene Ontology; HSP90 Heat-Shock Proteins; Humans; Kaempferols; Kidney; Mitogen-Activated Protein Kinase 8; Phenanthrenes; Phytotherapy; Protein Interaction Maps; Proto-Oncogene Proteins c-jun; Sitosterols; Stigmasterol; Tripterygium; Vascular Endothelial Growth Factor A

2020
Regulatory Mechanisms of Coicis Semen on Bionetwork of Liver Cancer Based on Network Pharmacology.
    BioMed research international, 2020, Volume: 2020

    At present, there is an increasing incidence and mortality of liver cancer. Despite surgery and chemoradiotherapy, there is a lack of effective oral medications with low side effects. In East Asia, Coicis Semen (CS) is used as both food and natural medicine and has a significant impact on the treatment of liver cancer. However, due to its multicomponent and multitarget characteristics, the mechanisms of CS against liver cancer remain unclear. This study collected CS compounds and target proteins in SymMap, then cross-matched with the liver cancer targets in the CTD database to construct an interaction network of CS-liver cancer proteins, and visualized by Cytoscape software. DAVID database was used to perform pathway enrichment analysis to find target proteins in core pathways and the related small molecules in CS. The results showed that a total of 103 common genes shared by CS and liver cancer were obtained, which were enriched for precancerous lesion pathways such as hepatitis B and fatty liver and biological signaling pathways such as HIF-1 and TNF. The combination of sitosterol and CASP3 in CS, acting on "pathways in cancer" and restoring normal cell apoptosis, could be the core mechanisms of CS in the treatment of liver cancer. Based on the system biology analysis, it is speculated that CS may not only participate in multiple mechanisms of action to treat liver cancer synergistically but may also be involved in factors that reduce the incidence of liver cancer.

    Topics: Carcinoma, Hepatocellular; Caspase 3; Coix; Gene Ontology; Humans; Liver Neoplasms; Sitosterols; Small Molecule Libraries; Sorafenib

2020
Network Pharmacology Approach to Uncover the Mechanism Governing the Effect of Simiao Powder on Knee Osteoarthritis.
    BioMed research international, 2020, Volume: 2020

    To explore the molecular mechanism of Simiao powder in the treatment of knee osteoarthritis.. Based on oral bioavailability and drug-likeness, the main active components of Simiao powder were screened using the Traditional Chinese Medicine Systems Pharmacology Database and Analysis Platform (TCMSP). GeneCard, OMIM, DisGeNET, DrugBank, PharmGkb, and the Therapeutic Target Database were used to establish target databases for knee osteoarthritis. Cytoscape software was used to construct a visual interactive network diagram of "active ingredient - action target - disease." The STRING database was used to construct a protein interaction network and analyze related protein interaction relationships. Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway and Gene Ontology (GO) biological process enrichment analysis were performed on the core targets. Additionally, Discovery Studio software was used for molecular docking verification of active pharmaceutical ingredients and disease targets.. Thirty-seven active components of Simiao powder were screened, including 106 common targets. The results of network analysis showed that the targets were mainly involved in regulating biological processes such as cell metabolism and apoptosis. Simiao powder components were predicted to exert their therapeutic effect on the AGE-RAGE signaling pathway in diabetic complications, IL-17 signaling pathway, TNF signaling pathway, Toll-like receptor signaling pathway, and HIF-1 signaling pathway. The molecular docking results showed that the active components of Simiao powder had a good match with the targets of IL1B, MMP9, CXCL8, MAPK8, JUN, IL6, MAPK1, EGF, VEGFA, AKT1, and PTGS2.. Simiao powder has multisystem, multicomponent, and multitarget characteristics in treating knee osteoarthritis. Its possible mechanism of action includes inhibiting the inflammatory response, regulating immune function, and resisting oxidative stress to control the occurrence and development of the disease. Quercetin, wogonin, kaempferol, beta-sitosterol, and other active ingredients may be the material basis for the treatment of knee osteoarthritis.

    Topics: Administration, Oral; Apoptosis; Drugs, Chinese Herbal; Flavanones; Humans; Inflammation; Kaempferols; Medicine, Chinese Traditional; Molecular Docking Simulation; Osteoarthritis, Knee; Oxidative Stress; Powders; Quercetin; Reproducibility of Results; Signal Transduction; Sitosterols; Software

2020
A new antimicrobial sesquiterpene isolated from endophytic fungus
    Natural product research, 2020, Volume: 34, Issue:10

    Chemical examination of Chinese mangrove

    Topics: Anti-Bacterial Agents; Anti-Infective Agents; Ascomycota; Humans; Molecular Structure; Rhizophoraceae; Sesquiterpenes; Sitosterols; Spectrum Analysis; Stigmasterol

2020
β-Sitosterol Attenuates the Intracranial Aneurysm Growth by Suppressing TNF-α-Mediated Mechanism.
    Pharmacology, 2019, Volume: 104, Issue:5-6

    Onset of inflammation associated with increased extracellular matrix degradation of vascular walls in the neuronal area is the pathophysiology of cerebral aneurysms. It has been documented well that β-sitosterol has protective effects on various brain-related diseases independent of their lipid-lowering effects; the current work was framed to examine the effect of β-sitosterol on CA progression.. To study whether β-sitosterol has a suppressive effect on the growth of CA, β-sitosterol administration started prior to aneurysm induction. CA was induced in Wistar male rats with or without oral administration of β-sitosterol. The expression of chemokines and inflammatory cytokines, tumor necrosis factor-α (TNF-α), interleukin (IL)-8, IL-1β, IL-17, IL-6, matrix metalloproteinases (MMP)-2 and -9, was elucidated by ELISA and RT-PCR.. Rats treated with β-sitosterol exhibited a significant reduction in aneurysmal size compared with control rats. In addition, β-sitosterol administration reduced the expression of chemokines and inflammatory cytokines, while gelatin zymography data revealed declined activity of MMP-2 and -9 in aneurismal walls. Furthermore, the levels of cytokines were significantly reduced in β-sitosterol-administered rats compared to CA rats.. Treatment with β-sitosterol suppresses the development of CA by inhibiting inflammatory reactions including TNF-α and thus β-sitosterol can be a suggestive candidate for the prevention of CA treatment and progression.

    Topics: Animals; Anti-Inflammatory Agents; Intracranial Aneurysm; Male; Rats, Wistar; Sitosterols; Tumor Necrosis Factor-alpha

2019
Metabolomics and physiological analyses reveal β-sitosterol as an important plant growth regulator inducing tolerance to water stress in white clover.
    Planta, 2019, Volume: 250, Issue:6

    β-sitosterol influences amino acids, carbohydrates, organic acids, and other metabolite metabolism and homeostasis largely contributing to better tolerance to water stress in white clover. β-sitosterol (BS) could act as an important plant growth regulator when plants are subjected to harsh environmental conditions. Objective of this study was to examine effects of BS on growth and water stress tolerance in white clover based on physiological responses and metabolomics. White clover was pretreated with or without BS and then subjected to water stress for 7 days in controlled growth chambers. Physiological analysis demonstrated that exogenous application of BS (120 μM) could significantly improve stress tolerance associated with better growth performance and photosynthesis, higher leaf relative water content, and less oxidative damage in white clover in response to water stress. Metabolic profiling identified 78 core metabolites involved in amino acids, organic acids, sugars, sugar alcohols, and other metabolites in leaves of white clover. For sugars and sugar alcohol metabolism, the BS treatment enhanced the accumulation of fructose, glucose, maltose, and myo-inositol contributing to better antioxidant capacity, growth maintenance, and osmotic adjustment in white clover under water stress. The application of BS was inclined to convert glutamic acid into proline, 5-oxoproline, and chlorophyll instead of going to pyruvate and alanine; the BS treatment did not significantly affect intermediates of tricarboxylic acid cycle (citrate, aconitate, and malate), but promoted the accumulation of other organic acids including lactic acid, glycolic acid, glyceric acid, shikimic acid, galacturonic acid, and quinic acid in white clover subjected to water stress. In addition, cysteine, an important antioxidant metabolite, was also significantly improved by BS in white clover under water stress. These altered amino acids and organic acids metabolism could play important roles in growth maintenance and modulation of osmotic and redox balance against water stress in white clover. Current findings provide a new insight into BS-induced metabolic homeostasis related to growth and water stress tolerance in plants.

    Topics: Cell Membrane; Dehydration; Gas Chromatography-Mass Spectrometry; Metabolomics; Oxidative Stress; Photosynthesis; Plant Growth Regulators; Sitosterols; Trifolium

2019
Exogenous application of β-sitosterol mediated growth and yield improvement in water-stressed wheat (Triticum aestivum) involves up-regulated antioxidant system.
    Journal of plant research, 2019, Volume: 132, Issue:6

    Water stress reduces crop production significantly, and climate change has further aggravated the problem mainly in arid and semi-arid regions. This was the first study on the possible effects of β-sitosterol application in ameliorating the deleterious changes in wheat induced by water stress under field condition and drip irrigation regimes. A field experiment with the split-plot design was conducted, and wheat plants were foliar sprayed with four β-sitosterol (BBS) concentrations (0, 25, 75, and 100 mg L

    Topics: Antioxidants; Dose-Response Relationship, Drug; Droughts; Protective Agents; Random Allocation; Sitosterols; Triticum; Up-Regulation

2019
Enhancement of Antioxidant Activity in O/W Emulsion and Cholesterol-Reducing Capacity of Epigallocatechin by Derivatization with Representative Phytosterols.
    Journal of agricultural and food chemistry, 2019, Nov-13, Volume: 67, Issue:45

    In this study, derivatization of epigallocatechin (EGC) by representative phytosterols (stigmasterol and β-sitosterol) was performed employing Steglich esterification. The structural identity and purity of epigallocatechin β-sitosterol (ESi) and epigallocatechin stigmasterol (ESt) were confirmed by NMR, FT-IR, and HPLC-MS. Further evaluation of ESi and ESt revealed their extraordinary antioxidant activities in O/W emulsion. Two different radical sources in oil or aqueous phase were applied to explore the antioxidant behavior in O/W emulsion. The mechanism was further investigated by fluorescent microscopy and transmission electron microscopy (TEM). Furthermore, incorporation of EGC with stigmasterol and β-sitosterol notably enhanced the cholesterol-reducing activity. TEM studies suggested the hydrogen bonding of EGC strengthened the aggregation network of ESi and ESt in the bile salt micelle. The exceptional properties of ESi and ESt signified their intriguing utilization in the food industry.

    Topics: Antioxidants; Catechin; Cholesterol; Emulsions; Esterification; Oxidation-Reduction; Phytosterols; Sitosterols; Stigmasterol

2019
A phytosterol-enriched saw palmetto supercritical CO
    BMC complementary and alternative medicine, 2019, Oct-17, Volume: 19, Issue:1

    Benign prostatic hyperplasia (BPH) is a pathological condition affecting older men. BPH complications often lead to deterioration in the quality of life. Serenoa repens (Saw Palmetto) is used for treating lower urinary tract infections in traditional medicine.. This study was performed to compare the efficacy of β-sitosterol enriched saw palmetto oil (VISPO) and conventional saw palmetto oil (SPO) extracted using supercritical fluid extraction, in alleviating the BPH complications using testosterone-induced BPH model rats. The animals received testosterone (5 mg/kg s.c.) with or without SPO and VISPO (200 and 400 mg/kg b.w.) or Finasteride (1 mg/kg b.w.) p.o. for 28 days. At the end of the experiment, overnight fasted animals were euthanized, blood samples collected for serum analysis of testosterone. Prostate tissue histomorphology was examined by hematoxylin and eosin (H&E) staining. Western blot analysis was performed using prostate tissue homogenates.. VISPO exhibited superior efficacy compared to SPO as evident from the significant decrease in prostate weight to body weight ratio, serum testosterone level and increase in growth inhibition of prostate tissue compared to BPH group (p < 0.001). Histological examination of prostate tissue samples showed that VISPO treatment was comparatively better than SPO in improving the hyperplastic patterns. Further, VISPO significantly regulated the expression of inflammatory and apoptotic marker proteins in BPH rats.. Our data provide experimental evidence that β-sitosterol enriched saw palmetto oil could be higher efficacious in treating the BPH complications compared to the conventional saw palmetto oil preparations.

    Topics: Animals; bcl-2-Associated X Protein; Chromatography, Supercritical Fluid; Humans; Male; Phytosterols; Phytotherapy; Plant Extracts; Prostate; Prostatic Hyperplasia; Proto-Oncogene Proteins c-bcl-2; Rats; Rats, Wistar; Serenoa; Sitosterols; Testosterone

2019
Estimating fetal cholesterol synthesis rates by cord blood analysis in intrauterine growth restriction and normally grown fetuses.
    Lipids in health and disease, 2019, Oct-25, Volume: 18, Issue:1

    Cholesterol is an essential component in human development. In fetuses affected by intrauterine growth restriction (IUGR), fetal blood cholesterol levels are low. Whether this is the result of a reduced materno-fetal cholesterol transport, or due to low fetal de novo synthesis rates, remains a matter of debate. By analyzing cholesterol interbolites and plant sterols we aimed at deeper insights into transplacental cholesterol transport and fetal cholesterol handling in IUGR with potential targets for future therapy. We hypothesized that placental insufficiency results in a diminished cholesterol supply to the fetus.. Venous umbilical cord sera were sampled post-partum from fetuses delivered between 24 weeks of gestation and at full term. IUGR fetuses were matched to 49 adequate-for-age delivered preterm and term neonates (CTRL) according to gestational age at delivery. Cholesterol was measured by gas chromatography-flame ionization detection using 5a-cholestane as internal standard. Cholesterol precursors and synthesis markers, such as lanosterol, lathosterol, and desmosterol, the absorption markers, 5α-cholestanol and plant sterols, such as campesterol and sitosterol, as well as enzymatically oxidized cholesterol metabolites (oxysterols), such as 24S- or 27-hydroxycholesterol, were analyzed by gas chromatography-mass spectrometry, using epicoprostanol as internal standard for the non-cholesterol sterols and deuterium labeled oxysterols for 24S- and 27-hydroxycholesterol.. Mean cholesterol levels were 25% lower in IUGR compared with CTRL (p < 0.0001). Lanosterol and lathosterol to cholesterol ratios were similar in IUGR and CTRL. In relation to cholesterol mean, desmosterol, 24S-hydroxycholesterol, and 27-hydroxycholesterol levels were higher by 30.0, 39.1 and 60.7%, respectively, in IUGR compared to CTRL (p < 0.0001). Equally, 5α-cholestanol, campesterol, and β-sitosterol to cholesterol ratios were higher in IUGR than in CTRL (17.2%, p < 0.004; 33.5%, p < 0.002; 29.3%, p < 0.021).. Cholesterol deficiency in IUGR is the result of diminished fetal de novo synthesis rates rather than diminished maternal supply. However, increased oxysterol- and phytosterol to cholesterol ratios suggest a lower sterol elimination rate. This is likely caused by a restricted hepatobiliary function. Understanding the fetal cholesterol metabolism is important, not only for neonatal nutrition, but also for the development of strategies to reduce the known risk of future cardiovascular diseases in the IUGR fetus.

    Topics: Adult; Cholesterol; Female; Fetal Blood; Fetal Growth Retardation; Gas Chromatography-Mass Spectrometry; Humans; Hydroxycholesterols; Infant, Newborn; Phytosterols; Placenta; Pregnancy; Sitosterols

2019
The protective effects of β-sitosterol and vermicularin from Thamnolia vermicularis (Sw.) Ach. against skin aging in vitro.
    Anais da Academia Brasileira de Ciencias, 2019, Volume: 91, Issue:4

    Aged skin, featured with dryness and wrinkles, has received mounting attention due to its adverse influences on beauty. β-Sitosterol and vermicularin are two common active ingredients of Thamnolia vermicularis (Sw.) Ach., a traditional Chinese medicine, of which the anti-aging effect has been discovered. Their protective performance against skin aging was assayed by co-culturing with skin cells in this work. Results showed that β-sitosterol promoted the biosynthesis of hyaluronic acid by increasing the expression of hyaluronic acid synthases in fibroblasts and enhanced the expression of skin barrier functional proteins including aquaporin 3, loricrin, filaggrin and involucrin in keratinocytes, which conduced to the moisture retention within skin. Moreover, vermicularin might function as an anti-wrinkle agent by preventing the loss of collagen type I. Specifically, vermicularin reduced the amount of reactive oxygen species within hydrogen-peroxide-induced fibroblasts; together with suppressing the activation of mitogen-activated protein kinases, it could inhibit the production of matrix metalloproteinases-1. The present research will contribute to the development of the compounds as anti-aging ingredients for future applications in cosmetic formulations and functional food as well as promote further studies of raw materials containing alike compounds.

    Topics: Cell Line; Fibroblasts; Filaggrin Proteins; Humans; Keratinocytes; Plant Extracts; Protective Agents; Sitosterols; Skin Aging

2019
Assessment of the hepatoprotective effect of developed lipid-polymer hybrid nanoparticles (LPHNPs) encapsulating naturally extracted β-Sitosterol against CCl
    Scientific reports, 2019, 12-24, Volume: 9, Issue:1

    Topics: Animals; Antioxidants; Carbon Tetrachloride Poisoning; Centaurea; Lipids; Liver; Male; Nanoparticles; Polyesters; Polyethylene Glycols; Rats; Sitosterols

2019
Chemical constituents and biological activities of
    Natural product research, 2019, Volume: 33, Issue:11

    Three new compounds (

    Topics: Animals; Anti-Infective Agents; Drug Evaluation, Preclinical; Insecticides; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Moths; Plant Extracts; Sitosterols; Viburnum

2019
Synthesis, characterization, and biological evaluations of some steryl 2-methoxybenzoates as anticancer agents.
    Natural product research, 2019, Volume: 33, Issue:8

    Using cholesterol, stigmasterol and sitosterol as starting materials, a series of 7-subsitituted-ster-3-yl 2-methoxybenzoate analogs were prepared through reacting with 2-methoxybenzoyl chloride and introducing some function groups, such as carbonyl, hydroxyl and various thiosemicarbazones, at 7-position of steroidal nucleus. The structures of these new compounds were characterized by IR, NMR and HRMS. Their antiproliferative activities were evaluated by using several types of cancer cells. Interestingly, the compounds displayed potent antiproliferative activity against CNE-2 (nasopharyngeal carcinoma cell lines), BEL-7402 (human liver cancer cell lines) and HepG2 (human liver cancer cell lines), suggesting that they have potential to be drug candidates for cancer treatment.

    Topics: Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Cholesterol; Drug Screening Assays, Antitumor; Hep G2 Cells; Humans; Hydroxybenzoate Ethers; Magnetic Resonance Spectroscopy; Salicylates; Sitosterols; Steroids; Stigmasterol; Structure-Activity Relationship; Thiosemicarbazones

2019
Apoptotic effect of a phytosterol-ingredient and its main phytosterol (β-sitosterol) in human cancer cell lines.
    International journal of food sciences and nutrition, 2019, Volume: 70, Issue:3

    Dietary interventions may effectively control cancer development, with phytosterols (PS) being a class of cancer chemopreventive dietary phytochemicals. The present study, for the first time, evaluates the antiproliferative effects of a PS-ingredient used for the enrichment of several foods and its main PS, β-sitosterol, at physiological serum levels, in the most prevalent cancer cells in women (breast (MCF-7), colon (HCT116) and cervical (HeLa)). In all three cell lines, these compounds induced significant cell viability reduction without a clear time- and dose-dependent response. Moreover, all treatments produced apoptotic cell death with the induction of DNA fragmentation through the appearance of a sub-G1 cell population. Thus, the use of PS as functional ingredients in the development of PS-enriched foods could exert a potential preventive effect against human breast, colon and cervical cancer, although further in vivo studies are required to confirm our preclinical findings.

    Topics: Apoptosis; Cell Proliferation; HCT116 Cells; HeLa Cells; Humans; MCF-7 Cells; Phytosterols; Sitosterols

2019
Phytosterols in supplements containing
    Natural product research, 2019, Volume: 33, Issue:15

    Topics: Cholesterol; Chromatography, Gas; Dietary Supplements; Phytosterols; Serenoa; Sitosterols; Stigmasterol

2019
Integration of (+)-catechin and β-sitosterol to achieve excellent radical-scavenging activity in emulsions.
    Food chemistry, 2019, Jan-30, Volume: 272

    Novel amphiphilic antioxidant, (+)-catechin-β-sitosterol (CS), was designed and successfully prepared with integration of (+)-catechin and β-sitosterol through the linkage of succinic acid. Sequential esterification was carried out to connect (+)-catechin and β-sitosterol. The identity of CS was confirmed by NMR, IR and MS spectroscopies. DSC analysis revealed that ΔH of CS was much lower than those of (+)-catechin and β-sitosterol, indicating ameliorated crystallinity. The logP measurement demonstrated significantly increased lipophilicity. Then excellent antioxidant activities of the novel antioxidant in typical polyunsaturated lipid O/W and W/O emulsions were unveiled applying β-sitosterol bleaching assay and 5-dodecanoylaminofluorescein (DAF) fluorescent probe method. The antioxidative behavior of CS in emulsion was beyond the polar paradox hypothesis and could be rationalized by effective accumulation at oil/water interface owing to its amphiphilic nature. This study offers a promising solution for development of naturally derived amphiphilic antioxidants for lipid-based systems.

    Topics: Calorimetry, Differential Scanning; Catechin; Emulsions; Free Radical Scavengers; Lipid Peroxidation; Lipids; Sitosterols; Stereoisomerism; Thermodynamics

2019
Chemical comparison of Prunus africana bark and pygeum products marketed for prostate health.
    Journal of pharmaceutical and biomedical analysis, 2019, Jan-30, Volume: 163

    The bark of Prunus africana may contain atranorin, atraric acid, beta-sitosterol and its esters, ferulic acid and its esters, and N-butylbenzene sulfonamide, compounds that have been shown to improve the conditions of benign prostatic hyperplasia, enlarged prostate. An analytical scheme, involving liquid-solid extractions, saponifications, and LC-APCI-MS (triple quadrupole) analysis, was developed, optimized, and validated to determine the compounds at μg/g levels. Limits of quantification were in the low ng/mL range except for beta-sitosterol. All of the compounds plus two internal standards eluted in under 10 min on a phenyl-hexyl column with gradient elution involving water-methanol and acetonitrile. The mass fraction of the compounds in Prunus africana bark (four samples) and commercial pygeum products (seven samples), derived from bark, were compared. Bark and pygeum were similar in their content of atranorin and atraric acid, found at low μg/g levels, and in the fact that ferulic acid was almost totally (> 90%) in the form of esters. In contrast, the total amount of ferulic acid was on average four times higher in bark (450 μg/g) than in pygeum while the opposite was true for total beta-sitosterol. Some pygeum samples had levels of total beta-sitosterol above 10,000 μg/g while the compound in bark was relatively invariant at about 680 μg/g. The fraction of free beta-sitosterol varied significantly between bark (33%) and pygeum (nearly all). In pygeum, the measured total beta-sitosterol concentration generally followed the labeled values for phytosterol content. No N-butylbenzene sulfonamide was found in any of the bark and pygeum samples.

    Topics: Chemical Fractionation; Chromatography, High Pressure Liquid; Drug Contamination; Humans; Hydroxybenzoates; Male; Mass Spectrometry; Plant Bark; Plant Extracts; Prostatic Hyperplasia; Prunus africana; Sitosterols; Sulfonamides

2019
Sewage contamination of Amazon streams crossing Manaus (Brazil) by sterol biomarkers.
    Environmental pollution (Barking, Essex : 1987), 2019, Volume: 244

    Sewage pollution is a principal factor of decreasing water quality, although it has not been considered a real impact in Amazonia that is still considered a pristine environment around the world. Thus, this study aimed to assess the levels of sewage contamination in sediments from three streams crossing Manaus - a Brazilian city of 2,403,796 inhabitants in the heart of the Amazon rain forest. Cholesterol, cholestanol, brassicasterol, ergosterol, stigmasterol, β-sitosterol, campesterol, stigmastanol, coprostanol, and epicoprostanol levels were determined by liquid chromatography tandem mass spectrometry (LC-MS/MS). The fecal indicator, coprostanol, was found in high concentrations (509-12 830 ng g

    Topics: Biomarkers; Brazil; Cholestadienols; Cholestanol; Cholestanols; Cholesterol; Chromatography, Liquid; Drug Contamination; Environmental Monitoring; Feces; Geologic Sediments; Phytosterols; Rivers; Sewage; Sitosterols; Sterols; Tandem Mass Spectrometry; Water Pollutants; Water Pollution; Water Quality

2019
Control of β-sitosterol biosynthesis under light and watering in desert plant Calotropis procera.
    Steroids, 2019, Volume: 141

    Most scientific studies on Calotropis procera refer to the plant as an important source of pharmaceutical compounds and its valuable benefits in medicine. One of the most important substances in this plant is the potential immunostimulant β-sitosterol (BS) that acts in improving human health. This study focused on the effects of lighting before and after irrigation on the BS accumulation pathway namely steroid biosynthesis. Studying the enzymes in BS biosynthetic pathway indicated the upregulation at dawn and predusk of the SMT2 and SMO2 genes encoding sterol methyltransferase 2 and methylsterol monooxygenase, two key enzymes in BS accumulation in C. procera. The results almost indicated no regulation at the different time points of the CYP710A gene encoding sterol 22-desaturase, an enzyme that acts in depleting β-sitosterol towards the biosynthesis of stigmasterol. RNA-Seq data was validated via quantitative RT-PCR and results were positive. The data of ultra-performance liquid chromatography-tandem mass spectrometry analysis with regard to BS accumulation also aligned with those of RNA-Seq analysis. We focused on the effects of light before and after watering on BS accumulation in C. procera. Our results show that BS accumulation is high at dawn in both dehydrated and well-watered condition. While, the BS was dramatically decrease at midday in well-watered plants. This increase/decrease in BS content is correlated with rates of expression of SMT 2 gene. This gene is a key convertor between the different branches in the cardiac glycoside biosynthesis. Accordingly, it could be suggested that BS (or one of the descendent product) may play an important role in C. procera tolerance to drought/light intensity conditions.

    Topics: Calotropis; Desert Climate; Light; Molecular Structure; Sitosterols; Water

2019
    Natural product research, 2019, Volume: 33, Issue:21

    The phytochemical investigation of both chloroform and ethyl acetate extracts of

    Topics: Asteraceae; Centaurea; Flavonoids; Glucosides; Molecular Structure; Nitriles; Plant Extracts; Sitosterols; Spectrum Analysis

2019
In silico and in vivo analysis to identify the antidiabetic activity of beta sitosterol in adipose tissue of high fat diet and sucrose induced type-2 diabetic experimental rats.
    Toxicology mechanisms and methods, 2019, Volume: 29, Issue:4

    Adipose tissue is the primary site of storage for excess energy as triglyceride and it helps in synthesizing a number of biologically active compounds that regulate metabolic homeostasis. Consumption of high dietary fat increases stored fat mass and is considered as a main risk factor for metabolic diseases. Beta-sitosterol (β-sitosterol) is a plant sterol. It has the similar chemical structure like cholesterol. Clinical and experimental studies have shown that β-sitosterol has anti-diabetic, hypolipidemic, anti-cancer, anti-arthritic, and hepatoprotective role. However, effect of β-sitosterol on insulin signaling molecules and glucose oxidation has not been explored. Hence in the present study we aimed to discover the protective role of β-sitosterol on the expression of insulin signaling molecules in the adipose tissue of high-fat diet and sucrose-induced type-2 diabetic experimental rats. Effect dose of β-sitosterol (20 mg/kg b.wt, orally for 30 days) was given to high fat diet and sucrose-induced type-2 diabetic rats to study its anti-diabetic activity. Results of the study showed that the treatment with β-sitosterol to diabetes-induced rats normalized the altered levels of blood glucose, serum insulin and testosterone, lipid profile, oxidative stress markers, antioxidant enzymes, insulin receptor (IR), and glucose transporter 4 (GLUT4) proteins. Our present findings indicate that β-sitosterol improves glycemic control through activation of IR and GLUT4 in the adipose tissue of high fat and sucrose-induced type-2 diabetic rats. Insilico analysis also coincides with invivo results. Hence it is very clear that β-sitosterol can act as potent antidiabetic agent.

    Topics: Adipose Tissue; Animals; Blood Glucose; Computer Simulation; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 2; Diet, High-Fat; Glucose Transporter Type 4; Hypoglycemic Agents; Insulin; Lipid Metabolism; Male; Molecular Docking Simulation; Rats, Wistar; Receptor, Insulin; Signal Transduction; Sitosterols

2019
β-Sitosterol improves experimental colitis in mice with a target against pathogenic bacteria.
    Journal of cellular biochemistry, 2019, Volume: 120, Issue:4

    In this article, we aim to examine the novel effects of β-sitosterol on murine experimental colitis. β-Sitosterol significantly reduces the weight loss, colon length, and alleviated microscopic appearances of colitis induced by dextran sulfate sodium. This compound also decreases the levels of TNF-α, IL-6, and IL-1β in intestinal tissue of mice with experimental colitis in a concentration-dependent manner. β-Sitosterol treatment to intestinal epithelial cells significantly increases expression of antimicrobial peptides and reduces survival of intracellular Salmonella typhimurium. These results showed the multiple effects of β-sitosterol against pathogenic bacteria for a novel approach to the treatment of colonic inflammation.

    Topics: Animals; Colitis; Dextran Sulfate; Disease Models, Animal; Hypolipidemic Agents; Inflammation; Intestinal Mucosa; Male; Mice; Mice, Inbred C57BL; Salmonella typhimurium; Sitosterols; Typhoid Fever

2019
A novel poly (NMA-co-DEA-co-EDMA) monolithic column as a sorbent for online solid-phase extraction and its application in the determination of β-sitosterol in plant oil samples.
    Food chemistry, 2019, Apr-25, Volume: 278

    A novel monolithic column was prepared by in-situ free radical polymerization using N-methylolacrylamide (NMA) and N,N-diethylacrylamide (DEA) as co-monomers. The monolith was characterized by scanning electron microscopy (SEM) and its nitrogen adsorption-desorption isotherm, and it was used as a solid phase extraction (SPE) absorbent for the online enrichment of β-sitosterol by high performance liquid chromatography. The optimized method had good linearity, and the linear regression coefficient was 0.998. The limit of detection (LOD) and the limit of quantification (LOQ) were 0.006 mg/mL and 0.02 mg/mL, respectively. The interday and intraday accuracies were less than 7.28%. The spiked recoveries of β-sitosterol in the six plant oil were 90.96-103.56%. The maximum amount of β-sitosterol adsorbed on the monolithic column was 12.69 mg/g, and the enrichment factor of β-sitosterol was 78. The results showed that the monolith could be used as an online SPE absorbent for the determination of β-sitosterol in plant oil samples.

    Topics: Adsorption; Chromatography, High Pressure Liquid; Limit of Detection; Plant Oils; Polymers; Reproducibility of Results; Sitosterols; Solid Phase Extraction

2019
Isolation and in silico prediction of potential drug-like compounds from Anethum sowa L. root extracts targeted towards cancer therapy.
    Computational biology and chemistry, 2019, Volume: 78

    Anethum sowa L. has been used as a spice herb in the Asian and European culinary systems to add flavour and taste. The studied plant has diverse folkloric medicinal value. Present study was designed to isolate phytochemicals from the hexane, chloroform and ethyl acetate extracts of the roots by various chromatographic techniques. Based on spectral analysis (IR, LC-MS, NMR) the isolated compounds were identified as physcione (1), β-sitosterol (2), stigmasterol (3), 2-oxo-3-propyl-2H-chromene-7-carboxylic acid (4), bergapten (5), 3-ethyl-7-hydroxy-2H-chromen-2-one (6) and graveolone (7). The mentioned compounds have been isolated for the first time from the roots part of the plant. Based on extensive literature review, physcione and bergapten were inferred to exhibit crucial bioactivities including inhibitory efficacy against various forms of cancer. Accordingly, in the present research approach molecular docking investigations of the isolated phytochemicals have been robustly executed with different oncogenes that have been reported to be actively involved in various forms of carcinoma. In silico investigations encompassing molecular docking analysis and drug-likeness profiling was executed to estimate the potential therapeutic tendencies of the phytochemicals targeted towards effective cancer therapy. Current investigation offers meaningful know-how pertaining to potential anticancer activities of the phytochemicals extracted from the roots of Anethum sowa L. and might open up new revenues towards effective drug development against cancer.

    Topics: 5-Methoxypsoralen; Antineoplastic Agents, Phytogenic; Apiaceae; Benzopyrans; Carboxylic Acids; Cell Proliferation; Drug Screening Assays, Antitumor; Humans; Methoxsalen; Molecular Docking Simulation; Plant Extracts; Plant Roots; Sitosterols; Stigmasterol

2019
Potent in Vitro α-Glucosidase Inhibition of Secondary Metabolites Derived from
    Molecules (Basel, Switzerland), 2019, Jan-24, Volume: 24, Issue:3

    α-glucosidase is responsible for the hydrolysis of complex carbohydrates into simple absorbable glucose and causes postprandial hyperglycemia. α-glucosidase inhibition is thus the ideal target to prevent postprandial hyperglycemia. The present study was therefore designed to analyze the effects of various compounds isolated from

    Topics: Acarbose; alpha-Glucosidases; Dryopteris; Galactose; Glycoside Hydrolase Inhibitors; Molecular Docking Simulation; Molecular Structure; Phytochemicals; Protein Binding; Quercetin; Secondary Metabolism; Sitosterols; Structure-Activity Relationship

2019
Anti-Diabetic Effect of a Flavonoid and Sitosterol - Rich Aqueous Extract of
    Endocrine, metabolic & immune disorders drug targets, 2019, Volume: 19, Issue:8

    Traditionally prepared infusions and decoctions are commonly used in the management of diabetes mellitus, in southern Nigeria; one of such is the aqueous extract of the sclerotia of Pleurotus tuberregium ("usu" milk). In this study, the effects of the extract on the body weights, tissue/ organ weights, fasting blood glucose, blood/plasma lipid profiles and atherogenic indices were investigated in normal and alloxan-induced diabetic rabbits.. Diabetes mellitus was induced by the injection of alloxan (120 mg/kg body weight) via the marginal ear vein. The extract was administered orally at 100, 200 and 300 mg/kg to normal and diabetic rabbits; while metformin was administered at 50 mg/kg. The crude extract was analyzed by gas chromatography, coupled to flame ionization detector.. Thirty-one known flavonoids were detected, consisting mainly of isoquercetin (28.5%), luteolin (24.3%), quercetin (18.8%) and kaempferol (11.3%). Sitosterol (82.0%) and stigmasterol (12.5%) were the most abundant of the seven phytosterols detected. Compared to the diabetic control, the treatment significantly (p<0.05) lowered the weights of the kidney and liver, as well as the levels of blood glucose and triglyceride, plasma VLDL, LDL and non-HDL cholesterol, atherogenic index of plasma, cardiac risk ratio, atherogenic coefficient and Castelli's risk index II. It, however, significantly (p<0.05) increased plasma HDL cholesterol, without significantly affecting blood total cholesterol levels.. This study showed that the extract was hypoglycemic, and improved lipid profile and atherogenic indices, thus highlighting its cardioprotective potential, thereby supporting its use in the management of diabetes mellitus.

    Topics: Alloxan; Animals; Biomarkers; Blood Glucose; Diabetes Mellitus, Experimental; Fasting; Flavonoids; Hypoglycemic Agents; Hypolipidemic Agents; Lipids; Plant Extracts; Pleurotus; Rabbits; Sitosterols

2019
Phytosterol containing diet increases plasma and whole body concentration of phytosterols in apoE-KO but not in LDLR-KO mice.
    Journal of bioenergetics and biomembranes, 2019, Volume: 51, Issue:2

    Phytosterol metabolism is unknown in the hypercholesterolemia of genetic origin. We investigated the metabolism of phytosterols in a cholesterol-free, phytosterol-containing standard diet in hypercholesterolemic mice knockouts for low density lipoprotein receptor (LDLR) and apolipoprotein E (apoE) mice compared to wild-type mice (controls). Phytosterols were measured in mice tissues by GCMS. ApoE-KO mice absorbed less phytosterols than LDLR-KO and the latter absorbed less phytosterols than control mice, because the intestinal campesterol content was low in both KO mice, and sitosterol was low in the intestine in apoE-KO mice as compared to LDLR-KO mice. Although the diet contained nine times more sitosterol than campesterol, the concentration of sitosterol was lower than that of campesterol in plasma in LDLR-KO, and in the liver in controls and in LDLR-KO, but only in apoE-KO. On the other hand, in the intestine sitosterol was higher than campesterol in controls, and in LDLR-KO but with a tendency only in apoE-KO. Because of the high dietary supply of sitosterol, sitosterol was better taken up by the intestine than campesterol, but the amount of sitosterol was lower than that of campesterol in the liver, while in the whole body the amounts of these phytosterols do not differ from each other. Therefore, via intestinal lymph less sitosterol than campesterol was transferred to the body. However, as compared to controls, in apoE-KO mice, but not in LDLR-KO mice, the increase in campesterol and sitosterol in plasma and in the whole body indicating that apoE-KO mice have a marked defect in the elimination of both phytosterols from the body.

    Topics: Animal Feed; Animals; Cholesterol; Liver; Mice; Mice, Knockout, ApoE; Phytosterols; Receptors, LDL; Sitosterols; Species Specificity

2019
A Multiplex Phytosterol Assay Utilizing Gas Chromatography-Mass Spectrometry for Diagnosis of Inherited Lipid Storage Disorders.
    Annals of laboratory medicine, 2019, Volume: 39, Issue:4

    Topics: Cholestanol; Cholesterol; Gas Chromatography-Mass Spectrometry; Humans; Hypercholesterolemia; Intestinal Diseases; Limit of Detection; Lipid Metabolism, Inborn Errors; Phytosterols; Reference Standards; Sitosterols; Xanthomatosis, Cerebrotendinous

2019
Enhancement of Galloylation Efficacy of Stigmasterol and β-Sitosterol Followed by Evaluation of Cholesterol-Reducing Activity.
    Journal of agricultural and food chemistry, 2019, Mar-20, Volume: 67, Issue:11

    In this study, incorporation of gallic acid into typical phytosterols (β-sitosterol and stigmasterol) through Steglich esterification was optimized employing the protection and deprotection strategy. A novel mechanism leading to side esterification was discovered. Complication of the phenolic hydroxyl groups and side reactions were successfully reduced under the optimized conditions. The structural identity and purity of galloyl stigmasterol and galloyl β-sitosterol were confirmed by NMR, FT-IR, and HPLC-MS. Evaluation of galloyl β-sitosterol and galloyl stigmasterol revealed their excellent antioxidant and cholesterol-reducing activities. Significant enhancement of cholesterol-reducing activity by galloylation was unveiled especially for β-sitosterol. Galloyl β-sitosterol had slightly better antioxidant activity at ambient temperature and better cholesterol-reducing activity. Molecular modeling suggested that a subtle difference of galloyl β-sitosterol and galloyl stigmasterol in activities could be attributed to variation of molecular rigidity and conformation. The excellent properties of galloyl β-sitosterol and galloyl stigmasterol suggested their great potential application in the food industry.

    Topics: Antioxidants; Cholesterol; Chromatography, High Pressure Liquid; Esterification; Mass Spectrometry; Sitosterols; Spectroscopy, Fourier Transform Infrared; Stigmasterol

2019
Toward a Scientific Nutritional Supplement Combination for Prostatism and Erectile Dysfunction I: From Known Pharmacology to Clinical Testing.
    Journal of medicinal food, 2019, Volume: 22, Issue:5

    Prostatism and erectile dysfunction (ED) are highly prevalent and closely comorbid. Prescription treatments are limitingly expensive but robust in mechanisms of action (MoA). Nutritional supplements (NS) are low-cost but inadequately supported by evidence. Do any NS use robust MoA? Could their efficacy be amplified via dosing, concentration of active principles, and/or use in combination? The goal is to develop an effective NS for prostatism and ED using the MoA of prescription treatments. Literature reviews were conducted on dietary supplements for prostatism or ED and MoA of relevant drugs. The most promising NS employing these MoA were chosen. A pilot study of a prototype combination was conducted. A protocol was created for an adequate dose-response trial to test the NS combination in men with ED and prostatism. The main measures were response rates, International Prostate Symptom Score, and International Index of Erectile Function. For drugs, the MoAs best proven for prostatism and ED were nitric oxide augmentation, mild androgen inhibition, and anti-inflammatory effects. The following NS best simulate these MoA and are best supported for efficacy; for prostatism: beta sitosterol; for ED: panax ginseng, arginine, and citrulline. Pilot clinical data provided support. A plan for a formal dose-response clinical trial was approved by a central institutional review board. NS using effective MoA might suffice for prostatism and ED. Pilot testing of a combination NS with the best-supported MoA supported further development. A dose-response trial should be conducted using adequate doses of L-citrulline, beta-sitosterol, ginseng, and vitamin D3.

    Topics: Arginine; Cholecalciferol; Citrulline; Clinical Trials as Topic; Dietary Supplements; Erectile Dysfunction; Humans; Male; Meta-Analysis as Topic; Middle Aged; Panax; Pilot Projects; Plant Extracts; Prostatism; Sitosterols; Urination

2019
New triterpenic acids produced in callus culture from fruit pulp of Acca sellowiana (O. Berg) Burret.
    Food research international (Ottawa, Ont.), 2019, Volume: 119

    The aim of this work was the study of the best conditions for obtaining a callus culture from the pulp of Acca sellowiana, and to perform a quali-quantitative analysis of the secondary metabolites yielded by the in vitro callus culture. To this end, callus was induced on both Murashige and Skoog and Gamborg B5 media containing various combinations of growth regulators. Three previously undescribed ursane-type triterpenoids, 2α,3β,6α,23-tetrahydroxy-18α,19α-urs-20-en-28-oic acid, 2α,3β,23-trihydroxy-18α,19α-urs-20-en-28-oic acid and 2α,3β,6β,23-tetrahydroxy-18α,19α-urs-20-en-28-oic acid were isolated from the methanolic extract of A. sellowiana culture and characterized by 1D and 2D NMR experiments. Moreover, the quali-quantitative analysis (ESI-MS

    Topics: Fruit; Gas Chromatography-Mass Spectrometry; Myrtaceae; Oleanolic Acid; Phlorhizin; Phytochemicals; Plant Extracts; Secondary Metabolism; Sitosterols; Triterpenes; Ursolic Acid

2019
Insights in cyanobacteria lipidomics: A sterols characterization from Phormidium autumnale biomass in heterotrophic cultivation.
    Food research international (Ottawa, Ont.), 2019, Volume: 119

    Sterol profiles were obtained from cyanobacteria Phormidium autumnale, cultivated in a heterotrophic system using three distinct sources of carbon: glucose, sucrose, and agroindustrial slaughterhouse wastewater. A simultaneous saponification-extraction ultrasound-assisted method was performed to determine sterol and other non-saponified compounds in the dry biomasses. A total of 24 compounds were observed in the biomasses, including hope-22,29-en-3-one, squalene, and 22 other sterols. Using wastewater as a carbon source, the microalgae biomass produced a diversity of sterols such as stigmasterol (455.3 μg g

    Topics: Biomass; Carbon; Culture Media; Cyanobacteria; Ergosterol; Lipidomics; Metabolic Networks and Pathways; Microalgae; Phormidium; Sitosterols; Squalene; Sterols; Stigmasterol; Wastewater

2019
β-Sitosterol modulates macrophage polarization and attenuates rheumatoid inflammation in mice.
    Pharmaceutical biology, 2019, Volume: 57, Issue:1

    β-Sitosterol (BS), the primary constituent of plants and vegetables, exhibits multiple biological effects.. This study explores its effect of immune-regulation on macrophages and its potential for rheumatoid arthritis (RA) therapy.. In vitro, bone marrow-derived macrophages (BMDMs) were treated with 5, 25 and 50 μM BS in the M1 or M2 polarization conditions. In vivo, either i.p. injection with 20 or 50 mg/kg BS every 2 d after boost immunization of collagen-induced arthritis (CIA) or adoptive transfer of 2 × 10. The phenotypes and function of BMDMs showed that 5, 25 and 50 μM BS significantly repressed the M1 polarization and augmented M2 polarization dependent upon concentration. The expression of iNOS, IL-1β, CD86 and MHCII in 25 μM BS-treated M1-polarized BMDMs was reduced by 50.2, 47.1, 87.1 and 31.3%, respectively. In contrast, the expression of arginase-1, IL-10, CD163 and CD206 in 25 μM BS-treated M2-polarized BMDMs was increased by 65.6, 107.4, 23.5 and 51.3%, respectively. In CIA mice, either i.p. injection with BS or adoptive transfer of BS-BMDMs could alleviate the symptoms of ankle swelling (vehicle group: 3.13 ± 0.102 mm; 20 mg/kg BS group: 2.64 ± 0.043 mm; 50 mg/kg BS group: 2.36 ± 0.084 mm; BMDMs group: 3.09 ± 0.174 mm; BS-BMDMs group: 2.43 ± 0.042 mm), reduce the levels of collagen-specific antibodies (IgG and IgG1, but not IgG2c, p < 0.05) and inhibit the production of pro-inflammatory cytokines (p < 0.05). Depletion of IL-10 counteracted the effect of BS treatment (α-IL-10 vs. RatIgG1, p < 0.01 on day 16), highlighting the role of IL-10 in the anti-inflammatory response.. These results suggested that BS could modulate the functions of macrophages and might be a promising agent for RA therapy.

    Topics: Animals; Arthritis, Experimental; Bone Marrow Cells; Cell Polarity; Cytokines; Dose-Response Relationship, Drug; Interleukin-10; Macrophage Activation; Macrophages; Male; Mice; Mice, Inbred C57BL; Sitosterols

2019
First international descriptive and interventional survey for cholesterol and non-cholesterol sterol determination by gas- and liquid-chromatography-Urgent need for harmonisation of analytical methods.
    The Journal of steroid biochemistry and molecular biology, 2019, Volume: 190

    Serum concentrations of lathosterol, the plant sterols campesterol and sitosterol and the cholesterol metabolite 5α-cholestanol are widely used as surrogate markers of cholesterol synthesis and absorption, respectively. Increasing numbers of laboratories utilize a broad spectrum of well-established and recently developed methods for the determination of cholesterol and non-cholesterol sterols (NCS). In order to evaluate the quality of these measurements and to identify possible sources of analytical errors our group initiated the first international survey for cholesterol and NCS. The cholesterol and NCS survey was structured as a two-part survey which took place in the years 2013 and 2014. The first survey part was designed as descriptive, providing information about the variation of reported results from different laboratories. A set of two lyophilized pooled sera (A and B) was sent to twenty laboratories specialized in chromatographic lipid analysis. The different sterols were quantified either by gas chromatography-flame ionization detection, gas chromatography- or liquid chromatography-mass selective detection. The participants were requested to determine cholesterol and NCS concentrations in the provided samples as part of their normal laboratory routine. The second part was designed as interventional survey. Twenty-two laboratories agreed to participate and received again two different lyophilized pooled sera (C and D). In contrast to the first international survey, each participant received standard stock solutions with defined concentrations of cholesterol and NCS. The participants were requested to use diluted calibration solutions from the provided standard stock solutions for quantification of cholesterol and NCS. In both surveys, each laboratory used its own internal standard (5α-cholestane, epicoprostanol or deuterium labelled sterols). Main outcome of the survey was, that unacceptably high interlaboratory variations for cholesterol and NCS concentrations are reported, even when the individual laboratories used the same calibration material. We discuss different sources of errors and recommend all laboratories analysing cholesterol and NCS to participate in regular quality control programs.

    Topics: Cholestanol; Cholesterol; Chromatography, Gas; Chromatography, Liquid; Humans; Phytosterols; Sitosterols; Surveys and Questionnaires

2019
A Plant like Cytochrome P450 Subfamily CYP710C1 Gene in Leishmania donovani Encodes Sterol C-22 Desaturase and its Over-expression Leads to Resistance to Amphotericin B.
    PLoS neglected tropical diseases, 2019, Volume: 13, Issue:4

    Leishmania donovani is a protozoan parasite, a primary causative agent of visceral leishmaniasis. Sterol produced via the mevalonate pathway, show differences in composition across biological kingdoms. The specific occurrence of Δ22-unsaturated sterols, containing a double bond at the C-22 position in the side chain occurs in fungi as ergosterol and as stigmasterol in plants. In the present study, we report the identification and functional characterization of a plant-like Cytochrome P450 subfamily CYP710C1 in L. donovani as the Leishmania C-22 desaturase.. In silico analysis predicted the presence of a plant like CYP710C1 gene that encodes a sterol C-22 desaturase, a key enzyme in stigmasterol biosynthesis. The enzymatic function of recombinant CYP710C1 as C-22 desaturase was determined. To further study the physiological role of CYP710C1 in Leishmania, we developed and characterized an overexpressing strain and a gene deletion mutant. C-22 desaturase activity and stigmasterol levels were estimated in the wild-type, overexpressing promastigotes and heterozygous mutants.. We for the first time report the presence of a CYP710C1 gene that encodes a plant like sterol C-22 desaturase leading to stigmasterol biosynthesis in Leishmania. The recombinant CYP710C1 exhibited C-22 desaturase activity by converting β-sitosterol to stigmasterol. Axenic amastigotes showed higher expression of CYP710C1 mRNA, protein and stigmasterol levels compared to the promastigotes. Sterol profiling of CYP710C1 overexpressing L. donovani and heterozygous mutant parasites demonstrated that CYP710C1 was responsible for stigmasterol production. Most importantly, we demonstrate that these CYP710C1 overexpressing promastigotes are resistant to amphotericin B, a drug of choice for use against leishmaniasis. We report that Leishmania sterol biosynthesis pathway has a chimeric organisation with characteristics of both plant and fungal pathways.

    Topics: Amphotericin B; Cytochrome P-450 Enzyme System; Drug Resistance; Genes, Plant; Leishmania donovani; Leishmaniasis, Visceral; Oxidoreductases; Sequence Deletion; Sitosterols; Sterols; Stigmasterol

2019
Epigenetic silencing of genes enhanced by collective role of reactive oxygen species and MAPK signaling downstream ERK/Snail axis: Ectopic application of hydrogen peroxide repress CDH1 gene by enhanced DNA methyltransferase activity in human breast cancer
    Biochimica et biophysica acta. Molecular basis of disease, 2019, 06-01, Volume: 1865, Issue:6

    Topics: Antigens, CD; Antioxidants; Breast Neoplasms; Butadienes; Cadherins; Cell Line; DNA (Cytosine-5-)-Methyltransferase 1; DNA Methylation; Epithelial-Mesenchymal Transition; Extracellular Signal-Regulated MAP Kinases; Female; Gene Expression Regulation, Neoplastic; Gene Silencing; Histone Deacetylase 1; Histones; Humans; Hydrogen Peroxide; Isoenzymes; Kaplan-Meier Estimate; MCF-7 Cells; Nitriles; Pentacyclic Triterpenes; Signal Transduction; Sitosterols; Snail Family Transcription Factors

2019
Inhibition of mitochondrial respiration prevents BRAF-mutant melanoma brain metastasis.
    Acta neuropathologica communications, 2019, 04-10, Volume: 7, Issue:1

    Melanoma patients carry a high risk of developing brain metastases, and improvements in survival are still measured in weeks or months. Durable disease control within the brain is impeded by poor drug penetration across the blood-brain barrier, as well as intrinsic and acquired drug resistance. Augmented mitochondrial respiration is a key resistance mechanism in BRAF-mutant melanomas but, as we show in this study, this dependence on mitochondrial respiration may also be exploited therapeutically. We first used high-throughput pharmacogenomic profiling to identify potentially repurposable compounds against BRAF-mutant melanoma brain metastases. One of the compounds identified was β-sitosterol, a well-tolerated and brain-penetrable phytosterol. Here we show that β-sitosterol attenuates melanoma cell growth in vitro and also inhibits brain metastasis formation in vivo. Functional analyses indicated that the therapeutic potential of β-sitosterol was linked to mitochondrial interference. Mechanistically, β-sitosterol effectively reduced mitochondrial respiratory capacity, mediated by an inhibition of mitochondrial complex I. The net result of this action was increased oxidative stress that led to apoptosis. This effect was only seen in tumor cells, and not in normal cells. Large-scale analyses of human melanoma brain metastases indicated a significant role of mitochondrial complex I compared to brain metastases from other cancers. Finally, we observed completely abrogated BRAF inhibitor resistance when vemurafenib was combined with either β-sitosterol or a functional knockdown of mitochondrial complex I. In conclusion, based on its favorable tolerability, excellent brain bioavailability, and capacity to inhibit mitochondrial respiration, β-sitosterol represents a promising adjuvant to BRAF inhibitor therapy in patients with, or at risk for, melanoma brain metastases.

    Topics: Animals; Apoptosis; Brain Neoplasms; Cell Line, Tumor; Drug Repositioning; Female; Humans; Melanoma; Mice, Transgenic; Mitochondria; Mutation; Oxidative Stress; Proto-Oncogene Proteins B-raf; Sitosterols; Transcriptome

2019
Isolation of Ceramides from Tagetes patula L. Yellow Flowers and Nematicidal Activity of the Fractions and Pure Compounds against Cyst Nematode, Heterodera zeae.
    Chemistry & biodiversity, 2019, Volume: 16, Issue:6

    Investigation of yellow flower extract of Tagetes patula L. led to the identification of an aggregate of five phytoceramides. Among them, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]icosanamide, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]heneicosanamide, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]docosanamide, and (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]tricosanamide were identified as new compounds and termed as tagetceramides, whereas (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]tetracosanamide was a known ceramide. A steroid (β-sitosterol glucoside) was also isolated from the subsequent fraction. The structures of these compounds were determined on the basis of spectroscopic analyses, as well as chemical method. Several other compounds were also identified by GC/MS analysis. The fractions and some commercial products, a ceramide HFA, β-sitosterol, and stigmasterol were evaluated against an economically important cyst nematode, Heterodera zeae. Ceramide HFA showed 100 % mortality, whereas, β-sitosterol and stigmasterol were 40-50 % active, at 1 % concentration after 24 h of exposure time, while β-sitosterol glucoside revealed no activity against the nematode.

    Topics: Animals; Antinematodal Agents; Ceramides; Flowers; Gas Chromatography-Mass Spectrometry; Molecular Conformation; Sitosterols; Stigmasterol; Tagetes; Tylenchoidea

2019
Development of Low-calorie Organogel fromsn-2 Position-modified Coconut Oil Rich in Polyunsaturated Fatty Acids.
    Journal of oleo science, 2019, Volume: 68, Issue:5

    Coconut oil rich in medium-chain saturated fatty acids was enzymatically modified at the sn-2 position with polyunsaturated fatty acids from fish oil by trans-esterification reaction. The modified coconut oil was combined with gelators (γ-oryzanol and β-sitosterol) to prepare organogels. The effects of different modified coconut oil contents and γ-oryzanol:β-sitosterol ratios on thermodynamic and rheological properties, and microstructures of organogels, as well as their relationships, were studied. The results showed that the addition of gelators increased the hardness, solid fat content, and oil binding capacity of organogels. In addition to its highest melting point and enthalpy change, the organogel containing γ-oryzanol:β-sitosterol (6:4) had the best texture properties that closely resemble the crystalline structure properties. Moreover, the developed organogels had the properties of a pseudoplastic fluid, as described by the power law equation. G' of organogel was found to be significantly higher than G'', which indicates that the organogel remains in solid state. The analysis of crystal morphology showed that the crystal of organogels were clusters, consisting of dense three-dimensional network of gel.

    Topics: Chemical Phenomena; Coconut Oil; Crystallization; Esterification; Fatty Acids; Fatty Acids, Unsaturated; Fish Oils; Gels; Phenylpropionates; Rheology; Sitosterols; Thermodynamics

2019
Phytochemical investigation of Hyoscyamus albus.
    Pakistan journal of pharmaceutical sciences, 2019, Volume: 32, Issue:2

    The work presented in this paper illustrates the isolation and structure elucidation of secondary metabolites of Hyoscyamus albus. Two new natural source and three known compounds were isolated from the Hyoscyamus albus. Among the isolated compounds, grivilloside H (1) and betulaplatoside (2) were isolated for the first time while scopolamine (3), β-sitosterol (4) and stigmasterol (5) have been reported previously from the same plant. The structures of all the isolated compounds were established by using modern spectroscopic technique (UV, IR, NMR, and EI-MS) and by comparing with those available in literature.

    Topics: Glucosides; Hyoscyamus; Magnetic Resonance Spectroscopy; Molecular Structure; Phytochemicals; Plants, Medicinal; Scopolamine; Secondary Metabolism; Sitosterols; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Stigmasterol

2019
Physicochemical Characterization of Yellow Cake Prepared with Structured Lipid Oleogels.
    Journal of food science, 2019, Volume: 84, Issue:6

    Oleogels were produced using a phytosterol blend of β-sitosterol/γ-oryzanol or a blend of sucrose stearate/ascorbyl palmitate (SSAP) as oleogelators. Four lipid phases were compared in oleogel formation for each oleogelator blend: menhaden oil, structured lipid (SL) of menhaden oil and 30 mol% caprylic acid (SL-C), SL of menhaden oil and 20 mol% stearic acid (SL-S), and SL of menhaden oil and 14 mol% each of caprylic and stearic acid (SL-CS). All SLs were produced enzymatically using a recombinant lipase from Candida antarctica as the biocatalyst. Menhaden oil, SL, phytosterol, or SSAP oleogels were evaluated as alternatives to shortening in the preparation of yellow cake in terms of batter and cake physicochemical properties. The shortening, phytosterol, and SSAP oleogel batters exhibited statistically similar specific gravities (0.85). The shortening, and menhaden oil phytosterol and SSAP oleogel batters, exhibited similar Power-Law values (n: 0.78, k: 31 Pa s

    Topics: Ascorbic Acid; Caprylates; Fat Substitutes; Fatty Acids; Fish Oils; Food Analysis; Food Handling; Gels; Organic Chemicals; Phenylpropionates; Phytosterols; Sitosterols; Stearic Acids; Sucrose

2019
Paederia foetida induces anticancer activity by modulating chromatin modification enzymes and altering pro-inflammatory cytokine gene expression in human prostate cancer cells.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2019, Volume: 130

    Aberrant epigenetic modifications are responsible for tumor development and cancer progression; however, readily reversible. Bioactive molecules from diets are promising to cure cancer by modulating epigenetic marks and changing immune response. These compounds specifically target the activity of DNMTs and HDACs to cure various human cancers. In view of this, we investigated the anticancer and epigenetic regulatory activities of an edible-plant Paederia foetida. The efficacy of methanolic extract of P. foetida leaves (MEPL) was tested for the modulation of epigenetic factors in gene silencing, i.e. DNMT and HDAC and expression pattern of certain tumor-suppressor genes. After treatment of prostate cancer cells (PC-3 and DU-145) with MEPL, lupeol and β-sitosterol; induction of apoptosis, decrease in cellular-viability and inhibition of cellular-migration were noticed. Simultaneously there was inhibition of DNMT1, HDACs and pro-inflammatory, IL-6, IL1-β, TNF-α and anti-inflammatory, IL-10 genes in cancer and THP1 cell lines. The DNMT1 protein content, enzyme activity and Bcl2 expression decreased significantly; however, expression of E-cadherin (CDH1) and pro-apoptotic gene Bax increased significantly after the treatment of cells with drugs. We conclude plant-derived compounds can be considered to target epigenetic machineries involved with malignant transformation and can open new avenues for cancer therapeutics provoking immune response.

    Topics: Cell Line, Tumor; Cell Survival; DNA (Cytosine-5-)-Methyltransferase 1; Gene Expression Regulation, Neoplastic; Histone Deacetylase 1; Histone Deacetylase 2; Humans; Inflammation; Male; Pentacyclic Triterpenes; Phytochemicals; Plant Extracts; Plant Leaves; Prostatic Neoplasms; RNA, Messenger; Rubiaceae; Sitosterols

2019
An Attempt of Using β-Sitosterol-Corn Oil Oleogels to Improve Water Barrier Properties of Gelatin Film.
    Journal of food science, 2019, Volume: 84, Issue:6

    Oleogel with tailored viscoelasticity is a great interest for food structuring, while its potential benefits for edible film performance are not clear. In this study, β-sitosterol (0, 5, 10, 15, and 20 wt%)-corn oil oleogel was developed and used in the formation of gelatin-based films. Importantly, adding oleogel significantly decreased water vapor permeability of the gelatin films, however, it had little negative influence on film strength. In addition, the results of this study demonstrated that increasing the sitosterol in oleogels led to an increasing number of ordered crystals formed in the oleogel, which contributed to compact and smooth surface of the film. Moreover, the incorporation of oleogel also caused some changes in molecule conformation and film barrier property. Therefore, the superior mechanical performance and moisture resistance properties of the film were obtained when 15% β-sitosterol was used to prepare oleogel. PRACTICAL APPLICATION: Corn oil oleogels β-sitosterol was incorporated with gelatin to prepare the gelatin film aiming to improve the water resistance of the films for its variety of practical production. The enhanced vapor permeability and accepted strength of the emulsion film indicated the potential application of it with a variety of edible packaging forms, such as films, pouch and sachet in medium and high humid condition.

    Topics: Corn Oil; Food Packaging; Gelatin; Organic Chemicals; Permeability; Sitosterols; Steam; Viscosity; Water

2019
Effect of β-sitosterol on the curcumin-loaded liposomes: Vesicle characteristics, physicochemical stability, in vitro release and bioavailability.
    Food chemistry, 2019, Sep-30, Volume: 293

    In this work, the effect of β-sitosterol (Sito) on vesicle characteristics, physicochemical stability as well as the in vitro release and bioavailability of curcumin-loaded liposomes (Cur-LP) was studied. When 20-33 mol% of Sito was incorporated, encapsulation efficiency of curcumin was improved due to the high amount of liquid-ordered domains in membranes. At 50 mol% Sito a lower encapsulation efficiency was observed possibly due to membrane defects. The physical, thermal and photo stability of curcumin in liposomes were markedly improved with increasing the amount of Sito. First-order kinetics fitted best the curcumin release dynamics of Sito containing liposomes, clearly showing that sustained release improved with increasing amounts of Sito in liposomes. Simulated digestion studies suggested that Sito concentration of about 20-33 mol% improved the bioavailability of curcumin in liposomes. These study shows that Sito is an applicable and potential route in forming healthier cholesterol-free curcumin-loaded liposomes for functional supplements.

    Topics: Biological Availability; Curcumin; Drug Liberation; Drug Stability; Liposomes; Membrane Fluidity; Microscopy, Electron, Transmission; Sitosterols; Temperature

2019
Alyssum homolocarpum seed oil (AHSO), containing natural alpha linolenic acid, stearic acid, myristic acid and β-sitosterol, increases proliferation and differentiation of neural stem cells in vitro.
    BMC complementary and alternative medicine, 2019, Jun-03, Volume: 19, Issue:1

    Embryonic neural stem cells (eNSCs) are immature precursors of the central nervous system (CNS), with self-renewal and multipotential differentiation capacities. These are regulated by endogenous and exogenous factors such as alpha-linolenic acid (ALA), a plant-based essential omega-3 polyunsaturated fatty acid.. In this study, we investigated the effects of various concentrations of Alyssum homolocarpum seed oil (AHSO), containing natural ALA, stearic acid (SA), myristic acid (MA), and β-sitosterol, on proliferation and differentiation of eNSCs, in comparison to controls and to synthetic pure ALA.. Treatment with natural AHSO (25 to 75 μM), similar to synthetic ALA, caused a significant ~ 2-fold increase in eNCSs viability, in comparison to controls. To confirm this proliferative activity, treatment of NSCs with 50 or 75 μM AHSO resulted in a significant increase in mRNA levels of notch1, hes-1 and Ki-67and NICD protein expression, in comparison to controls. Moreover, AHSO administration significantly increased the differentiation of eNSCs toward astrocytes (GFAP+) and oligodendrocytes (MBP+) in a dose dependent manner and was more potent than ALA, at similar concentrations, in comparison to controls. Indeed, only high concentrations of 100 μM AHSO, but not ALA, caused a significant increase in the frequency of neurons (β-III Tubulin+).. Our data demonstrated that AHSO, a rich source of ALA containing also other beneficial fatty acids, increased the proliferation and stimulated the differentiation of eNSCs. We suggest that AHSO's effects are caused by β-sitosterol, SA and MA, present within this oil. AHSO could be used in diet to prevent neurodevelopmental syndromes, cognitive decline during aging, and various psychiatric disorders.

    Topics: alpha-Linolenic Acid; Animals; Basic Helix-Loop-Helix Transcription Factors; Brassicaceae; Cell Differentiation; Cell Proliferation; Drug Evaluation, Preclinical; Ki-67 Antigen; Mice; Myristic Acid; Neural Stem Cells; Neurogenesis; Plant Oils; Seeds; Sitosterols; Stearic Acids

2019
A Validated HPTLC Densitometric Method for Determination of Lupeol, β-Sitosterol and Rotenone in Tephrosia purpurea: A Seasonal Study.
    Journal of chromatographic science, 2019, Aug-16, Volume: 57, Issue:8

    Tephrosia purpurea (L.) Pers., commonly known as "sarpunkha" and "wild indigo", is being used in traditional systems of medicine to treat liver disorders, spleen and kidney. In the present study, a validated High Performance Thin Layer Chromatography (HPTLC) method was established for the estimation of lupeol, β-sitosterol and rotenone in various extracts of T. purpurea with the aim to see the effect of seasons on the quantity of aforesaid phytoconstituents. The plant material was collected in summer (April), rainy (August) and winter (December) during 2013-2014 from Lucknow, India. The method was validated in terms of precision, repeatability, specificity, sensitivity linearity and robustness. The method permits reliable quantification and showed good resolution on silica gel with toluene-ethyl acetate-formic acid (9:1:1 v/v/v) as mobile phase, and characteristic bands of β-sitosterol, rotenone and lupeol were observed at Rf 0.38, 0.45 and 0.52, respectively. The content of aforesaid phytoconstituents varies from season to season and extract to extract. Our finding indicated that winter season (December) may not be appropriate for collection of T. purpurea for the preparation of therapeutic formulations because of the high content of rotenone, a known insecticide that is responsible for Parkinson's disease and associated with heart failure, fatty liver and liver necrosis.

    Topics: Chromatography, Thin Layer; India; Pentacyclic Triterpenes; Plant Extracts; Rotenone; Seasons; Sitosterols; Tephrosia

2019
Comparative study of fatty acid and sterol profiles for the investigation of potential milk fat adulteration.
    Journal of dairy science, 2019, Volume: 102, Issue:9

    Milk fat adulteration is a common issue in Central Asia. To assess the current situation in the commercial milk market, 17 milk samples were checked for fatty acid (FA) and sterol profiles to detect potential adulteration using multivariate analysis. Analysis of FA and sterols was performed using gas chromatography with flame ionization detection and gas chromatography with mass-spectrometric detection, respectively. Cluster analysis of FA profiles revealed 3 types of milk samples: (1) samples containing a higher proportion of short-chain FA, (2) samples containing a higher proportion of long-chain FA, and (3) samples with significant amounts of C18 FA. Analysis of sterols showed that samples included (1) milk fat containing 100% cholesterol, sometimes with traces of phytosterols, (2) milk fat with high proportions of β-sitosterol and campesterol, and (3) milk fat containing high proportions of brassicasterol. We found significant relationships between FA profiles and sterol profiles. The profiles were compared with vegetable oil patterns reported in the literature. More than 50% of the samples appeared to be counterfeited. We conclude that identification of adulteration in milk can be based solely on determination of sterol patterns.

    Topics: Animals; Cholestadienols; Cholesterol; Fatty Acids; Food Contamination; Gas Chromatography-Mass Spectrometry; Milk; Phytosterols; Plant Oils; Sitosterols; Sterols

2019
Hepatoprotective effect of Solanum surattense leaf extract against chemical- induced oxidative and apoptotic injury in rats.
    BMC complementary and alternative medicine, 2019, Jul-03, Volume: 19, Issue:1

    Of over 35 Saudi plants traditionally used to treat liver disorders, majority still lack scientific validations. We therefore, evaluated the anti-oxidative, anti-apoptotic and hepatoprotective potential of Solanum surattense leaves total ethanol-extract (SSEE).. Our findings suggest the therapeutic potential of S. surattense against chemical-induced oxidative stress and liver damage. However, isolation of the active principles and elucidation of mechanism of action remain to be addressed.

    Topics: Animals; Antioxidants; Apoptosis; Carbon Tetrachloride Poisoning; Chemical and Drug Induced Liver Injury; Drug Evaluation, Preclinical; Hep G2 Cells; Humans; Liver; Plant Extracts; Rats, Wistar; Sitosterols; Solanum

2019
Topical hydrogels with escin β-sitosterol phytosome and escin: Formulation development and in vivo assessment of antihyperalgesic activity.
    Drug development research, 2019, Volume: 80, Issue:7

    The physicochemical properties, stability, in vivo antihyperalgesic activity, and skin irritation potential of the carbomer hydrogels with the new chemical entity escin β-sitosterol (ES) phytosome were characterized and compared with those containing escin. Physicochemical characterization of the hydrogels (performed 48 hr after preparation) included organoleptic examination, pH measurement, light microscopy, differential scanning calorimetry analysis and rheological tests. The obtained results showed that increasing concentration of the active substances within 1-5% affected the appearance (color and transparency) of the hydrogels, their pH, consistency, and rheological behavior. Unlike acidic escin, which was dissolved in the liquid phase of the pseudoplastic hydrogels E1-E5 and reduced their maximal apparent viscosity (η

    Topics: Administration, Cutaneous; Animals; Chemical Phenomena; Dose-Response Relationship, Drug; Drug Compounding; Drug Stability; Escin; Hydrogels; Male; Pain Measurement; Rats; Sitosterols

2019
Design of bile-based vesicles (BBVs) for hepatocytes specific delivery of Daclatasvir: Comparison of ex-vivo transenterocytic transport, in-vitro protein adsorption resistance and HepG2 cellular uptake of charged and β-sitosterol decorated vesicles.
    PloS one, 2019, Volume: 14, Issue:7

    Daclatasvir is a new direct acting antiviral used in treatment of Hepatitis C virus, in an attempt to increase its hepatocytes specificity and uptake. It was encapsulated within bile based vesicles (BBVs) containing egg phosphatidyl choline, cholesterol and sodium deoxycholate fabricated by thin-film hydration method. A D-optimal mixture design was applied to study the effect of formulation variables on vesicular characteristics. The dependent variables picked were the particle size, polydispersity index, zeta potential and entrapment efficiency. The optimized bile based vesicles were subjected for further modifications to prepare miniaturized anionic (ABBVs), cationic (CBBVs) and Sito-G decorated BBVs (Sito-GBBVs) to be capable to penetrate liver fenestrae (<200 nm). The aim of the current work is to compare the potential of the ABBVs, CBBVs and Sito-GBBVs loaded with Daclatasvir for stability in simulated biological fluids, ex-vivo intestinal transenterocytic transport, HepG2 cellular uptake and resistance to blood protein adsorption. The miniaturized ABBVs, CBBVs and Sito-GBBVs showed acceptable stability in simulated biological fluids. CBBVs had the highest transenterocytic transport through intestinal membrane. The internalization of CBBVs into HepG2 cells was about 2.1 folds that of ABBVs and 1.45 folds that of Sito-GBBVs. ABBVs and Sito-GBBVs showed superior resistance to opsonization compared to CBBVs which showed significant increase in particle size (p˃0.05) due to protein adsorption. The miniaturized Sito-GBBVs constitute a promising strategy to overcome key biological barriers facing hepatocytes specific delivery of Daclatasvir.

    Topics: Adsorption; Animals; Antiviral Agents; Biological Transport; Carbamates; Cholesterol; Deoxycholic Acid; Drug Carriers; Drug Delivery Systems; Hep G2 Cells; Hepatocytes; Humans; Imidazoles; Liposomes; Liver; Male; Particle Size; Phosphatidylcholines; Pyrrolidines; Rats; Rats, Wistar; Sitosterols; Valine

2019
Effect of β-sitosterol self-microemulsion and β-sitosterol ester with linoleic acid on lipid-lowering in hyperlipidemic mice.
    Lipids in health and disease, 2019, Jul-27, Volume: 18, Issue:1

    The hypolipidemic effect of phytosterols has been wildely recognized, but its application is limited due to its insolubility in water and low solubility in oil. In this study, β-sitosterol ester with linoleic acids and β-sitosterol self-microemulsions were prepared and their hypolipidemic effects on hyperlipidemia mice were studied.. Firstly, the mice were randomly divided into normal group and model group,they were fed with basic diet and high-fat diet for 70 days respectively. After high-fat model mice was successfully established, the model group was further divided into eight groups: HFD (high-fat diet feeding), SELA-TSO(8 ml/kg, SELA:700 mg/kg), TSO (8 ml/kg), SSSM (8 ml/kg,SS:700 mg/kg), NLSM (8 ml/kg), SSHT-TSO (8 ml/kg, SS: 700 mg/kg) and SS-TSO (8 ml/kg, SS: 700 mg/kg) groups, and treated with β-sitosterol ester with linoleic acid, β-sitosterol self-microemulsion, commercial β-sitosterol health tablets and β-sitosterol powder for 35 days, respectively, and blank control groups were established. At the end of the treatment period, the blood lipid level, tissues, cholesterol and lipids in feces of mice in each group were investigated. Statistical and analytical data with SPSS 17.0 Software,statistical significance was set at p* < 0.05 and p** < 0.01 levels .. The order of lowering blood lipid effect is listed as: SSSM> SELA-TSO > SSHT-TSO > SS-TSO, which shows that β-sitosterolself-microemulsion have the highest treatment effect among the experimental groups.. In this study, a new formulation of β-sitosterol was developed, and its hypolipidemic effect was investigated. The results showed that β-sitosterol self-microemulsion has a good blood lipid lowering effect.

    Topics: Administration, Oral; Animals; Body Weight; Eating; Emulsions; Feces; Hyperlipidemias; Hypolipidemic Agents; Linoleic Acid; Lipids; Male; Mice; Microscopy, Electron, Transmission; Organ Size; Sitosterols; Tablets

2019
New tetranorlabdanoic acid from aerial parts of Salvia aethiopis.
    Natural product research, 2018, Volume: 32, Issue:1

    Salvia aethiopis is a perennial plant native to Eurasia and known by the common names Mediterranean sage or African sage. This plant has been used in Iranian medicine as a carminative and tonic. The ethanolic extract of aerial part of S. aethiopis exhibited moderate to weak activity towards delta and kappa opioid receptors (46.3 and 45.3% displacement, respectively). Chromatographic purification of the ethanolic extract on silica gel column led to isolation of one new: 3α-hydroxy-8α-acetoxy-13,14,15,16-tetranorlabdan-12-oic acid (I) and three known compounds: sesquiterpene spathulenol (II), β-sitosterol (III) and β-sitosterol-3-O-glucoside (IV). The structures of all isolated compounds were elucidated by their NMR (1D and 2D) and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding assays.

    Topics: Drug Evaluation, Preclinical; Iran; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Components, Aerial; Plant Extracts; Plants, Medicinal; Receptors, Cannabinoid; Receptors, Opioid, delta; Receptors, Opioid, kappa; Salvia; Sesquiterpenes; Sitosterols

2018
Chemometric profile, antioxidant and tyrosinase inhibitory activity of Camel's foot creeper leaves (Bauhinia vahlii).
    Natural product research, 2018, Volume: 32, Issue:5

    The present study is the first effort to a comprehensive evaluation of antityrosinase activity and chemometric analysis of Bauhinia vahlii. The experimental results revealed that the methanol extract of Bauhinia vahlii (BVM) possesses higher polyphenolic compounds and total antioxidant activity than those reported elsewhere for other more conventionally and geographically different varieties. The BVM contain saturated fatty acids such as hexadecanoic acid (10.15%), octadecanoic acid (1.97%), oleic acid (0.61%) and cis-vaccenic acid (2.43%) along with vitamin E (12.71%), α-amyrin (9.84%), methyl salicylate (2.39%) and β-sitosterol (17.35%), which were mainly responsible for antioxidant as well as tyrosinase inhibitory activity. Tyrosinase inhibitory activity of this extract was comparable to that of Kojic acid. These findings suggested that the B. vahlii leaves could be exploited as potential source of natural antioxidant and tyrosinase inhibitory agent, as well.

    Topics: Antioxidants; Bauhinia; Drug Evaluation, Preclinical; Enzyme Inhibitors; Fatty Acids; Gas Chromatography-Mass Spectrometry; Monophenol Monooxygenase; Oleanolic Acid; Oleic Acids; Plant Extracts; Plant Leaves; Sitosterols

2018
Two antidiabetic constituents from Roylea cinerea (D.Don) Baill.
    Natural product research, 2018, Volume: 32, Issue:11

    Two antidiabetic compounds named 4-methoxybenzo[b]azet-2(1H)-one (1) and 3β-hydroxy-35-(cyclohexyl-5'-propan-7'-one)-33-ethyl-34-methyl-bacteriohop-16-ene (2) together with stigmasterol and β-sitosterol were isolated from the aerial part of Roylea cinerea (D.Don) Baill. The structures of these compounds were elucidated by advanced spectroscopic methods, including two-dimensional NMR and MS techniques. These compounds were evaluated for their antidiabetic efficacy using in vitro and in vivo methods. Both compounds (1 and 2) showed a significant decline in blood glucose level of alloxan-induced diabetic rats at 10 mg/kg, p.o. when compared with glibenclamide at a similar dose. The in vitro studies revealed that compound 1 reduced α-amylase and α-glucosidase by 83.0 and 78.5%, respectively, whereas compound 2 reduced the same by 58.2 and 58.4%, respectively, at 100 μM. The present study supports the role of R. cinerea in Ayurvedic medicine for diabetes.

    Topics: Alloxan; alpha-Amylases; alpha-Glucosidases; Animals; Azetidines; Diabetes Mellitus, Experimental; Female; Glycoside Hydrolase Inhibitors; Hypoglycemic Agents; Lamiaceae; Male; Medicine, Ayurvedic; Molecular Structure; Plant Extracts; Rats; Sitosterols; Triterpenes

2018
Chemical and biological studies on Cichorium intybus L.
    Natural product research, 2018, Volume: 32, Issue:11

    Cichorium intybus L. (Asteraceae family) is a world-wide grown plant known as chicory. In traditional medicine, this plant is used as diuretic, anti-inflammatory, digestive, cardiotonic and liver tonic. Chromatographic purification of the supercritical fluid extract of aerial parts of C. intybus on silica gel column led to isolation of three compounds: new compound, 28β-hydroxytaraxasterol (I), and two known compounds usnic acid (II) and β-sitosterol (III). Purification of the ethanolic extract of aerial parts of this plant on silica gel column chromatography yielded four compounds: 1,3-dioleylglycerate (IV), sitoindoside II (V), 11β-13-dihydrolactucin (VI) and β-sitosterol-3-O-glucoside (VII). The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding, as well as antibacterial, antifungal and antimalarial activities. Compound I showed moderate activity (60.5% displacement) towards CB1 receptor.

    Topics: Anti-Bacterial Agents; Antifungal Agents; Antimalarials; Cichorium intybus; Drug Evaluation, Preclinical; Glucosides; Magnetic Resonance Spectroscopy; Medicine, Traditional; Molecular Structure; Plant Components, Aerial; Plant Extracts; Plants, Medicinal; Receptor, Cannabinoid, CB1; Receptors, Cannabinoid; Receptors, Opioid; Sitosterols

2018
Chemical profile and antihyperlipidemic effect of Portulaca oleracea L. seeds in streptozotocin-induced diabetic rats.
    Natural product research, 2018, Volume: 32, Issue:12

    Hypolipidemic effect of Portulaca oleracea L. seed extract and its fractions have been studied on streptozotocin (STZ) at dose 75 mg/kg b.wt. After fractionation of the alcoholic extract; petroleum ether fraction was the most active fraction that decreased different hyperlipidemia biochemical parameters. After chromatographic analysis; oleamide, ethylpalmitate, β-amyrin, stigmasterol and β-sitosterol were identified. The GLC analysis of unsaponifiable matter revealed the presence of; lignoceric acid as a major constituent in the most bioactive fraction. In conclusion, petroleum ether fraction possessed a hypolipidemic effect in STZ-induced diabetic rats, which may be attributed to its phytosterols, fatty acid and amide compounds. The finding of the present investigation strongly demonstrates the potential of non-polar fraction of P. oleracea L. seed in combating hyperlipidemia in diabetic condition. So the petroleum ether fractions and its constituents can be used as hypolipdemic supplement in the developing countries towards the development of new therapeutic agents.

    Topics: Animals; Diabetes Mellitus, Experimental; Hyperlipidemias; Hypolipidemic Agents; Male; Phytosterols; Phytotherapy; Plant Extracts; Portulaca; Rats; Seeds; Sitosterols; Stigmasterol; Streptozocin

2018
Effect of acaricidal components isolated from lettuce (Lactuca sativa) on carmine spider mite (Tetranychus cinnabarinus Boisd.).
    Bulletin of entomological research, 2018, Volume: 108, Issue:3

    This study aimed to evaluate the acaricidal activity of lettuce (Lactuca sativa) extracts against carmine spider mites (Tetranychus cinnabarinus Boisd.) and isolate the acaricidal components. Acaricidal activities of lettuce extracts isolated from different parts (the leaf, root and seed) using various solvents (petroleum ether, acetone and methanol) were evaluated with slide-dip bioassay and relatively high median lethal concentration (LC50) values were detected. Acetone extracts of lettuce leaves harvested in July and September were fractionated and isolated with silica gel and thin-layer chromatography. Consequently, acetone extracts of lettuce leaves harvested in July exhibited higher acaricidal activity than those harvested in September, with an LC50 value of 0.268 mg ml-1 at 72 h post-treatment. A total of 27 fractions were obtained from the acetone extract of lettuce leaves harvested in July, and mite mortalities with the 11th and 12th fractions were higher than those with the other 25 fractions (LC50: 0.751 and 1.258 mg ml-1 at 48 h post-treatment, respectively). Subsequently, active acaricidal components of the 11th fraction were identified by infrared, nuclear magnetic resonance and liquid chromatography/mass spectrometry. Five components were isolated from the 11th fraction, with components 11-a and 11-b showing relatively high acaricidal activities (LC50: 0.288 and 0.114 mg ml-1 at 48 h post-treatment, respectively). Component 11-a was identified as β-sitosterol. In conclusion, acetone extracts of lettuce leaves harvested in July might be used as a novel phytogenic acaricide to control mites.

    Topics: Acaricides; Animals; Lactuca; Lethal Dose 50; Sitosterols; Tetranychidae

2018
Rauvolfianine, a new antimycobacterial glyceroglycolipid and other constituents from Rauvolfia caffra. Sond (Apocynaceae).
    Natural product research, 2018, Volume: 32, Issue:16

    The chemical investigation of the extract of the dried leaves of Rauvolfia caffra (Sond) (synonym Rauvolfia macrophylla) (Apocynaceae) led to isolation of a new glycoside derivative, rauvolfianine (1) as well as six known compounds: oleanolic acid (2), sitosterol-3-O-β-D-glucopyranoside (3), betulinic acid (4), vellosimine (5), sarpagine (6) and D-fructofuranosyl-β-(2→1)-α-D-glucopyranoside (7). Compounds 1, 2, 3, 4 and 7 were evaluated for antitubercular activity. Compounds 1 and 2 were the most active (MIC = 7.8125 and 31.25 μg/mL) towards the Isoniazid resistant strain of Mycobacterium tuberculosis AC45. Their structures and relative stereochemistry were elucidated by spectroscopic methods.

    Topics: Antitubercular Agents; Apocynaceae; Betulinic Acid; Glycosides; Magnetic Resonance Spectroscopy; Molecular Structure; Mycobacterium tuberculosis; Oleanolic Acid; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Rauwolfia; Sitosterols; Triterpenes

2018
Development of an ultrasound assisted method for determination of phytosterols in vegetable oil.
    Food chemistry, 2018, Feb-01, Volume: 240

    The aims of this study were the optimization and validation of a new ultrasound assisted phytosterol method through analysis of response surface generated from Box-Behnken design. Variables quantity of sample (g), volume of KOH/MeOH (mL) and ultrasound time (s) were investigated in three levels. The evaluation process of the methodology was executed through determination of analytical parameters, such as selectivity, linearity, accuracy, dynamic linear range, "intra-day" accuracy and limits of detection and quantification. Optimized conditions for stigmasterol determination were 0.25g; 2.5mL; 300s; and β-sitosterol were 0.25g; 5.4mL; 300s. The evaluated conditions and all investigated analytical parameters showed that the method is effective for determination of analytes β-sitosterol and stigmasterol. This new analytical method has the same efficiency of the traditional method, while significantly reducing the total time of extraction for 300s regarding saponification step when compared to 3600s from the traditional method.

    Topics: Phytosterols; Plant Oils; Sitosterols; Stigmasterol; Ultrasonic Waves

2018
Effects of sodium β-sitosteryl sulfate on the phase behavior of dipalmitoylphosphatidylcholine.
    Colloids and surfaces. B, Biointerfaces, 2018, Jan-01, Volume: 161

    We have studied the phase behavior of dipalmitoylphosphatidylcholine (DPPC) containing sodium β-sitosteryl sulfate (PSO

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Cholesterol; Freeze Fracturing; Lipid Bilayers; Membrane Fluidity; Microscopy, Electron, Transmission; Phase Transition; Scattering, Small Angle; Sitosterols; Transition Temperature; X-Ray Diffraction

2018
Phytochemical analysis of non-polar solvent extracts of the Wisteria sinensis leaves.
    Natural product research, 2018, Volume: 32, Issue:20

    A comparative study on the phytochemical composition of the n-hexane and chloroform extracts from Wisteria sinensis leaves collected in June and October is described. Continuous extraction in Soxhlet apparatus, as well as ultrasound-assisted technique, was used for the preparation of the extracts. All the extracts were analysed by GC/MS method. As a result, α-tocopherol was identified as the main component (56%) of the extracts from October leaves, whereas, β-sitosterol was identified as the main compound (47%) in the extracts from the June leaves. Additionally, pure α-tocopherol was isolated from n-hexane extract of the October leaves using column chromatography. A total of 6.25 mg of α-tocopherol was isolated from 1 g of dried leaves. The presence of the vitamin E in extracts from W. sinensis leaves is described here for the first time.

    Topics: alpha-Tocopherol; Chloroform; Gas Chromatography-Mass Spectrometry; Hexanes; Phytochemicals; Plant Extracts; Plant Leaves; Seasons; Sitosterols; Solvents; Vitamin E; Wisteria

2018
Effect of the Harvest Time on Oil Yield, Fatty Acid, Tocopherol and Sterol Contents of Developing Almond and Walnut Kernels.
    Journal of oleo science, 2018, Volume: 67, Issue:1

    Oil content and bioactive properties of almond and walnut kernels were investigated in developing almond and walnut kernels at 10 days intervals. The oil contents of almond and walnuts after the first harvest (1.H) stage changed between 46.2% and 55.0% to 39.1% and 70.5%, respectively (p<0.05). Oleic acid contents of almond and walnut oils ranged from 71.98% (1.H) to 78.68% (5.H) and 10.51% (1.H) to 16.78% (2.H) depending on harvest (H) times, respectively (p<0.05). In addition, linolenic acid contents of walnut and almond oils were found between 62.35% and 67.78%, and 12.02% and 17.65%, respectively. The almond kernel oil after the first harvest stage contained 1.045, 1.058, 1.018, 0.995 and 0.819 mg/kg ɑ-tocopherol, respectively. γ-Tocopherol contents of walnut oil changed between 1.364 (3.H) and 2.954 mg/kg (1.H). The β-sitosterol contents of both almond and walnut oils were found between 1956.6 (5.H) and 2557.7 (1.H), and 1192.1 (3.H) and 4426.4 mg/kg (1.H). The study exhibited the presence of high percentage of oleic and linoleic for almond and walnut, respectively, and γ-tocopherol and β-sitosterol.

    Topics: alpha-Linolenic Acid; alpha-Tocopherol; Chromatography, Gas; Chromatography, High Pressure Liquid; Crops, Agricultural; gamma-Tocopherol; Juglans; Oleic Acids; Plant Oils; Prunus dulcis; Sitosterols; Time Factors

2018
Effects of Plant Sterols or β-Cryptoxanthin at Physiological Serum Concentrations on Suicidal Erythrocyte Death.
    Journal of agricultural and food chemistry, 2018, Feb-07, Volume: 66, Issue:5

    The eryptotic and hemolytic effects of a phytosterol (PS) mixture (β-sitosterol, campesterol, stigmasterol) or β-cryptoxanthin (β-Cx) at physiological serum concentration and their effect against oxidative stress induced by tert-butylhydroperoxide (tBOOH) (75 and 300 μM) were evaluated. β-Cryptoxanthin produced an increase in eryptotic cells, cell volume, hemolysis, and glutathione depletion (GSH) without ROS overproduction and intracellular Ca

    Topics: Beta-Cryptoxanthin; Cells, Cultured; Cholesterol; Eryptosis; Erythrocytes; Glutathione; Hemolysis; Humans; Oxidative Stress; Phytosterols; Sitosterols; Stigmasterol; tert-Butylhydroperoxide

2018
The natural history of phytosterolemia: Observations on its homeostasis.
    Atherosclerosis, 2018, Volume: 269

    Phytosterolemia is a rare genetic disease caused by mutation of the ABCG5/8 gene. Our aim was to elucidate the natural history and homeostasis of phytosterolemia.. We analyzed a Hutterite kindred consisting of 21 homozygotes with phytosterolemia assembled over a period of two decades, all of whom carried the ABCG8 S107X mutation and were treated with ezetimibe.. Most of these subjects were asymptomatic and devoid of clinical stigmata, and this, since they were ascertained primarily by a process of cascade testing, suggests that, relative to its true prevalence, phytosterolemia is a condition of low morbidity. All subjects have responded well to treatment with ezetimibe. Initial (pre-treatment) and post-ezetimibe levels of cholesterol and sitosterol were measured and percentage changes on ezetimibe were calculated. We found initial levels to be inversely related to subjects' ages as were percentage responses to ezetimibe therapy. There was also a direct correlation between initial levels and percentage responses to ezetimibe. Hence on-treatment levels were very uniform.. This evidence of a link with age leads us to propose that an age-related change in cholesterol and sterol homeostasis occurs at puberty in phytosterolemia and that the change is due to high sterol and/or stanol levels causing feedback inhibition of sterol regulatory element-binding protein (SREBP-2) processing. This would explain the well-documented phenomenon of depressed cholesterol synthesis in phytosterolemia. It is also well-known that LDL-receptor activity is increased, and this feasibly explains reduced LDL levels and consequent reduction of plasma cholesterol and sitosterol levels. Downregulated SREBP-2 processing would be expected to also lower proprotein convertase subtilisin/kexin type 9 (PCSK9) levels and this would explain high LDL-receptor activity. The above state could be termed disrupted homeostasis and the alternative, seen mostly in children and characterized by hypercholesterolemia and hypersterolemia, simple homeostasis.

    Topics: Adolescent; Adult; Age Factors; Anticholesteremic Agents; Asymptomatic Diseases; ATP Binding Cassette Transporter, Subfamily G, Member 8; Biomarkers; Canada; Child; Child, Preschool; Cholesterol; Ezetimibe; Female; Genetic Predisposition to Disease; Homeostasis; Humans; Hypercholesterolemia; Infant; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Male; Middle Aged; Mutation; Phenotype; Phytosterols; Prevalence; Puberty; Rare Diseases; Risk Factors; Sitosterols; Time Factors; Treatment Outcome; United States; Young Adult

2018
GC/MS analysis and characterization of 2-Hexadecen-1-ol and beta sitosterol from Schimpera arabica extract for its bioactive potential as antioxidant and antimicrobial.
    Journal of applied microbiology, 2018, Volume: 124, Issue:5

    We evaluated the in vitro antioxidant and antimicrobial potential of Schimpera arabica extract and fractions (2-Hexadecen-1-ol and beta sitosterol).. Free radical scavenging activity was estimated by using ABTS and DPPH methods, reducing power and iron chelation was studied to investigate antioxidant potential of the extracts. Well-diffusion method was utilized to evaluate the antimicrobial activity of the extracts. Gas chromatography-mass spectroscopy analysis of the extract revealed the presence of 27 compounds. Phenolic and flavonoid contents were found in high amount (7·6-18 mg GAE, mg g. Among all the extracts, 2-Hexadecen-1-ol and beta sitosterol were the major constituents of crude extract and exhibited significant antioxidant potential as well antimicrobial activity; however, all other fractions also exhibited fare degree of antioxidant potential. 93% DPPH was scavenged by 100 μg ml. Schimpera arabica is naturally present and used in food preparation in most Arabian nations. The characterization of S. arabica would provide an insight into its medicinal use as home remedial for bacterial infection and as antioxidant. Significant and comparable antimicrobial activity was demonstrated by both 2-Hexadecen-1-ol and beta sitosterol fractions. The results suggest that S. arabica contain a good amount of natural antioxidants of medicinal importance. However, further investigations are needed to characterize the further activity of 2-Hexadecen-1-ol and beta sitosterol in vivo.

    Topics: Anti-Bacterial Agents; Anti-Infective Agents; Antioxidants; Brassicaceae; Fatty Alcohols; Flavonoids; Gas Chromatography-Mass Spectrometry; Phenols; Plant Extracts; Sitosterols; Terpenes

2018
Probing the Antiallergic and Anti-inflammatory Activity of Biflavonoids and Dihydroflavonols from Dietes bicolor.
    Journal of natural products, 2018, 02-23, Volume: 81, Issue:2

    Dietes bicolor (Iridaceae) is an ornamental plant used by African local healers to treat diarrhea and dysentery. A new dihydroflavonol, (2R,3R)-3,5,7-trihydroxy-8-methoxyflavanone (1); two known dihydroflavonols, trans-3-hydroxy-5-methoxy-6,7-methylenedioxyflavanone (2) and trans-3-hydroxy-5,7-dimethoxyflavanone (3); the known isoflavone orobol 7,3'-di-O-methyl ether (4); the known biflavones lanaroflavone (5), robustaflavone (6), and amentoflavone (7); and β-sitosterol (8) were isolated from the CH

    Topics: Anti-Allergic Agents; Anti-Inflammatory Agents; Biflavonoids; Cell Line, Tumor; Humans; Iridaceae; Mast Cells; Plant Extracts; Plant Leaves; Sitosterols

2018
β-Sitosterol targets Trx/Trx1 reductase to induce apoptosis in A549 cells via ROS mediated mitochondrial dysregulation and p53 activation.
    Scientific reports, 2018, 02-01, Volume: 8, Issue:1

    β-Sitosterol (BS), a major bioactive constituent present in plants and vegetables has shown potent anticancer effect against many human cancer cells, but the underlying mechanism remain elusive on NSCLC cancers. We found that BS significantly inhibited the growth of A549 cells without harming normal human lung and PBMC cells. Further, BS treatment triggered apoptosis via ROS mediated mitochondrial dysregulation as evidenced by caspase-3 & 9 activation, Annexin-V/PI positive cells, PARP inactivation, loss of MMP, Bcl-2-Bax ratio alteration and cytochrome c release. Moreover, generation of ROS species and subsequent DNA stand break were found upon BS treatment which was reversed by addition of ROS scavenger (NAC). Indeed BS treatment increased p53 expression and its phosphorylation at Ser15, while silencing the p53 expression by pifithrin-α, BS induced apoptosis was reduced in A549 cells. Furthermore, BS induced apoptosis was also observed in NCI-H460 cells (p53 wild) but not in the NCI-H23 cells (p53 mutant). Down-regulation of Trx/Trx1 reductase contributed to the BS induced ROS accumulation and mitochondrial mediated apoptotic cell death in A549 and NCI-H460 cells. Taken together, our findings provide evidence for the novel anti-cancer mechanism of BS which could be developed as a promising chemotherapeutic drug against NSCLC cancers.

    Topics: Antineoplastic Agents; Apoptosis; Cell Line, Tumor; Humans; Intracellular Signaling Peptides and Proteins; Membrane Proteins; Mitochondria; Reactive Oxygen Species; Sitosterols; Tumor Suppressor Protein p53

2018
Enhancing stability of echium seed oil and beta-sitosterol by their coencapsulation by complex coacervation using different combinations of wall materials and crosslinkers.
    Food chemistry, 2018, Jun-30, Volume: 252

    Intake of omega-3 fatty acids and phytosterols aids in the reduction of cholesterol and serum triglycerides. However, both fatty acids and phytosterols are susceptible to oxidation. This work coencapsulated echium oil (source of stearidonic and alpha-linolenic fatty acids) and beta-sitosterol (phytosterol) by complex coacervation using different combinations of wall materials, and sinapic acid (SA) and transglutaminase as crosslinkers. High encapsulation yields were obtained (29-93% for SA; 68-100% for the mixture of oil and phytosterols) and retention of 49-99% and 16% for encapsulated and free SA, at 30 days-storage. Treatment with gelatin-arabic gum and 0.075 g SA/g gelatin showed the best results: 0.07 mg MDA/g capsule, and retention of 96, 90 and 74% for alpha-linolenic, stearidonic acid and beta-sitosterol at 30 days of storage, respectively. Thus, coencapsulation of echium oil and phytosterol using SA as the crosslinker was possible, obtaining effective vehicles for protection and application of these compounds in foods.

    Topics: Coumaric Acids; Cross-Linking Reagents; Echium; Fatty Acids, Omega-3; Phytosterols; Plant Oils; Seeds; Sitosterols

2018
Anti-tumour effects of beta-sitosterol are mediated by AMPK/PTEN/HSP90 axis in AGS human gastric adenocarcinoma cells and xenograft mouse models.
    Biochemical pharmacology, 2018, Volume: 152

    We investigated the anti-cancer effects of beta-sitosterol (BS), a plant-derived sterol in AGS human gastric adenocarcinoma cells and xenograft mouse models. BS significantly reduced cell viability by inducing apoptosis in AGS adenocarcinoma cells. This was accompanied by the formation of apoptotic bodies, as detected by Annexin V, caspase 3/7 activity, and MitoPotential assay. BS stimulated phosphatase and tensin homolog (PTEN) and phospho-AMP-activated protein kinase (p-AMPK) expression. Pharmacological inhibitors or siRNA were used to further analyse the relationship between the two proteins. AMPK was found to represent a likely upstream regulator of PTEN. Additionally, two-dimensional gel electrophoresis was used to identify related proteins in the treatment of BS. The decrease of Hsp90 protein by BS was observed. Induction of PTEN protein and reduction of Hsp90 was mediated by AICAR, an AMPK activator, indicating that AMPK is necessary for PTEN and Hsp90 expression. Additionally, BS was found to be effective through the regulation of cancer biomarker. Furthermore, BS suppressed tumour growth without toxicity in the AGS xenograft mouse models-. Taken together, the present results demonstrate that BS exerts anti-cancer effects in AGS cells and xenograft mouse models by mediating AMPK, PTEN, and Hsp90.

    Topics: Adenocarcinoma; Adenylate Kinase; Animals; Apoptosis; Biomarkers, Tumor; Cell Line, Tumor; Cell Survival; Gene Expression Regulation, Neoplastic; HSP90 Heat-Shock Proteins; Humans; Hypolipidemic Agents; Male; Mice; Mice, Nude; Neoplasms, Experimental; PTEN Phosphohydrolase; Sitosterols; Stomach Neoplasms

2018
Effects of Stigmasterol and β-Sitosterol on Nonalcoholic Fatty Liver Disease in a Mouse Model: A Lipidomic Analysis.
    Journal of agricultural and food chemistry, 2018, Apr-04, Volume: 66, Issue:13

    To study the effects of stigmasterol and β-sitosterol on high-fat Western diet (HFWD)-induced nonalcoholic fatty liver disease (NAFLD), lipidomic analyses were conducted in liver samples collected after 33 weeks of the treatment. Principal component analysis showed these phytosterols were effective in protecting against HFWD-induced NAFLD. Orthogonal projections to latent structures-discriminate analysis (OPLS-DA) and S-plots showed that triacylglycerols (TGs), phosphatidylcholines, cholesteryl esters, diacylglycerols, and free fatty acids (FFAs) were the major lipid species contributing to these discriminations. The alleviation of NAFLD is mainly associated with decreases in hepatic cholesterol, TGs with polyunsaturated fatty acids, and alterations of free hepatic FFA. In conclusion, phytosterols, at a dose comparable to that suggested for humans by the FDA for the reduction of plasma cholesterol levels, are shown to protect against NAFLD in this long-term (33-week) study.

    Topics: Animals; Cholesterol; Diet, High-Fat; Disease Models, Animal; Humans; Lipid Metabolism; Liver; Male; Mice; Mice, Inbred C57BL; Non-alcoholic Fatty Liver Disease; Sitosterols; Stigmasterol; Triglycerides

2018
Beta-sitosterol and its derivatives repress lipopolysaccharide/d-galactosamine-induced acute hepatic injury by inhibiting the oxidation and inflammation in mice.
    Bioorganic & medicinal chemistry letters, 2018, 05-15, Volume: 28, Issue:9

    Beta-sitosterol (Sit) widely exists in natural plants, is classed as phytosterol and known as the "key of life". Most pharmacological studies and clinical applications are limited because of the fact that Sit is difficult to be solved. Therefore, it is viable to enhance pharmacologic activities of Sit by using its derivatives which can be obtained through the modification of Sit. In this study, 4 kinds of new Sit derivatives were obtained by the esterification reaction. Further, the hepatoprotective effects of Sit and its derivatives were investigated against acute liver injury induced by lipopolysaccharide/d-galactosamine (LPS/GalN) in mice and its mechanism was illustrated by western blot analysis and real-time PCR. The results demonstrated that among its derivatives, 2-naphthoyl Sit ester (Sit-N) (50 mg/kg) showed the strongest activities against acute liver injury. Final experimental results showed that Sit-N significantly decreased the serum activity of aspartate transaminase (AST) and alanine aminotransferase (ALT); Sit-N also markedly reduced tumor necrosis factor (TNF-α), interleukin-1β (IL-1β) and interleukin-6 (IL-6) levels. Meanwhile, Sit-N drastically improved the activities of antioxidant enzymes such as superoxide dismutase (SOD), glutathione (GSH) and catalase (CAT), and suppressed the expression of malondialdehyde (MDA). Results also displayed that over-expression of Toll like receptor 4 (TLR4) and nuclear factor-kappa B (NF-κB) induced by LPS/Gal N were inhibited by Sit-N. Meanwhile, the expression of nuclear respiratory factor2 (Nrf2) and heme oxygenase-1 (HO-1) were enhanced. The results all above verified the effectiveness of Sit-N against acute liver injury induced by LPS/GalN mediated by TLR4 and Nrf2 pathways.

    Topics: Animals; Anti-Inflammatory Agents; Cell Survival; Chemical and Drug Induced Liver Injury; Dose-Response Relationship, Drug; Galactosamine; Inflammation; Lipopolysaccharides; Mice; Molecular Structure; Oxidation-Reduction; Sitosterols; Structure-Activity Relationship

2018
Antimicrobial activity of nanoemulsion on drug-resistant bacterial pathogens.
    Microbial pathogenesis, 2018, Volume: 120

    The appearance of drug-resistant (DR) bacteria in the community is a crucial development, and is associated with increased morbidity, mortality, healthcare costs, and antibiotic use. Natural oil nanoemulsions (NEs) have potential for antimicrobial applications. In the present study, we determined the antimicrobial activity of an NE against DR bacterial pathogens in vitro. The NE comprised Cleome viscosa essential oil, Tween 80 nonionic surfactant, and water. We found that an NE with a droplet size of 7 nm and an oil:surfactant (v/v) ratio of 1:3 was effective against methicillin-resistant Staphylococcus aureus (MRSA), DR Streptococcus pyogenes, and DR extended-spectrum beta-lactamase (ESBL)-producing Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa. Fourier-transform infrared (FTIR) spectroscopy revealed that NE treatment modified the functional groups of lipids, proteins, and nucleic acids in DR bacterial cells. Scanning electron microscopy (SEM) showed damage to the cell membranes and walls of NE-treated DR bacteria. These alterations were caused by bioactive compounds with wide-spectrum enzyme-inhibiting activity in the NE, such as β-sitosterol, demecolcine, campesterol, and heneicosyl formate. The results suggest that the nanoemulsion is effective against DR bacteria, and acts by inhibiting the drug efflux mechanism of DR strains.

    Topics: Anti-Bacterial Agents; Anti-Infective Agents; Cholesterol; Cleome; Demecolcine; Drug Resistance, Bacterial; Emulsions; Escherichia coli; Klebsiella pneumoniae; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Nanostructures; Oils, Volatile; Particle Size; Phytosterols; Plant Extracts; Polysorbates; Pseudomonas aeruginosa; Sitosterols; Sonication; Streptococcus pyogenes; Surface-Active Agents

2018
Propolis wax nanostructured lipid carrier for delivery of β sitosterol: Effect of formulation variables on physicochemical properties.
    Food chemistry, 2018, Sep-15, Volume: 260

    Preparation and characterization of novel functional nanostructured lipid carriers containing β sitosterol has been studied. The nanostructured lipid carrires (NLCs) were formulated with propolis wax (PW) alone or in mixture (1:1 w/w) with glyceryl behenate (GB), and pomegranate seed oil (PSO) and produced by a hot melt emulsification method. Response surface methodology was used to optimize formulations with respect to β sitosterol concentration, liquid lipid content and solid lipid composition. The NLCs formulated with less oil and higher drug content showed higher size and lower encapsulation efficiency. Solid state analysis exhibited lower crystallinity of optimal formulations compared to raw lipids and a drug amorphization into the NLC matrix. The compatibility between drug and encapsulating materials was confirmed by Fourier transform infrared spectroscopy. Transmission electron microscopy showed spherical particles ranged around 100 nm confirming the applicability of such formulations for the production of functional foods.

    Topics: Calorimetry, Differential Scanning; Drug Carriers; Fatty Acids; Lipids; Lythraceae; Microscopy, Electron, Transmission; Nanostructures; Particle Size; Plant Oils; Propolis; Sitosterols; Spectroscopy, Fourier Transform Infrared; Waxes; X-Ray Diffraction

2018
Baseline serum sitosterol level as predictor of adverse clinical events in acute coronary syndrome patients with dyslipidaemia: A sub-analysis of HIJ-PROPER.
    Atherosclerosis, 2018, Volume: 274

    We aimed to examine the effect of serum sitosterol, a cholesterol absorption marker, on clinical outcomes in acute coronary syndrome patients with dyslipidaemia.. This is a sub-analysis of the HIJ-PROPER trial that assesses the effect of aggressive low-density lipoprotein cholesterol (LDL-C) lowering treatment with pitavastatin + ezetimibe in 1734 acute coronary syndrome (ACS) patients with dyslipidaemia. Patients were divided into two groups based on sitosterol level at enrolment (cut-off value was 2.2 μg/mL; a median of baseline sitosterol level), and clinical outcomes were examined.. The mean LDL-C level after 3 years in the low sitosterol group was 84.8 ± 20.1 mg/dL with pitavastatin-monotherapy and 64.6 ± 20.3 mg/dL with pitavastatin + ezetimibe, while corresponding values in the high sitosterol group were 91.0 ± 22.9 mg/dL and 71.1 ± 23.3 mg/dL, respectively. In the high sitosterol group, the Kaplan-Meier event rate for the primary endpoint at 3 years was 26.0% in the pitavastatin + ezetimibe group, as compared with 34.3% in the pitavastatin-monotherapy group (hazard ratio, 0.71; 95% confidence interval, 0.56-0.91; p = 0.006, p-value for interaction = 0.010). However, in the low sitosterol group, there was no significant reduction of the primary endpoint by pitavastatin + ezetimibe therapy.. Aggressive lipid-lowering treatment with ezetimibe had a positive effect on clinical outcomes in the high sitosterol subset of ACS patients with dyslipidaemia, but not in the low sitosterol subset. This effect was independent of LDL-C reduction and suggests that sitosterol measurement on admission in ACS patients might contribute to a "personalised" lipid-lowering approach.

    Topics: Acute Coronary Syndrome; Aged; Biomarkers; Cholesterol, LDL; Dyslipidemias; Ezetimibe; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Japan; Male; Middle Aged; Predictive Value of Tests; Quinolines; Randomized Controlled Trials as Topic; Retrospective Studies; Risk Assessment; Risk Factors; Sitosterols; Time Factors; Treatment Outcome

2018
Graphene oxide-based composite monolith as new sorbent for the on-line solid phase extraction and high performance liquid chromatography determination of ß-sitosterol in food samples.
    Talanta, 2018, Aug-15, Volume: 186

    A composite monolithic column was prepared by redox initiation method for the on-line purification and enrichment of β-sitosterol, in which graphene oxide (GO) was embedded. The obtained monolithic column was characterized by scanning electron microscopy (SEM) and nitrogen adsorption-desorption isotherm measurement, which indicated that the monolith possessed characteristics of porous structure and high permeability. Under the optimum conditions for extraction and determination, the calibration equation was y = 47.92 × -0.1391; the linear range was 0.008-1.0 mg mL

    Topics: Adsorption; Chromatography, High Pressure Liquid; Food Contamination; Graphite; Microscopy, Electron, Scanning; Molecular Structure; Oxides; Plant Oils; Sitosterols; Solid Phase Extraction

2018
Effect of subcritical water and steam explosion pretreatments on the recovery of sterols, phenols and oil from olive pomace.
    Food chemistry, 2018, Nov-01, Volume: 265

    Hydrothermal pretreatments including steam explosion and subcritical water (SCW) facilitate hydrolyses of plant cell wall materials and supply environmentally friendly extraction solvents to recover value added compounds. In this study, effect of steam and SCW and temperature (160, 180 and 200 °C, 5 min) on yield and β-sitosterol content of pomace oil and phenolics were compared for value added utilization of olive pomace. Compared to acid hydrolysis, hydrothermal pretreatments yielded similar oil recovery. 54-76% of the bound oil and 18-32% of the bound β-sitosterol of the pomace were recovered by hydrothermal pretreatments. Steam pretreatment was more effective than SCW pretreatment at lower temperatures, however SCW showed increasing trend on oil yield related to steam pretreatment. As further research on process development, use of sequential temperature might be investigated, starting with steam explosion (<180 °C), followed by SCW pretreatment (>200 °C) to obtain multiple, aqueous and meal, fractions for total valorization of olive pomace.

    Topics: Chromatography, Gas; Color; Hot Temperature; Olea; Olive Oil; Phenols; Sitosterols; Smell; Steam; Sterols; Water

2018
A Validated, Fast Method for Quantification of Sterols and Gut Microbiome Derived 5α/β-Stanols in Human Feces by Isotope Dilution LC-High-Resolution MS.
    Analytical chemistry, 2018, 07-17, Volume: 90, Issue:14

    There has been an increasing interest during recent years in the role of the gut microbiome on health and disease. Therefore, metabolites in human feces related to microbial activity are attractive surrogate marker to track changes of microbiota induced by diet or disease. Such markers include 5α/β-stanols as microbiome-derived metabolites of sterols. Currently, reliable, robust, and fast methods to quantify fecal sterols and their related metabolites are missing. We developed a liquid chromatography-high-resolution mass spectrometry (LC-MS/HRMS) method for the quantification of sterols and their 5α/β-stanols in human fecal samples. Fecal sterols were extracted and derivatized to N, N-dimethylglycine esters. The method includes cholesterol, coprostanol, cholestanol and sitosterol, 5α/β-sitostanol, campesterol and 5α/β-campestanol. Application of a biphenyl column permits separation of isomeric 5α- and 5β-stanols. Sterols are detected in parallel reaction monitoring (PRM) mode and stanols in full scan mode. HRMS allows differentiation of isobaric β-stanols and the [M + 2] isotope peak of the coeluting sterol. Performance characteristics meet the criteria recommended by Food and Drug Administration (FDA) and European Medicines Agency (EMA) guidelines. Analysis of fecal samples from healthy volunteers revealed high interindividual variability of sterol and stanol fractions. Interestingly, cholesterol and sitosterol showed similar fractions of mainly 5β-stanols. In contrast, campesterol is substantially converted to 5α-campestanol and might be a poorer substrate for bacterial metabolism. Robust and fast quantification of fecal sterols and their related stanols by LC-MS/HRMS offers great potential to find novel microbiome-related biomarker in large-scale studies.

    Topics: Cholesterol; Chromatography, Liquid; Feces; Gastrointestinal Microbiome; Humans; Limit of Detection; Phytosterols; Sitosterols; Sterols; Tandem Mass Spectrometry

2018
Lecithin and phytosterols-based mixtures as hybrid structuring agents in different organic phases.
    Food research international (Ottawa, Ont.), 2018, Volume: 111

    In this study the effect of lecithin (L) addition and solvent quality in a well-established oleogel system formed by β-sitosterol and γ-oryzanol (BG) was investigated. Medium chain triglycerides (MCT) and sunflower oil (SFO) were used as triglycerides and hexadecane (HEX) as a model of linear hydrocarbon. Lecithin was proposed due to its natural and versatile properties, showing different functionalities such as emulsifier and co-oleogelator. A study based on hierarchical organization of structured oil was performed applying techniques for bulk, meso and nanoscale. Self-sustained structures could no longer be observed after 40 wt% of BG replacement by lecithin. Small-angle X-ray scattering showed that the formed nanostructures (building blocks) were dependent on type of solvent and BG:L ratio in the mixture of oleogelators. Differential scanning calorimetry showed that stability against temperature was improved decreasing the polarity of the oil, and a time-dependent self-assembly of hybrid systems was observed from thermal and rheological measurements. Microscopy images exhibited changes on typical fibril aggregation of BG as lecithin was added, which promoted to a certain extent the suppression of ribbons. Oscillatory shear and uniaxial compression measurements were influenced by BG:L ratio and solvent mainly at higher lecithin amount. The combination of BG and MCT appeared to be the most affected by lecithin incorporation whereas SFO rendered harder oleogels. These results could contribute to understand the role of both lecithin and solvent type influencing the host oleogelator structure. It was hypothesized that intermolecular BG complex formation is hindered by lecithin, besides this phospholipid also might coexist as a different phase, causing structural changes in the gel network. Addressing the role of co-oleogelator it can provide the opportunity to tune soft materials with adjusted properties.

    Topics: Calorimetry, Differential Scanning; Crystallization; Lecithins; Organic Chemicals; Phenylpropionates; Phytosterols; Sitosterols; Sunflower Oil; Triglycerides

2018
Apoptotic and antiproliferative effects of Stigmast-5-en-3-ol from Dendronephthya gigantea on human leukemia HL-60 and human breast cancer MCF-7 cells.
    Toxicology in vitro : an international journal published in association with BIBRA, 2018, Volume: 52

    Topics: Animals; Anthozoa; Antineoplastic Agents; Apoptosis; Cell Line; Cell Proliferation; DNA Damage; HL-60 Cells; Humans; MCF-7 Cells; Sitosterols

2018
Effect of gestational diabetes mellitus on newborn cholesterol metabolism.
    Atherosclerosis, 2018, Volume: 275

    Impaired glucose metabolism during pregnancy may associate with changes in fetal cholesterol metabolism. We investigated if gestational diabetes mellitus (GDM) affects newborn cholesterol metabolism as determined by cord blood squalene and non-cholesterol sterols. Furthermore, we examined potential correlations between cord blood and maternal serum non-cholesterol sterols.. Pregnant women at risk for GDM (BMI>30 kg/m. The ratios of squalene and non-cholesterol sterols to cholesterol (100 × μmol/mmol of cholesterol) in cord blood did not differ between the infants born to mothers with GDM (n = 15) or mothers with normal glucose tolerance (n = 13). The ratios of sitosterol and campesterol to cholesterol in the cord blood correlated with the corresponding maternal serum ratios (r = 0.70, p < 0.0001) in both groups.. In obese women under good glycaemic control, GDM did not affect newborn cholesterol metabolism. Cord blood sitosterol and campesterol ratios to cholesterol correlated with the corresponding maternal serum ratios thus potentially reflecting maternal-fetal cholesterol transport.

    Topics: Adult; Biomarkers; Blood Glucose; Case-Control Studies; Cholestanol; Cholesterol; Diabetes, Gestational; Female; Fetal Blood; Finland; Humans; Infant, Newborn; Maternal-Fetal Exchange; Obesity; Phytosterols; Pregnancy; Sitosterols; Squalene

2018
In-vitro osteoblast proliferation and in-vivo anti-osteoporotic activity of Bombax ceiba with quantification of Lupeol, gallic acid and β-sitosterol by HPTLC and HPLC.
    BMC complementary and alternative medicine, 2018, Aug-07, Volume: 18, Issue:1

    Bombax ceiba is used traditionally to treat bone disorders, rheumatism, and joint pain. The aim of the study is to carry out osteogenic activity in-vitro and anti-osteoporotic activity in-vivo of stem bark of B. ceiba in surgical ovariectomy model in female rats.. Plant drug: B. ceiba stem bark was extracted with solvents petroleum ether and methanol using Soxhlet extraction. In-vitro osteoblastic proliferation study was performed using UMR-106 cell lines. Both the extracts were undergone to acute toxicity study as per OECD423 guidelines. Female Wistar albino rats 180-240 g were used (n = 6). Surgical ovariectomy was performed under anesthesia to induce bone porosity and loss in all animals except normal control and sham control. Each extract was administered at two dose level: 100 and 200 mg/kg and the standard Raloxifene was given at 1 mg/kg orally for 28 days. The phytochemical study of both the extracts was performed using HPLC and HPTLC.. A significant osteoblast cell proliferation and alkaline phosphatase activity were observed with B. ceiba extracts in UMR-106 cell lines. Surgical removal of ovaries produced significant (p < 0.05) decline in bone mineral density, bone breaking strength, serum ALP, calcium, phosphorus, and estradiol level and marked bone tissue destruction in histology. Administration of petroleum ether and methanolic extract for 28 days significantly (p < 0.05) ameliorated the consequences of ovariectomy induced bone porosity and restored the normal architecture of bone, as compared to OVX control. The phytochemical screening of both the extracts were also carried out. The quantification of phytoconstituents showed the presence of β-sitosterol and lupeol in petroleum ether extract, whereas the lupeol is also quantified in the methanolic extract. The presence of gallic acid was quantified in methanolic extract using HPLC.. B. ceiba: stem bark ameliorated the state of bone fragility and fracture possibly due to estrogenic modulation, as also confirmed by in-vitro osteogenic activity which may be due to the presence of lupeol, gallic acid and β-sitosterol constituents of the plant.

    Topics: Animals; Body Weight; Bombax; Cell Proliferation; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Female; Gallic Acid; Osteoblasts; Osteoporosis; Ovariectomy; Pentacyclic Triterpenes; Plant Extracts; Rats; Rats, Wistar; Sitosterols

2018
Anti-breast-Cancer Activity Exerted by β-Sitosterol-d-glucoside from Sweet Potato via Upregulation of MicroRNA-10a and via the PI3K-Akt Signaling Pathway.
    Journal of agricultural and food chemistry, 2018, Sep-19, Volume: 66, Issue:37

    Breast cancer (BC) is a prominent source of cancer mortality in women throughout the world. β-Sitosterol-d-glucoside (β-SDG), a newly isolated phytosterol from sweet potato, possibly displays potent anticancer activity. However, the probable anticancer mechanisms involved are still unclear. This study sought to study how β-SDG from sweet potato affects two BC cell lines (MCF7 and MDA-MB-231) and nude mice bearing MCF7-induced tumors. In addition, we assessed how β-SDG affects tumor suppressor miR-10a and PI3K-Akt signaling in BC cells. Cell viability and proliferation were determined via MTT and colony-formation assays, and apoptosis was quantified by Hoechst staining and flow cytometry. In addition, miR-10a expression and apoptosis-related protein levels were measured. Our study indicated that β-SDG exhibited cytotoxic activities on MCF7 and MDA-MB-231 cells via inducing apoptosis and activating caspase proteases in these cells. Furthermore, the experimental results in nude mice bearing MCF7-induced tumors demonstrated that oral β-SDG administration at medium (60 mg/kg) or high (120 mg/kg) doses was sufficient to substantially impair the growth of tumors and to decrease the levels of CEA, CA125, and CA153 by 64.71, 74.64, and 85.32%, respectively, relative to those of the controls ( P < 0.01). β-SDG was further found to regulate the expression of PI3K, p-Akt, Bcl-2-family members, and other factors involved in the PI3K-Akt-mediated mitochondrial signaling pathway via the tumor suppressor miR-10a. These findings indicated that β-SDG suppresses tumor growth by upregulating miR-10a expression and inactivating the PI3K-Akt signaling pathway. Furthermore, β-SDG could be developed as a potential therapeutic agent against MCF7-cell-related BC.

    Topics: Animals; Antineoplastic Agents, Phytogenic; Apoptosis; Breast Neoplasms; Female; Glucosides; Humans; Ipomoea batatas; Mice; Mice, Inbred BALB C; Mice, Nude; MicroRNAs; Phosphatidylinositol 3-Kinases; Plant Extracts; Proto-Oncogene Proteins c-akt; Signal Transduction; Sitosterols; Up-Regulation

2018
β-Sitosterol-2-hydroxypropyl-β-cyclodextrin inclusion complex: Characterization and inhibitory effect on adipogenesis in 3T3-L1 pre-adipocytes.
    Steroids, 2018, Volume: 140

    β-Sitosterol (Sit) has been used as a functional food additive. Among its many beneficial effects, this phytosterol plays a role in controlling obesity by inhibiting the adipogenesis process of pre-adipocytes. However, the highly lipophilic character of Sit limits its bioavailability. In the present study, 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) was used to form a complex with Sit, namely the Sit-HP-β-CD inclusion complex, and the inhibitory effect of this complex on adipogenesis in the 3T3-L1 pre-adipocyte cell line was investigated. The results of DSC, TLC,

    Topics: 2-Hydroxypropyl-beta-cyclodextrin; 3T3-L1 Cells; Adipocytes; Adipogenesis; Animals; Mice; Sitosterols

2018
Ichnocarpus frutescens (L.) R. Br. root derived phyto-steroids defends inflammation and algesia by pulling down the pro-inflammatory and nociceptive pain mediators: An in-vitro and in-vivo appraisal.
    Steroids, 2018, Volume: 139

    Topics: Analgesics; Anti-Inflammatory Agents; Apocynaceae; Cytokines; Fatty Acids, Unsaturated; Glucosides; Humans; Inflammation; Interleukin-6; Leukocytes, Mononuclear; Lipopolysaccharides; Macrophages; Molecular Docking Simulation; Nociceptive Pain; Pain Perception; Plant Extracts; Plant Roots; Sitosterols; Steroids; Stigmasterol; Tumor Necrosis Factor-alpha

2018
Identification of β-Sitosterol as in Vitro Anti-Inflammatory Constituent in Moringa oleifera.
    Journal of agricultural and food chemistry, 2018, Oct-17, Volume: 66, Issue:41

    β-Sitosterol is a well known phytosterol in plants, but owing to its poor solubility in typical media, determining its cellular mechanisms has been proven to be difficult. In this study, we investigated the anti-inflammatory activity of β-sitosterol (BSS) isolated from Moringa oleifera in two cell lines. Over a dose range of 7.5 to 30 μM, BSS dispersed well in the medium as nanoparticles with diameters of 50 ± 5 nm and suppressed the secretion of inflammatory factors from keratinocytes and macrophages induced by PGN, TNF-α, or LPS, such as TNF-α, IL-1β, IL-6, IL-8, and ROS, separately. In addition, BSS significantly reduced the expression of NLRP3, a key component of NLRP3 inflammasomes, and inhibited the activation of caspase-1. There was partial inhibition of NF-κB in macrophages. This is the first study to report an increase in the solubility of nearly water-insoluble phytosterols via the formation of nanoparticles and to delineate the formulation's capacity to inhibit the signal transduction pathways of inflammation in macrophages.

    Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Caspase 1; Cell Line; Cell Survival; Cytokines; Drug Compounding; Humans; Keratinocytes; Macrophages; Mice; Moringa oleifera; Nanoparticles; Particle Size; Signal Transduction; Sitosterols; Solubility; Surface Properties

2018
Intake of stigmasterol and β-sitosterol alters lipid metabolism and alleviates NAFLD in mice fed a high-fat western-style diet.
    Biochimica et biophysica acta. Molecular and cell biology of lipids, 2018, Volume: 1863, Issue:10

    To investigate and compare the effects of two common dietary phytosterols, stigmasterol and β-sitosterol, in altering lipid metabolism and attenuating nonalcoholic fatty liver disease (NAFLD).. Stigmasterol and β-sitosterol were administered to mice at 0.4% in a high-fat western-style diet (HFWD) for 17 weeks.. Stigmasterol and β-sitosterol significantly ameliorated HFWD-induced fatty liver and metabolic abnormalities, including elevated levels of hepatic total lipids, triacylglycerols, cholesterol and liver histopathology. Both phytosterols decreased the levels of intestinal bile acids, accompanied by markedly increased fecal lipid levels. In addition, they altered the expression of genes involved in lipid metabolism. β-Sitosterol was less effective in affecting most of these parameters. Lipidomic analysis of liver and serum samples showed that stigmasterol prevented the HFWD-induced elevation of some di- and triacylglycerol species and lowering of some phospholipid species. Stigmasterol also decreased serum levels of ceramides.. Stigmasterol and β-sitosterol, at a dose corresponding to that suggested for humans by the FDA for lowering cholesterol levels, are shown to alleviate HFWD-induced NAFLD. Stigmasterol was more effective than β-sitosterol, possibly because of its suppression of hepatic lipogenic gene expression and modulation of circulating ceramide levels.

    Topics: Animals; Bile Acids and Salts; Ceramides; Diet, High-Fat; Disease Models, Animal; Feces; Lipid Metabolism; Mice; Non-alcoholic Fatty Liver Disease; Phospholipids; Sitosterols; Stigmasterol; Treatment Outcome; Triglycerides

2018
Determination of Key Active Components in Different Edible Oils Affecting Lipid Accumulation and Reactive Oxygen Species Production in HepG2 Cells.
    Journal of agricultural and food chemistry, 2018, Nov-14, Volume: 66, Issue:45

    Owing to the poor ability of cells to decompose triglycerides, most studies of edible oil have depended on animal or clinical trials. However, such trials are expensive and time-consuming, and the results are limited to considerable individual differences. This is the first study to comprehensively investigate the effect of different oils on the lipid accumulation and reactive oxygen species (ROS) production in HepG2 cells by hydrolyzing oil to fatty acids with integrated fat content. In addition, the key components of fatty acid composition, phytosterol, polyphenols, and tocopherol/tocotrienol in different oils, contributing to a decrease in content of lipid accumulation, cholesterol, ROS, and malondialdehyde (MDA), were analyzed using multivariate analysis. The results showed that the lipid accumulation content of coconut oil, Pu'er tea oil, olive oil, and flaxseed oil at a concentration of 200 μM decreased by 45.98 ± 0.75, 50.35 ± 1.37, 40.43 ± 2.44, and 42.76 ± 1.88%, respectively, compared with the lard. In addition, the ROS contents of Pu'er tea oil, olive oil, and flaxseed oil had no significant difference from that of control cells ( p < 0.05). In the results, (3β,5α)-stigmastan-3-yl, cholane-5,20(22)-diene-3b-ph, and β-sitosterol were determined to be the key components in edible oils associated with lipid accumulation and ROS production.

    Topics: Cholesterol; Hep G2 Cells; Humans; Lipid Metabolism; Malondialdehyde; Plant Oils; Polyphenols; Reactive Oxygen Species; Sitosterols; Triglycerides

2018
In vitro and in vivo antidiabetic activity of isolated fraction of Prosopis cineraria against streptozotocin-induced experimental diabetes: A mechanistic study.
    Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 2018, Volume: 108

    Topics: Animals; Antioxidants; Blood Glucose; Diabetes Complications; Diabetes Mellitus, Experimental; Glycated Hemoglobin; Hypoglycemic Agents; Insulin; Lipids; Liver; Male; Plant Extracts; Prosopis; Rats; Rats, Wistar; Sitosterols; Streptozocin

2018
Pharmacokinetics and pharmacodynamics of citrus peel extract in lipopolysaccharide-induced acute lung injury combined with Pinelliae Rhizoma Praeparatum.
    Food & function, 2018, Nov-14, Volume: 9, Issue:11

    Dry citrus peel (Chenpi) is not only consumed as a dietary supplement, but also used for the treatment of respiratory diseases. Pinelliae Rhizoma Praeparatum (Banxia) is always used with Chenpi for the treatment of respiratory diseases, but β-sitosterol, the main active component in Banxia, as a food additive, shows no respiratory system activity. In the present study, the pharmacokinetic characters showed that the absorption of the active components of Chenpi was accelerated under pathological conditions combined with Banxia. Although the bioavailability of active components did not significantly change, the distribution of active components in tissues increased, particularly in the target organ. These results are consistent with the combination of Chenpi with β-sitosterol. Furthermore, the pharmacodynamics result also indicated that Chenpi combined with Banxia or β-sitosterol was able to ameliorate histopathologic damage and decrease the levels of inflammatory factors. The results suggest that pharmacokinetic interactions improve the pharmacological activity of Chenpi in respiratory diseases.

    Topics: Acute Lung Injury; Animals; Citrus; Disease Models, Animal; Drugs, Chinese Herbal; Fruit; Lipopolysaccharides; Male; Pinellia; Plant Extracts; Rats; Rats, Sprague-Dawley; Reproducibility of Results; Sitosterols

2018
Vitamin D
    Scientific reports, 2018, 11-05, Volume: 8, Issue:1

    Vitamin D

    Topics: Arabidopsis; Sitosterols; Vitamin D

2018
First Report of Plant-Derived β-Sitosterol with Antithrombotic, in Vivo Anticoagulant, and Thrombus-Preventing Activities in a Mouse Model.
    Journal of natural products, 2018, 11-26, Volume: 81, Issue:11

    Inhibitors of thrombin, a key enzyme in the blood coagulation cascade, are of great interest because of their selective specificity and effectiveness in anticoagulation therapy against cardiovascular disorders. The natural soybean phytosterol, β-sitosterol (BSS) demonstrated anticoagulant activity by dose-dependent inhibition of thrombin in an uncompetitive manner with a K

    Topics: Animals; Anticoagulants; Antithrombins; Catalysis; Disease Models, Animal; Female; Fibrinogen; Humans; Male; Mice; Plants; Platelet Aggregation Inhibitors; Sitosterols; Thrombin; Thrombosis

2018
Elucidation of the anticancer potential and tubulin isotype-specific interactions of β-sitosterol.
    Journal of biomolecular structure & dynamics, 2018, Volume: 36, Issue:1

    Beta-sitosterol (β-SITO), a phytosterol present in many edible vegetables, has been reported to possess antineoplastic properties and cancer treatment potential. We have shown previously that it binds at a unique site (the 'SITO-site') compared to the colchicine binding site at the interface of α- and β-tubulin. In this study, we investigated the anticancer efficacy of β-SITO against invasive breast carcinoma using MCF-7 cells. Since 'isotypes' of β-tubulin show tissue-specific expression and many are associated with cancer drug resistance, using computer-assisted docking and atomistic molecular dynamic simulations, we also examined its binding interactions to all known isotypes of β-tubulin in αβ-tubulin dimer. β-SITO inhibited MCF-7 cell viability by up to 50%, compared to vehicle-treated control cells. Indicating its antimetastatic potential, the phytosterol strongly inhibited cell migration. Immunofluorescence imaging of β-SITO-treated MCF-7 cells exhibited disruption of the microtubules and chromosome organization. Far-UV circular dichroism spectra indicated loss of helical stability in tubulin when bound to β-SITO. Docking and MD simulation studies, combined with MM-PBSA and MM-GBSA calculations revealed that β-SITO preferentially binds with specific β-tubulin isotypes (β

    Topics: Antineoplastic Agents; Binding Sites; Breast Neoplasms; Female; Humans; MCF-7 Cells; Molecular Docking Simulation; Molecular Dynamics Simulation; Molecular Structure; Protein Binding; Protein Domains; Protein Multimerization; Sitosterols; Tubulin

2018
New flavonol glycoside from Scabiosa prolifera L. aerial parts with in vitro antioxidant and cytotoxic activities.
    Natural product research, 2017, Volume: 31, Issue:24

    Phytochemical investigation of the chemical constituents of the aerial parts of Scabiosa prolifera L. led to the isolation of one new flavonol glycoside, kaempferol-3-O-(4″,6″-di-E-p-coumaroyl)-β-D-galactopyranoside (1), along with ten other known compounds including luteolin-7-O-(2″-O-ethyl-β-glucopyranoside), β-sitosterol, β-sitosterylglucoside, ursolic acid, corosolic acid, ursolic acid 3-O-β-D-arabinopyranoside, apigenin, methyl-α-D-glucopyranoside, luteolin-7-O-β-glucopyranoside and isoorientin. The structures of all isolated compounds were established using chemical methods and spectroscopic methods including IR, UV, NMR (1D and 2D) and HRESIMS. All compounds were isolated for the first time from the plant. The antioxidant and cytotoxic activities of compounds 1 and 2 were also investigated.

    Topics: Antioxidants; Cardiac Glycosides; Cytotoxins; Dipsacaceae; Flavonols; Glycosides; Kaempferols; Molecular Structure; Plant Components, Aerial; Plant Extracts; Sitosterols; Triterpenes

2017
A UHPLC method for the rapid separation and quantification of phytosterols using tandem UV/Charged aerosol detection - A comparison of both detection techniques.
    Journal of pharmaceutical and biomedical analysis, 2017, Jun-05, Volume: 140

    The presented work describes the development and validation of a rapid UHPLC-UV/CAD method using a core-shell particle column for the separation and quantitative analysis of seven plant sterols and stanols. The phytosterols (ergosterol, brassicasterol, campesterol, fucosterol, stigmasterol, and β-sitosterol) and the phytostanol stigmastanol were separated and analyzed in 8.5min. The sample pre-treatment procedure was optimized to be less time-consuming than any other published method, especially due to no need of derivatization, evaporation and even reconstitution step. The chromatographic separation was performed on the Kinetex 1.7μ Phenyl-hexyl column (100×2.1mm) with a mobile phase acetonitrile/water according to the gradient program at a flow rate of 0.9mLmin

    Topics: Aerosols; Chromatography, High Pressure Liquid; Phytosterols; Sitosterols; Sterols

2017
Antibacterial and antibiotic potentiating activities of tropical marine sponge extracts.
    Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 2017, Volume: 196

    Increasing prevalence of antibiotic resistance has led research to focus on discovering new antimicrobial agents derived from the marine biome. Although ample studies have investigated sponges for their bioactive metabolites with promising prospects in drug discovery, the potentiating effects of sponge extracts on antibiotics still remains to be expounded. The present study aimed to investigate the antibacterial capacity of seven tropical sponges collected from Mauritian waters and their modulatory effect in association with three conventional antibiotics namely chloramphenicol, ampicillin and tetracycline. Disc diffusion assay was used to determine the inhibition zone diameter (IZD) of the sponge total crude extracts (CE), hexane (HF), ethyl acetate (EAF) and aqueous (AF) fractions against nine standard bacterial isolates whereas broth microdilution method was used to determine their minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and antibiotic potentiating activity of the most active sponge extract. MIC values of the sponge extracts ranged from 0.039 to 1.25mg/mL. Extracts from Neopetrosia exigua rich in beta-sitosterol and cholesterol displayed the widest activity spectrum against the 9 tested bacterial isolates whilst the best antibacterial profile was observed by its EAF particularly against Staphylococcus aureus and Bacillus cereus with MIC and MBC values of 0.039mg/mL and 0.078mg/mL, respectively. The greatest antibiotic potentiating effect was obtained with the EAF of N. exigua (MIC/2) and ampicillin combination against S. aureus. These findings suggest that the antibacterial properties of the tested marine sponge extracts may provide an alternative and complementary strategy to manage bacterial infections.

    Topics: Acetates; Ampicillin; Animals; Anti-Bacterial Agents; Aquatic Organisms; Biological Products; Chloramphenicol; Disk Diffusion Antimicrobial Tests; Drug Agonism; Drug Discovery; Drug Resistance, Bacterial; Gram-Negative Bacteria; Gram-Positive Bacteria; Indian Ocean; Mauritius; Microbial Sensitivity Tests; Porifera; Sitosterols; Solvents; Tetracycline

2017
A kaempferol triglycoside from Tephrosia preussii Taub. (Fabaceae).
    Natural product research, 2017, Volume: 31, Issue:21

    A phytochemical investigation of the MeOH extract of twigs and leaves of Tephrosia preussi was carried out to give a new kaempferol triglycoside, named tephrokaempferoside (1), together with five known compounds: tephrosin (2), betulinic acid (3), lupeol (4), β-sitosterol (5) and 3-O-β-d-glucopyranoside of β-sitosterol (6). The structure of the new compound was characterised by analyses of NMR (1D and 2D) and MS data, and chemical conversion. Tephrokaempferoside (1) had weak antibacterial activity against Klebsiella pneumoniae with an MIC value of 150 μg/mL.

    Topics: Anti-Bacterial Agents; Betulinic Acid; Drug Evaluation, Preclinical; Glycosides; Kaempferols; Klebsiella pneumoniae; Magnetic Resonance Spectroscopy; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Rotenone; Sitosterols; Tephrosia; Triterpenes

2017
A new pyranoxanthone from Garcinia nervosa.
    Natural product research, 2017, Volume: 31, Issue:21

    Phytochemical studies on the stem bark of Garcinia nervosa has resulted in the discovery of one new pyranoxanthone derivative, garner xanthone (1) and five other compounds, 1,5-dihydroxyxanthone (2), 6-deoxyisojacareubin (3), 12b-hydroxy-des-D-garcigerrin A (4) stigmasterol (5), and β-sitosterol (6). The structures of these compounds were elucidated with the aid of spectroscopic techniques, such as NMR and MS. The crude extracts of the plant were assessed for their antimicrobial activity.

    Topics: Anti-Infective Agents; Drug Evaluation, Preclinical; Garcinia; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Plant Bark; Pyrans; Sitosterols; Stigmasterol; Xanthenes; Xanthones

2017
Synthesis and characterization of redox-sensitive heparin-β-sitosterol micelles: Their application as carriers for the pharmaceutical agent, doxorubicin, and investigation of their antimetastatic activities in vitro.
    Materials science & engineering. C, Materials for biological applications, 2017, Jun-01, Volume: 75

    Although there are several clinical attempts to treat tumors at the primary site, only few therapies can inhibit the spread of metastatic cancers. In this study, we synthesized redox-sensitive heparin-β-sitosterol micelles that show antimetastatic activity. Proton nuclear magnetic resonance and Fourier transform infrared analyses confirmed the formation of bioreducible heparin-β-sitosterol (bHSC) conjugates, whereas dynamic light scattering was used to measure the particle size and zeta potential. Both 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide and flow cytometry assays confirmed the low toxicity of the synthesized micelles. Doxorubicin (Dox) was encapsulated via the dialysis method, and its loading and encapsulation efficiencies were 16.49±1.2% and 58.47±1.87%, respectively. An in vitro release study showed that approximately 89% and 52% of Dox were released after 48h in the presence and absence of reduced glutathione, respectively. The hemocompatibility and antimetastatic effects of bHSC were evaluated using the hemolysis and scratch assays, respectively. F-Actin fluorescence microscopy showed that heparin- and bHSC-treated HeLa cells had poorly oriented stress fibers. In summary, the synthesized bHSC micelles are good candidates as drug delivery systems owing to their low toxicity, excellent hemocompatibility, and antimetastatic effects.

    Topics: Doxorubicin; Drug Carriers; HeLa Cells; Heparin; Humans; Micelles; Neoplasm Metastasis; Neoplasms; Oxidation-Reduction; Sitosterols

2017
Influence of HDL particles on cell-cholesterol efflux under various pathological conditions.
    Journal of lipid research, 2017, Volume: 58, Issue:6

    It has been reported that low cell-cholesterol efflux capacity (CEC) of HDL is an independent risk factor for CVD. To better understand CEC regulation, we measured ABCA1- and scavenger receptor class B type I (SR-BI)-dependent cell-cholesterol efflux, HDL anti-oxidative capacity, HDL particles, lipids, and inflammatory- and oxidative-stress markers in 122 subjects with elevated plasma levels of triglyceride (TG), serum amyloid A (SAA), fibrinogen, myeloperoxidase (MPO), or β-sitosterol and in 146 controls. In controls, there were strong positive correlations between ABCA1-dependent cholesterol efflux and small preβ-1 concentrations (

    Topics: Antioxidants; ATP Binding Cassette Transporter 1; Biological Transport; CD36 Antigens; Cholesterol, HDL; Female; Fibrinogen; Humans; Male; Middle Aged; Peroxidase; Serum Amyloid A Protein; Sitosterols; Triglycerides

2017
Microstructure of β-Sitosterol:γ-Oryzanol Edible Organogels.
    Langmuir : the ACS journal of surfaces and colloids, 2017, 05-09, Volume: 33, Issue:18

    Rheology and atomic force microscopy (AFM) were employed to examine the microstructure of β-sitosterol:γ-oryzanol organogels in sunflower oil. Using time-resolved rheology, we followed gel formation, paying specific attention to the fibril aggregation process, which had not been studied in detail previously for this system. Using AFM, we observed gel structures directly and obtained detailed information on the gel structure, far exceeding previous studies. Our analysis suggests that though gels are formed by the self-assembly and aggregation of one-dimensional fibrils, the manner in which these fibrils aggregate into ribbons results in complex structures of higher dimensionality. We emphasize that it is a surprise to find ribbons and not twisted strands. Comparing AFM images of 10% w/w and 20% w/w gelator systems, we observed differences in the degree of branching which are consistent with the rheology. We also observed the individual self-assembled fibrils which make up these gels with much greater clarity than in previous microscopy studies, and the fibril diameters of ∼9.8 nm we measured agree excellently with those obtained from existing small-angle neutron scattering data. These results provide new insight into the structure and formation kinetics of this important organogel system.

    Topics: Gels; Phenylpropionates; Scattering, Small Angle; Sitosterols

2017
BAMBI overexpression together with β-sitosterol ameliorates NSCLC via inhibiting autophagy and inactivating TGF-β/Smad2/3 pathway.
    Oncology reports, 2017, Volume: 37, Issue:5

    Non-small cell lung cancer (NSCLC) has the highest mortality rate among all solid tumors with a poor prognosis. The BMP and activin receptor membrane bound inhibitor (BAMBI) has been identified as a hallmark of NSCLC and β-sitosterol possesses antitumor potentiality. This study explores the effect of BAMBI overexpression and β-sitosterol in the context of NSCLC. The results revealed that the transfection of pcDNA‑BAMBI and β-sitosterol treatment significantly reduced the levels of autophagy markers light chain 3 (LC3) II and Beclin 1, whereas the levels of LC3 I and p62 were promoted. The reduced punctate accumulations of GFP-LC3 were detected in pcDNA-BAMBI and β-sitosterol groups, especially in pcDNA-BAMBI + β-sitosterol group. BAMBI overexpression and β-sitosterol induced G0/G1 cell cycle arrest and inhibted cell proliferation in A549 cells. In addition, the levels of transforming growth factor-β (TGF‑β)/p-Smad2/3/c-Myc pathway proteins were decreased. The TGF-β overexpression further confirmed that BAMBI overexpression and β-sitosterol treatment suppre-ssed autohagy and viability of A549 cells was through TGF-β/Smad2/3/c-Myc pathway. Finally, the tumor growth was suppressed in NSCLC xenografts, and the inhibitory effect was stronger under treatment of pcDNA-BAMBI toge-ther with β-sitosterol. These results indicate that BAMBI overexpression and β-sitosterol may serve as novel targets for the treatment of NSCLC.

    Topics: A549 Cells; Animals; Autophagy; Carcinoma, Non-Small-Cell Lung; Cell Line, Tumor; Cell Proliferation; Gene Expression Regulation, Neoplastic; Genetic Vectors; Humans; Lung Neoplasms; Membrane Proteins; Mice; Signal Transduction; Sitosterols; Smad2 Protein; Smad3 Protein; Transforming Growth Factor beta; Up-Regulation

2017
EVALUATION OF THE ANTI-INFLAMMATORY CAPACITY OF BETA-SITOSTEROL IN RODENT ASSAYS.
    African journal of traditional, complementary, and alternative medicines : AJTCAM, 2017, Volume: 14, Issue:1

    Beta-sitosterol (BS) is a compound discovered to be present in numerous plants. A number of interesting biomedical properties have been attributed to BS, including immuno-modulating and anti-inflammatory activities. Therefore, the aim of this report was to evaluate its anti-inflammatory capacity by applying various rodent experimental tests.. To carry out the objective of the study we applied the methods indicated here. Two of the adopted methods were based on the passive reverse Arthus reaction: the rat paw edema test and the rat pleurisy assay. We also applied two methods related with the non-specific acute inflammation: the mouse ear edema test, and the mouse mieloperoxidase activity assay.. The results obtained in all tests established a significant anti-inflammatory potential of BS. In the rat paw edema test we found an inhibitory effect which goes from 50-70%; in the rat pleurisy assay our findings with respect to the volume of pleural exuded showed a reduction of 46%, as well as a 20% low amount of neutrophils in comparison with the level of the control group. In the mouse ear edema test we found a mean inflammatory inhibition of 75%, and with respect to mieloproxidase activity the results showed a significant inhibition induced by the three doses of BS.. In the present study we determined a potent anti-inflammatory capacity of BS in specific and non-specific types of acute inflammation in rodents.

    Topics: Animals; Anti-Inflammatory Agents; Drug Evaluation, Preclinical; Edema; Humans; Male; Mice; Plant Extracts; Pleurisy; Rats; Rats, Wistar; Sitosterols

2017
Beta sitosterol and Daucosterol (phytosterols identified in Grewia tiliaefolia) perturbs cell cycle and induces apoptotic cell death in A549 cells.
    Scientific reports, 2017, 06-13, Volume: 7, Issue:1

    Lung cancer is the leading cause of cancer related deaths both in developed and developing countries. Since majority of the existing therapeutic methods harms both normal and malignant cells, a viable alternative is to switch into safe and beneficial traditional medicinal plants. Hence the present study was framed to identify selective anti-lung cancer agents from the medicinal plant Grewia tiliaefolia (GT). Cell viability experiments showed that benzene extract of GT (BGT) leaf effectively inhibited the growth of A549 cells, while being non-toxic to normal human lung L132 and PBMC cells. Ames and comet assays demonstrated that BGT is of non-mutagenic and non-genotoxic nature in untransformed cells. The hematological and histopathological profiles of the in vivo acute and sub-acute toxicity studies demonstrated that BGT is safe and tolerable. Importantly, western blot analysis and Annexin V-FITC staining confirmed that BGT promotes mitochondrial dependent apoptotic cell death in A549 cells by arresting cell cycle at G2/M phase. Bio-assay guided fractionation revealed the presence of phytosteols (β-sitosterol and daucosterol) which significantly inhibited the growth of A549 cells both alone and in combination. This study warrants that these phytosterols in alone or in combination can be considered as safe and potential drug candidates for lung cancer treatment.

    Topics: Apoptosis; Cell Cycle; Cell Line, Tumor; Grewia; Humans; Sitosterols

2017
Pedologic Factors Affecting Virgin Olive Oil Quality of "Chemlali" Olive Trees (Olea europaea L.).
    Journal of oleo science, 2017, Aug-01, Volume: 66, Issue:8

    The aim of this study examined the characterization of extra virgin olive oil samples from the main cultivar Chemlali, grown in five olive orchards with different soil type (Sandy, Clay, Stony, Brown, Limestone and Gypsum). Volatile compounds were studied using headspace-solid phase micro-extraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) technics. Moreover, the sterol profile was established using gas chromatography-mass spectrometry. 35 different volatile compounds were identified: alcohols, esters, aldehydes, ketones and hydrocarbons. The chemical composition of the volatile fraction was characterized by the preeminence of 2-hexenal (32.75%) and 1-hexanol (31.88%). Three sterols were identified and characterized. For all olive oil samples, ß-sitosterol (302.25 mg/kg) was the most abundant sterol. Interestingly, our results showed significant qualitative and quantitative differences in the levels of the volatile compounds and sterols from oils obtained from olive trees grown in different soil type.

    Topics: Alcohols; Aldehydes; Esters; Food Quality; Gas Chromatography-Mass Spectrometry; Hexobarbital; Hydrocarbons; Ketones; Olea; Olive Oil; Sitosterols; Soil; Solid Phase Microextraction; Sterols; Volatile Organic Compounds

2017
Selection of Biodegrading Phytosterol Strains.
    Methods in molecular biology (Clifton, N.J.), 2017, Volume: 1645

    The phytosterol-biotransforming strains were selected from Mycobacterium sp., using a high concentration of β-sitosterol. The selection was made by culturing the strains in a medium enriched with 14 g β-sitosterol/L as the unique source of carbon. During 2 months, the bacterial cultures were transferred successively. The extraction of the biotransformation products was made with methanol and ethyl acetate. The qualitative and quantitative analysis was made by means of thin-layer chromatography, gas-liquid chromatography (GLC), and GLC-mass spectrometry. Under these conditions, it was observed that after seven transfers, the strains Mycobacterium sp. MB-3683 and the Mycobacterium fortuitum B-11045 increased their biotransformation capacity from 20% to 64% and from 34% to 55%, respectively. The products in the highest proportion identified for each trial were androstenedione and androstadienedione. The results suggest that the high substrate concentration could be a selective mechanism to obtain strains more efficient in the biotransformation of β-sitosterol into steroidal bases.

    Topics: Biotransformation; Gas Chromatography-Mass Spectrometry; Mycobacterium; Phytosterols; Sitosterols

2017
β-Sitosterol Bioconversion to Androstenedione in Microtiter Plates.
    Methods in molecular biology (Clifton, N.J.), 2017, Volume: 1645

    Microtiter plates are routinely used as low-cost miniaturized bioreactors due to the large number of experiments that can be conducted simultaneously under similar conditions and replicate all functions of bench-scale reactors at dramatically smaller volumes. These plates, due to the standard footprint, can be integrated with liquid-handling systems and associated equipment expanding considerably their application and use. However, care has to be taken to operate the microtiter plates in optimized mixing and oxygen transfer conditions, preventing medium evaporation in prolonged experiment runs. Here, we describe the production of 4-androstene-3,17-dione (androstenedione; AD), a key pharmaceutical steroid intermediate, by Mycobacterium sp. NRRL B-3805 via the selective cleavage of the side-chain of β-sitosterol using 24-well microtiter plates.

    Topics: Androstenedione; Bioreactors; Biotransformation; Metabolic Engineering; Mycobacterium; Sitosterols

2017
Biocatalysis of Steroids with Mycobacterium sp. in Aqueous and Organic Media.
    Methods in molecular biology (Clifton, N.J.), 2017, Volume: 1645

    Mycobacterium sp. can convert steroids such as β-sitosterol, campesterol, and cholesterol into commercially interesting products. In aqueous systems, the biocatalysis is limited by the low solubility of the steroids in water. This may be overcome by the introduction of an organic phase acting as a substrate and/or product reservoir.In this chapter, we describe the biocatalysis of β-sitosterol to 4-androstene-3,17-dione (AD) and 1,4-androstadiene-3,17-dione (ADD) both in aqueous and organic-aqueous systems. In the latter case, both traditional organic solvents and green solvents are proposed.

    Topics: Androstenedione; Biocatalysis; Mycobacterium; Sitosterols; Solvents; Steroids; Water

2017
    The Biochemical journal, 2017, 08-17, Volume: 474, Issue:17

    Arthritis is a chronic inflammatory disease which reduces the life quality of affected individuals. Therapeutic tools used for treating inflammatory pain are associated with several undesirable effects.

    Topics: Acute Pain; Administration, Cutaneous; Administration, Oral; Analgesics, Non-Narcotic; Animals; Anti-Inflammatory Agents, Non-Steroidal; Arthritis, Experimental; Brazil; Buddleja; Drug Stability; Drug Storage; Ethnopharmacology; Gels; Hot Temperature; Male; Mice; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Sitosterols; Stigmasterol; Viscosity

2017
Constituents from solid-cultured Antrodia camphorata.
    Natural product research, 2017, Volume: 31, Issue:21

    Topics: Antrodia; Benzoquinones; Culture Techniques; Hep G2 Cells; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Sitosterols; Taiwan; Terpenes

2017
Hair Regenerative Mechanisms of Red Ginseng Oil and Its Major Components in the Testosterone-Induced Delay of Anagen Entry in C57BL/6 Mice.
    Molecules (Basel, Switzerland), 2017, Sep-08, Volume: 22, Issue:9

    Hair loss (alopecia) is a universal problem for numerous people in the world. The present study was conducted to investigate the effects of red ginseng oil (RGO) and its major components on hair re-growth using testosterone (TES)-induced delay of anagen entry in C57BL/6 mice and their mechanisms of action. Seven-week-old C57BL/6 mice were daily treated with TES for 1 h prior to topical application of 10% RGO, 1% linoleic acid (LA), 1% β-sitosterol (SITOS), or 1% bicyclo(10.1.0)tridec-1-ene (BICYCLO) once a day for 28 days. Hair regenerative capacity was significantly restored by treatment of RGO and its major compounds in the TES-treated mice. Histological analysis showed that RGO along with LA and SITOS but not BICYCLO promoted hair growth through early inducing anagen phase that was delayed by TES in mice. Treatment of mice with RGO, LA, or SITOS up-regulated Wnt/β-catenin and Shh/Gli pathways-mediated expression of genes such as β-catenin, Lef-1, Sonic hedgehog, Smoothened, Gli-1, Cyclin D1, and Cyclin E in the TES-treated mice. In addition, RGO and its major components reduced the protein level of TGF-β but enhanced the expression of anti-apoptotic protein Bcl-2. These results suggest that RGO is a potent novel therapeutic natural product for treatment of androgenic alopecia possibly through hair re-growth activity of its major components such as LA and SITOS.

    Topics: Alopecia; Animals; beta Catenin; Cyclins; Disease Models, Animal; Gene Expression Regulation; Hair Follicle; Hedgehog Proteins; Linoleic Acid; Lymphoid Enhancer-Binding Factor 1; Male; Mice; Mice, Inbred C57BL; Panax; Plant Oils; Proto-Oncogene Proteins c-bcl-2; Regeneration; Sitosterols; Smoothened Receptor; Testosterone; Transforming Growth Factor beta; Zinc Finger Protein GLI1

2017
Metal ions accelerated phytosterol thermal degradation on Ring A & Ring B of steroid nucleus in oils.
    Food research international (Ottawa, Ont.), 2017, Volume: 100, Issue:Pt 2

    This study aimed to investigate the effect of metal ions on the degradation of phytosterols in oils. The oil was heated at 180°C for 1h with/without addition of Fe

    Topics: Antioxidants; Cholestadienols; Cholesterol; Food Analysis; Food Handling; Gas Chromatography-Mass Spectrometry; Hot Temperature; Nutritive Value; Oils; Phytosterols; Sitosterols; Steroids; Stigmasterol

2017
Nepeta deflersiana attenuates isoproterenol-induced myocardial injuries in rats: Possible involvement of oxidative stress, apoptosis, inflammation through nuclear factor (NF)-κB downregulation.
    Phytomedicine : international journal of phytotherapy and phytopharmacology, 2017, Oct-15, Volume: 34

    Nepeta deflersiana (Lamiaceae) is a perennial herb used in the Saudi and Yemeni folk medicine as an anti-inflammatory, carminative, and antirheumatic agent.. This study explores the phytochemistry of the plant and the cardioprotective effect of N. deflersiana ethanolic extract (NDEE) against isoproterenol (ISP)-induced myocardial injury in rats.. Cardiac function, serum cardiac enzymes, myocardial antioxidants, inflammatory, and apoptotic biomarkers, and histopathological parameters were studied in ISP-injured Wistar rat heart tissues.. To the best of our knowledge, this is the first study to report the isolation of nine secondary metabolites from this plant: 1α-hydroxy-7α,14α,18-triacetoxy-isopimara-8,15-diene (1), β-sitosterol (2), lupeol (3), ursolic acid (4), 2,3-dihydroxy ursolic acid (5), caffeic acid (6), methyl rosmarinate (7), rosmarinic acid (8), and an irridoid glucoside 8-epi-7-deoxyloganic acid (9). To explain the mechanisms underlying the cardioprotective effect of NDEE, we evaluated the redox-sensitivity of NDEE in ISP-induced cardiac injury. The oral administration of NDEE (50 and 100 mg/kg b.w) prevented the depletion of endogenous antioxidants (CAT, SOD, NP-SH, and NO) and myocyte injury marker enzymes and inhibited lipid peroxidation (MDA, MPO). Moreover, NDEE downregulated the expression of pro-inflammatory cytokines (TNFα, IL-6, and IL-10) and apoptotic markers (caspase-3 and Bax) and upregulated the anti-apoptotic protein Bcl2. Furthermore, NDEE pretreatment significantly downregulated cardiac NF-κB (p65) expression, NF-κB-DNA binding activity, and MPO activity. Histological data showed that NDEE pretreatment reduced myonecrosis, edema, and infiltration of inflammatory cells and restored the architecture of cardiomyocytes.. NDEE demonstrated strong antioxidant, cardioprotective, anti-inflammatory, and anti-apoptotic potential against myocardial damage. This further endorses the use of N. deflersiana in Yemeni folk medicine against cardiovascular diseases.

    Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Apoptosis; Caspase 3; Cytokines; Down-Regulation; Heart; Inflammation; Iridoids; Isoproterenol; Lipid Peroxidation; Male; Myocardium; Nepeta; NF-kappa B; Oxidative Stress; Plant Extracts; Rats; Rats, Wistar; Sitosterols

2017
Spectral phasor analysis reveals altered membrane order and function of root hair cells in Arabidopsis dry2/sqe1-5 drought hypersensitive mutant.
    Plant physiology and biochemistry : PPB, 2017, Volume: 119

    Biological membranes allow the regulation of numerous cellular processes, which are affected when unfavorable environmental factors are perceived. Lipids and proteins are the principal components of biological membranes. Each lipid has unique biophysical properties, and, therefore the lipid composition of the membrane is critical to maintaining the bilayer structure and functionality. Membrane composition and integrity are becoming the focus of studies aiming to understand how plants adapt to its environment. In this study, using a combination of di-4-ANEPPDHQ fluorescence and spectral phasor analysis, we report that the drought hypersensitive/squalene epoxidase (dry2/sqe1-5) mutant with reduced major sterols such as sitosterol and stigmasterol in roots presented higher membrane fluidity than the wild type. Moreover, analysis of endomembrane dynamics showed that vesicle formation was affected in dry2/sqe1-5. Further analysis of proteins associated with sterol rich micro domains showed that dry2/sqe1-5 presented micro domains function altered.

    Topics: Arabidopsis; Arabidopsis Proteins; Cell Membrane; Dehydration; Membrane Fluidity; Plant Roots; Sitosterols; Squalene Monooxygenase; Stigmasterol

2017
Antifungal activity of sterols and dipsacus saponins isolated from Dipsacus asper roots against phytopathogenic fungi.
    Pesticide biochemistry and physiology, 2017, Volume: 141

    The in vivo antifungal activity of crude extracts of Dipsacus asper roots was evaluated against the phytopathogenic fungi Botrytis cinerea, Colletotrichum coccodes, Blumeria graminis f. sp. hordei, Magnaporthe grisea, Phytophthora infestans, Puccinia recondita and Rhizoctonia solani using a whole-plant assay method. Ethyl acetate and acetone extracts, at 1000μg/mL, suppressed the development of tomato gray mold (TGM) and tomato late blight (TLB) by 90%. Through bioassay-guided isolation, five antifungal substances were isolated from the D. asper roots and identified as β-sitosterol (1), campesterol (2), stigmasterol (3), cauloside A (4) and a novel dipsacus saponin, named colchiside (3-O-β-d-xylopyranosyl-23-O-β-d-glucopyranosyl-28-O-β-d-(6-O-acetyl)-glucopyranosyl hederagenin) (5). Of those, cauloside A (4) displayed the greatest antifungal efficacy against rice blast, TGM and TLB. Colchiside (5) moderately suppressed the development of TLB, but exhibited little effect against the other diseases. The synergistic effects of the isolated compounds against TLB were also assessed. Synergistic and additive interactions were observed between several of the sterol compounds. This study indicated that the crude extracts of, and bioactive substances from, the roots of D. asper suppress TGM and TLB. In addition, cauloside A (4) and colchiside (5) could be used as antifungal lead compounds.

    Topics: Antifungal Agents; Cholesterol; Dipsacaceae; Oleanolic Acid; Phytosterols; Plant Roots; Saponins; Sitosterols; Sterols

2017
β-Sitosterol and stigmasterol ameliorate dextran sulfate sodium-induced colitis in mice fed a high fat Western-style diet.
    Food & function, 2017, Nov-15, Volume: 8, Issue:11

    Phytosterols, the plant analogues of cholesterol, widely occur in the human diet. In this study, we investigated and compared the effects of stigmasterol and β-sitosterol (both with purities ≥95%) on dextran sulfate sodium (DSS)-induced colitis in C57BL/6J male mice fed a high fat Western-style diet. Mice treated with DSS developed severe mucosal colitis, with a marked distortion and crypt loss of colonic surface epithelium. Both β-sitosterol and stigmasterol significantly inhibited colon shortening, lowered fecal hemoglobin content, and reduced the severity of colitis in the middle and distal colon (p < 0.05). These phytosterols also significantly suppressed the activation of nuclear factor-kappa B. They also significantly decreased colony stimulating factor-1 and the nuclear translocation of inflammatory master regulator nuclear factor-kappa B. Stigmasterol significantly lowered the colonic inflammation score and the expression of cyclooxygenase-2 and colony stimulating factor-1, while β-sitosterol was less or not effective. These results suggest that dietary intake of stigmasterol and β-sitosterol ameliorates colitis. Such activities of stigmasterol and β-sitosterol in humans remain to be investigated.

    Topics: Animals; Colitis; Dextran Sulfate; Diet, High-Fat; Humans; Male; Mice; Mice, Inbred C57BL; Sitosterols; Stigmasterol

2017
Evaluation of the Effect of Moringa peregrina Extract on Learning and Memory: Role of Oxidative Stress.
    Journal of molecular neuroscience : MN, 2017, Volume: 63, Issue:3-4

    Oxidative stress interferes with the functional roles of the hippocampus and results in cognitive decline. Antioxidant supplementation has a cognitive enhancing activity through protecting hippocampus brain cells from the damaging effects of the reactive oxygen species. The dried methanolic extract of the aboveground parts of Moringa peregrina (Forssk.) Fiori (Moringaceae) was hypothesized to have memory-enhancing activity via its antioxidative properties. HPLC and LC-MS methods were used for qualitative analysis of the marker compounds. Six major compounds of the methanolic extract of M. peregrina were identified, namely, rutin, myricetin, α-amyrin, β-amyrin, lupeol acetate, and β-sitosterol. Male Wistar rats were administered via oral gavage three dose levels (50, 100, and 500 mg/kg) of M. peregrina methanolic extract for 2 months. The radial arm water maze (RAWM) was used to test spatial learning and memory. In addition, ELISA was used to analyze the levels of brain-derived neurotrophic factor (BDNF) and to assess the level of some oxidative stress markers. M. peregrina (150 mg/kg) resulted in short- and long-term memory enhancement (P < 0.05). Moreover, M. peregrina administration elevated BDNF levels in the hippocampus (P < 0.05) and caused favorable changes in oxidative stress biomarkers. In particular, an increase in glutathione (GSH), a decrease in oxidized glutathione (GSSG), and an increase in the antioxidant enzyme glutathione peroxidase (GPx) levels in the hippocampus were elicited after treatment with M. peregrina. Taken together, our data show that oral administration of M. peregrina enhances both short- and long-term memory functions via combating oxidative stress and increasing BDNF levels in the hippocampus. Consuming this safe plant may thus help promote spatial learning and improve memory.

    Topics: Animals; Antioxidants; Brain-Derived Neurotrophic Factor; Flavonoids; Hippocampus; Male; Maze Learning; Memory; Moringa; Oleanolic Acid; Oxidative Stress; Pentacyclic Triterpenes; Plant Extracts; Rats; Rats, Wistar; Rutin; Sitosterols

2017
Combination of berberine and evodiamine inhibits intestinal cholesterol absorption in high fat diet induced hyperlipidemic rats.
    Lipids in health and disease, 2017, Dec-11, Volume: 16, Issue:1

    Hyperlipidemia characterized of elevated serum lipid levels is a prevalent disease frequently resulting in cardiovascular disease (CVD). Berberine and evodiamine are herbal products of traditional Chinese herb Coptis chinensis and Evodia rutaecarpa, which are indicated to exert regulation of lipid metabolism. Therefore, the objective of this study was to investigate the lipid-lowering effect of berberine and evodiamine combination in hyperlipidemic rats.. The rat model of hyperlipidemia was established by providing high-fat-diet (HFD) for 4 weeks. Berberine (BB), evodiamine (EV), and their combination (BB + EV) were orally administered to HFD induced rats for 4 weeks. Body weight, food utilization, histopathology of liver tissues, lipid profiles of serum and liver were measured. Gas chromatography (GC) analysis was applied to examine the level of plasma total cholesterol and ß- Sitosterol (BS) to estimate cholesterol absorption activity. Furthermore, intestinal NPC1L1, ACAT2, and ApoB48 protein expressions were evaluated by immunohistochemical assay.. According to the results, decreased levels of serum cholesterol (TC), triglycerides (TG), low density lipoprotein-cholesterol (LDL-C), as well as hepatic TC were showed in hyperlipidemic rats treated by combination of berberine and evodiamine. GC analysis indicated that the elevated plasma BS was significantly ameliorated by BB, EV, and BB + EV. In addition, immunohistochemical analysis revealed that BB + EV treatment down-regulated the expressions of intestinal NPC1L1 and ACAT2, and ApoB48 in HFD induced rats.. Based on the above results, combination of berberine and evodiamine exerted a promising preventive effect on hyperlipidemia, partially through inhibiting intestinal absorption of cholesterol.

    Topics: Administration, Oral; Animals; Apolipoprotein B-48; Berberine; Body Weight; Cholesterol, LDL; Coptis; Diet, High-Fat; Drug Combinations; Evodia; Gene Expression Regulation; Hyperlipidemias; Hypolipidemic Agents; Intestinal Absorption; Lipid Metabolism; Liver; Male; Membrane Transport Proteins; Quinazolines; Rats; Rats, Sprague-Dawley; Sitosterols; Sterol O-Acyltransferase; Sterol O-Acyltransferase 2; Triglycerides

2017
[Chemical constituents from petroleum ether fraction of Swertia chirayita and their activities in vitro].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2017, Volume: 42, Issue:19

    The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin (1), decussatin (2), 1,8-dihydroxy-3,5,7-trimethoxyxanthone (3), 1-hydroxy-3,5,7,8-tetramethoxyxanthone (4), bellidifolin (5), 1-hydroxy-3, 7-dimethoxyxanthone (6), methylswertianin (7), 1-hydroxy-3,5-dimethoxyxanthone (8), erythrodiol (9), oleanolic acid (10), gnetiolactone (11), scopoletin (12), sinapaldehyde (13), syringaldehyde (14), and β-sitosterol (15). Compounds 3, 4, 9, 11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1, 2, 5, 7 and 8 against human pancreatic cancer cell lines SW1990 and BxPC-3,and the protective effects of these compounds against hydrogen peroxide (H2O2)-induced oxidative stress in human endothelium-derived EA.hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 μmol•L⁻¹.

    Topics: Acrolein; Alkanes; Benzaldehydes; Cell Line, Tumor; Drugs, Chinese Herbal; Humans; Hydrogen Peroxide; Oleanolic Acid; Oxidative Stress; Phytochemicals; Plant Extracts; Scopoletin; Sitosterols; Swertia; Xanthones

2017
[Study on Material Basis and Mechanism of Erzhi Wan prevent Alzheimer's disease by network pharmacology].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2017, Volume: 42, Issue:21

    The present study is to explore the material basis and mechanism of Erzhi Wan the prevented Alzheimer's disease by using network pharmacology. The key target of Alzheimer's disease was docked with the Erzhi Wan compounds, and the drugs-target combined with target-signal pathway network model was established by Cytoscape 3.2.1 software. Thirty compounds have a strong interaction with key target of Alzheimer's disease and three key pathways related with Wnt, MAPK and PI3K-Akt-mTOR. There are 5 ingredients such as quercetin,geraniol,beta-sitosterol,nerol,eriodictyol that could be verified from literature.This result initially revealed the material basis for Erzhi Wan for Alzheimer's disease and the mechanism in terms of three signaling pathways. The network pharmacology method found that the active ingredients of Erzhi Wan for Alzheimer's disease may be quercetin,geraniol,beta-sitosterol,nerol,and eriodictyol, and the mechanism may be related to three signal pathways including Wnt, MAPK, and PI3K-Akt-mTOR.

    Topics: Acyclic Monoterpenes; Alzheimer Disease; Drugs, Chinese Herbal; Flavanones; Humans; Molecular Docking Simulation; Phytochemicals; Quercetin; Signal Transduction; Sitosterols; Terpenes

2017
Raphanus sativus Sprout Causes Selective Cytotoxic Effect on p53-Deficient Human Lung Cancer Cells in vitro.
    Natural product communications, 2017, Volume: 12, Issue:2

    Raphanus sativus L. (Brassicaceae) is widely consumed in many different forms worldwide. Its sprouts, in particular, are commonly consumed as a health food. R. stivus sprout has recently been shown to have anti-tumor activity on human colon cancer cells, suggesting that it may have potential use in.cancer prevention and treatment. The extent of this anti-tumor activity and its underlying mechanisms, however, remain to be investigated in other types-of cancer cells. In this study, we showed that the MeOH extract from R. sativus sprout exhibits significant but variable cytotoxic effects on human lung adenocarcinoma cells depending on their p53 status. The MeOH extract decreased the viability of p53-deleted human lung cancer cells (H1299 and Calu-6) by inducing apoptosis; this effect, however, did not occur for wild-type p53 cancer cells (A549), for cells expressing a p53 mutant lacking the C terminus (H1264), or for . non-tumor fibroblast cells (NIH3T3). Phytochemical analyses of the MeOH extract allowed us to identify and isolate 0-sitosterol as a major component of the MeOH extract. Direct treatment with P-sitosterol significantly reduced the viability of Calu-6 cells, suggesting that it may, in part, contribute to R. sativus sprout's anti-tumor activity. This work provides experimental evidence for a novel biological application of R. sativus sprout in treating human lung cancer, and it identifies the main component involved in this effect, further supporting its potential use as a functional food for cancer management.

    Topics: Adenocarcinoma of Lung; Animals; Apoptosis; Cell Line, Tumor; Functional Food; Humans; Mice; NIH 3T3 Cells; Plant Extracts; Raphanus; Sitosterols; Tumor Suppressor Protein p53

2017
Parenteral Plant Sterols Accumulate in the Liver Reflecting Their Increased Serum Levels and Portal Inflammation in Children With Intestinal Failure.
    JPEN. Journal of parenteral and enteral nutrition, 2017, Volume: 41, Issue:6

    Parenteral plant sterols (PSs) are considered hepatotoxic; however, liver PSs and their associations with liver injury in patients with intestinal failure (IF) have not been reported.. We analyzed liver and serum PS (avenasterol, campesterol, sitosterol, and stigmasterol) concentrations and ratios to cholesterol and their associations with biochemical and histologic liver damage in children with IF during (n = 7) parenteral nutrition (PN) and after weaning off it (n = 9), including vegetable oil-based lipid emulsions.. Liver avenasterol, sitosterol, and total PS concentrations and cholesterol ratios were 2.4-fold to 5.6-fold higher in PN-dependent patients ( P < .05). Parenteral PS delivery reflected liver avenasterol and sitosterol ratios to cholesterol ( r = 0.83-0.89, P = .02-.04), while serum and liver total PS levels were positively interrelated ( r = 0.98, P < .01). Any liver histopathology was equally common while portal inflammation more frequent (57 vs 0%, P = .02) in PN-dependent patients. All liver PS fractions correlated positively with histologic portal inflammation ( r = 0.53-0.66, P < .05), and their total concentration was significantly ( P = .01) higher among patients with versus without portal inflammation. In PN-dependent patients, liver fibrosis and any histopathology correlated with liver campesterol and stigmasterol levels ( r = 0.79-0.87, P ≤ .03).. Among children with IF, parenteral PSs accumulate in the liver, reflect their increased serum levels, and relate with biochemical liver injury, portal inflammation, and liver fibrosis, thus supporting their role in promoting liver damage.

    Topics: Alanine Transaminase; Aspartate Aminotransferases; Chemical and Drug Induced Liver Injury; Child; Child, Preschool; Cholesterol; Female; gamma-Glutamyltransferase; Humans; Infant; Inflammation; Intestinal Diseases; Liver; Male; Parenteral Nutrition; Phytosterols; Plant Oils; Portal Vein; Sitosterols; Stigmasterol; Triglycerides

2017
Environmental estrogens inhibit mRNA and functional expression of growth hormone receptors as well as growth hormone signaling pathways in vitro in rainbow trout (Oncorhynchus mykiss).
    General and comparative endocrinology, 2017, 05-15, Volume: 246

    Fish in aquatic habitats are exposed to increasing concentrations and types of environmental contaminants, including environmental estrogens (EE). While there is growing evidence to support the observation that endocrine-disrupting compounds (EDCs) possess growth-inhibiting effects, the mechanisms by which these physiological effects occur are poorly understood. In this study, we examined the direct effects of EE, specifically 17β-estradiol (E2), β-sitosterol (βS), and 4-n-nonylphenol (NP), on GH sensitivity as assessed by mRNA expression and functional expression of growth hormone receptor in hepatocytes, gill filaments, and muscle in rainbow trout (Oncorhynchus mykiss). Additionally, we examined the effects of EE on signaling cascades related to growth hormone signal transduction (i.e., JAK-STAT, MAPK, and PI3K-Akt). Environmental estrogens directly suppressed the expression of GHRs in a tissue- and compound-related manner. The potency and efficacy varied with EE; effects were most pronounced with E2 in liver. EE treatment deactivated the JAK-STAT, MAPK, and PI3K-Akt pathways in liver a time-, EE- and concentration-dependent manner. Generally, E2 and NP were most effective in deactivating pathway elements; maximum suppression for each pathway was rapid, typically occurring at 10-30min. The observed effects occurred via an estrogen-dependent pathway, as indicated by treatment with an ER antagonist, ICI 182,780. These findings suggest that EEs suppress growth by reducing GH sensitivity in terms of reduced GHR synthesis and reduced surface GHR expression and by repressing GH signaling pathways.

    Topics: Animals; Blotting, Western; Environmental Exposure; Estradiol; Estrogen Receptor Antagonists; Estrogens; Fulvestrant; Gene Expression Regulation; Gills; Growth Hormone; Hypolipidemic Agents; In Vitro Techniques; Liver; Muscles; Oncorhynchus mykiss; Real-Time Polymerase Chain Reaction; Receptors, Somatotropin; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Signal Transduction; Sitosterols

2017
Influence of cultivation sites on sterol, nitrate, total phenolic contents and antioxidant activity in endive and stem chicory edible products.
    International journal of food sciences and nutrition, 2017, Volume: 68, Issue:1

    Chicories produce a wide range of vegetables with important nutritional value. We determined the variation of sterol, total polyphenol, nitrate contents and antioxidant capacity (SC, TPC, NC, AC) in endive leaves and stem-chicory novel vegetables, cultivated in two Italian regions. Within a given area, the SC was similar in smooth- and curly leafed endives (106.3-176.0 mg/kg FW); sitosterol and stigmasterol were major fractions (45-56 versus 38-43%). The stem SC was independent of landrace (101.5-118.6 mg/kg FW); sitosterol prevailed on stigmasterol and fucosterol (73-76 versus 12-14% versus 8-9%); the latter reached 15.7 mg/kg FW, conferring value as potential antidiabetes food. The planting site affected the AC and TPC of endives (893.1-1571.4 μmTE/100 g FW, 30.8-76.1 GAE100/g FW) and chicory stems (729.8-1152.5 μmTE/100 g FW; 56.2-124.4 GAE100/g FW), while the NC was recurrently below dangerous thresholds. PCA showed that environment was the major cause of variation, though it modestly affected these parameters.

    Topics: Antioxidants; Asteraceae; Cichorium intybus; Crop Production; Crops, Agricultural; Food Contamination; Functional Food; Humans; Italy; Nitrates; Nutritive Value; Oxygen Radical Absorbance Capacity; Phenols; Phytosterols; Plant Leaves; Plant Stems; Principal Component Analysis; Sitosterols; Spatio-Temporal Analysis; Species Specificity; Stigmasterol

2017
Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of β-sitosterol.
    Steroids, 2017, Volume: 117

    Topics: Cell Survival; Humans; Hydrogen Bonding; Ionic Liquids; Lipase; Magnetic Resonance Spectroscopy; MCF-7 Cells; Microscopy, Atomic Force; Microscopy, Electron, Transmission; Sitosterols

2017
Identification of compounds from non-polar fractions of Blechnum spp and a multitarget approach involving enzymatic modulation and oxidative stress.
    The Journal of pharmacy and pharmacology, 2017, Volume: 69, Issue:1

    The hexane (HEX) and dichloromethane (DCM) fractions from Blechnum binervatum, Blechnum brasiliense and Blechnum occidentale were studied about phytochemicals and biological properties using multitarget approach.. The chemical composition was performed by gas chromatography coupled with mass spectrometry detector (GC-MS) analysis. Antioxidant capacity was evaluated against free radicals and on lipid peroxidation. Monoamine oxidases (MAO) and cholinesterases enzymatic modulation, as well as effects on rat and human cells, were assessed.. These findings encourage the search for multibinding natural products, mainly from B. brasiliense DCM fraction.

    Topics: Animals; Antioxidants; Ferns; Gas Chromatography-Mass Spectrometry; Humans; Lipid Peroxidation; Male; Monoamine Oxidase; Monoamine Oxidase Inhibitors; Oxidative Stress; Plant Extracts; Rats, Wistar; Sitosterols; Species Specificity; Terpenes

2017
Cryptoporic acid S, a new drimane-type sesquiterpene ether of isocitric acid from the fruiting bodies of Cryptoporus volvatus.
    Journal of Asian natural products research, 2017, Volume: 19, Issue:7

    A new drimane-type sesquiterpene with an isocitric acid moiety, cryptoporic acid S (1), together with six known compounds, cryptoporic acid D (2), β-sitosterol (3), β-daucosterol (4), stigmast-4-en-3-one (5), ergosterol (6), and (22E,24R)-ergosta-7,22-diene-3β,5α,6β-triol (7), was isolated from the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established on the basis of UV, IR, MS, 1D and 2D NMR analysis. In the meanwhile, compounds 1 and 2 were evaluated for antioxidant activity using the methods of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assay, and they exhibited moderate antioxidant activities.

    Topics: Antioxidants; Biphenyl Compounds; China; Coriolaceae; Ergosterol; Ethers; Fruiting Bodies, Fungal; Isocitrates; Molecular Structure; Picrates; Polycyclic Sesquiterpenes; Sesquiterpenes; Sitosterols; Stigmasterol

2017
Melicodenine I, a new quinolinone alkaloid from Melicope denhamii leaves.
    Natural product research, 2017, Volume: 31, Issue:8

    A new quinolinone alkaloid, Melicodenine I (1), along with five known compounds, bergapten (2), isoevodionol methyl ether (3), isoevodionol (4), ternatin (5), β-sitosteryl-3-O-β-D-glucopyranoside (6) and a mixture of β-sitosterol and stigmasterol were isolated from Melicope denhamii leaves, and their structures were elucidated using

    Topics: 5-Methoxypsoralen; Alkaloids; Flavonoids; Magnetic Resonance Spectroscopy; Mass Spectrometry; Methoxsalen; Molecular Structure; Plant Leaves; Plants, Medicinal; Quinolones; Rutaceae; Sitosterols; Stigmasterol

2017
Activity based evaluation of a traditional Ayurvedic medicinal plant: Saraca asoca (Roxb.) de Wilde flowers as estrogenic agents using ovariectomized rat model.
    Journal of ethnopharmacology, 2017, Jan-04, Volume: 195

    Saraca asoca (Roxb.) de Wilde, Ashok, is a popular traditional plant used for gynecological disorders. In India, the juice of Ashok flowers is traditionally consumed as a tonic by women in case of uterine disorders. But despite the use, its estrogenic potency is not yet evaluated and thus lacks the scientific recognition and acclaim.. This study is designed to investigate the estrogenic potential of standardized ethanolic extract of Saraca asoca flowers (SAF) using ovariectomized (OVX) female albino Wistar rat model.. Saraca asoca flowers were extracted in ethanol using hot maceration technique and the extract was standardized in terms of content of four phytoestrogens like quercetin, kaempferol, β-sitosterol and luteolin using HPTLC technique. Safety of the extract was evaluated at a dose of 2000mg/kg body weight in female albino Wistar rats as per the OECD guidelines. Bilateral ovariectomy surgery was performed for the excision of both the ovaries. The OVX animals were treated with the ethanolic extract of SAF at three dose levels- 100mg/kg, 200mg/kg and 400mg/kg body weight in distilled water as a vehicle, orally once a day for two weeks. Estradiol valerate was employed as a modern drug for comparative evaluation of the results. Estrogenic potency was studied by assaying the activities of serum and plasma marker enzymes and hormones viz. G6PDH, LDH, 17β-estradiol, progesterone along with cholesterol, triglycerides and HDL, and vaginal cornification. The uterotrophic effect was evaluated by studying the histoarchitecture of the uterus, effect on uterine weight and changes in the levels of uterine glycogen content.. HPTLC revealed the presence of markers like quercetin, kaempferol, β-sitosterol and luteolin from the ethanolic extract of SAF. The content of the four markers was found to be 1.543mg/g, 0.924mg/g, 4.481mg/g and 2.349mg/g, respectively. SAF extract was found to be safe at an oral dose of 2000mg/kg body weight in rats. Among the three doses administered to ovariectomized rats, treatment with high dose was found to be more efficacious when compared with ovariectomized rats.. The findings of this study firmly support the estrogenic potency of ethanolic extract of SAF which may be by the reason of phytoestrogens.

    Topics: Administration, Oral; Animals; Biomarkers; Chromatography, Thin Layer; Estradiol; Estrogen Replacement Therapy; Ethanol; Fabaceae; Female; Flowers; Glucosephosphate Dehydrogenase; Glycogen; Kaempferols; L-Lactate Dehydrogenase; Lipids; Luteolin; Medicine, Ayurvedic; Organ Size; Ovariectomy; Phytoestrogens; Phytotherapy; Plant Extracts; Plants, Medicinal; Progesterone; Quercetin; Rats, Wistar; Sitosterols; Solvents; Uterus; Vagina

2017
Encapsulation of β-Sitosterol in Polyurethane by Sol-Gel Electrospinning.
    Applied biochemistry and biotechnology, 2017, Volume: 182, Issue:2

    Pristine β-sitosterol or in combination with other phytosterols is utilized in an array of enriched commercial foods. Considering the presence of β-sitosterol in different functional foods and its potential role in prevention and cure of neurodegenerative diseases, the aims of our investigation were to encapsulate β-sitosterol in nanofibers and to estimate influence of β-sitosterol on proliferation of fibroblasts. Electrospun nanofibers have widely been used as scaffolds to mimic natural extracellular matrix. Herein, our group for the first time establishes an innovative scaffold based on β-sitosterol and polyurethane using electrospinning. β-Sitosterol promotes epithelialization and possesses anti-oxidant and anti-inflammatory activities, whereas polyurethane, besides possessing biomedical uses, also enhances epithelial growth. We optimized the concentration (5%) of β-sitosterol in polyurethane to obtain homogenous solution, which can be spun without difficulty for the synthesis of β-sitosterol amalgamated scaffold. The resulted twisted nanofibers have been characterized via scanning electron microscopy and Fourier transform infrared spectroscopy. The viability of cells on twisted scaffold was examined using NIH 3T3 fibroblasts as model cell line. Incorporation of β-sitosterol in polyurethane changed the structure and size of nanofibers, and the twisted scaffolds were non-cytotoxic. Thus, the twisted nanoribbons, which contain anti-inflammatory β-sitosterol, can be utilized as a promising future material, which will help to ease inflammation and also aid in wound healing. In conclusion, the outcome of the preliminary research evidently points out the potential of twisted scaffold in biomedical applications.

    Topics: Animals; Electrochemical Techniques; Materials Testing; Mice; Nanofibers; NIH 3T3 Cells; Phase Transition; Polyurethanes; Sitosterols

2017
Phytoestrogens and sterols in waters with cyanobacterial blooms - Analytical methods and estrogenic potencies.
    Chemosphere, 2017, Volume: 170

    Compounds with estrogenic potencies and their adverse effects in surface waters have received much attention. Both anthropogenic and natural compounds contribute to overall estrogenic activity in freshwaters. Recently, estrogenic potencies were also found to be associated with cyanobacteria and their blooms in surface waters. The present study developed and compared the solid phase extraction and LC-MS/MS analytical approaches for determination of phytoestrogens (8 flavonoids - biochanin A, coumestrol, daidzein, equol, formononetin, genistein, naringenin, apigenin - and 5 sterols - ergosterol, β-sitosterol, stigmasterol, campesterol, brassicasterol) and cholesterol in water. The method was used for analyses of samples collected in stagnant water bodies dominated by different cyanobacterial species. Concentrations of individual flavonoids ranged from below the limit of detection to 3.58 ng/L. Sterols were present in higher amounts up to 2.25 μg/L. Biological potencies of these phytoestrogens in vitro were characterized using the hERα-HeLa-9903 cell line. The relative estrogenic potencies (compared to model estrogen - 17β-estradiol) of flavonoids ranged from 2.25E-05 to 1.26E-03 with coumestrol being the most potent. None of the sterols elicited estrogenic response in the used bioassay. Estrogenic activity was detected in collected field water samples (maximum effect corresponding to 2.07 ng/L of 17β-estradiol equivalents, transcriptional assay). At maximum phytoestrogens accounted for only 1.56 pg/L of 17β-estradiol equivalents, contributing maximally 8.5% of the total estrogenicity of the water samples. Other compounds therefore, most likely of anthropogenic origin such as steroid estrogens, are probably the major drivers of total estrogenic effects in these surface waters.

    Topics: Cholestadienols; Cholesterol; Cyanobacteria; Estradiol; Estrogens; Estrone; Fresh Water; Genistein; HeLa Cells; Humans; Isoflavones; Phytoestrogens; Phytosterols; Receptors, Estrogen; Sitosterols; Sterols; Tandem Mass Spectrometry; Water; Water Pollutants, Chemical

2017
Tunable volatile release from organogel-emulsions based on the self-assembly of β-sitosterol and γ-oryzanol.
    Food chemistry, 2017, Apr-15, Volume: 221

    A current challenge in the area of food emulsion is the design of microstructure that provides controlled release of volatile compounds during storage and consumption. Here, a new strategy addressed this problem at the fundamental level by describing the design of organogel-based emulsion from the self-assembly of β-sitosterol and γ-oryzanol that are capable of tuning volatile release. The results showed that the release rate (v

    Topics: Emulsions; Phenylpropionates; Phytosterols; Sitosterols

2017
Discrimination of red and white rice bran from Indonesia using HPLC fingerprint analysis combined with chemometrics.
    Food chemistry, 2017, Apr-15, Volume: 221

    HPLC fingerprint analysis combined with chemometrics was developed to discriminate between the red and the white rice bran grown in Indonesia. The major component in rice bran is γ-oryzanol which consisted of 4 main compounds, namely cycloartenol ferulate, cyclobranol ferulate, campesterol ferulate and β-sitosterol ferulate. Separation of these four compounds along with other compounds was performed using C18 and methanol-acetonitrile with gradient elution system. By using these intensity variations, principal component and discriminant analysis were performed to discriminate the two samples. Discriminant analysis was successfully discriminated the red from the white rice bran with predictive ability of the model showed a satisfactory classification for the test samples. The results of this study indicated that the developed method was suitable as quality control method for rice bran in terms of identification and discrimination of the red and the white rice bran.

    Topics: Cholesterol; Chromatography, High Pressure Liquid; Indonesia; Oryza; Phenylpropionates; Phytosterols; Sitosterols; Triterpenes

2017
Variations in dietary intake and plasma concentrations of plant sterols across plant-based diets among North American adults.
    Molecular nutrition & food research, 2017, Volume: 61, Issue:8

    Phytosterols are bioactive compounds in plants with similar cholesterol-lowering properties as vegetarian diets. However, information on phytosterol intake and plasma plant sterols among vegetarians is sparse.. We examined dietary intake and plasma concentration of plant sterols and cholesterol across five dietary patterns in the Adventist Health Study-2 Calibration Sub-study (n = 861, 66% females, average age 61 years). To measure intake and plasma concentrations of these compounds, we used 24-h dietary recalls and gas-liquid chromatography-flame ionization detection, respectively. Mean (SD) total phytosterol and cholesterol intake were 363 (176) mg/day and 131 (111) mg/day; plasma β-sitosterol, campesterol, and cholesterol were 3.3 (1.7) μg/mL, 4.2 (2.3) μg/mL, and 1.9 (0.4) mg/mL, respectively. Total phytosterol intake was lowest among non-vegetarians (263 mg/day) and highest among vegans (428 mg/day) (p < 0.0001). Cholesterol intake was lowest among vegans (15.2 mg/day) and highest among non-vegetarians (124.6 mg/day) (p < 0.0001). Plasma plant sterols and cholesterol did not differ by diet. Cholesterol-adjusted plasma β-sitosterol and campesterol were significantly higher in Blacks than Whites, though no ethnic differences were observed in dietary intake of these plant sterols.. Dietary intake but not plasma concentration of plant sterols and cholesterol varies across distinct plant-based diets.

    Topics: Aged; Cholesterol; Cross-Sectional Studies; Diet; Diet, Vegetarian; Female; Humans; Male; Middle Aged; North America; Nutrition Surveys; Phytosterols; Sitosterols

2017
Beta-sitosterol upregulated paraoxonase-1 via peroxisome proliferator-activated receptor-γ in irradiated rats.
    Canadian journal of physiology and pharmacology, 2017, Volume: 95, Issue:6

    This study was designed to evaluate the effect of beta-sitosterol (BS) on the peroxisome proliferator-activated receptor gamma (PPAR-γ) gene expression role in the activity of paraoxonase (PON-1) enzyme in oxidative stress status of irradiated rats. Animals were exposed to whole body γ-radiation single dose 6 Gy and received BS dose (40 mg·(kg body mass)

    Topics: Animals; Aryldialkylphosphatase; Carboxylic Ester Hydrolases; Catalase; Gamma Rays; Lipids; Male; Malondialdehyde; Oxidative Stress; PPAR gamma; Rats; Sitosterols; Superoxide Dismutase; Up-Regulation

2017
Lipid nanovehicles with adjustable surface properties for overcoming multiple barriers simultaneously in oral administration.
    International journal of pharmaceutics, 2017, Mar-30, Volume: 520, Issue:1-2

    Lipid nanoparticles (LNs) are widely investigated for oral drug delivery, and for achieving significant advantages in colloidal stability, biocompatibility and scaled-up possibility. However, researchers face challenge of developing methods to improve the ability of LNs in overcoming multiple barriers (i.e., mucus and epithelium barrier) in gastrointestinal (GI) tract because of the contradictory requirement of nanoparticle (NP) surface properties in the two processes. Therefore, we designed novel LNs with adjustable surface properties by coating lipid core with hydrophobic substitutes grafting N-(2-hydroxypropyl) methacrylamide copolymer (pHPMA). In the present study, different substitutes (i.e., monocyclic, polycyclic, and linear segments) were grafted on pHPMA backbone. Screening studies demonstrated that type and grafting degree of substitutes both influenced hydrophilic-hydrophobic properties of NP surface and improved penetration through mucus. When a hydrophilic-hydrophobic balance was achieved, NPs showed elevated mucus permeability compared with bare LNs; this phenomenon subsequently contributed to higher cellular uptake. Moreover, β-sitosterol (SITO)-modified pHPMA-coated (grafting degree: 5%) LNs (5% SITO-LNs) exhibited the highest mucus permeability, transepithelial transport, and in situ absorption. Interestingly, even with the highest surface hydrophilicity, 5% SITO-LNs with Caco-2 cells did not show impaired membrane affinity, which was not observed in other groups. Further investigations of mechanism demonstrated that membrane affinity was significantly enhanced by β-SITO-mediated interaction with Niemann-Pick C1-like 1 (NPC1L1) protein on cell membranes. These results proved that hydrophobic substitutes play a critical role in altering hydrophilic-hydrophobic property of particle surface and improving penetration through multiple barriers. β-SITO-induced specific interaction can provide additional benefits to efficiency of oral delivery of LNs.

    Topics: Acrylamides; Administration, Oral; Drug Carriers; Gastrointestinal Absorption; Humans; Hydrophobic and Hydrophilic Interactions; Lipids; Mucus; Nanoparticles; Permeability; Sitosterols; Surface Properties

2017
Sterols in infant formulas: validation of a gas chromatographic method.
    International journal of food sciences and nutrition, 2017, Volume: 68, Issue:6

    Sterols are components present in the fat fraction of infant formulas (IFs). Their characterization is therefore of interest, though there are no official reference methods for their analysis in these matrices.. To validate a gas chromatographic method with flame ionization detection for the determination of animal (cholesterol and desmosterol) and plant sterols (brassicasterol, campesterol, stigmasterol, β-sitosterol and sitostanol) found in IFs. All correlation coefficients obtained for the calibration curves of sterols studied were >0.99. Limits of detection (<1 μg/100 mL) and quantification (<4 μg/100 mL) are suitable for sterols determination in IFs. The within-assay precision ranged from 1.6% to 8.8%, while the between-assay precision was <10% for most of sterols. Accuracy was satisfactory and was calculated by recovery assays (ranging 93-108%). The analytical parameters obtained showed the suitability of the proposed method for the determination of sterols in IFs.

    Topics: Calibration; Cholestadienols; Cholesterol; Chromatography, Gas; Desmosterol; Flame Ionization; Infant Formula; Limit of Detection; Phytosterols; Reproducibility of Results; Sitosterols; Stigmasterol

2017
A nor-diterpene from Salvia sahendica leaves.
    Natural product research, 2017, Volume: 31, Issue:15

    Phytochemical investigation of n-hexane extract of Salvia sahendica by normal phase column chromatography resulted in the isolation of six compounds. Structures were established by 1D and 2D NMR spectroscopy, and HRMS, as a new norditerpene 1, and known terpenoids, sclareol (2), oleanolic acid (3), β-sitosterol (4), salvigenin (5) and 3α-hydroxy-11α,12α-epoxyoleanan-28,13β-olide (6). The absolute configuration of 1 was confirmed by a combination of X-ray single crystal analysis and electronic circular dichroism spectroscopy. In vitro cytotoxic activity on breast cancer cell line (MDA-MB-231) and also the antimicrobial activity of the pure compounds were tested against Staphylococcus aureus, Bacilus cereus and Escherichia coli.

    Topics: Anti-Bacterial Agents; Antineoplastic Agents, Phytogenic; Breast Neoplasms; Cell Line, Tumor; Crystallography, X-Ray; Diterpenes; Female; Flavones; Hexanes; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plant Extracts; Plant Leaves; Salvia; Sitosterols; Staphylococcus aureus

2017
Phytochemical characterisation of an important medicinal plant, Chenopodium ambrosioides Linn.
    Natural product research, 2017, Volume: 31, Issue:19

    The project was intended to the phytochemical characterisation from the rudimentary methanolic extract of Chenopodium ambrosioides Linn., which escorts to the isolation of stigmasterol (1), β-sitosterol (2), octadecanoic acid (3), scopoletin (4) and 1-piperoylpiperidine (5). Literature validates the medicinal authentication of these compounds extorted from other sources, while our previous findings regarding microbial activities of different solvent systems fractions are favouring the presence of medicinally important compounds in this species. Herein, however, we report these natural products for the first time from this species.

    Topics: Alkaloids; Benzodioxoles; Chenopodium ambrosioides; Methanol; Phytochemicals; Piperidines; Plant Extracts; Plants, Medicinal; Polyunsaturated Alkamides; Sitosterols; Solvents; Stigmasterol

2017
[Chemical Constituents from Cynomorium songaricum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:1

    To study the chemical constituents from the fleshy stems of Cynomorium songaricum.. The chemical constituents were isolated and purified by chromatography on MCI, silica gel, Sephadex LH-20 columns, etc. The structures of compounds were elucidated by physicochemical property and spectral analyses.. 15 compounds were isolated and identified as choerospondin( 1), isolariciresinol-4-O-β-D-glucopyranoside( 2), lutelin-7-O-β-D-glucopyranoside( 3), 3, 4-dihydroxyphenethylacetate( 4),maslinic acid( 5),catechin ( 6),ursolic acid( 7),gentisic acid( 8),mannitol( 9), phloroglucinol( 10), β-sitosterol( 11), daucosterol( 12), rutin( 13), cetylic acid( 14) and epicatechin( 15).. Compounds 4,5,8,9 and 10 are obtained from this plant for the first time.

    Topics: Catechin; Cynomorium; Lignin; Naphthols; Phloroglucinol; Sitosterols; Triterpenes; Ursolic Acid

2016
[Chemical Constituents from Caragana changduensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:1

    To study the chemical constituents of the red heartwood of the stems and roots of Caragana changduensis.. The chemical constituents were isolated and purified by means of several column chromatographic techniques,and their structures were determined by spectroscopic methods.. Ten compounds were isolated and identified as kushenin( 1),( 6aR,11aR)-3-hydroxy-4,9-dimethoxy-pterocarpan( 2),(-)-4-methoxymaackiain( 3),(-)-homopterocarpin( 4),2,4-dimethoxybenzoic acid( 5),2-methoxy-4-ethoxybenzoic acid( 6),3-acetyl-oleanolic acid( 7),7-hydroxy-2,3-dimethylchromone( 8),liquiritigenin( 9),and β-sitosterol( 10).. Compounds 1,3,5,7,and 8 are obtained from this genus for the first time. All the compounds are obtained from this plant for the first time.

    Topics: Caragana; Flavanones; Oleanolic Acid; Plant Roots; Pterocarpans; Sitosterols

2016
[Chemical Constituents from Roots of Gentiana straminea of Tibetan Medicine].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:1

    To investigate the chemical constituent from the roots of Gentiana straminea.. The constituents were separated by microporous resin,silica gel,Sephadex LH-20 and preparative column chromatography and their structures were elucidated by NMR and MS spectral methods.. Twelve chemical constituents were isolated from the roots of Gentiana straminea and their structures were identified as daucosterol( 1),β-sitosterol( 2),ursolic acid( 3),sweroside( 4),swertiamarin( 5),gentiopicroside( 6),6’-O-acetyl-gentiopicroside( 7),6’-O-β-D-glucopyranosyl-sweroside( 8),protocatech uic aldehyde( 9),protocatechuic acid( 10),methyl gallate( 11) and dibutyl phthalate( 12).. The compounds 8,9,10,11 and 12 are obtained from this plant for the first time.

    Topics: Gentiana; Iridoid Glucosides; Magnetic Resonance Spectroscopy; Medicine, Tibetan Traditional; Plant Roots; Pyrones; Sitosterols; Triterpenes; Ursolic Acid

2016
[Study on Chemical Constituents of Delphinium caeruleum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:2

    To study the chemical constituents from the whole plant of Delphinium caeruleum.. The chemical constituents were isolated and purified by silica gel and Sephadex LH-20 column chromatography. The structures of the isolated compounds were elucidated by spectroscopic analysis and physicochemical properties.. Twelve compounds were isolated and purified from the ethanol extract of Delphinium caeruleum. They were identified as β-sitosterol( 1),kaempferol( 2),quercetin( 3),isovanillic acid( 4),apigenin( 5),luteolin( 6),8-methoxy-5,7,3’,4’-tetrahydroxy-flavone( 7),β-daucosterol( 8),kaempferol-3-O-β-D-glucoside( 9),3,5-dihydroxy-4’-methoxyflavone-7-yl-O-β-D-glucopyranosyl-( 1→4)-α-L-rhamnopyranoside( 10),rutin( 11) and sucrose( 12).. Compounds 1 ~ 12 are isolated from this plant for the first time.

    Topics: Apigenin; Delphinium; Glucosides; Kaempferols; Luteolin; Quercetin; Rutin; Sitosterols

2016
[Chemical Constituents from Mitrasacme pygmaea].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:2

    To study the chemical constituents from Mitrasacme pygmaea.. The compounds were isolated and purified by column chromatography and their structure were identified by NMR and MS,and comparison spectral data with literature.. Eleven compounds were isolated and identified as tricin-7-O-β-D-glucopyranoside( 1),massonianoid A( 2),kaempferol( 3),cinnamic acid( 4),quercetin( 5),tiliroside( 6),tricin( 7),β-sitosterol( 8),adenosine( 9),α-tocopherolquinone( 10)and β-daucosterol( 11).. All the compounds are isolated from this genus for the first time.

    Topics: Flavonoids; Kaempferols; Magnoliaceae; Quercetin; Sitosterols

2016
[Study on Chemical Constituents of Stalk from Pottsia laxifora].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:2

    To study the chemical constituents of stalk form Pottsia laxifora.. The chemical constituents were isolated by various chromatography methods,and the structures were elucidated by spectroscopic methods,physical and chemical properties.. Twelve compounds were isolated and their structures were identified as β-sitosterol( 1),salicylic acid( 2),resorcinol( 3),4-hydroxybenzoic acid( 4),protocatechuic acid( 5),vanillic acid( 6),syringic acid( 7),scopoletin( 8),cleomiscosin D( 9),( +)-lyoniresinol( 10),(-)-loliolide( 11) and daucosterol( 12).. Compounds 1 ~ 11 are isolated from this plant for the first time.

    Topics: Coumarins; Gallic Acid; Hydroxybenzoates; Magnoliaceae; Scopoletin; Sitosterols; Vanillic Acid

2016
[Chemical Constituents of Ethyl Acetate Fraction from Hypericum ascyron].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:2

    To study the chemical consituents of Hypericum ascyron.. The constituents were isolated and purified by chromatography on silica gel; the structure of the compound was determined by MS and NMR spectral analysis.. On the basis of spectroscopic analysis and comparison with the reported data, they were identified as hyperoside( 1),hypercalin B( 2),hypercalin C( 3),1,7-dihydroxyxanthone( 4),2,3-dimethoxyxanthone( 5),1-hydroxy-7-methoxyxanthone( 6),rutin( 7),kaempferol( 8),toxyloxanthone B( 9),quercetin( 10),quercitrin( 11),β-daucosterol( 12) and β-sitosterol( 13).. Compounds 2,3,6 and 9 are obtained from this plant for the first time.

    Topics: Acetates; Hypericum; Kaempferols; Quercetin; Rutin; Sitosterols

2016
[Study on Chemical Composition of Zingiberis Rhizome Carbonisata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:2

    To study the chemical constituents from Zingiberis Rhizome Carbonisata. g.. Compounds were isolated by Sephadex LH-20,ODS,MCI and silica gel column chromatography. Their structures were elucidated by physicochemical property and spectral analysis.. 16 compounds were isolated and identified as sitost-5-en-3β-ol acetate( 1),dibutyl phthalate( 2),4-[2-( 5-butylfuran-2-yl) ethyl]-2-methoxyphenol( 3),β-sitosterol( 4),8-paradol( 5),10-gingerdione( 6),6-shogaol( 7),6-paradol( 8),3,5-diacetoxy-6-gingerdiol( 9),1,2-benzenediol( 10),zingiberone( 11),6-gingerol( 12),1,2,4,5-tetrahydroxybenzene( 13),stigmasterol acetate( 14),8-dehydrogingerdione( 15) and 3,5-diacetoxy-7-( 4-hydroxy-3-methoxyphenyl)-1-( 4,5-dihydroxy-3-methoxyphenyl) heptane( 16).. All the compounds are isolated from Zingiberis Rhizome Carbonisata for the first time. And compounds 2,10,11,and13 are generated in the process of processing.

    Topics: Chromatography; Rhizome; Sitosterols; Stigmasterol

2016
Carissa congesta Wight and Benincasa hispida (Thunb.) Cogn. as budding immunomodulatory agents.
    Indian journal of experimental biology, 2016, Volume: 54, Issue:10

    Carissa congesta and Benincasa hispida are well-known medicinally important plants associated with diabetes, inflammation, protozal infections and cancer. Here, we emphasized up on the immunomodulatory potential of these plants as the source of lupeol, P-sitosterol and ursolic acid. Petroleum ether extracts of C. congesta roots and B. hispida seeds were subjected to acute toxicity studies. They were screened for its immunomodulatory prospective in rats by Haemagglutination Antibody (HA) titre and Delayed-Type Hypersensitivity (DTH) response using Sheep Red Blood Cells (SRBCs of-0.5x10⁹) as antigens. Carbon Clearance test (Phagocytic Index) was estimated by Indian ink suspension. Complete Freund's Adjuvant (CFA) induced arthritis model interpretation was done by paw edema, kene joint erosion (transverse section), body weights, arthritic index and biochemical levels (RBC, WBC and Hb levels). Both the extracts were found to be therapeutically safe up to 5000 mg/kg. Dosage of 100 mg/kg was not satisfactory; and 500 and 250 mg/kg showed significant immunostimmulation (HA Titre) and immunosuppression (DTH response, 48 h). Benincasa hispida seed and Carissa congesta root extracts showed phagocytic Index of 0.0163±0.003, 0.0145±0.003 and 0.0183±0.003, 0.0176±0.003 at 250 mg/kg and 500 mg/kg, respectively. CFA model revealed that the B. hispida seed and C. congesta root extracts decreased paw volume, knee joint erosion, increased body weights and biochemical parameters with an arthritic index of 1.31±0.12, 1.44±0.15 and 1. 16±0.09, 1.36±0.13 at 250 mg/kg and 500 mg, respectively. The results were interpreted by One- way ANOVA followed by Dunnett test. Extracts showed relevance as promising immunostimulators as compared to control.

    Topics: Animals; Apocynaceae; Arthritis, Experimental; Cucurbitaceae; Dose-Response Relationship, Drug; Female; Freund's Adjuvant; Hemagglutination; Hypersensitivity, Delayed; Immunologic Factors; Male; Pentacyclic Triterpenes; Phagocytosis; Phytotherapy; Plant Extracts; Plant Roots; Plants, Medicinal; Rats, Wistar; Seeds; Sitosterols; Triterpenes; Ursolic Acid

2016
[Chemical Constituents of Lowering LDL-C in Effective Part of Oroxylum indicum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:3

    To investigate the chemical constituents of effective part of Oroxylum indicum which related to lowering LDLC action.. The compounds were isolated with chromatography methods such as silica gel,polyamide and Sephadex LH-20. The structures were identified by physiochemical properties and spectral analysis.. 14 compounds were isolated from 95% alcohol extract and elucidated as β-sitosterol( 1), hexadecanoic acid( 2), oroxin A( 3), oroxin B( 4), chrysin( 5), quercetin( 6),quercetin-3-Orutinoside( 7),5,4’-dihydroxy-3,6,7-trimethoxyflavone( 8), diosmetin( 9), geniposide( 10),isoorientin( 11), quercitroside( 12), apigenin( 13) and gallicacid( 14).. Compounds 2,7 ~ 12 and 14 are reported from this plants for the first time.

    Topics: Apigenin; Cholesterol, LDL; Disaccharides; Flavones; Flavonoids; Luteolin; Plants, Medicinal; Sitosterols

2016
[Non-alkaloid Chemical Constituents from Macleaya cordata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:3

    To study the non-alkaloid chemical constituents of Macleaya cordata.. Alcohol extraction and liquidliquid partitionmethods were used to extract the chemical constituents. Silica gel,reverse-phase octadecylsilyl( ODS), and Sephadex LH-20 column chromatographic methods were applied for isolation and purification. Spectroscopic methods including MS and NMR were used to determine their structures.. Eleven non-alkaloid compounds were isolated from the fruits of Macleaya cordata, and their structures were identified as 3-( 3,4-dihydroxy) phenylpropanoic acid methyl ester( 1),ferulic acid( 2),1-octacosanol( 3),syringic acid( 4),p-hydroxy-benzoic acid( 5),p-coumaric acid( 6),quercetin-3-O-β-D-glucoside( 7),N-p-coumaroyl tyramine( 8),10-eicosenoic acid( 9) and β-sitosterol( 10) and daucosterol( 11).. Compounds 1,3 ~9 are isolated from Macleaya cordata for the first time.

    Topics: Alkaloids; Coumaric Acids; Gallic Acid; Glucosides; Papaveraceae; Quercetin; Sitosterols; Tyramine

2016
[Chemical Constituents of Ethyl Acetate Extract from Viola biflora].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:5

    To isolate the chemical constituents of ethyl acetate extract from Viola biflora.. Isolation and purification were carried out on repeated silica gel column chromatography,PTLC,and Sephadex LH-20. The structures of these compounds were elucidated by physico-chemical properties and spectral analyses.. Twelve compounds were isolated from Viola biflora,which identified as aurantiamide acetate( 1),solalyratin B( 2),esculetin( 3),scopoletin( 4),lupeol( 5),132S-hydroxypheophytin a( 6),vomifoliol( 7),dibutyl phthalate( 8),(-)-dihydrovomifoliol( 9),grasshopper ketone( 10),crassifol( 11) and β-sitosterol( 12).. All the compounds are isolated from Viola biflora for the first time. Compounds 2,7,9 ~ 11 are isolated from Viola genus for the first time.

    Topics: Acetates; Plant Extracts; Scopoletin; Sitosterols; Viola

2016
[Chemical Constituents from Rubus stans].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:5

    To study the chemical constituents of Rubus stans.. The chemical constituents were isolated and purified by silica gel and Sephadex LH-20 column chromatography. The structures were identified on the basis of spectroscopic analysis and physicochemical properties.. Eleven compounds were isolated and purified from the ethanol extract of Rubus stans. They were identified as β-sitosterol( 1),betulinic acid( 2),euscaphic acid( 3),ursolic acid( 4),corosolic acid( 5),kaempferol( 6),quercetin( 7),2α,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid( 8),β-daucosterol( 9),quercetin-3-O-β-D-glucoside( 10) and kaempferol-3-O-β-D-6-O-( p-hydroxycinnamoyl)-glucopyranoside( 11).. All the compounds are isolated from this plant for the first time.

    Topics: Betulinic Acid; Kaempferols; Pentacyclic Triterpenes; Rubus; Sitosterols; Triterpenes; Ursolic Acid

2016
[Study on Chemical Constituents of Stems from Altingia chinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:5

    To study the chemical constituents of the stems from Altingia chinensis.. The stems from Altingia chinensis were extracted with 95% ethanol for reflux,and the extract were evaporated. The chemical constituents were isolated by silica gel chromatography and Sephadex LH-20 column chromatography from petrol ether part and ethyl acetate part of extract. Their structures were identified on the basis of physico-chemical characters and spectroscopic analysis.. Eleven compounds were obtained from the stems from Altingia chinensis,which identified as myrsinene( 1),oleanonic aldehyde( 2),3β,23,28-trihydroxyolean-12-ene( 3),ursolic acid-3β-octadecanoate( 4),arjunglucoside Ⅱ( 5),β-sitosterol( 6),daucosterol( 7),trans-resveratrol-3-O-β-D-glucopyranoside( 8),ellagic acid 3,3’-dimethylether( 9),lyoniside( 10) and 3,3’-O-dimethylellagic acid-4’-O-α-L-rhamnoside( 11).. All the compounds are isolated from Altingia chinensis for the first time.

    Topics: Ellagic Acid; Saxifragaceae; Sitosterols; Triterpenes; Ursolic Acid

2016
[Chemical Constituents from the Roots of Rhodomyrtus tomentosa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:6

    To investigate the chemical constituents of the roots of Rhodomyrtus tomentosa and their antitumor activities.. Various column chromatographic techniques were used to isolate the compounds. The structures were elucidated by their physicochemical properties and spectra data. Moreover, MTT assay was used to evaluate the antitumor activity against melanoma SK-MEI-110 cells.. Thirteen compounds were obtained from the roots of Rhodomyrtus tomentosa, and their structures were determined as 2α, 3β, 23-trihydroxyoleana-11,13( 18)-dien-28-oic acid( 1),3β,23-dihydroxyolean-18-en-28-oic acid( 2), lupeol( 3), betulin( 4), betulinic acid( 5), friedelin( 6), β-sitosterol( 7), thero-2, 3-bis-( 4-hydroxy-3-methoxypheyl)-3-methoxy-propanol( 8), evafolin B( 9), β-hydroxypropiovanillone ( 10), 8, 8’-bis-( dihydroconiferyl)-diferuloylate( 11), gallate acid( 12) and methyl gallate( 13).. Compounds 1,2,8 ~ 10 and 13 are isolated from this plant for the first time. Compounds 1 ~ 6 exhibite inhibitory effects on melanoma SK-MEL-110 cells.

    Topics: Betulinic Acid; Magnoliaceae; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Triterpenes

2016
[Chemical Constituents of Lonicerae Japonicae Flos].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2016, Volume: 39, Issue:9

    To study the chemical constituents of the methylene chloride extract of Lonicerae Japonicae Flos.. The compounds were isolated and purified by silica gel column chromatography,Sephadex LH-20 gel column chromatography and recrystallization. The structures were elucidated by the physical and chemical properties,MS,1H-NMR and13C-NMR spectroscopy.. Nine compounds were isolated and their structures were identified as β-sitosterol( 1),benzoic acid( 2),5-hydroxy-7,3’,4’-trimethoxyflavone( 3),tetrapedic acid B( 4),tricin( 5),hydnocarpin D( 6),6,7,10-trihydroxy-8-octadecenoic acid( 7),5’-methoxyhydnocarpin-D( 8) and daucosterol( 9).. Compound 2,4,7,8 are isolated from this plant,compounds 2,7,8 are isolated from Caprifoliaceae family for the first time.

    Topics: Drugs, Chinese Herbal; Flavonoids; Lonicera; Plant Extracts; Sitosterols

2016
Amelioration of oxidative and inflammatory status in hearts of cholesterol-fed rats supplemented with oils or oil-products with extra virgin olive oil components.
    European journal of nutrition, 2016, Volume: 55, Issue:3

    The contribution of extra virgin olive oil (EVOO) macro- and micro-constituents in heart oxidative and inflammatory status in a hypercholesterolemic rat model was evaluated. Fatty acid profile as well as α-tocopherol, sterol, and squalene content was identified directly in rat hearts to distinguish the effect of individual components or to enlighten the potential synergisms.. Oils and oil-products with discernible lipid and polar phenolic content were used. Wistar rats were fed a high-cholesterol diet solely, or supplemented with one of the following oils, i.e., EVOO, sunflower oil (SO), and high-oleic sunflower oil (HOSO) or oil-products, i.e., phenolics-deprived EVOO [EVOO(-)], SO enriched with the EVOO phenolics [SO(+)], and HOSO enriched with the EVOO phenolics [HOSO(+)]. Dietary treatment lasted 9 weeks; at the end of the intervention blood and heart samples were collected.. High-cholesterol-diet-induced dyslipidemia was shown by increase in serum total cholesterol, low-density lipoprotein cholesterol, and triacylglycerols. Dyslipidemia resulted in increased malondialdehyde (MDA) and tumor necrosis factor-α (TNF-α) levels, while glutathione and interleukin 6 levels remained unaffected in all intervention groups. Augmentation observed in MDA and TNF-α was attenuated in EVOO, SO(+), and HOSO(+) groups. Heart squalene and cholesterol content remained unaffected among all groups studied. Heart α-tocopherol was determined by oil α-tocopherol content. Variations were observed for heart β-sitosterol, while heterogeneity was reported with respect to heart fatty acid profile in all intervention groups.. Overall, we suggest that the EVOO-polar phenolic compounds decreased MDA and TNF-α in hearts of cholesterol-fed rats.

    Topics: alpha-Tocopherol; Animals; Cholesterol, Dietary; Cholesterol, HDL; Cholesterol, LDL; Diet; Diet, High-Fat; Dyslipidemias; Fatty Acids; Glutathione; Hypercholesterolemia; Inflammation; Interleukin-6; Male; Malondialdehyde; Olive Oil; Oxidative Stress; Phenols; Plant Oils; Rats; Rats, Wistar; Sitosterols; Sunflower Oil; Triglycerides; Tumor Necrosis Factor-alpha

2016
A new 9,10-dihydrophenanthrene from Dendrobium moniliforme.
    Natural product research, 2016, Volume: 30, Issue:2

    A new 9,10-dihydrophenanthrene,1,5-dihydroxy-3,4,7-trimethoxy-9,10-dihydrophenanthrene (1) was isolated and identified from the whole plants of Dendrobium moniliforme, as well as 24 known compounds including hircinol (2), (2R*,3S*)-3-hydroxymethyl-9-methoxy-2-(4'-hydroxy-3',5'-dimethoxyphenyl)-2,3,6,7-tetrahydro-phenanthro[4,3-b]furan-5,11-diol (3), diospyrosin (4), aloifol I (5), moscatilin (6), 3,4'-dihydroxy-3',4,5-trimethoxybibenzyl (7), gigantol (8), 3,3'-dihydroxy-4,5-dimethoxybibenzyl (9), longicornuol A (10), N-trans-cinnamoyltyramine (11), paprazine (12), N-trans-feruloyl 3'-O-methyldopamine (13), moupinamide (14), dihydroconiferyl dihydro-p-coumarate (15), dihydrosinapyl dihydro-p-coumarate (16), 3-isopropyl-5-acetoxycyclohexene-2-one-1 (17), p-hydroxybenzaldehyde (18), vanillin (19), p-hydroxyphenylpropionic acid (20), vanillic acid (21), protocatechuic acid (22), (+)-syringaresinol (23), β-sitosterol (24) and daucosterol (25). Compounds 3, 4, 13, 16, 17 and 20 were isolated from the Dendrobium genus for the first time, and compounds 2, 5, 7, 9-12, 14, 15, 18, 21 and 22 were originally obtained from D. moniliforme.

    Topics: Benzaldehydes; Bibenzyls; Cinnamates; Coumaric Acids; Dendrobium; Furans; Guaiacol; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Phenanthrenes; Phenylpropionates; Plants, Medicinal; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Tyramine

2016
Anti-tumour-promoting and thermal-induced protein denaturation inhibitory activities of β-sitosterol and lupeol isolated from Diospyros lotus L.
    Natural product research, 2016, Volume: 30, Issue:10

    In this study, the anti-tumour-promoting and thermal-induced protein denaturation inhibitory activities of β-sitosterol (1) and lupeol (2), isolated from Diospyros lotus L., were explored. Compound 1 showed a marked concentration-dependent inhibition against 12-O-tetradecanoylphorbol-13-acetate (20 ng/32 pmol)-induced Epstein-Barr virus early antigen activation in Raji cells with IC50 of 270 μg/ml, without significant toxicity (70% viability). Compound 2 showed significant anti-tumour-promoting effect with IC50 of 412 μg/ml, without significant toxicity (60% viability). In heat-induced protein denaturation assay, compound 1 exhibited a concentration-dependent attenuation with a maximum effect of 73.5% at 500 μg/ml with EC50 of 117 μg/ml, while compound 2 exhibited a maximum effect of 59.2% at 500 μg/ml with EC50 of 355 μg/ml. Moreover, in silico docking studies against the phosphoinositide 3-kinase enzyme also show the inhibitory potency of these compounds. In short, both the compounds exhibited a marked anti-tumour-promoting and potent inhibitory effect on thermal-induced protein denaturation.

    Topics: Animals; Antigens, Viral; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Diospyros; Humans; Inhibitory Concentration 50; Mice; Molecular Docking Simulation; Molecular Structure; Pentacyclic Triterpenes; Phosphatidylinositol 3-Kinases; Phosphoinositide-3 Kinase Inhibitors; Plant Extracts; Plant Roots; Protein Denaturation; Sitosterols; Tetradecanoylphorbol Acetate

2016
Chemical profiling and anti-psoriatic activity of methanolic extract of Andrographis nallamalayana J.L.Ellis.
    Natural product research, 2016, Volume: 30, Issue:11

    Andrographis nallamalayana is being widely used as tribal medicine in the treatment of leucoderma and mouth ulcers. Chemical profiling of methanolic extract of the whole plant (PE), using GC-MS and LC-MS, revealed the presence of compounds viz. α-tocopherol, β-sitosterol, tetradecanoic acid, monostearin, flavones/flavanones and their glycosides, chromones, etc. Topical application of imiquimod on the dorsal portion of male BALB/C mice resulted in the development of psoriatic symptoms (erythema, scaling, thickening and folding) with a mean disease activity index (DAI) of >7.0. Topical treatment with 100-μL PE (~6.4%/12.8%) formulations, for 12-days, resulted in the alleviation of disease symptoms. Compared to water-based formulations, emu oil-based formulation, PE400EO was found more effective in reducing the mean DAI (>84%), keratinocyte count (>65%) (p < 0.01) and interleukin-22 (~70%) (p < 0.05). We report, for the first time, anti-psoriatic activity of A. nallamalayana having great potential in developing a potent phytomedicine against psoriasis.

    Topics: alpha-Tocopherol; Andrographis; Animals; Flavanones; Flavones; Gas Chromatography-Mass Spectrometry; Glycosides; Interleukin-22; Interleukins; Male; Methanol; Mice; Mice, Inbred BALB C; Plant Extracts; Psoriasis; Sitosterols

2016
Evaluation of antiurolithiatic and antioxidant potential of Lepidagathis prostrata: A Pashanbhed plant.
    Pharmaceutical biology, 2016, Volume: 54, Issue:7

    Oxidative stress acts as an essential mediator in the pathophysiology of urolithiasis. Lepidagathis prostrata Dalz. (Acanthaceae) is a Pashanbhed plant that is recommended for the management of urolithiasis; however, no scientific validation has been reported.. To evaluate the antiurolithiatic and antioxidant potential of L. prostrata.. Methanol extract (LPM) and fractions; petroleum ether (LPPE), ethyl acetate (LPEA), n-butanol (LPBU) and aqueous (LPAQ) were prepared. In vitro antiurolithiatic activity was evaluated by the capacity to inhibit calcium oxalate (CaOx) nucleation and aggregation at different concentrations of extract/fractions (0.04-3 mg/mL) for 30 min. Total phenol and flavonoid content and antioxidant potential were determined. A validated HPTLC method was performed to quantify lupeol and β-sitosterol.. LPEA exhibited the highest dose-dependent inhibition of CaOx nucleation (IC50: 336.23 ± 30.79 µg/mL) and aggregation (IC50: 149.63 ± 10.31 µg/mL), which was significantly (p < 0.05) better than standard Cystone®. The polar LPBU fraction was enriched with phenols (47.34 ± 0.19 mg GAE/g) and flavonoids (20.38 ± 0.05 mg QE/g), which correlates with its highest antioxidant potential in DPPH, ABTS, nitric oxide scavenging and iron chelating activities (IC50: 1.18-87.34 µg/mL). To our knowledge, this is the first study reporting the presence of lupeol and β-sitosterol in L. prostrata.. The antiurolithiatic activity of L. prostrata is probably mediated through the inhibition of CaOx crystallization. In addition to its free radical scavenging and antioxidant activities, it would act as an excellent agent for the prevention of urolithiasis.

    Topics: Acanthaceae; Antioxidants; Calcium Oxalate; Crystallization; Dose-Response Relationship, Drug; Iron Chelating Agents; Lipid Peroxidation; Oxidative Stress; Pentacyclic Triterpenes; Phytotherapy; Plant Extracts; Plants, Medicinal; Sitosterols; Urolithiasis; Urological Agents

2016
Effects of Different Carbon Sources on Growth, Membrane Permeability, β-Sitosterol Consumption, Androstadienedione and Androstenedione Production by Mycobacterium neoaurum.
    Interdisciplinary sciences, computational life sciences, 2016, Volume: 8, Issue:1

    Effects of different carbon sources on growth, membrane permeability, β-sitosterol consumption, androstadienedione and androstenedione (AD(D)) production by Mycobacterium neoaurum were investigated. The results indicated that glucose was advantageous to the growth and resulted in the adverse effects on the phytosterols consumption and AD(D) production compared to the results of propanol and isopropanol as sole carbon source. The cell wall widths of 9.76 by propanol and 8.00 nm by isopropanol were 38.3 and 49.4 % thinner than that of 15.82 nm by glucose, respectively. The partition coefficient of the cell grown in propanol and isopropanol was 18.1 and 22.2, which were 7.23- and 9.09-fold higher than that of the cell grown in glucose.

    Topics: Androstadienes; Androstenedione; Carbon; Cell Membrane Permeability; Cell Wall; Hydrophobic and Hydrophilic Interactions; Lipids; Mycobacterium; Sitosterols

2016
Phytosterols in onion contribute to a sensation of lingering of aroma, a koku attribute.
    Food chemistry, 2016, Feb-01, Volume: 192

    We aimed to examine the substance in a precipitate of heat-treated onion concentrate (HOC) that contributes to a sensation of lingering of aroma, a koku attribute induced by the sensing of richness and persistence in terms of taste, aroma and texture. Adding precipitate, separated from HOC, to consommé enhanced the lingering sensation of aroma in the consommé more than adding the supernatant from HOC. After the precipitate was washed with hot water and ethanol its enhancing effect disappeared. Analysis of the HOC precipitate showed that it contained phytosterols, such as beta-sitosterol and stigmasterol. Tests of binding to aroma compounds showed that both sterols, as well as the washed precipitate, were able to bind methyl propyl disulfide and N-hexanal. Thus phytosterols in the HOC precipitate seemed to bind and hold the aroma compounds and gradually release them, inducing a lingering sensation of aroma under the koku concept during consumption.

    Topics: Aldehydes; Ethanol; Gas Chromatography-Mass Spectrometry; Hot Temperature; Odorants; Onions; Phytosterols; Sitosterols; Sterols; Stigmasterol

2016
Quantification of polyphenols and flavonoid content and evaluation of anti-inflammatory and antimicrobial activities of Stenocereus stellatus extracts.
    Natural product research, 2016, Volume: 30, Issue:16

    The hexanic, ethyl acetate and methanolic extracts from branches of Stenocereus stellatus were tested in both the 12-O-tetradecanoylphorbol-13-acetate (TPA) - induced ear oedema model and antimicrobial activity assay. The % of oedema inhibition, the Minimum Inhibitory Concentration (MIC), as well as the polyphenolic and flavonoid content were determined. Also, extracts were analysed by gas chromatography-mass spectrometry (GC-MS). In TPA model, the three extracts showed moderate oedema inhibition. In the antimicrobial activity assay, methanolic extract shows better MIC against all strains. The lowest MICs were for Candida albicans (31 μg/mL) and Rhizopus sp. (15 μg/mL). Also, 50.78 mg eq. of gallic acid/g extract of polyphenol and 115.12 mg eq. of catequine/g extract of flavonoids content were founded in ethyl acetate extract. In the chromatographic analysis, β-sitosterol, β-amyrine, betulin and some other molecules were identified. The results show that S. stellatus possess antimicrobial activities against some fungus species.

    Topics: Animals; Anti-Infective Agents; Anti-Inflammatory Agents, Non-Steroidal; Antioxidants; Cactaceae; Candida albicans; Disease Models, Animal; Edema; Flavonoids; Gas Chromatography-Mass Spectrometry; Male; Microbial Sensitivity Tests; Phorbol Esters; Plant Extracts; Polyphenols; Rhizopus; Secondary Metabolism; Sitosterols

2016
Bioaccessibility study of plant sterol-enriched fermented milks.
    Food & function, 2016, Volume: 7, Issue:1

    The bioaccessibility (BA) of total and individual plant sterols (PS) of four commercial PS-enriched fermented milk beverages (designated as A to D) was evaluated using in vitro gastrointestinal digestion including the formation of mixed micelles. The fat content of the samples ranged from 1.1 to 2.2% (w/w), and PS enrichment was between 1.5 and 2.9% (w/w). β-Sitosterol, contained in all samples, was higher in samples A and B (around 80% of total PS). The campesterol content was C (22%) > A (7%) > B (5%). Sitostanol was the most abundant in sample D (85%). Stigmasterol was only present in sample C (33%). The greatest BA percentage for total PS corresponded to samples A and B (16-17%), followed by sample D (11%) and sample C (9%). The total BA was not related to the protein, lipid or PS content of the beverages, whereas samples with higher carbohydrates and fiber contents showed lower BA. The BA of the individual PS differed according to the sample considered, and was not related to the PS profile of the sample, thus indicating strong dependency upon the matrix (PS ingredient and other components). Although in vivo studies should be carried out to better assess the functionality of PS in functional foods such as enriched fermented milk beverages, our in vitro study is a useful preliminary contribution to evaluation of the efficacy of these products.

    Topics: Biological Availability; Cholesterol; Cultured Milk Products; Dietary Carbohydrates; Dietary Fats; Dietary Fiber; Digestion; Food, Fortified; Functional Food; Gastrointestinal Tract; Micelles; Models, Biological; Phytosterols; Sitosterols; Stigmasterol

2016
Lipophilic bioactive compounds in the oils recovered from cereal by-products.
    Journal of the science of food and agriculture, 2016, Volume: 96, Issue:9

    The by-products of seven different cereal grains were investigated as a source of extractable oil, rich in lipophilic bioactive compounds.. Oil yields (g kg(-1) DW) recovered from cereal by-products were as follows: 189 (rice bran) > 112 (wheat germ) > 74 (corn bran) > 58 (oat bran) > 41 (buckwheat bran) > 39 (spelt bran) > 33 (wheat bran) > 27 (rye bran). The main fatty acids identified in the studied oil samples were palmitic acid (11.39-17.23%), oleic acid (11.76-42.73%), linoleic acid (35.54-62.65%) and α-linolenic acid (1.05-9.46%). The range of total tocochromanols and phytosterols in the obtained oils was 0.369-3.763 and 1.19-35.24 g kg(-1) of oil, respectively. The oils recovered from buckwheat and corn bran, and wheat germ were dominated by tocopherols (99.9, 84.2 and 96.5%, respectively), whereas the oat, rice, rye, spelt, wheat bran oils were rich in tocotrienols (73.9, 79.6, 78.1, 90.6 and 73.8%, respectively). The campesterol and β-sitosterol constituted 10.1-32.5 and 30.4-63.7%, respectively, of total phytosterols contents identified in all of the studied samples.. The present study demonstrated that oils recovered from the cereal by-products are richer sources of bioactive compounds, compared with traditional oils. © 2015 Society of Chemical Industry.

    Topics: Cholesterol; Edible Grain; Fatty Acids; Phytosterols; Plant Extracts; Plant Oils; Seeds; Sitosterols; Squalene; Tocopherols; Tocotrienols; Triticum

2016
Bioactive Phenylpropanoids, Phenolic Acid and Phytosterol from Landolphia owariensis P. Beauv Stringy Seed Pulp.
    Phytotherapy research : PTR, 2016, Volume: 30, Issue:1

    Landolphia owariensis P. Beauv is economically important for latex/rubber and folklore medicine. Its stringy seed pulp is freely eaten by humans and animals. Thus, L. owariensis stringy seed pulp was extracted serially with hexane and acetone to isolate and characterize its active pharmaceutical ingredients. Solvent/solvent partition and chromatographic separations afforded four bioactive compounds, (E)-3-(3,4-Dihydroxylcinnamoyl)quinic acid [(E)-Chlorogenic acid], I; (E)-3-(3,4-Dihydroxylcinnamoyl)quinic acid methyl ester [(E)-Chlorogenic acid methyl ester], II; 3,4-Dihydroxylbenzoic acid, (Protocatechuic acid), III; and 22,23-Dihydrostigmaster-3β-ol (3β-Sitosterol) (IV). Structures of I, II and III were assigned by combinations of high-performance liquid chromatography-ultraviolet-visible spectroscopy, 1D and 2D nuclear magnetic resonance spectroscopy, high-performance liquid chromatography-mass spectrometry and reference to published literatures, while compound IV was identified by chemical methods and gas chromatography-mass spectrometry. The phenylpropanoids and phenolic acid (compounds I, II and III) are notable standard antioxidants with confirmed hepatic-protective activity and other exciting biological activities. Compound IV has been reported to possess anti-inflammatory activity, anti-colon cancer action and a cholesterol-lowering effect. The described compounds are important medicinal constituents of L. owariensis stringy seed pulp, and this is the first major report on the phytochemistry of L. owariensis P. Beauv.

    Topics: Apocynaceae; Chlorogenic Acid; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Hydroxybenzoates; Phytosterols; Plant Extracts; Quinic Acid; Seeds; Sitosterols

2016
Cholesterol absorption and synthesis markers in Portuguese hypercholesterolemic adults: A cross-sectional study.
    European journal of internal medicine, 2016, Volume: 28

    The dynamics of cholesterol homeostasis and the development of cardiovascular disease (CVD) are complex and multifactorial, to which adds individual variability in the proportion of cholesterol from exogenous versus endogenous sources. The aim of this study was to undertake the first characterization of cholesterol absorption and synthesis profiles in Portuguese hypercholesterolemic adults through the quantification of surrogate markers, and the analysis of the predictive value of age and sex on the cholesterol homeostasis biomarkers.. Serum samples for the measurement of lipid profiles and cholesterol homeostasis markers were obtained for 100 men and 112 women, aged 30-65, with TC ≥ 5.2 mmol/L (~200mg/dL) and/or LDL-C ≥ 2.6 mmol/L (~100mg/dL), none of whom were on any lipid-lowering therapy.. Overall, sex-specific significant differences were observed in the cholesterol homeostasis markers and lipid profiles; women had lower cholesterol synthesis marker concentrations (P<0.01 for lathosterol) and lipid parameters (except for HDL-C concentrations). Age-related significant differences were also found, including higher concentrations of cholesterol absorption markers in association with increasing age.. In our study, the predictors of higher levels of cholesterol absorption markers were higher age and female gender.

    Topics: Adult; Age Factors; Aged; Biomarkers; Cholestanol; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Cross-Sectional Studies; Desmosterol; Diet; Female; Homeostasis; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Portugal; Sex Factors; Sitosterols; Triglycerides

2016
Unsaturated lipid matrices protect plant sterols from degradation during heating treatment.
    Food chemistry, 2016, Apr-01, Volume: 196

    The interest in plant sterols enriched foods has recently enhanced due to their healthy properties. The influence of the unsaturation degree of different fatty acids methyl esters (FAME: stearate, oleate, linoletate and linolenate) on a mixture of three plant sterols (PS: campesterol, stigmasterol and β-sitosterol) was evaluated at 180 °C for up to 180 min. Sterols degraded slower in the presence of unsaturated FAME. Both PS and FAME degradation fit a first order kinetic model (R(2)>0.9). Maximum oxysterols concentrations were achieved at 20 min in neat PS and 120 min in lipid mixtures and this maximum amount decreased with increasing their unsaturation degree. In conclusion, the presence of FAME delayed PS degradation and postponed oxysterols formation. This protective effect was further promoted by increasing the unsaturation degree of FAME. This evidence could help industries to optimize the formulation of sterol-enriched products, so that they could maintain their healthy properties during cooking or processing.

    Topics: alpha-Linolenic Acid; Cholesterol; Fatty Acids; Food Handling; Hot Temperature; Linoleic Acid; Oleic Acid; Phytosterols; Protective Agents; Sitosterols; Stearates; Stigmasterol

2016
Distribution and factors affecting adsorption of sterols in the surface sediments of Bosten Lake and Manas Lake, Xinjiang.
    Environmental science and pollution research international, 2016, Volume: 23, Issue:6

    This study investigated the concentrations and distribution of eight sterol compounds in the surface sediments of Bosten Lake and Manas Lake, Xinjiang, China. The ratios of sterols as diagnostic indices were used to identify pollution sources. The sediment of the two lakes was selected as an adsorbent to investigate the adsorption behaviour of sterols. Results showed that the sterols were widely distributed in the sediments of the lakes in the study areas. The total concentrations of the detected sterols in Bosten Lake and in Manas Lake were 1.584-27.897 and 2.048-18.373 μg g(-1)∙dw, respectively. In all of the sampling sites, the amount of faecal sterols was less than that of plant sterols. β-sitosterol was the dominant plant sterol with a mean concentration of 2.378 ± 2.234 μg g(-1)∙dw; cholesterol was the most abundant faecal sterol with a mean concentration of 1.060 ± 1.402 μg g(-1)∙dw. The pollution level was higher in Bosten Lake than in Manas Lake. Majority of the ratios clearly demonstrated that the contamination by human faecal sources was occurring at stations which are adjacent to residential areas and water inlets. The adsorption behaviour of sterols to sediment suggested that the sterol adsorption coefficients were reduced as temperature increased. As salinity increased, the adsorption quantity also increased. As pH increased, the sediment adsorption of sterol slightly increased because the strong alkaline solution is not conducive to the adsorption of sterols. The ratios between sterols did not change largely with the change in external factors.

    Topics: Adsorption; China; Geologic Sediments; Humans; Lakes; Sitosterols; Sterols; Water Pollutants, Chemical

2016
Isolation, characterization and HPLC quantification of compounds from Aquilegia fragrans Benth: Their in vitro antibacterial activities against bovine mastitis pathogens.
    Journal of ethnopharmacology, 2016, Feb-03, Volume: 178

    The underground parts of Aquilegia fragrans are traditionally used for the treatment of wounds and various inflammatory diseases like bovine mastitis. However, there are no reports on the phytochemical characterization and antibacterial studies of A. fragrans.. To isolate compounds from the methanol extract of the underground parts of A. fragrans and determine their antibacterial activity against the pathogens of bovine mastitis. The study was undertaken in order to scientifically validate the traditional use of A. fragrans.. Five compounds were isolated from the methanol extract of the underground parts of A. fragrans using silica gel column chromatography. Structural elucidation of the isolated compounds was done using spectral data analysis and comparison with literature. High performance liquid chromatography (HPLC) was used for the qualitative and quantitative determination of isolated compounds in the crude methanol extract. The methanol extract and isolated compounds were evaluated for antibacterial activities against mastitis pathogens using broth micro-dilution technique.. The five isolated compounds were identified as (1) 2, 4-dihydroxyphenylacetic acid methyl ester (2) β-sitosterol (3) Aquilegiolide (4) Glochidionolactone-A and (5) Magnoflorine. A quick and sensitive HPLC method was developed for the first time for qualitative and quantitative determination of four isolated marker compounds from A. fragrans. The crude methanol extract and compound 5 exhibited weak antibacterial activities that varied between the bacterial species (MIC=500-3000 µg/ml).. The above results show that the crude methanol extract and isolated compounds from A. fragrans exhibit weak antibacterial activities. Further phytochemical and pharmacological studies are required for proper scientific validation of the folk use of this plant species in the treatment of various inflammatory diseases like bovine mastitis.

    Topics: Animals; Anti-Bacterial Agents; Aporphines; Aquilegia; Benzofurans; Cattle; Chromatography, High Pressure Liquid; Female; Mastitis, Bovine; Methanol; Microbial Sensitivity Tests; Plant Extracts; Sitosterols

2016
Spatial and temporal regulation of sterol biosynthesis in Nicotiana benthamiana.
    Physiologia plantarum, 2016, Volume: 157, Issue:2

    Nicotiana benthamiana was used as a model to investigate the spatial and developmental relationship between sterol synthesis rates and sterol content in plants. Stigmasterol levels were approximately twice the level in roots as that found in aerial tissues, while its progenitor sterol sitosterol was the inverse. When incorporation of radiolabeled precursors into sterols was used as measure of in vivo synthesis rates, acetate incorporation was similar across all tissue types, but approximately twofold greater in roots than any other tissue. In contrast, mevalonate incorporation exhibited the greatest differential with the rate of incorporation in roots approximately one-tenth that in apical shoots. Similar to acetate, incorporation of farnesol was higher in roots but remained fairly constant in aerial tissues, suggesting less regulation of the downstream sterol biosynthetic steps. Consistent with the precursor incorporation data, analysis of gene transcript and measurements of putative rate-limiting enzyme activities for 3-hydroxy-3-methylglutaryl-coenzyme A synthase (EC 2.3.3.10) and reductase (EC 1.1.1.34) showed the greatest modulation of levels, while the activity levels for isopentenyl diphosphate isomerase (EC 5.3.3.2) and prenyltransferases (EC 2.5.1.10 and EC 2.5.1.1) also exhibited a strong but moderate correlation with the development age of the aerial tissues of the plants. Overall, the data suggest a multitude of means from transcriptional to posttranslational control affecting sterol biosynthesis and accumulation across an entire plant, and point to some particular control points that might be manipulated using molecular genetic approaches to better probe the role of sterols in plant growth and development.

    Topics: Biosynthetic Pathways; Mevalonic Acid; Nicotiana; Organ Specificity; Phytosterols; Plant Roots; Sitosterols; Stigmasterol

2016
Sterol composition of virgin olive oil of forty-three olive cultivars from the World Collection Olive Germplasm Bank of Cordoba.
    Journal of the science of food and agriculture, 2016, Volume: 96, Issue:12

    In olive oil, sterols constitute the majority of the unsaponifiable fraction. In recent years there has been increased interest in the sterols of olive oil for their health benefits and their importance to virgin olive oil (VOO) quality regulation.. Forty-three olive (Olea europaea L.) cultivars from the World Olive Germplasm Bank, IFAPA Centro 'Alameda de Obispo', Cordoba, Spain were studied for their oil sterol composition and total content. The main sterols found in olive oil were β-sitosterol, Δ(5) -avenasterol, campesterol and stigmasterol, most of them showing high variability. Most cultivars showed total sterol contents within the limits established by EU regulations, although 28% of VOOs analysed were outside the limits established for total content and/or for individual sterols. Over the group of cultivars, total sterol contents ranged from 855 to 2185 mg kg(-1) .. The high variability observed was due to the genetic component, since other agronomic and technological factors were similar. Because of the high variability, the sterol fraction can be considered as a useful tool to characterize and discriminate monovarietal VOOs. The results can be useful for nutritionists for VOO inclusion in nutrition studies. Furthermore, the variability observed can be applied in olive breeding projects to select the parents of new olive cultivars with an improved sterol fraction. © 2016 Society of Chemical Industry.

    Topics: Chemical Industry; Fruit; Genotype; Olea; Olive Oil; Plant Breeding; Seed Bank; Sitosterols; Spain; Species Specificity; Sterols

2016
Phytosterol content and the campesterol:sitosterol ratio influence cotton fiber development: role of phytosterols in cell elongation.
    Science China. Life sciences, 2016, Volume: 59, Issue:2

    Phytosterols play an important role in plant growth and development, including cell division, cell elongation, embryogenesis, cellulose biosynthesis, and cell wall formation. Cotton fiber, which undergoes synchronous cell elongation and a large amount of cellulose synthesis, is an ideal model for the study of plant cell elongation and cell wall biogenesis. The role of phytosterols in fiber growth was investigated by treating the fibers with tridemorph, a sterol biosynthetic inhibitor. The inhibition of phytosterol biosynthesis resulted in an apparent suppression of fiber elongation in vitro or in planta. The determination of phytosterol quantity indicated that sitosterol and campesterol were the major phytosterols in cotton fibers; moreover, higher concentrations of these phytosterols were observed during the period of rapid elongation of fibers. Furthermore, the decrease and increase in campesterol:sitosterol ratio was associated with the increase and decease in speed of elongation, respectively, during the elongation stage. The increase in the ratio was associated with the transition from cell elongation to secondary cell wall synthesis. In addition, a number of phytosterol biosynthetic genes were down-regulated in the short fibers of ligon lintless-1 mutant, compared to its near-isogenic wild-type TM-1. These results demonstrated that phytosterols play a crucial role in cotton fiber development, and particularly in fiber elongation.

    Topics: Cholesterol; Cotton Fiber; Mass Spectrometry; Phytosterols; Sitosterols

2016
Human CYP27A1 catalyzes hydroxylation of β-sitosterol and ergosterol.
    Biological chemistry, 2016, 06-01, Volume: 397, Issue:6

    β-Sitosterol and ergosterol are the equivalents of cholesterol in plants and fungi, respectively, and common sterols in the human diet. In the current work, both were identified as novel CYP27A1 substrates by in vitro experiments applying purified human CYP27A1 and its redox partners adrenodoxin (Adx) and adrenodoxin reductase (AdR). A Bacillus megaterium based biocatalyst recombinantly expressing the same proteins was utilized for the conversion of the substrates to obtain sufficient amounts of the novel products for a structural NMR analysis. β-Sitosterol was found to be converted into 26-hydroxy-β-sitosterol and 29-hydroxy-β-sitosterol, whereas ergosterol was converted into 24-hydroxyergosterol, 26-hydroxyergosterol and 28-hydroxyergosterol.

    Topics: Biocatalysis; Cholestanetriol 26-Monooxygenase; Ergosterol; Humans; Hydroxylation; Oxidation-Reduction; Sitosterols

2016
Thonningiiflavanonol A and thonningiiflavanonol B, two novel flavonoids, and other constituents of Ficus thonningii Blume (Moraceae).
    Zeitschrift fur Naturforschung. C, Journal of biosciences, 2016, Volume: 71, Issue:3-4

    A phytochemical study of Ficus thonningii has led to the isolation of two previously unreported compounds, thonningiiflavanonol A and thonningiiflavanonol B together with 16 known compounds: shuterin, naringenin, syringic acid, p-hydroxybenzoic acid, genistein, 5,7,3',4',5'-pentahydroxyflavanone, luteolin, methylparaben, aromadendrin, garbanzol, dihydroquercetin, 5,7,3'-trihydroxyflavanone, β-sitosterol, sitosterolglucoside, lupeol acetate, and taraxerol. Their structures were elucidated on the basis of spectroscopic data. The new compounds and extracts displayed potent antioxidant activity.

    Topics: Antioxidants; Ficus; Flavanones; Flavonoids; Gallic Acid; Genistein; Luteolin; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Parabens; Plant Bark; Plant Extracts; Plant Roots; Plant Stems; Quercetin; Sitosterols

2016
Cyclopenta[b]benzofuran and Secodammarane Derivatives from the Stems of Aglaia stellatopilosa.
    Journal of natural products, 2016, Apr-22, Volume: 79, Issue:4

    Four new 2,3-secodammarane triterpenoids, stellatonins A-D (3-6), together with a new 3,4-secodammarane triterpenoid, stellatonin E (7), and the known silvestrol (1), 5‴-episilvestrol (2), and β-sitosterol, were isolated from a methanol extract of the stems of Aglaia stellatopilosa through bioassay-guided fractionation. The structures of the new compounds were elucidated using spectroscopic and chemical methods. The compounds were evaluated for their cytotoxic activity against three human cancer cell lines and for their antimicrobial activity using a microtiter plate assay against a panel of Gram-positive and Gram-negative bacteria and fungi.

    Topics: Aglaia; Antineoplastic Agents, Phytogenic; Benzofurans; Dammaranes; Drug Screening Assays, Antitumor; Female; Gram-Negative Bacteria; Gram-Positive Bacteria; HT29 Cells; Humans; Malaysia; Microbial Sensitivity Tests; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Stems; Saccharomyces cerevisiae; Sitosterols; Triterpenes

2016
Nephroprotective effect of β-sitosterol on N-diethylnitrosamine initiated and ferric nitrilotriacetate promoted acute nephrotoxicity in Wistar rats.
    Journal of basic and clinical physiology and pharmacology, 2016, Sep-01, Volume: 27, Issue:5

    The most abundant plant sterol β-sitosterol is widely used for treating heart diseases and chronic inflammatory conditions. The objective of the current study was to evaluate the nephroprotective effect of β-sitosterol against nephrotoxicants which were studied using renal function markers, antioxidant and lipid peroxidation status, and inflammatory markers.. Male albino Wistar rats were randomly grouped into four: group 1 was vehicle control rats (0.1% carboxymethyl cellulose [CMC]); group 2 was rats treated with N-diethylnitrosamine (DEN) (200 mg/kg body weight [bw] i.p. on the 15th day) and ferric nitrilotriacetate (Fe-NTA) (9 mg/kg bw i.p. on 30th and 32nd days); group 3 was rats that received β-sitosterol (20 mg/kg bw in 0.1% CMC, p.o. for 32 days) 2 weeks prior to the exposure to the nephrotoxicant; and group 4 was rats that received β-sitosterol alone. The experiment was terminated after the 24 h of last dosage of Fe-NTA, and all the animals were sacrificed. The blood, liver and kidney from each group were analyzed for biochemical, molecular and histological changes.. All the parameters showed significant changes in DEN and Fe-NTA treated animals, whereas β-sitosterol pretreated animals' altered biochemical parameters were restored to near normal. Histopathological and immunoexpression studies on tissues also corroborate the biochemical endpoints.. Administration of β-sitosterol to nephrotoxicity induced rats showed significant positive changes in biochemical parameters, histopathological and immunohistochemical observations, and up-regulation of Nrf2 gene expression. From this, it was clear that β-sitosterol showed renal protective function.

    Topics: Animals; Antioxidants; Biomarkers; Diethylnitrosamine; Ferric Compounds; Inflammation; Kidney; Lipid Peroxidation; Liver; Male; Nitrilotriacetic Acid; Protective Agents; Rats; Rats, Wistar; Sitosterols; Up-Regulation

2016
Impact of Cultivar on Profile and Concentration of Lipophilic Bioactive Compounds in Kernel Oils Recovered from Sweet Cherry (Prunus avium L.) by-Products.
    Plant foods for human nutrition (Dordrecht, Netherlands), 2016, Volume: 71, Issue:2

    Lipophilic bioactive compounds in oils recovered from the kernels of seven sweet cherry (Prunus avium L.) cultivars, harvested at single location in 2013, were studied. Oil yield in sweet cherry ranged between 30.3-40.3 % (w/w) dw. The main fatty acids were oleic acid (39.62-49.92 %), linoleic acid (31.13-38.81 %), α-eleostearic acid (7.23-10.73 %) and palmitic acid (5.59-7.10 %), all four represented approximately 95 % of the total detected fatty acids. The ranges of total tocochromanols and sterols were between 83.1-111.1 and 233.6-419.4 mg/100 g of oil, respectively. Regardless of the cultivar, the γ-tocopherol and β-sitosterol were the main lipophilic minor bioactive compounds. The content of the carotenoids and squalene were between 0.38-0.62 and 60.9-127.7 mg/100 g of oil, respectively. Three significant correlations were found between oil yield and total contents of sterols (r = -0.852), tocochromanols (r = -0.880) and carotenoids (r = -0.698) in sweet cherry kernel oils. The oil yield, as well as the content of lipophilic bioactive compounds in oil was significantly affected by the cultivar.

    Topics: Carotenoids; Linoleic Acid; Linolenic Acids; Phytosterols; Plant Oils; Prunus avium; Seeds; Sitosterols; Squalene; Sterols

2016
Pollution by oestrogenic endocrine disruptors and β-sitosterol in a south-western European river (Mira, Portugal).
    Environmental monitoring and assessment, 2016, Volume: 188, Issue:4

    The Mira River is a Portuguese water body widely known for its wilderness and is advertised as one of the less polluted European rivers. On this presumption, the levels of endocrine-disrupting compounds (EDCs) in Mira waters were never measured. However, because environmentalists have claimed that the Mira could be moderately polluted, a range of 17 EDCs were measured not only at the estuary but also along the river. The targeted EDCs included natural and pharmaceutical oestrogens (17β-oestradiol, oestrone and 17α-ethynylestradiol), industrial/household pollutants (octylphenols, nonylphenols and their monoethoxylates and diethoxylates and bisphenol A), phytoestrogens (formononetin, biochanin A, daidzein, genistein) and the phytosterol sitosterol (SITO). For this propose, waters from six sampling sites were taken every 2 months, over a 1-year period (2011), and analysed by gas chromatography-mass spectrometry. Unexpectedly high levels of oestrogens and of industrial/household pollutants were measured at all sampling sites, including those located inside natural protected areas. Indeed, the annual average sum of EDCs was ≈57 ng/L for oestrogens and ≈1.3 μg/L for industrial/household chemicals. In contrast, the global average levels of phytoestrogens (≈140 ng/L) and of SITO (≈295 ng/L) were lower than those reported worldwide. The EDC concentrations were normalised for ethynylestradiol equivalents (EE2eq). In view of these, the oestrogenic load of the Mira River attained ≈47 ng/L EE2eq. In addition, phosphates were above legal limits at both spring and summer (>1 mg/L). Overall, data show EDCs at toxicant relevant levels in the Mira and stress the need to monitor rivers that are allegedly less polluted.

    Topics: Benzhydryl Compounds; Endocrine Disruptors; Environmental Monitoring; Estrogens; Estrone; Estuaries; Gas Chromatography-Mass Spectrometry; Genistein; Phenols; Portugal; Rivers; Seasons; Sitosterols; Water Pollutants, Chemical

2016
Beneficial effects of β-sitosterol on type 1 cholecystokinin receptor dysfunction induced by elevated membrane cholesterol.
    Clinical nutrition (Edinburgh, Scotland), 2016, Volume: 35, Issue:6

    The type 1 cholecystokinin receptor (CCK1R) mediates the actions of CCK to support nutritional homeostasis, including post-cibal satiety. However, elevated levels of membrane cholesterol, such as have been observed in metabolic syndrome, interfere with CCK stimulus-activity coupling at the CCK1R, thereby disrupting this important servomechanism. We hypothesize that reversal of the negative impact of cholesterol on this receptor could be useful in the management of obesity.. We have studied the effects of β-sitosterol, a phytosterol structurally related to cholesterol, on CCK receptor function. This included CCK binding and biological activity at wild type CCK1R and CCK2R, as well as at CCK1R in a high cholesterol environment, and at a CCK1R mutant, Y140A, which mimics the behavior of wild type receptor in high cholesterol.. β-sitosterol (100 μM and 10 μM) significantly improved the defective signaling of the CCK1R present in high cholesterol (p < 0.05), without affecting CCK binding affinity. This effect was absent at the CCK1R present in a normal cholesterol environment, as well as at the structurally-related CCK2R. Furthermore, the cholesterol-insensitive Y140A mutant of CCK1R was resistant to the effects of β-sitosterol.. These data suggest that β-sitosterol affects CCK1R function in high cholesterol by competing with cholesterol at a receptor cholesterol-binding site and may shift its conformation toward normal. This phytosterol extends our understanding of the structure-activity relationships for developing a drug that can target the external surface of CCK1R. Since the concentrations of β-sitosterol shown to be effective in this study are similar to serum levels of this compound achievable during oral administration, it may be worthwhile to study possible beneficial effects of β-sitosterol in metabolic syndrome.

    Topics: Animals; CHO Cells; Cricetulus; Gene Expression Regulation; Hypercholesterolemia; Hypolipidemic Agents; Receptor, Cholecystokinin A; Signal Transduction; Sitosterols

2016
Gracilone, a new sesquiterpene lactone from Tanacetum gracile (Tansies).
    Natural product research, 2016, Volume: 30, Issue:20

    The methanolic extract of the Tanacetum gracile afforded the isolation of new sesquiterpene lactone, named gracilone (1) along with four known compounds as 14α-taraxeran-3-one (2), 14α-taraxeran-3-ol (3), apigenin (4) and β-sitosterol (5). The structure of compound 1 was elucidated on the basis of 1D, 2D NMR and MS spectroscopic analysis. Antimicrobial, antioxidant and anticancer activities of all compounds were evaluated, from which gracilone (1) showed a moderate antibacterial activity, while apigenin (4) showed comparatively more antibacterial activity against both gram-positive and gram-negative tested strains.

    Topics: Anti-Bacterial Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Cell Line, Tumor; Drug Evaluation, Preclinical; Humans; Inhibitory Concentration 50; Lactones; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Sesquiterpenes; Sitosterols; Tanacetum

2016
A new anthraquinone and eight constituents from Hedyotis caudatifolia Merr. et Metcalf: isolation, purification and structural identification.
    Natural product research, 2016, Volume: 30, Issue:19

    Hedyotis caudatifolia Merr. et Metcalf. (HC), a folk medicine in Yao nationalities areas in China, was used to investigate the chemical constituents. Through silica gel and Sephadex LH-20 column chromatography, nine compounds were isolated and purified. By physical and chemical properties, IR, MS (EI-MS, high resolution EI-MS), 1D NMR ((1)H NMR, (13)C NMR) and 2D NMR (HSQC, (1)H-(1)H COSY, HMBC), their structures were identified as β-sitosterol (1), stigmasterol (2), scopolin (3), 2-hydroxy-1,7,8-trimethoxyanthracene-9,10-dione (4), oleanolic acid (5), ursolic acid (6), methyl barbinervate (7), β-daucosterol (8) and p-Hydroxybenzoic acid (9). These compounds were isolated from HC for the first time, and 4 a new anthraquinone whose biological activities are worth to be investigated in future. These compounds may contribute to the HC's pharmacological effects on treating diseases, and may be used as candidates for control index in establishing the quality control standard of HC.

    Topics: Anthraquinones; China; Hedyotis; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plants, Medicinal; Sitosterols; Stigmasterol; Triterpenes; Ursolic Acid

2016
Cholesterol metabolism in cardiac sarcoidosis.
    Atherosclerosis, 2016, Volume: 248

    Patients with cardiac sarcoidosis (CS) suffer from myocardial inflammation, but atherosclerosis is not infrequent in these patients. However, the classical atherosclerotic risk factors, such as perturbed serum lipids and whole-body cholesterol metabolism, remain unravelled in CS.. We assessed serum non-cholesterol sterols, biomarkers of whole-body cholesterol synthesis and cholesterol absorption efficiency, with gas-liquid chromatography in 39 patients with histologically verified CS and in an age-adjusted random population sample (n = 124).. CS was inactive or responding to treatment in all patients. Concentrations of serum, LDL, and HDL cholesterol and serum triglycerides were similar in CS patients and in control subjects. Cholesterol absorption markers were higher in CS patients than in controls (eg serum campesterol to cholesterol ratio in CS 246 ± 18 vs in controls 190 ± 8 10(2) x μmol/mmol of cholesterol, p = 0.001). Cholesterol synthesis markers were lower in CS patients than in controls (eg serum lathosterol to cholesterol ratio in CS 102 ± 8 vs in controls 195 ± 5 10(2) x μmol/mmol of cholesterol, p = 0.000). In CS patients, cholesterol absorption markers significantly correlated with plasma prohormone brain natriuretic peptide (proBNP), a marker of hemodynamic load.. High cholesterol absorption efficiency, which is suggested to be atherogenic, characterized the metabolic profile of cholesterol in CS patients. The association between cholesterol absorption efficiency and plasma proBNP concentration, which suggests a link between inflammation, cholesterol homeostasis, and hemodynamic load, warrants further studies in order to confirm this finding and to reveal the underlying mechanisms.

    Topics: Adult; Aged; Atherosclerosis; Body Mass Index; Cardiomyopathies; Case-Control Studies; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Diet; Down-Regulation; Female; Finland; Heart Diseases; Hemodynamics; Homeostasis; Humans; Inflammation; Lipoproteins; Male; Middle Aged; Phytosterols; Risk Factors; Sarcoidosis; Sitosterols

2016
Exploration of anti-Malassezia potential of Nyctanthes arbor-tristis L. and their application to combat the infection caused by Mala s1 a novel allergen.
    BMC complementary and alternative medicine, 2016, Mar-31, Volume: 16

    Malassezia commensal yeasts along with multitude of antigens have been found to be associated with various skin disorders including Pityriasis versicolor (PV). Amongst them Mala s1, a 37 kDa protein has been proved to be a major allergen reacting with a large panel of sera. However, there exists no therapeutic alternative to combat such problems in form of plant based natural compounds. The purpose of this study is in the first place, to determine the anti-Malassezia activity of Nyctanthes arbor-tristis L. (NAT) ethanolic leaf extract through turbidimetric growth curves, disruption of plasma membrane and secondly, it aims to present in silico validation of its active constituents over Mala s1a novel allergen.. The antifungal susceptibility 50 % ethanolic extract of NAT was determined by broth microdilution method according to CLSI guidelines. Further MICs and IC50 were determined spectrophotometrically using the software SoftMax® Pro-5 (Molecular Devices, USA). Active constituents mediated disruption of plasma membrane was studied through flowcytometry by permeabilization of fluorescent dye Propidium Iodide (PI). Antioxidant activity of the extract was determined using the DPPH stable radical. Molecular validation of fungal DNA from the extract was observed using PCR amplification. In silico analysis of its active constituents over Mala s1 was performed using HEX software and visualized through Pymol.. The anti-Malassezia potential of NAT leaf extracts reflected moderate MIC 1.05 μg/μl against M. globosa, while least effective against M. restricta with MIC 1.47 μg/μl. A linear correlation coefficient R (2) = 0.866 was obtained in case of M. globosa while minimum was observed in M. restricta with R (2) = 0.732. The flow cytometric data reveal ~ 75 % cell death when treated with active constituents β-Sitosterol and Calceolarioside A. The docking confirmations and the interaction energies between Mala s1 and the active constituents (β-Sitosterol and Calceolarioside A) from extracts showed an effective binding which suggests Mala s1 as efficient allergen for site specific targeting.. This study revealed that Nyctanthes arbor-tristis L. (NAT) extracts possess high anti-Malassezia potential which is driven mainly by disruption of plasma membrane. Also in silico validation and molecular modeling studies establishes Mala s1 as a novel allergen that could be a potential target in disease treatment. Our results would also provide a foundation for the development of new therapeutic approach using NAT extract as lead compound with high antioxidant property as an added trait for skin care.

    Topics: Allergens; Antifungal Agents; Antigens, Fungal; Antioxidants; Caffeic Acids; Cell Membrane; Dermatomycoses; Glucosides; India; Malassezia; Microbial Sensitivity Tests; Oleaceae; Plant Extracts; Sitosterols

2016
The Role of fadD19 and echA19 in Sterol Side Chain Degradation by Mycobacterium smegmatis.
    Molecules (Basel, Switzerland), 2016, May-06, Volume: 21, Issue:5

    Mycobacteria are able to degrade natural sterols and use them as a source of carbon and energy. Several genes which play an important role in cholesterol ring degradation have been described in Mycobacterium smegmatis. However, there are limited data describing the molecular mechanism of the aliphatic side chain degradation by Mycobacterium spp. In this paper, we analyzed the role of the echA19 and fadD19 genes in the degradation process of the side chain of cholesterol and β-sitosterol. We demonstrated that the M. smegmatis fadD19 and echA19 genes are not essential for viability. FadD19 is required in the initial step of the biodegradation of C-24 branched sterol side chains in Mycobacterium smegmatis mc²155, but not those carrying a straight chain like cholesterol. Additionally, we have shown that echA19 is not essential in the degradation of either substrate. This is the first report, to our knowledge, on the molecular characterization of the genes playing an essential role in C-24 branched side chain sterol degradation in M. smegmatis mc²155.

    Topics: Bacterial Proteins; Cholesterol; Enoyl-CoA Hydratase; Ligases; Mutation; Mycobacterium smegmatis; Sitosterols; Sterols

2016
Distribution and sources of oxygenated non-hydrocarbons in topsoil of Beijing, China.
    Environmental science and pollution research international, 2016, Volume: 23, Issue:16

    The oxygenated non-hydrocarbon compounds are widely distributed in soil. To investigate the distribution and origin of these compounds in topsoil of Beijing, their contents and compositions were measured in topsoil from 62 sites in Beijing. The research results showed that oxygenated non-hydrocarbons were composed primarily of C6∼C28 n-fatty acids, C12∼C28 n-fatty alcohols, n-fatty acid methyl esters, phthalates, sterols, and dehydroabietic acid in the topsoil of Beijing. The contents and compositions of these compounds varied with the sampling site. The concentrations of n-fatty acids and phthalate esters were the highest at all sites, followed by sterols, n-fatty acid methyl esters, fatty alcohols, and dehydroabietic acid in order. The n-fatty acids had a main peak of C16, followed by C18. An odd or even carbon number predominance was not observed in the low-molecular-weight n-fatty acids, indicating a fossil fuel or organic matter source. However, some high-molecular-weight n-fatty acids with an even carbon predominance may derive from a biomass. The n-fatty alcohols showed a main peak of C22 and were predominated by an even carbon number, suggesting plant, microbial, or other natural origins. Phthalates, including diethyl phthalate (DEP), diisobutyl phthalate (DIBP), dibutyl phthalate (DBP), diethylhexyl phthalate (DEHP), and dimethylphthalate (DMP), were detected. The content of phthalate esters was higher in the samples collected from dense human activity areas. The concentrations of DBP, DEHP, and DIBP were relatively high, indicating an anthropogenic source. The sterols (predominantly β-sitosterol) originated from biological sources, especially plants. The n-fatty acid methyl esters and dehydroabietic acid in topsoil showed apparent even carbon predominance with the former mainly derived from microorganisms or plants and the latter from cork combustion products.

    Topics: Beijing; Carbon; China; Dibutyl Phthalate; Diethylhexyl Phthalate; Environmental Monitoring; Esters; Fatty Acids; Humans; Methyl Ethers; Oxygen; Phthalic Acids; Sitosterols; Soil; Soil Pollutants

2016
Amelioration of testosterone induced benign prostatic hyperplasia by Prunus species.
    Journal of ethnopharmacology, 2016, Aug-22, Volume: 190

    Benign prostatic hyperplasia (BPH) is a common urological disorder of men. The ethnomedicinal use of an African plant Prunus africana (Hook.f.) Kalkman (Pygeum) in treating men's problems made it a popular remedy all over the globe for the treatment of BPH and related disorders. However, rampant collections made from the wild in Africa have pushed the plant to Appendix II of CITES demanding conservation of the species.. In the present study, the aim was to unearth the protective effect of bark of different species of Prunus against BPH. The five selected Indian plants of family Rosaceae viz. Prunus amygdalus Stokes, Prunus armeniaca L., Prunus cerasoides Buch.-Ham. ex D. Don, Prunus domestica L. and Prunus persica (L.) Batsch were evaluated against P. africana (Hook.f.) Kalkman for a suitable comparison of efficacy as antiBPH agents.. The antiBPH activity was evaluated in testosterone (2mg/kg/day, s.c, 21 days) induced BPH in Wistar rats. The parameters studied were body weights; histopathological examination, immunohistochemistry (PCNA) and biochemical estimations of the prostate; supported by prostatic index, testicular index, creatinine, testosterone levels; antioxidant and anti-inflammatory evaluation. The study also included chemical profiling using three markers (β-sitosterol, docosyl ferulate and ursolic acid) and estimation of β-sitosterol content through GC.. The Prunus species showed the presence of all the three markers in their TLC fingerprint profile and maximum amount of β-sitosterol by GC was observed in P. domestica. Interestingly, all the species exhibited significant amelioration in testosterone induced parameters with P. domestica showing the most encouraging effect as indicated from histopathological examination, immunohistochemistry and biochemical studies. The Prunus species further showed remarkable anti-inflammatory and antioxidant activity signifying their role in interfering with various possible factors involved in BPH.. These findings are suggestive of a meaningful inhibitory effect of testosterone induced BPH by the bark of different species of Prunus in the order of P. domestica, P. persica, P. amygdalus, P. cerasoides and P. armeniaca with an efficacy of P. domestica comparable to P. africana and can be used as the potential backup of Pygeum for the management of BPH.

    Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Biomarkers; Chromatography, Gas; Chromatography, Thin Layer; Disease Models, Animal; Inflammation Mediators; Male; Oxidative Stress; Phytotherapy; Plant Bark; Plant Extracts; Plants, Medicinal; Prostate; Prostatic Hyperplasia; Prunus armeniaca; Prunus domestica; Prunus dulcis; Prunus persica; Rats, Wistar; Sitosterols; Testosterone; Triterpenes; Urological Agents; Ursolic Acid

2016
Exploring neuroprotective potential of Withania somnifera phytochemicals by inhibition of GluN2B-containing NMDA receptors: An in silico study.
    Medical hypotheses, 2016, Volume: 92

    N-methyl-d-aspartate receptors (NMDARs) mediated excitotoxicity has been implicated in multi-neurodegenerative diseases. Due to lack of efficacy and adverse effects of NMDA receptor antagonists, search for herbal remedies that may act as therapeutic agents is an active area of research to combat these diseases. Withania somnifera (WS) is being used for centuries as a nerve tonic and Nootropic agents. The present study targets the in silico evaluation of the neuroprotective efficacy of W. somnifera phytochemicals by inhibition of NMDA receptor-mediated excitotoxicity through allosteric inhibition of the GluN2B containing NMDARs. We predict Blood Brain Barrier (BBB) penetration, mutagenicity, drug-likeness and Human Intestinal Absorption properties of 25 WS phytochemicals. Further, molecular docking was performed to know whether these phytochemicals inhibit the GluN2B containing NMDARs or not. The results suggest that Anaferine, Beta-Sitosterol, Withaferin A, Withanolide A, Withanolide B and Withanolide D inhibit GluN2B containing NMDARs through allosteric mode similar to the well-known selective antagonist Ifenprodil. These phytochemicals have potential as an essentially useful oral drug to counter NMDARs mediated excitotoxicity and to treat multi-neurodegenerative diseases.

    Topics: Allosteric Site; Blood-Brain Barrier; Humans; Ligands; Molecular Conformation; Molecular Docking Simulation; Nerve Tissue Proteins; Neurodegenerative Diseases; Neuroprotection; Phytochemicals; Receptors, N-Methyl-D-Aspartate; Sitosterols; Withania; Withanolides

2016
Structural Features and Potent Antidepressant Effects of Total Sterols and β-sitosterol Extracted from Sargassum horneri.
    Marine drugs, 2016, Jun-28, Volume: 14, Issue:7

    The purified total sterols and β-sitosterol extracted from Sargassum horneri were evaluated for their antidepressant-like activity using the forced swim test (FST) and tail suspension test (TST) in mice. Total sterols and β-sitosterol significantly reduced the immobility time in the FST and TST. Total sterols were administered orally for 7 days at doses of 50, 100, and 200 mg/kg, and β-sitosterol was administered intraperitoneally at doses of 10, 20, and 30 mg/kg. β-sitosterol had no effect on locomotor activity in the open field test. In addition, total sterols and β-sitosterol significantly increased NE, 5-HT, and the metabolite 5-HIAA in the mouse brain, suggesting that the antidepressant-like activity may be mediated through these neurotransmitters.

    Topics: Animals; Antidepressive Agents; Behavior, Animal; Brain; Depression; Hindlimb Suspension; Hydroxyindoleacetic Acid; Male; Mice; Mice, Inbred ICR; Motor Activity; Neurotransmitter Agents; Sargassum; Serotonin; Sitosterols; Sterols; Swimming

2016
Novel Long-Circulating Liposomes Consisting of PEG Modified β-Sitosterol for Gambogic Acid Delivery.
    Journal of nanoscience and nanotechnology, 2016, Volume: 16, Issue:3

    Long-circulating liposome is an effective formulation in field of cancer treatment. However, high expenditure of formulation and high dose of cholesterol severely restrict its application. In this paper, we developed a method by grafting polyethylene glycol 2000 on β-sitosterol succinic anhydride ester to obtain relatively cheap polyethylene glycol-β-sitosterol conjugates, which were used to prepare long-circulating liposome without cholesterol. Gambogic acid which is an effective antitumor ingredient with very short half-life, was used as a model drug to prepare long-circulating liposome in this research. Meanwhile, the characteristics, pharmacokinetics and distribution of this novel long-circulating liposome were also investigated in comparison with other gambogic acid formulations. Polyethylene glycol-β-sitosterol conjugates were synthesized, different liposomal formulations were also prepared by ethanol injection method, and the obtained nanoparticles were characterized by dynamic light scattering and transmission electron microscope. The long-circulating effect, pharmacokinetics and distribution of gambogic acid in rats were also explored. 1HNMR confirmed that polyethylene glycol-β-sitosterol conjugates were synthesized successfully. Novel long-circulating liposome was successfully prepared by ethanol injection method attaining a entrapment efficiency of 89.4%, exhibiting a homogeneous particle size of 245.2 nm and -24.3 mV zeta potential with smooth continuous surface. This novel long-circulating liposome demonstrated better long-circulating effect than ordinary long-circulating liposome. The novel long-circulating liposome as-prepared not only could reduce cost of grafting polyethylene glycol on macromolecular phospholipid, but also no cholestrol in preparation was applied, expanding the application of liposome as a formulation in the field of lowering blood lipid. Therefore, polyethylene glycol-β-sitosterol conjugates are recommended substitute for polyethylene glycol modified phospholipid to prepare long-circulating liposomes.

    Topics: Animals; Chromatography, High Pressure Liquid; Liposomes; Microscopy, Electron, Transmission; Polyethylene Glycols; Proton Magnetic Resonance Spectroscopy; Rats; Rats, Sprague-Dawley; Sitosterols; Tissue Distribution; Xanthones

2016
Phytosterol structured algae oil nanoemulsions and powders: improving antioxidant and flavor properties.
    Food & function, 2016, Sep-14, Volume: 7, Issue:9

    Algae oil, enriched with omega-3 long-chain polyunsaturated fatty acids (ω-3 LC-PUFA), is known for its health benefits. However, protection against lipid oxidation as well as masking of unpleasant fishy malodors in algae oil enriched foods is a big challenge to achieve. In this study, we firstly achieved a one-pot ultrasound emulsification strategy (alternative heating-homogenization) to prepare phytosterol structured thermosensitive algae oil-in-water nanoemulsion stabilized by quillaja saponin. After spray drying, the resulting algae oil powders from the structured nanoemulsion templates exhibit an excellent reconstructed behavior, even after 30 d of storage. Furthermore, an enhanced oxidative stability was obtained by reducing both the primary and secondary oxidation products through formulation with β-sitosterol and γ-oryzanol, which are natural antioxidants. Following the results of headspace volatiles using dynamic headspace-gas chromatography-mass spectrometry (DHS-GC-MS), it was clear that the structured algae oil-loaded nanoemulsion and powder had lower levels of fishy off-flavour (e.g., (Z)-heptenal, decanal, ethanone, and hexadecenoic acid), whereas the control emulsion and oil powder without structure performed worse. This study demonstrated that the structure from phytosterols is an effective strategy to minimize the fishy off-flavour and maximize oxidative stability of both algae oil nanoemulsions and spray-dried powders, and opens up the possibility of formulation design in polyunsaturated oil encapsulates as novel delivery systems to apply in functional foods and beverages.

    Topics: Antioxidants; Drug Stability; Emulsions; Fatty Acids, Omega-3; Food, Fortified; Odorants; Oils; Phenylpropionates; Phytosterols; Powders; Quillaja Saponins; Sitosterols; Taste

2016
Fractional factorial design-based optimisation and application of an extraction and UPLC-MS/MS detection method for the quantification of phytosterols in food, feed and beverages low in phytosterols.
    Analytical and bioanalytical chemistry, 2016, Volume: 408, Issue:27

    Topics: Cholestadienols; Cholesterol; Chromatography, High Pressure Liquid; Edible Grain; Factor Analysis, Statistical; Fruit and Vegetable Juices; Humans; Limit of Detection; Liquid Phase Microextraction; Phytosterols; Pisum sativum; Poaceae; Reproducibility of Results; Sitosterols; Stigmasterol; Tandem Mass Spectrometry

2016
Simultaneous determination of β-sitosterol, campesterol, and stigmasterol in rat plasma by using LC-APCI-MS/MS: Application in a pharmacokinetic study of a titrated extract of the unsaponifiable fraction of Zea mays L.
    Journal of separation science, 2016, Volume: 39, Issue:21

    Topics: Animals; Cholesterol; Chromatography, High Pressure Liquid; Phytosterols; Rats; Reproducibility of Results; Sitosterols; Stigmasterol; Tandem Mass Spectrometry; Zea mays

2016
Involvement of metabolites in early defense mechanism of oil palm (Elaeis guineensis Jacq.) against Ganoderma disease.
    Plant physiology and biochemistry : PPB, 2016, Volume: 109

    Understanding the mechanism of interaction between the oil palm and its key pathogen, Ganoderma spp. is crucial as the disease caused by this fungal pathogen leads to a major loss of revenue in leading palm oil producing countries in Southeast Asia. Here in this study, we assess the morphological and biochemical changes in Ganoderma disease infected oil palm seedling roots in both resistant and susceptible progenies. Rubber woodblocks fully colonized by G. boninense were applied as a source of inoculum to artificially infect the roots of resistant and susceptible oil palm progenies. Gas chromatography-mass spectrometry was used to measure an array of plant metabolites in 100 resistant and susceptible oil palm seedling roots treated with pathogenic Ganoderma boninense fungus. Statistical effects, univariate and multivariate analyses were used to identify key-Ganoderma disease associated metabolic agitations in both resistant and susceptible oil palm root tissues. Ganoderma disease related defense shifts were characterized based on (i) increased antifungal activity in crude extracts, (ii) increased lipid levels, beta- and gamma-sitosterol particularly in the resistant progeny, (iii) detection of heterocyclic aromatic organic compounds, benzo [h] quinoline, pyridine, pyrimidine (iv) elevation in antioxidants, alpha- and beta-tocopherol (iv) degraded cortical cell wall layers, possibly resulting from fungal hydrolytic enzyme activity needed for initial penetration. The present study suggested that plant metabolites mainly lipids and heterocyclic aromatic organic metabolites could be potentially involved in early oil palm defense mechanism against G. boninense infection, which may also highlight biomarkers for disease detection, treatment, development of resistant variety and monitoring.

    Topics: alpha-Tocopherol; Arecaceae; beta-Tocopherol; Disease Resistance; Ganoderma; Gas Chromatography-Mass Spectrometry; Host-Pathogen Interactions; Microscopy, Electron, Scanning; Microscopy, Electron, Transmission; Multivariate Analysis; Palm Oil; Plant Diseases; Plant Extracts; Plant Oils; Plant Roots; Seedlings; Sitosterols; Time Factors

2016
The effect of a plant extract enriched in stigmasterol and β-sitosterol on glycaemic status and glucose metabolism in alloxan-induced diabetic rats.
    Food & function, 2016, Sep-14, Volume: 7, Issue:9

    Banana is an extensively cultivated plant worldwide, mainly for its fruit, while its ancillary product, the banana pseudostem, is consumed as a vegetable and is highly recommended for diabetics in the traditional Indian medicine system. The present study was aimed at elucidating the mechanism of antihyperglycaemia exerted by the ethanol extract of banana pseudostem (EE) and its isolated compounds viz., stigmasterol (C1) and β-sitosterol (C2), in an alloxan-induced diabetic rat model. Diabetic rats which were administered with C1, C2 and EE (100 and 200 mg per kg b. wt.) for 4 weeks showed reduced levels of fasting blood glucose and reversal of abnormalities in serum/urine protein, urea and creatinine in diabetic rats compared to the diabetic control group of rats. Diabetic symptoms such as polyphagia, polydipsia, polyuria, urine glucose and reduced body weight were ameliorated in the diabetic group of rats fed with EE, C1 and C2 (100 mg per kg b. wt., once daily) for 28 days. The levels of insulin and Hb were also increased, while the HbA1c level was reduced. The altered activities of hepatic marker enzymes viz., aspartate transaminase (AST), alanine transaminase (ALT) and alkaline phosphatase (ALP); glycolytic enzyme (hexokinase); shunt enzyme (glucose-6-phosphate dehydrogenase); gluconeogenic enzymes (glucose-6-phosphatase, fructose-1,6-bisphosphatase and lactate dehydrogenase) and pyruvate kinase were significantly reverted to normal levels by the administration of EE, C1 and C2. In addition, increased levels of hepatic glycogen and glycogen synthase and the corresponding decrease of glycogen phosphorylase activity in diabetic rats illustrated the antihyperglycaemic potential of EE and its components. The histological observations revealed a marked regeneration of the β-cells in the drug treated diabetic rats. These findings suggest that EE might exert its antidiabetic potential in the presence of C1 and C2, attributable to the enhanced glycolytic activity, besides increasing the hepatic glucose utilization in diabetic rats by stimulating insulin secretion from the remnant β-cells.

    Topics: Alloxan; Animals; Biomarkers; Cell Line, Tumor; Diabetes Mellitus, Experimental; Dietary Supplements; Ethnopharmacology; Female; Hyperglycemia; Hypoglycemic Agents; Insulin; Insulin Secretion; Insulin-Secreting Cells; Male; Medicine, Ayurvedic; Musa; Plant Extracts; Plant Leaves; Rats; Rats, Wistar; Sitosterols; Stigmasterol; Toxicity Tests, Acute

2016
Antimicrobial, cytotoxic, and anti-inflammatory activities of Pleopeltis polylepis.
    Journal of ethnopharmacology, 2016, Dec-24, Volume: 194

    Pleopeltis polylepis (Polypodaceae) is a fern used in the traditional Mexican medicine to treat fever, bleeding, typhoid, cough, pertussis, chest pain, and renal and hepatic diseases. The aim of this study was to analyze the bioactivities of different extracts, fractions and isolated compounds from this species to scientifically validate its medicinal applications.. Aerial parts of P. polylepis were macerated and extracted consecutively with hexane, chloroform, and methanol. These extracts were subsequently fractionated and compounds from hexane and methanol extracts were purified. The antimicrobial activity was assessed using a panel of eight Gram-positive and -negative bacterial and four fungal strains. The cytotoxicity of the compounds was assessed by flow cytometry using propidium iodide and the human-derived monocytic cell line THP-1. The anti-inflammatory activity was investigated by measuring the secretion of interleukin-6 and IL-10 using also the cell line THP-1.. Various extracts, fractions and compounds obtained from this plant showed antibacterial activity against both Gram-positive and -negative strains. Antifungal activity was confirmed only in Candida albicans and Tricophyton mentagrophytes. Two fractions and two isolated compounds (butyl myristate and β-sitosterol) showed no significant cytotoxicity and were further evaluated for their anti-inflammatory activity. All four samples tested showed an anti-inflammatory activity similar to prednisone used as a control.. The benefit of P. polylepis as a traditional plant related to its antimicrobial and anti-inflammatory activities was confirmed by in vitro assays. To the best of our knowledge, this is the first study reporting the isolation and bioactivities of extracts, fractions or isolated compounds from P. polylepis.

    Topics: Anti-Infective Agents; Anti-Inflammatory Agents; Cell Line; Cytotoxins; Fungi; Gram-Negative Bacteria; Gram-Positive Bacteria; Humans; Interleukin-10; Interleukin-6; Medicine, Traditional; Mexico; Myristic Acid; Plant Extracts; Polypodiaceae; Sitosterols

2016
Identification of Acyl Chain Oxidation Products upon Thermal Treatment of a Mixture of Phytosteryl/-stanyl Linoleates.
    Journal of agricultural and food chemistry, 2016, Dec-07, Volume: 64, Issue:48

    A mixture of phytosterols/-stanols, consisting of 75% β-sitosterol, 12% sitostanol, 10% campesterol, 2% campestanol, and 1% others, was esterified with linoleic acid. The resulting mixture of phytosteryl/-stanyl linoleates was subjected to thermal oxidation at 180 °C for 40 min. A silica solid-phase extraction was applied to separate a fraction containing the nonoxidized linoleates and nonpolar degradation products (heptanoates, octanoates) from polar oxidation products (oxo- and hydroxyalkanoates). In total, 15 sitosteryl, sitostanyl, and campesteryl esters, resulting from oxidation of the acyl chain, could be identified by GC-FID/MS. Synthetic routes were described for authentic reference compounds of phytosteryl/-stanyl 7-hydroxyheptanoates, 8-hydroxyoctanoates, 7-oxoheptanoates, 8-oxooctanoates, and 9-oxononanoates, which were characterized by GC-MS and two-dimensional NMR spectroscopy. The study provides data on the formation and identities of previously unreported classes of acyl chain oxidation products upon thermal treatment of phytosteryl/-stanyl fatty acid esters.

    Topics: Cholesterol; Esters; Hot Temperature; Linoleic Acids; Molecular Structure; Oxidation-Reduction; Phytosterols; Sitosterols

2016
Plasma cholesterol-raising potency of dietary free cholesterol versus cholesteryl ester and effect of β-sitosterol.
    Food chemistry, 2015, Feb-15, Volume: 169

    The present study (i) compared plasma cholesterol-raising activity of free cholesterol (FC) with that of cholesteryl palmitate (CP) and (ii) examined plasma cholesterol-reducing activity of β-sitosterol in FC-induced and CP-induced hypercholesterolemia. Male hamsters were divided into five groups and fed one of the five diets containing no cholesterol (NC), 2.6mmol cholesterol (C), 2.6mmol cholesterol plus 2.6mmol β-sitosterol (C+S), 2.6mmol cholesteryl palmitate (CP), and 2.6mmol CP plus 2.6mmol β-sitosterol (CP+S), respectively, for 8weeks. Hamsters fed diet C had plasma TC of 317.5mg/dl whereas hamsters fed diet CP has plasma TC of 281.3mg/dl. β-Sitosterol reduced plasma TC by 17.4% and 11.6%, respectively, in FC-induced and CP-induced hypercholesterolemia (not significant). It was concluded that plasma cholesterol-raising activity of dietary cholesterol was a function of its chemical forms in diet, and β-sitosterol could similarly suppress the hypercholesterolemia induced by both dietary FC and CP.

    Topics: Animals; Cholesterol Esters; Cholesterol, Dietary; Cholesterol, HDL; Cricetinae; Feces; Hypercholesterolemia; Liver; Male; Mesocricetus; Sitosterols; Triglycerides

2015
A new ester of fatty acid from a methanol extract of the whole plant of Amaranthus spinosus and its α-glucosidase inhibitory activity.
    Pharmaceutical biology, 2015, Volume: 53, Issue:4

    Amaranthus spinosus Linn. (Amaranthaceae), commonly known as "spiny pigweed", is used both in the Indian traditional system and in folk medicine to treat diabetes.. The present study evaluates the scientific basis of antidiabetic activity of chloroform fraction of methanol extract of A. spinosus and of an isolated constituent of A. spinosus.. HPLC analysis was performed to determine the purity and the amount of the constituent present in the plant extract. The yeast α-glucosidase inhibition technique was used to determine the antidiabetic activity of A. spinosus. Acarbose was used as a standard. An appropriate therapeutic approach for preventing diabetes mellitus and obesity is to retard the absorption of glucose by inhibition of α-glucosidase.. One novel fatty acid with strong α-glucosidase inhibitory activity - (14E, 18E, 22E, 26E) - methyl nonacosa-14, 18, 22, 26 tetraenoate [1] (IC50 value 6.52 µM/mL) and β-sitosterol [2] were purified. Compound 1 was found to be more potent than the methanol extract. HPLC quantitative analysis revealed that 0.15% of compound 1 and 0.06% of compound 2 were present in the plant extract.. This novel fatty acid can potentially be developed as a novel natural nutraceutical for the management of diabetes.

    Topics: alpha-Glucosidases; Amaranthus; Chromatography, High Pressure Liquid; Fatty Acids, Unsaturated; Glycoside Hydrolase Inhibitors; Hypoglycemic Agents; Methanol; Plant Extracts; Sitosterols; Yeasts

2015
Comparison of the physico-chemical and phytochemical characteristics of the oil of two Plukenetia species.
    Food chemistry, 2015, Apr-15, Volume: 173

    A physico-chemical and phytochemical characterisation of the oil of two rich sources of polyunsaturated fatty acids, tocopherols and phytosterols is presented for two close species of Plukenetia, endemic to the Amazon Region of Peru. Plukenetia huayllabambana presented approximately 9% more oil yield than Plukenetia volubilis. Fatty acid profiles were pretty similar for both species but P. huayllabambana presented a significantly higher content of α-linolenic acid than P. volubilis (51.3 and 45.6 g/100 g oil, respectively). Important contents of γ- and δ-tocopherol were evidenced in both oils (127.6 and 84.0 and, 93.3 and 47.5 mg/100 g oil, for P. volubilis and P. huayllabambana, respectively). β-Sitosterol was the most important and representative phytosterol in both oils (∼127 mg/100 g oil). The results of this study indicate P. huayllabambana as an important dietary source of health promoting phytochemicals.

    Topics: alpha-Linolenic Acid; Euphorbiaceae; Fatty Acids, Omega-3; Fatty Acids, Omega-6; Peru; Phytochemicals; Plant Oils; Sitosterols; Tocopherols

2015
Online solid-phase extraction-liquid chromatography-mass spectrometry to determine free sterols in human serum.
    Talanta, 2015, Volume: 132

    An automated method for analyzing free non-cholesterol sterols in human serum using online solid phase extraction-liquid chromatography-mass spectrometry is proposed herein. The method allows the determination of three phytosterols (sitosterol, stigmasterol and campesterol) and two cholesterol precursors (desmosterol and lanosterol). The analysis of sterols in human serum is critical in the study of cholesterol-related disorders, such as inherited familial hypercholesterolemias. Special effort was made to isolate the analytes from the serum lipoproteins, their natural conveyance through the bloodstream. The sample treatment consisted of a Bligh-Dyer extraction followed by dilution of the extract. This treatment allowed the sample to be injected into the online system and ensured the correct detection of the analytes, while avoiding the matrix effects commonly related to serum samples. The analytical performance showed linear ranges that covered two orders of magnitude, with correlation coefficients above 0.99. Limits of detection and quantification ranged from 0.2 ng/mL to 13 ng/mL and from 1.0 ng/mL to 43 ng/mL, respectively. Recovery when spiking serum with a half or a tenth of the average concentration reported in human serum ranged from 99% to 111% and from 102% to 120%, respectively. Intra-day precision and inter-day precision were below 20%.

    Topics: Cholesterol; Chromatography, Liquid; Desmosterol; Humans; Lanosterol; Limit of Detection; Mass Spectrometry; Phytosterols; Sitosterols; Solid Phase Extraction; Stigmasterol

2015
Simultaneous Quantification of Gymnemic Acid as Gymnemagenin and Charantin as β-Sitosterol Using Validated HPTLC Densitometric Method.
    Journal of chromatographic science, 2015, Volume: 53, Issue:7

    Gymnemic acid and charantin are well-established antidiabetic phytosterols found in Gymnema sylvestre and Momordica charantia, respectively. The fact that these plants are often used together in antidiabetic poly-herbal formulations lured us to develop an HPTLC densitometric method for the simultaneous quantification of their bioactive compounds. Indirect estimation of gymnemic acid as gymnemagenin and charantin as β-sitosterol after hydrolysis has been proposed. Aluminum-backed silica gel 60 F254 plates (20 × 10 cm) were used as stationary phase and toluene-ethyl acetate-methanol-formic acid (60 : 20 : 15 : 5, v/v) as mobile phase. Developed chromatogram was scanned at 550 nm after derivatization with modified vanillin-sulfuric acid reagent. Regression analysis of the calibration data showed an excellent linear relationship between peak area versus concentration of the analytes. Linearity was found to be in the range of 500-2,500 and 100-500 ng/band for gymnemagenin and β-sitosterol, respectively. The suitability of the developed HPTLC method for simultaneous estimation of analytes was established by validating it as per the ICH guidelines. The limits of detection and quantification for gymnemagenin were found to be ≈60 and ≈190 ng/band, and those for β-sitosterol ≈30 and ≈90 ng/band, respectively. The developed method was found to be linear (r(2) = 0.9987 and 0.9943), precise (relative standard deviation <1.5 and <2% for intra- and interday precision) and accurate (mean recovery ranged between 98.43-101.44 and 98.68-100.20%) for gymnemagenin and β-sitosterol, respectively. The proposed method was also found specific and robust for quantification of both the analytes and was successfully applied to herbal drugs and in-house herbal formulation without any interference.

    Topics: Alkaloids; Chemistry, Pharmaceutical; Chromatography, Thin Layer; Densitometry; Gymnema; Hypoglycemic Agents; Limit of Detection; Momordica; Saponins; Sitosterols; Triterpenes

2015
Cholesterol side chain analogs but not its ether analogs possess cholesterol-lowering activity.
    Food & function, 2015, Volume: 6, Issue:2

    Cholesterol analogs can be used to treat hypercholesterolemia. The present study was to test the effects of cholesteryl 3β-ethoxy (CE) and cholesteryl 3β-methoxy (CM) on plasma total cholesterol (TC) compared with that of β-sitosterol (SI) in hamsters fed a high cholesterol diet. CM and CE are the methoxy and ethoxy analogs of cholesterol while SI is an analog of cholesterol having an additional ethyl group on the side chain. Results showed that SI at a dose of 0.1% could effectively reduce plasma TC by 18%. The analysis of sterols in the plasma and liver did not detect the presence of SI, proving that it was poorly absorbed in the intestine. In contrast, both CE and CM had no effect on plasma TC. However, CE and CM were found to accumulate in both plasma and liver, indicating that they could be well absorbed in the intestine. It was therefore concluded that analogs having different side chains possessed plasma TC-lowering activity, while analogs or derivatives on the hydroxyl group had no hypocholesterolemic activity.

    Topics: Animals; Anticholesteremic Agents; Cholesterol; Cholesterol, Dietary; Cricetinae; Diet, High-Fat; Feces; Hypercholesterolemia; Liver; Male; Organ Size; Sitosterols; Sterols

2015
Curcuma ecalcarata - new natural source of pinocembrin and piperitenone.
    Natural product research, 2015, Volume: 29, Issue:13

    Phytochemical analysis of the rhizome extract of Curcuma ecalcarata, a hitherto uninvestigated south Western Ghats endemic species, resulted in the isolation and identification of the diaryl heptanoid trans, trans-1,7-diphenyl-5-hydroxy-4,6-heptadiene-3-one (1), steroid β-sitosterol (2), flavanone pinocembrin (4) and monoterpenoids piperitenone (3) and 8-hydroxy piperitone (5). HPTLC estimation of pinocembrin in the rhizome revealed the plant as a rich source of pinocembrin (0.37% dry wt.). The rhizome essential oil was isolated by hydrodistillation and analysed by GC-FID, GC-MS and (13)C NMR. Among the 30 constituents identified in the oil, monoterpenoids predominated (94.2%) followed by sesquiterpenoids (5.8%). The major compound consisting of 65.2% of the oil was isolated and identified as piperitenone (3). The study highlights the plant as a rich source of the flavanone pinocembrin and the volatile aroma compound piperitenone.

    Topics: Curcuma; Cyclohexane Monoterpenes; Flavanones; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Molecular Structure; Monoterpenes; Oils, Volatile; Plant Extracts; Plant Oils; Rhizome; Sitosterols; Volatile Organic Compounds

2015
Incorporation of β-sitosterol into the membrane prevents tumor necrosis factor-α-induced nuclear factor-κB activation and gonadotropin-releasing hormone decline.
    Steroids, 2015, Volume: 96

    It has been demonstrated that hypothalamus has a programmatic role in aging development, and this role of hypothalamus is mediated by nuclear factor-κB (NF-κB)-directed gonadotropin-releasing hormone (GnRH) decline. β-Sitosterol (BS), one of the most common phytosterols in the diet, is able to inhibit pro-inflammatory NF-κB signaling. It has been demonstrated that dietary BS can enter the brain and accumulates in brain cell membranes. However, it is unknown whether and how membrane BS affects GnRH release. Using GT1-7 cells, a cell line of GnRH neurons, this study investigated if membrane BS had an influence on GnRH release. It was found that incorporation of BS into the membrane could prevent tumor necrosis factor-α (TNF-α)-induced GnRH decline. The underlying basis involves inhibition of NF-κβ activation via estrogen receptor (ER)-mediated inhibition of inhibitor of nuclear factor κB (Iκβ) processing. These results extend existing data regarding the beneficial effects of BS, and suggest the use of BS-enriched foods as anti-aging nutrients.

    Topics: Biological Transport; Cell Line; Cell Membrane; Gonadotropin-Releasing Hormone; Neurons; NF-kappa B; Receptors, Estrogen; Sitosterols; Tumor Necrosis Factor-alpha

2015
Cholesterol oxidase with high catalytic activity from Pseudomonas aeruginosa: Screening, molecular genetic analysis, expression and characterization.
    Journal of bioscience and bioengineering, 2015, Volume: 120, Issue:1

    An extracellular cholesterol oxidase producer, Pseudomonas aeruginosa strain PA157, was isolated by a screening method to detect 6β-hydroperoxycholest-4-en-3-one-forming cholesterol oxidase. On the basis of a putative cholesterol oxidase gene sequence in the genome sequence data of P. aeruginosa strain PAO1, the cholesterol oxidase gene from strain PA157 was cloned. The mature form of the enzyme was overexpressed in Escherichia coli cells. The overexpressed enzyme formed inclusion bodies in recombinant E. coli cells grown at 20 °C and 30 °C. A soluble and active PA157 enzyme was obtained when the recombinant cells were grown at 10 °C. The purified enzyme was stable at pH 5.5 to 10 and was most active at pH 7.5-8.0, showing optimal activity at pH 7.0 and 70 °C. The enzyme retained about 90% of its activity after incubation for 30 min at 70 °C. The enzyme oxidized 3β-hydroxysteroids such as cholesterol, β-cholestanol, and β-sitosterol at high rates. The Km value and Vmax value for the cholesterol were 92.6 μM and 15.9 μmol/min/mg of protein, respectively. The Vmax value of the enzyme was higher than those of commercially available cholesterol oxidases. This is the first report to characterize a cholesterol oxidase from P. aeruginosa.

    Topics: Base Sequence; Biocatalysis; Cholestanol; Cholesterol; Cholesterol Oxidase; Cloning, Molecular; Escherichia coli; Hydrogen-Ion Concentration; Inclusion Bodies; Kinetics; Pseudomonas aeruginosa; Sitosterols; Solubility; Temperature

2015
Phytosterols as precursors for the synthesis of aromatase inhibitors: Hemisynthesis of testololactone and testolactone.
    Steroids, 2015, Volume: 96

    Using β-sitosterol and stigmasterol as precursor materials, a concise and efficient hemisynthesis of aromatase inhibitors: testololactone and testolactone was accomplished in a well-established reaction scheme. It involves highly effective Oppaneur oxidation of both β-sitosterol as well as stigmasterol to generate the required enone moiety in ring 'A' of the desired steroid system. The Oppaneur oxidation products of both β-sitosterol and stigmasterol were then subjected to oxidative cleavage of the side chain to produce 4-androstene-3,17-dione. Baeyer-Villiger oxidation of 4-androstene-3,17-dione using m-CPBA yielded testololactone. Dehydrogenation of 4-androstene-3,17-dione using phenylselenyl chloride in ethyl acetate followed by selenoxide elimination with H2O2 in dichloromethane furnished androstenedienone. Baeyer-Villiger oxidation of the resulting androstenedienone yielded the desired testolactone (overall yield 33%). This expeditious reaction scheme may be exploited for the bulk production of aromatase inhibitors (especially testolactone marketed under the brand name Teslac) from the most abundant and naturally occurring phytosterols like β-sitosterol.

    Topics: Aromatase Inhibitors; Chemistry Techniques, Synthetic; Oxidation-Reduction; Phytosterols; Sitosterols; Stigmasterol; Testolactone

2015
Validation of an isotope dilution gas chromatography-mass spectrometry method for combined analysis of oxysterols and oxyphytosterols in serum samples.
    Steroids, 2015, Volume: 99, Issue:Pt B

    We describe the validation of a method for the analysis of oxysterols, i.e. oxycholesterols and oxyphytosterols, in human serum using gas chromatography-mass spectrometry selected ion monitoring (GC-MS-SIM). Concentrations of 7α- and 7β-hydroxy-, and 7oxo-cholesterol, -campesterol, and -sitosterol as well as 4β-hydroxycholesterol and side-chain oxygenated 24S-, 25-, and 27-hydroxycholesterol were determined by isotope dilution methodology. After saponification at room temperature the oxysterols were extracted, separated from their substrates, cholesterol, campesterol, and sitosterol, by solid phase extraction, and subsequently derivatised to their corresponding trimethylsilyl-ethers prior to GC-MS-SIM. In order to prevent artificial autoxidation butylated hydroxytoluene and ethylenediaminetetraacetic acid were added. The validation of the method was performed according to the International Conference on Harmonisation guidance, including limits of detection and quantification, ranges, recovery and precision. Due to improved instrumental settings and work-up procedure, limits of detection and quantification ranged between 8.0-202.0pg/mL and 28.0-674pg/mL, respectively. Recovery data in five calibration points varied between 91.9% and 116.8% and in serum samples between 93.1% and 118.1%. The mean coefficient of variation (CV) for the recovery of all compounds was <10%. Well satisfying CVs for within-day precision (2.1-10.8%) and for between-day precision (2.3-12.1%) were obtained. More than 20 samples could be processed in a single routine day and test series of about 300 samples can be realised without impairment of the validation parameters during a sequence. Comparison of oxysterol and oxyphytosterol content in serum and plasma revealed no difference. A fully validated isotope dilution methodology for the quantification of oxycholesterols and oxyphytosterols from human serum or plasma is presented.

    Topics: Calibration; Cholesterol; Gas Chromatography-Mass Spectrometry; Humans; Hydrolysis; Indicator Dilution Techniques; Isotopes; Limit of Detection; Phytosterols; Reference Standards; Reproducibility of Results; Serum; Sitosterols; Solutions; Solvents; Time Factors

2015
Report: complexation of β-sitosterol with tris (dibenzylideneacetone) dipalladium and its anti-microbial activity.
    Pakistan journal of pharmaceutical sciences, 2015, Volume: 28, Issue:2

    β-sitosterol is a naturally occurring plant sterol (phytosterol) present in many fruits and vegetables. Scientific research has proven that β-sitosterol is helpful in maintaining the proper functioning of our body. Previously we described the complexation of β-sitosterol with trace metals (Mahmood et al., 2013). Trace metals after the formation of complex unable to absorb in the body and hence eliminated out from the body thus reducing metal toxicity (Marsha, 1996). The present article describes the complexation of μ-sitosterol with Palladium (Pd) metal. Palladium is a toxic metal and due to polluted and hazardous environment traces of this metal can be transferred into the body, which is harmful for human health. Our aim is to make Pd-sterol complex so that this toxic metal (Pd) does not absorb in the body and hence excreted out from the body in the complex form. In order to form this complex μ-sitosterol (Ib) is reacted with Tris (dibenzylideneacetone) dipalladium or [Pd(2) (DBA)(3)] (Ia) in 2:1 ratio in an inert atmosphere and dimethylformamid (DMF) added as a solvent. The resulting complex [Pd(2) (DBA)(3).(β-sitosterol) (Ic) was identified by various spectroscopic techniques such as IR, Mass and (1)H-NMR. This new organo metallic complex (Ic) also showed significant antibacterial and antifungal activity. The present work revealed that Pd-sterol complex does not only reduce metal toxicity but also helpful in minimizing bacterial and fungal infections present in the body. Our research also concluded that we must take plenty of fruits and vegetables in our diet so that natural plant sterol such as β-sitosterol can enhance our defense mechanism and maintain other functions of our body.

    Topics: Anti-Infective Agents; Magnetic Resonance Spectroscopy; Organometallic Compounds; Sitosterols; Spectrophotometry, Infrared

2015
Chemical constituents from rhizomes of Cautleya spicata (Sm.) Baker (Zingiberaceae).
    Natural product research, 2015, Volume: 29, Issue:21

    The chemical investigation of ethanolic extract from rhizomes of Cautleya spicata (Sm.) Baker (Zingiberaceae) has resulted in the isolation of eight compounds which were characterised as β-sitosterol (1), β-sitosterol β-D-glucoside (2), bergapten (3), zerumin A (4), (E)-labda-8(17),12-diene-15,16-dial (5), kaempferol (6), quercetin (7) and astragalin (8). All compounds were identified by spectroscopic and chemical methods. This paper describes the first phytochemical work on C. spicata.

    Topics: Glucosides; Kaempferols; Molecular Structure; Phytochemicals; Plant Extracts; Quercetin; Rhizome; Sitosterols; Zingiberaceae

2015
Structures of phytosterols and triterpenoids with potential anti-cancer activity in bran of black non-glutinous rice.
    Nutrients, 2015, Mar-06, Volume: 7, Issue:3

    Structures of some bioactive phytochemicals in bran extract of the black rice cv. Riceberry that had demonstrated anti-cancer activity in leukemic cell line were investigated. After saponification with potassium hydroxide, separation of the unsaponified fraction by reversed-phase high performance liquid chromatography (HPLC) resulted in four sub-fractions that had a certain degree of anti-proliferation against a mouse leukemic cell line (WEHI-3 cell), this being IC50 at 24 h ranging between 2.80-467.11 μg/mL. Further purification of the bioactive substances contained in these four sub-fractions was performed by normal-phase HPLC. Structural characterization by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) resulted in, overall, the structures of seven phytosterols and four triterpenoids. Four phytosterols, 24-methylene-ergosta-5-en-3β-ol, 24-methylene-ergosta-7-en-3β-ol, fucosterol, and gramisterol, along with three triterpenoids, cycloeucalenol, lupenone, and lupeol, were found in the two sub-fractions that showed strong anti-leukemic cell proliferation (IC50 = 2.80 and 32.89 μg/mL). The other sterols and triterpenoids were campesterol, stigmasterol, β-sitosterol and 24-methylenecycloartanol. Together with the data from in vitro biological analysis, we suggest that gramisterol is a significant anti-cancer lead compound in Riceberry bran extract.

    Topics: Animals; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cholesterol; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Leukemia; Mass Spectrometry; Mice; Molecular Structure; Oryza; Pentacyclic Triterpenes; Phytosterols; Phytotherapy; Plant Extracts; Seeds; Sitosterols; Stigmasterol; Triterpenes

2015
Vascular effects of oxysterols and oxyphytosterols in apoE -/- mice.
    Atherosclerosis, 2015, Volume: 240, Issue:1

    The aim of our study was to investigate vascular effects of oxysterols and oxyphytosterols on reactive oxygen species (ROS), endothelial progenitor cells, endothelial function and atherogenesis.. Male apoE-/-mice were treated with cholesterol, sitosterol, 7-ß-OH-cholesterol, 7-ß-OH-sitosterol, or cyclodextrin by daily intraperitoneal application. The respective concentrations in the plasma and in the arterial wall were determined by gas chromatography-flame ionization or mass spectrometry. ROS production was assessed by electron-spin resonance spectroscopy in the aorta, endothelial function of aortic rings and atherosclerosis in the aortic sinus was quantitated after 4 weeks.. Compared to vehicle, there was no difference in plasma cholesterol levels and arterial wall concentrations after i.p. application of cholesterol. 7-ß-OH-cholesterol concentrations were increased in the plasma (33.7±31.5 vs. 574.57.2±244.92 ng/ml) but not in the arterial wall (60.1±60.1 vs. 59.3±18.2 ng/mg). Sitosterol (3.39±0.96 vs. 8.16±4.11 mg/dL; 0.08±0.04 vs. 0.16±0.07 μg/mg, respectively) and 7-ß-OH-sitosterol concentrations (405.1±151.8 vs. 7497±3223 ng/ml; 0.24±0.13 vs. 16.82±11.58 ng/mg, respectively) increased in the plasma and in the aorta. The i.p-application of the non-oxidized cholesterol or sitosterol did not induce an increase of plasma oxysterols or oxyphytosterols concentrations. Oxidative stress in the aorta was increased in 7-ß-OH-sitosterol treated mice, but not in mice treated with cholesterol, sitosterol, or 7-ß-OH-cholesterol. Moreover, cholesterol, sitosterol, 7-ß-OH-cholesterol, and 7-ß-OH-sitosterol did not affect endothelial-dependent vasodilation, or early atherosclerosis.. Increased oxyphytosterol concentrations in plasma and arterial wall were associated with increased ROS production in aortic tissue, but did not affect endothelial progenitor cells, endothelial function, or early atherosclerosis.

    Topics: Animals; Aorta; Aortic Diseases; Apolipoproteins E; Atherosclerosis; Cell Movement; Cells, Cultured; Cholesterol; Cyclodextrins; Disease Models, Animal; Endothelial Progenitor Cells; Hydroxycholesterols; Male; Mice, Inbred C57BL; Mice, Knockout; Oxidative Stress; Reactive Oxygen Species; Sitosterols; Time Factors; Vasodilation

2015
Antichlamydial sterol from the Red Sea sponge Callyspongia aff. implexa.
    Planta medica, 2015, Volume: 81, Issue:5

    Marine sponges are rich sources of natural products exhibiting diverse biological activities. Bioactivity-guided fractionation of the Red Sea sponge Callyspongia aff. implexa led to the isolation of two new compounds, 26,27-bisnorcholest-5,16-dien-23-yn-3β,7α-diol, gelliusterol E (1) and C27-polyacetylene, callimplexen A (2), in addition to the known compound β-sitosterol (3). The structures of the isolated compounds were determined by 1D- and 2D-NMR techniques as well as high-resolution tandem mass spectrometry and by comparison to the literature. The three compounds (1-3) were tested against Chlamydia trachomatis, an obligate intracellular gram-negative bacterium, which is the leading cause of ocular and genital infections worldwide. Only gelliusterol E (1) inhibited the formation and growth of chlamydial inclusions in a dose-dependent manner with an IC50 value of 2.3 µM.

    Topics: Animals; Anti-Bacterial Agents; Biological Products; Callyspongia; Chlamydia trachomatis; Molecular Structure; Polyynes; Porifera; Sitosterols; Sterols

2015
Identification and characterization of β-sitosterol target proteins.
    Bioorganic & medicinal chemistry letters, 2015, Nov-01, Volume: 25, Issue:21

    β-Sitosterol is the most abundant plant sterol in the human diet. It is also the major component of several traditional medicines, including saw palmetto and devil's claw. Although β-sitosterol is effective against enlarged prostate in human clinical trials and has anti-cancer and anti-inflammatory activities, the mechanisms of action are poorly understood. Here, we report the identification of two new binding proteins for β-sitosterol that may underlie its beneficial effects.

    Topics: Animals; Binding Sites; Humans; Lipopolysaccharides; Macrophages; Mice; Molecular Conformation; Peroxisomal Multifunctional Protein-2; Protein Binding; Sitosterols; Synaptotagmin I

2015
Alyssum homolocarpum seeds: phytochemical analysis and effects of the seed oil on neural stem cell proliferation and differentiation.
    Journal of natural medicines, 2015, Volume: 69, Issue:3

    Pharmacognostic evaluation of medicinal plants may assess their current applications and possibly results in finding new active components. In this study, ash and extractive values and high performance thin layer chromatography fingerprints of Alyssum homolocarpum (Brassicaceae) seed extracts were investigated to elucidate its composition. Differential scanning calorimetry and gas chromatography-mass spectrometry analysis were employed to determine the components of A. homolocarpum seed oil (AHO). Neurosphere assay, in vitro differentiation and immunofluorescence analysis were performed to evaluate the effects of oral administration of AHO (0.5 or 1 g/kg/day for 14 days) on proliferation and differentiation of neural stem cells (NSCs) in adult male BALB/c mice. Total, acid-insoluble and water-soluble ash values were determined as 45.83 ± 5.85, 6.67 ± 2.89 and 28.33 ± 2.89 mg/g, respectively. The extractive values were 4.90, 0.43 and 0.56 % (w/w) for n-hexane, dichloromethane and ethanolic extracts, respectively. Interestingly, AHO was mainly composed of α-linolenic acid (89.71 %), β-sitosterol (3.3 mg/g) and campesterol (0.86 mg/g). Administration of AHO at 1 g/kg/day significantly increased proliferation of NSCs, as evidenced by an increase in mean neurosphere-forming frequency per brain (872.7 ± 15.17) and neurosphere diameter (101 ± 2.48 µm) compared to the control group (424.3 ± 59.29 and 78.63 ± 1.7 µm, respectively; P < 0.05). AHO treatment did not affect in vitro differentiation of the harvested NSCs. Our data show that A. homolocarpum seed oil is a rich source of α-linolenic acid and β-sitosterol with potential therapeutic application to enhance NSC proliferation and recruitment in neurological diseases.

    Topics: Animals; Brassicaceae; Cell Differentiation; Cell Proliferation; Cells, Cultured; Cholesterol; Drug Evaluation, Preclinical; Gas Chromatography-Mass Spectrometry; Male; Mice; Mice, Inbred BALB C; Neural Stem Cells; Phytosterols; Plant Extracts; Plant Oils; Seeds; Sitosterols

2015
Three-phase solvent systems for the comprehensive separation of a wide variety of compounds from Dicranostigma leptopodum by high-speed counter-current chromatography.
    Journal of separation science, 2015, Volume: 38, Issue:12

    A three-phase solvent system was efficiently applied for high-speed counter-current chromatography to separate secondary metabolites with a wide range of hydrophobicity in Dicranostigma leptopodum. The three-phase solvent system of n-hexane/methyl tert-butyl ether/acetonitrile/0.5% triethylamine (2:2:3:2, v/v/v/v) was selected for high-speed counter-current chromatography separation. The separation was initiated by filling the column with a mixture of intermediate phase and lower phase as a stationary phase followed by elution with upper phase to separate the hydrophobic compounds. Then the mobile phase was switched to the intermediate phase to elute the moderately hydrophobic compounds, and finally the polar compounds still retained in the column were fractionated by eluting the column with the lower phase. In this research, 12 peaks were eluted out in one-step operation within 110 min, among them, eight compounds with acceptable purity were obtained and identified. The purities of β-sitosterol, protopine, allocryptopine, isocorydione, isocorydine, coptisine, berberrubine, and berberine were 94.7, 96.5, 97.9, 86.6, 98.9, 97.6, 95.7, and 92.8%, respectively.

    Topics: Acetonitriles; Berberine; Chromatography; Chromatography, High Pressure Liquid; Countercurrent Distribution; Ethylamines; Hexanes; Hydrophobic and Hydrophilic Interactions; Magnetic Resonance Spectroscopy; Methyl Ethers; Papaveraceae; Plant Extracts; Sitosterols; Solvents

2015
Evaluation of antioxidant and anticancer activity of extract and fractions of Nardostachys jatamansi DC in breast carcinoma.
    BMC complementary and alternative medicine, 2015, Mar-10, Volume: 15

    Nardostachys jatamansi DC is a Himalayan medicinal herb that has been described in various traditional systems of medicine for its use in cancer. In view of its traditional claims, and chemical constituents, antioxidant and anticancer activities were evaluated in breast carcinoma.. Petroleum ether (NJPE), methanol extract (NJM) and subsequent diethyl ether (NJDE), ethyl acetate (NJEA) and aqueous (NJAQ) fractions of roots and rhizomes of N. jatamansi were prepared. Total phenolic, flavonoid content, and antioxidant activities were determined using suitable methods. Antiproliferative activity was assessed in estrogen receptor (ER)-positive (MCF-7) and ER-negative breast carcinoma (MDA-MB-231) cells by MTT and SRB assay. Cell cycle analysis, Hoechst staining, and clonogenic assay were employed to determine the mode of antiproliferative and pro-apoptotic activity in MDA-MB-231 cells.. NJM/fractions exhibited prominent antioxidant activity with significant correlation between phenolic content and ABTS (IC50) scavenging (R = -0.9680, P < 0.05), and total antioxidant capacity (R = 0.8396, P > 0.05). In MTT assay, NJM exhibited the highest antiproliferative activity (IC50: 58.01 ± 6.13 and 23.83 ± 0.69 μg/mL in MCF-7 and MDA-MB-231 respectively). Among the fractions, NJPE and NJDE were found to be most potent in MCF-7 (IC50: 60.59 ± 4.78 μg/mL) and MDA-MB-231 (IC50: 25.04 ± 0.90 μg/mL) cells respectively. Statistical analyses revealed NJM and NJDE exhibited significantly higher (P < 0.05) cytotoxicity in MDA-MB-231 cells. Cell cycle analysis demonstrated that NJM, NJPE and NJEA caused G2/M arrest while NJDE caused G0/G1 phase arrest in MDA-MB-231 cells. Further, NJM/fractions induced significant (P < 0.001) cell death by apoptosis characterized by apoptotic morphological changes in Hoechst staining and inhibited long-term proliferation (P < 0.001) of MDA-MB-231 cells in clonogenic assay. Lupeol and β-sitosterol were identified as anticancer principles in NJM/fractions by HPTLC.. Our results suggest that NJM/fractions possess significant antiproliferative potential which is mediated through cell cycle perturbation and pro-apoptotic effects in MDA-MB-231 cells. Moreover, this study highlights the antioxidant potential of NJM/fractions which can be attributed to the presence of phenols. NJDE emerged as the most potent fraction and further mechanistic and phytochemical investigations are under way to identify the active principles.

    Topics: Adenocarcinoma; Antineoplastic Agents, Phytogenic; Antioxidants; Apoptosis; Breast Neoplasms; Cell Cycle; Cell Proliferation; Female; Flavonoids; G1 Phase; Humans; MCF-7 Cells; Nardostachys; Pentacyclic Triterpenes; Phenols; Phytotherapy; Plant Extracts; Plant Roots; Plants, Medicinal; Polyphenols; Receptors, Estrogen; Rhizome; Sitosterols

2015
Chemical characterization and assessment of antioxidant potentiality of Streptocaulon sylvestre Wight, an endangered plant of sub-Himalayan plains of West Bengal and Sikkim.
    BMC complementary and alternative medicine, 2015, Apr-08, Volume: 15

    S. sylvestre Wright is an extremely rare plant, found only in the sub-Himalayan Terai region of West Bengal and neighboring Sikkim foot-hills. The plant has never been evaluated for any pharmaceutical properties. The phytochemical status of the plant is still unknown. Therefore, the aim of the study was to explore the antioxidant and free radical scavenging activities and analysis of bioactive compounds present in S. sylvestre.. S. sylvestre methanolic extract (SSME) was evaluated for different free radical scavenging activities such as hydroxyl radical, nitric oxide, singlet oxygen, hypochlorous acid, peroxynitrite, superoxide radical and hydrogen peroxide scavenging etc. Iron chelating capacity and inhibition of lipid peroxidation were studied in addition to the assessment of haemolytic activity and erythrocyte membrane stabilizing activity (EMSA). Chemical characterization of SSME were performed by high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS).. The results indicate that SSME possess potent antioxidant activity with IC50 value of 113.06 ± 5.67 μg/ml, 63.93 ± 4.16 μg/ml and 142.14 ± 6.13 μg/ml for hydroxyl radical, superoxide radical and hypochlorous acid, respectively. HPLC analysis revealed presence of different phenolic secondary metabolites such as gallic acid, ferulic acid, p-coumaric acid, syringic acid, myricetin, quercetin etc. GC-MS analysis displayed the predominance of γ-sitosterol, vitamin E and squalene in SSME.. The present study provides a convincing evidence that S. sylvestre not only possess potent antioxidant activity but also can be used as a source of natural bioactive phytochemicals in the future.

    Topics: Animals; Antioxidants; Apocynaceae; Chromatography, High Pressure Liquid; Coumaric Acids; Endangered Species; Flavonoids; Gas Chromatography-Mass Spectrometry; Hydrolyzable Tannins; Iron Chelating Agents; Lipid Peroxidation; Mice; Phenols; Plant Extracts; Propionates; Sikkim; Sitosterols; Squalene; Vitamin E

2015
A comparative calorimetric and spectroscopic study of the effects of cholesterol and of the plant sterols β-sitosterol and stigmasterol on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine bilayer membranes.
    Biochimica et biophysica acta, 2015, Volume: 1848, Issue:8

    We performed comparative DSC and FTIR spectroscopic measurements of the effects of β-sitosterol (Sito) and stigmasterol (Stig) on the thermotropic phase behavior and organization of DPPC bilayers. Sito and Stig are the major sterols in the biological membranes of higher plants, whereas cholesterol (Chol) is the major sterol in mammalian membranes. Sito differs in structure from Chol in having an ethyl group at C24 of the alkyl side-chain, and Stig in having both the C24 ethyl group and trans-double bond at C22. Our DSC studies indicate that the progressive incorporation of Sito and Stig decrease the temperature and cooperativity of the pretransition of DPPC to a slightly lesser and greater extent than Chol, respectively, but the pretransition persists to 10 mol % sterol concentration in all cases. All three sterols produce essentially identical effects on the thermodynamic parameters of the sharp component of the DPPC main phase transition. However, the ability to increase the temperature and decrease the cooperativity and enthalpy of the broad component decreases in the order Chol>Sito>Stig. Nevertheless, at higher Sito/Stig concentrations, there is no evidence of sterol crystallites. Our FTIR spectroscopic studies demonstrate that Sito and especially Stig incorporation produces a smaller ordering of the hydrocarbon chains of fluid DPPC bilayers than does Chol. In general, the presence of a C24 ethyl group in the alkyl side-chain reduces the characteristic effects of Chol on the thermotropic phase behavior and organization of DPPC bilayer membranes, and a trans-double bond at C22 magnifies this effect.

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Calorimetry, Differential Scanning; Cholestadienols; Cholesterol; Lipid Bilayers; Molecular Structure; Phase Transition; Phytosterols; Sitosterols; Spectroscopy, Fourier Transform Infrared; Stigmasterol; Temperature

2015
Biochemical characterization and molecular dynamic simulation of β-sitosterol as a tubulin-binding anticancer agent.
    European journal of pharmacology, 2015, Aug-05, Volume: 760

    Βeta-sitosterol (β-SITO), a phytosterol present in pomegranate, peanut, corn oil, almond, and avocado, has been recognized to offer health benefits and potential clinical uses. β-SITO is orally bioavailable and, as a constituent of edible natural products, is considered to have no undesired side effects. It has also been considered as a potent anticancer agent. However, the molecular mechanism of action of β-SITO as a tubulin-binding anticancer agent and its binding site on tubulin are poorly understood. Using a combination of biochemical analyses and molecular dynamic simulation, we investigated the molecular details of the binding interactions of β-SITO with tubulin. A polymer mass assay comparing the effects of β-SITO and of taxol and vinblastine on tubulin assembly showed that this phytosterol stabilized microtubule assembly in a manner similar to taxol. An 8-anilino-1-naphthalenesulfonic acid assay confirmed the direct interaction of β-SITO with tubulin. Although β-SITO did not show direct binding to the colchicine site on tubulin, it stabilized the colchicine binding. Interestingly, no sulfhydryl groups of tubulin were involved in the binding interaction of β-SITO with tubulin. Based on the results from the biochemical assays, we computationally modeled the binding of β-SITO with tubulin. Using molecular docking followed by molecular dynamic simulations, we found that β-SITO binds tubulin at a novel site (which we call the 'SITO site') adjacent to the colchicine and noscapine sites. Our data suggest that β-SITO is a potent anticancer compound that interferes with microtubule assembly dynamics by binding to a novel site on tubulin.

    Topics: Animals; Antineoplastic Agents; Apoptosis; Binding Sites; Cell Line, Tumor; Cell Proliferation; Crystallography, X-Ray; Dose-Response Relationship, Drug; Goats; Protein Structure, Secondary; Sitosterols; Tubulin

2015
[Chemical constituents of Taxus chinensis var. mairei cell cultures].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2015, Volume: 50, Issue:1

    The chemical constituents of Taxus chinensis var. mairei cell cultures were investigated by chromatographic methods, including silica gel column chromatography, Sephadex LH-20 and preparative HPLC. Thirteen compounds were isolated from the 80% ethanol extract of cultured cells and their structures were elucidated by spectral data and physicochemical properties, which were identified as 2α,4α,7β,9α,10β-pentaacetoxy-14β-hydroxytax-11-ene (1), 2α,4α,7β,9α,10β-pentaacetoxytax-11-ene (2), 1β-deoxybaccatin VI (3), 2α-acetoxytaxusin (4), taxuyunnanine C (5), yunnanxane (6), 2α,5α,10β-triacetoxy-14β-propionyloxy-4 (20), 11-taxadiene (7), 2α,5α,10β-triacetoxy-14β-isobutyryloxy-4 (20), 11-taxadiene (8), 2α,5α,10β-triacetoxy-14β-(2'-methyl)butyryloxy-4 (20), 11-taxadiene (9), 13-dehydroxylbaccatin III (10), 13-dehydroxy-10-deacetylbaccatin III (11), paclitaxel (12) and (13) β-sitosterol. Among them, compound 1 is a new compound, and compounds 2, 4, 10 and 11 are isolated from the cell culture of Taxus chinensis var. mairei for the first time.

    Topics: Alkenes; Cell Culture Techniques; Cells, Cultured; Diterpenes; Molecular Structure; Paclitaxel; Sitosterols; Taxoids; Taxus

2015
Polyamine derivatives of betulinic acid and β-sitosterol: A comparative investigation.
    Steroids, 2015, Volume: 100

    β-Sitosterol and betulinic acid were used in designing their conjugates with selected polyamines bearing either an amide bond, or an ester and an amide bond simultaneously in the target molecule. The synthesized compounds were subjected to basic cytotoxic and antimicrobial tests. The synthetic protocol is described separately for each of the three series of the target amides, because each series of compounds required a different synthetic approach. The cytotoxicity was tested on cells derived from human T-lymphoblastic leukemia, breast adenocarcinoma and cervical cancer, and compared with the tests on normal human fibroblasts. Most of the target compounds (5a-5c, 11a-11c and 16a-16c) showed medium to high cytotoxicity (0.7-7.8 μM), however, in some cases the compounds showed high cytotoxicity even toward normal human fibroblasts (11a-11c). Two compounds of this series (11c and 16c) also displayed antimicrobial activity with high and selective microbe specificity. The compound 11c was potent against Escherichia coli (minimal inhibition concentration (MIC) 6.25 μg mL(-1), i.e. 9.75 nM mL(-1)) and Staphylococcus aureus (MIC 12.5 μg mL(-1), i.e. 19.5 nM mL(-1)), and showed medium activity against Pseudomonas aeruginosa. The compound 16c was highly active against Enterococcus faecalis and S. aureus (both, MIC 3.125 μg mL(-1), i.e. 4.22 nM mL(-1)), both Gram-positive bacteria, however showed only weak activity against E. coli and no activity against P. aeruginosa, both Gram-negative bacteria, which indicates possible microbe specificity of 16c. Comparing β-sitosterol-based series (5a-5c) and betulinic acid series (11a-11c and 16a-16c) of the target compounds, the latter one gave more promising structures. The compounds 11c and 16c showed effects which may be described as multifarious activity (pleiotropic effects).

    Topics: Anti-Bacterial Agents; Betulinic Acid; Cell Survival; Escherichia coli; HeLa Cells; Humans; MCF-7 Cells; Microbial Sensitivity Tests; Pentacyclic Triterpenes; Polyamines; Pseudomonas aeruginosa; Sitosterols; Staphylococcus aureus; Triterpenes

2015
Subcritical extraction of flaxseed oil with n-propane: Composition and purity.
    Food chemistry, 2015, Dec-01, Volume: 188

    Flaxseed (Linum usitatissimum L.) oil was obtained via subcritical n-propane fluid extraction (SubFE) under different temperatures and pressures with an average yield of 28% and its composition, purity and oxidative stability were compared to oils obtained via conventional solvent extraction methods (SEMs). When the oxidative stability was measured by differential scanning calorimetry, the oil was found to be up to 5 times more resistant to lipid oxidation as compared to the SEM oils. Direct infusion electrospray ionization mass spectrometry (ESI-MS) analysis showed characteristic and similar TAG profiles for SubFE and SEMs oils but higher purity for the SubFE oil. The flaxseed oil content of β-tocopherol, campesterol, stigmasterol and sitosterol were quantified via GC-MS. SubFE showed to be a promising alternative to conventional SEM since SubFE provides an oil with higher purity and higher oxidation stability and with comparable levels of biologically active components.

    Topics: beta-Tocopherol; Calorimetry, Differential Scanning; Chemical Fractionation; Cholesterol; Gas Chromatography-Mass Spectrometry; Linseed Oil; Oxidation-Reduction; Phytosterols; Pressure; Principal Component Analysis; Propane; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Stigmasterol; Temperature

2015
A Study on the Specifications of Cold Pressed Colza Oil.
    Recent patents on food, nutrition & agriculture, 2015, Volume: 7, Issue:1

    Cold pressed oil extraction is the preferred method for seeds with high contents of oil, such as colza. Generally speaking, expeller pressing is less complex, more cost efficient and safer than solvent extraction. Moreover, cold pressed oils retain their natural properties better. Cold pressed colza oil has been found to have numerous health benefits. This was an original and unique study conducted as part of the research for the international Codex standard for cold pressed fats and oils, and aims to examine the chemical properties of two varieties of Iranian colza seed, Hyola and Okapi. The studied factors included (a) chemical properties, and (b) physicochemical and quality characteristics. Based on our findings, both varieties of colza seeds in this study had satisfactory levels of oleic and linoleic acid, and no trans-fatty acids. Although both samples had good nutritional properties, the Hyola variety was higher in oleic acid, indicating better oxidative stability. Due to the considerable amounts of β-sitosterol in both varieties, they may be effective in reducing cholesterol and preventing cancer.

    Topics: Brassica rapa; Cold Temperature; Dietary Fats, Unsaturated; Fatty Acids, Monounsaturated; Food Handling; Health; Humans; Iran; Linoleic Acid; Nutritive Value; Oleic Acid; Oxidation-Reduction; Patents as Topic; Plant Extracts; Plant Oils; Rapeseed Oil; Seeds; Sitosterols; Species Specificity; Trans Fatty Acids

2015
Transcriptome Analysis of the Carmine Spider Mite, Tetranychus cinnabarinus (Boisduval, 1867) (Acari: Tetranychidae), and Its Response to β-Sitosterol.
    BioMed research international, 2015, Volume: 2015

    Tetranychus cinnabarinus (Acari: Tetranychidae) is a worldwide polyphagous agricultural pest that has the title of resistance champion among arthropods. We reported previously the identification of the acaricidal compound β-sitosterol from Mentha piperita and Inula japonica. However, the acaricidal mechanism of β-sitosterol is unclear. Due to the limited genetic research carried out, we de novo assembled the transcriptome of T. cinnabarinus using Illumina sequencing and conducted a differential expression analysis of control and β-sitosterol-treated mites. In total, we obtained >5.4 G high-quality bases for each sample with unprecedented sequencing depth and assembled them into 22,941 unigenes. We identified 617 xenobiotic metabolism-related genes involved in detoxification, binding, and transporting of xenobiotics. A highly expanded xenobiotic metabolic system was found in mites. T. cinnabarinus detoxification genes-including carboxyl/cholinesterase and ABC transporter class C-were upregulated after β-sitosterol treatment. Defense-related proteins, such as Toll-like receptor, legumain, and serine proteases, were also activated. Furthermore, other important genes-such as the chloride channel protein, cytochrome b, carboxypeptidase, peritrophic membrane chitin binding protein, and calphostin-may also play important roles in mites' response to β-sitosterol. Our results demonstrate that high-throughput-omics tool facilitates identification of xenobiotic metabolism-related genes and illustration of the acaricidal mechanisms of β-sitosterol.

    Topics: Animals; Gene Expression Regulation; Insect Proteins; Insecticides; Sitosterols; Tetranychidae; Transcriptome

2015
Competitive Solubilization of Cholesterol/Cholesteryl Oleate and Seven Species of Sterol/Stanol in Model Intestinal Solution System.
    Journal of oleo science, 2015, Volume: 64, Issue:7

    The addition of plant sterols/stanols (sterols or stanols) can reduce the solubilization of cholesterol in a model intestinal solution system. We studied the molecular structure of seven different sterols/stanols and the effect they had on the solubilization of cholesterol or cholesterol ester in a model intestinal solution. The differences in the molecular structures of the sterol/stanol species influenced their abilities to reduce the solubility of cholesterol in the competitive solubilization experiments. Cholestanol whose molecular structure resembled cholesterol was the most effective at reducing the solubilization of cholesterol and cholesterol ester, with the solubilities of cholesterol and cholesteryl oleate being 41% and 39% respectively of the values observed for the single solubilizate systems. β-Sitosterol was also able to reduce the solubilities of cholesterol and cholesteryl oleate to 43% and 45% of those observed in a single solubilizate system. Both, stigmasterol and brassicasterol have an unsaturated double bond in a steroid side chain and did not exhibit major cholesterol-lowering effects. These results were reflected by the Gibbs free energy change values (ΔG(0)) for solubilization, where the sterol/stanol species with cholesterol-lowering effects had similar or larger negative ΔG(0) values than those observed for cholesterol.

    Topics: Body Fluids; Cholestadienols; Cholestanol; Cholesterol; Cholesterol Esters; Intestines; Models, Biological; Molecular Structure; Phytosterols; Sitosterols; Solubility; Stigmasterol; Structure-Activity Relationship

2015
Plasma cholesterol-lowering activity of dietary dihydrocholesterol in hypercholesterolemia hamsters.
    Atherosclerosis, 2015, Volume: 242, Issue:1

    Cholesterol analogs have been used to treat hypercholesterolemia. The present study was to examine the effect of dihydrocholesterol (DC) on plasma total cholesterol (TC) compared with that of β-sitosterol (SI) in hamsters fed a high cholesterol diet.. Forty-five male hamsters were randomly divided into 6 groups, fed either a non-cholesterol diet (NCD) or one of five high-cholesterol diets without addition of DC and SI (HCD) or with addition of 0.2% DC (DA), 0.3% DC (DB), 0.2% SI (SA), and 0.3% SI (SB), respectively, for 6 weeks. Results showed that DC added into diet at a dose of 0.2% could reduce plasma TC by 21%, comparable to that of SI (19%). At a higher dose of 0.3%, DC reduced plasma TC by 15%, less effective than SI (32%). Both DC and SI could increase the excretion of fecal sterols, however, DC was more effective in increasing the excretion of neutral sterols but it was less effective in increasing the excretion of acidic sterols compared with SI. Results on the incorporation of sterols in micellar solutions clearly demonstrated both DC and SI could displace the cholesterol from micelles with the former being more effective than the latter.. DC was equally effective in reducing plasma cholesterol as SI at a low dose. Plasma TC-lowering activity of DC was mediated by inhibiting the cholesterol absorption and increasing the fecal sterol excretion.

    Topics: Adipose Tissue; Animal Feed; Animals; Anticholesteremic Agents; Aortic Diseases; Atherosclerosis; Bile Acids and Salts; Cholestanol; Cholesterol; Cholesterol, Dietary; Cricetinae; Drug Evaluation, Preclinical; Feces; Gene Expression Profiling; Hyperlipoproteinemia Type II; Intestinal Absorption; Lipids; Lipoproteins; Liver; Male; Mesocricetus; Metabolic Networks and Pathways; Micelles; Molecular Structure; Organ Size; Plaque, Atherosclerotic; Random Allocation; RNA, Messenger; Sitosterols; Sterols; Viscera

2015
[Chemical Constituents with Anti-hypoxia Activity from Saussurea involucrata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:1

    To investigate the chemical constituents with anti-hypoxia activity from Saussurea involucrata.. The chemical constituents, isolated and purified by column chromatography from Saussurea involucrata, were identified by several spectroscopic methods. The anti-hypoxic activities of these compounds were examined using the normobaric hypoxic model of mice.. Twelve compounds were isolated from petroleum ether extract of Saussurea involucrata and identified as n-octacosane (1), 1-undecanol (2), heptadecan-l-ol(3), heptacosan-1-ol(4), myristicin (5), apiol(6), β-sitosterol(7), lupeol(8), moslosooflavone (9), mosloflavone (10), negletein(11), and 5, 6-dihydroxy-7, 8-dimethoxyflavone(12).. All compounds except 7 and 8 are isolated from this plant for the first time. Compound 1, 5 and 8 - 12 can significantly prolong the survival time of hypoxic mice.

    Topics: Alkanes; Animals; Flavonoids; Hypoxia; Mice; Phytochemicals; Plant Extracts; Saussurea; Sitosterols; Solvents

2015
[Study on Chemical Constituents of Petroleum Ether Fraction from Rubus alceaefolius].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:1

    To investigate the chemical constituents of Rubus alceaefolius.. Nine compounds were isolated and purified from the petroleum ether extract of 95% alcohol extract of Rubus alceaefolius by repeated column chromatography on silica, Sephadex LH-20 and structurally identified by spectral analysis.. The compounds were identified as chrysophanol(1), physcion (2), β-sitosterol(3), 3-oxotirucalla-7, 24-dien-21-oic acid(4), myricadiol(5), 19-α-hydroxy-3-acetyl-ursolic acid(6), N-benzoylphenylalaninyl-N-benzoylphenylalaninate(7), aurantiamide acetate(8) and euscaphic acid(9).. Compounds land 4~8 are isolated from this plant for the first time, and compounds 4 - 8 are found in plants of Rubus genus for the first time.

    Topics: Dipeptides; Emodin; Phytochemicals; Plant Extracts; Rubus; Sitosterols; Solvents; Triterpenes

2015
[Chemical Constituents from Cynanchum paniculatum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:1

    To investigate the chemical constituents from Gynanchum paniculatum.. The constituents were isolated and purified by silica gel, Sephadex LH-20 column chromatography, and preparative TLC. Their structures were identified on the basis of spectral data and physiochemical characteristics.. 15 compounds were isolated from 70% ethanol extract and identified as β-sitosterol(1), β-daucosterin (2), mudanoside A (3), paeonolide (4), santamarin (5), paeonol(6), annobraine (7), laricircsinol (8), α-asarone(9), 7-angelyheliotridine(10), β-amyrin(11), uridine(12), kaempferol-3-O-β-D-glucopyranosyl(1→2)α-L-arabinopyranoside(13), kaempferol-7-O-(4", 6"-di-p-hydroxycinnamoyl-2", 3"-diacetyl)-β-D-glucopyranoside(14), and (2S, E)-N-[2-hydroxy-2-(4-hydroxyphenyl) ethyl] ferulamide (15).. Compounds 4, 6, 8, 11, 12 and 15 are isolated from this plant for the first time, compounds 5 and 14 are firstly isolated from the palnts of Cynanchum genus.

    Topics: Allylbenzene Derivatives; Anisoles; Cynanchum; Kaempferols; Phytochemicals; Sitosterols

2015
[Chemical comparison of different Farfarae Flos by NMR-based metabolomic approaches].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2015, Volume: 50, Issue:5

    1H NMR-based metabolomic approach combined with multivariate statistical analysis was used to evaluate the quality of 21 Farfarae Flos (FF) samples from different growth regions. Principal component analysis showed that wild and cultivated FF could be separated clearly, suggesting a big chemical difference existed between them. Supervised PLS-DA analysis indicated that the wild samples showed higher levels of secondary metabolites, such as bauer-7-ene-3β, 16α-diol, chlorogenic acid, rutin, 7-(3'-ethylcrotonoyloxy)-1α-(2'-methyl-butyryloxy)-3, 14-dehydro-Z-notonipetranone (EMDNT), tussilagone, β-sitosterol and sitosterone. This is consistent with traditional experience that the quality of wild samples are better than that of cultivated ones. The content of pyrrolizidine alkaloids senkirkine also differed greatly among samples from different habitats. The Pearson correlation analysis showed that senkirkine is positively correlated with 4, 5-O-dicaffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, 3,4-O-dicaffeoylquinic acid, rutin, kampferol analogues, to a statistically significant extent. The correlation between the toxic compounds and the bioactive components in FF should be further studied.

    Topics: Chlorogenic Acid; Drugs, Chinese Herbal; Flowers; Magnetic Resonance Imaging; Magnetic Resonance Spectroscopy; Metabolomics; Quinic Acid; Rutin; Sitosterols; Tussilago

2015
Arum Palaestinum with isovanillin, linolenic acid and β-sitosterol inhibits prostate cancer spheroids and reduces the growth rate of prostate tumors in mice.
    BMC complementary and alternative medicine, 2015, Aug-05, Volume: 15

    Arum palaestinum is a plant commonly found in the Middle East that is ingested as an herbal remedy to fight cancer. However, no studies have examined the direct effect of the plant/plant extract on tumor growth in an animal model.. Verified prostate cancer cells were plated as 3D spheroids to determine the effect of extract from boiled Arum Palaestinum Boiss roots. In addition, male NU/NU mice (8 weeks old) with xenograft tumors derived from the prostate cancer cell line were treated daily with 1000 mg/kg body weight gavage of the suspension GZ17. The tumor growth was measured repeatedly with calipers and the excised tumors were weighed at the termination of the 3 week study. Control mice (10 mice in each group) received vehicle in the same manner and volume.. The number of live prostate cancer cells declined in a dose/dependent manner with a 24 h exposure to the extract at doses of 0.015 to 6.25 mg/mL. A fortified version of the extract (referred to as GZ17) that contained higher levels of isovanillin, linolenic acid and β-sitosterol had a stronger effect on the cell death rate, shifting the percentage of dead cells from 30 % to 55 % at the highest dose while the vehicle control had no effect on cell numbers. When GZ17 was applied to non-cancer tissue, in this case, human islets, there was no cell death at doses that were toxic to treated cancer cells. Preliminary toxicity studies were conducted on rats using an up-down design, with no signs of toxic effect at the highest dose. NU/NU mice with xenograft prostate tumors treated with GZ17 had a dramatic inhibition of tumor progression, while tumors in the control group grew steadily through the 3 weeks. The rate of tumor volume increase was 73 mm(3)/day for the vehicle group and 24 mm(3)/day for the GZ17 treated mice. While there was a trend towards lower excised tumor weight at study termination in the GZ17 treatment group, there was no statistical difference.. Fortified Arum palaestinum Boiss caused a reduction in live cells within prostate cancer spheroids and blocked tumor growth in xenografted prostate tumors in mice without signs of toxicity.

    Topics: alpha-Linolenic Acid; Animals; Antineoplastic Agents; Arum; Benzaldehydes; Cell Line, Tumor; Cell Proliferation; Male; Mice; Plant Extracts; Prostatic Neoplasms; Rats; Sitosterols; Spheroids, Cellular; Tumor Cells, Cultured; Xenograft Model Antitumor Assays

2015
Identification of beta-sitosterol and stigmasterol in Bambusa bambos (L.) Voss leaf extract using HPLC and its estrogenic effect in vitro.
    Journal of pharmaceutical and biomedical analysis, 2015, Nov-10, Volume: 115

    Focus of the study is to identify a safe alternate to Hormone Replacement Therapy by identifying the presence of β-sitosterol and stigmasterol in the hydroalcoholic extract of Bambusa bambos using HPTLC and RP-HPLC-PDA; by evaluating the estrogenic effects of extract containing β-sitosterol and stigmasterol on the growth of MCF-7 cells in vitro. Plant material was identified by DNA sequencing analysis. Presence of β-sitosterol and stigmasterol was confirmed by HPTLC and direct RP-HPLC-PDA. Peaks with retention time about 19.13 and 21.16min were found to be stigmasterol and β-sitosterol in extract. Extract was not cytotoxic to MCF-7 cells in any of the dilutions. It induced cell proliferation and all the dilutions except <500μg/ml have significantly increased cell multiplication. 15.6, 31.2, 62.5 and 125μg/ml of HEBB have shown influence on the proliferation rates similar to the standard 17β-estradiol. The results suggest that HEBB might be used as a safe alternative to estrogen replacement therapies.

    Topics: Bambusa; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Ethnopharmacology; Humans; MCF-7 Cells; Molecular Structure; Phytoestrogens; Plant Extracts; Plant Leaves; Sitosterols; Stigmasterol

2015
The potential anti-proliferative effect of β-sitosterol on human mast cell line-1 cells.
    Canadian journal of physiology and pharmacology, 2015, Volume: 93, Issue:11

    Thymic stromal lymphopoietin (TSLP) was reported to induce mast cell proliferation and aggravate allergic reactions through activation of mouse double minute 2 (MDM2). We aimed to ascertain that β-sitosterol (SI), which is one of the several phytosterols found mostly in foods, would regulate TSLP-induced mast cell proliferation. The results showed that SI significantly decreased the proliferation of human mast cell line (HMC-1) cells promoted by TSLP. SI significantly decreased the mRNA expression of Ki-67 in the TSLP-treated HMC-1 cells. SI significantly suppressed the production and mRNA expression of interleukin-13 in the TSLP-treated HMC-1 cells. Furthermore, SI downregulated the expression of MDM2 and phosphorylation of STAT6, whereas it upregulated the expression of p53, activation of caspase-3, and cleavage of poly ADP-ribose polymerase in the TSLP-treated HMC-1 cells. Results of this study suggest that SI may be a potential therapeutic agent for mast cell-mediated allergic diseases.

    Topics: Cell Line; Cell Proliferation; Dose-Response Relationship, Drug; Humans; Interleukin-13; Mast Cells; Sitosterols

2015
Flax Fiber Hydrophobic Extract Inhibits Human Skin Cells Inflammation and Causes Remodeling of Extracellular Matrix and Wound Closure Activation.
    BioMed research international, 2015, Volume: 2015

    Inflammation is the basis of many diseases, with chronic wounds amongst them, limiting cell proliferation and tissue regeneration. Our previous preclinical study of flax fiber applied as a wound dressing and analysis of its components impact on the fibroblast transcriptome suggested flax fiber hydrophobic extract use as an anti-inflammatory and wound healing preparation. The extract contains cannabidiol (CBD), phytosterols, and unsaturated fatty acids, showing great promise in wound healing. In in vitro proliferation and wound closure tests the extract activated cell migration and proliferation. The activity of matrix metalloproteinases in skin cells was increased, suggesting activation of extracellular components remodeling. The expression of cytokines was diminished by the extract in a cannabidiol-dependent manner, but β-sitosterol can act synergistically with CBD in inflammation inhibition. Extracellular matrix related genes were also analyzed, considering their importance in further stages of wound healing. The extract activated skin cell matrix remodeling, but the changes were only partially cannabidiol- and β-sitosterol-dependent. The possible role of fatty acids also present in the extract is suggested. The study shows the hydrophobic flax fiber components as wound healing activators, with anti-inflammatory cannabidiol acting in synergy with sterols, and migration and proliferation promoting agents, some of which still require experimental identification.

    Topics: Cannabidiol; Cell Movement; Cell Proliferation; Extracellular Matrix; Fibroblasts; Flax; Humans; Keratinocytes; Plant Extracts; Sitosterols; Wound Healing

2015
Characterization of Arabidopsis sterol glycosyltransferase TTG15/UGT80B1 role during freeze and heat stress.
    Plant signaling & behavior, 2015, Volume: 10, Issue:12

    Sterol glycosyltransferases regulate the properties of sterols by catalyzing the transfer of carbohydrate molecules to the sterol moiety for the synthesis of steryl glycosides and acyl steryl glycosides. We have analyzed the functional role of TTG15/UGT80B1 gene of Arabidopsis thaliana in freeze/thaw and heat shock stress using T-DNA insertional sgt knockout mutants. Quantitative study of spatial as well as temporal gene expression showed tissue-specific and dynamic expression patterns throughout the growth stages. Comparative responses of Col-0, TTG15/UGT80B1 knockout mutant and p35S:TTG15/UGT80B1 restored lines were analyzed under heat and freeze stress conditions. Heat tolerance was determined by survival of plants at 42°C for 3 h, MDA analysis and chlorophyll fluorescence image (CFI) analysis. Freezing tolerance was determined by survival of the plants at -1°C temperature in non-acclimatized (NA) and cold acclimatized (CA) conditions and also by CFI analysis, which revealed that, p35S:TTG15/UGT80B1 restored plants were more adapted to freeze stress than TTG15/UGT80B1 knockout mutant under CA condition. HPLC analysis of the plants showed reduced sterol glycoside in mutant seedlings as compared to other genotypes. Following CA condition, both β-sitosterol and sitosterol glycoside quantity was more in Col-0 and p35S:TTG15/UGT80B1 restored lines, whereas it was significantly less in TTG15/UGT80B1 knockout mutants. From these results, it may be concluded that due to low content of free sterols and sterol glycosides, the physiology of mutant plants was more affected during both, the chilling and heat stress.

    Topics: Acclimatization; Arabidopsis; Arabidopsis Proteins; Chromatography, High Pressure Liquid; Ecotype; Fluorescence; Freezing; Gene Expression Regulation, Plant; Genes, Plant; Glucosyltransferases; Hot Temperature; Lipid Peroxidation; Mutation; Phenotype; Promoter Regions, Genetic; Sitosterols; Stress, Physiological; Time Factors

2015
Antileishmanial Activity of Compounds Isolated from Sassafras albidum.
    Natural product communications, 2015, Volume: 10, Issue:7

    Leishmaniasis is a neglected tropical disease caused by Leishmania parasitic protozoa, which currently lacks efficient treatment. Natural products have shown promise as a potential source for antiprotozoal drugs. This work focuses on the antileishmanial potential of Sassafras albidum (Lauraceae) bark extract. The crude bark extract of S. albidum showed excellent antileishmanial activity with an IC50 value less than 12.5 μg/mL against promastigotes of L. amazonensis. The chloroform stem bark extract of S. albidum was subjected to preparative column chromatography. Five compounds were isolated, purified by recrystallization, and identified as sesamin, spinescin, β-sitosterol, hexatriacontanal, and 1-triacontanol. Antileishmanial and cytotoxic screening were performed on these compounds. Sesamin exhibited the best activity against L. amazonensis with an IC50 of 15.8 μg/mL and was not cytotoxic to mouse macrophage cells (CC50 > 100 μg/mL).

    Topics: Dioxoles; Fatty Alcohols; Leishmania; Lignans; Microbial Sensitivity Tests; Plant Extracts; Sassafras; Sitosterols; Trypanocidal Agents

2015
[Study on Chemical Constituents of Fermented Antrodia camphorata Powder].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:2

    To study the chemical constituents of fermented Antrodia camphorata powder.. 15 compounds were isolated from Antrodia camphorata by Silica gel column chromatography, ODS column chromatography, gel column chromatography, preparative liquid phase chromatography separation technique, as well as recrystallization.. On the basis of their physical and chemical properties and spectral data,their structures were identified as Ferulic acid (1), Inositol (2), β-Sitosterol (3),Vanillin (4),Vanillic acid (5), Butyric acid (6), Daucosterol (7), p-Hydroxycinnamic acid (8), Lauric acid (9), Inosine (10), Uridine (11), Adenine (12), D(+)-Sucrose (13), Arachidic acid (14) and Guanosine (15).. Compounds 1, 5, 6 and 8-15 are isolated from fermented powder for the first time.

    Topics: Antrodia; Chromatography, Liquid; Coumaric Acids; Fermentation; Phytochemicals; Plants, Medicinal; Powders; Propionates; Sitosterols; Vanillic Acid

2015
[Chemical Constituents from Leaves of "Chuju" Chrysanthemum morifolium and Their Antioxidant Activities in vitro].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:2

    To study the chemical constituents from the leaves of "Chuju" Chrysanthemum morifolium.. All compounds were separated and purified by column chromatography over silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by spectral methods including 1H-NMR and 13C-NMR.. 21 compounds were isolated and identified as octa-cosyl alcohol (1), β-sitosterol (2), lupeol (3), α-amyrin (4), daucosterol (5), ineupatorolide B (6), syringin (7), chlorogenic acid (8), petasiphenol (9), physcion (10), acacetin (11), eupatilin (12), quercetin (13), diosmetin (14), luteolin (15), apigenin (16), apigenin- 7-O-β-D-glucopyranoside (17), quercetin-3-O-β-D-glucopyranoside (18), luteolin-7-O-β-D-gluco pyranoside (19), apigenin-7-O-β-D- neospheroside (20), and acacetin-7-O-β-D-glucoside (21).. Compounds 1-12, 18 and 20 are isolated from this plant for the first time. Compounds 10, 13, 14, 15 and 16 have shown strong antioxidant activities by DPPH · scavenging activity better than Vit C.

    Topics: Antioxidants; Apigenin; Chlorogenic Acid; Chrysanthemum; Flavones; Flavonoids; Glucosides; Luteolin; Phenylpropionates; Phytochemicals; Plant Leaves; Plants, Medicinal; Quercetin; Sitosterols

2015
[Study on Chemical Constituents of Peanut Hull].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:2

    To investigate the chemical constituents of peanut hull.. Several chromatography methods such as silica gel and Sephadex LH-20 combined with recrystallization were applied to isolate the compounds. Based on spectrum technologies (MS,1H-NMR and 13C-NMR) and physico-chemical methods, structures of isolated compounds were identified.. Twelve compounds were isolated and elucidated as luteolin (1), diosmetin (2), 5,7,3',4'-tetrahydroxy-8-prenyflavone (3),5,7,3'-trihydroxy-4'- methoxy-8-prenylflavone(4), eriodicrtyol (5), racemoflavone (6), hydnocarpin (7), 5,7-dihydroxy chromone (8), 5-hydroxy-chromone- 7-O-β-D-glucoside (9), ferulic acid (10), β-sitosterol (11) and daucosterol(12).. Except compounds 1, 5 and 8, all compounds are obtained from peanut hull for the first time.

    Topics: Arachis; Coumaric Acids; Flavonoids; Luteolin; Phytochemicals; Seeds; Sitosterols

2015
Diversification of sterol methyltransferase enzymes in plants and a role for β-sitosterol in oriented cell plate formation and polarized growth.
    The Plant journal : for cell and molecular biology, 2015, Volume: 84, Issue:5

    Phytosterols are classified into C24-ethylsterols and C24-methylsterols according to the different C24-alkylation levels conferred by two types of sterol methyltransferases (SMTs). The first type of SMT (SMT1) is widely conserved, whereas the second type (SMT2) has diverged in charophytes and land plants. The Arabidopsis smt2 smt3 mutant is defective in the SMT2 step, leading to deficiency in C24-ethylsterols while the C24-methylsterol pathway is unchanged. smt2 smt3 plants exhibit severe dwarfism and abnormal development throughout their life cycle, with irregular cell division followed by collapsed cell files. Preprophase bands are occasionally formed in perpendicular directions in adjacent cells, and abnormal phragmoplasts with mislocalized KNOLLE syntaxin and tubulin are observed. Defects in auxin-dependent processes are exemplified by mislocalizations of the PIN2 auxin efflux carrier due to disrupted cell division and failure to distribute PIN2 asymmetrically after cytokinesis. Although endocytosis of PIN2-GFP from the plasma membrane (PM) is apparently unaffected in smt2 smt3, strong inhibition of the endocytic recycling is associated with a remarkable reduction in the level of PIN2-GFP on the PM. Aberrant localization of the cytoplasmic linker associated protein (CLASP) and microtubules is implicated in the disrupted endocytic recycling in smt2 smt3. Exogenous C24-ethylsterols partially recover lateral root development and auxin distribution in smt2 smt3 roots. These results indicate that C24-ethylsterols play a crucial role in division plane determination, directional auxin transport, and polar growth. It is proposed that the divergence of SMT2 genes together with the ability to produce C24-ethylsterols were critical events to achieve polarized growth in the plant lineage.

    Topics: Arabidopsis; Arabidopsis Proteins; Biological Transport; Cell Division; Cell Polarity; Endocytosis; Indoleacetic Acids; Methyltransferases; Sitosterols; Sterols

2015
[Chemical Constituents from Melissa officinalis Leaves].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:3

    To investigate the chemical constituents of Melissa officinalis leaves.. The chemical constituents were separated by silica gel column chromatography and their structures were determined by spectroscopic experiments.. 13 compounds were isolated and identified as protocatechuyl aldehyde(1), serratagenic acid(2), vanillin(3), 2α,3β-dihydroxy-urs-12-en-28-oic acid(4), ursolic acid(5), oleanolic acid(6), daucosterol(7),2α,3β,23,29-tetrahydroxyolean-12-en-28-oic acid-29-O-β-D-gluco- pyranoside(8), luteolin(9) rosmarinic acid(10), luteolin-7-O-β-D-glucoside (11), β-stitosterol(12) and palmitic acid(13).. Compounds 1 ~ 8 are separated from this plant for the first time and compounds 1-4 and 8 are isolated from this genus for the first time.

    Topics: Benzaldehydes; Cinnamates; Depsides; Melissa; Oleanolic Acid; Palmitic Acid; Phytochemicals; Plant Extracts; Rosmarinic Acid; Sitosterols; Triterpenes; Ursolic Acid

2015
β-sitosterol interacts with pneumolysin to prevent Streptococcus pneumoniae infection.
    Scientific reports, 2015, Dec-03, Volume: 5

    Pneumolysin is one of the major virulence factors elaborated by Streptococcus pneumoniae; this toxin is a member of the cholesterol-dependent cytolysins. Engagement of cholesterol induces the formation of a multi-subunit complex by pneumolysin that lyses host cells by forming pores on the membrane. Because pneumolysin released by bacteria which have been killed by conventional antibiotics is still active, agents capable of directly attacking the toxin are considered advantageous against antimicrobials in the treatment of S. pneumoniae infections. Here we found that the phytosterol, β-sitosterol, effectively protects against cell lysis caused by pneumolysin. This compound interacts with the toxin at Thr459 and Leu460, two sites important for being recognized by its natural ligand, cholesterol. Similar to cholesterol, β-sitosterol induces pneumolysin oligomerization. This compound also protects cells from damage by other cholesterol-dependent toxins. Finally, this compound protects mice against S. pneumoniae infection. Thus, β-sitosterol is a candidate for the development of anti-virulence agents against pathogens that rely on cholesterol-dependent toxins for successful infections.

    Topics: Animals; Anti-Bacterial Agents; Bacterial Proteins; Binding Sites; Cholesterol; Hemolysis; Humans; Lung; Male; Mice, Inbred C57BL; Models, Molecular; Pneumococcal Infections; Sitosterols; Streptococcus pneumoniae; Streptolysins; Surface Plasmon Resonance

2015
[Chemical Components from Leaves of Fatsia japonica and Their Antitumor Activities in vitro].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:4

    To study the chemical components from the leaves of Fatsia japonica and their antitumor activities in vitro.. All compounds were separated and purified by column chromatography over silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by physical and chemical properties and spectral methods including 1H-NMR and 13C-NMR. Antitumor assay was measured by MTT method.. 18 compounds were isolated and identified as palmitic acid (1), β-hydroxypropiovanillone (2), adenosine (3), β-sitosterol (4), daucosterol (5), oleanolic acid (6), echinocystic acid (7), betulinic acid (8), hederagenin(9), hederagenin-3-O-α-L-rhamnopyranosyl(1-->2)-α-L-arabinopyranoside(10), acacetin(11), quercetin(12), quercetin-3-O-β-D-glucopyranoside(13), isovitexin(14), isovitexin-7-O-glucoside(15), astragalin(16), methylpluviatolide(17), and syringaresinol-4-O-β-D-glucopyranoside(18).. All compounds are isolated from the leaves of Fatsia japonica for the first time except compound 1. The ethyl acetate extract and compounds 6, 10, 12 and 18 at the concentration of 0. 5 mg/mL showed inhibitory effect against the proliferation of colon cell line A549 with the inhibitory rate over 90% in vitro.

    Topics: Antineoplastic Agents, Phytogenic; Araliaceae; Betulinic Acid; Cell Line, Tumor; Chromatography, High Pressure Liquid; Flavones; Furans; Glucosides; Humans; Kaempferols; Lactones; Lignans; Oleanolic Acid; Pentacyclic Triterpenes; Phytochemicals; Plant Leaves; Sitosterols; Triterpenes

2015
[Chemical Constituents from Syzygium samarangense Branches and Leaves].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:4

    To investigate the chemical constituents from the branches and leaves of Syzygium samarangense.. The dried branches and leaves of Syzygium samarangense were powdered and extracted with 95% ethanol, then partitioned with petroleum ether, chloroform and ethyl acetate. The chloroform fraction was subjected to silica gel, Sephdex L-20 and preparative HPLC. The structures were identified by physicochemical properties and spectral data.. 14 compounds were respectively isolated and identified as ursolic aldehyde(1), betulin(2), betulinic aldehyde(3), betulinic acid(4), lupeol(5), β-sitosterol(6), 5, 7-dihydroxy-6-methylflavanone(7), 2', 4'-dihydroxy-6'-methoxy-3'-methyldihydrochalcone (8), 2', 4'-dihydroxy-6'-methoxy-3'-methylchalcone (9), 5, 7-dihydroxy-6, 8-dimethylflavanone (10), 5, 7-dihydroxyflavanone (11), 2', 4'-dihydroxy-6'-methoxy-3', 5'-dimethyldihydrochalcone (12), 2'-hydroxy-4', 6'-dimethoxy-3'-methylchalcone(13) and p-hydroxyb6nzaldehyde(14).. Compounds 1 - 4 and 14 are isolated from this plant for the first time.

    Topics: Betulinic Acid; Pentacyclic Triterpenes; Phytochemicals; Plant Extracts; Plant Leaves; Sitosterols; Syzygium; Triterpenes

2015
[Chemical Constituents of Ethyl Acetate Fraction of Suaeda glauca].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:4

    To study the chemical constituents of Suaeda glauca.. The chemical constituents were isolated and purified with several separation and purification techniques. Their structures were identified by physicochemical properties and various spectroscopic methods.. Ten compounds were isolated from the ethyl acetate fraction as lignoceric acid (1), β-amyrin-n-nonyl ether(2), β-sitosterol(3), β-daucosterol(4), quercetin(5), luteolin(6), luteolin-7-O-β-D-glucoside(7), isorhamnetin(8), scopoletin (9) and stigmasterol(10).. Compounds 1, 2, 6, 7, 8, 9 and 10 are isolated from Suaeda genus for the first time and compounds 3 - 5 are isolated from this plant for the first time.

    Topics: Acetates; Chenopodiaceae; Glucosides; Luteolin; Oleanolic Acid; Phytochemicals; Plant Extracts; Quercetin; Sitosterols; Stigmasterol

2015
[Chemical Constituents from Claoxylon indicum Stems].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:4

    To study the chemical constituents of Claoxylon indicum stems.. The chemical constituents were isolated, purified and identified by various chromatographic and spectral techniques.. Seven compounds including oleanolic acid (1), 6-amyrin(2), 7-ketositosterol(3), scopoletin(4), β-sitosterol-β-glucoside(5), L-pyroglutamic acid (6) and β-sitosterol (7) were isolated from ethanol extract of this plant stems.. Compounds 1 - 6 are obtained from this plant for the first time.

    Topics: Euphorbiaceae; Oleanolic Acid; Phytochemicals; Plant Stems; Sitosterols

2015
[Chemical Constituents From Rhus chinensis Fruit Dregs].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:6

    To isolate and elucidate the constituents from the fruit dregs of Rhus chinensis.. The constituents were isolated and purified by chromatography on silica gel,Sephadex LH-20, RP-C18 gel and recrystallization. The structures were elucidated on the basis of the chemical evidence and spectroscopic data.. Ten compounds were obtained: β-sitosterol (1), morolic acid (2), (2S) -1-O-heptatriacontanoyl glycerol (3), α-monpalmitin (4), palmitic acid (5), gallic acid (6), methyl gallate (7), ethyl gallate (8), propyl gallate (9), and protocatechuic acid (10).. Compounds 3, 4 and 9 are isolated from the plants of Rhus genus for the first time.

    Topics: Fruit; Gallic Acid; Rhus; Sitosterols; Triterpenes

2015
[Chemical Constituents from Leaves of Hibiscus syriacus and Their α-Glucosidase Inhibitory Activities].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:5

    To study the chemical constituents from Hibiscus syriacus leaves and their α-glucosidase inhibitory activities.. Column chromatography including macroporous resins, silica gel and Sephadex LH-20 were used for the isolation and purification of all compounds. Spectroscopic methods including physical and chemical properties, 1H-NMR and 13C-NMR were used for the identification of structures. Their α-glucosidase inhibitory activities were detected by a 96-well microplate.. 15 compounds were isolated and identified as β-sitosterol(1), β-daucostero (2), β-amyrin (3), oleanolic acid (4), stigmast-4-en-3-one (5), friedelin (6), syriacusin A (7), kaempferol (8), isovitexin (9), vitexin (10), apigenin (11), apigenin-7-O-β-D-glucopyranoside (12), luteolin-7-O-β-D-glucopyranoside (13), vitexin-7-O-β-D-glucopyranoside (14) and rutin (15).. All the compounds are isolated from the leaves of Hibiscus syriacus for the first time. Taking acarbose as positive control, the α-glucosidase inhibitory activities of 15 compounds were evaluated. Compounds 7 and 9 have shown strong α-glucosidase inhibitory activities with IC50 of 39.03 ± 0.38 and 32.12 ± 0.62 mg/L, inhibition ratio of 94.95% and 97.15%, respectively.

    Topics: alpha-Glucosidases; Apigenin; Glucosides; Glycoside Hydrolase Inhibitors; Hibiscus; Kaempferols; Luteolin; Oleanolic Acid; Phytochemicals; Plant Leaves; Sitosterols; Stigmasterol; Triterpenes

2015
[Chemical Constituents of Eucommia ulmoides in Guizhou Province].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:5

    To study the chemical constituents of Eucommia ulmoides in Guizhou Province.. Silica gel, Sephadex LH-20, RP-18, MCI and semi-preparative HPLC were used to study the chemical constituents of Eucommia ulmoides, and the chemical structures were elucidated by application of spectral data.. 16 compounds were isolated from the bark of Eucommia ulmoides. Their structures were identified as β-sitosterol (1), cycloeucalenol (2), betulinic acid (3), 24-methylenecycloartenone (4), cycloeucalenone (5), salicifoliol (6), pinoresinol (7), genipin (8) , alternariol (9), balanophonin (10), eucommidiol (11), pinoresinol-4'-O-β-D-glucopyranoside (12), eucommiol (13), deoxyeucommiol (14), 8-hydroxypinoresinol (15), and dehydrodiconiferyl alcohol -γ'-O-β-D-glucopyranoside (16).. Seven compounds, including compounds 2,4 - 6,9, 10 and 15 are isolated from Eucommia ulmoides for the first time, and compound 14 is isolated from the bark of Eucommia ulmoides for the first time.

    Topics: Betulinic Acid; Chromatography, High Pressure Liquid; Eucommiaceae; Furans; Lignans; Pentacyclic Triterpenes; Phenols; Phytochemicals; Plant Bark; Sitosterols; Triterpenes

2015
[Chemical Constituents from Processed Products of Aconitum Vilmoriniani Radix].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:5

    To investigate the chemical constituents of the processed products of Aconitum Vilmorinian Radix.. The constituents were isolated by repeated column chromatography over silica gel, alumina and RP-C18 as well as recrystallization. The structures were elucidated on the basis of spectral analysis and physicochemical properties.. Ten compounds were obtained from the methanol extract, and they were identified as yunaconitine (1), 8-deacetyl-yunaconitine (2), geniculatine C (3), vilmorrianine B (4), vilmorrianine C(5), vilmorrianine D (6), talatisamine (7), β-sitosterol (8), β-daucosterol (9) and β-sitosterol acetate (10).. All compounds are obtained from the processed products of Aconitum Vilmoriniani Radix for the first time.

    Topics: Aconitine; Aconitum; Phytochemicals; Plant Roots; Sitosterols

2015
[Chemical Constituents of Paris polyphylla var. chinensis Aerial Parts].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:9

    To study the chemical constituents of aerial parts of Paris polyphylla var. chinensis .. Aerial parts of Paris polyphylla var. chinensis was extracted with 95% EtOH, and separated and purified by silica gel, RP 18 and Sephadex LH-20 col- umn chromatography. The structures were identified by spectroscopic analysis.. A total of ten compounds were isolated and iden- tified as β-sitosterol (1) ergosta-7, 22-dien-3-one (2), β-ecdysone (3), kaempferol (4), daucosterol (5) luteolin (6) calonysterone (7), luteolin-7-O-glucoside (8), quercetin (9), and 3β, 5α, 9α-trihydroxyergosta-7, 22-dien-6-one (10).. Compounds 2,6 and 10 are isolated from Paris polyphylla var. chinensis for the first time.

    Topics: Ecdysterone; Flavones; Glucosides; Kaempferols; Liliaceae; Phytochemicals; Plant Components, Aerial; Plant Extracts; Plants, Medicinal; Quercetin; Sitosterols

2015
[Chemical Constituents from Young Fruits of Citrus maxima cv. Shatian].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:9

    To investigate the chemical constituents from the young fruits of Citrus maxima cv. Shatian.. The chemical constituents were isolated and purified by silica gel column chromatography and recrystallization, and their structures were identified on the basis of physicochemical properties and spectral analysis.. Seven compounds were isolated and identified as naringenin (I), marmin (II), naringin (III), β-sitosterol (IV) 5,7-dihydroxylcoumarin (V) 1, 3,5-trihydroxyhenzene (VI) and xanthotoxol (VII).. Except compound III, all compounds are isolated from the young fruits of Citrus maxima cv. Shatian for the first time.

    Topics: Citrus; Flavanones; Fruit; Phytochemicals; Sitosterols

2015
[Low Polar Constituents from Annona squamosa Fruit Pericarp].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:7

    To study the low polar constituents from Annona squamosa fruit pericarp.. The fruit pericarp was percolated with 95% EtOH at room temperature. The extract was subjected to Silica gel chromatography and eluted with gradually more polar and EtOAc-MeOH mixtures. The part eluted range Pet-EtOAc from 5:1 to 1:1 was subjected to repeated column chromatography. The constituents were identified by physicochemical property and NMR data.. Eight constituents were isolated and identified as tricosane(1), β-sitosterol(2), succinic acid (3), annosquamosin D(4), 4α-hydroxy-19-nor-(E)-kauran-17-oic acid(5), (E)-16β, 17-dihydroxy-kauran-19-oic acid(6), (E)-16α, 17-dihydroxy-kauran-19-oic acid(7), and 16β-hydroxy-17-acetoxy-(E)-kauran-19-oic acid(8).. All constituents are firstly isolated from Annona squamosa fruit pericarp except compound 6.

    Topics: Annona; Diterpenes; Fruit; Magnetic Resonance Spectroscopy; Plants, Medicinal; Sitosterols; Succinic Acid

2015
[Study on Chemical Constituents in Seeds of Datura metel from Xinjiang].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:8

    To study the chemical constituents in the seeds of Datura metel from Xinjiang Province.. The constituents were isolated and purified by silica gel, ODS and Sephadex LH-20 column chromatographic methods. Their chemical structures were analyzed and identified on the basis of physical and chemical properties and spectral data.. Ten compounds were isolated and identified as Isofraxidin (1), Scopatone (2), Daturadiol (3),1,4-Benzenediol (4), Arenarine D (5), Vanillin (6), N-trans-Feruloyl-tyramine (7), Scopoletin (8), G-Sitosterol (9) and Hyoscyamilactol (10).. Compounds 1 and 2 are firstly isolated from the plants in Solanaceae, compounds 3-8 are firstly isolated from this plant.

    Topics: Datura metel; Phytochemicals; Scopoletin; Seeds; Sitosterols; Triterpenes

2015
[Triterpenoids from Leaves of Ilex latifolia].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:8

    To investigate the chemical constituents from the leaves of Ilex latifolia.. The constituents were iso- lated and purified by various chromatographic techniques. Their structures were identified by UV, IR, MS and NMR spectroscopic analy- sis.. Ten compounds were isolated from the leaves of flex latifolia. Their structures were respectively identified as 3β,13β-Di- hydroxy-urs-11-en-28-oic acid-13-lactone (1), β-sitosterol (2) 3-hydroxy-11-oxours-12-ene (3), (20S,24S)-epoxydammarane-3β,25- diol (4), 25-deuteriostigmasterol (5), α-amyrin (6), foliasalacin A4 (7), 23-hydroxyursolic acid (8), p-coumaric acid (9) and β-dau- costerol (10).. Compounds 1,3-5,7 and 9 are isolated from this plant for the first time.

    Topics: Coumaric Acids; Drugs, Chinese Herbal; Ilex; Magnetic Resonance Spectroscopy; Oleanolic Acid; Plant Leaves; Propionates; Sitosterols; Triterpenes

2015
[Chemical Constituents from Macaranga denticulata Root].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:8

    To study the chemical constituents from Macaranga denticulata Root.. The chemical constituents were isolated and purified by silica-gel column chromatography and recrystallization, and their structures were identified by physicochemical properties and spectral data.. Nine compounds were isolated and identified as: gheddic acid (1), aleuritolic acid-3-acetate (2), β-sitosterol (3), stigmast-4-en-6β-ol-3 -one (4), 2α-hydroxyaleuritolic acid 3-p-hydroxybenzoate (5), scopoletin (6), daucosterol (7), 2, 6-dimethoxy-1,4-benzoquinone (8) and maslinic acid(9).. Compounds 1-9 are obtained from this plant for the first time.

    Topics: Benzoquinones; Euphorbiaceae; Parabens; Phytochemicals; Plant Roots; Plants, Medicinal; Scopoletin; Sitosterols; Stigmasterol; Triterpenes

2015
[Chemical Constituents in Petroleum Ether Extract of Mongolian Medicine Halenia corniculata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2015, Volume: 38, Issue:11

    To study the chemical constituents of Mongolian medicine Halenia corniculata.. Positive phase and reversed phase silica gel, as well as Sephadex LH-20 methods were used to separate and purify. The structure of the isolated constituents was identified according to the NMR spectroscopy data and the literature data.. Nine compounds were isolated from 95% ethanol extracts of petroleum ether part of Halenia corniculata and identified as: 1-hydroxy-2,3,4,6-tetramethoxyxanthone (1), 1-hydroxy-2,3, 5-trimethoxyxanthone (2) 1-hydroxy-3,7-dimethoxyxanthone (3), 1-hydroxy-3,5,6,7,8-pentamethoxyxanthone (4), 1-hydroxy-2,3,4, 7-tetramethoxyxanthone (5), 1-hydroxy-3,5-dimethoxyxanthone (6),1-hydroxy-2,3,4,5,7-pentamethoxyxanthone (7), palmitic acid (8) and β-sitosterol (9).. Compounds 3, 4 and 8 are isolated from this genus for the first time, Compound 1 is isolated from this plant for the first time.

    Topics: Alkanes; Gentianaceae; Medicine, Mongolian Traditional; Phytochemicals; Plant Extracts; Sitosterols; Solvents; Xanthones

2015
β-Sitosterol and flavonoids isolated from Bauhinia malabarica found during screening for Wnt signaling inhibitory activity.
    Journal of natural medicines, 2014, Volume: 68, Issue:1

    Screening with a cell-based luciferase assay was conducted to identify bioactive natural products which inhibit Wnt signaling activity-guided separation of an MeOH extract of Bauhinia malabarica (Caesalpiniaceae) leaves yielded five compounds, which were identified as β-sitosterol (1), quercetin (2), 6,8-C-dimethyl kaempferol-3-O-rhamnopyranoside (3), hyperin (4), and 6,8-C-dimethyl kaempferol-3-methyl ether (5). The tested compounds 1, 3, and 5 exhibited Wnt signaling inhibitory activity, with IC50 values of 0.77, 0.74, and 16.6 μM, respectively.

    Topics: Bauhinia; Cell Survival; Dose-Response Relationship, Drug; Flavonoids; Genes, Reporter; HCT116 Cells; HEK293 Cells; Humans; Inhibitory Concentration 50; Kaempferols; Luciferases; Methanol; Phytotherapy; Plant Extracts; Plant Leaves; Plants, Medicinal; Quercetin; Sitosterols; Solvents; Transfection; Wnt Signaling Pathway

2014
Reactive oxygen species-mediated activation of AMP-activated protein kinase and c-Jun N-terminal kinase plays a critical role in beta-sitosterol-induced apoptosis in multiple myeloma U266 cells.
    Phytotherapy research : PTR, 2014, Volume: 28, Issue:3

    Although beta-sitosterol has been well known to have anti-tumor activity in liver, lung, colon, stomach, breast and prostate cancers via cell cycle arrest and apoptosis induction, the underlying mechanism of anti-cancer effect of beta-sitosterol in multiple myeloma cells was never elucidated until now. Thus, in the present study, the role of reactive oxygen species (ROS) in association with AMP-activated protein kinase (AMPK) and c-Jun N-terminal kinase (JNK) pathways was demonstrated in beta-sitosterol-treated multiple myeloma U266 cells. Beta-sitosterol exerted cytotoxicity, increased sub-G1 apoptotic population and activated caspase-9 and -3, cleaved poly (ADP-ribose) polymerase (PARP) followed by decrease in mitochondrial potential in U266 cells. Beta-sitosterol promoted ROS production, activated AMPK, acetyl-CoA carboxylase (ACC) and JNK in U266 cells. Also, beta-sitosterol attenuated the phosphorylation of AKT, mammalian target of rapamycin and S6K, and the expression of cyclooxygenase-2 and VEGF in U266 cells. Conversely, AMPK inhibitor compound C and JNK inhibitor SP600125 suppressed apoptosis induced by beta-sitosterol in U266 cells. Furthermore, ROS scavenger N-acetyl L-cysteine attenuated beta-sitosterol-mediated sub-G1 accumulation, PARP cleavage, JNK and AMPK activation in U266 cells. Overall, these findings for the first time suggest that ROS-mediated activation of cancer metabolism-related genes such as AMPK and JNK plays an important role in beta-sitosterol-induced apoptosis in U266 multiple myeloma cells.

    Topics: Acetyl-CoA Carboxylase; Acetylcysteine; AMP-Activated Protein Kinases; Anthracenes; Apoptosis; Caspase 3; Caspase 9; Cell Cycle Checkpoints; Cell Line, Tumor; Cyclooxygenase 2; Humans; JNK Mitogen-Activated Protein Kinases; MAP Kinase Signaling System; Membrane Potential, Mitochondrial; Multiple Myeloma; Phosphorylation; Poly(ADP-ribose) Polymerases; Reactive Oxygen Species; Sitosterols

2014
Isolation, characterisation and antibacterial activity of new compounds from methanolic extract of seeds of Caesalpinia crista L. (Caesalpinaceae).
    Natural product research, 2014, Volume: 28, Issue:4

    Phytochemical study on the methanolic extract of Caesalpinia crista afforded two novel compounds, 2-hydroxytrideca-3,6-dienyl-pentanoate and octacosa-12,15-diene along with known compounds 3-O-methylellagic acid 3'O-α-rhamnopyranoside, β-sitosterol and sucrose. Compound 3-O-methylellagic acid 3'O-α-rhamnopyranoside is reported for the first time from the plant. Molecular structures, of isolated compounds, were elucidated by using the NMR spectroscopy in combination with IR and mass spectral data. All isolated compounds, extract and fractions were evaluated for in vitro antibacterial activity against various Gram-positive and Gram-negative bacterial strains and found to be significantly active against Staphylococcus aureus and methicillin-resistant S. aureus (minimum inhibitory concentration: 64-512 μg mL(- 1)).

    Topics: Anti-Bacterial Agents; Caesalpinia; Decanoates; Fatty Acids, Unsaturated; India; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Seeds; Sitosterols; Staphylococcus aureus; Valerates

2014
Evaluation of in silico, in vitro α-amylase inhibition potential and antidiabetic activity of Pterospermum acerifolium bark.
    Pharmaceutical biology, 2014, Volume: 52, Issue:2

    Pterospermum acerifolium (L.) Willd (Sterculiaceae) has been traditionally used in the treatment of diabetes mellitus but no scientific data has been published supporting the claimed ethnomedical use.. The present study was designed to estimate the in silico, in vitro α-amylase inhibition potential and anti-diabetic activity of Pterospermum acerifolium bark.. In silico studies were performed between human pancreatic α-amylase (HPA) and β-sitosterol by using autodock 4.2 software. In vitro α-amylase inhibition study was carried out with 50% ethanol extract of the bark (PABEE) and its various fractions. The active ethyl acetate fraction (PABEF) was sub-fractionated into three fractions (PABE1, PABE2 and PABE3). Two doses (15 and 30 mg/kg) based on acute toxicity studies, of the above fractions were subjected to antidiabetic screening in vivo by STZ-nicotinamide induced type II diabetic rats.. In silico studies showed the potent inhibition of β-sitosterol on human pancreatic amylase (HPA) with an estimated inhibition constant (Ki) of 269.35 nmol and two hydrogen bond interactions. PABEF showed marked α-amylase inhibition (69.94%) compared to other fractions. Diabetic rats treated with PABE3 (30 mg/kg) reduced the levels of fasting blood glucose, HbA1c, ALT, AST, ALP, triglycerides, total cholesterol, TBARS significantly (p < 0.01) and increased the levels of HDL-C, catalase, GSH, SOD significantly (p < 0.01) as compared to that of diabetic control animals. Histological studies on PABE3 treated group showed remarkable positive changes in β-cells.. The present study confirmed the antihyperglycemic activity along with its status on hepatic biomarkers, antihyperlipidemic and antioxidant properties of Pterospermum acerifolium bark.

    Topics: Animals; Computer Simulation; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 2; Dose-Response Relationship, Drug; Humans; Hydrogen Bonding; Hypoglycemic Agents; Male; Malvaceae; Niacinamide; Pancreatic alpha-Amylases; Plant Bark; Plant Extracts; Rats; Rats, Wistar; Sitosterols; Software; Streptozocin; Toxicity Tests, Acute

2014
Growth inhibition and antioxidative response of wood decay fungi exposed to plant extracts of Casearia species.
    Letters in applied microbiology, 2014, Volume: 58, Issue:1

    Ligninolytic fungi take part in critical processes in ecosystems such as nutrient recycling; however, some fungal species can be pathogenic to forest and urban trees and deteriorate wood products. The tropical flora is an important source of antimicrobial compounds environmentally safer than traditional wood preservatives. Therefore, this study aimed to evaluate the inhibitory activity of ethanol plant extracts of Casearia sylvestris and Casearia decandra on the white-rot wood decay basidiomycetes Trametes villosa and Pycnoporus sanguineus. In addition, the effect of the extracts on the fungal antioxidative metabolism was studied. Among the different substances present in the extracts, the phytochemical analyses identified a clerodane diterpenoid (C. sylvestris) and cinnamic acid, hydroquinone and β-sitosterol (C. decandra). The extracts inhibited the fungi up to 70% and caused hyphal morphology changes. The extracts triggered oxidative stress process as indicated by the increased levels of the antioxidant enzymes catalase and glutathione reductase. Therefore, the Casearia extracts are a potential source of natural biocides to control wood decay fungi, and one of the mechanisms of action is the oxidative stress.. The Casearia plant extracts exhibited important antifungal activity on wood decay fungi and triggered oxidative stress process, an inhibitory mechanism rarely studied in filamentous fungi exposed to plant extracts. Therefore, a starting point was provided for the development of natural compounds-based products as an alternative to chemical fungicides. In addition, subsidies were given to further studies in order to elucidate in more detail how compounds present in extracts of native tropical plants affect the physiology of fungi.

    Topics: Antifungal Agents; Biomass; Casearia; Catalase; Ecosystem; Fungicides, Industrial; Glutathione Reductase; Hydroquinones; Oxidative Stress; Plant Extracts; Pycnoporus; Sitosterols; Trametes; Trees; Wood

2014
Fathead minnow response to broad-range exposure of β-sitosterol concentrations during life-cycle testing.
    Environmental toxicology and chemistry, 2014, Volume: 33, Issue:2

    The β-sitosterol concentration in pulp and paper mill effluents is typically greater than that of other phytosterols and has been shown to cause a variety of effects in fish. The authors exposed fathead minnow (Pimephales promelas) to low (22 ± 0.93 µg/L), medium-low (70 ± 2.1 µg/L), medium-high (237 ± 5.5 µg/L), and high (745 ± 16.2 µg/L) concentrations of β-sitosterol as well as negative (water), positive (ethynyl estradiol, 16 ± 0.58 ng/L), and carrier (0.6 mL/L acetone) controls. Fish were monitored over a full life cycle for population-level endpoints including growth and survival, reproductive endpoints (e.g. fecundity, sex steroids and vitellogenin, gonado-/hepatosomatic indices, and gonad histology). No significant differences were seen in fish growth, mortality, or reproduction with β-sitosterol exposure, although a trend for lower egg production in β-sitosterol exposures relative to the water control may be related to the acetone carrier. All ethynyl estradiol-exposed fish were smaller, showed female characteristics, and did not spawn. Sex steroid and vitellogenin were highly variable with no detectable treatment-related differences. Gonadal tissue showed no β-sitosterol-related differences in reproductive development and spawning capability, although most ethynyl estradiol-exposed males had ovarian tissue and were not spawning-capable. The results indicate that β-sitosterol exposure had little apparent impact on fathead minnow survival, growth, and reproduction even at concentrations >10 times that of typical effluents, although small sample size and variability precluded fully evaluating treatment responses on sex steroids and vitellogenin.

    Topics: Animals; Cyprinidae; Female; Fertility; Gonads; Life Cycle Stages; Male; Reproduction; Sitosterols; Water Pollutants, Chemical

2014
Synthesis and cytotoxic activity of some 4,6-diaza-A,B-dihomo-steroid bilactams.
    Steroids, 2014, Volume: 79

    Using cholesterol, stigmasterol and sitosterol as starting materials, some 4,6-diaza-A,B-dihomo-steroid bilactams were synthesized via two different synthetic routes by oxidation, reduction, oximation, Beckman rearrangement, etc. The cytotoxic activity of the synthesized compounds against SGC 7901 (human ventriculi carcinoma), Bel-7404 (human liver carcinoma), HeLa (human cervical carcinoma) and HT-29 (colonic carcinoma) cancer cells were investigated. The results showed that compounds 2 and 7b displayed a good cytotoxic activity to the SGC 7901, Bel 7404 and HeLa tumor cell lines with the IC50 values of 11.6, 16.4, 13.9 and 13.1, 21.8, 13.1 μmol/L, respectively. Their cytotoxic activity is almost same as cisplatin to these cells. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.

    Topics: Antineoplastic Agents; Azasteroids; Cell Line, Tumor; Cell Survival; Cholesterol; Drug Screening Assays, Antitumor; HeLa Cells; Homosteroids; HT29 Cells; Humans; Inhibitory Concentration 50; Lactams; Models, Chemical; Molecular Structure; Neoplasms; Sitosterols; Steroids; Stigmasterol

2014
Impaired hepatic and intestinal ATP-binding cassette transporter G5/8 was associated with high exposure of β-sitosterol and the potential risks to blood-brain barrier integrity in diabetic rats.
    The Journal of pharmacy and pharmacology, 2014, Volume: 66, Issue:3

    Plant sterols are thought to treat hypercholesterolemia via inhibiting intestinal cholesterol absorption. The aim of this study was to evaluate the contribution of impaired ATP-binding cassette transporter G5/8 (ABCG5/8) expression by diabetes to the increased β-sitosterol (BS) exposure and impact of increased BS on integrity of blood-brain barrier (BBB).. Basal BS level in tissues of streptozotocin-inducted rats and ABCG5/8 protein levels in liver and intestine were investigated; pharmacokinetics of BS was studied following oral dose; and primarily cultured rat brain microvessel endothelial cells (rBMECs) were used to study BS transportation across BBB and effect of BS on BBB integrity.. Diabetic rats showed greatly upgraded basal levels of BS in plasma, intestine, cerebral and hippocampus, accompanied by impairment of ABCG5/8 protein expression in liver and intestine. Pharmacokinetics studies demonstrated higher AUC0-48 and Cmax , and lower faecal recoveries of BS after oral administration, indicating enhancement of absorption or efflux impairment. In-vitro data showed increased ratio of BS/cholesterol in high levels BS-treated rBMECs was associated with increased BBB permeability of some biomarkers including BS itself.. Impaired ABCG5/8 protein expression by diabetes led to increase in BS exposure, which may be harmful to BBB function.

    Topics: Administration, Oral; Animals; ATP-Binding Cassette Transporters; Biological Transport; Blood-Brain Barrier; Brain; Capillary Permeability; Cholesterol; Diabetes Mellitus, Experimental; Feces; Intestinal Mucosa; Liver; Male; Rats; Rats, Sprague-Dawley; Sitosterols

2014
β-Sitosterol enhances cellular glutathione redox cycling by reactive oxygen species generated from mitochondrial respiration: protection against oxidant injury in H9c2 cells and rat hearts.
    Phytotherapy research : PTR, 2014, Volume: 28, Issue:7

    Herba Cistanches (Cistanche deserticola Y. C. Ma) is a 'Yang-invigorating' tonic herb in Chinese medicine. Preliminary chemical analysis indicated that β-sitosterol (BS) is one of the chemical constituents in an active fraction of Herba Cistanches. To investigate whether BS is an active ingredient of Herba Cistanches, the effects of BS on H9c2 cells and rat hearts were examined. The results indicated that BS stimulated the mitochondrial ATP generation capacity in H9c2 cells, which was associated with the increased production of mitochondrial reactive oxygen species. BS also stimulated mitochondrial state 3 and state 4 respiration, with the resultant decrease in coupling efficiency. BS produced an up-regulation of cellular glutathione redox cycling and protected against hypoxia/reoxygenation-induced apoptosis in H9c2 cells. However, the protective effect of BS against myocardial ischemia/reperfusion injury was seen in female but not male rats ex vivo. The cardioprotection afforded by BS was likely mediated by an up-regulation of mitochondrial glutathione redox cycling in female rat hearts. In conclusion, the ensemble of results suggests that BS is an active ingredient of Herba Cistanches. The gender-dependent effect of BS on myocardial protection will further be investigated.

    Topics: Animals; Apoptosis; Cardiotonic Agents; Cell Line; Cell Respiration; Cistanche; Drugs, Chinese Herbal; Female; Glutathione; Heart; Male; Mitochondria, Heart; Myocardial Reperfusion Injury; Oxidants; Oxidation-Reduction; Rats; Rats, Sprague-Dawley; Reactive Oxygen Species; Sitosterols

2014
β-sitosteryl-3-O-β-glucopyranoside isolated from the bark of Sorbus commixta ameliorates pro-inflammatory mediators in RAW 264.7 macrophages.
    Immunopharmacology and immunotoxicology, 2014, Volume: 36, Issue:1

    The bark of Sorbus commixta has been used in Asian traditional medicine for treatment of cough, asthma, bronchial disorders, gastritis and dropsy. However, the anti-inflammatory effect of β-sitosteryl-3-O-β-glucopyranoside, a major compound of the bark of S. commixta, is poorly understood. In this study, we investigated the anti-inflammatory effect and the underlying molecular mechanisms of β-sitosteryl-3-O-β-glucopyranoside in lipopolysaccharide (LPS)-induced RAW 264.7 cells. Prostaglandin E₂ (PGE₂) and cytokines released from cells were measured using EIA assay kit. The expression of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2, Tumor necrosis factor-alpha (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6) was measured by real-time polymerase chain reaction (RT-PCR) and/or Western blot analysis. β-sitosteryl-3-O-β-glucopyranoside inhibited the production of nitric oxide (NO) and PGE₂ along with the expression of iNOS and COX-2 in LPS-stimulated RAW264.7 cells. In addition, β-sitosteryl-3-O-β-glucopyranoside reduced the release of pro-inflammatory cytokines, such as TNF-α, IL-1β and IL-6. Moreover, β-sitosteryl-3-O-β-glucopyranoside inhibited the NF-κB activation induced by LPS, which was associated with the abrogation of IκBα degradation and subsequent decreases in nuclear p65 levels. The result suggested that the β-sitosteryl-3-O-β-glucopyranoside inhibited NO and pro-inflammatory productions by down-regulating the gene expression of pro-inflammatory mediators via the negative regulation of the NF-кB pathway in LPS-stimulated RAW 264.7 cells.

    Topics: Animals; Cell Line; Cyclooxygenase 2; Cytokines; Inflammation Mediators; Lipopolysaccharides; Mice; Nitric Oxide; Plant Bark; Sitosterols; Sorbus

2014
Algal sterols are as effective as β-sitosterol in reducing plasma cholesterol concentration.
    Journal of agricultural and food chemistry, 2014, Jan-22, Volume: 62, Issue:3

    The present study examined the cholesterol-lowering activity of sterol extract (SE) derived from alga Schizochytrium sp. and its interaction with gene expression of transporters, receptors, and enzymes involved in cholesterol absorption and metabolism. GC-MS analyses found that SE was a mixture of various sterols including lathosterol, ergosterol, stigmasterol, 24-ethylcholesta-5,7,22-trienol, stigmasta-7,24(24(1))-dien-3β-ol, and cholesterol. Results showed that SE at doses of 0.06 and 0.30 g/kg diet were able to decrease plasma cholesterol concentration by 19.5 and 34%, respectively, compared with the control, in hamsters maintained on a 0.1% high-cholesterol diet. SE at a dose of 0.30 g/kg diet was as effective as β-sitosterol in reducing plasma total cholesterol (TC). SE-induced reduction in plasma TC was accompanied by down-regulation of intestinal acyl-CoA:cholesterol acyltransferase 2 (ACAT2) and hepatic 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase and up-regulation of hepatic low-density lipoprotein (LDL) receptor. Addition of SE to the diet increased the excretion of total fecal sterols. It was concluded that SE possessed the same cholesterol-lowering activity as β-sitosterol and the underlying mechanisms were mediated by increasing sterol excretion and decreasing cholesterol absorption and synthesis.

    Topics: Animals; Anticholesteremic Agents; Cholesterol; Cricetinae; Down-Regulation; Functional Food; Male; Mesocricetus; Microalgae; Sitosterols

2014
Biological variation of β-sitosterol, campesterol, and lathosterol as cholesterol absorption and synthesis biomarkers.
    Clinica chimica acta; international journal of clinical chemistry, 2014, Mar-20, Volume: 430

    The analysis of blood for β-sitosterol and campesterol is the measures of cholesterol absorption while lathosterol is a measure of cholesterol synthesis.. The biological variability of β-sitosterol, campesterol, and lathosterol was measured using liquid-chromatography tandem mass spectrometry from a cohort of 25 apparently healthy subjects, where blood was taken once every weeks for 6 weeks. The analytical, intra-individual, and group inter-individual variations (CVA, CV(I), and CV(G), respectively) were calculated.. Using absolute values, the CVI for β-sitosterol, campesterol, and lathosterol was 11.8%, 11.8%, and 22.5%, respectively, and the CV(G) was 28.5%, 28.8%, and 52.0%, respectively. This produced reference change values of about 24-36% for declining values and 32-47% for increasing values. The index of individuality was between 0.41 and 0.58, indicating that population based reference values are of little use for these biomarkers. The number of points needed for a homeostatic setpoint was 5 samples for β-sitosterol and campesterol, and 19 samples for lathosterol. Similar findings were observed for values when normalized to total cholesterol. These results were higher than the biological variation for total, low density and high density cholesterol obtained from the literature. Results were essentially identical when sterol values were corrected to their respective total cholesterol concentration.. The establishment of the biological variation for these biomarkers enables their use in the interpretation of results from clinical trials and lipid lowering treatment of patients at risk for cardiovascular disease in clinical practice.

    Topics: Absorption, Physicochemical; Biomarkers; Cholesterol; Humans; Phytosterols; Sitosterols

2014
β-Sitosterol attenuates high-fat diet-induced intestinal inflammation in mice by inhibiting the binding of lipopolysaccharide to toll-like receptor 4 in the NF-κB pathway.
    Molecular nutrition & food research, 2014, Volume: 58, Issue:5

    β-Sitosterol, a common phytosterol, has been shown to exhibit anti-inflammatory effects. Here, we investigated the effect of β-sitosterol on high-fat diet (HFD) induced colitis in mice and on LPS-stimulated mouse intestinal macrophages.. C57BL/6J mice were maintained on an LFD (10 kcal% fat), an HFD (60 kcal% fat), or an HFD with β-sitosterol (20 mg/kg) administration for 8 weeks. The increased levels of body weight and epididymal fat pad weight as well as the concentrations of circulating proinflammatory cytokines and LPS in HFD mice compared with LFD mice were decreased by oral administration of β-sitosterol. The HFD-induced colonic inflammation evidenced by the increased expression of proinflammatory cytokines and the activation of nuclear factor kappa B (NF-κB) in the colon was also inhibited by β-sitosterol. In LPS-stimulated intestinal macrophages, β-sitosterol inhibited the production of proinflammatory cytokines and inflammatory enzymes as well as NF-κB activation. In addition, β-sitosterol significantly prevented the binding of LPS to intestinal as well as peritoneal macrophages. Furthermore, β-sitosterol potently inhibited the interaction between LPS and toll-like receptor 4 in intestinal macrophages transfected with control siRNA or MyD88 siRNA.. These findings indicate that β-sitosterol ameliorates HFD-induced colitis by inhibiting the binding of LPS to toll-like receptor 4 in the NF-κB pathway.

    Topics: Animals; Colitis; Cytokines; Diet, High-Fat; Inflammation; Intestines; Lipopolysaccharides; Macrophages, Peritoneal; Male; Mice; Mice, Inbred C57BL; Mice, Inbred ICR; Myeloid Differentiation Factor 88; NF-kappa B; RNA, Small Interfering; Signal Transduction; Sitosterols; Toll-Like Receptor 4

2014
Reconstructing long-term trends in municipal sewage discharge into a small lake in northern Manitoba, Canada.
    Chemosphere, 2014, Volume: 103

    Ross Lake lies within the City of Flin Flon (Manitoba, Canada), a mining community originally formed by the Hudson Bay Mining and Smelting Company (now Hudbay Minerals Inc.) in 1927. At the time of this investigation, a continuous effluent stream from Hudbay Minerals (approximately 80 years) and a discontinuous and unknown amount of raw and minimally treated municipal sewage (>20 years, likely ending in 1951) was discharged into the north basin of the lake. Maximum concentrations of fecal sterols, such as coprostanol and terrestrial phytosterols, such as: β-sitosterol, campesterol, stigmastanol were measured in vertical sections of sediment cores, collected from Ross Lake, in the 15-16-cm section, which likely corresponds to the 1930s. Concentrations of coprostanol increased from <1 μg g(-1) in older sediments, to 252.3 μg g(-1) organic carbon at the peak. Observed changes in concentrations of sterols, in combination with radiometric dating and changes to sediment physicochemical characteristics, support the conclusion that sediments of a depth of less than 17.5-cm depth were deposited during the post-industrial era from approximately 1930 onwards. Ratios of coprostanol to cholesterol>1, peaking at 3.6 are consistent with anecdotal information that municipal sewage was discharged into Ross Lake during the early years of urbanization, prior to changes in treatment of sewage and discharge practices that began in 1951. Finally, historical concentrations of terrestrial phytosterols followed trends similar to those of coprostanol and cholesterol and may possibly be the result of an increase in the flux of terrestrial organic matter into Ross Lake as the result of regional deforestation due to logging and fire.

    Topics: Cholesterol; Environmental Monitoring; Feces; Geologic Sediments; History, 20th Century; History, 21st Century; Lakes; Manitoba; Phytosterols; Sewage; Sitosterols; Waste Disposal, Fluid; Water Pollutants; Water Purification

2014
Plant sterol feeding induces tumor formation and alters sterol metabolism in the intestine of Apc(Min) mice.
    Nutrition and cancer, 2014, Volume: 66, Issue:2

    Dietary plant sterols reduce the absorption of cholesterol and therefore increase intraluminal cholesterol concentration. We examined how plant sterol esters from functional foods affect intestinal tumorigenesis in tumor-prone adenomatous polyposis coli (Apc)(Min) mice. Feeding plant sterols at 0.8% increased the number of intestinal adenomas, and the effect was significant in female mice. The concentration of mucosal free sitosterol increased by eightfold in plant sterol males and by threefold in plant sterol females when compared with respective controls. The concentration of mucosal free cholesterol was significantly lower in plant sterol males than in control males, and the decrease in free cholesterol was accompanied with a significant increase in nuclear sterol regulatory element binding protein-2. No difference was found in the levels of β-catenin, cyclin D1, epidermal growth factor receptor, extracellular signal-regulated kinase 1/2, or caveolin-1 in either gender after plant sterol feeding. Among all measured parameters, higher levels of estrogen receptor β and free cholesterol in the mucosa were among the strongest predictors of increased intestinal tumorigenesis. In addition, gene expression data showed significant enrichment of up-regulated genes of cell cycle control and cholesterol biosynthesis in plant sterol females. The results indicate that high intake of plant sterols accelerates intestinal tumorigenesis in female Apc (Min)mice; however, the mechanism behind the adverse effect remains to be discovered.

    Topics: Adenomatous Polyposis Coli; Animals; beta Catenin; Caveolin 1; Cholesterol; Cyclin D1; Diet; ErbB Receptors; Female; Intestinal Absorption; Intestinal Mucosa; Intestines; Lipid Metabolism; Male; Mice; Mice, Inbred C57BL; Mitogen-Activated Protein Kinase 3; Phytosterols; Sitosterols; Sterol Regulatory Element Binding Protein 2

2014
Hemp ( Cannabis sativa L.) seed oil: analytical and phytochemical characterization of the unsaponifiable fraction.
    Journal of agricultural and food chemistry, 2014, Feb-05, Volume: 62, Issue:5

    Non-drug varieties of Cannabis sativa L., collectively namely as "hemp", have been an interesting source of food, fiber, and medicine for thousands of years. The ever-increasing demand for vegetables oils has made it essential to characterize additional vegetable oil through innovative uses of its components. The lipid profile showed that linoleic (55%), α-linolenic (16%), and oleic (11%) were the most abundant fatty acids. A yield (1.84-1.92%) of unsaponifiable matter was obtained, and the most interesting compounds were β-sitosterol (1905.00 ± 59.27 mg/kg of oil), campesterol (505.69 ± 32.04 mg/kg of oil), phytol (167.59 ± 1.81 mg/kg of oil), cycloartenol (90.55 ± 3.44 mg/kg of oil), and γ-tocopherol (73.38 ± 2.86 mg/100 g of oil). This study is an interesting contribution for C. sativa L. consideration as a source of bioactive compounds contributing to novel research applications for hemp seed oil in the pharmaceutical, cosmetic food, and other non-food industries.

    Topics: Cannabis; Phytosterols; Plant Oils; Seeds; Sitosterols; Tocopherols; Triterpenes

2014
Retama monosperma n-hexane extract induces cell cycle arrest and extrinsic pathway-dependent apoptosis in Jurkat cells.
    BMC complementary and alternative medicine, 2014, Jan-24, Volume: 14

    Retama monosperma L. (Boiss.) or Genista monosperma L. (Lam.), locally named as "R'tam", is an annual and spontaneous plant belonging to the Fabaceae family. In Morocco, Retama genus is located in desert regions and across the Middle Atlas and it has been widely used in traditional medicine in many countries. In this study, we show that Retama monosperma hexane extract presents significant anti-leukemic effects against human Jurkat cells.. Human Jurkat cells, together with other cell lines were screened with different concentrations of Retama monosperma hexane extract at different time intervals. Growth inhibition was determined using luminescent-based viability assays. Cell cycle arrest and apoptosis were measured by flow cytometry analysis. Combined caspase 3 and 7 activities were measured using luminometric caspase assays and immunoblots were performed to analyze expression of relevant pro- and anti-apoptotic proteins. GC-MS were used to determine the chemical constituents of the active extract.. Retama monosperma hexane extract (Rm-HE) showed significant cytotoxicity against Jurkat cells, whereas it proved to be essentially ineffective against both normal mouse fibroblasts (NIH3T3) and normal lymphocytes (TK-6). Cytometric analysis indicated that Rm-HE promoted cell cycle arrest and apoptosis induction accompanied by DNA damage induction indicated by an increase in p-H2A.X levels. Rm-HE induced apoptosis was partially JNK-dependent and characterized by an increase in Fas-L levels together with activation of caspases 8, 3, 7 and 9, whereas neither the pro-apoptotic nor anti-apoptotic mitochondrial membrane proteins analyzed were significantly altered. Chemical identification analysis indicated that α-linolenic acid, campesterol, stigmasterol and sitosterol were the major bioactive components within the extract.. Our data suggest that bioactive compounds present in Rm-HE show significant anti leukemic activity inducing cell cycle arrest and cell death that operates, at least partially, through the extrinsic apoptosis pathway.

    Topics: alpha-Linolenic Acid; Animals; Antineoplastic Agents, Phytogenic; Apoptosis; Apoptosis Regulatory Proteins; Caspase 3; Caspases; Cell Cycle Checkpoints; Cell Death; Cell Proliferation; Cholesterol; Fabaceae; Fas Ligand Protein; Humans; Jurkat Cells; Leukemia, T-Cell; MAP Kinase Kinase 4; Mice; NIH 3T3 Cells; Phytosterols; Phytotherapy; Plant Extracts; Signal Transduction; Sitosterols; Stigmasterol

2014
The β-sitosterol attenuates atopic dermatitis-like skin lesions through down-regulation of TSLP.
    Experimental biology and medicine (Maywood, N.J.), 2014, Volume: 239, Issue:4

    The compound β-sitosterol (BS) is one of the most common forms of phytosterols and has anti-cancer, anti-oxidant, anti-bacterial, and anti-inflammatory effects. However, the effect of BS on atopic dermatitis (AD) has not been elucidated. Therefore, we investigated whether BS would be an effective treatment against AD. We treated BS on 2,4-dinitrofluorobenzene (DNFB)-induced AD-like skin lesions in NC/Nga mice, anti-CD3/anti-CD28-stimulated splenocytes, and phorbol myristate acetate/calcium ionophore A23187-stimulated human mast cell line (HMC-1) cells. Histological analysis, ELISA, PCR, caspase-1 assay, and Western blot analysis were performed. BS reduced the total clinical severity in DNFB-treated NC/Nga mice. Infiltration of inflammatory cells and number of scratching were clearly reduced in the BS-treated group compared with the DNFB-treated group. BS significantly reduced the levels of inflammation-related mRNA and protein in the AD skin lesions. BS significantly reduced the levels of histamine, IgE, and interleukin-4 in the serum of DNFB-treated NC/Nga mice. The activation of mast cell-derived caspase-1 was decreased by treatment with BS in the AD skin lesions. BS also significantly decreased the production of tumor necrosis factor-α from the stimulated splenocytes. In the stimulated human mast cell line, HMC-1 cells, increased intracellular calcium levels were decreased by treatment with BS. Further, BS inhibited the production and mRNA expression of TSLP through blocking of caspase-1 and nuclear factor-κB signal pathways in the stimulated HMC-1 cells. These results provide additional evidence that BS may be considered an effective therapeutic drug for the treatment of AD.

    Topics: Animals; Caspase 1; Cell Line; Cytokines; Dermatitis, Atopic; Down-Regulation; Histamine; Humans; Immunoglobulin E; Interleukin-4; Mice; Mice, Inbred Strains; NF-kappa B; Receptor-Interacting Protein Serine-Threonine Kinase 2; Receptor-Interacting Protein Serine-Threonine Kinases; Sitosterols; Thymic Stromal Lymphopoietin

2014
Characterization of oilseed lipids from "DHA-producing Camelina sativa": a new transformed land plant containing long-chain omega-3 oils.
    Nutrients, 2014, Feb-21, Volume: 6, Issue:2

    New and sustainable sources of long-chain (LC, ≥C₂₀) omega-3 oils containing DHA (docosahexaenoic acid, 22:6ω3) are required to meet increasing demands. The lipid content of the oilseed of a novel transgenic, DHA-producing land plant, Camelina sativa, containing microalgal genes able to produce LC omega-3 oils, contained 36% lipid by weight with triacylglycerols (TAG) as the major lipid class in hexane extracts (96% of total lipid). Subsequent chloroform-methanol (CM) extraction recovered further lipid (~50% polar lipid, comprising glycolipids and phospholipids) and residual TAG. The main phospholipid species were phosphatidyl choline and phosphatidyl ethanolamine. The % DHA was: 6.8% (of total fatty acids) in the TAG-rich hexane extract and 4.2% in the polar lipid-rich CM extract. The relative level of ALA (α-linolenic acid, 18:3ω3) in DHA-camelina seed was higher than the control. Major sterols in both DHA- and control camelina seeds were: sitosterol, campesterol, cholesterol, brassicasterol and isofucosterol. C₁₆-C₂₂ fatty alcohols, including iso-branched and odd-chain alcohols were present, including high levels of iso-17:0, 17:0 and 19:0. Other alcohols present were: 16:0, iso-18:0, 18:0 and 18:1 and the proportions varied between the hexane and CM extracts. These iso-branched odd-chain fatty alcohols, to our knowledge, have not been previously reported. These components may be derived from wax esters, or free fatty alcohols.

    Topics: Brassicaceae; Cholestadienols; Cholesterol; Fatty Acids, Omega-3; Gas Chromatography-Mass Spectrometry; Phospholipids; Phytosterols; Plant Oils; Plants, Genetically Modified; Seeds; Sitosterols; Stigmasterol; Triglycerides

2014
Quercetin and beta-sitosterol prevent high fat diet induced dyslipidemia and hepatotoxicity in Swiss albino mice.
    Indian journal of experimental biology, 2014, Volume: 52, Issue:1

    High fat diet group showed a significant rise in serum and hepatic total cholesterol, triglyceride and atherogenic index which are major biomarkers of dyslipidemia and cardiovascular risk. The liver function markers, lipid peroxidation and proinflammatory cytokine levels were elevated in high fat diet group whereas antioxidant levels significantly reduced. These findings manifest hepatic damage which was further confirmed by histological findings. Quercetin and beta-sitosterol though structurally different yet both ameliorate the sickening changes in different mechanism. The current investigation is perhaps the first report of the mechanistic role of two polyphenols over dyslipidemia and subsequent hepatotoxicity.

    Topics: Animals; Antioxidants; Cardiovascular Diseases; Diet, High-Fat; Dyslipidemias; Lipid Peroxidation; Lipids; Liver; Mice; Quercetin; Sitosterols; Triglycerides

2014
The relationships of phytosterols and oxyphytosterols in plasma and aortic valve cusps in patients with severe aortic stenosis.
    Biochemical and biophysical research communications, 2014, Apr-11, Volume: 446, Issue:3

    Phytosterols such as campesterol and sitosterol are susceptible to oxidation by reactive oxygen species. We hypothesize that the plant sterols (PS) campesterol and sitosterol and their 7-oxygenated metabolites (POPs) correlate within and between human plasma and aortic valve cusps tissues. Plasma and tissue concentrations of PS and POPs were analyzed by gas chromatography-mass spectrometry-selected ion monitoring. Prior to analysis valve cusps tissue was mechanically separated from the calcified parts. PS and POP levels per dry cusps tissue weight were significantly higher compared with the concentrations in the calcified part. Against our hypothesis we found that despite the fact that there is a high correlation between plant sterols in and between plasma and valves cusps tissue, as well as a high correlation between plant sterols and oxyphytosterols and oxyphytosterols themselves within the valve cusps tissue, there was hardly any correlation in the amount of oxyphytosterols in plasma and between plasma and valves. Because plasma samples are easily accessible for large scale population based studies, we have to understand in more detail what the analysis of POPs implies in terms of CVD risk for the future.

    Topics: Adult; Aged; Aged, 80 and over; Aortic Valve; Aortic Valve Stenosis; Cholesterol; Female; Humans; Male; Middle Aged; Phytosterols; Sitosterols

2014
New ceramide from the aerial part of Tinospora oblongifolia with cytotoxic activities.
    Natural product research, 2014, Volume: 28, Issue:9

    A new ceramide, 2,3-dihydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyicosan-2-yl[tetracosanamide (1) along with four known compounds: 2-(4'-hydroxyphenyl)-ethyl lignocerate (2), docosyl-3,4-dihydroxy-trans-cinnamate (3), β-sitosterol (4) and β-sitosterol glycoside (5) were isolated from Tinospora oblongifolia (Menispermaceae). Their structures were determined on the basis of spectroscopic methods, mass spectrometry analysis as well as chemical transformation and by comparing their physical and spectral data with those reported in the literature. Compound 1 exhibited strong cytotoxic activity against KB cells with IC50 = 3.4 μM although less than that of camptothecin IC50 = 0.3 μM (positive control).

    Topics: Antineoplastic Agents, Phytogenic; Camptothecin; Ceramides; Drug Screening Assays, Antitumor; Humans; Inhibitory Concentration 50; KB Cells; Kenya; Molecular Structure; Plant Stems; Sitosterols; Tinospora

2014
Alkaline sphingomyelinase (NPP7) promotes cholesterol absorption by affecting sphingomyelin levels in the gut: A study with NPP7 knockout mice.
    American journal of physiology. Gastrointestinal and liver physiology, 2014, May-15, Volume: 306, Issue:10

    We previously showed that dietary sphingomyelin (SM) inhibited cholesterol absorption in animals. The key enzyme hydrolyzing SM in the gut is alkaline sphingomyelinase (alk-SMase, nucleotide pyrophosphatase/phosphodiesterase 7). Here using the fecal dual-isotope ratio method we compared cholesterol absorption in the wild-type (WT) and alk-SMase knockout (KO) mice. The animals were fed an emulsion containing [(14)C]cholesterol and [(3)H]sitosterol. The radioactivities in the lipids of the fecal samples collected 4, 8, and 24 h thereafter were determined, and the ratio of (14)C/(3)H was calculated. We found that the fecal [(14)C]cholesterol recovery in the KO mice was significantly higher than in the WT mice. A maximal 92% increase occurred 8 h after feeding. Recovery of [(3)H]sitosterol did not differ between the two groups. Accordingly, the (14)C-to-(3)H ratio of fecal lipids was 133% higher at 8 h and 75% higher at 24 h in the KO than in the WT mice. Decreased [(14)C]cholesterol was also found in the serum of the KO mice 4 h after feeding. Supplement of SM in the emulsion reduced the differences in fecal [(14)C]cholesterol recovery between the WT and KO mice because of a greater increase of [(14)C]cholesterol recovery in the WT mice. Without treatment, the KO mice had significantly higher SM levels in the intestinal content and feces, but not in the intestinal mucosa or serum. The expression of Niemann-Pick C1 like 1 protein in the small intestine was not changed. In conclusion, alk-SMase is a physiological factor promoting cholesterol absorption by reducing SM levels in the intestinal lumen.

    Topics: Animals; Cholesterol; Feces; Female; Intestinal Absorption; Intestine, Small; Male; Membrane Transport Proteins; Mice; Mice, Knockout; Sitosterols; Sphingomyelin Phosphodiesterase; Sphingomyelins

2014
Age-associated alterations in cholesterol homeostasis: evidence from a cross-sectional study in a Northern Italy population.
    Clinical interventions in aging, 2014, Volume: 9

    The modifications of cholesterol metabolism associated with aging are ill-defined. The objective of this study was to define age-associated alterations of the different metabolic pathways controlling cholesterol homeostasis by analyzing circulating sterols.. We analyzed serum samples collected from 201 adult (75 male, 126 female) subjects within the epidemiological MICOL study (Multicentrica Italiana Colelitiasi). The age range was 38-79 years; 103 had evidence of gallstones. The concentrations of the different sterols, recognized as markers of the main pathways of cholesterol homeostasis, were analyzed by gas chromatography-mass spectrometry, including lathosterol (synthesis), campesterol and sitosterol (absorption), and 7α-hydroxy-4-cholesten-3-one (degradation to bile acids).. A significant direct correlation was detected between age and cholesterol levels (r =0.34, P<0.01). The lathosterol/cholesterol ratio was lower in older age quartiles (P<0.05 by analysis of variance), with an inverse correlation between the lathosterol/cholesterol ratio and age (r=-0.32, P<0.01). Such correlation was particularly evident in females. The campesterol/cholesterol and sitosterol/cholesterol ratios were inversely correlated with aging in control, but not in gallstone patients. The levels of 7α-hydroxy-4-cholesten-3-one were not correlated with age.. These data show a reduction of cholesterol synthesis with aging which is associated with increased circulating cholesterol levels. The finding might be related to a reduced metabolic need for cholesterol in advancing age, leading to a downregulation of the main mechanisms of cholesterol intake in the liver. A different age-related behavior was observed in gallstone-free versus gallstone patients regarding cholesterol absorption. The possible implications in terms of the pharmacological management of hypercholesterolemia in the elderly remain to be defined.

    Topics: Adult; Age Factors; Aged; Aging; Cholestenones; Cholesterol; Cross-Sectional Studies; Female; Gallstones; Gas Chromatography-Mass Spectrometry; Homeostasis; Humans; Italy; Male; Middle Aged; Phytosterols; Sitosterols

2014
Rapid purification of gram quantities of β-sitosterol from a commercial phytosterol mixture.
    BMC research notes, 2014, Mar-27, Volume: 7

    β-Sitosterol, a plant sterol or phytosterol, has commercial uses in the nutraceutical and pharmaceutical industries, but is also employed frequently in biological research. Phytosterols always accumulate as mixtures, and obtaining highly pure β-sitosterol in larger quantities for biological assays has been a challenge.. An improved method for the rapid purification of β-sitosterol from a commercial phytosterol extract is presented. Fractional crystallization of soybean oil yielded a soluble and an insoluble fraction. β-Sitosterol was purified by silica gel and Na-Y zeolite chromatography.. The rapid and cost effective three-step purification described here afforded β-sitosterol in gram quantities with high purity (>92%) and yield (>22%).

    Topics: Chromatography; Crystallization; Silica Gel; Sitosterols; Solubility; Soybean Oil; Zeolites

2014
New cytotoxic cycloartane triterpene from Cassia italica aerial parts.
    Natural product research, 2014, Volume: 28, Issue:13

    Phytochemical study of the aerial parts of Cassiaitalica Mill. (family: Fabaceae) growing in Saudi Arabia afforded one new cycloartane triterpene, named (22E)-3-β-hydroxycycloart-22-en-24-one (2), together with eight known compounds: β-sitosterol (1), uvaol (3), daucosterol (4), methyl 3,4-dihydroxybenzoate (5), emodin (6), 4-hydroxypheny-O-β-D-glucopyranoside (7), aloin (8) and rutin (9). The structure of the isolated compounds was determined by physical, chemical and spectral data (UV, IR, MS, 1D ((1)H, (13)C and DEPT) and 2D ((1)H-(1)H COSY, HSQC and HMBC) NMR), as well as by comparing with authentic samples. Compounds 3-5 and 7-9 were isolated for the first time from the plant. Compound 2 was evaluated for its cytotoxic activity against the L5178Y and PC12 cell lines. The total methanolic extract and compounds 5-9 exhibited free radical-scavenging activity using DPPH assay.

    Topics: Algorithms; Animals; Biphenyl Compounds; Cassia; Free Radical Scavengers; Humans; Hydroxybenzoates; Nuclear Magnetic Resonance, Biomolecular; PC12 Cells; Picrates; Rats; Saudi Arabia; Sitosterols; Triterpenes

2014
Chinese yam extracts containing β-sitosterol and ethyl linoleate protect against atherosclerosis in apolipoprotein E-deficient mice and inhibit muscular expression of VCAM-1 in vitro.
    Journal of food science, 2014, Volume: 79, Issue:4

    Atherosclerosis is a chronic inflammatory disease, which is associated with increased expression of adhesion molecules and monocyte recruitment into the arterial wall. This study evaluated whether hexane extracts from the edible part (DB-H1) or bark region (DB-H2) of Dioscorea. batatas Decne have anti-atherosclerotic properties in vivo and in vitro experiments. We also identified bioactive components in the hexane extracts. Thirty-six apolipoprotein E (ApoE(-/-) ) mice and 12 control (C57BL/6J) mice were given a Western-type diet for 11 or 21 wk. To examine the effects of yam extracts on lesion development, ApoE(-/-) mice were orally administered DB-H1 or DB-H2 for the duration of the study (200 mg/kg b.w./day, 3 times per wk). Both DB-H1 and DB-H2 significantly reduced the total atherosclerotic lesion area in the aortic root. In addition, plasma concentrations of total cholesterol, oxidized-low-density lipoprotein, and c-reactive protein were decreased by administration of DB-H1 and DB-H2. Consistent with the in vivo observations, DB-H1 and DB-H2 inhibited tumor necrosis factor (TNF)-α-induced vascular cell adhesion molecule-1 expression and adhesion of THP-1 monocytes to TNF-α-activated vascular smooth muscle cells. It was also found that treatment with DB-H1 or DB-H2 resulted in the inhibition nitric oxide (NO) and reactive oxygen species production and iNOS expression in macrophages. Thus, DB-H1 and DB-H2 seem to influence atherosclerosis by affecting the production of inflammatory mediators in vivo. Our results suggest that yam extracts have the potential to be used in the prevention of atherosclerosis.

    Topics: Animals; Aorta; Apolipoproteins E; Atherosclerosis; C-Reactive Protein; Cardiovascular Agents; Dioscorea; In Vitro Techniques; Inflammation Mediators; Linoleic Acids; Lipoproteins, LDL; Macrophages; Male; Mice; Mice, Inbred C57BL; Monocytes; Muscle, Smooth, Vascular; Phytotherapy; Plant Extracts; Reactive Oxygen Species; Sitosterols; Tumor Necrosis Factor-alpha; Vascular Cell Adhesion Molecule-1

2014
First chemical evaluation and toxicity of Casinga-cheirosa to Balb-c male mice.
    Molecules (Basel, Switzerland), 2014, Apr-02, Volume: 19, Issue:4

    Laetia suaveolens, known as "casinga-cheirosa", crude extract EB719 has previously shown cytotoxic activity against prostate cancer and squamous cell carcinoma. For the first time, seven molecules were isolated from its apolar-α-tocopherol (1) and sitosterol (2)-and polar-3-O-caffeoylquinic acid (3), 4-O-caffeoylquinic acid (4), 5-O-feruloylquinic acid (5), hyperoside (6), and isoquercitrin (7)-fractions. Acute toxicity was determined in a two-stage experiment: (1) a reduced number of Balb-c male mice received 5000 mg/kg of EB719 to allow evaluation of general activity and other 27 parameters, plus death, up to the establishment of non-lethal dose (NLD), as well as lethal dose 50% (LD50); (2) NLD was administered and diazepam introduced as reference drug. EB719 showed LD50=178.0 mg/kg, and NLD 156.3 mg/kg. In stage one EB719 did not influence general activity, but provoked impairment in grasp reflexes, tail squeeze and breathing; piloerection and cyanosis were increased. In stage two, alterations occurred in auricular reflex, piloerection and breathing after diazepam administration, but not in response to EB719. Intestinal hemorrhage caused by local bleeding was observed after necropsy, and may be the main cause of animals' death other than a systemic effect of the extract. Although the isolated compounds are biologically and pharmacologically active in both men and animal systems, it is premature to relate their occurrence in EB719 to the observed intestine hemorrhage in mice.

    Topics: alpha-Tocopherol; Animals; Body Weight; Diazepam; Gastrointestinal Hemorrhage; Humans; Lethal Dose 50; Male; Mice; Mice, Inbred BALB C; Organ Size; Piloerection; Plant Extracts; Quercetin; Quinic Acid; Respiration; Salicaceae; Sitosterols

2014
Phytoestrogens β -sitosterol and genistein have limited effects on reproductive endpoints in a female fish, Betta splendens.
    BioMed research international, 2014, Volume: 2014

    Phytoestrogens are produced by plants and may cause endocrine disruption in vertebrates. The present study hypothesizes that phytoestrogen exposure of female Siamese fighting fish (Betta splendens) may disrupt endogenous steroid levels, change agonistic behavior expression, and potentially also disrupt oocyte development. However, only the pharmacologic dose of β-sitosterol had a significant effect on opercular flaring behavior, while we did not find significant effects of β-sitosterol or genistein on steroids or gonads. These findings are in direct contrast with previous studies on the effects of phytoestrogens in female fish. Results of the current study support previous work showing that the effects of phytoestrogen exposure may be less acute in mature female B. splendens than in other fish.

    Topics: Animals; Female; Fishes; Genistein; Oocytes; Phytoestrogens; Reproduction; Sitosterols

2014
New fatty acids from the Red Sea sponge Mycale euplectellioides.
    Natural product research, 2014, Volume: 28, Issue:14

    Chemical investigation of the Red Sea sponge Mycale euplectellioides afforded two new compounds; hexacosa-(6Z,10Z)-dienoic acid methyl ester (1) and hexacosa-(6Z,10Z)-dienoic acid (2), along with two known compounds: icosa-(8Z,11Z)-dienoic acid methyl ester (3) and β-sitosterol (4). The structures were elucidated by the interpretation of their spectral data. The total methanol extract (TME) of the sponge exhibited potent antimicrobial activity against the different strains at a concentration of 100 mg/mL. All tested fractions did not exhibit any activity against Serratia marcescens and tested fungal strains. The TME and different fractions displayed anti-inflammatory and antipyretic activities at doses of 100 and 200 mg/kg compared with indomethacin (8 mg). The TME exhibited a remarkable hepato-protective effect in CCl4-induced liver damage compared with silymarin. Furthermore, compounds 1 and 2 displayed weak activity against A549 non-small cell lung cancer, the U373 glioblastoma and the PC-3 prostate cancer cell lines.

    Topics: Animals; Anti-Inflammatory Agents; Antineoplastic Agents; Aspergillus flavus; Candida albicans; Drug Screening Assays, Antitumor; Escherichia coli; Fatty Acids, Unsaturated; Fusarium; Geotrichum; Humans; Indian Ocean; Liver; Male; Marine Biology; Microbial Sensitivity Tests; Molecular Structure; Porifera; Pseudomonas aeruginosa; Serratia marcescens; Sitosterols; Trichophyton

2014
Metabolic profiling of the resurrection plant Haberlea rhodopensis during desiccation and recovery.
    Physiologia plantarum, 2014, Volume: 152, Issue:4

    Desiccation tolerance is among the most important parameters for crop improvement under changing environments. Resurrection plants are useful models for both theoretical and practical studies. We performed metabolite profiling via gas chromatography coupled with mass spectrometry (GC-MS) and high-performance liquid chromatography (HPLC) and analyzed the antioxidant capacity of the endemic resurrection plant Haberlea rhodopensis at desiccation and recovery. More than 100 compounds were evaluated. Stress response included changes in both primary and secondary metabolic pathways. The high amounts of the specific glycoside myconoside and some phenolic acids - e.g. syringic and dihydrocaffeic acid under normal conditions tend to show their importance for the priming of H. rhodopensis to withstand severe desiccation and oxidative stress. The accumulation of sucrose (resulting from starch breakdown), total phenols, β-aminoisobutyric acid, β-sitosterol and α-tocopherol increased up to several times at later stages of desiccation. Extracts of H. rhodopensis showed high antioxidant capacity at stress and normal conditions. Myconoside was with the highest antioxidant properties among tested phenolic compounds. Probably, the evolution of resurrection plants under various local environments has resulted in unique desiccation tolerance with specific metabolic background. In our case, it includes the accumulation of a relatively rare compound (myconoside) that contributes alone and together with other common metabolites. Further systems biology studies on the involvement of carbohydrates, phenolic acids and glycosides in the desiccation tolerance and antioxidant capacity of H. rhodopensis will definitely help in achieving the final goal - improving crop drought tolerance.

    Topics: alpha-Tocopherol; Aminoisobutyric Acids; Antioxidants; Craterostigma; Desiccation; Magnoliopsida; Metabolomics; Phenols; Plant Leaves; Sitosterols; Stress, Physiological; Water

2014
Biotransformation of phytosterols under aerobic conditions.
    Water research, 2014, Jul-01, Volume: 58

    Phytosterols are plant-derived sterols present in pulp and paper wastewater and have been implicated in the endocrine disruption of aquatic species. Bioassays were performed to assess the effect of an additional carbon source and/or solubilizing agent on the aerobic biotransformation of a mixture of three common phytosterols (β-sitosterol, stigmasterol and campesterol). The aerobic biotransformation of the phytosterol mixture by a mixed culture developed from a pulp and paper wastewater treatment system was examined under three separate conditions: with phytosterols as the sole added carbon source, with phytosterols and dextrin as an additional carbon source, and with phytosterols added with ethanol as an additional carbon source and solubilizing agent. Significant phytosterol removal was not observed in assays set up with phytosterol powder, either with or without an additional carbon source. In contrast, all three phytosterols were aerobically degraded when added as a dissolved solution in ethanol. Thus, under the experimental conditions of this study, the bioavailability of phytosterols was limited without the presence of a solubilizing agent. The total phytosterol removal rate was linear for the first six days before re-spiking, with a rate of 0.47 mg/L-d (R(2) = 0.998). After the second spiking, the total phytosterol removal rate was linear for seven days, with a rate of 0.32 mg/L-d (R(2) = 0.968). Following the 7th day, the phytosterol removal rate markedly accelerated, suggesting two different mechanisms are involved in phytosterol biotransformation, more likely related to the production of enzyme(s) involved in phytosterol degradation, induced under different cell growth conditions. β-sitosterol was preferentially degraded, as compared to stigmasterol and campesterol, although all three phytosterols fell below detection limits by the 24th day of incubation.

    Topics: Bacteria, Aerobic; Biodegradation, Environmental; Biotechnology; Biotransformation; Carbon; Cholesterol; Dextrins; Ethanol; Phytosterols; Sitosterols; Stigmasterol; Water Pollutants, Chemical

2014
Sterol partitioning by HMGR and DXR for routing intermediates toward withanolide biosynthesis.
    Physiologia plantarum, 2014, Volume: 152, Issue:4

    Withanolides biosynthesis in the plant Withania somnifera (L.) Dunal is hypothesized to be diverged from sterol pathway at the level of 24-methylene cholesterol. The conversion and translocation of intermediates for sterols and withanolides are yet to be characterized in this plant. To understand the influence of mevalonate (MVA) and 2-C-methyl-d-erythritol-4-phosphate (MEP) pathways on sterols and withanolides biosynthesis in planta, we overexpressed the WsHMGR2 and WsDXR2 in tobacco, analyzed the effect of transient suppression through RNAi, inhibited MVA and MEP pathways and fed the leaf tissue with different sterols. Overexpression of WsHMGR2 increased cycloartenol, sitosterol, stigmasterol and campesterol compared to WsDXR2 transgene lines. Increase in cholesterol was, however, marginally higher in WsDXR2 transgenic lines. This was further validated through transient suppression analysis, and pathway inhibition where cholesterol reduction was found higher due to WsDXR2 suppression and all other sterols were affected predominantly by WsHMGR2 suppression in leaf. The transcript abundance and enzyme analysis data also correlate with sterol accumulation. Cholesterol feeding did not increase the withanolide content compared to cycloartenol, sitosterol, stigmasterol and campesterol. Hence, a preferential translocation of carbon from MVA and MEP pathways was found differentiating the sterols types. Overall results suggested that MVA pathway was predominant in contributing intermediates for withanolides synthesis mainly through the campesterol/stigmasterol route in planta.

    Topics: Base Sequence; Biosynthetic Pathways; Carbon; Cholesterol; Erythritol; Gene Expression; Gene Expression Regulation, Plant; Mevalonic Acid; Molecular Sequence Data; Nicotiana; Phylogeny; Phytosterols; Plant Leaves; Plant Proteins; Plants, Genetically Modified; Sequence Analysis, DNA; Sitosterols; Sterols; Stigmasterol; Sugar Phosphates; Triterpenes; Withania; Withanolides

2014
Cholesterol metabolism and serum non-cholesterol sterols: summary of 13 plant stanol ester interventions.
    Lipids in health and disease, 2014, Apr-27, Volume: 13

    The efficacy and safety of plant stanols added to food products as serum cholesterol lowering agents have been demonstrated convincingly, but their effects on cholesterol metabolism and on serum non-cholesterol sterols is less evaluated. The aim of this study was to assess the validity of serum non-cholesterol sterols and squalene as bioindices of cholesterol synthesis and absorption, and to examine how the individual serum non-cholesterol sterols respond to consumption of plant stanols.. We collected all randomized, controlled plant stanol ester (STAEST) interventions in which serum cholestanol, plant sterols campesterol and sitosterol, and at least two serum cholesterol precursors had been analysed. According to these criteria, there was a total of 13 studies (total 868 subjects without lipid-lowering medication; plant stanol doses varied from 0.8 to 8.8 g/d added in esterified form; the duration of the studies varied from 4 to 52 weeks). Serum non-cholesterol sterols were assayed with gas-liquid chromatography, cholesterol synthesis with the sterol balance technique, and fractional cholesterol absorption with the dual continuous isotope feeding method.. The results demonstrated that during the control and the STAEST periods, the serum plant sterol/cholesterol- and the cholestanol/cholesterol-ratios reflected fractional cholesterol absorption, and the precursor sterol/cholesterol-ratios reflected cholesterol synthesis. Plant sterol levels were dose-dependently reduced by STAEST so that 2 g of plant stanols reduced serum campesterol/cholesterol-ratio on average by 32%. Serum cholestanol/cholesterol-ratio was reduced less frequently than those of the plant sterols by STAEST, and the cholesterol precursor sterol ratios did not change consistently in the individual studies emphasizing the importance of monitoring more than one surrogate serum marker.. Serum non-cholesterol sterols are valid markers of cholesterol absorption and synthesis even during cholesterol absorption inhibition with STAEST. Serum plant sterol concentrations decrease dose-dependently in response to plant stanols suggesting that the higher the plant stanol dose, the more cholesterol absorption is inhibited and the greater the reduction in LDL cholesterol level is that can be achieved.. Clinical Trials Register # NCT00698256 [Eur J Nutr 2010, 49:111-117].

    Topics: Adult; Aged; Cholestanol; Cholesterol; Female; Humans; Hypercholesterolemia; Hypolipidemic Agents; Male; Middle Aged; Phytosterols; Randomized Controlled Trials as Topic; Sitosterols; Sterols; Young Adult

2014
Odorasides A and B, new sphingolipid glucosides from Klienia odora.
    Journal of Asian natural products research, 2014, Volume: 16, Issue:7

    Two new sphingolipid glucosides, odoraside A (1) and odoraside B (2), have been isolated from chloroform-soluble fraction of the total methanolic extract of Klienia odora, together with five known compounds, β-sitosterol (3), oleanolic acid (4), betulone (5), 2,3-dihydroxy-12-oleanen-28-oic acid (6), and β-sitosterol 3-O-β-d-glucopyranoside (7). Their structures were assigned from (1)H and (13)C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC, and HMBC experiments.

    Topics: Asteraceae; Glucosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Saudi Arabia; Sitosterols; Sphingolipids

2014
Lecithin-linker formulations for self-emulsifying delivery of nutraceuticals.
    International journal of pharmaceutics, 2014, Aug-25, Volume: 471, Issue:1-2

    Lecithin-linker microemulsions are formulations produced with soybean lecithin in combination with a highly lipophilic (lipophilic linker) and highly hydrophilic (hydrophilic linkers) surfactant-like additives. In this work, lecithin-linker systems were formulated to produce self-emulsifying delivery systems for β-carotene and β-sitosterol. The concentration of the lipophilic linker, sorbitan monooleate, was adjusted to minimize the formation of liquid crystals. The concentration of hydrophilic linkers, decaglyceryl caprylate/caprate and PEG-6-caprylic/capric glycerides, was gradually increased (scanned) until single phase clear microemulsions were obtained. For these scans, the oil (ethyl caprate) to water ratio was set to 1. The single phase, clear microemulsions were diluted with fed-state simulated intestinal fluid (FeSSIF) and produced stable emulsions, with drop sizes close to 200 nm. Using pseudo-ternary phase diagrams to evaluate the process of dilution of microemulsion preconcentrates (mixtures of oil, lecithin and linkers with little or no water) with FeSSIF, it was determined that self-emulsifying systems are obtained when the early stages of the dilution produce single phase microemulsions. If liquid crystals or multiple phase systems are obtained during those early stages, then the emulsification yields unstable emulsions with large drop sizes. An in vitro permeability study conducted using a Flow-Thru Dialyzer revealed that stable emulsions with drop sizes of 150-300 nm produce large and irreversible permeation of β-carotene to sheep intestine. On the other hand, unstable emulsions produced without the linker combination separated in the dialyzer chamber.

    Topics: Animals; beta Carotene; Chemistry, Pharmaceutical; Dietary Supplements; Drug Carriers; Emulsions; Glycine max; Hydrophobic and Hydrophilic Interactions; In Vitro Techniques; Jejunum; Lecithins; Molecular Structure; Permeability; Phase Transition; Sheep; Sitosterols; Surface Tension; Surface-Active Agents

2014
Dragmacidoside: a new nucleoside from the Red Sea sponge Dragmacidon coccinea.
    Natural product research, 2014, Volume: 28, Issue:15

    Chemical investigation of the Red Sea sponge Dragmacidon coccinea led to the isolation of a new nucleoside, dragmacidoside (1), along with eight known compounds: adenosine (2), inosine (3), deoxycytidine (4), methyl-α-d-glucopyranoside (5), clionasterol (6), stigmasterol (7), campesterol (8) and brassicasterol (9). The compounds were isolated from chloroform and ethyl acetate fractions of the methanolic extract of the sponge, and their structures were established based on various spectroscopic data including MS, 1D and 2D NMR (COSY, HSQC and HMBC). Biological testing revealed that the chloroform fraction possesses significant anti-inflammatory activity in the carrageenan-induced hind paw oedema in rats.

    Topics: Animals; Anti-Inflammatory Agents; Carrageenan; Edema; Indian Ocean; Marine Biology; Molecular Structure; Nucleosides; Porifera; Rats; Sitosterols; Stigmasterol

2014
Two new lignans with antioxidative activities from Jatropha curcas.
    Natural product research, 2014, Volume: 28, Issue:22

    Activity-guided isolation of dried seeds of Jatropha curcas L. led to the isolation of two new lignans along with eight known compounds. These compounds were determined by spectroscopic analysis to be jatrophasin C (1), jatrophasin D (2), β-sitosterol (3), jatrophasin A (4), daucosterol (5), isoamericanol A (6), ( ± )-3,3'-bisdemethylpinoresinol (7), 7'-epi-sesamin-dicatechol (8), isoprincepin (9) and americanol A (10), of which 1 and 2 were new compounds. The antioxidative activities along with peroxisome proliferator-activated receptor gamma exciting activity of these compounds were also determined.

    Topics: Jatropha; Lignans; PPAR gamma; Seeds; Sitosterols

2014
Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance.
    Natural product research, 2014, Volume: 28, Issue:15

    Eleven compounds, including four flavonoids [(2R,3R)-2,3-dihydro-3,5-dihydroxy-7,4'-dimethoxyflavone (1), 5-hydroxy-7,8,4'-trimethoxy-flavone (2), amentoflavone (10) and apigenin (11)], two penylpropanoids [sinapaldehyde (3) and 3-methoxy-4-hydroxy-cinnamic aldehyde (4)], three phenolic acids [4-hydroxyl-3,5-dimethoxy-benzaldehyde (5), 4-hydroxyacetophen-one (6) and p-hydroxybenzaldehyde (7)], one furan derivative [5-hydroxymethyl furfural (8)] and one steroid saponin [β-sitosterol-3-O-β-d-glucoside (9)], were isolated and identified from Aletris spicata. Among them, compounds 1-7, 9 and 10 were reported from the genus Aletris for the first time. Furthermore, seven of them (1-6, 10) were obtained from the family Liliaceae for the first time. Chemotaxonomy of the isolated compounds is discussed briefly.

    Topics: Apigenin; Benzaldehydes; Flavones; Flavonoids; Furaldehyde; Glucosides; Liliaceae; Magnoliopsida; Phylogeny; Plants, Medicinal; Sitosterols

2014
A new naphthol from the twigs and leaves of Pterospermum yunnanense.
    Natural product research, 2014, Volume: 28, Issue:19

    A new naphthol, 7-hydroxy-6-methyl-1-naphthoic acid methyl ester (1), together with eight known compounds, 6-hydroxy-7-(hydroxymethyl)-1-isopropyl-4-methyl-naphthalene (2), α-hydroxyacetosyringone (3), hexadecyl ferulate (4), scoparone (5), (+)-syringaresinol (6), stigmast-1,5-dien-3β-ol (7), β-sitosterol (8) and daucosterol (9), were isolated from the twigs and leaves of Pterospermum yunnanense Hsue. Their structures were elucidated by using spectroscopic analysis. All the compounds were isolated for the first time from P. yunnanense Hsue. Compound 1 was assessed for its cytotoxicity against five human tumour lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that it has no activity.

    Topics: Carboxylic Acids; Humans; Malvaceae; Molecular Structure; Naphthalenes; Naphthols; Plant Extracts; Plant Leaves; Sitosterols; Triterpenes

2014
Rare biscoumarin derivatives and flavonoids from Hypericum riparium.
    Phytochemistry, 2014, Volume: 105

    Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae. Chemical investigation of the methanol extract of the stem bark of H. riparium led to the isolation of four natural products, 7,7'-dihydroxy-6,6'-biscoumarin (1), 7,7'-dihydroxy-8,8'-biscoumarin (2), 7-methoxy-6,7'-dicoumarinyl ether (3), 2'-hydroxy-5'-(7″-methoxycoumarin-6″-yl)-4'-methoxyphenylpropanoic acid (4), together with one known 7,7'-dimethoxy-6,6'-biscoumarin (5), two flavones, 2'-methoxyflavone (6) and 3'-methoxy flavone (7), and two steroids, stigmast-4-en-3-one (8) and ergosta-4,6,8,22-tetraen-3-one (9). In addition, tetradecanoic acid (10), n-pentadecanoic acid (11), hexadecanoic acid (12), cis-10-heptadecenoic acid (13), octadecanoic acid (14) campesterol (15), stigmasterol (16), β-sitosterol (17), stigmastanol (18), β-eudesmol (19), 1-hexadecanol (20), and 1-octadecanol (21) were identified by GC-MS analysis. Compound 4 consists of a phenylpropanoic acid derivative fused with a coumarin unit, while compounds 2 and 3 are rare members of C8-C8' and C7-O-C6 linked biscoumarins. Their structures were elucidated by UV, IR, extensive 1D- and 2D-NMR experiments and electrospray (ESI) high resolution mass spectrometry (MS) including detailed MS/MS studies. This is the first report on the isolation of biscoumarins from the genus Hypericum, although simple coumarin derivatives have been reported from this genus in the literature. The cytotoxic activities of compounds 2-5 were evaluated against the human prostate cancer cell line PC-3 and the colon cancer cell line HT-29. They do not exhibit any significant cytotoxic activity.

    Topics: Antineoplastic Agents, Phytogenic; Cameroon; Coumarins; Drug Screening Assays, Antitumor; Flavonoids; HT29 Cells; Humans; Hypericum; Male; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plants, Medicinal; Sesquiterpenes, Eudesmane; Sitosterols; Stigmasterol

2014
Molecular mechanism of the synergistic effects of vitrification solutions on the stability of phospholipid bilayers.
    Biophysical journal, 2014, Jun-17, Volume: 106, Issue:12

    The vitrification solutions used in the cryopreservation of biological samples aim to minimize the deleterious formation of ice by dehydrating cells and promoting the formation of the glassy state of water. They contain a mixture of different cryoprotective agents (CPAs) in water, typically polyhydroxylated alcohols and/or dimethyl sulfoxide (DMSO), which can damage cell membranes. Molecular dynamics simulations have been used to investigate the behavior of pure DPPC, pure DOPC, and mixed DOPC-β-sitosterol bilayers solvated in a vitrification solution containing glycerol, ethylene glycol, and DMSO at concentrations that approximate the widely used plant vitrification solution 2. As in the case of solutions containing a single CPA, the vitrification solution causes the bilayer to thin and become disordered, and pores form in the case of some bilayers. Importantly, the degree of thinning is, however, substantially reduced compared to solutions of DMSO containing the same total CPA concentration. The reduction in the damage done to the bilayers is a result of the ability of the polyhydroxylated species (especially glycerol) to form hydrogen bonds to the lipid and sterol molecules of the bilayer. A decrease in the amount of DMSO in the vitrification solution with a corresponding increase in the amount of glycerol or ethylene glycol diminishes further its damaging effect due to increased hydrogen bonding of the polyol species to the bilayer headgroups. These findings rationalize, to our knowledge for the first time, the synergistic effects of combining different CPAs, and form the basis for the optimization of vitrification solutions.

    Topics: Cryoprotective Agents; Hydrogen Bonding; Lipid Bilayers; Models, Molecular; Phosphatidylcholines; Phospholipids; Sitosterols; Solutions; Solvents; Vitrification

2014
Triterpenes as uncompetitive inhibitors of α-glucosidase from flowers of Punica granatum L.
    Natural product research, 2014, Volume: 28, Issue:23

    The α-glucosidase and maltase inhibitory effects of Punica granatum L. flowers (PGF) were investigated. The methanol extract (PGFMe), n-hexane extract (PGFH), chloroform extract (PGFC) and the remaining water fraction (PGFW) were assayed for their α-glucosidase and maltase inhibitory effects. PGFW showed potent α-glucosidase inhibition with IC₅₀ of 0.8 μg/mL followed by PGFMe (IC₅₀ of 4.0 μg/mL) then PGFC (IC₅₀ of 5.21 μg/mL) in comparison to acarbose (0.9 μM). Due to its selectivity towards α-glucosidase, PGFC was subjected to bioactivity-guided isolation of its main active constituents. Five known compounds (1-5) were identified as β-sitosterol (1), oleanolic acid (2), ursolic acid (3), p-coumaric acid (4) and apigenin (5). Ursolic and oleanolic acids showed potent α-glucosidase inhibition (IC₅₀ of 39.0 and 35.0 μM, respectively), while they did not show significant maltase inhibition. Kinetic study using the double Lineweaver-Burk plot revealed that ursolic acid uncompetitively inhibited α-glucosidase in comparison with acarbose as a competitive inhibitor.

    Topics: alpha-Glucosidases; Coumaric Acids; Dose-Response Relationship, Drug; Flowers; Glycoside Hydrolase Inhibitors; Hypoglycemic Agents; Lythraceae; Oleanolic Acid; Propionates; Sitosterols; Triterpenes; Ursolic Acid

2014
[Preparation of novel gypenosides long-circulating liposomes consisted by sphingomyelin and beta-sitosterol modified by PEG].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2014, Volume: 39, Issue:6

    To explore the feasibility of preparing novel gypenosides long-circulating liposomes with PEG grafted on beta-sitosterol (PEG-Sito).. Succinicanhydride was adopted to connect beta-sitosterol and PEG 2000. Sphingomyelin and PEG-Sito was used as material to prepare gypenosides long-circulating liposomes by using ethanol injection method. Encapsulation efficiency was determined by using protamine precipitation method. H-NMR was used to verify the synthesis of PEG-Sito, the novel gypenosides long-circulating liposomes were characterized by particle size, zeta potential and atomic force microscope.. The synthesis of PEG-Sito was verified by 1H-NMR. Encapsulation efficiency of long-circulating liposomes prepared by ethanol injection method was 74.3%, particle size was 288.1 nm, zeta potential was -20.25 mV, the morphology were round observed by AFM.. The novel gypenosides long-circulating liposomes prepared with PEG-Sito was feasible, it had a high encapsulation efficiency and good morphology.

    Topics: Drug Compounding; Feasibility Studies; Gynostemma; Liposomes; Plant Extracts; Polyethylene Glycols; Reproducibility of Results; Sitosterols; Sphingomyelins

2014
Determination of sterols using liquid chromatography with off-line surface-assisted laser desorption/ionization mass spectrometry.
    Journal of chromatography. A, 2014, Sep-05, Volume: 1358

    A new method, reversed phase liquid chromatography with off-line surface-assisted laser desorption/ionization mass spectrometry (RPLC-SALDI MS) for the determination of brassicasterol (BR), cholesterol (CH), stigmasterol (ST), campesterol (CA) and β-sitosterol (SI) in oil samples has been developed. The sample preparation consisted of alkaline saponification followed by extraction of the unsaponificable fraction with diethyl ether. The recovery of the sterols ranged from 91 to 95% with RSD less than 4%. Separation of the five major sterols on a C18 column using methanol-water gradient was achieved in about 10min. An on-line UV detector was employed for the initial sterol detection prior to effluent deposition using a laboratory-built spotter with 1:73 splitter. Off-line SALDI MS was then applied for mass determination/identification and quantification of the separated sterols. Ionization of the nonpolar analytes was achieved by silver ion cationization with silver nanoparticles used as the SALDI matrix providing limits of detection 12, 6 and 11fmol for CH, ST and SI, respectively. Because of the incorporated splitter, the effective limits of detection of the RPLC-SALDI MS analysis were 4, 3 and 4pmol (or 0.08, 0.06 and 0.08μg/mL) for CH, ST and SI, respectively. For quantification, 6-ketocholestanol (KE) was used as the internal standard. The method has been applied for the identification and quantification of sterols in olive, linseed and sunflower oil samples. The described off-line coupling of RPLC to SALDI MS represents an alternative to GC-MS for analysis of nonpolar compounds.

    Topics: Cholestadienols; Cholesterol; Chromatography, Reverse-Phase; Ketocholesterols; Linseed Oil; Olive Oil; Phytosterols; Plant Oils; Reference Standards; Silver; Sitosterols; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Stigmasterol; Sunflower Oil

2014
In vitro cancer cell growth inhibition and antioxidant activity of Bombax ceiba (Bombacaceae) flower extracts.
    Natural product communications, 2014, Volume: 9, Issue:5

    The flowers of Bombax ceiba were investigated for their chemical composition, antioxidant effects and antiproliferative activity against seven human cancer cell lines. The antiproliferative responses of diethyl ether (DE) and light petroleum (PE) extracts were evaluated by sulforhodamine B (SRB) assay against MCF-7, HeLa, COR-L23, C32, A375, ACHN, and LNCaP cells in comparison with a human normal cell line, 142BR. Moreover, extracts were characterized by GC-MS analysis and tested for their antioxidant properties by different in vitro systems, namely DPPH, Fe-chelating activity and beta-carotene bleaching test. Both PE and DE extracts showed the highest antiproliferative activity against human renal adenocarcinoma (ACHN) in a concentration-dependent manner. PE extract showed the highest radical scavenging activity against the DPPH radical, while DE extract was more active in the beta-carotene bleaching test. The presence of beta-sitosterol and some fatty acids may contribute to the bioactivity of B. ceiba flower extracts.

    Topics: Antineoplastic Agents, Phytogenic; Antioxidants; Bombax; Cell Line, Tumor; Cell Proliferation; Flowers; Humans; Plant Extracts; Sitosterols

2014
[Chemical constituents from twigs of Piper hancei].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:1

    To investigate the chemical constituents from the twigs of Piper hancei.. The chemical constituents were isolated and purified by means of chromatographic techniques including silica gel,Sephadex LH-20 and preparative RP-HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral analysis.. Eight compounds were isolated and identified as 4-allylpyrocatechol(I), piperlonguminine(II), d-sesamin(Ill), beta-sitosterol (IV), pellitorine(V), piperolactam A(VI) and piperolactam D(VII), respectively.. Compound I, III, VI and VII are isolated from Piper hancei for the first time.

    Topics: Chromatography, High Pressure Liquid; Dioxolanes; Drugs, Chinese Herbal; Indole Alkaloids; Piper; Plant Stems; Plants, Medicinal; Sitosterols

2014
[Chemical constituents of pattra medicine Euodia lepta].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:1

    To study the chemical constituents of Pattra Medicine Euodia lepta in Xishuangbanna of Yunnan Province.. The chemical constituents were isolated and purified by chromatographic techniques, and identified by NMR, MS and other spectral methods.. In 60% ethanol extract from the stems,and 95% ethanol extract from the leaves, six compounds and two compounds were isolated and identified as pachypodol( 1) ,3-(3-methyl-but-2-enyl )umbelliferone(2),7-demethylsuberosin (3),beta-sitosterol (4),3,7-dimethoxy kaempferol(5), euolitrine(6), sesamin(7) and p-O-geranyl coumaric acid(8), respectively.. Compound 7 is obtained from Euodia genus for the first time,and compound 8 is obtained from domestic Euodia lepta for the first time.

    Topics: China; Coumaric Acids; Dioxoles; Evodia; Furocoumarins; Lignans; Plant Leaves; Plant Stems; Sitosterols

2014
Identification of a novel hypocholesterolemic protein, major royal jelly protein 1, derived from royal jelly.
    PloS one, 2014, Volume: 9, Issue:8

    Royal jelly (RJ) intake lowers serum cholesterol levels in animals and humans, but the active component in RJ that lowers serum cholesterol level and its molecular mechanism are unclear. In this study, we set out to identify the bile acid-binding protein contained in RJ, because dietary bile acid-binding proteins including soybean protein and its peptide are effective in ameliorating hypercholesterolemia. Using a cholic acid-conjugated column, we separated some bile acid-binding proteins from RJ and identified the major RJ protein 1 (MRJP1), MRJP2, and MRJP3 as novel bile acid-binding proteins from RJ, based on matrix-assisted laser desorption ionization time-of-flight mass spectrometry. Purified MRJP1, which is the most abundant protein of the bile acid-binding proteins in RJ, exhibited taurocholate-binding activity in vitro. The micellar solubility of cholesterol was significantly decreased in the presence of MRJP1 compared with casein in vitro. Liver bile acids levels were significantly increased, and cholesterol 7α-hydroxylase (CYP7A1) mRNA and protein tended to increase by MRJP1 feeding compared with the control. CYP7A1 mRNA and protein levels were significantly increased by MRJP1 tryptic hydrolysate treatment compared with that of casein tryptic hydrolysate in hepatocytes. MRJP1 hypocholesterolemic effect has been investigated in rats. The cholesterol-lowering action induced by MRJP1 occurs because MRJP1 interacts with bile acids induces a significant increase in fecal bile acids excretion and a tendency to increase in fecal cholesterol excretion and also enhances the hepatic cholesterol catabolism. We have identified, for the first time, a novel hypocholesterolemic protein, MRJP1, in RJ. Interestingly, MRJP1 exhibits greater hypocholesterolemic activity than the medicine β-sitosterol in rats.

    Topics: Animals; Blotting, Western; Caco-2 Cells; Caseins; Cholesterol; Chromatography, Gel; Electrophoresis, Polyacrylamide Gel; Fatty Acids; Glycoproteins; Hep G2 Cells; Humans; Insect Proteins; Liver; Rats; Sitosterols; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

2014
RP-HPLC characterization of lupenone and β-sitosterol in rhizoma musae and evaluation of the anti-diabetic activity of lupenone in diabetic Sprague-Dawley rats.
    Molecules (Basel, Switzerland), 2014, Sep-09, Volume: 19, Issue:9

    With the aim of characterizing the active ingredients lupenone and β-sitosterol in Rhizoma Musae samples a reversed-phase HPLC method for the separation of these two compounds in Rhizoma Musae samples was developed (regression coefficient>0.9996). The method was further applied to quantify lupenone and β-sitosterol content in Rhizoma Musae samples cultured in different growth environments. Different variables such as geographical location, growth stage, and harvest time, demonstrated differential effects on lupenone and β-sitosterol levels. Moreover, we determined the optimum conditions for cultivation and harvesting of Rhizoma Musae herbs. Lupenone administration caused a significant reduction in fasting blood glucose (FBG) levels in diabetic rats at doses of 1.78, 5.33, and 16.00 mg·kg⁻¹·day⁻¹ for 14 days, the glycated hemoglobin (HbA1c) levels of diabetic rats also significantly reduced at doses of 5.33, and 16.00 mg·kg⁻¹·day⁻¹, indicating a robust antidiabetic activity. To our knowledge, this is the first report of an optimized HPLC method successfully applied to quantify lupenone and β-sitosterol, and its applicability in optimizing Rhizoma Musae growth. Animal experiments also showed for the first time that lupenone from Rhizoma Musae has anti-diabetic activity.

    Topics: Animals; Chromatography, High Pressure Liquid; Chromatography, Reverse-Phase; Diabetes Mellitus, Experimental; Drug Evaluation, Preclinical; Hypoglycemic Agents; Limit of Detection; Male; Musa; Plant Extracts; Rats, Sprague-Dawley; Rhizome; Sitosterols; Triterpenes

2014
Effects of β-sitosterol derived from Artemisia capillaris on the activated human hepatic stellate cells and dimethylnitrosamine-induced mouse liver fibrosis.
    BMC complementary and alternative medicine, 2014, Sep-27, Volume: 14

    β-sitosterol is a cholesterol-like phytosterol, which widely distributed in the plant kingdom. Here, anti-fibrotic effect of the β-sitosterol was studied using the activated human hepatic stellate cell (HSC) model and dimethylnitrosamine (DMN)-induced mouse hepatic fibrosis model.. HSCs were activated by transforming growth factor-β (TGF-β) and the collagen-1 and α-smooth muscle actin (α-SMA) expressions were measured at the mRNA and protein level. We also studied the effect β-sitosterol using DMN-induced mouse hepatic fibrosis model. We then measured the collagen-1 and α-SMA expression levels in vivo to investigate anti-hepatofibrotic effect of β-sitosterol, at both of the mRNA and protein level.. β-sitosterol down regulated the mRNA and protein expression levels of collagen-1 and α-SMA in activated HSC. Oral administration of the β-sitosterol successfully alleviated the DMN-induced mouse liver damage and prevented collagen accumulation. The mRNA and protein expression levels of collagen-1 and α-SMA were also down regulated in β-sitosterol treated mouse group.. This study shows the effect of β-sitosterol on the TGF-β -or DMN-induced hepatofibrosis. Hence, we demonstrate the β-sitosterol as a potential therapeutic agent for the hepatofibrosis.

    Topics: Actins; Animals; Artemisia; Cell Line; Cell Survival; Collagen Type I; Dimethylnitrosamine; Gene Expression; Hepatic Stellate Cells; Humans; Liver Cirrhosis; Male; Mice; Mice, Inbred C57BL; Plant Extracts; Sitosterols

2014
Anti-inflammatory effect of 3-O-[(6'-O-palmitoyl)-β-D-glucopyranosyl sitosterol] from Agave angustifolia on ear edema in mice.
    Molecules (Basel, Switzerland), 2014, Sep-29, Volume: 19, Issue:10

    In Mexico Agave angustifolia has traditionally been used to treat inflammation. The aim of this study was to measure the anti-inflammatory effect of the extract of A. angustifolia, the isolation and identification of active compounds. From the acetone extract two active fractions were obtained, (AsF13 and AaF16). For the characterization of pharmacological activity, the acute inflammatory model of mouse ear edema induced with TPA was used. The tissue exposed to TPA and treatments were subjected to two analysis, cytokine quantification (IL-1β, IL-6, IL-10 and TNF-α) and histopathological evaluation. The active fraction (AaF16) consisted principally of 3-O-[(6'-O-palmitoyl)-β-D-glucopyranpsyl] sitosterol. In AaF13 fraction was identified β-sitosteryl glucoside (2) and stigmasterol (3). The three treatments tested showed a concentration-dependent anti-inflammatory effect (AaAc Emax = 33.10%, EC50 = 0.126 mg/ear; AaF13 Emax = 54.22%, EC50 = 0.0524 mg/ear; AaF16 Emax = 61.01%, EC50 = 0.050 mg/ear). The application of TPA caused a significant increase on level of IL-1β, IL-6 and TNFα compared with basal condition, which was countered by any of the experimental treatments. Moreover, the experimental treatments induced a significant increase in the levels of IL-4 and IL-10, compared to the level observed when stimulated with TPA. Therefore, the anti-inflammatory effect of Agave angustifolia, is associated with the presence of 3-O-[(6'-O-palmitoyl)-β-D-glucopyranosyl] sitosterol.

    Topics: Agave; Animals; Anti-Inflammatory Agents; Cytokines; Disease Models, Animal; Ear; Edema; Male; Mice; Plant Extracts; Sitosterols

2014
Bioassay-guided isolation of the antinociceptive compounds motiol and beta-sitosterol from Scorzonera latifolia root extract.
    Die Pharmazie, 2014, Volume: 69, Issue:9

    Scorzonera latifolia (Asteraceae) is a plant widely distributed in Central and East Anatolia. A mastic, named yaki sakizi, is prepared from the latex and roots of S. latifolia and similar species. This latex is used in Turkish folk medicine for its analgesic activity, as anthelmintic and against infertility. The aim of this study was to isolate the compounds responsible for the antinociceptive activity of S. latifolia using bioassay-guided fractionation. The methanolic extract of the S. latifolia roots was prepared and subjected to chromatographic purification. Isolated active compounds were identified by means of MS and NMR techniques. Writhing and tail-flick tests were used to determine antinociceptive activity. Motiol and beta-sitosterol were isolated as compounds with promising antinociceptive activity. It is suggested that antinociceptive activity of the plant extract is probably caused by the synergic interaction of the isolated compounds.

    Topics: Acetic Acid; Analgesics; Animals; Hexanes; Hot Temperature; Magnetic Resonance Spectroscopy; Male; Mice; Mice, Inbred BALB C; Pain Measurement; Plant Extracts; Plant Roots; Reaction Time; Scorzonera; Sitosterols; Solvents; Triterpenes

2014
Structure and antioxidant activity of phenolic compounds isolated from the edible fruits and stem bark of Harpephyllum caffrum.
    Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 2014, Volume: 49, Issue:12

    Antioxidant activity in edible fruits is an important characteristic in the choice of fruits for human consumption, and has profound influence on nutrition and health. Two pharmacologically active triterpenoids, β-sitosterol and lupeol, and the powerful flavan-3-ol antioxidant, (+)-catechin, were isolated from the edible fruits of Harpephyllum caffrum while a mixture of cardanols, an alkyl p-coumaric acid ester, and (+)-catechin were isolated from the stem bark. This is the first report of these compounds being isolated from this plant. The antioxidant capacity of (+)-catechin was higher than the other isolated compounds as well as the known antioxidant, ascorbic acid.

    Topics: Anacardiaceae; Antioxidants; Coumaric Acids; Flavonoids; Fruit; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Phenols; Plant Bark; Plants, Medicinal; Propionates; Sitosterols

2014
β-sitosterol protects against carbon tetrachloride hepatotoxicity but not gentamicin nephrotoxicity in rats via the induction of mitochondrial glutathione redox cycling.
    Molecules (Basel, Switzerland), 2014, Oct-30, Volume: 19, Issue:11

    Previous findings have demonstrated that β-sitosterol (BSS), an active component of Cistanches Herba, protected against oxidant injury in H9c2 cardiomyocytes and in rat hearts by enhancing mitochondrial glutathione redox cycling, possibly through the intermediacy of mitochondrial reactive oxygen species production. We therefore hypothesized that BSS pretreatment can also confer tissue protection against oxidant injury in other vital organs such as liver and kidney of rats. In this study, the effects of BSS pretreatment on rat models of carbon tetrachloride (CCl4) hepatotoxicity and gentamicin nephrotoxicity were investigated. The findings showed that BSS pretreatment protected against CCl4-induced hepatotoxicity, but not gentamicin nephrotoxicity in rats. The hepatoprotection afforded by BSS was associated with the improvement in mitochondrial glutathione redox status, presumably through the glutathione reductase-mediated enhancement in mitochondrial glutathione redox cycling. The hepatoprotection afforded by BSS was also accompanied by the improved mitochondrial functional ability in rat livers. The inability of BSS to protect against gentamicin nephrotoxicity was likely due to the relatively low bioavailability of BSS in rat kidneys. BSS may serve as potential mitohormetic agent for the prevention of oxidative stress-induced injury in livers.

    Topics: Animals; Antioxidants; Biological Availability; Carbon Tetrachloride; Chemical and Drug Induced Liver Injury; Female; Gentamicins; Glutathione; Glutathione Reductase; Kidney; Kidney Diseases; Liver; Mitochondria; Oxidants; Oxidation-Reduction; Oxidative Stress; Rats; Rats, Sprague-Dawley; Reactive Oxygen Species; Sitosterols

2014
Chemical characterization and antioxidant activity of Amazonian (Ecuador) Caryodendron orinocense Karst. and Bactris gasipaes Kunth seed oils.
    Journal of oleo science, 2014, Volume: 63, Issue:12

    Nowadays, data concerning the composition of Caryodendron orinocense Karst. (Euphorbiaceae) and Bactris gasipaes Kunth (Arecaceae) seed oils are lacking. In light of this fact, in this paper fatty acids and unsaponifiable fraction composition have been determined using GC-MS, HPLC-DAD (Diode Array Detector), NMR approaches and possible future applications have been preliminary investigated through estimation of antioxidant activity, performed with DPPH test. For C. orinocense linoleic acid (85.59%) was the main component, lauric (33.29%) and myristic (27.76%) acids were instead the most abundant in B. gasipaes. C. orinocense unsaponifiable fraction (8.06%) evidenced a remarkable content of β-sitosterol, campesterol, stigmasterol, squalene and vitamin E (816 ppm). B. gasipaes revealed instead β-sitosterol and squalene as main constituents of unsaponifiable matter (3.01%). Antioxidant capacity evidenced the best performance of C. orinocense seed oil. These preliminary results could be interesting to suggest the improvement of the population's incomes from Amazonian basin. In particular the knowledge of chemical composition of C. orinocense and B. gasipaes oils could be helpful to divulge and valorize these autochthones plants.

    Topics: Antioxidants; Arecaceae; Cholesterol; Chromatography, High Pressure Liquid; Euphorbiaceae; Fatty Acids; Free Radical Scavengers; Gas Chromatography-Mass Spectrometry; Lauric Acids; Linoleic Acid; Magnetic Resonance Spectroscopy; Myristic Acid; Nuts; Phytosterols; Plant Oils; Seeds; Sitosterols; Squalene; Stigmasterol; Vitamin E

2014
[Chemical constituents from roots of Rubus parvifolius].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:6

    To investigate the chemical constituents from the roots of Rubus parvifolius.. The chemical constituents were isolated by silica gel column chromatography, Sephadex LH-20, as well as preparative high performance liquid chromatography. Their structures were identified on the basis of physicochemical properties and NMR analysis.. Six comounds were isolated and identified as 3-O-Acetyl-11α, 12α-epoxy-oleanan-28,β-olide( I ) ,3-O-Acetyl-pomolic acid( II ), Ursolic acid( Ill),Ursolic acid acetate (1V ), Euscaphic acid ( V) and β-Sitosterol ( VI).. Compounds I , II and IV are isolated from Rubus parvifolius for the first time.

    Topics: Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Oleanolic Acid; Plant Roots; Rubus; Sitosterols; Triterpenes; Ursolic Acid

2014
Metabonomic analysis of Bombyx mori (Heterocera: Bombysidae) treated with acetaminophen.
    Journal of insect science (Online), 2014, Volume: 14

    The feasibility of using Bombyx mori as model animal is attracting more attention. Whether the effect of drugs on the metabolite profiling was consistent with those in mammals was an aspect to evaluate the feasibility of B. mori as model animal. In this study, we used acetaminophen to treat Dazao fifth-instar B. mori, and its metabolites in hemolymph were detected by gas chromatography-mass spectrometry. The corresponding data were processed and analyzed by total model analysis, principal component analysis, partial least squares-discriminant analysis, orthogonal partial least squares-discriminant analysis, and finally, the difference metabolites between acetaminophen group and control group were selected and identified by our reference material database and the National Institute of Standard and Technology database. The results showed that acetaminophen administration induced elevation of metabolites related to energy source, the intermediate of cholesterol synthesis, and the metabolites related to melanization and also induced the decrease of metabolites in pathway of Krebs cycle, the cholesterol, and sitosterol, which suggested that acetaminophen administration inhibited energy metabolism and promoted the expenditure and imbalance of hormone and melanization.

    Topics: Acetaminophen; Analgesics, Non-Narcotic; Animals; Bombyx; Cholesterol; Citric Acid Cycle; Gas Chromatography-Mass Spectrometry; Hemolymph; Larva; Melanins; Metabolome; Metabolomics; Sitosterols

2014
[Chemical constituents from leaf of Rhododendron przewalskii].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:8

    To study the chemical constituents from the leaf of Rhododendron przewalskii.. Isolate and purify compounds by chromatographic methods, and identify structures by spectroscopic methods.. Six compounds were isolated and identified as hyperin (1), avicularin (2), gossypetin-3-O-β-D-galactoside (3), quercetin (4), betuloside (5) and β-sitosterol (6).. Compounds 1-4 and 6 are isolated from Rhododendron przewalskii for the frist time.

    Topics: Flavonoids; Plant Leaves; Quercetin; Rhododendron; Sitosterols

2014
[Chemical constituents of Mallotus paniculatus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:8

    To study the chemical constituents of Mallotus paniculatus.. Column chromatography were used for the isolation and purification. Spectroscopic methods including 1H-NMR, 13C-NMR and MS were used for the identification of structures.. Six compounds were isolated from the CHCl3 extract of 75% alcohol extract of the whole plant and identified to be quercetin( 1), kaempherol(2), hesperetin (3), 7,3'-O-dimethylluteolin (4), p-sitosterol (5) and syringaresinol (6).. All the compounds above were isolated from this plant for the first time.

    Topics: Furans; Lignans; Mallotus Plant; Quercetin; Sitosterols

2014
[Chemical constituents from aerial part of Aconitum brachypodum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:8

    To study the chemical constituents from the aerial part of Aconitum brachypodum.. The constituents were isolated and purified by silica gel, activated alumina and Sephadex LH-20 column chromatography. their structures were elucidated on the basis of spectral data and physiochemical evidence.. Eleven compounds were isolated from 80% ethanol extract and identified as secokaraconitine (1), brachyaconitines A (2), C (3), talatisamine (4), hypaconitine (5), songrine (6), bullatine A (7), 7-carbony sitosterone (8), lupeol (9), β-sitosterol (10) and daucosterol (11).. All compounds are isolated from the aerial part of Aconitum brachypodum for the first time.

    Topics: Aconitum; Dextrans; Pentacyclic Triterpenes; Plant Components, Aerial; Sitosterols

2014
[Chemical constituents of Clerodendrum trichotomum Leaves].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:9

    To investigate the chemical constituents of the leaves of Clerodendrum trichotomum.. The chemical constituents of petroleum ether extract of the leaves of Clerodendrum trichotomum were isolated and purified by various chromatographic techniques, such as silica gel, ODS, Sephadex LH-20, semi-preparative HPLC and recrystallization. The structures of these isolated compounds were identified by spectroscopic analysis (1 H-NMR,13 C-NMR,2D-NMR and MS).. Ten compounds were isolated and identified from petroleum ether extract, containing four triterpenes, lupeol(1), friedelin(2), betulinic acid(3) and taraxerol(4); four sterols, 22-dehydroclerosterol(5), clerosterol(6), stigmasterol(7) and sitosterol(8); one diterpenoid, transphytol(9), and one alkaloid, 1H-indole-3-carboxylic acid(10).. Compound 10 is obtained from the genus Clerodendrum for the first time, and seven compounds (1,3-4, and 7-10) are firstly isolated from this plant.

    Topics: Betulinic Acid; Clerodendrum; Indoles; Oleanolic Acid; Pentacyclic Triterpenes; Plant Leaves; Sitosterols; Sterols; Stigmasterol; Triterpenes

2014
[Chemical constituents of Scrophularia ningpoensis root].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:9

    To investigate the chemical constituents from Scrophularia ningpoensis root.. The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography. The structures of these compounds were elucidated on the basis of spectroscopic analysis.. Eleven compounds were isolated and identified as vanillin (1), eugenol (2), isoeugenol methyl ether(3), ferulic acid(4), benzoic acid(5), syringic acid(6) ,rhamnopyranosyl vanilloyl(7), syringic acid-4-O-alpha-L-rhamnopyr-anoside(8), beta-sitosterol(9), adenosine (10) and dibutyl phthalate(11).. Compound 1-3 and 6-8 are obtained from this plant for the first time.

    Topics: Chromatography, Liquid; Gallic Acid; Plant Roots; Scrophularia; Sitosterols

2014
[Study on chemical constituents of Toddalia asiatica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:9

    To investigate the chemical constituents of Toddalia asiatica.. The compounds were isolated and pu- rified by column chromatography and their structures were identified on the basis of physicochemical properties and spectral data analysis.. Sixteen compounds were isolated and identified as zanthocadinanine A(1), pimpinellin(2), isopimpinellin(3), phellopterin (4), armottianamide(5), chelerythrine(6), nitidine(7), chlorogenic acid (8), toddalolactone (9), protopine(10), skimmianine(11), dictamine(12), toddalenone(13), beta-sitosterol(14), bergapten(15) and 8-hydroxy-6-methoxycoumarin(16).. Compound 1 and 16 are isolated from Toddalia genus for the first time.

    Topics: 5-Methoxypsoralen; Coumarins; Furocoumarins; Methoxsalen; Rutaceae; Sitosterols

2014
[Study on chemical constituents from Schisandra chinensis stem].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:10

    To separate and identify the chemical constituents from the stem of Schisandra chinensis.. Various chromatographic techniques were used to separate and purify the chemical constituents from 95% ethanol extraction of the stem of Schisandra chinensis. Their structures were elucidated based on the physico-chemical properties and spectral data.. Ten compounds were obtained and elucidated as (+)-deoxyschizandrin (1), γ-schizandrin (2), wuweizisu C (3), gomisin N (4), schizandrin (5), anwuweizic acid (6), (-)-dihydroguaiaretic acid (7), tetradecanoic acid (8), β-sitosterol (9) and daucosterol (10).. Compounds 6-8 are obtained from the stem of Schisandra chinensis for the first time.

    Topics: Cyclooctanes; Guaiacol; Lignans; Phytochemicals; Plant Stems; Polycyclic Compounds; Schisandra; Sitosterols

2014
[Chemical constituents from traditional Chinese medicine Siegesbeckia pubescens].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2014, Volume: 39, Issue:24

    Column chromatography on silica gel was used to study the chemical constituents of traditional Chinese medicine Siegesbeckia pubescens. The chemical structures of the separated compounds were elucidated by spectroscopic data analyses. As a result, eighteen compounds were obtained and identified as 3, 4'-dimethoxy quercetin(1), 3, 3', 4'-trimethoxy quercetin(2), 3, 3'-dimethoxy quercetin(3), 7, 3', 4'-trimethoxy luteolin(4), ursolic acid(5), 2β,19α-dihydroxyursolic acid(6), 2β-hydroxyursolic acid (7), stigmasterol-7-one(8), 5α, 8α-epidioxy-24(R)-methyl-cholesta-6, 22-diene-3β-ol(9), β-sitosterol(10), 2, 6-di(3-hydroxy-4-methoxyphenyl)-3, 7-dioxacyclo [3. 3. 0] octane (11), aurantiamide acetate (12), 3-(m-hydroxyl-p-methoxy)-N-(2'-p-hydroxyl-phenethyl)-2E-acrylamide(13), p-hydroxy benzaldehyde (14), m-hydroxy-p-methoxy benzaldehyde (15), 3, 4, 5-trimethoxybenzoic acid(16), monoethyl malonate(17), and p-hydroxylcinnamic acid(18). Among them, compounds 1-9, 11-18 were isolated from this plant for the first time.

    Topics: Asteraceae; Drugs, Chinese Herbal; Luteolin; Medicine, Chinese Traditional; Plants, Medicinal; Quercetin; Sitosterols; Triterpenes; Ursolic Acid

2014
[Determination of β-sitosterol and total sterols content and antioxidant activity of oil in acai (Euterpe oleracea)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2014, Volume: 39, Issue:23

    In order to establish a method for the determination of the sterols of the oil in the freeze-dried acai (Euterpe oleracea Mart.) and to evaluate its antioxidant activities, a saponification/extraction procedure and high performance liquid chromatography (HPLC) analysis method were developed and validated for the analysis of phytosterols in PEE (Petroleum ether extract). Separation was achieved on a Purosper STAR LP C18 column with a binary, gradient solvent system of acetonitrile and isopropanol. Evaporative light scattering detection (ELSD) was used to quantify β-sitosterol and the total sterols. Peak identification was verified by retention times and spikes with external standards. Standard curves were constructed (r = 0.999 2) to allow for sample quantification. Recovery of the saponification and extraction was demonstrated via analysis of spiked samples. The highest content of total sterols is β-sitosterol. The antioxidant activities of the extracts were evaluated using the total oxyradical scavenging capacity assay (TOSC assay). The result showed that the PEE exhibited significant antioxidant properties, sample concentration and the antioxidant capacity had a certain relevance.

    Topics: Antioxidants; Arecaceae; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Phytosterols; Sitosterols

2014
[Study on anti-tumor chemical constituents from pericarps of Juglans mandshurica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:11

    To study the anti-tumor chemical components of the pericarps of Juglans mandshurica.. The chemical constituents were isolated and purified by AB-8 macroporous adsorption resin, silica gel, Sephadex LH-20 columns and recrystallization. The structures were elucidated on the basis of physicochemical properties and NMR spectral data analysis.. From the pericarps of Juglans mandshurica, twelve compounds were separated and identified as 3-methoxy juglone(1), 3-ethoxy juglone(2), 1,8-di-hydroxy anthraquinone (3), juglone (4), 2α, 3α, 19α-trihydroxy ursolic acid (5), 1α, 3β-dihydroxy-olean-18-ene (6), methyl gallate (7), pterocarine(8), quercetin(9), kaempferol(10), daucosterol(11), and β-sitosterol(12).. Compounds 1 - 3 and 6 are isolated from the pericarps of Juglans mandshurica for the first time. Compounds 5 and 7 are isolated from Juglans genus for the first time.

    Topics: Anthraquinones; Antineoplastic Agents, Phytogenic; Drugs, Chinese Herbal; Gallic Acid; Juglans; Kaempferols; Naphthoquinones; Phytochemicals; Seeds; Sitosterols; Triterpenes; Ursolic Acid

2014
[Chemical constituents from supercritical CO2 extraction of Schisandra chinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:11

    To study the chemical constituents from the supercritical CO2 extraction of Schisandra chinensis.. The compounds were separated and purified by conventional column chromatography and their structures were identified by spectroscopic methods.. Nine compounds were isolated from the supercritical CO2 extraction of Schisandra chinensis, and their structures were identified as chrysophanol(1),schisandrin B(2), β-sitosterol(3), schisandrin C(4),schisandrol A(5), angeloylgomisin H(6), daucosterol(7) 1, 5-dimethyl citrate (8), and shikimic acid (9).. Compounds 1, 8 and 9 are isolated from Schisandra chinensis for the first time,and compound 1 as an anthraquinone is isolated from this genus for the first time.

    Topics: Cyclooctanes; Lignans; Phytochemicals; Polycyclic Compounds; Schisandra; Sitosterols

2014
[Studies on chemical constituents from seeds of Euryale ferox].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:11

    To study the chemical constituents from the seeds of Euryale ferox.. The chemical constituents were isolated by silica gel column, Sephadex LH-20 and their structures were identified by physico-chemical and spectral analysis.. Seven compounds were purified from the 95% ethanol extract. These constituents were elucidated as protocatechuic acid (1), gallic acid (2), gallic acid ethyl ester(3),5 ,7-dihydroxychromone(4), β-sitosterol(5), daucosterol(6), and 5,7-dihydroxy-6,4'-dimethoxyflavone(7), respectively.. All compounds are isolated from this plant for the first time.

    Topics: Gallic Acid; Hydroxybenzoates; Nymphaeaceae; Phytochemicals; Seeds; Sitosterols

2014
[Study on Chemical Constituents from Roots of Lonicera macranthoides].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:12

    To study chemical constituents of the roots of Lonicera macranthoides.. The chemical constituents were isolated and purified by means of several chromatographic techniques and their structures were elucidated by spectroscopic methods.. Seven compounds were isolated and identified as ribenol (1), excoecarin C (2), 18-hydroxy-13-epi-manoyloxide (3), asiatic acid (4), oleanolic acid (5), β-sitosterol (6) and β-daucosterol (7).. Compounds 1-4 are obtained from this genus for the first time. Compound 5 is obtained from this plant for the first time. All the compounds are found from the roots of Lonicera mac- ranthoides for the first time.

    Topics: Lonicera; Oleanolic Acid; Pentacyclic Triterpenes; Phytochemicals; Plant Roots; Sitosterols

2014
[Chemical Constituents of Seaweed Sargassum naozhouense].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:12

    To investigate the chemical constituents in the seaweed Sargassum naozhouense collected from the sea around Zhanjiang.. The compounds were isolated and purified by various chromatographic techniques including silica gel chromatography, Sephadex LH-20 gel chromatography as well as preparative thin layer chromatography, and their structures were identified by spectral analysis.. Ten compounds were isolated and identified as 1-O-hexadecanoyl glycerol (1), pheophytin a(2), β-sitosterol (3), mannitol (4), uracil (5), thymine(6),p-hydroxybenzoic acid(7) 3,4-dihydroxybenzoic acid (8) 4-hydroxyphthalide (9), and 2'-de-cxythymidine( 10).. All the compounds are isolated from the seaweed Sargassum naozhouense for the first time.

    Topics: Chromatography, Gel; Hydroxybenzoates; Pheophytins; Sargassum; Seaweed; Sitosterols

2014
[Study on Chemical Constituents of Oldenlandia diffusa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2014, Volume: 37, Issue:12

    To study the chemical constituents of Oldenlandia diffusa.. The chemical constituents were isolated and purified by silica gel and Sephadex LH-20 column chromatography as well as recrystallization method, and their structures were elucidated on the basis of physical and spectral analyses.. Nine compounds were isolated and their structures were identified as quercetin (1), kaempferol (2), scopoletin (3), 2-hydroxy-3-methylanthraquinone (4), 2-hydroxy-l-methoxyanthraquinone (5), α-linolenic acid (6), vanillic acid (7), p-hydroxyphenylethanol (8) and, β-sitosterol (9).. Compound 6 is obtained from this genus for the first time. Compounds 7 and 8 are obtained from this plant for the first time.

    Topics: alpha-Linolenic Acid; Anthraquinones; Kaempferols; Oldenlandia; Phenylethyl Alcohol; Phytochemicals; Quercetin; Scopoletin; Sitosterols; Vanillic Acid

2014
Role of the ABCG8 19H risk allele in cholesterol absorption and gallstone disease.
    BMC gastroenterology, 2013, Feb-13, Volume: 13

    Gallstone disease is associated with p.D19H of ABCG8 as well as alterations of cholesterol and bile acid metabolism. However, molecular mechanisms have not been fully elucidated. It is important to understand the link between the sterol transporters ABCG5/8 and NPC1L1 and intestinal cholesterol absorption as well as de novo synthesis in gallstone patients stratified according to 19H risk allele. Moreover, the functional importance of the 19H variant on intestinal ABCG8 feature remains to be clarified.. Measurements of serum surrogate markers of cholesterol absorption (plant sterols: sitosterol, campesterol) and synthesis (cholesterol precursor: lathosterol) were carried out by gas chromatography/mass spectrometry (GC/MS). For expression studies, total RNA was isolated from 168 ileal biopsies of study participants with (34) and without gallstone disease (134). Messenger RNA was measured by LightCycler real-time PCR. Genomic DNA was obtained from blood leukocytes. Genotype frequencies of p.D19H were established using MALDI-TOF mass spectrometry.. Compared to controls, cholesterol absorption but not synthesis in gallstone carriers was diminished by about 21% based on low serum sitosterol (P = 0.0269) and campesterol (P = 0.0231) to cholesterol ratios. D19H was found to be significantly associated with gallstones (odds ratio [OR] = 2.9, P = 0.0220, 95% confidence interval [CI]:1.22-6.89), particularly in the overweight cohort (OR = 3.2, P = 0.0430, 95% CI:1.07-9.26). Cholesterol absorption was about 24% lower in individuals carrying p.D19H compared to wild type (Psitosterol = 0.0080, Pcampesterol = 0.0206). Moreover, irrespective of phenotype, carriers of p.D19H displayed a significant lower absorption than carriers of the major allele. The most pronounced effect on cholesterol absorption ratio was observed for serum campesterol levels (wild type controls to mutated controls 28%, P = 0.0347 and wild type controls to gallstone carriers with 19H allele 37%, P = 0.0030). Notably, ABCG5/8 and NPC1L1 expression was similar in gallstone carriers and controls regardless of p.D19H presence.. Both gallstone disease and p.D19H of ABCG8 are associated with diminished cholesterol absorption. However, p.D19H is not responsible for the differences in small intestinal sterol transporter expression.

    Topics: Adult; Alleles; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Biopsy; Cholesterol; Female; Gallstones; Genetic Predisposition to Disease; Humans; Ileum; Intestinal Absorption; Male; Middle Aged; Phytosterols; Polymorphism, Genetic; Risk Factors; Sitosterols; Sterols

2013
Plant sterol metabolism. Δ(7)-Sterol-C5-desaturase (STE1/DWARF7), Δ(5,7)-sterol-Δ(7)-reductase (DWARF5) and Δ(24)-sterol-Δ(24)-reductase (DIMINUTO/DWARF1) show multiple subcellular localizations in Arabidopsis thaliana (Heynh) L.
    PloS one, 2013, Volume: 8, Issue:2

    Sterols are crucial lipid components that regulate membrane permeability and fluidity and are the precursors of bioactive steroids. The plant sterols exist as three major forms, free sterols, steryl glycosides and steryl esters. The storage of steryl esters in lipid droplets has been shown to contribute to cellular sterol homeostasis. To further document cellular aspects of sterol biosynthesis in plants, we addressed the question of the subcellular localization of the enzymes implicated in the final steps of the post-squalene biosynthetic pathway. In order to create a clear localization map of steroidogenic enzymes in cells, the coding regions of Δ(7)-sterol-C(5)-desaturase (STE1/DWARF7), Δ(24)-sterol-Δ(24)-reductase (DIMINUTO/DWARF1) and Δ(5,7)-sterol-Δ(7)-reductase (DWARF5) were fused to the yellow fluorescent protein (YFP) and transformed into Arabidopsis thaliana mutant lines deficient in the corresponding enzymes. All fusion proteins were found to localize in the endoplasmic reticulum in functionally complemented plants. The results show that both Δ(5,7)-sterol-Δ(7)-reductase and Δ(24)-sterol-Δ(24)-reductase are in addition localized to the plasma membrane, whereas Δ(7)-sterol-C(5)-desaturase was clearly detected in lipid particles. These findings raise new challenging questions about the spatial and dynamic cellular organization of sterol biosynthesis in plants.

    Topics: Arabidopsis; Arabidopsis Proteins; Intracellular Space; Oxidoreductases Acting on CH-CH Group Donors; Phytosterols; Protein Transport; Saccharomyces cerevisiae; Sitosterols

2013
Common sources and composition of phytosterols and their estimated intake by the population in the city of São Paulo, Brazil.
    Nutrition (Burbank, Los Angeles County, Calif.), 2013, Volume: 29, Issue:6

    Phytosterols have been used alone, or combined with lipid-altering drugs, to reduce cholesterol levels and the burden of cardiovascular disease. Considerable variation in the composition of phytosterols exists and its consumption, in a regular diet, by the Brazilian population is still unknown. Thus, the aim of the present study was to determine the phytosterols content of the most consumed plant foods and to estimate the phytosterols intake by this population.. Intake of plant foods of a representative population of the city of São Paulo (n = 1609), randomly selected on the basis of the Brazilian Institute for Geography and Statistics census data (2010), was obtained by a food frequency questionnaire (FFQ). Foods were chosen on the basis of the Consume Expenditure Survey (2002-2003) and from answers to the FFQ. Phytosterols composition of most consumed greens, legumes, cereals, and seeds, fruits, and vegetable oils was determined by gas chromatography (flame ionization detection). Daily phytosterols intake was estimated in terms of mg per 100 g (mg/100 g(-1)) of edible portion. Underreporters and overreporters were excluded.. Mean (SE) daily phytosterols intake in the diet of the study population was 100.6 (1.2) mg, with β-sitosterol as the largest sterol component (65.4%), followed by campesterol (23.2%), and stigmasterol (10%). No significant changes in daily phytosterols intake were observed after exclusion of underreporters and overreporters. Considerable variation was observed in phytosterols content among the most consumed plant foods.. Analysis of phytosterols composition in most consumed plant foods has shown that phytosterols content varied among food groups. Dietary intake of phytosterols in a large population of the city of São Paulo is in the same range of some countries.

    Topics: Adult; Aged; Brazil; Cholesterol; Chromatography, Gas; Cross-Sectional Studies; Edible Grain; Fabaceae; Feeding Behavior; Female; Fruit; Humans; Male; Middle Aged; Nutrition Assessment; Phytosterols; Plant Oils; Plants, Edible; Seeds; Sitosterols; Stigmasterol; Surveys and Questionnaires; Vegetables; Young Adult

2013
Dietary crystalline common-, micro-, nanoscale and emulsified nanoscale sitosterol reduce equally the cholesterol pool in guinea pigs, but varying nanosystems result in different sterol concentrations in serosal jejunum.
    Nanomedicine : nanotechnology, biology, and medicine, 2013, Volume: 9, Issue:7

    Due to hypocholesterolemic effects, sitosterol is used in functional foods and nanoscale dispersions. To investigate the influence of dietary sitosterol on sterol concentrations in Dunkin Hartley guinea pigs, seven groups consisting of eight animals each were fed either a basal diet (BD), a high-cholesterol diet (HC) or a high-cholesterol diet supplemented with crystalline commonscale (CCS), microscale (CMS, low-dosed: CMLS), nanoscale (CNS) or emulsified nanoscale (ENS) sitosterol. When compared to HC group, all sitosterol formulations decreased liver cholesterol concentrations. No differences in cholesterol or sitosterol concentration were found in plasma and liver between CCS, CMS, CNS, and ENS groups. Apparent cholesterol digestibility decreased by increasing crystalline microscale sitosterol doses. Despite a lower sitosterol intake, ENS group had higher serosal sitosterol concentrations in jejunum than CNS group. To elucidate an impact of the sitosterol nanosystem on gut tissues further studies are necessary.. In this study, the use of sitosterols in a rat model led to contradicting conclusions regarding their ability to reduce cholesterol levels efficiently in guinea pigs, suggesting that more preclinical data is needed before this method could become applicable to human studies.

    Topics: Animals; Cholesterol; Crystallization; Diet; Emulsions; Female; Guinea Pigs; Humans; Jejunum; Liver; Nanoparticles; Particle Size; Rats; Serous Membrane; Sitosterols

2013
Anti-ulcerative colitis activity of compounds from Euphorbia granuleta Forssk.
    Phytotherapy research : PTR, 2013, Volume: 27, Issue:11

    The aim of the present study was to evaluate the anti-ulcerative colitis (UC) activity of the total alcohol extracts of Euphorbia granuleta Forssk. (Euphorpiaceae), isolate and identify the active compounds that could be responsible for the activity, in addition to determination of the possible mechanism of action. Six compounds were isolated and identified from this plant: three phenolic compounds (kampferol, kampferol-3-glucoside and kampferol-3-galactoside) in addition to three steroidal compounds (1-ethoxypentacosane, heptacosan-1-ol and β-sitosterol). Three compounds (heptacosan-1-ol, β-sitosterol and kampferol-3-galactoside) were found to be responsible for the anti-UC activity of E. granuleta extract. The anti-UC activity of these compounds may be explained by reducing the pro-inflammatory cytokine tumor necrosis factor-alpha (TNF-α), in addition to reduction of colonic malondialdehyde (MDA) contents. No side effects were reported on liver and kidney functions. The active compounds reduced both serum TNF-α and mucosal MDA levels.

    Topics: Animals; Anti-Ulcer Agents; Colitis, Ulcerative; Euphorbia; Female; Kidney; Lethal Dose 50; Liver; Male; Malondialdehyde; Mice; Phenols; Plant Components, Aerial; Plant Extracts; Rats; Rats, Wistar; Sitosterols; Steroids; Toxicity Tests, Subchronic; Tumor Necrosis Factor-alpha

2013
Investigation of sterols as potential biomarkers for the detection of pig (S. s. domesticus) decomposition fluid in soils.
    Forensic science international, 2013, Jul-10, Volume: 230, Issue:1-3

    This study was carried out to evaluate the potential of using cholesterol and coprostanol, as indicators for the detection of decomposition fluid of buried pigs (S. s. domesticus) in soils. In May 2007, four pig carcasses (∼35kg) were buried in shallow graves (∼40 cm depth) at the University of Ontario Institute of Technology in Canada. Two pigs were exhumed after three months (Pig 1, Pig 2) and six months (Pig 3, Pig 4) post burial. Soil samples were collected beneath the pig carcasses (∼40cm depth) and from grave walls (∼15-20 cm depth) as well as from a parallel control site. Coprostanol and cholesterol were extracted from soils, purified with solid phase extraction (SPE) and analysed with gas chromatography/mass spectrometry (GC/MS). A significant increase in cholesterol concentrations (p<0.05) and amounts of coprostanol were detected in soil located beneath the pig carcasses after three months of burial. It is assumed that during the putrefaction and liquefaction stages of decomposition pig fluid which contains cholesterol and coprostanol is released into the underlying soil. Therefore, cholesterol and coprostanol could be used as potential biomarkers to detect the presence of decomposition fluid three months after burial under comparable soil and environmental conditions. Further research is suggested for additional soil sampling before and after three months to investigate the abundance of these and other sterols.

    Topics: Animals; Biomarkers; Burial; Cholestanol; Cholesterol; Exhumation; Forensic Anthropology; Forensic Pathology; Gas Chromatography-Mass Spectrometry; Models, Animal; Postmortem Changes; Sitosterols; Soil; Solid Phase Extraction; Swine

2013
Nitric oxide mediates the insulin sensitizing effects of β-sitosterol in high fat diet-fed rats.
    Nitric oxide : biology and chemistry, 2013, Aug-01, Volume: 32

    β-Sitosterol has been shown to have antidiabetic and antioxidant effects in animal models. The objective of the study is to investigate the effects of β-sitosterol on insulin sensitivity, oxidative and nitrosative stress and lipid abnormalities in liver of high fat-fed rat model of insulin resistance (IR) and to assess whether nitric oxide (NO) is involved in its action. Adult male albino Wistar rats of body weight 150-180g were fed either control diet (CON) or high fat diet (HFD). Each dietary group was divided into two and treated or untreated with β-sitosterol (10mg/kgb.w.(-1)day(-1)) for 4weeks. Inhibition of total nitric oxide synthase (NOS) by administration of nitro-l-arginine methyl ester (L-NAME) and inducible NOS (iNOS) by aminoguanidine (AG) in HFD and HFD+ β-sitosterol groups were accomplished to identify the role of NO. After 28days, assays were performed in plasma and liver. HFD-fed rats showed hyperglycemia, hyperinsulinemia, IR, oxidative damage, nitrosative stress, lipid accumulation and elevated serum aminotransferases. Increased expression of iNOS and decreased expression of endothelial NOS (eNOS) were observed in them. Hepatic fat accumulation was further confirmed by histology. The biochemical and histological abnormalities associated with HFD feeding were significantly reduced by β-sitosterol administration. Administration of L-NAME to HFD-fed rats caused decrease in insulin sensitivity and increase in oxidative stress. Co-administration of L-NAME for the last seven days to β-sitosterol-treated HFD rats abolished the glucose lowering effect of β-sitosterol, but the ability to decrease oxidative stress remained unaltered. On the other hand, administration of AG resulted in improved glucose homeostasis and antioxidant levels but decreased oxidative stress and enhanced antioxidant potential in both HFD and HFD+ β-sitosterol treated groups. Thus, β-sitosterol promotes insulin sensitivity in rats fed HFD possibly by improving NO levels. With additional studies, β-sitosterol might be used as a functional drug or as an adjuvant in the management of IR and associated fatty liver disease.

    Topics: Analysis of Variance; Animals; Blood Glucose; Body Weight; Diet, High-Fat; Guanidines; Hepatocytes; Insulin; Insulin Resistance; Lipid Metabolism; Liver; Male; NG-Nitroarginine Methyl Ester; Nitric Oxide; Nitric Oxide Synthase Type III; Nitrites; Organ Size; Oxidative Stress; Rats; Rats, Wistar; Sitosterols

2013
Nutritional evaluation and health promoting activities of nuts and seeds cultivated in Greece.
    International journal of food sciences and nutrition, 2013, Volume: 64, Issue:6

    Available data suggest that genetic as well as environmental factors may influence nuts and seeds nutrients content. In this context nuts and seeds cultivated in Greece were studied. Macronutrients content was in agreement with that from other areas. Total phenolics content was in the range of 43.0 ± 2.1-1512.7 ± 60.7 mg GAE/100 g for chestnut and walnut, respectively. Thirteen to 22 individual phenolics were identified in the studied species. Oleanolic acid was in the range of 0.10-9.03 mg/100 g. Pumpkin seeds contained the higher squalene content (71.6 mg/100 g). β-Sitosterol predominated in all samples except pumpkin seeds. Tocopherols ranged from 8.9 mg/100 g (chestnut) to 29.3 mg/100 g (almond). Nuts and seeds hydrophilic extracts at quantities corresponding to the estimated daily consumption by the Greeks succeeded in inhibiting LDL oxidation in vitro by increasing lag time 1.1-14.1 times. One serving of nuts or seeds may cover a significant fraction of health promoting microconstituents daily intake.

    Topics: Antioxidants; Cucurbita; Fagaceae; Functional Food; Greece; Humans; Juglans; Lipoproteins, LDL; Nutritive Value; Nuts; Oleanolic Acid; Oxidation-Reduction; Phenols; Plant Extracts; Prunus; Seeds; Sitosterols; Squalene; Tocopherols

2013
Substitution of membrane cholesterol with β-sitosterol promotes nonamyloidogenic cleavage of endogenous amyloid precursor protein.
    Neuroscience, 2013, Sep-05, Volume: 247

    Increasing evidence has linked membrane cholesterol to amyloid precursor protein (APP) processing. β-Sitosterol (BS) is one of the most common forms of plant sterols, with the structure very similar to that of cholesterol. Using HT22 mouse hippocampal cells, this study investigated whether the substitution of membrane cholesterol with BS influences APP metabolism. It was found that cholesterol/BS substitution promoted nonamyloidogenic processing of APP without affecting membrane fluidity. Additional experiments suggest that the effect of membrane BS on APP metabolism is associated with the migration of APP from lipid rafts toward non-raft regions. Given that dietary BS can enter the brain and accumulates in the plasma membrane of brain cells, these results suggest a potential use of BS in the prevention of Alzheimer's disease.

    Topics: Amyloid beta-Protein Precursor; Animals; Cell Line; Cell Membrane; Cholesterol; Mice; Protein Processing, Post-Translational; Sitosterols

2013
Development and validation of a GC-MS method for the evaluation of 17 endocrine disruptor compounds, including phytoestrogens and sitosterol, in coastal waters - their spatial and seasonal levels in Porto costal region (Portugal).
    Journal of water and health, 2013, Volume: 11, Issue:2

    A gas chromatography with mass spectrometric detection (GC-MS) method was developed and optimized for the determination of 17 endocrine disrupting compounds (EDCs) in coastal water samples. The evaluated EDCs were from different origins and included estrogens, bisphenol A, alkylphenolethoxylates, alkylphenols, phytoestrogens and sitosterol (SITO). The EDCs were extracted from samples using Oasis HLB (Hydrophilic-Lipophilic Balance) cartridges and derivatized with N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) added with 1% trimethylchlorosilane (TMCS). The validation parameters revealed that this method was highly specific for all assayed compounds (>99%) and the linearity of the calibration curves showed a correlation higher than 0.99. The detection limits were at low ng/L level and the recovery rates were higher than 70%. The performance of the method was checked using coastal water samples taken every 2 months during 2009-2010 from the Douro River estuary and the Porto coastline (Portugal). These data revealed that approximately 98.0% of the analyzed compounds showed levels above their limits of detection (LODs). The measured estrogens (2-20 ng/L) and industrial pollutants (up to 1.1 μg/L) were in biologic hazardous concentrations. Besides, a clear seasonal pattern of fluctuation was established for phytoestrogens and SITO. The physicochemical data, namely the amounts of nitrates, nitrites and phosphorous, confirmed the low water quality of this area.

    Topics: Atlantic Ocean; Endocrine Disruptors; Estuaries; Gas Chromatography-Mass Spectrometry; Phytoestrogens; Portugal; Reproducibility of Results; Rivers; Seawater; Sitosterols; Water Pollutants, Chemical

2013
The effect of β-sitosterol on the properties of cholesterol/phosphatidylcholine/ganglioside monolayers--the impact of monolayer fluidity.
    Colloids and surfaces. B, Biointerfaces, 2013, Oct-01, Volume: 110

    In this paper the influence of one of phytosterols, namely β-sitosterol on cholesterol (Chol)/phosphatidylcholine (PC)/ganglioside (GM3) monolayers was examined to find the correlation between the properties of model system and the effect of phytocompound. The studied monolayers differed in condensation and fluidity, which were modified by the structure of phosphatidylcholine. It was found that the incorporation of β-sitosterol into cholesterol/phosphatidylcholine/ganglioside films changes their morphology, condensation and interactions between the lipids. The substitution of cholesterol more strongly decreased the condensation and stability of the film containing PC molecules having monounsaturated chains than more densely packed monolayer composed of saturated phosphatidylcholine. However, thorough analysis of data obtained so far suggests that the magnitude of β-sitosterol effect is determined by the composition of the system rather than its fluidity itself. Moreover, the results collected herein correlate well with the findings that phytosterol more strongly inhibits the growth of cancer cells, which at a given proportion of cholesterol to phospholipids in membranes, have more unsaturated fatty acids within phospholipids molecules.

    Topics: Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Cholesterol; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Gangliosides; Humans; Membrane Fluidity; Phosphatidylcholines; Sitosterols; Structure-Activity Relationship

2013
Analysis of fatty acids and phytosterols in ethanol extracts of Nelumbo nucifera seeds and rhizomes by GC-MS.
    Journal of agricultural and food chemistry, 2013, Jul-17, Volume: 61, Issue:28

    The purpose of this study was to investigate the fatty acid and phytosterol contents in ethanol extracts of lotus seeds and rhizomes. These ethanol extracts were extracted with hexane. The hexane extracts were hydrolyzed in a microwave reactor, and total fatty acids and phytosterols were analyzed. The hexane extracts were also subjected to silica gel column chromatography. Nonpolar components (triglycerides and steryl-fatty acid esters) were hydrolyzed, and then the contents were analyzed. Polar components (diglycerides, monoglycerides, fatty acids, and phytosterols) were analyzed directly. Seeds contained higher concentrations of fatty acids and phytosterols compared to rhizomes. Linoleic acid, palmitic acid, and oleic acid were the main fatty acid components in seeds and rhizomes, and most of them in seeds were in the ester form. In seeds, phytosterols existed mainly in the free form rather than in steryl-fatty acid ester form. β-Sitosterol was the most abundant phytosterol in seeds and rhizomes.

    Topics: Ethanol; Fatty Acids; Hexanes; Linoleic Acid; Nelumbo; Oleic Acid; Palmitic Acid; Phytosterols; Plant Extracts; Rhizome; Seeds; Sitosterols

2013
Antiplasmodial and cytotoxic flavans and diarylpropanes from the stems of Combretum griffithii.
    Journal of natural products, 2013, Jul-26, Volume: 76, Issue:7

    Four new flavans, griffinoids A-D (1-4), and two new diarylpropanes, griffithanes E and F (7 and 8), together with two known flavans (5 and 6), four known diarylpropanes, and β-sitosterol, were isolated from the EtOAc extract of the stems of Combretum griffithii. Compounds 3, 4, 5, and 9 exhibited weak antiplasmodial activity, with IC50 values of 15.74, 13.04, 9.66, and 14.45 μM, respectively. In addition, compounds 4, 5, and 8 also exhibited weak cytotoxicity toward one or more cancer cell lines including human epidermoid carcinoma, human breast cancer, and human small cell lung cancer cell lines.

    Topics: Antimalarials; Antineoplastic Agents, Phytogenic; Combretum; Drug Screening Assays, Antitumor; Female; Flavonoids; Humans; Molecular Structure; Mycobacterium tuberculosis; Nuclear Magnetic Resonance, Biomolecular; Plant Stems; Sitosterols; Thailand

2013
A new natural naphtho[1,2-b]furan from the leaves of Cassia fistula.
    Journal of Asian natural products research, 2013, Volume: 15, Issue:11

    A new naphtho[1,2-b]furan, 2,9-dihydroxy-7-methoxy-4-methylnaphtha[1,2-b]furan-3(2H)-one (1), along with 10 known compounds vanillic acid (2), naringenin (3), glyceryl-1-tetracosanoate (4), moracin J (5), 1,3,8-trihydroxyanthraquinone (6), esculetin (7), mauritianin (8), kaempferol 3-neohesperidoside (9), β-sitosterol (10), and β-daucosterol (11), was isolated from the leaves of Cassia fistula. The structure of the new compound was determined by NMR and X-ray analysis. Compounds 1, 3, 5-9 were isolated from this plant for the first time. The naphtha[1,2-b]furan was firstly isolated from the natural resources.

    Topics: Cassia; Drugs, Chinese Herbal; Furans; Kaempferols; Molecular Structure; Naphthalenes; Nuclear Magnetic Resonance, Biomolecular; Plant Leaves; Sitosterols

2013
Studies on β-sitosterol and ceramide-induced alterations in the properties of cholesterol/sphingomyelin/ganglioside monolayers.
    Biochimica et biophysica acta, 2013, Volume: 1828, Issue:11

    Phytosterol-β-sitosterol promotes apoptosis in various cancer cells and inhibits their growth. Supplementation of cancer cells with this compound causes modifications in membrane composition, namely, substitution of cholesterol (Chol), decrease of sphingomyelin (SM) content and increase of ceramide (Cer) level. The aim of this work was to investigate the influence of partial replacement of cholesterol by plant sterol, substitution of sphingomyelin by ceramide and both these factors simultaneously on the properties of the monolayers composed of major lipids identified in breast cancer membranes, namely Chol/SM/GM3 mixtures. Brewster Angle Microcopy experiments and the analysis of the isotherms recorded during films compression and resulting parameters evidenced that β-sitosterol weakens the interactions between molecules, decreases films stability and condensation. The influence of ceramide on sterol/SM/GM3 films was reflected in strong modifications of their texture, however, the morphology of monolayer was determined by the structure of sterol present in the system. It was also found, that simultaneous replacement of 50mol% of Chol and SM by phytosterol and Cer, respectively, induces lipids segregation, which is manifested in large diversity of phases observed in BAM images. To facilitate the analysis of the data collected for multicomponent monolayers, the properties of selected sterol/GM3, sterol/Cer, SM/GM3, Cer/GM3 binary films were also investigated. The obtained results evidenced that the studied herein modifications in the composition of Chol/SM/GM3 monolayer, reflecting compositional alterations induced by phytosterol in cancer membranes, strongly affect the organization of model system, therefore they should be considered in the studies on anticancer mechanism of β-sitosterol.

    Topics: Ceramides; Cholesterol; Gangliosides; Microscopy; Sitosterols; Sphingomyelins

2013
Thermal properties and nanodispersion behavior of synthesized β-sitosteryl acyl esters: a structure-activity relationship study.
    Journal of colloid and interface science, 2013, Oct-01, Volume: 407

    The efficiency (dose response) of cholesterol-lowering effect of phytosterols in humans depends on their chemical forms (derived or non-derived) and formulation methods in a delivery system. With a series of synthesized β-sitosteryl fatty acid esters (C2:0-C18:0 and C18:1-C18:3), this work examined their thermal properties and applications in preparation of nanodispersion with β-sitosterol as a comparison. Inspection of the melting point (Tm) and the heat of fusion (ΔH) of β-sitosteryl fatty acid esters and the chain length and unsaturation degree of fatty acyl moiety revealed a pronounced structure-property relationship. The nanodispersions prepared with β-sitosterol and β-sitosteryl saturated fatty acid (SFA) esters displayed different particle size distribution patterns (polymodal vs bimodal), mean diameter (115 nm vs less than 100 nm), and polydispersity index (PDI) (0.50 vs 0.23-0.38). β-sitosteryl unsaturated fatty acid (USFA) esters showed a distinctly different dispersion behavior to form nanoemulsions, rather than nanodispersions, with more homogeneous particle size distribution (monomodal, mean diameter 27-63 nm and PDI 0.18-0.25). The nanodispersion of β-sitosteryl medium chain SFA ester (C14:0) demonstrated a best storage stability.

    Topics: Calorimetry, Differential Scanning; Esters; Microscopy, Electron, Transmission; Nanoparticles; Sitosterols; Structure-Activity Relationship; Temperature

2013
Identification and isolation of non-polar compounds from the chloroform extract of Scutellaria ramosissima.
    Natural product research, 2013, Volume: 27, Issue:21

    In the present study, chloroform extract obtained from aerial parts of Scutellaria ramosissima was phytochemically investigated. A non-polar fraction was obtained from the chloroform extract and the chemical composition of this fraction was identified by GC-MS. The major components of the non-polar fraction of S. ramosissima were determined as heneicosane (12.18%), palmitic acid (11.79%), acetovanillone (6.28%), 5,6-dihydroxy-7,8-dimethoxyflavone (31.87%), (9Z)-octadecenoic (oleic) acid (8.21%), stigmasterol (2.68%), β-sitosterol (2.65%) and 5,2'-dihydroxy-6,7,8,6'-tetramethoxyflavone (2.13%). In addition, 5,6-dihydroxy-7,8-dimethoxyflavone was isolated from the same fraction by PTLC.

    Topics: Chloroform; Flavones; Gas Chromatography-Mass Spectrometry; Plant Extracts; Scutellaria; Sitosterols; Stigmasterol

2013
Quantitative analysis of phytosterols in edible oils using APCI liquid chromatography-tandem mass spectrometry.
    Lipids, 2013, Volume: 48, Issue:9

    Previous methods for the quantitative analysis of phytosterols have usually used GC-MS and require elaborate sample preparation including chemical derivatization. Other common methods such as HPLC with absorbance detection do not provide information regarding the identity of the analytes. To address the need for an assay that utilizes mass selectivity while avoiding derivatization, a quantitative method based on LC-tandem mass spectrometry (LC-MS-MS) was developed and validated for the measurement of six abundant dietary phytosterols and structurally related triterpene alcohols including brassicasterol, campesterol, cycloartenol, β-sitosterol, stigmasterol, and lupeol in edible oils. Samples were saponified, extracted with hexane and then analyzed using reversed phase HPLC with positive ion atmospheric pressure chemical ionization tandem mass spectrometry and selected reaction monitoring. The utility of the LC-MS-MS method was demonstrated by analyzing 14 edible oils. All six compounds were present in at least some of the edible oils. The most abundant phytosterol in all samples was β-sitosterol, which was highest in corn oil at 4.35 ± 0.03 mg/g, followed by campesterol in canola oil at 1.84 ± 0.01 mg/g. The new LC-MS-MS method for the quantitative analysis of phytosterols provides a combination of speed, selectivity and sensitivity that exceed those of previous assays.

    Topics: Cholestadienols; Cholesterol; Chromatography, Liquid; Molecular Structure; Pentacyclic Triterpenes; Phytosterols; Plant Oils; Reproducibility of Results; Sitosterols; Stigmasterol; Tandem Mass Spectrometry; Triterpenes

2013
Studies on tracheorelaxant and anti-inflammatory activities of rhizomes of Polygonatum verticillatum.
    BMC complementary and alternative medicine, 2013, Jul-29, Volume: 13

    The present study describes the tracheorelaxant and anti-inflammatory effects of Polygonatum verticillatum which may support its medicinal use in hyperactive airway complaints and inflammatory disorders.. The tracheorelaxant activity of crude extract of the rhizomes of P. verticillatum (PR) was assessed in isolated guinea-pig tracheal tissues immersed in tissue organ bath filled with Tyrode's solution and a continuous supply of carbogen gas (95% O2 and 5% CO2). The contractile and relaxant responses of the tissue were measured using isometric transducers coupled with Power-Lab data acquisition system. The anti-inflammatory effect was evaluated in carrageenan-induced rat paw edema model, while the lipoxygenase inhibitory activity was performed in the in-vitro assay. Various chromatographic and spectroscopic techniques were used for the isolation and characterization of pure molecules.. In isolated guinea-pig tracheal preparations, PR caused complete inhibition of the high K+ (80 mM) and carbachol-induced contractions however, it was more potent against K+ than CCh, similar to verapamil. Pretreatment of the tissue with PR, displaced the Ca2+ concentration-response curves to the right, similar to that induced by verapamil, indicating the presence of Ca2+ channel blocking like activity. When tested on carrageenan-induced rat paw edema, PR demonstrated a marked reduction in edema with 65.22% protection at 200 mg/kg, similar to aspirin. In the in-vitro assay, PR showed lipoxygenase inhibitory activity (IC50: 102 ± 0.19 μg/mL), similar to baicalein. Bioactivity-guided fractionation led to the isolation of 2-hydroxybenzoic acid and β-sitosterol.. These results indicate that the plant possesses tracheorelaxant, mediated possibly through a Ca2+ channel blockade mechanism, and anti-inflammatory activities, which may explain the medicinal use of this plant in airway disorders and inflammation.

    Topics: Animals; Anti-Inflammatory Agents; Calcium Channel Blockers; Carbachol; Carrageenan; Edema; Female; Guinea Pigs; Inflammation; Male; Muscle Contraction; Muscle, Smooth; Phytotherapy; Plant Extracts; Polygonatum; Rats; Rats, Wistar; Respiratory Tract Diseases; Rhizome; Salicylic Acid; Sitosterols; Trachea; Verapamil

2013
[Chemical constituents of Conioselinum vaginatum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2013, Volume: 38, Issue:10

    Sixteen compounds were isolated from Conioselinum vaginatum by silica column chromatography over silica gel and Sephadex LH-20, as well as recrystallization. On the basis of their physical and chemical properties and spectral data, their structures were identified as ligustilide (1), 1,3-dilinolein (2), coniferaldehyde (3), myristicin (4), stigmasterol (5), beta-sitosterol (6), vanillin (7), pregnenolone (8), bergapten (9), xanthotoxin (10), methyl indole-3-carboxylate (11), ferulic acid (12), (E)-3-methoxy-4,5-methylenedioxy-cinnamic alcohol (13), p-hydroxybenzaldehyde (14), 3-methoxy-4,5-methylenedioxy-acetophenone (15), and alpha-(ethoxymethyl)-4-hydroxy- benzenemethanol (16). Among them, compound 15 was a new natural product, and compounds 2, 3, 10, 11, 14, and 16 were obtained from this genus for the first time.

    Topics: Apiaceae; Benzaldehydes; Dextrans; Drugs, Chinese Herbal; Mass Spectrometry; Molecular Structure; Sitosterols

2013
Cyclosporine A impairs the macrophage reverse cholesterol transport in mice by reducing sterol fecal excretion.
    PloS one, 2013, Volume: 8, Issue:8

    Despite the efficacy in reducing acute rejection events in organ transplanted subjects, long term therapy with cyclosporine A is associated with increased atherosclerotic cardiovascular morbidity. We studied whether this drug affects the antiatherogenic process of the reverse cholesterol transport from macrophages in vivo. Cyclosporine A 50 mg/kg/d was administered to C57BL/6 mice by subcutaneous injection for 14 days. Macrophage reverse cholesterol transport was assessed by following [(3)H]-cholesterol mobilization from pre-labeled intraperitoneally injected macrophages, expressing or not apolipoprotein E, to plasma, liver and feces. The pharmacological treatment significantly reduced the amount of radioactive sterols in the feces, independently on the expression of apolipoprotein E in the macrophages injected into recipient mice and in absence of changes of plasma levels of high density lipoprotein-cholesterol. Gene expression analysis revealed that cyclosporine A inhibited the hepatic levels of cholesterol 7-alpha-hydroxylase, concomitantly with the increase in hepatic and intestinal expression of ATP Binding Cassette G5. However, the in vivo relevance of the last observation was challenged by the demonstration that mice treated or not with cyclosporine A showed the same levels of circulating beta-sitosterol. These results indicate that treatment of mice with cyclosporine A impaired the macrophage reverse cholesterol transport by reducing fecal sterol excretion, possibly through the inhibition of cholesterol 7-alpha-hydroxylase expression. The current observation may provide a potential mechanism for the high incidence of atherosclerotic coronary artery disease following the immunosuppressant therapy in organ transplanted recipients.

    Topics: Animals; Apolipoproteins E; ATP-Binding Cassette Transporters; Biological Transport; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Cyclosporine; Feces; Gene Expression Regulation; Intestinal Mucosa; Intestines; Kinetics; Liver; Macrophages, Peritoneal; Male; Mice; Mice, Inbred C57BL; Sitosterols; Tritium

2013
Lipidated steroid saponins from Dioscorea villosa (wild yam).
    Fitoterapia, 2013, Volume: 91

    Two groups of lipidated steroid saponins including seven new compounds (2, 3, 5, and 7-10) were isolated from the widely used botanical, wild yam (Dioscorea villosa), employing a fractionation protocol of metabolomic mining. This methodology recently led to the isolation of 14 diarylheptanoids from the same plant. Together with these lipidated steroid saponins, they establish additional new markers for D. villosa. The lipidation of steroids with analog long-chain fatty acids containing different degrees of unsaturation generates an entire series of compounds which are difficult to purify and analyze. The structures of the two series of lipidated steroid saponins (series A and B) were established by a combination of 1D and 2D NMR as well as GC-MS after chemical modification. Series A was determined to be a mixture of lipidated spirostanol glycosides (1-5), while series B (6-10) was proved to be a mixture of five lipidated clionasterol glucosides. The latter group represents the first derivatives of clionasterol to be found in D. villosa. The discovery of this specific structural type of aliphatic esters of steroid saponins expands the characterization of the secondary metabolome of D. villosa. It may also inspire biological studies which take into account the lipophilic character and significantly altered physiochemical characteristics of these otherwise relatively polar phytoconstituents.

    Topics: Diarylheptanoids; Dioscorea; Fatty Acids; Glycosides; Metabolomics; Molecular Structure; Plant Extracts; Saponins; Sitosterols; Spirostans

2013
Role of complimentary therapy for male LUTS.
    Current urology reports, 2013, Volume: 14, Issue:6

    Phytotherapy, the use of plant based extracts (derived from fruits, seeds, roots, or bark) as medicines or health-promoting agents are often used as first-line treatments for bothersome male lower urinary tract symptoms (LUTS). Their use, either as monotherapy or in conjunction with conventional pharmaceutical treatments is becoming increasingly popular worldwide. There are now over 30 of these phytotherapeutic compounds available, with saw palmetto and pygeum being the most widely used. This paper discusses the mechanism of action, reported efficacies and potential side effects of a number of the most common phytotherapies being used for male LUTS, as well as summarizes outcome data relevant to these agents from the most current peer-reviewed publications.

    Topics: Androgen Antagonists; Complementary Therapies; Flax; Humans; Hypoxis; Lower Urinary Tract Symptoms; Male; Phytotherapy; Picea; Pinus; Plant Extracts; Prostatic Hyperplasia; Prunus africana; Secale; Serenoa; Sitosterols; Urtica dioica

2013
Molecular characterization of Glycine max squalene synthase genes in seed phytosterol biosynthesis.
    Plant physiology and biochemistry : PPB, 2013, Volume: 73

    The reaction catalyzed by squalene synthase (EC.2.5.1.21) that converts two molecules of farnesyl pyrophosphate to squalene represents a crucial branch point of the isoprenoid pathway in diverting carbon flux towards the biosynthesis of sterols. In the present study two soybean squalene synthase genes, GmSQS1 and GmSQS2, were identified in the soybean genome and functionally characterized for their roles in sterol biosynthesis. Both genes encode a deduced protein of 413 amino acids. Complementation assays showed that the two genes were able to convert yeast sterol auxotrophy erg9 mutant to sterol prototrophy. Expression of GmSQS1 and GmSQS2 was ubiquitous in roots, stem, leaves, flower and young seeds of soybean, however GmSQS1 transcript was preferential in roots while GmSQS2 transcript was more in leaves. Their expression was lower in response to dehydration treatments suggesting they might be negative regulators of water stress adaptation. Transgenic Arabidopsis plants overexpressing GmSQS1 driven by either constitutive or seed-specific promoters showed increases in the major end product sterols: campesterol, sitosterol and stigmasterol, which resulted in up to 50% increase in total sterol content in the seeds. The increase in the end product sterols by GmSQS1 overexpression was at the level achievable by previously reported overexpression of individual or combination of other key enzymes in the sterol pathway. Together the data demonstrate that soybean SQS genes play an important role in diverting carbon flux to the biosynthesis of the end product sterols in the seeds.

    Topics: Adaptation, Physiological; Amino Acid Sequence; Carbon; Cholesterol; Droughts; Farnesyl-Diphosphate Farnesyltransferase; Gene Expression Regulation, Plant; Genes, Plant; Glycine max; Molecular Sequence Data; Mutation; Phytosterols; Plant Leaves; Plant Proteins; Polyisoprenyl Phosphates; Promoter Regions, Genetic; Seeds; Sesquiterpenes; Sitosterols; Squalene; Stigmasterol; Stress, Physiological; Water

2013
[Chemical constituents of roots of Celastrus orbiculatus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:4

    To study the chemical constitutes of roots of Celastrus orbiculatus.. The compounds were isolated by column chromatography and identified by spectroscopic methods including IR, MS and NMR.. Nine compounds were isolated and identified as sugiol (1), friedelane-3-one (2), salapermic acid (3), 28-hydroxyfriedelane-3-one (4), pristimerin (5), celastrol (6), beta-sitosterol (7), beta-daucosterol (8) and benzoic acid (9), respectively.. Compounds 2 and 4 are isolated from this plant for the first time.

    Topics: Celastrus; Diterpenes; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Triterpenes

2013
β-Sitosterol induces G1 arrest and causes depolarization of mitochondrial membrane potential in breast carcinoma MDA-MB-231 cells.
    BMC complementary and alternative medicine, 2013, Oct-25, Volume: 13

    It is suggested that dietary phytosterols, such as β-sitosterol (ST), have cancer chemopreventive effects; however, studies are limited to support such claims. Here, we evaluated the efficacy of ST on three different human cancer cell lines including skin epidermoid carcinoma A431 cells, lung epithelial carcinoma A549 cells and breast adenocarcinoma MDA-MB-231.. Cell growth assay, cell cycle analysis, FACS, JC-1 staining, annexin V staining and immunoblotting were used to study the efficacy of ST on cancer cells.. ST (30-90 μM) treatments for 48 h and 72 h did not show any significant effect on cell growth and death in A431 cells. Whereas similar ST treatments moderately inhibited the growth of A549 cells by up to 13% (p ≤ 0.05) in 48 h and 14% (p ≤ 0.05-0.0001) in 72 h. In MDA-MB-231 cells, ST caused a significant dose-dependent cell growth inhibition by 31- 63% (p ≤ 0.0001) in 48 h and 40-50% (p ≤ 0.0001) in 72 h. While exploring the molecular changes associated with strong ST efficacy in breast cancer cells, we observed that ST induced cell cycle arrest as well as cell death. ST caused G0/G1 cell cycle arrest which was accompanied by a decrease in CDK4 and cyclin D1, and an increase in p21/Cip1and p27/Kip1 protein levels. Further, cell death effect of ST was associated with induction of apoptosis. ST also caused the depolarization of mitochondrial membrane potential and increased Bax/Bcl-2 protein ratio.. These results suggest prominent in vitro anti-proliferative and pro-apoptotic effects of ST in MDA-MB-231 cells. This study provides valuable insight into the chemopreventive efficacy and associated molecular alterations of ST in breast cancer cells whereas it had only moderate efficacy on lung cancer cells and did not show any considerable effect on skin cancer cells. These findings would form the basis for further studies to understand the mechanisms and assess the potential utility of ST as a cancer chemopreventive agent against breast cancer.

    Topics: Apoptosis; bcl-2-Associated X Protein; Breast Neoplasms; Carcinoma; Cell Line, Tumor; Cell Proliferation; Cyclin D1; Cyclin-Dependent Kinase 4; G1 Phase Cell Cycle Checkpoints; Humans; Membrane Potential, Mitochondrial; Sitosterols

2013
Online LC-GC-based analysis of minor lipids in various tree nuts and peanuts.
    Journal of agricultural and food chemistry, 2013, Nov-27, Volume: 61, Issue:47

    As information on free sterols/stanols and steryl/stanyl esters in nuts is lacking, the compositions and contents of these lipid constituents in ten different nut types were analyzed. The applied approach was based on online liquid chromatography-gas chromatography and enabled the simultaneous analysis of free sterols/stanols and individual steryl/stanyl fatty acid esters, and additionally of tocopherols and squalene. Total contents of free sterols/stanols ranged from 0.62 mg/g nut in hazelnuts to 1.61 mg/g nut in pistachios, with sitosterol as the predominant compound. Total contents of steryl/stanyl fatty acid esters were in the range of 0.11-1.26 mg/g nut, being lowest in Brazil nuts and highest in pistachios. There were considerable differences between the various nut types not only regarding the contents, but also the compositions of both classes. The levels of tocopherols were highest in pine nuts (0.33 mg/g nut); those of squalene were remarkably high in Brazil nuts (1.11 mg/g nut).

    Topics: Arachis; Chromatography, Gas; Corylus; Fatty Acids; Food Analysis; Lipids; Nuts; Online Systems; Phytosterols; Pistacia; Sitosterols; Squalene; Tocopherols

2013
(+)-rumphiin and polyalthurea, new compounds from the stems of Polyalthia rumphii.
    Natural product communications, 2013, Volume: 8, Issue:10

    Two new compounds, (+)-rumphiin (3) and polyalthurea (7), together with seven known ones, 3,4,5-trimethoxy benzoic acid (1), (-)-seselinone (2), cannabisin D (4), allantoin (5), oxostephanine (6) and a mixture of beta-sitosterol (8) and stigmasterol (9) were isolated from the stems of Polyalthia rumphii. The chemical structures of 3 and 7 were elucidated by the combination of spectroscopic data, and the absolute configuration of 3 at C-2 was determined by the matrix method to be R. All compounds were evaluated for their cytotoxicity on four human cancer cell lines, which demonstrated that 3 was a moderate bioactive lignan, and 6 showed significant anticancer activity against SPC-A-1 and BEL-7402 cell lines with IC50 values of 1.47 and 1.73 microg/mL, respectively.

    Topics: Allantoin; Antineoplastic Agents, Phytogenic; Drug Screening Assays, Antitumor; Gallic Acid; Humans; K562 Cells; Lignans; Plant Stems; Polyalthia; Sitosterols; Stigmasterol

2013
[Addition of pomegranate juice to statin inhibits cholesterol accumulation in macrophages: protective role for the phytosterol beta-sitosterol and for the polyphenolic antioxidant punicalagin].
    Harefuah, 2013, Volume: 152, Issue:9

    Macrophage cholesterol and oxidized lipids accumulation and foam cell formation occur in the early stages of atherosclerosis development. In the current study we used the J774A.1 murine macrophage cell line in order to analyze two atherogenic functions: a. the ability of the cells to produce reactive oxygen species (ROS), and to increase cellular oxidative stress, and b. the ability of the cells to synthesize cholesterol, leading to cholesterol accumulation in the cells. The addition of punicalagin, or beta-sitosterol, or pomegranate juice (which contains both of the above) to simvastatin, significantly improved the statin's ability to inhibit macrophage cholesterol biosynthesis. Furthermore, the addition of pomegranate juice (or punicalagin, but not beta sitosterol) to simvastatin significantly increased the statin ability to protect the cells from oxidative stress. Taken together, the current research provides evidence for the additional cardio protection of statins, that is provided by pomegranate juice antioxidant and hypocholesterolemic effects. The use of statins in combination with pomegranate juice in hypercholesterolemic patients, may allow for the use of lower dosages of statin in order to prevent statin deleterious side effects.

    Topics: Animals; Anticholesteremic Agents; Antioxidants; Beverages; Cell Line; Cholesterol; Drug Therapy, Combination; Hydrolyzable Tannins; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Lythraceae; Macrophages; Mice; Oxidative Stress; Polyphenols; Reactive Oxygen Species; Simvastatin; Sitosterols

2013
[Chemical constituents of Aconitum bulleyanum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:6

    To study the chemical constituents of chloroform fraction from Aconitum bulleyanum.. The compounds were isolated by various chromatographic techniques and identified by spectroscopic methods.. 7 compounds were obtained and identified as yunaconitine (1), crassicaudine (2), foresaconitine (3), chasmaconitine (4), bulleyaconitine A (5), franchetine (6), and beta-sitosterol (7), CONCLUSION: Compounds 2-7 are isolated from this plant for the first time.

    Topics: Aconitine; Aconitum; Alkaloids; Diterpenes; Drugs, Chinese Herbal; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Roots; Sitosterols

2013
[Study on the chemical constituents of mori cortex].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:7

    To study the chemical constituents of Mori Cortex.. The compounds from the dichloromethane-methanol extracts were isolated by the silica gel column chromatography, and their structures were identified by the spectral analysis and chemical evidence.. Eight compounds were obtained and their structures were identified as 3-acetyl-beta-amyranol (1), neotocopherol (2), alpha-amyrin (3), clionasterol (4), betulinic acid (5), moracin O (6), morusin (7) and morusignin L (8).. Componds 2 and 4 are obtained from this plant for the first time.

    Topics: Chromatography, Thin Layer; Molecular Structure; Morus; Oleanolic Acid; Plant Bark; Plant Roots; Sitosterols; Vitamin E

2013
[Study on chemical constituents of triterpenoids from Potentilla discolor].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:7

    To study the triterpenoids constituents in Potentilla discolor.. The compounds were isolated by silica gel chromatography, macroporous resins and polyamide column chromatography from the 70% ethanol extract, and their structures were identified by spectral analysis.. Six compounds were obtained and their structures were identified as 3-O-beta-D-glucopyranosyl-(1 --> 2) -beta-D-xylopyranosyl-19a-hydroxyurs-12-en-28-acid (1), 2alpha, 3/beta, 19alpha-trihydroxyurs-12-en-28-acid (2), 3beta, 19alpha-trihydroxyurs-12-en-24, 28-acid (3), 2alpha, 3beta-dihydroxyolean-12-en-28-acid (4), 2alpha, 3alpha, 19alpha-trihydroxyurs-12-en-28-acid (5), beta-sitosterol (6).. Compounds 1 and 3 are obtained from this plant for the fisrt time.

    Topics: Chromatography, Thin Layer; Molecular Structure; Oleanolic Acid; Potentilla; Sitosterols; Triterpenes

2013
[Chemical constituents of Cudrania cochinchinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:9

    To study the chemical constituents of Cudrania cochinchinensis.. Compounds were isolated and purified by silica gel column, sephadex LH-20 chromatography and recrystallization. Their structures were elucidated by physicochemical properties and spectral data.. Thirteen compounds were isolated from the 70% ethanol extract of the root of Cudrania cochinchinensis and identified as beta-sitosterol (1), butyrospermol (2), butyrospermol acetate (3), (+) syringarenol (4), 1, 3, 6-trihydroxy-7-methoxy xanthone (5), 1, 3, 6, 7-tetrahydroxy-8-prenylxanthone (6), kaempferol (7), dihydrokaempferol (8), umbelliferone (9),4-hydroxybenzyl ethyl ether (10), 2,4-dihydroxybenzaldehyde (11), 4-hydrox-ybenzaldehyde (12) and vanillin (13).. Compounds 2 - 6, 10 - 13 are isolated from Cudrania cochinchinensis for the first time.

    Topics: Benzaldehydes; Chromatography, Thin Layer; Molecular Structure; Moraceae; Plant Extracts; Plant Roots; Plants, Medicinal; Sitosterols; Xanthones

2013
[Chemical constituents from Ajuga nipponensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:12

    To study the chemical constituents of Ajuga nipponensis.. The chemical constituents were isolated by repeated silica gel column chromatography and their structures were elucidated by phyisochemical properties and spectral analysis.. Ten compounds were isolated and identified as:hexadecanoic acid(1), ajuforrestin A(2), beta-sitosterol(3), acacetin(4), apigenin(5), ajugamacrin B(6), ursolic acid(7), beta-ecdysone(8), 8-acetylharpagide(9) and daucosterol(10).. Compounds 1-7 and 10 are isolated from this plant for the first time.

    Topics: Ajuga; Apigenin; Flavones; Molecular Structure; Palmitic Acid; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet

2013
[Study on chemical constituents from twig and leaf of Juniperus sabina].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:12

    To isolate and determine chemical constituents from twig and leaf of Juniperus sabina.. Five compounds were isolated and purified by extraction and different kinds of column chromatography. The structures were determined on the basis of the physicochemical properties and spectral analysis.. The structures were elucidated as quercetin-3-O-(6"-O-acetyl)-beta-D-glucopyranoside(1), hypolaetin-7-O-beta-D-glucopyranoside(2), isoquercetin(3),4-epi-abietic acid(4), beta-sitosterol(5).. Compounds 1-3 are obtained from Juniperus genus for the first time.

    Topics: China; Chromatography, Thin Layer; Drugs, Chinese Herbal; Glucosides; Juniperus; Molecular Structure; Plant Leaves; Quercetin; Sitosterols; Trees

2013
[Chemical constituents of Salix matsudana leaf].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2013, Volume: 36, Issue:12

    To study the chemical constituents of the leaf of Salix matsudana.. The chemical constituents were isolated by column chromatography on silica gel, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of spectral analysis.. Eight compounds were isolated and their structures were identified as beta-Sitosterol(1),5,7-Dihydroxychromone-7-O-beta-D-glucopyranoside(2), (2S)-Helichrysin A(3), (2R)-Helichrysin A(4), Luteolin-7-O-beta-D-glucoside(5), Salicin(6), Apigenin-7-O-beta-D-glucopyranside(7), Lutelion-3'-methylether-7-O-f-D-glucopyranside(8).. Compounds 1-4 are isolated from this plant for the first time.

    Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Luteolin; Molecular Structure; Plant Leaves; Salix; Sitosterols

2013
Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves.
    Natural product research, 2013, Volume: 27, Issue:1

    The essential oils obtained by hydrodistillation from the leaves of Tabernaemontana catharinensis had their composition analysed by GC-MS. A total of 18 substances were identified, consisting of a complex mixture of sesquiterpenes (83.52%), monoterpenes (5.46%) and triterpenes (4.56%). The main components in the oil were β-caryophyllene (56.87%), α-cadinol (12.52%), 8S,13-cedran-diol (5.41%), α-terpineol (3.99%), β-eudesmol (2.54%), caryophyllene oxide (2.51%) and ethyl iso-allocholate (2.03%) along with β-cubebene, γ-cadinene, cubenol, 1,8-cineol, o-cymene, curcumenol, spathulenol, friedeline and β-sitosterol as minor constituents. An antioxidant property was tested with the oil obtained by means of 1,1-diphenyl-2-picrylhydrazyl assay; the oil presented interesting radical scavenging activity. To the best of our knowledge, this is the first study of the composition and antioxidant activity of essential oil from the T. catharinensis collected from Brazil.

    Topics: Antioxidants; Cyclohexane Monoterpenes; Cyclohexanols; Cyclohexenes; Eucalyptol; Monoterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Sitosterols; Tabernaemontana; Terpenes

2013
Grewialin and optivanin new constituents from the stem bark of Grewia optiva Drummond ex Burret (Tiliaceae).
    Natural product research, 2013, Volume: 27, Issue:3

    Studies on the chemical constituents from the stem bark of Grewia optiva have led to the isolation of two new compounds, grewialin (1) and optivanin (2), along with three known constituents which were hitherto unreported from this species. The structures of the new constituents have been elucidated by spectral studies including 1D and 2D NMR experiments (HSQC, HMBC, COSY, NOESY and J-resolved) as well as HR EI-MS spectroscopic data analysis, as 2S*-(3-hydroxy-4-methoxyphenyl)-3R*-methyl-2H-[1,4]-dioxin [2,3]-chromen-7(3H)-one (1); a coumarinolignan and 3-hydroxy-1-(3-hydroxy-4-methoxyphenyl) propan-1-one (2). The known compounds were identified as β-sitosterol, stigmasterol and lupeol by comparing their spectral data with those reported in the literature.

    Topics: Grewia; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Sitosterols; Stigmasterol

2013
Characterisation and phenolic profiles of two rare olive oils from southern Tunisia: Dhokar and Gemri-Dhokar cultivars.
    Journal of the science of food and agriculture, 2013, Volume: 93, Issue:3

    The aim of this work was to study the chemical characteristics of two Tunisian cultivars, namely Dhokar and Gemri-Dhokar, to analyse the fatty acids, sterols, triacylglycerols, triterpenic alcohols, and to determine the phenolic composition and oxidative stability.. Among the rare varieties, Gemri-Dhokar olive oil had the highest value of oleic acid (69.39%) whereas Dhokar oil was noteworthy for its lower content of phenolic compounds (94.56 mg kg(-1) gallic acid equivalents of oil) and presented the highest level of palmitic acid (19.37%). The main sterols found in all olive oil samples were β-sitosterol and Δ5-avenasterol, whereas cholesterol and 24-methylenecholesterol were also found in all samples but in lower amounts. Two triterpenic dialcohols (erythrodiol and uvaol) were also detected and their content ranged from 1.45 to 2.30%, in Gemri-Dhokar and Dhokar olive oil, respectively. Ten phenolic compounds were identified. In all samples, the main phenols found were oleuropein aglycon and pinoresinol. These phenolic compounds showed significant correlations with oxidative stability.. The analytical parameters of two oils that were determined in this study were greatly influenced by genetic factors (cultivar).

    Topics: Alcohols; Drug Stability; Fatty Acids; Furans; Iridoid Glucosides; Iridoids; Lignans; Oleanolic Acid; Olive Oil; Oxidation-Reduction; Palmitic Acid; Phenols; Phytosterols; Plant Oils; Pyrans; Sitosterols; Species Specificity; Triglycerides; Triterpenes; Tunisia

2013
Evaluation of bioactive potential of an Aloe vera sterol extract.
    Phytotherapy research : PTR, 2013, Volume: 27, Issue:6

    We prepared a crude gel material from Aloe vera succulent leaf tissues. The ethanolic extract of lyophilized A. vera gel was used for the GC-MS analysis. Hexadecanoic acid (22.22%) was identified as major compound. Sitosterol and stigmasterol were found to be 2.89% and 2.1% in the extract. HPLC analysis was carried out to confirm the presence of stigmasterol. The concentration of sterol extract needed to scavenge DPPH free radical by 50% was calculated as 5.2 mg mL(-1). In the FRAP assay, the sterol extract showed significant hydroxyl radical scavenging in a dose-dependent manner (IC50 value 1.17 µg mL(-1)). Concentration of the sample required to reduce lipid peroxidation was found to be 4.18 µg mL(-1), and the extract also possessed acetylcholinesterase activity (IC50 - 5.26 µg mL(-1)). Catalase activity was 0.196 μM H2 O2 decomposed min(-1) µg(-1) protein, whereas the peroxidase activity was 17.01 μM of pyragallol oxidized min(-1) µg(-1) protein. The extract recorded higher activity against growth of S. greseus and C. albicans in the experiments carried out to determine antibacterial and antifungal activity, respectively.

    Topics: Acetylcholinesterase; Aloe; Anti-Bacterial Agents; Antifungal Agents; Catalase; Chromatography, High Pressure Liquid; Free Radical Scavengers; Gas Chromatography-Mass Spectrometry; Gels; Lipid Peroxidation; Palmitic Acid; Peroxidase; Plant Extracts; Sitosterols; Stigmasterol

2013
Sphaeranthus indicus induces apoptosis through mitochondrial-dependent pathway in HL-60 cells and exerts cytotoxic potential on several human cancer cell lines.
    Integrative cancer therapies, 2013, Volume: 12, Issue:3

    The study was designed to screen Sphaeranthus indicus, Ganoderma lucidum, and Urtica dioica for their anticancer activity against human cancer cell lines. Phytochemical screening of active extracts was also planned.. Petroleum ether, ethanolic, and aqueous extracts of S indicus Linn, G lucidum P Karst, and U dioica Linn were subjected to cytotoxicity studies using 7 different cancer cell lines. Potent cytotoxicity was noted in petroleum ether extract of S indicus (SIP), which inhibited proliferation of various cancer cell lines. Growth inhibition was determined by sulforhodamine B assay. Two biochemical markers, namely β-sitosterol and 7-hydroxyfrullanolide were isolated and characterized using high-performance thin layer chromatography, melting point, Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass analysis. Cytotoxicity of isolated β-sitosterol and 7-hydroxyfrullanolide were also determined. The IC(50) of SIP was calculated in the HL-60 cells and was found to be 53 µg/mL. Furthermore, SIP induced apoptosis in human leukemia HL-60 cells as measured by several biological end points. Cell cycle analysis and change in mitochondrial membrane potential was quantified by flow cytometry. Subsequently, using annexin V/PI assay, proportion of cells actively undergoing apoptosis was determined. Changes in DNA were observed by DNA ladder assay.. SIP induced apoptotic bodies formation, induced DNA laddering, enhanced annexin-V-FITC binding of the cells, increased sub-G(0) DNA fraction, and induced loss of mitochondrial membrane potential (ΔΨm) in HL-60 cells. SIP also elevated the caspase 3 and caspase 9 levels in the HL-60 cells, which clearly indicates the involvement of the intrinsic proteins in inducing apoptosis.. All the above parameters revealed that SIP induced apoptosis through the mitochondrial-dependent pathway in HL-60 cells. The criterion for anticancer activity in cytotoxicity assay was ≥70% growth inhibition at 100 µg/mL against at least 4 cell lines. As G lucidum and U dioica did not exhibit appreciable inhibitory activity against human cancer cell lines (less than 50%), they were not included in the study thereafter. The results established that SIP has apoptosis-inducing effect against HL-60 cells in vitro and is a promising candidate for further anticancer study. β-Sitosterol and 7-hydroxyfrullanolide can be considered to be potent anticancer compounds isolated from SIP on the basis of present studies.

    Topics: Annexin A5; Antineoplastic Agents, Phytogenic; Apoptosis; Asteraceae; Caspase 3; Caspase 9; Cell Cycle; Cell Line, Tumor; Cell Proliferation; DNA; HL-60 Cells; Humans; Membrane Potential, Mitochondrial; Mitochondria; Plant Extracts; Reishi; Sesquiterpenes; Sitosterols; Urtica dioica

2013
A novel methylated sesquiterpene from seagrass Posidonia oceanica (L.) Delile.
    Natural product research, 2013, Volume: 27, Issue:14

    Phytochemical investigation of chloroform extract from the leaves of the marine plant Posidonia oceanica (L.) Delile (Posidoniaceae), yielded posidozinol, a new methylated sesquiterpene along with β-sitosterol and four known fatty acids: palmitic, palmitoleic, oleic and linoleic acids. The structure elucidation has been established on the basis of 1D- and 2D-NMR spectroscopy, GS/MS and ES mass spectrometry. Antibacterial effects of crude extracts from P. oceanica were evaluated against: Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Staphylococcus epidermidis and Micrococcus luteus microorganisms.

    Topics: Alismatales; Chloroform; Chromatography, Thin Layer; Colony Count, Microbial; Disk Diffusion Antimicrobial Tests; Escherichia coli; Fatty Acids; Magnetic Resonance Spectroscopy; Mass Spectrometry; Methylation; Micrococcus luteus; Molecular Structure; Plant Extracts; Plant Leaves; Pseudomonas aeruginosa; Sesquiterpenes; Sitosterols; Staphylococcus

2013
Antiophidic activity of the extract of the Amazon plant Humirianthera ampla and constituents.
    Journal of ethnopharmacology, 2013, Jan-09, Volume: 145, Issue:1

    Although serotherapy against snakebite has been discovered more than one hundred years ago, antivenom is not available all over Brazil. The use of plants from folk medicine is common mainly in the Brazilian Amazon area. One of these plants is named Humirianthera ampla (HA).. We have investigated HA extract and constituents' antiophidic activity in different experimental protocols against some Bothrops snake venoms (Bothrops jararacussu, Bothrops atrox and Bothrops jararaca). The protocols investigated include phospholipase, proteolytic, pro-coagulant, hemorrhagic, edematogenic and myotoxic activities induced by these venoms in Swiss mice.. All the venoms caused an increase in the rate of creatine kinase (CK) release from isolated muscles, indicating damage to the sarcolemma. The crude extract of HA decreased the myotoxic activity in a concentration-dependent fashion. The presence of HA 300 μg/mL decreased up to 96% of Bothrops jararacussu and 94% of Bothrops atrox myotoxicity after 90 min of exposure. In vivo myotoxicity of Bothrops atrox venom was decreased in 75% when the venom was preincubated with HA 500 mg/kg. Similar results were observed with lupeol against Bothrops jararacussu and Bothrops atrox venoms. The hemorrhagic activity was evaluated by intradermal injection of Bothrops atrox venom. Preincubation and oral pre- and posttreatment with HA decreased hemorrhage by 100%, 45% and 45%, respectively. Bothrops atrox venom also induced formation of edema, which was significantly inhibited by pre- and posttreatment with HA. All the venoms showed extensive pro-coagulating properties, and these activities were inhibited by up to 90% with HA, which presented concentration-dependent inhibition. Finally, proteolytic and phospholipase activities of the venoms were all inhibited by increasing concentrations of HA, lupeol and sitosterol. The inhibition of these activities might help explain the actions against in vivo myotoxicity and the in vivo effects observed, i.e., edema, myotoxicity, pro-coagulation and hemorrhage.. Altogether, our results give support for the popular use of HA extracts in cases of accidents with snakes, suggesting that it can be used as an adjunct in the management of venomous snakebites.

    Topics: Animals; Antivenins; Bothrops; Brazil; Crotalid Venoms; Edema; Ethanol; Hemorrhage; Magnoliopsida; Male; Mice; Muscles; Pentacyclic Triterpenes; Phospholipases; Phytotherapy; Plant Extracts; Plant Roots; Sitosterols

2013
Chemical constituents of Machaerium hirtum Vell. (Fabaceae) leaves and branches and its anti-inflammatory activity evaluation.
    Natural product research, 2013, Volume: 27, Issue:17

    Leaves and branches of Machaerium hirtum Vell. (Fabaceae), native to South America, were subjected to phytopharmacological investigation in order to identify its major chemical constituents and evaluate its extracts, fractions and isolated compounds in assays for anti-inflammatory activities. These were performed using mouse ear edema model, pleurisy and myeloperoxidase activity assays. Six compounds were isolated and identified as the flavanones swertisin and isovitexin, the alkaloid 4-hydroxy-N-methylproline, the triterpenes friedelin and lupeol, and the steroids sitosterol and stigmasterol. These compounds were identified by nuclear magnetic resonance of (1)H and (13)C data, in comparison with literature.

    Topics: Animals; Anti-Inflammatory Agents; Apigenin; Edema; Fabaceae; Magnetic Resonance Spectroscopy; Mice; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Proline; Sitosterols; Stigmasterol; Triterpenes

2013
Dietary Aloe vera components' effects on cholesterol lowering and estrogenic responses in juvenile goldfish, Carassius auratus.
    Fish physiology and biochemistry, 2013, Volume: 39, Issue:4

    Aloes are now considered a very interesting source of bioactive compounds among which phytosterols should play a major role. The present study is an attempt to investigate the hypocholesterolemic activity of Aloe vera associated with its impact on the reproductive status of juvenile goldfish. Therefore, the short- and long-term effects of feeding supplementary diet containing aloe components (20 mg aloe/g diet; 2%) on plasma lipids, plasma vitellogenin, and hepatic estrogen receptor α/β1 mRNA levels in goldfish were examined. Results of GC-MS for phytosterols show high abundance of β-sitosterol in freeze-dried powder of Aloe vera whole leaves. Moreover, a 2% aloe powder dietary supplement was not found estrogenic in juvenile goldfish after either 7- or 30-day treatment, but was consistent in plasma hypocholesterolemic effects following long-term exposure. The present data further support that plasma cholesterol modulation induced by phytosterols may not be related to estrogen-like activity.

    Topics: Aloe; Animals; Biomarkers; Goldfish; Gonads; Hypothalamo-Hypophyseal System; Lipids; Liver; Phytoestrogens; Plant Preparations; Receptors, Estrogen; RNA, Messenger; Sitosterols; Vitellogenins

2013
Pomegranate phytosterol (β-sitosterol) and polyphenolic antioxidant (punicalagin) addition to statin, significantly protected against macrophage foam cells formation.
    Atherosclerosis, 2013, Volume: 226, Issue:1

    To assess the anti-atherogenic effects on macrophage cholesterol biosynthesis rate, and on cellular oxidative stress by the combination of simvastatin with a potent polyphenolic antioxidant (punicalagin), or with a phytosterol (β-sitosterol), or with pomegranate juice (POM, that contains both of them).. Simvastatin (15 μg/ml) decreased J774A.1 macrophage cholesterol biosynthesis rate by 42% as compared to control cells. The addition to the statin of either punicalagin (15 or 30 μM), or β-sitosterol (50 or 100 μM), increased the inhibitory effect of the statin up to 62% or 57%, respectively. Similarly, the combination of POM and simvastatin, resulted in an inhibitory effect up to 59%. While simvastatin inhibited the rate limiting enzyme HMGCoA-reductase, punicalagin, β-sitosterol or POM inhibited macrophage cholesterol biosynthesis downstream to mevalonate. Simvastatin (15 μg/ml) also modestly decreased macrophage reactive oxygen species (ROS) formation by 11%. In the presence of punicalagin (15 or 30 μM) however, a remarkable further inhibition was noted (by 61% or 79%, respectively). Although β-sitosterol alone showed some pro-oxidant activity, the combination of simvastatin, β-sitosterol and punicalagin, clearly demonstrated a remarkable 73% reduction in ROS production. Similarly, simvastatin + POM decreased the extent of ROS formation by up to 63%. These improved antioxidant effects of the combinations could be related to various anti-oxidative properties of the different compounds, including free radicals scavenging capacity, upregulation of paraoxonase 2, and stimulation of reduced glutathione.. The combination of simvastatin with potent antioxidant and phytosterol (such as present in pomegranate) could lead to attenuation of macrophage foam cell formation and atherogenesis.

    Topics: Animals; Antioxidants; Beverages; Cells, Cultured; Cholesterol; Drug Combinations; Foam Cells; Hydrolyzable Tannins; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Lythraceae; Mice; Simvastatin; Sitosterols

2013
Preclinical evaluation of hypoglycemic activity of Ipomoea digitata tuber in streptozotocin-induced diabetic rats.
    Journal of basic and clinical physiology and pharmacology, 2013, Volume: 24, Issue:1

    The use of medicinal plants has turned out to be an alternative method for the treatment of diseases, such as diabetes mellitus. The recommendation of the World Health Organization Committee on Diabetes encouraging research on hypoglycemic agents of plant origin used in traditional medicine has greatly motivated research in this area. The hypoglycemic activity of Ipomoea digitata tuber extract was investigated in streptozotocin-induced diabetic rats.. An oral administration of the hydroalcoholic extract of I. digitata tuber (100 and 200 mg/kg) and glibenclamide was given for 28 days. Blood glucose levels were measured at 0, 2, 4, 6, and 24 h in the acute study and at 0, 7, 14, 21, and 28 days in the chronic study. The weight of rats was recorded before and after the study period of 28 days.. In the acute study, both doses of the extract showed a significant reduction in the blood glucose level compared with the control but less significant than glibenclamide. In the chronic study, all treatments showed a significant blood glucose reduction in diabetic rats. The extract and glibenclamide not only prevented a further body weight loss but also maintained the body weight during the study period.. The result of the study concluded that I. digitata exhibits a considerable hypoglycemic activity, which could be due to the presence of flavonoids and β-sitosterol as active principles, although the mechanism of action remains to be determined. Thus, the plant can be the key contributor in the treatment of diabetes as an alternative medicine.

    Topics: Administration, Oral; Animals; Blood Glucose; Body Weight; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 2; Dose-Response Relationship, Drug; Flavonoids; Glyburide; Hypoglycemic Agents; Ipomoea; Plant Extracts; Rats; Rats, Wistar; Sitosterols; Streptozocin; Time Factors

2013
Sitosterol as an antioxidant in frying oils.
    Food chemistry, 2013, Apr-15, Volume: 137, Issue:1-4

    The antioxidative effect of sitosterol at 1, 2 and 5% levels, in triolein, refined canola, high oleic sunflower and flaxseed oils, continuously heated for a period of up to 72 h at frying temperature of 180 °C, was studied. High Pressure Size Exclusion Chromatography (HPSEC) was used to monitor changes in peak areas of triacylglycerol (TG) polymer, monomer and ester hydrolysis products. The presence of enhanced levels of sitosterol was found to significantly decrease TG polymer formation in triolein and the vegetable oil samples after heating at 180 °C for a period of 72 h. A corresponding increase in the level of intact TG monomer and the extent of TG ester hydrolysis was observed in all samples with enhanced levels of sitosterol. Conversion of sterol to steradiene, by the 1, 2 elimination of water, may be responsible for the antioxidative effect of sitosterol at frying temperatures.

    Topics: Antioxidants; Cooking; Food Additives; Hot Temperature; Hydrolysis; Plant Oils; Sitosterols

2013
Acute effect of β-sitosterol on calcium uptake mediates anti-inflammatory effect in murine activated neutrophils.
    The Journal of pharmacy and pharmacology, 2013, Volume: 65, Issue:1

    To evaluate the effect of β-sitosterol on ⁴⁵Ca²⁺ uptake in activated murine neutrophils, and upon myeloperoxidase and adenosine deaminase activity, and interleukin-1β (IL-1β) and tumour necrosis factor-α (TNF-α) levels, in carrageenan-induced inflammation in the mouse air pouch model.. Dried Esenbeckia leiocarpa bark was macerated and extracted resulting in a crude hydroalcoholic extract (CHE) that was partitioned to obtain an alkaloid fraction. The alkaloid was then partitioned in polar and nonpolar subfractions. β-Sitosterol was isolated from the nonpolar subfraction and identified by comparison with the literature. The effect of β-sitosterol on ⁴⁵Ca²⁺ uptake in activated murine neutrophils, and upon myeloperoxidase and adenosine deaminase activity, IL-1β and TNF-α levels in carrageenan-induced inflammation in mice were evaluated.. β-Sitosterol promoted a time- and dose-dependent increase of the calcium uptake in activated neutrophils that was promptly reversed by nifedipine, BAPTA-AM, LY294002, and colchicine. β-Sitosterol inhibited myeloperoxidase and adenosine deaminase activity, and IL-1β and TNF-α levels.. β-Sitosterol inhibited either myeloperoxidase and adenosine deaminase activity or IL-1β and TNF-α levels. This effect seemed to be mediated by the calcium uptake in activated neutrophils in a time- and concentration-dependent manner through L-type voltage dependent calcium channels, intracellular calcium, phosphoinositide kinase-3, and microtubule modulation.

    Topics: Adenosine Deaminase; Adenosine Deaminase Inhibitors; Animals; Anti-Inflammatory Agents; Calcium Channel Blockers; Calcium Channels, L-Type; Calcium Signaling; Dose-Response Relationship, Drug; Enzyme Inhibitors; Hypolipidemic Agents; Injections, Intraperitoneal; Interleukin-1beta; Mice; Microtubules; Neutrophil Activation; Neutrophils; Peroxidase; Phosphatidylinositol 3-Kinase; Phosphoinositide-3 Kinase Inhibitors; Pleurisy; Sitosterols; Tubulin Modulators; Tumor Necrosis Factor-alpha

2013
Comparative seasonal sterol profiles in edible parts of Mediterranean fish and shellfish species.
    International journal of food sciences and nutrition, 2013, Volume: 64, Issue:4

    The effect of different seasons on sterol content of seafoods was investigated. There were four sterols (cholesterol, sitosterol, desmosterol and stigmasterol) identified, with cholesterol being the predominant sterol. Stigmasterol was a minor component in fish muscle, whilst sitosterol was one of the main phytosterols found in fish muscle. Cholesterol content of fish consisted of 38-100% of total sterols in fish and 54-80% of total sterols in shellfish. The highest cholesterol content of fish muscle was found in summer and the lowest in autumn, whereas season did not have any effect on cholesterol level of green tiger prawn and speckled shrimp. Total sterol content of fish muscle ranged from 49 to 110 mg/100 g, although the range of total sterols in shrimp muscle was between 62 and 91 mg/100 g. The result of the study showed that total sterols in fish were generally found at lower levels in winter compared with other seasons.

    Topics: Animals; Cholesterol; Crustacea; Desmosterol; Fishes; Mollusca; Muscles; Seafood; Seasons; Shellfish; Sitosterols; Sterols; Stigmasterol

2013
Incorporation of β-sitosterol into mitochondrial membrane enhances mitochondrial function by promoting inner mitochondrial membrane fluidity.
    Journal of bioenergetics and biomembranes, 2013, Volume: 45, Issue:3

    Recent findings suggest that mitochondrial membrane fluidity could influence mitochondrial energy metabolism. β-sitosterol (BS) is a common plant sterol that is prevalent in plant oils, nuts, cereals and plant food products. Its chemical structure is very similar to that of cholesterol. As a cholesterol analog, BS is highly lipid soluble and largely resides in the membranes of cells or organelles where it may have an influence on the membrane fluidity. The present study reports that, with the cholesterol chelator 2-hydroxypropyl-β-cyclodextrin (HPβCD) as its carrier, BS is able to increase the fluidity of the inner mitochondrial membrane (IMM) without affecting the fluidity of the outer mitochondrial membrane (OMM), and consequently to increase the mitochondrial membrane potential (∆Ψm) and mitochondrial ATP content. It has been previously proposed that a therapeutical boost in adenosine triphosphate (ATP) levels in mitochondria may be beneficial for neurodegenerative diseases such as Alzheimer's disease (AD). Given that dietary administration of plant sterols could increase brain BS concentrations, these results may provide a better understanding of the beneficial effects of plant sterol-enriched nutrients on neurodegenerative diseases such as AD.

    Topics: Alzheimer Disease; Cell Line; Humans; Hypolipidemic Agents; Membrane Fluidity; Mitochondria; Mitochondrial Membranes; Sitosterols

2013
β-Sitosterol oxidation products attenuate vasorelaxation by increasing reactive oxygen species and cyclooxygenase-2.
    Cardiovascular research, 2013, Mar-01, Volume: 97, Issue:3

    β-Sitosterol has become a popular cholesterol-lowering functional food product worldwide. β-Sitosterol can be oxidized to β-sitosterol oxidation products (SOPs) during food processing. Little is known about the impact of SOPs and β-sitosterol on the functionality of arteries. This study investigated the effects of SOPs and β-sitosterol on vasorelaxation and the possible cellular mechanisms involved.. By isometric tension measurement, SOPs but not β-sitosterol blunted relaxation induced by acetylcholine or Ca(2+) ionophore A23187 in endothelium-intact aortae. SOPs-impaired vasorelaxation was completely reversed by cyclooxygenase (COX)-2 inhibitor DuP-697, whereas the reversal by COX-1 inhibitor SC-560 was only partial. Western blotting and immunohistochemistry showed that SOPs increased the protein expression of COX-2 but not COX-1 in the endothelium. Using dihydroethidium staining and electron paramagnetic resonance spin trapping techniques, SOPs were found to elevate the level of reactive oxygen species in rat aortic endothelial cells, and the effects were reversed by antioxidants tempol, tiron, or diphenylene iodonium. Consistently, these antioxidants reversed SOPs-induced impairment of endothelium-dependent relaxation. Up-regulation of COX-2 expression by SOPs was also reversed by tempol. Moreover, SOPs attenuated nitric oxide donor sodium nitroprusside-induced relaxation in endothelium-intact, but not endothelium-denuded rings, confirming that SOPs act on the endothelium. Interestingly, a thromboxane-prostanoid (TP) receptor blocker S18886 reversed SOPs-impaired vasorelaxation, suggesting the involvement of TP receptor in mediating the downstream effect. SOPs decreased cGMP production, and the effect could be reversed by inhibiting COX-2 or TP receptor.. This study provides novel experimental evidence showing the harmful effects of SOPs on endothelial function.

    Topics: Acetylcholine; Animals; Aorta; Calcimycin; Cells, Cultured; Cyclooxygenase 2; Endothelium, Vascular; Enzyme Inhibitors; Male; Models, Animal; Oxidation-Reduction; Pyrazoles; Rats; Rats, Sprague-Dawley; Reactive Oxygen Species; Sitosterols; Thiophenes; Vasodilation

2013
Betulinol and wood sterols in sediments contaminated by pulp and paper mill effluents: dissolution and spatial distribution.
    Environmental science and pollution research international, 2013, Volume: 20, Issue:7

    The goal was to determine dissolution potency of betulinol and wood sterols (WSs) from pulp and paper mill-contaminated sediments and the current stratification for assessment the load due to potential erosion in the river-like watercourse. Both compounds are wood extractives, which may be toxic to benthos and fish. This research continues a study in which other wood extractives, resin acids and their derivative, retene, were analysed. Sediments were collected from 1, 3.5, 12, 15, and 33 km downstream from the pulp and paper mills, and from 2 upstream reference sites. The dissolution potency into sediment-water elutriates (1 + 4 v/v) was studied by two agitation times and temperatures. The vertical amounts of extractives were determined from the uppermost 20 cm of sediment. The amounts of extractives potentially released were estimated from the sediment layers 0-2 and 2-5 cm by using spatial interpolation. According to the interpolation, the total amount of betulinol and β-sitosterol was calculated as kg/ha in the whole sediment area. Significant concentrations of betulinol (1,666 μg/g, dw) and WSs (2,886 μg/g, dw) were measured from the sediments. According spatial interpolation, the highest calculated amount of betulinol (4,726 kg/ha) and that of the most abundant WS, β-sitosterol (3,571 kg/ha), were in the lake where the effluents were discharged. In the dissolution experiment, the highest concentration of betulinol in sediment (0-10 cm) and elutriate was 412 μg/g (dw) and 165 μg/l, respectively. For WSs, concentrations were 768 μg/g (dw) in sediment and 273 μg/l in elutriate. In a worst-case scenario, betulinol may be desorbed to water in concentrations which are hazardous to aquatic animals. Instead WSs are not a risk in this study area. The amount of desorption varied depending on the concentration of contaminants in sediment, the nature of disturbance, and the sediment organic carbon content.

    Topics: Acids; Environmental Monitoring; Geologic Sediments; Industrial Waste; Paper; Phenanthrenes; Resins, Plant; Sitosterols; Triterpenes; Water Pollutants, Chemical; Wood

2013
Incorporation of beta-sitosterol into the membrane increases resistance to oxidative stress and lipid peroxidation via estrogen receptor-mediated PI3K/GSK3beta signaling.
    Biochimica et biophysica acta, 2013, Volume: 1830, Issue:3

    Brain lipid peroxidation has long been considered a potential therapeutic target for Alzheimer's disease (AD). beta-sitosterol (BS), a plant sterol that is prevalent in plant plasma membrane, has been suggested to have antioxidant activity. Previous studies have demonstrated that dietary BS can enter the brain and accumulates in the plasma membrane of brain cells. However, it is unknown whether and how BS exerts its antioxidant activity in plasma membrane.. To incorporate BS into the plasma membrane in vitro, HT22 cells and primarily cultured hippocampal cells were supplemented with BS using 2-hydroxypropyl-beta-cyclodextrin (HPbetaCD) as a carrier. The present study then tested the antioxidant effect of membrane BS against glucose oxidase (GOX)-induced oxidative stress and lipid peroxidation, and whether the antioxidant effect of membrane BS was associated with estrogen receptor (ER)-mediated phosphatidyl inositol 3-kinase (PL3K)/glycogen synthase kinase 3 (GSK3beta) signaling.. Incorporation of BS into cell membrane prevented GOX-induced oxidative stress and lipid peroxidation, which could be suppressed by the ER antagonists and PI3K inhibitor. Additional experiments showed that incorporation of BS into cell membrane induced an up-regulation of PI3K activity and a recruitment of PI3K to lipid rafts, which could be inhibited by the ER antagonist. Membrane BS also increased the expression of p-GSK3beta, which could be suppressed in the presence of the ER antagonist and PI3K inhibitor.. Given that BS is prevalent in foods such as plant oil, the results provide a better understanding of the beneficial effects of these BS-enriched nutrients on neurodegenerative diseases such as AD.

    Topics: 2-Hydroxypropyl-beta-cyclodextrin; Animals; Animals, Newborn; Antioxidants; beta-Cyclodextrins; Cell Line; Cell Survival; Drug Carriers; Gene Expression Regulation; Glucose Oxidase; Glycogen Synthase Kinase 3; Glycogen Synthase Kinase 3 beta; Hippocampus; Membrane Microdomains; Neurons; Oxidation-Reduction; Oxidative Stress; Phosphatidylinositol 3-Kinases; Primary Cell Culture; Rats; Rats, Sprague-Dawley; Receptors, Estrogen; Signal Transduction; Sitosterols

2013
Effect of pigeon pea (Cajanus cajan L.) on high-fat diet-induced hypercholesterolemia in hamsters.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2013, Volume: 53

    Obesity is associated with increased systemic and airway oxidative stress, which may result from a combination of adipokine imbalance and antioxidant defenses reduction. Obesity-mediated oxidative stress plays an important role in the pathogenesis of dyslipidemia, vascular disease, and nonalcoholic hepatic steatosis. The antidyslipidemic activity of pigeon pea were evaluated by high-fat diet (HFD) hamsters model, in which the level of high-density lipoprotein-cholesterol (HDL-C), low-density lipoprotein-cholesterol (LDL-C), total cholesterol (TC), and total triglyceride (TG) were examined. We found that pigeon pea administration promoted cholesterol converting to bile acid in HFD-induced hamsters, thereby exerting hypolipidemic activity. In the statistical results, pigeon pea significantly increased hepatic carnitine palmitoyltransferase-1 (CPT-1), LDL receptor, and cholesterol 7α-hydroxylase (also known as cytochrome P450 7A1, CYP7A1) expression to attenuate dyslipidemia in HFD-fed hamsters; and markedly elevated antioxidant enzymes in the liver of HFD-induced hamsters, further alleviating lipid peroxidation. These effects may attribute to pigeon pea contained large of unsaturated fatty acids (UFA; C18:2) and phytosterol (β-sitosterol, campesterol, and stigmasterol). Moreover, the effects of pigeon pea on dyslipidemia were greater than β-sitosterol administration (4%), suggesting that phytosterone in pigeon pea could prevent metabolic syndrome.

    Topics: Animals; Antioxidants; Cajanus; Carnitine O-Palmitoyltransferase; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Cholesterol, HDL; Cholesterol, LDL; Chromatography, High Pressure Liquid; Cricetinae; Diet, High-Fat; Disease Models, Animal; Hypercholesterolemia; Lipid Peroxidation; Liver; Male; Obesity; Oxidative Stress; Phytosterols; Receptors, LDL; Sitosterols; Stigmasterol; Triglycerides

2013
Unsaturated fatty acids and phytosterols regulate cholesterol transporter genes in Caco-2 and HepG2 cell lines.
    Nutrition research (New York, N.Y.), 2013, Volume: 33, Issue:2

    Dietary consumption of phytosterols and certain fatty acids has been shown to reduce cholesterol absorption and plasma cholesterol concentrations. However, it has not been fully elucidated whether phytosterols or fatty acids can alter the expression of cholesterol transporters by functioning as signaling molecules. This study tested the hypothesis that various fatty acids and phytosterols commonly found in the food supply can modulate the expression of transporters including Niemann-Pick C1-like 1, low-density lipoprotein receptor, and scavenger receptor class B type I and 3-hydroxy-3-methylglutaryl-coenzyme A reductase in the intestine and liver. Caco-2 cells were used as models of enterocytes, and HepG2 cells were used as a model of hepatocytes. The cells were treated for 18 hours with 100 μmol/L of a fatty acid, or for 24 hours with 10 μmol/L of 25α-hydroxycholesterol, or 100 μmol/L of cholesterol, sitosterol, and stigmasterol to measure expression of genes involved in cholesterol transport using quantitative real-time polymerase chain reaction. Polyunsaturated fatty acids in Caco-2 cells and sterols in HepG2 cells significantly reduced the messenger RNA expression levels of Niemann-Pick C1-like 1, scavenger receptor class B type I, low-density lipoprotein receptor, and 3-hydroxy-3-methylglutaryl-coenzyme A reductase. Importantly, sitosterol and stigmasterol reduced the messenger RNA levels of genes to a similar extent as cholesterol. The data support the hypothesis that unsaturated fatty acid and phytosterols can act as signaling molecules and alter the expression of genes involved in cholesterol transport and metabolism.

    Topics: Acyl Coenzyme A; Caco-2 Cells; Carrier Proteins; Cholesterol; Diet; Dietary Fats; Fatty Acids, Unsaturated; Gene Expression; Hep G2 Cells; Humans; Intestinal Mucosa; Liver; Oxidoreductases; Phytosterols; Real-Time Polymerase Chain Reaction; Receptors, LDL; RNA, Messenger; Scavenger Receptors, Class B; Signal Transduction; Sitosterols; Stigmasterol

2013
[Composition and content of biologically active substances in rose hips].
    Voprosy pitaniia, 2012, Volume: 81, Issue:6

    The paper studies the chemical composition of the powders obtained from the pulp with the skins and seeds of fruits of wild rose hips. Research results have shown that the main fraction of the powder is dietary fiber, powder of seeds of insoluble fiber in 1,6 and 2,3 higher than in the powder of the fruit with a thin skin and pulp, respectively. The greatest amount of carbohydrates and protein found in powders and pulp of the fruit with a thin skin, and lipids predominate in the powder from the seeds. Found that the lipid powder rosehip richest in oleic, linoleic and linolenic acids, the share of oleic acid has 6,4-19,2%, linoleic and linolenic 19,7-45,8 and 23,3-33,9% of the amount of fatty acids. Lipids powders of hips and seeds of rose have higher levels of essential linoleic acid and powder from the pulp with the skins - linolenic acid. In the study established the presence of sterols 7 fractions, the predominant of which is the beta-sitosterol. In the powder from the pulp with the skins found the greatest amount of ascorbic acid, carotenoids, and the powder of seeds - vitamin E. Carotenoids in powders are beta-carotene and lycopene. The high content of ascorbic acid, vitamin E and carotenoids in powder from wild rose hips makes them a good source of antioxidants. Therefore, we studied the possibility of using vegetable powders obtained from hips of wild rose, to enrich biologically active substances such as vitamins C, E and carotenoids, food supply, particularly of health care use. Rosehip powder from the pulp with the skins had the highest antioxidant activity, antioxidant activity of hips powders was 74% of the activity of powder from the pulp with the skins, the lowest antioxidant activity was observed in the powder from the wild rose seeds. That's way, based on the analysis of the chemical composition of rose hip powder found high levels they ascorbic acid, carotenoids, flavonoids,found their high antioxidant activity. It allows to recommend powders produced from the hips, as a source of physiologically functional ingredients for the production of fortified food products, especially medical and prophylactic purposes. The use of such additives will fill the gap in the body of P-active substances, vitamins C and E, beta-carotene, pectin substances.

    Topics: Ascorbic Acid; Carotenoids; Fatty Acids, Unsaturated; Food Analysis; Food, Fortified; Fruit; Pectins; Rosa; Sitosterols; Vitamin E

2012
[Study on the chemical constituents in Pouzolzia zeylanica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:11

    To study the chemical constituents of Pouzolzia zeylanica.. Many chromatography means were used in separation and purification, and the structures of all compounds were identified by the means of spectroscopic analysis and physicochemical properties.. 14 compounds were elucidated as: beta-sitosterol (1), daucosterol (2), oleanolic acid (3), epicatechin (4), alpha-amyrin (5), eugenyl-beta-rutinoside (6), 2alpha, 3alpha, 19alpha-trihydroxyurs-12-en-28-oic (7), scopolin (8), scutellarein-7-O-alpha-L-rhamnoside (9), scopoletin (10), quercetin (11), quercetin-3-O-beta-D-glucoside (12), apigenin (13), 2alpha-hydroxyursolic acid (14).. All compounds are obtained from this plant for the first time.

    Topics: Catechin; Chromatography, Thin Layer; Glycosides; Oleanolic Acid; Sitosterols; Urticaceae

2012
[Study on chemical constituents from the roots and rhizomes of Sinopodophyllum emodi].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:10

    To investigate the chemical constituents in the roots and rhizomes of Sinopodophyllum emodi.. The compounds were isolated by many different chromatographic methods such as silica gel, Sephadex LH-20, and ODS column. Their structures were identified by their physicochemical properties and spectrascopic data.. Nine compounds were isolated and identified as isopicrodeoxypodophyllotoxin(I), 3beta-hydroxy-7alpha-methoxy-24beta-ethyl-cholest-5-ene(II), 5alpha, 8alpha-epidioxy-(22E,24R)-erg-osta-6,22-dien-3beta-ol(III), 7beta-hydroxysitosterol (IV), beta-sitosterol (V), daucosterol (VI), alpha-glyceryl palmitate (VII), alpha-D-glucose (VIII), 5-hydromethyl furaldehyde (IX).. Compounds I - IV, VII - IX are obtained from this genus for the first time.

    Topics: Berberidaceae; Glucose; Glycerides; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Roots; Plants, Medicinal; Rhizome; Sitosterols

2012
[Effect of banxia xiexin decoction on leptin and endothelin-1 of gastric ulcer rat and the optimal combination screening of active components].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:10

    To select the optimal combination of five active component of Banxia Xiexin Decoction on gastric ulcer rat, and observe its effect on Leptin and ET-1.. Eighty-seven SD rats were randomly divided into normal group, sham-operated group and acetic acid-induced gastric ulcer group, omeprazole group as a positive control, five active components (glycyrrhetic acid, beta-sitosterol, berberine, baicalin and ginsenoside) of Banxia Xiexin Decoction were divided into groups by L16 orthogonal design. The ulcer area, and the content of Leptin and ET-1, and the mRNA expression level of both were detected.. Among the sixteen orthogonal design groups, the ulcer area of these groups using both beta-sitosterol and berberine was the smallest (P < 0.05), the content of Leptin of these groups using both glycyrrhetic acid and ginsenoside was the highest in blood serum (P < 0.05), the group using glycyrrhetic acid had the minimum concentration of ET-1 in blood plasma. Compared with model group, berberine could raise the mRNA expression level of Leptin (P < 0.01), and beta-sitosterol could lower the mRNA expression level of ET-1 (P < 0.01).. The pathogenesis of gastric ulcer may be related with the down-regulation of concentration and mRNA expression level of Leptin, and upregulation of concentration and mRNA expression level of ET-1, the active components in Banxia Xiexin Decoction may upregulated Leptin and inhibit ET-1 to accelerate the healing of gastric ulcer.

    Topics: Acetates; Animals; Berberine; Disease Models, Animal; Drugs, Chinese Herbal; Endothelin-1; Flavonoids; Gastric Mucosa; Leptin; Male; Plants, Medicinal; Random Allocation; Rats; Rats, Sprague-Dawley; RNA, Messenger; Sitosterols; Stomach Ulcer

2012
Non-cholesterol sterols in different forms of primary hyperlipemias.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2012, Volume: 22, Issue:3

    We investigated the behaviour of non-cholesterol sterols, surrogate markers of cholesterol absorption (campesterol and sitosterol) and synthesis (lathosterol), in primary hyperlipemias.. We studied 53 patients with polygenic hypercholesterolemia (PH), 38 patients with familial combined hyperlipemia (FCH), and 19 age- and sex-matched healthy control subjects. In all participants, plasma sitosterol, campesterol and lathosterol were determined by gas chromatography coupled to mass spectrometry. To correct for the effect of plasma lipid levels, non-cholesterol sterol concentrations were adjusted for plasma cholesterol (10² μmol/mmol cholesterol). Patients with FCH were more frequently men, and had higher body mass index (BMI), fasting glucose, insulin and HOMA-IR. Lathosterol was higher in FCH than in pH or controls (p < 0.05). Campesterol was significantly lower in FCH (p < 0.05), while no differences were found between pH and controls. Sitosterol displayed higher values in pH compared to FCH (p < 0.001) and controls (p < 0.05). Spearman's rank correlations showed positive correlations of lathosterol with BMI, waist circumference, HOMA-IR, triglycerides, apoprotein B, and a negative one with HDL-cholesterol. Sitosterol had a negative correlation with BMI, waist circumference, HOMA-IR, triglycerides, and a positive one with HDL-cholesterol and apoprotein AI. Multivariate regression analyses showed that cholesterol absorption markers predicted higher HDL-cholesterol levels, while HOMA-IR was a negative predictor of sitosterol and BMI a positive predictor of lathosterol.. Our findings suggest the occurrence of an increased cholesterol synthesis in FCH, and an increased cholesterol absorption in pH. Markers of cholesterol synthesis cluster with clinical and laboratory markers of obesity and insulin resistance.

    Topics: Adult; Aged; Biomarkers; Case-Control Studies; Cholesterol; Female; Gas Chromatography-Mass Spectrometry; Humans; Hypercholesterolemia; Hyperlipidemia, Familial Combined; Intestinal Absorption; Italy; Linear Models; Male; Middle Aged; Multifactorial Inheritance; Multivariate Analysis; Phytosterols; Risk Assessment; Risk Factors; Sitosterols; Sterols; Young Adult

2012
Chemical composition, anti-inflammatory, molluscicidal and free-radical scavenging activities of the leaves of Ficus radicans 'Variegata' (Moraceae).
    Natural product research, 2012, Volume: 26, Issue:4

    The methanol crude extract of the leaves of Ficus radicans Roxb. 'Variegata' (Moraceae) and the n-hexane, ethyl acetate and aqueous methanol fractions resulting from its fractionation were evaluated for their anti-inflammatory, molluscicidal and free-radical scavenging activities. The crude extract and fractions exhibited significant inhibition of inflammation in both croton oil (CO)-induced ear oedema in mice (p<0.001) and carrageenan-induced rat paw oedema models (p<0.01). The molluscicidal assay against Biomphalaria glabrata showed a weak activity for the n-hexane fraction (DL(50)= 400 µg mL(-1)). A moderated 1,1-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging activity was observed for the ethyl acetate fraction (IC(50)= 66.2 µg mL(-1)). Fractionation of the extracts through chromatographic methods afforded the coumarins 7-methoxycoumarin, 7-hydroxy-6-methoxycoumarin and methoxy-3,4-dihydrocoumarin, the steroids β-sitosterol and β-sitosterol 3-O-β-glucopyranoside, as well as a cinnamic acid derivative and a flavonoid identified as trans-4-methoxy-2-β-D-glucopyranosyloxy cinnamic acid and quercetin 3-O-β-D-xylopyranosyl-(1 → 2)-α-L-rhamnopyranoside, respectively. The compounds were identified on the basis of their NMR spectral data and comparison with those previously reported in the literature.

    Topics: Animals; Anti-Inflammatory Agents; Biomphalaria; Biphenyl Compounds; Carrageenan; Cinnamates; Croton Oil; Drug Evaluation, Preclinical; Edema; Ficus; Free Radical Scavengers; Glucosides; Male; Mice; Molecular Structure; Molluscacides; Monosaccharides; Picrates; Plant Extracts; Plant Leaves; Quercetin; Rats; Rats, Wistar; Scopoletin; Sitosterols

2012
Visceral fat positively correlates with cholesterol synthesis in dyslipidaemic patients.
    European journal of clinical investigation, 2012, Volume: 42, Issue:2

    Quantification of plasma noncholesterol sterols allows the study of cholesterol absorption and synthesis. A pattern of low cholesterol absorption and high synthesis has been demonstrated in patients with obesity and insulin resistance. To understand the relationship between cholesterol absorption/synthesis and visceral obesity, we investigated surrogate markers of cholesterol absorption (campesterol and sitosterol) and synthesis (lathosterol) in dyslipidaemic patients with different representation of abdominal fat, estimated by ultrasonographic measurement of visceral fat area (VFA).. In 126 patients with primary hyperlipaemias, plasma sitosterol, campesterol and lathosterol were determined by gas chromatography coupled with mass spectrometry. Visceral and subcutaneous fats were evaluated by ultrasonography. The study population was divided into two groups on the basis of VFA median values, below/equal and above 154 cm(2) . RESULTS Patients with higher VFA had significantly higher lathosterol levels (median 109 vs. 76 × 10(2) μmol/mmol cholesterol P < 0·004), body mass index, waist circumference, blood pressure, triglycerides, insulin, homoeostatic model assessment (HOMA)-IR and lower high-density lipoprotein (HDL)-C. VFA was positively correlated with lathosterol (ρ = 0·35, P < 0·001) and negatively with HDL-C (ρ = -0·43, P < 0·001), campesterol (ρ = -0·23, P = 0.01) and sitosterol (ρ = -0·35, P < 0·001). VFA was an independent predictor of lathosterol values (β = 0·389, P < 0·0001, P of the model < 0·0001);age, systolic blood pressure, BMI, waist circumference, triglycerides, HDL-C and HOMA failed to enter the final equation..   In hyperlipidaemic patients, the amount of visceral fat correlates with cholesterol synthesis; the use of ultrasonographic detection of abdominal adiposity allows a better characterization of cholesterol pathway, potentially useful for a tailored therapeutic approach.

    Topics: Adult; Body Fat Distribution; Body Mass Index; Cholesterol; Chromatography, Gas; Dyslipidemias; Female; Humans; Intra-Abdominal Fat; Male; Mass Spectrometry; Middle Aged; Phytosterols; Sitosterols; Statistics as Topic; Ultrasonography; Waist Circumference

2012
Bioactive metabolites from Phoma species, an endophytic fungus from the Chinese medicinal plant Arisaema erubescens.
    Applied microbiology and biotechnology, 2012, Volume: 93, Issue:3

    Through bioassay-guided fractionation, the EtOAc extract of a culture broth of the endophytic fungus Phoma species ZJWCF006 in Arisaema erubescens afforded a new α-tetralone derivative, (3S)-3,6,7-trihydroxy-α-tetralone (1), together with cercosporamide (2), β-sitosterol (3), and trichodermin (4). The structures of compounds were established on the basis of spectroscopic analyses. Compounds 1, 2, and 3 were obtained from Phoma species for the first time. Additionally, the compounds were subjected to bioactivity assays, including antimicrobial activity, against four plant pathogenic fungi (Fusarium oxysporium, Rhizoctonia solani, Colletotrichum gloeosporioides, and Magnaporthe oryzae) and two plant pathogenic bacteria (Xanthomonas campestris and Xanthomonas oryzae), as well as in vitro antitumor activities against HT-29, SMMC-772, MCF-7, HL-60, MGC80-3, and P388 cell lines. Compound 1 showed growth inhibition against F. oxysporium and R. solani with EC₅₀ values of 413.22 and 48.5 μg/mL, respectively. Additionally, compound 1 showed no cytotoxicity, whereas compound 2 exhibited cytotoxic activity against the six tumor cell lines tested, with IC₅₀ values of 9.3 ± 2.8, 27.87 ± 1.78, 48.79 ± 2.56, 37.57 ± 1.65, 27.83 ± 0.48, and 30.37 ± 0.28 μM, respectively. We conclude that endophytic Phoma are promising sources of natural bioactive and novel metabolites.

    Topics: Anti-Bacterial Agents; Antifungal Agents; Antineoplastic Agents; Arisaema; Ascomycota; Benzofurans; Cell Line, Tumor; Culture Media, Conditioned; Endophytes; Fungi; HL-60 Cells; HT29 Cells; Humans; Medicine, Chinese Traditional; Plant Diseases; Sitosterols; Species Specificity; Tetralones; Trichodermin; Xanthomonas

2012
Isolation and chromatographic analysis of bioactive triterpenoids from the bark extract of Cariniana domestica (Mart) Miers.
    Natural product research, 2012, Volume: 26, Issue:1

    The Lecythidaceae family is composed of 25 genera and 400 species that occur in the form of trees with a pantropical distribution. The genera Cariniana belongs to the family Lecythidaceae, and there are few reports considering these species. In this work, fractionation of the dichloromethane fraction obtained from the aqueous extract of the stem bark of Cariniana domestica (Mart) Miers, popularly known as Jequitibá-roxo, led to the isolation of two mixtures of triterpenoids: lupeol and β-amyrin and β-sitosterol and stigmasterol. The structures of the isolated compounds were elucidated by spectroscopic (NMR) and chromatographic (GC-MS) techniques as well as literature data comparisons. β-Sitosterol, stigmasterol, lupeol and β-amyrin were quantified in dichloromethane fraction by high-performance liquid chromatography (HPLC/DAD). The dichloromethane fraction was also investigated for antioxidant and antifungal activities. The isolated compounds and their biological activities are reported for the first time for the species C. domestica.

    Topics: Antifungal Agents; Antioxidants; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Lecythidaceae; Magnetic Resonance Spectroscopy; Methylene Chloride; Molecular Structure; Oleanolic Acid; Pentacyclic Triterpenes; Plant Bark; Plant Extracts; Saccharomyces cerevisiae; Sitosterols; Stigmasterol; Triterpenes

2012
Cholesterol oxidase ChoD is not a critical enzyme accounting for oxidation of sterols to 3-keto-4-ene steroids in fast-growing Mycobacterium sp. VKM Ac-1815D.
    The Journal of steroid biochemistry and molecular biology, 2012, Volume: 129, Issue:1-2

    Fast-growing strain of Mycobacterium sp. VKM Ac-1815D is capable of effective oxidizing of sterols (phytosterol, cholesterol, ergosterol) to androstenedione and other valuable 3-oxo-steroids. To elucidate the role of cholesterol oxidase in sterol catabolism by the strain, the choD gene has been cloned and sequenced. The deduced gene product (M(r) 63.5kDa) showed homologies over its entire length to a large number of proteins belonging to the InterPro-family EPR006076, which includes various FAD dependent oxidoreductases. The expression of choD in Escherichia coli was shown to result in the synthesis of membrane associated cholesterol oxidase. In addition to cholesterol, the enzyme oxidized β-sitosterol, dehydroepiandrosterone, ergosterol, pregnenolone, and lithocholic acid. Knock-out of choD in Mycobacterium sp. VKM Ac-1815D strain was obtained by the gene replacement technique. The mutant strain transformed sitosterol forming exclusively 3-keto-4-ene steroids with androstenedione as a major product, thus evidencing that choD knock out did not abrogate sterol A-ring oxidation. The results indicated that ChoD is not a critical enzyme responsible for modification of 3β-hydroxy-5-ene- to 3-keto-4-ene steroids in Mycobacterium sp. VKM Ac-1815D. Article from a special issue on steroids and microorganisms.

    Topics: Cholesterol Oxidase; Cloning, Molecular; Escherichia coli; Mycobacterium; Sitosterols; Sterols

2012
A new highly hydroxylated triterpene from Salvia atropatana Bunge.
    Natural product research, 2012, Volume: 26, Issue:20

    One new triterpenoid olean-18-ene-1β, 2α, 3β-triol (1) along with four known compounds were isolated from the chloroform extract of the aerial part of Salvia atropatana Bunge. The known compounds were two flavonoids, 5-hydroxy-7,4'-dimethoxyflavone (2) and 5-hydroxy-6,7,4'-trimethoxyflavone (3), an abietane-type diterpene namely taxodione (4) and a phytosterol namely γ -sitosterol (5). The structure of (1) was elucidated by comprehensive spectroscopic analysis including electron ionization-mass spectra (EI-MS), (1)H NMR, (13)C NMR, distortionless enhancement by polarization transfer (DEPT), H,H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond correlation (HMBC). The structure of known compounds 2-5 were identified by comparison of their spectral data with those reported in the literature.

    Topics: Apigenin; Diterpenes; Flavones; Flavonoids; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Components, Aerial; Salvia; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Triterpenes

2012
Competitive solubilization of cholesterol and β-sitosterol with changing biliary lipid compositions in model intestinal solution.
    Chemistry and physics of lipids, 2012, Volume: 165, Issue:1

    We used a model intestinal solution to understand the mechanisms of cholesterol lowering by the addition of plant sterols. The experimental results of the competitive solubilization of cholesterol and β-sitosterol in vitro give useful information about these mechanisms. The states of the model intestinal solution as a solubilizer were analyzed by transmission electron microscopy (TEM) and dynamic light scattering (DLS) by changing the number of components, and the bile salt and phosphatidylcholine concentrations. There were aggregates of different sizes: liposomes and mixed micelles depending on their components and concentrations. The maximum solubilization of cholesterol increased from 0.2mM to 1.3mM when adding fatty compounds in the pure bile salts system, which is almost the same as the full components model intestinal solution. Therefore, an excessive intake of fatty compounds may also increase cholesterol absorption in vivo. Even if the components of the model intestinal solution were modified from the standard condition, there were not remarkable differences in the selectivity of cholesterol and β-sitosterol in competitive solubilization. With the addition of β-sitosterol, the maximum solubilization of cholesterol decreases to almost half of that in the system with only cholesterol, except for PC-rich systems. In general, the different structures of aggregates considerably influence the maximum solubilization of sterols but not the selectivity of cholesterol and β-sitosterol in the competitive solubilization. The Gibbs energy change (ΔG°) of the solubilization of β-sitosterol showed a more negative value than cholesterol by -4 to -6kJmol(-1), which indicates that β-sitosterol is energetically favored relative to cholesterol in the model intestinal solution, regardless of the different systems.

    Topics: Cholesterol; Light; Lipid Bilayers; Liposomes; Micelles; Models, Biological; Phosphatidylcholines; Scattering, Radiation; Sitosterols; Solubility; Spectrophotometry, Ultraviolet; Thermodynamics

2012
Molecular docking of γ-sitosterol with some targets related to diabetes.
    European journal of medicinal chemistry, 2012, Volume: 47, Issue:1

    γ-sitosterol isolated from Lippia nodiflora was taken as ligand for molecular docking. The molecular targets, glucokinase, Fructose 1, 6- bisphosphatase 1, Human multidrug resistance protein 1 and Cytochromes P450 whose crystallographic structures are available on the PDB database as 1V4S, 2JJK, 3LC4, 2CBZ respectively, were used for the docking analysis using the Autodock tool v 4.2 and ADT v1.5.4 programs. The docking studies of the ligand γ- sitosterol with four different target proteins showed that this is a good molecule which docks well with various targets related to diabetes mellitus. Hence γ-sitosterol can be considered for developing into a potent antidiabetic drug.

    Topics: Computational Biology; Diabetes Mellitus; Humans; Hypoglycemic Agents; Models, Molecular; Protein Conformation; Sitosterols

2012
A new fatty aldol ester from the aerial part of Mimosa invisa (Mimosaceae).
    Natural product research, 2012, Volume: 26, Issue:19

    A new aldol ester named 17-O-triacontanoylheptadecanal (1) was isolated from the aerial part of Mimosa invisa (Mimosaceae) together with eight known compounds identified as β-sitosterol (2), α-amyrine (3), lupeol (4), 4'-O-methylepinumisoflavone (5), alpinumisoflavone (6), betulinic acid (7), 3-O-β-D-glucopyranoside of sitosterol (8) and epirobinetinidol (9). The structures of compounds were determined on the basis of NMR and mass spectrometry data as well as by comparing the data reported in the literatures. The antimicrobial activities of the crude extract and compounds 1 and 9 were investigated against seven microbial species. The natural products showed moderate activities compared to that of the crude extract.

    Topics: Anti-Infective Agents; Betulinic Acid; Drug Evaluation, Preclinical; Fatty Acids; Klebsiella pneumoniae; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Mimosa; Molecular Structure; Pentacyclic Triterpenes; Plant Components, Aerial; Plant Extracts; Plants, Medicinal; Sitosterols; Triterpenes

2012
An ultra performance liquid chromatographic method for determining phytosterol uptake by Caco-2 cells.
    Analytical biochemistry, 2012, Feb-01, Volume: 421, Issue:1

    A simple method for the determination of cellular uptake of phytosterols by Caco-2 cells has been developed by ultra performance liquid chromatography with ultraviolet detection (UPLC-UV). UPLC-UV was established using an ODS column, acetonitrile/H(2)O (9:1, v/v) as a mobile phase, and a detection wavelength at 210 nm. As analytes, β-sitosterol, campesterol, stigmasterol, and brassicasterol were selected based on the abundance in foods and the similarity of their structures. A linear relation was observed between the peak area and the amount of sterol injected from 50 to 2000 pmol (r>0.999) with a relative standard deviation (RSD) of less than 2.5% (n=6). This method was applied to the determination of cellular uptake of phytosterols by Caco-2 cells. Recovery tests showed that phytosterols were extracted from the cell lysates by chloroform and determined by UPLC-UV with a recovery rate of more than 80.2% and an RSD of less than 11.3% (n=3). When Caco-2 cells were incubated with phytosterols at 37°C, their uptake was increased with time in a concentration-dependent manner. This method will be useful for the simultaneous determination of cellular phytosterols in an in vitro intestine model.

    Topics: Biological Transport, Active; Caco-2 Cells; Cholestadienols; Cholesterol; Chromatography, Liquid; Humans; Kinetics; Phytosterols; Sitosterols; Stigmasterol

2012
Langmuir monolayers studies on the relationship between the content of cholesterol in model erythrocyte membranes and the influence of β-sitosterol.
    Colloids and surfaces. B, Biointerfaces, 2012, Mar-01, Volume: 91

    Plant sterols, which are well known dietary taken cholesterol lowering agents, can incorporate into erythrocyte membranes. However, the influence of these compounds on membrane properties seems to be unclear. Since the composition of erythrocytes undergoes changes, e.g., in pathological cases, in this work the relationship between the proportion of lipids in model membranes (Langmuir monolayers) and the effect of β-sitosterol was analyzed. The investigations were carried out for cholesterol/phosphatidylcholine (POPC)/sphingomyelin films differing in the proportion of cholesterol and containing the plant sterol in various concentrations. Additionally, the experiments based on systematic replacement of cholesterol in model membranes were performed. Based on the analysis of mean area and the excess area per molecule, compressional modulus and the excess free energy of mixing values as well as BAM images it was evidenced that the effect of the plant sterol depends on the composition of model membrane. However, it was also found that, in the investigated range of monolayer composition, the increase of total sterol content in the mixed film caused by the presence of β-sitosterol practically does not influence the molecular packing and interactions in the investigated monolayers. On the other hand, the replacement of cholesterol by β-sitosterol causes a decrease of condensation and weakens the interactions between molecules in the mixed film. These effects are the strongest for the systems of the highest content of cholesterol. The most important finding is that the variations in the composition of membranes, widely occurring in natural systems, may influence the effect of phytosterols.

    Topics: Cholesterol; Erythrocyte Membrane; Sitosterols

2012
Anti-snake venom activities of extracts and fractions from callus cultures of Sapindus saponaria.
    Pharmaceutical biology, 2012, Volume: 50, Issue:3

    Sapindus saponaria L. (Sapindaceae) bark, root, and fruits are used as sedatives and to treat gastric ulcer and also demonstrate diuretic and expectorant effects.. The anti-snake venom properties of callus of S. saponaria are investigated here for the first time.. In vitro cultivated callus of Sapindus saponaria were lyophilized, and the extracts were prepared with different solvents, before submitting to phytochemical studies and evaluation of the anti-ophidian activity. Crude extracts were fractionated by liquid-liquid partition and the fractions were monitored by thin layer chromatography (TLC). Subsequently, anti-ophidian activities were analyzed toward Bothrops jararacussu Lacerda (Viperidae), B. moojeni Hoge (Viperidae), B. alternates Duméril (Viperidea) and Crotalus durissus terrificus Lineu (Viperidae) venoms and isolated myotoxins and phospholipase A(2) (PLA(2)).. Fractions A1, A2 and the extract in MeOH:H(2)O (9:1) significantly inhibited the toxic and pharmacological activities induced by snake venoms and toxins, when compared to other extracts and fractions. The lethal, clotting, phospholipase, edema-inducing, hemorrhagic and myotoxic activities were partially inhibited by the different extracts and fractions. TLC profiles of the crude extracts (B and C) and fractions (A1 and A2) showed β-sitosterol and stigmasterol as their main compounds. Stigmasterol exhibited inhibitory effects on enzymatic and myotoxic activities of PLA(2).. Sapindus saponaria extracts and fractions presented anti-ophidian activity and could be used as an adjuvant to serum therapy or for its supplementation, and in addition, as a rich source of potential inhibitors of enzymes involved in several pathophysiological human and animal diseases.

    Topics: Animals; Antivenins; Bothrops; Chromatography, Thin Layer; Crotalus; Male; Mice; Phospholipases A2; Plant Extracts; Sapindus; Sitosterols; Stigmasterol; Viper Venoms

2012
Euterpe oleracea (açai) modifies sterol metabolism and attenuates experimentally-induced atherosclerosis.
    Journal of atherosclerosis and thrombosis, 2012, Volume: 19, Issue:3

    Euterpe Oleracea (açai) is a fruit from the Amazon region whose chemical composition may be beneficial for individuals with atherosclerosis. We hypothesized that consumption of Euterpe Oleracea would reduce atherosclerosis development by decreasing cholesterol absorption and synthesis.. Male New Zealand rabbits were fed a cholesterol-enriched diet (0.5%) for 12 weeks, when they were randomized to receive Euterpe Oleracea extract (n = 15) or water (n = 12) plus a 0.05% cholesterol-enriched diet for an additional 12 weeks. Plasma phytosterols and desmosterol were determined by ultra-performance liquid chromatography and mass spectrometry. Atherosclerotic lesions were estimated by computerized planimetry and histomorphometry.. At sacrifice, animals treated with Euterpe Oleracea had lower levels of total cholesterol (p =0.03), non-HDL-cholesterol (p = 0.03) and triglycerides (p = 0.02) than controls. These animals had smaller atherosclerotic plaque area in their aortas (p = 0.001) and a smaller intima/media ratio (p = 0.002) than controls, without differences in plaque composition. At the end of the study, campesterol, β-sitosterol, and desmosterol plasma levels did not differ between groups; however, animals treated with Euterpe Oleracea showed lower desmosterol/campesterol (p = 0.026) and desmosterol/ β-sitosterol (p =0.006) ratios than controls.. Consumption of Euterpe Oleracea extract markedly improved the lipid profile and attenuated atherosclerosis. These effects were related in part to a better balance in the synthesis and absorption of sterols.

    Topics: Animals; Arecaceae; Atherosclerosis; Cholesterol; Cholesterol, Dietary; Chromatography, High Pressure Liquid; Desmosterol; Immunoenzyme Techniques; Lipids; Male; Phytosterols; Phytotherapy; Plant Extracts; Rabbits; Sitosterols; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

2012
Development and characterization of phyto-vesicles of β-sitosterol for the treatment of androgenetic alopecia.
    Archives of dermatological research, 2012, Volume: 304, Issue:7

    Alopecia is a psychologically distressing phenomenon. Androgenetic alopecia (AGA) is the most common form of alopecia, which affects millions of men and women worldwide, and is an androgen driven disorder. To study the effect of β-sitosterol phyto-vesicles on AGA, the testosterone-induced alopecia model was used. For the study, the albino rats were used and the period of study was 21 days. β-Sitosterol is a phytosterol which is chemically similar to cholesterol. This compound was found suitable for the preparation of phyto-vesicles by the process involving its complexation with phosphatidyl choline. Pharmacokinetic studies of β-sitosterol reveal its poor absorption through the intestine. The objective of the present study is to enhance the bioavailability of β-sitosterol by its complexation with phosphatidyl choline and then to formulate it as phyto-vesicles for the treatment of alopecia. The complex of β-sitosterol was prepared with phosphatidyl choline and characterized on the basis of solubility, melting point, TLC, UV, IR and NMR spectroscopy. This complex was then formulated as phyto-vesicles and then characterized. The results revealed that effect on alopecia is better in case of phyto-vesicles as compared to the complex, physical mixture and the β-sitosterol itself. Enhanced bioavailability of the β-sitosterol complex may be due to the amphiphilic nature of the complex, which greatly enhance the water and lipid solubility of the compound. The present study clearly indicates the superiority of phyto-vesicles over the complex and β-sitosterol, in terms of better absorption and improved activity for the treatment of alopecia.

    Topics: Absorption; Alopecia; Animals; Biological Availability; Disease Models, Animal; Drug Delivery Systems; Humans; Intestines; Male; Phosphatidylcholines; Rats; Rats, Wistar; Sitosterols; Solubility; Testosterone

2012
Analgesic and anti-inflammatory activity of β-sitosterol isolated from Nyctanthes arbortristis leaves.
    Inflammopharmacology, 2012, Volume: 20, Issue:4

    Nyctanthes arbortristis Linn. (Oleaceae) is one of the well-known Indian medicinal plant. Various extracts of leaves of the plant were screened for analgesic activity by hot plate test and acetic acid-induced writhings and anti-inflammatory activity by carrageenan-induced hind paw edema method at the dose of 50 mg/kg, i.p. Petroleum ether extract was found to be most active and hence subjected to activity-guided fractionation. Results showed that β-sitosterol (5, 10 and 20 mg/kg, i.p.) was responsible for the significant and dose-dependent activity comparable with the standard extract. β-Sitosterol from N. arbortristis leaves might be responsible for analgesic and anti-inflammatory activity.

    Topics: Analgesics; Animals; Anti-Inflammatory Agents; Chromatography, Thin Layer; Dose-Response Relationship, Drug; India; Magnetic Resonance Spectroscopy; Male; Mice; Oleaceae; Plant Extracts; Plant Leaves; Plants, Medicinal; Sitosterols

2012
Simultaneous quantification of five marker compounds of Betula utilis stem bark using a validated high-performance thin-layer chromatography method.
    Journal of separation science, 2012, Volume: 35, Issue:3

    A sensitive, selective and robust densitometric high-performance thin-layer chromatographic method was developed and validated for five marker compounds, namely betulin, lupeol, oleanolic acid, 3-acetyloleanolic acid and β-sitosterol, known for their various therapeutic activities. The marker compounds have been isolated from the stem bark of Betula utilis, well characterized by the spectral analysis, and their simultaneous quantitative determination carried out by high-performance thin-layer chromatography (HPTLC) method. The resolution of marker compounds was carried out on silica-gel 60 plates, using n-hexane:ethyl acetate (8:2 v/v) as the mobile phase. The HPTLC densitometry was performed at 500-nm wavelength after the post chromatographic derivatization with ceric ammonium sulfate reagent. The optimized method provided good linear relation (r>0.9960) for all the investigated analytes. The method is simple, and reproducible, which may be applied for quantitative analysis of the above-mentioned marker compounds.

    Topics: Betula; Chromatography, High Pressure Liquid; Oleanolic Acid; Pentacyclic Triterpenes; Plant Bark; Plant Extracts; Plant Stems; Sitosterols; Triterpenes

2012
Multi-molecular markers and metals as tracers of organic matter inputs and contamination status from an Environmental Protection Area in the SW Atlantic (Laranjeiras Bay, Brazil).
    The Science of the total environment, 2012, Feb-15, Volume: 417-418

    The sources and concentrations of aliphatic hydrocarbons (AHs) and polycyclic aromatic hydrocarbons (PAHs), faecal and biogenic sterols, and trace metals at 10 sampling sites located in Laranjeiras Bay, a large Environmental Protection Area in the southern Atlantic region of Brazil, were determined to assess the sources of organic matter and the contamination status of estuarine sediments. Organic compounds were determined by GC-FID and GC-MS, and ICP-OES was used to evaluate trace metals. The total AHs concentration ranged from 0.28 to 8.19 μg g(-1), and n-C(29) and n-C(31) alkanes were predominant, indicating significant inputs from higher terrestrial plants. Unresolved complex mixtures (UCM) were not detected at any site, suggesting that the study area was not significantly contaminated by fossil fuels. The total PAH concentration varied from 3.85 to 89.2 ng g(-1). The ratio between selected PAH isomers showed that combustion of biomass, coal, and petroleum is the main source of PAHs in the study area. The concentrations of the faecal sterols coprostanol and epicoprostanol were below the detection limits, suggesting that sewage was not a significant contributor to sedimentary organic matter. The concentrations of the trace metals (As, Cr, Cu, Ni, Pb and Zn) were low, except near sites located at the mouths of rivers that discharge into the study area and near urbanised regions (Paranaguá city and the adjoining harbour). In general, the concentrations of PAHs were below the threshold effect concentrations (TEL) levels. Although the As, Cr and Ni concentrations were above the TEL levels, the study area can be considered as preserved from human activities.

    Topics: Alkanes; Bays; Brazil; Ergosterol; Geologic Sediments; Polycyclic Aromatic Hydrocarbons; Sitosterols; Trace Elements; Water Pollutants, Chemical

2012
An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens.
    Phytochemistry, 2012, Volume: 76

    This work reports isolation of an unusual lignan with a bicyclic [2.2.2] octene skeleton, named rufescenolide (1), from stems of Cordia rufescens, along with β-sitosterol, stigmasterol, syringaldehyde, 3-β-O-D-glucopyranosyl-sitosterol, methyl caffeate, 4-methoxy-protocatechuic acid and methyl rosmarinate. Structural characterizations employed IR spectroscopic, ESIHRMS and mono and dimensional NMR spectroscopy.

    Topics: Bridged Bicyclo Compounds; Caffeic Acids; Cordia; Hydroxybenzoates; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Octanes; Plant Stems; Sitosterols; Stigmasterol

2012
Dietary intake of plant sterols stably increases plant sterol levels in the murine brain.
    Journal of lipid research, 2012, Volume: 53, Issue:4

    Plant sterols such as sitosterol and campesterol are frequently administered as cholesterol-lowering supplements in food. Recently, it has been shown in mice that, in contrast to the structurally related cholesterol, circulating plant sterols can enter the brain. We questioned whether the accumulation of plant sterols in murine brain is reversible. After being fed a plant sterol ester-enriched diet for 6 weeks, C57BL/6NCrl mice displayed significantly increased concentrations of plant sterols in serum, liver, and brain by 2- to 3-fold. Blocking intestinal sterol uptake for the next 6 months while feeding the mice with a plant stanol ester-enriched diet resulted in strongly decreased plant sterol levels in serum and liver, without affecting brain plant sterol levels. Relative to plasma concentrations, brain levels of campesterol were higher than sitosterol, suggesting that campesterol traverses the blood-brain barrier more efficiently. In vitro experiments with brain endothelial cell cultures showed that campesterol crossed the blood-brain barrier more efficiently than sitosterol. We conclude that, over a 6-month period, plant sterol accumulation in murine brain is virtually irreversible.

    Topics: Animals; Astrocytoma; Blood-Brain Barrier; Brain; Cell Line, Tumor; Cholesterol; Diet; Dose-Response Relationship, Drug; Endothelial Cells; Humans; Liver; Male; Membrane Microdomains; Mice; Mice, Inbred C57BL; Phytosterols; Sitosterols; Stigmasterol; Time Factors

2012
Macrothrombocytopenia/stomatocytosis specially associated with phytosterolemia.
    Clinical and applied thrombosis/hemostasis : official journal of the International Academy of Clinical and Applied Thrombosis/Hemostasis, 2012, Volume: 18, Issue:6

    Phytosterolemia is a rare autosomal recessive disease of plant sterol metabolism, the pathophysiological features of which are high plasma levels of plant sterols and xanthomatosis caused by mutations of ABCG5 and ABCG8 genes, and the combination of hemolysis and macrothrombocytopenia is an unusual clinical manifestation. All the patients of the 3 unrelated phytosterolemia first presented with prominent macrothrombocytopenia and stomatocytosis. They were either homozygous or compound heterozygous for ABCG5/ABCG8 gene mutations and had significantly elevated serum plant sterols levels quantified using high-performance liquid chromatography. The in vitro study demonstrated that sitosterol can cause changes in shape and osmotic fragility of red blood cells. These findings suggest that macrothrombocytopenia and stomatocytosis could be initial and main features in some patients with phytosterolemia and that serum phytosterols and relevant genes should be analyzed in patients whose macrothrombocytopenia and/or stomatocytosis are unexplained, especially whose parents are of consanguineous marriage.

    Topics: ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Erythrocytes, Abnormal; Female; Heterozygote; Homozygote; Humans; Hypercholesterolemia; Intestinal Diseases; Lipid Metabolism, Inborn Errors; Lipoproteins; Male; Mutation; Osmotic Fragility; Pedigree; Phytosterols; Sitosterols; Xanthomatosis

2012
In-vitro cytotoxic activity of β-Sitosterol triacontenate isolated from Capparis decidua (Forsk.) Edgew.
    Asian Pacific journal of tropical medicine, 2012, Volume: 5, Issue:3

    To study the isolation and characterization of the constituent responsible for the cytotoxic activity of the ethanolic extract of stem of Capparis decidua (C. decidua).. The preliminary cytotoxic effect of isolated compound (β-Sitosterol triacontenate) was investigated by MTT assay on A549 solid tumor cells.. IC(50) value of the β-Sitosterol triacontenate was found to be 1 μM. The cytotoxic activity increased in a dose dependent manner in case of β-Sitosterol triacontenate.. The data therefore provide direct evidence for the role of β-Sitosterol triacontenate as a potent antimetastatic agent, which can markedly inhibit the metastatic and invasive capacity of malignant cells.

    Topics: Antineoplastic Agents; Capparis; Cell Line, Tumor; Enzyme-Linked Immunosorbent Assay; Humans; Lung Neoplasms; Magnetic Resonance Spectroscopy; Neoplasm Invasiveness; Neoplasm Metastasis; Plant Extracts; Plant Stems; Sitosterols

2012
β-sitosterol prevents lipid peroxidation and improves antioxidant status and histoarchitecture in rats with 1,2-dimethylhydrazine-induced colon cancer.
    Journal of medicinal food, 2012, Volume: 15, Issue:4

    Oxidative stress has become widely viewed as an underlying condition in diseases such as ischemia/reperfusion disorders, central nervous system disorders, cardiovascular disease, cancer, diabetes, etc. The role that antioxidants play in the process of carcinogenesis has recently gained considerable attention. β-Sitosterol, a naturally occurring sterol molecule, is a relatively mild to moderate antioxidant and exerts beneficial effects in vitro by decreasing the level of reactive oxygen species. The present study evaluated the antioxidant potential of β-sitosterol in 1,2-dimethylhydrazine (DMH)-induced colon carcinogenesis. The enzymatic and nonenzymatic antioxidants and lipid peroxides in colonic and hepatic tissues were evaluated. Generation of reactive oxygen species, beyond the body's endogenous antioxidant capacity, causes a severe imbalance of cellular antioxidant defense mechanisms. Elevated levels of liver lipid peroxides by DMH induction were effectively decreased by β-sitosterol supplementation. β-Sitosterol also exhibited a protective action against DMH-induced depletion of antioxidants such as catalase, superoxide dismutase, glutathione peroxidase, glutathione reductase, glutathione S-transferase, and reduced glutathione in colonic and hepatic tissues of experimental animals. Supplementation with β-sitosterol restored the levels of nonenzymatic antioxidants (vitamin C, vitamin E, and glutathione). Histopathological alterations in DMH-induced animals were restored to near normal in rats treated with β-sitosterol. Thus, β-sitosterol by virtue of its antioxidant potential may be used as an effective agent to reduce DMH-induced oxidative stress in Wistar rats and may be an effective chemopreventive drug for colon carcinogenesis.

    Topics: 1,2-Dimethylhydrazine; Animals; Anticarcinogenic Agents; Antioxidants; Ascorbic Acid; Catalase; Colon; Colonic Neoplasms; Glutathione; Glutathione Peroxidase; Glutathione Reductase; Glutathione Transferase; Lipid Peroxidation; Male; Oxidative Stress; Rats; Rats, Wistar; Reactive Oxygen Species; Sitosterols; Superoxide Dismutase; Vitamin E

2012
Bioactive phenolic amides from Celtis africana.
    Molecules (Basel, Switzerland), 2012, Mar-05, Volume: 17, Issue:3

    Nine compounds have been isolated for the first time from Celtis africana, namely trans-N-coumaroyltyramine (1), trans-N-feruloyltyramine (2), trans-N-caffeoyltyramine (3), lauric acid (4), oleic acid (5), palmitic acid (6), lupeol (7), β-sitosterol (8) and oleanolic acid (9), respectively. Their structures have been elucidated by different spectroscopic techniques. The isolated compounds were screened for their antioxidant, anti-inflammatory and acetylcholinestrease enzyme inhibitory activities. Compounds 1-3 showed significant antioxidant and anti-inflammatory activities and weak to moderate acetylcholinestrease enzyme inhibition activity.

    Topics: Amines; Animals; Cannabaceae; Carrageenan; Cholinesterase Inhibitors; Edema; Fatty Acids; Female; Free Radical Scavengers; Male; Oleanolic Acid; Pentacyclic Triterpenes; Phenols; Plant Components, Aerial; Plant Extracts; Rats; Rats, Wistar; Sitosterols

2012
Organogel-emulsions with mixtures of β-sitosterol and γ-oryzanol: influence of water activity and type of oil phase on gelling capability.
    Journal of agricultural and food chemistry, 2012, Apr-04, Volume: 60, Issue:13

    In this study, water-in-oil emulsions were prepared from water containing different salt concentrations dispersed in an oil phase containing a mixture of β-sitosterol and γ-oryzanol. In pure oil, the β-sitosterol and γ-oryzanol molecules self-assemble into tubular microstructures to produce a firm organogel. However, in the emulsion, the water molecules bind to the β-sitosterol molecules, forming monohydrate crystals that hinder the formation of the tubules and resulting in a weaker emulsion-gel. Addition of salt to the water phase decreases the water activity, thereby suppressing the formation of sitosterol monohydrate crystals even after prolonged storage times (∼1 year). When the emulsions were prepared with less polar oils, the tubular microstructure was promoted, which significantly increased the firmness of the emulsion-gel. The main conclusion of this study is that the formation of oryzanol and sitosterol tubular microstructure in the emulsion can be promoted by reducing the water activity and/or by using oils of low polarity.

    Topics: Emulsions; Phenylpropionates; Plant Oils; Sitosterols; Sunflower Oil; Water

2012
γ-Sitosterol from Acacia nilotica L. induces G2/M cell cycle arrest and apoptosis through c-Myc suppression in MCF-7 and A549 cells.
    Journal of ethnopharmacology, 2012, Jun-14, Volume: 141, Issue:3

    Acacia nilotica is widely distributed in Asia. In India, it occupies an important place in the indigenous system of medicine against anti-inflammatory, antioxidant, cancers, and/or tumors.. The purpose of this study is to investigate the inhibitory effect of Acacia nilotica leaves extract and γ-Sitosterol on cell proliferation, the apoptotic effect and cell cycle arrest in breast and lung cancer cells.. GC-MS and HPLC were used to determine the chemical constituents of this extract and γ-Sitosterol respectively. Human MCF-7 and A549 cell lines were treated with Acacia nilotica extract and γ-Sitosterol. Cell viability was determined by MTT assay. Cell proliferation was determined by BrdU incorporation assay. Apoptosis was detected by cell morphologic observation through AO/EtBr staining, cell cycle analysis, and immunoblot analysis on the expression of protein associated with cell cycle arrest.. Experimental results of bioactive compound analysis indicate that γ-Sitosterol, bioactive ingredients of Acacia nilotica extract. The IC(50) value of extract on MCF-7 and A549 cancer cells was 493.3±15.2 and 696.6±11.5 μg/ml, respectively. Acacia nilotica extract and γ-Sitosterol were inhibited the cell proliferation by 54.34±1.8 and 42.18±3.9% for MCF-7 and 58.26±1.5 and 44.36±3.05% for A549 cells. The percentage of apoptotic cells observed in the MCF-7 and A549 cell lines were increased to 42.46 and 36.8% of extract; 46.68 and 43.24% for γ-Sitosterol respectively. Flow cytometric analysis results demonstrate that cells were arrested at the G2/M phase and decrease the c-Myc expression.. This study demonstrates in vitro results, which support the ethnomedical use of γ-Sitosterol against cancer. Experimental results of this study suggest that γ-Sitosterol exerts potential anticancer activity through the growth inhibition, cell cycle arrest and the apoptosis on cancer cells.

    Topics: Acacia; Antineoplastic Agents, Phytogenic; Apoptosis; Cell Cycle; Cell Cycle Checkpoints; Cell Line, Tumor; Cell Proliferation; Cyclin B; Cyclin E; Humans; Plant Extracts; Plant Leaves; Proto-Oncogene Proteins c-myc; Sitosterols

2012
Inhibitory effect of β-sitosterol on TNBS-induced colitis in mice.
    Planta medica, 2012, Volume: 78, Issue:9

    β-Sitosterol, a common sterol in herbal medicines, exhibits anti-inflammatory effects beneficial in the treatment of lung inflammation, asthma, and bronchospasm. To evaluate whether β-sitosterol also has anticolitic benefits, we tested the effect of β-sitosterol on 2,4,6-trinitrobenzene sulfonic acid (TNBS)-induced colitis in mice. β-Sitosterol inhibited colon shortening and led to lowered macroscopic scores and myeloperoxidase activity in TNBS-treated colitic mice. β-Sitosterol also inhibited the expression of proinflammatory cytokines TNF-α, IL-1β, and IL-6, and an inflammatory enzyme, cyclooxygenase (COX)-2, in the colons of TNBS-induced colitic mice, as well as the activation of NF-κB. Based on these findings, β-sitosterol may ameliorate colitis by inhibiting the NF-κB pathway.

    Topics: Animals; Colitis; Cyclooxygenase 2; Interleukin-1beta; Interleukin-6; Male; Mice; Mice, Inbred C57BL; NF-kappa B; Peroxidase; Sitosterols; Trinitrobenzenesulfonic Acid; Tumor Necrosis Factor-alpha

2012
Oxidized derivatives of dihydrobrassicasterol: cytotoxic and apoptotic potential in U937 and HepG2 cells.
    Journal of agricultural and food chemistry, 2012, Jun-13, Volume: 60, Issue:23

    The ability of phytosterol compounds to reduce plasma serum cholesterol levels in humans is well investigated. However, phytosterols are structurally similar to cholesterol with a double bond at the C5-6 position and are therefore susceptible to oxidation. Much research has been carried out on the biological effects of cholesterol oxidation products (COPs) in vitro. In contrast, there is less known about phytosterol oxidation products (POPs). From previous studies, it is apparent that oxidized derivatives of the phytosterols, β-sitosterol and stigmasterol, are cytotoxic in vitro but are less potent than their COP counterparts. In the present study, the cytotoxic and apoptotic potential of oxidized derivatives of dihydrobrassicasterol (DHB) including 5α,6α-epoxyergostan-3β-ol (α-epoxide), 5β,6β-epoxyergostan-3β-ol (β-epoxide), ergost-5-en-7-on-3β-ol (7-keto), ergost-5-ene-3β,7β-diol (7-β-OH), and ergostane-3β,5α,6β-triol (triol) were evaluated in the U937 and HepG2 cell lines. In general, 7-keto, 7-β-OH, and triol derivatives had a significant cytotoxic impact on U937 and HepG2 cells. The oxides appear to be more toxic toward U937 cells. In line with previous findings, the POPs investigated in this study were less potent than the equivalent COPs. The results add to the body of data on the toxicity of individual POPs.

    Topics: Apoptosis; Caspase 3; Caspase 7; Cell Survival; Cholesterol; DNA Fragmentation; Hep G2 Cells; Humans; Oxidation-Reduction; Phytosterols; Sitosterols; Stigmasterol; U937 Cells

2012
Immunomodulatory properties of beta-sitosterol in pig immune responses.
    International immunopharmacology, 2012, Volume: 13, Issue:3

    The ability to control an immune response for the benefit and production efficiency of animals is the objective of immunomodulation in food-producing animals; substances that exert this control are called immunomodulators. A Spanish product (Inmunicín MAYMO®), based on food plant phytosterols, is being commercialized as complementary feed. The main component of this product is Beta-sitosterol (BSS). BSS and its glycoside (BSSG) have been shown to exhibit anti-inflammatory, anti-neoplasic, anti-pyretic and immune-modulating activity demonstrated by in vitro and in vivo experiments. The objective of the present study was to characterize the effect of BSS on the pig immune system using in vitro cell cultures first and to elucidate whether BSS possesses any in vivo activity in fattener pigs after vaccination with porcine reproductive and respiratory syndrome virus (PRRSV) modified life vaccine (MLV). Firstly, our in vitro results showed that BSS increased viable peripheral blood mononuclear cell (PBMC) numbers and it activated swine dendritic cells (DCs) in culture. Secondly, pigs treated with phytosterols prior to vaccination with PRRSV-MLV vaccine exhibited some changes in immunological parameters at different times post-vaccination, such as the proliferation ability of PBMC after phytohemaglutinin stimulation and increased apolipoprotein A1 plasma concentration which may contribute to enhance PRRSV vaccine response. In conclusion, the data in this report show that BSS can be considered an immunomodulator in pigs.

    Topics: Animal Feed; Animals; Apolipoprotein A-I; Dendritic Cells; Female; Immunologic Factors; In Vitro Techniques; Leukocyte Count; Lymphocyte Activation; Male; Porcine respiratory and reproductive syndrome virus; Sitosterols; Spain; Sus scrofa; Viral Vaccines

2012
Rhinacanthus nasutus extracts prevent glutamate and amyloid-β neurotoxicity in HT-22 mouse hippocampal cells: possible active compounds include lupeol, stigmasterol and β-sitosterol.
    International journal of molecular sciences, 2012, Volume: 13, Issue:4

    The Herb Rhinacanthus nasutus (L.) Kurz, which is native to Thailand and Southeast Asia, has become known for its antioxidant properties. Neuronal loss in a number of diseases including Alzheimer's disease is thought to result, in part, from oxidative stress. Glutamate causes cell death in the mouse hippocampal cell line, HT-22, by unbalancing redox homeostasis, brought about by a reduction in glutathione levels, and amyloid-β has been shown to induce reactive oxygen species (ROS) production. Here in, we show that ethanol extracts of R. nasutus leaf and root are capable of dose dependently attenuating the neuron cell death caused by both glutamate and amyloid-β treatment. We used free radical scavenging assays to measure the extracts antioxidant activities and as well as quantifying phenolic, flavonoid and sterol content. Molecules found in R. nasutus, lupeol, stigmasterol and β-sitosterol are protective against glutamate toxicity.

    Topics: Acanthaceae; Alzheimer Disease; Amyloid beta-Peptides; Animals; Antioxidants; Cell Line; Glutamic Acid; Glutathione; Hippocampus; Mice; Neuroprotective Agents; Neurotoxicity Syndromes; Oxidative Stress; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Plant Roots; Reactive Oxygen Species; Sitosterols; Stigmasterol

2012
Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols.
    Steroids, 2012, Volume: 77, Issue:11

    Using cholesterol, β-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 5(6→7)abeo-sterols with different substituted groups and various side chains were synthesized and the antiproliferative activity of these compounds against HeLa, SMMC 7404 and MGC 7901 cells was investigated. The results revealed that the presence of a cholesterol-type side chain was very important for their cytotoxicity, and in particular a thiosemicarbazone at the C-6 position significantly enhanced the antiproliferative activity of these compounds. Although the elimination of 5-hydroxyl has no an obvious effect on their cytotoxic function, removal of the hydroxyl at the C-3 position decreased markedly the antiproliferative activity of the compounds. Some compounds have similar cytotoxic capability as cisplatin does.

    Topics: Antineoplastic Agents; Cell Line, Tumor; Cell Survival; Cholesterol; Dehydroepiandrosterone; Drug Screening Assays, Antitumor; Humans; Inhibitory Concentration 50; Pregnenolone; Sitosterols; Sterols; Structure-Activity Relationship; Thiosemicarbazones

2012
Two new flavanols from Glycosmis pentaphylla.
    Journal of Asian natural products research, 2012, Volume: 14, Issue:8

    Two new flavanols, glycoflavanones A (1) and B (2), which were found to possess α-pyrone moiety, together with five known compounds 4'-O-methylgallocatechine (3), β-sitosterol (4), alphitol (5), 3,4-dimethoxy-5-hydroxy-trans-cinnamyl alcohol (6), and oxyresveratrol (7), were isolated from the stems of Glycosmis pentaphylla by normal-phase and reverse-phase silica gel column chromatography. Their structures were determined on the basis of chemical and spectroscopic analyses.

    Topics: Drugs, Chinese Herbal; Flavonoids; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Stems; Rutaceae; Sitosterols

2012
[Chemical constituents from stems of Lonicera macranthoides].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:1

    To study the chemical constituents of Lonicera macranthoides.. Many chromatography means were used in separation and purification, and the structures of all compounds were identified by the means of spectroscopic analysis (MS, 1H-NMR, 13C-NMR) and physicochemical properties.. 13 compounds were elucidated as beta-sitosterol (1), daucosterol (2), chlorogenic acid (3), luteolin (4), quercetin (5), diosmetin-7-O-beta-D-glucoside (6), kaempferol-3-O-beta-D-glucoside (7), 3,4-O-di-caffeoylquinic acid methylester (8), 1,3-O-di-caffeoylquinic acid (9), scopoletin (10), macranthoidin B (11), macranthoidin A (12), eriodictyol (13).. The compounds 6,7 and 13 are obtained from this plant for the first time.

    Topics: Flavanones; Kaempferols; Lonicera; Monosaccharides; Plant Extracts; Plant Stems; Plants, Medicinal; Sitosterols

2012
Phytochemical composition and toxicity of an antioxidant extract from Pimpinella brachycarpa (Kom.) Nakai.
    Environmental toxicology and pharmacology, 2012, Volume: 34, Issue:2

    Pimpinella brachycarpa (Kom.) Nakai (PB) is one of the most favored edible greens grown in Asian regions. In our previously study, we found PB extract had antioxidant effects in vitro. In the present study, an EtOAc soluble extract (PBet) was isolated from PB. Then the antioxidant properties at cellular level, phytochemical composition and toxicity of PBet were examined. The results indicated that PBet (0.5-2mg/mL) could protect Bel-7404 cells from H(2)O(2) induced cell damage through scavenging of intracellular ROS. Moreover, myristic acid, 24ζ-methyl-5α-lanosta-25-one, β-sitosterol, pregnenolone and β-daucosterol were firstly isolated from PB. In addition, PBet (0.75g/kg BW, ig) had no acute toxicity and it (0.03-0.12g/kg BW, ig, 7 d) could not influence the rate of bone marrow polychromatic erythrocytes micronucleus and chromosome aberration in KM mice. All above findings suggested that PBet could be considered as a safe functional food with antioxidant activities.

    Topics: Animals; Antioxidants; Cell Line, Tumor; Cell Survival; Humans; Mice; Mutagenicity Tests; Pimpinella; Plant Extracts; Reactive Oxygen Species; Sitosterols; Toxicity Tests, Acute

2012
Comparative evaluation of traditional prescriptions from Cichorium intybus L. for wound healing: stepwise isolation of an active component by in vivo bioassay and its mode of activity.
    Journal of ethnopharmacology, 2012, Aug-30, Volume: 143, Issue:1

    Ethnobotanical field surveys revealed that various parts of Cichorium intybus L. has been used for wound healing in Turkish folk medicine.. The present study aimed at verifying the efficiency of various traditional prescriptions prepared from the aerial parts and roots of C. intybus experimentally and to define the components responsible from the activity by bioassay-guided procedures.. Initially, wound healing activity of the aerial parts, leaves, and roots as well as ashes of either leaves or roots were investigated. Subsequently, roots of the plant were submitted to further detailed investigations. The wound healing activity of the methanolic extract, its subextracts, and fractions were evaluated by using in vivo linear incision and circular excision wound models in rats. The hydroxyproline content of the tissues treated with test ointments were also assessed for the activity evaluation. Moreover, in order to find out a possible involvement of antioxidant activity in wound healing, the test samples were also investigated by DPPH radical scavenging activity and total phenolic concentration were also determined. Additionally anti-inflammatory activity was assessed by using the method of Whittle, which is based on the inhibition of acetic acid-induced increase in capillary permeability. Through the bioassay guided fractionation one compound was isolated and its structure was elucidated by spectroscopic methods. For the determination of the activity mechanisms, the fractions were screened for hyaluronidase, collagenase and elastase enzyme inhibitory activities.. Methanolic extract of C. intybus roots was found to possess potent wound healing activity. Then this extract was subjected to successive solvent extraction with n-hexane, dichloromethane (DCM), ethyl acetate and n-butanol. Each solvent extracts were also applied on the same wound models. DCM subextract was found to be the most active one and through chromatographic techniques DCM subextract was fractionated into several fractions and compound 1 was isolated as the compound being responsible from the wound healing activity.. The experimental study revealed that C. intybus methanolic extract displays wound healing effect and β-sitosterol was determined as the active compound responsible from the activity.

    Topics: Animals; Cichorium intybus; Male; Medicine, Traditional; Mice; Mice, Inbred Strains; Phytotherapy; Plant Components, Aerial; Plant Preparations; Plant Roots; Rats; Rats, Sprague-Dawley; Sitosterols; Turkey; Wound Healing; Wounds and Injuries

2012
Bioactive constituents in Prunus africana: geographical variation throughout Africa and associations with environmental and genetic parameters.
    Phytochemistry, 2012, Volume: 83

    Prunus africana--an evergreen tree found in Afromontane forests--is used in traditional medicine to cure benign prostate hyperplasia. Different bioactive constituents derived from bark extracts from 20 tree populations sampled throughout the species' natural range in Africa were studied by means of GC-MSD. The average concentration [mg/kgw/w] in increasing order was: lauric acid (18), myristic acid (22), n-docosanol (25), ferulic acid (49), β-sitostenone (198), β-sitosterol (490), and ursolic acid (743). The concentrations of many bark constituents were significantly correlated and concentration of n-docosanol was highly significantly correlated with all other analytes. Estimates of variance components revealed the highest variation among populations for ursolic acid (66%) and the lowest for β-sitosterol (20%). In general, environmental parameters recorded (temperature, precipitation, altitude) for the samples sites were not correlated with the concentration of most constituents; however, concentration of ferulic acid was significantly correlated with annual precipitation. Because the concentration of compounds in bark extracts may be affected by tree size, the diameter of sampled plants at 1.3m tree height (as proxy of age) was recorded. The only relationship with tree diameter was a negative correlation with ursolic acid. Under the assumption that genetically less variable populations have less variable concentrations of bark compounds, correlations between variation parameters of the concentration and the respective genetic composition based on chloroplast and nuclear DNA markers were assessed. Only variation of β-sitosterol concentration was significantly correlated with haplotypic diversity. The fixation index (F(IS)) was positively correlated with the variation in concentration of ferulic acid. Principal Components Analysis (PCA) indicated a weak geographic pattern. Mantel tests, however, revealed associations between the geographic patterns of bioactive constituents and the phylogenetic relationship among the populations sampled. This suggests an independent evolution of bark metabolism within different phylogeographical lineages, and the molecular phylogeographic pattern is partly reflected in the variation in concentration of bark constituents. The results have important implications for the design of strategies for the sustainable use and conservation of this important African tree species.

    Topics: Africa; Coumaric Acids; DNA, Chloroplast; DNA, Ribosomal; Fatty Alcohols; Genetic Markers; Lauric Acids; Myristic Acid; Plant Extracts; Principal Component Analysis; Prunus africana; Sitosterols; Temperature; Triterpenes; Ursolic Acid

2012
The sterols isolated from Evening Primrose oil modulate the release of proinflammatory mediators.
    Phytomedicine : international journal of phytotherapy and phytopharmacology, 2012, Sep-15, Volume: 19, Issue:12

    Evening Primrose oil is a natural product extracted by cold-pressed from Oenothera biennis L. seeds. The unsaponifiable matter of this oil is an important source of interesting minor compounds, like long-chain fatty alcohols, sterols and tocopherols. In the present study, sterols were isolated from the unsaponifiable matter of Evening Primrose oil, and the composition was identified and quantified by GC and GC-MS. The major components of sterols fraction were β-Sitosterol and campesterol. We investigated the ability of sterols from Evening Primrose oil to inhibit the release of different proinflammatory mediators in vitro by murine peritoneal macrophages stimulated with lipopolysaccharide. Sterols significantly and dose-dependently decreased nitric oxide production. Western blot analysis showed that nitric oxide reduction was a consequence of the inhibition of inducible nitric oxide synthetase expression. Sterols also reduced tumor necrosis factor-α, interleukine 1β and tromboxane B₂. However, sterols did not reduce prostaglandin E₂. The reduction of eicosanoid release was related to the inhibition of cyclooxygenase-2 expression. These results showed that sterols may have a protective effect on some mediators involved in inflammatory damage development, suggesting its potential value as a putative functional component of Evening Primrose oil.

    Topics: Animals; Cholesterol; Cyclooxygenase 2 Inhibitors; Dose-Response Relationship, Drug; Inflammation; Inflammation Mediators; Lipopolysaccharides; Macrophages; Mice; Nitric Oxide; Nitric Oxide Synthase Type II; Oenothera biennis; Phytosterols; Phytotherapy; Plant Oils; Seeds; Sitosterols

2012
Clionosterol and ethyl cholestan-22-enol isolated from the rhizome of Polygala tenuifolia inhibit phosphatidylinositol 3-kinase/Akt pathway.
    Biological & pharmaceutical bulletin, 2012, Volume: 35, Issue:8

    Phosphatidylinositol 3-kinase (PI3K)/Akt inhibitors were isolated from the rhizome of Polygala tenuifolia WILLD (PT, Polygalaceae), which has been used in traditional Chinese medicine for inflammation, dementia, amnesia, neurasthenia and cancer, by activity-guided fractionation. For the assay of PI3K/Akt pathway, cytoprotective Tat-transduced CHME5 cells, which are the cytoprotective phenotype against lypopolysaccharide (LPS)/cycloheximide (CHX), were used. We isolated 4 anti-cytoprotective compounds, clionasterol (1), ethyl cholestan-22-enol (2), 3-O-β-D-glucosyl ethyl cholestan-22-enol (3), and 3-O-β-D-glucopyranosyl clionasterol (4) from EtOAc fraction of PT against Tat-transduced CHME5 cells. Of them, (1) and (2) most potently abolished cytoprotective effect of Tat-transduced CHME5 cells. These constituents (1) and (2) inhibited the activation of 3-phosphoinositide-dependent kinase 1 (PDK1) and its downstream molecules, Akt/glycogen synthase kinase (GSK)3β, in PI3K/Akt cell survival signaling pathway, but did not suppress the activation of PI3K. Based on these finding, (1) and (2) may abolish the cytoprotective phenotype of Tat-transduced CHME5 cells by inhibiting PDK1 phosphorylation in PI3K/Akt pathway.

    Topics: Cell Line; Cholestanols; Cycloheximide; Cytoprotection; Enzyme Inhibitors; Gene Products, tat; Humans; Lipopolysaccharides; Phosphoinositide-3 Kinase Inhibitors; Plant Extracts; Polygala; Proto-Oncogene Proteins c-akt; Rhizome; Signal Transduction; Sitosterols; Viral Proteins

2012
Liver fat content is associated with an increase in cholesterol synthesis independent of statin therapy use in patients with type 2 diabetes.
    Atherosclerosis, 2012, Volume: 224, Issue:2

    We investigated how liver fat content (LFC) influences cholesterol metabolism by quantifying liver fat using proton magnetic resonance spectroscopy and by measuring the serum concentrations of lathosterol, a marker of cholesterol synthesis, and sitosterol and campesterol, two markers of cholesterol absorption. We also evaluated whether this relationship could be modified by statin therapy. The study was conducted in 263 patients with type 2 diabetes, 137 of whom (52.0%) received statin therapy.. One hundred and sixty-five patients (62.7%) had steatosis (LFC>5.5%). We performed specific analyses in patients without statin therapy and in patients treated with statin therapy. In both groups, the lathosterol to cholesterol ratio correlated positively with LFC, and in multivariate analysis, the lathosterol to cholesterol ratio was associated with LFC independently of age, gender and BMI. Sitosterol and campesterol concentrations were not associated with LFC.. Our study suggests that in patients with type 2 diabetes, LFC is associated with an increase in cholesterol synthesis that is independent of obesity or diabetes mellitus. Statin therapy does not modify this relationship.

    Topics: Aged; Biomarkers; Cholesterol; Diabetes Mellitus, Type 2; Dyslipidemias; Fatty Liver; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Linear Models; Liver; Magnetic Resonance Spectroscopy; Male; Middle Aged; Multivariate Analysis; Non-alcoholic Fatty Liver Disease; Phytosterols; Risk Factors; Sitosterols; Treatment Outcome

2012
[Study on the chemical constituents from Cyathea spinulosa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:4

    To study the chemical constituents from Cyathea spinulosa.. Compounds were isolated by chromatographic techniques. Their structures were elucidated by spectral methods.. Eight compounds were isolated from the ethanol extract of Cyathea spinulosa and identified as stigmast-4-ene-3,6-dione (1), stigmast-3,6-dione (2), ergosterol (3), protocatechuic aldehyde (4), 1-O-beta-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl) amido]-4,8- octadecadiene-1,3-diol (5), (2S,3S, 4R)-2-[(2'R) -2'-hydroxytetracosanoylamino]-1,3,4-octadecanetriol (6), beta-sitosterol (7), daucosterol (8).. Compounds 1-6 are isolated from this plant for the first time.

    Topics: Benzaldehydes; Catechols; Cholestenones; Ergosterol; Ferns; Molecular Structure; Plant Stems; Sitosterols

2012
Mechanistic examination of walnuts in prevention of breast cancer.
    Nutrition and cancer, 2012, Volume: 64, Issue:7

    Walnuts contain bioactive molecules that may contribute to their beneficial effects, including alpha-linolenic acid (ALA) and phytosterols. In these studies, extracts of walnut, purified compounds, or postprandial serum were examined for effects on breast cancer cell proliferation and gene expression. Extracts derived from walnut oil decreased proliferation of MCF-7 cells, as did ALA and β-sitosterol. The gene expression response of ALA in the mouse breast cancer cell line TM2H indicates this molecule has multiple cellular targets with peroxisome proliferator-activated receptor (PPAR) target genes, liver X receptor (LXR), and farnesoid X receptor (FXR) target genes being affected. In transactivation assays, walnut oil extracts increased activity of FXR to a greater extent than the other tested nuclear receptors. When examined separately, walnut components ALA and β-sitosterol were the most efficacious activators of FXR. When serum from individuals fed walnut components were applied to MCF-7 cells, there was a correlation between body mass index and breast cancer cell proliferation in vitro. Taken together, these data support an effect of walnut and its bioactive constituents on mammary epithelial cells and that multiple molecular targets may be involved.

    Topics: 3T3 Cells; alpha-Linolenic Acid; Animals; Anticarcinogenic Agents; Breast Neoplasms; Cell Proliferation; Chemoprevention; Epithelial Cells; Female; Humans; Juglans; Liver X Receptors; MCF-7 Cells; Mice; Nuts; Orphan Nuclear Receptors; Peroxisome Proliferator-Activated Receptors; Plant Extracts; Plant Oils; Real-Time Polymerase Chain Reaction; Receptors, Cytoplasmic and Nuclear; Sitosterols

2012
Novel bio-active lipid nanocarriers for the stabilization and sustained release of sitosterol.
    Nanotechnology, 2012, Nov-16, Volume: 23, Issue:45

    In this work, new stable and efficiently bio-active lipid nanocarriers (NLCs) with antioxidant properties have been developed for the transport of active ingredients in food. The novel NLCs loaded with β-sitosterol/β-sitosterol and green tea extract (GTE) and prepared by a combination of natural oils (grape seed oil, fish oil and squalene) and biological lipids with food grade surfactants, were physico-chemically examined by DLS, TEM, electrokinetic potential, DSC and HPLC and found to have main diameters less than 200 nm, a spherical morphology, excellent physical stability, an imperfect crystalline lattice and high entrapment efficiency. The novel loaded-NLCs have demonstrated the potential to develop a high blocking action of chain reactions, trapping up to 92% of the free-oxygen radicals, as compared to the native β-sitosterol (AA%=36.5). Another advantage of this study is associated with the quality of bio-active NLCs based on grape seed oil and squalene to manifest a better sitosterol-sustained release behaviour as compared to their related nanoemulsions. By coupling both in vitro results, i.e. the enhanced antioxidant activity and superior release properties, this study emphasizes the sustainability of novel bio-active nanocarriers to gain specific bio-food features for development of functional foods with a high applicability spectrum.

    Topics: Antioxidants; Delayed-Action Preparations; Food Additives; Lipids; Nanostructures; Oils; Plant Extracts; Sitosterols; Surface-Active Agents; Tea

2012
Anti-nociceptive activity of Pereskia bleo Kunth. (Cactaceae) leaves extracts.
    Journal of ethnopharmacology, 2012, Dec-18, Volume: 144, Issue:3

    Local communities in Malaysia consume Pereskia bleo Kunth. (Cactaceae) leaves as raw vegetables or as a concoction and drink as a tea to treat diabetes, hypertension, rheumatism, cancer-related diseases, inflammation, gastric pain, ulcers, and for revitalizing the body.. To evaluate anti-nociceptive activity of the extracts and vitexin, isolated for the first time in this species, in two analgesic models; formalin-induced licking and acetic acid-induced abdominal writhing.. Three and a half kilos of P. bleo leaves were extracted using Soxhlet apparatus with ethanol for 72 h. The crude ethanol extract was treated with activated charcoal overnight and subjected to a liquid-liquid partition yielding hexane, dichloromethane, ethyl acetate and butanol extracts. All extracts, including the crude ethanol and vitexin isolated from the ethyl acetate partition were tested for peripheral anti-nociceptive activity using formalin test and acetic acid-induced abdominal writhing, besides having their acute toxicity assays performed.. The phytochemical analyses resulted in the isolation of vitexin (1), β-sitosterol glucoside (2) and β-sitosterol (3) isolated from the ethyl acetate, dichloromethane and hexane extracts, respectively. This is the first time vitexin and β-sitosterol glucoside are isolated from this species. The anti-nociceptive activities for all extracts were only moderate. Vitexin, which was isolated from the ethyl acetate extract did not show any activity in all models tested when used alone at the same concentration as it appears in the extract.. This study showed that all the extracts possess moderate anti-nociceptive activity. Vitexin is not the compound responsible for the anti-nociceptive effect in the ethyl acetate extract. Further investigations are needed to identify the compound(s) that might be responsible for the anti-nociceptive activity in this plant.

    Topics: Acetic Acid; Analgesics; Animals; Apigenin; Behavior, Animal; Cactaceae; Formaldehyde; Male; Mice; Pain; Plant Extracts; Plant Leaves; Sitosterols; Toxicity Tests, Acute

2012
[Chemical constituents of Pileostegia viburnoides var. glabrescens].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:5

    To study the chemical constituents of Pileostegia viburnoides var. glabrescens.. The compounds were isolated and purified by various techniques. Their structures were determined by physicochemical properties and spectral analysis.. Five compounds were isolated and identified as friedelin (1), beta-sitosterol (2), umbelliferone (3), daucosterol (4) and skimmin (5).. All the compounds were isolated from this genus for the first time.

    Topics: Magnetic Resonance Spectroscopy; Molecular Structure; Saxifragaceae; Sitosterols; Triterpenes; Umbelliferones

2012
[Chemical constituents from Astilbe myriantha].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2012, Volume: 35, Issue:7

    To study the chemical constituents from Astilbe myriantha.. The constituents were isolated and purified by column chromatography methods and recrystallization. Their structures were identified on the basis of physiochemical properties and special analysis.. Ten compounds were isolated from 95% ethanol extract of Astilbe myriantha and their structures were identified as: beta-sitosterol (1), methyl p-hydroxy benzoate (2), ferulic acid (3), bergenin (4), gallic acid (5), (+)-catechin (6), 3beta-acetoxy-6beta-hydroxyolean-12-en-27-oic acid (7), 3beta-hydroxyolean-12-en-27-oic acid (8),3beta,6beta-dihydrolean-12-en-27-oic acid (9) and 3beta-hydroxyurs-12-en-27-oic acid (10).. Compounds 1-7 are isolated from this plant for the first time.

    Topics: Benzopyrans; Coumaric Acids; Ethanol; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Rhizome; Saxifragaceae; Sitosterols; Triterpenes

2012
Chemical constituents of three Allium species from Romania.
    Molecules (Basel, Switzerland), 2012, Dec-21, Volume: 18, Issue:1

    The aim of this work was to study the chemical composition of Allium obliquum L., A. senescens L. subsp. montanum (Fries) Holub, and A. schoenoprasum L. subsp. schoenoprasum. Sulphur-containing compounds analysis was performed by an LC-MS method, the identification and quantification of polyphenolic compounds through a HPLC-UV-MS method, and the presence of five sterols was simultaneously assessed by HPLC-MS-MS. Alliin was identified only in A. obliquum and A. senescens subsp. montanum extracts, whilst allicin was present in all extracts, with higher amounts in A. schoenoprasum and A. obliquum. The pattern of phenol carboxylic acids shows the presence of p-coumaric and ferulic acids in all species. Isoquercitrin was identified in A. obliquum and A. schoenoprasum, and rutin in A. senescens subsp. montanum and A. schoenoprasum. Luteolin and apigenin were identified only in A. obliquum. All three species contain glycosides of kaempferol and quercetol. β-Sitosterol and campesterol were identified in all species. The results obtained showed significant differences in the composition of the three Allium species.

    Topics: Allium; Chromatography, High Pressure Liquid; Chromatography, Liquid; Cysteine; Disulfides; Glycosides; Kaempferols; Phenols; Phytosterols; Plant Extracts; Polyphenols; Romania; Sitosterols; Sulfinic Acids; Tandem Mass Spectrometry

2012
Association of plasma markers of cholesterol homeostasis with metabolic syndrome components. A cross-sectional study.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2011, Volume: 21, Issue:9

    Increased plasma phytosterols, which reflect enhanced cholesterol absorption, have been related to an increased risk of cardiovascular disease (CVD). However, high CVD risk conditions, such as obesity, diabetes and the metabolic syndrome (MetS) have been associated with reduced cholesterol absorption. We investigated associations between plasma noncholesterol sterols and MetS components.. With a cross-sectional design, we related MetS components to plasma noncholesterol sterol-to-cholesterol ratios measured by gas chromatography in 674 dyslipidemic patients and 361 healthy subjects participating in a prospective cohort study. Plasma phytosterol-to-cholesterol ratios were inversely associated with all components of the MetS. In the dyslipidemic group, multivariable analyses showed that a 1-SD increase in sitosterol-to-cholesterol ratio was associated with a reduced risk for any MetS feature, ranging from 0.57 (95% CI, 0.45 to 0.71) for visceral adiposity to 0.82 (95% CI, 0.69 to 0.98) for high blood pressure. The risk of having MetS was nearly halved, with ORs of 0.49 (95% CI, 0.38 to 0.64) or 0.56 (95% CI, 0.44-0.70), depending on the definition. Results were opposed for plasma lathosterol, a marker of cholesterol synthesis. Most findings were reproduced in the healthy cohort. ApoE genotype was unrelated to plasma noncholesterol sterols.. In both dyslipidemic and healthy populations, MetS is associated with increased plasma lathosterol, a cholesterol synthesis marker, and decreased plasma sitosterol, a marker of cholesterol absorption. Elevated plasma phytosterols related to a lower frequency of cardiometabolic risk factors, suggesting that they are associated with a reduced CVD risk.

    Topics: Adult; Apolipoproteins E; Biomarkers; Cardiovascular Diseases; Cholesterol; Cross-Sectional Studies; Female; Genotype; Homeostasis; Humans; Lipid Metabolism; Male; Metabolic Syndrome; Middle Aged; Phenotype; Phytosterols; Prospective Studies; Risk Factors; Sitosterols

2011
Reproductive consequences of exposure to waterborne phytoestrogens in male fighting fish Betta splendens.
    Archives of environmental contamination and toxicology, 2011, Volume: 60, Issue:3

    Phytoestrogens are plant compounds that can act as endocrine disruptors in vertebrates. Biologically active levels of phytoestrogens have been found in aquatic habitats near wood pulp and paper mills, biofuel manufacturing plants, sewage-treatment plants, and agricultural fields. Phytoestrogens are known to cause hormonal and gonadal changes in male fish, but few studies have connected these effects to outcomes relevant to reproductive success. In one experiment, we exposed sexually mature male fighting fish Betta splendens to environmentally relevant (1 μg L(-1)) and pharmacological concentrations (1000 μg L(-1)) of the phytoestrogen genistein as well as to a positive control of waterborne 17β-estradiol (E2; 1 μg L(-1)), and a negative control of untreated water. In a second experiment, we exposed male B. splendens to environmentally relevant concentrations (1 μg L(-1)) of genistein and β-sitosterol singly and in combination as well as to the positive and negative controls. All exposures were 21 days in duration. We measured sex-steroid hormone levels, gonadosomatic index (GSI), sperm concentration and motility, and fertilization success in these fish. We found that exposure to genistein did not affect circulating levels of the androgen 11-ketotestosterone or the estrogen E2 relative to negative-control fish. We also found that neither of the compounds nor their mixture affected GSI, sperm concentration or motility, or fertilization success in exposed fish relative to negative-control fish. However, fish exposed to phytoestrogens showed some evidence of fewer but more motile sperm than fish exposed to the positive control E2. We conclude that sexually mature male B. splendens are relatively immune to reproductive impairments from short-term exposure to waterborne phytoestrogens.

    Topics: Animals; Endocrine Disruptors; Estradiol; Fertilization; Genistein; Male; Perciformes; Phytoestrogens; Sitosterols; Sperm Motility; Testis; Testosterone; Water Pollutants, Chemical

2011
Suppression of ovalbumin-induced Th2-driven airway inflammation by β-sitosterol in a guinea pig model of asthma.
    European journal of pharmacology, 2011, Jan-10, Volume: 650, Issue:1

    In the present study, the efficacy of β-sitosterol isolated from an n-butanol extract of the seeds of the plant Moringa oleifera (Moringaceae) was examined against ovalbumin-induced airway inflammation in guinea pigs. All animals (except group I) were sensitized subcutaneously and challenged with aerosolized 0.5% ovalbumin. The test drugs, β-sitosterol (2.5mg/kg) or dexamethasone (2.5mg/kg), were administered to the animals (p.o.) prior to challenge with ovalbumin. During the experimental period (on days 18, 21, 24 and 29), a bronchoconstriction test (0.25% acetylcholine for 30s) was performed and lung function parameters (tidal volume and respiration rate) were measured for each animal. On day 30, blood and bronchoalveolar lavaged fluid were collected to assess cellular content, and serum was collected for cytokine assays. Lung tissue was utilized for a histamine assay and for histopathology. β-sitosterol significantly increased the tidal volume (V(t)) and decreased the respiration rate (f) of sensitized and challenged guinea pigs to the level of non-sensitized control guinea pigs and lowered both the total and differential cell counts, particularly eosinophils and neutrophils, in blood and bronchoalveolar lavaged fluid. Furthermore, β-sitosterol treatment suppressed the increase in cytokine levels (TNFα, IL-4 and IL-5), with the exception of IL-6, in serum and in bronchoalveolar lavaged fluid detected in model control animals. Moreover, treatment with β-sitosterol protected against airway inflammation in lung tissue histopathology. β-sitosterol possesses anti-asthmatic actions that might be mediated by inhibiting the cellular responses and subsequent release/synthesis of Th2 cytokines. This compound may have therapeutic potential in allergic asthma.

    Topics: Acetylcholine; Animals; Anti-Asthmatic Agents; Asthma; Body Weight; Bronchial Spasm; Bronchoalveolar Lavage Fluid; Bronchoconstriction; Cell Count; Cytokines; Disease Models, Animal; Guinea Pigs; Histamine; Inflammation; Lung; Male; Ovalbumin; Respiratory System; Sitosterols; Th2 Cells

2011
Cholesterol synthesis is increased and absorption decreased in non-alcoholic fatty liver disease independent of obesity.
    Journal of hepatology, 2011, Volume: 54, Issue:1

    Non-alcoholic fatty liver disease (NAFLD) is associated with impaired glucose and lipoprotein metabolism. However, the metabolism of cholesterol in NAFLD remains unexplored. We investigated how fatty liver influences cholesterol metabolism in 242 non-diabetic subjects.. Liver fat content was measured with proton magnetic resonance spectroscopy. Cholesterol metabolism was assayed with serum non-cholesterol sterols, surrogate markers of cholesterol synthesis and absorption. The analyses were performed with gas-liquid chromatography.. A total of 114 subjects had NAFLD and 128 subjects had normal liver fat content. Non-cholesterol sterols reflecting cholesterol synthesis (cholestenol, desmosterol, and lathosterol) were higher, and those reflecting cholesterol absorption (cholestanol and plant sterols) were lower in subjects with NAFLD than in controls, independent of body mass index. Liver fat content was positively associated with markers of cholesterol synthesis (r = from 0.262 to 0.344, p < 0.001 for all) and inversely associated with markers of cholesterol absorption (r = from -0.299 to -0.336, p < 0.001 for all). In the entire study group, synthesis and absorption markers were interrelated, indicating that the homeostasis of cholesterol metabolism was maintained. LDL cholesterol was similar in the two groups.. We demonstrated that although LDL cholesterol concentrations are unchanged, cholesterol metabolism in NAFLD is characterized by increased synthesis and diminished absorption of cholesterol. These changes are associated with liver fat content independent of body weight.

    Topics: Adult; Aged; Body Mass Index; Case-Control Studies; Cholesterol; Cholesterol, Dietary; Cholesterol, LDL; Fatty Liver; Female; Humans; Insulin; Intestinal Absorption; Liver; Magnetic Resonance Spectroscopy; Male; Middle Aged; Non-alcoholic Fatty Liver Disease; Obesity; Sitosterols; Young Adult

2011
The effects of cholesterol and β-sitosterol on the structure of saturated diacylphosphatidylcholine bilayers.
    European biophysics journal : EBJ, 2011, Volume: 40, Issue:2

    The structures of DMPC and DPPC bilayers in unilamellar liposomes, in the presence of 33.3 mol% cholesterol or the plant sterol β-sitosterol, have been studied by small-angle neutron scattering. The bilayer thickness d(L) increases in a similar way for both sterols. The repeat distance in multilamellar liposomes, as determined by small-angle X-ray diffraction, is larger in the presence of β-sitosterol than in the presence of cholesterol. We observe that each sterol modifies the interlamellar water layer differently, cholesterol reducing its thickness more efficiently than β-sitosterol, and conclude that cholesterol suppresses bilayer undulations more effectively than β-sitosterol.

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Cholesterol; Lipid Bilayers; Liposomes; Scattering, Small Angle; Sitosterols; X-Ray Diffraction

2011
Phytosterols differentially influence ABC transporter expression, cholesterol efflux and inflammatory cytokine secretion in macrophage foam cells.
    The Journal of nutritional biochemistry, 2011, Volume: 22, Issue:8

    Phytosterol supplements lower low-density lipoprotein (LDL) cholesterol, but accumulate in vascular lesions of patients and limit the anti-atherosclerotic effects of LDL lowering in apolipoprotein E (Apo E)-deficient mice, suggesting that the cholesterol-lowering benefit of phytosterol supplementation may not be fully realized. Individual phytosterols have cell-type specific effects that may be either beneficial or deleterious with respect to atherosclerosis, but little is known concerning their effects on macrophage function. The effects of phytosterols on ABCA1 and ABCG1 abundance, cholesterol efflux and inflammatory cytokine secretion were determined in cultured macrophage foam cells. Among the commonly consumed phytosterols, stigmasterol increased expression of ABCA1 and ABCG1 and increased efflux of cholesterol to apolipoprotein (Apo) AI and high-density lipoprotein (HDL). Campesterol and sitosterol had no effect on ABCA1 or ABCG1 levels. Sitosterol had no effect on cholesterol efflux to Apo AI or HDL, whereas campesterol had a modest but significant reduction in cholesterol efflux to HDL in THP-1 macrophages. Whereas stigmasterol blunted aggregated LDL (agLDL) induced increases in tumor necrosis factor (TNF)-α, interleukin (IL)-6 and IL-1β secretion, sitosterol exacerbated these effects. The presence of campesterol had no effect on agLDL-induced inflammatory cytokine secretion from THP-1 macrophages. In conclusion, the presence of stigmasterol in modified lipoproteins promoted cholesterol efflux and suppressed inflammatory cytokine secretion in response to lipid loading in macrophage foam cells. While campesterol was largely inert, the presence of sitosterol increased the proinflammatory cytokine secretion.

    Topics: Animals; Apolipoprotein A-I; ATP Binding Cassette Transporter 1; ATP Binding Cassette Transporter, Subfamily G, Member 1; ATP-Binding Cassette Transporters; Cells, Cultured; Cholesterol; Foam Cells; Humans; Interleukin-1beta; Interleukin-6; Interleukin-8; Lipoproteins; Lipoproteins, HDL; Lipoproteins, LDL; Male; Mice; Mice, Inbred C57BL; Phytosterols; Sitosterols; Stigmasterol; Tumor Necrosis Factor-alpha

2011
Antidiabetic and antioxidant potential of β-sitosterol in streptozotocin-induced experimental hyperglycemia.
    Journal of diabetes, 2011, Volume: 3, Issue:1

    Oxidative stress, produced under diabetic conditions, may cause tissue damage. Although several drugs are currently available for the treatment of diabetes, their continued use may cause unwanted side effects. The aim of the present study was to evaluate the antioxidant potential of β-sitosterol (BS), a phytosterol from Solanum surattense, using an experimental model for diabetes-induced oxidative damage.. The effects of 21 days treatment with BS (10, 15 and 20 mg/kg, p.o.) on blood, serum, and tissue biochemical parameters were evaluated in control and streptozotocin-induced diabetic rats. Nine experimental groups, including a control group, a diabetic group, and BS- and glibenclamide-treated diabetic groups, were evaluated.. All three dose levels dose dependently resulted in decreases in glycated hemoglobin, serum glucose, and nitric oxide, with concomitant increases in serum insulin levels. Furthermore, treatment with BS doses also increased pancreatic antioxidant levels, with a concomitant decrease in thiobarbituric acid-reactive substances.. β-Sitosterol has promising antidiabetic as well as antioxidant effects and may be considered in clinical studies for drug development.

    Topics: Animals; Antioxidants; Blood Glucose; Catalase; Diabetes Mellitus, Experimental; Dose-Response Relationship, Drug; Female; Glutathione; Glyburide; Glycated Hemoglobin; Glycosuria; Hyperglycemia; Hypoglycemic Agents; Insulin; Islets of Langerhans; Male; Molecular Structure; Nitric Oxide; Rats; Rats, Wistar; Sitosterols; Solanum; Streptozocin; Superoxide Dismutase; Treatment Outcome

2011
A potential biochemical mechanism underlying the influence of sterol deprivation stress on Caenorhabditis elegans longevity.
    The Journal of biological chemistry, 2011, Mar-04, Volume: 286, Issue:9

    To investigate the biochemical mechanism underlying the effect of sterol deprivation on longevity in Caenorhabditis elegans, we treated parent worms (P0) with 25-azacoprostane (Aza), which inhibits sitosterol-to-cholesterol conversion, and measured mean lifespan (MLS) in F2 worms. At 25 μM (∼EC(50)), Aza reduced total body sterol by 82.5%, confirming sterol depletion. Aza (25 μM) treatment of wild-type (N2) C. elegans grown in sitosterol (5 μg/ml) reduced MLS by 35%. Similar results were obtained for the stress-related mutants daf-16(mu86) and gas-1(fc21). Unexpectedly, Aza had essentially no effect on MLS in the stress-resistant daf-2(e1370) or mitochondrial complex II mutant mev-1(kn1) strains, indicating that Aza may target both insulin/IGF-1 signaling (IIS) and mitochondrial complex II. Aza increased reactive oxygen species (ROS) levels 2.7-fold in N2 worms, but did not affect ROS production by mev-1(kn1), suggesting a direct link between Aza treatment and mitochondrial ROS production. Moreover, expression of the stress-response transcription factor SKN-1 was decreased in amphid neurons by Aza and that of DAF-28 was increased when DAF-6 was involved, contributing to lifespan reduction.

    Topics: Aging; Animals; Animals, Genetically Modified; Azasteroids; Caenorhabditis elegans; Cholesterol; Lipid Metabolism; Longevity; Mitochondria; Oxidative Stress; Reactive Oxygen Species; Sitosterols

2011
Prognostic significance of serum cholesterol, lathosterol, and sitosterol in old age; a 17-year population study.
    Annals of medicine, 2011, Volume: 43, Issue:4

    BACKGROUND. Low serum total cholesterol is frequently associated with worse survival in older people, but mechanisms of this association are poorly understood. AIMS. Characteristics of cholesterol metabolism were related to survival in a random 75 + population sample. METHODS. Serum cholesterol and lathosterol, and sitosterol were measured in random persons (n = 623) of birth cohorts (1904, 1909, and 1914) in 1990, and all persons were followed for 17 years. RESULTS. Total cholesterol declined in old age, and low cholesterol was associated with poor health and multi-morbidity. Cholesterol below 5.0 mmol/L was associated with accelerated all-cause mortality (age- and gender-adjusted hazard ratio (HR) 1.54; 95% CI 1.21-1.97; P < 0.001) and vascular mortality (HR 2.13 (1.42-3.07); P < 0.001). Lathosterol (indicating cholesterol synthesis) and sitosterol (indicating cholesterol absorption) also decreased with deteriorating health. Low lathosterol, sitosterol, and cholesterol predicted mortality additively and independently of each other. When all three sterols were high (> median) or low, the age- and gender-adjusted survival was 9.9 and 5.6 years (P < 0.001). CONCLUSION. Lower synthesis and absorption of cholesterol, and low serum cholesterol level are associated with deteriorating health and indicate impaired survival in old age.

    Topics: Age Factors; Aged; Aged, 80 and over; Aging; Blood Pressure; Body Mass Index; Cause of Death; Cholesterol; Cognition; Finland; Humans; Kaplan-Meier Estimate; Longitudinal Studies; Male; Peak Expiratory Flow Rate; Predictive Value of Tests; Proportional Hazards Models; Sitosterols; Survival Analysis; Vascular Diseases

2011
Antiproliferative constituents of the roots of Conyza canadensis.
    Planta medica, 2011, Volume: 77, Issue:11

    Bioassay-guided fractionation of the N-hexane and CHCl₃ phases of the methanol extract of the roots of Conyza canadensis (L.) Cronquist led to the isolation of two new dihydropyranones named conyzapyranone A (1) and B (2), and the known 4 Z,8 Z-matricaria- γ-lactone (3), 4 E,8 Z-matricaria- γ-lactone (4), 9,12,13-trihydroxy-10(E)-octadecenoic acid (5), epifriedelanol (6), friedeline (7), taraxerol (8), simiarenol (9), spinasterol (10), stigmasterol, β-sitosterol, and apigenin. The structures were determined by means of ESIMS and 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, NOESY, HSQC, and HMBC experiments. The isolated compounds were evaluated for their antiproliferative activities and were demonstrated to exert considerable cell growth-inhibitory activity against human cervix adenocarcinoma (HeLa), skin carcinoma (A431), and breast adenocarcinoma (MCF-7) cells. Some of the active components, including 2, 4, and 10, proved to be substantially more potent against these cell lines than against noncancerous human foetal fibroblasts (MRC-5) and can therefore be considered selective antiproliferative natural products.

    Topics: Antineoplastic Agents, Phytogenic; Apigenin; Cell Line, Tumor; Chemical Fractionation; Chromatography, High Pressure Liquid; Conyza; Female; Humans; Hydroxy Acids; Magnetic Resonance Spectroscopy; Molecular Structure; Oils, Volatile; Oleanolic Acid; Oleic Acids; Plant Extracts; Plant Roots; Pyrones; Sitosterols; Stigmasterol

2011
Active components from Siberian ginseng (Eleutherococcus senticosus) for protection of amyloid β(25-35)-induced neuritic atrophy in cultured rat cortical neurons.
    Journal of natural medicines, 2011, Volume: 65, Issue:3-4

    Not only neuronal death but also neuritic atrophy and synaptic loss underlie the pathogenesis of Alzheimer's disease as direct causes of the memory deficit. Extracts of Siberian ginseng (the rhizome of Eleutherococcus senticosus) were shown to have protective effects on the regeneration of neurites and the reconstruction of synapses in rat cultured cortical neurons damaged by amyloid β (Aβ)(25-35), and eleutheroside B was one of the active constituents. In this study, a comprehensive evaluation of constituents was conducted to explore active components from Siberian ginseng which can protect against neuritic atrophy induced by Aβ(25-35) in cultured rat cortical neurons. The ethyl acetate, n-butanol and water fractions from the methanol extract of Siberian ginseng showed protective effects against Aβ-induced neuritic atrophy. Twelve compounds were isolated from the active fractions and identified. Among them, eleutheroside B, eleutheroside E and isofraxidin showed obvious protective effects against Aβ(25-35)-induced atrophies of axons and dendrites at 1 and 10 μM.

    Topics: Amyloid beta-Peptides; Animals; Atrophy; Axons; Benzaldehydes; Cells, Cultured; Cerebral Cortex; Coumarins; Dendrites; Eleutherococcus; Fatty Acids; Female; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Neurites; Neurons; Phenylpropionates; Plant Extracts; Pregnancy; Rats; Rats, Sprague-Dawley; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Stigmasterol

2011
Marked accumulation of 27-hydroxycholesterol in the brains of Alzheimer's patients with the Swedish APP 670/671 mutation.
    Journal of lipid research, 2011, Volume: 52, Issue:5

    There is a significant flux of the neurotoxic oxysterol 27-hydroxycholesterol (27OHC) from the circulation across the blood-brain barrier. Because there is a correlation between 27OHC and cholesterol in the circulation and lipoprotein-bound cholesterol does not pass the blood-brain barrier, we have suggested that 27OHC may mediate the effects of hypercholesterolemia on the brain. We previously demonstrated a modest accumulation of 27OHC in brains of patients with sporadic Alzheimer's disease (AD), consistent with a role of 27OHC as a primary pathogenetic factor. We show here that there is a 4-fold accumulation of 27OHC in different regions of the cortexes of patients carrying the Swedish amyloid precursor protein (APPswe) 670/671 mutation. The brain levels of sitosterol and campesterol were not significantly different in the AD patients compared with the controls, suggesting that the blood-brain barrier was intact in the AD patients. We conclude that accumulation of 27OHC is likely to be secondary to neurodegeneration, possibly a result of reduced activity of CYP7B1, the neuronal enzyme responsible for metabolism of 27OHC. We discuss the possibility of a vicious circle in the brains of the patients with familial AD whereby neurodegenerative changes cause an accumulation of 27OHC that further accelerates neurodegeneration.

    Topics: Aged; Alzheimer Disease; Amyloid beta-Protein Precursor; Blotting, Western; Brain; Cholesterol; Female; Humans; Hydroxycholesterols; Male; Middle Aged; Mutation; Phytosterols; Sitosterols

2011
Downregulation of matrix metalloproteinase-13 by the root extract of Cyathula officinalis Kuan and its constituents in IL-1β-treated chondrocytes.
    Planta medica, 2011, Volume: 77, Issue:13

    The roots of Cyathula officinalis Kuan are widely used in Chinese medicine for the treatment of inflammatory disorders. Here, the ability of C. officinalis Kuan to downregulate matrix metalloproteinase (MMP)-13 was examined since MMP-13 is an important enzyme for the degradation of the cartilage collagen matrix, especially under arthritic conditions. The ethanol extract of C. officinalis Kuan as well as the N-hexane and chloroform soluble fractions were found to potently inhibit MMP-13 induction in IL-1 β-treated SW1353 cells, a human chondrosarcoma cell line, at 50-200 µg/mL. Activity-guided separation led to the isolation of six compounds, palmitic acid (1), β-sitosterol (2), α-spinasterol (3), atractylenolide I (4), 1,3-diacetoxy-tetradeca-6E,12E-dien-8,10-dyn (5), and N-trans-feruloyl-3-methyldopamine (6). Among these, 4 and 5 exhibited MMP-13 downregulating activity in IL-1 β-treated SW1353 cells. And 4 also showed anti-oedematous activity against λ-carageenan-induced paw edema in mice at 20-200 mg/kg, p. o. The results of this study provide information that can help elucidate the action mechanism of C. officinalis Kuan. In addition, the results presented here suggest that C. officinalis Kuan and its constituents may have the potential for chondroprotection against cartilage degrading disorders.

    Topics: Acetates; Alkynes; Amaranthaceae; Animals; Carrageenan; Cartilage; Cell Line, Tumor; Chondrocytes; Chondrosarcoma; Disease Models, Animal; Dopamine; Down-Regulation; Edema; Humans; Hypolipidemic Agents; Interleukin-1beta; Lactones; Male; Matrix Metalloproteinase 13; Medicine, Chinese Traditional; Mice; Mice, Inbred ICR; Phytotherapy; Plant Extracts; Plant Roots; Sesquiterpenes; Sitosterols; Stigmasterol

2011
β-Sitosterol down-regulates some pro-inflammatory signal transduction pathways by increasing the activity of tyrosine phosphatase SHP-1 in J774A.1 murine macrophages.
    International immunopharmacology, 2011, Volume: 11, Issue:8

    The objective of the present study was to examine the anti-inflammatory effects of β-sitosterol (SIT), the most common phytosterol in the diet, and to investigate its involvement in NF-κB and STAT1 pathways as potential mechanisms. In addition, the activity of the phosphatase SHP-1 as a negative modulator to these pathways, was investigated. Utilizing murine J774A.1 macrophages, cells were treated with various physiological concentrations of SIT and stimulated with LPS (100 ng/ml) for 6h. Results indicate that 1 and 16 μM SITs increased SHP-1 activity by 300% and 200%, respectively. Similar results were obtained using western blot analysis. Additionally, we observed reductions in the release of some pro-inflammatory cytokines and chemokines as well as an increase in anti-inflammatory IL-10 with SIT treatments. The results also demonstrate the inhibition of STAT1 with SIT treatment. Moreover, translocation of NF-κB to the nucleus was inhibited with SIT as indicated by decreased phosphorylation and the use of ImageStream cytometry. In conclusion, the present study demonstrates the anti-inflammatory effect on macrophages by inactivating STAT1 and NF-κB, which could be mediated by the activation of SHP-1.

    Topics: Animals; Cells, Cultured; Chemokines; Cytokines; Down-Regulation; Inflammation; Interleukin-10; Lipopolysaccharides; Macrophages; Mice; NF-kappa B; Protein Tyrosine Phosphatase, Non-Receptor Type 6; Signal Transduction; Sitosterols; STAT1 Transcription Factor

2011
Quantification of sterol lipids in plants by quadrupole time-of-flight mass spectrometry.
    Journal of lipid research, 2011, Volume: 52, Issue:5

    Glycerolipids, sphingolipids, and sterol lipids constitute the major lipid classes in plants. Sterol lipids are composed of free and conjugated sterols, i.e., sterol esters, sterol glycosides, and acylated sterol glycosides. Sterol lipids play crucial roles during adaption to abiotic stresses and plant-pathogen interactions. Presently, no comprehensive method for sterol lipid quantification in plants is available. We used nanospray ionization quadrupole-time-of-flight mass spectrometry (Q-TOF MS) to resolve and identify the molecular species of all four sterol lipid classes from Arabidopsis thaliana. Free sterols were derivatized with chlorobetainyl chloride. Sterol esters, sterol glycosides, and acylated sterol glycosides were ionized as ammonium adducts. Quantification of molecular species was achieved in the positive mode after fragmentation in the presence of internal standards. The amounts of sterol lipids quantified by Q-TOF MS/MS were validated by comparison with results obtained with TLC/GC. Quantification of sterol lipids from leaves and roots of phosphate-deprived A. thaliana plants revealed changes in the amounts and molecular species composition. The Q-TOF method is far more sensitive than GC or HPLC. Therefore, Q-TOF MS/MS provides a comprehensive strategy for sterol lipid quantification that can be adapted to other tandem mass spectrometers.

    Topics: Arabidopsis; Cholesterol; Chromatography, Gas; Chromatography, Thin Layer; Lipids; Mass Spectrometry; Phytosterols; Plants; Sitosterols; Sterols; Stigmasterol

2011
Molecular aspects of the interaction between plants sterols and DPPC bilayers: an experimental and theoretical approach.
    Journal of colloid and interface science, 2011, Jun-01, Volume: 358, Issue:1

    The effect of sterols composition in a lipid bilayer was investigated on membranes of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and mixtures with the plant sterols β-sitosterol and stigmasterol. Differential scanning calorimetry, 1,6-diphenyl-1,3,5-hexatriene (DPH) fluorescence polarization and infrared spectroscopy studies showed that both sterols changed the packing of the membrane and the hydration of the polar headgroup of the phospholipids, disordering the gel phase and, vice versa, ordering the membrane in the liquid crystalline phase. In all cases some differences among β-sitosterol and stigmasterol could be observed, being β-sitosterol slightly more efficient than stigmasterol in ordering a fluid membrane, bringing the membrane to a more packed liquid ordered phase. Molecular dynamic simulations were carried out to better characterize the distinct behavior of both sterols in a DPPC-membrane. The calculated parameters agreed quite well with the experimental results and a molecular model is proposed to explain differences in the sterols molecules and their effect on the DPPC-bilayer.

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Calorimetry, Differential Scanning; Diffusion; Fluorescence Polarization; Lipid Bilayers; Molecular Dynamics Simulation; Plants; Sitosterols; Spectrophotometry, Infrared; Stigmasterol

2011
Cerebral accumulation of dietary derivable plant sterols does not interfere with memory and anxiety related behavior in Abcg5-/- mice.
    Plant foods for human nutrition (Dordrecht, Netherlands), 2011, Volume: 66, Issue:2

    Plant sterols such as sitosterol and campesterol are frequently applied as functional food in the prevention of atherosclerosis. Recently, it became clear that plasma derived plant sterols accumulate in murine brains. We questioned whether plant sterols in the brain are associated with alterations in brain cholesterol homeostasis and subsequently with brain functions. ATP binding cassette (Abc)g5-/- mice, a phytosterolemia model, were compared to Abcg5+/+ mice for serum and brain plant sterol accumulation and behavioral and cognitive performance. Serum and brain plant sterol concentrations were respectively 35-70-fold and 5-12-fold increased in Abcg5-/- mice (P<0.001). Plant sterol accumulation resulted in decreased levels of desmosterol (P<0.01) and 24(S)-hydroxycholesterol (P<0.01) in the hippocampus, the brain region important for learning and memory functions, and increased lanosterol levels (P<0.01) in the cortex. However, Abcg5-/- and Abcg5+/+ displayed no differences in memory functions or in anxiety and mood related behavior. The swimming speed of the Abcg5-/- mice was slightly higher compared to Abcg5+/+ mice (P<0.001). In conclusion, plant sterols in the brains of Abcg5-/- mice did have consequences for brain cholesterol metabolism, but did not lead to an overt phenotype of memory or anxiety related behavior. Thus, our data provide no contra-indication for nutritional intake of plant sterol enriched nutrition.

    Topics: Affect; Animals; Anxiety Disorders; Atherosclerosis; ATP-Binding Cassette Transporters; Behavior, Animal; Brain; Cholesterol; Desmosterol; Diet; Hippocampus; Homeostasis; Hydroxycholesterols; Hypercholesterolemia; Intestinal Diseases; Lanosterol; Lipid Metabolism, Inborn Errors; Male; Maze Learning; Memory; Mice; Mice, Mutant Strains; Phytosterols; Sitosterols; Stigmasterol

2011
High-speed counter-current chromatographic separation of phytosterols.
    Analytical and bioanalytical chemistry, 2011, Volume: 400, Issue:10

    Phytosterols are bioactive compounds which occur in low concentrations in plant oils. Due to their beneficial effects on human health, phytosterols have already been supplemented to food. Commercial phytosterol standards show insufficient purity and/or are very expensive. In this study, we developed a high-speed counter-current chromatography (HSCCC) method for the fractionation and analysis of a commercial crude β-sitosterol standard (purity ∼60% according to supplier). Different solvent systems were tested in shake-flask experiments, and the system n-hexane/methanol/aqueous silver nitrate solution (34/24/1, v/v/v) was finally used for HSCCC fractionation. About 50 mg phytosterols was injected and distributed into 57 fractions. Selected fractions were condensed and re-injected into the HSCCC system. This measure provided pure sitostanol (>99%) and β-sitosterol (∼99%), as well as a mixture of campesterol and stigmasterol without further phytosterols. An enriched HSCCC fraction facilitated the mass spectrometric analysis of further 11 minor phytosterols (after trimethylsilylation). It was also shown that the commercial product contained about 0.3% carotinoids which eluted without delay into an early HSCCC fraction and which were separated from the phytosterols.

    Topics: Cholesterol; Countercurrent Distribution; Mass Spectrometry; Phytosterols; Sitosterols; Solvents; Stigmasterol

2011
[A new aristolochic acid derivative from Asarum himalaicum].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2011, Volume: 46, Issue:2

    To study the chemical constituents of Asarum himalaicum, fifteen compounds were isolated from a 70% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and semi-preparative HPLC. By spectroscopic techniques including 1H NMR, 13C NMR, and HR-ESI-MS, these compounds were identified as 4-demethoxyaristolochic acid BII (1), aristolochic acid I (2), aristolochic acid Ia (3), 7-hydroxyaristolochic acid I (4), aristolochic acid IV (5), aristolic acid II (6), debilic acid (7), aristololactam I (8), 9-hydroxyaristololactam I (9), 7-methoxyaristololactam IV (10), (2S)-narigenin-5, 7-di-O-beta-D-pyranosylglucoside (11), 4-hydroxybenzoic acid (12), 3, 4-dihydroxybenzoic acid (13), 4-hydroxycinnamic acid (14), and beta-sitosterol (15). All of these compounds (1-15) were obtained from A. himalaicum for the first time. Among them, 1 was identified as a new compound, and compounds 3-6, 9, 12-14 were isolated from Asarum genus for the first time. Since the kidney toxicity of aristolochic acids and aristololactams has been reported, the result of this investigation suggests that it should be cautioned to use A. himalaicum as a medicine.

    Topics: Aristolochic Acids; Asarum; Chromatography, High Pressure Liquid; Coumaric Acids; Hydroxybenzoates; Magnetic Resonance Spectroscopy; Molecular Structure; Parabens; Plants, Medicinal; Propionates; Sitosterols; Spectrometry, Mass, Electrospray Ionization

2011
Effects of long-term parenteral nutrition on serum lipids, plant sterols, cholesterol metabolism, and liver histology in pediatric intestinal failure.
    Journal of pediatric gastroenterology and nutrition, 2011, Volume: 53, Issue:4

    Plant sterols (PS) in parenteral nutrition (PN) may contribute to intestinal failure-associated liver disease. We investigated interrelations between serum PS, liver function and histology, cholesterol metabolism, and characteristics of PN.. Eleven patients with intestinal failure (mean age 6.3 years) receiving long-term PN were studied prospectively (mean 254 days) and underwent repeated measurements of serum lipids, noncholesterol sterols, including PS, and liver enzymes. PS contents of PN were analyzed. Liver biopsy was obtained in 8 patients. Twenty healthy children (mean age 5.7 years) served as controls.. Median percentage of parenteral energy of total daily energy (PN%) was 48%, including 0.9 g · kg(-1) · day(-1) of lipids. Respective amounts of PN sitosterol, campesterol, avenasterol, and stigmasterol were 683, 71, 57, and 45 μg · kg(-1) · day(-1). Median serum concentrations of sitosterol (48 vs 7.5 μmol/L, P < 0.001), avenasterol (2.9 vs 1.9, P < 0.01), stigmasterol (1.9 vs 1.2, P < 0.005), but not that of campesterol (9.8 vs 12, P = 0.22), were increased among patients in relation to controls, and correlated with PN% (r = 0.81-0.88, P < 0.005), but not with PN fat. Serum cholesterol precursors were higher in patients than in controls. Serum liver enzymes remained close to normal range. Glutamyl transferase correlated with serum PS (r = 0.61-0.62, P < 0.05). Liver fibrosis in 5 patients reflected increased serum PS (r = 0.55-0.60, P = 0.16-0.12).. Serum PS moderately increase during olive oil-based PN, and correlate positively with PN% and glutamyl transferase. Despite well-preserved liver function, histology often revealed significant liver damage.

    Topics: Adolescent; Biomarkers; Case-Control Studies; Child; Child, Preschool; Cholestasis; Cholesterol; Female; Follow-Up Studies; Humans; Infant; Intestines; Lipid Metabolism; Lipids; Liver; Liver Failure; Male; Olive Oil; Parenteral Nutrition; Phytosterols; Plant Oils; Prospective Studies; Sitosterols

2011
Validation of an isotope dilution gas chromatography-mass spectrometry method for analysis of 7-oxygenated campesterol and sitosterol in human serum.
    Chemistry and physics of lipids, 2011, Volume: 164, Issue:6

    High dose daily intake of plant sterols decreases the uptake of cholesterol in the intestine by competitive mechanisms and thus leads to reduced serum levels of total and LDL-cholesterol. By this, the commercialization of plant sterol enriched 'functional food' products is rapidly increasing. Subjects using these kinds of diet present a duplication of their serum plant sterol levels after long-term intake. In analogy to cholesterol, plant sterols such as campesterol and sitosterol can be oxidized to oxyphytosterols and these may counteract the primary anti-atherosclerotic action of cholesterol lowering. In order to investigate the whole spectrum of the consequences following high plant sterol intake a highly sensitive and specific isotope dilution gas chromatography-mass spectrometry method for the analysis of 7-oxygenated campesterol/sitosterol in trace amounts in human serum is presented in this paper. The validation was based on limits for detection and quantification, recovery, precision and minimization of autoxidation during work-up. Our results show an overall coefficient of variation ≤10% for the precision. The lowest limits for detection and quantification for 7α-hydroxy-campesterol were 7 pg/mL and 23 pg/mL, respectively. Data for overall sum recovery ranged from 92% to 115%. We practically used this method for analysis of oxyphytosterols simultaneously with plant sterol concentrations in serum from healthy volunteers. Sixteen subjects were treated with plant sterol enriched margarine (3 g/day) for 28 days. The results showed a significant increase of the oxyphytosterol 7β-hydroxy-sitosterol from 1.19±0.54 (before intake) to 2.24±1.24 ng/mL (mean±SD; +86.7%; P=0.007) after intake of the margarine. There was a highly significant correlation between the serum levels of campesterol and the sum of 7-oxygenated campesterol (R(2)=0.915; P<0.001) and sitosterol and the sum of 7-oxygenated sitosterol (R(2)=0.915; P<0.001). We can conclude from this study that the analytic method is well suited for detection of OPS, even at trace amounts.

    Topics: Adult; Blood Chemical Analysis; Cholesterol; Female; Gas Chromatography-Mass Spectrometry; Humans; Limit of Detection; Linear Models; Male; Margarine; Oxygen; Phytosterols; Sitosterols

2011
Simultaneous determination of trace sterols in complicated biological samples by gas chromatography-mass spectrometry coupled with extraction using β-sitosterol magnetic molecularly imprinted polymer beads.
    Journal of chromatography. A, 2011, Jul-15, Volume: 1218, Issue:28

    In this paper, an efficient and sensitive analytical method for the simultaneous determination of three trace sterols including ergosterol, stigmasterol and β-sitosterol in complicated biological samples was developed by gas chromatography-mass spectrometry (GC-MS) coupled with extraction using novel β-sitosterol magnetic molecularly imprinted polymer (mag-MIP) beads. Physical tests suggested that β-sitosterol mag-MIP beads prepared by a rapid microwave synthesis method possessed the porous morphology, narrow size distribution, stable chemical and thermal property. Due to the greatly enlarging surface area and the strong recognition to the target molecules, β-sitosterol mag-MIP beads have a higher enrichment factor for β-sitosterol (∼20-fold) and the higher selectivity for β-sitosterol and its analogs than that of β-sitosterol magnetic nonimprinted polymer (mag-NIP) beads. Under the optimum analytical conditions, all the target compounds achieved good chromatographic separation and sensitive detection without matrix interference. It was interesting that three target sterols were actually found in mushroom samples, and stigmasterol and β-sitosterol were actually found in serum and watermelon samples. The recoveries of spiked sample tests were in range of 71.6-88.2% with RSDs of 2.4-10.0% (n=3). This method is reliable and applicable for the simultaneous determination of trace sterols in real biological samples based on the β-sitosterol mag-MIP bead extraction.

    Topics: Agaricales; Chemical Fractionation; Citrullus; Gas Chromatography-Mass Spectrometry; Humans; Microscopy, Electron, Scanning; Microspheres; Molecular Imprinting; Particle Size; Reproducibility of Results; Sensitivity and Specificity; Sitosterols; Sterols

2011
Antidiabetic activity of γ-sitosterol isolated from Lippia nodiflora L. in streptozotocin induced diabetic rats.
    European journal of pharmacology, 2011, Sep-30, Volume: 667, Issue:1-3

    Lippia nodiflora L. (Verbenaceae) is a creeping perennial herb widely used in traditional system of medicine to treat ulcers, bronchitis and heart diseases; it also possesses antidiabetic property. In the present study, γ-sitosterol isolated from Lippia nodiflora was screened for its antidiabetic property in streptozotocin (STZ) induced diabetic rats. Insulin secretion in response to glucose was evaluated in isolated rat islets. Oral administration of γ-sitosterol (20 mg/kg body weight) once daily for 21 days in STZ-induced diabetic rats resulted in a significant decrease in blood glucose and glycosylated hemoglobin with a significant increase in plasma insulin level, body weight and food intake. Furthermore γ-sitosterol showed antihyperlipidemic activity as evidenced by significant decrease in serum total cholesterol, triglycerides and very low density lipoprotein-cholesterol levels coupled with elevation of high density lipoprotein-cholesterol levels in treated rats. A significant decrease in the activities of alanine aminotransaminase, aspartate aminotransaminase, alkaline phosphatase and acid phosphatase in γ-sitosterol treated rats when compared to diabetic control rats indicated its protective role against liver damage. γ-Sitosterol increased insulin secretion in response to glucose. Immunohistochemical study of pancreas also confirmed the biochemical findings. These results indicated that γ-sitosterol, the compound isolated from L. nodiflora, possessed antihyperglycemic activity.

    Topics: Animals; Biomarkers; Blood Glucose; Body Weight; Carbohydrate Metabolism; Diabetes Mellitus, Experimental; Fasting; Glycated Hemoglobin; Glycogen; Hypoglycemic Agents; Insulin; Insulin Secretion; Lipid Metabolism; Lippia; Liver; Male; Muscles; Rats; Rats, Wistar; Sitosterols

2011
Ripening, storage temperature, ethylene action, and oxidative stress alter apple peel phytosterol metabolism.
    Phytochemistry, 2011, Volume: 72, Issue:11-12

    The chilling conditions of apple cold storage can provoke an economically significant necrotic peel disorder called superficial scald (scald) in susceptible cultivars. Disorder development can be reduced by inhibiting ethylene action or oxidative stress as well as intermittent warming. It was previously demonstrated that scald is preceded by a metabolomic shift that results in altered levels of various classes of triterpenoids, including metabolites with mass spectral features similar to β-sitosterol. In this study, a key class of phytosterol metabolites was identified. Changes in peel tissue levels of conjugates of β-sitosterol and campesterol, including acylated steryl glycosides (ASG), steryl glycosides (SG) and steryl esters (SE), as well as free sterols (FS), were determined during the period of scald development. Responses to pre-storage treatment with the ethylene action inhibitor, 1-methylcyclopropene, or an antioxidant (diphenylamine), rapid temperature elevation, and cold acclimation using intermittent warming treatments were evaluated. Diphenylamine, 1-MCP, and intermittent warming all reduced or prevented scald development. ASG levels increased and SE levels decreased in untreated control fruit during storage. Removing fruit from cold storage to ambient temperature induced rapid shifts in ASG and SE fatty acyl moieties from unsaturated to saturated. FS and SG levels remained relatively stable during storage but SG levels increased following a temperature increase after storage. ASG, SE, and SG levels did not increase during 6 months cold storage in fruit subjected to intermittent warming treatment. Overall, the results show that apple peel phytosteryl conjugate metabolism is influenced by storage duration, oxidative stress, ethylene action/ripening, and storage temperature.

    Topics: Acclimatization; Antioxidants; Cyclopropanes; Diphenylamine; Ethylenes; Food Preservation; Fruit; Malus; Oxidative Stress; Phytosterols; Plant Diseases; Sitosterols; Temperature

2011
[Studies on identification and secondary metabolites of endophytic fungi strain E8 from Curcuma wenyujin].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:6

    To identify the endophyte strain E8 with high activity from Curcuma wenyujin and study its secondary metabolites.. The strain E8 was identified by morphological observation and ITS sequence analysis. Manifold chromatographic methods were used to separate and purify the chemical constituents of fermentation broth from strain E8, and their structures were identified by physiochemical properties and spectral data.. The strain E8 belongs to P. oxalicum. Four compounds were isolated from the fermentation broth of this strain and elucidated as chrysophanol, emodin, secalonic acid A and beta-sitosterol.. The endophyte P. oxalicum was isolated from medicinal plant Curcuma wenyujin for the first time. Four compounds were first isolated from endophytic fungus in C. wenyujin. Thus, microbial fermentation is a new access for these compounds production.

    Topics: Anthraquinones; Curcuma; Emodin; Fermentation; Penicillium; Sitosterols; Xanthones

2011
Phytosterols can impair vitamin D intestinal absorption in vitro and in mice.
    Molecular nutrition & food research, 2011, Volume: 55 Suppl 2

    Adequate vitamin D status is necessary and beneficial for health, although deficiency and insufficiency are very common. As cholecalciferol (vitamin D(3) ) structure is close to cholesterol structure, we hypothesized that phytosterols, frequently used to decrease cholesterol, intestinal absorption and consequently to reduce hypercholesterolemia, may also interact with cholecalciferol absorption.. β-Sitosterol effect on cholecalciferol postprandial response was first assessed in mice. We then evaluated the effect of different sterols on (i) cholecalciferol micellar incorporation, (ii) cholecalciferol apical uptake and (iii) basolateral efflux in vitro or ex vivo. In mice, cholecalciferol bioavailability was 15-fold lower in the presence of β-sitosterol (p<0.05). This can partly be explained by the fact that phytosterols significantly impaired cholecalciferol incorporation into mixed micelles (from -16 to -36% depending on sterol micellar composition). This can also be due to the fact that in Caco-2 cells and mouse intestinal explants, phytosterols significantly lowered cholecalciferol apical uptake (from -13 to -39%). Conversely, phytosterols had no effect on cholecalciferol secretion at the basolateral side of Caco-2 cells.. The present data suggest for the first time that phytosterols can interact with vitamin D(3) intestinal absorption. This interaction can be explained by a competition for micellar incorporation and for apical uptake.

    Topics: Animals; Caco-2 Cells; Cholecalciferol; Cholesterol; Enterocytes; Humans; In Vitro Techniques; Intestinal Absorption; Intestinal Mucosa; Male; Mice; Mice, Inbred C57BL; Micelles; Phytosterols; Postprandial Period; Sitosterols; Vitamin D

2011
Effect of phytosterols and their oxidation products on lipoprotein profiles and vascular function in hamster fed a high cholesterol diet.
    Atherosclerosis, 2011, Volume: 219, Issue:1

    Human diets contain phytosterols and their oxidation products. We investigated effect of β-sitosterol (Si), stigmasterol (St), β-sitosterol oxidation products (SiOP) and stigmasterol oxidation products (StOP) on plasma total cholesterol and their interaction with the gene expression of enzymes, proteins and transporters involved in cholesterol absorption and metabolism. Sixty male hamsters were fed the control diet or one of four experimental diets containing 0.1% Si, 0.1% SiOP, 0.1% St and 0.1% StOP, respectively, for six weeks. SiOP and StOP groups had the relative liver weights greater than their corresponding non-oxidized forms, indicating they were possibly toxic. Results showed both Si and St groups reduced while SiOP and StOP hamsters lost the capacity of lowering plasma total cholesterol (TC), low-density lipoprotein cholesterol (LDL) and triacylglycerols (TG) compared with the control group. Si and St but not SiOP and StOP were anti-atherosclerotic. RT-PCR analysis demonstrated Si and St but not SiOP and StOP down-regulated mRNA levels of intestinal acyl CoA: cholesterol acyltransferase (ACAT2) and microsomal triglyceride protein (MTP). Aortas from Si and St hamsters relaxed better than those from the control and their corresponding SiOP and StOP-treated hamsters. It was concluded that Si and St not SiOP and StOP were beneficial in improving lipoprotein profile and aortic function.

    Topics: Animals; Aorta, Thoracic; Cholesterol; Cholesterol, Dietary; Cricetinae; Lipoproteins; Liver; Male; Mesocricetus; Organ Size; Oxidation-Reduction; Plaque, Atherosclerotic; Sitosterols; Stigmasterol; Triglycerides; Vasoconstriction; Vasodilation

2011
Effects of sterol-binding agent nystatin on wheat roots: the changes in membrane permeability, sterols and glycoceramides.
    Phytochemistry, 2011, Volume: 72, Issue:14-15

    Plant sterols are important multifunctional lipids, which are involved in determining membrane properties. Biophysical characteristics of model lipid and isolated animal membranes with altered sterol component have been intensively studied. In plants however, the precise mechanisms of involvement of sterols in membrane functioning remain unclear. In present work the possible interactions between sterols and other membrane lipids in plant cells were studied. A useful experimental approach for elucidating the roles of sterols in membrane activity is to use agents that specifically bind with endogenous sterols, for example the antibiotic nystatin. Membrane characteristics and the composition of membrane lipids in the roots of wheat (Triticum aestivum L.) seedlings treated with nystatin were analyzed. The application of nystatin greatly increased the permeability of the plasma membrane for ions and SH-containing molecules and decreased the total sterol level mainly as a consequence of a reduction in the amount of β-sitosterol and campesterol. Dynamic light-scattering was used to confirm the in vitro formation of stable complexes between nystatin and β-sitosterol or cholesterol. Sterol depletion was accompanied by a significant rise in total glycoceramide (GlCer) content after 2h treatment with nystatin. Analysis of the GlCer composition using mass spectrometry with electrospray ionization demonstrated that nystatin induced changes in the ratio of molecular species of GlCer. Our results suggest that changes in the sphingolipid composition can contribute to the changes in plasma membrane functioning induced by sterol depletion.

    Topics: Biological Transport; Cell Membrane; Cell Membrane Permeability; Ceramides; Cholesterol; Ionophores; Membrane Lipids; Nystatin; Phytosterols; Plant Roots; Potassium; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Sphingolipids; Time Factors; Triticum

2011
Minor pregnanes from Caralluma adscendens var. gracilis and Caralluma pauciflora.
    Fitoterapia, 2011, Volume: 82, Issue:7

    Phytochemical investigation of Caralluma adscendens var. gracilis and Caralluma pauciflora (Asclepiadaceae) whole plant extracts allowed to isolate one pregnane glycoside and two pregnanes characterized as 12β,20-O-dibenzoyl-5α,6-dihydrosarcostin β-oleandropyranosyl-(1→4)-β-cymaropyranosyl-(1→4)-β-digitoxypyranosyl-(1→4)-β-cymaropyranosyl-(1→4)-β-cymaropyranoside (1), 12β-O-benzoyl-3β,11α,14β,20R-pentahydroxy-pregn-5-ene (2), and 11α-O-benzoyl-3β,12β,14β,20R-pentahydroxy-pregn-5-ene (3), respectively. Their structural characterization was obtained on the basis of extensive NMR spectral studies. Three known pregnane glycosides along with lupeol and β-sitosterol were also isolated and characterized.

    Topics: Apocynaceae; Glycosides; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Extracts; Pregnanes; Sitosterols

2011
Paniculacin, a new coumarin derivative from Murraya paniculata.
    Journal of Asian natural products research, 2011, Volume: 13, Issue:8

    Paniculacin (1), a new coumarin derivative, has been isolated from the ethyl acetate soluble fraction of the ethanolic extract of Murraya paniculata along with umbelliferone, scopoletin, 4-hydroxybenzoic acid, trans-cinnamic acid, and β-sitosterol. Their structures were elucidated on the basis of spectral data.

    Topics: Cinnamates; Coumarins; Molecular Structure; Murraya; Nuclear Magnetic Resonance, Biomolecular; Pakistan; Parabens; Scopoletin; Sitosterols

2011
Determination of β-sitosterol and cholesterol in oils after reverse micelles with Triton X-100 coupled with ultrasound-assisted back-extraction by a water/chloroform binary system prior to gas chromatography with flame ionization detection.
    Analytica chimica acta, 2011, Sep-09, Volume: 701, Issue:2

    Ultrasonic back-extraction of Triton X-100 reverse micelles by a water/chloroform binary system and gas chromatography with flame ionization detection (GC-FID) was developed for extraction and determination of β-sitosterol and cholesterol in soybean and sunflower oil samples. After the homogenization of the oil samples with Triton X-100, an aliquot of 200 μL of methanol was added to the samples to form two phases. The clear Triton X-100 extract obtained by centrifugation was treated with a mixture of water (1000 μL) and chloroform (300 μL) for back-extraction of the analytes into the chloroform phase by ultrasonication. After centrifugation, the sedimented chloroform layer was withdrawn easily by a microsyringe and directly injected into the GC-FID system. The influence of several important parameters on the extraction efficiencies of the analytes was evaluated. Under optimized experimental conditions, the calibration graphs were linear in the range of 1.0-30.0 mg L(-1) with coefficient of determination more than 0.994 for both analytes. The method detection limit values were in the range of 0.2-0.7 mg L(-1). The lower limit of quantification values were in the range of 0.7-2.4 mg L(-1). Intra-day relative standard deviations were in the range of 1.0-2.7%. This procedure was successfully applied with satisfactory results to the determination of β-sitosterol and cholesterol in spiked oil samples. The relative mean recoveries of oil samples ranged from 93.6% to 105.0%.

    Topics: Chemical Fractionation; Chloroform; Cholesterol; Chromatography, Gas; Flame Ionization; Micelles; Octoxynol; Oils; Sitosterols; Ultrasonics; Water

2011
[Effect of different fertilizing levels on yields and efficiency components of Pinellia ternata from Sichuan].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:8

    The effect of the different fertilizing levels on yields and main active components of Pinellia ternata from Sichuan was studied under the cultivated condition, in order to provide theoretical basis for the standardized cultivation.. Using one of the wild populations of P. ternate from Sichuan as tested material, the experiment was performed with orthogonal designing methods L25 (5(3)). During growth and development period, agronomic traits such as number of sprouting, inflorescence and bulblets were counted. After harvesting, main chemical compositions, growth and proliferation rates were determined.. In different fertilizing levels, the P. ternata from Sichuan showed the same growth rhythm, though there were significant difference (P < 0.05) among the average emergence rate,whereas extremely significant difference (P < 0.01) were detected among the average ratio of bolting, the average bulbils, individual growth rate, individual proliferation rate, beta-sitosterol and alkaloid content under different fertilizing levels. Nitrogenous fertilizer that affected the content of alkaloids and beta-sitosterol were extremely significant (P < 0.01), whereas phosphate and potassium fertilizer had no significant effect. The effect of fertilizer factor and inter effects on beta-sitosterol showed no significant effect, but have influence on other indexes.. The optimum fertilizer composition was 315 kg x hm(-2) of nitrogen, 225 kg x hm(-2) of P2O5 and 270 kg x hm(-2) of K2O.

    Topics: Alkaloids; Fertilizers; Nitrogen Compounds; Phosphates; Phosphorus Compounds; Pinellia; Potassium Compounds; Sitosterols

2011
[Chemical constituents of Ammopiptanthus mongolicus].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:8

    To study the chemical constituents of aerial parts of Ammopiptanthus mongolicus.. Isolation and purification were carried out on silica gel, Sephadex LH-20 and HPLC column chromatography. The structures of the compounds were identified by physico-chemical properties and spectral analysis.. Nine compounds were isolated and identified as (+)-maackiain (1), brevifolin (2), 7-hydroxy-4'-methoxy isoflavanone (3), daidzein 4',7-diglucoside (4), genistein 4', 7-di-O-beta-D-glucoside (5), isolupalbigenin (6), ononin (7), beta-sitosterol (8), beta-daucosterol (9).. Compounds 2, 4 - 6 were obtained from the genus Ammopiptanthus for the first time.

    Topics: Chromatography, Agarose; Chromatography, High Pressure Liquid; Fabaceae; Glucosides; Isoflavones; Plant Extracts; Plant Leaves; Pterocarpans; Silica Gel; Sitosterols; Taxoids

2011
[Studies on the diterpenoids of Wedelia prostrata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:3

    To study the chemical constituents of Wedelia prostrata.. Chromatography and spectroscopic analysis were employed to isolate and elucidate the chemical constituents in the plant.. Seven compounds were obtained and identified as ent-kaur-16-en-19-oic acid (I), ent-kaur-16alpha, 17-dihydroxy-19-oic acid (II), ent-kaur-15alpha-senecioyloxy-16-en-19-oic acid (III), beta-sitosterol (IV), stigmasterol (V), stigmasterol-3-O-beta-D-glucopyranoside (VI) and n-hexacosanol (VII).. Compounds I-III are isolated from this plant for the first time.

    Topics: Diterpenes; Fatty Alcohols; Glucosides; Molecular Structure; Plant Components, Aerial; Sitosterols; Spectrophotometry, Ultraviolet; Stigmasterol; Wedelia

2011
[Studies on the chemical constituents of Laportea bulbifera].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:2

    To study the chemical constituents of Laportea bulbifera.. 70% EtOH was used for constituent extraction, silica gel column chromatography for constituent seperation, physical and chemical properties together with spectroscopic methods for chemical structure identification.. six compounds were obtained from root of L. bulbifera. Their chemical structures were elucidated as p3-sitosterol(1) , P-daucosterol (2), 2,2'-oxy-bis(1-phenylethanol (3), 1-(2-phenylcarbonyloxy acetyl) benzene (4) , methyl linoleate(5),1,4-diphenyl-1,4-butanedione(6).. All compounds are isolated from L. bulbifera and among compounds 3 and 4 are reported as natural products for the first time.

    Topics: Linoleic Acids; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Plants, Medicinal; Rhizome; Sitosterols; Urticaceae

2011
[Studies on the chemical constituents in fruits of Acanthopanax gracilistylus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:2

    To study the chemical constituents in the fruits of Acanthopanax gracilistylus.. The chemical components were isolated and purified by silica gel, ODS C-18, and Sephadex LH-20 column chromatogram. The chemical structures were elucidated on the basis of physicochemical properties and spectral data.. Ten compounds were isolated and identified as acankoreoside D(1), 3alpha, 11alpha-dihydroxylup-20(29)-en-28-oic acid(2), 3/3-([O-beta-D-glucopyranuronosyl] oxy) -olean-12-ene-28-olc acid (3),3beta-([O-beta-D-glucopyranuronosyl]oxy)-28-O-P3-D-glucopyranosyl-olean-12-ene-28-olc acid(4),oleanolic acid-3-O-6'-O-methyl-beta-D-glucuronopyranoside(5), acantrifoside A(6), acankoreoside A(7), (-)-kaur-16-en-19-oic acid(8), protocatechuic acid (9),beta-sitosterol(10).. Compounds 2-5 are obtained from the fruits of the plant for the first time.

    Topics: Eleutherococcus; Ethanol; Fruit; Hydroxybenzoates; Magnetic Resonance Spectroscopy; Plants, Medicinal; Saponins; Sitosterols; Triterpenes

2011
[Studies on the chemical constituents of Salsola collina].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:2

    To study the chemical constituents of Salsola collina.. The compounds were isolated by column chromatography, and their structures were identified by physical and chemical properties and spectral data.. Seven compounds were isolated and identified as n-lignoceric acid (1), n-dotriacontanic acid (2), beta-sitosterol (3), 5, 2'-dihydroxy-6, 7-methylenedioxy-isoflavone (4), vanillic acid (5), (-)syringaresinol 4,4'-bis-O-beta-D-glucopyranoside (6), salicylic acid (7).. The compounds of 1, 2, 4, 5 and 6 are isolated from the plant for the first time.

    Topics: Antihypertensive Agents; Chromatography, Thin Layer; Disaccharides; Fatty Acids; Isoflavones; Molecular Structure; Naphthalenes; Plant Components, Aerial; Plants, Medicinal; Salsola; Sitosterols; Vanillic Acid

2011
[Studies on the chemical constituents from the leave of Paulownia tomentosa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:2

    To study the chemical constituents of the leave of Paulownia tomentosa.. The constituents were isolated by column chromatography and their structures were elucidated through spectroscopic analysis.. The compounds were identified as apigenin(I), uteolin(II), homoeriodictyol(III), 3alpha-hydroxyurs-12-en-28-oic acid (IV),3beta,19alpha-dihydroxyurs-12en-28-oic acid (pomolic acid)(V),2alpha,3a-dihydroxyurs-12-en-28-oic acid(VI),ursolic acid (VII),2alpha,3beta-dihydroxyolean-12-en-28-oic acid (maslinic acid) (VIII), daucosterol(IX),beta-sitosterol(X).. The compound I-X are obtained from the leave of Paulownia tomentosa (Thunb.) Steud for the first time.

    Topics: Ethanol; Flavones; Molecular Structure; Plant Leaves; Plants, Medicinal; Scrophulariaceae; Sitosterols; Triterpenes; Ursolic Acid

2011
[Studies on the chemical constituents of Artemisia lavandulaefolia].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:2

    To investigate the chemical constituents from aerial part of Aremisia lavandulaefolia.. Compounds were isolated by using silicagel, Sephadex LH-20 chromatography and their structures were elucidated by means of spectral data analysiy.. Eight compounds were isolated and identifies as P-amyrin(1), P-sitosterol(2), ursolic acid(3), erpatilin(4), naringenin(5), apigenin(6), luteolin(7), quercetin(8).. All these compounds are isolated from this plant for the first time.

    Topics: Artemisia; Flavones; Molecular Structure; Oleanolic Acid; Plant Components, Aerial; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

2011
[Chemical constituents from Exochorda racemosa].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:9

    To study the chemical constituents of Exochorda racemosa.. Compounds were isolated and purified by silica gel, Sephadex LH-20, MCI gel and RP-18 column chromatography, and their structures were determined by spectroscopic analysis.. Twenty compounds were isolated and identified as N-p-coumaroyl-N'-caffeoylputrescine (1), sutherlandin trans-p-coumarate (2), apigenin 7-O-methylglucuronide (3), astragalin (4), nicotiflorin (5), kaempferol 3-neohesperidoside (6), rutin (7), apigenin (8), luteolin (9), linalool-1-oic acid (10), betulalbuside A (11), ursolic acid (12) , corosolic acid (13), gynuramide II (14), beta-sitosterol (15), daucosterol (16), uridine (17), adenosine (18), syringin (19), and trans4-hydroxycinnamic acid (20), respectively.. All compounds were obtained from this plant for the first time, moreover, 1 was reported as a new natural product, and 2 is a naturally rare cyanogenic glycoside.

    Topics: Apigenin; Flavonoids; Glucosides; Glucuronides; Kaempferols; Luteolin; Magnetic Resonance Spectroscopy; Phenols; Phenylpropionates; Rosaceae; Sitosterols; Triterpenes; Ursolic Acid

2011
[Studies on chemical constituents in roots of Helicteres angustifolia].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:9

    To study the chemical constituents of the roots of Helicteres angustifolia.. The compounds were isolated and purified by column chromatographic methods on silica gel, Sephadex LH-20, ODS and preparative HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral data.. Fourteen compounds were isolated from this plant. Their structures were identified as methyl helicterate(1),3-acetoxybetulin(2),3beta-acetoxy-27-(p-hydroxyl)benzoyloxylup-20(29)-en-28-oic acid methyl ester(3),3beta-acetoxy-27-benzoyloxylup-20(29)-en-28-oic acid(4),3beta-acetoxybetulinic acid(5),pyracrenic acid(6),cucurbitacin D(7),cucurbitacin B(8),isocucurbitacin D(9),3beta-acetoxy-27-[(4-hydroxybenzoyl)oxy]olean-12-en-28-oic acid methyl ester (10),beta-sitosterol(11),2alpha,7beta,20alpha-trihydroxy-3beta,21-dimethoxy-5-pregnene(12), hexadecanoic acid(13), and daucosterol(14), respectively.. Compounds 5,8,9,13, 14 were isolated from this plant for the first time.

    Topics: Magnetic Resonance Spectroscopy; Malvaceae; Plant Roots; Sitosterols; Triterpenes

2011
Protected effect of Esenbeckia leiocarpa upon the inflammatory response induced by carrageenan in a murine air pouch model.
    International immunopharmacology, 2011, Volume: 11, Issue:12

    This study was conducted to investigate the anti-inflammatory efficacy of Esenbeckia leiocarpa against the inflammation caused by the carrageenan using a murine air pouch model.. The effects of the crude hydroalcoholic extract (CHE), fractions (n-hexane (Hex) and ethyl acetate (AcOEt)), subfractions (polar (Pol) and nonpolar (Nonpol)), or isolated compounds (dihydrocorynantheol (DHC) and beta-sitosterol (β-Sit)) isolated from CHE upon leukocytes, exudate, myeloperoxidase (MPO) adenosine-deaminase (ADA), nitrate/nitrite (NO(x)), interleukin-1 beta (IL-1β), tumor necrosis factor-alpha (TNF-α), and inhibitory kappa-B-alpha (IκB-α) degradation were evaluated. The CHE, Alk, Pol, Nonpol, DHC and β-Sit, inhibited leukocytes, exudate, MPO and ADA, NO(x), IL-1β, and TNF-α (P<0.05). The Hex and AcOEt fractions inhibited all of the proinflammatory parameters, except the exudate. The compound DHC prevented the IκB-α degradation.. E. leiocarpa possesses important anti-inflammatory properties. These inhibitory effects occurred along with the downregulation of nitric oxide, IL-1β and TNF-α levels. The isolated compounds DHC and β-Sit may be partially responsible for these anti-inflammatory effects.

    Topics: Adenosine Deaminase; Alkaloids; Animals; Anti-Inflammatory Agents; Carrageenan; Cytokines; Down-Regulation; Inflammation; Leukocytes; Magnoliopsida; Mice; Plant Bark; Plant Extracts; Sitosterols; Treatment Outcome

2011
Wound healing efficacy of Jatyadi Taila: in vivo evaluation in rat using excision wound model.
    Journal of ethnopharmacology, 2011, Oct-31, Volume: 138, Issue:1

    In traditional Indian medicinal treatise there are several Ayurvedic formulations mentioned which have been claimed as potential wound healing agents like Madhu Ghrita and Jatyadi Taila. Jatyadi Taila (JT) is a medicated oil formulation (Taila) popularly used in the treatment of various topical wounds.. Though JT has its composition recorded in ancient Ayurvedic texts, there have been minimal attempts to standardize its use in the management of wound. The current work evaluates the wound healing efficacy of JT and also provides evidence of the dermal absorption kinetics of Karanjin from JT.. JT was subjected to preliminary phytochemical evaluation. Therapeutically active marker components β-sitosterol, lupeol and karanjin were detected and separated using HPTLC. As a part of safety evaluation, skin irritation potential of JT was evaluated on rabbit skin. Excision wound model in rats were used to evaluate the wound healing efficacy of JT. Histopathological and biochemical evaluations of excised skin tissues at wound sites were carried out. The HPTLC method developed was also validated to evaluate the pharmacokinetics of Karanjin from JT after topical application on pinna of rabbit.. Preliminary phytochemical evaluation of JT revealed presence of flavonoids, essential oils, tannins, glycosides, steroids and alkaloids while resins were found to be absent. HPTLC confirmed the presence of karanjin, lupeol and β-sitosterol in JT. JT was found to be non-irritant when applied to the skin of rabbits. Topical application of JT on excision wounds caused significantly faster reduction in wound area as compared to the application of modern topical formulation (Neosporin(®)) and untreated control wounds. Animals treated with JT showed significant increase in protein, hydroxyproline and hexosamine content in the granulation tissue when compared with the untreated controls. Wound healing potential of JT was found to be dose dependant. HPTLC method was successfully used to evaluate the pharmacokinetics of Karanjin after topical application of JT on rabbit pinna.. Current work demonstrates a modern approach towards standardization of the use of traditional topical formulation JT. The results justify the traditional claim of JT for its use in the management of wounds.

    Topics: Administration, Topical; Amines; Animals; Bacitracin; Benzopyrans; Disease Models, Animal; Dose-Response Relationship, Drug; Drug Combinations; Female; Granulation Tissue; Hydroxyproline; Male; Medicine, Ayurvedic; Neomycin; Pentacyclic Triterpenes; Phytotherapy; Plant Extracts; Polymyxin B; Proteins; Rabbits; Rats; Rats, Wistar; Sitosterols; Skin; Wound Healing; Wounds and Injuries

2011
Isolation and in vivo hepatoprotective activity of Melothria heterophylla (Lour.) Cogn. against chemically induced liver injuries in rats.
    Asian Pacific journal of tropical medicine, 2011, Volume: 4, Issue:8

    To investigate hepatoprotective activity of ethanol extract of Melothria heterophylla Lour Cogn. (EEMH) against CCl(4)-induced hepatic damage in rats.. β-sitosterol was isolated by column chromatography and characterized spectroscopically. Two different doses (200 and 400 mg/kg bw) of EEMH were administered orally in alternate days. The hepatoprotective activity was studied in liver by measuring biochemical parameters such as serum aspartate amino transferase (AST), alanine amino transferase (ALT), alkaline phosphatase (ALP), total protein and total bilirubin. Lipid peroxidation product and different antioxidant enzyme activities were assessed in liver homogenate.. EEMH reduced all biochemical parameters and lipid peroxidation, as well as it increased the antioxidant enzyme activities in comparison with silymarin. The protective effect of the extract on CCl(4) induced damage was confirmed by histopathological examination of the liver.. This result strongly supports the protective effect of EEMH against acute liver injury, and may be attributed to its antioxidative activity.

    Topics: Alanine Transaminase; Alkaline Phosphatase; Animals; Antioxidants; Aspartate Aminotransferases; Carbon Tetrachloride; Chemical and Drug Induced Liver Injury; Cucurbitaceae; Lipid Peroxidation; Liver; Male; Oxidative Stress; Plant Extracts; Protective Agents; Rats; Rats, Wistar; Silymarin; Sitosterols

2011
Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae).
    Natural product research, 2011, Volume: 25, Issue:18

    The first phytochemical study of Simira eliezeriana Peixoto (Rubiaceae) allowed the isolation and structural determination of two new diterpenes named simirane A [(5R,6R,8R,9R,10S,11S,13S)-6β,11β-dihydroxy-2,4(18),15-erythroxylatrien-1-one] (1) and simirane B [(5S,8R,9R,10S,11S,13S)-11β-hydroxy-2,4(18),15-erythroxylatrien-1-one] (2), together with seven known compounds: sitosterol (3), stigmasterol (4), campesterol (5), coniferaldehyde (6), vanillin (7), pinoresinol (8) and harman (9) from the bark of the plant. The structures of the compounds were established on the basis of spectroscopic methods, including 1-D and 2-D NMR, HRESI-MS and CD analysis and comparisons with available literature data of known compounds.

    Topics: Acrolein; Benzaldehydes; Cholesterol; Diterpenes; Ethanol; Furans; Harmine; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Phytosterols; Plant Bark; Plant Extracts; Rubiaceae; Sitosterols

2011
A new insight into application for barley chromosome addition lines of common wheat: achievement of stigmasterol accumulation.
    Plant physiology, 2011, Volume: 157, Issue:3

    Barley (Hordeum vulgare) has a much higher content of bioactive substances than wheat (Triticum aestivum). In order to investigate additive and/or synergistic effect(s) on the phytosterol content of barley chromosomes, we used a series of barley chromosome addition lines of common wheat that were produced by normal crossing. In determining the plant sterol levels in 2-week-old seedlings and dry seeds, we found that the level of stigmasterol in the barley chromosome 3 addition (3H) line in the seedlings was 1.5-fold higher than that in the original wheat line and in the other barley chromosome addition lines, but not in the seeds. Simultaneously, we determined the overall expression pattern of genes related to plant sterol biosynthesis in the seedlings of wheat and each addition line to assess the relative expression of each gene in the sterol pathway. Since we elucidated the CYP710A8 (cytochrome P450 subfamily)-encoding sterol C-22 desaturase as a key characteristic for the higher level of stigmasterol, full-length cDNAs of wheat and barley CYP710A8 genes were isolated. These CYP710A8 genes were mapped on chromosome 3 in barley (3H) and wheat (3A, 3B, and 3D), and the expression of CYP710A8 genes increased in the 3H addition line, indicating that it is responsible for stigmasterol accumulation. Overexpression of the CYP710A8 genes in Arabidopsis increased the stigmasterol content but did not alter the total sterol level. Our results provide new insight into the accumulation of bioactive compounds in common wheat and a new approach for assessing plant metabolism profiles.

    Topics: Amino Acid Sequence; Arabidopsis; Biosynthetic Pathways; Chromosomes, Plant; Crosses, Genetic; Gene Expression Regulation, Plant; Genes, Plant; Genetic Techniques; Hordeum; Molecular Sequence Data; Plant Leaves; Plant Proteins; Plants, Genetically Modified; Seedlings; Seeds; Sitosterols; Stigmasterol; Triticum

2011
Chronic effects of Pinus radiata and Eucalyptus globulus kraft mill effluents and phytosterols on Daphnia magna.
    Bulletin of environmental contamination and toxicology, 2011, Volume: 87, Issue:6

    Two kraft pulp mill effluents were compared in terms of their chronic toxicity to Daphnia magna. One resulted from pulping Pinus radiata and the other came from a parallel processing of Pinus radiata and Eucalyptus globulus (mixed kraft pulp mill effluent). The concentration of phytosterols found in the mixed kraft pulp mill effluent was higher than in the effluent from Pinus radiata, with values of 0.1082 and 0.02 μg/L, respectively. The phytosterols per se are responsible for 12.9% and 8.1% of the deviation from the natural shape, while the kraft pulp mill effluents account for 25.6%-27.8% of shape deviation. The role of β-sitosterol and stigmasterol is discussed in relation to endocrine disruption.

    Topics: Animals; Daphnia; Endocrine Disruptors; Eucalyptus; Industrial Waste; Pinus; Sitosterols; Stigmasterol; Water Pollutants, Chemical

2011
Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities.
    Journal of Asian natural products research, 2011, Volume: 13, Issue:11

    Nine indoloquinazoline alkaloids (1-9) were isolated from the dried and nearly ripe fruits of Euodia rutaecarpa (Juss.) Benth. (Euodiae Fructus), along with limonin and β-sitosterol. Their structures were elucidated on the basis of their spectroscopic data. Among them, compounds 1 and 2 were new compounds and characterized as (7R,8S)-7-hydroxy-8-methoxy-rutaecarpine and (7R,8S)-7-hydroxy-8-ethoxy-rutaecarpine, respectively, and 1-hydroxy-rutaecarpine (3) and (7R,8S)-7,8-dihydroxy-rutaecarpine (4) were isolated from Euodiae Fructus for the first time. The nine indoloquinazoline alkaloids were evaluated for their cytotoxic activities against human promyelocytic leukemia HL-60 cells and human gastric carcinoma N-87 cells.

    Topics: Alkaloids; Antineoplastic Agents, Phytogenic; Cyclohexane Monoterpenes; Drug Screening Assays, Antitumor; Evodia; Fruit; HL-60 Cells; Humans; Indoles; Molecular Structure; Monoterpenes; Nuclear Magnetic Resonance, Biomolecular; Quinazolines; Sitosterols

2011
Two new epoxysteroids from Helianthus tuberosus.
    Molecules (Basel, Switzerland), 2011, Oct-13, Volume: 16, Issue:10

    Two new epoxy steroids, 5α,8α-epidioxy-22β,23β-epoxyergosta-6-en-3β-ol (1) and 5α,8α-epidioxy-22α,23α-epoxyergosta-6-en-3β-ol (2), and ten known steroids including (24R)-5α,8α-epidioxyergosta-6-en-3β-ol (3), (22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (4), (22E,24R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol (5), β-sitosterol (6), sitost-5-en-3β-ol acetate (7), 7α-hydroxysitosterol (8), schleicheol 2 (9), (24R)-24-ethyl-5α-cholestane-3β,5α,6β-triol (10), 7α-hydroxystigmasterol (11), and stigmasterol (12) were isolated from Helianthus tuberosus grown in Laizhou salinized land of coastal zone of Bohai Sea, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The new compounds 1 and 2 exhibited weak antibacterial activity and no antifungal activity.

    Topics: Animals; Anti-Infective Agents; Artemia; China; Colletotrichum; Ergosterol; Escherichia coli; Fusarium; Helianthus; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Plant Extracts; Sitosterols; Staphylococcus aureus; Steroids; Stigmasterol

2011
[Study on the chemical constituents of Phellinus lonicerinus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:6

    To study the chemical constituents of Phellinus lonicerinus.. The constituents were seperated and purified by silica column chromatography, Sephadex LH-20 and other column chromatography, then their structures were identified by spectral methods.. Six compounds were isolated and identified as ergosta-6,22-dien-3beta, 5beta, 8beta-triol (1), erogosterol (2), vanillin (3), 3,4-dihydroxy benzalacetone (4), beta-sitosterol (5), docosanoic acid (6).. All compounds are isolated from Phellinus lonicerinus for the first time and compound 4 isa new natural product.

    Topics: Benzaldehydes; Caffeic Acids; Ergosterol; Fatty Acids; Fruiting Bodies, Fungal; Magnetic Resonance Spectroscopy; Molecular Structure; Polyporaceae; Sitosterols

2011
[Study on the chemical constituents of aerial part of Ligusticum jeholense].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:7

    To study the chemical constituents of the aerial part of Ligusticum jeholense.. The constituents were isolated by sillica gel column chromatography, Sephadex LH-20 column chromatography and their structures were elucidated by spectral analysis.. Seven compounds were separated from the EtOH extracts. Their structures were identified as psoralen (1), beta-sitosterol (2), daucosterol (3), kaempferol-3-O-(2",4"-di-E-p-coumaroyl)-alpha-L-rhamnoside (4), kaempferol-3-O-beta-D-galactoside (5), quercetin-3-O-beta-D-galactoside (6), sucrose (7).. Compounds 1, 4, 5 and 6 are isolated from the genus for the first time. Compounds 2, 3 and 7 are isolated from the aerial part of the plant for the first time.

    Topics: Ethanol; Ficusin; Kaempferols; Ligusticum; Molecular Structure; Monosaccharides; Plant Components, Aerial; Plants, Medicinal; Quercetin; Sitosterols; Sucrose

2011
[Antiproliferative effects mechanism of beta-sitosterul in hepatoma HepG2 cells].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:15

    To study the antiproliferative effects of beta-sitosterul and its mechanism in hepatoma HepG2 cells.. Cell proliferation was assessed by MTT assay. Cell cycle distribution, apoptosis and mitochondrial membrane potential were measured by high content screening (HCS). The protein expression of caspase-3, caspase-8, caspase-9, Bcl-2, Bax, tBid and cytochrome c in the HepG2 cells were evaluated by Western Blots.. beta-Sitosterul exerted significant antiproliferative effects in HepG2 cells. Furthermore, beta-sitosterul also induced HepG2 cells apoptosis, lost mitochondrial membrane potential, activated caspase-3, caspase-8 and caspase-9, up-regulate Bax, tBid protein, down-regulation Bcl-2 protein. However, beta-sitosterul had hardly any effects on QSG7701 cells.. beta-Sitosterul exerted antiproliferative effects and induced HepG2 cells apoptosis via mitochondrial pathway and membrane death receptor pathway.

    Topics: Antineoplastic Agents; Apoptosis; Apoptosis Regulatory Proteins; Carcinoma, Hepatocellular; Cell Cycle; Cell Line, Tumor; Cell Proliferation; Hep G2 Cells; Humans; Liver Neoplasms; Membrane Potential, Mitochondrial; Sitosterols

2011
Chemical composition fluctuations in roots of Plumbago scandens L. in relation to floral development.
    Anais da Academia Brasileira de Ciencias, 2011, Volume: 83, Issue:4

    Plumbago scandens L. is a Brazilian tropical/subtropical species that occurs along the coast. Chemically it is mainly represented by naphthoquinones, flavonoids, terpenoids and steroids. The aim of the present work is to study quantitative changes in the root metabolic production of Plumbago scandens during different physiologic developmental stages relative to floration. The results indicated the presence of four substances in the extracts: plumbagin, epi-isoshinanolone, palmitic acid and sitosterol, independent on developmental stage. The naphthoquinone plumbagin has always showed to be the major component of all extracts. Naphthoquinones exhibited their highest content during floration, while the content of the two others components decreased during this stage, revealing an inverse profile. The chemical composition changed depending on the plant requirements.

    Topics: Chromatography, Gas; Naphthoquinones; Palmitic Acid; Plant Roots; Plumbaginaceae; Sitosterols; Tetrahydronaphthalenes

2011
[Study on the chemical constituents in roots of Gentiana dahurica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:8

    To systematically study the chemical constituents in the roots of Gentiana dahurica.. Various column chromatographic techniques were used for isolation and purification. The structures were elucidated on the basis of spectral data (UV, IR, MS, NMR) and identified by comparing with the authentic substance.. Seven compounds were isolated and identified as: roburic acid (1), oleanolic acid (2), beta-sitosterol (3), daucosterol (4), gentiopicroside(5), swertiamarine (6), sweroside (7).. Compounds 1, 2 and 4 are isolated from this plant for the first time.

    Topics: Gentiana; Molecular Structure; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet; Triterpenes

2011
[Chemical constituents from root bark of Tripterygium hypoglaucum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:18

    To investigate chemical constituents of the root bark of Tripterygium hypoglaucum.. Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and their structures were identified on the basis of spectral data (MS, 1H-NMR and 13C-NMR).. Twelve compounds were isolated and identified as friedelin (1), 3-oxo-olean-9(11),12-diene (2), canophyllal (3), 3-acetoxy oleanolic acid (4), triptophenolide (5), triptonoterpene methyl ether (6), tricosanoic acid (7), beta-sitosterol (8), stearic acid (9), glut-5-en-3beta,28-diol (10), palmitic acid (11) and daucostorol (12).. Compounds 1, 2, 3, 7 and 10 were isolated from T. hypoglaucum and 7 from the genus Tripterygium for the first time.

    Topics: Chromatography; Diterpenes; Fatty Acids, Unsaturated; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oleanolic Acid; Organic Chemicals; Palmitic Acid; Plant Roots; Sitosterols; Stearic Acids; Tripterygium; Triterpenes

2011
[Study on chemical constituents of the root of Liriope platyphylla].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:10

    To study the constituents from the root of Liriope platypgylla.. Six chemical constituents were isolated from the chloroform fraction and n-BuOH fraction from EtOH extract of Liriope platyphylla.. Their structures were elucidated as beta-sitosterol-3-O-beta-D-glucopyranosile(I), palmic acid (II), ruscogenin (III), LP-C(IV), LP-D(V), 25 (S) -ruscogenin 1-O-beta-D-xylopyranoside-3-O-alpha-L-rhamnopyranoside (VI), respectively.. All these compounds are isolated from this plant for the first time.

    Topics: Liriope Plant; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Plant Roots; Plants, Medicinal; Sitosterols; Spirostans

2011
[Research on chemical constituents of xuefu zhuyu decoction].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:10

    To investigate the chemical constituents of Xufu Zhuyu decoction.. Silica gel column chromatography, Sephadex LH-20 chromatography and crystallization were employed for the isolation and purification. The structures were elucidated by physicochemical properties and spectral analysis.. Eleven compounds were isolated and identified as follows: palmitic acid (1), stearic acid (2), beta-sitosterol (3), oleanolic acid (4), pregnenolone (5), tangeratin (6), 4-hydroxy-3-butylphthalide (7), sorhamnetin (8), friedelinol (9), beta-ecdysone (10), ferulic acid (11).. All these compounds are isolated from Xuefu Zhuyu decoction for the first time.

    Topics: Drugs, Chinese Herbal; Magnetic Resonance Imaging; Molecular Structure; Oleanolic Acid; Palmitic Acid; Plants, Medicinal; Pregnenolone; Sitosterols; Stearic Acids; Water

2011
[Study on the chemical constituents of vinegar Schisandra chinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2011, Volume: 34, Issue:11

    To study the chemical constituents of vinegar Schisandra chinensis.. Column chromatography was used in the isolation procedure. The structures of isolated compounds were elucidated by spectral data.. Five compounds were isolated and their structures were identified as kadsuranin (I), beta-sitosterol (II), schizandrin (III), 5,5'-[oxybis (methylene)] bis-2-furancarboxaldehyde (IV) and (NH)-form-2-Hydroxyquinoline4-carboxylic acid (V).. Compound 5 is isolated from this genus for the first time.

    Topics: Acetic Acid; Cyclooctanes; Fruit; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Plants, Medicinal; Polycyclic Compounds; Schisandra; Sitosterols; Technology, Pharmaceutical

2011
[Chemical constituents of Halenia elliptica].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2011, Volume: 36, Issue:11

    To study the chemical constituents of Halenia elliptica.. The air-dried whole plants of Halenia elliptica were extracted with 90% EtOH. The EtOH extract was condensed to a small amount of volume and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR).. 12 compounds were isolated from H. elliptica, and characterized as 8-hydroxy-2-methylchromone (1), 5-methoxy-2-methylchromone (2), 7-epi-vogeloside (3), coniferl aldehyde (4), sinapaldehyde (5), norbellidifolin (6), 1-hydroxyl-2,3,4,6-tetramethoxyxanthone (7), 1-hydroxyl-2,3,4,7-tetramethoxyxanthone (8), 1-hydroxyl-2,3,5-trimethoxyxanthone (9), together with azelaic acid, beta-sitosterol, and oleanolic acid.. Compounds 1, 2 were new natural compounds and compounds 3-6, 10 were obtained from H. elliptica for the first time and compound 6 showed inhibitory activities against HBsAg and HBeAg secretion with IC50 value of 0.77 and < 0.62 mmol x L(-1), respectively.

    Topics: Acrolein; Chromatography; Dicarboxylic Acids; Gentianaceae; Iridoid Glycosides; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oleanolic Acid; Plant Extracts; Sitosterols; Xanthones

2011
The effects of sterol structure upon sterol esterification.
    Atherosclerosis, 2010, Volume: 208, Issue:1

    Cholesterol is esterified in mammals by two enzymes: LCAT (lecithin cholesterol acyltransferase) in plasma and ACAT(1) and ACAT(2) (acyl-CoA cholesterol acyltransferases) in the tissues. We hypothesized that the sterol structure may have significant effects on the outcome of esterification by these enzymes. To test this hypothesis, we analyzed sterol esters in plasma and tissues in patients having non-cholesterol sterols (sitosterolemia and Smith-Lemli-Opitz syndrome). The esterification of a given sterol was defined as the sterol ester percentage of total sterols. The esterification of cholesterol in plasma by LCAT was 67% and in tissues by ACAT was 64%. Esterification of nine sterols (cholesterol, cholestanol, campesterol, stigmasterol, sitosterol, campestanol, sitostanol, 7-dehydrocholesterol and 8-dehydrocholesterol) was examined. The relative esterification (cholesterol being 1.0) of these sterols by the plasma LCAT was 1.00, 0.95, 0.89, 0.40, 0.85, 0.82 and 0.80, 0.69 and 0.82, respectively. The esterification by the tissue ACAT was 1.00, 1.29, 0.75, 0.49, 0.45, 1.21 and 0.74, respectively. The predominant fatty acid of the sterol esters was linoleic acid for LCAT and oleic acid for ACAT. We compared the esterification of two sterols differing by only one functional group (a chemical group attached to sterol nucleus) and were able to quantify the effects of individual functional groups on sterol esterification. The saturation of the A ring of cholesterol increased ester formation by ACAT by 29% and decreased the esterification by LCAT by 5.9%. Esterification by ACAT and LCAT was reduced, respectively, by 25 and 11% by the presence of an additional methyl group on the side chain of cholesterol at the C-24 position. This data supports our hypothesis that the structure of the sterol substrate has a significant effect on its esterification by ACAT or LCAT.

    Topics: Adolescent; Adult; Child; Child, Preschool; Esterification; Female; Humans; Infant; Infant, Newborn; Lipid Metabolism Disorders; Male; Phosphatidylcholine-Sterol O-Acyltransferase; Sitosterols; Smith-Lemli-Opitz Syndrome; Sterol O-Acyltransferase; Sterol O-Acyltransferase 2; Sterols; Young Adult

2010
Abscisic acid is involved in the response of grape (Vitis vinifera L.) cv. Malbec leaf tissues to ultraviolet-B radiation by enhancing ultraviolet-absorbing compounds, antioxidant enzymes and membrane sterols.
    Plant, cell & environment, 2010, Volume: 33, Issue:1

    We investigated the interactions of abscisic acid (ABA) in the responses of grape leaf tissues to contrasting ultraviolet (UV)-B treatments. One-year-old field-grown plants of Vitis vinifera L. were exposed to photosynthetically active radiation (PAR) where solar UV-B was eliminated by using polyester filters, or where PAR was supplemented with UV-B irradiation. Treatments combinations included weekly foliar sprays of ABA or a water control. The levels of UV-B absorbing flavonols, quercetin and kaempferol were significantly decreased by filtering out UV-B, while applied ABA increased their content. Concentration of two hydroxycinnamic acids, caffeic and ferulic acids, were also increased by ABA, but not affected by plus UV-B (+UV-B) treatments. Levels of carotenoids and activities of the antioxidant enzymes, catalase, ascorbate peroxidase and peroxidase were elevated by +ABA treatments, but only if +UV-B was given. Cell membrane beta-sitosterol was enhanced by ABA independently of +UV-B. Changes in photoprotective compounds, antioxidant enzymatic activities and sterols were correlated with lessened membrane harm by UV-B, as assessed by ion leakage. Oxidative damage expressed as malondialdehyde content was increased under +UV-B treatments. Our results suggest that the defence system of grape leaf tissues against UV-B is activated by UV-B irradiation with ABA acting downstream in the signalling pathway.

    Topics: Abscisic Acid; Anthocyanins; Antioxidants; Carotenoids; Catalase; Chlorophyll; Kaempferols; Lipid Peroxidation; Oxidative Stress; Peroxidases; Plant Leaves; Quercetin; Sitosterols; Ultraviolet Rays; Vitis

2010
Familial combined hyperlipidemia is associated with alterations in the cholesterol synthesis pathway.
    Arteriosclerosis, thrombosis, and vascular biology, 2010, Volume: 30, Issue:1

    Familial combined hyperlipidemia (FCH) is a common familial lipid disorder characterized by increases in plasma total cholesterol, triglyceride, and apolipoprotein B-100 levels. In light of prior metabolic and genetic research, our purpose was to ascertain whether FCH cases had significant abnormalities of plasma markers of cholesterol synthesis and absorption as compared to unaffected kindred members.. Plasma levels of squalene, desmosterol, and lathosterol (cholesterol synthesis markers) and campesterol, sitosterol, and cholestanol (cholesterol absorption markers) were measured by gas-liquid chromatography in 103 FCH patients and 240 normolipidemic relatives (NLR). Squalene, desmosterol, and lathosterol levels were 6% (0.078), 31%, (P<0.001) and 51% (P<0.001) higher in FCH as compared to NLR, and these differences were especially pronounced in women. An interaction with obesity was also noted for a subset of these markers. We did not observe any apparent differences for the cholesterol absorption markers among FCH patients and NLR.. Our data indicate that both men and women with FCH have alterations in the cholesterol synthesis pathway, resulting in 51% higher levels of lathosterol (and additionally desmosterol in women). Plasma levels of the cholesterol precursor sterol squalene were only slightly increased (6%), suggesting enhanced conversion of squalene to lathosterol in this disorder.

    Topics: Adult; Aged; Biomarkers; Cholestanol; Cholesterol; Desmosterol; Female; Humans; Hyperlipidemia, Familial Combined; Intestinal Absorption; Male; Middle Aged; Phytosterols; Sex Characteristics; Sitosterols; Squalene

2010
ACE inhibition by astilbin isolated from Erythroxylum gonocladum (Mart.) O.E. Schulz.
    Phytomedicine : international journal of phytotherapy and phytopharmacology, 2010, Volume: 17, Issue:5

    Erythroxylum species have several traditional uses in different countries, including the treatment of hypertension. The ethanol extract from E. gonocladum aerial parts, a species endemic to the Brazilian cerrado, elicited a concentration-dependent inhibition of angiotensin converting enzyme (ACE) (pIC(50)=4.53+/-0.05). Extract fractionation led to the isolation of two compounds, whose structures were assigned by spectrometric data as astilbin and beta-sitosterol, along with a mixture of palmitic, stearic and linolenic acids. This is the first report on the occurrence of these compounds on E. gonocladum. Astilbin promoted significant ACE inhibition in vitro (pIC(50)=5.86+/-0.33) and its activity did not differ from captopril, when both compounds were assayed at 10 microM concentration.

    Topics: Angiotensin-Converting Enzyme Inhibitors; Animals; Antihypertensive Agents; Brazil; Captopril; Dose-Response Relationship, Drug; Erythroxylaceae; Fatty Acids; Flavonols; Peptidyl-Dipeptidase A; Plant Components, Aerial; Plant Extracts; Rats; Sitosterols

2010
Beta-sitosterol exhibits anti-inflammatory activity in human aortic endothelial cells.
    Molecular nutrition & food research, 2010, Volume: 54, Issue:4

    beta-Sitosterol, normally present in vegetable-containing diets, comprises an important component of cholesterol controlling functional foods. It has been associated with cardiovascular protection, exerting its effect mainly through increasing the antioxidant defense system and effectively lowering the serum cholesterol levels in humans. However, its anti-inflammatory effect on endothelium is unknown. Attachment of leukocytes to the vascular endothelium and the subsequent migration of cells into the vessel wall are early events in atherogenesis, this process requiring the expression of endothelial adhesion molecules. We examined the effect of beta-sitosterol (0.1-200 microM) on (i) the expression of vascular adhesion molecule 1 and intracellular adhesion molecule 1 by cell ELISA and (ii) the attachment of monocytes (U937 cells) in tumor necrosis factor-alpha (TNF-alpha)-stimulated human aortic endothelial cells (HAECs) by adhesion assay. The effect on nuclear factor-kB phosphorylation was also examined via a cell-based ELISA kit. Results showed that beta-sitosterol inhibits significantly vascular adhesion molecule 1 and intracellular adhesion molecule 1 expression in TNF-alpha-stimulated HAEC as well as the binding of U937 cells to TNF-alpha-stimulated HAEC and attenuates the phosphorylation of nuclear factor-kB p65. This study extends existing data regarding the cardioprotective effect of beta-sitosterol and provides new insights into understanding the molecular mechanism underlying the beneficial effect of beta-sitosterol on endothelial function.

    Topics: Anti-Inflammatory Agents; Aorta; Cardiotonic Agents; Cell Adhesion; Cell Line; Cells, Cultured; Endothelial Cells; Enzyme-Linked Immunosorbent Assay; Fluorescent Dyes; Humans; Intercellular Adhesion Molecule-1; Monocytes; NF-kappa B; Phosphorylation; Sitosterols; Tumor Necrosis Factor-alpha; Vascular Cell Adhesion Molecule-1

2010
Relation of non-cholesterol sterols to coronary risk factors and carotid intima-media thickness: the Cardiovascular Risk in Young Finns Study.
    Atherosclerosis, 2010, Volume: 209, Issue:2

    The aim of the present study was to evaluate the role of cholesterol metabolism in the development of atheromatous artery disease.. Serum synthesis (cholesterol precursors) and absorption markers (cholestanol, campesterol, sitosterol, and avenasterol) were related to coronary risk factors and vascular structure in a population-based sample of 468 randomly selected 33-39-year-old men on their regular habitual diet. Carotid artery intima-media thickness (IMT) and serum lipids (including cholesterol) and sterols were measured in 2001, and the subjects were ranked to decreasing cholesterol synthesis depicted by serum cholestanol quartiles defined 21 years earlier in adolescence.. Serum cholesterol was correlated with absorption (e.g. serum campesterol, p<0.05), but not with synthesis, or with cholestanol quartiles. Cholesterol metabolism (synthesis/absorption markers) decreased linearly (about 50%) with the increasing cholestanol quartiles. IMT differed between the age groups, but not between cholestanol quartiles. Serum triglycerides, apoprotein B, and body mass index decreased, and non-HDL cholesterol/apoprotein B values increased between the cholestanol quartiles, whereas LDL cholesterol was unchanged. Cholesterol synthesis markers were related to blood pressure and serum triglycerides, and negatively to HDL cholesterol level in total population and in most of the cholestanol quartiles (p from 0.05 to 0.001).. Variables of metabolic syndrome accumulated in quartiles of high synthesis of cholesterol. Non-cholesterol sterols were related to many classic coronary risk factors, but virtually not to serum cholesterol or vascular structure.

    Topics: Adolescent; Adult; Carotid Arteries; Child; Cholestanol; Cholesterol; Coronary Disease; Follow-Up Studies; Humans; Male; Phytosterols; Risk Factors; Sitosterols; Sterols; Tunica Intima; Tunica Media; Ultrasonography

2010
The effects of pomegranate seed extract and beta-sitosterol on rat uterine contractions.
    Reproductive sciences (Thousand Oaks, Calif.), 2010, Volume: 17, Issue:3

    The aim of this study was to investigate the effects of pomegranate (Punica granatum L., Punicaceae) seed extract on uterine contractility. Pomegranate seeds were methanolic extracted and their constituents analyzed using gas chromatography and mass spectrometry. Isometric force was measured in strips of longitudinal rat myometrium and the effects of pomegranate seed extract studied. We found beta-sitosterol to be the main constituent of the extract (16%) and its effects were also investigated. Pomegranate seed extract and beta-sitosterol increased spontaneous contractions in a concentration-dependent manner with a maximum effect at 250 mg/100 mL and 1 mg/100 mL, respectively. The amplitude and frequency of the phasic contraction were significantly increased along with basal tension. The effects of pomegranate seed extract were very similar to those of beta-sitosterol. Force produced in the presence of pomegranate seed extract was abolished by the inhibition of L-type calcium channels or myosin light chain kinase (MLCK). Contractions were not potentiated by pomegranate extract following the inhibition of K channels or inhibition of the sarcoplasmic reticulum calcium ATPase (SERCA). The actions of beta-sitosterol and the extract were not blocked by the estrogen receptor blocker, fulvestrant. We conclude that pomegranate seed extract is a potent stimulator of phasic activity in rat uterus. Our data suggest that the uterotonic effect is due to nonestrogenic effects of beta-sitosterol acting to inhibit K channels and SERCA and thereby increasing contraction via calcium entry on L-type calcium channels and MLCK. We suggest that pomegranate extract and beta-sitosterol may be a useful uterine stimulant.

    Topics: Animals; Calcium Channel Blockers; Dose-Response Relationship, Drug; Enzyme Inhibitors; Estradiol; Estrogen Antagonists; Female; Fulvestrant; Gas Chromatography-Mass Spectrometry; In Vitro Techniques; Lythraceae; Myosin-Light-Chain Kinase; Plant Extracts; Potassium Channel Blockers; Potassium Channels; Rats; Rats, Wistar; Sarcoplasmic Reticulum; Sarcoplasmic Reticulum Calcium-Transporting ATPases; Seeds; Sitosterols; Uterine Contraction

2010
Involvement of angiotensin II in intestinal cholesterol absorption.
    Pharmacological research, 2010, Volume: 61, Issue:5

    Niemann-Pick C1-like 1 (NPC1L1) protein is identified as a key molecule of cholesterol absorption into the intestine. Although there is a controversy about the association between sitosterol levels and cardiovascular disease (CVD), cholesterol absorption may contribute to the increased risk for CVD because increased levels of sitosterol, a marker of cholesterol absorption, are associated with future cardiovascular events in high-risk patients. However, which anthropometric and metabolic variables could regulate serum levels of sitosterol in humans and whether serum sitosterol levels might reflect transport function of NPC1L1 are largely unknown. In this study, we first investigated the independent determinants of serum sitosterol levels in apparently healthy patients not taking lipid-lowering agents. We next examined the effects of angiotensin II on NPC1L1 gene and protein expression in differentiated Caco-2 cells. Seventy apparently health patients not taking lipid-lowering agents (28 men and 42 women, mean age 73.7+/-10.1 years old) underwent a complete history and physical examination, determination of blood chemistries, including serum levels of sitosterol. Univariate regression analysis showed that serum levels of sitosterol were associated with low-density-lipoprotein (LDL)-cholesterol (r=0.284, p=0.021) and use of the renin-angiotensin system (RAS) inhibitors (r=-0.289, p=0.018). By the use of multiple stepwise regression analyses, use of RAS inhibitors (p=0.025) was remained significant independently. Further, angiotensin II was found to up-regulate NPC1L1 mRNA and protein levels in Caco-2 cells, which were completely blocked by an angiotensin II type 1 receptor blocker or an anti-oxidant, N-acetylcysteine. The present study suggests the possible involvement of RAS in NPC1L1 expression in vitro and cholesterol absorption in humans.

    Topics: Aged; Alkaline Phosphatase; Angiotensin II; Blotting, Western; Caco-2 Cells; Cholesterol; Female; Gene Expression; Humans; Hypolipidemic Agents; Intestinal Absorption; Male; Membrane Proteins; Membrane Transport Proteins; Middle Aged; Regression Analysis; Renin-Angiotensin System; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Sitosterols

2010
Modulation of monoamine neurotransmitters in fighting fish Betta splendens exposed to waterborne phytoestrogens.
    Fish physiology and biochemistry, 2010, Volume: 36, Issue:4

    Endogenous estrogens are known to affect the activity of monoamine neurotransmitters in vertebrate animals, but the effects of exogenous estrogens on neurotransmitters are relatively poorly understood. We exposed sexually mature male fighting fish Betta splendens to environmentally relevant and pharmacological doses of three phytoestrogens that are potential endocrine disruptors in wild fish populations: genistein, equol, and β-sitosterol. We also exposed fish to two doses of the endogenous estrogen 17β-estradiol, which we selected as a positive control because phytoestrogens are putative estrogen mimics. Our results were variable, but the effects were generally modest. Genistein increased dopamine levels in the forebrains of B. splendens at both environmentally relevant and pharmacological doses. The environmentally relevant dose of equol increased dopamine levels in B. splendens forebrains, and the pharmacological dose decreased norepinephrine (forebrain), dopamine (hindbrain), and serotonin (forebrain) levels. The environmentally relevant dose of β-sitosterol decreased norepinephrine and dopamine in the forebrain and hindbrain, respectively. Our results suggest that sources of environmental phytoestrogens, such as runoff or effluent from agricultural fields, wood pulp mills, and sewage treatment plants, have the potential to modulate neurotransmitter activity in free-living fishes in a way that could interfere with normal behavioral processes.

    Topics: Analysis of Variance; Animals; Brain; Chromatography, High Pressure Liquid; Dopamine; Equol; Genistein; Isoflavones; Male; Norepinephrine; Perciformes; Phytoestrogens; Serotonin; Sitosterols; Vesicular Monoamine Transport Proteins; Water Pollutants, Chemical

2010
The spectrum of plant and animal sterols in different oil-derived intravenous emulsions.
    Lipids, 2010, Volume: 45, Issue:1

    Intravenous lipid constituents have different effects on various biological processes. Some of these effects are protective, while others are potentially adverse. Phytosterols, in particular, seem to be implicated with parenteral nutrition-associated cholestasis. The aim of this study is to determine the amount of plant and animal sterols present in lipid formulations derived from different oil sources. To this end, animal (cholesterol) and plant (beta-sitosterol, campesterol, and stigmasterol) sterols in seven different commercially available intravenous lipid emulsions (ILEs) were quantified by capillary gas chromatography after performing a lipid extraction procedure. The two major constituents of the lipid emulsions were cholesterol (range 14-57% of total lipids) and beta-sitosterol (range 24-55%), followed by campesterol (range 8-18%) and stigmasterol (range 5-16%). The fish oil-derived formulation was an exception, as it contained only cholesterol. The mean values of the different sterols were statistically different across ILEs (P = 0.0000). A large percentage of pairwise comparisons were also statistically significant (P = 0.000), most notably for cholesterol and stigmasterol (14 out of 21 for both), followed by campesterol (12 out 21) and beta-sitosterol (11 out 21). In conclusion, most ILEs combined significant amounts of phytosterols and cholesterol. However, their phytosterols:cholesterol ratios were reversed compared to the normal human diet.

    Topics: Cholestasis; Cholesterol; Fat Emulsions, Intravenous; Fish Oils; Humans; Parenteral Nutrition, Total; Phytosterols; Sitosterols; Stigmasterol

2010
Lipase-catalyzed synthesis of conjugated linoleyl beta-sitosterol and its cholesterol-lowering properties in mice.
    Journal of agricultural and food chemistry, 2010, Feb-10, Volume: 58, Issue:3

    Conjugated linoleyl beta-sitosterol (CLS) was prepared from beta-sitosterol and conjugated linoleic acid (CLA) via lipase-catalyzed synthesis in n-hexane in the presence of molecular sieves. Its plasma cholesterol-lowering properties were also studied. The optimal biosynthesis conditions were as follows: beta-sitosterol concentration of 50 micromol/mL, the molar ratio of CLA to beta-sitosterol of 1:1, the lipase concentration of 20 mg/mL, and 4 A molecular sieve concentration of 60 mg/mL in n-hexane at 50 degrees C with vigorous shaking of 150 rpm for 72 h, and the highest yield of CLS reached 72.6%. The isolated CLS mixed with mice feed had good cholesterol-lowering properties. It decreased serum total cholesterol (TC), serum triacylglycerols (TAGs), serum low-density lipoprotein cholesterol (LDL-C), atherogenic index (AI), liver weight (LW), liver index (LI), liver TC, and TAGs of mice, which was shown that CLS could prevent the formation of atherosclerosis and moderate the fat pathologic changes of liver. However, the HDL-C was not decreased, which proved the advantage of CLS over the other cholesterol-lowering products.

    Topics: Animals; Anticholesteremic Agents; Biocatalysis; Candida; Cholesterol; Cholesterol, LDL; Fungal Proteins; Linoleic Acids, Conjugated; Lipase; Liver; Male; Mice; Random Allocation; Sitosterols; Triglycerides

2010
Ethnobotanical survey and cytotoxicity testing of plants of South-western Nigeria used to treat cancer, with isolation of cytotoxic constituents from Cajanus cajan Millsp. leaves.
    Journal of ethnopharmacology, 2010, Mar-24, Volume: 128, Issue:2

    There is only scant literature on the anticancer components of medicinal plants from Nigeria, yet traditional healers in the area under study claim to have been managing the disease in their patients with some success using the species studied.. To document plants commonly used to treat cancer in South-western Nigeria and to test the scientific basis of the claims using in vitro cytotoxicity tests.. Structured questionnaires were used to explore the ethnobotanical practices amongst the traditional healers. Methanol extracts of the most common species cited were screened for cytotoxicity using the sulforhodamine B (SRB) assay in both exposure and recovery experiments. Three cancer cell lines (human breast adenocarcinoma cell line MCF-7, human large cell lung carcinoma cell line COR-L23 and human amelanotic melanoma C32) and one normal cell line (normal human keratinocytes SVK-14) were used for the screening of the extracts and the fractions obtained. The extract of Cajanus cajan showed considerable activity and was further partitioned and the dichloromethane fraction was subjected to preparative chomatography to yield six compounds: hexadecanoic acid methyl ester, alpha-amyrin, beta-sitosterol, pinostrobin, longistylin A and longistylin C. Pinostrobin and longistylins A and C were tested for cytotoxicity on the cancer cell lines. In addition, an adriamycin-sensitive acute T-lymphoblastic leukaemia cell line (CCRF-CEM) and its multidrug-resistant sub-line (CEM/ADR5000) were used in an XTT assay to evaluate the activity of the pure compounds obtained.. A total of 30 healers from S W Nigeria were involved in the study. 45 species were recorded with their local names with parts used in the traditional therapeutic preparations. Cytotoxicity (IC(50) values less than 50 microg/mL) was observed in 5 species (Acanthospermum hispidum, Cajanus cajan, Morinda lucida, Nymphaea lotus and Pycnanthus angolensis). Acanthospermum hispidum and Cajanus cajan were the most active. The dichloromethane fraction of Cajanus cajan had IC(50) value 5-10 microg/mL, with the two constituent stilbenes, longistylins A and C, being primarily responsible, with IC(50) values of 0.7-14.7 microM against the range of cancer cell lines.. Most of the species tested had some cytotoxic effect on the cancer cell lines, which to some extent supports their traditional inclusion in herbal preparations for treatment of cancer. However, little selectivity for cancer cells was observed, which raises concerns over their safety and efficacy in traditional treatment. The longistylins A and C appear to be responsible for much of the activity of Cajanus cajan extract.

    Topics: Cajanus; Cell Line, Tumor; Data Collection; Ethnobotany; Ethnopharmacology; Flavanones; Humans; Male; Neoplasms; Nigeria; Oleanolic Acid; Plant Leaves; Plants; Plants, Medicinal; Sitosterols

2010
Plasma non-cholesterol sterols: a useful diagnostic tool in pediatric hypercholesterolemia.
    Pediatric research, 2010, Volume: 67, Issue:2

    Current guidelines strongly recommend the identification of genetic forms of hypercholesterolemia (HC) during childhood.The usefulness of non-cholesterol sterols (NCS) in the diagnosis of genetic HC has not been fully explored. Plasma NCS were measured by gas chromatography/mass spectrometry (GC/MS) in 113 children with hypercholesterolemia affected by: autosomal dominant hypercholesterolemia (ADH), familial combined hyperlipidemia(FCHL), polygenic hypercholesterolemia (PHC), and in 79 controls to evaluate: i) plasma NCS profile in different genetic HC and ii) the usefulness of NCS for the diagnosis of HC beyond current clinical criteria. ADH was characterized by raised lathosterol/total cholesterol (TC) and reduced phytosterols/TC ratios, indicative of increased cholesterol synthesis. FCHL showed a slight increase of lathosterol/TC ratio, whereas PHC showed increased phytosterols/TC ratios, indicative of increased cholesterol absorption. In a post hoc discriminant analysis of patients with HC, lipid values correctly classified the 73% (14 of 19) of ADH, whereas the inclusion of plasma sterols allowed the correct identification of all 19 patients with ADH. FCHL was not differentiated from PHC (62 versus 69%).In conclusion, NCS measurement showed that cholesterol plasma levels are related to the cholesterol synthesis in ADH and to cholesterol absorption in PHC. NCS improve the detection of ADH in pediatric patients, whereas FCHL diagnosis is not improved.

    Topics: Adolescent; Biomarkers; Case-Control Studies; Child; Cholesterol; Discriminant Analysis; Female; Gas Chromatography-Mass Spectrometry; Genetic Predisposition to Disease; Humans; Hyperlipidemia, Familial Combined; Hyperlipoproteinemia Type II; Italy; Male; Multifactorial Inheritance; Phytosterols; Predictive Value of Tests; Sitosterols; Sterols

2010
Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots.
    Phytochemistry, 2010, Volume: 71, Issue:5-6

    A phytochemical analysis of cassava (Manihot esculenta Crantz) fresh roots and roots suffering from post-harvest physiological deterioration (PPD) has been carried out. The first isolation and identification of galactosyl diacylglycerides from fresh cassava roots is reported, as well as beta-carotene, linamarin, and beta-sitosterol glucopyranoside. The hydroxycoumarin scopoletin and its glucoside scopolin were identified from cassava roots during PPD, as well as trace quantities of esculetin and its glucoside esculin. There is no isoscopoletin in cassava roots during PPD.

    Topics: beta Carotene; Biological Factors; Coumarins; Esculin; Food Handling; Galactolipids; Glucosides; Manihot; Metabolome; Molecular Structure; Nitriles; Plant Roots; Scopoletin; Sitosterols; Umbelliferones

2010
Increased reproductive success in the white American mink (Neovison vison) with chronic dietary beta-sitosterol supplement.
    Animal reproduction science, 2010, Volume: 119, Issue:3-4

    Beta-sitosterol is a weakly estrogenic phytosterol used in functional foods to lower elevated serum cholesterol concentrations. It has been reported to cause reproductive disturbances in fish and lower the sperm count of rodents but, in contrast, there were indications of enhanced reproduction in a preliminary study on the brown American mink (Neovison vison). In the present experiment the effects of chronic dietary beta-sitosterol exposure on the reproduction of the American mink were evaluated with a large number of experimental animals. Male and female finnwhite mink (n=200)--a previously uninvestigated color type with lower reproductive success compared to brown mink--were exposed to 50 mg beta-sitosterol kg(-1)d(-1) for 10 months and compared with 200 control animals. After 3 months in November, 15 males per group were sacrificed and their biochemical variables determined. The serum glucose and high-density lipoprotein cholesterol concentrations were lower in the beta-sitosterol-exposed group, while other effects were minor. The females were mated with the top-rated males (4-5:1) in March and their reproductive performance was determined. The reproductive success increased in the beta-sitosterol group with significantly fewer barren females and a higher number of successfully reproducing females than in the control group, which supports previous studies on brown mink and voles indicating that beta-sitosterol could be used to enhance the reproductive performance of these mammals.

    Topics: Animals; Anticholesteremic Agents; Blood Glucose; Breeding; Cholesterol, HDL; Diet; Female; Male; Mink; Pregnancy; Reproduction; Sitosterols

2010
The associations of cholesterol metabolism and plasma plant sterols with all-cause and cardiovascular mortality.
    Journal of lipid research, 2010, Volume: 51, Issue:8

    Moderately elevated levels of plasma plant sterols have been suspected to be causally involved in atherosclerosis. The aim of this study was to investigate whether plant sterols and other markers of sterol metabolism predicted all-cause and cardiovascular mortality in participants of the Ludwigshafen Risk and Cardiovascular health (LURIC) study. A total of 1,257 individuals who did not use statins and at baseline had a mean (+/- SD) age of 62.8 (+/- 11.0) years were included in the present analysis. Lathosterol, cholestanol, campesterol, and sitosterol were measured to estimate cholesterol synthesis and absorption. The mean (+/- SD) time of the follow-up for all-cause and cardiovascular mortality was 7.32 (+/- 2.3) years. All-cause (P = 0.001) and cardiovascular (P = 0.006) mortality were decreased in the highest versus the lowest lathosterol to cholesterol tertile. In contrast, subjects in the third cholestanol to cholesterol tertile had increased all-cause (P < 0.001) and cardiovascular mortality (P = 0.010) compared with individuals in the first tertile. The third campesterol to cholesterol tertile was associated with increased all-cause mortality (P = 0.025). Sitosterol to cholesterol tertiles were not significantly related to all-cause or cardiovascular mortality. The data suggest that high absorption and low synthesis of cholesterol predict increased all-cause and cardiovascular mortality in LURIC participants.

    Topics: Absorption; Cardiovascular Diseases; Cholestanol; Cholesterol; Humans; Male; Middle Aged; Phytosterols; Prognosis; Risk; Sitosterols

2010
A microwell platform for the scale-up of a multistep bioconversion to bench-scale reactors: sitosterol side-chain cleavage.
    Biotechnology journal, 2010, Volume: 5, Issue:4

    The microwell-scale approach is widely used for screening purposes and one-pot biotransformations, but it has seldom been applied to complex whole cell multistep bioconversions, requiring prolonged incubation periods. The present study aims to contribute to filling this gap. The side-chain cleavage of sitosterol to androstenedione (AD) with Mycobacterium sp. NRRL B-3805 cells was used as a model system, and focus was given to the screening of suitable bioconversion media with 24-well microwell plates. Results show that to perform this particular bioconversion growing cells are preferred over resting cells due to higher conversion yields obtained in aqueous medium. The use of resting cells may nevertheless present an interesting approach provided catalytic activity is retained throughout successive runs. Maintaining suitable aeration levels (air flow of 1 mL/min) allowed minimizing the decay of catalytic activity typically observed alongside consecutive bioconversion runs with resting cells. Microwell plates with dedicated oxygen and pH monitoring capabilities proved effective in media development for complex multistep bioconversions using relatively slow-growing bacteria. Under constant k(L)a (0.044/s) similar AD production and dissolved oxygen profiles were observed in microwell plates and in a bench-scale reactor. Selection of a suitable k(L)a value proved critical, since under lower k(L)a values scale-up proved unsuccessful. The same pattern was observed when other scale-up criteria were evaluated to perform the scale-up of this particular bioconversion. Results gathered seem to validate the proposed approach "from microwell plate to bench-scale fermentor".

    Topics: Bioreactors; Cell Culture Techniques; Equipment Design; Equipment Failure Analysis; Mycobacterium; Pilot Projects; Sitosterols; Testosterone

2010
Analysis of sterol and other components present in unsaponifiable matters of mahua, sal and mango kernel oil.
    Journal of oleo science, 2010, Volume: 59, Issue:4

    The amount and characterization of phytosterol and other minor components present in three Indian minor seed oils, mahua (Madhuca latifolia), sal (Shorea robusta) and mango kernel (Mangifera indica), have been done. Theses oils have shown commercial importance as cocoa-butter substitutes because of their high symmetrical triglycerides content. The conventional thin layer chromatography (TLC), gas chromatography (GC) & gas chromatography-mass spectroscopy (GC-MS) techniques were used to characterize the components and the high performance thin layer chromatography (HPTLC) technique was used to quantify the each group of components. The experimental data showed that the all the three oils are rich in sterol content and among all the sterols, beta-sitosterol occupies the highest amount. Sal oil contains appreciable amount of cardenolides, gitoxigenin. Tocopherol is present only in mahua oil and oleyl alcohol is present in mango kernel oil. Hydrocarbon, squalene, is present in all the three oils. The characterization of these minor components will help to detect the presence of the particular oil in specific formulations and to assess its stability as well as nutritional quality of the specific oil.

    Topics: Cardenolides; Chromatography, Thin Layer; Fatty Alcohols; Food Analysis; Gas Chromatography-Mass Spectrometry; Hydrocarbons; Phytosterols; Plant Oils; Seeds; Sitosterols; Squalene; Tocopherols

2010
Ergosterol triggers characteristic elicitation steps in Beta vulgaris leaf tissues.
    Journal of experimental botany, 2010, Volume: 61, Issue:6

    This study investigates the role of the fungal sterol ergosterol as a general elicitor in the triggering of plant innate immunity in sugar beet. Evidence for this specific function of ergosterol is provided by careful comparison with cholesterol and three plant sterols (stigmasterol, campesterol, sitosterol), which do not enable the integrity of responses leading to elicitation. Our results demonstrate the modification of H(+) flux by ergosterol, due to the direct inhibition of the H(+)-ATPase activity on plasma membrane vesicles purified from leaves. The ergosterol-induced oxidative burst is related to enhanced NADPH-oxidase and superoxide dismutase activities. The similar effects obtained with the fungal elicitor chitosan further reinforce the particular role of ergosterol in the induced defences. The involvement of salicylic acid and/or jasmonic acid signalling in the ergosterol-enhanced plant non-host resistance is also studied. The possible link between ergosterol-triggered plant innate immunity and its putative impact on the structural organization of plant plasma membrane are discussed in terms of the ability of this fungal sterol to promote the formation of lipid rafts.

    Topics: Beta vulgaris; Biological Transport; Blotting, Western; Cell Membrane; Cholesterol; Electrophoresis, Polyacrylamide Gel; Enzyme Activation; Enzyme-Linked Immunosorbent Assay; Ergosterol; Hydrogen Peroxide; Hydrogen-Ion Concentration; Phytosterols; Plant Leaves; Sitosterols; Stigmasterol

2010
Nematicidal natural products from the aerial parts of Rubus niveus.
    Natural product research, 2010, Volume: 24, Issue:5

    Studies on the aerial parts of Rubus niveus yielded six known compounds, 3,5-dihydroxy benzoic acid C(7)H(6)O(4), (1), gallic acid C(7)H(6)O(5) (2), ethyl galactoside (3), oleanolic acid (4), beta-sitosterol (5) and 3-O-[beta-D-galactopyranosyl-(12)-D-glucopyranoside (6). Besides this, a gallic acid derivative with methyl substitution was synthesised as tetramethyl gallate (3). Together with this derivative, compounds 1, 2, the alcohol soluble, chloroform soluble and petroleum ether soluble extracts of the aerial parts of R. niveus were screened for its nematicidal activity against freshly hatched second stage juveniles of Meloidogyne incognita (root-knot nematode), exhibiting 100, 94, 100, 52, 45 and 14% mortality, respectively of M. incognita after 48 h at 0.5% concentration. Compounds 1, 2 and 3 were found to be more potent than the nematicide Azadirachta indica at the same concentration. Negative results were obtained for nematicidal activity of the petroleum ether extract of R. niveus leaf extract. This is the first report on the isolation of chemical constituents as well as the nematicidal activity of compounds and any part of R. niveus.

    Topics: Animals; Antinematodal Agents; Galactosides; Gallic Acid; Hydroxybenzoates; Mass Spectrometry; Nematoda; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Optical Rotation; Plant Components, Aerial; Plant Extracts; Resorcinols; Rosaceae; Sitosterols; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet

2010
Influence of colour type and previous cultivation on secondary metabolites in hypocotyls and leaves of maca (Lepidium meyenii Walpers).
    Journal of the science of food and agriculture, 2010, Apr-15, Volume: 90, Issue:5

    Maca is an Andean crop of the Brassicaceae family which is mainly known for its fertility-enhancing properties following consumption. The hypocotyls display various colours ranging from white to black. Each colour has different biological effects. The aim of this study was to analyse the concentrations of major secondary metabolites in hypocotyls and leaves of maca in a controlled planting experiment in the Peruvian Andes at 4130 m above sea level. The effects of colour type and of previous cultivation of the field were examined.. In the hypocotyls, the colour type effect was significant for most secondary metabolites; exceptions were beta-sitosterol and campesterol. The lead-coloured, yellow and violet maca hypocotyls were rich in glucosinolates, macaene and macamides, respectively. Previous cultivation affected macaene, campesterol and indole glucosinolate concentrations. Effects on metabolite concentrations in the leaves were minor. Hypocotyls were richer in macaene, macamides and glucosinolates than were leaves, and were poorer in beta-sitosterol and total phenols.. Colour type has to be considered in maca production, as colour associates with variations in concentrations of distinct bioactive metabolites. Leaves may be interesting for animal nutrition purposes as they contain essentially the same secondary metabolites as the hypocotyls but in clearly lower concentrations.

    Topics: Agriculture; Altitude; Cholesterol; Glucosinolates; Hypocotyl; Indoles; Lepidium; Linoleic Acids; Linolenic Acids; Nutritive Value; Organ Specificity; Palmitic Acids; Peru; Phytosterols; Pigmentation; Plant Leaves; Polyunsaturated Alkamides; Sitosterols; Soil; Species Specificity

2010
An anti-influenza component of the bark of Alnus japonica.
    Archives of pharmacal research, 2010, Volume: 33, Issue:3

    This study to identify anti-influenza components of the bark of Alnus japonica resulted in the isolation of four lupane-type triterpenes (1-4) and one steroid (5). Their structures were characterized on the basis of physicochemical properties, NMR evidence, and ESI-MS data compared with reported data in the literature. Betulinic aldehyde (3) exhibited a particularly strong anti-influenza effect against KBNP-0028 relative to a positive control.

    Topics: Alnus; Animals; Antiviral Agents; Cell Survival; Cells, Cultured; Chick Embryo; Dose-Response Relationship, Drug; Fibroblasts; Influenza A Virus, H9N2 Subtype; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Bark; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Steroids; Structure-Activity Relationship; Triterpenes

2010
Hepatoprotective effects of Rubus aleaefolius Poir. and identification of its active constituents.
    Journal of ethnopharmacology, 2010, May-27, Volume: 129, Issue:2

    The purpose of this study was to study the hepatoprotective effects of the most promising extract of the root from Rubus aleaefolius Poir. and to isolate and identify the active components. Various crude forms of Rubus aleaefolius have been evaluated for their effects on CCl(4)-induced acute liver injury in mice vivo experimental model. Treatment groups contained 5 sub-groups that were ethanol crude extract; the high/low dosage ethyl acetate or n-butanol fraction; extracted with ethyl acetate or n-butanol after the residues and major constituent; intragastrically administrated with 35 mg/kg; 35, 4.6 mg/kg; 35, 5.8 mg/kg; 35 mg/kg and 3.5 mg/kg for 7 days. The serum samples were collected for biological analysis and also carried out histopathological studies. The low-dosage ethyl acetate fraction was the most active when the fractions were compared. It was found to decrease AST, ALT; to prevent formation of hepatic MDA, NO and intensify the activity of SOD. The histopathological changes induced by CCl(4) were also significantly reduced. The separation revealed the presence of six constituents by a bioassay-guided fractionation, beta-Sitosterol (1), 1beta-Hydroxyeuscaphic acid (2), Oleanolic acid (3), Myrianthic acid (4), Euscaphic acid (5), and Tomentic acid (6). Among them, compounds 2, 4, 5 in Rubus aleaefolius root is reported here for the first time. 1beta-Hydroxyeuscaphic acid (major constituent) showed a tremendous activity and the results confirm the traditional uses of Rubus aleaefolius in treating hepatitis.

    Topics: Alanine Transaminase; Animals; Antioxidants; Aspartate Aminotransferases; Carbon Tetrachloride Poisoning; Chemical and Drug Induced Liver Injury; Liver; Male; Malondialdehyde; Mice; Mice, Inbred ICR; Nitric Oxide; Oleanolic Acid; Phytotherapy; Plant Extracts; Plant Roots; Rosaceae; Sitosterols; Superoxide Dismutase; Triterpenes

2010
Microbial side-chain degradation of ergosterol and its 3-substituted derivatives: a new route for obtaining of deltanoids.
    Steroids, 2010, Volume: 75, Issue:10

    The strain of Mycobacterium sp. VKM Ac-1815D was found to convert ergosterol and its 3-acetate mainly to androst-4-ene-3,17-dione (AD) thus demonstrating ability to reduce 7(8)-double bond and hydrolyze sterol ester in addition to oxidation of 3beta-hydroxy group, Delta(5)-Delta(4) isomerization and side-chain degradation. Ergosterol bioconversion in the presence of isoflavones and ions of some bivalent metals - known inhibitors of 3beta-hydroxysteroid dehydrogenase, did not alter products composition. Protection of ergosterol 3beta-hydroxyl with methoxymethyl group allowed the formation of bioconversion products retaining the Delta(5,7)-configuration. The major product was identified by mass-spectrometry and proton NMR as 3-methoxymethoxy-androsta-5,7-diene-17-one (MA). The MA producing activity was found to be inducible with sterols, cholestenone or lithocholic acid, but not with dehydroepiandrosterone, AD, androsta-1,4-ene-3,17-dione or organic acids. Under the optimized conditions, the yield of MA reached 5g/l from 10g/l O-methoxymethyl-ergosterol (approx. 60% molar conversion) for 120h. The results might be applied at the production of novel vitamin D derivatives.

    Topics: Androstenediols; Chromatography, Thin Layer; Ergosterol; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Mycobacterium; Sitosterols

2010
[Chemical contituents in leaves of Ehretia thyrsiflora].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2010, Volume: 35, Issue:3

    To investigate the chemical constituents of Ehretia thyrsiflora.. Compounds were isolated with silica gel, Sephadex LH-20 and RP-C18 colum chromatography. Their structures were elucidated by means of physico-chemical properties and spectral analysis.. Six compounds were isolated and identified as beta-sitosterol (1), ethyl caffeate (2), 2-methoxyl benzoic acid octyl ester (3), tetradecenoic acid, 2,3-dihydroxypropyl ester (4), daucoster (5), allantoin (6).. Compounds 1-5 were obtained from this species for the first time. Compounds 2-5 were obtained from the genus Ehretia for the first time.

    Topics: Allantoin; Boraginaceae; Caffeic Acids; Magnetic Resonance Spectroscopy; Plant Leaves; Sitosterols

2010
Comparative studies on the influence of beta-sitosterol and stigmasterol on model sphingomyelin membranes: a grazing-incidence X-ray diffraction study.
    The journal of physical chemistry. B, 2010, May-27, Volume: 114, Issue:20

    Sterols are essential constituents of membranes, both in the plant world and in human organisms. Therefore, their activity on model lipid systems has systematically been studied. Despite intensive investigations, differences in the effect induced by beta-sitosterol (beta-sito) and stigmasterol (stigma) (two major phytosterols) are very controversial and still under debate. To compare the influence of these compounds on model membranes, we have performed grazing incidence X-ray diffraction (GIXD) experiments on phytosterol/sphingomyelin (Sph) monolayers. The analysis of the X-ray scattering and the resulting in-plane parameters provided information on the lateral organization of pure lipid films and the mixed systems. The obtained results prove a nonideal mixing between the investigated lipids in the monolayers and the existence of strong interactions between phytosterols and Sph. Both the plant sterols incorporated into sphingolipid film condense the monolayer and order Sph chains. The results of GIXD experiments, compared with those obtained previously from Langmuir monolayer studies allowed us to observe the comparable influence of beta-sito and stigma on model membrane organization.

    Topics: Models, Molecular; Sitosterols; Sphingomyelins; Stigmasterol; X-Ray Diffraction

2010
Exploratory characterization of the unsaponifiable fraction of tunisian virgin olive oils by a global approach with HPLC-APCI-IT MS/MS analysis.
    Journal of agricultural and food chemistry, 2010, May-26, Volume: 58, Issue:10

    The unsaponifiable fraction of six Tunisian monovarietal virgin olive oils from the region of Medenine was evaluated within a single chromatographic run by using HPLC-APCI-tandem MS. Separation of the compounds under study was achieved by the RP-LC method, giving a reasonable analysis time and good resolution. Detection was done by an ion trap (working alternatively in MS and MS/MS modes), the fact which made our method suitable to unequivocally identify a high number of compounds belonging to different families of the unsaponifiable fraction of oil and to carry out their reliable and sensitive quantification. A great amount of qualitative information was generated in every analysis, although we focused on the quantification of sterols, tocopherols, and triterpenic dialcohols since their standards were commercially available. The limits of detections achieved were within the range of 1.21 and 10.31 microg/kg for sitostanol and beta-sitosterol, respectively. Significant differences were observed in the composition of the studied olive cultivars. Jemri Ben Guerdane oil was the richest one in terms of all of the sterols under study. alpha-Tocopherol was the main vitamin E isomer in all samples, ranging from 70.14 to 130.72 mg/kg. Principal component analysis (PCA) and cluster analysis were applied to the whole data set in order to explore the distribution of the olive cultivars according to their oil composition.

    Topics: Alcohols; Chromatography, High Pressure Liquid; Olive Oil; Phytosterols; Plant Oils; Saponins; Sitosterols; Species Specificity; Tandem Mass Spectrometry; Tocopherols; Triterpenes; Tunisia

2010
A role for beta-sitosterol to stigmasterol conversion in plant-pathogen interactions.
    The Plant journal : for cell and molecular biology, 2010, Volume: 63, Issue:2

    Upon inoculation with pathogenic microbes, plants induce an array of metabolic changes that potentially contribute to induced resistance or even enhance susceptibility. When analysing leaf lipid composition during the Arabidopsis thaliana-Pseudomonas syringae interaction, we found that accumulation of the phytosterol stigmasterol is a significant plant metabolic process that occurs upon bacterial leaf infection. Stigmasterol is synthesized from beta-sitosterol by the cytochrome P450 CYP710A1 via C22 desaturation. Arabidopsis cyp710A1 mutant lines impaired in pathogen-inducible expression of the C22 desaturase and concomitant stigmasterol accumulation are more resistant to both avirulent and virulent P. syringae strains than wild-type plants, and exogenous application of stigmasterol attenuates this resistance phenotype. These data indicate that induced sterol desaturation in wild-type plants favours pathogen multiplication and plant susceptibility. Stigmasterol formation is triggered through perception of pathogen-associated molecular patterns such as flagellin and lipopolysaccharides, and through production of reactive oxygen species, but does not depend on the salicylic acid, jasmonic acid or ethylene defence pathways. Isolated microsomal and plasma membrane preparations exhibited a similar increase in the stigmasterol/beta-sitosterol ratio as whole-leaf extracts after leaf inoculation with P. syringae, indicating that the stigmasterol produced is incorporated into plant membranes. The increased contents of stigmasterol in leaves after pathogen attack do not influence salicylic acid-mediated defence signalling but attenuate pathogen-induced expression of the defence regulator flavin-dependent monooxygenase 1. P. syringae thus promotes plant disease susceptibility through stimulation of sterol C22 desaturation in leaves, which increases the stigmasterol to beta-sitosterol ratio in plant membranes.

    Topics: Arabidopsis; Arabidopsis Proteins; Botrytis; Cytochrome P-450 Enzyme System; Gene Expression Regulation, Plant; Host-Pathogen Interactions; Plant Diseases; Plant Growth Regulators; Plant Leaves; Pseudomonas syringae; Sitosterols; Stigmasterol

2010
β-Sitosterol: supercritical carbon dioxide extraction from sea buckthorn (Hippophae rhamnoides L.) seeds.
    International journal of molecular sciences, 2010, Apr-22, Volume: 11, Issue:4

    Supercritical fluid extraction represents an efficient and environmentally friendly technique for isolation of phytosterols from different plant sources. Sea buckthorn (Hippophae rhamnoides L.) seeds were extracted with supercritical carbon dioxide at pressures ranging from 15-60 MPa and temperatures of 40-80 degrees C. Oil and β-sitosterol yields were measured in the extraction course and compared with Soxhlet extraction with hexane. The average yield of β-sitosterol was 0.31 mg/g of seeds. The maximum concentration of β-sitosterol in the extract, 0.5% w/w, was achieved at 15 MPa, 40 degrees C, and a carbon dioxide consumption of 50 g/g of seeds. The extraction rate was maximal at 60 MPa and 40 degrees C. Both β-sitosterol yield and its concentration in the extract obtained with hexane were lower than with carbon dioxide.

    Topics: Carbon Dioxide; Chromatography, High Pressure Liquid; Chromatography, Supercritical Fluid; Hippophae; Plant Oils; Pressure; Seeds; Sitosterols; Temperature

2010
Estrogenic and anti-estrogenic effects of wood extractives present in pulp and paper mill effluents on rainbow trout.
    Aquatic toxicology (Amsterdam, Netherlands), 2010, Aug-15, Volume: 99, Issue:2

    Wood extractives present in pulp and paper mill effluents may cause reproductive disturbances in fish. A chronic-exposure toxicity experiment using immature rainbow trout (Oncorhynchus mykiss) was conducted in order to assess the endocrine disrupting effects of two Chilean pulp and paper mill specific extracts (solid phase extraction, SPE) obtained from primary and secondary treated effluents. The (anti)estrogenic potencies and toxicity of the wood extractives regularly present in pulp mill effluent such as dehydroabietic acid (DHAA), beta-sitosterol (BS), and model estrogen 17beta-estradiol (E2) were evaluated by analysis of plasma vitellogenin (VTG) levels, gonadal somatic index (GSI) and liver ethoxyresorufin-O-deethylase (EROD) activity, respectively. The protocol involved the use of multiple intra-peritoneal injections (1 injection every 7 days for a total exposure period of 28 days). Analysis of variance/covariance, demonstrated no differences associated with fish gender other than GSI. The phytosterol BS, E2 and both pulp mill effluent extracts showed significant inductions of EROD and increased VTG levels after 4, 7, 14, 21 and 28 of exposure. While fish injected with secondary treated effluent extract showed a delayed induction in VTG levels compared to primary effluent injected fish, no effects on VTG and EROD levels were observed in DHAA injected fish. Moreover simultaneous injection of DHAA+E2 reduced the VTG levels found in E2 injected fish, indicating a potential indirect anti-estrogenic effect of this resin acid. The results of this study indicate that Chilean pulp and paper mill effluent extracts are estrogenic in rainbow trout males and females.

    Topics: Animals; Cytochrome P-450 CYP1A1; Endocrine Disruptors; Estradiol; Female; Industrial Waste; Liver; Male; Oncorhynchus mykiss; Paper; Sitosterols; Vitellogenins; Water Pollutants, Chemical; Wood

2010
Scaling-up of complex whole-cell bioconversions in conventional and non-conventional media.
    Biotechnology and bioengineering, 2010, Jul-01, Volume: 106, Issue:4

    The use of whole cells is becoming a more common approach in pharmaceutical and agrochemical industries in order to obtain pure compounds with fewer production steps, higher yields, and cleaner processes, as compared to those achieved with traditional strategies. Whole cells are often used as enzymes pools, in particular when multi-step reactions and/or co-factor regeneration are envisaged. Nonetheless, published information on the scale-up of such systems both in aqueous and in two-phase aqueous-organic systems is relatively scarce. The present work aims to evaluate suitable scale-up criteria in conventional and non-conventional medium for a whole-cell bioconversion that uses resting cells of Mycobacterium sp. NRRL B-3805 to cleave the side chain of beta-sitosterol, a poorly water-soluble substrate. The experiments were performed in 24-well microtiter plates and in 250 mL shaken flasks as orbital stirred systems, and in 300 mL stirred tanks as mechanically stirred systems. Results show that productivity yields were similar in all scales tested, when maintaining oxygen mass transfer coefficients constant in aqueous systems, or when maintaining constant volumetric power consumption in aqueous-organic two-phase systems.

    Topics: Bioreactors; Biotechnology; Biotransformation; Culture Media; Mycobacterium; Sitosterols

2010
Sitosterol thermo-oxidative degradation leads to the formation of dimers, trimers and oligomers: a study using combined size exclusion chromatography/mass spectrometry.
    Lipids, 2010, Volume: 45, Issue:6

    Phytosterols are recognized as functional food components with cholesterol reducing properties in humans. The formation of phytosterol oligomers as a result of the thermo-oxidative degradation of sitosterol is shown to occur. The existence of oligomers is demonstrated by size exclusion chromatography (SEC) and confirmed by combined SEC-atmospheric pressure chemical ionization mass spectrometry (SEC/APCI-MS). A speculative structure for the sitosterol dimer with 3,7' linkage is proposed consistent with data from tandem mass spectrometry and exact mass measurements. Higher molecular weight species arising from the formation of trimers or higher oligomers are seen in the mass spectra. Fragments of sitosterol formed by thermo-oxidative processes are also shown to oligomerize and their common structural characteristics are demonstrated by tandem mass spectrometry. The results presented provide evidence for the possible formation of oligomeric species involving sterols in addition to those known for acylglycerides in vegetable oils subjected to extreme oxidative stress such as in frying.

    Topics: Chromatography, Gel; Dimerization; Mass Spectrometry; Oxidation-Reduction; Sitosterols

2010
[Study on the chemical constituents of Humulus scandens].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:1

    To study the chemical constituents of Humulus scandens.. The compounds were isolated by column chromatography on silica gel and Sephadex LH-20. The structures were identified by means of IR, 1H-NMR,13C-NMR and MS analyses.. Seven compounds were isolated and identified as friedelanone (I), cis-asarone (II), epifriedelanol (III), stigmasta-4-ene-3,6-dione (IV), gamma-sitosterol (V), n-hexadecanoic acid (VI), and linoleic acid (VII), respectively.. All compounds are isolated from this species for the first time and compounds I - V are obtained from this genus for the first time.

    Topics: Cholestenones; Gas Chromatography-Mass Spectrometry; Humulus; Linoleic Acid; Molecular Structure; Palmitic Acid; Plants, Medicinal; Sitosterols; Triterpenes

2010
Chemopreventive potential of beta-Sitosterol in experimental colon cancer model--an in vitro and In vivo study.
    BMC complementary and alternative medicine, 2010, Jun-04, Volume: 10

    Asclepias curassavica Linn. is a traditional medicinal plant used by tribal people in the western ghats, India, to treat piles, gonorrhoea, roundworm infestation and abdominal tumours. We have determined the protective effect of beta-sitosterol isolated from A. curassavica in colon cancer, using in vitro and in vivo models.. The active molecule was isolated, based upon bioassay guided fractionation, and identified as beta-sitosterol on spectral evidence. The ability to induce apoptosis was determined by its in vitro antiradical activity, cytotoxic studies using human colon adenocarcinoma and normal monkey kidney cell lines, and the expression of beta-catenin and proliferating cell nuclear antigen (PCNA) in human colon cancer cell lines (COLO 320 DM). The chemopreventive potential of beta-sitosterol in colon carcinogenesis was assessed by injecting 1,2-dimethylhydrazine (DMH, 20 mg/kg b.w.) into male Wistar rats and supplementing this with beta-sitosterol throughout the experimental period of 16 weeks at 5, 10, and 20 mg/kg b.w.. beta-sitosterol induced significant dose-dependent growth inhibition of COLO 320 DM cells (IC50 266.2 microM), induced apoptosis by scavenging reactive oxygen species, and suppressed the expression of beta-catenin and PCNA antigens in human colon cancer cells. beta-sitosterol supplementation reduced the number of aberrant crypt and crypt multiplicity in DMH-initiated rats in a dose-dependent manner with no toxic effects.. We found doses of 10-20 mg/kg b.w. beta-sitosterol to be effective for future in vivo studies. beta-sitosterol had chemopreventive potential by virtue of its radical quenching ability in vitro, with minimal toxicity to normal cells. It also attenuated beta-catenin and PCNA expression, making it a potential anticancer drug for colon carcinogenesis.

    Topics: Adenocarcinoma; Animals; Antineoplastic Agents, Phytogenic; Antioxidants; Apoptosis; Asclepias; beta Catenin; Cell Line; Cell Line, Tumor; Colon; Colonic Neoplasms; Disease Models, Animal; Dose-Response Relationship, Drug; Haplorhini; Humans; Kidney; Male; Phytotherapy; Plant Extracts; Proliferating Cell Nuclear Antigen; Rats; Rats, Wistar; Sitosterols

2010
Metabolic engineering by plastid transformation as a strategy to modulate isoprenoid yield in plants.
    Methods in molecular biology (Clifton, N.J.), 2010, Volume: 643

    Plants synthesize a large number of isoprenoid compounds that have diverse structures and functions. All isoprenoids are synthesized through consecutive condensation of five-carbon precursors, isopentenyl diphosphate (IPP) and its allyl isomer dimethylallyl diphosphate (DMAPP). With recent success in the cloning of genes that encode the enzymes of isoprenoid biosynthesis, genetic engineering strategies for the improvement of plant isoprenoid metabolism have emerged. Plastid transformation technology offers attractive features in plant genetic engineering. It has many advantages over nuclear genome transformation: high-level foreign protein expression, no need for a transit peptide, absence of gene silencing, and convenient transgene stacking in operons. We demonstrated that this technology is a remarkable tool for the production of isoprenoids in plants through metabolic engineering. The expression of bacterial genes encoding CrtW (beta-carotene ketolase) and CrtZ (beta-carotene hydroxylase) or cyanobacterial genes encoding DXR (1-deoxy-D-xylulose-5-phosphate reductoisomerase) in the plastid genome leads to alteration in isoprenoid content of tobacco leaves.

    Topics: Aldose-Ketose Isomerases; Cyanobacteria; Genetic Engineering; Multienzyme Complexes; Neoprene; Nicotiana; Oxidoreductases; Phytol; Pigments, Biological; Plant Proteins; Plastids; Sitosterols; Terpenes; Transformation, Genetic

2010
Molecular dynamics simulation and binding studies of beta-sitosterol with human serum albumin and its biological relevance.
    The journal of physical chemistry. B, 2010, Jul-15, Volume: 114, Issue:27

    Beta-sitosterol is a naturally occurring phytosterol that is widely used to cure atherosclerosis, diabetes, cancer, and inflammation and is also an antioxidant. Here, we studied the interaction of beta-sitosterol, isolated from the aerial roots of Ficus bengalensis, with human serum albumin (HSA) at physiological pH 7.2 by using fluorescence, circular dichroism (CD), molecular docking, and molecular dynamics simulation methods. The experimental results show that the intrinsic fluorescence of HSA is quenched by addition of beta-sitosterol through a static quenching mechanism. The binding constant of the compound to HSA, calculated from fluorescence data, was found to be K(beta-sitosterol) = 4.6 +/- 0.01 x 10(3) M(-1), which corresponds to -5.0 kcal M(-1) of free energy. Upon binding of beta-sitosterol to HSA, the protein secondary structure was partially unfolded. Specifically, the molecular dynamics study makes an important contribution to understanding the effect of the binding of beta-sitosterol on conformational changes of HSA and the stability of a protein-drug complex system in aqueous solution. Molecular docking studies revealed that the beta-sitosterol can bind in the large hydrophobic cavity of subdomain IIA, mainly by the hydrophobic interaction but also by hydrogen bond interactions between the hydroxyl (OH) group of carbon-3 of beta-sitosterol to Arg(257), Ser(287), and Ala(261) of HSA, with hydrogen bond distances of 1.9, 2.4, and 2.2 A, respectively.

    Topics: Binding Sites; Circular Dichroism; Ficus; Humans; Hydrogen-Ion Concentration; Molecular Dynamics Simulation; Plant Roots; Protein Binding; Protein Conformation; Serum Albumin; Sitosterols; Spectrometry, Fluorescence; Spectrometry, Mass, Electrospray Ionization; Thermodynamics; Time Factors

2010
[Study on the chemical constituents from pine needles of Cedrus deodara].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:2

    To study the chemical constituents from pine needles of Cedrus deodara.. Chemical constituents were isolated by silica gel and Sephadex LH-20 column chromatography. The structures of the isolated compounds were elucidated through spectroscopic analysis.. The compounds were identified as 9-hydroxy-dodecanoic acid (I), ethyl laurate (II), ethyl stearate (III), 3beta-hydroxy-oleanolic acid methyl ester (IV), beta-sitosterol (V), shikimic acid (VI), methylconiferin (VII), ferulic acid beta-glucoside (VIII).. Compounds I-IV, VI-VIII are isolated and identified from this genus for the first time, compound V is isolated from pine needles of this genus for the first time.

    Topics: Cedrus; Chromatography, Thin Layer; Laurates; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plant Leaves; Saponins; Shikimic Acid; Sitosterols; Stearates

2010
Characterization of a potential nutraceutical ingredient: pomegranate (Punica granatum L.) seed oil unsaponifiable fraction.
    Plant foods for human nutrition (Dordrecht, Netherlands), 2010, Volume: 65, Issue:3

    The chemical fingerprinting of the unsaponifiable fraction of different Punica granatum seed oils was performed in order to evaluate their potential as a functional food ingredient. Qualitative and quantitative determinations of tocopherol, aliphatic alcohol (including policosanol), squalene, phytosterols and triterpene contents were performed by GC-MS. A high yield (3.1-4.2%) of unsaponifiable matter was obtained and consistent levels of squalene (up to 800 mg/kg) and policosanol (118-185 mg/kg) were noticed. β-sitosterol (up to 8069 mg/kg) and cycloartenol (5916-7766 mg/kg) were predominant in phytosterol and triterpene fractions, while β- and δ-tocopherol were the most abundant vitamin E forms. Some minor variations were noticed between samples. From the results obtained, it can be suggested that the seed oil of P. granatum can be considered an interesting alimentary source of substances of nutraceutical value involved in the modulation of cholesterol metabolism.

    Topics: beta-Tocopherol; Dietary Supplements; Fatty Alcohols; Functional Food; Lythraceae; Phytosterols; Plant Oils; Seeds; Sitosterols; Squalene; Tocopherols; Triterpenes

2010
Quantum chemical treatment of beta-sitosterol molecule.
    Pharmaceutical biology, 2010, Volume: 48, Issue:6

    Beta-sitosterol is used as a dietary supplement for lowering plasma cholesterol, and has atherosclerosis preventive, anti-inflammatory, antimicrobial, antipyretic, induced apoptosis, and anticancer effects. In order to understand the effect of the molecule we have investigated the molecule theoretically. The structural, vibrational, and electronic properties of the beta-sitosterol molecule have been investigated theoretically by performing molecular mechanics (MM+ force field), semiempirical self-consistent-field molecular-orbital (PM3), and density functional theory (B3LYP) calculations. The geometry of the considered molecule has been optimized; the vibrational dynamics and the electronic properties have been calculated in its ground state in the gas phase. The optimized structure of the molecule is not planar, and its heat of formation is exothermic. The calculated infrared spectrum for beta-sitosterol agrees well qualitatively with the experimentally determined FTIR spectrum. The interfrontier molecular orbitals are localized mainly on the double C-C bond, and the energy difference of the corresponding orbitals is relatively small, which makes the molecule kinetically stable. According to the calculated dipole moment, beta-sitosterol is a polar molecule. The calculated results for the beta-sitosterol molecule in the present study will aid in elucidation of the mechanism of action and may further be used in lipid metabolism drug design studies.

    Topics: Electronics; Hypolipidemic Agents; Models, Molecular; Quantum Theory; Sitosterols; Spectrophotometry, Infrared; Spectroscopy, Fourier Transform Infrared; Vibration

2010
The replacement of cholesterol by phytosterols and the increase of total sterol content in model erythrocyte membranes.
    Chemistry and physics of lipids, 2010, Volume: 163, Issue:7

    The activity of phytosterols on human organism includes the ability of these compounds to incorporate into membranes. In the consequence the plant sterols are able to increase total sterol concentration in membrane or/and to replace cholesterol molecules. The aim of this work was to compare the influence of both these effects on the properties of model erythrocyte membranes. Moreover, the interactions between the plant sterols (beta-sitosterol and stigmasterol) and saturated-monounsaturated phosphatidylcholine were investigated and the condensing and ordering potency of these phytocompounds on membrane phospholipids were thoroughly analyzed. It was found that the addition of the plant sterols into model membrane modifies the condensation, ordering and interactions in the system. Moreover, the replacement of mammalian sterol by phytosterol more strongly influences the model system than even a 10% increase of total sterol concentration induced by the incorporation of the plant sterol, at constant content of cholesterol. The investigated plant sterols at their lower concentration in the mixed system are of similar effect on its properties. At higher content stigmasterol was found to modify the properties of model membrane more strongly than beta-sitosterol.

    Topics: Cholesterol; Erythrocyte Membrane; Humans; Membranes, Artificial; Phosphatidylcholines; Phytosterols; Sitosterols; Stigmasterol; Thermodynamics

2010
A concise synthesis of beta-sitosterol and other phytosterols.
    Steroids, 2010, Volume: 75, Issue:12

    A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of beta-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Delta(22-23) phytosterols.

    Topics: Alkenes; Cholesterol; Epoxy Compounds; Phytosterols; Sitosterols

2010
Chemical constituents of Citrus sinensis var. Shukri from Pakistan.
    Journal of Asian natural products research, 2010, Volume: 12, Issue:8

    The variety 'Shukri' is a new hybrid of Citrus sinensis and is frequently grown for its sweet edible fruits in the southern part of Pakistan. The leaves of this hybrid variety have been investigated in search of secondary metabolites for the first time. As a result of chromatographic analysis of the methanolic extract, a new ceramide along with a flavonone glycoside and two steroids has been isolated, which were spectroscopically characterized as (E)-N-(1,3,4,5-tetrahydroxyhexadecan-2-yl)dec-4-enamide (1), atripliside B (2), beta-sitosterol (3), and beta-sitosterol-3-O-beta-D-glucopyranoside (4), respectively. Compound 1 was found to be a new addition in the list of natural products, whereas, to the best of our knowledge, compounds 2-4 have been isolated for the first time from this source.

    Topics: Ceramides; Citrus sinensis; Flavonoids; Glucosides; Glycosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pakistan; Plant Leaves; Sitosterols

2010
Identification by whole-genome resequencing of gene defect responsible for severe hypercholesterolemia.
    Human molecular genetics, 2010, Nov-15, Volume: 19, Issue:22

    Whole-genome sequencing is a potentially powerful tool for the diagnosis of genetic diseases. Here, we used sequencing-by-ligation to sequence the genome of an 11-month-old breast-fed girl with xanthomas and very high plasma cholesterol levels (1023 mg/dl). Her parents had normal plasma cholesterol levels and reported no family history of hypercholesterolemia, suggesting either an autosomal recessive disorder or a de novo mutation. Known genetic causes of severe hypercholesterolemia were ruled out by sequencing the responsible genes (LDLRAP, LDLR, PCSK9, APOE and APOB), and sitosterolemia was ruled out by documenting a normal plasma sitosterol:cholesterol ratio. Sequencing revealed 3 797 207 deviations from the reference sequence, of which 9726 were nonsynonymous single-nucleotide substitutions. A total of 9027 of the nonsynonymous substitutions were present in dbSNP or in 21 additional individuals from whom complete exonic sequences were available. The 699 novel nonsynonymous substitutions were distributed among 604 genes, 23 of which were single-copy genes that each contained 2 nonsynonymous substitutions consistent with an autosomal recessive model. One gene, ABCG5, had two nonsense mutations (Q16X and R446X). This finding indicated that the infant has sitosterolemia. Thus, whole-genome sequencing led to the diagnosis of a known disease with an atypical presentation. Diagnosis was confirmed by the finding of severe sitosterolemia in a blood sample obtained after the infant had been weaned. These findings demonstrate that whole-genome (or exome) sequencing can be a valuable aid to diagnose genetic diseases, even in individual patients.

    Topics: Base Sequence; Cholesterol; Female; Genome; Humans; Hypercholesterolemia; Infant; Pedigree; Sequence Analysis, DNA; Sitosterols

2010
Effect of vitamin D and β-sitosterol on immune function of macrophages.
    International immunopharmacology, 2010, Volume: 10, Issue:11

    Among the many functions of vitamin D (VD) is its role in the immunomodulation of macrophage. As VD deficiency is a wide-spread nutritional problem, there is a tendency for the public to overdose with vitamin D supplementation which can result in hypercalcemia and several associated disorders. The present study was designed to investigate the possibility that combining low doses of vitamin D with β-sitosterol (SIT), a common phytosterol in the diet without toxicity, enhances the efficacy of the vitamin. Murine macrophages were stimulated with LPS and supplemented with VD3 (80 nM) and SIT (8 μM) for 24 hr and examined for cell proliferation, release of nitric oxide (NO) and cytokines and the activation of NFκB. SIT (8 μM) was found to reduce cell proliferation by 62% while VD3 was found to be not effective. In combination, SIT and VD3 reduced cell proliferation by 75%.The amount of NO released, as influenced by 8 μM SIT or 80 nM VD3 treatments, was not significantly different from control. Combining SIT and VD3, resulted in a 220% greater increase in NO release compared to control. The SIT + VD3 treatment brought about significant increase in all the cytokine release, regardless of whether they were pro- or anti-inflammatory. The effects were either additive or synergistic. We conclude that SIT enhances the action of VD3 on the immune function of macrophages which could be beneficial to vitamin D deficient individuals and to those with autoimmune diseases such as multiple sclerosis.

    Topics: Animals; Cell Line; Cell Proliferation; Cholecalciferol; Cytokines; Drug Synergism; Immunologic Factors; Lipopolysaccharides; Macrophage Activation; Macrophages; Mice; NF-kappa B; Nitric Oxide; Sitosterols; Vitamins

2010
β-Sitosterol inhibits cell cycle progression of rat aortic smooth muscle cells through increases of p21cip1 protein.
    Journal of agricultural and food chemistry, 2010, Sep-22, Volume: 58, Issue:18

    Abnormal proliferation of vascular smooth muscle cells (VSMCs) plays a central role in the pathogenesis of atherosclerosis. β-Sitosterol, an important phytosterol found in plant food, is known to exert antiatherosclerosis activity. However, the molecular mechanisms underlying β-sitosterol-induced antiproliferation of VSMCs were still not clear. This study demonstrated that β-sitosterol (1-20 μM) concentration-dependently inhibited proliferation of rat aortic smooth muscle cells (RASMCs) without cytotoxic effect. Flow cytometric analysis revealed that β-sitosterol arrested cell cycle progression through down-regulation of cyclin E and cyclin-dependent kinase (CDK)2 and up-regulation of p21cip1. In the β-sitosterol-treated RASMCs, the formation of the CDK2-p21cip1 complex was increased and the assayable CDK2 activity was decreased. Knockdown of the expression of p21cip1 gene prevented β-sitosterol-induced cell cycle arrest in RASMCs. In conclusion, β-sitosterol inhibited VSMC proliferation by increasing the levels of p21cip1 protein, which in turn inhibited the CDK2 activity, and finally interrupted the progress of the cell cycle.

    Topics: Animals; Aorta, Thoracic; Atherosclerosis; Cell Cycle; Cell Proliferation; Cells, Cultured; Cyclin-Dependent Kinase Inhibitor p21; Hypolipidemic Agents; Male; Muscle, Smooth, Vascular; Rats; Rats, Sprague-Dawley; Sitosterols; Up-Regulation

2010
Lipid components of olive oil from Tunisian Cv. Sayali: characterization and authenticity.
    Comptes rendus biologies, 2010, Volume: 333, Issue:9

    The analysis of the total lipid fraction from the Sayali variety of olive oil was accomplished in the present investigation. Glyceridic, unsaponifiable and flavour fractions of the oil were isolated and identified using several analytical methods. Chromatographic techniques have proven to be suitable for these determinations, especially capillary gas chromatography. Gas chromatography coupled to mass spectrometry was successfully used to identify sterols, triterpenes alcohols, 4-monomethylsterols, aliphatic alcohols and aroma compounds in our samples. Furthermore, solid phase microextraction was used to isolate volatiles from the total lipid fraction. Results from the quantitative characterization of Sayali olive oil showed that oleic acid (77.4%) and triolein (47.4%) were the dominant glyceridic components. However, the main compounds of the unsaponifiable fraction were beta-sitosterol (147.5mg/100g oil), 24-methylene cycloartenol (146.4mg/100g oil) and hexacosanol (49.3mg/100g oil). Moreover, results showed that the aldehydic compounds were the major flavours present in Sayali olive oil.

    Topics: Alcohols; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Fatty Acids; Fatty Alcohols; Flame Ionization; Gas Chromatography-Mass Spectrometry; Lipids; Oleic Acid; Olive Oil; Phytosterols; Plant Oils; Sitosterols; Sterols; Triglycerides; Triolein; Tunisia

2010
5-Hydroxydictamnine, a new alkaloid from Atalantia monophylla.
    Natural product research, 2010, Volume: 24, Issue:16

    A new furoquinoline alkaloid, 5-hydroxydictamnine, along with β-sitosterol was isolated from the heartwood of Atalantia monophylla. The structure of this alkaloid was established by chemical and spectral evidences together with a nuclear overhauser effect (NOE) experiment.

    Topics: Alkaloids; Molecular Structure; Plants, Medicinal; Quinolines; Rutaceae; Sitosterols; Wood

2010
[Studies on the chemical constituents of Kalimeris indica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:4

    To study the chemical constituents from Kalimeris indica.. Compounds were isolated and purified with silica gel and Sephadex LH-20 column chromatography, their structures were determined by using spectroscopic analysis including MS and NMR.. Nine compounds were isolated and identified as tritriacontane (I), hexadecanol (II), chrysophanol (III), vanillin (IV), physcion (V), beta-sitosterol (VI), stigmasterol (VII), leinoleic acid (VII), emodin (IX).. All of them, except compound IV, VI, are isolated from this genus for the first time. Compound III, IV had the protective effects with the toxicity of CCl4 on primary cultered hepatocytes.

    Topics: Anthraquinones; Anti-Inflammatory Agents; Asteraceae; Benzaldehydes; Carbon Tetrachloride; Cell Survival; Cells, Cultured; Chemical and Drug Induced Liver Injury; Emodin; Fatty Alcohols; Hepatocytes; Magnetic Resonance Spectroscopy; Paraffin; Plants, Medicinal; Sitosterols

2010
[Studies on the chemical constituents of Solanum nigrum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:4

    To study the chemical constituents from Solanum nigrum.. Compounds were isolated and purified by silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by physicochemical properties and spectral analysis.. Six compounds were isolated and identified as (+)-pinoresinol (I), (+)-syringaresinol (II), (+)-medioresinol (III), scopoletin (IV), tetracosanoic acid (V) and beta-sitosterol (VI).. Compounds I - III are isolated from this genus for the first time, while compounds IV and V are isolated from this plant for the first time.

    Topics: Anti-Inflammatory Agents; Chromatography, High Pressure Liquid; Fatty Acids; Furans; Lignans; Plants, Medicinal; Scopoletin; Sitosterols; Solanum nigrum

2010
[Studies on the chemical constituents from Radix Ranunculi Ternate].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:5

    To study the chemical constituents from Radix Ranunculi Ternate.. The compounds were isolated by silica gel, Sephadex LH-20, and ODS column chromatography, and their structures were elucidated by means of spectral analysis.. Eight compounds were isolated and identified as phillygenin (I), bis-(2-ethylhexyl) phthalate (DEHP, II), henicosanoic acid methyl ester (III), 5-hydroxymethyl-furfural (IV), mixture of stigmasterol and sitosterol (V and VI), daucosterol (VII).. Compounds I-III are isolated from the genus for the first time.

    Topics: Diethylhexyl Phthalate; Furaldehyde; Lignans; Magnetic Resonance Spectroscopy; Plant Roots; Plants, Medicinal; Ranunculus; Sitosterols; Stigmasterol

2010
[Studies on the chemical constituents of Ficus microcarpa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:6

    To study the chemical constituents of the Ficus microcarpa.. Isolation and identification were carried out by using various chromatography techniques and spectral methods.. Eight compounds were isolated. Their structures were identified as beta-amyrone (I), lupeol (II), lupeol acetate (III), maslinic acid (IV), epifriedelinol (V), stearic acid (VI), beta-sitosterol (VI), daucosterol (VI).. Compounds I, II, VI are isolated from this plant for the first time.

    Topics: Ficus; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Leaves; Sitosterols; Stearic Acids; Triterpenes

2010
Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia.
    Molecules (Basel, Switzerland), 2010, Nov-18, Volume: 15, Issue:11

    Four phenolics, salviaplebeiaside (1), γ-tocopherol (2), chrysosplenol-D (4), and isovitexin (5), along with α-tocoquinone (3) and β-sitosterol (6) were isolated from the aerial parts of Vitex negundo var. cannabifolia. The isolation was performed using bio-assay tracking experiments. The structures of compounds 1-5 were established by spectroscopic means. The antibacterial activities of the compounds were assessed against Escherichia coli, Bacillus subtilis, Micrococcus tetragenus and Pseudomonas fluorescens. Chrysosplenol-D (4) exhibited activities against all the four spoilage microorganisms.

    Topics: Anti-Bacterial Agents; Apigenin; Bacillus subtilis; Escherichia coli; Flavonoids; gamma-Tocopherol; Micrococcus; Phenols; Plant Components, Aerial; Plant Extracts; Pseudomonas fluorescens; Sitosterols; Vitamin E; Vitex

2010
A new sesquiterpene and other constituents from Saussurea lappa root.
    Natural product communications, 2010, Volume: 5, Issue:10

    Five sesquiterpenes, dehydrocostus lactone (1), santamarine (5), beta-cyclocostunolide (6), 4alpha-hydroxy-4beta-methyldihydrocostol (7) and 10alpha-hydroxyl-artemisinic acid (9), along with four other compounds, beta-sitosterol (2), daucosterol (3), 5-hydroxymethyl-furaldehyde (4), and trans-syingin (8), were isolated and identified from the roots of Saussurea lappa (Compositae). Based on previous reports and our study, sesquiterpene derivatives are common and characteristic constituents of the genus Saussurea. Among the nine compounds obtained, 9 is a new sesquiterpene. It is an artemisinic acid derivative, whose structural skeleton has not been reported for Saussurea species before, but artemisinic acid is a common compound in another Compositae species, Artemisia annua. Dehydrocostus lactone (1) is present in high-content and is a possible bioprecursor of 10alpha-hydroxyartemisinic acid (9).

    Topics: Furaldehyde; Plant Roots; Saussurea; Sesquiterpenes; Sitosterols

2010
Chemical and biological investigations of Delonix regia (Bojer ex Hook.) Raf.
    Acta pharmaceutica (Zagreb, Croatia), 2010, Volume: 60, Issue:2

    In this study, five compounds, lupeol (1), epilupeol (2), β-sitosterol (3), stigmasterol (4) and p-methoxybenzaldehyde (5) were isolated from the petroleum ether and dichloromethane fractions of a methanolic extract of the stem bark of Delonix regia. Antimicrobial screening of the different extracts (15 μg mm-2) was conducted by the disc diffusion method. The zones of inhibition demonstrated by the petroleum ether, carbon tetrachloride and dichloromethane fractions ranged from 9-14 mm, 11-13 mm and 9-20 mm, respectively, compared to kanamycin standard with the zone of inhibition of 20-25 mm. In brine shrimp lethality bioassay, the carbon tetrachloride soluble materials demonstrated the highest toxicity with LC50 of 0.83 μg mL-1, while petroleum ether and dichloromethane soluble partitionates of the methanolic extract revealed LC50 of 14.94 and 3.29 μg mL-1, respectively, in comparison with standard vincristine sulphate with LC50 of 0.812 μg mL-1. This is the first report on compounds separation from D. regia, their antimicrobial activity and cytotoxicity.

    Topics: Animals; Anti-Bacterial Agents; Antifungal Agents; Benzaldehydes; Fabaceae; Kanamycin; Microbial Sensitivity Tests; Pentacyclic Triterpenes; Plant Extracts; Sitosterols; Stigmasterol

2010
[Studies on the chemical constituents of Wikstroemia indica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:7

    To study the chemical constituents of Wikstroemia indica.. The constituents were isolated and purified by silica gel chromatography repeatedly, and the structures were determined by spectral data and chemical envidance.. Six compounds were isolated from its petroleum ether, dichloromethane, acetone and methanol extracts and identified as: daphnoretin-7-O-beta-D-glucoside (1), aloe-emodin (2), kaempferol (3), 29-nonacosanolide (4), 1-octadecanol (5), beta-sitosterol (6).. Compounds 2, 4, 5 are isolated from this plant for the first time.

    Topics: Anthraquinones; Fatty Alcohols; Kaempferols; Molecular Structure; Plant Bark; Plant Roots; Plants, Medicinal; Sitosterols; Wikstroemia

2010
[Studies on the chemical constituents from the antithrombus activity extract of Radix Aerio Fici Microcarpae].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:8

    To study the chemical constituent from the antithrombus activity extract of Radix Aerio Fici Microcarpae.. The isolation and purification of the extract were conducted by means of silica gel column chromatography, polyamide column chromatography and recrytallization. The structures of these compounds were elucidated based on the physicochemical properties and spectroscopic analysis.. 7 compounds were isolated from the extract. They were identified as isovanillic acid (1), 4-hydroxybenzoic acid(2),3,4-dihydroxybenzoic acid (3), friedelane (4), alpha-amyrin acetate (5), lanosterol (6) and beta-sitosterol (7) .. Compound 3,4 and 7 are isolated from this plant for the first time.

    Topics: Fibrinolytic Agents; Ficus; Hydroxybenzoates; Lanosterol; Molecular Structure; Oleanolic Acid; Parabens; Plant Roots; Sitosterols; Triterpenes; Vanillic Acid

2010
Studies on the chemical constituents from the stem and leaves of Tagetes erecta.
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:9

    To investigate the chemical constituents of the stem and leaves of Tagetes erecta.. The materials extracted with ethanol were first purified with D101 resin and then separated by repeated silica gel column chromatography as well as recrystallization to get single compounds. The chemical structures of the compounds were elucidated on the basis of physicochemical properties, spectroscopic analysis and comparing with standard sample and literatures.. Six compounds were identified as 4'-methoxy-eupatolitin-3-O-glucoside (I), kaempferitrin (II), rutin (III), beta-sitosterol (IV), daucosterol (V) and gallic acid (VI).. Compounds I, II, III are isolated from the plant for the first time; the compounds IV, V, VI are isolated from the stem and leaves of the plant for the first time.

    Topics: Ethanol; Gallic Acid; Kaempferols; Molecular Structure; Plant Leaves; Plant Stems; Resins, Synthetic; Rutin; Sitosterols; Tagetes

2010
[Study on the chemical constituents from fresh roots of Euphorbia fischeriana].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:9

    To study the chemical constituents in ethyl acetate fraction from the Euphorbia fischeriana.. The compounds were isolated by silica gel column chromatography and HPLC, and their structures were elucidated by means of spectral analyses.. Fourteen compounds were identified as 2,4-dihydroxy-6-methoxy-3-methylacetophenone (1), 12-deoxyphorbol-13-hexadecanoate (2), ethylgallate (3), esculetin (4), 2,4-dihydroxy-6-methoxy-acetophenone (5), 12-deoxyphorbol-13-acetate (6), 12-deoxyphorbol-13,20-diacetete (7), jolkinolide B (8), 17-hydroxyjolkinolide B (9), 17-hydroxy-jolkinolide A (10), langduin C (11), 3-methylp-hydroxybenzoic acid (12), methyl gallate (13), 3, 3'-diacetyl-pyridine-4,4'-dimethoxy-2, 2', 6, 6'-tetrahydroxydiphenylmethane (14).. Compounds 3, 5, 12, 13 are isolated from this plant for the first time.

    Topics: Acetophenones; Chromatography, Thin Layer; Euphorbia; Gallic Acid; Nitrates; Plant Roots; Plants, Medicinal; Salicylates; Sitosterols

2010
[Two new sesquiterpene lactones from the pericarp of Illicium macranthum].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2010, Volume: 45, Issue:3

    Silica gel column chromatography was used for the isolation and purification of the chemical constituents of the pericarp of Illicium macranthum. From dichloromethane-EtOAc (1:1) fraction and EtOAc fraction of the methanol extracts, eleven compounds were identified on the basis of chemical and spectral data. Two new compounds were elucidated to be 6-deoxyneomajucin (1) and 2-oxo-6-deoxyneomajucin (2), along with nine known compounds 6-deoxypseudoanisatin (3), pseudoanisatin (4), anisatin (5), pseudomajucin (6), protocatecheuic acid (7), shikimic acid (8), shikimic acid methylester (9), beta-sitosterol (10) and daucosterol (11). Compounds 1 and 2 are new majucin-type sesquiterpene lactones.

    Topics: Drugs, Chinese Herbal; Fruit; Illicium; Lactones; Magnetic Resonance Spectroscopy; Molecular Structure; Plants, Medicinal; Sesquiterpenes; Shikimic Acid; Sitosterols; Spiro Compounds

2010
[Studies on the chemical constituents from Cissus pteroclada].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:10

    To study the chemical constituents of Yao Medicine Cissus pteroclada.. The compounds were isolated and purified by column chromatography with silica gel, TLC and recrystallization. Their structures were elucidated on the basis of physicochemical properties and spectra analysis.. Six compounds were isolated and identified as beta-sitosterol (I), bergenin (II), 11-O-galloylbergenin (III), 11-O-(4-hydroxy benzoyl) bergenin (IV), gallic acid (V), daucosterol (VI).. Compounds III and NIV are obtained from the genus for the first time. All the compounds are isolated from this plant for the first time except the compound II.

    Topics: Benzopyrans; Cissus; Gallic Acid; Molecular Structure; Plant Stems; Plants, Medicinal; Sitosterols; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet

2010
[Studies on the chemical constituents of Toricellia angulata var. intermedia].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:11

    To study the chemical constituents of Toricellia angulata var. intermedia.. The constituents were isolated and purified by repeated column chromatography and their structures were elucidated by spectroscopic analysis.. Twelve compounds including beta-sitoterol (1), 7-hydroxy-3-ethylphthalide (2), 3beta-methoxy-stigmast-7-ene (3), stigmast-5-ene (4), trans-p-methylcinnamaldehyde (5), stigmate-7-en-3beta-ol (6), o. p-dimethoxybenzoicacid (7), beta-daucosterol (8), ursolicacid (9), stearic acid (10), docosanoic acid (11), palmitic acid (12) were isolated and identified from this plant.. All the compounds are isolated from the plant for the first time, compounds 3 -7, 10 -12 are isolated from this genus for the first time.

    Topics: beta Carotene; Cornaceae; Fatty Acids; Magnetic Resonance Spectroscopy; Molecular Structure; Palmitic Acid; Plants, Medicinal; Sitosterols; Stearic Acids

2010
[Studies on the chemical constituents of the root tube from Pteroxygonum giraldii].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2010, Volume: 33, Issue:11

    To study the chemical constituents of the root tube from Pteroxygonum giraldii.. Column chromatography and spectral analysis were used to isolate and identify the constituents.. Ten compounds were isolated and identified as beta-sitosterol (I), beta-sitosterol glucoside (II), 4', 5,5', 7-tetrahydroxy-3'-methoxy-3'-O-alpha-L-arabinopyranosyl flavone (III), gallic acid (IV), myricetin (V), annulatin (VI), 5,5', 7-trihydroxy-2',3-dimethoxy-4'-O-beta-D-glucopyranosyl flavone (VII), 2', 5,5',7-tetrahydroxy -3-methoxy-4'-O-beta-D-glucopyranoside flavone (VIII), myricetin-3-O-alpha-L-rhamnopyranoside (IX) and myricetin-3,4'-dimethyl ether( X).. Compounds I, II, V, VIII and X are isolated from Pteroxygonum giraldii for the first time.

    Topics: Flavonoids; Gallic Acid; Molecular Structure; Plant Roots; Plants, Medicinal; Polygonaceae; Sitosterols

2010
Association of plasma phytosterol concentrations with incident coronary heart disease Data from the CORA study, a case-control study of coronary artery disease in women.
    Atherosclerosis, 2009, Volume: 203, Issue:1

    Phytosterols have been proposed to be atherogenic. This research investigates whether plasma concentrations of phytosterols correlate with the manifestation of coronary heart disease.. The CORA study compares clinical, biochemical, and lifestyle factors in consecutive pre- and postmenopausal women with incident coronary heart disease to those in age-matched population-based controls. Controls (n=231) had significantly higher plasma concentrations of the major phytosterol species than cases (n=186) (4.649mg/l vs. 4.092mg/l; p<0.001). Cases had a higher dietary intake of phytosterols, but the ratio of lathosterol over sitosterol did not significantly differ. Phytosterols correlated with cholesterol concentrations of LDL and HDL, the phytosterol-carrying lipoproteins. The age-adjusted odds ratio for the association of total phytosterols and risk of coronary heart disease was 0.69 per 5mg/dl (95% CI 0.46-0.99). After adjustment for LDL- and HDL-cholesterol the odds ratio approached 1 (0.89; 95% CI 0.61-1.30), which was reached after additional adjustment for major risk factors, particularly those reflecting the metabolic syndrome (1.05; 95% CI 0.64-1.97).. Healthy controls had higher unadjusted concentrations of plasma phytosterols, but the adjusted odds ratio for coronary heart disease did not point to an impact of plasma phytosterols on coronary heart disease.

    Topics: Adult; Aged; Aged, 80 and over; Case-Control Studies; Cholesterol; Coronary Artery Disease; Female; Humans; Metabolic Syndrome; Middle Aged; Odds Ratio; Phytosterols; Risk Factors; Sitosterols

2009
The relationships of cholesterol metabolism and plasma plant sterols with the severity of coronary artery disease.
    Journal of lipid research, 2009, Volume: 50, Issue:2

    Changes in the balance of cholesterol absorption and synthesis and moderately elevated plasma plant sterols have been suggested to be atherogenic. Measuring cholestanol, lathosterol, campesterol, and sitosterol, we investigated the relationships of cholesterol metabolism and plasma plant sterols with the severity of coronary artery disease (CAD) in 2,440 participants of the Ludwigshafen Risk and Cardiovascular health (LURIC) study. The coronary status was determined by angiography, and the severity of CAD was assessed by the Friesinger Score (FS). An increase in the ratio of cholestanol to cholesterol was associated with high FS (P = 0.006). In contrast, a high ratio of lathosterol to cholesterol went in parallel with low FS (P < 0.001). Whereas the campesterol to cholesterol ratio significantly correlated with the FS (P = 0.026), the relationship of the sitosterol to cholesterol ratio with the FS did not reach statistical significance in the whole group. Increased campesterol, sitosterol, and cholestanol to lathosterol ratios were associated high FS (P < 0.001). To conclude, there is a modest association of high cholesterol absorption and low cholesterol synthesis with an increased severity of CAD. An atherogenic role of plasma plant sterols themselves, however, seems unlikely in subjects without sitosterolaemia.

    Topics: Aged; Cholestanol; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Coronary Artery Disease; Female; Humans; Male; Middle Aged; Phytosterols; Radiography; Sitosterols

2009
Comparison of the immunomodulatory effects of the plant sterol beta-sitosterol to simvastatin in peripheral blood cells from multiple sclerosis patients.
    International immunopharmacology, 2009, Volume: 9, Issue:1

    Statins as hypocholesterolimic drugs have recently shown to have ant-inflammatory properties and thus are being assessed for the treatment of multiple sclerosis (MS). Dietary phytosterols such as beta-sitosterol (SIT) are also hypocholesterolemic compounds and from preliminary studies they appear to have also anti-inflammatory properties. In this communication, we report on studies to investigate the immunomodulatory effects of SIT on proliferation and release of key cytokines from peripheral blood mononuclear cells (PBMC) of MS patients. In PBMC of MS patients, 16 microM SIT had no effect on cell proliferation; however simvastatin (SV) at 10 and 20 microM reduced cell proliferation by as much as 60%. SIT (4 microM) reduced TNF-alpha release by 24% in PBMC of MS patients whereas 10 microM SV reduced TNF-alpha release by 94%. SIT reduced IL-12 release in MS patients at 4 and 16 microM by 27% and 30%, respectively. In healthy subjects, 16 microM SIT increased the anti-inflammatory cytokine IL-10 by 47% whereas 10 microM SV decreased IL-10 by 30%. In PBMC of MS patients, SIT had no effect on IL-10 release whereas 10 microM SV reduced IL-10 by 62%. SIT (4 microM) reduced IL-5 release by 47% in MS patients while 10 microM SV reduced IL-5 by 89%. The results show that SIT is effective in modulating the secretion of pro/anti-inflammatory cytokines and suggest a potential beneficial effect of SIT in MS management without the side effects associated with statin therapy.

    Topics: Adolescent; Adult; Aged; Blood Cells; Cell Proliferation; Cell Survival; Cytokines; Dose-Response Relationship, Drug; Female; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Immunologic Factors; Interleukin-10; Interleukin-12; Interleukin-5; Middle Aged; Multiple Sclerosis; Simvastatin; Sitosterols; Tumor Necrosis Factor-alpha; Young Adult

2009
Characterizing components of the Saw Palmetto Berry Extract (SPBE) on prostate cancer cell growth and traction.
    Biochemical and biophysical research communications, 2009, Feb-13, Volume: 379, Issue:3

    Saw Palmetto Berry Extract (SPBE) is applied for prostate health and treatment of urinary tract infections, nonbacterial prostitis and Benign Prostatic Hyperplasia (BPH) in man. An assumption is that SPBE affects tumor cell progression and migration in breast and prostate tissue. In this work, DU-145 cells were used to demonstrate that SPBE and its sterol components, beta-sitosterol and stigmasterol, inhibit prostate cancer growth by increasing p53 protein expression and also inhibit carcinoma development by decreasing p21 and p27 protein expression. In the presence of cholesterol, these features are not only reversed but increased significantly. The results show for the first time the potential of SPBE, beta-sitosterol and stigmasterol as potential anti-tumor agents. Since the protein p53 is also regarded as nuclear matrix protein facilitating actin cytoskeletal binding, 2D tractions were measured. The cell adhesion strength in the presence of SPBE, beta-sitosterol and cholesterol and the observation was that the increase in p53 expression triggered an increase in the intracellular force generation. The results suggest a dual function of p53 in cells.

    Topics: Cell Line, Tumor; Cell Proliferation; Cell Survival; Cyclin-Dependent Kinase Inhibitor p21; Cyclin-Dependent Kinase Inhibitor p27; Humans; Male; Plant Extracts; Prostatic Neoplasms; Serenoa; Sitosterols; Stigmasterol

2009
Oil and fatty acid diversity in genetically variable clones of Moringa oleifera from India.
    Journal of oleo science, 2009, Volume: 58, Issue:1

    The physico-chemical properties of oil from Moringa oleifera seeds from India were determined in the present study. The petroleum ether extracted oil ranged from 27.83 - 45.07% on kernel basis and 15.1-28.4% on whole seed basis in 20 different clones. Leaves and pods showed a good source of vitamin C. Oleic acid (C18:1) has been found to be the major fatty acid being 78.91-85.52% as compared to olive oil, which is considered to be richest source of oleic acid. All the clones from India did not show any presence of behenic acid (C 22:0). The oil was also found to contain high levels of beta-sitosterol ranged from 42.29-47.94% stigmasterol from 13.66-16.61%, campesterol from 12.53-16.63%. The gamma- and delta-tocopherol were found to be in the range of 128.0-146.95, 51.88-63.5 and 55.23-63.84 mg/kg, respectively.

    Topics: Ascorbic Acid; Cholesterol; Fatty Acids; gamma-Tocopherol; Genetic Variation; India; Moringa oleifera; Oleic Acid; Olive Oil; Phytosterols; Plant Oils; Seeds; Sitosterols; Stigmasterol; Tocopherols

2009
Plasma plant sterol levels do not reflect cholesterol absorption in children with Smith-Lemli-Opitz syndrome.
    The Journal of pediatrics, 2009, Volume: 154, Issue:4

    To test the hypothesis that there is a correlation between the ratio of plant sterols to cholesterol in plasma and dietary cholesterol absorption in children with Smith-Lemli-Opitz syndrome (SLOS), a cholesterol synthesis disorder.. We obtained measurements of cholesterol absorption with a direct radioisotope cholesterol absorption method during 9 visits of children with SLOS. We measured plasma sterols in 22 children with SLOS and 16 control children, and we measured dietary intake of cholesterol and sitosterol (n=11 SLOS).. The correlations of 2 plasma plant sterol ratios (sitosterol/cholesterol and campesterol/cholesterol) with direct cholesterol absorption measurement were poor (R= -0.33 and R= -0.25, respectively), significantly lower than the published correlation in adults (R=0.73; P< .02).. Although the ratios of plant sterols to cholesterol in plasma has been used as a surrogate for cholesterol absorption in adults and children, these ratios may not accurately reflect cholesterol absorption in children with SLOS. These ratios should not be used as a surrogate for cholesterol absorption in children without further validation.

    Topics: Adolescent; Adult; Biomarkers; Case-Control Studies; Child; Child, Preschool; Cholesterol, Dietary; Female; Humans; Infant; Intestinal Absorption; Male; Phytosterols; Sensitivity and Specificity; Sitosterols; Smith-Lemli-Opitz Syndrome

2009
Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis.
    Proceedings of the National Academy of Sciences of the United States of America, 2009, Jan-20, Volume: 106, Issue:3

    The differences between the biosynthesis of sterols in higher plants and yeast/mammals are believed to originate at the cyclization step of oxidosqualene, which is cyclized to cycloartenol in higher plants and lanosterol in yeast/mammals. Recently, lanosterol synthase genes were identified from dicotyledonous plant species including Arabidopsis, suggesting that higher plants possess dual biosynthetic pathways to phytosterols via lanosterol, and through cycloartenol. To identify the biosynthetic pathway to phytosterol via lanosterol, and to reveal the contributions to phytosterol biosynthesis via each cycloartenol and lanosterol, we performed feeding experiments by using [6-(13)C(2)H(3)]mevalonate with Arabidopsis seedlings. Applying (13)C-{(1)H}{(2)H} nuclear magnetic resonance (NMR) techniques, the elucidation of deuterium on C-19 behavior of phytosterol provided evidence that small amounts of phytosterol were biosynthesized via lanosterol. The levels of phytosterol increased on overexpression of LAS1, and phytosterols derived from lanosterol were not observed in a LAS1-knockout plant. This is direct evidence to indicate that the biosynthetic pathway for phytosterol via lanosterol exists in plant cells. We designate the biosynthetic pathway to phytosterols via lanosterol "the lanosterol pathway." LAS1 expression is reported to be induced by the application of jasmonate and is thought to have evolved from an ancestral cycloartenol synthase to a triterpenoid synthase, such as beta-amyrin synthase and lupeol synthase. Considering this background, the lanosterol pathway may contribute to the biosynthesis of not only phytosterols, but also steroids as secondary metabolites.

    Topics: Arabidopsis; Arabidopsis Proteins; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Intramolecular Transferases; Lanosterol; Mevalonic Acid; Phytosterols; Seedlings; Sitosterols; Triterpenes

2009
Unusual sterolic mixture, and 24-isopropylcholesterol, from the sponge Ciocalypta sp. reduce cholesterol uptake and basolateral secretion in Caco-2 cells.
    Journal of cellular biochemistry, 2009, Mar-01, Volume: 106, Issue:4

    An unusual sterolic mixture (82.3% of 24-isopropylated sterols) and its major component, 24-isopropylcholesterol, isolated from a marine sponge, Ciocalypta sp. (Halichondriidae), reduce cholesterol uptake, basolateral secretion and ACAT-2 mRNA expression and increase the expression of ABCA1 mRNA in Caco-2 cells. The decreases of cholesterol uptake and secretion induced by 24-isopropylcholesterol alone were more than that of both the sterolic mixture and beta-sitosterol. These data add a new sterol, 24-isopropylcholesterol, to sterols that may reduce intestinal cholesterol absorption.

    Topics: Animals; Caco-2 Cells; Cholesterol; Dehydrocholesterols; Humans; Intestinal Absorption; Porifera; RNA, Messenger; Sitosterols; Sterol O-Acyltransferase; Sterol O-Acyltransferase 2; Sterols

2009
Activated sludge versus aerated lagoon treatment of kraft mill effluents containing beta-sitosterol and stigmasterol.
    Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering, 2009, Volume: 44, Issue:4

    In the present study the performance of an activated sludge system (AS) and an aerated lagoon (AL) are compared for the treatment of kraft cellulose effluents. Both reactors were operated at organic loading rates (OLR) up to 9 g COD/L. d. The activated sludge system presented better performance at high OLR than the aerated lagoon with removal percentages of 57-67% and 95% of COD and BOD(5), respectively. The removal percentages of specific compounds were always slightly higher in the case of the AS than in the AL with exception of the total phenolic compounds which concentration increased in the former. Furthermore the analyzed fractions from the effluents indicated that in the AS the compounds were fully removed while in the case of the aerated lagoon were transformed into compound with low molecular weight P2 (5 kD < MW < 10 kD). In the case of the AS system the increase of the total phenolic compounds concentrations was corroborated with the increase of the fractions P2, P3 and P4. The studied phytosterol were removed from the effluent at concentrations up to 2 mg/L in percentages close to 100% mainly by adsorption in the case of the AL and by a combining adsorption and mainly degradation in the AS. The BOD(5) concentration in the effluent of both systems fulfilled the requirements of the Chilean regulations for effluent discharge indicating the feasibility of aerobic treatment of this kind of effluents.

    Topics: Air; Industrial Waste; Molecular Weight; Sewage; Sitosterols; Stigmasterol; Water Pollutants, Chemical

2009
Twenty-one year tracking of serum non-cholesterol sterols. The Cardiovascular Risk in Young Finns study.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2009, Volume: 19, Issue:8

    To show tracking of cholesterol metabolism, the ratios to cholesterol of e.g. serum cholestenol, desmosterol, and lathosterol, reflecting cholesterol synthesis, and cholestanol, campesterol, avenasterol and sitosterol, reflecting cholesterol absorption, were measured 21 years apart.. In random population samples initially comprising 12- (n=162), 15- (n=158), and 18-year-old (n=148) males participating in the Cardiovascular Risk in Young Finns Study, serum sterols and squalene were measured with gas-liquid chromatography in 1980 and 2001. Quartiles of cholestanol, indicating low to high cholesterol absorption, were defined from the cholestanol values in 1980. Serum cholesterol increased in the oldest age group only, but synthesis markers (except desmosterol) increased in all age groups after the follow-up (e.g. lathosterol, total population +47.3+/-2.6% (SE), P<0.001). Campesterol (+69.0+/-3.0%, P<0.001) and sitosterol increased, avenasterol was unchanged, and cholestanol decreased (-6.2+/-0.7%, P<0.001), respectively. The 1980 synthesis and absorption markers were interrelated with respective values 21 years later in all age groups and quartiles (e.g. lathosterol, total population 1980 vs. 2001 r=0.460, cholestanol 1980 vs. 2001 r=0.593, P<0.001 for both). Synthesis markers were highest in the first and lowest in the fourth quartile both in 1980 and 2001 (e.g. 2001, desmosterol, quartile 1, 99+/-9, quartile 4, 83+/-2 microg/mg of cholesterol, P<0.05).. Cholesterol metabolism is significantly tracked in adolescent males over the follow-up of 21 years. Thus, high cholesterol synthesis and low absorption characterize subjects with the lowest cholestanol quartile, while those with the highest quartile have low synthesis and high absorption in both adolescence and later in young adult life.

    Topics: Adolescent; Adult; Age Factors; Biomarkers; Body Mass Index; Cardiovascular Diseases; Child; Child, Preschool; Cholestanol; Cholesterol; Chromatography, Gas; Chromatography, Liquid; Desmosterol; Female; Finland; Follow-Up Studies; Humans; Intestinal Absorption; Male; Phytosterols; Population Surveillance; Registries; Risk Factors; Sitosterols; Time Factors

2009
Rapid screening and isolation of a fungus for sitosterol to androstenedione biotransformation.
    Applied biochemistry and biotechnology, 2009, Volume: 158, Issue:2

    Androstenedione (AD) is a steroid intermediate used in the pharmaceutical industry for the production of several important anabolic drugs. An important route for producing AD is by the microbial transformation of sterols. Microbes capable of efficiently transforming sterols to AD are few and newer strains need to be isolated. Conventional procedures for screening and isolation are time consuming. A new procedure was used for screening and isolation of fungal microorganisms capable of biotransformation of sitosterol to androstenedione. In this procedure, Basic Alignment Search Tool (BLAST) and Position-Specific Iterative BLAST were employed to obtain a parent set of candidate microorganisms. The parent set was reduced using heuristics and constraints to obtain a manageable number of microorganisms that may be tested experimentally. For this work, screening of the entire NCBI database yielded a parent set containing 64 microorganisms. Among these, only two microorganisms, Aspergillus oryzae and Aspergillus nidulans FGSC A4, qualified to the experimental stage. Sitosterol biotransformation experiments were carried out using A. oryzae and the production of AD in culture medium was confirmed.

    Topics: Androstenedione; Aspergillus nidulans; Aspergillus oryzae; Chromatography, Thin Layer; Computational Biology; Fungi; Molecular Structure; Sitosterols

2009
Missense mutation in Abcg5 in SHRSP rats does not accelerate intestinal absorption of plant sterols: comparison with Wistar rats.
    Bioscience, biotechnology, and biochemistry, 2009, Volume: 73, Issue:2

    Stroke-prone spontaneously hypertensive rats (SHRSP) deposit plant sterols in their bodies and have a mutation in ATP binding cassette transporter G5 (Abcg5). Lymphatic recovery rates of campesterol and sitosterol in SHRSP rats were comparable to those in Wistar rats, a strain that does not deposit plant sterols in the body and has no mutation in Abcg5. Higher absorption of stigmasterol and sitostanol was observed in SHRSP rats than in Wistar rats, but the differences between SHRSP and Wistar rats were quite small, because the absorbed amounts of these two sterols were much lower than those of campesterol and sitosterol. The in situ uptake of (3)H-sitosterol and (14)C-cholesterol solubilized in the bile salt micelle into intestinal mucosa was comparable between SHRSP and Wistar rats. These observations suggest that a mutation in Abcg5 does not greatly influence intestinal absorption of plant sterols in SHRSP rats, at least in comparison with Wistar rats.

    Topics: Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Cholesterol; Intestinal Absorption; Lipoproteins; Lymph; Male; Mutation, Missense; Phytosterols; Rats; Rats, Inbred SHR; Rats, Wistar; Sitosterols

2009
The targeting of the oxysterol-binding protein ORP3a to the endoplasmic reticulum relies on the plant VAP33 homolog PVA12.
    The Plant journal : for cell and molecular biology, 2009, Volume: 58, Issue:5

    In plants, sterols play fundamental roles as membrane constituents in the biosynthesis of steroid hormones, and act as precursors for cell wall deposition. Sterols are synthesized in the endoplasmic reticulum (ER), but mainly accumulate in the plasma membrane. How sterols are trafficked in plant cells is largely unknown. In non-plant systems, oxysterol-binding proteins have been involved in sterol trafficking and homeostasis. There are at least twelve homologs of oxysterol-binding proteins in the Arabidopsis genome, but the biology of these proteins remains for the most part obscure. Here, we report our analysis of the targeting requirements and the sterol-binding properties of a small Arabidopsis oxysterol-binding protein, ORP3a. We have determined that ORP3a is a bona fide sterol-binding protein with sitosterol-binding properties. Live-cell imaging analyses revealed that ORP3a is localized at the ER, and that binding to this organelle depends on a direct interaction with PVA12, a member of the largely uncharacterized VAP33 family of plant proteins. Molecular modeling analyses and site-directed mutagenesis led to the identification of a novel protein domain that is responsible for the PVA12-ORP3a interaction. Disruption of the integrity of this domain caused redistribution of ORP3a to the Golgi apparatus, suggesting that ORP3a may cycle between the ER and the Golgi. These results represent new insights into the biology of sterol-binding proteins in plant cells, and elucidate a hitherto unknown relationship between members of oxysterol-binding protein and VAP33 families of plant proteins in the early plant secretory pathway.

    Topics: Amino Acid Sequence; Arabidopsis; Arabidopsis Proteins; Cloning, Molecular; Endoplasmic Reticulum; Golgi Apparatus; Models, Molecular; Molecular Sequence Data; Mutagenesis, Site-Directed; Protein Transport; Receptors, Steroid; Recombinant Proteins; Sitosterols

2009
Biological activity of secondary metabolites from Peltostigma guatemalense.
    Natural product research, 2009, Volume: 23, Issue:4

    Leaves and wood of Peltostigma guatemalense, a novel species of the family Rutaceae, yielded a total of 14 secondary metabolites, i.e. methyl p-hydroxy benzoate, phenylacetic acid, beta-sitosterol, lupeol, syringaresinol, scopoletin, gardenin B (1), and seven alkaloids: gamma-fagarine (2), skimmianine (3), kokusaginine (4), 7-O-isopentenyl-gamma-fagarine (5), anhydro-evoxine (6), evoxine (7) and 4-methoxy-1-methyl-quinolin-2-one (8). The compounds have been identified by spectroscopic methods. Antibacterial and antimalarial in vitro activity of the isolated compounds were also determined. Methyl p-hydroxy benzoate and quinolone (8) were the most effective on Plasmodium falciparium strains.

    Topics: Alkaloids; Animals; Anti-Bacterial Agents; Antimalarials; Bacteria; Furans; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Extracts; Plasmodium falciparum; Quinolines; Rutaceae; Sitosterols; Triterpenes

2009
CYP710A genes encoding sterol C22-desaturase in Physcomitrella patens as molecular evidence for the evolutionary conservation of a sterol biosynthetic pathway in plants.
    Planta, 2009, Volume: 229, Issue:6

    We have characterized cytochromes P450, CYP710A13, and CYP710A14, as the sterol C22-desaturase in the moss Physcomitrella patens. GC-MS analyses demonstrated that P. patens accumulated stigmasterol as the major sterol (56-60% of total sterol) and sitosterol to a lesser extent (8-12%); this sterol profile contrasts with those in higher plants accumulating stigmasterol as a minor component. Recombinant CYP710A13 and CYP710A14 proteins prepared using a baculovirus/insect cell system exhibited the C22-desaturase activity with beta-sitosterol to produce stigmasterol, while campesterol and 24-epi-campesterol were not accepted as the substrates. The K(m) values for beta-sitosterol of CYP710A13 (1.0 +/- 0.043 microM) and CYP710A14 (2.1 +/- 0.17 microM) were at comparable levels of those reported with higher plant CYP710A proteins. In Arabidopsis T87 cells over-expressing CYP710A14, stigmasterol contents reached a level 20- to 72-fold higher than those in the basal level of T87 cells, confirming the C22-desaturase activity of this P450 enzyme. The occurrence of the end-products together with the enzymes involved in the last step of the pathway substantiated the presence of an entire sterol biosynthetic pathway in P. patens, providing evidence for the conservation of the sterol biosynthetic pathway through the evolutionary process of land plants.

    Topics: Amino Acid Sequence; Animals; Biosynthetic Pathways; Bryopsida; Cell Line; Conserved Sequence; Cytochrome P-450 Enzyme System; Electrophoresis, Polyacrylamide Gel; Evolution, Molecular; Gas Chromatography-Mass Spectrometry; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Isoenzymes; Kinetics; Molecular Sequence Data; Molecular Structure; Oxidoreductases; Phytosterols; Plants; Recombinant Proteins; Reverse Transcriptase Polymerase Chain Reaction; Sequence Homology, Amino Acid; Sitosterols; Spodoptera; Stigmasterol

2009
Sitosterol bioconversion with resting cells in liquid polymer based systems.
    Bioresource technology, 2009, Volume: 100, Issue:17

    The use of a biocompatible water-immiscible organic phase as a substrate and product pool has been acknowledged as an effective tool to overcome the low volumetric productivity of aqueous bioconversion systems involving hydrophobic compounds. The growing environmental and public health awareness is nevertheless leading to restrictions in the use of organic solvents in industrial processes, in order to render these more environmentally friendly. Different approaches are hence being assessed for the design of alternative bioconversion media, involving the use of supercritical fluids, ionic liquids and natural oils and liquid polymers, among others. In this work, the use of liquid polymers as key components in the bioconversion media for a multi-step microbial bioconversion was assessed. The model system used was the selective cleavage of the side-chain of beta-sitosterol by free resting cells of Mycobacterium sp. NRRL B-3805, a well established industrial multi-enzymatic process involving the use of nine catabolic enzymes in a fourteen-step metabolic pathway. High product yields were obtained when silicone B oil was used as substrate carrier/product pool, both in single oil and in oil:buffer two liquid phase system.

    Topics: Androstadienes; Buffers; Mycobacterium; Polymers; Sitosterols; Solubility; Time Factors

2009
Lack of genoprotective effect of phytosterols and conjugated linoleic acids on Caco-2 cells.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2009, Volume: 47, Issue:8

    Much interest has focused on the cholesterol-lowering effects of phytosterols (plant sterols) but limited data suggests they may also possess anti-carcinogenic activity. Conjugated linoleic acids (CLA), sourced from meat and dairy products of ruminant animals, has also received considerable attention as a potential anti-cancer agent. Therefore, the aims of this project were to (i) examine the effects of phytosterols and CLA on the viability and growth of human intestinal Caco-2 cells and (ii) determine their potential genoprotective (comet assay), COX-2 modulatory (ELISA) and apoptotic (Hoechst staining) activities. Caco-2 cells were supplemented with the phytosterols campesterol, beta-sitosterol, or beta-sitostanol, or a CLA mixture, or individual CLA isomers (c10t12-CLA, t9t11-CLA) for 48 h. The three phytosterols, at the highest levels tested, were found to reduce both the viability and growth of Caco-2 cells while CLA exhibited isomer-specific effects. None of the phytosterols protected against DNA damage. At a concentration of 25 microM, both c10t12-CLA and t9t11-CLA enhanced (P<0.05) oxidant-induced, but not mutagen-induced, DNA damage. Neither the phytosterols nor CLA induced apoptosis or modulated COX-2 production. In conclusion, campesterol, beta-sitosterol, beta-sitostanol, c10t12-CLA, and t9t11-CLA were not toxic to Caco-2 cells, at the lower levels tested, and did not exhibit potential anti-carcinogenic activity.

    Topics: Caco-2 Cells; Cell Membrane; Cell Survival; Cholesterol; Comet Assay; Cyclooxygenase 2; DNA Damage; Enzyme-Linked Immunosorbent Assay; Humans; Hydrogen Peroxide; L-Lactate Dehydrogenase; Linoleic Acid; Methylnitronitrosoguanidine; Mutagens; Phytosterols; Protective Agents; Sitosterols

2009
Iridoid glucosides from leaves and stem barks of Parkia javanica.
    Journal of Asian natural products research, 2009, Volume: 11, Issue:3

    Two new iridoid glucosides, javanicosides A (1) and B (2) along with the known compounds, ursolic acid and beta-sitosterol were isolated from the leaf and stem bark of Parkia javanica and the structures were established on the basis of detailed spectroscopic analysis (MS, 1D, and 2D NMR experiments). The new compounds were identified as 8-O-p-hydroxybenzoyl-6'-O-p-coumaroyl-mussaenosidic acid (1) and 7-O-E-3,4-dimethoxycinnamoyl-6'-O-beta-D-glucopyranosylloganic acid (2).

    Topics: Fabaceae; India; Iridoid Glucosides; Iridoids; Mimosa; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Bark; Plant Leaves; Plant Stems; Sitosterols

2009
[Analysis of phytosterol contents in food plant materials and Chinese traditional medicines].
    Wei sheng yan jiu = Journal of hygiene research, 2009, Volume: 38, Issue:2

    To analyze the phytosterol content in food plant materials and Chinese traditional herbal medicines commonly used in China.. 18 kinds of food plant materials and 32 kinds of Chinese traditional herbal medicines, which were commonly used in functional food, were chosen as samples. The contents of beta-sitosterol, campesterol, stigmasterol, beta-sitostanol were analyzed by GC methods and the percent of each ingredient were calculated.. The contents of phytosterols in 18 kinds of food plant materials were from 14.8 mg/100 g to 208.3 mg/100 g, while the content of phytosterols in 32 Chinese traditional herbal medicines were from 9.4 mg/100 g to 280.3 mg/100 g. In most samples, beta-sitosterol is the largest part of total phytosterol.. Phytosterols were existed in 50 kinds of food plant materials and Chinese traditional herbal medicines commonly used in functional food, maybe phytosterol is an important functional ingredient in some plant materials.

    Topics: Cholesterol; Chromatography, Gas; Drugs, Chinese Herbal; Phytosterols; Plants, Medicinal; Sitosterols; Stigmasterol; Vegetables

2009
A new rearranged abietane diterpene and other constituents from Clerodendrum philipinum.
    Natural product communications, 2009, Volume: 4, Issue:3

    From the methanolic extract of the roots of Clerodendrum philipinum, a new rearranged abietane diterpene (1) and eight known compounds were isolated by various chromatography methods. Their structures were identified by means of spectroscopic methods, including 1D- and 2D-NMR, as 17(15-->16),18(4-->3)-bisabeo-11,12,14,16-tetrahydroxy-3,5,8,11,13,15-abietahexaen-7-one (1), binankadsurin A, clerodenoside A, martynoside, acteoside, isoacteoside, astragalin, p3-sitosterol, and daucosterol. Binankadsurin A was found for the first time from a Clerodendrum species.

    Topics: Abietanes; Chromatography; Clerodendrum; Glucosides; Kaempferols; Lignans; Magnetic Resonance Spectroscopy; Methanol; Molecular Structure; Phenols; Sitosterols

2009
Characterization of 24-well microtiter plate reactors for a complex multistep bioconversion: from sitosterol to androstenedione.
    Journal of biotechnology, 2009, May-20, Volume: 141, Issue:3-4

    Microtiter plates are commonly used for screening purposes and one-pot biotransformations. Nonetheless, there are scarce systematic studies focused on the application of these systems to complex whole cell multistep bioconversions, which typically require prolonged incubation periods, and on the evaluation of the reproducibility of data generated in such shaken miniature reactors. The present study aims to contribute to fill in this gap. The model system selected was the side-chain cleavage of beta-sitosterol performed by whole cells of Mycobacterium sp. NRRL B-3805 in 24-well microtiter plates. Reproducibility of the data was assessed within the 24 wells of the microtiter plate as well as matching different plates placed in different positions on the shaking platform. Results show the suitability of microtiter plates with proper oxygen and pH monitoring capabilities to carry out complex multistep bioconversion using relatively slow growing bacteria. Reproducibility levels are in the range of an interval of confidence of 92%.

    Topics: Analysis of Variance; Androstenedione; Bioreactors; Biosensing Techniques; Cell Culture Techniques; Cell Proliferation; Equipment Design; Hydrogen-Ion Concentration; Mechanical Phenomena; Mycobacterium; Oxygen Consumption; Reproducibility of Results; Sitosterols

2009
The regulation of inflammatory cytokine secretion in macrophage cell line by the chemical constituents of Rhus sylvestris.
    Bioorganic & medicinal chemistry letters, 2009, Jul-01, Volume: 19, Issue:13

    In our preliminary screening study on the anti-inflammatory activity, eight triterpenes, one sterol, and one chalcone were isolated from the CH(2)Cl(2)-soluble extract of the stems and leaves of Rhus sylvestris Siebold and Zucc (Anacardiaceae). On the basis of their spectroscopic data, these compounds were identified as 10alpha-cucurbitadienol (1), glut-5-en-3-ol (2), beta-amyrin acetate (3), beta-amyrin (4) and lupeol (5), cycloart-24-en-3-one (6), cycloart-25-en-3,24-dione (7), 24-hydroxycycloart-25-en-3-one (8), beta-sitosterol (9), and 2'-hydroxy-4,4'-dimethoxychalcone (10). All of them were isolated from this plant for the first. Furthermore, the compounds in non-cytotoxic concentrations (0-1.0microM) were tested for their ability to block inflammatory cytokine secretion in the presence of LPS in the murine RAW264.7 macrophage cell line. Among the compounds that were tested, compounds 8 and 9 reduced the LPS-induced secretion of IL-6, as well as TNF-alpha, in a mouse RAW264.7 macrophage cell line. Moreover, compounds 2, 3, 7, and 10 specifically diminished only the secretion of TNF-alpha even in 0.01microM concentrations. It is thus suggested that they are potential therapeutics of TNF-alpha-related diseases and conditions, such as transplant rejection, type II diabetes, and atherosclerosis.

    Topics: Anacardiaceae; Animals; Anti-Inflammatory Agents; Cell Line; Cytokines; Humans; Interleukin-6; Lipopolysaccharides; Macrophages; Mice; Plant Leaves; Sitosterols; Triterpenes; Tumor Necrosis Factor-alpha

2009
Beta-sitosterol inhibits cell growth and induces apoptosis in SGC-7901 human stomach cancer cells.
    Journal of agricultural and food chemistry, 2009, Jun-24, Volume: 57, Issue:12

    Beta-sitosterol is an important phytosterol found in plant food. It has been shown to have antiproliferative effects on cancers of the colon, breast, and prostate, but its effect on stomach cancer cells in vitro is unknown. Proliferation, cytotoxicity, and apoptosis in SGC-7901 human stomach cancer cells were examined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, clone formation, lactate dehydrogenase (LDH) leakage assay, acridine orange (AO)/ethidium bromide (EB) double staining, 4',6-diamidine-2'-phenylindole dihydrochloride (DAPI) staining, comet assay, and Western blotting. The results showed that beta-sitosterol suppresses the proliferation and induces the cell cytotoxicity of SGC-7901 stomach cancer cells in a time- and dose-dependent manner. Cells treated with different concentrations of beta-sitosterol also showed changes typical of apoptosis: morphological changes, DNA damage, increased expression of pro-caspase-3 and bax (p < 0.05), and activation of pro-caspase-3 and suppression of bcl-2 expression (p < 0.05). This study therefore revealed that beta-sitosterol significantly inhibits the growth and induces the apoptosis of SGC-7901 human stomach cancer cells in vitro. The decrease of the bcl-2/bax ratio and DNA damage may be the critical mechanisms of apoptosis induced by beta-sitosterol in SGC-7901 human stomach cancer cells.

    Topics: Apoptosis; Cell Proliferation; Down-Regulation; Gene Expression Regulation, Neoplastic; Humans; Sitosterols; Stomach Neoplasms

2009
Effects of oxidation on the hydrolysis by cholesterol esterase of sitosteryl esters as compared to a cholesteryl ester.
    Steroids, 2009, Volume: 74, Issue:10-11

    Phytosteryl esters (PE) are used as ingredients in functional food to decrease plasma concentration of low density lipoprotein-cholesterol (LDL-C). Effective impairment of cholesterol absorption by PE suggests that these esters are hydrolyzed by the pancreatic cholesterol esterase (CEase, EC 3.1.1.13) and the liberated sterol may interfere with cholesterol reducing its intestinal absorption. PE-enriched foods are marketed for cooking purposes, and temperature is one of the most important factors leading to the formation of oxidation products. Very little is known about the outcome of PE oxides during the digestive process. A new analytical method based on mass spectrometric detection directly after enzymatic reaction was developed to determine in vitro the activity of CEase on PE and their oxides present in functional food. Using this method, we identified a new inhibitor of CEase: sitosteryl 9,10-dihydroxystearate, which behaves as a non-competitive inhibitor of the hydrolysis of cholesteryl oleate and sitosteryl oleate.

    Topics: Animals; Cholesterol Esters; Esters; Hydrolysis; Hypolipidemic Agents; Oleic Acid; Oxidation-Reduction; Oxides; Sitosterols; Stearates; Sterol Esterase; Swine

2009
Cytotoxic components of Pereskia bleo (Kunth) DC. (Cactaceae) leaves.
    Molecules (Basel, Switzerland), 2009, May-06, Volume: 14, Issue:5

    Dihydroactinidiolide (1) and a mixture of sterols [campesterol (2), stigmasterol (3) and beta-sitosterol (4)], together with the previously isolated individual compounds beta-sitosterol (4), 2,4-di-tert-butylphenol (5), alpha-tocopherol (6), phytol (7) were isolated from the active ethyl acetate fraction of Pereskia bleo (Kunth) DC. (Cactaceae) leaves. Cytotoxic activities of the above mentioned compounds against five human carcinoma cell lines, namely the human nasopharyngeal epidermoid carcinoma cell line (KB), human cervical carcinoma cell line (CasKi), human colon carcinoma cell line (HCT 116), human hormone-dependent breast carcinoma cell line (MCF7) and human lung carcinoma cell line (A549); and non-cancer human fibroblast cell line (MRC-5) were investigated. Compound 5 possessed very remarkable cytotoxic activity against KB cells, with an IC(50 )value of 0.81microg/mL. This is the first report on the cytotoxic activities of the compounds isolated from Pereskia bleo.

    Topics: alpha-Tocopherol; Antineoplastic Agents, Phytogenic; Cactaceae; Cell Line, Tumor; Cholesterol; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Phenols; Phytol; Phytosterols; Plant Leaves; Sitosterols; Stigmasterol

2009
Chemical constituents from the leaves of Machilus zuihoensis Hayata var. mushaensis (Lu) Y.C. Liu.
    Natural product research, 2009, Volume: 23, Issue:9

    One new lignan, machilolin-A (1), was isolated from the leaves of Machilus zuihoensis Hayata var. mushaensis (Lu) Y. C. Liu (Lauraceae), together with three known compounds, vanillin (2), beta-sitosterol (3) and stigmasterol (4). The structure of 1 was elucidated based on chemical analysis and spectral methods (IR, 1D and 2D NMR, HR-FAB-MS, EI-MS).

    Topics: Benzaldehydes; Lauraceae; Lignans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Leaves; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Spectrometry, Mass, Fast Atom Bombardment; Stigmasterol

2009
Mutiniside, new antioxidant phenolic glucoside from Abutilon muticum.
    Journal of Asian natural products research, 2009, Volume: 11, Issue:5

    Mutiniside (1), new phenolic glucoside, and the flavonoidal glucoside cephacoside (2) have been isolated from the n-BuOH soluble fraction, along with lupeol (3), beta-sitosterol (4), stigmasterol (5), methyl-4-hydroxybenzoate (6), taraxacin (7), ursolic acid (8), and beta-sitosterol-3-O-beta-D-glucopyranoside (9), have been isolated from the EtOAc soluble fraction of Abutilon muticum. Compounds 2-9 are reported for the first time from this species. Compound 1 showed significant antioxidant activity while moderate inhibitory activity was observed against the enzyme lipoxygenase.

    Topics: Antioxidants; Biphenyl Compounds; Free Radical Scavengers; Glucosides; Lipoxygenase Inhibitors; Malvaceae; Molecular Structure; Pakistan; Phenols; Picrates; Plants, Medicinal; Sitosterols

2009
[Studies on the chemical constituents of Phellodendron chinense].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:2

    To isolate and identify chemical constituents from Phellodendron chinense.. Chemical constituents were isolated by silica gel and Sephadex LH-20 column chromatography. The structures of the isolated compounds were determined by spectral means.. Ten compounds were isolated and identified as berberine (1), caffeic acid ethyl ester (2), iso-vanillin (3), ferulic acid (4), (+/-)-5,5'-dimethoxylariciresinol (5), Methyl beta-orsellinate (6), gamma-fagirine (7), (+/-)-Lyoniresinol (8), beta-sitosterol (9), stigmasterine (10).. Compounds 2-6 are isolated and identified from this genus for the first time.

    Topics: Berberine; Caffeic Acids; Coumaric Acids; Phellodendron; Plant Bark; Plants, Medicinal; Resorcinols; Sitosterols

2009
New methylethers of cordatolides from Calophyllum cordato-oblongum and their synthesis.
    Natural product research, 2009, Volume: 23, Issue:10

    Twigs of Calophyllum cordato-oblongum Thw. have been shown to contain cordatolide A-OMe, cordatolide B-OMe, cordatolide C-OMe, cordatolide A, cordatolide B, oblongulide, cordatooblongic acid, friedelin, canophyllol, and sitosterol. Methylation of cordatolide B and the attempted methylation of cordatolide A under acidic conditions gave cordatolide B-OMe and 11,12-anhydrocordatolide. Cordatolide A-OMe, cordatolide C-OMe and 11,12-anhydrocordatolide are new compounds.

    Topics: Anti-HIV Agents; Calophyllum; Coumarins; Magnetic Resonance Spectroscopy; Methyl Ethers; Methylation; Molecular Structure; Plant Extracts; Sitosterols; Triterpenes

2009
Analysis of beta-sitosterol in seeds and nuts using pressurized liquid extraction and liquid chromatography.
    Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 2009, Volume: 25, Issue:6

    Pressurized liquid extraction (PLE) has been used for the extraction of beta-sitosterol from food samples. In the present work, extractions were performed by mixing ground samples with Hydromatrix celite with methanol at 50 degrees C and 110 bar, using two 5-min cycles. After extraction, beta-sitosterol was analyzed directly by liquid chromatography with diode array detection. The extraction recovery was 92%, with relative standard deviations of 3.7% for intra-day precision and 4.3% for inter-day precision. The presence of beta-sitosterol was confirmed by gas chromatography-mass spectrometry. The proposed method was validated and applied successfully to the determination of free beta-sitosterol in seed and nut samples (almonds, pistachios, peanuts, and sunflower seeds).

    Topics: Chemical Fractionation; Chromatography, Liquid; Gas Chromatography-Mass Spectrometry; Nuts; Pressure; Reproducibility of Results; Seeds; Sitosterols

2009
Phytosterols accumulation in the seeds of Linum usitatissimum L.
    Plant physiology and biochemistry : PPB, 2009, Volume: 47, Issue:10

    A comparative study was performed to determine the free sterols content and composition during the development of three varieties of linseed (H52, O116 and P129). Seed samples were collected at regular intervals from 7 to 60 days after flowering (DAF). Ten compounds were identified: cholesterol, campesterol, brassicasterol, stigmasterol, beta-sitosterol, Delta5-avenasterol, cycloartenol; 24-methylene cycloartanol, obtusifoliol, citrostadienol. The maximum level of 4-desmethylsterols (1,515 mg/100g oil) was reached at 7 DAF in P129 variety. H52 had the highest level of 4-4 dimethylsterols (355 mg/100g oil) at 28 DAF. The greatest amount of 4-monomethylsterols (35 mg/100g oil) was detected in H52 at 14 DAF. During linseed development, beta sitosterol (830 mg/100g oil) was the major 4-desmethylsterols, followed by campesterol (564 mg/100g oil) and stigmasterol (265 mg/100g oil). Some of these compounds followed nearly the same accumulation pattern during linseed maturation.

    Topics: Cholestadienols; Cholesterol; Chromatography, Thin Layer; Flax; Flowers; Gas Chromatography-Mass Spectrometry; Phytosterols; Seeds; Sitosterols; Species Specificity; Stigmasterol; Time Factors; Triterpenes

2009
Isopimarane diterpenoids from Aeollanthus rydingianus and their antimicrobial activity.
    Phytochemistry, 2009, Volume: 70, Issue:9

    Four acyloxy-isopimarane derivatives along with two known isopimarane diterpenoids, the flavone cirsimaritin and the sterols beta-sitosterol and stigmasterol were isolated from the aerial parts of Aeollanthus rydingianus. The structures of the compounds were established on the basis of spectroscopic analysis and chemical evidence. The isolated substances were screened for antimicrobial activity against Gram-positive and Gram-negative bacteria and a yeast strain. 19-Acetoxy-7,15-isopimaradien-3beta-ol and 7,15-isopimaradien-19-ol showed minimum inhibitory concentration (MIC) values of 3.90-15.62 microg/ml for Staphylococcus aureus and of 7.81microg/ml for Enterococcus hirae.

    Topics: Anti-Bacterial Agents; Diterpenes; Enterococcus; Gram-Negative Bacteria; Gram-Positive Bacteria; Lamiaceae; Microbial Sensitivity Tests; Molecular Structure; Plants, Medicinal; Sitosterols; Staphylococcus aureus; Vancomycin

2009
A new sesquiterpene from the roots of Vladimiria souliei.
    Natural product communications, 2009, Volume: 4, Issue:6

    A new sesquiterpene lactone, 1beta-hydroxy-4alpha-methoxy-5alphaH, 7alphaH, 6betaH-eudesm-11(13)-en-6, 12-olide 1, and three known compounds, 4alpha-hydroxy-5alphaH, 7alphaH, 6betaH-eudesm-11(13)-en-6, 12-olide 2, mokko lactone 3, beta-sitosterol 4 were isolated from the roots of Vladimiria souliei. Their structures were elucidated by spectroscopic methods.

    Topics: 4-Butyrolactone; Molecular Structure; Plant Roots; Plants, Medicinal; Sesquiterpenes; Sitosterols

2009
[Chemical constituents from Neo-Taraxacum siphonathum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2009, Volume: 34, Issue:8

    To study the chemical constituents from the antioxidant fraction of Neo-Taraxacum siphonathum.. Various chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated on the basis of chemical evidence and spectral analysis.. Ten compounds were isolated and identified from Neo-T. siphonathum, caffeic acid (1), chlorogenic acid (2), quercetin (3), luteolin (4), quercetin-3-O-beta-D-glucopyranoside (5), quercetin-3-O-alpha-D-arabinofuranoside (6), quercetin-3-O-alpha-D-arabinopyranoside (7), luteolin-7-O-beta-D-glucopyranoside (8), beta-sitosterol (9) and daucosterol (10).. Compounds 1-10 were isolated from this plant for the first time.

    Topics: Caffeic Acids; Chlorogenic Acid; Glucosides; Luteolin; Magnetic Resonance Spectroscopy; Quercetin; Sitosterols; Taraxacum

2009
[Studies on chemical constituents of herbs of Oxytropis microphylla].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2009, Volume: 34, Issue:8

    To study the chemical constituents of Oxytropis microphylla.. The compounds were isolated and purified by various column chromatographic techniques and their structures were elucidated on the basis of spectral analysis (EI-MS, 1H-NMR, 13C-NMR).. Eight compounds were isolated and identified as kaempferol (1), baicalein (2), 5-hydroxy-7, 8, 4'-trimethoxyflavone (3), stigmasterol (4), stigmast-4-en-3beta-ol (5), beta-sitosterol (6), lupenol (7), dehydrocostus lactone (8).. All compounds were isolated for the first time from this plant, compounds 2, 3, 5, and 8 were isolated for the first time from this genus.

    Topics: Chromatography, High Pressure Liquid; Flavanones; Flavonoids; Kaempferols; Lactones; Oxytropis; Sesquiterpenes; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Stigmasterol; Triterpenes

2009
[Chemical study on petroleum ether portion of Sarcandra hainanensis].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2009, Volume: 34, Issue:8

    To study the chemical constituents in the whole plants of Sarcandra hainanensis.. The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data.. Nine compounds, palmitic acid (1), icosanoic acid (2), beta-sitosterol (3), octadecanoic (4), acidchrysophanol (5), emodin (6), 2', 3'-dihydroxy-4', 6'-dimethoxychalcone (7), 2'-hydroxy4', 6'-dimethoxychalcone (8), cardamonin (9) were isolated and identified.. Compounds 1-9 were obtained from this plant for the first time. Compounds 2, 5-9 were isolated from family Chloranthaceae for the first time.

    Topics: Alkanes; Chalcones; Eicosanoids; Emodin; Magnetic Resonance Spectroscopy; Magnoliopsida; Palmitic Acid; Sitosterols; Stearic Acids

2009
[Studies on chemical constituents of Daphne genkwa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:4

    To study the chemical constituents of the flower buds of Daphne genkwa.. The constituents of petroleum ether and ethyl acetate-soluble portions were isolated and purified by means of chromatography, then they were identified by their physico-chemical characteristics and spectral features.. Ten compounds were isolated and identified as octacosane (1), dotriacontane (2), beta-sitosterol (3), 4', 7-dimethoxy-5-hydroxyflovone (4), aurantiamide acetate (5), genkwanin (6), luteolin (7), apigenin (8), 3'-hydroxygenkwanin (9) and daphnoretin (10).. Compound 1 and 2 are isolated from this plant for the first time.

    Topics: Alkanes; Apigenin; Coumarins; Daphne; Diacetyl; Dipeptides; Flavones; Flowers; Luteolin; Molecular Structure; Plants, Medicinal; Sitosterols

2009
[Studies on chemical constituents of Ligularia altaica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:4

    To study the chemical constituents of Lighularia altaica.. Various chromatographic techniques were used to isolate and purify the chemical compounds, their structure were elucidated by means of mass, physico-chemical properties and NMR spectral data.. Nine compounds were obtained as: lupeol (1), oleanolic acid (2), 3beta, 16beta-dihydroxy-12-oleanen-28-al (3), ergosterol peroxide (4), stigmasta-7-en-ol (5), 11-hydroxy-10,11-dihydro-euparin (6), 5-hydroxybenzofuran-2(3H) -one- (7), except for beta-sitosterol (8) and daucostrol (9).. Compounds 3 - 7 are isolated for the first time from this genus, the other compounds are obtained from this plant for the first time.

    Topics: Asteraceae; Ergosterol; Oleanolic Acid; Pentacyclic Triterpenes; Plants, Medicinal; Rhizome; Sitosterols; Solvents; Spectrometry, Mass, Electrospray Ionization

2009
[Studies on chemical constituents from leaves and stems of Aconitum coreanum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2009, Volume: 34, Issue:10

    To study the chemical constituents in the leaves and stems of Aconitum coreanum.. The isolation and purification of chemical constituents were carried out on silica gel and polyamide column chromatographic. Their structures were identified by physico-chemical properties and spectral analysis.. Five compounds were obtained and their structures were identified as guan-fu base I (1), guan-fu base R (2), beta-sitosterol (3), D-mannitol (4), daucosterol (5).. Compound 2 is a new compound. Compounds 1 and 3, 4 are isolated from the leaves and stems of A. coreanum for the first time.

    Topics: Aconitum; Molecular Structure; Plant Leaves; Plant Stems; Sitosterols

2009
[Study on chemical constituents from roots of Saussurea lappa].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2009, Volume: 34, Issue:10

    To study the chemical constituents in roots of Saussurea lappa.. Isolation and purification were carried out by silica gel, Sephadex LH-20 and RP-18 column chromatography. The chemical structures of constituents were elucidated on the basis of spectral data.. Eleven compounds were isolated and identified as: 5,7-dihydroxy-2-methylchromone (1), p-hydroxybenzaldehyde (2), 3,5-dimethoxy-4-hydroxy-benzaldehyde (3), 3,5-dimethoxy-4-hydroxy-acetophenone (4), ethyl 2-pyrrolidinone-5(s)-carboxylate (5), 5-hydroxymethyl-furaldehyde (6), palmitic acid (7), succinic acid (8), glucose (9), daucosterol (10), beta-sitosterol (11).. Compounds 1, 2, 4, 5, 7, 9 were isolated from the genus Saussurea for the first time.

    Topics: Benzaldehydes; Palmitic Acid; Plant Roots; Pyrrolidinones; Saussurea; Sitosterols

2009
[Studies on chemical constituents from bee-collected rape pollen].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2009, Volume: 34, Issue:10

    To study the chemical constituents of the bee-collected rape pollen.. The compounds were isolated by column chromatography on silica gel; Sephadex LH-20 and C18. Their structures were elucidated on the basis of spectral analysis.. Nine compounds were isolated from the bee-collected rape pollen and the structures of them were kaemferol-3-O-beta-D-glucosyl-(2-->1)-beta-D-glucoside (1), kaemferol-3,4'-di-O-beta-D-glucoside (2), quercetin-3-O-beta-D-glucosyl-(2-->1)-beta-D-glucoside (3), nicotinic acid (4), nicotinamide (5), trans-p-coumaric acid-4-O-beta-D-glucopyranoside (6), kaemferol (7), beta-sitosterol (8) and 5-hydroxymethylfurfural (9).. Compounds 1-6 were isolated from the bee-collected rape pollen for the first time.

    Topics: Animals; Bees; Brassica napus; Coumaric Acids; Dextrans; Glucosides; Molecular Structure; Plant Extracts; Pollen; Propionates; Sitosterols

2009
The potential of Pleurotus-treated olive mill solid waste as cattle feed.
    Bioresource technology, 2009, Volume: 100, Issue:24

    The aims of the current study were to follow: (1) the capability of the edible mushroom Pleurotus ostreatus to degrade cell wall components and soluble phenols of the olive mill solid waste (OMSW), and improve it for ruminant nutrition (2) the fate of oil and the lipid-soluble compounds tocopherols, squalene and beta-sitosterol in the fermented OMSW. A significant decrease in oil and lipid-soluble compounds with a concomitant shift in the fatty acid profile and degradation of soluble phenols took place already after 14 d. The utilization of lipids by the fungus shifted the degradation of the structural carbohydrates to a later stage, and significantly reduced the metabolizable energy of the OMSW. We propose that edible fungi with reduced lipase activity would preserve the energy and health promoting ingredients of the oil, and force the fungus to degrade structural carbohydrates, thus improving its digestibility.

    Topics: alpha-Tocopherol; Animal Feed; Animals; Biodegradation, Environmental; Cattle; Fatty Acids; gamma-Tocopherol; Industrial Waste; Oils; Olea; Pleurotus; Refuse Disposal; Sitosterols; Solubility; Squalene; Time Factors

2009
Chemical composition of the stem bark and leaves of Ficus pandurata Hance.
    Natural product research, 2009, Volume: 23, Issue:13

    A new compound, 3-O-alpha-L-arabinopyranosyl-4-hydroxybenzoic acid (13), in addition to 16 newly reported compounds: alpha-amyrin acetate (1), beta-amyrone (2), 3beta-acetoxy-20-taraxasten-22-one (3), alpha-amyrin (4), ceryl alcohol (5), stigmasterol (6), beta-sitosterol (7), 2alpha,3alpha-dihydroxy-lup-20(29)-en-28-oate (8), ursolic acid (9), beta-sitosterol-3-O-glucosoide (10), protocatechuic acid (11), betulinic acid (12), quercetin (14), quercetin-3-O-beta-D-glucoside (15), kampferol-3-O-beta-neohesperidoside (16) and rutin (17) were isolated from the stem bark and leaves of Ficus pandurata (Hance) cultivated in Egypt. Identification of these compounds has been established by physical, chemical and spectral data (UV, IR, MS, (1)H- and (13)C-NMR), as well as comparison with authentic samples.

    Topics: Betulinic Acid; Ficus; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Pentacyclic Triterpenes; Plant Bark; Plant Leaves; Sitosterols; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Stigmasterol; Triterpenes; Ursolic Acid

2009
A new fungicidal lactone from Xylocarpus granatum (Meliaceae).
    Natural product research, 2009, Volume: 23, Issue:14

    A new lactone was isolated from the leaves of Xylocarpus granatum, along with three known compounds: triacontanol, beta-sitosterol and kaempferol-3-O-beta-D-glucoside. Its structure was elucidated as 3-(1-hydroxyethyl)-4,4-dimethyl-4-butyrolactone (1) by infrared, (1)H and (13)C NMR and ESI-MS data. At a concentration of 20 microg mL(-1), the new lactone gave a 67.4% inhibition rate against wheat powdery mildew.

    Topics: Ascomycota; Fatty Alcohols; Fungicides, Industrial; Glucosides; Magnetic Resonance Spectroscopy; Meliaceae; Microbial Sensitivity Tests; Molecular Structure; Mycelium; Plant Diseases; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Infrared; Triticum

2009
Oxidation of cholesterol and beta-sitosterol and prevention by natural antioxidants.
    Journal of agricultural and food chemistry, 2009, Oct-14, Volume: 57, Issue:19

    Consumption of cholesterol oxidation products (COPs) is a growing health concern, but little is known about the intake of beta-sitosterol oxidation products (SOPs). The present study was performed (i) to compare the oxidative stability of cholesterol with that of beta-sitosterol; (ii) to investigate the oxidative pattern of cholesterol and beta-sitosterol in lard, corn oil, and olive oil; and (iii) to examine the effectiveness of green tea catechins (GTC), alpha-tocopherol, and quercetin in prevention of cholesterol and beta-sitosterol oxidation compared with butylated hydroxytoluene (BHT). Results showed both cholesterol and beta-sitosterol were thermally unstable with 75% of cholesterol and beta-sitosterol being oxidized at 180 degrees C for 2 h. The oxidation behavior of beta-sitosterol was similar to that of cholesterol in terms of oxidative rate and oxidation products. The major COPs produced were 7-ketocholesterol, 7alpha-hydroxycholesterol, 7beta-hydroxycholesterol 5,6alpha-epoxycholesterol, and 5,6beta-epoxycholesterol, whereas the major SOPs were 7-ketositosterol, 7alpha-hydroxysitosterol, 7beta-hydroxysitosterol, 5,6alpha-epoxysitosterol, and 5,6beta-epoxysitosterol. Under the same experimental conditions, both cholesterol and beta-sitosterol were oxidized more slowly in corn oil, lard, and olive oil, attributable to the unsaponified antioxidants present in these fat and oils. GTC, alpha-tocopherol, and quercetin were more effective than BHT in preventing the oxidation of cholesterol and beta-sitosterol.

    Topics: alpha-Tocopherol; Antioxidants; Butylated Hydroxytoluene; Cholesterol; Chromatography, Gas; Corn Oil; Dietary Fats; Drug Stability; Kinetics; Olive Oil; Oxidation-Reduction; Plant Oils; Quercetin; Sitosterols; Tea

2009
[Studies on the chemical constituents of the leaves of Polygonum multiflorum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:6

    To study the chemical constituents of the leaves of Polygonum multiflorum.. The chemical constituents were extracted with water and separated by manifold chromatography technique, and their structures were determined by spectral analysis.. Eleven compounds were isolated and identified as physcion (I), emodin (II), noreugenin (III), apigenin (IV), hyperoside (V), rutin (VI), vitexin (VII), 2,3,5 ,4'-tetrahydroxy-stibene-2-O-beta-D-glucoside (VIII), beta-amyrin (IX), beta-sitosterol (X), daucosterol( XI).. Among these compounds, I - IV, VI - XI are isolated from the leaves of Polygonum multiflorum for the first time.

    Topics: Apigenin; Emodin; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plant Leaves; Plants, Medicinal; Polygonum; Rutin; Sitosterols

2009
Cloning, functional expression and phylogenetic analysis of plant sterol 24C-methyltransferases involved in sitosterol biosynthesis.
    Phytochemistry, 2009, Volume: 70, Issue:17-18

    Sterol 24C-methyltransferases (SMTs) constitute a group of sequence-related proteins that catalyze the distinct patterns of 24-alkyl sterols that occur throughout nature. Two SMT cDNAs (SMT2-1 and SMT2-2) were cloned by homology based PCR methods from young leaves of Glycine max (soybean) and the corresponding enzymes were expressed functionally in Escherichia coli. The full-length cDNA for SMT2-1 and SMT2-2 have open reading frames of 1086 bp and 1092 bp, respectively, and encode proteins of 361 and 363 residues with a calculated molecular mass of 40.3 and 40.4 kDa, respectively. The substrate preference of the two isoforms was similar yet they differed from SMT1; kinetically SMT2-1 and SMT2-2 generated k(cat) values for the optimal substrate 24(28)methylene lophenol of 0.8 min(-1) and 1.34 min(-1), respectively, compared to the activity of SMT1 that generated a k(cat) for the optimal substrate cycloartenol of 0.6 min(-1). SMT2-2 was purified to homogeneity and the subunit organization shown to be tetrameric in similar fashion to other cloned SMTs. Analysis of the accumulated products catalyzed by the recombinant enzymes demonstrated that soybean SMT2-1 and SMT2-2 operate transalkylation activities analogous to the soybean plant SMT1. Metabolite analyses correlated with transcript profiling of the three SMT isoforms during soybean maturation clearly demonstrated that SMT isoform expression determines specific C24-methyl to C24-ethyl ratios to flowering whereas with seed development there is a disconnection such that the SMT transcript levels decrease against an increase in sterol content; generally SMT2-2 is expressed more than SMT2-1 or SMT1. These observations suggest that the genes that encode SMT1 and SMT2 in sitosterol biosynthesis may have undergone divergent evolution. In support of this proposition, the genomic organization for SMT1 of fungi and protozoa align very closely with one another and to those of the plant SMT2; both sets of SMTs lack introns. Unexpectedly, the SMT1 from Glycine max and other embryophytes of diverse origin possess disparate intron-exon characteristics that can be shown relates back to the algae. Our results suggest that the order of SMT1 appearing before SMT2 in phytosterol synthesis arose recently in plant evolution in response to duplication of a more primitive SMT gene likely to have been bifunctional and catalytically promiscuous.

    Topics: Amino Acid Sequence; DNA, Complementary; Eukaryota; Evolution, Molecular; Exons; Flowers; Fungi; Gene Expression; Genes, Plant; Glycine max; Introns; Methyltransferases; Molecular Sequence Data; Phylogeny; Plant Leaves; Protein Isoforms; Seeds; Sequence Alignment; Sitosterols; Soybean Proteins; Substrate Specificity

2009
Effect of the solvent type and temperature on phytosterol contents and compositions of wheat straw, bran, and germ extracts.
    Journal of agricultural and food chemistry, 2009, Nov-25, Volume: 57, Issue:22

    Wheat fractions, such as bran, germ, and straw, are rich in a number of health beneficial bioactive compounds. However, they have not been exploited to their full capacity for value-added product development. This study examines the potential of recovering phytosterol (PS)-enriched extracts from wheat germ, bran, and straw. The main objective of the study was to evaluate the effect of solvent type and temperature on PS content and composition in straw, bran, and germ extracts. Petroleum ether, chloroform, n-hexane, and ethanol were used as solvents. A pressurized solvent extraction system was used for extraction of wheat fractions. Germ extracts had the highest total PS content followed by straw and bran extracts. Beta-sitosterol, campesterol, and stigmasterol were the main PSs in all of the extracts. Ethanol extraction resulted in the lowest total PS recovery from germ. Solvent type had a significant effect on PS composition in straw extracts. beta-Sitosterol was the most abundant PS in straw hexane extracts (74% of total PS). Petroleum ether, chloroform, and ethanol extracted more stigmasterol than beta-sitosterol from straw. This study demonstrated that the solvent type and temperature had significant effects on both PS content and composition of extracts collected from wheat fractions. Because of the complex nature of the agricultural materials, solvent selection and process optimization need to be based on experimental data. Pressurized solvent extraction is a useful technique to screen complex biological materials for their composition and to determine processing conditions to be optimized.

    Topics: Alkanes; Chloroform; Dietary Fiber; Ethanol; Hexanes; Phytosterols; Plant Extracts; Pressure; Seeds; Sitosterols; Solvents; Temperature; Triticum

2009
Dietary phytosterols and phytostanols alter the expression of sterol-regulatory genes in SHRSP and WKY inbred rats.
    Annals of nutrition & metabolism, 2009, Volume: 55, Issue:4

    We elucidated the molecular mechanism(s) underlying sterol trafficking by investigating alterations in gene expression in response to increased retention of dietary phytosterols and phytostanols in stroke-prone spontaneously hypertensive (SHRSP) and normotensive Wistar Kyoto (WKY) inbred rats.. SHRSP and WKY inbred rats were fed a control diet or a diet supplemented with phytosterols or phytostanols (2 g/kg diet).. Intake of phytosterols and phytostanols increased their incorporation in plasma, red blood cells, liver, aorta and kidney, but decreased cholesterol levels in liver and aorta in both rat strains. Phytosterol intake up-regulated mRNA expression of intestinal Npc1l1 and Abcg8, and hepatic Abcg5, Abca1, Cyp27a1 and Hmgcr. Phytostanol intake up-regulated Npc1l1 and Srebp2, but down-regulated Abcg5 mRNA expression in small intestine. Phytostanols also up-regulated Abca1 expression in SHRSP rats, but down-regulated Abca1 expression in WKY inbred rats. Compared to phytosterols, dietary phytostanols reduced phytosterol levels in plasma, red blood cells, and kidney, as well as altered mRNA levels of hepatic Abca1,Cyp27a1, and Hmgcr and intestinal Abcg5/8, Hmgcr and Srebp2.. Altered expression of multiple sterol-regulatory genes may contribute to the incorporation and cholesterol-lowering actions of phytosterols and phytostanols. Phytosterols and phytostanols may act through different mechanism(s) on cholesterol and phytosterol/phytostanol trafficking.

    Topics: Animals; Anticholesteremic Agents; Cholestadienols; Cholesterol; Gene Expression Regulation; Hypolipidemic Agents; Jejunum; Liver; Male; Organ Specificity; Phytosterols; Rats; Rats, Inbred SHR; Rats, Inbred WKY; RNA, Messenger; Sitosterols; Sterols

2009
[Studies on the chemical constituents of Epimedium brevicornum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:7

    To study the chemical constituents of Epimedium breviconum.. Compounds were purificated with various chromatographic techniques such as silica vacuum liquid chromatography and Sephadex LH-20 column chromatography. Their structures were elucidated by physico-chemical methods and spectral analysis.. Ten compounds were obtained and indentified as (7R, 8S) 4,9-dihydroxyl-3,3'-dimethyoxyl-7, 8-dihydrobenzofunan-1'-propanolneolignan-9'-O-alpha-L-rhamnopyranoside (1), (7R, 8S, 8' R) 4, 4', 8', 9-tetrahydroxyl-3, 3'-dimethyoxyl-7, 9'-monoepoxylignan (2), (+)-cycloolivil (3), (3, 5, 7, 4')-tetrahydroxyl-8-isopentene group flavonoids-3-O-alpha-L-rhamnopyranoside (4), beta-sitosterol (5), p-hydroxybenzaldehyde (6), succinic acid (7) and p-hydroxyphenethyl (8).. Compound 1 is isolated from this genus for the first time. Compounds 2,3,5 -8 are isolated from the plant for the first time.

    Topics: 2-Hydroxyphenethylamine; Benzaldehydes; Epimedium; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Monosaccharides; Phenols; Plant Leaves; Plants, Medicinal; Sitosterols; Succinic Acid

2009
[Study on the chemical constituents of the fruit handles from Schizandra chinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:7

    To study the chemical constituents of the fruit handles from Schizandra chinensis.. Compounds from the 85% ethanol extracts were isolated by silica gel, Sephadex LH-20, recrystal, etc., and their structures were identified by the spectral analysis and chemical evidence.. Eight compounds were isolated and identified as wuweizisu C (I), ganwuweizic acid(II), beta-sitosterol(III), gomisin A(IV), schizandrin(V), daucosterol(VI), wuweizisu A(VII), gamma-schizandrin (VIII).. Compounds I - VIII are isolated from the fruit handles of Schizandra chinensis for the first time.

    Topics: Chromatography, Thin Layer; Cyclooctanes; Dioxoles; Fruit; Lignans; Magnetic Resonance Spectroscopy; Plants, Medicinal; Polycyclic Compounds; Schisandra; Sitosterols

2009
[Study on the constituents of petroleum ether fraction of Buxus microphylla].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:7

    To study the chemical constituents from the petroleum ether fraction of Buxus microphylla.. The petroleum ether fraction of Buxus microphylla was isolated and identified by silica gel column chromatography. And the anticancer activity of different chemical constituents was measured by MTT reduction test.. Eight compounds were isolated and identified as lupeol (1), butulin (3), beta-sitosterol (4), stigmasterol (5), dibutyl phthalate (6), 3beta, 30-dihydroxy-lup-20 (29) ene (7), daucosterol (8). Compound 7 inhibited KB cells' proliferation in a dose-dependent manner.. Compounds 2 - 5, 7, 8 are isolated from this genus for the first time. Compound 7 has certainly anticancer effects.

    Topics: Buxus; Chromatography, Thin Layer; Dibutyl Phthalate; Ethers; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Stigmasterol

2009
Chemometric approach to validating faecal sterols as source tracer for faecal contamination in water.
    Water research, 2009, Volume: 43, Issue:20

    Faecal sterols detection is a promising method for identifying sources of faecal pollution. In this study, faecal contamination in water samples from point source (sewage treatment plants, chicken farms, quail farms and horse stables) was extracted using the solid phase extraction (SPE) technique. Faecal sterols (coprostanol, cholesterol, stigmasterol, beta-sitosterol and stigmastanol) were selected as parameters to differentiate the source of faecal pollution. The results indicated that coprostanol, cholesterol and beta-sitosterol were the most significant parameters that can be used as source tracers for faecal contamination. Chemometric techniques, such as cluster analysis, principal component analysis and discriminant analysis were applied to the data set on faecal contamination in water from various pollution sources in order to validate the faecal sterols' profiles. Cluster analysis generated three clusters: coprostanol was in cluster 1, cholesterol and beta-sitosterol formed cluster 2, while cluster 3 contained stigmasterol and stigmastanol. Discriminant analysis suggested that coprostanol, cholesterol and beta-sitosterol were the most significant parameters to discriminate between the faecal pollution source. The use of chemometric techniques provides useful and promising indicators in tracing the source of faecal contamination.

    Topics: Cholestanol; Cholesterol; Environmental Monitoring; Feces; Sitosterols; Solid Phase Extraction; Sterols; Stigmasterol; Water Pollutants

2009
Bioactive azafluorenone alkaloids from Polyalthia debilis (Pierre) Finet & Gagnep.
    Molecules (Basel, Switzerland), 2009, Nov-03, Volume: 14, Issue:11

    This study investigated bioactive extracts of Polyalthia debilis (Annonaceae) with antimicrobial, antimalarial and cytotoxic activities. Extensive chromatographic isolations provided azafluorenone alkaloids; onychine (1) and 7-methoxyonychine (2) together with a mixture of beta-sitosterol and stigmasterol. The two alkaloids were isolated from the P. debilis for the first time. Isolated fractions containing a mixture of triterpenoids (C7, C8 and C9) exhibited the most potent antimicrobial activity against many bacterial strains with minimum inhibitory concentration of 64 microg/mL. Fractions with antimalarial and cytotoxic activities were also observed. The findings suggest the potential use of P. debilis in medicinal applications.

    Topics: Alkaloids; Anti-Infective Agents; Antimalarials; Cell Line; Cell Line, Tumor; Cell Survival; Flavanones; Humans; Microbial Sensitivity Tests; Molecular Structure; Plant Extracts; Plasmodium falciparum; Polyalthia; Pyridones; Sitosterols; Stigmasterol; Triterpenes

2009
[Studies on chemical constituents of fructus broussonetiae].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:8

    To study the chemical constituents of Fructus Broussonetiae.. Column chromatography with silic gel was employed to isolate and purify the 80% alcohol extract of Fructus Broussonetia, and the constituents were identified by spectral methods.. Six compounds were isolated from 80% ethanol extract. Their structures were identified as Isoterihanine (1), Chelerythrine (2), Trillin (3), Sucrose (4), beta-sitosterol (5) and Fucosterol (6).. These compounds are isolated from Fructus Broussonetiae for the first time.

    Topics: Benzophenanthridines; Broussonetia; Fruit; Molecular Structure; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet; Stigmasterol; Sucrose

2009
[Studies on the chemical constituents of Dryopteris fragrans].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:8

    To study the chemical constituents of Dryopteris fragrans.. The constituents of CHCl3-soluble portion and ethyl acetate-soluble portion from the alcohol extract were isolated and purified by means of chromatography. All the compounds were identified by their physical characteristics and spectral features.. Five compounds were isolated and identified as beta-sitosterol (I), rutin (II), quercetin (III), quercetin-3-O-beta-D-pyranglucoside (IV) and 5,7-dihydroxy-2-hydroxymethyl chromone (V).. Compounds II - V are isolated from this plant for the first time.

    Topics: Acetates; Dryopteris; Ethanol; Magnetic Resonance Spectroscopy; Molecular Structure; Plants, Medicinal; Quercetin; Rutin; Sitosterols

2009
Missense mutation of Abcg5 in stroke-prone spontaneously hypertensive rats does not influence lymphatic sitosterol absorption regardless of the dose: comparison with Wistar rats.
    Bioscience, biotechnology, and biochemistry, 2009, Volume: 73, Issue:12

    The lymphatic recovery of radiolabeled sitosterol administered in various amounts to the stomach was almost the same between stroke-prone spontaneously hypertensive rats (SHRSPs), a strain having a missense mutation in ATP binding cassette transporter g5 (Abcg5), and Wistar rats, a normal strain. The results suggest that the mutation of Abcg5 in SHRSPs, compared with Wistar rats, did not influence the ability for intestinal sitosterol absorption regardless of the dose.

    Topics: Absorption; Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Dose-Response Relationship, Drug; Gastric Mucosa; Hypertension; Lipoproteins; Lymphatic System; Male; Mutation, Missense; Rats; Rats, Inbred SHR; Rats, Wistar; Sitosterols; Stroke

2009
[Studies on the chemical constituents from Euphorbia chrysocoma].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:9

    To study the chemical constituents from the aerial part of Euphorbia chrysocoma.. All compounds were isolated and purified by many methods, including siliga gel and reversed phase RP-18 column chromatographies, preparative thin layer chromatography, Sephadex LH-20, and recrystallization. Their structures were mainly elucidated by ESI-MS and NMR spectra and their physical characters.. Six compounds were isolated from the petroleum ether section from 75% ethanol extraction of the material. Their structures were identified as taraxerol (1), epitaraxerol (2), beta-sistosterol (3), beta-sitostenone (4), jolkinolide E (5), and sesamin (6).. Compounds 1, 2, 4, 5, and 6 are isolated from this plant for the first time.

    Topics: Dioxoles; Diterpenes; Euphorbia; Lignans; Molecular Structure; Oleanolic Acid; Plant Components, Aerial; Plants, Medicinal; Sitosterols

2009
[Studies on the chemical constituents of ethyl acetate extraction from Reineckea carnea].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:9

    To study the chemical constituents of Reineckea carnea.. The compounds were isolated by extraction, silica gel and reversed phase silica gel column chromatography. The structures were identified by various spectroscopic methods including 1D and 2D-NMR spectrum, MS, IR, etc.. Six compounds were isolated and identified as beta-sitosterol (1), isorhodeasapogenin (2), isorhodeasapogenin (3), (25S)-1beta,3beta,4beta-trihydroxyspirotan-5beta-yl-O-beta-D-glucopyranoside (4), kitigenin-5-O-beta-D-glucopyranoside (5) and nicotianoside B (6).. Compounds 4, 6 are obtained from this plant for the first time.

    Topics: Acetates; Drugs, Chinese Herbal; Glucosides; Liliaceae; Magnetic Resonance Spectroscopy; Plants, Medicinal; Rhizome; Saponins; Sitosterols; Spectrophotometry, Infrared; Steroids

2009
[Study on the chemical constituents from Clematis brevicaudata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:10

    To study the chemical constituents from Clematis brevicaudata.. The compounds were isolated by column chromatography and their structures were elucidated through spectroscopic analysis (NMR).. Eight compounds were isolated and identified as: palmitic acid (1), 1-docosanol (2), pentacosanoic acid-2', 3'-dihydroxypropyl ester (3), beta-sitosterol (4), daucosterol (5), a mixture of the trans-p-coumarate of the n-alkanols (6), 3,4-dihydroxy-trans coumatate ethyl ester (7), syringaresinol-O-D-glucopyranoside (8).. All these compounds are obtained from Clematis brevicaudata for the first time.

    Topics: Clematis; Drugs, Chinese Herbal; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Palmitic Acid; Plants, Medicinal; Sitosterols

2009
[Study on chemical constituents of tress of Toona ciliata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:10

    To study the chemical constituents of the tress of Toona ciliata.. The compounds were isolated by many kinds of chromatography methods and identified on the basis of physico-chemical characters and spectroscopic analysis.. Seven compounds were obtained from the petrol and chloroform extracts of the tress of Toona ciliata, and their structures were identified as 3-Acetoxy-17-furan-3-yl-1-hydroxy-1, 4, 4, 10, 13-pentamethyl-12-oxo-tetradecahydro-16, 20-dioxa-cyclopropa [14, 15] cyclopenta [alpha] phenanthrene-7-carboxylic acid methyl ester (I), beta-sitosterol (II), stigmasterol (III), n-C35H72 (IV), palmitinic acid (V), n-C20H42 (VI), 3-(3-Propyl-[1,1',3',1"]tercyclohexan-3"-yl)-propan-1-ol (VII).. Compounds I, IV, VI, VII are isolated from this plant for the first time and compound I is a new compound.

    Topics: Meliaceae; Molecular Structure; Palmitic Acid; Plant Extracts; Plant Leaves; Plants, Medicinal; Sitosterols; Stigmasterol

2009
Triterpenoids from the roots of Pterospermum heterophyllum Hance.
    Journal of Asian natural products research, 2009, Volume: 11, Issue:7

    Two new triterpenoids taraxer-14-ene-1alpha,3beta-diol (1) and 3beta-hydroxytaraxer-14-ene-1-one (2), together with the known triterpenes taraxerol (3), betulin (4), betulinic acid (5), sumaresinolic acid (6), and 5-hydroxy-2-methoxy-1,4-naphthoquinone (7), 5,7-dihydroxy-6,8-dimethylchromone (8), alpha-monpalmitin (9), palmitic acid (10), 6beta-hydroxystigmast-4-en-3-one (11), beta-sitostero1 (12), have been isolated from the petroleum ether fraction of the ethanolic extract of Pterospermum heterophyllum. Their structures were established by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-8 were evaluated against several human cancer cell lines. Compound 1 showed in vitro selective cytotoxicity against human lung cancer cell lines (A549) with an IC(50) value of 1.22 microM. Compound 7 showed significant cytotoxicity against the A549, HCT-8, Bel7402, BGC-823, and A2780 cancer cell lines with IC(50) values of 0.21, 0.55, 0.40, 0.59, and 0.34 microM, respectively. However, the other compounds were inactive (IC(50)>10 microM).

    Topics: Antineoplastic Agents, Phytogenic; Betulinic Acid; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Female; Humans; Malvaceae; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Palmitic Acid; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Stereoisomerism; Terpenes; Triterpenes

2009
A moderate intake of phytosterols from habitual diet affects cholesterol metabolism.
    Journal of physiology and biochemistry, 2009, Volume: 65, Issue:4

    Cholesterol metabolism homeostasis is the result of a balance between synthesis, degradation and intestinal absorption. It is well established that intestinal cholesterol absorption efficiency can be modified by the intake of phytosterol-enriched food and, therefore, have a serum cholesterol-lowering effect. Recent epidemiological and clinical studies have shown that presence of phytosterols at normal diet levels could also be effective on lowering total and LDL serum cholesterol since they affect whole-body cholesterol metabolism even at those moderate doses. The aim of this study was to analyze the effect of the levels of the naturally-occurring phytosterols in the diet on cholesterol metabolism parameters. In order to do that a group of 99 healthy volunteers was studied for their dietary habits and surrogate markers of cholesterol synthesis and absorption. The mean daily dietary intake of phytosterols, measured by a food semiquantitative frequency questionnaire, was found to be 494 mg being beta-sitosterol the major contributor to it. Subjects were classified into tertiles according to their total phytosterol intake and comparisons were done between subgroups. No statistical differences were observed for surrogate markers of intestinal cholesterol absorption, but a significant increase in the cholesterol synthesis surrogate marker lathosterol-to-cholesterol ratio associated to highest dietary phytosterol intake was observed. Regardless of this, only a non significant trend toward a less atherogenic lipid profile was observed in the upper tertile. In conclusion, the intake of moderate amounts of phytosterols naturally present in habitual diet may affect cholesterol metabolism and specially the rate of cholesterol synthesis as estimated by the surrogate marker lathosterol-to-cholesterol ratio in serum.

    Topics: Absorption; Adult; Aged; Anthropometry; Body Mass Index; Cholesterol; Diet; Female; Homeostasis; Humans; Male; Middle Aged; Models, Biological; Phytosterols; Sitosterols

2009
[Studies on the chemical constituents of Rumex crispus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:12

    To study the chemical constituents of Rumex crispus.. Compounds were isolated and purified repeatedly by silica gel, Sephadex gel and ODS C18 column chromatographies, and structure identifications of compounds were carried out by physical, chemical methods and spectral data.. Fifteen compounds were obtained from the petroleum ether and ethyl acetate fractions of R. crispus, and were identified as beta-sitosterol(1), hexadecanoic acid(2), hexadecanoic-2,3-dihydroxy propyleste(3), chrysophanol(4), physcion(5), emodin(6), chrysophanol-8-O-beta-D-glucopyranoside(7), physcion-8-O-beta-D-glucopyranoside(8), emodin-8O-beta-D-glucopyranoside(9), gallic acid(10), (+)-catechin(11), kaempferol(12), quercetin(13), kaempferol-3-O-alpha-L-rhamnopyranoside(14), quercetin-3-O-alpha-L-rhamnopyranoside(15).. Compounds 3,8-12,14 and 15 are obtained from R. crispus for the first time.

    Topics: Catechin; Emodin; Gallic Acid; Glycosides; Kaempferols; Magnetic Resonance Spectroscopy; Monosaccharides; Plants, Medicinal; Quercetin; Rumex; Sitosterols; Spectrophotometry, Infrared

2009
[Studies on the chemical constituents from Daphne tangutica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2009, Volume: 32, Issue:12

    To research the chemical constituents from Daphne tangutica.. Column chromatography with silica gel, ODS-C18, Sephadex LH-20 and re-crystallization were employed to isolate and purify the constituents. According to physical and chemical properties and spectral data to identify the structure of compounds.. Eight compounds were isolated and identified as palmitic acid (1), laurostearic acid(2), beta-sitosterol(3), 7-methoxy-8-hydroxycumarin(4), daphnetin(5), genkwanin(6), hydroxygenkwanin(7), p-hydroxybenzoic acid(8).. Compounds 1,2,7 and 8 are isolated from Daphne tangutica for the first time.

    Topics: Daphne; Flavones; Flavonoids; Magnetic Resonance Spectroscopy; Palmitic Acid; Parabens; Plant Bark; Plants, Medicinal; Sitosterols

2009
Do plant sterol concentrations correlate with coronary artery disease in type 1 diabetes? A report from the Pittsburgh Epidemiology of Diabetes Complications Study.
    Journal of diabetes, 2009, Volume: 1, Issue:2

    It has been suggested that plant sterol absorption is increased in type 1 diabetes mellitus (T1DM) and that this may relate to the increased cardiovascular risk seen in T1DM. The cardiovascular benefit of lowering low-density lipoprotein-cholesterol with statin medication has also been shown to be influenced by plant sterol absorption.. The relationship between sterol concentrations, coronary artery disease (CAD), and the use of statin medications in T1DM was compared between participants with CAD (Minnesota codes 1.1, 1.2, 1.3, 4.1-4.3, 5.1-5.3, and 7.1; n = 82), from the Pittsburgh Epidemiology of Diabetes Complications (EDC) study, and those without (n = 213). Serum sterol concentrations reflecting cholesterol absorption (β-sitosterol and campesterol) and synthesis (desmosterol and lathosterol) were assayed and analyzed by gas chromatography and were expressed as a ratio of total cholesterol (×10(3)).. No differences were observed in markers of cholesterol absorption between individuals with and without CAD. In patients with CAD, significantly lower levels were observed for both sterol markers reflecting cholesterol synthesis compared with individuals without CAD [desmosterol: 0.34 vs 0.42, respectively (P = 0.003); lathosterol 0.47 vs 0.54, respectively (P = 0.019)]. Further stratification by statin medication use revealed significantly lower levels of synthesis-reflecting sterols in individuals taking statin medication, particularly those with CAD.. Although previous reports suggest that higher levels of cholesterol absorption in T1DM potentially increase cardiovascular risk in this population, the present data suggest no differences in cholesterol absorption between T1DM individuals with and without CAD.

    Topics: Adult; Cholesterol; Cholesterol, LDL; Coronary Artery Disease; Desmosterol; Diabetes Mellitus, Type 1; Female; Humans; Male; Middle Aged; Phytosterols; Sitosterols

2009
[Triterpenoids and steroids from Excoecaria agallocha].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:4

    To study the chemical constituents of Excoecaria agallocha L.. The constituents were isolated and purified by repeated column chromatography and their structures were elucidated by spectroscopic analysis.. Six triterpenoids including taraxerone (1), beta-amyrin acetate (2), 3beta-[(2E,4E)-6-oxo-decadienoyloxy]-olean-12-ene (3), taraxerol (4), acetylaleuritolic acid (5), and cycloart-22-ene-3beta, 25-diol (6), and three steroids including beta-sitostenone (7), (24R)-24-ethylcholesta-4,22-dien-3-one (8), and beta-sitosterol (9) were isolated and identified from the stems and twigs of the mangrove plant E. agallocha.. Compounds 5-8 were isolated from E. agallocha for the first time.

    Topics: Euphorbiaceae; Magnetic Resonance Spectroscopy; Oleanolic Acid; Sitosterols; Steroids; Triterpenes

2008
[Studies on chemical constituents of Heliciopsis lobata II].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:4

    To study the constituents of the leaves of Heliciopsis lobata.. Compounds were isolated by column chromatography on silica gel, neutral aluminum oxide and Sephadex LH -20, and their structures were identified by spectroscopic and physicochemical data.. Seven known compounds were isolated and identified as: myricetin (1), myricitrin (2), syringetin-3-O-beta-D-glucopyranoside (3), medioresinol (4), D-1-O-methyl-myo-inositol (5), hydroquinone (6), and beta-sitosterol (7).. All of these compounds were isolated from genus Heliciopsis for the first time.

    Topics: Flavonoids; Hydroquinones; Magnetic Resonance Spectroscopy; Plant Leaves; Proteaceae; Sitosterols

2008
Study of thermodynamic parameters for solubilization of plant sterol and stanol in bile salt micelles.
    Chemistry and physics of lipids, 2008, Volume: 154, Issue:2

    We investigated the difference between the molecular structures of plant sterols and stanols that affect the solubilization of cholesterol in bile salt micelles (in vitro study). First, the aqueous solubility of beta-sitosterol, beta-sitostanol, and campesterol was determined by considering the specific radioactivity by using a fairly small quantity of each radiolabeled compound. The order of their aqueous solubilities was as follows: cholesterol > campesterol > beta-sitostanol > beta-sitosterol. The maximum solubility of cholesterol and the above mentioned sterol/stanol in sodium taurodeoxycholate and sodium taurocholate solutions (single solubilizate system) was measured. Moreover, the preferential solubilization of cholesterol in bile salt solutions was systematically studied by using different types of plant sterols/stanols. The solubilization results showed that the cholesterol-lowering effect was similar for sterols and stanol. Thermodynamic analysis was applied to these experimental results. The Gibbs energy change (Delta G degrees ) for the solubilization of plant sterols/stanols showed a negative value larger than that for cholesterol.

    Topics: Cholesterol; Micelles; Phytosterols; Sitosterols; Solubility; Taurocholic Acid; Taurodeoxycholic Acid; Thermodynamics

2008
Antibacterial activity of labdane diterpenoids from Stemodia foliosa.
    Journal of natural products, 2008, Volume: 71, Issue:7

    As part of a continuing interest in exploring the chemistry of Brazilian medicinal plants, three new labdane diterpenoids, 6alpha-acetoxymanoyl oxide (1), 6alpha-malonyloxymanoyl oxide (2), and 6alpha-malonyloxy-n-butyl ester manoyl oxide (3), together with the known betulinic acid, lupeol, sitosterol, and stigmasterol, were isolated from the aerial parts of Stemodia foliosa. The structures of 1-3 were established on the basis of interpretation of spectroscopic data, including HRESIMS, and 1D and 2D NMR techniques. All compounds were tested against a bacteria panel consisting of Staphylococcus aureus, Bacillus cereus, B. subtilis, B. anthracis, Micrococcus luteus, Mycobacterium smegmatis, and M. phlei. Compound 2 showed moderate activity against these strains, with MIC values in the range 7-20 microg/mL.

    Topics: Anti-Bacterial Agents; Bacillus anthracis; Bacillus cereus; Bacillus subtilis; Betulinic Acid; Brazil; Diterpenes; Microbial Sensitivity Tests; Micrococcus luteus; Molecular Structure; Mycobacterium phlei; Mycobacterium smegmatis; Pentacyclic Triterpenes; Plants, Medicinal; Scrophulariaceae; Sitosterols; Staphylococcus aureus; Stigmasterol; Triterpenes

2008
[Studies on chemical constituents of Primula sikkmensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:1

    To study the chemical constituents of Primula sikkmensis Hook.. The chemical constituents of the plant were isolated and purified by column chromatography and their structures were elucidated by spectroscopic analysis.. Seven compounds were isolated and identified as kaempferol, quercetin, Prunetin, hexacosanol, Apigenin, beta-sitosterol, quercetin-3-O-beta-D-glucoside, respectively.. Compounds I--VII are obtained for the first time from this plant.

    Topics: Apigenin; Fatty Alcohols; Flavones; Flowers; Isoflavones; Kaempferols; Plants, Medicinal; Primula; Quercetin; Sitosterols; Spectrophotometry, Ultraviolet

2008
[Chemical constituents of Changium smyrnioides].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:1

    To study chemical constituents of Changium smyrnioides Wolff.. The chemical components were isolated and purified by silica gel column and recrystallization. The chemical structures were elucidated on the basis of physico-chemical properties and spectral data.. Ten compounds were isolated and identified as lignoceric acid (1), beta-sitosterol (2), stigmasterol (3), 5-hydroxy-8-methoxypsoralen (4), glycerylmonopalmitate (5), L-pyroglutamic acid (6), succinic acid (7), vanillic acid-4-O-beta-D-glucopyranoside (8 ), vanillic acid (9), daucosterol (10).. Compounds 1, 4, 5, 6, 8 and 9 are obtained from the plant for the first time.

    Topics: Apiaceae; Fatty Acids; Hydrolyzable Tannins; Plant Roots; Plants, Medicinal; Pyrrolidonecarboxylic Acid; Sitosterols; Stigmasterol; Succinic Acid; Vanillic Acid

2008
[Studies on anti-inflammation chemical constitutes of Patrinia villosa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:1

    Patrinia villosa (Thunb. ) Juss. is a Chinese folk medicine, in order to find the material basis that were related to anti-inflammation pharmacodynamic action, we investigated for chemical constituents by chemical and spectroscopic analysis. By phytochemical research, 9 compounds were isolated from the acetic acid ethyl ester & N-Butanol of P. villosa and identified 7 compounds (beta-sitosterol, Villosol, Quercetin, Ferulic acid, Ursolic acid, beta-daucosterol, Rutin), and three compounds (Ferulic acid, Ursolic acid and Rutin) are firstly obtained from P. villosa.

    Topics: Anti-Inflammatory Agents, Non-Steroidal; Coumaric Acids; Lactones; Molecular Structure; Patrinia; Plants, Medicinal; Quercetin; Rutin; Sitosterols; Triterpenes; Ursolic Acid

2008
[Isolation and identification of diterpenoids from Pinus koraiensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:1

    To study chemical compounds from Pinus koraiensis.. The constituents were isolated by chromatographic method and the structures were identified on the basis of spectral alanlysis.. Eight compounds were identified as 8 (14)-podocarpen-13-on-18-oic acid (1), 15-hydroxydehydroabietic acid (2), 12-hydroxyabietic acid (3), lambertianic acid (4), dehydroabietic acid (5), sandaracopimaric acid (6), beta-sitosterol (7), daucosterol (8).. Compounds 1--6 are isolated from this plant for the first time.

    Topics: Abietanes; Carboxylic Acids; Diterpenes; Fruit; Molecular Structure; Naphthalenes; Pinus; Plants, Medicinal; Sitosterols

2008
Report: quantitative estimation of beta-sitosterol, lupeol, quercetin and quercetin glycosides from leaflets of Soymida febrifuga using HPTLC technique.
    Pakistan journal of pharmaceutical sciences, 2008, Volume: 21, Issue:3

    Soymida febrifuga (Meliaceae) dried leaflets (10 gm) were extracted with petroleum ether. Unsaponifiable matter quantitatively used for sample preparation, labeled as SF-U. Another 10 gm leaflet powder was extracted with methanol and quantitatively used for sample preparation labeled as SF-A. Sample and standard solution were dosage on three different plates and developed in its respective mobile phase plates were scanned using TLC scanner III and estimated using integration software CATs 4.05. Calculations for percentage were done considering standard and sample R(f), AUC and dilution factor. Estimation of beta Sitosterol, Lupeol, Quercetin, Quercetin-3-O-galactoside, Quercetin-3-O-xyloside and Quercetin-3-O-rutinoside were determined as 0.02146% w/w, 0.0377% w/w, 0.4079% w/w, 0.6197% w/w, 2.974% w/w and 3.235% w/w respectively with the help of HPLC techniques.

    Topics: Chromatography, Thin Layer; Glycosides; Meliaceae; Pentacyclic Triterpenes; Plant Leaves; Quercetin; Sitosterols; Triterpenes

2008
Effects of hydrophilic and lipophilic beta-sitosterol derivatives on cholesterol absorption and plasma cholesterol levels in rats.
    Journal of agricultural and food chemistry, 2008, Aug-13, Volume: 56, Issue:15

    The effects of two phytosterol derivatives of beta-sitosterol, a lipophilic derivative (LPSS) and a hydrophilic derivative (HPSS), on cholesterol uptake and blood lipoprotein levels in rats were compared with those of beta-sitosterol. LPSS and HPSS have solubilities of up to 0.05 g/mL in edible oil and 0.15 g/mL in water at 25 degrees C, respectively. The intragastric administration of either 30 or 50 mg of phytosterols with 10 mg of [4- (14)C]-cholesterol per kg of body weight once a day for 3 consecutive days reduced cholesterol uptake by approximately 30% compared to controls that received cholesterol alone. Feeding a cholesterol-enriched diet containing 1% or 3% beta-sitosterol, LPSS, or HPSS for 2 and 4 weeks resulted in lowered levels of total blood cholesterol and reduced the atherogenic index in all groups. These results indicate that LPSS and HPSS have comparable effects to beta-sitosterol in lowering blood cholesterol levels but they differ from beta-sitosterol in having a solubility advantage.

    Topics: Animals; Cholesterol; Cholesterol, Dietary; Intestinal Absorption; Male; Rats; Rats, Sprague-Dawley; Sitosterols; Specific Pathogen-Free Organisms

2008
[Studies on chemical constituents of the seeds of Allium cepa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:2

    To study the chemical constituents from the seeds of Allium cepa L., the constituents of the seeds of Allium cepa L.. To isolate and purify by silica gel, macroporous resin HP-20, Sephadex LH-20, RP-18 column.. Seven compounds were isolated from the EtOH extract of the seeds of Allium cepa., their structures were elucidated by physico-chemical properties and spectroscopic analysis as tianshic acid (I), N-trans-feruloyl tyramine (II), beta-sitosterol-3 beta-glucopyranoside-6'-palmitate (III), sitosterol (IV), daucosterol (V), tryptophane (VI), adenine riboside (VI).. Compounds V-VIII are obtained from this plant for the first time, compounds I-IV are isolated from the genus Allium for the first time.

    Topics: Adenosine; Ethanol; Onions; Seeds; Sitosterols; Tryptophan

2008
The composition of cell wall skeleton and outermost lipids of Mycobacterium vaccae is modified by ethambutol treatment.
    Polish journal of microbiology, 2008, Volume: 57, Issue:2

    Ethambutol (EMB) is a first line drug in tuberculosis treatment inhibiting the biosynthesis of arabinogalactan, which is a component of the mycobacterial cell wall. The growth of Mycobacterium vaccae cells in the presence of EMB increases cell wall permeability, which was monitored by beta-sitosterol biotransformation. GC/MS and GLC/MS (gas chromatography/mass spectrometry) analysis revealed dramatic changes in the content of covalently bound mycolic acids and in molar ratio galactose (Gal) to arabinose (Ara) in the cell envelopes of EMB-treated cells. The detected variations in the compositions of fatty acids indicate that both the cell wall skeleton and outer layer (free lipids) are decomposed due to EMB treatment.

    Topics: Antitubercular Agents; Arabinose; Cell Membrane Permeability; Cell Wall Skeleton; Ethambutol; Galactans; Galactose; Gas Chromatography-Mass Spectrometry; Glycolipids; Mycobacterium; Mycolic Acids; Phospholipids; Polysaccharides, Bacterial; Sitosterols

2008
[Studies on chemical constituents and volatile oil of Xiaochengqi decoction].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:9

    To study the chemical constituents and volatile oil of Xiaochengqi decoction.. The constituents in decoction were separated by means of column chromatography and their structures were identified by spectral data and compared with literature data. As well as the volatile oil of Xiaochengqi Fang were analyzed and identified by GC-MS.. Eleven compounds were isolated and identified as chrysophanol (1), physcion (2), magnolol (3), beta-sitosterol (4), sitosterol trans-cinnamic acid (5), emodin (6), aloe emodin (7), rhein (8), gallic acid (9), chrysophanol-8-O-beta-D-glucopyranoside (10), aurantiamarin (11). The volatile oils extracted with steam distillation from Xiaochengqi were identified 67 components, and the main components are including.. All of the eleven compounds were isolated from Xiaochengqi decoction for the first time and the study on their activities in Chinese prescription is being carried out. D-limonene (42.61%), p-cymene (16.43%), and 8-terpinene (14.46%).

    Topics: Anthraquinones; Biphenyl Compounds; Cinnamates; Cyclohexenes; Cymenes; Drugs, Chinese Herbal; Emodin; Gallic Acid; Gas Chromatography-Mass Spectrometry; Lignans; Limonene; Monoterpenes; Oils, Volatile; Sitosterols; Terpenes

2008
Preferential campesterol incorporation into various tissues in apolipoprotein E*3-Leiden mice consuming plant sterols or stanols.
    Metabolism: clinical and experimental, 2008, Volume: 57, Issue:9

    Intestinal absorption of plant sterols and stanols is much lower as compared with that of cholesterol; and therefore, serum concentrations are low. Circulating plant sterols and stanols are incorporated into tissues. However, hardly any data are available about tissue distributions of individual plant sterols and stanols, particularly in relation to their serum concentrations. We therefore fed female apolipoprotein E*3-Leiden mice a control diet, a plant sterol-enriched diet (1g/100 g diet), or a plant stanol-enriched diet (1g/100 g diet) for 8 weeks. In the sterol group, serum cholesterol-standardized campesterol and sitosterol concentrations were, respectively, 8 and 7 times higher as compared with those in the control group. Consequently, the serum campesterol-sitosterol ratio remained essentially unchanged. Cholesterol-standardized plant sterol concentrations increased significantly in all analyzed tissues, except brain. However, the campesterol-sitosterol ratio also increased in all tissues (except in liver and spleen), suggesting that campesterol is preferentially incorporated over sitosterol in those tissues. For the stanol group, serum plant stanol concentrations also increased; but the increase was but less pronounced. We conclude that, in apolipoprotein E*3-Leiden mice, campesterol is preferentially incorporated into most tissues over sitosterol, which cannot be deduced from changes in serum concentrations.

    Topics: Animals; Apolipoprotein E3; Cholesterol; Diet; Female; Mice; Mice, Transgenic; Osmolar Concentration; Phytosterols; Sitosterols; Tissue Distribution

2008
Iridoid glucoside and sterol galactoside from Mussaenda macrophylla.
    Journal of natural medicines, 2008, Volume: 62, Issue:4

    A new iridoid glucoside, 6-epi-barlerin, and a new unusual sterol galactoside along with beta-sitosterol were isolated from the stem bark of Mussaenda macrophylla. The structures were established on the basis of the spectral and chemical evidence.

    Topics: Cation Transport Proteins; Galactosides; Iridoids; Plant Bark; Plant Extracts; Rubiaceae; Sitosterols; Spectrum Analysis; Sterols

2008
Nutrient broth/PEG200/TritonX114/Tween80/Chloroform microemulsion as a reservoir of solubilized sitosterol for biotransformation to androstenedione.
    Journal of industrial microbiology & biotechnology, 2008, Volume: 35, Issue:11

    Microemulsions (ME) can act as a reservoir of solubilized hydrophobic substrates. The biotransformation of hydrophobic sitosterol to androstenedione (AD) with MEs prepared from nutrient broth and PEG 200 (1:1) as aqueous phase, 40 g/l sitosterol dissolved in chloroform as organic phase, Triton X114 and Tween 80 (1:1) as surfactant phase, was investigated. The phase behavior of this system was studied for ten different ratios(w/w), 10:0, 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, 1:9 and 0:10 of the organic phase and surfactant at 30 degrees C. A pseudoternary phase diagram was constructed to demarcate the region giving stable MEs. The maximum solubility of sitosterol in ME medium was observed to be 8 g/l, which is 3 orders of magnitude higher than the reported sitosterol solubility of 2-4 mg/l in aqueous medium. The ME medium was used for biotransformation studies and a comparative result has been reported. Transmission electron microscopy of cells grown in ME having oil, surfactant and aqueous phase in the ratio of 6:14:80 showed a weakened cell wall structure that permitted production of 465.86 mg/l AD.

    Topics: Androstenedione; Biotransformation; Chloroform; Culture Media; Emulsifying Agents; Emulsions; Mycobacterium; Octoxynol; Polyethylene Glycols; Polysorbates; Sitosterols

2008
Enhanced biotransformation of sitosterol to androstenedione by Mycobacterium sp. using cell wall permeabilizing antibiotics.
    Journal of industrial microbiology & biotechnology, 2008, Volume: 35, Issue:11

    Mycobacterial cell wall is rigid and offers a high resistance to the transport of sitosterol into cytosol. The effect of ethambutol, penicillin, polymixin and bacitracin on biotransformation of sitosterol to androstenedione by modification of cell wall permeability was examined. Drug sensitivity assay results established that bacitracin increased the permeability of the cell wall to hydrophobic compounds. Growth inhibitory study of bacitracin and rifamycin, individually as well as in combination showed that these two antibiotics act synergistically to reduce cell growth. A comparison of transmission electron micrograph results of the bacitracin-treated cells with untreated cells, revealed deformities caused in the cell wall structure by bacitracin treatment. These deformities increased the cell wall permeability and transport of sitosterol inside the cell, and thus enhanced androstenedione (AD) production. A maximum of 1.37, 1.44, 1.65 and 1.76 g AD per gram dry cell weight of mycobacterial cells was produced in the presence of ethambutol, penicillin, polymixin and bacitracin, respectively. Below the minimum inhibitory concentration, bacitracin can be used as potent enhancer of permeability of hydrophobic substances across the mycobacterial cell wall.

    Topics: Androstenedione; Anti-Bacterial Agents; Biotransformation; Cell Wall; Mycobacterium; Permeability; Sitosterols

2008
Hydrophobic thickness, lipid surface area and polar region hydration in monounsaturated diacylphosphatidylcholine bilayers: SANS study of effects of cholesterol and beta-sitosterol in unilamellar vesicles.
    Biochimica et biophysica acta, 2008, Volume: 1778, Issue:11

    The influence of a mammalian sterol cholesterol and a plant sterol beta-sitosterol on the structural parameters and hydration of bilayers in unilamellar vesicles made of monounsaturated diacylphosphatidylcholines (diCn:1PC, n=14-22 is the even number of acyl chain carbons) was studied at 30 degrees C using small-angle neutron scattering (SANS). Recently published advanced model of lipid bilayer as a three-strip structure was used with a triangular shape of polar head group probability distribution (Kucerka et al., Models to analyze small-angle neutron scattering from unilamellar lipid vesicles, Physical Review E 69 (2004) Art. No. 051903). It was found that 33 mol% of both sterols increased the thickness of diCn:1PC bilayers with n=18-22 similarly. beta-sitosterol increased the thickness of diC14:1PC and diC16:1PC bilayers a little more than cholesterol. Both sterols increased the surface area per unit cell by cca 12 A(2) and the number of water molecules located in the head group region by cca 4 molecules, irrespective to the acyl chain length of diCn:1PC. The structural difference in the side chain between cholesterol and beta-sitosterol plays a negligible role in influencing the structural parameters of bilayers studied.

    Topics: Cholesterol; Hydrophobic and Hydrophilic Interactions; Lipid Bilayers; Neutron Diffraction; Phosphatidylcholines; Scattering, Small Angle; Sitosterols; Surface Properties; Unilamellar Liposomes; Water

2008
Development of dissolution tests for the quality control of complementary/alternate and traditional medicines: application to African potato products.
    Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques, 2008, Volume: 11, Issue:3

    Unlike orthodox medicines, specific guidelines for dissolution testing of complementary/alternate (CAMs) and traditional medicines (TMs) have not been developed nor is dissolution testing a requirement for the quality control of such products. In this report, the dissolution of African Potato (AP) products, an African traditional medicine (ATM) which has been ingested by man for a diversity of ailments, has been investigated. A norlignan glycoside namely hypoxoside and a sterol, beta-sitosterol (BSS) are purported to be the most important phytochemicals in marketed products of AP. Dissolution testing of AP products containing labelled content of sterols and those containing only hypoxoside is proposed whereby BSS and hypoxoside are monitored as markers for the release of the contents of the abovementioned products, respectively.. The FDA dissolution guidance for industry was used to study the best dissolution condition for several formulations of AP. Buffers in the range of pH 1.2 to 7.5 were used to investigate the dissolution of AP products containing hypoxoside as a marker compound. Similarly, biorelevant dissolution media such as fasted state simulation fluid (FaSSIF) and fed state simulation fluid (FeSSIF) at different pH were used to investigate the release of BSS in AP formulations labelled to contain sterols which exhibited poor water solubility.. Dissolution testing of AP products containing hypoxoside, conducted at pH 1.2 using USP Apparatus 1 indicated that more than 75% of hypoxoside was released within 1 hr. Dissolution testing of products containing sterols, conducted in FeSSIF at a pH of 5.0 resulted in a release of at least 75% of BSS after 1 hr for all but one of the products tested.. Dissolution testing conditions have been developed for AP products containing two different marker compounds where one of the components, hypoxoside, is water soluble, whereas another component, BSS is poorly water soluble. This necessitated the use of different dissolution media and pHs in order to monitor the respective release of hypoxoside and BSS from AP products. The results of this study indicate the necessity and possibility of developing appropriate dissolution testing procedures for use in the quality control of CAMs/TMs.

    Topics: Alkynes; Drug Labeling; Glucosides; Guidelines as Topic; Hydrogen-Ion Concentration; Hypoxis; Medicine, African Traditional; Phytotherapy; Quality Control; Sitosterols; Solubility; Time Factors; United States; United States Food and Drug Administration

2008
Elevated cholesterol precursors other than cholestanol can also be a hallmark for CTX.
    Journal of inherited metabolic disease, 2008, Volume: 31 Suppl 2

    Cerebrotendinous xanthomatosis (CTX) is an inborn error of bile acid synthesis in which hepatic conversion of cholesterol to cholic and chenodeoxycholic acids is impaired. Patients have abnormal bile alcohols in urine, normal to increased plasma cholesterol concentrations and increased concentrations of plasma cholestanol. Little is known about cholesterol precursors in CTX, however. We studied cholesterol and phytosterol profiles in two siblings with CTX during follow-up. While cholesterol concentrations were low in both patients, plasma cholestanol was 6-fold higher compared to control values. In addition, both siblings had a more than 100-fold increase in 7-dehydrocholesterol (7DHC) and 8-dehydrocholesterol (8DHC). Lathosterol, lanosterol and sitosterol were increased in both patients while concentrations of desmosterol and campesterol were normal. In addition, plasma lathosterol/cholesterol ratios were significantly elevated. After treatment with chenodeoxycholate, both patients showed a marked decrease in cholestanol, 7DHC, 8DHC, lathosterol, lanosterol and sitosterol. In addition, the lathosterol/cholesterol ratio normalized, indicating that overall cholesterol synthesis was sufficiently suppressed. This study shows that elevated cholesterol precursors, other than cholestanol, can be a hallmark for CTX.

    Topics: Biomarkers; Chenodeoxycholic Acid; Child; Child, Preschool; Cholestadienols; Cholestanol; Cholesterol; Dehydrocholesterols; Humans; Lanosterol; Male; Predictive Value of Tests; Sitosterols; Time Factors; Treatment Outcome; Up-Regulation; Xanthomatosis, Cerebrotendinous

2008
Validation of a method for the determination of sterols and triterpenes in the aerial part of Justicia anselliana (Nees) T. Anders by capillary gas chromatography.
    Journal of pharmaceutical and biomedical analysis, 2008, Dec-01, Volume: 48, Issue:4

    An accurate and sensitive method, combining soxhlet extraction, solid phase-extraction and capillary gas chromatography is described for the quantitative determination of one triterpene (lupeol) and three sterols (stigmasterol, campesterol and beta-sitosterol) and the detection of another triterpene (alpha-amyrin) from the aerial part of Justicia anselliana. This is the first method allowing the quantification of sterols and triterpenes in this plant. It has been fully validated in order to be able to compare the sterol and triterpene composition of different samples of J. anselliana and therefore help to explain the allelopathic activity due to these compounds. This method showed that the aerial part of J. anselliana contained (292+/-2)mg/kg of lupeol, (206+/-1)mg/kg of stigmasterol, (266+/-2)mg/kg of campesterol and (184+/-9)mg/kg of beta-sitosterol.

    Topics: Acanthaceae; Calibration; Cholesterol; Chromatography, Gas; Molecular Structure; Pentacyclic Triterpenes; Phytosterols; Plant Components, Aerial; Reference Standards; Reproducibility of Results; Sensitivity and Specificity; Sitosterols; Solid Phase Extraction; Sterols; Stigmasterol; Triterpenes

2008
[Study on the chemical constituents of Rhizoma Cyperi].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:7

    To study the chemical constituents of Rhizoma Cyperi.. The constituents were separated and purified by silica gel column chromatography, their structures were identified on the basis of physico-chemical properties and spectral data.. Six compounds were isolated and identified as physicion (1), hexadecanoic acid (2), beta-sitosterol (3), stigmasterol (4), catenarin (5), daucosterol (6).. Compounds 1, 4, 5 were isolated from this plant for the first fime.

    Topics: Cyperus; Emodin; Magnetic Resonance Spectroscopy; Palmitic Acid; Plants, Medicinal; Rhizome; Sitosterols; Spectrophotometry, Ultraviolet; Stigmasterol

2008
Beneficial effects of beta-sitosterol on glucose and lipid metabolism in L6 myotube cells are mediated by AMP-activated protein kinase.
    Biochemical and biophysical research communications, 2008, Dec-26, Volume: 377, Issue:4

    AMP-activated protein kinase (AMPK) is an energy-sensing enzyme that has been implicated as a key factor for controlling intracellular lipids and glucose metabolism. Beta-sitosterol, a plant sterol known to prevent cardiovascular disease was identified from Schizonepeta tenuifolia to an AMPK activator. In L6 myotube cells, beta-sitosterol significantly increased phosphorylation of the AMPKalpha subunit and acetyl-CoA carboxylase (ACC) with stimulating glucose uptake. In contrast, beta-sitosterol treatment reduced intracellular levels of triglycerides and cholesterol in L6 cells. These effects were all reversed by pretreatment with AMPK inhibitor Compound C or LKB1 destabilizer radicicol. Similarly, beta-sitosterol-induced phosphorylation of AMPK and ACC was not increased in HeLa cells lacking LKB1. These results together suggest that beta-sitosterol-mediated enhancement of glucose uptake and reduction of triglycerides and cholesterol in L6 cells is predominantly accomplished by LKB1-mediated AMPK activation. Our findings further reveal a molecular mechanism underlying the beneficial effects of beta-sitosterol on glucose and lipid metabolism.

    Topics: AMP-Activated Protein Kinase Kinases; AMP-Activated Protein Kinases; Animals; Cell Line; Cholesterol; Enzyme Activation; Glucose; Glucose Transporter Type 4; Humans; Hypolipidemic Agents; Lipid Metabolism; Muscle Fibers, Skeletal; Protein Serine-Threonine Kinases; Protein Transport; Rats; Signal Transduction; Sitosterols; Triglycerides

2008
[Chemical constituents from leaves of Paulownia fortunei].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:6

    To study the chemical constituents of leaves of Paulownia fortunei (Seem.) Hemsl.. The constituents were isolated by column chromatography and their structures were elucidated through spectroscopic analysis.. The compounds were identified as mimulone (I), apigenin (II), luteolin (III), 2alpha, 3beta, 19beta-trihydroxyurs-28-O-beta-D-galactonopyranos ylester (anserinoside, IV), 3alpha-hydroxyl-ursolicacid (V), ursolicacid (VI), daucosterol (VII), beta-sitosterol (VIII).. The compounds I - V are obtained from leaves of Paulownia fortunei (Seem.) Hemsl for the first time.

    Topics: Apigenin; China; Luteolin; Magnetic Resonance Spectroscopy; Plant Leaves; Plants, Medicinal; Sapogenins; Scrophulariaceae; Sitosterols

2008
[Studies on chemical constituents of alpinia katsumadai].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:6

    To study the chemical constituents from the ethanolic extract of Alpinia katsumadai Hayata.. The compounds were separated with the column chromatographic, and their structures were identified by chemical and spectroscopic methods.. Eight compounds were isolated from the ethanol extract. On the basis of their physical and chemical properties and spectroscopic analysis, the structures of seven compounds were identified. They were 1,7-Diphenyl-5-hydroxy-4, 6-heptadien-3-one(I), 1,7-Diphenyl4, 6-heptadien-3-one(II), Pinocembrin (III), Cardamomin (IV), Alpinetin (V), 7,4'-Dihydroxy-5-methoxy flavanones(VI) and beta-Sitosterol(VIII), respectively.. Compounds I , II and VII are separated from this plant for the first time. Compounds I and II are also obtained from this genus of Alpinetin for the first time.

    Topics: Chalcones; Flavanones; Plants, Medicinal; Seeds; Sitosterols; Spectrophotometry, Ultraviolet; Zingiberaceae

2008
A new chalcone glycoside from Rhamnus nipalensis.
    Natural product research, 2008, Volume: 22, Issue:18

    A new chalcone glycoside, chalcone-2',4-dihydroxy-4'-O-beta-D-glucoside has been isolated from Rhamnus nipalensis together with sitosterol, lupeol, di-O-methyldaidzein, kaempferol-4'-methylether, quercetin, physcion, sitosterol glucoside, emodin and their structures established by spectroscopic data. Isolation of these compounds are the first report from this plant.

    Topics: Chalcones; Emodin; Glucosides; India; Kaempferols; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pentacyclic Triterpenes; Plants, Medicinal; Quercetin; Rhamnus; Sitosterols; Triterpenes

2008
[Studies on chemical constituents from roots of Pterospermum heterophyllum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:16

    To study the chemical constituents from the roots of Pterospermum heterophyllum.. The chemical constituents of P. heterophyllum were isolated and purified by silica gel and sephadex LH-20 column chromatography. Their structures were identified on the basis of spectroscopic data and physicochemical properties.. Nine compounds were isolated and identified as taraxerol (1), betulin (2), betulinic acid (3), sumaresinolic acid (4), 2-methoxy-5-hydroxy-1, 4-naphthoquinone (5), 5, 7-dihydroxy-6, 8-dimethylchromone (6), alpha-monpalmitin (7), palmitic acid (8), beta-sitosterol (9).. Compounds 2-7 were isolated from this genus for the first time.

    Topics: Betulinic Acid; Chromatography; Malvaceae; Naphthoquinones; Oleanolic Acid; Palmitic Acid; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Triterpenes

2008
[Studies on chemical constituents of Peucedanum delavayi].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:8

    To study the chemical constituents of the radix and rhizome of Peucedanum delavayi.. The chemical constituents had been separated by manifold chromato-graphy methods, and their structures were determined by spectral analysis.. Fifteen compounds were isolated and identified as Umbelliferone(I), Coumurayin(II), Mexoticin(III), Marmesin (IV), Ammijin(V), Delton (VI), Selinidin(VII), Anomalin(VII), Isopteryxin(IX), Ferulic acid(X), Falcarindiol(XI), Stearic acid(XII), beta-sitosterol(X III), Daucosterol(XIV) and d-Mannitol(XV).. All these compounds are isolated from Peucedanum delavayi for the first time.

    Topics: Apiaceae; Bisphenol A-Glycidyl Methacrylate; Coumaric Acids; Coumarins; Plant Roots; Plant Stems; Plants, Medicinal; Sitosterols; Umbelliferones

2008
[Studies on chemical constituents from rattan of Polygonum multiflorum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:8

    To study on the chemical constituents from rattan of Polygonum multiflorum.. The chemical constituents were extracted with alcohol and were separated with manifold chromatography technique. Their structures were determined by spectral analysis.. Thirteen compounds were isolated and identified as Chrysophanol(I), Physcion(II), Emodin(III), Aloeemodin(IV), Rhein(V), Physcion-8-O-beta-D-glucoside(VI), Emodin-8-O-beta-D-glucoside (VII),2,3,5,4'-Tetrahydroxy-stibene-2-O-beta-D-glucoside(VIII), Noreugenin(IX), Apigenin(X), Daucosterol(XI), beta-Sitosterol(XII), Stearic acid(XIII).. Among these, compounds I, IV-VI, VIII-XI, XIII are isolated from rattan of Polygonum multiflorum for the first time.

    Topics: Anthraquinones; Apigenin; Emodin; Glucosides; Molecular Structure; Plant Stems; Plants, Medicinal; Polygonum; Sitosterols; Spectrophotometry, Ultraviolet

2008
Uterolytic effect of Hypoxis hemerocallidea Fisch. & C.A. Mey. (Hypoxidaceae) corm [;African Potato'] aqueous extract.
    Journal of smooth muscle research = Nihon Heikatsukin Gakkai kikanshi, 2008, Volume: 44, Issue:5

    Extracts of Hypoxis hemerocallidea corm (African potato) are commonly used by some traditional health practitioners in KwaZulu-Natal Province of South Africa as natural antenatal remedy to prevent threatening or premature abortion and miscarriage, and to ensure successful confinement. In this study, we investigated the uterolytic activity of H. hemerocallidea corm aqueous extract on spontaneous, rhythmic contractions of uterine horns taken from pregnant rats and guinea-pigs, as well as on spasmogen-provoked contractions of stilboesterol-primed, oestrogen-dominated, non-pregnant rat and guinea-pig isolated uterine horns. Relatively low to high concentrations of H. hemerocallidea corm aqueous extract (APE, 25-400 mg/ml) inhibited the amplitude of the spontaneous, rhythmic contractions of, and relaxed, uterine horns isolated from pregnant rats and guinea-pigs in a concentration-related manner. Furthermore, relatively low to high concentrations of APE (25-400 mg/ml) relaxed basal tones of uterine horns taken from non-pregnant, oestrogen-dominated rats and guinea-pigs in a concentration-dependent manner. The same moderately low to high concentrations of APE (25-400 mg/ml) inhibited acetylcholine-, oxytocin-, bradykinin-, and potassium chloride (K(+))-induced contractions of oestrogen-dominated rat and guinea-pig isolated uterine horns in a concentration-related manner. Although the mechanism of uterolytic action of APE could not be established, the results of the present study lend pharmacological credence to the folkloric, ethnomedical uses of APE as a natural antenatal remedy for threatening or premature abortion, and suggest that the uterolytic action of the corm's extract is unlikely to be mediated via beta(2)-adrenoceptor stimulation, but probably mediated through a non-specific spasmolytic mechanism.

    Topics: Abortion, Threatened; Alkynes; Animals; Catechols; Female; Glucosides; Guinea Pigs; Humans; Hypoxis; In Vitro Techniques; Parasympatholytics; Phytotherapy; Plant Extracts; Plants, Medicinal; Pregnancy; Rats; Rats, Wistar; Sitosterols; Uterine Contraction

2008
[Studies on chemical constituents of rhizomes of Smilax china].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:21

    To study the chemical constituents of the rhizomes of Smilax china.. The constituents of the rhizomes of S. china were isolated and purified by repeated silica gel and Sephadex LH-20 chromatography, and their structures were elucidated on the basis of spectral analysis.. Thirteen compounds were obtained and identified as kaemperol-7-O-beta-D-glucopyranoside (1), engeletin (2), isoengeletin (3), kaempferol (4), dihydrokaempferol (5), dihydrokaempferol-5-O-P-D-glucopyranoside (6), rutin (7), kaempferol- 5-O-beta-D-glucopyranoside (8), 3, 5, 4'-trihydroxystibene (9), vanillic acid (10), 3, 5-dimethoxy4-O-beta-D-glu-copyranosylcinnamic acid (11), beta-sitosterol (12), and beta-daucosterol (13) , respectively.. Compounds 1, 3, 7, 8, and 11 were isolated from this plant for the first time, and compounds 8 and 11 were isolated from the genus Smilax for the first time.

    Topics: Chromatography; Flavonoids; Flavonols; Glycosides; Kaempferols; Magnetic Resonance Spectroscopy; Plants, Medicinal; Rhizome; Sitosterols; Smilax; Vanillic Acid

2008
[Chemical constituents from barks of Garcinia tetralata].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:20

    To study the chemical constituents of the barks of Garcinia tetralata.. Compounds were isolated and purified repeatedly by silica gel and ODS column chromatography and their chemical structures were elucidated by their physicochemical properties and spectral data analysis.. Ten compounds were obtained and identified as 1, 7-dihydroxyxanthone (1), buchanaxanthone (2), garciniaxanthone H (3), 1, 2, 5-trihydroxyxanthone (4), subelliptenone H (5), 6-desoxyjacareubin (6), 6-deoxyisojacreubin (7), subelliptenone G (8), methyl orsellinate (9) and beta-sitosterol (10).. Compounds 1-10 were isolated from this plant and compound 9 was obtained from the genus Garcinia for the first time.

    Topics: Drugs, Chinese Herbal; Garcinia; Magnetic Resonance Spectroscopy; Plant Bark; Resorcinols; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Xanthones

2008
[Studies on chemical constituents from leaves of Vaccinium bracteatum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:18

    To investigate the chemical constituents from the leaves of Vaccinium bracteatum.. Many column chromatographic techniques were used for the isolation and separation of chemical constituents. Their structures were elucidated on the basis of spectral analysis and chemical evidences.. Twelve compounds were isolated from the plant, and they were identified as chrysoeriol (1), scopoletin (2), trans-p-hydroxycinnamic acid (3), trans-p-hydroxycinnamic acid ethyl ester (4), cafeic acid ethyl ester (5), beta-sitosterol (6), iuteolin (7), quercetin (8), esculetin (9), cafeic acid (10), isolariciresinol-9-O-beta-D-xyloside (11), 10-O-trans-p-coumaroylsandoside (12).. Compounds 4, 5, 11, 12 were isolated from the genus Vaccinium for the first time, and compounds 1, 2, 9, 10 were isolated from this plant for the first time.

    Topics: Coumaric Acids; Flavones; Flavonoids; Furans; Glycosides; Lignin; Molecular Structure; Plant Leaves; Scopoletin; Sitosterols; Umbelliferones; Vaccinium

2008
[Studies on chemical constituents of aerial parts of Ammopiptanthus mongolicus].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:19

    To investigate the chemical constituents of the aerial parts of Ammopiptanthus mongolicus.. The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data.. Ten compounds were isolated and identified as m-hydroxybenzoic acid (1), 1-(4-hydroxyphenyl) ethanone (2), beta-sitosterol (3), (-)-syringaresinol (4), (+)-lariciresinol (5), blumenol A (6), blumenol B (7), beta-daucosterol (8), coniferin (9), syringin (10).. The ten compounds were obtained from the genus Ammopiptanthus for the first time.

    Topics: Cinnamates; Cyclohexanones; Drugs, Chinese Herbal; Fabaceae; Glucosides; Magnetic Resonance Spectroscopy; Phenylpropionates; Plant Components, Aerial; Sitosterols

2008
[Chemical constituents of Solanum cathayanum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:9

    To study the chemical constituents of Solanum cathayanum.. Chemical constituents were isolated by chromatographic methods and identified by NMR analysis.. Five compounds were isolated and identified as lignoceric acid (I), beta-sitosterol (II), lupeol (III) 8-hydroxy-3-methoxy-5H-pyrido [2, 1-c] pyrazin-5-one (IV), ethly 2,6-dioxo-1,2,3,6-tetrahy-dropyrimidine-4-carboxylate (V).. Compound I and III are isolated from this plant for the first time. Compound IV and V are isolated from the genus of Solanum for the first time.

    Topics: China; Chromatography, High Pressure Liquid; Fatty Acids; Magnetic Resonance Spectroscopy; Molecular Structure; Plants, Medicinal; Sitosterols; Solanum; Triterpenes

2008
[Studies on chemical constituents from herbs of Botrychium lanuginosum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:22

    To study the chemical constituents of Botrychium lanuginosum.. Various chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated by chemical evidence and spectroscopic methods.. Ten compounds were isolated from the 95% ethanol extract of the herb of B. lanuginosum and their structures were elucidated as 30-nor-21beta-hopan-22-one (1), beta-sitosterol (2), luteolin (3), thunberginol A (4), apigenin (5), (6'-O-palmitoyl)-sitosterol-3-O-beta-D-glucoside (6), daucosterol (7), 1-O-beta-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2R-hydroxy hexadecanoyl) amino]-4, 8-octadecadiene-1, 3-diol (8), luteolin-7-O-glucoside (9), sucrose (10).. Compounds 1-10 were isolated from this genus for the first time.

    Topics: Apigenin; Chromatography; Drugs, Chinese Herbal; Ferns; Isocoumarins; Luteolin; Sitosterols; Sucrose

2008
[Studies on chemical constituents from Grewia biloba].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:10

    To investigate the chemical constituents of Grewia biloba and find its bioactive compounds.. Compounds were isolated by silica gel, MCI, Sephadex LH-20 and Rp-18 column chromatography, and purified by recrystallization. Their structures were elucidated by spectral analysis and other methods.. Six compounds were isolated and identified as friedelin (1) epi-friedelan-3-ol (2), heneicosanoic acid (3), beta-sitosterol (4), Propyl palmitate (5), eatechin (6), respectively.. Compounds 1-3, 5, 6 are isolated from Grewia genus for the first time and compounds 4 is isolated from Grewia biloba for the first time.

    Topics: Fatty Acids; Grewia; Magnetic Resonance Spectroscopy; Palmitates; Plant Bark; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

2008
[Studies on chemical constituents from Zephyranthes candida].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:10

    To study on the chemical constituents of Zephyranthes candida.. Compounds were isolated and repeatedly purified by chromatographic techniques on silica gel column. Their structures were elucidated by chemical and spectral methods.. Eight compounds were isolated from the whole plant of Zephyranthes candida, and identified as (2S)-3',7-dihydroxy-4'-methoxyflavan (I), beta-sitosterol (II), stigmasta-5,22-dien-3beta-ol (III), stigmasterol (IV), beta-daucosterin (V), Butylisobutyl phthalat (VI), Heptacosane (VII) and Ambrettolide (VIII).. I-XIII are all isolated from this plant for the first time.

    Topics: Dicarboxylic Acids; Flavonoids; Liliaceae; Magnetic Resonance Spectroscopy; Molecular Structure; Plants, Medicinal; Sitosterols; Stigmasterol

2008
[Triterpenoids and steroids of root of Rubus biflorus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2008, Volume: 31, Issue:11

    To investigate the chemical constituents of root of Rubus biflorus.. Isolation and purification were carried out by silica gel column chromatography and recrystallization and so on. Structural determination of the pure compounds was based on physico-chemical properties and various spectral data analysis (1H-NMR, 13C-NMR, IR, EI-MS).. Five compounds were isolated and identified as follows: lupeol acetate (I), corosolic acid (II), oleanic acid (III), 2alpha-hydroxyoleanolic acid (IV), sitosterol (V).. All these compounds are isolated from this plant for the first time.

    Topics: Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plant Roots; Plants, Medicinal; Rosaceae; Sitosterols; Steroids; Triterpenes

2008
Moderately elevated plant sterol levels are associated with reduced cardiovascular risk--the LASA study.
    Atherosclerosis, 2008, Volume: 196, Issue:1

    Functional foods with supplementation of plant sterols are already used by millions of people. However, at the same time it is current scientific thinking that elevation of plant sterols in the circulation causes coronary heart disease. Therefore, this study aimed to define the risk for coronary heart disease associated with moderately high plant sterol plasma levels in a cohort of elderly. In this study, we evaluated the association between plant sterols and coronary heart disease in a cohort of 1242 subjects older than 65 years, participating at the Longitudinal Aging Study Amsterdam (LASA). Concentrations of sitosterol, campesterol, brassicasterol and stigmasterol were assessed using highly sensitive and specific gas chromatography-mass spectrometry-selected ion-monitoring. Plant sterol concentrations (and their ratios to cholesterol) were slightly, however, significantly lower in patients with coronary heart disease. Moreover, high plasma concentrations of a marker plant sterol, sitosterol, were associated with a markedly reduced risk for coronary heart disease (OR 0.78, CI 0.62-0.98, p<0.05). In contrast neither plant stanols (sitostanol or campestanol) nor the cholesterol synthesis markers (lathosterol, lanosterol and desmosterol) nor their ratios to cholesterol were significantly different in the study groups. These data suggest that plant sterols could have neutral or even protective effects on development of coronary heart disease, which have to be confirmed in interventional trials.

    Topics: Aged; Aged, 80 and over; Cholesterol; Coronary Disease; Cross-Sectional Studies; Female; Humans; Logistic Models; Male; Peripheral Vascular Diseases; Phytosterols; Risk Factors; Sitosterols

2008
Immobilization of mycobacterial cells onto silicone--assessing the feasibility of the immobilized biocatalyst in the production of androstenedione from sitosterol.
    Bioresource technology, 2008, Volume: 99, Issue:7

    Silicone rubbers are hydrophobic, a feature that may prove advantageous if this material is to be used as immobilization matrix in bioconversion systems where hydrophobic species are present, such as sterols and mycobacterial cells. Mycobacterium sp. cells with sitosterol side chain cleavage activity were accordingly effectively adsorbed onto silicone and the potential application of the concept was assessed by matching the behavior of the resulting immobilized biocatalyst with free cells and Celite immobilized cells. Mass transfer, kinetics, thermal and storage stability characterization of a biotransformation system based in the use of the silicone immobilized biocatalyst was performed. The feasibility of biocatalyst reutilization was tentatively explored.

    Topics: Androstenedione; Bacterial Adhesion; Catalysis; Chromatography, High Pressure Liquid; Feasibility Studies; Mycobacterium; Sitosterols

2008
Responses of surrogate markers of cholesterol absorption and synthesis to changes in cholesterol metabolism during various amounts of fat and cholesterol feeding among healthy men.
    The British journal of nutrition, 2008, Volume: 99, Issue:2

    Serum ratios to cholesterol of lathosterol, and of cholestanol, campesterol and sitosterol measure respective relative cholesterol synthesis and absorption, but their clinical applicability is not known in evaluation of cholesterol metabolism under different dietary conditions. We compared relative synthesis and absorption of cholesterol to the respective absolute ones in healthy male volunteers (n 29) on four subsequent diets: baseline home (HD), low-cholesterol low-fat (LCLF), high-cholesterol low-fat (HCLF) and low-cholesterol high-fat (LCHF). Serum lipids, lipoproteins, sterols, fractional cholesterol absorption and sterol synthesis were examined. HCLF and LCHF decreased fractional cholesterol absorption by approximately 23-27 % from baseline HD (P < 0.05) and increased the levels of total and LDL-cholesterol in serum from LCLF by approximately 9-14 % (P < 0.05). On HCLF, bile acid synthesis was high (P < 0.05 for each), and absolute cholesterol synthesis tended to be higher than on HD and LCHF (NS). Relative synthesis was positively associated with absolute cholesterol synthesis, but inversely with relative absorption during each diet (P < 0.05). The relative absorption markers were interrelated in each diet, and were also associated with fractional absorption of cholesterol in each diet but HD. In conclusion, relative markers of cholesterol absorption and synthesis reflect changes in cholesterol metabolism despite the amount of dietary fat and cholesterol consumed, but their validity with this respect is strengthened by controlled diets in metabolic studies. Additions of cholesterol and fat to a diet low in fat and cholesterol cause practically equal changes in the serum lipid profiles, whereas synthesis of cholesterol (NS) and bile acids (P < 0.05) were higher with the high-cholesterol feeding.

    Topics: Biomarkers; Cholesterol; Cholesterol, Dietary; Diet; Dietary Fats; Feces; Follow-Up Studies; Humans; Intestinal Absorption; Lipids; Lipoproteins; Male; Middle Aged; Phytosterols; Sitosterols; Sterols

2008
Overexpression of CYP710A1 and CYP710A4 in transgenic Arabidopsis plants increases the level of stigmasterol at the expense of sitosterol.
    Planta, 2008, Volume: 227, Issue:2

    Sitosterol and stigmasterol are major sterols in vascular plants. An altered stigmasterol:sitosterol ratio has been proposed to influence the properties of cell membranes, particularly in relation to various stresses, but biosynthesis of stigmasterol is poorly understood. Recently, however, Morikawa et al. (Plant Cell 18:1008-1022, 2006) showed in Arabidopsis thaliana that synthesis of stigmasterol and brassicasterol is catalyzed by two separate sterol C-22 desaturases, encoded by the genes CYP710A1 and CYP710A2, respectively. The proteins belong to a small cytochrome P450 subfamily having four members, denoted by CYP710A1-A4, and are related to the yeast sterol C-22 desaturase Erg5p acting in ergosterol synthesis. Here, we report on our parallel investigation of the Arabidopsis CYP710A family. To elucidate the function of CYP710A proteins, transgenic Arabidopsis plants were generated overexpressing CYP710A1 and CYP710A4. Compared to wild-type plants, both types of transformant displayed a normal phenotype, but contained increased levels of free stigmasterol and a concomitant decrease in the level of free sitosterol. CYP710A1 transformants also displayed higher levels of esterified forms of stigmasterol, cholesterol, 24-methylcholesterol and isofucosterol. The results confirm the findings of Morikawa et al. (Plant Cell 18:1008-1022, 2006) regarding the function of CYP710A1 in stigmasterol synthesis, and show that CYP710A4 also has this capacity. Furthermore, our results suggest that an increased stigmasterol level alone is sufficient to stimulate esterification of other major sterols.

    Topics: Amino Acid Sequence; Arabidopsis; Arabidopsis Proteins; Cytochrome P-450 Enzyme System; Gene Expression Regulation, Plant; Molecular Sequence Data; Molecular Structure; Oxidoreductases; Phylogeny; Plants, Genetically Modified; Sitosterols; Stigmasterol

2008
Evaluation of reproductive safety of beta-sitosterol on the American mink (Neovison vison).
    Chemosphere, 2008, Volume: 71, Issue:3

    beta-Sitosterol is a weakly estrogenic phytosterol used extensively in functional foods to lower elevated serum cholesterol concentrations due to its inhibitory action on intestinal cholesterol absorption. It caused previously decreased sex steroid concentrations in fish and lowered sperm counts in rats. In the American mink (Neovison vison), litter size increased slightly due to dietary beta-sitosterol supplement. The aim of the present experiment was to conduct a dose-response study on the effects of beta-sitosterol on the reproduction of the American mink. Juvenile male and female mink (n=480) were exposed to 0, 5, 10 or 50 mg of peroral beta-sitosterol kg(-1)d(-1) for 10 months. After 3 months of exposure in November, 15 males per group were sacrificed and general biochemical variables reflecting overall health were determined. The beta-sitosterol-treated male mink had increased absolute and relative masses of intraabdominal fat and higher blood hemoglobin and serum high-density lipoprotein cholesterol concentrations. In spring, the top-rated male mink were mated with multiple females within each study group and reproductive success was assessed. No differences in the reproductive performance of the males (10-11 per group) or females (47-50 per group) could be detected in the exposed groups and the kits of all groups developed in a similar manner. The results suggest that dietary beta-sitosterol presents no significant risk to mammalian fertility.

    Topics: Animals; Animals, Newborn; Cholesterol; Female; Hypolipidemic Agents; Male; Mink; Pregnancy; Reproduction; Sitosterols

2008
Withanolides from Withania somnifera roots.
    Phytochemistry, 2008, Volume: 69, Issue:4

    Two new and seven known withanolides along with beta-sitosterol, stigmasterol, beta-sitosterol glucoside, stigmasterol glucoside, alpha+beta glucose were isolated from the roots of Withania somnifera. Among the known compounds, Viscosa lactone B, stigmasterol, stigmasterol glucoside and alpha+beta glucose are being reported from the roots of W. somnifera for the first time. One of the new compounds contained the rare 16beta-acetoxy-17(20)-ene the other contained unusual 6alpha-hydroxy-5,7alpha-epoxy functional groups in the withasteroid skeleton. The structures were elucidated by spectroscopic methods and chemical transformations.

    Topics: Glucosides; Molecular Structure; Plant Extracts; Plant Roots; Sitosterols; Stigmasterol; Withania; Withanolides

2008
Effect of resveratrol, tyrosol and beta-sitosterol on oxidised low-density lipoprotein-stimulated oxidative stress, arachidonic acid release and prostaglandin E2 synthesis by RAW 264.7 macrophages.
    The British journal of nutrition, 2008, Volume: 99, Issue:6

    Oxidation of LDL is hypothesised as an early and critical event in atherogenesis. Oxidised LDL (oxLDL) favour the transformation of macrophages into foam cells, an important cell involved in atherosclerosis. Furthermore, oxLDL cause multiple changes in macrophage functions. Thus, oxLDL induces certain genes, suppresses others and alters cell lipid metabolism. Consumption of a Mediterranean diet is associated with a low incidence of atherosclerotic disease, but data about the specific dietary constituents involved and mechanisms conferring cardioprotection are still sparse. The aim of the present study was to determine the effect of representative minor components of wine and olive oil on reactive oxygen species and eicosanoid synthesis induced by oxLDL-stimulated macrophages. We observed that exposure to non-toxic oxLDL concentrations leads to the production of H2O2 by RAW 264.7 macrophages and this effect was reverted by apocynin, a NADPH oxidase inhibitor. Moreover, oxLDL induced arachidonic acid (AA) release, cyclo-oxygenase-2 overexpression and subsequent PGE2 release. We observed that resveratrol and tyrosol revert H2O2 production induced by oxLDL as well as AA release and PGE2 synthesis and that these effects were not as a consequence of these compounds interfering with the oxLDL binding to their receptors. Interestingly, beta-sitosterol presence enhances these polyphenol actions. Thus, we found a synergistic action of polyphenols of olive oil and wine and beta-sitosterol of olive oil led to the modulation of the effects of oxLDL on oxidative stress and PGE2 synthesis.

    Topics: Animals; Antioxidants; Arachidonic Acid; Atherosclerosis; Cells, Cultured; Dinoprostone; Hydrogen Peroxide; Lipid Metabolism; Lipoproteins, LDL; Macrophages; Mice; Olive Oil; Oxidative Stress; Phenylethyl Alcohol; Plant Oils; Protein Binding; Resveratrol; Sitosterols; Stilbenes; Wine

2008
Sterol oxidation in ready-to-eat infant foods during storage.
    Journal of agricultural and food chemistry, 2008, Jan-23, Volume: 56, Issue:2

    The effect of storage on sterol oxidation of ready-to-eat infant foods was evaluated. Two different liquid infant foods (honey or fruits flavors), prepared with milk and cereals, were stored for 0, 2, 4, 7 and 9 months at 25 degrees C. Sterol oxidation products (SOP) were isolated by cold saponification, purified by silica solid-phase extraction, and analyzed by gas chromatography (GC) and GC-mass spectrometry. beta-Sitosterol was the most representative sterol, followed by cholesterol and campesterol. No significant differences in the total and single SOP content (0.8-1 mg/kg of product) were observed with respect to storage time and type of sample; the main SOP found was 7-ketositosterol (<0.2 mg/kg of product). The extent of stigmasterol oxidation (2.9%) was higher than that of cholesterol (1.9%) and beta-sitosterol (1.4%). The type and quality of raw materials, as well as the processing conditions, seem to greatly influence SOP formation and accumulation in infant foods.

    Topics: Cholesterol; Fatty Acids; Food Preservation; Infant Food; Oxidation-Reduction; Phytosterols; Sitosterols; Sterols

2008
Isolation and identification of mosquito larvicidal compound from Abutilon indicum (Linn.) Sweet.
    Parasitology research, 2008, Volume: 102, Issue:5

    Larvicidal activity of crude hexane, ethyl acetate, petroleum ether, acetone and methanol extracts of five medicinal plants, Abutilon indicum, Aegle marmelos, Euphorbia thymifolia, Jatropha gossypifolia and Solanum torvum were assayed for their toxicity against the early fourth-instar larvae of Culex quinquefasciatus. The larval mortality was observed after 24 h exposure. All extracts showed moderate larvicidal effects; however, the highest larval mortality was found in petroleum ether extract of A. indicum. In the present study, bioassay-guided fractionation of A. indicum led to the separation and identification of a beta-sitosterol as a potential new mosquito larvicidal compound with LC50 value of 11.49, 3.58 and 26.67 ppm against Aedes aegypti L, Anopheles stephensi Liston and C. quinquefasciatus Say (Diptera: Culicidae), respectively. 1H NMR, 13C NMR and mass spectral data confirmed the identification of the active compound. beta-sitosterol has been recognized as the active ingredient of many medicinal plant extracts. All the crude extracts when screened for their larvicidal activities indicated toxicity against the larvae of C. quinquefasciatus. This article reports the isolation and identification of the beta-sitosterol as well as bioassay data for the crude extracts. There are no reports of beta-sitosterol in the genus A. indicum, and their larvicidal activities are being evaluated for the first time. Results of this study show that the petroleum ether extract of A. indicum may be considered as a potent source and beta-sitosterol as a new natural mosquito larvicidal agent.

    Topics: Aedes; Animals; Anopheles; Culex; Culicidae; Insecticides; Larva; Malvaceae; Plant Extracts; Plant Leaves; Sitosterols; Solvents

2008
Madin-Darby canine kidney II cells: a pharmacologically validated system for NPC1L1-mediated cholesterol uptake.
    Molecular pharmacology, 2008, Volume: 73, Issue:4

    Absorption of dietary cholesterol in the proximal region of the intestine is mediated by Niemann-Pick C1-like protein (NPC1L1) and is sensitive to the cholesterol absorption inhibitor ezetimibe (EZE). Although a correlation exists between EZE binding to NPC1L1 in vitro and efficacy in vivo, the precise nature of interaction(s) between NPC1L1, EZE, and cholesterol remain unclear. Here, we analyze the direct relationship between EZE analog binding to NPC1L1 and its influence on cholesterol influx in a novel in vitro system. Using the EZE analog [(3)H]AS, an assay that quantitatively measures the expression of NPC1L1 on the cell surface has been developed. It is noteworthy that whereas two cell lines (CaCo-2 and HepG2) commonly used for studying NPC1L1-dependent processes express almost undetectable levels of NPC1L1 at the cell surface, polarized Madin-Darby canine kidney (MDCKII) cells endogenously express 4 x 10(5) [(3)H]AS sites/cell under basal conditions. Depleting endogenous cholesterol with the HMG CoA reductase inhibitor lovastatin leads to a 2-fold increase in the surface expression of NPC1L1, supporting the contention that MDCKII cells respond to changes in cholesterol homeostasis by up-regulating a pathway for cholesterol influx. However, a significant increase in surface expression levels of NPC1L1 is necessary to characterize a pharmacologically sensitive, EZE-dependent pathway of cholesterol uptake in these cells. Remarkably, the affinity of EZE analogs for binding to NPC1L1 is almost identical to the IC(50) blocking cholesterol flux through NPC1L1 in MDCKII cells. From a mechanistic standpoint, these observations support the contention that EZE analogs and cholesterol share the same/overlapping binding site(s) or are tightly coupled through allosteric interactions.

    Topics: Animals; Azetidines; beta-Lactams; Caco-2 Cells; Cell Line; Cholesterol; Cloning, Molecular; Dogs; Ezetimibe; Humans; Membrane Proteins; Membrane Transport Proteins; Reproducibility of Results; Sitosterols; Sulfonamides; Transfection; Tritium

2008
Liver X receptor beta (LXRbeta): a link between beta-sitosterol and amyotrophic lateral sclerosis-Parkinson's dementia.
    Proceedings of the National Academy of Sciences of the United States of America, 2008, Feb-12, Volume: 105, Issue:6

    Administration of beta-sitosterol (42 mg/kg per day) for 3 weeks to 8-month-old male LXRbeta-/- mice resulted in the death of motor neurons in the lumbar region of the spinal cord and loss of tyrosine hydroxylase-positive dopaminergic neurons in the substantia nigra. In mice at 5 months of age, beta-sitosterol had no observed toxicity but at 16 months of age, it caused severe paralysis and symptoms typical of dopaminergic dysfunction in LXRbeta-/- mice. WT mice were not affected by these doses of beta-sitosterol. In 5-month-old mice, levels of the intestinal transporters, ABCG5/8 and Niemann-Pick C1 Like 1, were not affected by loss of liver X receptor (LXR) beta and/or treatment with beta-sitosterol nor were there changes in plasma levels of cholesterol or beta-sitosterol. In 8-month-old LXRbeta-/- mice there was activation of microglia in the substantia nigra pars reticulata and aggregates of ubiquitin and TDP-43 in the cytoplasm of large motor neurons in the lumbar spinal cord. Brain cholesterol concentrations were higher in LXRbeta-/- than in their WT counterparts, and treatment with beta-sitosterol reduced brain cholesterol in both WT and LXRbeta-/- mice. In LXRbeta-/- mice but not in WT mice levels of 24-hydrocholesterol were increased upon beta-sitosterol treatment. These data indicate that multiple mechanisms are involved in the sensitivity of LXRbeta-/- mice to beta-sitosterol. These include activation of microglia, accumulation of protein aggregates in the cytoplasm of large motor neurons, and depletion of brain cholesterol.

    Topics: Amyotrophic Lateral Sclerosis; Animals; ATP-Binding Cassette Transporters; Cholesterol; DNA-Binding Proteins; Dopamine; Immunohistochemistry; Intestinal Mucosa; Liver X Receptors; Male; Mice; Mice, Knockout; Motor Neurons; Orphan Nuclear Receptors; Parkinsonian Disorders; Receptors, Cytoplasmic and Nuclear; Sitosterols; Spinal Cord; Substantia Nigra; Tyrosine 3-Monooxygenase

2008
Beta-sitosterol sensitizes MDA-MB-231 cells to TRAIL-induced apoptosis.
    Acta pharmacologica Sinica, 2008, Volume: 29, Issue:3

    To investigate whether subtoxic concentration of beta-sitosterol (SITO) combined with TNF-related apoptosis-inducing ligand (TRAIL) induces apoptosis in TRAIL-resistant MDA-MB-231 breast cancer cells.. Cell viability and growth were assessed by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphnyl-2H-tetrazolim bromide assays, chromatin condensation, release of lactate dehydrogenase (LDH), and Annexin V+ cells. The apoptosis-related proteins were detected by Western blotting.. Treatment with TRAIL in combination with subtoxic concentrations of SITO sensitized MDA-MB-231 breast cancer cells to TRAIL-mediated apoptosis. The synergistic treatment induced chromatin condensation, DNA fragmentation, the release of LDH, and Annexin V+ cells. The indicators of apoptosis are correlated to the induction of caspase activities, which results in the cleavage of poly(ADP-ribose)polymerase. Both the cytotoxic effects and apoptotic characteristics induced by the synergistic treatment were significantly inhibited by a pan-caspase inhibitor z-VAD-fmk, demonstrating the important role of caspases. These results indicate that caspases are crucial regulators of apoptosis induced by the combined treatment of SITO and TRAIL in MDA-MB-231 cells.. The synergistic treatment of SITO and TRAIL induces apoptosis, which can serve as a potential preventive and therapeutic agent.

    Topics: Annexin A5; Apoptosis; Breast Neoplasms; Cell Line, Tumor; Cell Survival; Dose-Response Relationship, Drug; Drug Synergism; Female; Fluorescein-5-isothiocyanate; Fluorescent Dyes; Formazans; Humans; Hypolipidemic Agents; Sitosterols; Tetrazolium Salts; TNF-Related Apoptosis-Inducing Ligand

2008
Chemoprevention of tumor metastasis by liposomal beta-sitosterol intake.
    Biological & pharmaceutical bulletin, 2008, Volume: 31, Issue:3

    To investigate chemopreventive effect of liposomal beta-sitosterol on tumor metastasis, we prepared liposomal beta-sitosterol composed of egg yolk phosphatidylcholine for oral delivery. Although orally administered beta-sitosterol (4 micromol as beta-sitosterol/mouse) was not absorbed into plasma, the amount of immune response cytokines such as IL-12 and IL-18 was increased in the small intestine after the liposome intake. Moreover, after daily oral administration of the liposome for 7 d, natural killer (NK) cell activity in the mice was increased, suggesting that the immune surveillance activity of mice was enhanced by the liposomal beta-sitosterol intake. Thus, we examined metastatic potential of B16BL6 melanoma cells, which were intravenously injected into mice after sequential administration of liposomal beta-sitosterol for 7 d. The number of metastatic colonies in the lungs was significantly less than that of control group two weeks after the injections of the cells. These results suggest that daily liposomal beta-sitosterol intake prevents tumor metastasis may be due to enhancement of gut immune surveillance systems.

    Topics: Animals; Antineoplastic Agents; Interleukin-12; Interleukin-18; Intestine, Small; Killer Cells, Natural; Liposomes; Lung Neoplasms; Male; Melanoma, Experimental; Mice; Mice, Inbred C57BL; Microscopy, Confocal; Sitosterols; Tissue Distribution

2008
beta-Sitosterol induces G2/M arrest, endoreduplication, and apoptosis through the Bcl-2 and PI3K/Akt signaling pathways.
    Cancer letters, 2008, Jun-18, Volume: 264, Issue:2

    beta-Sitosterol (SITO) is a potentially valuable candidate for cancer chemotherapy, however the cellular and molecular mechanisms responsible for its anti-cancer activity are unknown. Therefore, we attempted to elucidate the mechanisms responsible for SITO-induced anti-proliferation in human leukemia cells. Treatment with SITO increased caspase-3 activation and DNA fragmentation in U937 and HL60 cells. This effect was associated with significant G2/M arrest and endoreduplication. We also demonstrated that SITO treatment significantly increases levels of polymeric alpha-tubulin and promoted microtubule polymerization. We next elucidated that ectopic expression of Bcl-2 accelerates endoreduplication in U937 cells. Furthermore, the specific Bcl-2 inhibitor, HA14-1, prevented endoreduplication through G2 phase arrest. Interestingly, SITO treatment did not significantly promote endoreduplication or decrease cell viability in Bcl-2 null K562 cells. SITO treatment also induced a gradual increase of phosphatidyl-inositol 3-kinase (PI3K) and Akt phosphorylation. Treatment with the selective PI3K/Akt inhibitor LY29004 completely blocked endoreduplication and apoptosis in the presence of SITO. In addition, treatment with SITO-induced phosphorylation of extracellular signal-regulated protein kinase (ERK), however significance of ERK activation in the execution of apoptosis and endoreduplication is unknown. These results suggest that SITO induces endoreduplication by promoting spindle microtubule dynamics through the Bcl-2 and PI3K/Akt signaling pathways.

    Topics: Antineoplastic Agents; Apoptosis; Blotting, Western; Caspase 3; Cell Cycle; Cell Line, Tumor; Cell Proliferation; Enzyme Activation; Extracellular Signal-Regulated MAP Kinases; Fluorescent Antibody Technique; Humans; Microtubules; Phosphatidylinositol 3-Kinases; Proto-Oncogene Proteins c-akt; Proto-Oncogene Proteins c-bcl-2; Signal Transduction; Sitosterols; Tubulin

2008
beta-Sitosterol enhances tamoxifen effectiveness on breast cancer cells by affecting ceramide metabolism.
    Molecular nutrition & food research, 2008, Volume: 52, Issue:4

    The objective of this study was to investigate the effects of the dietary phytosterol beta-sitosterol (SIT) and the antiestrogen drug tamoxifen (TAM) on cell growth and ceramide (CER) metabolism in MCF-7 and MDA-MB-231 human breast cancer cells. The MCF-7 and MDA-MB-231 cell lines were studied as models of estrogen receptor positive and estrogen receptor negative breast cancer cells. Growth of both cell lines as determined using the sulforhodamine B assay was inhibited by treatment with 16 microM SIT but only MCF-7 cell growth was inhibited by treatment with 1 microM TAM. The combination of SIT and TAM further inhibited growth in both cell lines, most significantly in MDA-MB-231 cells. CER is a proapoptotic signal and CER levels were increased in both MCF-7 and MDA-MB-231 cells by individual treatment with SIT and TAM and the combined treatment raised cellular CER content even further. SIT and TAM raised CER levels by different means. SIT potently activated de novo CER synthesis in both MCF-7 and MDA-MB-231 cells by stimulating serine palmitoyltransferase activity; whereas TAM promoted CER accumulation in both cell types by inhibiting CER glycosylation. These results suggest that the combination regimen of dietary SIT and TAM chemotherapy may be beneficial in the management of breast cancer patients.

    Topics: Antineoplastic Agents, Hormonal; Breast Neoplasms; Cell Division; Cell Line, Tumor; Cell Survival; Ceramides; Drug Synergism; Female; Humans; Serine C-Palmitoyltransferase; Sitosterols; Sphingolipids; Tamoxifen

2008
[Studies on chemical constituents from roots of Mirabilis jalapa].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2008, Volume: 33, Issue:1

    To investigate the anti-HIV constituents from the root of Mirabilis jalapa.. The compounds were isolated by column chromatography on silica gel, Sephadex LH - 20, MCI-gel CHP-20P and RP-18. The structure were identified by means of NMR and MS analyses (1H-NMR, 13C-NMR, MS).. Eleven compounds were isolated and identified as astragaloside II (1), astragaloside II (2), astragaloside IV (3), astragaloside VI (4), flazin (5), 4'-hydroxy-2, 3-dihydroflavone 7-beta-D-glucopyranoside (6), gingerglycolipid A (7), 3, 4-dihydroxybenzaldehyd (8), p-hydroxybenzaldehyde (9), beta-sitosterol (10) and daucosterol (11).. Compounds 1-9 were obtained from this genus for the first time.

    Topics: Benzaldehydes; Carbolines; Chromatography, Gel; Furans; Galactolipids; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mirabilis; Plant Roots; Sitosterols

2008
Inhibition of cholesterol transport into skin cells in cultures by phytosterol-loaded microemulsion.
    Chemistry and physics of lipids, 2008, Volume: 153, Issue:2

    Cholesterol and plant phytosterols are lipophilic compounds solubilized by intestinal micelles in a competitive manner. In this work, we used radioactive cholesterol- and phytosterol-loaded oil-in-water microemulsions to follow their incorporation and mutual competition in HaCaT keratinocytes, SZ95 sebocytes, and skin pieces in cultures. Dynamic light scattering showed homogenous nanostructures of 10.5+/-1.5 nm diameter and cryo-transmission electron microscopy confirmed the presence of uniform spherical droplets of 7.0+/-1.0 nm diameter. Up to 320 nmol/ml of cholesterol can be solubilized and transported into cells with minimal toxic effect by 0.5 wt% nanodroplets in a cell medium. Phytosterols inhibit incorporation of cholesterol into cells, in vitro, at molar ratios (phytosterols/cholesterol) of 4 and above. The loaded nanodroplets accumulate in intracellular vesicles (presumably endosomes). No metabolic conversion of cholesterol or phytosterols was found in these cells, in vitro, after 24 h, at 37 degrees C.

    Topics: Cell Survival; Cells, Cultured; Cholestadienols; Cholesterol; Cryoelectron Microscopy; Emulsions; Humans; Keratinocytes; Microscopy, Electron, Transmission; Phytosterols; Sitosterols

2008
Antitubercular triterpenes and phytosterols from Pandanus tectorius Soland. var. laevis.
    Journal of natural medicines, 2008, Volume: 62, Issue:2

    Bioassay-guided chromatographic purification of the antitubercular chloroform extract of Pandanus tectorius Soland. var. laevis leaves afforded a new tirucallane-type triterpene, 24,24-dimethyl-5 beta-tirucall-9(11),25-dien-3-one (1), squalene and a mixture of the phytosterols stigmasterol and beta-sitosterol. Microplate Alamar Blue Assay (MABA) showed that 1 inhibited the growth of Mycobacterium tuberculosis H(37)Rv with a MIC of 64 microg/mL, while squalene and the sterol mixture have MICs of 100 and 128 microg/mL, respectively.

    Topics: Antitubercular Agents; Microbial Sensitivity Tests; Mycobacterium tuberculosis; Pandanaceae; Phytosterols; Plant Extracts; Plant Leaves; Sitosterols; Squalene; Stigmasterol; Triterpenes

2008
Natural wax constituents of a supercritical fluid CO(2) extract from quince (Cydonia oblonga Mill.) pomace.
    Analytical and bioanalytical chemistry, 2008, Volume: 391, Issue:2

    The chemical constituents of a lipophilic extract from quince (Cydonia oblonga Mill.), obtained by supercritical fluid CO(2) extraction of the dried fruit pomace were investigated. Solvent partition of quince wax with n-hexane or acetone yielded an insoluble (crystalline) and a soluble (oily) fraction. Both fractions were analyzed separately using gas chromatography/mass spectrometry (GC/MS). The insoluble fraction consisted of saturated n-aldehydes, n-alcohols and free n-alkanoic acids of carbon chain lengths between 22 and 32, with carbon chain lengths of 26 and 28 dominating. Also odd-numbered unbranched hydrocarbons, mainly C27, C29 and C31, were detected particularly in the acetone-insoluble fraction (total, 15.8%). By means of vacuum liquid chromatography, triterpenoic acids were separated from the hexane-insoluble matter and identified as a mixture of ursolic, oleanolic and betulinic acids. The major constituents of the hexane-soluble fraction were glycerides of linoleic [Δ(9,12), 18:2] and oleic [Δ(9), 18:1] acids, accompanied by free linoleic, oleic and palmitic acids (C16). Moreover β-sitosterol, Δ(5)-avenasterol as well as trace amounts of other sterols were assigned. Finally the carotenoids phytoene and phytofluene were identified and quantified by UV/vis and high-performance liquid chromatography/MS techniques, yielding 1.0 and 0.3% of the quince wax, respectively. It is anticipated that the complex of lipid constituents from quince wax may exert interesting biological activities, the elucidation of which awaits further studies.

    Topics: Acetone; Alcohols; Alkanes; Carotenoids; Chemical Fractionation; Fatty Acids; Fruit; Gas Chromatography-Mass Spectrometry; Hexanes; Nuclear Magnetic Resonance, Biomolecular; Plant Extracts; Rosaceae; Sitosterols; Triterpenes; Waxes

2008
Beneficial or harmful influence of phytosterols on human cells?
    The British journal of nutrition, 2008, Volume: 100, Issue:6

    So far, a protective influence of phytosterols on the human organism and atherogenesis has been suggested. Most studies have concentrated on the cytotoxic efficacy of phytosterols on cancer cells. However, there are only a few reports showing their influence on normal cells. The aim of the present study was to determine whether dietary plant sterols and their thermal processing products could influence the viability of normal, abdominal endothelial cells that play a crucial role in atherogenesis. Thus, we studied the effect of rapeseed oil-extract components, beta-sitosterol, cholesterol and their epoxy-derivatives, 5 alpha,6 alpha-epoxy-beta-sitosterol and 5 alpha,6 alpha-epoxycholesterol, on the proliferation and viability of human abdominal aorta endothelial cells HAAE-2 in vitro. We showed strong cytotoxic properties of beta-sitosterol in HAAE-2 cells (half maximal inhibitory concentration (IC50) = 1.99 (SEM 0.56) microm) and, interestingly, a weaker cytotoxic effect of 5 alpha,6 alpha-epoxy-beta-sitosterol (IC50>200 microm). Moreover, we observed a significantly stronger cytotoxic activity of beta-sitosterol than cholesterol (IC50 = 8.99 (SEM 2.74) microm). We also revealed that beta-sitosterol as well as cholesterol caused apoptosis, inducing caspase-3 activity in the cells (60 % increase compared with control cells) that corresponded to the DNA fragmentation analysis in a terminal uridine deoxynucleotidyl transferase-mediated deoxyuridine triphosphate nick-end labelling (TUNEL) study. Although absorption of plant sterols is low compared with cholesterol, they can still influence other physiological functions. Since they effectively reduce serum LDL-cholesterol and atherosclerotic risk but also decrease the viability of cancer cells as well as normal cells in a time- and dose-dependent manner in vitro, their influence on other metabolic processes remains to be elucidated.

    Topics: Aorta, Abdominal; Apoptosis; Caspase 3; Cell Death; Cell Proliferation; Cells, Cultured; Cholesterol; DNA Fragmentation; Dose-Response Relationship, Drug; Endothelium, Vascular; Fatty Acids, Monounsaturated; Humans; Phytosterols; Plant Oils; Rapeseed Oil; Sitosterols

2008
Ripening-specific stigmasterol increase in tomato fruit is associated with increased sterol C-22 desaturase (CYP710A11) gene expression.
    Journal of agricultural and food chemistry, 2008, May-28, Volume: 56, Issue:10

    Phytosterol content and composition and sterol C-22 desaturase (LeSD1; CYP710A11) transcript levels in pericarp tissue of 'Rutgers' tomato fruit were compared in the wild-type (wt) and isogenic lines of the nonripening mutants nor and rin at four stages of ripening/aging. Wild-type fruit were harvested at the mature-green (MG), breaker (BK), breaker plus 3 days (B + 3), and breaker plus 6 days (B + 6) stages, whereas nor and rin fruits were harvested at comparable chronological ages (days after pollination). At the MG stage, wt and mutant fruits had closely similar sterol contents, compositions, and conjugations, with >91% of the total sterols in the acylated steryl glycoside plus steryl glycoside (ASG + SG) fraction. During ripening/aging, there were substantial increases in total sterols and the percentage of sterols in the free plus esterified (FS + SE) fraction. Both changes were greater in wt than in nor or rin. In fruit of wt, rin, and nor, respectively, the increases in total sterols between MG and B + 6 were 2.1-, 1.9-, and 1.5-fold, and at B + 6 the percentages of total sterols in FS + SE were 42, 21, and 24. Among all sterol lipids (ASG, SG, FS, and SE), the ratio of stigmasterol (stigmasta-5,22-dien-3beta-ol) to beta-sitosterol (stigmast-5-en-3beta-ol), the two major sterols in tomato, increased 2.3-fold during ripening of wt fruit but declined slightly during comparable aging of nor and rin fruits. In accord with these changes, the abundance of LeSD1 transcript increased 4-fold in pericarp of ripening wt fruit, peaking at B + 3, whereas transcript levels in nor and rin fruits fluctuated but never exceeded the abundance in wt fruit at the MG stage. These findings indicate that the ripening-specific increase in stigmasterol in wt fruit results from a marked increase in LeSD1 transcription and translation, which accelerates C-22 desaturation of the precursor sterol, beta-sitosterol.

    Topics: Amino Acid Sequence; Base Sequence; Cytochrome P-450 Enzyme System; DNA, Complementary; Fruit; Gene Expression; Phytosterols; RNA, Messenger; Sitosterols; Solanum lycopersicum; Stigmasterol

2008
Modulation of cytokine production by plant sterols in stimulated human Jurkat T cells.
    Molecular nutrition & food research, 2008, Volume: 52, Issue:6

    The plant sterols campesterol, beta-sitosterol and beta-sitostanol were investigated for potential immunomodulatory effects in Jurkat T cells. Treatments involved supplementing cells with or without concanavalin A (ConA) or phorbol-12-myristate-13-acetate plus ionomycin (PMA+IoM) in the presence or absence of increasing concentrations (10-100 microM) of each plant sterol for 24 h. None of the plant sterols significantly affected mitogen-stimulated IL-4, IL-10 or IFN-gamma production. However, campesterol, beta-sitosterol and beta-sitostanol significantly suppressed mitogen-induced IL-2 production in a dose-dependent manner. Both bisindolylmaleimide-I (BIM-I), a specific protein kinase C (PKC) inhibitor, and the immunosuppressant drug known as Tacrolimus (FK506), an IL-2 inhibitor, prevented mitogen-stimulated IL-2 production in Jurkat cells. Treatment with PMA+IoM alone significantly increased PKC activity and the presence of BIM-I prevented PKC activation by PMA+IoM. Following 24 h treatments, the plant sterols did not affect PMA+IoM-enhanced PKC activity, cellular calcium content or calcineurin activity. Intracellular cyclic 3',5'-adenosine monophosphate (cAMP) levels were significantly reduced by PMA+IoM. The presence of FK506 prevented a PMA+IoM-induced reduction of intracellular cAMP. Likewise the plant sterols behaved in a similar manner as FK506. Our findings suggest that the suppression of IL-2 by the plant sterols was not mediated via PKC inhibition and that their effects occurred possibly via cAMP modulation and/or a calcium/calcineurin-independent pathway.

    Topics: Cell Division; Cell Survival; Cholesterol; Concanavalin A; Cytokines; Enzyme Inhibitors; Humans; Immunologic Factors; Immunosuppressive Agents; Indoles; Interleukin-2; Jurkat Cells; Lymphocyte Activation; Maleimides; Phytosterols; Protein Kinase C; Sitosterols; T-Lymphocytes; Tacrolimus; Tetradecanoylphorbol Acetate

2008
Variations in phytosterol composition during the ripening of Tunisian safflower (Carthamus tinctorius L.) seeds.
    Pakistan journal of biological sciences : PJBS, 2007, Nov-01, Volume: 10, Issue:21

    Phytosterols are bioactive components of all vegetable foods. Their most studied and outstanding properties being their cholesterol-lowering activity. This property has led to the development of functional foods enriched with plant sterols. In the present study, total and conjugated sterols of Tunisian safflower seeds were investigated and their kinetic of accumulation was surveyed during the ripening stages. The results obtained revealed that total and individual phytosterols were actively accumulated during the first stages of seed development then their levels decreased until full maturity. In the other hand, the sterol profile was marked by the predominance of beta-sitosterol during all ripening stages. As for Free Sterols (FS) and Esterified Sterols (ES), they were the major components and were actively accumulated from the beginning of seed development. Nevertheless, their amounts decreased at the end of maturity while Steryl Glycosides (SG) and acylated sterylglycosides (ASG) were practically stable during the ripening of seeds.

    Topics: Animals; Botany; Carthamus tinctorius; Cholesterol; Chromatography, Gas; Chromatography, Thin Layer; Kinetics; Mass Spectrometry; Phytosterols; Seeds; Sitosterols; Sterols; Time Factors

2007
Isolation of stigmasterol and beta-sitosterol from methanolic extract of root bark of Calotropis gigantea (Linn).
    Pakistan journal of biological sciences : PJBS, 2007, Nov-15, Volume: 10, Issue:22

    Aim of this study is to identify and characterize the bioactive principles from the root bark of Calotropis gigantea. It has wide folk medicinal use. For isolation of the compounds, the dried root bark's powder of Calotropis gigantea were subjected to hot extraction and then the crude methanol (MeOH) extract was fractionated with petroleum ether, chloroform and ethyl acetate. Two compounds were isolated and purified from petroleum ether fraction of crude methanol extract and the structures were determined as stigmasterol and beta-sitosterol by analysis of physical, chemical and spectral characteristics (1D NMR and mass spectrometry).

    Topics: Acetates; Alcohols; Alkanes; Calotropis; Chloroform; Hot Temperature; Magnetic Resonance Spectroscopy; Mass Spectrometry; Methanol; Models, Chemical; Plant Roots; Sitosterols; Spectrophotometry; Stigmasterol

2007
Sitosterol and cholesterol in chylomicrons of type 2 diabetic and non-diabetic subjects: the relationship with ATP binding cassette proteins G5 and G8 and Niemann-Pick C1-like 1 mRNA.
    Diabetologia, 2007, Volume: 50, Issue:1

    Topics: Aged; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Case-Control Studies; Cholesterol; Cholesterol, Dietary; Chylomicrons; Diabetes Mellitus, Type 2; Female; Gene Expression Regulation; Humans; Lipoproteins; Male; Membrane Proteins; Membrane Transport Proteins; Middle Aged; RNA, Messenger; Sitosterols

2007
Niemann-Pick C1-like 1 overexpression facilitates ezetimibe-sensitive cholesterol and beta-sitosterol uptake in CaCo-2 cells.
    The Journal of pharmacology and experimental therapeutics, 2007, Volume: 320, Issue:2

    Previous in vivo studies including those with knockout mice suggested that Niemann-Pick C1-like 1 (NPC1L1) plays an essential role in the intestinal absorption of cholesterol. To characterize the mechanism of cholesterol uptake mediated by NPC1L1, an in vitro system reflecting the function of this transporter needs to be established. In the present study, we constructed NPC1L1 overexpressing CaCo-2 cells as an in vitro model and characterized the transport properties of NPC1L1. Immunohistochemical staining revealed that CaCo-2 cells express NPC1L1 on the apical membrane. It was also demonstrated that the uptakes of both cholesterol and beta-sitosterol are increased by NPC1L1 overexpression. In addition, the uptake of cholesterol was increased in a dose-dependent manner by an increase in the content of taurocholate in micelles, whereas micellar phosphatidylcholine showed a negative correlation with cholesterol uptake. Furthermore, it was confirmed that sterol uptake increased by NPC1L1 overexpression was inhibited by ezetimibe. We could thus establish an in vitro intestinal model to study the mechanism of NPC1L1-dependent sterol uptake and to screen drug candidates whose target is NPC1L1.

    Topics: Anticholesteremic Agents; Azetidines; Caco-2 Cells; Cholesterol; Ezetimibe; Humans; Membrane Transport Proteins; Micelles; Phosphatidylcholines; Sitosterols; Taurocholic Acid

2007
Steroid-1-dehydrogenase of Mycobacterium sp. VKM Ac-1817D strain producing 9alpha-hydroxy-androst-4-ene-3,17-dione from sitosterol.
    Applied microbiology and biotechnology, 2007, Volume: 74, Issue:4

    The strain of Mycobacterium sp. VKM Ac-1817D forms 9alpha-hydroxy-androst-4-ene-3,17-dione (9-OH-AD) as a major product from sitosterol. The formation of 9-OH-AD was accompanied with its partial destruction due to residual steroid-1-dehydrogenase (St1DH) activity. The activity was found to be induced by androst-4-ene-3,17-dione (AD), while other intermediates of sitosterol oxidation did not influence 1(2)-dehydrogenation. The enzyme is located mainly in the cytosolic fraction. The cytosolic St1DH (dimer, M (r) approximately 58 kDa) was partially purified by ammonium sulfate fractionation, ion-exchange chromatography on DEAE-Sepharose and Phenyl-Sepharose, and gel filtration on Bio-Gel A-0.5M. It expressed the St1DH activity toward both AD and 9-OH-AD.

    Topics: Ammonium Sulfate; Androstenedione; Chemical Fractionation; Chromatography, Gel; Chromatography, Ion Exchange; Cytosol; Enzyme Induction; Models, Biological; Molecular Structure; Molecular Weight; Mycobacterium; Oxidoreductases; Sitosterols

2007
Preparative isolation and purification of chemical constituents from the root of Adenophora tetraphlla by high-speed counter-current chromatography with evaporative light scattering detection.
    Journal of chromatography. A, 2007, Jan-19, Volume: 1139, Issue:2

    Preparative high-speed counter-current chromatography (HSCCC), as a continuous liquid-liquid partition chromatography with no solid support matrix, combined with evaporative light scattering detection (ELSD) was employed for systematic separation and purification of non-chromophoric chemical components from Chinese medicinal herb Adenophora tetraphlla (Thunb.), Fisch. Nine compounds, including alpha-spinasterol, beta-sitosterol, nonacosan-10-ol, 24-methylene cycloartanol, lupenone, 3-O-palmitoyl-beta-sitosterol, 3-O-beta-d-glucose-beta-sitosterol, eicosanoic acid and an unknown compound, were obtained. The compounds were all above 95% determined by high-performance liquid chromatography (HPLC)-ELSD, and their structures were identified by (1)H NMR and chemical ionization mass spectroscopy (CI-MS). The results demonstrate that HSCCC coupled with ELSD is a feasible and efficient technique for systematic isolation of non-chromophoric components from traditional medicinal herbs.

    Topics: Campanulaceae; Chromatography, High Pressure Liquid; Countercurrent Distribution; Light; Phytosterols; Plant Roots; Sitosterols; Stigmasterol; Triterpenes

2007
Beta-sitosterol and 17beta-estradiol alter gonadal steroidogenic acute regulatory protein (StAR) expression in goldfish, Carassius auratus.
    General and comparative endocrinology, 2007, Volume: 151, Issue:1

    Fish exposed to the phytosterol beta-sitosterol (beta-sit) have decreased circulating hormone and cholesterol concentrations, and decreased gonadal intra-mitochondrial cholesterol pools. The current study examined the potential for beta-sit to alter abundance of the key cholesterol transport protein, steroidogenic acute regulatory (StAR) protein, which delivers cholesterol to the first and rate-limiting steroidogenic enzyme P450 side chain cleavage (P450(scc)) inside the mitochondria. Plasma testosterone (T) and lipids (cholesterol, lipoproteins and triglycerides) were also measured. Goldfish were exposed to 200 microg/g beta-sit (97% pure or as a 72.6% pure phytosterol mixture) and 10 microg/g 17beta-estradiol (E(2); estrogenic control) by intra-peritoneal Silastic implants for 21-days or for five-months. Plasma T was significantly decreased in male fish exposed to the phytosterol mixture following the long-term exposure (p<0.001). There were no differences in total cholesterol concentrations among treatments in the short- or long-term exposure, but male fish in the long-term exposure had significantly lower HDL as compared to control fish (p<0.025) with a corresponding increase in LDL. StAR transcript levels were unchanged following the short-term exposure, but were reduced after five months in male beta-sit fish (p=0.05) and E(2)-treated female fish (p=0.05). This reduction in StAR transcript abundance in conjunction with decreased plasma T and altered plasma lipoprotein fractions demonstrates a non-estrogenic effect of beta-sit. This is the first study to show that beta-sit has the capacity to alter gonadal StAR transcript abundance, offering a mechanism by which beta-sit disrupts reproductive endocrine endpoints.

    Topics: Animals; Cholesterol; Estradiol; Female; Goldfish; Gonads; Lipids; Male; Molecular Structure; Phosphoproteins; Radioimmunoassay; Reverse Transcriptase Polymerase Chain Reaction; Sitosterols; Testosterone; Transcription, Genetic

2007
Sitosterol xanthomatosis.
    Journal of the European Academy of Dermatology and Venereology : JEADV, 2007, Volume: 21, Issue:1

    Sitosterolaemia is a lipid disorder in which plasma plant sterol levels are extremely elevated. Sitosterolaemia is clinically characterized by tuberous and tendon xanthomas, premature vascular disease and arthritis.. To report a case of sitosterolaemia diagnosed by cutaneous manifestations and to review this rare disease.. We report the case of a 60-year-old woman who presented with cutaneous xanthomas, arterial hypertension and polyarthralgias. The patient had had hypercholesterolaemia for many years without reduction of serum cholesterol, despite treatment with fenofibrate.. Ezetimibe therapy was started, decreasing sitosterol plasmatic levels and tuberous xanthomas after 3 months of treatment.. It is important to detect levels of sitosterol in plasma in patients with premature vascular disease, presence of xanthomas, and uncontrolled hypercholesterolaemia. Ezetimibe therapy is effective.

    Topics: Azetidines; Ezetimibe; Female; Humans; Hypolipidemic Agents; Middle Aged; Sitosterols; Xanthomatosis

2007
Triterpenoids from Eugenia grandis: structure elucidation by NMR spectroscopy.
    Magnetic resonance in chemistry : MRC, 2007, Volume: 45, Issue:3

    A new pentacyclic triterpenoid, 2alpha,3beta-dihydroxylup-12-en-28-oic acid (1) and a rarely encountered pentacyclic triterpenoid, 3beta-hydroxylup-12-en-28-oic acid (2), together with five known compounds, friedelin (3), 3beta-friedelinol (4), betulinic acid (5), oleanolic acid (6) and beta-sitosterol (7) were isolated from the chloroform extract of stem bark of Eugenia grandis (Syn: Syzygium grande). The structure and stereochemistry of the new compound (1) and the rarely encountered compound (2) were established by 1D and 2D NMR spectroscopic techniques. All the above isolated compounds from this plant are reported for the first time.

    Topics: Betulinic Acid; Deuterium; Magnetic Resonance Spectroscopy; Molecular Conformation; Oleanolic Acid; Pentacyclic Triterpenes; Protons; Reference Standards; Sensitivity and Specificity; Sitosterols; Stereoisomerism; Syzygium; Triterpenes

2007
Chemical compositions of fine particulate organic matter emitted from Chinese cooking.
    Environmental science & technology, 2007, Jan-01, Volume: 41, Issue:1

    Food cooking can be a significant source of atmospheric particulate organic matter. In this study, the chemical composition of particulate organic matter (POM) in PM2.5 emitted from four different Chinese cooking styles were examined by gas chromotography-mass spectrometry (GC-MS). The identified species are consistent in the emissions from different Chinese cooking styles and the quantified compounds account for 5-10% of total POM in PM2.5. The dominant homologue is fatty acids, constituting 73-85% of the quantified compounds. The pattern of n-alkanes and the presence of beta-sitosterol and levoglucosan indicate that vegetables are consumed during Chinese cooking operations. Furthermore, the emissions of different compounds are impacted significantly by the cooking ingredients. The candidates of organic tracers used to describe and distinguish emissions from Chinese cooking in Guangzhou are tetradecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, levoglucosan, mannosan, galactosan, nonanal, and lactones. During the sampling period, the relative contribution of Chinese cooking to the mass concentration of atmospheric hexadecanoic acid should be less than 1.3% in Guangzhou.

    Topics: Air Pollution, Indoor; Alkanes; China; Cooking; Dicarboxylic Acids; Fatty Acids; Food Analysis; Gas Chromatography-Mass Spectrometry; Glucose; Palmitic Acid; Particle Size; Particulate Matter; Polycyclic Aromatic Hydrocarbons; Restaurants; Sitosterols

2007
Highly sensitive analysis of cholesterol and sitosterol in foods and human biosamples by liquid chromatography with fluorescence detection.
    Journal of chromatography. A, 2007, Jul-13, Volume: 1156, Issue:1-2

    A simple and sensitive method is described for the quantitative analysis of important animal and plant sterols (cholesterol and sitosterol) by liquid chromatography with fluorimetric detection. The method is based on the derivatization of cholesterol and sitosterol with a fluorescent reagent (naproxen acyl chloride) in toluene. The resulting derivatives were isocratically separated on a C(8) column with a mixed solvent of methanol-isopropanol-water (90:5:5, v/v) as a mobile phase and monitored with a fluorimetric detector (excitation 231 nm and emission 352 nm). The linear range for the quantitation of cholesterol or sitosterol was 0.1-2.0 microM with a detection limit (S/N=3 with 10 microl injected) of about 25 nM. Recoveries of cholesterol spiked in milk (n=5) ranged over 99-104% with relative standard deviations (RSD) less than 6.0%. Application of the method to the analysis of cholesterol or sitosterol in milk, saliva and urine proved simple and feasible.

    Topics: Animals; Cattle; Cholesterol; Chromatography, High Pressure Liquid; Food Analysis; Humans; Milk; Saliva; Sensitivity and Specificity; Sitosterols; Soy Foods

2007
Viper and cobra venom neutralization by beta-sitosterol and stigmasterol isolated from the root extract of Pluchea indica Less. (Asteraceae).
    Phytomedicine : international journal of phytotherapy and phytopharmacology, 2007, Volume: 14, Issue:9

    We reported previously that the methanolic root extract of the Indian medicinal plant Pluchea indica Less. (Asteraceae) could neutralize viper venom-induced action [Alam, M.I., Auddy, B., Gomes, A., 1996. Viper venom neutralization by Indian medicinal plant (Hemidesmus indicus and P. indica) root extracts. Phytother. Res. 10, 58-61]. The present study reports the neutralization of viper and cobra venom by beta-sitosterol and stigmasterol isolated from the root extract of P. indica Less. (Asteraceae). The active fraction (containing the major compound beta-sitosterol and the minor compound stigmasterol) was isolated and purified by silica gel column chromatography and the structure was determined using spectroscopic analysis (EIMS, (1)H NMR, (13)C NMR). Anti-snake venom activity was studied in experimental animals. The active fraction was found to significantly neutralize viper venom-induced lethal, hemorrhagic, defibrinogenation, edema and PLA(2) activity. Cobra venom-induced lethality, cardiotoxicity, neurotoxicity, respiratory changes and PLA(2) activity were also antagonized by the active component. It potentiated commercial snake venom antiserum action against venom-induced lethality in male albino mice. The active fraction could antagonize venom-induced changes in lipid peroxidation and superoxide dismutase activity. This study suggests that beta-sitosterol and stigmasterol may play an important role, along with antiserum, in neutralizing snake venom-induced actions.

    Topics: Animals; Antivenins; Asteraceae; Elapid Venoms; Male; Mice; Phytotherapy; Plant Extracts; Plant Roots; Sitosterols; Stigmasterol; Viper Venoms

2007
Plant sterols in "rafts": a better way to regulate membrane thermal shocks.
    FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 2007, Volume: 21, Issue:8

    Specialized lipid domains (rafts) that are generally enriched in sterols and sphingolipids, are most likely present in cell membranes of animals, plants and fungi. While cholesterol and ergosterol are predominant in vertebrates and fungi, plants possess complex sterol profiles, dominated by sitosterol and stigmasterol in Arabidopsis thaliana. Fully hydrated model membranes of composition approaching those found in rafts of mammals, fungi and plants were investigated by means of solid-state 2H-NMR, using deuterated dipalmitoylphosphatidylcholine (2H(62)-DPPC). The dynamics of such membranes was determined through measuring of membrane ordering or disordering properties. The presence of the liquid-ordered, lo, phase, which may be an indicator of rigid sterol-sphingolipid domains, was detected in all binary or ternary mixtures of all sterols investigated. Of great interest, the dynamics of ternary mixtures mimicking rafts in plants (phytosterol/glucosylcerebroside/DPPC), showed a lesser temperature sensitivity to thermal shocks, on comparing to systems mimicking rafts in mammals and fungi. This effect was particularly marked with sitosterol. The presence of an ethyl group branched on the alkyl chain of sitosterol and stigmasterol is proposed as reinforcing the membrane cohesion by additional attractive van der Waals interactions with the alkyl chains of sphingolipids and phospholipids. As a side result, the elevated resolution of NMR spectra in the presence of sitosterol also suggests domains of smaller size than with other sterols. Finally, the role of phytosterols in maintaining plant membranes in a state of dynamics less sensitive to temperature shocks is discussed.

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Deuterium; Liposomes; Magnetic Resonance Spectroscopy; Membrane Microdomains; Models, Biological; Phytosterols; Plants; Sitosterols; Sterols; Stigmasterol; Temperature

2007
beta-Sitosterol activates Fas signaling in human breast cancer cells.
    Phytomedicine : international journal of phytotherapy and phytopharmacology, 2007, Volume: 14, Issue:11

    beta-Sitosterol is the most abundant phytosterol. Phytosterols are enriched in legumes, oil seeds and unrefined plant oils as found in foods such as peanut butter, pistachios and sunflower seeds. beta-Sitosterol inhibits the growth of several specific types of tumor cells in vitro and decreases the size and the extent of tumor metastases in vivo. The effects of beta-sitosterol on the extrinsic apoptotic programmed cell death pathway in human breast MCF-7 and MDA-MB-231 adenocarcinoma cells were examined, along with the extent of its incorporation into cellular membranes and its effects on cell growth, expression of Fas receptor pathway proteins, and caspase-8 activity. The results show that beta-sitosterol exposure promotes its enrichment in transformed cell membranes and significantly inhibits tumor cell growth. Concurrently, Fas levels and caspase-8 activity are significantly increased. These actions are specific, as expression of other proteins of the Fas receptor pathway, including Fas ligand, FADD, p-FADD and caspase-8, remain unchanged. These findings support the hypothesis that beta-sitosterol is an effective apoptosis-promoting agent and that incorporation of more phytosterols in the diet may serve a preventive measure for breast cancer.

    Topics: Antineoplastic Agents, Phytogenic; Apoptosis; Breast Neoplasms; Cell Line, Tumor; Fas Ligand Protein; Female; Humans; Phytotherapy; Plants, Medicinal; Signal Transduction; Sitosterols

2007
Isolation of fatty acids and aromatics from cell suspension cultures of Lavandula angustifolia.
    Natural product research, 2007, Volume: 21, Issue:2

    Cell suspension cultures of Lavandula angustifolia Mill. ssp. angustifolia (syn.: L. officinalis Chaix.) afforded a fatty acid composition, cis and trans p-coumaric acids (=p-hydroxy cinnamic acids), and beta-sitosterol. The fatty acid composition was analyzed by GC-MS, and the structures of the isolated three compounds were determined by 1H- and 13C-NMR, and MS spectroscopic techniques.

    Topics: Cells, Cultured; Coumaric Acids; Fatty Acids; Gas Chromatography-Mass Spectrometry; Lavandula; Magnetic Resonance Spectroscopy; Sitosterols

2007
Endocrine modulating actions of a phytosterol mixture and its oxidation products in zebrafish (Danio rerio).
    Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 2007, Volume: 145, Issue:4

    In this study, a phytosterol preparation ("ultrasitosterol"; 80% beta-sitosterol) and an oxidized ultrasitosterol preparation were evaluated for reproductive effects in zebrafish. Adults were exposed in a continuous flow to 10 microg/L and 100 microg/L ultrasitosterol and oxidized ultrasitosterol, and to 0.27 microg/L 17beta-estradiol and 0.28 microg/L testosterone for 3 weeks. Biomarkers analysed included plasma vitellogenin, testosterone, 11-ketotestosterone, 17beta-estradiol, and gonadal histopathology. Ovarian steroid production of testosterone and 17beta-estradiol was examined in isolated zebrafish follicles exposed in vitro to the compounds at the same concentrations as in vivo. Vtg was induced in males exposed to ultrasitosterol, and in males and females exposed to 17beta-estradiol. Males exposed to oxidized phytosterols showed increased levels of testosterone and 11-ketotestosterone, and accelerated spermatogenesis. Increased follicular atresia was observed in females exposed to oxidized phytosterols and 17beta-estradiol. Correlation analyses between biomarkers revealed more intercorrelated values for females than for males, and the strongest associations were found in females exposed to oxidized phytosterols. Testosterone production was significantly increased in follicles exposed to the oxidized phytosterol preparations. These findings indicate that the phytosterol mixture is weakly estrogenic in male fish, and that the oxidized phytosterol mixture contains substances that may interfere with spermatogenesis, oogenesis and gonadal steroidogenesis in zebrafish.

    Topics: Animals; Biomarkers; Female; Gonadal Steroid Hormones; Gonads; Male; Oxidation-Reduction; Reproduction; Sitosterols; Vitellogenins; Zebrafish

2007
beta-sitosterol decreases irradiation-induced thymocyte early damage by regulation of the intracellular redox balance and maintenance of mitochondrial membrane stability.
    Journal of cellular biochemistry, 2007, Oct-15, Volume: 102, Issue:3

    Both radiation injury and oxidation toxicity occur when cells are exposed to ion irradiation (IR), ultimately leading to apoptosis. This study was designed to determine the effect of beta-sitosterol (BSS) on early cellular damage in irradiated thymocytes and a possible mechanism of effect on irradiation-mediated activation of the apoptotic pathways. Thymocytes were irradiated (6 Gy) with or without BSS. Cell apoptosis and apoptosis-related proteins were evaluated. BSS decreased irradiation-induced cell death and nuclear DNA strand breaks while attenuating intracellular reactive oxygen species (ROS) and increasing the activities of antioxidant enzymes, including superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx). BSS decreased the release of cytochrome c from mitochondria to the cytosol and the mitochondrio-nuclear translocation of apoptosis-inducing factor (AIF). Furthermore, BSS partially inhibited the radiation-induced increase of cleaved caspase 3 and cleaved PARP, and attenuated the activation of JNK and AP-1. In addition, evidence suggests that ROS generated by irradiation are involved in this course of cell damage. The results indicate that BSS confers a radioprotective effect on thymocytes by regulation of the intracellular redox balance which is carried out via the scavenging of ROS and maintenance of mitochondrial membrane stability.

    Topics: Animals; Apoptosis; Apoptosis Inducing Factor; Female; Glutathione Peroxidase; Hypolipidemic Agents; Mice; Mice, Inbred BALB C; Mitochondrial Membranes; Models, Biological; Oxidation-Reduction; Signal Transduction; Sitosterols; Superoxide Dismutase; Thymus Gland

2007
Lipid dynamics in goldfish (Carassius auratus) during a period of gonadal recrudescence: Effects of beta-sitosterol and 17beta-estradiol exposure.
    Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 2007, Volume: 145, Issue:4

    The potential for contaminants to alter lipid or cholesterol dynamics in fish is rarely investigated and may include critical physiological endpoints that are impacted by exposure to endocrine-active substances. The current study investigated plasma and tissue lipid dynamics over a period of recrudescence in goldfish, while also examining the potential for beta-sitosterol (beta-sit), a phytosterol and 17beta-estradiol (E(2)), an endogenous estrogen, to alter lipid homeostasis. Goldfish were exposed to 0 microg/g (no chemical; control), 200 microg/g beta-sit (72.3% sitosterol mixture) or 10 microg/g 17beta-estradiol (E2) via Silastic implants for a period of five months. Plasma lipids peaked in control fish coincident with maximum liver size, while gonadal cholesterol concentration was highest concomitant with maximum gonad size. Plasma lipid concentrations were highly affected by E2 but not beta-sit exposure; E2 elevated total cholesterol (p<0.001) and triglyceride (TG; p<0.001) and decreased high-density lipoprotein (HDL) concentration (p<0.001) in male fish. Tissue cholesterol concentrations were minimally affected by beta-sit exposure, while hepatic cholesterol concentrations were increased in E2 exposed females (p=0.041), indicating elevated liver lipogenesis in response to E2, but not beta-sit, exposure. The present study demonstrates differential effects by beta-sit and E2 on plasma lipoprotein profile and TG concentration and indicates estrogen-specific effects on hepatic lipid metabolism during gonadal development.

    Topics: Animals; Cholesterol; Estradiol; Female; Goldfish; Gonads; Lipids; Liver; Male; Sitosterols; Testosterone; Triglycerides

2007
[Studies on chemical constituents from the fruiting bodies of Ganoderma sinense Zhao, Xu et Zhang].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:3

    To study the chemical constituents from the fruiting bodies of Ganoderma sinense Zhao, Xu et Zhang.. To isolated the compounds by silica gel and sephadex LH -20 column chromatography and their structures were elucidate by means of spectral analysis.. Six sterols, one fatty acid and one of diketopiperazines were obtained from CHCl3 fraction of EtOH extract and identified as ergosta-7, 22-dien-3beta-ol (1), ergosterol (2), 6, 9-epidioxyergosta-7, 22-dien-3beta-ol (3), 5, 8-epidioxiergosta-6, 22-dien-3beta-ol (4), ergosta-7, 22-dien-3-one (5), beta-sitosterol (6), alpha-Hydroxytetracosanoic acid (7), cyclo (D-Pro-D-Val) (8).. Componds 1-8 are isolated from G. sinense Zhao, Xu et Zhang for the first time.

    Topics: Chromatography, Gel; Ergosterol; Fruiting Bodies, Fungal; Ganoderma; Sitosterols; Spectrum Analysis

2007
Monolayers (Langmuir films) behavior of multi-component systems composed of a bile acid with different sterols and with their 1:1 mixtures.
    Colloids and surfaces. B, Biointerfaces, 2007, Aug-01, Volume: 58, Issue:2

    Different physicochemical properties of Langmuir films (monolayers) composed of 10 mixed systems of a bile acid, deoxycholic acid (DC) with various plant sterols, such as stigmasterol (Stig), beta-sitosterol (Sito) and campesterol (Camp) and a stanol, cholestanol (Chsta) in addition to an animal sterol, cholesterol (Ch) [these sterols and Chsta are abbreviated as St] and DC with 1:1 St mixtures; (Ch+Chsta), (Ch+Stig), (Stig+Chsta), (Ch+Sito) and (Ch+Camp) on the substrate of 5M aqueous NaCl solution (pH 1.2) at 25 degrees C, were investigated in terms of mean surface area per molecule (A(m)), the partial molecular area (PMA), surface excess Gibbs energy (DeltaG((ex))), interaction parameter (I(p)) as well as activity coefficients (f(1) and f(2)) in 2-D phase of each binary (or ternary) component system and elasticity (Cs(-1)) of formed films; these were analyzed on the basis of the respective surface pressure (pi) versus A(m) isotherms as a function of mole fraction of Sts (X(st)) in the DC/St(s) mixtures at discrete surface pressures. Notable findings are: (i) all the binary component systems did form patched film type monolayers consisting of (a) DC-dominant film solubilizing a trace amount of St molecules and (b) St dominant film dissolving a small amount of DC molecules, (ii) DC in 2-D phase exhibited a transition from LE film to LC film at a constant pressure (pi(C)(1)) accompanied by compression and (iii) DeltaG((ex)) as well as I(p) was found to be greatly dependent on (a) the combinations of DC with different St species and (b) to be markedly varied by a difference in mixing ratio of DC to Sts. Compressibility (or elasticity) analyses and fluorescence microscopy images could support the above findings as well as interpretation.

    Topics: Cholesterol; Deoxycholic Acid; Phytosterols; Sitosterols; Unilamellar Liposomes

2007
Inhibition of colon cancer cell growth and antioxidant activity of bioactive compounds from Poncirus trifoliata (L.) Raf.
    Bioorganic & medicinal chemistry, 2007, Jul-15, Volume: 15, Issue:14

    Recently several plant derived natural compounds have been screened for their anticancer activity in order to identify putative compounds with novel structures or mechanism of action. In the present study, fruits of Poncirus trifoliata were extracted with acetone and loaded onto silica gel column chromatography. The column was eluted with different solvents to obtain two bioactive compounds. The purity of compounds was analyzed by HPLC and their structures were identified by 1H and 13C NMR experiments as beta-sitosterol and 2-hydroxy-1,2,3-propanetricarboxylic acid 2-methyl ester (HPCME). beta-Sitosterol, HPCME, and trolox were tested for their antioxidant capacity by oxygen radical absorbance capacity (ORAC) measurement. Further, these compounds were tested for their inhibition of cancer cell proliferation and apoptosis using human colon cancer cell line (HT-29). These results were compared with the corresponding activity on non-cancerous (COS-1 fibroblast) cells. Cell proliferation and induction of apoptosis were determined by MTT assay and nuclear staining. The MTT assay indicated that both the compounds exhibited differential inhibition at various concentrations. Significant arrest of cell growth was observed with beta-sitosterol even at low concentration such as 0.63 microM in 48 h and none of the compounds exerted any apparent cytostatic effects on the non-cancerous COS-1 fibroblast cells. Growth inhibition assay suggested the potential use of bioactive compounds as cancer chemopreventive and therapeutic agents. This is the first report on HPCME isolation and identification from Rutaceae family and beta-sitosterol from P. trifoliata.

    Topics: Animals; Antioxidants; Carboxylic Acids; Cell Extracts; Cell Line; Cell Proliferation; Chlorocebus aethiops; Chromatography, High Pressure Liquid; Colonic Neoplasms; Esters; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Poncirus; Sitosterols

2007
[Chemical constituents from flos Sesamum indicum L].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2007, Volume: 42, Issue:3

    Sesame (Sesamum indicum L. ) belongs to Pedaliaceae, and its dry flowers have been used to cure alopecia, frostbite and constipation as a Traditional Chinese Medicine. Interestingly, the Flos Sesamum indicum L. was usually used to cure verruca vulgaris and verruca plana in folk of China, and showed a pleasant result. Previous chemical investigations of this plant mainly concentrate on its seeds, showed the presence of proteins and fat oils, herein we make a systematic chemical research on the dry flowers of this plant. Column chromatography including silica gel, C18 and Sephadex LH-20 were used to separate the chemical constituents and the structures were determined by chemical and spectroscopic methods. Ten compounds were isolated from the 95% ethanol extract of the plant and elucidated as latifonin (1), momor-cerebroside (2), soya-cerebroside II (3), 1-O-beta-D-glucopyranosyl-(2S, 3S, 4R, 5E,9Z)-2-N-(2'-hydroxytetracosanoyl) 1,3,4-trihydroxy-5,9-octadienine (4), 1-O-beta-D-glucopyranosyl-(2S, 3S, 4R, 8Z)-2-N-(2' R) 2'-hydroxytetracosanoyl) 3,4-dihydroxy-8-octadene (5), (2S, 1" S) -aurantiamide acetate (6), benzyl alcohol-O-(2'-O-beta-D-xylopyranosyl, 3'-O-beta-D-glucopyranoside)-beta-D-glucopyranoside (7), beta-sitosterol (8), daucosterol (9) and D-galacititol (10). Among them, 4 is a new compound, and others were isolated from the flowers of the plant for the first time. Compounds 2 to 4 belong to cerebroside, which is rare to be found in land plants and was proved to possess many bioactivities.

    Topics: Cerebrosides; Flowers; Glycolipids; Molecular Conformation; Molecular Structure; Plants, Medicinal; Sesamum; Sitosterols

2007
NPC1L1 (Niemann-Pick C1-like 1) mediates sterol-specific unidirectional transport of non-esterified cholesterol in McArdle-RH7777 hepatoma cells.
    The Biochemical journal, 2007, Sep-01, Volume: 406, Issue:2

    Recent evidence suggests that NPC1L1 (Niemann-Pick C1-like 1) is critical for intestinal sterol absorption in mice, yet mechanisms by which NPC1L1 regulates cellular sterol transport are lacking. In the study we used a McArdle-RH7777 rat hepatoma cell line stably expressing NPC1L1 to examine the sterol-specificity and directionality of NPC1L1-mediated sterol transport. As previously described, cholesterol-depletion-driven recycling of NPC1L1 to the cell surface facilitates cellular uptake of non-esterified (free) cholesterol. However, it has no impact on the uptake of esterified cholesterol, indicating free sterol specificity. Interestingly, the endocytic recycling of NPC1L1 was also without effect on beta-sitosterol uptake, indicating that NPC1L1 can differentiate between free sterols of animal and plant origin in hepatoma cells. Furthermore, NPC1L1-driven free cholesterol transport was unidirectional, since cellular cholesterol efflux to apolipoprotein A-I, high-density lipoprotein or serum was unaffected by NPC1L1 expression or localization. Additionally, NPC1L1 facilitates mass non-esterified-cholesterol uptake only when it is located on the cell surface and not when it resides intracellularly. Finally, NPC1L1-dependent cholesterol uptake required adequate intracellular K(+), yet did not rely on intracellular Ca(2+), the cytoskeleton or signalling downstream of protein kinase A, protein kinase C or pertussis-toxin-sensitive G-protein-coupled receptors. Collectively, these findings support the notion that NPC1L1 can selectively recognize non-esterified cholesterol and promote its unidirectional transport into hepatoma cells.

    Topics: Animals; Biological Transport; Calcium; Carcinoma, Hepatocellular; Cell Line, Tumor; Cell Membrane; Cholesterol; Cyclic AMP-Dependent Protein Kinases; Esters; Membrane Proteins; Membrane Transport Proteins; Mutation; Niemann-Pick Diseases; Oleic Acid; Potassium; Protein Kinase C; Rats; Receptors, G-Protein-Coupled; Signal Transduction; Sitosterols

2007
Thermodynamic study on competitive solubilization of cholesterol and beta-sitosterol in bile salt micelles.
    Chemistry and physics of lipids, 2007, Volume: 148, Issue:1

    Differences in the preferential solubilization of cholesterol and competitive solubilizates (beta-sitosterol and aromatic compounds) in bile salt micelles was systematically studied by changing the molar ratio of cholesterol to competitive solubilizates. The cholesterol solubility in a mixed binary system (cholesterol and beta-sitosterol) was almost half that of the cholesterol alone system, regardless of the excess beta-sitosterol quantity added. On the other hand, the mutual solubilities of cholesterol and pyrene were not inhibited by their presence in binary mixed crystals. Finally, the cholesterol solubility was measured by changing the alkyl chain length of n-alkylbenzenes. When tetradecylbenzene was added to the bile solution, the cholesterol solubility decreased slightly and was below the original cholesterol solubility. Based on Gibbs energy change (DeltaG degrees ) for solubilization, chemicals that inhibit cholesterol solubility in their combined crystal systems showed a larger negative DeltaG degrees value than cholesterol alone.

    Topics: Bile Acids and Salts; Chemistry, Physical; Cholesterol; Hydrocarbons, Aromatic; Micelles; Sitosterols; Solubility; Thermodynamics

2007
[Study on the active components of Nardostachys chinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:1

    To study on the active components of Nardostachys chinensis Batal, the compounds were isolated and purified by chromatographic methods, with their structures identified by spectral analysis and comparison with published data. 9 compounds were obtained and their structures were identified as acaciin, ursolie acid, octacosanol, kanshone A, nardosinonediol, nardosinone, aristolen-9beta-ol, oleanolic acid and beta-sitosterol. Acaciin, ursolie acid and octacosanol were obtained from Nardostachys chinensis Batal. for the first time. Acaciin and ursolie are the active components of antihiotics and anti-inflammatory.

    Topics: Ethanol; Fatty Alcohols; Glycosides; Molecular Structure; Nardostachys; Oleanolic Acid; Plants, Medicinal; Sitosterols

2007
[Studies on the chemical constituents of Vaccinium iteophyllum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:1

    7 compounds were isolated from the ethyl-acetate extract of Vaccinium iteophyllum Hance by using repeated silical gel column chromatography. These 7 compounds were identified by means of physico-chemical propertic and spectroscopic analysis as beta-sitosterol (I), ursolic acid (II), taraxerol (III), taraxerone (IV), friedelin (V), friedelinol (VI), 19,24-dihydroxyurs-12-en-3-one-28-oic acid (VII). The chemical constituents from this plant were reported here for the first time.

    Topics: Acetates; Drugs, Chinese Herbal; Oleanolic Acid; Plant Leaves; Plant Stems; Plants, Medicinal; Sitosterols; Triterpenes; Vaccinium

2007
[Studies on chemical constituents in fruits of Eucalyptus globulus].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:6

    To study the chemical constituents in the fruits of Eucalyptus globulus Labill.. The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by IR, NMR and MS evidences.. Fifteen compounds were obtained and identified as beta-sitosterol (1), betulinic acid (2), stigmasterol (3), euscaphic acid (4), 2a-Hydroxybetulinic acid (5), macrocarpal B (6), macrocarpal A (7), oleanolic acid (8), 3,4,3'-O-trimethylellagic acid (9), 3-O-methylellagic acid 4'-O-(2"-O-acetyl )-alpha-L-rhamnopyranoside (10), camaldulenside (cypellocarpin C, 11), 3-O-methylellagic acid 4'-O-alpha-L-rhamnopyranoside (12), 3-O-methylellagic acid (13), ellagic acid (14), and gallic acid (15).. Compounds 4 and 5 from genera Eucalyptus, 1, 3 and 11 from plant E. globulus, and 6, 7, 9 and 15 from the fruits of E. globulus were isolated for the first time.

    Topics: Cyclohexanecarboxylic Acids; Eucalyptus; Fruit; Glucosides; Molecular Structure; Phloroglucinol; Plants, Medicinal; Sesquiterpenes; Sitosterols; Stigmasterol

2007
Beta-sitosterol-induced-apoptosis is mediated by the activation of ERK and the downregulation of Akt in MCA-102 murine fibrosarcoma cells.
    International immunopharmacology, 2007, Volume: 7, Issue:8

    Beta-sitosterol (SITO) is a potential candidate for cancer chemotherapy, however, little is known about the cellular and molecular mechanisms in cancer cells. We herein identified how SITO induces anti-proliferation and cell death in MCA-102 fibrosarcoma cells. SITO exposure induced-apoptosis and the cell death resulted from a significant loss of the Bcl-2 and the inhibitor of apoptosis protein (IAP) family (XIAP, cIAP-1 and cIAP-2), and increased Bax with an alteration of p53 and p21. SITO-induced cell death significantly also increased caspase activity and poly(ADP-ribose) polymerase (PARP) cleavage, and caspase-3 inhibitor z-DEVD-fmk significantly inhibited SITO-induced cell death. These data suggest that the activation of caspase-3 is associated with SITO-induced-apoptosis. Treatment with SITO also induced phosphorylation of extracellular-signal regulating kinase (ERK) and p38 mitogen-activated protein kinase (MARK), but not c-Jun N-terminal kinase (JNK). A specific ERK inhibitor PD98059 significantly blocks SITO-induced-apoptosis, whereas a JNK inhibitor SP600125 has no affect. A p38 MAPK inhibitor SB203580 very slightly suppressed cell death. The induction of apoptosis was also accompanied by an inactivation of phosphatidylinositol 3-kinase (PI3K)/Akt, and PI3K inhibitor LY29004 significantly increases SITO-induced cell death. These findings provide evidence demonstrating that the proapoptotic effect of SITO is mediated through the activation of ERK and the block of the PI3K/Akt signal pathway in MCA-102 cells. Therefore, SITO has a strong potential as a therapeutic agent for preventing cancers such as fibrosarcoma.

    Topics: Animals; Anthracenes; Apoptosis; Apoptosis Regulatory Proteins; Caspase Inhibitors; Caspases; Cell Line, Tumor; Cell Survival; Chromones; Dose-Response Relationship, Drug; Down-Regulation; Extracellular Signal-Regulated MAP Kinases; Fibrosarcoma; G1 Phase; Hypolipidemic Agents; Imidazoles; Mice; Models, Biological; Morpholines; Oligopeptides; Phosphatidylinositol 3-Kinases; Phosphoinositide-3 Kinase Inhibitors; Proto-Oncogene Proteins; Proto-Oncogene Proteins c-akt; Proto-Oncogene Proteins c-bcl-2; Pyridines; Signal Transduction; Sitosterols; Tumor Suppressor Protein p53

2007
Beta-sitosterol induces anti-proliferation and apoptosis in human leukemic U937 cells through activation of caspase-3 and induction of Bax/Bcl-2 ratio.
    Biological & pharmaceutical bulletin, 2007, Volume: 30, Issue:7

    Beta-sitosterol is the main dietary phytosterol found in plants and has been shown to inhibit proliferation and induce apoptosis in human solid tumors such as colon and breast cancers. However, the mechanism by which beta-sitosterol induces apoptosis is not completely understood in leukemic cells. This study investigated the mechanism of apoptosis induced by beta-sitosterol in human leukemic U937 cells. beta-Sitosterol induced cytotoxicity and apoptosis in U937 cells in a concentration dependent manner, as measured by hemocytometer counts, fluorescence microscopy, agarose gel electrophoresis, and flow cytometry analysis. The increase in apoptosis induced by beta-sitosterol was associated with down-regulation of Bcl-2, degradation of poly-(ADP-ribose) polymerase (PARP) and phospholipase C (PLC)-gamma1 protein, and activation of caspase-3. beta-Sitosterol induced apoptosis was not associated with changes in the expression of Bcl-xL, Bax, or inhibitor of apoptosis proteins (IAPs). z-DEVD-fmk, a caspase-3 specific inhibitor, blocked caspase-3 activation and PARP degradation, and significantly attenuated beta-sitosterol-induced apoptosis. This suggests that caspase-3 activation is partially essential for beta-sitosterol-induced apoptosis. Bcl-2 overexpression also significantly blocked caspase-3 activation and the decrease in PARP cleavage by beta-sitosterol, and effectively attenuated the apoptotic response to beta-sitosterol. These results show that beta-sitosterol potently induces apoptosis in U937 cells and that beta-sitosterol-induced apoptosis is related to the selective activation of caspase-3 and induction of Bax/Bcl-2 ratio.

    Topics: Apoptosis; bcl-2-Associated X Protein; Caspase 3; Caspase Inhibitors; Cell Proliferation; Enzyme Activation; Humans; Proto-Oncogene Proteins c-bcl-2; Sitosterols; U937 Cells

2007
[Studies on chemical constituents from roots of Caragana microphylla].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:8

    To study the chemical constituents in roots of Caragana microphylla.. The constituents were isolated by silica gel column chromatography, and their structures were identified by spectroscopic methods and chemical evidence.. Eight compounds were identified as beta-sitosterol (1), pseudobaptigenin (2), pentacosanylferulates (3), heptadecanylferulates (4), ferulic acid (5), daucosterol (6), trifolirhizin (7), ononin (8) respectively.. Compounds 1, 3-7 were obtained from the plant for the first time, and 3, 4, 5 and 7 were obtained from the genus Caragana for the first time.

    Topics: Caragana; Coumaric Acids; Glucosides; Heterocyclic Compounds, 4 or More Rings; Plant Roots; Plants, Medicinal; Sitosterols

2007
[Chemical constituents from Cirsium pendulum Fisch. ex DC].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:3

    To study the chemical constituents of Cirsium pendulum Fisch. ex DC. Thirteen compounds were obtained from ethanol extract of Cirsium pendulum Fisch. ex DC. These compounds were characterized by spectroscopic analysis and comparison with published data to be beta-sitosterol(1), alpha-spinastenorl(2), taraxasterol(3), triacontanol(4), chlorophylla(5), lutein(6), linarin(7), 3-sitosterol-3-O-beta-D-glucopyranoside (8), 3', 4'-dihydroxy phenylethanol glucoside(9),3-(4'-methoxy-3',5'-dihydroxyphenyl)-allyl alcohol glucoside (10), uracil (11), methyl chlorogenate (12), chlorogenic (13). All of them were isolated from this plant for the first time.

    Topics: Cirsium; Drugs, Chinese Herbal; Glucosides; Glycosides; Sitosterols; Sterols; Triterpenes

2007
[Studies on chemical constituents of Eriophyton wallichii].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:9

    To study the chemical constituents of Eriophyton wallichii.. The constituents were isolated and purified by silica gel column and Sephadex LH-20 chromatography. Their structures are elucidated by physicochemical properties and spectral analysis.. Seven compounds were obtained and identified as beta-sitosterol (1), marrubiin (2), ursolic acid (3), cimigoside (4), 5-deoxyantirrhinoside (5), 8-epiloganic acid (6) and apigenin 7-(6"-p-coumaroyl) glucoside (7).. Compounds 1-7 were isolated from this plant for the first time.

    Topics: Apigenin; Chromatography, Gel; Diterpenes; Glucosides; Iridoids; Lamiaceae; Magnetic Resonance Spectroscopy; Mass Spectrometry; Plant Components, Aerial; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

2007
[Studies on chemical constituents of Patrinia villosa].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:4

    To inverstigate the chemical constituents of Patrinia villosa.. Under the direction of tetrazolium salt (MTf) assay, the chemical constituents were isolated by silica gel column chromatography and identified by physicochemical properties and spectral analysis (MS, FAB-MS, 1H NMR, 13C NMR).. Five compounds were isolated from petroleum ether and ethyl acetate extract and identified as: ursolic acid(I), beta-sitosterol (II), patrinalloside(III), kaempferol-3-O-beta-D-glucopyranoside(IV), and kaempferol-3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside(V).. Compounds I and V were obtained from the plant of genus Patrinia for the first time. Ursolic acid showed powerful anticancer activity through tetrazolium salt(MTT) assay, and its IC50 was 15.0 microg/ml.

    Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cell Survival; Humans; Inhibitory Concentration 50; Kaempferols; Patrinia; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

2007
Terpenoids and flavonoids from Laggera pterodonta.
    Yao xue xue bao = Acta pharmaceutica Sinica, 2007, Volume: 42, Issue:5

    To study the chemical constituents of aerial parts of Laggera pterodonta (DC.) Benth., the air-dried aerial parts of this plant were powered and extracted with boiling water and purified by silica gel column chromatography and recrystallized. Eleven compounds were obtained from L. pterodonta. They were identified as to be 6-O-beta-D-glucopyranosyl-carvotanacetone (1), pterodontic acid (2), 1beta-hydroxy pterondontic acid (3), pterodontoside A (4), pterodondiol (5), pterodontriol B (6), 5-hydroxy-3,4', 6,7-tetramethoxyflavone (7), artemitin (8), chrysosplenetin B (9), quercetin (10) and beta-sitosterol (11). Compound 1 is a new monoterpene glucoside. Compounds 10 and 11 were isolated from this plant for the first time. Compounds 2 and 5 showed moderate activity against bacteria including Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Mycobacteium phlei and Bacillus circulans by paper disc diffusion method, while they both displayed no activity against Escherichia coli.

    Topics: Anti-Bacterial Agents; Asteraceae; Chromatography, Gel; Flavonoids; Glucosides; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Components, Aerial; Plants, Medicinal; Pseudomonas aeruginosa; Quercetin; Sesquiterpenes; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Staphylococcus aureus; Terpenes

2007
Identification of beta-sitosterol, stigmasterol and ergosterin in A. roxburghii using supercritical fluid extraction followed by liquid chromatography/atmospheric pressure chemical ionization ion trap mass spectrometry.
    Rapid communications in mass spectrometry : RCM, 2007, Volume: 21, Issue:18

    beta-Sitosterol and stigmasterol are the most common phytosterols in traditional Chinese medicine. They have been proved to have many important bioactivities. To the best of our knowledge, this is the first report that beta-sitosterol, stigmasterol and ergosterol coexisting in A. roxburghii herbs can be simultaneously extracted by a supercritical fluid extraction (SFE) procedure; then a simple high-performance liquid chromatography/atmospheric pressure chemical ionization ion trap mass spectrometry (HPLC/APCI/MS) method was developed for simultaneous identification and determination of these three compounds. The ion trap MS/MS detector was equipped with an atmospheric pressure chemical ionization source operating in the positive ion mode, APCI(+). The linear responses were obtained in the concentration range of 0.50-150 microg/mL (r = 0.9999) for ergosterol, 5-400 microg/mL (r = 0.9999) for stigmasterol, and 10-2000 microg/mL (r = 0.9998) for beta-sitosterol. An orthogonal L(9) (3(3)) test design was employed for optimization of the SFE process. Under the optimized conditions, i.e. pressure of 25 mPa, temperature of 45 degrees C and ethanol as modifier, the concentrations of sterols in the extract were found to be 2.89% (g/g) for beta-sitosterol, 3.56% (g/g) for stigmasterol and 2.96% (g/g) for ergosterin. The SFE method was also compared with a previously developed Soxhlet extraction. The SFE method produced higher yields of sterols than that of the Soxhlet extraction. The proposed method has been successfully used for identification and quantitation of beta-sitosterol, stigmasterol and ergosterin in a real A. roxburghii sample.

    Topics: Atmospheric Pressure; Chromatography, High Pressure Liquid; Chromatography, Supercritical Fluid; Ergosterol; Orchidaceae; Plant Extracts; Reproducibility of Results; Sensitivity and Specificity; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Stigmasterol

2007
[Analysis of phytosterol contents in Chinese plant food and primary estimation of its intake of people].
    Wei sheng yan jiu = Journal of hygiene research, 2007, Volume: 36, Issue:3

    To analyze the phytosterol content in plant food commonly consumed in China, and to estimate the intake of phytosterols in Chinese people.. More than 160 types of plant food in 7 kinds were chosen as samples. The contents of beta-sitosterol, campesterol, stigmasterol, beta-sitostanol, campestanol were analyzed by GC methods and the total phytosterols were calculated. The intake of phytosteols in Chinese people was estimated using the data of "Survey on the Status of Nutrition and Health of the Chinese People" in 2002.. The contents of phytosterols in edible oils, nuts, and soybeans were higher than those in other plant food. In cereals, phytosterol contents of wheat flour were much higher than those of rice, the refinements of cereals may decrease the phytosterol contents. The phytosterol contents in vegetables and fruits were lower. The total intake of phytosterols in Chinese people was estimated to be 322.41mg/day, in which 40% may be of edible oil origin and 40% may be of cereal origin.. The results indicated that in the current dietary pattern, increase the intake of wheat, soybean, vegetable and fruit would enhance the phytosterol intake in Chinese.

    Topics: China; Fabaceae; Food Analysis; Humans; Oryza; Phytosterols; Sitosterols; Triticum; Vegetables

2007
[Chemical constituents from aerial parts of Plumbago zeylanica Linn].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:5

    To investigate the chemical constituents of the aerial parts of Plumbago zeylanica Linn.. The constituents of the EtOAc-soluble portion in the 95% ethanol extract were isolated and purified by means of chromatography. Compounds were identified by their physical characteristics and spectral features.. Nine compounds were isolated as plumbagin (I), isoshinanolone (II), plumbagic acid (III), beta-sitosterol (IV), 4-hydroxybenzaldehyde (V), trans-cinnamic acid (VI), vanillic acid (VII), 2, 5-dimethyl-7-hydroxychromone (VIII), indole-3-carboxaldehyde (IX).. Compounds V, VII, VIII and IX were isolated for the first time from Plumbago Linn.

    Topics: Benzaldehydes; Cinnamates; Indoles; Magnetic Resonance Spectroscopy; Molecular Structure; Naphthoquinones; Plant Components, Aerial; Plants, Medicinal; Plumbaginaceae; Sitosterols; Tetrahydronaphthalenes; Vanillic Acid

2007
Influence of harvest time on the quality of oil-based compounds in sea buckthorn (Hippophae rhamnoides L. ssp. sinensis) seed and fruit.
    Journal of agricultural and food chemistry, 2007, Oct-03, Volume: 55, Issue:20

    The effect of the harvest time on oil-based bioactive compounds in sea buckthorn berries ( Hippophae rhamnoides L. ssp. sinensis) was investigated. Sea buckthorn berries were collected at early maturity (September), maturity (November), and postmaturity (January) during the 2003-2004 harvest year. Whole berries were analyzed for physical characteristics, and fruit and seed fractions were analyzed for bioactive content. November-harvested berries yielded the highest values for berry sizes, CIELab factor a*, and total carotenoid content in the fruit fraction ( p < 0.05). September yielded significantly higher ( p < 0.05) levels of major compounds, alpha-tocopherol and beta-sitosterol, in the fruit fraction. Seed characteristics and bioactive compounds did not vary significantly with respect to the harvest time ( p > 0.05). These results have identified the most suitable level of maturity for the optimization of certain compounds and the losses that may occur with winter harvest, commonly practiced in cold climates.

    Topics: alpha-Tocopherol; Carotenoids; Fatty Acids; Fruit; Hippophae; Plant Oils; Seasons; Seeds; Sitosterols; Time Factors

2007
Anti-Helicobacter pylori activity of anacardic acids from Amphipterygium adstringens.
    Journal of ethnopharmacology, 2007, Oct-08, Volume: 114, Issue:1

    Amphipterygium adstringens (Schltdl.) Standl. (Anacardiaceae) is widely used in traditional Mexican medicine for the treatment of gastritis and ulcers. In this work, we studied the anti-Helicobacter pylori activity of its bark, this Gram-negative bacterium is considered the major etiological agent of chronic active gastritis and peptic ulcer disease, and it is linked to gastric carcinoma. From a bio-guided assay of the fractions obtained form a continuous Soxhlet extraction of the bark, we identified that petroleum ether fraction had significant antimicrobial activity against Helicobacter pylori. From this fraction, we isolated an anacardic acids mixture and three known triterpenes: masticadienonic acid; 3alpha-hydroxymasticadienonic acid; 3-epi-oleanolic; as well as the sterol beta-sitosterol. Only the anacardic acids mixture exhibits a potent dose-dependent antibacterial activity (MIC=10 microg/ml in broth cultures). It is enriched in saturated alkyl phenolic acids (C15:0, C16:0, C17:0 C19:0) which represents a novel source of these compounds with potent anti-Helicobacter pylori activity. The promising use of anacardic acids and Amphipterygium adstringens bark in the development of an integral treatment of Helicobacter pylori diseases is discussed.

    Topics: Anacardiaceae; Anacardic Acids; Anti-Bacterial Agents; Dose-Response Relationship, Drug; Helicobacter pylori; Humans; Hydroxybenzoates; Medicine, Traditional; Mexico; Microbial Sensitivity Tests; Oleanolic Acid; Plant Bark; Plant Extracts; Sitosterols; Triterpenes

2007
Bioactivity-guided isolation of beta-sitosterol and some fatty acids as active compounds in the anxiolytic and sedative effects of Tilia americana var. mexicana.
    Planta medica, 2007, Volume: 73, Issue:11

    Tilia species have been used as anxiolytics for many years. In a previous study anxiolytic-like effects of a hexane extract of Tilia americana var. mexicana inflorescences were observed in experimental models in mice. To get additional insights into the neuroactive actions of this particular Tilia species, in this study we report a bioactivity guided-fractionation of the extract and separation by column chromatographic methods to isolate three fatty acids and a triterpene identified as beta-sitosterol as major constituents. Our results revealed that the crude extract at 10 and 30 mg/kg I. P. and some pooled fractions at the same dosages potentiated sodium pentobarbital-induced sleeping time and caused a significant increase in the time spent at the open-arm sides in the plus-maze test. A reduction in the exploratory behavioral pattern manifested as ambulatory activity, as well as head dipping and rearing tests was also observed. Further fractionation and purification yielded four major fractions containing fatty acids and beta-sitosterol as the active compounds. A dose-response curve of beta-sitosterol in the range 1 to 30 mg/kg doses indicated that this compound produced an anxiolytic-like action from 1 to 10 mg/kg and a sedative response when the dose was increased to 30 mg/kg, these effects resemble those produced by diazepam (0.1 mg/kg). Our results suggest that hexane extract of Tilia americana var. mexicana produces depressant actions on the central nervous system, at least in part, because of the presence of beta-sitosterol and some fatty acids that remain to be identified.

    Topics: Animals; Anti-Anxiety Agents; Dose-Response Relationship, Drug; Fatty Acids; Injections, Intraperitoneal; Male; Maze Learning; Mice; Phytotherapy; Plant Extracts; Sitosterols; Sleep; Tilia

2007
A new isocoumarin from Hypericum annulatum.
    Natural product research, 2007, Volume: 21, Issue:12

    A new isocoumarin, annulatomarin (1), together with the known physcion and beta-sitosterol were isolated from the aerial parts of Hypericum annulatum. The structure of the new compound was established as 6,8-dihydroxy-7-methoxy-3-phenyl-3,4-dihydro-1H-isochromen-1-one on the basis of detailed spectroscopic analysis. Annulatomarin exhibited a modest growth-inhibitory activity in vitro against human chronic myeloid leukaemia LAMA-84 cells with an IC(50) = 111 microM.

    Topics: Cell Line, Tumor; Emodin; Humans; Hypericum; Inhibitory Concentration 50; Isocoumarins; Molecular Biology; Sitosterols

2007
[Studies on the chemical constituents of Urtica dioica L. grown in Tibet Autonomous Region].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:6

    Studies on the whole herb of Urtica dioica L. grown in Nyingchi area, China's Tibet Autonomous Region, resulted in the isolated of nine compounds: beta-sitosterol, trans-ferulic acid, dotriacotane, erucic acid, ursolic acid, scopoletin, rutin, quercetin and p-hydroxylbenzalcohol. Dotriacotane, erucic acid, scopoletin, rutin and p-hydroxylbenzalcohol were obtained from Urtica L. for the first time. Their structures were confirmed by modem spectral analysis (NMR, MS, etc).

    Topics: Erucic Acids; Molecular Structure; Plants, Medicinal; Quercetin; Rutin; Scopoletin; Sitosterols; Tibet; Triterpenes; Ursolic Acid; Urtica dioica

2007
[Analysis of lipid compounds of high-yielded rhizoma pinelliae growing in the west of Hubei province by gas chromatography-mass spectrometry].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:6

    To investigate lipid components of high-yielded Pinellia ternata rhizomes growing in the west of Hubei province.. To determine the lipid chemical components in Pinellia ternata rhizomes with GC-MS method and NIST atlas.. Ten components have been found: palmitic acid (I), 9,12-octadecadienoic acid (II), pyrrolidine,1-(1-oxo-7,10-hexadecadienyl) (III), alpha-monpalmitin (IV), 1,3,12-nonadecatriene (V), campesterol (VI), stigmasta-5,22-dien-3-ol (VII), beta-sitosterol (VIII), stigmasta-5,24-dien-3-ol (IX), cycloartenol (X).. The relative contents of five kinds of phytosterol: campesterol 28.96%, stigmasta-5,22-dien-3-ol 9.24%, beta-sitosterol 50.77%, stigmasta-5,24-dien-3-ol 4.74%, cycloartenol 6.25%. Component II, III, V, VI, IX are the first time reported in Pinellia ternata.

    Topics: China; Cholesterol; Gas Chromatography-Mass Spectrometry; Linoleic Acid; Palmitic Acid; Phytosterols; Pinellia; Plant Tubers; Plants, Medicinal; Sitosterols; Stigmasterol

2007
Effects of lactose-beta-sitosterol and beta-sitosterol on ovalbumin-induced lung inflammation in actively sensitized mice.
    International immunopharmacology, 2007, Dec-05, Volume: 7, Issue:12

    Asthma is a disease marked by chronic lung inflammation and the number of patients suffering from asthma increases annually. Both beta-sitosterol (BS) and beta-sitosterol glucoside exist in a variety of plants and have anti-tumor, anti-microbial, and immunomodulatory activities. However, the precise role of BS and beta-sitosterol glucoside in asthma has not been well understood. The aim of this study was to investigate the inhibitory effects of BS and lactose-BS (L-BS) on the pathophysiological process in ovalbumin-induced asthmatic mice. The total cells and eosinophils in the bronchoalveolar lavage (BAL) fluid markedly decreased (p<0.05) after L-BS or BS administration (1 mg/kg; i.p.), and the ROS production also decreased in comparison to the asthma control. Histopathological features were detected by performing histochemistry, including H&E and alcian blue & P.A.S staining. Both L-BS and BS mitigated the inflammation by eosinophil infiltration and mucus hypersecretion by goblet hyperplasia. These effects of L-BS were superior to those of BS. L-BS and BS inhibited the increased mRNA and protein expression of IL-4 and IL-5 in the lung tissue and BAL fluid, respectively. The IgE concentration in the BAL fluid and serum was measured by performing ELISA and the ovalbumin-specific IgE in the BAL fluid was uniquely inhibited by L-BS (p<0.05). The splenocytes were isolated from the normal and asthmatic mice and incubated in the absence and presence of 100 microg/ml ovalbumin, respectively. L-BS blocked the survival rate of the splenocytes of the mice (p<0.01). This finding indicates the possibility of L-BS and BS as potential therapeutic molecules in asthma and may contribute to the need to improve current therapeutic drugs.

    Topics: Animals; Anti-Asthmatic Agents; Asthma; Bronchoalveolar Lavage Fluid; Cell Survival; Enzyme-Linked Immunosorbent Assay; Eosinophils; Female; Gene Expression; Glycosides; Immunoglobulin E; Interleukin-13; Interleukin-4; Interleukin-5; Lactose; Leukocytes; Lung; Mice; Mice, Inbred BALB C; Molecular Structure; Ovalbumin; Pneumonia; Reverse Transcriptase Polymerase Chain Reaction; Sitosterols; Vaccination

2007
[Studies on the chemical constituents from herba anoectochili].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:7

    To study the chemical constituents in the whole herb of Anoectochiluts roxburghii (Wall) Lindl.. The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by IR, NMR and MS evidences.. Fourteen compounds were obtained and there into ten were identified as beta-sitosterol(2), ferulic acid(3), oleanolic acid(6), lanosterol(7), p-hydroxybenzaldehyde(8), 3-methoxyl-p-hydroxybenzaldehlde(9), daucosterol(10),3',4',7-trimethoxy-3, 5-dihydroxyflavone(11), isorhamnetin-3-O-beta-D-rutinoside(12) and rutin(13).. Compounds 6,7,9 and 11 from genera Anoeetochilus were isolated for the first time.

    Topics: Coumaric Acids; Flavones; Lanosterol; Molecular Structure; Oleanolic Acid; Orchidaceae; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet

2007
Beta-sitosterolaemia: a new nonsense mutation in the ABCG5 gene.
    European journal of clinical investigation, 2007, Volume: 37, Issue:12

    Sitosterolaemia is a rare autosomal recessive disorder characterised by elevated plasma levels of plant sterols and cholesterol. Sitosterolaemia is caused by gene mutations in either of two ATP-binding cassette (ABC) half transporters, ABCG5 and ABCG8. The plasma sterol profile and genetic analysis of a 10-year-old girl who had tuberous xanthomas is the subject of this report.. Genomic DNA was isolated from white blood cells from the proband, her family and a control group of healthy people. All exons of ABCG5 and ABCG8 were sequenced. Plasma cholesterol and triglycerides were measured by routine methods. All other plasma sterols were measured by Gas Chromatography coupled to Mass Spectrometry.. The proband was found to be homozygous for a single nucleotide mutation in exon 10 of the ABCG5 gene, consisting of a C to T transition at nucleotide 1336 of the coding sequence, which results in the premature termination of the ABCG5 protein at amino acid 446 (Arg446X). Her mother and brother were also homozygous for the same mutation and all had elevated plasma beta-sitosterol levels. The father was heterozygous and showed normal beta-sitosterol levels. This mutation was not found in healthy normolipidaemic subjects.. We describe a novel nonsense mutation in exon 10 of the ABCG5 gene in a 10-year-old girl showing clinical and biochemical features of sitosterolaemia. This family study broadens the spectrum of the ABCG5/ABCG8 mutations causing sitosterolaemia and helps highlight the correlations between such gene mutations, biochemical phenotype and the development of cardiovascular disease.

    Topics: Adult; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Child; Cholesterol; Exons; Family; Female; Humans; Iran; Lipoproteins; Male; Middle Aged; Mutation; Sitosterols; Sterols; Triglycerides; Xanthomatosis

2007
[Chemical constituents of Oxytropis chiliophylla].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:16

    To study the chemical constituents of Oxytropis chiliophylla.. The air-dried whole plants of O. chiliophylla were extracted with EtOH (90%) three times at room temperature. The compounds were isolated by silica-gel, polyamide, C-18 and Sphadex LH -20 columns. The structures were identified based on spectral analysis.. 8 compounds were isolated from O. chiliophylla and identified as azukisapogenol (1), (22E, 24R) -24-methyl-5alpha-cholesta-7, 22-diene-3beta, 5alpha, 6beta-triol (2), apigein (3), 3', 4'-dimethoxy-quercetin-3-O-beta-D-galactopyranoside (4), 7, 3', 4'-trimethoxy-quercetin-3-O-alpha-L-rhamopyranosyl-(1-->2)-beta-D-glucopyranoside (5), (2S, 3S, 4R)-N-[(R)-2'-hydroxytetracosanoyl]-1, 3, 4-trihydroxy-2-amino-octadeca-6-ene (6), beta-sitosterol (7), daucosterol (8).. All the compounds were isolated from O. chiliophylla for the first time.

    Topics: Oxytropis; Plants, Medicinal; Sapogenins; Sitosterols

2007
[Chemical constituents from root of Actinidia chinensis].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:16

    To study the chemical constituents from the root of Actinidia chinensis.. The roots of A. chinensis were extracted with 95% EtOH. The EtOH extract was suspended in H2O and extracted with petroleum ether, EtOAc and BuOH successively. The compounds were isolated with column chromatography from the EtOAc fraction, and elucidated on the basis of spectral analysis(MS, IR, 1H-NMR, 13C-NMR).. Seven compounds were isolated from the root of A. chinensis, and the structures were identified as 2alpha-hydroxyoleanolic acid (1), 2alpha-hydroxyursolic acid (2), euscaphic acid (3), 23-hydroxyursolic acid (4), 3beta-O-acetylursolic acid (5), ergosta4, 6, 8, (14), 22-tetraen-3-one (6), beta-steriol (7).. All the compounds were obtained from the root of A. chinensis for the first time.

    Topics: Actinidia; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

2007
[Studies on the chemical constituents of Gueldenstaedtia stenophylla].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:8

    To study the chemical constituents of Gueldenstaeditia stenophylla.. The constituents were isolated by alcohol extraction, column chromatography on silica gel. Their structures were elucidated by chemical and spectroscopic methods.. Six compounds were obtained, and five of them were identified as n-hexadecanioc acid (I), beta-sitosterol (II), daucosterol (III), apigenin (IV), D-fructose (VI). Compound V was being determined.. Five compounds are isolated from Gueldenstaedtia stenophylla and compounds I, III are extracted from Gueldenstaedtia Fisch for the first time.

    Topics: Apigenin; Fabaceae; Palmitic Acid; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet

2007
[Studies on chemical constituents of Heterosmilax yunnanensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:8

    To study the chemical constituents of Heterosmilax yunianensis.. The compounds were isolated and repeatedly purified with chromatograph and the structures were elucidated by physico-chemical properties and spectral analysis.. Eight compounds were obtained and elucidated as beta-sitosterol (I), glycerol monopalmitate (II), daucosterol (IIl), hexacosanoic acid (IV), 5-hydroxymethyl furaldehyde (V), hergapen (VI), ursolic acid (VII), liquiritigenin (VIII).. They have been isolated from this plant for the first time, and IV - VIII are obtained from the plants of Heterosmilax for the first time.

    Topics: Fatty Acids; Flavanones; Lactones; Molecular Structure; Plants, Medicinal; Rhizome; Sitosterols; Smilacaceae; Triterpenes; Ursolic Acid

2007
[Studies on chemical constituents of Liriope platyphylla].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:9

    Seven chemical constituents were isolated from the CHCl3 fraction and n-BuOH fraction from EtOH ext. of Liriope platyphylla Wang et Tang. Their structures were elucidated as lupenone (I), lupeol (II), ursolic acid (III), beta-sitosterol (IV), diosgenin (V), LP-A (VI) and LP-B (VII) respectively. Compound I, II and V were isolated from this genus of Liriope for the first time. Compound III and IV were isolated from this plant for the first time.

    Topics: Diosgenin; Liriope Plant; Molecular Structure; Pentacyclic Triterpenes; Plant Tubers; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

2007
[Study on the chemical constituents of Heterosmilax japonica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:9

    To analyze the chemical constituents of Heterosmilax japonica Kunth.. The sample was separated and analyzed by GC-MS.. 62 ingredients were elucidated. The major components were steroids and fatty acids.. The method is reliable, and the result provides a reference for further study of Heterosmilax japonica Kunth.

    Topics: Fatty Acids; Gas Chromatography-Mass Spectrometry; Linoleic Acid; Molecular Weight; Plants, Medicinal; Rhizome; Sitosterols; Smilacaceae; Steroids

2007
[Studies on chemical constituents from Rhizoma Heterosmilacis Japonicae].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:10

    Six compounds were isolated from Rhizoma Heterosmilacis Japonicae. They were identified as beta-sitosterol (I) dau-costerol (II),3,3',5,5'-tetrahydroxy-4'-methoxystilbene (III), naringenin (IV), alpha-L-butylsorbopyranoside (V) and macrozamin (VI). The compounds III, IV, V and VI were isolated from this genus for the first time.

    Topics: Flavanones; Liliaceae; Malpighiaceae; Methylazoxymethanol Acetate; Molecular Structure; Plant Tubers; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet

2007
[Study on chemical constituents of Orobanche coerulescens].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:10

    Six compounds were isolated and purified from Orobanche coerulescens by extraction and different kinds of column chromatography. The structures were determined on the basis of spectral analysis. The structures were elucidated as D-mannitol(I), beta-sitosterol(II), succinic acid(III), caffeic acid(IV), protocatechuic aldehyde(V) and daucosterol(VI). All compounds are obtained from this plant for the first time.

    Topics: Benzaldehydes; Caffeic Acids; Catechols; Chromatography, Thin Layer; Ethanol; Mannitol; Orobanche; Plants, Medicinal; Rhizome; Sitosterols; Succinic Acid

2007
[Study on chemical constituents from rhizomes of Actaea asiatica].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:21

    To investigate the chemical constituents of the rhizomes of Actaea asiatica in order to obtain a more comprehensive understanding of its effective components.. Compounds were separated by silica gel chromatography, RP-C18 chromatography and semi-preparative high performance liquid chromatography, and their structures were established by spectral analysis and chemical evidence.. Six compounds were isolated from the ethyl acetate extract. Their structures were identified as 25-O-acetylcimigenol (1), 12beta-hydroxycimigenol (2), 23-epi-26-deoxyactein (3), 27-deoxyacetylacteol (4), 26-deoxycimicifugenin (5) and beta-sitosterol (6).. All these compounds mentioned above were isolated from the plant for the first time.

    Topics: Actaea; Lanosterol; Plants, Medicinal; Rhizome; Saponins; Sitosterols; Triterpenes

2007
[Chemical constituents in unsaponifiable matter from seeds of Trichosanthes hupehensis].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:21

    To study the chemical constituents of unsaponifiable matter from the seed oil of Trichosanthes hupehensis.. The fatty oil from the seeds of T. hupehensis was extracted with petroleum ether. The saponification was carried out with potassium hydroxide. The unsaponifiable matter was isolated and purified by silica gel column chromatography. Their structures were elucidated by means of MS, IR, UV, and 1H-NMR.. Karounidiol, isokarounidiol, 5-dehydrokarounidiol, 7-oxodihydrokarounidiol, stigmast-7-en-3beta-ol, stigmast-7, 22-dien-3beta-ol, 10alpha-Cucurbitadienol, beta-sitosterol, stigmast-7, 22-dien-3beta-O-beta-D-glucoside were elucidated.. All of these compounds were found in this plant for the first time.

    Topics: Oleanolic Acid; Plant Oils; Plants, Medicinal; Seeds; Sitosterols; Trichosanthes; Triterpenes

2007
[Studies on chemical constituents of Valeriana officinalis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:11

    From Valeriana officinalis L., 4 compounds were isolated and identified by various spectral analysis and chemical conversion, as valerenic acid, beta-sitosterol, ursolic acid, 4, 4', 8, 8'-tetrahydroxy-3, 3'-dimethoxyl-dibenzyl-ditetrahydrofuran and caryophyllene acide,valerane, naphthalene, linoleic acid, ethyl ester, myrtenyl acetate were identified by GC-MS. Ursolic acid and 4, 4', 8, 8'-tetrahydroxy-3, 3'-dimethoxyl-dibenzyl-ditetrahydrofuran were discovered in this plant for the first time.

    Topics: Acetates; Gas Chromatography-Mass Spectrometry; Indenes; Linoleic Acid; Naphthalenes; Plant Roots; Plants, Medicinal; Rhizome; Sesquiterpenes; Sitosterols; Triterpenes; Ursolic Acid; Valerian

2007
[Studies on chemical constituents of Taxillus sutchuenenisis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2007, Volume: 30, Issue:11

    To study the chemical constituents of Taxillus sutchuenenisis (Lecomte) Danser.. Chromatography and spectrum analysis were employed to isolated and elucidate the chemical constituents in the plant.. 9 compounds were isolated and identified as quercetin (I), quervetin 3-O-beta-D-galactoside (II), isoquercitrin (III), quercitrin (IV), rutin (V), gallic acid (VI), ferulic acid (VII), beta-sitosterol (VIII), daucosterol (IX), respectively.. Compounds III-IX are isolated from this plant for the first time. The work provide evidence for the exploitation and utilization of this plant resouce.

    Topics: Coumaric Acids; Gallic Acid; Loranthaceae; Molecular Structure; Plants, Medicinal; Quercetin; Rhizome; Rutin; Sitosterols; Spectrophotometry, Ultraviolet

2007
Chemical constituents from aerial part of Curcuma wenyujin.
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2007, Volume: 32, Issue:24

    To investigate the chemical constituents from aerial part of Curcuma wenyujin.. Compounds were isolated by repeated column chromatography on silica gel. Their structures were elucidated on the basis of spectral analysis and comparison with literature data.. Six compounds were isolated and identified as codonolactone (1), voleneol (2), octacosanoic acid (3), beta-sitosterol (4), mangdesisterol (5), and daucosterol (6).. Compounds 1, 2, and 5 were isolated from the plant for the first time.

    Topics: Curcuma; Fatty Acids; Phytosterols; Plant Components, Aerial; Plants, Medicinal; Sesquiterpenes; Sitosterols

2007
Seasonal pollution characteristics of organic compounds in atmospheric fine particles in Beijing.
    The Science of the total environment, 2006, Apr-15, Volume: 359, Issue:1-3

    Beijing is a rapidly developing city with severe and unique air pollution problems. Organic matter is the most abundant fraction in fine particles in Beijing, occupying 30-50% of the total mass, indicating its key role in air pollution control. However, detailed chemical characterization of particulate organic matter in Beijing has never been reported. In this study, fine particles in the urban atmosphere in Beijing were investigated for its organic components by GC/MS technique. Over 100 individual organic compounds were identified and quantified in 25 PM2.5 samples from the summer, autumn and winter of 2002-2003. Alkanes, fatty acids, dicarboxylic acids, polycyclic aromatic hydrocarbons and some important tracer compounds (hopanes, levoglucosan and steroids) were the major constituents with the sum of their concentrations of 502, 1471 and 1403 ng m(-3) in summer, autumn and winter, respectively. Different organic compounds presented apparently different seasonal characteristics, reflecting their different dominant emission sources, such as coal combustion, biomass burning and cooking emission. The abundance and origin of these organic compounds are discussed to reveal seasonal air pollution characteristics of Beijing.

    Topics: Air Pollutants; Air Pollution; China; Cholesterol; Cities; Dust; Environmental Monitoring; Gas Chromatography-Mass Spectrometry; Glucose; Organic Chemicals; Particle Size; Seasons; Sitosterols

2006
Ester percentages of plant sterols and cholesterol in chylomicrons and VLDL of humans with low and high sterol absorption.
    Atherosclerosis, 2006, Volume: 187, Issue:1

    Ester percentages of cholesterol and non-cholesterol sterols were measured in chylomicrons and very low density lipoproteins (VLDL) in 15 subjects. Our hypothesis was that in humans, in contrast to animal experiments, plant sterols in chylomicrons are esterified similarly to cholesterol. In fact, the mean ester percentage of chylomicron sitosterol (approximately 40%), but not of campesterol ( approximately 51%), was lower than that of cholesterol (approximately 54%) in the whole study population. In high cholesterol absorbers (high serum total campesterol, > or = 2.8 mmol/mol of cholesterol), the ester percentages of sitosterol and other non-cholesterol sterols were similar to that of cholesterol in chylomicrons, and the percentages tended to be higher than those in low absorbers. In contrast to chylomicrons, the ester percentages of sterols in VLDL tended to be lower in the high than low absorbers. In conclusion, percentages of plant sterol esters are not consistently lower than those of cholesterol in chylomicrons.

    Topics: Absorption; Adult; Aged; Cholesterol; Chylomicrons; Esters; Humans; Lipids; Lipoproteins, VLDL; Male; Middle Aged; Phytosterols; Plants; Sitosterols

2006
Effect of beta-sitosterol concentration and high pressure homogenization on the chlorhexidine release from vesicular gels.
    International journal of pharmaceutics, 2006, Jan-03, Volume: 307, Issue:1

    Previous studies have confirmed that the phase transition of vesicular gels of hydrogenated phospholipids to the less ordered fluid vesicular state was induced by the increase of the beta-sitosterol ratio in the whole gel system and consequently in the lipid bilayer. The purpose of the present study was to evaluate the influence of the beta-sitosterol portion in the lipid bilayer and the effect of high pressure homogenization on the structural characteristics of the prepared gel systems. In addition the influence of beta-sitosterol on the consequent chlorhexidine release from the obtained vesicles and liposomes was also examined. Lipid mixtures were prepared from different molar ratios of lecithin:sterol components (90:10-65:35 mol%). The obtained mixtures were hydrated with the aqueous solution of chlorhexidine digluconate in order to achieve a 30% (w/w) final concentration of the lipid mixtures and a 4% (w/w) concentration of the drug. One portion of the resultant multilamellar vesicles was homogenized by using high pressure. To characterize the homogenized and non-homogenized systems, transmission electron microscopy of the freeze-fractured samples and differential scanning calorimetry (DSC) were carried out. A vertical type diffusion cell was applied to determine the amount of released chlorhexidine digluconate. Along with the increase in beta-sitosterol concentration, the fluidity of the membrane as well as its permeability also increased. The increased permeability--caused by the higher beta-sitosterol concentration--and the high pressure homogenization, which increased the dispersity and therefore the surface area, enabled a higher amount of chlorhexidine to be released. The increase of drug release was more pronounced in the case of samples prepared with high pressure homogenization.

    Topics: Anti-Infective Agents, Local; Calorimetry, Differential Scanning; Chlorhexidine; Delayed-Action Preparations; Drug Compounding; Gels; Hypolipidemic Agents; Lipid Bilayers; Liposomes; Microscopy, Electron, Transmission; Sitosterols

2006
Identification of biologically active triterpenes and sterols present in hexane extracts from Miconia species using high-resolution gas chromatography.
    Biomedical chromatography : BMC, 2006, Volume: 20, Issue:8

    In this work we describe the identification of the biologically active triterpenes and sterols present in the hexane extracts of six species of Miconia using gas chromatography. The main compounds present in these extracts are beta-amyrin, alpha-amyrin, and beta-sitosterol. The technique employed herein is shown to be a valuable and rapid tool for determining biologically active triterpenes and sterols present in non-polar extracts.

    Topics: Chromatography, Gas; Hexanes; Melastomataceae; Oleanolic Acid; Phytosterols; Plant Components, Aerial; Plant Extracts; Sitosterols; Triterpenes

2006
Plasma sitosterol elevations are associated with an increased incidence of coronary events in men: results of a nested case-control analysis of the Prospective Cardiovascular Münster (PROCAM) study.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2006, Volume: 16, Issue:1

    Sitosterolemia, a rare genetic disorder characterized by profoundly elevated plasma sitosterol concentrations, is associated with premature atherosclerosis in some individuals. This study was conducted to evaluate if the modest sitosterol elevations seen in the general population are also associated with the occurrence of coronary events.. A nested case-control study using stored samples from male participants in the Prospective Cardiovascular Münster (PROCAM) study was performed. Each of 159 men who suffered a myocardial infarction or sudden coronary death (major coronary event) within 10 years of follow-up in PROCAM was matched with 2 controls (N = 318) by age, smoking status, and date of investigation. Analysis was performed using conditional logistic regression. Plasma sitosterol concentrations were elevated in cases compared with controls (4.94 +/- 3.44 micromol/L versus 4.27 +/- 2.38 micromol/L; P = 0.028). The upper quartile of sitosterol (>5.25 micromol/L) was associated with a 1.8-fold increase in risk (P < 0.05) compared with the lower three quartiles. Among men with an absolute coronary risk > or = 20% in 10 years as calculated using the PROCAM algorithm, high sitosterol concentrations were associated with an additional 3-fold increase in the incidence of coronary events (P = 0.032); a similar, significant relationship was observed between a high sitosterol/cholesterol ratio and coronary risk (P = 0.030).. Elevations in sitosterol concentrations and the sitosterol/cholesterol ratio appear to be associated with an increased occurrence of major coronary events in men at high global risk of coronary heart disease. Further evaluations are warranted to confirm these preliminary findings.

    Topics: Adolescent; Adult; Aged; Case-Control Studies; Cholesterol; Cohort Studies; Coronary Disease; Germany; Humans; Incidence; Logistic Models; Male; Middle Aged; Prospective Studies; Risk Factors; Sitosterols; Smoking

2006
Endocrine and metabolic alterations in the mink (Mustela vison) due to chronic phytoestrogen exposure.
    Chemosphere, 2006, Volume: 64, Issue:10

    Phytoestrogens are natural components of plant-based food items with beneficial health effects. The aim of the present study was to investigate the chronic effects of dietary phytoestrogens, genistein (8 mg kg(-1) day(-1)) and beta-sitosterol (50 mg kg(-1) day(-1)), on the weight regulation of the mink (Mustela vison). The parental generation was exposed from August 2002 to May-June 2003 to either beta-sitosterol or genistein, while the kits were exposed through gestation and lactation. Food consumption and body masses were monitored monthly. Plasma lipid, glucose, total protein and hormone (ghrelin, leptin, triiodothyronine and thyroxine) concentrations were measured from the parents in August 2002, January 2003 and at the end of the experiment in May-June 2003 when the kits were 21 days of age. Relative food intake was higher in the beta-sitosterol-exposed minks than in the control or genistein minks in September 2002. Plasma leptin and total protein concentrations were lower in the beta-sitosterol kits compared to the control kits. Furthermore, plasma ghrelin levels and liver phosphorylase activities of the mink kits were higher due to genistein exposure. In mink kits, exposure to both phytoestrogens reduced the plasma thyroxine concentrations. The kidney glycogen concentrations and the muscle phosphorylase activities of phytoestrogen-treated adult minks were elevated. The results of this study suggest that minks are sensitive to perinatal phytoestrogen exposure.

    Topics: Animals; Female; Genistein; Ghrelin; Leptin; Male; Mink; Peptide Hormones; Phytoestrogens; Sitosterols

2006
Liver transplantation in a patient with sitosterolemia and cirrhosis.
    Gastroenterology, 2006, Volume: 130, Issue:2

    Sitosterolemia (MIM 210250) is a rare genetic disorder caused by disruption of the normal mechanisms that regulate dietary cholesterol absorption and prevent the accumulation of noncholesterol sterols. As a result of this defect, affected individuals accumulate high concentrations of plant sterols in plasma and tissues. They present clinically with tendon or tuberoeruptive xanthomas, premature coronary artery disease, and/or hemolytic anemia. Two genes, ABCG5 and ABCG8, compose the STSL locus, and complete mutation in either, but not both, results in disease. The expression of these genes is confined to the intestine and liver. They are thought to function as sterol efflux pumps. It is not clear which organ, liver or intestine, is of greater importance in maintaining sterol balance with respect to noncholesterol sterols. We report here a case of a patient who presented with "chronic active liver disease" and was found to have sitosterolemia by chance and subsequently underwent orthotopic liver transplantation. Following transplantation, the grossly elevated pretransplantation serum plant sterol levels decreased to values only slightly higher than those of the patient's heterozygous father. This case highlights 2 important features: (1) The liver functions as the predominant organ for maintaining noncholesterol sterol balance (because the intestinal defect was not altered), and (2) a new clinical feature of undiagnosed sitosterolemia may be "idiopathic" liver disease. Because the diagnosis of sitosterolemia is based on specialized plasma analyses, we would propose that some consideration to this diagnosis should be given in appropriate cases.

    Topics: Adult; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Chromosome Mapping; Female; Humans; Lipid Metabolism, Inborn Errors; Lipoproteins; Liver; Liver Cirrhosis; Liver Transplantation; Male; Sitosterols

2006
Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat.
    Metabolism: clinical and experimental, 2006, Volume: 55, Issue:3

    Plant sterols compete with cholesterol (cholest-5-en-3beta-ol) for intestinal absorption to limit absorption and lower plasma concentrations of cholesterol. Stigmasterol (24-ethyl-cholesta-5,22-dien-3beta-ol; Delta(22) derivative of sitosterol [24-ethyl-cholest-5-en-3beta-ol]), but not campesterol (24-methyl-cholest-5-en-3beta-ol) and sitosterol, is reported to inhibit cholesterol biosynthesis via inhibition of sterol Delta(24)-reductase in human Caco-2 and HL-60 cell lines. We studied the effect of feeding 0.5% stigmasterol on plasma and liver sterols and intestinal cholesterol and sitosterol absorption in 12 wild-type Kyoto (WKY) and 12 Wistar rats. After 3 weeks of feeding, cholesterol and sitosterol absorption was determined in 6 rats from each group by plasma dual-isotope ratio method. After 3 more weeks, plasma and hepatic sterols and hepatic enzyme activities were determined in all rats. After feeding stigmasterol, baseline plasma cholesterol was 1.3 times and plant sterols 3 times greater in WKY compared with Wistar rats. Stigmasterol feeding lowered plasma cholesterol by approximately 11%, whereas plasma campesterol and sitosterol levels were virtually unchanged in both rat strains, and stigmasterol constituted 3.2% of plasma sterols in WKY rats and 1% in Wistar rats. After 6 weeks of feeding, cholesterol and sitosterol absorption decreased 23% and 30%, respectively, in WKY, and 22% and 16%, respectively, in the Wistar rats as compared with untreated rats. The intestinal bacteria in both rat strains metabolized stigmasterol to mainly the 5beta-H stanol (>40%), with only small amounts of 5alpha-H derivative (approximately 1.5%), whereas the C-22 double bond was resistant to bacterial metabolism. Hepatic stigmasterol levels increased from 11 microg/g liver tissue to 104 mug/g in WKY rats and from 5 microg/g liver tissue to 21 microg/g in Wistar rats. 3-Hydroxy-3-methylglutaryl coenzyme A reductase activity was suppressed 4-fold in the WKY and almost 1.8-fold in Wistar rats, cholesterol 7alpha-hydroxylase activity was suppressed 1.6-fold in the WKY and 3.5-fold in Wistar rats, whereas cholesterol 27-hydroxylase activity was unchanged after feeding. In conclusion, stigmasterol, when fed, lowers plasma cholesterol levels, inhibits intestinal cholesterol and plant sterol absorption, and suppresses hepatic cholesterol and classic bile acid synthesis in Wistar as well as WKY rats. However, plasma and hepatic incorporation of stigmasterol is low.

    Topics: Animals; Bile Acids and Salts; Cholesterol; Intestinal Absorption; Liver; Male; Rats; Rats, Inbred WKY; Rats, Wistar; Sitosterols; Sterols; Stigmasterol

2006
Determination of stigmasterol, beta-sitosterol and stigmastanol in oral dosage forms using high performance liquid chromatography with evaporative light scattering detection.
    Journal of pharmaceutical and biomedical analysis, 2006, Jun-07, Volume: 41, Issue:3

    A validated and repeatable high performance liquid chromatography (HPLC) method with online evaporative light scattering (ELSD) was developed for the analysis of two sterols, stigmasterol, beta-sitosterol and a stanol, stigmastanol, found to be common in many herbal formulations and health care supplements. The method is based on the separation of the three marker compounds on a C8 column (Phenomenex Luna, 5 microm, 150 mmx4.6 mm i.d.) using methanol:water (95:5 v/v) as the mobile phase, and a flow rate of 1 ml/min to separate all the marker compounds within 12 min. Cholesterol (50 microg/ml) was used as internal standard and methanol as the extraction solvent. The ELSD response parameters were optimised and the limits of detection (LOD) and quantification (LOQ) were calculated to be 2 and 5 microg/ml, respectively, which is more sensitive than obtained by photo diode array detection (5 and 7 microg/ml). Using ELSD, the percentage relative standard deviation (%R.S.D.) of intra-day and inter-day (3 days) precision for each marker was better than 3%, the accuracy data were within 97-103% and the recovery data were found to be within 95-107% for the five commercially available products examined. This method was used to assay commercially available products formulated as oral dosage forms purported to contain African Potato and associated sterols and stanol and proved to be suitable for the routine analysis and quality control of such products.

    Topics: Administration, Oral; Chromatography, High Pressure Liquid; Dosage Forms; Light; Reference Standards; Reproducibility of Results; Scattering, Radiation; Sensitivity and Specificity; Sitosterols; Stigmasterol

2006
Purification and ATPase activity of human ABCA1.
    The Journal of biological chemistry, 2006, Apr-21, Volume: 281, Issue:16

    ATP-binding cassette protein A1 (ABCA1) plays a major role in cholesterol homeostasis and high density lipoprotein metabolism. Apolipoprotein A-I binds to ABCA1 and cellular cholesterol and phospholipids, mainly phosphatidylcholine, are loaded onto apoA-I to form pre-beta high density lipoprotein (HDL). It is proposed that ABCA1 translocates phospholipids and cholesterol directly or indirectly to form pre-beta HDL. To explore the mechanism of ABCA1-mediated pre-beta HDL formation, we expressed human ABCA1 in insect Sf9 cells and purified it. Trypsin limited-digestion of purified ABCA1 in the detergent-soluble form suggested that it retained conformation similar to ABCA1 expressed in the membranes of human fibroblast WI-38 cells. Purified ABCA1 showed robust ATPase activity when reconstituted in liposomes made of synthetic phosphatidylcholine. ABCA1 showed lower ATPase activity when reconstituted in liposomes containing phosphatidylserine, phosphatidylethanolamine, or phosphatidylglycerol and also showed weak specificity in acyl chain species. ATPase activity was reduced by the addition of cholesterol and decreased by 25% in the presence of 20% cholesterol. Beta-sitosterol and campesterol showed similar inhibitory effects but stigmasterol did not, suggesting structure-specific interaction between ABCA1 and sterols. Glibenclamide suppressed ABCA1 ATPase, suggesting that it inhibits apoA-I-dependent cellular cholesterol efflux by suppressing ABCA1 ATPase activity. These results suggest that the ATPase activity of ABCA1 is stimulated preferentially by phospholipids with choline head groups, phosphatidylcholine and sphingomyelin. This study with purified human ABCA1 provides the first biochemical basis of the mechanism for HDL formation mediated by ABCA1.

    Topics: Adenosine Triphosphatases; Animals; ATP Binding Cassette Transporter 1; ATP-Binding Cassette Transporters; Baculoviridae; Cell Line; Cell Membrane; Cholesterol; Choline; Chromatography, Ion Exchange; Detergents; DNA, Complementary; Dose-Response Relationship, Drug; Fibroblasts; Genetic Vectors; Glyburide; Glycosylation; Humans; Insecta; Intracellular Membranes; Lipids; Lipoproteins, HDL; Liposomes; Microsomes; Models, Biological; Phosphatidylcholines; Phosphatidylethanolamines; Phosphatidylglycerols; Phosphatidylserines; Phospholipids; Phytosterols; Protein Binding; Sepharose; Sitosterols; Time Factors; Trypsin

2006
Scavenging of reactive oxygen species by Eriobotrya japonica seed extract.
    Biological & pharmaceutical bulletin, 2006, Volume: 29, Issue:3

    We have clarified that Eriobotrya japonica seed extract has strong antioxidative activity, and is effective for the prevention and treatment of various diseases, such as hepatopathy and nephropathy. In this study, to investigate the influences of components of Eriobotrya japonica seed extract on its antioxidative activity, extracts were prepared using various solvents (n-hexane (Hex), ethyl acetate (EtOAc), n-butanol (n-BuOH), methanol (MeOH) and H2O) and the antioxidative activity of the solvent fractions and components was evaluated based on the scavenging of various radicals (DPPH and O2(-)) measured by the ESR method and the inhibition of Fe3+-ADP induced NADPH dependent lipid peroxidation in rat liver microsomes. The radical scavenging activities and inhibitory activities on lipid peroxidation differed among the solvent fractions and components. In the n-BuOH, MeOH and H2O fractions, radical scavenging activity and inhibitory activity on lipid peroxidation were high. In addition, these fractions contained abundant polyphenols, and the radical scavenging activity increased with the polyphenol content. In the low-polar Hex and EtOAc fractions, the radical scavenging activity was low, but the lipid peroxidation inhibition activity was high. These fractions contained beta-sitosterol, and the inhibitory activity on lipid peroxidation was high. Based on these findings, the antioxidative activity of Eriobotrya japonica seed extract may be derived from many components involved in a complex mechanism, resulting in high activity.

    Topics: Adenosine Diphosphate; Animals; Biphenyl Compounds; Electron Spin Resonance Spectroscopy; Eriobotrya; Free Radical Scavengers; In Vitro Techniques; Indicators and Reagents; Iron; Lipid Peroxidation; Magnetic Resonance Spectroscopy; Male; Microsomes, Liver; NADP; Oxidants; Picrates; Plant Extracts; Rats; Seeds; Sitosterols; Superoxides

2006
Cytochrome P450 CYP710A encodes the sterol C-22 desaturase in Arabidopsis and tomato.
    The Plant cell, 2006, Volume: 18, Issue:4

    Delta22-unsaturated sterols, containing a double bond at the C-22 position in the side chain, occur specifically in fungi and plants. Here, we describe the identification and characterization of cytochrome P450s belonging to the CYP710A family as the plant C-22 desaturase. Recombinant proteins of CYP710A1 and CYP710A2 from Arabidopsis thaliana and CYP710A11 from tomato (Lycopersicon esculentum) were expressed using a baculovirus/insect system. The Arabidopsis CYP710A1 and tomato CYP710A11 proteins exhibited C-22 desaturase activity with beta-sitosterol to produce stigmasterol (CYP710A1, K(m) = 1.0 microM and kinetic constant [k(cat)] = 0.53 min(-1); CYP710A11, K(m) = 3.7 microM and k(cat) = 10 min(-1)). In Arabidopsis transgenic lines with CYP710A1 and CYP710A11 overexpression, stigmasterol levels increased by 6- to 32-fold. Arabidopsis CYP710A2 was able to produce brassicasterol and stigmasterol from 24-epi-campesterol and beta-sitosterol, respectively. Sterol profiling analyses for CYP710A2 overexpression and a T-DNA insertion event into CYP710A2 clearly demonstrated in planta that CYP710A2 was responsible for both brassicasterol and stigmasterol production. Semiquantitative PCR analyses and promoter:beta-glucuronidase transgenic approaches indicated strict tissue/organ-specific regulation for each CYP710A gene, implicating differential tissue distributions of the Delta(22)-unsaturated sterols in Arabidopsis. Our results support the possibility that the CYP710 family may encode P450s of sterol C-22 desaturases in different organisms.

    Topics: Amino Acid Sequence; Arabidopsis; Arabidopsis Proteins; Conserved Sequence; Cytochrome P-450 Enzyme System; Kinetics; Molecular Sequence Data; Oxidoreductases; Plant Proteins; Plants, Genetically Modified; Sequence Alignment; Sequence Homology, Amino Acid; Sitosterols; Solanum lycopersicum; Sterols; Stigmasterol

2006
Antineoplastic activity of selected constituents of Duguetia glabriuscula.
    Fitoterapia, 2006, Volume: 77, Issue:3

    The cytotoxic effects of seven constituents isolated from Duguetia glabriuscula were evaluated against Hep2 human larynx carcinoma cells. The cytotoxicity exhibited by beta-sitosterol was as strong as that of cis-platin. (+)-Alloaromadendran-10,14beta-diol caused inhibition of cellular growth with IC50 values lower than 25 microg/ml, a feature that was considered as revealing significant activity. Polycarpol showed borderline cytotoxicity, whereas the other compounds were inactive.

    Topics: Annonaceae; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cisplatin; Humans; Inhibitory Concentration 50; Plant Bark; Plant Extracts; Plant Leaves; Polycyclic Aromatic Hydrocarbons; Sitosterols; Toxicity Tests

2006
[Chemical constituents from roots of Ficus hirta].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2006, Volume: 31, Issue:2

    To study the chemical constituents from the roots of Ficus hirta.. Compounds were isolated by chromatographic techniques on silica gel and HP-20 resin columns. Their structures were elucidated by chemical and spectroscopic methods.. Ten compounds were identified as beta-sitosterol (1), stigmasterol (2), psoralene (3), 3beta-hydroxy-stigmast-5-en-7-one (4), 5-hydroxy-4', 6, 7, 8-tetramethoxy flavone (5), 4', 5, 6, 7, 8-pentamethoxy flavone (6), 4', 5, 7-trihydroxy-flavone (7), 3beta-acetoxy-beta-amyrin (8), 3beta-acetoxy-alpha-amyrin (9) and hesperidin (10).. The compounds 4, 5, 6 were obtained from this genus for the first time, and all the compounds were obtained from this plant for the first time.

    Topics: Ficus; Ficusin; Flavones; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Stigmasterol

2006
Behavioral changes in fish exposed to phytoestrogens.
    Environmental pollution (Barking, Essex : 1987), 2006, Volume: 144, Issue:3

    We investigated the behavioral effects of exposure to waterborne phytoestrogens in male fighting fish, Betta splendens. Adult fish were exposed to a range of concentrations of genistein, equol, beta-sitosterol, and the positive control 17beta-estradiol. The following behaviors were measured: spontaneous swimming activity, latency to respond to a perceived intruder (mirror reflection), intensity of aggressive response toward a perceived intruder, probability of constructing a nest in the presence of a female, and the size of the nest constructed. We found few changes in spontaneous swimming activity, the latency to respond to the mirror, and nest size, and modest changes in the probability of constructing a nest. There were significant decreases, however, in the intensity of aggressive behavior toward the mirror following exposure to several concentrations, including environmentally relevant ones, of 17beta-estradiol, genistein, and equol. This suggests that phytoestrogen contamination has the potential to significantly affect the behavior of free-living fishes.

    Topics: Aggression; Animals; Behavior, Animal; Equol; Estradiol; Female; Fishes; Genistein; Isoflavones; Male; Nesting Behavior; Phytoestrogens; Sexual Behavior, Animal; Sitosterols; Swimming; Water Pollutants, Chemical

2006
Afzeliixanthones A and B, two new prenylated xanthones from Garcinia afzelii ENGL. (Guttiferae).
    Chemical & pharmaceutical bulletin, 2006, Volume: 54, Issue:4

    Two new prenylated xanthones, afzeliixanthones A (1) and B (2), together with three known xanthones (3-5) and two phytosterols, beta-sitosterol and stigmasterol, were isolated from the CH2Cl2/MeOH (1:1) extract of the stem bark of Garcinia afzelii ENGL. collected in the South West Province of Cameroon. Structures were mainly established using one and two-dimensional NMR and mass spectroscopies. The antioxidant activities of the crude extracts as well as the new compounds (1) and (2) were evaluated.

    Topics: Antioxidants; Garcinia; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Bark; Plant Extracts; Plants, Medicinal; Sitosterols; Stigmasterol; Xanthones

2006
Beta-sitosterol-3-O-beta-D-glucopyranoside: a eukaryotic DNA polymerase lambda inhibitor.
    The Journal of steroid biochemistry and molecular biology, 2006, Volume: 99, Issue:2-3

    Beta-sitosterol-3-O-beta-D-glucopyranoside (compound 1), a steroidal glycoside isolated from onion (Allium cepa L.) selectively inhibited the activity of mammalian DNA polymerase lambda (pol lambda) in vitro. The compound did not influence the activities of replicative DNA polymerases such as alpha, delta and epsilon, but also showed no effect even on the activity of pol beta which is thought to have a very similar three-dimensional structure to the pol beta-like region of pol lambda. Since parts of compound 1 such as beta-sitosterol (compound 2) and D-glucose (compound 3) did not influence the activities of any enzymes tested, the converted structure of compounds 2 and 3 might be important for pol lambda inhibition. The inhibitory effect of compound 1 on both intact pol lambda (i.e. residues 1-575) and a truncated pol lambda lacking the N-terminal BRCA1 C-terminus (BRCT) domain (133-575, del-1 pol lambda) was dose-dependent, and 50% inhibition was observed at a concentration of 9.1 and 5.4 microM, respectively. The compound 1-induced inhibition of del-1 pol lambda activity was non-competitive with respect to both the DNA template-primer and the dNTP substrate. On the basis of these results, the pol lambda inhibitory mechanism of compound 1 is discussed.

    Topics: Animals; Binding Sites; Catalysis; Cattle; DNA Polymerase beta; Dose-Response Relationship, Drug; Drosophila melanogaster; Enzyme Inhibitors; Eukaryotic Cells; Glucose; Glucosides; Humans; Kinetics; Magnetic Resonance Spectroscopy; Molecular Structure; Mutation; Onions; Peptide Fragments; Rats; Sitosterols; Structure-Activity Relationship

2006
Incorporation of phytosterols in human keratinocytes. Consequences on UVA-induced lipid peroxidation and calcium ionophore-induced prostaglandin release.
    Chemistry and physics of lipids, 2006, Volume: 141, Issue:1-2

    We have designed experimental conditions allowing the replacement of 50% of cholesterol of human keratinocytes (SVK14 line) with sitosterol or stigmasterol without affecting cellular viability. We have investigated the influence of incorporating phytosterol on the ultraviolet-A-induced formation of lipid-peroxidation products (thiobarbituric reactive substances (TBARS)) in these cells. Our results show that ultraviolet-A-induced lipid peroxidation depends on the nature of the phytosterol. Sitosterol induces a significant decrease (-30%) of TBARS relative to the control whereas stigmasterol markedly increases lipid peroxidation (+70%). We have also studied the effect of plant sterols on prostaglandin release by using the Ca(2+) ionophore A23187 as an in vitro model of the inflammation induced by UVA radiation. We show that in the presence of 50% of phytosterol (particularly stigmasterol), the release of prostaglandin (6-ketoPG(1alpha), PGE(2)) is increased compared to untreated cells. This pro-inflammatory effect of phytosterols is correlated with a loss of the regulation of the intracellular Ca(2+) concentration.

    Topics: Calcium; Cations, Divalent; Cell Survival; Cells, Cultured; Cholesterol; Humans; Keratinocytes; Kinetics; Lipid Peroxidation; Phytosterols; Prostaglandins; Sitosterols; Stigmasterol; Ultraviolet Rays

2006
Common sources and estimated intake of plant sterols in the Spanish diet.
    Journal of agricultural and food chemistry, 2006, May-03, Volume: 54, Issue:9

    Plant sterols (PS) are minor lipid components of plants, which may have potential health benefits, mainly based in their cholesterol-lowering effect. The aim of this study was to determine the composition and content of PS in plant-based foods commonly consumed in Spain and to estimate the PS intake in the Spanish diet. For this purpose, the determination of PS content, using a modern methodology to measure free, esterified, and glycosidic sterol forms, was done. Second, an estimation of the intake of PS, using the Spanish National Food Consumption data, was made. The daily intake per person of PS--campesterol, beta-sitosterol, stigmasterol, and stigmastanol--in the Spanish diet was estimated at 276 mg, the largest component being beta-sitosterol (79.7%). Other unknown compounds, tentatively identified as PS, may constitute a considerable potential intake (99 mg). When the daily PS intake among European diets was compared in terms of campesterol, beta-sitosterol, stigmasterol, and stigmastanol, the PS intake in the Spanish diet was in the same range of other countries such as Finland (15.7% higher) or The Netherlands (equal). However, some qualitative differences in the PS sources were detected, that is, the predominant brown bread and vegetable fat consumption in the northern diets versus the white bread and vegetable oil consumption in the Spanish diet. These differences may help to provide a link between the consumption of PS and healthy effects of the diet.

    Topics: Bread; Diet; Edible Grain; Food Analysis; Fruit; Phytosterols; Plant Oils; Sitosterols; Spain; Vegetables

2006
Assessment of the reproductive-endocrine disrupting potential of chlorine dioxide oxidation products of plant sterols.
    Environmental science & technology, 2006, Apr-15, Volume: 40, Issue:8

    This study examined the hypothesis that chlorine dioxide bleaching used in pulp and paper production causes the formation of reproductive-endocrine disrupting compounds from plant sterols. This was tested by conducting a laboratory simulation of the chlorine dioxide oxidation of two plant sterols, beta-sitosterol and stigmasterol. Oxidation products of the plant sterol beta-sitosterol were purified and identified and found to be cholestan-24-ethyl-3-one, 4-cholestene-24-ethyl-3-one, and 4-cholestene-24-ethyl-3,6-dione. The first two compounds were found in a number of pulp and paper effluents and biosolids. The sterols and their oxidation products were tested in vitro using bioassays for androgenicity and estrogenicity. A 28 d in vivo bioassay was employed to examine masculinization in female mosquitofish. In vitro bioassays revealed little estrogenic activity in the parent sterols or in mixtures of their oxidation products. Androgenic activity as measured by the androgen receptor binding bioassay was in the order of 19-96 microg/g testosterone equivalents but with no increase or decrease with chlorine dioxide oxidation. The mosquitofish bioassay did not show significant masculinization for any of the preparations tested. A number of androstane steroids were identified in the sterols tested, however, those compounds could only account for a small fraction of the androgenic activity in the sterols. It was clear that the parent sterols were not themselves acting as androgens in the bioassays used. This study indicated that chlorine dioxide oxidation of sterols produced predominantly oxidized sterols that were not likely to act through androgenic or estrogenic mechanisms.

    Topics: Animals; Binding, Competitive; Chlorine Compounds; Cyprinodontiformes; Endocrine Disruptors; Female; In Vitro Techniques; Industrial Waste; Male; Oncorhynchus mykiss; Oxidation-Reduction; Oxides; Paper; Plants; Receptors, Androgen; Receptors, Estrogen; Sitosterols; Stigmasterol; Virilism; Waste Disposal, Fluid; Water Pollutants, Chemical

2006
Intestinal cholesterol absorption inhibitor ezetimibe added to cholestyramine for sitosterolemia and xanthomatosis.
    Gastroenterology, 2006, Volume: 130, Issue:6

    Sitosterolemia is a rare, recessively inherited disorder characterized by increased absorption and delayed removal of noncholesterol sterols, which is associated with accelerated atherosclerosis, premature coronary artery disease, hemolysis, and xanthomatosis. Treatments include low-sterol diet and bile salt-binding resins; however, these often do not reduce the xanthomatosis. We examined the effects of the intestinal cholesterol/phytosterol transporter inhibitor ezetimibe added to cholestyramine in a young female patient with sitosterolemia and associated xanthomatosis. The patient was an 11-year-old female with sitosterolemia presenting with prominent xanthomas in the subcutaneous tissue of both elbows who was receiving treatment with cholestyramine 2 g once daily. Bilateral carotid bruits were audible, and a grade II/VI systolic murmur was detected at the left upper sternal border. She also had a low platelet count of 111,000/microL. Ezetimibe 10 mg once daily was added to the patient's ongoing cholestyramine regimen, and she was evaluated for 1 year. The patient followed an unrestricted diet during the 1-year treatment period. After 1 year of treatment with ezetimibe added to ongoing cholestyramine therapy, the patient's plasma sitosterol and campesterol levels decreased by approximately 50%. Her carotid bruits completely resolved, her systolic murmur diminished, and her platelet count rose to 268,000/microL. More remarkably, the tuberous xanthomas on her elbows had completely regressed. Ezetimibe added to ongoing low-dose cholestyramine therapy led to a marked improvement in plasma sterol concentrations, complete regression of xanthomatosis, resolution of carotid bruits, and improvement in cardiac murmur in a young female patient with sitosterolemia.

    Topics: Anticholesteremic Agents; Azetidines; Child; Cholestyramine Resin; Dose-Response Relationship, Drug; Drug Administration Schedule; Drug Therapy, Combination; Ezetimibe; Female; Follow-Up Studies; Humans; Risk Assessment; Severity of Illness Index; Sitosterols; Treatment Outcome; Xanthomatosis

2006
[Steroids isolated from fruit of Hovenia acerba].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2006, Volume: 29, Issue:1

    To study on the chemical constituents of Hovenia acerba.. Compounds were isolated with stratography and solvent, and identified by spectroscopy.. beta-sitoseterol, 3 beta-hydroxy-3-deoxymoronic acid and beta-sitoseteryl-3-O-beta-D-glucopyranoside were obtained from fruit of Hovenia acerba.. The three compounds were steroids isolated from Hovenia acerba Thunb. for the frist time.

    Topics: Fruit; Gas Chromatography-Mass Spectrometry; Molecular Structure; Oleanolic Acid; Plants, Medicinal; Rhamnaceae; Sitosterols; Steroids

2006
Scanning electron microscopy investigations on bis(2-ethylhexyl)phthalate treated Mycobacterium cells.
    Microscopy research and technique, 2006, Volume: 69, Issue:8

    Comparative investigation of steroid transforming activity and ultrastructural changes of bis(2-ethylhexyl)phthalate (BEHP, phthalate) treated Mycobacterium sp. NRRL B-3805 cells was carried out. Transformation of beta-sitosterol into androstenedione (AD) and androstadienedione (ADD) was performed in phthalate medium by resting cells preincubated in the organic solvent for a period from 3 to 24 h. It was observed that a preincubation greater than 12 h leads to the development of dense formations on the cells surface, reduction in the cell turgor, disruption in the cell walls, and formation of zones with reduced electron density. The preincubation for 24 h causes deeper changes in the cell ultrastructure but the treated cells retain their steroid transforming activity, allowing up to 80% of the substrate to be converted into AD and ADD. A preincubation of the resting Mycobacterium cells in BEHP for 6 h might be recommended as it leads to an achievement of stoichiometrical transformation of the substrate into AD and ADD and slightly higher initial rate of the reaction performed.

    Topics: Androstenedione; Diethylhexyl Phthalate; Microscopy, Electron, Scanning; Mycobacterium; Sitosterols; Time Factors

2006
Constituents of Salvia microphylla.
    Natural product research, 2006, Jul-10, Volume: 20, Issue:8

    A new phenolic ester 2-( p-hydroxyphenyl)ethyl eicosaheptanoic acid ester (1) and a known one hexacosylferulate (2) were isolated from the acetone extract of Salvia microphylla. In addition, two sesquiterpenes beta-eudesmol (3) and 8alpha-hydroxy-beta-eudesmol (4), a diterpene carnosic acid 12-methyl ether (12-methoxycarnosic acid) (5), three triterpenes erithrodiol 3-acetate, oleanolic acid, lupeol and beta-sitosterol were obtained as known compounds from this plant extract. The structures of the isolated compounds were elucidated by spectroscopic methods, including one- and two- dimensional 1H- and 13C-NMR and MS spectroscopies. The selected compounds were tested for antimicrobial activity against standard bacterial strains, and only carnosic acid 12-methyl ether showed antimicrobial activity against S. aureus at 78 microg mL(-1).

    Topics: Esters; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Phenols; Salvia; Sitosterols; Terpenes

2006
Extracts from Pygeum africanum and other ethnobotanical species with antiandrogenic activity.
    Planta medica, 2006, Volume: 72, Issue:9

    Extracts from Pygeum africanum, Serenoa repens and Cucurbita pepo are used in the treatment of benign prostatic hyperplasia (BPH) and prostate cancer (PCa). The activity of the androgen receptor (AR) is known to control growth of the prostate. Here, we examined extracts of these plants for their antiandrogenic activity using an AR responsive reporter gene assay for drug discovery. A selective dichloromethane extract from the stem barks of Pygeum africanum revealed the highest antiandrogenic effect. Bioactivity-directed fractionation of this extract led to the isolation of N-butylbenzenesulfonamide (NBBS) indicating that extracts of the stem bark of P. africanum harbour androgen antagonistic activity. This compound may provide a novel approach for the prevention and treatment of BPH and human PCa.

    Topics: Androgen Antagonists; Animals; Cell Line; Cucurbita; Genes, Reporter; Haplorhini; Luciferases; Oleanolic Acid; Plant Extracts; Prunus africana; Serenoa; Sitosterols; Sulfonamides; Triterpenes; Ursolic Acid

2006
Ketosteroids and hydroxyketosteroids, minor metabolites of sugarcane wax.
    Steroids, 2006, Volume: 71, Issue:8

    Besides beta-sitosterol and stigmasterol, the major steroids of sugarcane, the following minor steroids have been isolated and identified from sugarcane wax: 3,6-diketosteroids, Delta(4)-3-keto steroids, and Delta(4)-6-hydroxy-3-keto steroids. Their structures were established by spectroscopic techniques and chemical correlations.

    Topics: Gas Chromatography-Mass Spectrometry; Hydroxysteroids; Ketosteroids; Magnetic Resonance Spectroscopy; Models, Biological; Plant Structures; Saccharum; Sitosterols; Stigmasterol; Waxes

2006
[Studies on chemical constituents in roots of Heracleum rapula].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2006, Volume: 31, Issue:8

    To study the chemical constituents in roots of Heracleum rapula.. The constituents were isolated by column chromatography on silica gel and ODS, and identified by spectroscopic methods.. Eight compounds, xanthotoxol (I), 8-geranyloxypsoralen (II), (+)-marmesin (III), beta-sitosterol (IV), stigmasterol (V), oleanolic acid (VI), ferulic (VII), scopoletin (VIII) were isolated and identified.. Compounds IV, V, VI, VII, VIII were isolated from this plant for the first time.

    Topics: Coumaric Acids; Heracleum; Oleanolic Acid; Plant Roots; Plants, Medicinal; Scopoletin; Sitosterols; Stigmasterol

2006
In-vitro effects of polyphenols from cocoa and beta-sitosterol on the growth of human prostate cancer and normal cells.
    European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP), 2006, Volume: 15, Issue:4

    Cocoa contains many different types of physiologically active components. It was shown that cocoa beans are rich in specific antioxidants such as flavonoids, catechins, epicatechins and proanthocyanidins. Additionally, beta-sitosterol, the most common phytosterol, may play a protective role in the development of cancer. The aim of this in-vitro study was to evaluate the inhibitory effect of different cocoa polyphenols extracts, alone or combined with beta-sitosterol, on two human prostate cancer cell lines (nonmetastatic 22Rv1 cells and metastatic DU145 cells) and a normal human prostate cell line (RWEP-1). A synergy between beta-sitosterol and cocoa polyphenols extract was also researched. Cells were treated independently with five products from 1 to 72 h: (1/) synthetic beta-sitosterol, (2/) a cocoa polyphenols extract supplemented with beta-sitosterol, (3/) three different cocoa polyphenols extracts naturally containing beta-sitosterol. In the experiment, beta-sitosterol was tested from 10(-6) to 10(-3)%; cocoa polyphenols extract supplementation was with 0.72% beta-sitosterol; finally cocoa polyphenols extracts were added to the cells at very low concentrations ranging from 0.001 to 0.2%. The growth and viability of cells were measured using colorimetric assay at 1, 3, 6, 24, 48 and 72 h of treatment. IC50 and IC100 corresponding to the concentration leading to a decrease of 50% and 100% of cell growth were determined. At the highest tested concentration, cocoa polyphenols extracts induced a complete inhibition of growth of metastatic and nonmetastatic cancer cell lines. In addition, cocoa polyphenols extracts were more active against local cancer cells than against metastatic cells. Moreover, at the highest tested concentration, cocoa polyphenols extracts are not effective on a normal prostate cell lines. Beta-sitosterol induced low growth inhibition of both cancer cell line. Cocoa polyphenols extracts, however, were significantly more active and showed a strong and fast inhibition of cell growth than beta-sitosterol alone. No synergy or addition was observed when beta-sitosterol was tested together with the cocoa polyphenols extract. Our results show that cocoa polyphenols extracts have an antiproliferative effect on prostate cancer cell growth but not on normal cells, at the highest tested concentration.

    Topics: Antineoplastic Agents; Cacao; Carcinoma; Cell Proliferation; Dose-Response Relationship, Drug; Flavonoids; Humans; Male; Phenols; Polyphenols; Prostate; Prostatic Neoplasms; Sitosterols; Time Factors; Tumor Cells, Cultured

2006
Analysis of sterols by high-performance liquid chromatography/mass spectrometry combined with chemometrics.
    Rapid communications in mass spectrometry : RCM, 2006, Volume: 20, Issue:16

    A newly developed high-performance liquid chromatography/mass spectrometry (HPLC/MS) method has been successfully used to analyze plasma concentrations of various phytosterols (cholestanol and beta-sitosterol) and cholesterol metabolites (desmosterol and lathosterol). This was based on an unusual solvent combination of water/methanol vs. methanol/acetone/n-hexane applied on a Purospher Star RP-18e (125 x 2 mm, 3 microm) column, which proved excellent for the separation, identification and quantification of plasma sterols. Simple solid-phase extraction preparation of plasma samples was performed, followed by the developed fast and robust HPLC separation. Results on four groups of people were compared, those with low, normal and high plasma cholesterol levels and those with high cholesterol levels on statin therapy, and the results were evaluated using linear discriminant analysis (LDA). Variable selection for LDA was achieved using backward removal selection. Highly discriminatory variables were the ratios of desmosterol to sitosterol and of lathosterol to total plasma cholesterol. The latter ratio was also excellent for distinguishing subjects on statin therapy. The success rate of classification was 100%. The present pilot study shows the potential of HPLC/MS analysis and chemometrics for studying cholesterol-related disorders and warrants future full-scale medical study.

    Topics: Cholestanol; Cholesterol; Chromatography, High Pressure Liquid; Desmosterol; Discriminant Analysis; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypercholesterolemia; Mass Spectrometry; Pilot Projects; Sitosterols; Sterols

2006
Quantitative analysis of beta-sitosterol oxides induced in vegetable oils by natural sunlight, artificially generated light, and irradiation.
    Journal of agricultural and food chemistry, 2006, Jul-26, Volume: 54, Issue:15

    UV radiation is able to induce lipid peroxidation. Photooxidation-induced beta-sitosterol oxides were monitored in four vegetable oils exposed to sunlight for 10, 20, and 30 days during May 2005 (northeastern France), exposed to artificial light generated by a high-pressure Hg lamp for 21, 42, and 63 h at room temperature, and exposed to a 10 MeV electron beam at 0.93, 2.69, and 9.30 kGy at 8 degrees C. Quantification was performed by capillary gas chromatography-mass spectrometry according to the total ion current mode and using a reconstructed ion trace chromatogram with specific ion fragments. Sunlight induced the formation of higher amounts of oxides than UV light, while no significant oxidizing effect was observed with electron beam irradiation. However, data suggested that the amount of the main oxides formed was strongly dependent on the dose rate (length of exposure). Accordingly, shorter but more intense treatments had lower oxidizing effects.

    Topics: Fatty Acids, Monounsaturated; Gas Chromatography-Mass Spectrometry; Light; Lipid Peroxidation; Olive Oil; Oxides; Photochemistry; Plant Oils; Rapeseed Oil; Sitosterols; Soybean Oil; Sunflower Oil; Sunlight; Ultraviolet Rays

2006
Sterol intermediates from cholesterol biosynthetic pathway as liver X receptor ligands.
    The Journal of biological chemistry, 2006, Sep-22, Volume: 281, Issue:38

    The liver X receptors (LXRs) are ligand-activated transcription factors that regulate the expression of genes controlling lipid metabolism. Oxysterols bind LXRs with high affinity in vitro and are implicated as ligands for the receptor. We showed previously that accumulation of selected dietary sterols, in particular stigmasterol, is associated with activation of LXR in vivo. In the course of the defining of structural features of stigmasterol that confer LXR agonist activity, we determined that the presence of an unsaturated bond in the side chain of the sterol was necessary and sufficient for activity, with the C-24 unsaturated cholesterol precursor sterols desmosterol and zymosterol exerting the largest effects. Desmosterol failed to increase expression of the LXR target gene, ABCA1, in LXRalpha/beta-deficient mouse fibroblasts, but was fully active in cells lacking cholesterol 24-, 25-, and 27-hydroxylase; thus, the effect of desmosterol was LXR-dependent and did not require conversion to a side chain oxysterol. Desmosterol bound to purified LXRalpha and LXRbeta in vitro and supported the recruitment of steroid receptor coactivator 1. Desmosterol also inhibited processing of the sterol response element-binding protein-2 and reduced expression of hydroxymethylglutaryl-CoA reductase. These observations are consistent with specific intermediates in the cholesterol biosynthetic pathway regulating lipid homeostasis through both the LXR and sterol response element-binding protein pathways.

    Topics: Animals; ATP Binding Cassette Transporter 1; ATP-Binding Cassette Transporters; CHO Cells; Cholesterol; Cricetinae; Desmosterol; DNA-Binding Proteins; Dose-Response Relationship, Drug; Histone Acetyltransferases; Intracellular Signaling Peptides and Proteins; Ligands; Liver X Receptors; Membrane Proteins; Mice; Nuclear Receptor Coactivator 1; Orphan Nuclear Receptors; Receptors, Cytoplasmic and Nuclear; Sitosterols; Sterol Regulatory Element Binding Protein 2; Sterols; Stigmasterol; Transcription Factors

2006
Influence of rosemary (Rosmarinus officinalis, L.) on plant sterol oxidation in extra virgin olive oil.
    Molecular nutrition & food research, 2006, Volume: 50, Issue:9

    The objective of this study was to investigate the potential role of rosemary compounds in inhibiting the plant sterol oxidation in extra virgin olive oil during heating. The stability of plant sterols was measured by quantification of plant sterol and sterol oxide formation upon 6 h of heating in both the extra virgin olive oil and its respective oil at 10% rosemary concentration (ROE). The total sterol and sitosterol oxide contents were determined by GC-flame ionization detection (GC-FID) and GC-MS techniques, respectively. Heating experiments were carried out at 180 degrees C for 0, 1, 3 and 6 h. The total sterol content in the extra virgin olive oil was 255 mg/100 g and that in the ROE 270 mg/100 g. Sitosterol was the most abundant sterol in both samples (50% of total sterol). The ROE showed a lower content of sitosterol oxides with respect to the extra virgin olive oil during heating: after 6 h of heating only 6.1% of sitosterol oxides were formed, while up to 11.5% of sitosterol oxidized in the extra virgin olive oil. Our findings suggested that rosemary compounds were able to counteract the oxidation of plant sterols in the extra virgin olive oil during heating, preventing formation of potentially harmful compounds to human health.

    Topics: Antioxidants; Hot Temperature; Olive Oil; Oxidation-Reduction; Oxides; Phytosterols; Plant Leaves; Plant Oils; Rosmarinus; Sitosterols

2006
Sitosterol-containing lipoproteins trigger free sterol-induced caspase-independent death in ACAT-competent macrophages.
    The Journal of biological chemistry, 2006, Nov-03, Volume: 281, Issue:44

    Sitosterolemia is a disease characterized by very high levels of sitosterol and other plant sterols and premature atherothrombotic vascular disease. One theory holds that plant sterols can directly promote atherosclerosis, but the mechanism is not known. Unesterified, or "free," cholesterol (FC) is a potent inducer of macrophage death, which causes plaque necrosis, a precursor to atherothrombosis. FC-induced macrophage death, however, requires dysfunction of the sterol esterifying enzyme acyl-coenzyme A-cholesterol acyltransferase (ACAT), which likely occurs slowly during lesion progression. In contrast, plant sterols are relatively poorly esterified by ACAT, and so they may cause macrophage death and plaque necrosis in an accelerated manner. In support of this hypothesis, we show here that macrophages incubated with sitosterol-containing lipoproteins accumulate free sterols and undergo death in the absence of an ACAT inhibitor. As with FC loading, sitosterol-induced macrophage death requires sterol trafficking to the endoplasmic reticulum, and sitosterol-enriched endoplasmic reticulum membranes show evidence of membrane protein dysfunction. However, whereas FC induces caspase-dependent apoptosis through activation of the unfolded protein response and JNK, sitosterol-induced death is caspase-independent and involves neither the unfolded protein response nor JNK. Rather, cell death shows signs of necroptosis and autophagy and is suppressed by inhibitors of both processes. These data establish two new concepts. First, a relatively subtle change in sterol structure fundamentally alters the type of death program triggered in macrophages. Understanding the basis of this alteration should provide new insights into the molecular basis of death pathway signaling. Second, sitosterol-induced macrophage death does not require ACAT dysfunction and so may occur in an accelerated fashion. Pending future in vivo studies, this concept may provide at least one mechanism for accelerated plaque necrosis and atherothrombotic disease in patients with sitosterolemia.

    Topics: Animals; Apoptosis; Biological Transport; Caspases; Cells, Cultured; Endoplasmic Reticulum; Enzyme Inhibitors; Female; Imidazoles; Indoles; Intracellular Membranes; Lipoproteins; Macrophages; Mice; Mice, Inbred C57BL; Mice, Knockout; p38 Mitogen-Activated Protein Kinases; Sarcoplasmic Reticulum Calcium-Transporting ATPases; Sitosterols; Sterol O-Acyltransferase; Sterols

2006
Herbicidal effects of statin pharmaceuticals in Lemna gibba.
    Environmental science & technology, 2006, Aug-15, Volume: 40, Issue:16

    Statin pharmaceuticals, heavily prescribed in the treatment of hypercholesterolemia, are competitive inhibitors of 3-hydroxy-3-methylglutaryl coenzyme-A reductase (HMGR). In plants, these compounds also inhibit HMGR, which regulates cytosolic isoprenoid biosynthesis in the mevalonic acid (MVA) pathway. Phytotoxicity was evaluated in the higher aquatic plant Lemna gibba exposed to atorvastatin and lovastatin for 7-days by measuring the concentrations of sterols and ubiquinone; products downstream in the MVA pathway. The efficiency of the parallel and unaffected methylerythritol phosphate pathway (MEP) was also evaluated by measuring the end product, plastoquinone. Statin treatment caused an accumulation of plastoquinone, and unexpectedly, ubiquinone, an artifact likely due to metabolite sharing from the plastidial MEP pathway. Statins were, however, highly phytotoxic to L. gibba and HPLC-UV analysis of plant extracts showed significantly decreased concentrations of both stigmasterol and beta-sitosterol, which are critical components of plant membranes and regulate morphogenesis and development. EC10 values for atorvastatin and lovastatin were as small as 26.1 and 32.8 microg/L, respectively. However, hazard quotients indicated that statins present little risk to the model higher aquatic plant Lemna gibba at environmentally relevant concentrations, even though pathway-specific endpoints were 2-3 times more sensitive than traditional gross morphological endpoints typically used in risk assessment.

    Topics: Atorvastatin; Chromatography, High Pressure Liquid; Heptanoic Acids; Herbicides; Hydroxymethylglutaryl CoA Reductases; Lovastatin; Mevalonic Acid; Models, Chemical; Pharmaceutical Preparations; Plants; Plastoquinone; Pyrroles; Risk Assessment; Sitosterols; Sterols; Ubiquinone; Ultraviolet Rays

2006
Solubility in and affinity for the bile salt micelle of plant sterols are important determinants of their intestinal absorption in rats.
    Lipids, 2006, Volume: 41, Issue:6

    Intestinal absorption of various plant sterols was investigated in thoracic duct-cannulated normal rats. Lymphatic recovery was the highest in campesterol, intermediate in brassicasterol and sitosterol, and the lowest in stigmasterol and sitostanol. Higher solubility in the bile salt micelle was observed in sitosterol, campesterol, and sitostanol than in brassicasterol and stigmasterol. The solubility of the latter two sterols was extremely low. When the affinity of plant sterols for the bile salt micelle was compared in an in vitro model system, which assessed sterol transfer from the micellar to the oil phase, the transfer rate was the highest in brassicasterol, intermediate in campesterol and stigmasterol, and lowest in sitosterol and sitostanol. Although no significant correlations between lymphatic recovery of plant sterols and their micellar solubility or transfer rate from the bile salt micelle were observed, highly positive correlation was obtained between the lymphatic recovery and the multiplication value of the micellar solubility and the transfer rate. These observations strongly suggest that both solubility in and affinity for the bile salt micelle of plant sterols are important determinants of their intestinal absorption in rats.

    Topics: Animals; Bile Acids and Salts; Cholestadienols; Cholesterol; Intestinal Absorption; Lymph; Male; Micelles; Models, Biological; Phytosterols; Rats; Rats, Wistar; Sitosterols; Solubility; Stigmasterol; Triolein

2006
Bioassay-guided isolation of antiatherosclerotic phytochemicals from Artocarpus altilis.
    Phytotherapy research : PTR, 2006, Volume: 20, Issue:12

    The cytoprotective effects of various solvent extracts of Artocarpus altilis (Parkinson) Fosberg were evaluated. The cytoprotective effects were determined in human U937 cells incubated with oxidized LDL (OxLDL) using the 4-[3-(4-iodophenyl)-2-(4-nitrophenyl)-2H-5-tetrazolio]-1, 3-benzene disulfonate (WST-1) assay. The results demonstrated that the ethyl acetate extract showed cytoprotective activities. To identify the main cytoprotective components, a bioassay guided isolation of the ethyl acetate extract afforded b-sitosterol (1) and six flavonoids (2-7). Their chemical structures were established on the basis of spectroscopic evidence and comparison with literature data. Of these compounds, compound 6 was obtained from A. altilis for the first time. The cytoprotective effect offers good prospects for the medicinal applications of A. altilis.

    Topics: Artocarpus; Atherosclerosis; Biological Assay; Cell Survival; Flavonoids; Humans; Lipoproteins, LDL; Plant Extracts; Plant Leaves; Sitosterols; U937 Cells

2006
[Study on the chemical constituents of Mitragyna rotundifolia].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2006, Volume: 29, Issue:6

    Twelve compounds were isolated from the EtOAc-soluble and ButOH-soluble portions of the EtOH extract from the bark of Mitragyna rotundifolia. These compounds were identified by their spectral data as dauricine (1), 3,4-dihydroxybezoic acid (2), beta-sitosterol (3), scopleton (4),3,4,5-trimethyoxyphenol-1-glucopyranoside (5), taraxerol (6), 4-hydroxy-3-methyloxybenzoic acid (7), 3-hydroxy-4-methyloxybenzoic acid (8), caffeic acid (9), gambirine (10), gambireine (11),1,1-dimetheyl-2-acetl-diethyl ether (12), respectively. All compounds were isolated from this genus for the first time.

    Topics: Alkaloids; Caffeic Acids; Mitragyna; Oleanolic Acid; Plant Bark; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet

2006
[Compounds from marine mangrove plant Bruguiera sexangula var. rhynchopetala].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2006, Volume: 31, Issue:14

    To investigate the chemical constituents in Bruguiera sexangula var. rhynchopetala.. Silica gel flash chromatography together with Sephadex LH - 20 were performed for the isolation and purification of the petrol ether fraction of this plant, and the structures were elucidated by spectral analysis as well as the comparison of the spectral data with those reported in the literatures.. Nine compounds were obtained and identified as lupeol (1), lupeone (2), trans-hydroxy-cinnamoyl ester of lupeol (3), taraxerone (4), beta-amyril-palmitate (5), squalene (6),beta-sitosterol (7), daucosterol (8) and 7alpha-hydroxy-sitosterol (9).. All the compounds were first isolated from B. sexangula var. rhynchopetala.

    Topics: Oleanolic Acid; Pentacyclic Triterpenes; Plants, Medicinal; Rhizophoraceae; Sitosterols; Triterpenes

2006
Separation of free sterols by high temperature liquid chromatography.
    Journal of chromatography. A, 2006, Dec-29, Volume: 1137, Issue:2

    Increasing the column temperature accelerates markedly elution in HPLC. The separation of five free sterols was studied on three packing materials that can withstand high temperatures. These stationary phases included graphitic carbon, a polymeric C18 silica, and a zirconia-based adsorbent. Measurements of retention data were made at up to 150 degrees C with mobile phases of different compositions. Since the columns tested afford different retention mechanisms, a variety of elution patterns were observed, with some being more advantageous than others for certain sterol separations. Effects observed include some selectivity improvements and some elution order reversals. The separation of free sterols in selected fruit juices is also presented. Albeit at the expense of a longer analysis time, the graphitic carbon column produced the best separation of the sterols in this study.

    Topics: Alkanes; Beverages; Cholesterol; Chromatography, High Pressure Liquid; Citrus; Ergosterol; Graphite; Hot Temperature; Lanosterol; Sitosterols; Sterols; Stigmasterol; Zirconium

2006
Investigation of de novo cholesterol synthetic capacity in the gonads of goldfish (Carassius auratus) exposed to the phytosterol beta-sitosterol.
    Reproductive biology and endocrinology : RB&E, 2006, Nov-21, Volume: 4

    Total and intra-mitochondrial gonadal cholesterol concentrations are decreased in fish exposed to the phytoestrogen beta-sitosterol (beta-sit). The present study examined the potential for beta-sit to disrupt de novo cholesterol synthesis in the gonads of goldfish exposed to 200 microgram/g beta-sit and 10 microgram/g 17beta-estradiol (E2; estrogenic control) by intra-peritoneal Silastic implants for 21 days. The de novo cholesterol synthetic capacity was estimated by incubating gonadal tissue with 14C-acetate for a period of 18 hours, followed by chloroform/methanol lipid extraction and thin layer chromatography (TLC) lipid separation. Lipid classes were confirmed using infrared spectroscopy. Plasma testosterone (T) and total cholesterol concentration were measured and gonadosomatic index (GSI) was calculated. Plasma T was significantly reduced in male beta-sit-treated fish compared to control and E2-treated fish (p < 0.001). 14C-Acetate incorporation into cholesterol and cholesterol esters was not significantly different among treatment groups for male and female fish, however, 14C-enrichment was higher than expected in both triglycerides (TG) and free fatty acids (FFA). FFA incorporation was significantly higher in male control fish than either beta-sit or E2 treatments (p = 0.005). Plasma cholesterol concentration was significantly increased in the male beta-sit treatment group compared to controls (p = 0.027). These results indicate gonadal de novo cholesterol biosynthetic capacity is not disrupted by beta-sit or E2 treatment in early recrudescing male or female goldfish, while plasma cholesterol and steroid concentrations are sensitive to beta-sit exposure.

    Topics: Animals; Cholesterol; Drug Implants; Female; Goldfish; Hypolipidemic Agents; Male; Organ Size; Ovary; Sex Factors; Sitosterols; Testis; Testosterone

2006
Differential scanning calorimetry evidence of the enhancement of beta-sitosterol absorption across biological membranes mediated by beta-cyclodextrins.
    Journal of agricultural and food chemistry, 2006, Dec-27, Volume: 54, Issue:26

    beta-Sitosterol is a plant sterol that has received much attention because of its effectiveness in reducing the absorption of dietary cholesterol, as well as in offering protection from cardiovascular diseases and cancer development. Thus, the knowledge of the interaction of beta-sitosterol with biological membranes can help in understanding its mechanism of action. In the present paper, the differential scanning calorimetry technique has been used to study the interaction of beta-sitosterol with a biomembrane model constituted by dimyristoylphosphatidylcholine multilamellar vesicles. Furthermore, kinetic experiments have been carried out to follow the uptake of beta-sitosterol by biomembranes and the effect of beta-cyclodextrins on such a process. Our results indicate that opportune concentrations of beta-cyclodextrins improve the uptake of beta-sitosterol by phospholipid membranes.

    Topics: Absorption; beta-Cyclodextrins; Calorimetry, Differential Scanning; Cell Membrane Permeability; Kinetics; Lipid Bilayers; Liposomes; Sitosterols; Thermodynamics

2006
A novel type of membrane based on cholesteryl phosphocholine, cholesteryl phosphate, or sitosteryl phosphate, and dimyristoylglycerol.
    Chemistry & biodiversity, 2006, Volume: 3, Issue:2

    Mixtures of amphiphilic cholesteryl phosphate (CP), sitosteryl phosphate (SP), or cholesteryl phosphocholine (CPC) with the nonphosphoryl diacyl lipid dimyristoylglycerol (DMG) or with cholesterol give self-organized systems (giant vesicles) in a wide range of pH, as demonstrated by fluorescence microscopy, differential scanning calorimetry, and small-angle X-ray scattering. The water permeability of a 1 : 1 molar mixture of CPC and DMG was also measured by a stopped-flow/light-scattering method. The novel self-organized systems are akin to natural eukaryotic ones, the only difference being the site of the phosphate-containing head-group, located on cholesterol instead of DMG. They might be present in some organisms not yet studied for the composition of their membranes.

    Topics: Cholesterol Esters; Glycerophospholipids; Membranes, Artificial; Phosphorylcholine; Sitosterols

2006
[Effects of beta-sitosterol on microtubular systems in cervical cancer cells].
    Zhonghua yi xue za zhi, 2006, Oct-24, Volume: 86, Issue:39

    To investigate beta-sitosterol's inhibitory effects on SiHa cells' growth, and the effects on microtubular system in SiHa cell.. Proliferation inhibition of SiHa cell line was evaluated by MTT assay. Cell cycle of SiHa cells treated with beta-sitosterol was analyzed by flow cytometry. The expression and distribution of microtubule and microtubule associated protein 2 in SiHa cells were investigated by confocal microscopy. Immunoblotting analysis was used to determine tubulin alpha, microtubule associated protein 2, and the proportion of polymerization of tubulin.. beta-sitosterol could obviously inhibit the proliferation of SiHa cells, and induce the accumulation of cells in S phase (rather than the G2/M phase) and mitotic arrest in the cell cycle. Confocal microscopy showed an abnormal microtubular network in SiHa cell treated with beta-sitosterol for 5 days, and the expression of microtubule associated protein 2 was marked down-regulated. Further analysis by immunoblotting confirmed the down-regulation of beta-sitosterol on the expression for both microtubule associated protein 2 and tubulin alpha. Moreover, beta-sitosterol reduced the proportion of polymerization of microtubule in a time-dependent manner.. beta-sitosterol could down-regulate the expression of tubulin alpha and microtubule associated protein 2 in SiHa cells, and inhibit the microtubular polymerization. Our results suggested an anti-microtubule characteristic of beta-sitosterol which might contribute to the proliferation inhibition of SiHa cells.

    Topics: Cell Line, Tumor; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Female; Humans; Immunoblotting; Microscopy, Confocal; Microtubule-Associated Proteins; Microtubules; Sitosterols; Tubulin; Uterine Cervical Neoplasms

2006
[Study on the chemical constituents of Sambucus chinensis Lindl].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2006, Volume: 29, Issue:9

    To study the chemical constituents of Sambucus chinensis Lindl.. The constituents were isolated and purified by various chromatographic methods and structurally identified by spectral analysis.. 5 compounds were obtained as beta-sitosterol (I), oleanolic acid (II), ursolic acid (III), kaempferol-3-O-beta-D-(6-O-acetylglucopyranosid)-7-O-beta-D-glucopyranoside (IV), and kaempferol-3-O-beta-D-glucopyranosid-7-O-beta-D-glucopyranoside (V).. The compound IV and compound V were obtained from these plants for the first time.

    Topics: Flavonols; Magnetic Resonance Imaging; Molecular Structure; Oleanolic Acid; Plants, Medicinal; Sambucus; Sitosterols; Triterpenes; Ursolic Acid

2006
[Studies on chemical constituents from root of Clematis hexapetala].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2006, Volume: 31, Issue:20

    To study the chemical constituents from the roots and rhizomes of Clematis hexapetala.. The compounds were separated by means of solvent extraction, repeated chromatography with silica gel and HPLC. The structures were determined by spectral analysis.. Nine compounds were isolated as friedelin (1) , anemonin (2) , beta-sitosterol (3) , palmitic acid (4) , vanillic acid (5) , isolariciresinol (6) , 5-hydroxumethyl-5H-furan-2-one (7) , n-nonane (8) , daucosterol (9).. All the compounds were isolated from the plant for the first time.

    Topics: Clematis; Furans; Lignin; Naphthols; Palmitic Acid; Plant Roots; Plants, Medicinal; Rhizome; Sitosterols; Triterpenes

2006
Rapid quantification of free and esterified phytosterols in human serum using APPI-LC-MS/MS.
    Journal of lipid research, 2005, Volume: 46, Issue:1

    A novel analytical platform based on liquid chromatography and tandem mass spectrometry using atmospheric pressure photoionization was applied for the simultaneous quantification of free and esterified beta-sitosterol, campesterol, brassicasterol, and stigmasterol. The total time for sample pretreatment and analysis could be reduced from approximately 3 h [gas chromatography-mass spectrometry (GC-MS)] to 15 min. The detection limits of the different phytosterols ranged between 0.25 and 0.68 microg/l. Linear ranges were between 1 and 1,000 microg/l. The within-run and between-run variabilities ranged between 1.4% and 9.9%. The analytical sensitivity was at least 150-fold higher compared with GC-MS. Our new method allows a rapid and simultaneous determination of free and esterified phytosterols in serum.

    Topics: Cholestadienols; Cholesterol; Chromatography, Liquid; Esters; Humans; Mass Spectrometry; Methods; Phytosterols; Reproducibility of Results; Sitosterols; Stigmasterol

2005
Common sequence variations in ABCG8 are related to plant sterol metabolism in healthy volunteers.
    Journal of lipid research, 2005, Volume: 46, Issue:1

    Polymorphisms in the ATP binding cassette (ABC) transporters ABCG5 and ABCG8 are related to plasma plant sterol concentrations. It is not known whether these polymorphisms are also associated with variations in serum plant sterol concentrations during interventions affecting plant sterol metabolism. We therefore decided to study changes in serum plant sterol concentrations with ABCG5/G8 polymorphisms after consumption of plant stanol esters, which decrease plasma plant sterol concentrations. Cholesterol-standardized serum campesterol and sitosterol concentrations were significantly associated with the ABCG8 T400K genotype, as were changes in serum plant sterol concentrations after consumption of plant stanols. The reduction of -57.1 +/- 38.3 10(2) x micromol/mmol cholesterol for sitosterol in TT subjects was significantly greater compared with the -36.0 +/- 18.7 reduction in subjects with the TK genotype (P = 0.021) and the -16.9 +/- 13.0 reduction in subjects with the KK genotype (P = 0.047). Changes in serum campesterol concentrations showed a comparable association. No association with serum LDL cholesterol was found. Genetic variation in ABCG8 not only explains cross-sectional differences in serum plant sterol concentrations but also determines a subject's responsiveness to changes in serum plant sterols during interventions known to affect plant sterol metabolism.

    Topics: Adolescent; Adult; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Cholesterol; Diet; Energy Metabolism; Female; Genotype; Humans; Lipids; Lipoproteins; Male; Middle Aged; Phytosterols; Polymorphism, Genetic; Sitosterols

2005
Phytoestrogens alter the reproductive organ development in the mink (Mustela vison).
    Toxicology and applied pharmacology, 2005, Jan-15, Volume: 202, Issue:2

    The aim of the present study was to examine the reproductive effects of two perorally applied phytoestrogens, genistein (8 mg/kg/day) and beta-sitosterol (50 mg/kg/day), on the mink (Mustela vison) at human dietary exposure levels. Parental generations were exposed over 9 months to these phytoestrogens and their offspring were exposed via gestation and lactation. Parents and their offspring were sampled 21 days after the birth of the kits. Sex hormone levels, sperm quality, organ weights, and development of the kits were examined. The exposed females were heavier than the control females at the 1st postnatal day (PND). The control kits were heavier than the exposed kits from the 1st to the 21st PND. Phytoestrogens did not affect the organ weights of the adult minks, but the relative testicular weight of the exposed kits was higher than in the control kits. The relative prostate weight was higher and the relative uterine weight lower in the beta-sitosterol-exposed kits than in the control kits. Moreover, the plasma dihydrotestosterone levels were lower in the genistein-exposed male kits compared to the control male kits. This study could not explain the mechanisms behind these alterations. The results indicate that perinatal phytoestrogen exposures cause alterations in the weight of the reproductive organs of the mink kits.

    Topics: Administration, Oral; Aging; Animals; Animals, Newborn; Body Mass Index; Dihydrotestosterone; Drug Administration Schedule; Estradiol; Female; Finland; Genitalia, Female; Genitalia, Male; Gonadal Steroid Hormones; Male; Mink; Organ Size; Phytoestrogens; Pregnancy; Prenatal Exposure Delayed Effects; Reproduction; Semen; Sex Characteristics; Sitosterols; Species Specificity; Sperm Count; Testis; Testosterone

2005
Mycobacterium sp. mutant strain producing 9alpha-hydroxyandrostenedione from sitosterol.
    Applied microbiology and biotechnology, 2005, Volume: 67, Issue:5

    Mycobacterium sp. VKM Ac-1815D and its derivatives with altered resistance to antibacterial agents were able to produce androst-4-ene-3,17-dione (AD) as a major product from sitosterol. In this study, those strains were subjected to subsequent mutagenization by chemical agents and UV irradiation in combination with sitosterol selection pressure. The mutant Mycobacterium sp. 2-4 M was selected, being capable of producing 9alpha-hydroxyandrost-4-ene-3,17-dione (9-OH-AD) as a major product from sitosterol, with a 50% molar yield. Along with 9-OH-AD, both AD and 9alpha-hydroxylated metabolites with a partially degraded side-chain were formed from sitosterol by the mutant strain. The strain was unable to degrade 9-OH-AD, but degraded androsta-1,4-diene-3,17-dione (ADD), thus indicating a deficiency in steroid 1(2)-dehydrogenase and the presence of 9alpha-hydroxylase activity.

    Topics: Androstadienes; Androstenedione; Biotransformation; Molecular Structure; Mutagenesis; Mycobacterium; Oxidoreductases; Selection, Genetic; Sitosterols

2005
Effect of resveratrol and beta-sitosterol in combination on reactive oxygen species and prostaglandin release by PC-3 cells.
    Prostaglandins, leukotrienes, and essential fatty acids, 2005, Volume: 72, Issue:3

    The objective of this project was to identify some possible mechanisms by which two common phytochemicals, resveratrol and beta-sitosterol, inhibit the growth of human prostate cancer PC-3 cells. These mechanisms include the effect of the phytochemicals on apoptosis, cell cycle progression, prostaglandin synthesis and the production of reactive oxygen species (ROS). Prostaglandins have been known to play a role in regulating cell growth and apoptosis. PC-3 cells were supplemented with 50 microM resveratrol or 16 microM beta-sitosterol alone or in combination for up to 5 days. Phytochemical supplementation resulted in inhibition in cell growth. beta-Sitosterol was more potent than resveratrol and the combination of the two resulted in greater inhibition than supplementation with either alone. Long-term supplementation with resveratrol or beta-sitosterol elevated basal prostaglandin release but beta-sitosterol was much more potent than resveratrol in this regard. beta-Sitosterol was more effective than resveratrol in inducing apoptosis and the combination had an intermediate effect after 1 day of supplementation. Cells supplemented with resveratrol were arrested at the G1 phase and at the G2/M phase in the case of beta-sitosterol while the combination resulted in cell arrest at the two phases of the cell cycle. beta-Sitosterol increased ROS production while resveratrol decreased ROS production. The combination of the two phytochemicals resulted in an intermediate level of ROS. The observed changes in prostaglandin levels and ROS production by these two phytochemicals may suggest their mediation in the growth inhibition. The reduction in ROS level and increase by resveratrol supplementation in PC-3 cells reflects the antioxidant properties of resveratrol. It was concluded that these phytochemicals may induce the inhibition of tumor growth by stimulating apoptosis and arresting cells at different locations in the cell cycle and the mechanism may involve alterations in ROS and prostaglandin production.

    Topics: 6-Ketoprostaglandin F1 alpha; Cell Cycle; Cell Line, Tumor; Cell Proliferation; Cyclooxygenase 1; Cyclooxygenase 2; Dinoprostone; Drug Synergism; Humans; Male; Phospholipases A; Prostaglandins; Reactive Oxygen Species; Resveratrol; Sitosterols; Stilbenes

2005
Sterol parameters as markers of liver function in primary biliary cirrhosis before and after liver transplantation.
    Transplant international : official journal of the European Society for Organ Transplantation, 2005, Volume: 18, Issue:2

    Serum cholesterol reflects poorly cholesterol metabolism. From serum noncholesterol sterols cholestanol, campesterol, and sitosterol are surrogate markers of cholesterol absorption, but reflect also cholestasis, while those of lathosterol reflect cholesterol synthesis and hepatic parenchymal function. We investigated these sterols at end-stage of primary biliary cirrhosis (PBC) - prior to liver transplantation and shortly after transplantation in 67 patients to show their role as index of cholestasis and parenchymal liver function. Median preoperative values of cholestanol were increased 7.6 times, those of plant sterols 1.6-3.7 times above and the campesterol/sitosterol ratio was decreased twice below our control values, respective lathosterol levels being mainly subnormal. After transplantation, the proportions to cholesterol of the absorption markers decreased, and those of synthesis markers and the ratios of campesterol/sitosterol increased significantly. Thus, surrogate sterol markers of cholesterol absorption and synthesis in serum are also good clinical markers of chronic cholestasis and degree of hepatic parenchymal cell function in PBC. Postoperative improvement of serum sterol profile indicate clinically good function of the liver graft.

    Topics: Adult; Aged; Bilirubin; Biomarkers; Cholestanol; Cholesterol; Female; Humans; Liver Cirrhosis, Biliary; Liver Function Tests; Liver Transplantation; Male; Middle Aged; Phytosterols; Sitosterols; Sterols

2005
[Studies on the chemical constituents in vine stem of Bauhinia championii (I)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:1

    To study the chemical constituents of Bauhinia championii.. Compounds were isolated from the ethanolic extract of B. championii by silica gel column Chromatography, and their structures were elucidated by spectral analyses.. Five compounds were isolated and elucidated as 2,4,6-trimethoxyphenol 1-O-beta-D-(6'-O-galloyl)-glucopyranoside (1), (+/-)-lyoniresinol (2), daucosterol (3), beta-sitosterol (4) and gallic acid (5).. Compounds 1-4 were isolated from B. championii for the first time.

    Topics: Anisoles; Bauhinia; Gallic Acid; Glucosides; Molecular Structure; Naphthalenes; Plant Stems; Plants, Medicinal; Sitosterols

2005
[Studies on chemical constituents in bark of Larix olgensis var. koreana].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:4

    To study the chemical constituents in bark of Larix olgensis var. koreana.. The compounds were isolated with silica gel column chromatography and their structures were elucidated on the basis of spectral analysis (IR, EI-MS, 1H-NMR, 13C-NMR).. Eight compounds were isolated and identified as isopimaric acid (I), beta-sitosterol (II), 24R,5alpha-stigmast-3,6-dione (III), larixol (IV), ferulic acid (V), lariciresinol (VI), secroisolariciresinol (VII) and isolariciresinol (VIII).. All the compounds were isolated from this plant for the first time.

    Topics: Carboxylic Acids; Furans; Larix; Lignans; Phenanthrenes; Plant Bark; Plants, Medicinal; Sitosterols

2005
In vitro antiprotozoal activity from the roots of Geranium mexicanum and its constituents on Entamoeba histolytica and Giardia lamblia.
    Journal of ethnopharmacology, 2005, Apr-08, Volume: 98, Issue:1-2

    This paper examines the antiprotozoal activity of the dichloromethane-MeOH extract, fractions and pure compounds from the roots of Geranium mexicanum on Entamoeba histolytica and Giardia lamblia. The result indicated that the extract, organic fraction and a pure flavonoid were active against both protozoa with IC50 values ranging from 1.9 to 79.2 microg/ml for Entamoeba histolytica and from 1.6 to 100.4 microg/ml in the case of Giardia lamblia. The main active compound was the flavan-3-ol, (-)-epicatechin. In addition, the moderate active compounds (+)-catechin, tyramine and beta-sitosterol 3-O-beta-D-glucopyranoside, also were isolated. These results support the anecdotal reports for the traditional use of Geranium mexicanum roots in the management of diarrhoea and dysentery, illnesses caused in some cases by enteric protozoa.

    Topics: Animals; Antiprotozoal Agents; Catechin; Drug Evaluation, Preclinical; Entamoeba histolytica; Ethanol; Flavonoids; Geranium; Giardia lamblia; Glucosides; Inhibitory Concentration 50; Methylene Chloride; Plant Extracts; Plant Roots; Sitosterols

2005
[Isolation and indentification of chemical compounds from Drynaria fortunei].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:6

    To study the chemical components of Drynaria fortunei.. The herbal material was extracted with 75% ethanol. The chemical components were isolated by silica gel and sephadex LH-20 column chromatography. The structures were identified on the basis of chemical and spectroscopic data.. Four compounds were isolated, three of which were identified as (-)-epiafzelechin-3-O-beta-D-allopyranoside, (-)-epiafzelechin and beta-sitosterol.. (-)-epiafzelechin-3-O-beta-D-allopyranoside, (-)-epiafzelechin were obtained from D. fortunei for the first time.

    Topics: Catechin; Glycosides; Plants, Medicinal; Polypodiaceae; Rhizome; Sitosterols

2005
ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects.
    Clinical science (London, England : 1979), 2005, Volume: 109, Issue:2

    The ratio of serum plant sterols to cholesterol is positively correlated with the fractional cholesterol absorption, whereas serum precursors of cholesterol synthesis are positively correlated with cholesterol synthesis. Recently, two ABC (ATP-binding cassette) transporters, ABCG5 and ABCG8, have been described as playing an important role in the absorption and excretion of sterols. In the present study, we tested the hypothesis that genetic variation in ABCG5/ABCG8 influences the levels of serum plant sterol (sitosterol) and cholesterol precursor (lathosterol) in Japanese primary hypercholesterolaemic patients (n = 100). We identified a novel mutation [859T/C (C287R)] and a novel polymorphism [1285A/G (M429V)] at the ABCG5/ABCG8 loci, as well as four polymorphisms reported previously [1810C/G (Q604E), 161G/A (C54Y), 1199C/A (T400K) and 1895C/T (A632V)]. In carriers of the novel M429V variant, the serum level of sitosterol and the sitosterol/cholesterol ratio were significantly higher than those in non-carriers (3.64 compared with 2.56 microg/ml, and 1.45 microg/mg compared with 1.00 microg/mg respectively; P < 0.01 for both), and serum lathosterol tended to be lower (1.95 microg/ml compared with 3.03 microg/ml; P = 0.08), whereas no significant difference was observed in other lipid profiles. These four polymorphisms (1810C/G, 161G/A, 1199C/A and 1285A/G) generated six haplotypes, and the C/G/C/G haplotype was significantly associated with a higher sitosterol level and sitosterol/cholesterol ratio compared with the other five haplotypes (P < 0.05 for both). We conclude that, in 8% of patients with hypercholesterolaemia, the novel ABCG8 M429V variant was associated with higher cholesterol absorption efficiency. Future studies should investigate whether these findings have implications for the optimal cholesterol-lowering drug treatment in hypercholesterolaemic patients.

    Topics: Adult; Aged; Aged, 80 and over; ATP-Binding Cassette Transporters; Biomarkers; Cholesterol; Female; Genetic Markers; Heterozygote; Humans; Hypercholesterolemia; Intestinal Absorption; Japan; Male; Middle Aged; Polymorphism, Genetic; Polymorphism, Restriction Fragment Length; Sitosterols

2005
Effect of dietary intake of phytoestrogens on estrogen receptor status in premenopausal women with breast cancer.
    Nutrition and cancer, 2005, Volume: 51, Issue:2

    Although many dietary studies have focused on breast cancer risk, few have examined dietary influence on tumor characteristics such as estrogen receptor (ER) status. Because phytoestrogens may modulate hormone levels and ER expression, we analyzed ER status and phytoestrogen intake in a case-case study of 124 premenopausal breast cancer patients. We assessed intake with a food-frequency questionnaire and obtained ER status from medical records. Rather than focusing on risk, we evaluated whether low intakes were more strongly associated with ER-negative tumors than with ER-positive disease. In logistic regression adjusting for potential confounders, threefold greater risks of ER-negative tumors relative to ER-positive tumors were associated with low intake of the isoflavones genistein (odds ratio, OR=3.50; 95% confidence interval, CI=1.43-8.58) and daidzein (OR=3.10; 95% CI=1.31-7.30). Low intake of the flavonoid kaempferol (OR=0.36; 95% CI=0.16-0.83), the trace element boron (OR=0.33; 95% CI=0.13-0.83), and the phytosterol beta-sitosterol (OR=0.42; 95% CI=0.18-0.98) were associated with decreased risk of ER-negative tumors relative to ER-positive disease. Other phytoestrogens were not significantly associated with ER status. Thus, in premenopausal patients, some phytoestrogens may affect breast carcinogenesis by influencing ER status. Such findings suggest new directions for mechanistic research on dietary factors in breast carcinogenesis that may have relevance for prevention and clinical treatment.

    Topics: Adult; Anticarcinogenic Agents; Boron; Breast Neoplasms; Diet; Female; Genistein; Humans; Hypolipidemic Agents; Isoflavones; Kaempferols; Middle Aged; Nutritional Status; Odds Ratio; Phytoestrogens; Premenopause; Receptors, Estrogen; Risk Factors; Sitosterols; Surveys and Questionnaires

2005
Inhibition of the growth of premalignant and malignant human oral cell lines by extracts and components of black raspberries.
    Nutrition and cancer, 2005, Volume: 51, Issue:2

    Black raspberries are a rich natural source of chemopreventive phytochemicals. Recent studies have shown that freeze-dried black raspberries inhibit the development of oral, esophageal, and colon cancer in rodents, and extracts of black raspberries inhibit benzo(a)pyrene-induced cell transformation of hamster embryo fibroblasts. However, the molecular mechanisms and the active components responsible for black raspberry chemoprevention are unclear. In this study, we found that 2 major chemopreventive components of black raspberries, ferulic acid and beta-sitosterol, and a fraction eluted with ethanol (RO-ET) during silica column chromatography of the organic extract of freeze-dried black raspberries inhibit the growth of premalignant and malignant but not normal human oral epithelial cell lines. Another fraction eluted with CH2Cl2/ethanol (DM:ET) and ellagic acid inhibited the growth of normal as well as premalignant and malignant human oral cell lines. We investigated the molecular mechanisms by which ferulic acid and beta-sitosterol and the RO-ET fraction selectively inhibited the growth of premalignant and malignant oral cells using flow cytometry and Western blotting of cell cycle regulatory proteins. There was no discernable change in the cell cycle distribution following treatment of cells with the RO-ET fraction. Premalignant and malignant cells redistributed to the G2/M phase of the cell cycle following incubation with ferulic acid. beta-sitosterol treated premalignant and malignant cells accumulated in the G0/G1 and G2/M phases, respectively. The RO-ET fraction reduced the levels of cyclin A and cell division cycle gene 2 (cdc2) in premalignant cells and cyclin B1, cyclin D1, and cdc2 in the malignant cell lines. This fraction also elevated the levels of p21waf1/cip1 in the malignant cell line. Ferulic acid treatment led to increased levels of cyclin B1 and cdc2 in both cell lines, and p21waf1/cip1 was induced in the malignant cell line. beta-sitosterol reduced the levels of cyclin B1 and cdc2 while increasing p21waf1/cip1 in both the premalignant and malignant cell lines. These results show for the first time that the growth inhibitory effects of black raspberries on premalignant and malignant human oral cells may reside in specific components that target aberrant signaling pathways regulating cell cycle progression.

    Topics: Blotting, Western; Cell Cycle; Cell Division; Cell Line; Chemoprevention; Coumaric Acids; Dose-Response Relationship, Drug; Ellagic Acid; Ethanol; Flow Cytometry; Fruit; Humans; In Vitro Techniques; Models, Biological; Mouth Mucosa; Mouth Neoplasms; Plant Extracts; Precancerous Conditions; Sitosterols; Tumor Cells, Cultured

2005
Beta-sitosterol from psyllium seed husk (Plantago ovata Forsk) restores gap junctional intercellular communication in Ha-ras transfected rat liver cells.
    Nutrition and cancer, 2005, Volume: 51, Issue:2

    We purified compounds from the husks of psyllium seeds (Plantago ovata Forsk; desert Indian wheat), beginning with an ethanol extraction then followed by HP-20 and silica gel chromatography, which restored gap junctional intercellular communication (GJIC) in v-Ha-ras transfected rat liver epithelial WB-F344 cell line (WB-Ha-ras). GJIC was assessed by a scrape loading dye transfer assay. The active compound was identified as beta-sitosterol based on gas chromatography retention times and electron ionization mass spectroscopy (EI-MS) spectrum of authentic beta-sitosterol. Authentic beta-sitosterol restored GJIC in the tumorigenic WB-Ha-ras GJIC-deficient cells at a dose of 2.4 microM. In addition, a similar phytosterol, stigmasterol, also restored GJIC, albeit at a lower activity. beta-sitosterol and stigmasterol increased the level of connexin43 protein (Cx43) and restored phosphorylation of Cx43 to levels similar to the parental nontransfected cell line. We concluded that the restoration of intercellular communication in the GJIC-deficient, tumorigenic WB-Ha-ras cell line by the ethanol soluble fraction of psyllium seed husks is largely due to the presence of the phytosterol, beta-sitosterol. We discuss implications for dietary modulation of cancer by beta-sitosterol.

    Topics: Animals; Blotting, Western; Cell Communication; Cell Transformation, Neoplastic; Cells, Cultured; Gap Junctions; Gas Chromatography-Mass Spectrometry; Genes, ras; Hepatocytes; Hypolipidemic Agents; In Vitro Techniques; Male; Psyllium; Rats; Seeds; Sitosterols

2005
Quantitative determination of cholesterol, sitosterol, and sitostanol in cultured Caco-2 cells by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.
    Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 2005, Jul-25, Volume: 821, Issue:2

    In this study, we describe a simple liquid extraction (methanol/choloroform, 1:1, v/v) method for endogenous free cholesterol and administered sterols extracted from cultured Caco-2 cells. To quantify sterol contents in Caco-2 cells, a new HPLC-APCI-MS method was developed. All the sterols were baseline separated using reversed-phase column (C8, 2.1 mm x 150 mm, 3.5 microm) and isocratic conditions (90%, v/v, methanol-water mixture containing 0.2 mM ammonium acetate). The full scan mass spectra of sterols were measured by an ion trap mass spectrometer equipped with an APCI ion source. The intense fragment ions resulting from the loss of water [M+H-H2O]+ (m/z 369, 395, 397 and 399 for cholesterol, stigmasterol, sitosterol, and sitostanol, respectively) were used for determinations. The absolute extraction recovery of sterols from the spiked cell samples were 109.7+/-26.2, 105.7+/-5.1, 109.8+/-5.0 and 99.0+/-7.0% for cholesterol, stigmasterol, sitosterol, and sitostanol, respectively. Furthermore, no significant matrix effect was observed for the sterols in the cell samples. The sample assay was based on the internal standard method using stigmasterol as an internal standard. The method was linear over the concentration ranges of 0.45-9.0 microM (cholesterol) and 0.225-7.2 microM (sitosterol and sitostanol). The within- and between-day precision was less than 7% and accuracy ranged from 93.51 to 101.77%. The lowest limit of quantitation (LLOQ) was 0.225 microM for sitosterol and sitostanol, and 0.45 microM for cholesterol. The accuracy range was 95-106% and precision was lower than 9% for all LLOQ values.

    Topics: Caco-2 Cells; Cholesterol; Chromatography, Liquid; Humans; Mass Spectrometry; Reproducibility of Results; Sitosterols; Sterols

2005
beta-Sitosterol modulates antioxidant enzyme response in RAW 264.7 macrophages.
    Free radical biology & medicine, 2005, Jul-01, Volume: 39, Issue:1

    Uncontrolled production of reactive oxygen species contributes to the pathogenesis of diseases such as cancer and cardiovascular disorders. Olive oil exerts remarkable preventive effects on the development of these diseases, which may be due to the action of various components of the olive oil. In fact, several findings suggest that minor components, like phytosterols such as beta-sitosterol, are responsible, at least in part, for these beneficial effects. Our results show that beta-sitosterol reverts the impairment of the glutathione/oxidized glutathione ratio induced by phorbol esters in RAW 264.7 macrophage cultures. These data can be correlated with the increase in manganese superoxide dismutase and glutathione peroxidase activities and the decrease in catalase activity. We also demonstrate that the effects of beta-sitosterol on antioxidant enzymes depend on the estrogen/phosphatidylinositol 3-kinase pathway.

    Topics: Animals; Antioxidants; Catalase; Cell Line; Glutathione; Glutathione Peroxidase; Macrophages; Mice; Olive Oil; Plant Oils; Sitosterols; Superoxide Dismutase; Tetradecanoylphorbol Acetate

2005
Ezetimibe normalizes metabolic defects in mice lacking ABCG5 and ABCG8.
    Journal of lipid research, 2005, Volume: 46, Issue:8

    The ATP binding cassette transporters ABCG5 (G5) and ABCG8 (G8) limit the accumulation of neutral sterols by restricting sterol uptake from the intestine and promoting sterol excretion into bile. Humans and mice lacking G5 and G8 (G5G8-/-) accumulate plant sterols in the blood and tissues. However, despite impaired biliary cholesterol secretion, plasma and liver cholesterol levels are lower in G5G8-/- mice than in wild-type littermates. To determine whether the observed changes in hepatic sterol metabolism were a direct result of decreased biliary sterol secretion or a metabolic consequence of the accumulation of dietary noncholesterol sterols, we treated G5G8-/- mice with ezetimibe, a drug that reduces the absorption of both plant- and animal-derived sterols. Ezetimibe feeding for 1 month sharply decreased sterol absorption and plasma levels of sitosterol and campesterol but increased cholesterol in both the plasma (from 60.4 to 75.2 mg/dl) and the liver (from 1.1 to 1.87 mg/g) of the ezetimibe-treated G5G8-/- mice. Paradoxically, the increase in hepatic cholesterol was associated with an increase in mRNA levels of HMG-CoA reductase and synthase. Together, these results indicate that pharmacological blockade of sterol absorption can ameliorate the deleterious metabolic effects of plant sterols even in the absence of G5 and G8.

    Topics: Absorption; Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Azetidines; Cholesterol; Ezetimibe; Lipoproteins; Liver; Mice; Mice, Knockout; Phytosterols; Sitosterols; Sterols

2005
[Studies on chemical constituents of Smilax china].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2005, Volume: 28, Issue:1

    To study the chemical constituents of the 95% ethanol extract from the rhizome of Smilax china.. Seven compounds were isolated from ethyl acetate fraction of 95% ethanol extract by using repeated silica column chromatography, partition chromatography, preparing TLC, and other methods. Structure of three compounds of them was identified based on chemical methods and spectroscopic methods.. The structure of them were established as dihydrokaempferol-5-O-beta-D-glucoside (I), beta-sitosterol (II), daucosterol (III).. Compound I was a novel compound which was first found from natural plants.

    Topics: Flavonoids; Glucosides; Molecular Structure; Plants, Medicinal; Rhizome; Sitosterols; Smilax; Spectrophotometry, Ultraviolet

2005
Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy.
    Journal of the American College of Cardiology, 2005, Jun-07, Volume: 45, Issue:11

    The purpose of this research was to determine whether serum plant sterol levels are associated with those in atheromatous plaque.. Cholesterol of low-density lipoprotein (LDL) particles contributes to atheromatous plaque formation; LDL also contains most serum non-cholesterol sterols, including plant sterols. The role of plant sterols in atheromatous plaque formation is open.. Free, ester, and total cholesterol and the respective non-cholesterol sterols were measured by gas-liquid chromatography in serum and arterial tissue of 25 consecutive patients undergoing carotid endarterectomy. The population was ranked to triads according to tissue cholesterol concentration.. Cholesterol concentration increased markedly in tissues but not in serum with triads. The ester percentage was lower in the third than in the first triad (47% vs. 56%; p < 0.01) and lower than in serum triads (70%; p < 0.001). Ratios to cholesterol of non-cholesterol sterols decreased in increasing tissue triads, but were unchanged in serum. A major new observation was that the higher the ratio to cholesterol of the surrogate absorption sterols (cholestanol, campesterol, sitosterol, and avenasterol) in serum, the higher was their ratio also in the carotid artery wall (e.g., r = 0.683 for campesterol). Despite undetectable differences in serum and tissue cholesterol concentrations off and on statins, an additional important novel finding was that statin treatment was associated with increased ratios of the absorption sterols in serum and also in the arterial plaque.. The higher the absorption of cholesterol, the higher are the plant sterol contents in serum resulting also in their higher contents in atherosclerotic plaque. However, the role of dietary plant sterols in the development of atherosclerotic plaque is not known.

    Topics: Absorption; Aged; Aged, 80 and over; Carotid Arteries; Carotid Artery Diseases; Cholestanol; Cholesterol; Cholesterol, HDL; Chromatography, Gas; Endarterectomy, Carotid; Female; Humans; Middle Aged; Phytosterols; Sitosterols

2005
DNA damaging activities of methanol extract of Ajuga postii and iridoid glucoside reptoside.
    Natural product research, 2005, Volume: 19, Issue:5

    An iridoid glucoside reptoside (1) has been isolated as a DNA damaging active agent by bioassay-guided fractionation of the methanol extract of Ajuga postii. Furthermore, from the acetone extract of A. postii two known triterpenic compounds ursolic acid, alpha-amyrin and two steroidal compounds (24S)-24-ethylcholesta-5,25-dien-3beta-ol and beta-sitosterol were isolated. Their structures were elucidated based on 1D and 2D NMR techniques and mass data.

    Topics: Ajuga; DNA Damage; Iridoids; Oleanolic Acid; Plant Extracts; Sitosterols; Sterols; Triterpenes; Ursolic Acid

2005
Identification of delta7 phytosterols and phytosteryl glucosides in the wood and bark of several Acacia species.
    Lipids, 2005, Volume: 40, Issue:3

    The wood and bark of four Acacia species growing in Portugal, namely, A. longifolia, A. dealbata, A. melanoxylon, and A. retinodes, were investigated for their sterol content. The lipids fractions of the different wood and bark samples were isolated, and the sterols were identified and quantified by GC-MS. Two delta7 sterols, specifically, spinasterol and dihydrospinasterol, were the main sterols found in considerable amounts, particularly in wood tissues (more than 0.5 g/kg of dry wood in the case of A. melanoxylon and A. retinodes). The corresponding unusual steryl glucosides were also identified in significant amounts in the wood and bark extracts.

    Topics: Acacia; Gas Chromatography-Mass Spectrometry; Glucosides; Phytosterols; Plant Stems; Portugal; Sitosterols; Stigmasterol; Wood

2005
[Studies on chemical constituents from pine cone of Pinus armandii].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:7

    To study chemical constituents from pine cone of Pinus annandii.. The constituents were isolated by chromatographic method and the structures were identified on the basis of spectral analysis.. Seven compounds were identified as sandaracopimaric acid (I), isodextropimaric acid (II), 12-hydroxyabietic acid (III), dehydroabietic acid (IV), 15-hydroxydehydroabietic acid (V), beta-sitosterol (VI) and daucosterol (VII).. Compounds I-IV were isolated from this plant for the first time.

    Topics: Abietanes; Diterpenes; Fruit; Pinus; Plants, Medicinal; Sitosterols

2005
[Studies on chemical constituents in herb of Chondrilla piptocoma].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:8

    To study the chemical constituents of Chondrilla piptocoma.. The chemical constituents were isolated and repeatedly purified on silica gel column and the structures were elucidated by the NMR spectra and physico-chemical properties.. Seven compounds were obtained and they are identified as luteolin, 5,7,4'-trihydroxy-3'-methoxy flavone, luteolin-7-O-beta-D-glucoside, apigenin, beta-sitosterol, stigmasterol, ursolic acid.. All the compounds were obtained from C. piptocoma for the first time.

    Topics: Apigenin; Asteraceae; Luteolin; Plants, Medicinal; Sitosterols; Stigmasterol

2005
Identification and quantitative analysis of beta-sitosterol oxides in vegetable oils by capillary gas chromatography-mass spectrometry.
    Steroids, 2005, Dec-01, Volume: 70, Issue:13

    As vegetable oils and phytosterol-enriched spreads are marketed for frying food or cooking purposes, temperature is one of the most important factors leading to the formation of phytosterol oxides in food matrix. A methodology based on saponification, organic solvent extraction, solid-phase extraction (SPE), followed by mass spectrometric identification and quantitation of beta-sitosterol oxides using capillary gas chromatography-mass spectrometry (GC-MS) in selected ion monitoring (SIM) mode was developed and characterized. Relative response factors of six beta-sitosterol oxides, including 7alpha-hydroxy, 7beta-hydroxy, 5,6alpha-epoxy, 5,6beta-epoxy, 7-keto, and 5alpha,6beta-dihydroxysitosterol, were calculated against authentic standards of 19-hydroxycholesterol or cholestanol. Linear calibration data, limit of detection, and sample recoveries during analytical process. Recoveries of these oxidation compounds in spiked samples ranged from 88 to 115%, while relative standard derivation (R.S.D.) values were below 10% in most cases. The analytical method was applied to quantify beta-sitosterol oxides formed in thermal-oxidized vegetable oils which were heated at different temperatures and for varying time periods. Sitosterol oxidation is strikingly higher in sunflower oil relative to olive oil under all conditions of temperature and heating time.

    Topics: Gas Chromatography-Mass Spectrometry; Hot Temperature; Olive Oil; Oxides; Phytosterols; Plant Oils; Sitosterols; Sunflower Oil

2005
Gram-scale chromatographic purification of beta-sitosterol. Synthesis and characterization of beta-sitosterol oxides.
    Steroids, 2005, Dec-01, Volume: 70, Issue:13

    An effective purification method for beta-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. beta-Sitosterol (> or = 95% purity) was obtained on a gram-scale. Thus, the synthesis of six beta-sitosterol oxides, including 7alpha-hydroxy, 7beta-hydroxy, 5,6alpha-epoxy, 5,6beta-epoxy, 7-keto, and 5alpha,6beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (approximately 95% purity) were well-documented.

    Topics: Chromatography; Oxides; Phytosterols; Sitosterols; Spectrum Analysis

2005
[Studies on the chemical constituents in seeds of Atriplex centralasiatica].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:9

    To study the chemical constituents in seeds of Atriplex centralasiatica.. The chemical components were isolated by solvents extractions and column chromatography. The chemical structures were identified on the basis of physicochemical constants and spectral data.. Six compounds were isolated and identified as isorhamnetin(I), tricin(II), querecetin-7-O-alpha-L-rhamnoside(III), isoorientin(IV), beta-sitosterol(V), beta-daucosterlo(VI).. Compound I, II, III, IV are isolated from genus Atriplex for the first time.

    Topics: Atriplex; Flavonoids; Flavonols; Luteolin; Plants, Medicinal; Quercetin; Seeds; Sitosterols

2005
beta-Sitosterol stimulates ceramide metabolism in differentiated Caco2 cells.
    The Journal of nutritional biochemistry, 2005, Volume: 16, Issue:11

    Previous studies from our laboratory on tumor cells suggest that phytosterols stimulate ceramide production, which was associated with cell growth inhibition and stimulation of apoptosis. The objective of the present study was to examine the effect of phytosterols on ceramide metabolism in small intestinal cells that represent the first cells in contact with dietary phytosterols. Caco(2) cells, an accepted model for human intestinal epithelial cells, were used in this study. Ceramide and ceramide-containing lipids were examined by labeling the ceramide pool with (3)H-serine. Cells were supplemented with 16 microM of sterols (cholesterol, beta-sitosterol or campesterol) for 16 days postconfluence and continued to differentiate. Of the two phytosterols, beta-sitosterol, but not campesterol, induced more than double the serine labeling when compared with cholesterol. This increase was uniform in sphingomyelin (SM), ceramide and sphingosine labeling. Sterols had no effect on SM concentration in the cells. In addition, sterol had no effect on the activity of SM synthase or sphingomyelinases. There was an inhibition of ceramidases with campesterol supplementation. These data suggest that the observed increases in SM and sphingosine labeling were due to an increase in ceramide turnover. The increase in ceramide turnover with beta-sitosterol supplementation was not associated with growth inhibition but was with increases in ceramide glycosylation products such as cerebrosides and gangliosides. It was concluded that beta-sitosterol has no effect on differential Caco(2), a model of normal small intestinal cells. The increase in the glycosylated ceramide products may offer a means to protect the cells from the harmful effect of ceramide by excreting them with lipoproteins.

    Topics: Caco-2 Cells; Cell Differentiation; Cell Division; Ceramides; Cholesterol; Enterocytes; Humans; Phytosterols; Sitosterols; Sphingomyelins; Sphingosine

2005
Lipoxygenase inhibitory constituents from Indigofera oblongifolia.
    Archives of pharmacal research, 2005, Volume: 28, Issue:7

    Indigin, alkylated xanthene (1) and indigoferic acid (2) have been isolated from the chloroform soluble fraction of Indigofera oblongifolia, along with beta-sitosterol (3) and 3-hydroxybenzoic acid (4), which are reported for the first time from this species. Their structures were determined through spectroscopic techniques. Both the new compounds 1 and 2 showed significant activity against enzyme lipoxygenase, while 2 further showed moderate inhibition against BChE.

    Topics: Cholinesterase Inhibitors; Cinnamates; Fatty Acids; Hydroxybenzoates; Indigofera; Inhibitory Concentration 50; Lipoxygenase Inhibitors; Magnetic Resonance Spectroscopy; Plant Extracts; Sitosterols; Xanthenes

2005
Margarine phytosterols decrease the secretion of atherogenic lipoproteins from HepG2 liver and Caco2 intestinal cells.
    Atherosclerosis, 2005, Volume: 182, Issue:1

    Several studies in humans have demonstrated the hypocholesterolemic effect of plant sterol consumption. It is unclear whether plant sterols regulate lipoprotein metabolism in the liver and intestines, thereby decreasing the levels of circulating atherogenic lipoproteins. We investigated the effect of the three main phytosterols: stigmasterol, campesterol, and beta-sitosterol on lipoprotein production in HepG2 human liver cells and Caco2 human intestinal cells and the mechanisms involved. Cells were incubated for 24h with 50 micromol/L of the different phytosterols or 10 micromol/L of atorvastatin. Very low-density lipoprotein levels (measured by apolipoprotein (apo) B100) in HepG2 cells and chylomicron levels (measured by apoB48) in Caco2 cells were measured using western blotting. Intracellular cholesterol levels were measured using gas chromatography. Analysis was carried out using Student's t-test and ANOVA. Secretion levels of apoB100 significantly decreased by approximately 30% after incubation with all phytosterols compared to control. In addition, cholesterol ester (CE) concentrations significantly decreased when HepG2 cells were incubated with the phytosterols compared to control cells. Secretion of apoB48 from intestinal cells significantly decreased by 15% with stigmasterol, 16% with campesterol and 19% beta-sitosterol compared to control. Collectively the data suggests that plant sterols limit lipid (CE) availability in cells. Decreases in circulating levels of LDL and chylomicron remnants seen in humans with the consumption of margarine phytosterols are possibly due to their effect on lipid production in cells and would therefore reduce the risk of developing cardiovascular disease.

    Topics: Anticholesteremic Agents; Apolipoprotein B-100; Apolipoprotein B-48; Apolipoproteins B; Atherosclerosis; Atorvastatin; Caco-2 Cells; Carcinoma, Hepatocellular; Cholesterol; Drug Synergism; Enterocytes; Hepatocytes; Heptanoic Acids; Humans; Liver Neoplasms; Margarine; Phytosterols; Pyrroles; Sitosterols; Stigmasterol

2005
[Studies on the chemical constituents from the roots of Chloranthus henryi].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2005, Volume: 40, Issue:6

    To study the chemical constituents of the roots of Chloranthus henryi.. The constituents of Chloranthus henryi were separated with various chromatographic techniques. structures were elucidated by physico-chemical properties and spectral data.. Eight compounds were isolated from Chloranthus henryi. They were identified as curcolonol (I), zedoarofuran (II), shizukanolide E (III) , skimmin (IV), calucanthoside (V), chloracoumarin (VI), beta-sitosterol (VII), daucosterin (VIII).. Chloracoumarin (VI) is a new compound and characterized as 6,8-dimethoxy-7-O-[beta-D-apiofunanosyl(l --> 3 )-D-glucopyranosyl]-2H-benzopyran-2-one. Compounds I, II were isolated from Chloranthus henryi for the first time.

    Topics: Coumarins; Glucosides; Heterocyclic Compounds, 3-Ring; Magnoliopsida; Molecular Conformation; Molecular Structure; Plant Roots; Plants, Medicinal; Sitosterols

2005
Plant sterols and stanols: effects on mixed micellar composition and LXR (target gene) activation.
    Journal of lipid research, 2005, Volume: 46, Issue:11

    Plant stanols and sterols of the 4-desmethyl family (e.g., sitostanol and sitosterol) effectively decrease LDL cholesterol concentrations, whereas 4,4-dimethylsterols (alpha-amyrin and lupeol) do not. Serum carotenoid concentrations, however, are decreased by both plant sterol families. The exact mechanisms underlying these effects are not known, although effects on micellar composition have been suggested. With a liver X receptor (LXR) coactivator peptide recruitment assay, we showed that plant sterols and stanols from the 4-desmethylsterol family activated both LXRalpha and LXRbeta, whereas 4,4-dimethyl plant sterols did not. In fully differentiated Caco-2 cells, the functionality of this effect was shown by the increased expression of ABCA1, one of the known LXR target genes expressed by Caco-2 cells in measurable amounts. The LXR-activating potential of the various plant sterols/stanols correlated positively with ABCA1 mRNA expression. Reductions in serum hydrocarbon carotenoids could be explained by the effects of the 4-desmethyl family and 4,4-dimethylsterols on micellar carotenoid incorporation. Our findings indicate that the decreased intestinal absorption of cholesterol and carotenoids by plant sterols and stanols is caused by two distinct mechanisms.

    Topics: Antioxidants; ATP Binding Cassette Transporter 1; ATP-Binding Cassette Transporters; Caco-2 Cells; Carotenoids; Cholesterol; Cholesterol, LDL; DNA-Binding Proteins; Humans; Hydrocarbons; Intestinal Absorption; Intestines; Liver X Receptors; Micelles; Models, Chemical; Oleanolic Acid; Orphan Nuclear Receptors; Pentacyclic Triterpenes; Peptides; Phytosterols; Plant Extracts; Receptors, Cytoplasmic and Nuclear; Receptors, Steroid; RNA, Messenger; Sitosterols; Sterol Regulatory Element Binding Protein 2; Triterpenes

2005
Synthesis, isolation and characterisation of beta-sitosterol and beta-sitosterol oxide derivatives.
    Organic & biomolecular chemistry, 2005, Aug-21, Volume: 3, Issue:16

    Beta-sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to beta-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of beta-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including beta-sitosterol, hinders the collection of significant toxicity data on the individual beta-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure beta-sitosterol is described here, together with the first syntheses and characterisation of pure beta-sitosterol oxides.

    Topics: Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Oxides; Sitosterols

2005
Levels of phytosterol oxides in enriched and nonenriched spreads: application of a thin-layer chromatography-gas chromatography methodology.
    Journal of agricultural and food chemistry, 2005, Oct-05, Volume: 53, Issue:20

    The content of phytosterol oxidation products (POPs) in enriched and nonenriched commercial spreads was evaluated by thin-layer chromatography-gas chromatography (TLC-GC). Oxides of beta-sitosterol, campesterol, and stigmasterol were produced by thermo-oxidation (7-hydroxy, 7-keto, and epoxy derivatives) and chemical synthesis (triol derivatives), which were then separated and identified by TLC-GC. Their identification was further confirmed by GC-mass spectrometry (GC-MS). The total amounts of phytosterols found were 6.07 and 0.33 g/100 g of sample in phytosterol-enriched and nonenriched spread, respectively, whereas the total POPs contents were 45.60 and 13.31 mg/kg of sample in the enriched and nonenriched products. The main POPs found were the 7-keto derivatives of all phytosterols analyzed; 7-ketositosterol was the most abundant one (14.96 and 5.93 mg/kg of sample in phytosterol-enriched and nonenriched spread). No beta-epoxy and triol derivatives were detected in both types of samples. The enriched spread presented a lower phytosterol oxidation rate (0.07%) than the nonenriched one (0.41%).

    Topics: Cholesterol; Chromatography, Gas; Chromatography, Thin Layer; Food Analysis; Food, Fortified; Margarine; Oxidation-Reduction; Oxides; Phytosterols; Sitosterols; Stigmasterol

2005
Dual roles for cholesterol in mammalian cells.
    Proceedings of the National Academy of Sciences of the United States of America, 2005, Oct-11, Volume: 102, Issue:41

    The structural features of sterols required to support mammalian cell growth have not been fully defined. Here, we use mutant CHO cells that synthesize only small amounts of cholesterol to test the capacity of various sterols to support growth. Sterols with minor modifications of the side chain (e.g., campesterol, beta-sitosterol, and desmosterol) supported long-term growth of mutant cells, but sterols with more complex modifications of the side chain, the sterol nucleus, or the 3-hydroxy group did not. After 60 days in culture, the exogenous sterol comprised >90% of cellular sterols. Inactivation of residual endogenous synthesis with the squalene epoxidase inhibitor NB-598 prevented growth in beta-sitosterol and greatly reduced growth in campesterol. Growth of cells cultured in beta-sitosterol and NB-598 was restored by adding small amounts of cholesterol to the medium. Surprisingly, enantiomeric cholesterol also supported cell growth, even in the presence of NB-598. Thus, sterols fulfill two roles in mammalian cells: (i) a bulk membrane requirement in which phytosterols can substitute for cholesterol and (ii) other processes that specifically require small amounts of cholesterol but are not enantioselective.

    Topics: Animals; Benzylamines; Cell Proliferation; CHO Cells; Cholesterol; Cricetinae; Cricetulus; Phytosterols; Sitosterols; Thiophenes

2005
[Chemical constituents from rhizome of Pulsatilla dahurica].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2005, Volume: 30, Issue:15

    To study the chemical constituents from rhizome of Pulsatilla dahurica.. The constituents were isolated and purified by various chromatographic methods. AR compounds were identified on the basis of spectral analysis and physico-chemical characters.. Six compounds were isolated from the 70% alcohol extract of the rhizome identified as hederagenin ( I ), hederagenin 3-O-alpha-L-arabinopyranoside (II), hederagenin 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranoside (III), hederagenin 3-O-beta-D-glucopyranosyl(1 -->2) [beta-D-glucopyranosyl(1-->4)]-alpha-L-arabinopyranoside (IV), beta-sitosterol (V) and daucosterol (VI), respectively.. Compounds I approximately VI were isolated from this plant for the first time.

    Topics: Oleanolic Acid; Plants, Medicinal; Pulsatilla; Rhizome; Saponins; Sitosterols

2005
Confirmation of potential herbicidal agents in hulls of rice, Oryza sativa.
    Journal of chemical ecology, 2005, Volume: 31, Issue:6

    An ethyl acetate extract of Oryza sativa (rice) hulls yielded seven compounds: hentriacontane, 1-tetratriacontanol, beta-sitosterol, momilactone A, momilactone B, tricin (a flavonoid), and beta-sitosterol-3-O-beta-D-glucoside. The structures of these compounds were elucidated with 500 MHz nuclear magnetic resonance (NMR), using 1D and 2D spectral methods, aided by electron ionization mass spectrometry (EI-MS), fast atom bombardment mass spectrometry (FAB-MS), infrared (IR), and ultraviolet (UV) spectrophotometry. The complete 1H NMR assignments for momilactone A and B and 13C NMR assignments for tricin are discussed. To the best of our knowledge, hentriacontane, 1-tetratriacontanol, and beta-sitosterol-3-O-beta-D-glucoside were identified for the first time in rice hulls. In biological activity tests using these identified compounds, momilactone A and B showed potent inhibitory activity against duckweed (Lemna paucicostata). 1-Tetratriacontanol and beta-sitosterol-3-O-beta-D-glucoside also showed about 13-20% inhibitory activity based on chlorophyll reduction. Hentriacontane and beta-sitosterol did not show any herbicidal activity. In a germination assay of three weed species (Leptochloa chinenesis L., Amaranthus retroflexus L., and Cyperus difformis L.) in culture tubes both momilactones A and B had high inhibitory effects. Momilactone B completely inhibited germination of all three weed species at 20 ppm. Germination of L. chinensis L. was completely inhibited by a 4 ppm solution of momilactone B.

    Topics: Amaranthus; Cyperus; Diterpenes; Fatty Alcohols; Flavonoids; Germination; Herbicides; Hydrocarbons; Lactones; Oryza; Plant Development; Plants; Sitosterols; Spectrum Analysis

2005
New acylated clionasterol glycosides from Valeriana officinalis.
    Planta medica, 2005, Volume: 71, Issue:10

    The chloroform extract of Valeriana officinalis led to the isolation of clionasterol-3-O-beta-D-glucopyranoside and a mixture of 6'-O-acyl-beta-D-glucosyl-clionasterols. The acyl moieties were identified as hexadecanoyl, 8 E,11 E-octadecadienoyl and 14-methylpentadecanoyl by alkaline hydrolysis followed by GC-MS analysis. The isolated compounds did not exhibit any anti-inflammatory, anticancer or cytotoxic activity when tested in a variety of in vitro cell-based assays.

    Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Chlorocebus aethiops; Gas Chromatography-Mass Spectrometry; Glycosides; Humans; LLC-PK1 Cells; Macrophages; Mice; Phytotherapy; Plant Extracts; Sitosterols; Swine; Valerian; Vero Cells

2005
Sperm motility inhibiting activity of a phytosterol from Alstonia macrophylla Wall ex A. DC. leaf extract: a tribal medicine.
    Indian journal of experimental biology, 2005, Volume: 43, Issue:11

    The role of methanolic extract and n-butanol fraction of A. macrophylla leaves was investigated on the forward motility of goat spermatozoa. The methanol extract (600 micro/g/ml) and one n-butanol fraction (Fraction A; 100 microg/ml) showed marked inhibition of sperm forward motility, tested by microscopic and spectrophotometric methods. Approximately, 50-60% of the spermatozoa lost their motility when treated with 600 microg/ml of methanol extract or 100 microg/ml of Fraction A. The Fraction A at 400 microg/ml concentration showed complete inhibition of sperm forward motility at 0 min. The inhibitory activity increased with the increasing concentrations of the fraction. The motility inhibitory activity of the Fraction A was stable to heat treatment at 100 degrees C for 2 min. The compound showed high inhibitory effect in the pH range 6.7-7.6. Fraction A also showed high efficacy for inhibiting human sperm motility, assessed by the microscopic method. The phytochemical analysis of methanolic extract of A. macrophylla leaves revealed the presence of sterols, triterpene, flavonoid, alkaloid, tannin and reducing sugar, while the Fraction A contains beta-sitosterol, a common phytosterol. The results demonstrate that Fraction A (beta-sitosterol) is a potent inhibitor of sperm motility and thus it has the potential to serve as a vaginal contraceptive.

    Topics: Alstonia; Animals; Anti-Infective Agents; Antifungal Agents; Butanols; Contraceptive Agents; Dose-Response Relationship, Drug; Female; Goats; Hydrogen-Ion Concentration; Male; Medicine, Traditional; Methanol; Phytosterols; Plant Extracts; Plant Leaves; Sitosterols; Sperm Motility; Spermatozoa; Time Factors

2005
Dietary sitostanol and campestanol: accumulation in the blood of humans with sitosterolemia and xanthomatosis and in rat tissues.
    Lipids, 2005, Volume: 40, Issue:9

    Dietary sitostanol has a hypocholesterolemic effect because it decreases the absorption of cholesterol. However, its effects on the sitostanol concentrations in the blood and tissues are relatively unknown, especially in patients with sitosterolemia and xanthomatosis. These patients hyperabsorb all sterols and fail to excrete ingested sitosterol and other plant sterols as normal people do. The goal of the present study was to examine the absorbability of dietary sitostanol in humans and animals and its potential long-term effect. Two patients with sitosterolemia were fed the margarine Benecol (McNeill Nutritionals, Ft. Washington, PA), which is enriched in sitostanol and campestanol, for 7-18 wk. Their plasma cholesterol levels decreased from 180 to 167 mg/dL and 153 to 113 mg/dL, respectively. Campesterol and sitosterol also decreased. However, their plasma sitostanol levels increased from 1.6 to 10.1 mg/dL and from 2.8 to 7.9 mg/dL, respectively. Plasma campestanol also increased. After Benecol withdrawal, the decline in plasma of both sitostanol and campestanol was very sluggish. In an animal study, two groups of rats were fed high-cholesterol diets with and without sitostanol for 4 wk. As expected, plasma and liver cholesterol levels decreased 18 and 53%, respectively. The sitostanol in plasma increased fourfold, and sitostanol increased threefold in skeletal muscle and twofold in heart muscle. Campestanol also increased significantly in both plasma and tissues. Our data indicate that dietary sitostanol and campestanol are absorbed by patients with sitosterolemia and xanthomatosis and also by rats. The absorbed plant stanols were deposited in rat tissues. Once absorbed by sitosterolemic patients, the prolonged retention of sitostanol and campestanol in plasma might increase their atherogenic potential.

    Topics: Adolescent; Animals; Cholesterol; Diet; Female; Humans; Male; Metabolism, Inborn Errors; Middle Aged; Phytosterols; Rats; Rats, Wistar; Sitosterols; Tissue Distribution; Xanthomatosis

2005
Physical changes of beta-sitosterol crystals in oily suspensions during heating.
    AAPS PharmSciTech, 2005, Oct-19, Volume: 6, Issue:3

    The aim of this research was to describe the thermal behavior of beta-sitosterol crystals in oil-suspensions with a focus on the role of water during heating. The suspensions were prepared by recrystallization in order to achieve a microcrystalline particle size. The structural changes together with the mechanical properties of the suspensions during heating were studied by using variable temperature X-ray powder diffractometry (VT-XRPD), differential scanning calorimetry (DSC), and dynamic mechanical analysis (DMA). Hydrated beta-sitosterol crystals in an oil-suspension dehydrated, despite the composition of the suspensions, at low temperatures. At high beta-sitosterol concentration, the monohydrate crystal form changed partially to a hemihydrated form, and when only a small amount of water was initially incorporated, the hemihydrate crystal form dehydrated to a mostly anhydrate crystal form. The released water, which was immiscible in the surrounding oil, caused the recrystallization of hydrated beta-sitosterol during cooling. This procedure indicated a reversible dehydration process. Structural and thermal analysis of beta-sitosterol crystals in suspensions, together with mechanical analysis made it possible to understand various physical changes during heating.

    Topics: Chemical Phenomena; Chemistry, Physical; Crystallization; Hot Temperature; Oils; Sitosterols; Suspensions

2005
[Study on chemical constituents from stem of Mallotus apelta].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2005, Volume: 28, Issue:9

    Eight compounds were isolated from the ethyl-acetate extract of the stem of Mallotus apelta Muell. -Arg. The structures of eight compounds were identified by means of spectroscopic analysis as 12-ursen-3-one (I), 3-hydroxy-12-ursen (II), mussaenoside (III), 6-methoxy-2H-1-benzopyron4-one (IV), ursolic acid (V), acetyl aleuritolic acid (VI), beta-sitosterol-3-O-beta-D-glucopyranoside (daucosterol VII), beta-sitosterol (VII). Compound I to approximately V were obtained from this plant for the first time.

    Topics: Chromatography, Thin Layer; Iridoids; Mallotus Plant; Molecular Weight; Plant Stems; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

2005
[Study of water-soluble compounds from fungus garden of Odontotermes formosanus].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2005, Volume: 28, Issue:10

    To study water-soluble compounds from fungus garden of Odontotermes formosanus.. The chemical constituents of fungus garden were analyzed and identified by GC-MS.. 28 compounds were separated and 11 chemical constituents were identified.. The main constituents in water-solubles from fungus garden of Odontotermes formosanus are palmitic acid, linolei acid and oleic aid.

    Topics: Animals; Fatty Acids; Fungi; Gas Chromatography-Mass Spectrometry; Isoptera; Materia Medica; Oleic Acid; Sitosterols; Solubility; Stearic Acids; Water

2005
[Chemical constituents of the aerial parts of Rhamnus crenatus].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2005, Volume: 40, Issue:12

    To study chemical constituents of the aerial parts of Rhamnus crenatus sieb. et zucc.. The chemical constituents were isolated by chromatographic methods and their structures were elucidated on the basis of spectral analysis.. Five compounds were isolated and their structures were identified as crenatoside (1), torachrysone (2), emodin (3), emodin-1-O-beta-D-glucopyranoside (4) and beta-sitosterol (5) respectively.. Compound 1 is a new compound and the others were isolated from Rhamnus crenatus for the first time.

    Topics: Caffeic Acids; Emodin; Glucosides; Molecular Conformation; Molecular Structure; Plant Components, Aerial; Plants, Medicinal; Rhamnus; Sitosterols

2005
[Research on chemical ingredients of the root from cultivar Aralia cordata Thunb].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2005, Volume: 28, Issue:11

    Eight components were isolated and purified from the ethereal extract from cultivar Aralia cordata Thumb. By means of UV, IR, 1H-NMR, 13CNMR, they were identified as (I) kaur-16-en-19-oic acid, (II) docosanoic, (III) hexadecanoic acid, (V) stigmasterol, (V) 16-formyl-kaur-15-en-19-oic acid, (VI) 7-oxo-ent-pimara-8 (14), 15-dien-19-oic acid, (VII) 17-Hydroxy-ent-kaur-15-en-19-oic acid, (VlII) sitosterol. Among them, components II, III, V were isolated from the gunus of Aralia for the first time.

    Topics: Aralia; Diterpenes; Fatty Acids; Molecular Weight; Palmitic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Stigmasterol

2005
Down-regulation of hepatic and intestinal Abcg5 and Abcg8 expression associated with altered sterol fluxes in rats with streptozotocin-induced diabetes.
    Diabetologia, 2004, Volume: 47, Issue:1

    Type I diabetes is associated with altered hepatic bile formation and increased intestinal cholesterol absorption. The aim of this study was to evaluate whether altered expression of the ATP-Binding Cassette half-transporters Abcg5 and Abcg8, recently implicated in control of both hepatobiliary cholesterol secretion and intestinal cholesterol absorption, contributes to changed cholesterol metabolism in experimental diabetes.. mRNA and protein expression of Abcg5 and Abcg8 were determined in the liver and intestine of rats with streptozotozin-induced diabetes and related to relevant metabolic parameters in plasma, liver and bile.. Hepatic mRNA expression of both Abcg5 (-76%) and Abcg8 (-71%) was reduced in diabetic rats when compared to control rats. In spite of increased HDL cholesterol, considered a major source of biliary cholesterol, secretion of the sterol into bile relative to that of bile salts was reduced by 65% in diabetic animals. Intestinal mRNA expression of Abcg5 (-47%) and Abcg8 (-43%) as well as Abcg5 protein contents were also reduced in insulin-deficient animals. This was accompanied by a three- to four-fold increase in plasma beta-sitosterol and campesterol concentrations and by a doubling of the calculated apparent cholesterol absorption. These effects partially normalized upon insulin supplementation.. Our data indicate that effects of insulin-deficiency on bile composition and cholesterol absorption in rats are, at least partly, attributable to changes in hepatic and intestinal Abcg5 and Abcg8 expression.

    Topics: Animals; Apolipoprotein A-I; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile; Cholesterol; Diabetes Mellitus, Experimental; Gene Expression Regulation; Intestinal Mucosa; Lipoproteins; Liver; Male; Phytosterols; Rats; Rats, Wistar; RNA, Messenger; Sitosterols; Transcription, Genetic; Triglycerides

2004
Behaviour of Mycobacterium sp. NRRL B-3805 whole cells in aqueous, organic-aqueous and organic media studied by fluorescence microscopy.
    Applied microbiology and biotechnology, 2004, Volume: 64, Issue:5

    The present work aimed at quantifying the viability and morphological changes occurring during the time course of the side-chain cleavage of beta-sitosterol, in aqueous, two-phase organic-aqueous and organic media by free resting cells of Mycobacterium sp. NRRL B-3805. The solvent used was bis(2-ethylhexyl) phthalate (BEHP). A 66.3% reduction in cell viability was observed after 24 h when the cells were incubated in phosphate buffer only, but the percentage of viable cells was constant thereafter. In biphasic systems with BEHP, cell viability was maintained at higher values in the first 48 h, during which complete degradation of substrate was achieved. The availability of oxygen, which should be higher in the biphasic system than in the aqueous system, and of a carbon and energy source, thus seem important for the cells to retain their viability. In biphasic systems, cells tended to shrink and decrease their surface roughness, i.e. to decrease their surface area, possibly as a way to protect themselves from mechanical stress due to the presence of organic-aqueous interfacial forces, which resulted in disaggregation of cell clusters. A method used to visualise BEHP droplets with a standard optical microscope showed that the cells adhered to the surface of the solvent droplets, but no cells were observed inside these. In pure BEHP medium, cells retained their viability level for at least 150 h, independently of a pre-incubation period, which did not seem to induce any adaptation effect. Solvent biocompatibility, higher oxygen availability and reduced interfacial stress could have contributed to this maintenance of viability.

    Topics: Androstenedione; Culture Media; Diethylhexyl Phthalate; Emulsions; Image Processing, Computer-Assisted; Microscopy, Fluorescence; Mycobacterium; Sitosterols; Solvents

2004
Sitosterolemia in ABC-transporter G5-deficient mice is aggravated on activation of the liver-X receptor.
    Gastroenterology, 2004, Volume: 126, Issue:1

    Mutations in either adenosine triphosphate- binding cassette (ABC) half-transporter G5 or G8 cause sitosterolemia. It has been proposed that ABCG5/ABCG8 heterodimers mediate secretion of plant sterols and cholesterol by hepatocytes into bile and their efflux from enterocytes into the intestinal lumen.. To test whether deficiency of ABCG5 alone is sufficient to induce sitosterolemia, Abcg5-null mice were generated and characterized with respect to sterol metabolism.. Abcg5 deficiency was associated with strongly elevated plasma levels of beta-sitosterol (37-fold) and campesterol (7.7-fold) as well as reduced plasma cholesterol concentrations (-40%). Retention of orally administered [(3)H]beta-sitosterol in the intestinal wall (+550%) and plasma (+640%) was higher in Abcg5-null mice than in wild-type controls. Surprisingly, high plasma beta-sitosterol and campesterol concentrations were even further elevated in Abcg5-null mice on treatment with the synthetic LXR agonist T0901317 (0.015% dietary supplementation, 10 days), whereas these concentrations were reduced by approximately 75% in wild-type mice. Both cholesterol and phospholipid concentrations in gallbladder bile were decreased, but, unexpectedly, cholesterol/phospholipid ratios were unchanged in the absence of Abcg5 and increased in both genotypes on LXR activation. Hepatic expression of Abcg8 was reduced by about 35% in Abcg5-deficient mice when compared with controls. No compensatory overexpression of other ABC transporters potentially involved in hepatic cholesterol trafficking was observed on messenger RNA level.. Our data show that disruption of the Abcg5 gene alone is sufficient to cause hyperabsorption of dietary plant sterols and sitosterolemia in mice, whereas the ability to secrete cholesterol into bile is maintained.

    Topics: Animals; Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Bile; Bile Acids and Salts; Cholesterol; DNA-Binding Proteins; Gallbladder; Genotype; Hydrocarbons, Fluorinated; Lipoproteins; Liver X Receptors; Mice; Mice, Knockout; Orphan Nuclear Receptors; Phospholipids; Phytosterols; Receptors, Cytoplasmic and Nuclear; Sitosterols; Sulfonamides

2004
Can cholesterol absorption be reduced by phytosterols and phytostanols via a cocrystallization mechanism?
    Chemistry and physics of lipids, 2004, Volume: 127, Issue:1

    The formation of mixed water-insoluble poorly absorbable crystals between cholesterol (CH) and phytosterols (PS) or phytostanols (PSS) in the intestinal lumen has been considered for a long time as a plausible mechanism of the PS/PSS-induced reduction of serum CH concentration. In this report, we demonstrated with the use of the powder X-ray diffraction (XRD) and the differential scanning calorimetry (DSC) techniques that mixed CH:beta-sitosterol (SI) crystals can be formed by recrystallization of corresponding mixtures from melts and also from mixed CH:SI solutions in triglyceride oil. Formation of mixed CH:SI crystals takes place in a wide interval of CH:SI ratios, from approximately 10 up to approximately 75 wt.% of SI in the mixture. Formation of mixed CH:sitostanol (SS) crystals from melts and solutions in triglyceride oil was also detected, but in a more narrow interval of CH:SS ratios. However, during the lipolysis of model dietary emulsions under in vitro conditions, the formation of crystalline material was not detected due to the relatively high solubility of free sterols/stanols in products of fat hydrolysis. We found that the solubility of free CH, SI, and SS raises upon the increase in the solvent polarity, i.e. free fatty acid > diglycerideoil > triglyceride oil. Therefore, we believe that the cocrystallization mechanism of phytosterol-induced serum CH lowering has relatively low importance, unless the diet is specially designed to include relatively little amounts of dietary fats. The presented experimental evidence demonstrates that it is unlikely that the formation of poorly absorbable mixed crystals largely affects the intestinal absorption of CH and, therefore, that this is a prime mechanism by which PS and PSS effect CH absorption.

    Topics: Absorption; Calorimetry, Differential Scanning; Cholesterol; Crystallization; Lipase; Phytosterols; Sitosterols; Solubility; Triglycerides; X-Ray Diffraction

2004
Preparation and mass spectrometry of 14 pure and 18O(2)-labeled oxidation products from the phytosterols beta-sitosterol and stigmasterol.
    Analytical biochemistry, 2004, Feb-01, Volume: 325, Issue:1

    To lower cholesterol, phytosterols are currently introduced as food additives, where they may become oxidized. In addition, specific biological effects of oxyphytosterols are suggested by the recent molecular clarification of the phytosterol storage disease as a dysfunctional mutation of an active sterol reexporter potentially regulated by oxidized phytosterols. We therefore studied the hydroxybenzotriazole-mediated PbO(2)-driven oxidation of phytosterols and compared it to the oxidation of cholesterol. We prepared, identified, and purified standards of 14 oxidation products of two major phytosterols. The gas chromatographic mass spectrometric characteristics of the 7alpha- and 7beta-hydroxy-, 5alpha,6alpha-epoxy, 5beta,6beta-epoxy, 7keto-, 3beta,5alpha,6beta-trihydroxy-, 3keto-, and 7-dehydro-derivatives of beta-sitosterol and stigmasterol are presented. The method also provided a convenient access to prepare 18O-labeled oxyphytosterols of high chemical and isotopic purity and can easily be extended to further phytosterols and -stanols. This enables the gas chromatography-mass spectrometry analysis of oxyphytosterols and the study of their biological effects.

    Topics: Hematoporphyrins; Isotope Labeling; Lead; Mass Spectrometry; Oxidants, Photochemical; Oxidation-Reduction; Oxides; Oxygen Isotopes; Phytosterols; Sitosterols; Stigmasterol; Triazoles

2004
Effect of phytosterols and phytostanols on the solubilization of cholesterol by dietary mixed micelles: an in vitro study.
    Chemistry and physics of lipids, 2004, Volume: 127, Issue:2

    The effect of a plant sterol, beta-sitosterol (SI), and a plant stanol, sitostanol (SS), on the solubilization of cholesterol (CH) by model dietary mixed micelles was examined under in vitro conditions with the use of gas chromatography, isothermal titration calorimetry, NMR spectroscopy and cryogenic transmission electron microscopy techniques. Free SI and SS were shown to reduce the concentration of CH in dietary mixed micelles via a dynamic competition mechanism. CH, SI and SS affect the microstructure of lipid vesicles and influence the process of amphiphilic self-assembly of nutrients in the gut with the formation of dietary mixed micelles in a similar manner. Therefore, substitution of CH by phytosterols and phytostanols in the diet does not lead to the notable changes in the mechanism of dietary mixed micelle formation and does not affect the process of the intestinal transport of nutrients and drugs via the micellar diffusion mechanism. Our experimental findings demonstrate that the introduction of plant sterols and plant stanols into the diet is clearly beneficial for the reduction of the intestinal uptake of cholesterol. Due to the limited capacity of dietary mixed micelles to embody hydrophobic sterol/stanol molecules, the micellar concentration of cholesterol is reduced and hence, its transport towards the intestinal brush border membrane decreases.

    Topics: Bile Acids and Salts; Calorimetry; Cholesterol; Cholesterol, Dietary; Chromatography, Gas; Cryoelectron Microscopy; Hypolipidemic Agents; Micelles; Nuclear Magnetic Resonance, Biomolecular; Oleic Acid; Phosphatidylcholines; Sitosterols; Solubility; Thermodynamics

2004
LXR/RXR ligand activation enhances basolateral efflux of beta-sitosterol in CaCo-2 cells.
    Journal of lipid research, 2004, Volume: 45, Issue:5

    To examine whether intestinal ABCA1 was responsible for the differences observed between cholesterol and beta-sitosterol absorption, ABCA1-facilitated beta-sitosterol efflux was investigated in CaCo-2 cells following liver X receptor/retinoid X receptor (LXR/RXR) activation. Both the LXR agonist T0901317 and the natural RXR/LXR agonists 22-hydroxycholesterol and 9-cis retinoic acid enhanced the basolateral efflux of beta-sitosterol without altering apical efflux. LXR-mediated enhanced beta-sitosterol efflux occurred between 6 h and 12 h after activation, suggesting that transcription, protein synthesis, and trafficking was likely necessary prior to facilitating efflux. The transcription inhibitor actinomycin D prevented the increase in beta-sitosterol efflux by T0901317. Glybenclamide, an inhibitor of ABCA1 activity, and arachidonic acid, a fatty acid that interferes with LXR activation, also prevented beta-sitosterol efflux in response to the LXR ligand activation. Influx of beta-sitosterol mass did not alter the basolateral or apical efflux of the plant sterol, nor did it alter ABCA1, ABCG1, ABCG5, or ABCG8 gene expression or ABCA1 mass. Similar to results observed with intestinal ABCA1-facilitated cholesterol efflux, LXR/RXR ligand activation enhanced the basolateral efflux of beta-sitosterol without affecting apical efflux. The results suggest that ABCA1 does not differentiate between cholesterol and beta-sitosterol and thus is not responsible for the selectivity of sterol absorption by the intestine. ABCA1, however, may play a role in beta-sitosterol absorption.

    Topics: ATP Binding Cassette Transporter 1; ATP-Binding Cassette Transporters; Caco-2 Cells; DNA-Binding Proteins; Enzyme Activation; Humans; Ligands; Liver X Receptors; Orphan Nuclear Receptors; Receptors, Cytoplasmic and Nuclear; Retinoid X Receptors; Sitosterols

2004
A mouse model of sitosterolemia: absence of Abcg8/sterolin-2 results in failure to secrete biliary cholesterol.
    BMC medicine, 2004, Mar-24, Volume: 2

    Mutations in either of two genes comprising the STSL locus, ATP-binding cassette (ABC)-transporters ABCG5 (encoding sterolin-1) and ABCG8 (encoding sterolin-2), result in sitosterolemia, a rare autosomal recessive disorder of sterol trafficking characterized by increased plasma plant sterol levels. Based upon the genetics of sitosterolemia, ABCG5/sterolin-1 and ABCG8/sterolin-2 are hypothesized to function as obligate heterodimers. No phenotypic difference has yet been described in humans with complete defects in either ABCG5 or ABCG8. These proteins, based upon the defects in humans, are responsible for regulating dietary sterol entry and biliary sterol secretion.. In order to mimic the human disease, we created, by a targeted disruption, a mouse model of sitosterolemia resulting in Abcg8/sterolin-2 deficiency alone. Homozygous knockout mice are viable and exhibit sitosterolemia.. Mice deficient in Abcg8 have significantly increased plasma and tissue plant sterol levels (sitosterol and campesterol) consistent with sitosterolemia. Interestingly, Abcg5/sterolin-1 was expressed in both liver and intestine in Abcg8/sterolin-2 deficient mice and continued to show an apical expression. Remarkably, Abcg8 deficient mice had an impaired ability to secrete cholesterol into bile, but still maintained the ability to secrete sitosterol. We also report an intermediate phenotype in the heterozygous Abcg8+/- mice that are not sitosterolemic, but have a decreased level of biliary sterol secretion relative to wild-type mice.. These data indicate that Abcg8/sterolin-2 is necessary for biliary sterol secretion and that loss of Abcg8/sterolin-2 has a more profound effect upon biliary cholesterol secretion than sitosterol. Since biliary sitosterol secretion is preserved, although not elevated in the sitosterolemic mice, this observation suggests that mechanisms other than by Abcg8/sterolin-2 may be responsible for its secretion into bile.

    Topics: Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile; Bile Acids and Salts; Cholesterol; Female; Gene Expression; Intestines; Lipoproteins; Male; Mice; Mice, Inbred C57BL; Mice, Knockout; Models, Animal; Mutation; Phytosterols; Sitosterols

2004
Biomass burning as the main source of organic aerosol particulate matter in Malaysia during haze episodes.
    Chemosphere, 2004, Volume: 55, Issue:8

    The haze episodes that occurred in Malaysia in September-October 1991, August-October 1994 and September-October 1997 have been attributed to suspended smoke particulate matter from biomass burning in southern Sumatra and Kalimantan, Indonesia. In the present study, polar organic compounds in aerosol particulate matter from Malaysia are converted to their trimethylsilyl derivatives and analyzed by gas chromatography-mass spectrometry in order to better assess the contribution of the biomass burning component during the haze episodes. On the basis of this analysis, levoglucosan was found to be the most abundant organic compound detected in almost all samples. The monosaccharides, alpha- and beta-mannose, the lignin breakdown products, vanillic and syringic acids and the minor steroids, cholesterol and beta-sitosterol were also present in some samples. The presence of the tracers from smoke overwhelmed the typical signatures of emissions from traffic and other anthropogenic activities in the urban areas.

    Topics: Air Pollution; Biomass; Cholesterol; Gallic Acid; Gas Chromatography-Mass Spectrometry; Glucose; Incineration; Malaysia; Mannose; Sitosterols; Smoke; Trimethylsilyl Compounds; Vanillic Acid

2004
Effects of plant stanol and sterol esters on serum phytosterols in a family with familial hypercholesterolemia including a homozygous subject.
    The Journal of laboratory and clinical medicine, 2004, Volume: 143, Issue:4

    We studied the concentrations and ratios to cholesterol of noncholesterol sterols reflecting absorption (eg, campesterol) or synthesis (eg, lathosterol) of cholesterol off and on plant sterol and stanol ester spreads in serum and in different lipoproteins of a family with familial hypercholesterolemia, including heterozygous parents receiving no treatment and their homozygous offspring undergoing long-term treatment with statins and apheresis. Serum cholesterol levels were similar in the homozygous and heterozygous individuals, but the concentrations of sterols reflecting cholesterol absorption were as much as 10 times greater in the homozygous child than in the heterozygous parents, whereas the respective markers of cholesterol synthesis only tended to be higher. About 70% of squalene in the homozygous individual (60% in the heterozygous family members) and 85% to 90% of noncholesterol sterols (60%-80% in the heterozygous subjects) were transported by low-density lipoprotein. The ratios of absorption sterols to cholesterol were higher in high-density lipoprotein (HDL) than in very low-density lipoprotein (VLDL), whereas those of synthesis markers and plant stanols were highest in VLDL. The ratios of absorption sterols in serum were mostly lower than those in HDL but higher than in VLDL, whereas the ratios of synthesis sterols in serum were lower than they were in VLDL. Both spreads reduced serum total cholesterol by about 14% in the heterozygous family members and 9% in the homozygous individual. The sterol ester spread increased serum plant sterol concentrations (eg, campesterol in the homozygous family member increased from 5 to 9 mg/dL) and the ratios to cholesterol, but the stanol ester spread decreased them. Plant sterol esters seemed to similarly decrease serum cholesterol in this family with familial hypercholesterolemia, but the clinical role of increased plant sterol concentrations, almost doubled in the LDL of homozygous individuals, is not known.

    Topics: Adult; Blood Component Removal; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Dietary Fats; Double-Blind Method; Female; Heterozygote; Homozygote; Humans; Hyperlipoproteinemia Type II; Hypolipidemic Agents; Male; Margarine; Middle Aged; Phytosterols; Sitosterols; Squalene; Triglycerides

2004
beta-Sitosterol, beta-Sitosterol Glucoside, and a Mixture of beta-Sitosterol and beta-Sitosterol Glucoside Modulate the Growth of Estrogen-Responsive Breast Cancer Cells In Vitro and in Ovariectomized Athymic Mice.
    The Journal of nutrition, 2004, Volume: 134, Issue:5

    We hypothesized that the phytosterols beta-sitosterol (BSS), beta-sitosterol glucoside (BSSG), and Moducare (MC; BSS:BSSG = 99:1) could modulate the growth of estrogen-dependent human breast cancer cells in vitro and in vivo. The present study evaluated the estrogenic and antiestrogenic effects of BSS, BSSG, and MC (0.001 to 150 micromol/L) on the proliferation of Michigan Cancer Foundation 7 (MCF-7) cells in vitro. Both BSS (>1 micromol/L) and MC (>50 micromol/L) increased MCF-7 cell proliferation. Treatment with 150 micro mol/L of BSS and MC increased cell growth by 2.4 and 1.5 times, respectively, compared to the negative control (NC) group. However, BSSG had no effect at the concentrations tested. The effects of dietary BSS, BSSG, and MC on the growth of MCF-7 cells implanted in ovariectomized athymic mice were also evaluated. Estrogenic effects of the phytosterols were evaluated in the NC, BSS, BSSG, and MC treatment groups, and antiestrogenic effects were evaluated in the 17 beta-estradiol (E(2)), E(2) + BSS, E(2) + BSSG, and E(2) + MC treatment groups. Mice were treated with dietary BSS (9.8 g/kg AIN93G diet), BSSG (0.2 g/kg diet), or MC (10.0 g/kg diet) for 11 wk. Dietary BSS, BSSG, and MC did not stimulate MCF-7 tumor growth. However, dietary BSS, BSSG, and MC reduced E(2)-induced MCF-7 tumor growth by 38.9% (P < 0.05), 31.6% (P = 0.08), and 42.13% (P < 0.05), respectively. The dietary phytosterols lowered serum E(2) levels by 35.1, 30.2, and 36.5% in the E(2) + BSS, E(2) + BSSG, and E(2) + MC groups, respectively (P < 0.05), compared to that of the E(2) treatment group. Estrogen-responsive pS2 mRNA expression in tumors did not differ among groups, but expression of the antiapoptotic marker B-cell lymphoma/leukemia-2 (bcl-2) in tumors from the E(2) + MC group was downregulated, compared to that of the E(2) treatment group. In summary, BSS and MC stimulated MCF-7 cell growth in vitro. Although BSSG comprises only 1% of MC, BSSG made MC less estrogenic than BSS alone in vitro. However, dietary BSS and MC protected against E(2)-stimulated MCF-7 tumor growth and lowered circulating E(2) levels.

    Topics: Animals; Breast Neoplasms; Cell Division; Cell Line, Tumor; Drug Combinations; Drug Implants; Estradiol; Estrogen Antagonists; Female; Humans; Mammary Neoplasms, Experimental; Membrane Proteins; Mice; Mice, Nude; Neoplasm Transplantation; Organ Size; Ovariectomy; Phytosterols; Presenilin-2; Proto-Oncogene Proteins c-bcl-2; Sitosterols; Uterus

2004
Effect of a new beta-sitosterol analogue on plasma lipid concentrations in rats.
    Chemical & pharmaceutical bulletin, 2004, Volume: 52, Issue:5

    N-Substituted succinamic acid beta-sitosteryl ester derivatives were prepared and evaluated. Compounds 1 and 2 were prepared in 76-92% yields by the reaction of beta-sitosterol and succinic anhydride, followed by the activation of the resulting acid compound 1 by thionyl chloride or methyl chloroformate, and finally by amination with appropriate amines. Compound 2a (DANA87) was also easily obtained in one step by the direct addition of beta-sitosterol to dicyclohexylcarbodiimide (DCC) in 80% yield. Administration of the dietary compound DANA87 resulted in significant decreases in total plasma cholesterol (TC) and low-density lipoprotein (LDL) cholesterol concentrations compared with controls in a rat model. High-density lipoprotein cholesterol and plasma triglyceride levels were not affected. These findings indicate that DANA87 functions as TC and LDL cholesterol-reducing agent.

    Topics: Animals; Anticholesteremic Agents; Cholesterol, HDL; Cholesterol, LDL; Male; Rats; Rats, Sprague-Dawley; Sitosterols

2004
Oral absorption of phytosterols and emulsified phytosterols by Sprague-Dawley rats.
    The Journal of nutritional biochemistry, 2004, Volume: 15, Issue:5

    Clinical studies have demonstrated that consumption of phytosterol esters in lipid-based foods decreases serum concentrations of total and LDL cholesterol. These substances represent minimal potential for adverse effects when consumed orally because of their low bioavailability. However, some studies have reported estrogenic and other effects in laboratory animals treated parenterally with phytosterols, demonstrating that these substances may have the potential to cause adverse effects if absorbed. Water-soluble phytosterols have been prepared by formulation with emulsifiers to expand delivery options to include non-lipid-based foods. However, emulsifiers are used as excipients in the formulation of lipophilic pharmaceuticals to increase solubility, thereby increasing their absorption. Therefore, oral consumption of emulsified water-soluble phytosterols could potentially increase their absorption. In the current study, absorption of phytosterols prepared as water-soluble emulsified micelles with two different food-grade emulsifiers was evaluated in Sprague-Dawley rats and compared with absorption of non-micellar free phytosterols and esterified phytosterol mixtures dissolved in a lipophilic vehicle (soybean oil). Rats were dosed via gavage with 42 mg/kg of formulated phytosterol preparations. Blood was collected at 8, 16, 24, and 32 hours, extracted with hexane, derivatized with benzoyl chloride, and analyzed by high-performance liquid chromatography to determine concentrations of beta-sitosterol, and campesterol. Plasma concentrations and AUC(0-32 hours) [microg/mL/h] of beta-sitosterol and campesterol were lower in plasma obtained from rats treated with emulsified phytosterol preparations than in animals treated with free phytosterols dissolved in soybean oil. Because the pharmacokinetic profile of water-soluble phytosterols is similar to that of phytosterols administered in a lipid vehicle, the safety profile is likely to be the same as that of phytosterols and phytosterol esters in currently used applications.

    Topics: Absorption; Animals; Cholesterol; Chromatography, High Pressure Liquid; Diet; Emulsions; Esterification; Kinetics; Micelles; Mouth; Phosphatidylcholines; Phytosterols; Rats; Rats, Sprague-Dawley; Sitosterols; Solubility; Water

2004
Effect of beta-sitosterol on the characteristics of vesicular gels containing chlorhexidine.
    International journal of pharmaceutics, 2004, Jun-18, Volume: 278, Issue:1

    Previous studies confirm that beta-sitosterol is very effective in altering the molecular packing of soybean lecithin bilayers even more than the cholesterol. The primary aim of the present study was to evaluate the influence of the beta-sitosterol portion in the lipid bilayer on the physical-chemical characteristics of the prepared gel systems, and its influence on the consequent drug release from the liposomes obtained from vesicular phospholipid gels (VPG-s) by redispersion. VPG-s were prepared of different molar ratios of lecithin:sterol components (10:90-35:65 mol%). The mixture was hydrated with the aqueous solution of chlorhexidin digluconate in order to achieve 30% (w/w) final concentration of the lipid mixtures and 4% (w/w) concentration of the drug in each homogenized VPG sample. To characterize the obtained VPG systems optical microscopic examinations using polarized light, differential scanning calorimetry (DSC), photon correlation spectroscopy (PCS), and dynamic surface tension measurements were carried out. Vertical type diffusion cell was applied to determine the amount of released chlorhexidine digluconate. As a result of the surface tension-decreasing effect of beta-sitosterol, the membrane deformability and the dispersity of the system increased. The increased dispersity and fluidity significantly increased the extent of released chlorhexidine from the vesicles.

    Topics: Chlorhexidine; Gels; Liposomes; Sitosterols; Solubility; Surface Properties

2004
A new 3,4-seco-lupane derivative from Lasianthus gardneri.
    Journal of natural products, 2004, Volume: 67, Issue:5

    A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, beta-sitosterol, ursolic acid, and stigmasterol 3-O-beta-d-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of (13)C and (1)H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.

    Topics: Glucosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pentacyclic Triterpenes; Plant Stems; Rubiaceae; Sitosterols; Sri Lanka; Stigmasterol; Triterpenes; Ursolic Acid

2004
Niemann-Pick C1 Like 1 (NPC1L1) is the intestinal phytosterol and cholesterol transporter and a key modulator of whole-body cholesterol homeostasis.
    The Journal of biological chemistry, 2004, Aug-06, Volume: 279, Issue:32

    Niemann-Pick C1 Like 1 (NPC1L1) is a protein localized in jejunal enterocytes that is critical for intestinal cholesterol absorption. The uptake of intestinal phytosterols and cholesterol into absorptive enterocytes in the intestine is not fully defined on a molecular level, and the role of NPC1L1 in maintaining whole body cholesterol homeostasis is not known. NPC1L1 null mice had substantially reduced intestinal uptake of cholesterol and sitosterol, with dramatically reduced plasma phytosterol levels. The NPC1L1 null mice were completely resistant to diet-induced hypercholesterolemia, with plasma lipoprotein and hepatic cholesterol profiles similar to those of wild type mice treated with the cholesterol absorption inhibitor ezetimibe. Cholesterol/cholate feeding resulted in down-regulation of intestinal NPC1L1 mRNA expression in wild type mice. NPC1L1 deficiency resulted in up-regulation of intestinal hydroxymethylglutaryl-CoA synthase mRNA and an increase in intestinal cholesterol synthesis, down-regulation of ABCA1 mRNA, and no change in ABCG5 and ABCG8 mRNA expression. NPC1L1 is required for intestinal uptake of both cholesterol and phytosterols and plays a major role in cholesterol homeostasis. Thus, NPC1L1 may be a useful drug target for the treatment of hypercholesterolemia and sitosterolemia.

    Topics: Animals; Biological Transport; Cholesterol; Cholesterol, Dietary; Homeostasis; Hypercholesterolemia; Intestinal Absorption; Intestinal Mucosa; Lipoproteins; Liver; Membrane Transport Proteins; Mice; Mice, Inbred C57BL; Mice, Knockout; Phytosterols; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Sitosterols; Triglycerides

2004
[Can ezetimib also be used as a treatment for beta-sitosterol].
    Deutsche medizinische Wochenschrift (1946), 2004, Jun-11, Volume: 129, Issue:24

    Topics: Anticholesteremic Agents; Azetidines; Ezetimibe; Humans; Sitosterols

2004
Lipid rafts in higher plant cells: purification and characterization of Triton X-100-insoluble microdomains from tobacco plasma membrane.
    The Journal of biological chemistry, 2004, Aug-27, Volume: 279, Issue:35

    A large body of evidence from the past decade supports the existence of functional microdomains in membranes of animal and yeast cells, which play important roles in protein sorting, signal transduction, or infection by pathogens. They are based on the dynamic clustering of sphingolipids and cholesterol or ergosterol and are characterized by their insolubility, at low temperature, in nonionic detergents. Here we show that similar microdomains also exist in plant plasma membrane isolated from both tobacco leaves and BY2 cells. Tobacco lipid rafts were found to be greatly enriched in a sphingolipid, identified as glycosylceramide, as well as in a mixture of stigmasterol, sitosterol, 24-methylcholesterol, and cholesterol. Phospho- and glycoglycerolipids of the plasma membrane were largely excluded from lipid rafts. Membrane proteins were separated by one- and two-dimensional gel electrophoresis and identified by tandem mass spectrometry or use of specific antibody. The data clearly indicate that tobacco microdomains are able to recruit a specific set of the plasma membrane proteins and exclude others. We demonstrate the recruitment of the NADPH oxidase after elicitation by cryptogein and the presence of the small G protein NtRac5, a negative regulator of NADPH oxidase, in lipid rafts.

    Topics: Blotting, Western; Cell Membrane; Centrifugation, Density Gradient; Cholesterol; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Detergents; Electrophoresis, Gel, Two-Dimensional; Electrophoresis, Polyacrylamide Gel; Ergosterol; Ions; Lipid Metabolism; Lipids; Mass Spectrometry; Membrane Microdomains; Microscopy, Electron; NADPH Oxidases; Nicotiana; Octoxynol; Phytosterols; Plant Leaves; Protein Structure, Tertiary; Signal Transduction; Sitosterols; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Stigmasterol; Sucrose; Temperature

2004
Extracellular 3beta-hydroxysteroid oxidase of Mycobacterium vaccae VKM Ac-1815D.
    The Journal of steroid biochemistry and molecular biology, 2004, Volume: 91, Issue:1-2

    Extracellular 3beta-hydroxysteroid oxidase (SO) has been isolated from cell-free cultivation broth at the growth of Mycobacterium vaccae VKM Ac-1815D on glycerol-mineral medium in the presence of sitosterol. The enzyme is responsible for the transformation of 3beta-hydroxy-5-ene- to 3-keto-4-ene-moiety of steroids including dehydrogenation of 3beta-hydroxy function followed by delta5-->delta4 isomerization. 6-Hydroxy-4-sitosten-3-one and 6-hydroxy-4-androsten-3,17-dione were revealed among the metabolites at the incubation of the enzyme preparations with sitosterol and dehydroepiandrosterone (DHEA), respectively. The enzyme was strongly NADH or NADPH dependent. SO has been purified over 300-fold using cultivation broth concentration on hollow fibers followed by fractionation by ammonium sulphate, column chromatography on DEAE-Toyopearl, hydroxyapatite Bio-Gel HTP and double gel-filtration on Bio-Gel A 0.5 M. SDS-electrophoresis gave a molecular mass estimate of 62 +/- 4 kDa. The purified SO obeyed Michaelis-Menten kinetics, double reciprocal plots kinetics revealed Km value towards DHEA 5 x 10(-4) M. Along with SO activity, 17-hydroxysteroid dehydrogenase (17-OH SDH) and 3-ketosteroid-1(2)-dehydrogenase (1(2)-SDH) activities were detected in cell-free cultivation broth. The extracellular steroid transforming activities of C-17-ketosteroid producing mycobacteria were hitherto unreported.

    Topics: 3-Hydroxysteroid Dehydrogenases; Androstenedione; Cell Wall; Cell-Free System; Chromatography, Gel; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Dehydroepiandrosterone; Electrophoresis, Polyacrylamide Gel; Glycerol; Hydrogen; Hydroxysteroid Dehydrogenases; Kinetics; Mass Spectrometry; Models, Chemical; Mycobacterium; NAD; NADP; Oxidoreductases; Sitosterols; Steroids; Testosterone

2004
[Chemical constituents from Typhonium flagelliforme].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2004, Volume: 27, Issue:3

    To study the major chemical constituents from the root tuber of Typhyonium flagelliforme.. Compounds were separated and purified with silica gel column and preparative HPLC, and their structures were elucidated on the basis of spectroscopic evidence (UV, IR, MS, NMR and 2D NMR).. Four compounds were identified as 1-O-beta-glucopyranosyl-2-[(2-hydroxyloctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (1), coniferin (2), beta-sitosterol (3) and beta-daucosterol (4).. A cerebroside with significant antihepatotoxic activity and a phenylpropanoid glycoside were isolated from Typhyonium flagelliforme for the first time.

    Topics: Araceae; Cinnamates; Glucosides; Molecular Conformation; Molecular Structure; Plant Roots; Plants, Medicinal; Sitosterols

2004
Brassinosteroid deficiency due to truncated steroid 5alpha-reductase causes dwarfism in the lk mutant of pea.
    Plant physiology, 2004, Volume: 135, Issue:4

    The endogenous brassinosteroids in the dwarf mutant lk of pea (Pisum sativum) were quantified by gas chromatography-selected ion monitoring. The levels of castasterone, 6-deoxocastasterone, and 6-deoxotyphasterol in lk shoots were reduced 4-, 70-, and 6-fold, respectively, compared with those of the wild type. The fact that the application of brassinolide restored the growth of the mutant indicated that the dwarf mutant lk is brassinosteroid deficient. Gas chromatography-selected ion monitoring analysis of the endogenous sterols in lk shoots revealed that the levels of campestanol and sitostanol were reduced 160- and 10-fold, respectively, compared with those of wild-type plants. These data, along with metabolic studies, showed that the lk mutant has a defect in the conversion of campest-4-en-3-one to 5alpha-campestan-3-one, which is a key hydrogenation step in the synthesis of campestanol from campesterol. This defect is the same as that found in the Arabidopsis det2 mutant and the Ipomoea nil kbt mutant. The pea gene homologous to the DET2 gene, PsDET2, was cloned, and it was found that the lk mutation would result in a putative truncated PsDET2 protein. Thus it was concluded that the short stature of the lk mutant is due to a defect in the steroidal 5alpha-reductase gene. This defect was also observed in the callus induced from the lk mutant. Biosynthetic pathways involved in the conversion of campesterol to campestanol are discussed in detail.

    Topics: 3-Oxo-5-alpha-Steroid 4-Dehydrogenase; Amino Acid Sequence; Brassinosteroids; Cholestanols; Cholesterol; Conserved Sequence; Dwarfism; Gene Expression Regulation, Plant; Molecular Sequence Data; Mutation; Phytosterols; Pisum sativum; Plant Diseases; Sequence Alignment; Sequence Deletion; Sequence Homology, Amino Acid; Sitosterols; Steroids, Heterocyclic

2004
Growth hormone selectively improves intestinal cholesterol absorption after jejunoileal autotransplantation in pigs.
    Journal of pediatric surgery, 2004, Volume: 39, Issue:8

    Small bowel transplantation impairs enteric function and causes malabsorption of cholesterol and bile acids. Growth hormone stimulates intestinal absorptive function. The authors hypothesized that long-term growth hormone therapy could improve absorption of bile acids and cholesterol after autotransplantation of the jejunoileum.. Sixteen pigs with similar food, cholesterol, and fat intake underwent either sham laparotomy or a model of jejunoileal autotransplantation, including extrinsic autonomic denervation, lymphatic interruption, and in situ cold ischemia. Five randomly chosen autotransplanted animals received daily growth hormone treatment for 8 weeks. Serum lipids, absorption, and excretion of cholesterol, bile acids, and fat were determined after 8 weeks. Mucosal morphometrics, proliferation, and enzyme activities were determined. Plasma cholesterol precursors and plant sterols, respective markers of cholesterol synthesis and absorption, were measured after 2 and 8 weeks.. After jejunoileal autotransplantation, growth hormone treatment significantly increased body weight gain, cholesterol absorption efficiency from 45.1% to 62.1%, plasma campesterol to cholesterol proportions, and biliary secretion of cholesterol. With or without growth hormone treatment, autotransplantation significantly increased fecal bile acid excretion, plasma cholesterol precursors, fecal bacterially modified neutral sterols, mucosal thickness of the ileum (but not jejunum), and intestinal transit time when compared with sham-operated animals. Crypt cell proliferation, mucosal enzyme activities, and microvilli showed no differences between the groups.. These findings suggest that growth hormone treatment selectively improves cholesterol, but not bile acid absorption, after autotransplantation of the jejunoileum.

    Topics: Animals; Autonomic Denervation; Bile Acids and Salts; Cholesterol; Cholesterol, Dietary; Drug Evaluation, Preclinical; Feces; Female; Human Growth Hormone; Ileum; Intestinal Absorption; Intestinal Mucosa; Jejunum; Laparotomy; Lipids; Malabsorption Syndromes; Phytosterols; Postoperative Complications; Recombinant Proteins; Sitosterols; Sus scrofa; Transplantation, Autologous

2004
Studies on the chemical constituents of the roots of Rhododendron molle G. Don.
    Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban, 2004, Volume: 24, Issue:2

    The compounds from the root of Rhododendron molle G. Don were isolated, purified by various chromatographic techniques, and their structures were identified according to the physical and chemical features and spectral data. Three compounds were separated from the root of Rhododendron molle G. Don and identified as Rhodojaponin-III, taraxerol, beta-sitosterol for the first time.

    Topics: Diterpenes; Drugs, Chinese Herbal; Oleanolic Acid; Plant Roots; Rhododendron; Sitosterols

2004
Disruption of cholesterol homeostasis by plant sterols.
    The Journal of clinical investigation, 2004, Volume: 114, Issue:6

    The ABC transporters ABCG5 and ABCG8 limit absorption and promote excretion of dietary plant sterols. It is not known why plant sterols are so assiduously excluded from the body. Here we show that accumulation of plant sterols in mice lacking ABCG5 and ABCG8 (G5G8-/- mice) profoundly perturbs cholesterol homeostasis in the adrenal gland. The adrenal glands of the G5G8-/- mice were grossly abnormal in appearance (brown, not white) due to a 91% reduction in cholesterol content. Despite the very low cholesterol levels, there was no compensatory increase in cholesterol synthesis or in lipoprotein receptor expression. Moreover, levels of ABCA1, which mediates sterol efflux, were increased 10-fold in the G5G8-/- adrenals. Adrenal cholesterol levels returned to near-normal levels in mice treated with ezetimibe, which blocks phytosterol absorption. To determine which plant sterol(s) caused the metabolic changes, we examined the effects of individual plant sterols on cholesterol metabolism in cultured adrenal cells. Addition of stigmasterol, but not sitosterol, inhibited SREBP-2 processing and reduced cholesterol synthesis. Stigmasterol also activated the liver X receptor in a cell-based reporter assay. These data indicate that selected dietary plant sterols disrupt cholesterol homeostasis by affecting two critical regulatory pathways of lipid metabolism.

    Topics: Adrenal Cortex Hormones; Adrenal Glands; Animals; ATP Binding Cassette Transporter, Subfamily G; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP-Binding Cassette Transporters; Cholesterol; Homeostasis; Lipoproteins; Mice; Mice, Knockout; Phytosterols; Sitosterols

2004
Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae).
    Phytochemistry, 2004, Volume: 65, Issue:17

    The incorporation of [1-13C]-labeled glucose into the irregular monoterpene artemisia ketone, the regular monoterpenes camphor and beta-thujone, the sesquiterpene germacrene D, the diterpene trans-phytol and beta-sitosterol and isofucosterol has been studied in axenic cultures of Tanacetum vulgare L. (Asteraceae). Quantitative 13C NMR spectroscopic analysis of the resulting labeling patterns showed that the isoprene units of the monoterpenes and the diterpene are formed via the methylerythritol phosphate (MEP) pathway, whereas the isoprene building blocks of the sesquiterpene and the sterols originate from the mevalonic acid (MVA) pathway.

    Topics: Bicyclic Monoterpenes; Camphor; Diterpenes; Magnetic Resonance Spectroscopy; Monoterpenes; Sesquiterpenes, Germacrane; Sitosterols; Stigmasterol; Tanacetum; Terpenes

2004
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds.
    Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 2004, Volume: 60, Issue:13

    The wood resin in Scots pine (Pinus sylvestris) stemwood and branch wood were studied using UV resonance Raman (UVRR) spectroscopy. UVRR spectra of the sapwood and heartwood hexane extracts, solid wood samples and model compounds (six resin acids, three fatty acids, a fatty acid ester, sitosterol and sitosterol acetate) were collected using excitation wavelengths of 229, 244 and 257 nm. In addition, visible Raman spectra of the fatty and resin acids were recorded. Resin compositions of heartwood and sapwood hexane extracts were determined using gas chromatography. Raman signals of both conjugated and isolated double bonds of all the model compounds were resonance enhanced by UV excitation. The oleophilic structures showed strong bands in the region of 1660-1630 cm(-1). Distinct structures were enhanced depending on the excitation wavelength. The UVRR spectra of the hexane extracts showed characteristic bands for resin and fatty acids. It was possible to identify certain resin acids from the spectra. UV Raman spectra collected from the solid wood samples containing wood resin showed a band at approximately 1650 cm(-1) due to unsaturated resin components. The Raman signals from extractives in the resin rich branch wood sample gave even more strongly enhanced signals than the aromatic lignin.

    Topics: Abietanes; Alkenes; Diterpenes; Lipids; Molecular Structure; Phenanthrenes; Pinus sylvestris; Plant Extracts; Sitosterols; Spectrophotometry, Ultraviolet; Spectrum Analysis, Raman; Vibration; Wood

2004
[Studies on chemical constituents in dried buds of Lonicera confusa].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2004, Volume: 29, Issue:9

    To investigate the chemical constituents of the dried buds of Lonicera confusa.. Chromatography and spectral analysis were respectively used to isolate and identify the constituents.. Seven compounds were isolated from the dried buds of L. confusa, and identified as rutin, quercetin, luteilin-7-O-beta-D-galactoside, lonicerin, chlorogenic acid, beta-sitosterol and tetratriacontane.. Rutin was isolated from the genus for the first time, and the others were isolated from the species for the first time.

    Topics: Chlorogenic Acid; Flowers; Lonicera; Plants, Medicinal; Quercetin; Rutin; Sitosterols

2004
[Study on the chemical constituents from the herb of Gentianopsis paludosa].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2004, Volume: 29, Issue:11

    To study the chemical constituents from the herb of Gentianopsis paludosa.. Column chromatogrophy and spectral analysis were used to isolate and identify the constituents.. Six compounds were isolated and identified as 1,7-dihydroxy-3,8-dimethoxyxanthone (I), 1-hydroxy-3, 7, 8-trimethoxyxanthone (II), 1, 8-dihydroxy-3, 7-dimethoxyxanthone (III), 1-hydroxy-3, 7-dimethoxyxanthone (IV), beta-sitosterol (V), daucosterol (VI).. Compounds III-VI were isolated from the plant for the first time.

    Topics: Gentianaceae; Plants, Medicinal; Sitosterols; Xanthones

2004
[Studies on chemical constituents from branch of Trema angustifolia].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2004, Volume: 29, Issue:3

    To study the chemical constituents from the branch of Trema angustifolia.. The compounds were isolated by silica gel column chromatography, and their structures were elucidated by means of spectral analysis.. Six compounds were identified as beta-sitosterol (I), viminalol (II), acetylursolic acid (III), oleanolic acid (IV), paprazine (V), moupinamide (VI).. All the compounds were isolated from this plant for the first time.

    Topics: Chromatography, Gel; Coumaric Acids; Oleanolic Acid; Plant Stems; Plants, Medicinal; Sitosterols; Trema; Tyramine

2004
[Studies on chemical constituents in bud of Artemisia scoparia (III)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2004, Volume: 29, Issue:5

    To investigate the chemical constituents in flower bud of Artemisia scoparia.. The methanol extract was isolated by column chromatography with silica gel, polyamide and Sephadex LH-20 as packing materials and HPLC, six compounds were obtained and their structures were identified by UV, NMR and MS.. Six compounds were identified as beta-sitosterol (IX), 6,7-dimethoxycoumarin (X), 6-demethylcapillarisin (XI), capillartemisin B (XII), kumatakenin (XIII), isoscoploletin-beta-D-glucoside (XIV).. XI, XII, XIII and XIV were obtained from the plant for the first time, and XI is a new compound.

    Topics: Artemisia; Chromones; Flowers; Molecular Conformation; Molecular Structure; Phenylpropionates; Plants, Medicinal; Sitosterols

2004
[Study on the chemical constituents from Picria fel-tarrae].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2004, Volume: 29, Issue:2

    To isolate and identify compounds from Picria fel-tarrae in order to utilize it better.. Constituents from Picria fel-tarrae were isolated by several column chromatography and their structures were elucidated on the basis of chemical and spectral analysis.. Six compounds, N-benzoylphenylalanyl-L-phenylalaninol acetate (1), 1-hydroxy-7-hydroxymethyl-9,10-anthraquinone (2), 9, 16-dioxo-10,12,14-octadeca-trienoic acid (3), 5,7,4'-trihydroxy-flavone (4), beta-sitosterol (5), and daucosterol (6) were obtained from the fraction with relatively low polarity of EtOH extract of Picria fel-tarrae.. Compounds 1-6 were isolated from picria fel-tarrae Lour for the first time, and the 13C-NMR data of compounds 1-3 are provided firstly in the literature.

    Topics: Apigenin; Dipeptides; Molecular Structure; Plants, Medicinal; Scrophulariaceae; Sitosterols

2004
Regional intestinal absorption of FITC-dextran 4,400 with nanoparticles based on beta-sitosterol beta-D-glucoside in rats.
    Journal of pharmaceutical sciences, 2003, Volume: 92, Issue:2

    Nanoparticles (NP) are potential carriers for drug delivery to the targeted intestine. NP based on beta-sitosterol beta-D-glucoside (Sit-G) enhanced the colon-specific absorption of FITC-dextran 4,400 (FD-4), because the concentration-dependent increase of bioavailability appeared in only the colon. In a permeation study, the absorption enhancement in the colon was suppressed in the following conditions: (1) the addition of Sit-G NP to serosa; (2) a permeation study at 4 degrees C; (3) the addition of endocytosis inhibitor, cytochalasin B. NP based on sitosterol, the aglycon of Sit-G, did not increase the FD-4 colonic permeation. The addition of Sit-G NP to the mucosal side induced a decrease of transepithelial resistance (TEER), but this phenomenon was suppressed by an inhibitor of Na(+)-dependent specific glucose transporter, phrolidzin, which did not affect FD-4 permeation. These findings suggested that absorption enhancement by Sit-G NP may not be due to opening of a tight junction, but might be related to endocytosis via glucose residue of Sit-G.

    Topics: Algorithms; Animals; Dextrans; Diffusion Chambers, Culture; Endocytosis; Excipients; Fluorescein-5-isothiocyanate; Freeze Fracturing; Glycosides; Intestinal Absorption; Male; Microspheres; Rats; Rats, Wistar; Sitosterols; Suspensions

2003
Effects of a phytosterol mixture on male fish plasma lipoprotein fractions and testis P450scc activity.
    General and comparative endocrinology, 2003, Feb-01, Volume: 130, Issue:2

    Plant sterols (phytosterols) have been identified as one potential source of reproductive effects in fish living downstream of pulp mills. beta-Sitosterol, the predominant plant sterol in pulp mill effluent, has previously been shown to decrease plasma sex steroid and cholesterol levels and in vitro gonadal steroid production in fish. In this study, male brook trout (Salvelinus fontinalis) and goldfish (Carassius auratus) were exposed to a phytosterol mixture (72% beta-sitosterol) via Silastic intraperitoneal implants to help elucidate the mechanisms of action of phytosterols on steroid depression. As cholesterol is exogenously supplied for gonadal steroidogenesis, changes in plasma cholesterol fractions were examined. In male brook trout, low-density lipoprotein cholesterol and triglyceride levels decreased significantly, 43 and 50%, respectively, in phytosterol-treated fish. It is improbable, however, that these decreases are linked to depressed gonadal steroidogenesis in fish. The activity of P450scc, which converts cholesterol to pregnenolone (the first step in the steroidogenic pathway), was not affected in testis mitochondria isolated from brook trout or goldfish. Further investigation of the mechanisms of action of phytosterols is required.

    Topics: Animals; Cholesterol; Cholesterol Side-Chain Cleavage Enzyme; Cholesterol, LDL; Environmental Exposure; Goldfish; Industrial Waste; Lipoproteins; Male; Mitochondria; Phytosterols; Random Allocation; Reproduction; Sitosterols; Testis; Triglycerides; Trout; Water Pollutants, Chemical

2003
Stimulation of cholesterol excretion by the liver X receptor agonist requires ATP-binding cassette transporters G5 and G8.
    The Journal of biological chemistry, 2003, May-02, Volume: 278, Issue:18

    Liver X receptor (LXR) is a nuclear receptor that plays a crucial role in orchestrating the trafficking of sterols between tissues. Treatment of mice with a potent and specific LXR agonist, T0901317, is associated with increased biliary cholesterol secretion, decreased fractional cholesterol absorption, and increased fecal neutral sterol excretion. Here we show that expression of two target genes of LXRalpha, the ATP-binding cassette (ABC) transporters Abcg5 and Abcg8, is required for both the increase in sterol excretion and the decrease in fractional cholesterol absorption associated with LXR agonist treatment. Mice expressing no ABCG5 and ABCG8 (G5G8(-/-) mice) and their littermate controls were treated for 7 days with T0901317. In wild type animals, treatment with the LXR agonist resulted in a 3-fold increase in biliary cholesterol concentrations, a 25% reduction in fractional cholesterol absorption, and a 4-fold elevation in fecal neutral sterol excretion. In contrast, the LXR agonist did not significantly affect biliary cholesterol levels, fractional cholesterol absorption, or neutral fecal sterol excretion in the G5G8(-/-) mice. Thus Abcg5 and Abcg8 are required for LXR agonist-associated changes in dietary and biliary sterol trafficking. These results establish a central role for ABCG5 and ABCG8 in promoting cholesterol excretion in vivo.

    Topics: Animals; Anticholesteremic Agents; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile; Cholesterol; DNA-Binding Proteins; Feces; Hydrocarbons, Fluorinated; Lipoproteins; Liver; Liver X Receptors; Mice; Mice, Inbred C57BL; Orphan Nuclear Receptors; Receptors, Cytoplasmic and Nuclear; RNA, Messenger; Sitosterols; Sulfonamides

2003
Effect of beta-sitosterol on precipitation of cholesterol from non-aqueous and aqueous solutions.
    International journal of pharmaceutics, 2003, Mar-26, Volume: 254, Issue:2

    The aim of the present work was to study the solubility and phase behaviour of the beta-sitosterol-cholesterol mixed crystals in the presence and absence of water. Cholesterol, beta-sitosterol and 3:1, 1:1 and 1:3 mixtures of these were co-precipitated from acetone and acetone-water solutions. Precipitated crystals were analysed using powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), optical microscopy and Karl-Fischer titrimetry. The quantification of the sterols in solutions was preformed using GC-MS. The solubility of the sterols was mutually limiting. In the aqueous system, the solubility of both the sterols were significantly lower than in the absence of water, but the decrease in the solubility was considerably greater with the more hydrophobic beta-sitosterol. In the aqueous system, the total sterol solubility decreased with the increasing proportion of beta-sitosterol. The formation of new crystal structures, solid solutions of cholesterol and beta-sitosterol, was observed in non-aqueous as well as in aqueous environments except with the lowest cholesterol proportion in the system, in which case mixed crystals with eutectic behaviour were formed.

    Topics: Acetone; Calorimetry, Differential Scanning; Chemical Precipitation; Cholesterol; Crystallization; Gas Chromatography-Mass Spectrometry; Sitosterols; Solubility; Solutions; Titrimetry; Water; X-Ray Diffraction

2003
Clionasterol: a potent inhibitor of complement component C1.
    Planta medica, 2003, Volume: 69, Issue:2

    Clionasterol (1a), clionasterol monoacetate (1b) and 5alpha,8alpha-epidioxy-24alpha-ethylcholest-6-en-3-ol (2), isolated from the marine sponge Xestospongia exigua, and beta-sitosterol (3) were tested for their influence on the classical (CP) and alternative (AP) pathways of activation of the human complement system in vitro. All the sterols inhibited the CP in a dose-dependent manner but no detectable effect was observed in the AP even at concentrations of 400 microM. Clionasterol was found to be a potent inhibitor of CP (IC50 = 4.1 microM) being ten-fold more active than beta-sitosterol. The presence of the epidioxy group on C-5 and C-8 of compound 2 caused a pronounced decrease of the inhibitory effect. Mechanistic studies on the anticomplementary effect of clionasterol revealed that it interferes with the complement component C1.

    Topics: Animals; Complement Inactivator Proteins; Complement Pathway, Alternative; Complement Pathway, Classical; Dose-Response Relationship, Drug; Hemolysis; Humans; Inhibitory Concentration 50; Porifera; Sitosterols

2003
A general class of association tests for family-based data using weight functions.
    Genetic epidemiology, 2003, Volume: 24, Issue:3

    Based on the symmetry of transmitted/nontransmitted alleles from heterozygous parents under the null hypothesis of no association, the work proposed here establishes a general statistical framework for constructing association tests with data from nuclear families with multiple affected children. A class of association tests is proposed for both diallelic and multiallelic markers. The proposed test statistics reduce to the transmission disequilibrium test for trios, to T(su) by Martin et al. ([1997] Am. J. Hum. Genet. 61:439-448) for affected sib pairs, and to the pedigree disequilibrium test by Martin et al. ([2000] Am. J. Hum. Genet. 67:146-154); [2001] Am. J. Hum. Genet. 68:1065-1067) when using affected sibships only. The association test used in simulation and for real data (sitosterolemia) is the one which has the best overall power in detecting association. This association test is generally more powerful than the association tests proposed by Martin et al. ([2000] Am. J. Hum. Genet. 67:146-154); [2001] Am. J. Hum. Genet. 68:1065-1067) when using only affected sibships. For the sitosterolemia data set, the association test has its most significant result (P-value=0.0012) for the marker locus on the same bacterial artificial chromosome as the disease locus.

    Topics: Alleles; Genotype; Humans; Linkage Disequilibrium; Models, Genetic; Models, Statistical; Nuclear Family; Pedigree; Phenotype; Sitosterols

2003
Effect of phytosterols on cholesterol metabolism and MAP kinase in MDA-MB-231 human breast cancer cells.
    The Journal of nutritional biochemistry, 2003, Volume: 14, Issue:2

    Epidemiological studies suggest that dietary phytosterols may offer protection form some types of cancer including breast cancer. In an attempt to investigate the mechanism by which phytosterols offer this protection, we investigated the effect of the two most common dietary phytosterols, beta-sitosterol and campesterol, on the mevalonate and MAP Kinase (MAPK) pathways in MDA-MB-231 cells. These pathways play a role in cell growth and apoptosis. MDA-MB-231 cell line was used in this study since it is a hormone-insensitive tumor cell line which represents the majority of advanced breast cancer cases. Cells grown in the presence of 16 microM beta-sitosterol or campesterol for 3 days exhibited a 70% and 6% reduction in cell growth, respectively, while cholesterol treatment had no effect on growth as compared to the control. Studies investigating the effect of sterol supplementation on the relative and total sterol composition of cells, showed that cells supplemented with cholesterol contained 23% more cholesterol than the control. Cells supplemented with campesterol had almost one-half the cholesterol of controls but accumulated campesterol to account for 40% of the total sterols. In the case of cells supplemented with beta-sitosterol, cells had only 25% of their sterols as cholesterol and the rest was in the form of beta-sitosterol. All sterols tested equally inhibited de novo cholesterol synthesis using 14C-acetate as substrate. beta-Sitosterol supplemented cells had reduced cholesterol synthesis when using 3H-mevalonolactone as substrate, which suggests that the inhibition in this pathway is downstream of mevalonate where processes such as isoprenylation of proteins may take place. Mevalonate supplementation to cells treated with beta-sitosterol did not completely correct the observed growth inhibition by beta-sitosterol. There was no effect of sterols on the concentrations of both low (21-26 kDa) or high (44-74 kDa) molecular weight isoprenylated proteins in these cells. On the other hand, both the quantity and activity of MAPK was elevated in the cells supplemented with beta-sitosterol. These data suggest that the down regulation of cholesterol synthesis from mevalonate and stimulation of the MAPK pathway may play roles in the inhibition of MDA-MB-231 cell growth by beta-sitosterol.

    Topics: Breast Neoplasms; Cell Division; Cholesterol; Humans; Mevalonic Acid; Mitogen-Activated Protein Kinases; Phytosterols; Protein Prenylation; Sitosterols; Tumor Cells, Cultured

2003
Comparison of the contents of the main biochemical compounds and the antioxidant activity of some Spanish olive oils as determined by four different radical scavenging tests.
    The Journal of nutritional biochemistry, 2003, Volume: 14, Issue:3

    The aim of this study was to compare the contents of the main biochemical compounds and the antioxidant capacity of five Spanish olive oils by four different antioxidant tests and to find out the most valuable oil for disease preventing diets. Fatty acids, sterols and individual antioxidant compounds in Arbequina, Hojiblanca, Extra Virgin, Picual and Lampante Spanish olive oils were determined. Antioxidant activities were done as well using different radical scavenging activities: total radical-trapping antioxidative potential by ABAP (TRAP-ABAP), radical scavenging activity by DPPH (RSA-DPPH), antioxidant assay by beta-carotene-linoleate model system (AA-beta-carotene) and total antioxidant status by ABTS (TAA-ABTS). The highest content of all studied antioxidant compounds (353; 329; 4.6 and 2.7 mg/kg for tocopherols, tocotrienols, polyphenols and o-diphenols, respectively) was found in Extra Virgin oil. Also the highest antioxidant capacity was observed in Extra Virgin oil (668 nM/ml; 29.4%; 40.4% and 2.64 mM TE/kg for TRAP-ABAP, RSA-DPPH, AA- beta-carotene and TAA-ABTS, respectively). The correlation between total phenols and antioxidant capacities measured by four methods was very high, but the highest for the beta-carotene (R = 0.9958). In conclusion, the best method for determination of the antioxidant capacity of olive oils is the beta-carotene test. Extra Virgin olive oil has high organoleptic properties and the highest antioxidant activity. The above-mentioned makes this oil a preferable choice for diseases preventing diets.

    Topics: alpha-Linolenic Acid; Antioxidants; Cholesterol; Fatty Acids, Monounsaturated; Flavonoids; Free Radical Scavengers; Linoleic Acid; Myristic Acid; Oleic Acid; Olive Oil; Palmitic Acid; Phenols; Phytosterols; Plant Oils; Polymers; Polyphenols; Sitosterols; Spain; Stearic Acids

2003
Nonspecific lipid-transfer protein genes expression in grape (Vitis sp.) cells in response to fungal elicitor treatments.
    Molecular plant-microbe interactions : MPMI, 2003, Volume: 16, Issue:5

    Nonspecific lipid transfer proteins (nsLTPs) are small, basic cystein-rich proteins believed to be involved in plant defense mechanisms. Three cDNAs coding nsLTPs from grape (Vitis vinifera sp.) were cloned by reverse-transcriptase-polymerase chain reaction (RT-PCR) and PCR. The expression of nsLTP genes was investigated in 41B-rootstock grape cell suspension, in response to various defense-related signal molecules. Ergosterol (a fungi-specific sterol) and a proteinaceous elicitor purified from Botrytis cinerea strongly and rapidly induced the accumulation of nsLTP mRNAs. Jasmonic acid, cholesterol, and sitosterol also promoted nsLTPs mRNA accumulation, although to a lesser extent, whereas salicylic acid had no effect. High performance liquid chromatography analysis indicated that the amounts of three LTP isoforms (previously named P1, P2, and P4) were increased by ergosterol. None of the four isoforms displayed any significant antifungal properties, with the exception of the P4 isoform, which reduced Botrytis mycelium growth in vitro, but only in calcium-free medium. The results are discussed in the context of plant-pathogen interactions.

    Topics: Amino Acid Sequence; Botrytis; Carrier Proteins; Cells, Cultured; Cholesterol; Cloning, Molecular; Cyclopentanes; DNA, Complementary; Ergosterol; Gene Expression Regulation, Plant; Molecular Sequence Data; Oxylipins; Plant Diseases; Plant Proteins; Protein Isoforms; Salicylic Acid; Sequence Analysis, DNA; Sequence Homology, Amino Acid; Sitosterols; Vitis

2003
Sitosterolaemia and xanthomatosis in a child.
    Hong Kong medical journal = Xianggang yi xue za zhi, 2003, Volume: 9, Issue:3

    A 4-year-old boy presented with multiple tuberous xanthomata and a fasting plasma sterol concentration of 18.3 mmol/L, consisting primarily of cholesterol. Two months after changing from an unrestricted diet to a cholesterol-lowering diet, the plasma sterol concentration decreased to 4 mmol/L. Fasting plasma cholesterol levels for his father and mother were 7.3 mmol/L and 6.0 mmol/L, respectively. The degree and rapidity of the child's response to dietary control, together with the fasting cholesterol results of both parents suggested a diagnosis of sitosterolaemia. Gas chromatography and mass spectrometry of the patient's plasma sterol levels showed that the percentage of beta-sitosterol was raised at 12.76%, as was campesterol (6.26%), and stigmasterol (0.71%), confirming the diagnosis of sitosterolaemia. The addition of cholestyramine 4 g/day to a low sterol diet maintained the plasma sterol concentration at 4 to 5 mmol/L, and gradual regression of the xanthoma was observed. These findings indicate that a diagnosis of sitosterolaemia, a treatable cause of premature atherosclerosis, should be considered in children with severe hypercholesterolaemia whose plasma cholesterol level is highly responsive to dietary manipulation.

    Topics: Child, Preschool; Cholesterol; Humans; Male; Sitosterols; Xanthomatosis

2003
Effects of various amounts of dietary plant sterol esters on plasma and hepatic sterol concentration and aortic foam cell formation of cholesterol-fed hamsters.
    Atherosclerosis, 2003, Volume: 169, Issue:1

    Dietary intake of plant sterol esters (PSE) lowers plasma LDL-cholesterol (LDL-C), but can modestly increase plasma plant sterol concentrations. The objective of the present study was to investigate the impact of increasing doses of dietary PSE on plasma and liver sterol concentrations as well as on aortic foam cell development as a marker of atherogenesis. One-hundred and twenty F(1)B hybrid Syrian golden hamsters (20 per group) were fed a basal atherogenic diet containing 30% of energy as fat and 0.12% (w/w) cholesterol and supplemented with 0, 0.24, 0.48, 0.96, 1.92 and 2.84% (w/w) PSE. After 12 weeks, plasma total cholesterol (TC) and LDL-C were significantly lower in the groups fed PSE compared with control. Plasma plant sterol concentrations increased with increasing dietary PSE intake up to the dietary level of 1.92% and then reached a plateau. On the other hand, hepatic campesterol and sitosterol concentrations plateaued at 0.24% PSE. Foam cell presence in the aortic arch showed an inverse relationship with dietary PSE intake (P<0.0001). Lipid-filled foam cell areas of hamsters receiving 0.24, 0.48 or 2.84% PSE were approximately 70, 90 and 100% smaller than in control hamsters fed no PSE. In summary, dietary PSE lowered plasma TC and LDL-C. Despite an increase in plasma plant sterol concentrations they did not contribute to aortic foam cell development. In fact dietary PSE significantly inhibited aortic foam cell formation. This study supports the concept that PSE through their cholesterol-lowering action prevent development of atherogenesis in this animal model.

    Topics: Animals; Aorta; Cholesterol; Cholesterol, Dietary; Cholesterol, LDL; Cricetinae; Diet, Atherogenic; Endothelium, Vascular; Foam Cells; Liver; Male; Mesocricetus; Phytosterols; Sitosterols

2003
Physical stability of a microcrystalline beta-sitosterol suspension in oil.
    European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 2003, Volume: 19, Issue:4

    Sterols have been shown to reduce plasma cholesterol by blocking the absorption of cholesterol from the gut. The physical properties of crystalline plant sterols limit their use in foods. A coarse-grained structure can be avoided by recrystallisation, a method that affords a reduction in the particle size. A previous work described how to produce a microcrystalline beta-sitosterol suspension. The present study deals with the stability of that suspension. Recrystallisation was carried out by two different methods; one based on rapid the other based on slow cooling, whereby six different compositions were made containing 5-30% of beta-sitosterol and secondly either 5 or 20% water was added. The particle size and habit were evaluated during a 16 weeks storage period (+4 or -19 degrees C) by way of optical microscopy. The crystal structure and degree of crystallinity was analysed by X-ray diffraction. Suspensions can, in most cases, be stored for 16 weeks without any changes to the size and habit. The only evidence of crystal growth came from a suspension with a low sterol concentration at a temperature of +4 degrees C. This is due to the dissolution-diffusion process which is affected by temperature and viscosity. Suspensions containing higher amounts of sterol remained stable, if stored at +4 or -19 degrees C, for 16 weeks. The suspensions included both hemihydrous and monohydrous beta-sitosterol crystals. Suspensions containing less sterol showed greater amounts of monohydrated crystals. This illustrates more water penetration into the crystals. A higher sterol concentration led to a larger number of smaller crystals creating reflections similar to hemihydrated crystals.

    Topics: Cholesterol; Drug Stability; Hypolipidemic Agents; Phytosterols; Sitosterols; Soil; Suspensions; Time Factors; Viscosity; Water; X-Ray Diffraction

2003
Characterization of sterol uptake in leaf tissues of sugar beet.
    Planta, 2003, Volume: 218, Issue:2

    The uptake of cholesterol has been characterized in leaf discs from mature leaves of sugar beet ( Beta vulgaris L.). This transport system exhibited a simple saturable phase with an apparent Michaelis constant ranging from 30 to 190 microM depending on the sample. When present at 10 M excess, other sterols were able to inhibit cholesterol uptake. Moreover, binding assays demonstrated the presence of high-affinity binding sites for cholesterol in purified plasma membrane vesicles. In the range 1-60 microM, cholesterol uptake showed an active component evidenced by action of the protonophore carbonyl cyanide m-chlorophenylhydrazone. Energy was required as shown by the inhibition of uptake induced by respiration inhibitors (NaN(3)), darkness and photosynthesis inhibitors [3-(3,4-dichlorophenyl)-1,1-dimethylurea, methyl viologen]. Moreover, the process was strongly dependent on the experimental temperature. Uptake was optimal at acidic pH (4.0), sensitive to ATPase modulators, inhibited by thiol reagents (N-ethylmaleimide, p-chloromercuribenzenesulfonic acid, Mersalyl) and by the histidyl-group reagent diethyl pyrocarbonate. The addition of cholesterol did not modify H(+) flux from tissues, indicating that H(+)-co-transport was unlikely to be involved. MgATP did not increase the uptake, arguing against involvement of an ABC cassette-type transporter. By contrast, cryptogein, a sterol carrier protein from the Oomycete Phytophtora cryptogea, greatly increased absorption. Taken together, the results reported in this work suggest that plant cells contain a specific plasma membrane transport system for sterols.

    Topics: Adenosine Triphosphatases; Beta vulgaris; Binding Sites; Binding, Competitive; Cholesterol; Dose-Response Relationship, Drug; Drug Antagonism; Ergosterol; Glycosides; Hydrogen-Ion Concentration; Plant Leaves; Sitosterols; Stigmasterol; Sulfhydryl Compounds; Temperature; Time Factors

2003
Analysis of plant sterol and stanol esters in cholesterol-lowering spreads and beverages using high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectroscopy.
    Journal of agricultural and food chemistry, 2003, Sep-10, Volume: 51, Issue:19

    Plant sterol and stanol esters were separated on a Luna hexyl-phenyl column using a gradient of acetonitrile (90-100%) in water. The eluted compounds were detected by atmospheric pressure chemical ionization (APCI)-mass spectroscopy (MS) in the positive mode. Sterol and stanol esters produced [M + H - HOOCR](+) ions. Application of the hyphenated technique-LC-MS-allowed differentiation between a number of esters of sitosterol, campesterol, stigmasterol, and (tentatively) avenasterol, as well as sitostanol and campestanol esters. With cholesteryl decanoate used as the internal standard, the method showed good linearity, precision, and reproducibility. The method required minimal sample pretreatment and can be applied to samples with high water content (juices) as well as samples with high oil content (margarine spreads). The method could be useful for the analysis of sterol and stanol esters in fortified food products.

    Topics: Anticholesteremic Agents; Beverages; Cholesterol; Chromatography, High Pressure Liquid; Citrus; Esters; Fruit; Margarine; Mass Spectrometry; Phytosterols; Sensitivity and Specificity; Sitosterols; Stigmasterol

2003
Compared with Acyl-CoA:cholesterol O-acyltransferase (ACAT) 1 and lecithin:cholesterol acyltransferase, ACAT2 displays the greatest capacity to differentiate cholesterol from sitosterol.
    The Journal of biological chemistry, 2003, Nov-28, Volume: 278, Issue:48

    The capacity of acyl-CoA:cholesterol O-acyltransferase (ACAT) 2 to differentiate cholesterol from the plant sterol, sitosterol, was compared with that of the sterol esterifying enzymes, ACAT1 and lecithin:cholesterol acyltransferase (LCAT). Cholesterol-loaded microsomes from transfected cells containing either ACAT1 or ACAT2 exhibited significantly more ACAT activity than their sitosterol-loaded counterparts. In sitosterol-loaded microsomes, both ACAT1 and ACAT2 were able to esterify sitosterol albeit with lower efficiencies than cholesterol. The mass ratios of cholesterol ester to sitosterol ester formed by ACAT1 and ACAT2 were 1.6 and 7.2, respectively. Compared with ACAT1, ACAT2 selectively esterified cholesterol even when sitosterol was loaded into the microsomes. To further characterize the difference in sterol specificity, ACAT1 and ACAT2 were compared in intact cells loaded with either cholesterol or sitosterol. Despite a lower level of ACAT activity, the ACAT1-expressing cells esterified 4-fold more sitosterol than the ACAT2 cells. The data showed that compared with ACAT1, ACAT2 displayed significantly greater selectively for cholesterol compared with sitosterol. The plasma cholesterol esterification enzyme lecithin:cholesterol acyltransferase was also compared. With recombinant high density lipoprotein particles, the esterification rate of cholesterol by LCAT was only 15% greater than for sitosterol. Thus, LCAT was able to efficiently esterify both cholesterol and sitosterol. In contrast, ACAT2 demonstrated a strong preference for cholesterol rather than sitosterol. This sterol selectivity by ACAT2 may reflect a role in the sorting of dietary sterols during their absorption by the intestine in vivo.

    Topics: 2-Hydroxypropyl-beta-cyclodextrin; Animals; beta-Cyclodextrins; Cell Line; Chlorocebus aethiops; Cholesterol; Cyclodextrins; Esters; Lipoproteins, HDL; Mice; Microsomes; Phosphatidylcholines; Recombinant Proteins; Sitosterols; Sterol O-Acyltransferase; Sterol O-Acyltransferase 2; Time Factors; Transfection

2003
Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells.
    The British journal of nutrition, 2003, Volume: 90, Issue:4

    Phytosterols are plant sterols found in foods such as oils, nuts and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation. The objective of the present study was to assess the potential toxic effects of beta-sitosterol oxides on U937 cells. The effects of increasing concentrations (0-120 microm) of beta-sitosterol oxides on cellular cytotoxicity, apoptosis, antioxidant status and genotoxicity was assessed over 12, 24 and 48 h exposure periods. Following 12 h, the viability of cells treated with 120 microm-beta-sitosterol oxides was reduced to 51.7 % relative to control. At 24 and 48 h, both 60 and 120 microm-beta-sitosterol oxides caused a significant decrease in cell viability. For comparison, a decrease in viability of cells treated with a cholesterol oxide, 7beta-hydroxycholesterol (7beta-OH, 30 microm), was evident at 24 h. An increase in apoptotic cells, assessed using Hoechst 33342, indicates that the mode of cell death in U937 cells following exposure to 7beta-OH (30 microm) and beta-sitosterol oxides (60 and 120 microm) was by apoptosis. The increase in apoptotic cells after 12 h following treatment with 120 microm-beta-sitosterol oxides was accompanied by a decrease in cellular glutathione. Similarly, 7beta-OH (30 microm) treatment resulted in decreased glutathione at 12 h. Catalase activity was not affected by any of the treatments. beta-Sitosterol oxides had no genotoxic effects on U937 and V79 cells as assessed by the comet and sister chromatid exchange assays respectively. In general, the results indicate that thermally oxidised derivatives of beta-sitosterol demonstrate similar biological effects as 7beta-OH in U937 cells, but at higher concentrations.

    Topics: Antioxidants; Apoptosis; Catalase; Chromatography, Thin Layer; DNA Fragmentation; Glutathione; Humans; Hypolipidemic Agents; Mutation; Oxidation-Reduction; Sister Chromatid Exchange; Sitosterols; U937 Cells

2003
ABCG5 and ABCG8 are obligate heterodimers for protein trafficking and biliary cholesterol excretion.
    The Journal of biological chemistry, 2003, Nov-28, Volume: 278, Issue:48

    ABCG5 (G5) and ABCG8 (G8) are ATP-binding cassette (ABC) transporters that limit intestinal absorption and promote biliary excretion of neutral sterols. Mutations in either ABCG5 or ABCG8 result in an identical clinical phenotype, suggesting that these two half-transporters function as heterodimers. Expression of both G5 and G8 is required for either protein to be transported to the plasma membrane of cultured cells. In this paper we used immunofluorescence microscopy to confirm, in vivo, that G5 is localized to the apical membranes of mouse enterocytes and hepatocytes. Other ABC half-transporters function as homodimers or as heterodimers with other subfamily members. To determine whether G5 or G8 complex with other ABCG half-transporters, we co-expressed G1, G2, and G4 with either G5 or G8 in cultured cells. G1, G2, and G4 co-immunoprecipitated with G5, and G4 co-immunoprecipitated with G8, but the putative dimers were retained in the endoplasmic reticulum (ER). Adenovirus-mediated expression of either G5 or G8 in the liver of G5G8 null mice resulted in ER retention of the expressed proteins and no increase in biliary cholesterol. In contrast, co-expression of G5 and G8 resulted in transit of the proteins out of the ER and a 10-fold increase in biliary cholesterol concentration. Finally, adenoviral expression of G2 in the presence or absence of G5 or G8 failed to promote sterol excretion into bile. These experiments indicate that G5 and G8 function as obligate heterodimers to promote sterol excretion into bile.

    Topics: Adenosine Triphosphate; Adenoviridae; Amino Acid Sequence; Animals; Antibodies, Monoclonal; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile Ducts; Biological Transport; Cell Membrane; CHO Cells; Cholesterol; Cloning, Molecular; Cricetinae; Dimerization; DNA, Complementary; Endoplasmic Reticulum; Enterocytes; Epitopes; Evolution, Molecular; Hepatocytes; Humans; Hypolipidemic Agents; Lipoproteins; Liver; Mice; Microscopy, Fluorescence; Molecular Sequence Data; Mutation; Phenotype; Phylogeny; Phytosterols; Precipitin Tests; Protein Transport; Recombinant Proteins; Sequence Homology, Amino Acid; Sitosterols; Transfection

2003
Effect of olive oil minor components on oxidative stress and arachidonic acid mobilization and metabolism by macrophages RAW 264.7.
    Free radical biology & medicine, 2003, Nov-01, Volume: 35, Issue:9

    Minor components of virgin olive oil may explain the healthy effects of the Mediterranean diet on the cardiovascular system and cancer development. The uncontrolled production of reactive oxygen species (ROS) and arachidonic acid (AA) metabolites contributes to the pathogenesis of cardiovascular disease and cancer, and inflammatory cells infiltrated in the atheroma plaque or tumor are a major source of ROS and eicosanoids. We aimed to determine the effects of squalene, beta-sitosterol, and tyrosol, which are representative of the hydrocarbons, sterols, and polyphenols of olive oil, respectively, on superoxide anion (O2(-)), hydrogen peroxide (H2O2), and nitric oxide (*NO) levels. We also studied AA release and eicosanoid production by phorbol esters (PMA)-stimulated macrophages RAW 264.7. beta-Sitosterol and tyrosol decreased the O2(-) and H2O2 production induced by PMA, and tyrosol scavenged the O2(-) released by a ROS generating system. These effects were correlated with the impairment of [3H]AA release, cyclooxygenase-2 (COX-2) expression, and prostaglandin E(2)/leukotriene B(4) synthesis in RAW 264.7 cultures stimulated by PMA. beta-Sitosterol exerted its effects after 3-6 h of preincubation. Tyrosol inhibited the [3H]AA release induced by exogenous ROS. beta-Sitosterol and tyrosol also reduced the *NO release induced by PMA, which was correlated with the impairment of inducible nitric oxide synthase (iNOS) levels. This may be correlated with the modulation of NF-kappaB activation. Further studies are required to gain more insight into the potential healthy effects of minor components of extra virgin olive oil.

    Topics: Animals; Arachidonic Acid; Cell Line; Cyclooxygenase 2; Dinoprostone; Hydrogen Peroxide; Isoenzymes; Leukotriene B4; Macrophages; Mice; NF-kappa B; Nitric Oxide; Nitric Oxide Synthase; Nitric Oxide Synthase Type II; Olive Oil; Oxidative Stress; Phenylethyl Alcohol; Plant Oils; Prostaglandin-Endoperoxide Synthases; Reactive Oxygen Species; Sitosterols; Squalene; Superoxides; Tetradecanoylphorbol Acetate

2003
Kimchi and an active component, beta-sitosterol, reduce oncogenic H-Ras(v12)-induced DNA synthesis.
    Journal of medicinal food, 2003,Fall, Volume: 6, Issue:3

    The Korean fermented vegetable food, kimchi, has been demonstrated to have anticancer functional properties. This study examined the effect of kimchi samples, methanol extracts of commercially grown baechu cabbage kimchi (CK) and organically grown baechu cabbage kimchi (OK), as well as the dichloromethane fraction (DCM fr.) from CK, and the active compound (AC), which has been identified as largely beta-sitosterol, from DCM fr., on the Ras-dependent signaling pathway. CK, OK, and DCM fr. exhibited a greater inhibition against the proliferation of Rat2 fibroblasts transformed with Ras(v12) (HO6) than parental Rat2 fibroblasts. In addition, OK and DCM fr. showed a higher inhibitory effect than CK. Furthermore, we employed the single-cell microinjection technique, combined with 3-bromo-5'-deoxyuridine incorporation, to examine the effects of kimchi samples on DNA synthesis induced by microinjected oncogenic Ras(v12). When the DCM fr. and AC were used to treat Rat1 fibroblasts overexpressing human insulin receptors (HIRc-B) and microinjected with oncogenic H-Ras(v12), the DNA synthesis of injected cells was decreased, suggesting that kimchi might block the signaling pathway of oncogenic Ras(v12), thus preventing the proliferation of transformed cells. This study provides additional evidence that kimchi and its active components, including beta-sitosterol, have potential in both the prevention and treatment of cancer, and presents convincing evidence that the anticancer effects may be a result of an inhibition of Ras oncogene signaling.

    Topics: Animals; Anticarcinogenic Agents; Brassica; Cell Line; Cell Line, Transformed; Cell Survival; DNA; Fermentation; Fibroblasts; Genes, ras; Microinjections; Microscopy, Fluorescence; ras Proteins; Rats; Signal Transduction; Sitosterols; Transcriptional Activation; Transfection

2003
Antioxidant effects of phytosterol and its components.
    Journal of nutritional science and vitaminology, 2003, Volume: 49, Issue:4

    Phytosterol contained in vegetable oils is known to exert a hypocholesterolemic function. In the present study, the antioxidant effects of phytosterol and its components, beta-sitosterol, stigmasterol, and campesterol, against lipid peroxidation were examined by making a comparison with 2,2,5,7,8-pentamethyl-6-chromanol (PMC). It was found that these compounds exerted antioxidant effects on the oxidation of methyl linoleate in solution and its effect decreased in the order of: PMC >> phytosterol approximately campesterol approximately beta-sitosterol > stigmasterol. Phytosterol also suppressed the oxidation and consumption of alpha-tocopherol in beta-linoleoyl-gamma-palmitoyl phosphatidylcholine (PLPC) liposomal membranes, the effects being more significant than dimyristoyl PC of the same concentration. Stigmasterol accelerated the oxidation of both methyl linoleate in solution and PLPC liposomal membranes in aqueous dispersions, which was ascribed to the oxidation of allylic hydrogens at the 21- and 24-positions. Taken together, the present study shows that phytosterol chemically acts as an antioxidant, a modest radical scavenger, and physically as a stabilizer in the membranes.

    Topics: Anticholesteremic Agents; Antioxidants; Cholesterol; Chromans; Free Radical Scavengers; Lipid Peroxidation; Liposomes; Membranes, Artificial; Oxidation-Reduction; Phytosterols; Sitosterols; Stigmasterol

2003
Induction of Bax and activation of caspases during beta-sitosterol-mediated apoptosis in human colon cancer cells.
    International journal of oncology, 2003, Volume: 23, Issue:6

    beta-sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. The purpose of the present study was to examine the effect of beta-sitosterol on the growth of HT116 human colon cancer cells. Treatment with beta-sitosterol resulted in a dose-dependent growth inhibition coupled with the characteristic morphological features of apoptosis and with the increase of a sub-G1 cell population. Apoptosis-inducing concentrations of beta-sitosterol induced caspase-3 and caspase-9 activation accompanied by proteolytic cleavage of poly(ADP-ribose)-polymerase. In addition, beta-sitosterol-induced apoptosis in HT116 cells was associated with a decreased expression of the anti-apototic Bcl-2 protein and mRNA and a concomitant increase of the pro-apototic Bax protein and mRNA, and with release of cytochrome c from the mitochondria into the cytosol. beta-sitosterol treatment also inhibited the expression of cIAP-1 without significant changes in the level of cIAP-2. Taken together, these findings provide important new insights into the possible molecular mechanisms of the anti-cancer activity of beta-sitosterol.

    Topics: Antineoplastic Agents; Apoptosis; bcl-2-Associated X Protein; Caspase 3; Caspase 9; Caspases; Cell Line, Tumor; Cell Survival; Dose-Response Relationship, Drug; Enzyme Activation; Flow Cytometry; Humans; Hypolipidemic Agents; Immunoblotting; Poly(ADP-ribose) Polymerases; Proto-Oncogene Proteins; Proto-Oncogene Proteins c-bcl-2; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Sitosterols

2003
Optimizing the crystal size and habit of beta-sitosterol in suspension.
    AAPS PharmSciTech, 2003, Volume: 4, Issue:3

    The aim of this work was to survey how processing parameters affect the crystal growth of beta-sitosterol in suspension. The process variables studied were the cooling temperature, stirring time and stirring rate during recrystallization. In addition, we investigated the effect a commonly used surfactant, polysorbate 80, has on crystal size distribution and the polymorphic form. This study describes the optimization of the crystallization process, with the object of preparing crystals as small as possible. Particle size distribution and habit were analyzed using optical microscopy, and the crystal structure was analyzed using X-ray diffractometry. The cooling temperature had a remarkable influence on the crystal size. Crystals with a median crystal length of approximately 23 microm were achieved with a low cooling temperature (<10 degrees C); however, a fairly large number of crystals over 50 microm appeared. Higher cooling temperatures (>30 degrees C) caused notable crystal growth both in length and width. Rapid (250 rpm), continuous stirring until the suspensions had cooled to room temperature created small, less than 50 micro m long (median <20 microm), needle-shaped crystals. The addition of surfactant slightly reduced the size of the initially large crystals. Both hemihydrate and monohydrate crystal forms occurred throughout, regardless of the processing parameters. By using an optimized process, it was possible to obtain a microcrystalline suspension, with a smooth texture.

    Topics: Chemistry, Pharmaceutical; Cold Temperature; Crystallization; Particle Size; Sitosterols; Surface-Active Agents; Suspensions; Temperature; Time Factors; X-Ray Diffraction

2003
In vivo implants of beta-sitosterol cause reductions of reactive cholesterol pools in mitochondria isolated from gonads of male goldfish (Carassius auratus).
    General and comparative endocrinology, 2003, Volume: 134, Issue:3

    beta-Sitosterol, a phytosterol found in high concentrations in pulp mill effluents, has been proposed as one of the causative agents for steroid depressions observed in fish exposed to pulp mill effluents. Previous studies have suggested a cholesterol-mediated mechanism; however, it is unknown how beta-sitosterol depresses gonadal steroidogenesis. In this study, adult male goldfish (Carassius auratus) were exposed for 24-31 days to beta-sitosterol (55% of a phytosterol mixture or 96% pure; 150 microg/g; Silastic implant) after which gonadal mitochondria were isolated. Pregnenolone production, an indicator of the size of the pool of reactive cholesterol, was then measured in the isolated mitochondria. Sterol exposure did not affect P450 side-chain cleavage enzyme (converts cholesterol to pregnenolone) activity but did decrease the size of the mitochondrial pool of reactive cholesterol, suggesting beta-sitosterol is impeding cholesterol transfer across the mitochondrial membrane. This finding is supported by the observation that 25-hydroxycholesterol, which passes through mitochondrial membranes without need for a membrane transporter, restores beta-sitosterol-induced reductions in pregnenolone production.

    Topics: Animals; Biological Transport; Cholesterol; Goldfish; Hypolipidemic Agents; Male; Mitochondria; Pregnenolone; Sitosterols; Testis

2003
Inhibition of sortase, a bacterial surface protein anchoring transpeptidase, by beta-sitosterol-3-O-glucopyranoside from Fritillaria verticillata.
    Bioscience, biotechnology, and biochemistry, 2003, Volume: 67, Issue:11

    A glucosylsterol, beta-sitosterol-3-O-glucopyranoside, has been isolated as an active principle with sortase inhibitory effect from the bulbs of Fritillaria verticillata by bioassay-guided chromatographic fractionation. The isolate was a potent inhibitor of sortase, with an IC(50) value of 18.3 microg/ml and had antibacterial activity against Bacillus subtilis, Staphylococcus aureus, and Micrococcus leuteus with MIC values of 50, 200, and 400 microg/ml, respectively, indicating that this compound is a possible candidate for the development of a bacterial sortase inhibitor. In addition, sitosterol was found to be inactive upon sortase and bacterial cell growth. These results suggest that the inhibitory potency of beta-sitosterol-3-O-glucopyranoside is sensitively dependent upon the glucopyranoside side chain moiety.

    Topics: Aminoacyltransferases; Anti-Bacterial Agents; Bacillus subtilis; Bacterial Proteins; Cell Membrane; Cysteine Endopeptidases; Enzyme Inhibitors; Glucosides; Liliaceae; Microbial Sensitivity Tests; Micrococcus luteus; Peptidyl Transferases; Plant Roots; Sitosterols; Staphylococcus aureus

2003
Purification of gastroprotective triterpenoids from the stem bark of Amphipterygium adstringens; role of prostaglandins, sulfhydryls, nitric oxide and capsaicin-sensitive neurons.
    Planta medica, 2003, Volume: 69, Issue:10

    In this investigation three bioactive compounds, responsible for the gastroprotective property of Amphipterygium adstringens, were purified from an active dichloromethane fraction. These compounds were 3alpha-hydroxymasticadienonic acid, beta-sitosterol and 3- epi-oleanolic acid. The latter was the most active compound (88.8 % of gastroprotection) followed by 3alpha-hydroxymasticadienoic acid and beta-sitosterol (69.8 and 42.5 % of gastroprotection, respectively). Carbenoxolone was used as positive control and it showed 88.4 % of gastroprotection. Masticadienonic acid was also isolated from the active fraction, but it was unable to inhibit the ethanol-induced gastric lesions. The gastroprotection of the methanol extract was completely inhibited by the pretreatment with l-NAME and attenuated by pretreatment with indomethacin and N-ethylmaleimide. These results suggest that endogenous nitric oxide plays an important role in the gastroprotection of A. adstringens methanol extract on ethanol-induced gastric mucosal lesions and that there is partial participation by prostaglandins and endogenous sulfhydryls. The effect of 3alpha-hydroxymasticadienonic acid was attenuated only by pretreatment with N-ethylmaleimide, indicating that endogenous sulfhydryls (thiols) participate in its gastroprotective mechanism. Capsaicin-sensitive afferent neurons do not participate in the gastroprotection of either the methanol extract or 3alpha-hydroxymasticadienoic acid.

    Topics: Animals; Capsaicin; Dose-Response Relationship, Drug; Ethanol; Gastric Mucosa; Gastrointestinal Agents; Male; Neurons, Afferent; Nitric Oxide; Oleanolic Acid; Phytotherapy; Plant Extracts; Plant Stems; Plants, Medicinal; Prostaglandins; Rats; Rats, Wistar; Sitosterols; Stomach Ulcer; Sulfhydryl Compounds; Triterpenes

2003
Unraveling the mystery surrounding cholesterol's condensing effect.
    Journal of the American Chemical Society, 2003, Dec-31, Volume: 125, Issue:52

    The results of nearest-neighbor recognition experiments that have been carried out with exchangeable dimers derived from 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine, in the presence of cholesterol, dihydrocholesterol, coprostanol, cholestane, cholesteryl methy ether, and sitosterol, provide strong support for a condensing mechanism in which the flexible acyl chains of the phospholipids complement, perfectly, the shape of neighboring sterols, thereby leading to a high number of hydrophobic contacts and tight packing.

    Topics: Cholesterol; Hydrogen Bonding; Hydrophobic and Hydrophilic Interactions; Kinetics; Lipid Bilayers; Phospholipids; Sitosterols; Structure-Activity Relationship

2003
Effect of beta-sitosterol as inhibitor of 5 alpha-reductase in hamster prostate.
    Proceedings of the Western Pharmacology Society, 2003, Volume: 46

    Topics: 5-alpha Reductase Inhibitors; Animals; Binding, Competitive; Cricetinae; Dihydrotestosterone; Enzyme Inhibitors; Finasteride; Male; Mesocricetus; Orchiectomy; Organ Size; Prostate; Receptors, Androgen; Sitosterols

2003
[Chemical constituents of Cyanotis arachnoidea].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2003, Volume: 38, Issue:10

    To investigate the chemical constituents of Cyanotis arachnoidea.. By using chromatographic methods for separation and combination with spectral analysis, their chemical structures were determined.. Six compounds were identified as ajugasterone C-20, 22-acetonide (1), 20-hydroxyecdysone-20, 22-acetonide (2), 22-oxo-ajugasterone C (3), 22-oxo-20-hydroxyecdysone (4), beta-sitosterol (5), daucosterol (6).. Compound 3 is a new compound, 4 was a new natural compound.

    Topics: Commelinaceae; Ecdysone; Ecdysterone; Molecular Structure; Plants, Medicinal; Sitosterols

2003
Serum and aortic levels of phytosterols in rabbits fed sitosterol or sitostanol ester preparations.
    Lipids, 2003, Volume: 38, Issue:11

    Campesterol is present in all the phytosterol-containing dietary hypocholesterolemic agents in current use. Campesterol is absorbed more efficiently than sitosterol, and the question of its possible atherogenicity has been raised. To test this possibility, rabbits were fed either a semipurified, cholesterol-free diet that has been shown to be atherogenic for this species or the same diet augmented with 0.5 g of phytosterol-rich diet preparations (spreads) containing either sitosterol or sitostanol. The diets contained 295 mg phytosterol per 100 g. After 60 d, serum cholesterol levels in the two phytosterol groups were 78 +/- 4 mg/dL (sitosterol) and 76 +/- 4 mg/dL (sitostanol), respectively. The serum cholesterol level of rabbits fed the control diet was 105 +/- 8 mg/dL. Serum campesterol (microg/mL) levels were higher than sitosterol or sitostanol levels in all groups. Aortic phytosterols were present in nanogram quantities compared to cholesterol, which was present in microgram quantities. The ratio of campesterol/sitosterol/sitostanol in the aortas was: control, 1.00:0.43:0.02; sitosterol, 1:00:0.32:0.01; sitostanol, 1:00:0.34:0.11. Aortic campesterol was present at 4% the concentration of aortic cholesterol, sitosterol at 1.4%, and sitostanol at 0.14%. Aortic lesions were not present in any of the animals.

    Topics: Animals; Aorta; Cholesterol; Chromatography, Gas; Diet; Esters; Male; Phytosterols; Rabbits; Sitosterols; Weight Gain

2003
Effects of microcrystalline plant sterol suspension and a powdered plant sterol supplement on hypercholesterolemia in genetically obese Zucker rats.
    The Journal of pharmacy and pharmacology, 2003, Volume: 55, Issue:12

    Because dietary fat appears to be an effective vehicle for dispensing plant sterols into the diet, a special plant-sterol-containing ingredient has recently been developed. This ingredient is a plant sterol suspension in oil in which the sterols are in microcrystalline form. The objective of the present study was to analyse the cholesterol-lowering effects and safety of two different plant sterol preparations, an orally administered microcrystalline plant sterol suspension (MPS) in rapeseed oil and a powdered plant sterol supplement, in obese Zucker rats. Dietary plant sterol supplements (0.5%, w/w) were given concurrently with a high cholesterol diet (HCD, 1% cholesterol and 18% fat, w/w). No significant changes in serum triglyceride, blood glucose, serum glutamate oxaloacetic transaminase and glutamic pyruvic transaminase values or body and liver weights were observed. The powdered plant sterol supplement lowered the serum cholesterol by 25% (P < 0.05) and the MPS diet by 35% (P < 0.001) compared with HCD by the end of the 12-week experiment. Interestingly, the plant sterol supplements also produced a marked reduction in serum ubiquinone levels, suggesting a possible effect on isoprene synthesis. Unlike the powdered plant sterol, both MPS and plain rapeseed oil decreased the serum baseline diene conjugation values, suggesting that they protect against oxidative stress-induced lipid peroxidation in rats. This lipid peroxidation diminishing effect is probably due to some antioxidative components in rapeseed oil. These findings indicate that an unesterified plant sterol, such as the microcrystalline suspension in oil, effectively prevents cholesterol absorption in obese Zucker rats.

    Topics: Administration, Oral; Animals; Chemistry, Pharmaceutical; Cholesterol, Dietary; Fatty Acids, Monounsaturated; Female; Hypercholesterolemia; Hypolipidemic Agents; Intestinal Absorption; Lipid Peroxidation; Obesity; Phytosterols; Plant Oils; Powders; Rapeseed Oil; Rats; Rats, Zucker; Sitosterols

2003
Pfaffia paniculata-induced changes in plasma estradiol-17beta, progesterone and testosterone levels in mice.
    The Journal of reproduction and development, 2003, Volume: 49, Issue:2

    The present study undertook chemical analysis of components of Pfaffia paniculata roots. In addition, an animal experiment was conducted in which mice had ad libitum access to water enriched with powdered P. paniculata root for 30 days. Changes in plasma concentrations of estradiol-17beta and progesterone in female mice and of testosterone in male mice were ascertained. The results revealed that P. paniculata roots contain two types of phytosteroids, beta-sitosterol and stigmasterol, in addition to other compounds such as pfaffic acid, allantoin, saponins, beta-sitosteryl-beta-D-glucoside, and stigmasteryl-beta-D-glucoside. Regarding changes in plasma concentrations of hormones, levels of the sex hormones estradiol-17beta, progesterone and testosterone were clearly higher for mice that drank P. paniculata root-enriched water than for mice that drank plain water. Powdered P. paniculata root is easily dissolved in feed or water, and as no adverse reactions were seen in mice within 30 days of oral intake, consumption of P. paniculata for long periods of time appears safe.

    Topics: Amaranthaceae; Animals; Estradiol; Female; Male; Mice; Mice, Inbred ICR; Plant Extracts; Plant Roots; Progesterone; Sitosterols; Stigmasterol; Testosterone

2003
[Studies on chemical constituents in the peels of Citrus changshan-huyou (I)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:3

    To reveal the pharmacological activities of the components for their further utilization and development by studying the chemical constituents of Citrus changshan-huyou.. The structures were determined by repeated silica gel chromatographic separation and spectral analysis.. Five compounds were obtained, and identified as 3-oxo friedelin (I), limonin (II), beta-sitosterol (III), 8-(2',3'-dihydroxy-4'-methylbutane)-7-methoxycoumarin (IV), sucrose (V).. The five compounds were obtained from this plant for the first time.

    Topics: Citrus; Fruit; Limonins; Plants, Medicinal; Sitosterols; Sucrose

2003
[Studies on chemical constituents in herb of Lamium maculatum L. var Kansuense].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:8

    To study the chemical constituents from Lamium maculatum L. var Kansuense.. The chemical constituents were isolated and repeatedly purified by silica gel column chromatography and the structures were elucidated by the NMR spectra and physico-chemical properties.. Ten compounds were obtained and they were identified as D-mannitol, beta-sitosterol, stigmasterol, rutin, 3'-methylquercetin-3-O-rutinoside, n-butyl-beta-D-fructopyranoside, daucosterol, acteoside, 20-hydroxyecdysone, allantoin.. All the compounds were obtained from L. maculatum L. var Kansuense for the first time.

    Topics: Allantoin; Ecdysterone; Glucosides; Lamiaceae; Mannitol; Phenols; Plants, Medicinal; Rutin; Sitosterols; Stigmasterol

2003
[Chemical constituents of Geranium eristemon].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:7

    To study the chemical constituents of Geranium eristemon.. Chromatography and spectral analysis were used to isolate the constituents and elucidate their structures.. Five compounds were isolated from acetone extract of the whole grass of G. eristemon, and identified as beta-sitosterol, protocatechuic acid, myricetin, kaempferol-7-O-alpha-L-arabifuranoside and kaempferol-3-O-alpha-L-arabifuranoside.. kaempferol-7-O-alpha-L-arabifuranoside and kaempferol-3-O-alpha-L-arabifuranoside were isolated from G. genus for the first time.

    Topics: Arabinose; Flavonoids; Geranium; Hydroxybenzoates; Kaempferols; Plants, Medicinal; Sitosterols

2003
[An experimental study(II) on the inhibition of prostatic hyperplasia by extract of seeds of Brassica alba].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:7

    To study the active components and their functionary mechanism of the extract of Brassica alba seeds, which inhibits experimental mice prostatic hyperplasia.. Prostatic hyperplasia of castrated male mice induced by testosterone propionate, the penetrability of capillary vessel of mice skin induced by histamine and the endermic flesh bud of rat induced by filter paper were used as experimental models. Sinalbin and beta-sitosterol separated from seeds of Brassica alba were used to test the activities.. Sinalbin and beta-sitosterol(16.0 mg.kg-1.d-1 and 8.0 mg.kg-1.d-1) could significantly inhibit mice prostatic hyperplasia induced by testosterone propionate and activity of serum acid phosphatase(P < 0.01 or P < 0.05), Sinalbin(16.0 mg.kg-1.d-1)could significantly inhibit the hyperplasia of endermic flesh bud in rat induced by filter paper(P < 0.05), beta-sitosterol(16.0 mg.kg-1.d-1 and 8.0 mg.kg-1.d-1) could significantly decrease the penetrability of capillary vessel of mice skin induced by histamine.. Sinalbin and beta-sitosterol have anti-androgen and anti-inflammation activities.

    Topics: Androgen Antagonists; Animals; Anti-Inflammatory Agents, Non-Steroidal; Capillary Permeability; Choline; Female; Male; Mice; Mustard Plant; Orchiectomy; Plants, Medicinal; Prostatic Hyperplasia; Rats; Rats, Sprague-Dawley; Seeds; Sitosterols; Testosterone Propionate

2003
Amaranth as a rich dietary source of beta-sitosterol and other phytosterols.
    Plant foods for human nutrition (Dordrecht, Netherlands), 2003, Volume: 58, Issue:3

    The analysis of 4 commonly available amaranth varieties (Amaranthus K343, RRC1011, K433, K432) revealed the presence of all three major phytosterols (beta-sitosterol, campesterol, stigmas-terol) with a total sterol content being several fold higher than those found in other studied plants. Substantial differences in total phytosterol content and beta-sitosterol content were found between the amaranth varieties. The most commonly cultivated amaranth variety in the United States, i.e., Amaranthus K343 was found to possess the highest levels of phytosterols of the varieties tested. The possibility of screening for superior amaranth varieties with various health properties is outlined.

    Topics: Amaranthus; Cholesterol; Food, Organic; Nutritive Value; Phytosterols; Sitosterols; Stigmasterol

2003
[Studies on chemical constituents of Clerodendrum bungei].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:11

    To study the constituents from Clerodendrum bungei.. The constituents were isolated and purified with chromatographic methods, and identified by NMR, MS and IR.. Five compounds were isolated, beta-sitosterol (1), taraxerol (2), glochidone (3), glochidonol (4), glochidiol (5).. Compounds (3), (4) and (5) were isolated for the first time from C. bungei.

    Topics: Clerodendrum; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols

2003
[Studies on chemical constituents of Ervatamia hainanensis].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:11

    To study the chemical constituents of Ervatamia hainanensis.. The compounds were separated and purified by column chromatography with silica gel, and identified by IR, MS, NMR and 2D-NMR.. Five compounds were identified as I (isolariciresinol 9-O-beta-D-glucopyranoside), II (cycloartenol), III (beta-amyrin acetate), IV (beta-sitosterol), V (daucosterol), respectively.. All the compounds were isolated from this plant for the first time.

    Topics: Apocynaceae; Glucosides; Oleanolic Acid; Phytosterols; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

2003
[Studies on chemical constituents from the root of Mirablis jalapa].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:12

    To investigate the chemical constituents from the root of Mirabilis jalapa.. Compounds were isolated from 75% ethanolic extract of the titled herb by silica gel column chromatography, and their structures were elucidated by physical and chemical evidences and spectroscopic analysis.. Four compounds were obtained and identified as (2, 5-dioxoimidazolidin-4-yl)-urea (1), glycerin monoeicosate (2), boeravinone (3) and beta-sitosterol (4).. Compound (2) is a new compound, and compound (1) was obtained from this plant for the first time.

    Topics: Allantoin; Eicosanoids; Glycerol; Mirabilis; Plant Roots; Plants, Medicinal; Sitosterols

2003
[Studies on chemical constituents in leafs of Clerodendron fragrans].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2003, Volume: 28, Issue:10

    To separate and identify the constituents from Clerodendron fragrans.. The constituents were isolated and purified with chromatographic methods, identified by NMR, MS, IR.. Beta-sitosterol (1), clerosterol (2), daucosterol (3), caffeic acid (4), kaempferol (5), 5,4'-dihydroxy-kaempferol-7-O-beta-rutinoside (6), acteoside (7) and leucoseceptoside A (8), were isolated and identified.. Compound 7 and 8 were identified for the first time from Clerodendron fragrans.

    Topics: Clerodendrum; Glucosides; Glycosides; Phenols; Plant Leaves; Plants, Medicinal; Sitosterols

2003
Herbal medications in the treatment of benign prostatic hyperplasia (BPH).
    The Urologic clinics of North America, 2002, Volume: 29, Issue:1

    Herbal medications are used widely in the treatment of BPH. Recent studies suggest a benefit for some of these products with few side effects. The results of these studies are summarized and the possible mechanism of action of these medications are reviewed.

    Topics: Humans; Hypoxis; Male; Phytotherapy; Plant Extracts; Plants, Medicinal; Prostatic Hyperplasia; Secale; Serenoa; Sitosterols; Urtica dioica

2002
LDL cholesterol lowering by bile acid malabsorption during inhibited synthesis and absorption of cholesterol in hypercholesterolemic coronary subjects.
    Nutrition, metabolism, and cardiovascular diseases : NMCD, 2002, Volume: 12, Issue:1

    Recent large-scale trials have consistently documented the fact that a 25-35% reduction in low-density lipoprotein cholesterol (LDL-C) can delay the progression of atherosclerosis. This raises the question as to how much it is possible to reduce serum cholesterol using feasible therapies. The aim of this study was to investigate the cholesterol-lowering efficacy of a triple therapy combining bile acid malabsorption with the inhibition of cholesterol synthesis and absorption.. Eleven consecutive hypercholesterolemic coronary patients from Lipid Clinics on a low-fat, low-cholesterol baseline diet added simvastatin (20 mg/day) for three months, and then dietary plant stanol ester margarine (2.25 g of stanols/day) for eight weeks; finally, cholestyramine 8 g/day was added for another eight weeks. This was a before-after trial, in which the results of each period were compared with baseline and those of the previous period. Serum lipids were quantitated using commercial kits, and serum sterols by means of gas-liquid chromatography. Simvastatin lowered LDL-C by 39% (p < 0.001), and additional stanol ester margarine by a further 13% (p < 0.05). The triple treatment led to 67% reduction from baseline (p < 0.001), with all LDL-C values being < 2.6 mmol/L, and increased high-density lipoprotein cholesterol (HDL-C) by 15% (p < 0.01). It also increased the serum lathosterol/cholesterol ratio (p < 0.01), thus indicating an upregulation of cholesterol synthesis, and increased the serum sitosterol ratio (p < 0.01) despite the simultaneous consumption of plant stanols.. The massive reduction in LDL and increase in HDL-C obtained using our triple therapy suggests that the combination of stanol ester with only moderate doses of statin and resin makes it possible to control LDL-C levels effectively in hypercholesterolemic subjects.

    Topics: Aged; Anticholesteremic Agents; Bile Acids and Salts; Cholesterol; Cholesterol, Dietary; Cholesterol, HDL; Cholesterol, LDL; Cholestyramine Resin; Coronary Artery Disease; Diet, Fat-Restricted; Drug Therapy, Combination; Female; Humans; Hypercholesterolemia; Intestinal Absorption; Male; Simvastatin; Sitosterols; Treatment Outcome

2002
Sphingolipid and other constituents from almond nuts (Prunus amygdalus Batsch).
    Journal of agricultural and food chemistry, 2002, Jul-31, Volume: 50, Issue:16

    One sphingolipid, 1-O-beta-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2R)-2-hydroxyhexadecanoylamino]-4,8-octadecadiene-1,3-diol, and four other constituents, beta-sitosterol, daucosterol, uridine, and adenosine, have been isolated from the nuts of almond (Prunus amygdalus). Complete assignments of the proton and carbon chemical shifts for the sphingolipid were accomplished on the basis of high-resolution 1D and 2D NMR data. All of these compounds are being reported from almond nuts (P. amygdalus)for the first time.

    Topics: Adenosine; Chromatography; Magnetic Resonance Spectroscopy; Nuts; Prunus; Sitosterols; Sphingolipids; Uridine

2002
Characterisation and some possible uses of Plukenetia conophora and Adenopus breviflorus seeds and seed oils.
    Bioresource technology, 2002, Volume: 85, Issue:1

    Two non-conventional seeds, Plukenetia conophora (PKCP) and Adenopus breviflorus (ADB) were analysed for their proximate, fatty acids, sterols composition and physico-chemical characteristics. Crude protein was 25.65% for PKCP and 28.25% for ADB. ADB had lower moisture content (4.5%) than PKCP (8.0%) indicating that the former has better shelf life. Oil yields of the seeds were 49.58% for PKCP and 56.22% for ADB. The major sterols were stigmasterol and beta-sitosterol in PKCP and ADB respectively. PKCP oil had 98.8% unsaturated fatty acids with linolenic acid predominating (70.1%) while ADB had 85.1% unsaturated fatty acids with linoleic acid being most abundant (65.3%). The very high saponification and iodine values of PKCP oil suggest its utilisation in alkyd resin, shoe polish, liquid soap and shampoo production. There is the possibility of using ADB oil in these regards as well as for edible purposes.

    Topics: Chemical Phenomena; Chemistry, Physical; Color; Fatty Acids; Molecular Weight; Phytosterols; Plant Oils; Plants, Edible; Plants, Medicinal; Powders; Refractometry; Seeds; Sitosterols; Specific Gravity; Stigmasterol; Water

2002
Coumarin glycoside from Cissus sicyoides.
    Natural product letters, 2002, Volume: 16, Issue:4

    From the aerial parts of Cissus sicyoides, a new coumarin glycoside 5,6,7,8-tetrahydroxycoumarin-5beta-xylopyranoside was obtained together with known coumarin sabandin, two flavonoids kaempferol 3-rhamnoside and quercetin 3-rhamnoside and two steroids, sitosterol and 3beta-O-beta-D-glucopyranosylsitosterol. The structure of compounds was elucidated by spectral analyses.

    Topics: Brazil; Cissus; Coumarins; Flavonoids; Glycosides; Medicine, Traditional; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plants, Medicinal; Sitosterols; Stereoisomerism

2002
Clerodane diterpenoids from Ajuga bracteosa Wall.
    Natural product letters, 2002, Volume: 16, Issue:4

    The whole plant of Ajuga bracteosa afforded five compounds including one new clerodane diterpenoid designated as Bracteonin-A (1) 6alpha-acetoxy, 15 (R&S)-methoxy, 18-(4'-hydroxy, 3'-beta-methyl, 3'-alpha-acetoxy, butyryloxy) neoclerodane. The other compounds identified were 14,15-dihydroajugapitin, 14-hydro-15-hydroxy ajugapitin, beta-sitosterol, and stigmasterol. The structural elucidation was carried out by spectroscopic techniques.

    Topics: Ajuga; Chromatography, Thin Layer; Diterpenes; Diterpenes, Clerodane; India; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plants, Medicinal; Sitosterols; Spectroscopy, Fourier Transform Infrared; Stereoisomerism; Stigmasterol

2002
Bioactivity studies on beta-sitosterol and its glucoside.
    Phytotherapy research : PTR, 2002, Volume: 16, Issue:5

    Beta-sitosterol and beta-sitosteryl-beta-D-glucoside were isolated as analgesic constituents from the leaves of Mentha cordifolia Opiz. The acetic acid-induced writhing test showed that beta-sitosterol and beta-sitosteryl-beta-D-glucoside decreased the number of squirms induced by acetic acid by 70.0% and 73.0%, respectively, at a dose of 100 mg / kg mouse. Statistical analysis using the Kruskall Wallis one-way analysis of variance by ranks showed that these isolates approximate the analgesic activity of mefenamic acid at a 0.001 level of significance. The hot plate method confirmed their analgesic activities, as beta-sitosterol and beta-sitosteryl-beta-D-glucoside exhibited a 300% and 157% increase in pain tolerance, respectively, while mefenamic acid, a known analgesic, showed a 171% increase. Neither isolate exhibited antiinflammatory activity using the carrageenan-induced mouse paw oedema assay. Beta-sitosterol also exhibited anthelminthic and antimutagenic activities. In vitro tests using live Ascaris suum as test animals showed that the behaviour of worms treated with beta-sitosterol approximated that of the positive controls, Combantrin and Antiox. An in vivo micronucleus test showed that beta-sitosterol inhibited the mutagenicity of tetracycline by 65.3% at a dose of 0.5 mg /kg mouse. At the same dose, it did not exhibit chromosome-breaking activity.

    Topics: Acetic Acid; Analgesics; Animals; Anthelmintics; Anti-Inflammatory Agents; Ascaris suum; Drug Evaluation, Preclinical; Edema; Extremities; Gas Chromatography-Mass Spectrometry; Hot Temperature; Mefenamic Acid; Mentha; Mice; Micronucleus Tests; Pain; Pain Threshold; Plant Extracts; Plant Leaves; Plants, Medicinal; Sitosterols

2002
Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed.
    Plant physiology, 2002, Volume: 130, Issue:1

    The first committed step in the conversion of cycloartenol into Delta(5) C24-alkyl sterols in plants is catalyzed by an S-adenosyl-methionine-dependent sterol-C24-methyltransferase type 1 (SMT1). We report the consequences of overexpressing SMT1 in tobacco (Nicotiana tabacum), under control of either the constitutive carnation etched ring virus promoter or the seed-specific Brassica napus acyl-carrier protein promoter, on sterol biosynthesis in seed tissue. Overexpression of SMT1 with either promoter increased the amount of total sterols in seed tissue by up to 44%. The sterol composition was also perturbed with levels of sitosterol increased by up to 50% and levels of isofucosterol and campesterol increased by up to 80%, whereas levels of cycloartenol and cholesterol were decreased by up to 53% and 34%, respectively. Concomitant with the enhanced SMT1 activity was an increase in endogenous 3-hydroxy-3-methylglutaryl coenzyme A reductase activity, from which one can speculate that reduced levels of cycloartenol feed back to up-regulate 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and thereby control the carbon flux into sterol biosynthesis. This potential regulatory role of SMT1 in seed sterol biosynthesis is discussed.

    Topics: Biological Transport; Carbon; Cholesterol; Cloning, Molecular; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Hydroxymethylglutaryl CoA Reductases; Methyltransferases; Nicotiana; Phytosterols; Plant Leaves; Plants, Genetically Modified; Seeds; Sitosterols; Stigmasterol; Triterpenes

2002
Plasma membrane lipids in the resurrection plant Ramonda serbica following dehydration and rehydration.
    Journal of experimental botany, 2002, Volume: 53, Issue:378

    Plants of Ramonda serbica were dehydrated to 3.6% relative water content (RWC) by withholding water for 3 weeks, afterwards the plants were rehydrated for 1 week to 93.8% RWC. Plasma membranes were isolated from leaves using a two-phase aqueous polymer partition system. Compared with well-hydrated (control) leaves, dehydrated leaves suffered a reduction of about 75% in their plasma membrane lipid content, which returned to the control level following rewatering. Also the lipid to protein ratio decreased after dehydration, almost regaining the initial value after rehydration. Lipids extracted from the plasma membrane of fully-hydrated leaves were characterized by a high level of free sterols and a much lower level of phospholipids. Smaller amounts of cerebrosides, acylated steryl glycosides and steryl glycosides were also detected. The main phospholipids of control leaves were phosphatidylcholine and phosphatidylethanolamine, whereas sitosterol was the free sterol present in the highest amount. Following dehydration, leaf plasma membrane lipids showed a constant level of free sterols and a reduction in phospholipids compared with the well-hydrated leaves. Both phosphatidylcholine and phosphatidylethanolamine decreased following dehydration, their molar ratio remaining unchanged. Among free sterols, the remarkably high cholesterol level present in the control leaves (about 14 mol%) increased 2-fold as a result of dehydration. Dehydration caused a general decrease in the unsaturation level of individual phospholipids and total lipids as well. Upon rehydration the lipid composition of leaf plasma membranes restored very quickly approaching the levels of well-hydrated leaves.

    Topics: Cerebrosides; Cholesterol; Desiccation; Enzymes; Glycosides; Magnoliopsida; Membrane Lipids; Phosphatidylcholines; Phosphatidylethanolamines; Phospholipids; Plant Leaves; Sitosterols; Sterols; Water

2002
The association between low birth weight and high levels of cholesterol is not due to an increased cholesterol synthesis or absorption: analysis in twins.
    Pediatric research, 2002, Volume: 52, Issue:6

    Low birth weight may be associated with high levels of cholesterol in later life through genetic factors that affect both birth weight and cholesterol metabolism. Alterations in cholesterol synthesis and absorption may play an important role in this association. We examined birth weight and plasma ratios of a precursor of cholesterol, lathosterol (an estimate of cholesterol synthesis), and plant sterols, campesterol and beta-sitosterol (estimates of cholesterol absorption), to cholesterol in 53 dizygotic and 58 monozygotic adolescent twin pairs. After adjustment for current weight, birth weight was not associated with the ratios of lathosterol, campesterol, and beta-sitosterol either in the overall sample [+0.07 micro mol/mmol/kg (95% confidence interval: -0.11 to 0.25), p = 0.5; +0.02 micro mol/mmol/kg (-0.33 to 0.37), p = 0.9; and -0.04 micro mol/mmol/kg (-0.23 to 0.15), p = 0.8, respectively] or in the intrapair analysis in dizygotic twins [+0.27 micro mol/mmol/kg (-0.28 to 0.82), p = 0.3; -0.03 micro mol/mmol/kg (-1.07 to 1.01), p = 1.0; and +0.04 micro mol/mmol/kg (-0.56 to 0.64), p = 0.9, respectively] or in the intrapair analysis in monozygotic twins [+0.54 micro mol/mmol/kg (-0.09 to 1.18), p = 0.09; -0.60 micro mol/mmol/kg (-1.59 to 0.39), p = 0.2; and -0.43 micro mol/mmol/kg (-0.99 to 0.14), p = 0.14, respectively]. Plasma levels of lathosterol, campesterol, and beta-sitosterol, which are indicators of cholesterol synthesis and absorption, thus do not explain the association of low birth weight with high levels of total and LDL cholesterol. As an alternative hypothesis, we suggest that a decrease in cholesterol clearance may play an important role.

    Topics: Absorption; Adolescent; Biomarkers; Birth Weight; Cholesterol; Diseases in Twins; Female; Humans; Hypercholesterolemia; Infant, Low Birth Weight; Infant, Newborn; Male; Phytosterols; Risk Factors; Sitosterols; Twins, Dizygotic; Twins, Monozygotic

2002
Disruption of Abcg5 and Abcg8 in mice reveals their crucial role in biliary cholesterol secretion.
    Proceedings of the National Academy of Sciences of the United States of America, 2002, Dec-10, Volume: 99, Issue:25

    Cholesterol and other sterols exit the body primarily by secretion into bile. In patients with sitosterolemia, mutations in either of two ATP-binding cassette (ABC) half-transporters, ABCG5 or ABCG8, lead to reduced secretion of sterols into bile, implicating these transporters in this process. To elucidate the roles of ABCG5 and ABCG8 in the trafficking of sterols, we disrupted Abcg5 and Abcg8 in mice (G5G8(-/-)). The G5G8(-/-) mice had a 2- to 3-fold increase in the fractional absorption of dietary plant sterols, which was associated with an approximately 30-fold increase in plasma sitosterol. Biliary cholesterol concentrations were extremely low in the G5G8(-/-) mice when compared with wild-type animals (mean = 0.4 vs. 5.5 micromol ml) and increased only modestly with cholesterol feeding. Plasma and liver cholesterol levels were reduced by 50% in the chow-fed G5G8(-/-) mice and increased 2.4- and 18-fold, respectively, after cholesterol feeding. These data indicate that ABCG5 and ABCG8 are required for efficient secretion of cholesterol into bile and that disruption of these genes increases dramatically the responsiveness of plasma and hepatic cholesterol levels to changes in dietary cholesterol content.

    Topics: Animal Feed; Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Bile; Biological Transport; Chimera; Cholestanol; Cholesterol; Cholesterol, Dietary; Crosses, Genetic; Dietary Fats; Female; Gene Targeting; Intestinal Absorption; Intestinal Mucosa; Lipoproteins; Liver; Male; Mice; Mice, Inbred C57BL; Mice, Knockout; Phytosterols; Sitosterols

2002
Loci on chromosomes 14 and 2, distinct from ABCG5/ABCG8, regulate plasma plant sterol levels in a C57BL/6J x CASA/Rk intercross.
    Proceedings of the National Academy of Sciences of the United States of America, 2002, Dec-10, Volume: 99, Issue:25

    Plasma plant sterol levels differ among humans due to genetic and dietary factors. A disease characterized by high plasma plant sterol levels, beta-sitosterolemia, was recently found to be due to mutations at the ABCG5ABCG8 locus. To detect variants at this and other loci, a genetic cross was carried out between two laboratory mouse strains. Parental C57BL6J had almost twice the campesterol and sitosterol levels compared with parental CASARk mice, and F(1) mice had levels halfway between the parentals. An intercross between F(1)s was performed and plasma plant sterol levels measured in 102 male and 99 female F(2) mice. Plasma plant sterols in F(2)s displayed a unimodal distribution, suggesting the effects of several rather a single major gene. In the F(2) mice, a full genome scan revealed significant linkages on chromosomes 14 and 2. With regard to chromosome 14, analysis showed a single peak for linkage at 17 cM with a logarithm of odds (LOD) score of 9.9, designated plasma plant sterol 14 (Plast14). With regard to chromosome 2, analysis showed two significant peaks for linkage at 18 and 65 cMs with LOD scores of 4.1 and 3.65, respectively, designated Plast2a and Plast2b, respectively. Four interactions between loci, predominantly of an additive nature, were also demonstrated, the most significant between Plast14 and Plast2b (LOD 16.44). No significant linkage or gene interaction was detected for the ABCG5ABCG8 locus on chromosome 17. Therefore, other genes besides ABCG5ABCG8 influence plasma plant sterol levels and now become candidates to explain differences in plasma plant sterol levels between humans.

    Topics: Animals; ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Biomarkers; Cholesterol; Chromosome Mapping; Crosses, Genetic; Dietary Fats; Epistasis, Genetic; Female; Genotype; Lipoproteins; Male; Mice; Mice, Inbred C57BL; Mice, Inbred Strains; Phytosterols; Sitosterols; Species Specificity

2002
Microbial transformation of (+)-androsta-1 ,4-diene-3,17-dione by Cephalosporium aphidicola.
    Natural product letters, 2002, Volume: 16, Issue:6

    Fermentation of (+)-androsta-1,4-diene-3,17-dione ([structure: see text]) with Cephalosporium aphidicola for 8 days yielded oxidative and reductive metabolites, androst-4-ene-3,17-dione ([structure: see text]), 17beta-hydroxyandrosta-1,4-diene-3-one ([structure: see text]), 11alpha-hydroxyandrosta-1,4-diene-3,17-dione ([structure: see text]), 11alpha-hydroxyandrost-4-ene-3,17-dione ([structure: see text]), 11alpha,17beta-dihydroxyandrost-4-ene-3-one ([structure: see text]) and 11alpha,17beta-dihydroxyandrosta-1,4-diene-3-one ([structure: see text]). The fermentation of [structure: see text] with Fusarium lini also yielded metabolites [structure: see text]. The structures of these metabolites were elucidated on the basis of spectroscopic techniques.

    Topics: Acremonium; Androstadienes; Cholesterol; Fermentation; Fusarium; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Sitosterols; Spectrophotometry, Infrared; Spectroscopy, Fourier Transform Infrared; Stereoisomerism

2002
Inhibition of type 1 and type 2 5alpha-reductase activity by free fatty acids, active ingredients of Permixon.
    The Journal of steroid biochemistry and molecular biology, 2002, Volume: 82, Issue:2-3

    In different cell systems, the lipido-sterolic extract of Serenoa repens (LSESr, Permixon inhibits both type 1 and type 2 5alpha-reductase activity (5alphaR1 and 5alphaR2). LSESr is mainly constituted of fatty acids (90+/-5%) essentially as free fatty acids (80%). Among these free fatty acids, the main components are oleic and lauric acids which represent 65% and linoleic and myristic acids 15%. To evaluate the inhibitory effect of the different components of LSESr on 5alphaR1 or 5alphaR2 activity, the corresponding type 1 and type 2 human genes have been cloned and expressed in the baculovirus-directed insect cell expression system Sf9. The cells were incubated at pH 5.5 (5alphaR2) and pH 7.4 (5alphaR1) with 1 or 3nM testosterone in presence or absence of various concentrations of LSESr or of its different components. Dihydrotestosterone formation was measured with an automatic system combining HPLC and an on-line radiodetector. The inhibition of 5alphaR1 and 5alphaR2 activity was only observed with free fatty acids: esterified fatty acids, alcohols as well as sterols assayed were inactive. A specificity of the fatty acids in 5alphaR1 or 5alphaR2 inhibition has been found. Long unsaturated chains (oleic and linolenic) were active (IC(50)=4+/-2 and 13+/-3 microg/ml, respectively) on 5alphaR1 but to a much lesser extent (IC(50)>100 and 35+/-21 microg/ml, respectively) on 5alphaR2. Palmitic and stearic acids were inactive on the two isoforms. Lauric acid was active on 5alphaR1 (IC(50)=17+/-3 microg/ml) and 5alphaR2 (IC(50)=19+/-9 microg/ml). The inhibitory activity of myristic acid was evaluated on 5alphaR2 only and found active on this isoform (IC(50)=4+/-2 microg/ml). The dual inhibitory activity of LSESr on 5alpha-reductase type 1 and type 2 can be attributed to its high content in free fatty acids.

    Topics: Androgen Antagonists; Animals; Cell Line; Cholestenone 5 alpha-Reductase; Fatty Acids, Nonesterified; Fatty Alcohols; Humans; Hypolipidemic Agents; Isoenzymes; Oxidoreductases; Plant Extracts; Serenoa; Sitosterols; Tocopherols

2002
Functional analysis of candidate ABC transporter proteins for sitosterol transport.
    Biochimica et biophysica acta, 2002, Dec-23, Volume: 1567, Issue:1-2

    Two ATP-binding cassette (ABC) proteins, ABCG5 and ABCG8, have recently been associated with the accumulation of dietary cholesterol in the sterol storage disease sitosterolemia. These two 'half-transporters' are assumed to dimerize to form the complete sitosterol transporter which reduces the absorption of sitosterol and related molecules in the intestine by pumping them back into the lumen. Although mutations altering ABCG5 and ABCG8 are found in affected patients, no functional demonstration of sitosterol transport has been achieved. In this study, we investigated whether other ABC transporters implicated in lipid movement and expressed in tissues with a role in sterol synthesis and absorption, might also be involved in sitosterol transport. Transport by the multidrug resistance P-glycoprotein (P-gp; Abcb1), the multidrug resistance-associated protein (Mrp1; Abcc1), the breast cancer resistance protein (Bcrp; Abcg2) and the bile salt export pump (Bsep; Abcb11) was assessed using several assays. Unexpectedly, none of the candidate proteins mediated significant sitosterol transport. This has implications for the pathology of sitosterolemia. In addition, the data suggest that otherwise broad-specific ABC transporters have acquired specificity to exclude sitosterol and related sterols like cholesterol presumably because the abundance of cholesterol in the membrane would interfere with their action; in consequence, specific transporters have evolved to handle these sterols.

    Topics: 3T3 Cells; Animals; ATP Binding Cassette Transporter, Subfamily B, Member 1; ATP Binding Cassette Transporter, Subfamily G, Member 2; ATP-Binding Cassette Transporters; Biological Transport; Flow Cytometry; Mice; Mice, Knockout; Microscopy, Confocal; Multidrug Resistance-Associated Proteins; Neoplasm Proteins; Sitosterols; Spodoptera

2002
Serum plant sterols as a potential risk factor for coronary heart disease.
    Metabolism: clinical and experimental, 2002, Volume: 51, Issue:12

    In patients with the inherited disease of phytosterolemia, elevated concentrations of plant sterols (eg, campesterol and sitosterol) have been implicated as a risk factor for premature atherosclerosis. Whether plasma concentrations of campesterol and sitosterol are risk factors for coronary heart disease (CHD) in nonphytosterolemia subjects has not been established. Therefore, the present study examined the role of plant sterols in patients admitted for elective artery coronary bypass graft (ACBG). Serum concentrations of campesterol and sitosterol, as well as lathosterol, desmosterol, cholestanol, and lipoproteins were analyzed in 42 men and 11 women without lipid-lowering treatment during the past. Twenty-six patients reported a positive family history in their first-degree relatives for CHD. Lipid profile and other risk factors were comparable in both groups. Patients with a positive family history for CHD had significant higher plasma levels of campesterol (.50 +/-.17 v.38 +/-.16 mg/dL; P =.011), sitosterol (.40 +/-.11 v.31 +/-.11 mg/dL; P =.004) and their ratios to cholesterol. Lathosterol, desmosterol, cholestanol, and their ratios to cholesterol were not significantly different. Analysis of covariance (ANCOVA) analysis showed no influence of sex, age, triglycerides, total-, low-density lipoprotein (LDL)-, and high-density lipoprotein (HDL)-cholesterol on the results, but confirmed a strong influence of plant sterols. These findings support the hypothesis that plant sterols might be an additional risk factor for CHD.

    Topics: Aged; Cholesterol; Coronary Disease; Family; Female; Humans; Male; Medical Records; Middle Aged; Osmolar Concentration; Phytosterols; Risk Factors; Sitosterols

2002
Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis.
    Journal of natural products, 2002, Volume: 65, Issue:12

    A new isoflavone, 4',5,7-trihydroxy-6,8-dimethylisoflavone (1), and a new sesterterpenoic acid (2), together with five known compounds, lichexanthone (3), (-)-pinoresinol (4), betulinic acid, palmitic acid, and beta-sitosterol, were isolated from a dichloromethane extract of the branches of Henriettella fascicularis. Their structures were established by extensive spectroscopic methods. An attempt to determine the absolute stereochemistry of (2E,6S)-6-[(1R,5Z,3aS,9R,10Z,12aR)-1,2,3,3a,4,7,8,9,12,12a-decahydro-9-hydroxy-3a,6,10-trimethylcyclopentanocycloundecen-1-yl]-2-methylhept-2-enoic acid (2) was performed by single-crystal X-ray analysis, using Cu Kalpha radiation. Compound 1 showed significant competitive binding to estrogen receptor beta and moderate antiestrogenic activity with cultured Ishikawa cells.

    Topics: Alkaline Phosphatase; Binding Sites; Cell Line; Crystallography, X-Ray; Endometrium; Estrogen Antagonists; Estrogen Receptor Modulators; Female; Furans; Humans; Isoflavones; Lignans; Melastomataceae; Methylation; Molecular Conformation; Molecular Structure; Palmitic Acid; Panama; Phytosterols; Plant Shoots; Plants, Medicinal; Sitosterols; Stereoisomerism; Terpenes

2002
Biosynthesis of sterols and triterpenes in cell suspension cultures of Uncaria tomentosa.
    Plant & cell physiology, 2002, Volume: 43, Issue:12

    Pectin administered to Uncaria tomentosa cell suspension cultures, was found to increase the production of triterpene acids (ursolic and oleanolic acid), however, neither growth nor sterol accumulation were affected. Cell cultures showed that pectin treatment caused a rapid threefold increase in the activities of enzymes involved in the biosynthesis of C(5) and C(30 )isoprenoid, such as isopentenyl diphosphate isomerase and squalene synthase. The activity of a farnesyl diphosphatase, which could divert the flux of farnesyl diphosphate to farnesol, was two times lower in elicited than in control cells. Elicited cells also transformed more rapidly a higher percentage of [5-(3)H]mevalonic acid into triterpene acids. Interestingly, addition of terbinafine, an inhibitor of squalene epoxidase, to elicited cell cultures inhibited sterol accumulation while triterpene production was not inhibited. These results suggest that in U. tomentosa cells, both the previously mentioned enzymes and those involved in squalene 2,3-oxide formation play an important regulatory role in the biosynthesis of sterols and triterpenes.

    Topics: Carbon-Carbon Double Bond Isomerases; Cat's Claw; Cells, Cultured; Enzyme Inhibitors; Farnesyl-Diphosphate Farnesyltransferase; Hemiterpenes; Mevalonic Acid; Naphthalenes; Oleanolic Acid; Oxygenases; Pectins; Phosphoric Monoester Hydrolases; Phytosterols; Sitosterols; Squalene; Squalene Monooxygenase; Terbinafine; Triterpenes; Tritium; Ursolic Acid

2002
[Studies on flavoniod constituents of Hedysarum multijugum].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2002, Volume: 37, Issue:3

    To study the chemical constituents from Hedysarum multijugum.. The compounds were separated by chromatography methods, their structures were identified by spectral analysis.. Six compounds were isolated and identified as beta-sitosterol (1), 7-hydroxy-4'-methoxy isoflavone (2), betulic acid (3), 1,7-dihydroxy-3, 9-dimethoxy pterocarpene (4), 5, 7-dihydroxy-8-C-prenyl-4'-methoxy isoflavone (5) and 5, 7-dihydroxy-4'-methoxy isoflavone (6).. Compound 4 is a new compound and the others were obtained from the plant for the first time.

    Topics: Benzofurans; Benzopyrans; Betulinic Acid; Fabaceae; Molecular Structure; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Triterpenes

2002
[Studies on chemical constituents of Uvaria macrophylia].
    Yao xue xue bao = Acta pharmaceutica Sinica, 2002, Volume: 37, Issue:2

    To study the chemical constituents from Uvaria macrophylla Roxb. (Annonaceae).. Various chromatography techniques were used to separate and purify the constituents. Their structures were elucidated by UV, IR, MS, 1HNMR, 13CNMR, 1H-1H COSY, HMQC and HMBC spectral analysis.. Seven compounds have been isolated from the CHCl3 extract of the roots of the U. macrophylla. They were identified as macrophyllin (1), onysilin (2), taraxerol (3), 3,5-dimethoxy benzyl benzoic acid ester (4), benzoic acid (5), beta-sitosterol (6) and daucosterol (7).. Compound 1 is a new compound. Compounds 2-7 were obtained from this plant for the first time.

    Topics: Flavonoids; Molecular Structure; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Uvaria

2002
[Study on the constituents from Neonauclea sessilifolia].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2002, Volume: 25, Issue:12

    Seven compounds were isolated from Neonauclea sessilifolia. They are paeonol, 3,4-dihydroxybenzoic acid, scopoletin, anthraquinnones chrysophanol, 4H-1-benzopyran-4-one,5,7-dihydroxy-2-methyl, beta-sitosterol and stigmasterol glucoside. These compounds were isolated at first time from this genus and this plant.

    Topics: Acetophenones; Gas Chromatography-Mass Spectrometry; Glucosides; Hydroxybenzoates; Plant Stems; Plants, Medicinal; Rubiaceae; Scopoletin; Sitosterols; Stigmasterol

2002
[Studies on chemical constituents of effective part of Gastrodia elata].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2002, Volume: 27, Issue:1

    To study the chemical constituents of effective part of Gastrodia elata.. The constituens were isolated by column chromatographies with silica gel and ODS, and identified by NMR, MS spectra.. Six compounds were isolated and identified.. Three compounds were isolated from this plant for the first time.

    Topics: Gastrodia; Molecular Structure; Phenanthrenes; Plants, Medicinal; Quinones; Sitosterols; Sulfides

2002
[Studies on chemical constituents from Tibetan medicine wangla(rhizome of Coeloglossum viride var. bracteatum)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2002, Volume: 27, Issue:2

    To study the chemical constituents of Tibetan Madicine Wangla.. Sepearing the chemical constituents by means of chromatography and identifying their structures on the basis of MS and NMR spectra and TLC with authentic samples.. Eight compounds were isolated as 4-[(4-hydroxyphenyl) methoxy]benzenemethanol(I), 4,4'-dihydroxydiphenyl methane(II), 4,4'-dihydroxydibenzyl ether(III), gastrodin(IV), 4-hydroxy benzenemethanol(V), 4-hydroxybenz aldehyde(VI), beta-sitosterol(VII) and beta-daucosterol(VIII).. All the compounds were obtained from genus Coeloglassum for the first time. The compound I is a new natural product.

    Topics: Benzyl Alcohols; Glucosides; Orchidaceae; Plants, Medicinal; Rhizome; Sitosterols; Tibet

2002
[Studies on chemical constituents of Alpinia jianganfeng].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2002, Volume: 27, Issue:2

    To study the chemical constituents of Alpinia jianganfeng (Zingiberaceae) distributed in Sichuan province.. Chromatography and spectral analyses were used to isolate the constituents and elucidate their structure.. Four compounds were isolated from the rhizome of A. jianganfeng and elucidated as kaempferol-3-O-glucuronide(1), docosanoic acid(2), 3-hydroxy-stigmast-5-en-7-one(3) and beta-sitosterol(4).. All these compounds were obtained from this plant for the first time.

    Topics: Alpinia; Fatty Acids; Plants, Medicinal; Rhizome; Sitosterols

2002
[Studies on chemical constituents in the leaf of Ligustrum delavayanum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2002, Volume: 27, Issue:10

    To study the chemical constituents in the leaf of Ligustrum delavayanum Hariot.. The constituents were isolated with column chromatographies and the structures were identified by MS, IR, UV and NMR.. Four compounds were isolated and identified as beta-sitosterol, oleanic acid, 2 alpha-hydroxyursolic acid, and acteoside.. All the compounds were isolated from the plant for the first time.

    Topics: Glucosides; Ligustrum; Oleanolic Acid; Phenols; Plant Leaves; Plants, Medicinal; Sitosterols

2002
[Studies on chemical constituents of Salvia roborowskii Maxim].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2002, Volume: 25, Issue:11

    To study the chemical constituents from Salvia roborowskii Maxim.. Chromatography and spectroscopic analysis were employed to isolate and elucidate the chemical constituents in the plant.. Six compounds were isolated and elucidated as lupeol (I), 11 beta-hydroxy-lupeol(II),3 beta-acetyl-11 beta-hydroxy-lupeol(III), ursolic acid (IV), beta-sitosterol(V), daucosterol (VI).. I approximately VI were isolated from this plant for the first time.

    Topics: Chromatography, Thin Layer; Molecular Structure; Pentacyclic Triterpenes; Plants, Medicinal; Salvia; Sitosterols; Triterpenes; Ursolic Acid

2002
[Studies on chemical constituents of Caesalpinia decapetala (Roth) Alston].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2002, Volume: 25, Issue:11

    To study the chemical constituents from Caesalpinia decapetala (Roth) Alston.. Chromatography and spectroscopic analysis were employed to isolate and elucidate the chemical constituents in the plant.. Seven compounds were isolated and elucidated as lupeol acetate(I), lupeol(II), oleanoic acid(III), pentacosanoic acid 2,3-dihydroxypropyl ester(IV), 1-(26-hydroxyhexacosanoyl)-glycerol(V), stigmasterol(VI), beta-sitosterol(VI).. I approximattely VII were isolated from this plant for the first time.

    Topics: Caesalpinia; Chromatography, Thin Layer; Glycerides; Molecular Structure; Oleanolic Acid; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Stigmasterol; Triterpenes

2002
Plant biology. Prime time for cellulose.
    Science (New York, N.Y.), 2002, Jan-04, Volume: 295, Issue:5552

    Topics: Arabidopsis Proteins; Binding Sites; Carbohydrate Conformation; Catalysis; Cell Membrane; Cellulase; Cellulose; Dextrins; Glucans; Glucose; Glucosyltransferases; Gossypium; Membrane Proteins; Models, Biological; Organisms, Genetically Modified; Plants; Sitosterols; Uridine Diphosphate Glucose; Yeasts

2002
Sitosterol-beta-glucoside as primer for cellulose synthesis in plants.
    Science (New York, N.Y.), 2002, Jan-04, Volume: 295, Issue:5552

    Cellulose synthesis in plants requires beta-1,4-glucan chain initiation, elongation, and termination. The process of chain elongation is likely to be distinct from the process of chain initiation. We demonstrate that a CesA glucosyltransferase initiates glucan polymerization by using sitosterol-beta-glucoside (SG) as primer. Cotton fiber membranes synthesize sitosterol-cellodextrins (SCDs) from SG and uridine 5'-diphosphate-glucose (UDP-Glc) under conditions that also favor cellulose synthesis. The cellulase encoded by the Korrigan (Kor) gene, required for cellulose synthesis in plants, may function to cleave SG from the growing polymer chain.

    Topics: Arabidopsis Proteins; Calcium; Cell Wall; Cellobiose; Cellulase; Cellulose; Dextrins; Egtazic Acid; Glucans; Glucose; Glucosyltransferases; Gossypium; Herbicides; Membrane Proteins; Nitriles; Recombinant Proteins; Sitosterols; Uridine Diphosphate Glucose; Yeasts

2002
Phytosterols act as endocrine and metabolic disruptors in the European polecat (Mustela putorius).
    Toxicology and applied pharmacology, 2002, Jan-01, Volume: 178, Issue:1

    Phytosterols or plant sterols (PS) are consumed as natural remedies and margarines by the general population in developed countries to lower elevated serum cholesterol levels. They are also present in high concentrations in pulp mill effluents. The aim of the study was to screen the endocrine and metabolic parameters of the European polecat (Mustela putorius) for the effects of PS. The results showed an increase in the plasma estradiol and TH levels with no effects on the hypophyseal regulatory hormones. The plasma ghrelin levels decreased. PS also affected intermediary metabolism. The liver glycogen content increased as did the kidney glucose-6-phosphatase activity. The liver lipase esterase activity, on the other hand, decreased due to PS. In serum lipids the total cholesterol did not change, but the low-density lipoprotein levels increased and the high-density lipoprotein-cholesterol ratio decreased. PS had widespread previously unreported effects on the physiology of the polecat. The multiple effects indicate the need of a thorough risk assessment of the effects and interactions of PS.

    Topics: Animals; Body Weight; Carnivora; Dose-Response Relationship, Drug; Endocrine Glands; Estradiol Congeners; Estrogens, Non-Steroidal; Female; Glycogen; Hormones; Hypolipidemic Agents; Inactivation, Metabolic; Isoflavones; Kidney; Lipids; Liver; Male; Metabolism; Organ Size; Phytoestrogens; Phytosterols; Plant Preparations; Sitosterols

2002
Phytosterol content in American ginseng seed oil.
    Journal of agricultural and food chemistry, 2002, Feb-13, Volume: 50, Issue:4

    North American ginseng (Panax quinquefolium L.) oil was saponifed and the unsaponifiable matter trimethylsilylated. The phytosterol fraction of hexane-extracted, air-dried seed was quantified and identified by GC and GC-MS. Phytosterol contents (milligrams per 100 g of oil) were as follows: squalene (514-569), oxidosqualene (8.97-48.2), campesterol (9.96-12.4), stigmasterol (93.2-113), clerosterol (1.91-2.14), beta-sitosterol (153-186), beta-amyrin (11.7-19.5), delta(5)-avenasterol (12.4-20.5), delta(5,24(25))-stigmasterol (3.70-.76), lupeol (14.4-15.2), delta(7)-sitosterol (12.5-14.6), delta(7)-avenasterol (4.11-8.09), 24-methylenecycloartanol (1.94-4.76), and citrostadienol (2.50-3.81). Seed stratification lowered the phytosterol levels. Oven-drying gave mixed results, and phytosterols varied slightly between the 1999 and 2000 harvests.

    Topics: Cholesterol; Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Oleanolic Acid; Panax; Phytosterols; Plant Oils; Seeds; Sitosterols; Squalene; Stigmasterol; Triterpenes

2002
Original study of the biochemical and oil composition of the Cambodia nut Irvingia malayana.
    Journal of agricultural and food chemistry, 2002, Mar-13, Volume: 50, Issue:6

    Analysis of the biochemical composition of Irvingia malayana was carried out. This Cambodian nut contains 7.5% water and 70% oil. Most of the fatty acids are saturated and include 42% C12:0 and 41.8% C14:0; the sterol composition is similar to that of other vegetable oils. This oil is less rich in alpha-tocopherol than in gamma-tocopherol. Analysis of the solid content of the oil with respect to the temperature by NMR shows a fast fall of solid content around its fusion range at 38-39 degrees C. The main differences in the properties of the indigenous Cambodia nut from other known oleaginous seeds are in its selenium content, fatty acid composition, fusion temperature profile, and content of antioxidants. These important characteristics can soon make possible its application in pharmacology, cosmetics, the margarine industry, etc.

    Topics: alpha-Tocopherol; Antioxidants; Cambodia; Fatty Acids; gamma-Tocopherol; Magnetic Resonance Spectroscopy; Minerals; Nuts; Plant Oils; Plant Proteins; Selenium; Sitosterols; Temperature; Trees; Water

2002
A novel method of producing a microcrystalline beta-sitosterol suspension in oil.
    European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 2002, Volume: 15, Issue:3

    This paper describes a novel method of producing a microcrystalline oral suspension containing beta-sitosterol in oil for the treatment of hypercholesterolaemia. beta-Sitosterol pseudopolymorphs with different water contents were crystallized from acetone and acetone-water solutions. Structural analyses of the crystals were performed by Karl-Fisher titration, thermogravimetric analyses, X-ray diffraction and near infrared spectroscopy. The suspensions studied were composed of different concentrations of beta-sitosterol, oil and water. Suspensions were prepared by crystallization of hot concentrated solution of beta-sitosterol in oil by cooling with simultaneous agitation and water addition. The structural analyses of the suspensions were performed by X-ray diffraction, near infrared spectroscopy and optical microscopy. The viscosity of the suspensions was analysed as a function of shear stress. beta-Sitosterol was observed to exist in three different forms: anhydrous, hemihydrated and monohydrated crystals. By changing both the beta-sitosterol and the water concentration of the suspension, the crystal size and shape could be controlled. Addition of water resulted in the formation of monohydrated needle-shaped crystals instead of platy-like anhydrous crystals. Needle-shaped particles formed structured suspensions with shear thinning behaviour. By increasing the volume fraction of solid particles in suspension by increasing the water and/or sterol concentration, the viscosity increased. A high sterol concentration resulted in high supersaturation and thus formation of small crystals.

    Topics: Administration, Oral; Chemistry, Pharmaceutical; Crystallization; Hypercholesterolemia; Hypolipidemic Agents; Oils; Rheology; Sitosterols; Spectroscopy, Near-Infrared; Suspensions; Technology, Pharmaceutical; Thermogravimetry; X-Ray Diffraction

2002
A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).
    Phytochemistry, 2002, Volume: 59, Issue:8

    Mentha longifolia (Lamiaceae), an aromatic herb yielded a new halogenated chloro-derivative of menthone (longifone), two new derivatives of beta-sitosterol glycoside (longiside-A and -B) and a new flavanone-glycoside (longitin). The beta-sitosterol and flavanone glycosides were purified as their acetate derivatives. Structures of all the isolated constituents were elucidated with the aid of HMBC techniques. However, the structure of longifone was also determined through X-ray crystallography.

    Topics: Acylation; Chlorine; Crystallography, X-Ray; Flavanones; Flavonoids; Glycosides; Lamiaceae; Magnetic Resonance Spectroscopy; Menthol; Molecular Conformation; Sitosterols; Spectrum Analysis; Terpenes

2002
My hand was on the doorknob to leave.
    Biochemical and biophysical research communications, 2002, Apr-19, Volume: 292, Issue:5

    Topics: Animals; Biochemistry; Cholesterol; Education, Graduate; Ergosterol; History, 20th Century; Insecta; Sitosterols; United States

2002
Angiogenic activity of beta-sitosterol in the ischaemia/reperfusion-damaged brain of Mongolian gerbil.
    Planta medica, 2002, Volume: 68, Issue:4

    Aloe vera continues to be used for wound healing as a folk medicine. We previously reported that A. vera gel has angiogenic activity. In this study, we report upon the isolation of an angiogenic component beta-sitosterol from A. vera and examination of its effect upon damaged blood vessels of the Mongolian gerbil. In a chick embryo chorioallantoic membrane assay, beta-sitosterol was found to have an angiogenic effect. It enhanced new vessel formation in gerbil brains damaged by ischaemia/reperfusion, especially in the cingulated cortex and septal regions, in a dose-dependent fashion (up to 500 microg/kg, p < 0.05, n = 34 - 40). beta-Sitosterol also enhanced the expressions of proteins related to angiogenesis, namely von Willebrand factors, vascular endothelial growth factor (VEGF), VEGF receptor Flk-1, and blood vessel matrix laminin (p < 0.05, n = 6). In addition, the intraperitoneal administration of beta-sitosterol at 500 microg/kg/day for a period of 19 days significantly improved the motion recovery of ischaemia/reperfusion-damaged gerbils as assessed by rota-rod testing (p < 0.001, n = 10). Our results suggest that beta-sitosterol has therapeutic angiogenic effects on damaged blood vessels.

    Topics: Aloe; Angiogenesis Inducing Agents; Animals; Behavior, Animal; Blood Vessels; Blotting, Western; Brain; Chick Embryo; Dose-Response Relationship, Drug; Endothelial Growth Factors; Gerbillinae; Immunohistochemistry; Laminin; Lymphokines; Plant Extracts; Plant Leaves; Receptor Protein-Tyrosine Kinases; Receptors, Growth Factor; Receptors, Vascular Endothelial Growth Factor; Reperfusion Injury; Sitosterols; Vascular Endothelial Growth Factor A; Vascular Endothelial Growth Factors; von Willebrand Factor

2002
A new naphthoquinone from Polygonum aviculare.
    Natural product letters, 2002, Volume: 16, Issue:2

    A new naphthoquinone, 6-methoxyplumbagin was isolated from the acetone extracts of Polygonum aviculare. Its structure was elucidated by various spectroscopic methods. The known compounds sitosterol, oleanolic acid and 5,6,7,4'-tetramethoxyflavanone were also obtained from this natural source.

    Topics: Flavanones; Flavonoids; Molecular Structure; Naphthoquinones; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Plants, Medicinal; Polygonaceae; Saudi Arabia; Sitosterols

2002
Organic carbonate from Calotropis procera leaves.
    Fitoterapia, 2002, Volume: 73, Issue:3

    The leaves of Calotropis procera yielded an organic carbonate (1), along with stigmasterol and beta-sitosterol, identified by spectroscopic methods.

    Topics: Apocynaceae; Brazil; Carbonates; Medicine, Traditional; Molecular Structure; Plant Extracts; Plant Leaves; Plants, Medicinal; Propane; Sitosterols; Stigmasterol

2002
[Lipid chemical constituents of Salvia sochifolia C. Y. Wu].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:4

    To study the lipid chemical constituents of Salvia sochifolia growing in Yunnan province.. Chromatographic techniques were used to isolate the compounds and the structures were identified by spectral analysis.. Five compounds were isolated from the plant and identified as 2 alpha, 3 alpha-dihydroxyurs-12-en-28-oic acid, 2 alpha, 3 alpha, 24-trihydroxyurs-12-en-28-oic acid, ursolic acid, daucosterol and beta-sitosterol.. These compounds were isolated from the plant for the first time.

    Topics: Plant Roots; Plants, Medicinal; Salvia; Sitosterols; Triterpenes; Ursolic Acid

2001
[Studies on chemical constituents from Chinese medicinal plant Hemistepta lyrata Bunge].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:6

    To separate and identify the chemical constituents of the whole plant.. The compounds were extracted with solvents, isolated by column chromatography and identified by spectroscopic methods, such as IR, MS and 1H NMR.. Five compounds were identified as hentriantane I, taraxasteryl acetate II, taraxasterol III, beta-sitosterol IV, and stigmasterol V.. The compounds III and V were obtained from the plant for the first time.

    Topics: Asteraceae; Plants, Medicinal; Sitosterols; Sterols; Stigmasterol; Triterpenes

2001
[Isolation and elucidation of chemical constituents of Shandanshaoyao Decoction(I)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:6

    To study the chemical constituents of Shandanshaoyao Decoction.. The sample was prepared using boiling water, then precipitated by 75% ethanol. The ethanol soluble fraction was extracted by chloroform, ethyl acetate and n-butanol respectively. The extracts were isolated using silica gel and polyamide column chromatography, and the chemical constituents were identified by chemical and spectroscopic methods.. Six compounds were isolated from the chloroform and ethyl acetate extracts, and elucidated as tanshinone IIA, benzoic acid, ferulic acid, cryptotanshinone, beta-stitosterol and ursolic acid respectively.. A preliminary study on the chemical constituents in traditional Chinese compound recipe Shandanshaoyao Decoction is reported.

    Topics: Abietanes; Crataegus; Drug Combinations; Drugs, Chinese Herbal; Hypolipidemic Agents; Paeonia; Phenanthrenes; Plants, Medicinal; Salvia miltiorrhiza; Sitosterols; Triterpenes; Ursolic Acid

2001
[Comparative study on three types of chemicals extracted from tubers of populations of Pinellia ternata (Thunb.) Breit].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:5

    To study the genetic diversity of Pinellia ternata. on the chemical composition.. Fifteen populations of Pinellia ternata. originated mostly from middle and lower reaches of Yangtze River valley were collected and cultivated in Weigang Experimental Farm of Nanjing Agricultural University with same cultural conditions, and contents in three types of index chemicals extracted from tubers of the populations have been compared continuously.. The difference in contents of beta-sitosterol and Val and Arg extracted from tubers of the populations has been observed, and those contents are also different with harvesting time. But the mean contents of each of the three types of chemicals in autumn are all higher than those in summer respectively.

    Topics: Arginine; Genetic Variation; Pinellia; Seasons; Sitosterols; Valine

2001
[The research on the chemical components of Schizonepeta tenuifolia Briq].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2001, Volume: 24, Issue:3

    Eicosane acid, beta-sitosterol, oleanolic acid, ursolic acid and daucosterol have been firstly isolated and identified from Schizonepeta tenuifolia Briq..

    Topics: Eicosanoic Acids; Lamiaceae; Oleanolic Acid; Sitosterols; Triterpenes; Ursolic Acid

2001
[Studies on the chemical constituents of the herba of Cuscuta chinensis].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2001, Volume: 24, Issue:5

    The chemical constituents of the herb of Cuscuta chinensis Lam. were investigated. Five compounds were isolated from petroleum ether and chloroform fraction. Their structures were identified as beta-sitosterol, d-sesamin, 9(R)-hydroxy-d-sesamin, d-pinoresinol and daucosterol by chemical and spectroscopical methods. All these compounds were isolated from the stem for the first time.

    Topics: Chemical Fractionation; Cuscuta; Dioxoles; Drugs, Chinese Herbal; Furans; Lignans; Sitosterols; Spectrum Analysis

2001
[Studies on flavonoids from leaves of Callicarpa bodinieri Levl].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:12

    To study the constituents of Callicarpa bodinieri.. The compounds were isolated by chromatography. Their structures were identified by physical and spectral data.. Seven compounds were isolated and elucidated as 5-hydroxy-4',3,6,7-tetramethoxy flavone(I), luteolin-7-O-glucoside (II), chrysoeriol-4'-O-glucoside(III), luteolin-4'-O-glucoside(IV), beta-sitosterol(V), ursolic acid(VI), betulinic acid(VII).. All the compounds were isolated from this plant for the first time; Compounds I, III, IV were isolated from Callicarpa genus for the first time.

    Topics: Callicarpa; Flavonoids; Glucosides; Luteolin; Plant Leaves; Plants, Medicinal; Sitosterols

2001
[Studies on the chemical constituents of Asarum longerhizomatosum C. F. Liang et C. S. Yang].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:11

    To study the chemical constituents of the roots and rhizomes of Asarum longerhizomatosum.. Chromatography and spectral analysis were used to isolate the constituents and elucidate their structures.. Five compounds were isolated from the ethanol extracts of the roots and rhizomes, and identified as asarone(I), beta-sitosterol(II), 2,4,5-trimethoxybenzaldehyde(III), 4-(2,4,5-trimethoxyphenyl)-3-en-butylone(IV) and 3 beta-hydroxystigmast-5-en-7-one(V).. All the compounds were isolated from the plant for the first time, and IV is a new natural product.

    Topics: Allylbenzene Derivatives; Anisoles; Asarum; Plant Roots; Plants, Medicinal; Rhizome; Sitosterols

2001
[Studies on constituents of the leaves of Lindera aggregata (Sims) Kosterm].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:11

    To study the antibacterial and anti-inflammatory constituents of the leaves of Lindera aggrega.. Compounds were isolated by colum chromatography, and the structures were identified by spectroscopic methods.. Six compounds were isolated and identified as mixture of 6-Acetyllindenanolide B-1 and B-2(I), dehydrolindestrenolide (II), hydroxylinderstrenolide (III), linderalactone (IV), kameofero (V), beta-sitosterol (VI).. These compounds were obtained from the leaves of Lindera aggregata for the first time.

    Topics: Anti-Inflammatory Agents, Non-Steroidal; Lindera; Plant Leaves; Plants, Medicinal; Sesquiterpenes; Sitosterols

2001
[Studies on the chemical constituents from Aquilegia ecalcarata Maxim].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:7

    To study the chemical constituents from Aquilegia ecalcarata.. Compounds were isolated with silica gel and polyamide chromatography and their structures were determined by spectral analysis and chemical evidence.. Five compounds were obtained and identified as beta-sitosterol, isoorientin-7-O-glucoside, isovitexin-4'-O-glucoside, isovitexin-2'-O-rhamnoside, luteolin-7-O-glucoside.. All the compounds were isolated from this plant for the first time.

    Topics: Aquilegia; Flavonoids; Glucosides; Isoflavones; Luteolin; Plants, Medicinal; Sitosterols

2001
[Non-anthraquinone constituents from Rheum sublanceolatum C. Y. Cheng et Kao].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:8

    Study on the non-anthraquinone constituents from rhizoma and radix of Rheum sublanceolatum.. The constituents were isolated through column chromatography and identified on the basis of their physiochemical and spectral data.. Six non-anthraquinone constituents were isolated and identified as n-octacosanic acid, sitosterol, daucosterol, 2-methyl-5-carboxymethyl-7-hydroxychromone, piceatannol and 6-hydroxymusizin-8-O-beta-D-glucopyranoside.. All these compounds were firstly isolated from R. sublanceolatum.

    Topics: Plant Roots; Plants, Medicinal; Rheum; Rhizome; Sitosterols; Stilbenes

2001
[A study on quality standard of Sambucus chinensis Lindl].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:9

    To offer evidences for exploiting the plant resources and drafting the quality standards.. Studies of pharmacognosy.. The medicinal properties and the microscopic characteristics of the stem, leaves, rhizome and powder were described, drawn and physicochemically identified.. A convenient and effective method for identifying the herb has been established.

    Topics: Plant Leaves; Plant Stems; Plants, Medicinal; Quality Control; Rhizome; Sambucus; Sitosterols

2001
[Chemical constituents from Salix oritrepha Schneid].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:9

    To study chemical constituents of the above ground part of Salix oritrepha.. Using chromatography to isolate compounds and their structure were identified by physical, chemical and spectral techniques.. Four compounds were isolated and elucidated as beta-sitosterol, beta-sitosteryl-3-O-glucoside, friedelin, luteolin-7-O-glucoside.. All of them were isolated from S. oritrepha for the first time. Friedelin from the plants of genus Salix for the first time.

    Topics: Flavonoids; Glucosides; Luteolin; Plant Components, Aerial; Plants, Medicinal; Salix; Sitosterols; Tibet; Triterpenes

2001
[Studies on chemical constituents of Fragaria ananassa Duch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2001, Volume: 26, Issue:9

    To study the chemical constituents from the fruit of Fragaria ananassa.. Using chromatographic methods to isolate compounds and chemical and spectral methods to elucidate their structures.. Three compounds, 9, 19-cyclolanost-24-en-3-ol(1), 14-methyl-stigmasta-7, 24(28)-dien-3-ol(2) and beta-sitosterol(3) were isolated from the freeze-dried powder.. All of the compounds were obtained from this plant for the first time.

    Topics: Fragaria; Fruit; Phytosterols; Plants, Medicinal; Sitosterols; Triterpenes

2001
Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst.
    Journal of agricultural and food chemistry, 2001, Volume: 49, Issue:1

    Sterols (sitosterol, cholesterol, stigmasterol, ergosterol, and 7-dehydrocholesterol) and sitostanol have been converted in high to near-quantitative yields to the corresponding long-chain acyl esters via esterification with fatty acids or transesterification with methyl esters of fatty acids or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20-40 mbar) at 40 degrees C. Neither organic solvent nor water is added in these reactions. Under similar conditions, cholesterol has been converted to cholesteryl butyrate and steroids (5alpha-pregnan-3beta-ol-20-one or 5-pregnen-3beta-ol-20-one) have been converted to their propionic acid esters, both in moderate to high yields, via transesterification with tributyrin and tripropionin, respectively. Reaction parameters studied in esterification include the temperature and the molar ratio of the substrates as well as the amount and reuse properties of the C. rugosa lipase. Lipases from porcine pancreas, Rhizopus arrhizus, and Chromobacterium viscosum are quite ineffective as biocatalysts for the esterification of cholesterol with oleic acid under the above conditions.

    Topics: Candida; Catalysis; Cholesterol; Dehydrocholesterols; Ergosterol; Esterification; Fatty Acids; Kinetics; Lipase; Sitosterols; Sterols; Stigmasterol; Substrate Specificity; Triglycerides; Vacuum

2001
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.
    Biochemical and biophysical research communications, 2001, Feb-16, Volume: 281, Issue:1

    This study was designed to clarify the mechanisms of hypocholesterolemic action of beta-lactoglobuline tryptic hydrolysate (LTH) and to identify the novel hypocholesterolemic peptide derived from LTH by screening using Caco-2 cells and animal studies. Serum and liver cholesterol levels were significantly lower in rats fed LTH than in those fed casein tryptic hydrolysate (CTH). The present study suggests that the inhibition of micellar solubility of cholesterol which causes the suppression of cholesterol absorption by a direct interaction between cholesterol mixed micelles, and LTH in the jejunal epithelia is part of the mechanism underlying the hypocholesterolemic action of LTH. Though no one could trace the hypocholesterolemic peptide to any protein origin, we identified, for the first time, a novel hypocholesterolemic peptide, Ile-Ile-Ala-Glu-Lys (IIAEK). Surprisingly, the present study provides the first direct evidence that a new hypocholesterolemic peptide derived from beta-lactoglobuline can powerfully influence serum cholesterol levels and exhibit a greater hypocholesterolemic activity in comparison with that of medicine, beta-sitosterol, in animal studies.

    Topics: Administration, Oral; Animals; Anticholesteremic Agents; Body Weight; Caco-2 Cells; Caseins; Cattle; Cholesterol; Chromatography, High Pressure Liquid; Feces; Food Deprivation; Humans; Jejunum; Lactoglobulins; Liver; Male; Micelles; Milk; Organ Size; Peptide Fragments; Peptides; Protein Hydrolysates; Rats; Rats, Wistar; Sitosterols; Taurocholic Acid

2001
Mechanisms for cholesterol homeostasis in rat jejunal mucosa: effects of cholesterol, sitosterol, and lovastatin.
    Journal of lipid research, 2001, Volume: 42, Issue:2

    The effects of feeding cholesterol, sitosterol, and lovastatin on cholesterol absorption, biosynthesis, esterification, and LDL receptor function were examined in the rat jejunal mucosa. Cholesterol absorption was measured by the dual-isotope plasma ratio method; the rate-limiting enzyme of cholesterol biosynthesis, 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, was measured as total and expressed enzyme activities (in the absence and presence of a phosphatase inhibitor, NaF, respectively); mucosal total and esterified cholesterol concentrations were determined by gas-liquid chromatography; LDL receptor function was assayed as receptor-mediated binding of (125)I-labeled LDL to mucosal membranes. Feeding 2% sitosterol or 0.04% lovastatin for 1 week significantly (P < 0.01) decreased the amounts of cholesterol absorbed per day (-85% and -63%, respectively). In contrast, feeding 2% cholesterol for 1 week increased the amounts of absorbed cholesterol 27-fold, even though the percent absorption significantly decreased. With all three treatments, there was a coordinate regulation of total HMG-CoA reductase activity and receptor-mediated LDL binding. Cholesterol feeding downregulated both total jejunal HMG-CoA reductase activity (P < 0.05) and receptor-mediated LDL binding (P < 0.01), whereas lovastatin- and sitosterol-supplemented diets significantly upregulated both of these parameters. In the control, cholesterol-fed, and sitosterol-fed animals, about half of the total jejunal HMG-CoA reductase activity was expressed (in functional dephosphorylated form). However, in the lovastatin-treated rats with 4-fold stimulation of HMG-CoA reductase, only 23% of the total enzyme activity was expressed. Changes in total HMG-CoA reductase activity and receptor-mediated LDL binding in all tested groups occurred with no change in total concentrations of mucosal cholesterol, and only cholesterol-fed animals had increased mucosal esterified cholesterol concentrations. Thus, in response to various fluxes of dietary or newly formed cholesterol, HMG-CoA reductase and receptor-mediated LDL binding are coordinately regulated to maintain constant cellular cholesterol concentrations in the jejunum.

    Topics: Animals; Anticholesteremic Agents; Cholesterol; Cholesterol, Dietary; Homeostasis; Hydroxymethylglutaryl CoA Reductases; Jejunum; Lovastatin; Male; Microsomes; Rats; Rats, Sprague-Dawley; Sitosterols

2001
Regulating cholesterol by A, B, C.
    Nature reviews. Genetics, 2001, Volume: 2, Issue:1

    Topics: ATP-Binding Cassette Transporters; Cholesterol; Humans; Hyperlipidemias; Mutation; Sitosterols

2001
An anti-inflammatory principle from cactus.
    Fitoterapia, 2001, Volume: 72, Issue:3

    In previous studies, the ethanol extract of cactus (Opuntia ficus-indica) showed potent anti-inflammatory action. In the present study, following fractionation of the methanol extract of cactus stems guided by adjuvant-induced chronic inflammation model in mice, an active anti-inflammatory principle has been isolated and identified as beta-sitosterol.

    Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Drugs, Chinese Herbal; Granuloma; Male; Mice; Mice, Inbred ICR; Plants, Medicinal; Sitosterols

2001
Effects of endocrine modulating substances on reproduction in the hermaphroditic snail Lymnaea stagnalis L.
    Aquatic toxicology (Amsterdam, Netherlands), 2001, Volume: 53, Issue:2

    Various man-made agents like pesticides, industrial chemicals and some natural substances have the potential to alter hormonal pathways that regulate reproductive processes in certain species of wildlife. Until now, only a few investigations have been undertaken to determine the effects of these substances on reproductive capacities (fecundity and fertility) in exposed invertebrate aquatic species. In this study one of the most abundant mollusc of European limnic systems, the hermaphroditic gastropod Lymnaea stagnalis was investigated to determine the effects of endocrine modulating substances on reproductive parameters. Known endocrine modulating substances were tested using the following nominal concentrations; Tributyltin (TBT in ng Sn/l) and beta-sitosterol at 1, 10 and 100 ng/l, respectively, and 4-nonylphenol (4-NP) at 1, 10 and 100 microg/l. In addition, experiments were carried out with 1, 10 and 100 ng/l of t-methyltestosterone. All the testing was carried out on recently matured adults of Lymnaea. Fifteen to twenty snails per treatment were exposed for between 7 and 12 weeks in a semi-static test with a weekly exchange of testwater. Shell height and weight and mortality of the adults, egg production, hatching rate of the eggs, and histopathology of the adult snails were analysed. The same parameters were investigated on F(1) generation snails from exposed parents at two dates (1 week after exposure and at the end of the exposure duration). Treatments with TBT and 4-NP had only slight effects on the egg production of the adults and hatching rate of the eggs. However, increased histopathological changes were observed in epithelial tissues of the adult snails, e.g. lung and foot also characterised by extreme inflammatory processes. While beta-sitosterol and t-methyltestosterone had no effect on the shell height and weight or the mortality of adult snails nor on the egg production or ensuing egg hatching rate, beta-sitosterol treated snails presented a distinct atrophy of the albumen gland and so did t-methyltestosterone, albeit with a lower degree of atrophy. The observed histopathological effects due to exposure to tributyltin or 4-NP are suggested to lead to long-term adverse reproductive effects mediated by an impairment of the fitness of the snails. In the experiments the steroid-dependant (beta-sitosterol and t-methyltestosterone) degeneration of the albumen gland caused no obvious adverse effects on the fecundity nor fertility of the adults o

    Topics: Animals; Body Weight; Fertility; Lymnaea; Methyltestosterone; Phenols; Reproduction; Sitosterols; Time Factors; Trialkyltin Compounds

2001
The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by STEROL METHYLTRANSFERASE 2;1.
    The Plant journal : for cell and molecular biology, 2001, Volume: 25, Issue:6

    The Arabidopsis genome contains three distinct genes encoding sterol-C24-methyltransferases (SMTs) involved in sterol biosynthesis. The expression of one of them, STEROL METHYLTRANSFERASE 2;1, was modulated in 35S:SMT2;1 Arabidopsis in order to study its physiological function. Plants overexpressing the transgene accumulate sitosterol, a 24-ethylsterol which is thought to be the typical plant membrane reinforcer, at the expense of campesterol. These plants displayed a reduced stature and growth that could be restored by brassinosteroid treatment. Plants showing co-suppression of SMT2;1 were characterized by a predominant 24-methylsterol biosynthetic pathway leading to a high campesterol content and a depletion in sitosterol. Pleiotropic effects on development such as reduced growth, increased branching, and low fertility of high-campesterol plants were not modified by exogenous brassinosteroids, indicating specific sterol requirements to promote normal development. Thus SMT2;1 has a crucial role in balancing the ratio of campesterol to sitosterol in order to fit both growth requirements and membrane integrity.

    Topics: Amino Acid Sequence; Arabidopsis; Blotting, Northern; Brassinosteroids; Cholestanols; Cholesterol; Fruit; Gene Expression Regulation, Plant; Methyltransferases; Molecular Sequence Data; Phenotype; Phytosterols; Plant Growth Regulators; Plant Roots; Plant Stems; Plants, Genetically Modified; Sitosterols; Steroids, Heterocyclic; Sterols; Transgenes

2001
Avocado fruit is a rich source of beta-sitosterol.
    Journal of the American Dietetic Association, 2001, Volume: 101, Issue:4

    Topics: Food Analysis; Food, Organic; Humans; Hypolipidemic Agents; Lauraceae; Sitosterols

2001
Fate of intravenously administered squalene and plant sterols in human subjects.
    Journal of lipid research, 2001, Volume: 42, Issue:6

    We have studied metabolism of plant sterols and squalene administered intravenously in the form of lipid emulsion mimicking chylomicrons (CM). The CM-like lipid emulsion was prepared by dissolving squalene in commercially available Intralipid. The emulsion was given as an intravenous bolus injection of 30 ml containing 6.3 mg of cholesterol, 1.9 mg of campesterol, 5.7 mg of sitosterol, 1.6 mg of stigmasterol, 18.1 mg of squalene, and 6 g of triglycerides in six healthy volunteers. Blood samples were drawn from the opposite arm before and serially 2.5 -180 min after the injections. The decay of CM squalene, plant sterols, and triglycerides was monoexponential. The half-life of CM squalene was 74 +/- 8 min, that of campesterol was 37 +/- 5 min (P < 0.01 from squalene), and those of sitosterol, stigmasterol, and triglycerides were 17 +/- 2, 15 +/- 1, and 17 +/- 2 min, respectively (P < 0.01 from squalene and campesterol). The CM squalene concentration still exceeded the baseline level 180 min after injection (P = 0.02), whereas plant sterols and triglycerides returned to the baseline level between 45 and 120 min after injection. The half-lives of squalene and campesterol were positively correlated with their fasting CM concentrations. In addition, VLDL squalene, campesterol, and triglyceride concentrations, VLDL, LDL, and HDL sitosterol concentrations, as well as VLDL and LDL stigmasterol concentrations were increased significantly. Cholesterol concentrations increased in VLDL (P < 0.05), but were unchanged in CM after injection. These data suggest that squalene clearance occurs more slowly than that of plant sterols and triglycerides from CM, and that squalene is more tightly associated with triglyceride-rich lipoproteins than are plant sterols in injected CM-like emulsions.

    Topics: Adult; Cholesterol; Humans; Hypolipidemic Agents; Lipoproteins, HDL; Lipoproteins, LDL; Lipoproteins, VLDL; Male; Middle Aged; Phytosterols; Postprandial Period; Sitosterols; Squalene; Stigmasterol; Time Factors; Triglycerides

2001
Pregnene derivatives from Solenostemma argel leaves.
    Phytochemistry, 2001, Volume: 57, Issue:4

    Two new pregnene derivatives 14beta-15alpha-dihydroxy-delta4pregnene-3,20 dione and 3beta-14beta,15alpha-16alpha hydroxy-20-oxo-delta5pregnene-tetra-ol, in addition to alpha- and beta-amyrin and beta-sitosterol, were isolated from Solenostemma argel leaves. The structures were established by extensive spectral analysis as well as comparison with reference materials.

    Topics: Africa, Northern; Biological Factors; Medicine, Traditional; Oleanolic Acid; Plant Leaves; Plants, Medicinal; Sitosterols; Triterpenes

2001
Plant sterols regulate rat vascular smooth muscle cell growth and prostacyclin release in culture.
    Prostaglandins, leukotrienes, and essential fatty acids, 2001, Volume: 64, Issue:6

    Cardiovascular disease (CVD) is the leading cause of death in the USA and other industrialized countries. A large number of epidemiological studies have established a direct correlation between diet and the development and progression of atherosclerosis. Several studies have shown the incidence of CVD to be lower in populations consuming a predominantly plant-based diet, as compared to meat-based diets. Besides being low in fat and cholesterol, vegetarian and Asian diets contain a large variety of phytochemicals, which may function in the body. For example, phytosterols (PS) are plant sterols that interfere with the absorption of cholesterol from the intestine when present in adequate amounts. Although PS may also function at a cellular level in the body, there are few studies examining the action of PS on cells involved in atherosclerosis. The purpose of this study was to examine the effect of dietary PS on vascular smooth muscle cell (VSMC) growth and function, since VSMC play a central role in the development of atherosclerosis. VSMC were treated with 16 microM cholesterol, 25-hydroxycholesterol, campesterol and beta-sitosterol (SIT) using an ethanol as a vehicle. Cell growth was determined by cell counting and cell proliferation by DNA synthesis, which was measured by [(3)H]-thymidine incorporation. Cholesterol supplementation had no effect on cell growth and proliferation. 25-Hydroxycholesterol decreased cell growth by 68% and DNA synthesis by 99%. SIT was found to inhibit VSMC growth more effectively than campesterol. Of the two PS, campesterol decreased cell growth by 16% and SIT decreased cell growth by 30%. DNA synthesis was decreased 25% by SIT supplementation but was not influenced by campesterol or cholesterol supplementation. Cholesterol, campesterol and SIT were not cytotoxic to VSMC and did not significantly alter cell viability. 25-Hydroxycholesterol, however, was cytotoxic and decreased cell viability by 45% as determined by lactate dehydrogenase release and a trypan blue dye exclusion test. De novo cholesterol synthesis was decreased 28% by campesterol, 49% by SIT and 23% by cholesterol. Beta-sitosterol exhibited a greater effect on cholesterol synthesis than campesterol or cholesterol supplementation. Measurement of cell sterol content demonstrated incorporation of PS into VSMC at the expense of cholesterol. Campesterol decreased VSMC cholesterol content by 36%, representing 40% of the total sterol content following treatment. Beta-sito

    Topics: Animals; Cell Culture Techniques; Cell Division; Cholesterol; Epoprostenol; Hypolipidemic Agents; Muscle, Smooth, Vascular; Phytosterols; Rats; Rats, Wistar; Sitosterols; Sterols

2001
Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention.
    European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP), 2001, Volume: 10, Issue:3

    Phytosterols are plant sterols that are structurally similar to cholesterol and are characterized by anti-carcinogenic and anti-atherogenic properties. Beta-sitosterol and campesterol are the predominant phytosterols in blood. The present study aimed to analyse the reproducibility and overtime reliability of plasma beta-sitosterol and campesterol measurements. In order to study the reproducibility of the measurement (technical variability), three healthy premenopausal women donated a sample of their blood. Each blood sample was subdivided into six aliquots and analysed within the same run by the same laboratory technician. The intraclass correlation coefficients (ICCs) of the assay for plasma beta-sitosterol and campesterol were 0.88 and 0.94 (95% confidence intervals low bounds (95% CI(low)) were 0.66 and 0.82), respectively. To study the reliability of beta-sitosterol and campesterol measurement over time, seven premenopausal women were recruited. Over a 6-month period, each woman provided a fasting blood sample once a month at the same time of day, and the same numerical day of the luteal phase of her menstrual cycle (between the 20th and 24th day of her menstrual cycle). All plasma samples from the same individual were processed together at the same time by the same technician at the end of the 6-month period. The overtime ICCs of plasma beta-sitosterol and campesterol were 0.91 (95% CI(low) 0.49) and 0.58 (95% CI(low) 0.31), respectively. The high reproducibility and good overtime reliability of plasma beta-sitosterol and campesterol measurements indicate that they may be suitable for potential clinical and population-based studies on cancer prevention.

    Topics: Adult; Anticarcinogenic Agents; Biomarkers, Tumor; Cholesterol; Female; Humans; Luteal Phase; Middle Aged; Neoplasms; Phytosterols; Reproducibility of Results; Sitosterols

2001
Plant sterol intakes and colorectal cancer risk in the Netherlands Cohort Study on Diet and Cancer.
    The American journal of clinical nutrition, 2001, Volume: 74, Issue:1

    Plant sterols in vegetable foods might prevent colorectal cancer.. The objective was to study plant sterol intakes in relation to colorectal cancer risk in an epidemiologic study.. The study was performed within the framework of the Netherlands Cohort Study on Diet and Cancer in 120852 subjects who completed a baseline questionnaire in 1986. After 6.3 y of follow-up, 620 colon and 344 rectal cancer cases were detected. A case-cohort approach was used to calculate confounder-adjusted rate ratios (RRs) and their 95% CIs for quintiles of plant sterol intake.. The total mean (+/-SD) intake of campesterol, stigmasterol, beta-sitosterol, campestanol, and beta-sitostanol was 285 +/- 97 mg/d. Major contributors to plant sterol intake were bread (38%), vegetable fats (26%), and fruit and vegetables (21%). For men, there was no clear association between intake of any of the plant sterols and colon cancer risk when age, smoking, alcohol use, family history of colorectal cancer, education level, and cholecystectomy were controlled for. Adjustment for energy did not alter the result. For rectal cancer, adjustment for energy resulted in positive associations between risk and campesterol and stigmasterol intakes. For women, there was no clear association between intake of any of the plant sterols and colorectal cancer risk.. A high dietary intake of plant sterols was not associated with a lower risk of colon and rectal cancers in the Netherlands Cohort Study on Diet and Cancer.

    Topics: Aged; Bread; Case-Control Studies; Cholesterol; Cohort Studies; Colorectal Neoplasms; Confounding Factors, Epidemiologic; Dietary Fats; Female; Follow-Up Studies; Fruit; Humans; Hypolipidemic Agents; Male; Middle Aged; Netherlands; Phytosterols; Prospective Studies; Rectal Neoplasms; Risk Factors; Sitosterols; Stigmasterol; Surveys and Questionnaires; Vegetables

2001
Haplophytin-A and B: the alkaloidal constituents of Haplophyllum acutifolium.
    Phytochemistry, 2001, Volume: 57, Issue:8

    During the phytochemical investigation of Haplophyllum acutifolium, two alkaloids named haplophytin-A (1) and B (2) have been obtained. In addition, some known constituents: flindersine (3), kusunokinin (4), beta-sitosterol, oleanolic acid, cholesterol and hexadecanoic acid, have also been obtained. The known constituents have never been obtained from this source. The structures of all the isolated constituents were elucidated by spectroscopic means. However, the structures of constituents 1 and 2 were further confirmed through HMBC technique.

    Topics: Alkaloids; Cholesterol; Magnetic Resonance Spectroscopy; Oleanolic Acid; Pakistan; Palmitic Acid; Plants; Sitosterols; Spectrophotometry, Infrared

2001
Polycations increase the permeability of Mycobacterium vaccae cell envelopes to hydrophobic compounds.
    Microbiology (Reading, England), 2001, Volume: 147, Issue:Pt 10

    Polycations [protamine, polymyxin B nonapeptide (PMBN) and polyethyleneimine (PEI)] have been shown to increase the cell wall permeability of Mycobacterium vaccae to highly hydrophobic compounds, as manifested in enhanced intracellular bioconversion of beta-sitosterol to 4-androsten-3,17-dione (AD) and 1,4-androstadien-3,17-dione (ADD), and cell sensitization to erythromycin and rifampicin. The quantity of AD(D) formed per biomass unit was twice as high in the presence of PMBN and PEI, and three times higher with protamine. The sensitization factor, i.e. the MIC(50) ratio of the control bacteria to those exposed to polycations, ranged from 4 to 16, depending on the polycation/antibiotic combination. Non-covalently bound free lipids were extracted from the control and polycation-treated cells and fractionated with the use of chloroform, acetone and methanol. Chloroform- and acetone-eluted fractions (mainly neutral lipids and glycolipids, respectively) showed significant polycation-induced alterations in their quantitative and qualitative composition. The fatty acid profile of neutral lipids was reduced in comparison to control, whereas acetone-derived lipids were characterized by a much higher level of octadecenoic acid (C(18:1)) and a considerably lower content of docosanoic acid (C(22:0)), the marker compound of mycolate-containing glycolipids. Methanol-eluted fractions remained unaltered. Cell-wall-linked mycolates obtained from delipidated cells were apparently unaffected by the action of polycations, as judged from the TLC pattern of mycolic acid subclasses, the mean weight of mycolate preparations and the C(22:0) acid content in the mycolates, determined by GC/MS and pyrolysis GC. The results suggest the involvement of the components of non-covalently bound lipids in the outer layer in the M. vaccae permeability barrier.

    Topics: Anti-Bacterial Agents; Cell Membrane Permeability; Cell Wall; Erythromycin; Fatty Acids; Microbial Sensitivity Tests; Mycobacterium; Mycolic Acids; Polyamines; Polyelectrolytes; Rifampin; Sitosterols; Surface Properties

2001
[Residual chemicals in natural rubber products for food contact use].
    Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan, 2001, Volume: 42, Issue:3

    The residues of additives and other chemicals were investigated by GC/MS in natural rubber products for food contact, which included nipples, packing, gloves and a net for ham. The packings and gloves contained 980-6,570 micrograms/g of vulcanization accelerators, such as zinc dimethyldithiocarbamate, zinc diethyldithiocarbamate (EZ), zinc di-n-buthyldithiocarbamate (BZ) and 2-mercaptobenzothiazole. Some samples contained BHT, Irganox 1076 and Yoshinox 2246R as antioxidants; dibutyl phthalate and di(2-ethylhexyl) phthalate as plasticizers; and palmitic acid, stearic acid, palmitamide, stearamide and hydrocarbons as lubricants. Two unknown peaks were identified as stigmasterol and beta-sitosterol, and others were estimated to be fucosterol, oryzanol and alpha-sitosterol. These sterols are widely distributed in plants, so their origin was presumed to be the rubber plants. The sterols were detected at a level of 340-2,940 micrograms/g in all natural rubber samples. A migration test was carried out for some samples. No chemicals were released into water, 4% acetic acid or 20% ethanol at 60 degrees C for 30 min, though BHT, Yoshinox 2246R, EZ, BZ and sterols were released into n-heptane at 25 degrees C for 60 min.

    Topics: Antioxidants; Food Packaging; Product Packaging; Rubber; Sitosterols; Stigmasterol

2001
Mutations in ATP-cassette binding proteins G5 (ABCG5) and G8 (ABCG8) causing sitosterolemia.
    Human mutation, 2001, Volume: 18, Issue:4

    Sitosterolemia is an autosomal recessive disorder caused by mutations in two adjacent genes encoding coordinately regulated ATP binding cassette (ABC) half transporters (ABCG5 and ABCG8). In this paper we describe three novel mutations causing sitosterolemia: 1) a frameshift mutation (c.336-337insA) in ABCG5 that results in premature termination of the protein at amino acid 197; 2) a missense mutation that changes a conserved residue c.1311C>G; N437K) in ABCG5 and 3) a splice site mutation in ABCG8 (IVS1-2A>G). This study expands the spectrum of the ABCG5 and ABCG8 mutations that cause sitosterolemia. Nine nonsynonymous polymorphisms are also reported: I523V, C600Y, Q604E, and M622V in ABCG5; and D19H, Y54C, T400K, A632V, and Y641F in ABCG8.

    Topics: ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Cholesterol; DNA Mutational Analysis; Exons; Female; Gene Frequency; Humans; Introns; Lipid Metabolism, Inborn Errors; Lipoproteins; Male; Mutation; Polymorphism, Genetic; RNA Splice Sites; Sitosterols; White People

2001
Diet and disease: the "phyte" over intestinal cholesterol.
    Gastroenterology, 2001, Volume: 121, Issue:5

    Topics: ATP Binding Cassette Transporter, Subfamily G, Member 5; ATP Binding Cassette Transporter, Subfamily G, Member 8; ATP-Binding Cassette Transporters; Cholesterol, Dietary; Humans; Hypercholesterolemia; Lipoproteins; Mutation; Sitosterols

2001
Mechanisms of phytosterolemia in stroke-prone spontaneously hypertensive and WKY rats.
    Metabolism: clinical and experimental, 2001, Volume: 50, Issue:11

    Analysis of sterol composition in serum, liver, adipose tissue, adrenals, and abdominal aorta demonstrated that the contents of plant sterols, campesterol and sitosterol, were evidently higher in WKY and stroke-prone spontaneously hypertensive (SHRSP) rats than in Wistar and WKA rats fed a diet containing a 0.5% plant sterol mixture. Lymphatic 24-hour recovery of 3H-sitosterol was about 2-fold higher in the WKY and SHRSP rats than in the WKA rats. Lymphatic absorption of 14C-cholesterol was also higher in WKY and SHRSP rats compared with WKA rats, but the difference was smaller than in the case of sitosterol. The remarkable increase of sitosterol absorption in WKY and SHRSP rats was observed between 9 and 24 hours after the administration. In SHRSP rats, lymphatic absorption of sitosterol between 0 and 3 hours was also higher than those in the other rat strains. Markedly less esterified 3H-sitosterol was detected in lymph than 14C-cholesterol in all strains, and in WKY and SHRSP rats, only a small increase in the esterified forms of sitosterol and cholesterol was observed. Although the incorporation of micellar 3H-sitosterol and 14C-cholesterol into intestinal brush border membranes was higher in SHRSP rats than in WKA rats, no difference was observed between WKY and WKA rats. These observations suggest that the incorporation into the brush border membranes and the esterification of sterols are not the major determinants for the hyperabsorption of sitosterol and cholesterol in SHRSP and WKY rats. Secretion of sitosterol and cholesterol in the bile of rats fed a plant sterol mixture was lower in SHRSP than in WKA rats. These results suggest that WKY and SHRSP strains deposit plant sterols in the body by enhancing the absorption and lowering the excretion of plant sterols. These strains of rats may be suitable models for studying mechanisms of differential absorption of various sterols.

    Topics: Adipose Tissue; Adrenal Glands; Animals; Aorta, Abdominal; Bile; Cholesterol; Dietary Supplements; Genetic Predisposition to Disease; Hypolipidemic Agents; Intestinal Mucosa; Liver; Lymphatic System; Male; Microvilli; Organ Specificity; Phytosterols; Rats; Rats, Inbred SHR; Rats, Inbred WKY; Rats, Wistar; Sitosterols; Species Specificity; Stroke

2001
Enhancement of beta-sitosterol transformation in Mycobacterium vaccae with increased cell wall permeability.
    Acta microbiologica Polonica, 2001, Volume: 50, Issue:2

    Mycobacterium vaccae exposed to compounds which are known to disorganise the cell wall composition and architecture (protamine, glycine) showed increased specific activity in beta-sitosterol biotransformation to androstene derivatives, intennediates in the production of most medical steroids. GC/MS analysis of free lipid fatty acids revealed higher content of unsaturated compounds, mainly C16:1 and C18:1 in protamine- and glycine-treated cells than that in control cells, which seems to change the permeability features of the cell wall barrier, facilitating hydrophobic beta-sitosterol diffusion.

    Topics: Androstadienes; Androstenedione; Biotransformation; Cell Membrane Permeability; Cell Wall; Fatty Acids; Glycine; Mycobacterium; Protamines; Sitosterols

2001
Phytochemical and antimicrobial studies on Drynaria quercifolia.
    Fitoterapia, 2001, Volume: 72, Issue:8

    Friedelin, epifriedelinol, beta-amyrin, beta-sitosterol, beta-sitosterol 3-beta-D-glucopyranoside, and naringin were isolated from the dried rhizome of Drynaria quercifolia. The methanol extract showed broad and concentration-dependent antibacterial activity.

    Topics: Anti-Bacterial Agents; Anti-Infective Agents; Bacteria; Candida albicans; Dose-Response Relationship, Drug; Flavanones; Flavonoids; Humans; Microbial Sensitivity Tests; Oleanolic Acid; Phytotherapy; Plant Extracts; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

2001
Cytostatic activity of Achillea ageratum L.
    Phytotherapy research : PTR, 2001, Volume: 15, Issue:7

    The cytostatic activity of a chloroform extract and two isolated compounds from Achillea ageratum L. (Asteraceae) was determined in vitro against Hep-2 and McCoy cells. The chloroform extract exhibited a high degree of growth inhibition compared with the values obtained with the 6-mercaptopurine (positive control) against both cultures. Stigmasterol and beta-sitosterol, isolated from the chloroform extract, showed a high degree of growth inhibition.

    Topics: Antineoplastic Agents; Asteraceae; Humans; Inhibitory Concentration 50; Phytotherapy; Plant Extracts; Sitosterols; Stigmasterol; Tumor Cells, Cultured

2001
Selection of Mycobacterium sp. strains with capacity to biotransform high concentrations of beta-sitosterol.
    Applied microbiology and biotechnology, 2001, Volume: 57, Issue:3

    In this work, phytosterol-biotransforming strains were selected from Mycobacterium sp., using a high concentration of beta-sitosterol. The selection was made by culturing the strains in a medium enriched with 14 g beta-sitosterol/l as the unique source of carbon. During 2 months, the bacterial cultures were transferred successively. The extraction of the biotransformation products was made with methanol and ethyl acetate. The qualitative and quantitative analysis was made by means of thin-layer chromatography, gas-liquid chromatography (GLC) and GLC-mass spectrometry. Under these conditions, it was observed that after seven transfers, the strains MYcobacterium sp. MB-3683 and the Mycobacterium fortuitum B-11045 increased their biotransformation capacity from 20% to 64% and from 34% to 55%, respectively. The products in the highest proportion identified for each trial were androstenedione and androstadienedione. The results suggest that the high substrate concentration could be a selective mechanism to obtain strains more efficient in the biotransformation of beta-sitosterol into steroidal bases.

    Topics: Androstadienes; Androstenedione; Chromatography, Thin Layer; Gas Chromatography-Mass Spectrometry; Mycobacterium; Nuclear Magnetic Resonance, Biomolecular; Sitosterols

2001
Liquid chromatography-UV determination and liquid chromatography-atmospheric pressure chemical ionization mass spectrometric characterization of sitosterol and stigmasterol in soybean oil.
    Journal of chromatography. A, 2001, Nov-23, Volume: 935, Issue:1-2

    A narrow-bore HPLC-UV method was developed for the analysis of two of the more abundant naturally occurring phytosterols in vegetable oils: sitosterol and stigmasterol. The method enabled detection of the compounds at a concentration of 0.42 microg/ml and quantitation at concentrations of 0.52 and 0.54 microg/ml for sitosterol and stigmasterol, respectively. An excellent linearity was determined over two orders of concentration magnitude (r2 0.999-1.000) and verified by applying the Mandel fitting test (p>0.099) and the lack-of-fit test (p>0.057) performed at the 95% confidence level. A good intra-day precision ranging from 0.15 to 1.16% was calculated at two concentration levels (2 and 100 microg/ml). The inter-day reproducibility was verified on 3 different days by performing an homoscedasticity test and analysis of variance. A solid-phase extraction method was developed on silica cartridges for the isolation of phytosterols from soybean oil providing recovery values of 101+/-9 and 106+/-7% for sitosterol and stigmasterol, respectively. Good accuracy of the method was statistically demonstrated since no matrix effect was found for both the analytes. The developed method was applied to the quantitative assay of phytosterols in a soybean oil sample (61+/-5 mg/100 g of stigmasterol and 118+/-4 mg/100 g sitosterol). The HPLC-atmospheric pressure chemical ionization MS technique enabled the identification of stigmasterol, sitosterol and campesterol in the oil sample.

    Topics: Atmospheric Pressure; Chromatography, High Pressure Liquid; Mass Spectrometry; Reproducibility of Results; Sensitivity and Specificity; Sitosterols; Soybean Oil; Spectrophotometry, Ultraviolet; Stigmasterol

2001
Too young to be having a heart attack.
    Lancet (London, England), 2001, Volume: 358 Suppl

    Topics: Aged; Cholesterol; Female; Humans; Hyperlipoproteinemia Type II; Myocardial Infarction; Sitosterols

2001
[Constituents of the leaves of Holodiscus discolor (Pursh) Maxim].
    Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti, 2001, Volume: 50, Issue:6

    The paper deals with the isolation of constituents from light petrol and methanol extracts of the leaves of Holodiscus discolor (PURSH) MAXIM., Rosaceae. beta-sitosterol and taraxasterol were isolated from the light petrol extract, luteolin-7-O-glucoside was isolated from the methanol extract. The isolated compounds were identified by spectroscopic means and by comparison with authentic samples.

    Topics: Flavonoids; Glucosides; Luteolin; Plant Leaves; Plants, Medicinal; Rosaceae; Sitosterols; Sterols; Triterpenes

2001
[Study on the constituents from freeze-dried power of blackberries (Rubus ursinus)].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2001, Volume: 24, Issue:9

    Three Compounds were isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. The structures of them were identified as stigmasta-5,22-dien-3-ol],beta-sitosterol and beta-sitosterol-3 beta-D-glucose. All these compounds were isolated at the first time from the plant.

    Topics: Fruit; Powders; Rosaceae; Sitosterols; Stigmasterol

2001
In vitro and in vivo (SCID mice) effects of phytosterols on the growth and dissemination of human prostate cancer PC-3 cells.
    European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP), 2001, Volume: 10, Issue:6

    The dietary effect of phytosterols (PS) versus cholesterol on the growth and metastasis of the PC-3 human prostate cancer cells in SCID mice was studied. Also, their direct effect on the growth and migration of these cells in vitro was analysed. In the in vivo experiment, SCID mice were fed a diet containing 2% of either PS mixture or cholesterol plus 0.2% cholic acid and implanted with 2 x 10(6) tumour cells per mouse. Tumour growth was monitored for 8 weeks post inoculation. Animals fed the PS diet had tumours 40-43% smaller than those fed the cholesterol diet. Furthermore, the number of mice with lymph node and lung metastasis was almost one-half that of the cholesterol-fed group. In the in vitro studies, both beta-sitosterol and campesterol inhibited the growth of PC-3 cells by 70% and 14%, respectively, while cholesterol supplementation increased the growth by 18% when compared with controls. PS inhibited the invasion of PC-3 cells into Matrigel-coated membranes by 78% while cholesterol increased it by 43% as compared with the cells in the control media. Migration of tumour cells through 8 microm pore membranes was reduced by 60-93% when the PC-3 cells were in PS media, as compared with a 67% increase after cholesterol supplementation. PS supplementation reduced the binding of PC-3 cells to laminin by 15-38% and fibronectin by 23% while cholesterol increased binding to type IV collagen by 36%. It was concluded that PS indirectly (in vivo as a dietary supplement) and directly (in tissue culture media) inhibited the growth and metastasis of PC-3 cells. beta-Sitosterol was more effective than campesterol in offering this protection in most of the parameters studied.

    Topics: Animals; Body Weight; Cell Adhesion; Cholesterol; Humans; Male; Mice; Mice, SCID; Models, Animal; Neoplasm Metastasis; Phytosterols; Prostatic Neoplasms; Sitosterols; Tumor Cells, Cultured

2001
Effects of lyophilized black raspberries on azoxymethane-induced colon cancer and 8-hydroxy-2'-deoxyguanosine levels in the Fischer 344 rat.
    Nutrition and cancer, 2001, Volume: 40, Issue:2

    This study examined the effects of lyophilized black raspberries (BRB) on azoxymethane (AOM)-induced aberrant crypt foci (ACF), colon tumors, and urinary 8-hydroxy-2'-deoxyguanosine (8-OHdG) levels in male Fischer 344 rats. AOM was injected (15 mg/kg body wt i.p.) once per week for 2 wk. At 24 h after the final injection, AOM-treated rats began consuming diets containing 0%, 2.5%, 5%, or 10% (wt/wt) BRB. Vehicle controls received 5% BRB or diet only. Rats were sacrificed after 9 and 33 wk of BRB feeding for ACF enumeration and tumor analysis. ACF multiplicity decreased 36%, 24%, and 21% (P < 0.01 for all groups) in the 2.5%, 5%, and 10% BRB groups, respectively, relative to the AOM-only group. Total tumor multiplicity declined 42%, 45%, and 71% (P < 0.05 for all groups). Although not significant, a decrease in tumor burden (28%, 42%, and 75%) was observed in all BRB groups. Adenocarcinoma multiplicity decreased 28%, 35%, and 80% (P < 0.01) in the same treatment groups. Urinary 8-OHdG levels were reduced by 73%, 81%, and 83% (P < 0.01 for all groups). These results indicate that BRB inhibit several measures of AOM-induced colon carcinogenesis and modulate an important marker of oxidative stress in the Fischer 344 rat.

    Topics: 8-Hydroxy-2'-Deoxyguanosine; Adenocarcinoma; Adenoma; Animals; Anthocyanins; Anticarcinogenic Agents; Azoxymethane; Calcium; Cholesterol; Colonic Neoplasms; Coumaric Acids; Deoxyguanosine; Diet; Ellagic Acid; Freeze Drying; Fruit; Oxidative Stress; Rats; Rats, Inbred F344; Rosaceae; Sitosterols

2001
Phytosterols reduce in vitro metastatic ability of MDA-MB-231 human breast cancer cells.
    Nutrition and cancer, 2001, Volume: 40, Issue:2

    Metastasis plays a major role in morbidity and mortality from breast cancer. Differences in the incidence and mortality of breast cancer between societies suggest that environmental factors such as diet may play a role in the disease. Previous work from this laboratory suggests that dietary phytosterols (PS) may offer protection from breast cancer by inhibiting growth of the tumor and its metastasis in severe combined immunodeficient mice. Because metastasis is a multistep process, the aim of the present study was to investigate the effect of PS on some steps of the metastatic process: tumor cell invasion, adhesion, and migration. In addition, cell growth and cell cycle progression were evaluated. MDA-MB-231 cells were supplemented with cholesterol, beta-sitosterol, and campesterol. Cells were treated for 3 days with 16 microM sterol that was loaded on 5 mM cyclodextrin. beta-Sitosterol inhibited tumor cell invasion through Matrigel and adhesion of cells to plates coated with collagen I, collagen IV, fibronectin, and laminin compared with cholesterol treatments and controls. Cholesterol treatment resulted in increased adhesion to laminin and collagen IV, two basement membrane (BM) components that are implicated in signaling tumor cell invasion in this cell line. Only cholesterol treatment increased cellular migration. beta-Sitosterol inhibited cell growth by 70% compared with controls and induced cell cycle arrest at the G2/M phase. It is concluded that, among PS, beta-sitosterol may offer protection from breast cancer metastasis by inhibiting cell invasion of the BM, which may be mediated by its ability to limit the adhesive interaction of the tumor cell and the BM.

    Topics: Breast Neoplasms; Cell Adhesion; Cell Division; Cell Movement; Collagen; Collagen Type I; Collagen Type IV; Drug Combinations; Fibronectins; G2 Phase; Humans; Laminin; Mitosis; Neoplasm Invasiveness; Neoplasm Metastasis; Phytosterols; Proteoglycans; Sitosterols; Sterols; Tumor Cells, Cultured

2001
[Studies on the chemical constituents from Sophora flavescens ait].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:1

    To study the constituents from Sophora flavescens.. Separating the constituents by means of chromatography and identifying their structures on the basis of spectral analysis.. The five compounds obtained were identified as sucrose, lignoceric acid, beta-sitosterol, sinapic acid hexadecyl ester and umbelliferon.. Sinapic acid hexadecyl ester is a new compound. These compounds were obtained from the plant for the first time.

    Topics: Coumaric Acids; Fatty Acids; Plants, Medicinal; Sitosterols; Sophora; Umbelliferones

2000
[Chemical constituents from Eremurus chinensis Fedtsch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:6

    To investigate the chemical constituents from the herb Eremurus chinensis.. The chemical constituents were extracted with solvent and separated with column chromatography.. The structures were identified as chrysophanol 8-Me ether, aloesaponol III, daucosterol and beta-sitosterol.. These compounds were separated from genus Eremurus first time.

    Topics: Liliaceae; Plants, Medicinal; Sitosterols

2000
[Studies on chemical components of Gentiana tizuensis Franch. (I)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:4

    To study the chemical components of Gentiana tizuensis distributed in Qinghai Province.. Chromatography and spectral analyses were used to isolate the constituents and elucidate their structure.. Four compounds were isolated and identified as uvaol, L-(+)-l-O-methyl-myo-inositol, ursolic acid,beta-sitosterol.. All these components were obtained from the plant for the first time.

    Topics: Gentiana; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

2000
[Chemical constituents from Speranskia tuberculata (Bge.) Baill].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:5

    To investigate the chemical constituents from the herb Speranskia tuberculata.. The chemical constituents were extracted with solvent and separated with column chromatography. The structures were elucidated by spectral analysis.. Two compounds were isolated from the plant and identified as 18-hydroxy(-)-manool and beta-sitosterol.. Both were separated from this plant first time.

    Topics: Diterpenes; Euphorbiaceae; Plant Extracts; Plants, Medicinal; Sitosterols

2000
[Studies on constituents in Uncaria macrophylla Wall].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:8

    To study the chemical constituents of Uncaria macrophylla.. Compounds were isolated by Columu Chromatography, and the structures were identified by NMR spectral data and other methods.. Six compounds were isolated and identified as ursolic acid, 3 beta-6 beta-23-trihydroxyurs-12-en-28-oic acid, 3 beta, 6 beta, 19 alpha-trihydroxyurs-12-en-28-oic acid, epicatechin, beta-sitosterol and daucosterin. All the compounds were isolated for the first time from the plant.

    Topics: Catechin; Plant Stems; Plants, Medicinal; Sitosterols; Triterpenes; Uncaria; Ursolic Acid

2000
[Studies on chemical constituents of Lagopsis supina (Steph.) Ik.-GaI].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:7

    To study the chemical constituents of Lagopsis supina.. Compounds were separated by solvent extraction, column chromatography and TLC, and the structures were determined by chemical and spectral analyses.. Six compounds were isolated from the ethanol extract of L. supina and identified as eicosanoic acid octadecyl ester, eicosanoic acid-16-methyl-15, 16-hetadecenyl ester, palmitic acid, beta-sitosterol, oleanolic acid and daucosterol.. Except beta-sitosterol, all the compounds were isolated from this genus for the first time.

    Topics: Lamiaceae; Oleanolic Acid; Palmitic Acid; Plants, Medicinal; Sitosterols

2000
[Studies on chemical constituents in the root of Desmos grandifolius (I)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 2000, Volume: 25, Issue:7

    To investigate new compounds with anti-tumor activities from the root of Desmos grandifolius of Annonaceae.. The chemical constituents were isolated by silica gel column chromatography, and the structures were elucidated by UV, IR, MS, 1H NMR, 13C NMR, H-H COSY and NOESY analysis.. Six compounds have been isolated from the CHCl3 extract of this plant and identified as lawinal(I), isolawinal(II), desmethoxymatteucinol(III), benzoic acid(IV), beta-sitosterol(V) and sitgmasterol (VI).. All compounds were found from this plant for the first time. Three dihydroflavonoids isolated from this species are characterized by A-ring substitution and no B-ring substitution.

    Topics: Annonaceae; Benzoic Acid; Flavonoids; Plant Roots; Plants, Medicinal; Sitosterols; Stigmasterol

2000
[Pharmacognostical studies on the roots of Stellera chamaejasme and S. chamaejasme f. chrysantha].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2000, Volume: 23, Issue:1

    Morphological and histological characters of the roots of Stellera chamaejasme L. and S. chamaejasme L. f. chrysantha S. C. Huang, used as the origins of the Chinese medicine Langdu, were described and illustrated with line drawings. TLC analyses of the above two drugs were also undertaken. These studies provide referencial informations for the quality control, development and identification of these two drugs.

    Topics: Chromatography, Thin Layer; Pharmacognosy; Plant Roots; Plants, Medicinal; Quality Control; Sitosterols; Thymelaeaceae

2000
[Pharmacognostical studies on the stem and leaf of Mussaenda pubescens].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2000, Volume: 23, Issue:4

    Morphological and microscopic chracteristics of Mussaenda pubescens Ait. f, a traditional Chinese medicine were described and illustrated with line drawings. TLC and UV analysis of the medicinal material were also undertaken. These studies provide referential information for identification and development of this medicinal material.

    Topics: Chromatography, Thin Layer; Pharmacognosy; Plant Leaves; Plant Stems; Plants, Medicinal; Powders; Rubiaceae; Sitosterols

2000
[Pharmacognostical studies on the roots of Euphorbia stracheyi].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2000, Volume: 23, Issue:2

    Morphological and histological characters of the roots of Euphorbia stracheyi Boiss., a traditional Chinese medicine, were described and illustrated with line drawings. TLC analysis of the above drug was also undertaken. These studies provide referencial information for clinics, quality control, development and identification of this crude drug.

    Topics: Chromatography, Thin Layer; Euphorbia; Pharmacognosy; Plant Roots; Plants, Medicinal; Powders; Quality Control; Sitosterols

2000
[Chemical study of Alpinia officinarum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2000, Volume: 23, Issue:2

    Seven compounds were isolated from Alinia officinarum Hance and were identified as beta-sitoterol, 1,7-diphenyl-5-ol-3-heptone, 1-phenyl-7-(3'-methoxyl-4'-hydroxyl) phenyl-5-ol-3-heptone, glandin, kaempferol-4'-methylether and 3,4-dihydroxylbenzoic acid by IR, 1HNMR, 13CNMR, FAB-MS and EA. Among these compounds, 3,4-dihydroxylbenzoic acid was the first time obtained from Alpinia officinarum Hance. Furthermore, 1-phenyl-7-(3'-methoxyl-4'-hydroxyl) phenyl-5-ol-3-heptone and a new compound 1,7-diphenyl-3,5-heptandiol-phenyl-7-(3'-methoxyl-4'-hydroxyl) phenyl-3,5-heptaxdiol were obtained from 1,7-diphenyl-5-ol-3-heptone and 1-phenyl-7-(3'-methoxyl-4'-hydroxyl) phenyl-5-ol-3-heptone via chemical reductions.

    Topics: Alpinia; Flavonoids; Hydroxybenzoates; Kaempferols; Plant Roots; Plants, Medicinal; Sitosterols

2000
[Pharmacognostical studies on the roots of Euphorbia fischeriana].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 2000, Volume: 23, Issue:5

    Morphological and histological characters of the roots of Euphorbia fischeriana Steud., used as one of the origins of traditional Chinese medicine Langdu, were described and illustrated with line drawings. TLC analysis of the above drug was also undertaken. These studies provide referencial informations for clinics, quality control, development and identification of this crude drug.

    Topics: Chromatography, Thin Layer; Euphorbia; Pharmacognosy; Plant Roots; Plants, Medicinal; Powders; Quality Control; Sitosterols

2000
3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts.
    The Journal of laboratory and clinical medicine, 2000, Volume: 135, Issue:2

    Sitosterolemia is an inherited recessive disease characterized by abnormally increased plasma and tissue plant sterol concentrations. Patients hyperabsorb sitosterol. In addition, hepatic, ileal, and mononuclear leukocyte 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, the rate-controlling enzyme in the cholesterol biosynthetic pathway, is markedly suppressed in this disease. It is still controversial whether the down-regulation is due to accumulated sitosterol, but the effect of sitosterol on HMG-CoA reductase activity has not been studied in sitosterolemic tissues. To investigate whether sitosterol inhibits HMG-CoA reductase activity in sitosterolemia, we measured the enzyme activities in liver and cultured skin flbroblasts from patients. Hepatic HMG-CoA reductase activities in patients were decreased 76% (P < .05) as compared with results in control subjects. In contrast, HMG-CoA reductase activities in sitosterolemic fibroblasts were not decreased as compared with results in control fibroblasts, and the activities in all cells were up-regulated similarly when they were exposed to delipidated medium. Because the cultured sitosterolemic fibroblasts contained only trace amounts of plant sterols, we added 20 microg/mL sitosterol directly to the cell medium. Raising the intracellular sitosterol concentration to 7% of cellular cholesterol level increased HMG-CoA reductase activity 23% (P < .05), while the addition of the same amount of cholesterol to the cells reduced the activity 46% (P < .05). Thus, when sitosterolemic skin fibroblasts were used, it was possible to distinguish between the effects of cholesterol and those of sitosterol on the activity of HMG-CoA reductase. These results suggest that reduced HMG-CoA reductase activity in this disease is caused by secondary effects of unknown regulator(s) other than sitosterol.

    Topics: Adolescent; Adult; Aorta, Thoracic; Arteriosclerosis; Cells, Cultured; Cholesterol; Female; Fibroblasts; Humans; Hydroxymethylglutaryl CoA Reductases; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Lipid Metabolism, Inborn Errors; Male; Reference Values; Sitosterols

2000
Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women.
    Journal of the American College of Cardiology, 2000, Volume: 35, Issue:5

    The purpose of the study was to investigate whether cholesterol metabolism is associated with coronary artery disease (CAD) in postmenopausal women.. Although hypercholesterolemia, a predominant risk factor of CAD, is related to cholesterol metabolism, the association between cholesterol metabolism and CAD is not well known.. In addition to conventional coronary risk factors, fasting serum squalene, delta8-cholestenol, desmosterol, lathosterol (indicators of cholesterol synthesis), cholestanol, campesterol and sitosterol (indicators of cholesterol absorption) were measured in 48 50- to 55-year-old consecutive women with angiographically verified CAD and in 61 age-matched healthy controls.. The coronary patients had elevated ratios of squalene (p < 0.001), desmosterol (p = 0.005), campesterol (p = 0.028) and sitosterol (p = 0.022) to cholesterol, but had lower respective lathosterol value (p = 0.041) compared with the controls, despite similar serum cholesterol levels. Adjusted for age, body mass index, family history of CAD, smoking, hypertension, serum triglycerides, low-density lipoprotein (LDL) and high-density lipoprotein (HDL) cholesterol level and glycosylated hemoglobin A1c% (GHbA1c), the ratios of squalene (odds ratio, 1.36; 95% confidence interval, 1.17 to 1.57), lathosterol (0.98; 0.97 to 0.99), campesterol (1.01; 1.00 to 1.01) and sitosterol (1.01; 1.00 to 1.03) were significantly associated with the risk of CAD. In addition, family history of CAD and GHbA1c% were also independently related to the presence of CAD.. The results suggest that women with elevated ratios of serum squalene, campesterol and sitosterol to cholesterol and low respective lathosterol values have enhanced risk for CAD. Thus, enhanced absorption and reduced synthesis of cholesterol may be related to coronary atherosclerosis.

    Topics: Case-Control Studies; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Coronary Disease; Desmosterol; Fasting; Female; Glycated Hemoglobin; Humans; Middle Aged; Phytosterols; Postmenopause; Prevalence; Radiography; Reproducibility of Results; Risk Factors; Sensitivity and Specificity; Sitosterols; Squalene

2000
Inhibition of growth and stimulation of apoptosis by beta-sitosterol treatment of MDA-MB-231 human breast cancer cells in culture.
    International journal of molecular medicine, 2000, Volume: 5, Issue:5

    Epidemiological and experimental studies have suggested a protective role of phytosterols (PS) in the development of some types of cancer such as colon and prostate cancer. No work has been reported on the role of PS in the development of breast cancer, the second leading cancer in woman. The present study was designed to examine the effect of the two most common dietary PS, beta-sitosterol (SIT) and campesterol, as compared to cholesterol, the main sterol in the Western diet, on growth, apoptosis and cytotoxicity of MDA-MB-231 human breast cancer cells in culture. In addition, we investigated the possible role of protein phosphatase 2A (PP2A), an enzyme that has been shown to regulate growth and apoptosis in tumor parameters studied. Breast cancer cell growth was found to be inhibited by 66% after 3 days and 80% after 5 days with 16 microM SIT. Both campesterol and cholesterol sustained tumor growth at levels comparable to that of the vehicle control. None of the sterols tested at this level (16 microM) induced cytotoxicity as measured by lactic dehydrogenase release. SIT supplementation for 3 days at 16 microM resulted in a 6-fold increase in apoptosis in cells when compared to cholesterol treated cells. SIT treatment was found to have no effect on the level and content of tumor cell PP2A. It is concluded that SIT, by a still unknown mechanism, may offer protection from breast cancer by inhibiting growth and stimulating apoptosis.

    Topics: Apoptosis; Breast Neoplasms; Cell Division; Cholesterol; Dose-Response Relationship, Drug; Female; Humans; L-Lactate Dehydrogenase; Phosphoprotein Phosphatases; Phytosterols; Protein Phosphatase 2; Sitosterols; Tumor Cells, Cultured

2000
Plant sterol-C24-methyl transferases: different profiles of tobacco transformed with SMT1 or SMT2.
    Lipids, 2000, Volume: 35, Issue:3

    Higher plant cells contain a mixture of 24-desmethyl, 24-methyl(ene), and 24-ethyl(idene) sterols in given proportions according to species but also to cell type. As a first step to investigate the function of such sterol compositions in the physiology of a plant, we have illustrated in the present work the coexistence of two distinct (S)-adenosyl-L-methionine sterol-C24-methyltransferases (SMT) in transgenic Nicotiana tabacum L. Indeed, modulation of the expression of the tobacco gene SMT1-1, which encodes a cycloartenol-C24-methyltransferase, results in variations of the proportion of cycloartenol and a concomitant effect on the proportion of 24-ethyl sterols. Overexpression in tobacco of the Arabidopsis thaliana (L.) Heynh. gene SMT2-1 which encodes a 24-methylene lophenol-C24(1)-methyltransferase, results in a dramatic modification of the ratio of 24-methyl cholesterol to sitosterol associated with a reduced growth, a topic discussed in the present work.

    Topics: Arabidopsis; Cholesterol; Methyltransferases; Nicotiana; Phytosterols; Plants, Genetically Modified; Plants, Toxic; Sitosterols; Sterols

2000
Effect of beta-sitosterol, a plant sterol, on growth, protein phosphatase 2A, and phospholipase D in LNCaP cells.
    Nutrition and cancer, 2000, Volume: 36, Issue:1

    Previous work from this laboratory suggests an activation of the sphingomyelin cycle as a mechanism for growth inhibition with the incorporation of beta-sitosterol (SIT) into human prostate cancer LNCaP cells. In the present study we examined two key enzymes that have been shown to play a role in the sphingomyelin cycle. Dietary sterols (SIT and cholesterol) were compared for their effect on LNCaP cell growth, phospholipase D (PLD) activity, and protein phosphatase 2A (PP 2A) activity and expression. PP 2A has been suggested as a direct in vitro target of ceramide action on cell growth and apoptosis. Ceramide also inhibits phorbol myristate acetate-stimulated PLD. SIT (16 microM) increased PP 2A activity by 50% compared with cholesterol treatment in LNCaP prostate cells; however, SIT did not alter protein levels of PP 2A. There was an increase in PLD activity in the presence of phorbol myristate acetate in cells supplemented with 16 microM SIT compared with those supplemented with cholesterol after five days of treatment. The present study suggests that the activation of PP 2A added support to the role of the activation of the sphingomyelin cycle by SIT treatment. However, the increase in PLD activity, which was modest but significant, with SIT supplementation suggests that this pathway may be modulated by other mechanisms. This includes the incorporation of SIT into cell membranes that may alter fluidity and, thus, influence the activation of membrane-bound enzymes such as PLD.

    Topics: Apoptosis; Cell Division; Ceramides; Enzyme Activation; Humans; Male; Phospholipase D; Phosphoprotein Phosphatases; Prostatic Neoplasms; Protein Phosphatase 2; Sitosterols; Sphingomyelins; Tetradecanoylphorbol Acetate; Tumor Cells, Cultured

2000
Serum, biliary, and fecal cholesterol and plant sterols in colectomized patients before and during consumption of stanol ester margarine.
    The American journal of clinical nutrition, 2000, Volume: 71, Issue:5

    Cholesterol metabolic studies are simplified in colectomized patients because of rapid intestinal passage and reduced bacterial action.. Our objective was to study the effect on cholesterol and plant sterol metabolism of feeding a margarine containing stanol ester to 11 colectomized patients.. A margarine containing 2 g stanol was consumed for 7-18 d. Serum, biliary, and fecal lipids were measured before and during consumption of the margarine.. Serum cholesterol concentrations and the ratio of plant sterol to cholesterol decreased after 1 d of consumption of stanol esters (P < 0.05). After 7 d, serum cholesterol decreased by 16% (P < 0.01), cholesterol absorption efficiency decreased by approximately 40%, and fecal output of cholesterol as neutral sterols (but not as bile acids) increased by 36%. Biliary bile acid composition and the molar percentage of biliary cholesterol were unchanged. Increased ratios of cholesterol precursor sterols in serum and bile indicated enhanced cholesterol synthesis during consumption of stanol esters; the percentage absorption of plant sterols and the ratios of plant sterols to cholesterol decreased, whereas serum and biliary plant stanols and their biliary secretion gradually increased. In feces, 95% of cholesterol and 90% of plant stanols were in unesterified form.. In colectomized patients, effective inhibition of cholesterol absorption and lowering of serum cholesterol concentrations and plant sterol ratios occurs within 1 d of the start of consumption of stanol esters. The composition of major bile lipids is unchanged, indicating that gallstone formation is unlikely. Small amounts of plant stanols are recovered in serum and bile during consumption of stanol esters but effectively are secreted through bile, thereby balancing the intake-induced increase in their absorption.

    Topics: Adult; Bile Acids and Salts; Biliary Tract; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Cholesterol, VLDL; Colectomy; Feces; Humans; Hypolipidemic Agents; Margarine; Middle Aged; Phospholipids; Phytosterols; Sitosterols; Triglycerides

2000
The safety evaluation of phytosterol esters. Part 6. The comparative absorption and tissue distribution of phytosterols in the rat.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2000, Volume: 38, Issue:6

    As part of an extensive safety evaluation programme, a series of studies has been conducted to determine the fate of phytosterols in the rat. Rats were dosed by oral gavage with 14C-labelled samples of cholesterol, beta-sitosterol or beta-sitostanol or (3)H-labelled samples of beta-sitostanol, campesterol, campestanol or stigmasterol dissolved in sunflower seed oil. Urine and faeces were collected for up to 96 hours after dosing. There was no quantification of biliary excreted material in these studies. Animals were sacrificed and either prepared for whole body autoradiography or tissues and carcass remains were assayed for 14C or (3)H. The overall absorption of phytosterols was low as judged by tissue and carcass levels of radioactivity. Elimination from the body was mainly in the faeces and was initially very rapid, but traces of material were still being excreted at 4 days after dosing. While total absorption of the phytosterols could not be fully quantified without biliary excretion data, it was clear that cholesterol was absorbed to the greatest extent (27% of the dose in females at 24 hours). Campesterol (13%) was absorbed more than beta-sitosterol and stigmasterol (both 4%) which were absorbed more than beta-sitostanol and campestanol (1-2%). The absorption of phytosterols was slightly greater in females than males. For each test material, the overall pattern of tissue distribution of radioactivity was similar, with the adrenal glands, ovaries and intestinal epithelia showing the highest levels and the longest retention of radioactivity.

    Topics: Animals; Autoradiography; Cholesterol; Female; Intestinal Absorption; Male; Phytosterols; Rats; Sitosterols; Stigmasterol; Tissue Distribution

2000
Effect of beta-sitosterol on transforming growth factor-beta-1 expression and translocation protein kinase C alpha in human prostate stromal cells in vitro.
    European urology, 2000, Volume: 37, Issue:6

    Today, plant extracts are widely used in the treatment of benign prostatic hyperplasia (BPH). However, the complete mode of action of the active substance, beta-sitosterol, is under investigation. The purpose of this study was to investigate the effect of beta-sitosterol on the expression of transforming growth factor beta 1 (TGF-beta1) and the activity of protein kinase C alpha (PKC-alpha) in primary prostate stromal cell cultures in vitro.. Tissue samples for primary cell cultures were obtained from patients undergoing transurethral resection of the prostate (TURP). TGF-beta1 levels in stromal cell conditioned media following a culture with beta-sitosterol were detected in a TGF-beta1 specific ELISA assay. Following different incubation periods with beta-sitosterol, cells were lysed and fractionated into a Triton-soluble membrane fraction and a cytosol fraction. PKC-alpha protein was detected using immunoblot analysis.. Beta-sitosterol was able to induce the expression and secretion of TGF-beta1 significantly between 1.26- and 1.86-fold compared to a cholesterol and the nonsupplemented control in 6 of 8 individual cultures. The total amount of secreted TGF-beta1 varied in cells from different patients. Based on its presence in both membrane fraction and cytosol, PKC-alpha appeared to be constitutively expressed in stromal cells. In the absence of beta-sitosterol PKC-alpha was predominantly found in its membrane-associated active form. Following a culture with beta-sitosterol, a translocation of PKC-alpha from the membrane to the cytosol was observed. This effect was specific for beta-sitosterol as compared to cholesterol.. This study describes the effect of beta-sitosterol on the expression of a multifunctional growth factor (TGF-beta1) and the activity of PKC-alpha membrane in stromal cells of the human prostate in vitro.

    Topics: Cell Division; Cells, Cultured; Humans; Isoenzymes; Male; Prostate; Protein Kinase C; Protein Kinase C-alpha; Sitosterols; Time Factors; Transforming Growth Factor beta

2000
Influence of sources of dietary oils on the life span of stroke-prone spontaneously hypertensive rats.
    Lipids, 2000, Volume: 35, Issue:4

    In recent studies, the life span of stroke-prone spontaneously hypertensive (SHRSP) rats was altered by a variety of dietary fats. It was relatively shorter in rats fed canola oil as the sole source of fat. The present study was performed to find out whether the fatty acid profile and the high content of sulfur compounds in canola oil could modulate the life span of SHRSP rats. SHRSP rats (47 d old, n = 23/group) were matched by body weight and systolic blood pressure and fed semipurified diets containing 10% canola oil, high-palmitic canola oil, low-sulfur canola oil, soybean oil, high-oleic safflower oil, a fat blend that mimicked the fatty acid composition of canola oil, or a fat blend high in saturated fatty acids. A 1% sodium chloride solution was used as drinking water to induce hypertension. After consuming the diets for 37 d, five rats from each dietary group were killed for collection of blood and tissue samples for biochemical analysis. The 18 remaining animals from each group were used for determining their life span. The mean survival time of SHRSP rats fed canola oil (87.4+/-4.0 d) was not significantly different (P > 0.05) from those fed low-sulfur canola oil (89.7+/-8.5 d), suggesting that content of sulfur in canola oil has no effect on the life span of SHRSP rats. The SHRSP rats fed the noncanola oil-based diets lived longer (mean survival time difference was 6-13 d, P < 0.05) than those fed canola and low-sulfur canola oils. No marked differences in the survival times were observed among the noncanola oil-based groups. The fatty acid composition of the dietary oils and of red blood cells and liver of SHRSP rats killed after 37 d of treatment showed no relationship with the survival times. These results suggest that the fatty acid profile of vegetable oils plays no important role on the life span of SHRSP rat. However, phytosterols in the dietary oils and in liver and brain were inversely correlated with the mean survival times,indicating that the differential effects of vegetable oils might be ascribed, at least partly, to their different phytosterol contents.

    Topics: Animals; Brain Chemistry; Cholesterol; Dietary Fats, Unsaturated; Fatty Acids; Fatty Acids, Monounsaturated; Hypertension; Liver; Phytosterols; Rapeseed Oil; Rats; Rats, Inbred SHR; Sitosterols; Stroke; Survival Rate; Thiobarbituric Acid Reactive Substances; Vitamin E

2000
Peanuts as a source of beta-sitosterol, a sterol with anticancer properties.
    Nutrition and cancer, 2000, Volume: 36, Issue:2

    Work from our laboratory, as well as others, suggests a protective role of phytosterols (PS), especially beta-sitosterol, from colon, prostate, and breast cancer. Asians and vegetarians consume higher amounts of PS than Western societies. The latter societies have a higher incidence of these cancers than Asians and vegetarians. The aim of this study was to evaluate peanuts and its products as sources of PS in the American diet. Roasted peanuts contain 61-114 mg PS/100 g depending on the peanut variety, 78-83% of which is in the form of beta-sitosterol. Unrefined peanut oil contains 207 mg PS/100 g, which is similar to that of the US Department of Agriculture Nutrient Database. This value is higher than that of unrefined olive oil. Refining these oils results in reduction in PS concentration in the oil. This loss is greater in the case of olive oil than peanut oil. Further refining, such as deodorization, results in significant loss in PS, but hydrogenation after refining has a minimal effect on PS loss. Peanut butter, which represents 50% of the peanuts consumed in the United States, contains 144-157 mg PS/100 g. Peanut flour, which results from partial removal of oil from peanuts, contains 55-60 mg PS/100 g. The data suggest that peanuts and its products, such as peanut oil, peanut butter, and peanut flour, are good sources of PS.

    Topics: Antineoplastic Agents; Arachis; Breast Neoplasms; Colonic Neoplasms; Female; Humans; In Vitro Techniques; Male; Phytosterols; Phytotherapy; Prostatic Neoplasms; Sitosterols

2000
Cytotoxic components from the bark of Stauranthus perforatus from Monteverde, Costa Rica.
    Planta medica, 2000, Volume: 66, Issue:5

    Topics: Antineoplastic Agents, Phytogenic; Chromatography; Costa Rica; Furocoumarins; Magnetic Resonance Spectroscopy; Methoxsalen; Plant Extracts; Plant Stems; Quinolines; Sitosterols; Trees; Tumor Cells, Cultured; X-Ray Diffraction

2000
Lysophosphatidylcholine-induced cellular injury in cultured fibroblasts involves oxidative events.
    Journal of lipid research, 2000, Volume: 41, Issue:8

    Lysophosphatidylcholine (lysoPC), formed during LDL oxidation and located within atherosclerotic plaques, induces numerous cellular responses, but via unknown mechanisms. Cellular events involved in sublethal lysoPC-induced injury were examined because these are relevant to mechanisms by which lysoPC alters cell behavior. LysoPC evoked transient membrane permeabilization in fibroblasts within 10 min. Cells underwent reversible rounding within 2 h, returning 3 h later to grossly normal appearance and a normal response to growth stimulation. We asked whether this sublethal permeabilization resulted from physical perturbation of the plasma membrane or if it required cellular events. LysoPC induced leakage of fluorescent dye from unilamellar phospholipid vesicles, suggesting physical membrane perturbation was a significant contributor. To characterize this further we increased the cholesterol content of cells and vesicles to stabilize membranes, and found decreased lysoPC-induced permeabilization in both cell and cell-free systems as cholesterol levels increased. Interestingly, vitamin E, a known antioxidant, blunted lysoPC-induced permeabilization and morphological changes in cells. Thus, lysoPC appeared to cause an unexpected oxidant stress-dependent enhancement of cell injury. To confirm this, several structurally distinct antioxidants, including N, N'-diphenyl-1,4-phenylenediamine, Desferal, Tiron, and 4-hydroxy TEMPO, were applied and these also were inhibitory. Oxidant stress was observed by a lysoPC-induced increase in fluorescence of 5- and 6-carboxy-2',7'-dichlorodihydrofluorescein diacetate, an intracellular marker of reactive oxygen species. Lysophosphatidylethanolamine (lysoPE) caused qualitatively similar morphological changes to cells and induced permeabilization, but injury by lysoPE was not inhibited by antioxidants. These data suggest that generation of intracellular reactive oxygen species follows lysoPC-induced plasma membrane destabilization and that this lysoPC-specific oxidant stress enhances cell injury. This intracellular oxidant stress in response to lysoPC may be an integral part of the multiple influences lysoPC has on gene expression and cell function.

    Topics: Adenine; Antioxidants; Carbon Radioisotopes; Cell Membrane Permeability; Cells, Cultured; Cholesterol; Fibroblasts; Glutathione; Humans; Infant, Newborn; Kinetics; Lysophosphatidylcholines; Lysophospholipids; Male; Oxidation-Reduction; Oxidative Stress; Phenylenediamines; Reactive Oxygen Species; Sitosterols; Stigmasterol; Vitamin E

2000
[Sterols in Lilium candidum L].
    Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti, 2000, Volume: 49, Issue:1

    From the butanolic extract of petals of Lilium candidum L., beta-sitosterol and beta-sitosterol glucoside were isolated. The isolated compounds were identified by spectroscopic means and by comparison with literature data; beta-sitosterol glucoside was isolated in genus Lilium L. for the first time.

    Topics: Plant Extracts; Sitosterols

2000
Does increased crypt cell proliferation impair cholesterol absorption after proximal gut resection?
    Scandinavian journal of gastroenterology, 2000, Volume: 35, Issue:7

    The effects of proximal small-bowel resection on absorption and synthesis of cholesterol are unclear.. To study cholesterol absorption and synthesis after proximal gut resections of variable length, plasma plant sterols, cholestanol, and cholesterol precursors were measured 1 and 2 months after 50% and 75% proximal small-bowel resection or transection. To examine the effect of increased crypt cell proliferation and brush border development on cholesterol absorption, the results were related to the mucosal morphology, crypt cell proliferation, and disaccharidase activities of the remaining small bowel.. Campesterol levels in proportion to cholesterol decreased markedly more, and those of cholestanol markedly less, than would be expected simply due to the amount of proximal small intestine removed, whereas sitosterol proportions decreased in proportion to the length of gut resection. Campesterol proportions markedly (P = 0.06) increased between 1 and 2 months after 50% resection but remained unchanged after 75% resection. Crypt cell proliferation was only increased in the 75% resection group (P < 0.05). The longer the proximal gut resection, the lower was the mucosal enzyme activity. Both resection groups showed increased plasma cholesterol precursor proportions and crypt depth (P < 0.05), whereas villus height remained unchanged. After massive proximal resection campesterol and sitosterol proportions were inversely related to crypt cell proliferation (r = -0.86-0.83, P < 0.01).. Increased crypt cell proliferation activated by massive proximal gut resection may act as a previously unrecognized factor in aggravating cholesterol malabsorption and retarding its recovery during the early postoperative period. These findings warrant further investigation.

    Topics: Animals; Cell Division; Cholesterol; Disaccharidases; Intestinal Absorption; Intestinal Mucosa; Intestine, Small; Phytosterols; Sitosterols; Swine

2000
Exposure of Chironomus riparius larvae (diptera) to lead, mercury and beta-sitosterol: effects on mouthpart deformation and moulting.
    Chemosphere, 2000, Volume: 41, Issue:10

    Mouthpart deformation in chironomid larvae is induced by exposure to chemical contaminants and is becoming an established bio-indicator in sediment assessment programmes. However, concentration-response relationships with causal agents have only been established occasionally and with varying success. In this laboratory study, instar II and III larvae were exposed to sub-lethal concentrations of lead, mercury and beta-sitosterol. A significant deformation response was induced in the pecten with lead and mercury. Deformation frequencies of the mentum after metal exposures were not significantly different from the control. Moulting was retarded by both metals and was well correlated with mouthpart deformation. The beta-sitosterol is an endocrine disruptor, which was used to test the hypothetical cause-effect relation between disruption of ecdyson functioning and chironomid deformation. In the present study, exposure to sublethal concentrations of beta-sitosterol did not result in any effect on deformation or moulting. As such, the proposed hypothesis of endocrine disruptors as primary causal agents of chironomid deformation could not be substantiated. Acetone, which was used as a solvent to apply beta-sitosterol caused a significant increase of mentum deformation. The ground filtration paper used as substrate seemed to induce deformities as well. Substrate contamination, acetone and (especially) inbreeding were most probably responsible for the high deformation frequencies in the control conditions.

    Topics: Animals; Chironomidae; Environmental Pollutants; Larva; Lead; Mercury; Molting; Mouth; Sitosterols

2000
Hyperabsorption and retention of campestanol in a sitosterolemic homozygote: comparison with her mother and three control subjects.
    Journal of lipid research, 2000, Volume: 41, Issue:11

    We measured the percent absorption, turnover, and distribution of campestanol (24-methyl-5alpha-cholestan-3beta-ol) in a sitosterolemic homozygote, her obligate heterozygous mother, and three healthy human control subjects. For reasons relating to sterol hyperabsorption, the homozygote consumed a diet low in plant sterols that contained campestanol at about 2 mg/day. The heterozygote and three control subjects were fed a diet supplemented with a spread that contained campestanol at 540 mg/day and sitostanol (24-ethyl-5alpha-cholestan-3beta-ol) at 1.9 g/day as fatty acid esters. Plasma campestanol concentrations determined by capillary gas-liquid chromatography were 0.72 +/- 0.03 mg/dl in the homozygote, 0.09 +/- 0.04 mg/dl in the heterozygote, and 0.05 +/- 0.03 mg/dl for the control mean. After simultaneous pulse labeling with [3alpha-(3)H]campestanol intravenously and [23-(14)C]campestanol orally, the maximum percent absorption measured by the plasma dual-isotope ratio method as a single time point was 80% in the homozygote, 14.3% in the heterozygote, and 5.5 +/- 4.3% as the mean for three control subjects. Turnover (pool size) values estimated by mathematical analysis of the specific activity versus time [3alpha-(3)H]campestanol decay curves were as follows: 261 mg in the homozygote, 27.3 mg in the heterozygote, and 12.8 +/- 7.6 mg in the three control subjects (homogygote vs. controls, P < 0.001). The calculated production rate (mg/24 h) equivalent to actual absorption in the presence of dietary sterols and stanols was 0.67 mg/day or 31% of intake in the homozygote, 2.1 mg/day or 0.3% of intake in the heterozygote, and 0.7 +/- 0.3 mg/day or 0.1% of intake in the three control subjects. However, the excretion constant from pool A (K(A)) was prolonged markedly in the homozygote, but was 100 times more rapid in the heterozygote and three control subjects.Thus, campestanol, like other noncholesterol sterols, is hyperabsorbed and retained in sitosterolemic homozygotes. However, campestanol absorption was only slightly increased in the sitosterolemic heterozygote and removal was as rapid as in control subjects.

    Topics: Adolescent; Adult; Carbon Radioisotopes; Cholesterol; Diet; Female; Half-Life; Heterozygote; Homozygote; Humans; Intestinal Absorption; Kinetics; Lipid Metabolism, Inborn Errors; Male; Middle Aged; Phytosterols; Sitosterols; Tritium

2000
Synergistic effects of alpha-tocopherol, beta-sitosterol and squalene on antioxidant activity assayed by crocin bleaching method.
    Die Nahrung, 2000, Volume: 44, Issue:5

    Topics: Algorithms; Antioxidants; Carotenoids; Drug Synergism; Hypolipidemic Agents; Kinetics; Sitosterols; Squalene; Vitamin E

2000
Identification of metabolites of phytosterols in rat feces using GC/MS.
    Archives of pharmacal research, 2000, Volume: 23, Issue:6

    Beta-sitosterol, campesterol and stigmasterol have been known to the phytosterols the most frequently found in plants. Metabolism of phytosterols was investigated using rat feces and liver microsomes. Feces were collected after phytosterols (a well characterized mixture of beta-sitosterol 40%, campesterol 30% and dihydrobrasicasterol) were administered orally (0.5 g/kg) to rats. Metabolites of phytosterols were identified using GC/MS. Three peaks were eluted at 12.47, 12.65, 12.87 min and had characteristic molecular ions m/z 428, 430, 432, respectively. Three fecal metabolites were identified as androstadienedione, androstenedione, and androstanedione. No metabolites could be detected in the rat liver microsomal reaction mixture. The results suggest that the metabolites of phytosterols in rat feces are formed by oxidation at 3- position, saturation at 5- and 6- position, and 17- side chain cleavage in the rat large intestine.

    Topics: Animals; Cholesterol; Feces; Gas Chromatography-Mass Spectrometry; In Vitro Techniques; Male; Microsomes, Liver; Phytosterols; Rats; Rats, Sprague-Dawley; Sitosterols

2000
A comparative study of the effects of cholesterol, beta-sitosterol, beta-sitosterol glucoside, dehydroepiandrosterone sulphate and melatonin on in vitro lipid peroxidation.
    Metabolic brain disease, 2000, Volume: 15, Issue:4

    The free radical scavenging abilities of the structurally related steroids beta-sitosterol, beta-sitosterol glucoside (plant sterols and sterolins), cholesterol, and dehydroepiandrosterone sulphate (DHEAS) were compared with melatonin (an efficient free radical scavenger) in an in vitro system which measures lipid peroxidation of platelet membranes in the presence of iron (Fe2+). Lipid peroxidation is a process whereby cellular membranes are damaged due to the oxidative deterioration of polyunsaturated lipids, which may lead to cell death and disease in living organisms. Substances such as vitamin E protect cellular membranes against oxidative damage due to their chemical structures. The steroids cholesterol, beta-sitosterol, beta-sitosterol glucoside and dehydroepiandrosterone (DHEA) are structurally related to each other. During aging, serum concentrations of DHEA, DHEAS and melatonin decrease, while the concentration of cholesterol tends to increase. The aim of the present study was to compare the role these substances play in lipid peroxidation over a wide concentration range. At concentrations lower than the free iron in the reaction mixture, all the steroids investigated decreased lipid peroxidation. At higher concentrations, cholesterol and beta-sitosterol increased lipid peroxidation, while DHEAS and melatonin continued to decrease lipid peroxidation.

    Topics: Aging; Androsterone; Antioxidants; Blood Platelets; Cholesterol; Free Radical Scavengers; Humans; Hypolipidemic Agents; In Vitro Techniques; Lipid Peroxidation; Melatonin; Sitosterols

2000
[Studies on chemical constituents of Forsythia suspensa (Thunb) Vahl].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1999, Volume: 24, Issue:5

    To study the chemical constituents of Forsythia suspensa.. Basedon silicacolumn chromatography, of which six compounds were obtained from the alcohol extract of F. suspensa, three identified by physicochemical and spectroscopic analyses.. The three compounds were identified as stearic acid, palmitic acid and beta-sitosterol.. The three compounds were separated from F. suspensa fruits for the first time.

    Topics: Forsythia; Fruit; Palmitic Acid; Plants, Medicinal; Sitosterols; Stearic Acids

1999
[A study on chemical components of Tetrastigma hemsleyanum Diels et Gilg. Native to China].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1999, Volume: 24, Issue:10

    To investigate the chemical constituents of Tetrastigma hemsleyanum native to China.. Compounds were separated by column chronatography with silica gel and elucidated by chemical evidence and spectral analysis.. Four compounds were isolated from the petroleum ether extract. Their structures were identifies as taraxerone, taraxerol,beta-sitosterol and ergosterol.. These compounds were isolated from the plant for the first time.

    Topics: Ergosterol; Oleanolic Acid; Plants, Medicinal; Sitosterols; Vitaceae

1999
[Studies on chemical constituents of the roots of Gypsophila oldhamiana Miq].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1999, Volume: 24, Issue:11

    To separate compounds from the root of Gypsophila oldhamiana.. Chemical and chromatographic methods were used to separate the compounds. IR, MS, NMR were used to determine the structures of compounds.. Compound pentacosanoic acid, lacceroic acid, beta-sitosterol, alpha-spinasterol, daucosterol and sucrose were identified.. All the above compounds were obtained from this genus for the first time.

    Topics: Caryophyllaceae; Plant Roots; Plants, Medicinal; Sitosterols; Stigmasterol

1999
[Studies on chemical constituents of Thalictrum atriplex Finet et Gagnep].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1999, Volume: 24, Issue:3

    To study the chemical constituents in the aerial part of Thalictrum atriplex.. Chromatography and spectral analysis were used to isolate and elucidate the constituents.. Six compounds were isolated from the aerial part of Thalictrum atriplex, and elucidated as protocatechuic acid, caffeic acid, p-coumaric acid, kaempferol, beta-sitosterol and N-methylcorydaldine.. They are all isolated from the plant for the first time.

    Topics: Caffeic Acids; Coumaric Acids; Drugs, Chinese Herbal; Flavonoids; Hydroxybenzoates; Kaempferols; Plants, Medicinal; Propionates; Sitosterols; Thalictrum

1999
[Chemical composition of Fordia cauliflora Hemsl].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1999, Volume: 24, Issue:2

    To study chemical constituents of the root of Fordia cauliflora.. Three compounds were obtained from the ethanolic extract of the roots of F. cauliflora by silica column chromatography, and identified by physico-chemical and spectroscopic analysis.. The compounds were identified as stearic acid, palmitic acid and beta-sitosterol.. These compounds were obtained from this plant for the first time.

    Topics: Fabaceae; Palmitic Acid; Plants, Medicinal; Sitosterols; Stearic Acids

1999
[Studies on the chemical constituents of Adina rubella (II)].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1999, Volume: 22, Issue:9

    Three constituents were isolated from Adina rubella. Their structures were identified as beta-sitosterol, quinovic acid, 3-oxo-urs-12-ene-27, 28-dioic acid.

    Topics: Plants, Medicinal; Rubiaceae; Sitosterols; Triterpenes

1999
[Studies on chemical constituents of the stem bark of Taxus cuspidata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1999, Volume: 22, Issue:7

    In order to study the active constituents in the stem barks of Taxus cuspidata Sieb. et Zucc., led to the isolation and structural determination of three compounds. On the basis of chemical evidences and spectral analysis (UV, IR, 1HNMR, 13CNMR and FAB-MS,) the structures of I, II and III were elucidated as baccatin I 1-hydroxy, taxinine J 2-deacetoxy and beta-sitosterol. Compound I was found from this plant for the first time.

    Topics: Alkaloids; Plant Bark; Plants, Medicinal; Sitosterols; Taxoids; Taxus

1999
[Studies on chemical constituents of Lysimachia pentapetala].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1999, Volume: 22, Issue:1

    From the ethanol extract of Lysimachia pentapetala, six compounds have been isolated. These compounds were identified as triacontanol, beta-sitosterol, glycerol monopalmitate, succinic acid, flavonol glycosides and hitrite upon the date of mp, IR, MS and 1HNMR tests.

    Topics: Drugs, Chinese Herbal; Fatty Alcohols; Plants, Medicinal; Primulaceae; Sitosterols; Succinic Acid

1999
[Pharmacognostical studies on the roots of Euphorbia soongarica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1999, Volume: 22, Issue:5

    Morphological and microscopical characters of the roots of Euphorbia soongarica Boiss. used as one of the origins of the Chinese medicine Daji in Xinjiang Autonomous Region of China were described and illustrated with line drawings. TLC and HPLC analysis of the above drug was also undertaken. These studies provide referencial informations for clinics, quality control, development and identification of this crude drug.

    Topics: Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Euphorbia; Pharmacognosy; Plant Roots; Plants, Medicinal; Powders; Quality Control; Sitosterols

1999
[Chemical constituents of Girardinia palmata ssp ciliata].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1999, Volume: 22, Issue:4

    Thirteen constituents were identified from Girardinia palmata ssp ciliata C. J. Chen by using GC-MS, which amounted to 84.5% of the total peaks, the main constituent were linoleic acid (52.01%) and dimethyl fumarate (10.05%). The dissociated amino acids and KNO(3) in the sample amounted to 43.30 mg/100 g and 3.0%. Five compounds were isolated and elucidated as octadecane, hexadecylic acid, beta-sitosterol, p-coumaric acid and potasium nitrate.

    Topics: Alkanes; Coumaric Acids; Dimethyl Fumarate; Fumarates; Gas Chromatography-Mass Spectrometry; Linoleic Acid; Plants, Medicinal; Propionates; Sitosterols; Urticaceae

1999
Effects of wood-related sterols on the reproduction, egg survival, and offspring of brown trout (Salmo trutta lacustris L.).
    Ecotoxicology and environmental safety, 1999, Volume: 42, Issue:1

    Maturing lake trout (Salmo trutta lacustris) of both sexes were exposed to 10 and 20 microg/liter phytosterols, mainly ss-sitosterol, for 4.5 months prior to spawning. Eggs from preexposed females were artificially fertilized with milt from preexposed males in clean water, whereupon the eggs were incubated in clean water until hatching. Yolk sac fry were followed until swim-up, and mortality as well as deformities was recorded. The physiological status of the parent fish was documented, as was the occurrence of phytosterols in bile liquid and gonads. In addition, eggs from preexposed females were fertilized with milt from unexposed males to evaluate the existence of possible sex-linked differences. The results indicate a markedly increased dose-dependent egg mortality, smaller egg size, and lower mean weight of the the yolk sac stage larvae. There was a higher prevalence of deformed or otherwise diseased larvae, especially at the higher dose, but also in the groups where unexposed males were used for fertilization, indicating a female-linked effect mechanism. A causal link between effects on eggs and brood was obtained through a dose-dependent increase in phytosterols in the roe. Several physiological parameters (higher plasma estradiol, higher 7-ethoxyresorufin O-deethylase activity) implied slower maturation of the exposed female fish, whereas indications of accelerated maturation were obtained for the male fish from the same groups. The results indicate that naturally occurring wood-derived compounds in pulp mill effluents may be responsible for reproductive impacts previously observed in fish both in the laboratory and in the receiving waters of pulp mill effluents. The results also suggest that more attention should be paid to process streams emanating from the unbleached part of the mill.

    Topics: Animals; Bile; Female; Male; Ovum; Reproduction; Sitosterols; Sterols; Trout; Wood; Zygote

1999
Saw palmetto extracts potently and noncompetitively inhibit human alpha1-adrenoceptors in vitro.
    The Prostate, 1999, Feb-15, Volume: 38, Issue:3

    We wanted to test whether phytotherapeutic agents used in the treatment of lower urinary tract symptoms have alpha1-adrenoceptor antagonistic properties in vitro.. Preparations of beta-sitosterol and extracts of stinging nettle, medicinal pumpkin, and saw palmetto were obtained from several pharmaceutical companies. They were tested for their ability to inhibit [3H]tamsulosin binding to human prostatic alpha1-adrenoceptors and [3H]prazosin binding to cloned human alpha1A- and alpha1B-adrenoceptors. Inhibition of phenylephrine-stimulated [3H]inositol phosphate formation by cloned receptors was also investigated.. Up to the highest concentration which could be tested, preparations of beta-sitosterol, stinging nettle, and medicinal pumpkin were without consistent inhibitory effect in all assays. In contrast, all tested saw palmetto extracts inhibited radioligand binding to human alpha1-adrenoceptors and agonist-induced [3H]inositol phosphate formation. Saturation binding experiments in the presence of a single saw palmetto extract concentration indicated a noncompetitive antagonism. The relationship between active concentrations in vitro and recommended therapeutic doses for the saw palmetto extracts was slightly lower than that for several chemically defined alpha1-adrenoceptor antagonists.. Saw palmetto extracts have alpha1-adrenoceptor-inhibitory properties. If bioavailability and other pharmacokinetic properties of these ingredients are similar to those of the chemically defined alpha1-adrenoceptor antagonists, alpha1-adrenoceptor antagonism might be involved in the therapeutic effects of these extracts in patients with lower urinary tract symptoms suggestive of benign prostatic obstruction.

    Topics: Adrenergic alpha-1 Receptor Antagonists; Adrenergic alpha-Antagonists; Binding, Competitive; Cell Line; Cloning, Molecular; Humans; Logistic Models; Male; Plant Extracts; Plants, Medicinal; Prostate; Radioligand Assay; Sitosterols

1999
Safety evaluation of phytosterol esters. Part 1. Assessment of oestrogenicity using a combination of in vivo and in vitro assays.
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 1999, Volume: 37, Issue:1

    Phytosterols are natural constituents of the human diet, and as part of an extensive programme of safety evaluation studies investigating their use as a novel food ingredient, the possible oestrogenic effects of phytosterols have been investigated using a combination of in vitro and in vivo assays. Competitive binding with the immature rat uterine oestrogen receptor (ER) has been used to measure the ability of phytosterols to bind to ERs while the transcriptional activation of oestrogen-responsive genes has been examined in an oestrogen-inducible yeast screen. Phytosterols did not display any activity in these in vitro assays. Uterotrophic assays have been conducted to investigate the potential for phytosterols to elicit an oestrogenic response when administered orally to immature female rats (n = 10) at doses of 0, 5, 50 or 500 mg/kg/day for 3 consecutive days. Phytosterols (a well characterized mixture of beta-sitosterol, campesterol and stigmasterol) and phytosterol esters (the previous phytosterol mixture esterified with fatty acids from sunflower oil) did not exhibit oestrogenic activity in the immature female rat using uterine wet weight as the endpoint. Beta-oestradiol (0.4 mg/kg/day) consistently produced a significant increase in uterus weights. Coumestrol (a known phytoestrogen) was also tested as a weak positive control and produced a dose response at doses of 20, 40 and 80 mg/kg/day in the uterotrophic assay. In conclusion, we have shown that phytosterols do not bind to the ER and do not stimulate transcriptional activity of the human ER in a recombinant yeast strain. In addition, there was no indication of oestrogenicity from the uterotrophic assay when the material was administered by oral gavage to immature female rats.

    Topics: Administration, Oral; Animals; Binding, Competitive; Cholesterol; Coumestrol; Dose-Response Relationship, Drug; Esters; Estradiol; Estrogens, Non-Steroidal; Female; Organ Size; Phytosterols; Rats; Rats, Wistar; Receptors, Estrogen; Saccharomyces cerevisiae; Sitosterols; Stigmasterol; Uterus

1999
Transformation of bile acids and sterols by clostridia (fusiform bacteria) in Wistar rats.
    Lipids, 1999, Volume: 34, Issue:3

    The effects on bile acid and sterol transformation of clostridia (fusiform bacteria), the dominant intestinal bacteria in rodents (ca. 10(10) counts per g wet feces) were examined in Wistar rats. After inoculation of clostridia into germ-free rats and into rats previously inoculated solely with Escherichia coli, most of the endogenous bile acids were deconjugated, and cholic acid and chenodeoxycholic acid were 7alpha-dehydroxylated to deoxycholic acid and lithocholic acid, respectively. Tauro-beta-muricholic acid, another major bile acid in rats, was deconjugated, but only part of it (ca. 30%) was transformed into hyodeoxycholic acid. Cholesterol and sitosterol were also reduced to coprostanol and sitostanol, respectively. Escherichia coli transformed neither bile acids nor sterols. These data suggest that clostridia play an important role in the formation of secondary bile acids and coprostanol in rats.

    Topics: Animals; Bile Acids and Salts; Cholestanol; Cholesterol; Cholic Acid; Clostridium; Escherichia coli; Feces; Female; Germ-Free Life; Male; Rats; Rats, Wistar; Sitosterols; Sterols; Taurocholic Acid

1999
Biosynthesis of bitter acids in hops. A (13)C-NMR and (2)H-NMR study on the building blocks of humulone.
    European journal of biochemistry, 1999, Volume: 263, Issue:2

    The biosynthesis of humulone, an antibacterial bitter acid from hops, was studied by isotope-incorporation experiments using (13)C-labelled glucose or (2)H(2)O. (13)C enrichments, (2)H enrichments and (13)C(13)C coupling patterns identify isovaleryl-CoA, malonyl-CoA and dimethylallyl pyrophosphate as precursors for humulone. Dimethylallyl pyrophosphate, which serves as a building block for the bitter acid, is generated via the deoxyxylulose pathway of terpenoid biosynthesis. The data confirm that a symmetrical intermediate is involved in humulone formation.

    Topics: Acyl Coenzyme A; Cyclohexenes; Magnetic Resonance Spectroscopy; Models, Chemical; Plants; Sitosterols; Terpenes

1999
Cholesterol-lowering margarines.
    The Medical letter on drugs and therapeutics, 1999, Jun-18, Volume: 41, Issue:1055

    Topics: Administration, Oral; Anticholesteremic Agents; Cross-Over Studies; Double-Blind Method; Drug Administration Schedule; Female; Humans; Male; Margarine; Phytosterols; Randomized Controlled Trials as Topic; Sitosterols

1999
Optimisation of plant sterols incorporation in human keratinocyte plasma membrane and modulation of membrane fluidity.
    Chemistry and physics of lipids, 1999, Volume: 101, Issue:2

    The in vitro effects of plant sterols were investigated with regard to their uptake and membrane lipid fluidity in human keratinocytes. Among the different media tested to transport sterols (liposomes, micelles and organic solvents), the best results in terms of incorporation and viability were obtained by the use of the organic solvents dimethylsulfoxide and ethanol. After 48 h incubation exogenous sterol can account for about 30% of the total cell sterol content. The total sterol amount in plasma membranes increased 2-fold after incubation with cholesterol, whereas it was not altered when phytosterols were incorporated. The incorporation of cholesterol, sitosterol and stigmasterol led to an increase in the percent of unsaturated fatty acid C18:1 in the plasma membrane. The effect of this uptake on membrane fluidity was studied by means of fluorescence polarisation using DPH and TMA-DPH as fluorescent probes. Whereas cholesterol and sitosterol had no significant effect on the DPH fluorescence anisotropy (rs), the presence of stigmasterol induced a 12% decrease of rs reflecting an increase in membrane fluidity. We can conclude from this study that in the presence of sitosterol, the mean fluidity of the membrane is regulated whereas stigmasterol triggers a looseness of molecular packing of phospholipids acyl chains, in accordance with previous results obtained on purely lipid model membranes.

    Topics: Cell Line; Cell Membrane; Fluorescence Polarization; Humans; Keratinocytes; Membrane Fluidity; Models, Chemical; Phytosterols; Sitosterols

1999
Mass spectrometry characterization of the 5alpha-, 7alpha-, and 7beta-hydroxy derivatives of beta-sitosterol, campesterol, stigmasterol, and brassicasterol.
    Journal of agricultural and food chemistry, 1999, Volume: 47, Issue:8

    The 5alpha-hydroperoxides of beta-sitosterol, campesterol, stigmasterol, and brassicasterol were obtained by photooxidation of the respective sterols in pyridine in the presence of hematoporphyrine as sensitizer. The reduction of the hydroperoxides gives the corresponding 5alpha-hydroxy derivatives. The 7alpha- and 7beta-hydroperoxides of the sterols were obtained by allowing an aliquot of the 5alpha-hydroperoxides to isomerize to 7alpha-hydroperoxides, which in turn epimerize to 7beta-hydroperoxides. The reduction gave the corresponding 7alpha- and 7beta-hydroxy derivatives. The 5alpha-, 7alpha-, and 7beta-hydroxy derivatives of beta-sitosterol, campesterol, stigmasterol, and brassicasterol were identified by comparing thin-layer chromatography mobilities, specific color reactions, and mass spectral data with those of the corresponding hydroxy derivatives of cholesterol, which were synthesized in the same manner. The phytosterols had the same behavior to photooxidation as cholesterol and, moreover, the different phytosterols photooxidized at about the same rate. The mass spectra of the trimethylsilyl ethers of the hydroxy derivatives of the phytosterols investigated and of the corresponding hydroxy derivatives of cholesterol have the same fragmentation patterns and similar relative ion abundances.

    Topics: Cholestadienols; Cholesterol; Gas Chromatography-Mass Spectrometry; Hydroxylation; Mass Spectrometry; Peroxides; Phytosterols; Sitosterols; Stigmasterol

1999
The effect of cell wall components on glycine-enhanced sterol side chain degradation to androstene derivatives by mycobacteria.
    Applied microbiology and biotechnology, 1999, Volume: 52, Issue:4

    beta-Sitosterol side chain degradation by Mycobacterium sp. NRRL MB 3683 results in the formation of androstene derivatives and is increased in the presence of glycine. As the sterol transformation is carried out inside the cell, higher product accumulation could indicate faster diffusion of highly hydrophobic substrate through the cell wall permeability barrier. Cell wall preparations were obtained to analyse the effect of glycine on peptidoglycan components. Peptidoglycan is known to be the target for glycine action. In glycine-treated preparations, the molar ratio of diaminopimelic acid:muramic acid, the marker compounds of tetrapeptides and glycan strands respectively, was about 60% lower than in the control. This indicates a possible reduction in cross-linking between peptide units and the destruction of peptidoglycan. Unexpectedly, glycine also caused changes in the relative proportion of mycolic acids to other lipids occurring in the strain used for this study. The enhancement of beta-sitosterol side chain degradation is likely to result from disturbing the integrity of the cell wall components responsible for the permeability barrier in mycobacteria.

    Topics: Androstenes; Biomass; Biotransformation; Cell Wall; Densitometry; Glycine; Mass Spectrometry; Membrane Lipids; Mycobacterium; Mycolic Acids; Peptidoglycan; Sitosterols

1999
Apolipoprotein E participates in the regulation of very low density lipoprotein-triglyceride secretion by the liver.
    The Journal of biological chemistry, 1999, Dec-10, Volume: 274, Issue:50

    ApoE-deficient mice on low fat diet show hepatic triglyceride accumulation and a reduced very low density lipoprotein (VLDL) triglyceride production rate. To establish the role of apoE in the regulation of hepatic VLDL production, the human APOE3 gene was introduced into apoE-deficient mice by cross-breeding with APOE3 transgenics (APOE3/apoe-/- mice) or by adenoviral transduction. APOE3 was expressed in the liver and, to a lesser extent, in brain, spleen, and lung of transgenic APOE3/apoe-/- mice similar to endogenous apoe. Plasma cholesterol levels in APOE/apoe-/- mice (3.4 +/- 0.5 mM) were reduced when compared with apoe-/- mice (12.6 +/- 1.4 mM) but still elevated when compared with wild type control values (1.9 +/- 0.1 mM). Hepatic triglyceride accumulation in apoE-deficient mice was completely reversed by introduction of the APOE3 transgene. The in vivo hepatic VLDL-triglyceride production rate was reduced to 36% of control values in apoE-deficient mice but normalized in APOE3/apoe-/- mice. Hepatic secretion of apoB was not affected in either of the strains. Secretion of (3)H-labeled triglycerides synthesized from [(3)H]glycerol by cultured hepatocytes from apoE-deficient mice was four times lower than by APOE3/apoe-/- or control hepatocytes. The average size of secreted VLDL particles produced by cultured apoE-deficient hepatocytes was significantly reduced when compared with those of APOE3/apoe-/- and wild type mice. Hepatic expression of human APOE3 cDNA via adenovirus-mediated gene transfer in apoE-deficient mice resulted in a reduction of plasma cholesterol depending on plasma apoE3 levels. The in vivo VLDL-triglyceride production rate in these mice was increased up to 500% compared with LacZ-injected controls and correlated with the amount of apoE3 per particle. These findings indicate a regulatory role of apoE in hepatic VLDL-triglyceride secretion, independent from its role in lipoprotein clearance.

    Topics: Animals; Apolipoproteins E; Cells, Cultured; Cholesterol; Crosses, Genetic; Fatty Acids, Nonesterified; Glycerol; Homeostasis; Humans; Lipoproteins; Lipoproteins, VLDL; Liver; Mice; Mice, Knockout; Mice, Transgenic; Microscopy, Immunoelectron; Phytosterols; Sitosterols; Sterols; Triglycerides; Tritium

1999
Study of the topical anti-inflammatory activity of Achillea ageratum on chronic and acute inflammation models.
    Zeitschrift fur Naturforschung. C, Journal of biosciences, 1999, Volume: 54, Issue:11

    We have produced a chloroform extract from Achillea which includes stigmasterol and sitosterol. By comparing it with the pure compounds an anti-inflammatory effect (with mouse ears) is assumed. The topical anti-inflammatory effect of the chloroform extract from Achillea ageratum (Asteraceae) and of stigmasterol and beta-sitosterol, isolated of this extract has been evaluated, against to 12-0-tetradecanoylphorbol acetate (TPA)-induced mouse ear edema, using simple (acute model) and multiple applications (chronic model) of the phlogistic agent. Myeloperoxydase activity also was studied in the inflamed ears. In the acute model the extract exerted a dose-dependent effect. All the doses assayed (1, 3 and 5 mg/ear) significantly reduced the edema (50%, 66% and 82%, respectively). The isolated sterols stigmasterol and beta-sitosterol (with doses of 0.5 mg/ear) had similar effect as the extract with doses of 1 and 3 mg (59% and 65% respectively). In the chronic model the anti-inflammatory effect generally was a more moderate one. The highest dose of the extract decreased the edema reduction to 26% with the highest dose of the extract applied. With the compounds the effect decreased to 36% with stigmasterol, and 40.6% with beta-sitosterol. Myeloperoxydase activity (MPO) was reduced by the extract and the compounds in the acute model, however, in the chronic edema, the enzyme inhibition was very weak with all treatments even with the standard substance. These results indicate that the chloroform extract of Achillea ageratum and some of the its components stigmasterol and beta-sitosterol are more effective as topical anti-inflammatory agents in acute than in the chronic process and their action is markedly influenced by the inhibition of neutrophil migration into inflamed tissue.

    Topics: Acute Disease; Animals; Anti-Inflammatory Agents; Chloroform; Chronic Disease; Dexamethasone; Disease Models, Animal; Ear; Edema; Indomethacin; Mice; Peroxidase; Plant Extracts; Plants, Medicinal; Sitosterols; Stigmasterol; Tetradecanoylphorbol Acetate

1999
[Chemical constituents of fruits of Gardenia sootepensis Hutch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1999, Volume: 24, Issue:1

    To demonstrate the chemical constituents of the fruits of Gardenia sootepensis.. Column chromatographic technology was employed to separate the water soluble part, and the compounds obtained were elucidated by spectral and chemical analysis.. Ten compounds have been isolated, seven of which elucidated respectively as D-mannitol, beta-sitosterol, deacetylasperulosidic acid methyl ester, geniposidic acid, geniposide, scandoside methyl ester and dimeric molecule of quinide.. All the compounds were obtained from this plant for the first time.

    Topics: Drugs, Chinese Herbal; Fruit; Gardenia; Glucosides; Iridoid Glucosides; Iridoids; Mannitol; Plants, Medicinal; Pyrans; Sitosterols

1999
[Effects of different amount of ginger juice on prepared products of Rhizoma Pinelliae].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1998, Volume: 21, Issue:6

    Rhizoma Pinelliae were diged in Ginger juice of different propertion, the total alkaloid contents of these products were all higher than the raw Rhizoma Pinelliae, and related to the actions of anti-tumous cell. The contents of beta-sitosterol of these products were related to the amount of Ginger juice which is added in Pinelliae Rhizoma, but only the content of beta-sitosterol of the Pinelliae product which is prepared by same amount of Ginger juice was slight higher than the raw Rhizoma Pinelliae. The stimulations of five kinds of products on mice have no obvious relation to the amounts of Ginger juice which were added in Rhizoma Pinelliae, but the stimulation of the Pinellia product which was prepared by same amount of Ginger juice was the lowest of all products on mice. Dependent on above experiment results, we suggest that Rhizoma Pinelliae processed by Ginger juice should be prepared by same amount of Ginger juice with Rhizoma Pinelliae.

    Topics: Alkaloids; Animals; Antineoplastic Agents; Behavior, Animal; Dose-Response Relationship, Drug; Drugs, Chinese Herbal; Humans; K562 Cells; Mice; Mice, Inbred ICR; Pinellia; Sitosterols; Technology, Pharmaceutical; Zingiber officinale

1998
[Studies on the chemical constituents of Quercus mongolica].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1998, Volume: 21, Issue:4

    Seven compounds were isolated from Quercus mongolica Fisch., six (1-VI) of them were identified as fridelin (I), beta-amyrin (II), 1-octadecanol (III), beta-sitosterol (IV), daucosterol (V) and gallic acid (VI) by means of chemical, physical and spectrosopic evidiences.

    Topics: Fatty Alcohols; Gallic Acid; Oleanolic Acid; Plant Leaves; Plants, Medicinal; Quercus; Sitosterols; Spectrophotometry, Ultraviolet; Triterpenes

1998
[Study on the chemical components of Alpinia officinarum].
    Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 1998, Volume: 21, Issue:7

    Four crystalline substances were isolated from rhizome of Alpinia officinarum Hance. They were identified as beta-Sitosterol (I), Galangin (II), Emodin (III) and Quercetin (IV), I and III were separated from this plant for the first time.

    Topics: Alpinia; Emodin; Flavonoids; Quercetin; Rhizome; Sitosterols; Spectrophotometry, Ultraviolet; Spectroscopy, Near-Infrared

1998
Down-regulation of cholesterol biosynthesis in sitosterolemia: diminished activities of acetoacetyl-CoA thiolase, 3-hydroxy-3-methylglutaryl-CoA synthase, reductase, squalene synthase, and 7-dehydrocholesterol delta7-reductase in liver and mononuclear leu
    Journal of lipid research, 1998, Volume: 39, Issue:1

    Sitosterolemia is a recessively inherited disorder characterized by abnormally increased plasma and tissue plant sterol concentrations. Patients have markedly reduced whole body cholesterol biosynthesis associated with suppressed hepatic, ileal, and mononuclear leukocyte 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, the rate-controlling enzyme in cholesterol biosynthetic pathway, coupled with significantly increased low density lipoprotein (LDL) receptor expression. To investigate the mechanism of down-regulated cholesterol biosynthesis, we assayed several other key enzymes in the cholesterol biosynthetic pathway including acetoacetyl-CoA thiolase, HMG-CoA synthase, squalene synthase, and 7-dehydrocholesterol delta7-reductase activities in liver and freshly isolated mononuclear leukocytes from four sitosterolemic patients and 19 controls. Hepatic acetoacetyl-CoA thiolase, HMG-CoA synthase, reductase, and squalene synthase activities were significantly decreased (P < 0.05) -39%, -54%, -76%, and -57%, respectively, and 7-dehydrocholesterol delta7-reductase activity tended to be lower (-35%) in the sitosterolemic compared with control subjects. The reduced HMG-CoA synthase, reductase, and squalene synthase activities were also found in mononuclear leukocytes from a sitosterolemic patient. Thus, reduced cholesterol synthesis is caused not only by decreased HMG-CoA reductase but also by the coordinate down-regulation of entire pathway of cholesterol biosynthesis. These results suggest that inadequate cholesterol production in sitosterolemia is due to abnormal down-regulation of early, intermediate, and late enzymes in the cholesterol biosynthetic pathway rather than a single inherited defect in the HMG-CoA reductase gene.

    Topics: Acetyl-CoA C-Acetyltransferase; Adult; Cholesterol; Farnesyl-Diphosphate Farnesyltransferase; Humans; Hydroxymethylglutaryl CoA Reductases; Hydroxymethylglutaryl-CoA Synthase; Leukocytes, Mononuclear; Liver; Male; Oxidoreductases; Oxidoreductases Acting on CH-CH Group Donors; Sitosterols

1998
Absorption, excretion, and distribution of plant sterols after proximal gut resection and autotransplantation of porcine ileum.
    Lipids, 1998, Volume: 33, Issue:3

    Contribution of different gut segments to plant sterol absorption, adaptation of plant sterol absorption after partial small bowel resection, and effects of gut transplantation (necessitates extrinsic autonomic denervation and lymphatic disruption) on plant sterol biodynamics are unclear. We studied the consequences of massive proximal small bowel resection and autotransplantation of the remaining ileum on the adaptive absorption and biodynamics of plant sterols. Dietary, fecal, biliary, hepatic and plasma plant sterols, fecal elimination and absorption of cholesterol, small bowel morphology, and intestinal transit were determined before (n = 5) and at 4, 8, and 14 wk after resection of the proximal 75% of the jejunoileum (n = 15) and autotransplantation of the remaining ileum (n = 15) or transection (n = 5). Proximal gut resection significantly reduced cholesterol absorption efficiency; percentage absorption and biliary secretion of plant sterols; plasma, biliary and hepatic campesterol-to-cholesterol proportions; and sitosterol proportions in plasma and bile. Autotransplantation of the remaining ileum further significantly decreased cholesterol absorption efficiency; percentage absorption and biliary secretion of campesterol; campesterol proportions in plasma, bile and liver; and plasma proportions of sitosterol while increasing fecal excretion of neutral and acidic steroids. Plasma proportions of the two plant sterols, but absorption of just campesterol, were gradually improved with increasing cholesterol absorption and villus height after proximal gut resection; the same result was observed to a lesser degree after ileal autotransplantation. In addition, significant positive correlations were found between percentage cholesterol and campesterol absorption and the plasma plant sterol proportions in both proximal resection groups, between campesterol absorption and ileal villus height in the resection group, and between campesterol absorption and intestinal transit time in the autotransplantation group. In conclusion, plasma campesterol and sitosterol closely reflect absorption of cholesterol and plant sterols from intact and autotransplanted ileum during adaptation to proximal gut resection. A loss of proximal gut absorptive surface impairs cholesterol and campesterol absorption more than sitosterol absorption, the latter being apparently less dependent on available jejunal villus surface area.

    Topics: Animals; Bile; Cholesterol; Denervation; Feces; Ileum; Intestinal Absorption; Phytosterols; Sitosterols; Swine; Transplantation, Autologous

1998
Effect of beta-sitosterol on ultrastructure of liver cells in young and aged mice.
    International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition, 1998, Volume: 68, Issue:2

    The effects of beta-sitosterol on liver ultrastructure were studied using young and aged male mice. Both groups of mice were fed a beta-sitosterol or a control diet. The beta-sitosterol diet contained 1% beta-sitosterol. Ultrastructural differences in the liver cells were evident between two groups fed the two diets. The number of peroxisomes was significantly greater in the liver cells of both young and aged mice fed the beta-sitosterol diet than in those fed the control diet. There were also significant differences in the maximum length of lipid droplets between the young and aged mice fed the beta-sitosterol diet. These results suggest that beta-sitosterol affects liver ultrastructure, and that some ultrastructural differences in liver cells exist between young and aged mice fed the beta-sitosterol diets.

    Topics: Aging; Animals; Diet; Liver; Male; Mice; Microbodies; Microscopy, Electron; Sitosterols

1998
Weight as a surrogate marker of treatment response in tuberculosis.
    The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, 1998, Volume: 2, Issue:6

    Topics: Antitubercular Agents; Drug Therapy, Combination; Humans; Sitosterols; Treatment Outcome; Tuberculosis, Pulmonary; Weight Gain

1998
Diet and cholesterol: foods that help.
    Harvard men's health watch, 1998, Volume: 3, Issue:1

    Topics: Alcohol Drinking; Cholesterol; Dietary Fiber; Female; Garlic; Humans; Hypercholesterolemia; Male; Nuts; Plants, Medicinal; Sitosterols; Soybean Proteins

1998
Plant derived estrogens relax rat mesenteric artery in vitro.
    Life sciences, 1998, Volume: 63, Issue:6

    The aim of this study was to investigate whether plant derived estrogens have the same relaxing effects in vitro as estradiol-17beta on arterial smooth muscle. The mesenteric arterial rings of female and male Wistar rats were studied. The relaxing effects of estradiol-17beta, genistein, daidzein and beta-sitosterol were determined, with particular focus on the role of endothelium. B-sitosterol had no relaxing effect on the arteries. Estradiol-17beta, genistein and daidzein relaxed noradrenaline, potassium chloride and calcium chloride precontracted arterial rings endothelium-independently. The relaxation responses were also independent of gender. Neither the removal of endothelium, nor the inhibition prostacyclin or nitric oxide synthesis, had any effect on the relaxation responses. The exact mechanism of these findings is still unclear.

    Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Calcium Chloride; Estradiol; Estrogens; Female; Genistein; Indomethacin; Isoflavones; Male; Mesenteric Arteries; Muscle, Smooth, Vascular; NG-Nitroarginine Methyl Ester; Norepinephrine; Plant Extracts; Potassium Chloride; Rats; Rats, Wistar; Sitosterols; Vasoconstrictor Agents; Vasodilation

1998
Mapping a gene involved in regulating dietary cholesterol absorption. The sitosterolemia locus is found at chromosome 2p21.
    The Journal of clinical investigation, 1998, Sep-01, Volume: 102, Issue:5

    The molecular mechanisms regulating the amount of dietary cholesterol retained in the body as well as the body's ability to selectively exclude other dietary sterols are poorly understood. Studies of the rare autosomal recessively inherited disease sitosterolemia (OMIM 210250) may shed some light on these processes. Patients suffering from this disease appear to hyperabsorb both cholesterol and plant sterols from the intestine. Additionally, there is failure of the liver's ability to preferentially and rapidly excrete these non-cholesterol sterols into bile. Consequently, people who suffer from this disease have very elevated plasma plant sterol levels and develop tendon and tuberous xanthomas, accelerated atherosclerosis, and premature coronary artery disease. Identification of this gene defect may therefore throw light on regulation of net dietary cholesterol absorption and lead to an advancement in the management of this important cardiovascular risk factor. By studying 10 well-characterized families with this disorder, we have localized the genetic defect to chromosome 2p21, between microsatellite markers D2S1788 and D2S1352 (maximum lodscore 4.49, theta = 0.0).

    Topics: Cardiovascular Diseases; Cholesterol, Dietary; Chromosome Mapping; Chromosomes, Human, Pair 2; Genes, Recessive; Genetic Linkage; Haplotypes; Humans; Intestinal Absorption; Lod Score; Microsatellite Repeats; Pedigree; Phytosterols; Risk Factors; Sitosterols

1998
Analysis of fecal bile acids and neutral steroids using gas-liquid chromatography.
    Annals of nutrition & metabolism, 1998, Volume: 42, Issue:4

    In the present pilot study, for investigating the physiological effects of different types of nondigestible oligosaccharides, we have validated the application of methodologies for the analysis of bile acids and neutral steroids in feces of human subjects. The accuracy of the extraction and chromatographic procedures for the analyses of bile acids and neutral steroids was determined by recovery of added compounds to fecal homogenate. The precision of the above procedures was checked by analyzing these compounds in samples (n = 5) of the same fecal homogenate. Recoveries of added bile acids ranged from 86 and 96%, and those of neutral steroids varied from 81 to 97%. The precision expressed as coefficients of variation of bile acids and neutral steroids ranged from 2.3 to 8.3% and from 6.3 to 11.8%, respectively. The intra- and interindividual variabilities expressed as coefficients of variation of bile acids varied from 1 to 58 and from 0 to 74%, respectively. The same variabilities for neutral steroids ranged from 0.5 to 107% and from 1 to 168%, respectively. The methods validated in the present pilot study were adequate for applying to our forthcoming European Union coordinated major study on the physiological effects of different types of nondigestible oligosaccharides and involving large numbers of samples.

    Topics: Bile Acids and Salts; Cholestanol; Cholesterol; Chromatography, Gas; Feces; Humans; Phytosterols; Sensitivity and Specificity; Sitosterols; Steroids; Stigmasterol

1998
Overexpression of an Arabidopsis cDNA encoding a sterol-C24(1)-methyltransferase in tobacco modifies the ratio of 24-methyl cholesterol to sitosterol and is associated with growth reduction.
    Plant physiology, 1998, Volume: 118, Issue:2

    Higher plants synthesize 24-methyl sterols and 24-ethyl sterols in defined proportions. As a first step in investigating the physiological function of this balance, an Arabidopsis cDNA encoding an S-adenosyl-L-methionine 24-methylene lophenol-C24(1)-methyltransferase, the typical plant enzyme responsible for the production of 24-ethyl sterols, was expressed in tobacco (Nicotiana tabacum L.) under the control of a constitutive promoter. Transgenic plants displayed a novel 24-alkyl-Delta5-sterol profile: the ratio of 24-methyl cholesterol to sitosterol, which is close to 1 in the wild type, decreased dramatically to values ranging from 0.01 to 0.31. In succeeding generations of transgenic tobacco, a high S-adenosyl-L-methionine 24-methylene lophenol-C24(1)-methyltransferase enzyme activity and, consequently, a low ratio of 24-methyl cholesterol to sitosterol, was associated with reduced growth compared with the wild type. However, this new morphological phenotype appeared only below the threshold ratio of 24-methyl cholesterol to sitosterol of approximately 0.1. Because the size of cells was unchanged in small, transgenic plants, we hypothesize that a radical decrease of 24-methyl cholesterol and/or a concomitant increase of sitosterol would be responsible for a change in cell division through as-yet unknown mechanisms.

    Topics: Arabidopsis; Base Sequence; Cholesterol; Cloning, Molecular; DNA Primers; DNA, Complementary; Methyltransferases; Nicotiana; Phytosterols; Plants, Genetically Modified; Plants, Toxic; Sitosterols

1998
beta-Sitosterol activates the sphingomyelin cycle and induces apoptosis in LNCaP human prostate cancer cells.
    Nutrition and cancer, 1998, Volume: 32, Issue:1

    Epidemiological evidence has shown that men consuming a low-fat, high-fiber diet containing high amounts of plant products have a lower risk of prostate cancer than men consuming a Western diet. One of the main differences between these two diets is the type of dietary fat, including dietary sterols. This study was undertaken to compare the effect of two dietary sterols on prostate cancer cells in vitro. beta-Sitosterol (SIT), the most common plant sterol, and cholesterol, an animal sterol, were compared for effect on LNCaP cell growth, differentiation, apoptosis, and sphingomyelin cycle intermediates. Cells were treated for up to seven days with sterols delivered by a cyclodextrin vehicle. Compared with cholesterol, SIT (16 microM) decreased growth by 24% and induced apoptosis fourfold, which was accompanied by cell rounding and a 50% increase in ceramide production. No effect was observed on differentiation as measured by prostate-specific antigen and prostatic acid phosphatase, although total acid phosphatase increased with SIT treatment for up to seven days. The results suggest that the decrease in cell number and increase in apoptosis associated with SIT treatment are mediated by activating the sphingomyelin cycle.

    Topics: Apoptosis; Biomarkers, Tumor; Cell Differentiation; Cell Division; Cholesterol; Humans; Male; Prostatic Neoplasms; Sitosterols; Sphingomyelins; Tumor Cells, Cultured

1998
Cholesterol and its derivatives, are the principal steroids isolated from the leech species Hirudo medicinalis.
    Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology, 1998, Volume: 120, Issue:2

    Steroids were isolated from the blood-sucking leech species Hirudo medicinalis and their structure was studied with one- and two-dimensional NMR spectroscopy (DQF-COSY and HMQC), GC-MS and ESI-MS spectrometry. Fractionating leech lipid using silicic acid chromatography led to the isolation of cholesterol in an early chloroform-eluted peak. Only minor traces of cholest-4-en-3-one, 4 beta-methylcholesterol, and sitosterol were present. The subsequent acetone-eluted fraction contained steroidtriols that were further purified by preparative TLC; these included cholest-7-ene-3,5,6 triol, cholest-4,7-diene-3,6,15 triol and to a lesser amount, cholestane-3,5,6 triol. A developmental study on cholesterol content in the leech showed that it is also the principal steroid in embryonic and freshly hatched leeches prior to feeding. The abundance of cholesterol, comprising approximately 5% of the total leech lipid, suggests that H. medicinalis, a blood sucking leech, has adapted itself fully to its mammalian host in terms of its steroid content. It remains to be seen whether lipids are directly transferred from the host to the parasite or whether leeches have evolved mechanisms to synthesize their own steroids.

    Topics: Animals; Cholestanols; Cholestenones; Cholesterol; Chromatography, Thin Layer; Gas Chromatography-Mass Spectrometry; Hydroxycholesterols; Leeches; Magnetic Resonance Spectroscopy; Sitosterols

1998
Stereochemistry of the reduction of 24-ethyldesmosterol to sitosterol in tissue cultures of Oryza sativa.
    Bioorganic & medicinal chemistry letters, 1998, Feb-03, Volume: 8, Issue:3

    Feeding of [26-13C]- and [27-13C]-24-ethyldesmosterols to cultured cells of Oryza sativa followed by 13C-NMR analysis of the biosynthesized sitosterol revealed that the reduction of 24(25)-double bond proceeds with an anti-addition of hydrogen atoms, thus the E-methyl group of the olefinic precursor becomes the pro-S-methyl on C-25 of sitosterol.

    Topics: Chromatography, Gas; Chromatography, High Pressure Liquid; Culture Techniques; Desmosterol; Magnetic Resonance Spectroscopy; Molecular Structure; Oryza; Oxidation-Reduction; Sitosterols; Stereoisomerism

1998
Characterisation of a new host-vector system for fast-growing mycobacteria.
    Acta microbiologica Polonica, 1998, Volume: 47, Issue:4

    In this paper we describe the development of a host-vector system for genetic studies of fast-growing mycobacteria able to biotransform sterols. A wild strain Mycobacterium smegmatis SN38 and a biotechnological mutant Mycobacterium vaccae B3805 were transformed by electroporation with the pSMT3 E. coli-Mycobacterium shuttle plasmid harbouring the hygromycin resistance gene. Both, the pSMT3 plasmid and its derivative pSMT3-ksdD carrying the 3-ketosteroid-delta 1-dehydrogenase gene (ksdD) from Arthrobacter simplex were stably maintained in M. vaccae B3805. The presence of the pSMT3 vector did not affect biotransformation activities of the host strain. We consider the M. vaccae B3805 strain and the pSMT3 plasmid to be a good host-vector system for cloning in mycobacteria genes coding enzymes involved in steroid degradation pathway.

    Topics: Biotransformation; Chromatography, Thin Layer; Culture Media; DNA, Bacterial; Electrophoresis, Polyacrylamide Gel; Electroporation; Escherichia coli; Genetic Vectors; Mycobacterium; Oxidoreductases; Plasmids; Sitosterols; Transformation, Genetic

1998
[Chemical constituents of the stem and root of Syzygium buxifolium Hook. Et Arn].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1998, Volume: 23, Issue:3

    Six crystalline substances were isolated from the stem and root of Syzygium buxifolium and identified as friedelin, beta-sitosterol, ursolic acid, pomolic acid, oleanolic acid and beta-daucosterol.

    Topics: Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plant Roots; Plant Stems; Plants, Medicinal; Sitosterols; Syzygium; Triterpenes; Ursolic Acid

1998
[Chemical constituents of Cichorium intybus L].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1998, Volume: 23, Issue:11

    To investigate the chemical constituents of Cichorium intybus.. Constituents were separated by means of solvent extraction and chromatography on silical gel. The structures were established by spectral analysis and chemical evidence.. Seven compounds were isolated from the roots of C. intybus and four of them were identified as alpha-amyrin, taraxerone, baurenyl acetate and beta-sitosterol.. All the four compounds were obtained from the plant for the first time.

    Topics: Cichorium intybus; Drugs, Chinese Herbal; Molecular Structure; Oleanolic Acid; Plants, Medicinal; Sitosterols; Triterpenes

1998
[Chemical constituents of Quercus mongolica Fisch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1998, Volume: 23, Issue:9

    To study the chemical constituents of the leaves of Quercus mongolica.. Using techniques of silical gel column chromatography and HNMR, 13CNMR.. Four compounds were isolated and identified as friedelin, glutinol, lupeo and beta-sitosterol respectively.. All the compounds were isolated from this plant for the first time.

    Topics: Drugs, Chinese Herbal; Molecular Structure; Pentacyclic Triterpenes; Plant Leaves; Plants, Medicinal; Quercus; Sitosterols; Triterpenes

1998
[Chemical constituents in aerial part of Ampelopsis grossedentata(Hand.-Mazz.) W.T. Wang].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1998, Volume: 23, Issue:6

    Five compounds were isolated from the aerial part of Ampelopsis grossedentata and identified as ampelopsin, ambrein, beta-sitosterol, myricetin and myricitrin by means of UV, IR, 1HNMR and MS spectral analysis. They were isolated from this plant for the first time.

    Topics: Drugs, Chinese Herbal; Flavonoids; Magnoliopsida; Molecular Structure; Naphthols; Plants, Medicinal; Sitosterols; Triterpenes

1998
[Chemical constituents of Tetrastigma hemsleyanum Diels. et Gilg].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1998, Volume: 23, Issue:7

    To investigate the chemical constituents of Tetrastigma hemsleyanum.. Compounds were separated by rechromatography on silica gel from the chloroform solubles of its ethanol extracts, and the structures were determined by spectral analysis and chemical evidence.. Three compounds were isolated and elucidated as 6'-O-benzoyldaucosterol, daucosterol and beta-sitosterol.. All the three compounds were isolated from this plant for the first time, of which 6'-O-benzoyldaucosterol is a new natural product.

    Topics: Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plants, Medicinal; Sitosterols

1998
[Studies on chemical constituents of Lilium brownii].
    Yao xue xue bao = Acta pharmaceutica Sinica, 1998, Volume: 33, Issue:12

    Lilium brownii F. E. Brown var. viridulum Baker is a well-known and very important traditional Chinese medicine. It has been used as sedative, antitussive, anti-inflammatory or as a nutrient. Five compounds were isolated from the bulbs of Lilium brownii. On the basis of spectroscopic analysis (IR, FAB-MS, 1HNMR, 13CNMR, DEPT, HMQC, HMBC) and their physicochemical properties, they were identified as beta-sitosterol (I), daucosterol (II), n-butyl-beta-D-fructopyranoside (III), 26-O-beta-D-glucopyranosyl-3 beta, 26-dihydroxy-5-cholesten-16, 22-dioxo-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (IV), 26-O-beta-D-glucopyranosyl-3beta, 26-dihydroxy cholestan-16, 22-dioxo-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside(V). Among them, I, II and III were isolated from this plant for the first time, IV and V are new compounds.

    Topics: Drugs, Chinese Herbal; Lilium; Molecular Structure; Saponins; Sitosterols

1998
beta-Sitosterolemia with generalized eruptive xanthomatosis.
    Endocrine journal, 1997, Volume: 44, Issue:1

    The clinical features of the first case of a patient with sitosterolemia and generalized eruptive xanthomatosis are described. A six-year-old girl with generalized eruption was referred to the lipid clinic because of the high plasma cholesterol levels determined by the enzymatic method. Neither clinical signs nor results of laboratory examinations appeared to be abnormal, except for the eruption and the increase in the plasma cholesterol concentration. A family survey revealed high plasma cholesterol concentrations in the mother and one of two other siblings. Histological examination showed the eruption to be a xanthoma. Plasma sterol analysis by high-performance liquid chromatography revealed a noticeable increase in plasma plant sterol as well as cholestanol concentrations in the proband and the hypercholesterolemic sibling. The other family members had slightly high plasma sterol concentrations. This is the first case of a sitosterolemic patient with eruptive xanthomatosis. The case indicates that the clinical features of the xanthoma in sitosterolemia are not only tuberous or tendon but also eruptive, and also suggests that sitosterolemia should be considered in the differential diagnosis of hypercholesterolemia in almost every case with tuberous or eruptive xanthoma. The diagnosis is clinically important, since the disease can be treated successfully by diet therapy and bile acid binding resins.

    Topics: Child; Cholesterol; Chromatography, High Pressure Liquid; Female; Humans; Lipid Metabolism, Inborn Errors; Lipids; Sitosterols; Skin; Xanthomatosis

1997
Effect of micellar beta-sitosterol on cholesterol metabolism in CaCo-2 cells.
    Journal of lipid research, 1997, Volume: 38, Issue:2

    CaCo-2 cells were used to address the effect of the plant sterol, beta-sitosterol, on cholesterol trafficking, cholesterol metabolism, and apoB secretion. Compared to cells incubated with micelles (5 mM taurocholate and 250 microM oleic acid) containing cholesterol, which caused an increase in the influx of plasma membrane cholesterol to the endoplasmic reticulum and increased the secretion of cholesteryl esters derived from the plasma membrane, beta-sitosterol did not alter cholesterol trafficking or cholesteryl ester secretion. Including beta-sitosterol in the micelle together with cholesterol attenuated the influx of plasma membrane cholesterol and prevented the secretion of cholesteryl esters derived from the plasma membrane. Stigmasterol and campesterol had effects similar to beta-sitosterol, although campesterol did not promote a modest influx of plasma membrane cholesterol. Including beta-sitosterol in the micelle with cholesterol decreased the uptake of cholesterol. Compared to cholesterol, 60% less beta-sitosterol was taken up by CaCo-2 cells. No observable esterification of beta-sitosterol was appreciated and the transport of the plant sterol to the basolateral medium was negligible. Cholesterol synthesis and HMG-CoA reductase activities were decreased in cells incubated with beta-sitosterol. This was associated with a decrease in reductase mass and mRNA levels. Cholesteryl ester synthesis and ACAT activities were unaltered by beta-sitosterol. Both stigmasterol and campesterol decreased reductase activity, but only campesterol increased ACAT activity. beta-sitosterol did not affect the secretion of apoB mass. The results suggest that beta-sitosterol does not promote cholesterol trafficking from the plasma membrane to the endoplasmic reticulum. beta-sitosterol interferes with the uptake of micellar cholesterol causing less plasma membrane cholesterol to influx and less cholesteryl ester to be secreted. Despite its lack of effect on cholesterol trafficking, beta-sitosterol decreases cholesterol synthesis at the level of HMG-CoA reductase gene expression.

    Topics: Caco-2 Cells; Cell Membrane; Cholesterol; Cholesterol Esters; Esterification; Humans; Hydroxymethylglutaryl CoA Reductases; Intestinal Mucosa; Intestines; Micelles; Oleic Acid; Phytosterols; Sitosterols; Sterol O-Acyltransferase; Stigmasterol; Taurocholic Acid; Time Factors

1997
Comparison of cholesterol and sitosterol uptake in different brush border membrane models.
    Biochemistry, 1997, Jun-03, Volume: 36, Issue:22

    (I) There is little discrimination between cholesterol and the plant sterol sitosterol in the uptake at the brush border membrane (BBM). (II) This difference cannot account for the marked discrimination between cholesterol and sitosterol observed in the absorption of these two sterols by the small-intestinal epithelium. (III) This discrimination occurs during intracellular processing involving the esterification and incorporation into lipoprotein particles of the two sterols. This conclusion is based on a comparative study of sterol uptake by brush border membrane vesicles (BBMV) and sterol absorption by Caco-2 cells. (IV) The uptake of sitosterol by the BBM is energy-independent and facilitated in a manner analogous to cholesterol uptake [Thurnhofer, H., & Hauser, H. (1990a) Biochemistry 29, 2142-2148]. (V) The rate of cholesterol and sitosterol uptake by BBMV from both mixed bile salt micelles and small unilamellar vesicles (SUV) as the donor is directly proportional to the sterol content of the donor. (VI) The pseudo-first-order rate constants k1 for sterol uptake from SUV are independent of the sterol content up to 10-20 mol %. Above that, competition between the two sterols leads to a reduction of the k1 values.

    Topics: Animals; Caco-2 Cells; Cholesterol; Duodenum; Humans; Infant, Newborn; Intestinal Absorption; Jejunum; Kinetics; Micelles; Microvilli; Models, Biological; Rabbits; Sitosterols; Taurocholic Acid

1997
Allylic nitration of 3 beta-sitosterol and cholesterol acetate: preparation of 7-nitro derivatives.
    Steroids, 1997, Volume: 62, Issue:6

    Topics: Cholesterol Esters; Hot Temperature; Infrared Rays; Microwaves; Nitrates; Sitosterols

1997
Cerebrosides alter the lyotropic and thermotropic phase transitions of DOPE:DOPC and DOPE:DOPC:sterol mixtures.
    Biochimica et biophysica acta, 1997, Jun-12, Volume: 1326, Issue:2

    Freezing injury in rye and oat is a consequence of the formation of the inverted hexagonal (H(II)) phase in regions where the plasma membrane is brought into close proximity with cytoplasmic membranes during freeze-induced dehydration. Susceptibility to plasma membrane destabilization and H(II) phase formation during freezing is associated with alterations in plasma membrane lipid composition. This paper examines the influence of lipid composition and hydration on the propensity of lipid mixtures of DOPE:DOPC and DOPE:DOPC:sterols with added cerebrosides (CER) to form the H(II) phase during dehydration. The addition of CER to DOPE:DOPC:beta-sitosterol mixtures decreased the water content of the dispersions in a manner suggesting that most or all of the water in the dehydrated mixtures was associated with the phospholipids. The addition of CER significantly decreased the osmotic pressure at which the L(alpha) --> H(II) phase transition occurred from an osmotic pressure of 76.1 MPa for DOPE:DOPC (50:50) to 20 MPa in DOPE:DOPC:beta-sitosterol:CER (22.5:22.5:50:5) and 8 MPa in DOPE:DOPC:beta-sitosterol:CER (15:15:50:20). Experiments examining the effects of CER on the thermally-induced formation of the H(II) phase in fully hydrated mixtures and examining the influence of CER on the formation of the H(II) phase in DOPE:DOPC mixtures lacking beta-sitosterol suggested that CER facilitated the L(alpha) --> H(II) phase transition by effecting a decrease in bilayer hydration and by increased lateral packing pressures within the acyl domain of the bilayer. Taken in sum, these data indicate that the differential propensity of the rye and oat plasma membranes to undergo freeze-induced formation of the L(alpha) --> H(II) phase cannot be attributed to one lipid species. Rather, the propensity towards freeze-induced membrane destabilization is a consequence of the summation of physical characteristics of the membrane lipid components that included bilayer hydration, packing pressures within the hydrophobic domain of the membrane, the propensity of the lipid components to demix, and the relative proportions of the various lipid components.

    Topics: Avena; Calorimetry, Differential Scanning; Cell Membrane; Cerebrosides; Freezing; Lipid Bilayers; Microscopy, Electron; Osmotic Pressure; Phosphatidylcholines; Phosphatidylethanolamines; Secale; Sitosterols; Sterols; Temperature; Water; X-Ray Diffraction

1997
[Chemical constituents of Strychnos nitida G. Don].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:1

    Six compounds were isolated from the root and stem of Strychnos nitida for the first time. On the basis of chemical properties and spectral data, the compounds were identified as beta-sitosterol, strychnine, brucine, cantieyine, lignoceric acid and palmitic acid.

    Topics: Alkaloids; Drugs, Chinese Herbal; Magnoliopsida; Plant Roots; Plant Stems; Sitosterols; Strychnine

1997
[Chemical constituents of Cistanche tubulosa (Schenk) Wight].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:3

    From the dry bulbs of Cistanche tubulosa six compounds were isolated and identified as beta-sitosterol, D-mannitol, daucosterol, succinic acid, D-glucose and D-fructose by spectral and chemical analyses. All of them were isolated from the plant for the first time.

    Topics: Cycadopsida; Drugs, Chinese Herbal; Mannitol; Plants, Medicinal; Sitosterols; Succinic Acid

1997
[Fat soluble constituents of the leaves of Vaccinium bracteatum Thunb].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:7

    Four compounds were isolated from the fat soluble fraction of the leaves of Vaccinium bracteatum and identified as friedelin (I), epifriedelinol (II), beta-sitosterol(III) and ursolic acid(IV) by IR, NMR and MS. Compound III and IV are isolated from the leaves of this plant for the first time.

    Topics: Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plant Leaves; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

1997
[Separation and identification of the compounds from Achyranthes bidentata Bl].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:5

    Eight compounds were separated from the roots of Achyrathes bidentata by repeated chromatography. On the basis of physicochemical properties and spectral analysis their structures were elucidated as alpha-spinasterol (1), beta-sitosterol (2), chrysophanol (3), dibutyl phthalate (4), palmitic acid (5), alpha-spinasterol-3-O-beta-D-glucoside (6), daucosterol (7) and ecdysterone (8). Compounds 1-7 were isolated from the plant for the first time.

    Topics: Anthraquinones; Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plants, Medicinal; Sitosterols; Stigmasterol

1997
[Chemical constituents of Begonia evansiana Andr].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:5

    Six compounds were isolated from Begonia evansiana. By means of TLC, mp, 1H and 13CNMR, they were idenified as beta-sitosterol, beta-amyrin, daucosterol, stigmasterol, stigmasterol-3-O-beta-D-glucopyranoside and 4', 5', 7-trihydroxy-flavone-6-O-beta-D-glucopyranoside. All the compounds were isolated from this plant for the first time.

    Topics: Drugs, Chinese Herbal; Flavonoids; Glucosides; Magnoliopsida; Molecular Structure; Oleanolic Acid; Plants, Medicinal; Sitosterols; Stigmasterol; Triterpenes

1997
[Chemical constituents of the roots of Glycyrrhiza eurycarpa P.C.Li].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:11

    Four compounds were isolated from the roots of Glycyrrhiza eurycarpa. They were identified as licochalcone A, glabrol, betulic acid and beta-sitosterol by chemical and physical properties and spectral analysis.

    Topics: Betulinic Acid; Chalcone; Chalcones; Drugs, Chinese Herbal; Flavonoids; Glycyrrhiza; Pentacyclic Triterpenes; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

1997
[Chemical studies on Campylotropis hirtella (Franch. Schindl.)].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1997, Volume: 22, Issue:11

    From the roots of Campylotropis hirtella 6 compounds were isolated. Based on the extensive spectrae analysis their chemical structures were identified as beta-sitosterol, oleanolic acid, ursolic acid, euscaphic acid, tomentic acid and rosamultin.

    Topics: Drugs, Chinese Herbal; Fabaceae; Molecular Structure; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

1997
[Studies on chemical constituents of Kadsura Longepedunculata].
    Yao xue xue bao = Acta pharmaceutica Sinica, 1997, Volume: 32, Issue:6

    The chemical constituents of Kadsura Longepedunculata collected from Zhejiang province were studied. Six compounds were isolated and their structures were elucidated based on physical and spectral analysis. Among them, one is a new compound, which is named kadsulactone acid (I) and the others are kadsulactone (II), (+)-anwulignan (III), mesodihydroguaiaretic acid (IV), d-epidalbacin(V) and beta-sitosterol (VI).

    Topics: Drugs, Chinese Herbal; Lactones; Magnoliopsida; Molecular Structure; Plants, Medicinal; Sitosterols

1997
[Chemical components of Lindernia ciliata (Colsm) Pennell].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1996, Volume: 21, Issue:1

    Three known compounds were isolated from the petroleum ether extract of the whole plant of Lindernia ciliata. They are beta-sitosterol, stigmasterol and lup-20(29)-en-3 beta-ol. Their structures were established by IR, MS, 1HNMR and 13CNMR spectroscopy.

    Topics: Drugs, Chinese Herbal; Pentacyclic Triterpenes; Sitosterols; Stigmasterol; Triterpenes

1996
Steroid transformation by mutants of Mycobacterium sp. with altered response to antibiotics.
    Journal of basic microbiology, 1996, Volume: 36, Issue:6

    Mycobacterium sp. NRRLB3683 which is capable to convert beta-sitosterol to 1,4-androstadiene-3,17-dione (ADD) was treated with methyl methane sulfonate and two strains with altered sensitivity to various antibiotics were obtained. One of the strain was steroid 1(2)-dehydrogenase negative and the other positive. Efficiency of utilization of sterols followed the order beta-sitosterol > cholesterol > soluble cholesterol. The steroid 1(2)-dehydrogenase negative strain was capable of producing 17KS (AD) from beta-sitosterol and converting AD to testosterone and ADD to AD suggesting the negative role of 1(2)-dehydrogenase in sterol side chain cleavage and decrease in hydrogenase activity by mutation. But this enzyme can perform the reverse reaction under aerobic condition.

    Topics: Androstenedione; Cholesterol; Culture Media; Drug Resistance, Microbial; Mutagenesis; Mycobacterium; Oxidoreductases; Sitosterols; Sulfonic Acids

1996
[Relevance of general practitioner's prescriptions for hospital pharmacotherapy. A survey of hospital physicians].
    Deutsche medizinische Wochenschrift (1946), 1996, Nov-22, Volume: 121, Issue:47

    At hospital admission drugs prescribed by the general practitioner (GP) are often changed. This may have a negative impact on the relationship between family and hospital physicians as well as on the family doctor-patient-relationship. The study set out to examine the attitudes of hospital physicians towards GPs' prior ambulatory medication, especially in the case of drugs of unproven efficacy (e.g. certain drug combinations and homeopathic or herbal drugs).. A total of 129 doctors of the surgical and medical wards of the Göttingen University Hospital received a standardized questionnaire focusing on drugs prescribed by referring GPs (response rate: 65.9%). Three case vignettes were presented describing "popular" GP prescriptions. Doctors of surgical and medical departments were asked whether or not they would follow these prescriptions. Differences in the answers between the groups of doctors were tested by Fisher's exact test.. More doctors on the surgical than on the medical wards would usually follow GPs' medication (82 vs 25%; P < 0.001). According to these attitudes, more doctors of medical departments would stop the prescription of drug combination (82 vs 41%; P < 0.001); both groups would be hesitant to accept homeopathic drugs (89 vs 59%; P < 0.01) or herbal drugs (89 vs 55%; P < 0.01) as prescribed by the GP. The critical attitude especially of doctors of the medical departments towards drug combinations and herbal drugs was in line with their decision in the case vignettes (e.g. Capozide, Tebonin forte).. Especially doctors working in medical departments keep in line with conventional clinical pharmacological criteria. If they have to decide whether or not to follow patients' ambulatory medication, they may overlook GPs' decision-making process underlying their prescribing.

    Topics: Aged; Attitude of Health Personnel; Captopril; Data Interpretation, Statistical; Diabetes Mellitus; Drug Combinations; Drug Prescriptions; Drug Therapy; Family Practice; Female; Flavonoids; Ginkgo biloba; Hemostatics; Humans; Hydrochlorothiazide; Hypertension; Male; Medical Staff, Hospital; Middle Aged; Plant Extracts; Prostatic Hyperplasia; Sitosterols; Surveys and Questionnaires

1996
[Chemical constituents of Notopterygium forbesii Boiss].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1996, Volume: 21, Issue:5

    Nine compounds were isolated from the under-ground part of Notopterygium forbesii. On the basis of physicochemical properties and spectroscopic analysis, they were identified as phellopterin, isoimperattorin, notopterol, nodakenitin, nodakenin, 6-O-trans-feruoylnodakenin, p-hydroxyphenethyl anisate, pregnenolone and beta-sitosteroi, of which phellopterin was obtained from the plant of Notopterygium genus for the first time.

    Topics: Drugs, Chinese Herbal; Furocoumarins; Plant Roots; Plants, Medicinal; Sitosterols

1996
[Chemical constituents of the root of Boehmeira nivea (L.) Gaud].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1996, Volume: 21, Issue:7

    Three compounds were isolated from the root of Boehmeria nivea and elucidated according to their spectroscopic data as beta-sitosterol, daucosterol and 19 alpha-hydroxyursolic acid. They are obtained from the herb for the first time.

    Topics: Drugs, Chinese Herbal; Magnoliopsida; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

1996
[Chemical constituents in the bark of Illicium jadifengpi B. N. Chang].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1996, Volume: 21, Issue:9

    Four compounds were isolated from the bark of illicium jadi feng pi for the first time. Their structures were identified as 4-epi-isopimaric acid, 8,11,13,15-abietatetran-19-oic acid, 15-hydroxydehydroabietic acid and beta-sitosterol by physico-chemical constants and specral analyses.

    Topics: Carboxylic Acids; Diterpenes; Drugs, Chinese Herbal; Magnoliopsida; Phenanthrenes; Sitosterols

1996
[Orthogonal experiment design in the optimization of processing technology for Rhizoma Pinelliae by ginger and alum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1996, Volume: 21, Issue:11

    Based on the L9(3)1 orthogonal design with the amount of ginger, amount of alum and decocting time as working factors, and using the method of recording comprehensive scores, an experimental study has been made on the optimization of processing technology for Rhizoma Pinelliae by ginger and alum as stipulated in the Pharmacopoeia. The result shows that the best process is to use 15 kg of ginger juice and 8 kg of alum per 100 kg of Pinellia ternata and decoct them together for 2-3 hours till the juice is fully absorbed by Rhizoma Pinelliae.

    Topics: Alkaloids; Alum Compounds; Animals; Drugs, Chinese Herbal; Female; Hot Temperature; Magnoliopsida; Male; Mice; Mice, Inbred ICR; Sitosterols; Technology, Pharmaceutical; Zingiberales

1996
[Chemical constituents in the roots of Lycium chinense Mill].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1996, Volume: 21, Issue:11

    Four compounds were isolated from the roots of Lycium chinense and identified as beta-sitosterol, betaine hydrochloride, scopoletin and E-ferulic acid octacosyl ester. The last one was isolated from the genus for the first time.

    Topics: Betaine; Coumaric Acids; Drugs, Chinese Herbal; Plant Roots; Scopoletin; Sitosterols; Solanaceae

1996
[Chemical components of Seseli yunnanense Franch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:5

    Topics: Coumarins; Drugs, Chinese Herbal; Sitosterols

1995
[Chemical constituents in the leaves of Mangifera persiciformis C.Y. Wu et Y.L. Ming].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:5

    Eleven crystalline constituents have been isolated from the leaves of Mangifera persiciformis, of which five were identified as taraxerol, friedelin, beta-sitosterol, mangiferin and quercetin by comparing their physicochemical and spectroscopic data. They were isolated from this plant for the first time.

    Topics: Antiviral Agents; Drugs, Chinese Herbal; Oleanolic Acid; Plant Leaves; Plants, Medicinal; Sitosterols; Xanthenes; Xanthones

1995
Antibacterial activity and phytochemical analysis of Vochysia divergens (Vochysiaceae).
    Journal of ethnopharmacology, 1995, Jul-07, Volume: 47, Issue:2

    Vochysia divergens Pohl (Vochysiaceae) is a tree commonly found in wet soils of 'Pantanal' of Mato Grosso, Brazil, and used in folk medicine against infections and asthma. We have studied different extracts and some isolated compounds from this plant for antibacterial activity. From the extracts of the stem bark beta-sitosterol, betulinic acid and sericic acid were isolated. The minimal inhibitory concentration (MIC) for Staphylococcus aureus were: ethanolic extract (MIC = 1.5 mg/ml); ethyl acetate extract (MIC = 2.0 mg/ml); and sericic acid (MIC = 1.0 mg/ml). Escherichia coli was resistant until 5 mg/ml.

    Topics: Anti-Bacterial Agents; Antineoplastic Agents, Phytogenic; Betulinic Acid; Brazil; Escherichia coli; Magnetic Resonance Spectroscopy; Medicine, Traditional; Microbial Sensitivity Tests; Oleanolic Acid; Pentacyclic Triterpenes; Plant Extracts; Plant Stems; Sitosterols; Spectrophotometry, Infrared; Staphylococcus aureus; Triterpenes

1995
The phytoestrogen beta-sitosterol alters the reproductive endocrine status of goldfish.
    Toxicology and applied pharmacology, 1995, Volume: 134, Issue:2

    There is a growing awareness that chemicals in the environment may function as hormone mimics and affect endocrine function in wildlife. In this study, the effects of beta-sitosterol, a phytoestrogen present in high concentration in bleached kraft pulp mill effluent (BKME), on reproductive fitness of goldfish were investigated. Plasma reproductive hormone levels were measured in male and female goldfish on Day 4 following two intraperitoneal injections of beta-sitosterol or an oxidized sitosterol preparation. In some experiments, plasma hormone levels were also measured after fish were injected with Ovaprim, which contains a superactive analog of salmon GnRH and the dopamine receptor antagonist domperidone and leads to increased secretion of gonadotropin (GtH)-II (LH-type GtH). Plasma testosterone (T) and 11-ketotestosterone levels in males and T and 17 beta-estradiol levels in females were significantly decreased in beta-sitosterol-treated fish on Day 4 and 24 hr after an injection of Ovaprim. Plasma GtH-II levels were elevated in male fish treated with beta-sitosterol on Day 4 and further increased in response to Ovaprim, suggesting that reduced plasma steroid levels were not due to effects on pituitary function. In other studies, testes pieces from beta-sitosterol-treated goldfish produced reduced levels of T and pregnenolone in vitro both basally and in response to the GtH-II agonist human chorionic gonadotropin (hCG) when compared to the testes from control fish. Basal and hCG-stimulated pregnenolone and hCG-stimulated T were reduced in follicles from beta-sitosterol-treated fish; however, basal T production was not different from controls. These results suggest that beta-sitosterol reduces the gonadal steroid biosynthetic capacity through effects on cholesterol availability or the activity of the side chain cleavage enzyme P450SCC. These findings raise the possibility that beta-sitosterol could be a contributing factor to the reproductive dysfunction observed in fish exposed to BKME.

    Topics: Animals; Female; Goldfish; Gonadotropins; Male; Reproduction; Sitosterols; Testosterone; Water Pollutants, Chemical

1995
Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment.
    Journal of lipid research, 1995, Volume: 36, Issue:8

    Absorption of dietary cholesterol, campesterol, and sitosterol, cholesterol balance, and fecal excretion of plant sterols were determined in three unrelated patients with phytosterolemia and three healthy volunteers during constant intake of cholesterol and plant sterols using accurate gas-liquid chromatography-mass spectrometry techniques. Each subject received a mixture of [26,26,26,27,27,27-2H6]cholesterol, [6,7,7-2H3]sitostanol, and [6,7,7-2H3]campesterol together with two non-absorbable markers, [5,6,22,23-2H4]sitostanol and chromic oxide. Feces were collected from days 5 to 7 and absorption of different sterols was calculated from the intestinal disappearance of the different sterols relative to [5,6,22,23-2H4]sitostanol and chromic oxide. The results obtained by the two markers were not different and the absorption of cholesterol averaged 53 +/- 4% for the patients (mean +/- SD) and 43 +/- 3% for the volunteers. Campesterol absorption averaged 24 +/- 4% in patients and 16 +/- 3% in healthy volunteers, whereas sitosterol absorption averaged 16 +/- 1% and 5 +/- 1%, respectively. Cholesterol synthesis expressed by body weight varied considerably in the two groups but appeared to be about 5 times lower in patients than in controls. Administration of a high dose of sitostanol (0.5 g t.i.d.) to two patients was followed by a reduction in cholesterol absorption by 24% and 44%, an increase in fecal output of cholesterol and steroids derived from cholesterol and plant steroids, and a marked reduction of serum cholesterol, campesterol, and sitosterol. Under the conditions used, inhibition of cholesterol absorption by sitostanol was not followed by a significant rise in cholesterol synthesis. The time of observation was, however, too short to allow final conclusion on this. The results show that the absolute difference in absorption rate of different sterols between the patients and healthy volunteers was about the same. As a consequence, increasing hydrophobicity causes a relative decrease of absorption rates. Thus, patients with phytosterolemia seem to have a generally increased absorption of sterols rather than a loss of a specific discriminatory mechanism, and oral administration of sitostanol seems to be an interesting new approach for treatment of phytosterolemia.

    Topics: Absorption; Adult; Anticholesteremic Agents; Bile Acids and Salts; Cholesterol; Cholesterol, Dietary; Deuterium; Dietary Fats; Feces; Female; Humans; Intestinal Mucosa; Lipid Metabolism, Inborn Errors; Lipoproteins; Male; Middle Aged; Phytosterols; Sitosterols; Steroids; Sterols

1995
Side-chain structure is critical for the transport of sterols from lysosomes to cytoplasm.
    Biochimica et biophysica acta, 1995, Jun-27, Volume: 1257, Issue:1

    Macrophages take up and metabolize negatively charged liposomes containing free cholesterol efficiently, resulting in a massive accumulation of cholesteryl esters and triacylglycerols in their cytoplasm (Nishikawa, K., Arai, H. and Inoue, K. (1990) J. Biol. Chem. 265, 5226-5231). This system was used to assess the effects of structural variation of sterol on the intracellular transport and the metabolism of endocytosed sterols by the cells. Liposomes containing phytosterols with an extra one (campesterol) or two (beta-sitosterol, stigmasterol, fucosterol) carbons at the C-24 position of the cholesterol side-chain were endocytosed as efficiently as those containing cholesterol without exhibiting any apparent toxicity on the cells. Esterification of endocyotosed phytosterols was, however, extremely low; campesterol esterification was only 20% that of cholesterol and either beta-sitosterol or stigmasterol was not esterified appreciably. A morphological study showed that the endocytosed phytosterols were accumulated in the phagolysosomes of the cells. Blocking of esterification of endocytosed cholesterol by an acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor did not lead to cholesterol accumulation in the phagolysosomes. These data suggest that accumulation of endocytosed phytosterols in phagolysosomes is not a consequence of the inability of the cell to esterify sterols in the endoplasmic reticulum. In the light of these observations, we conclude that cultured macrophages can discriminate between sterols that differ only by a methyl or ethyl group at the C-24 position at their lysosomal compartment.

    Topics: Animals; Biological Transport; Cells, Cultured; Cytoplasm; Endocytosis; Histocytochemistry; Lysosomes; Macrophages, Peritoneal; Mice; Molecular Structure; Sitosterols; Sterols

1995
[Chemical constituents of Euphorbia nematocypha Hand.-Mazz].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:3

    Four compounds were isolated from the roots of Euphorbia nematocypha. Three of them were identified as A'-neogammacer-22(29)-en-3 beta-ol (18 beta.21 alpha) (II), jolkinolide E (III) and beta-sitoesterol (IV). Among them, II was obtained from the genus Euphorbia and III from this plant for the first time.

    Topics: Diterpenes; Drugs, Chinese Herbal; Sitosterols; Triterpenes

1995
[Chemical constituents of Sparganium stoloniferum Buch.-Ham].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:6

    Topics: Drugs, Chinese Herbal; Isoflavones; Sitosterols; Stigmasterol

1995
Simultaneous measurement of phytosterols (campesterol and beta-sitosterol) and 7-ketocholesterol in human lipoproteins by capillary column gas chromatography.
    Journal of chromatography. B, Biomedical applications, 1995, Jan-06, Volume: 663, Issue:1

    7-Ketocholesterol (a major cholesterol oxidation product) and phytosterols are important indicators of lipoprotein oxidation and lipoprotein metabolism respectively. We describe a simple, sensitive and reproducible method for the simultaneous measurement of these sterols in human lipoprotein samples by capillary column gas liquid chromatography. The method is suitable for clinical studies as small quantities of lipoprotein are required. Sterols are analysed after extraction from lipoprotein samples obtained by sequential flotation ultracentrifugation. The method involves briefly: extraction from lipoprotein samples using chloroform-methanol, saponification of sterol esters using cold potassium hydroxide, purification and derivatisation to trimethylsilyl ethers using BSTFA and 1% TMCS. Oxidation is prevented by drying under nitrogen and the use of powerful antioxidants. Separation is achieved using a DB-1 capillary column and a two-stage temperature ramp from 180-250 degrees C and detection using FID. The identity of sterols can be confirmed by GC-MS. Phytosterols and 7-ketocholesterol are present at low concentration in all the major lipoproteins. Using [3,4-13C]cholesterol and GC-MS we present evidence that cholesterol oxidation does not occur during the processing of lipoproteins using this technique.

    Topics: Capillary Action; Cholesterol; Chromatography, Gas; Humans; Ketocholesterols; Lipoproteins; Male; Oxidation-Reduction; Phytosterols; Reproducibility of Results; Sitosterols

1995
Unexpected inhibition of cholesterol 7 alpha-hydroxylase by cholesterol in New Zealand white and Watanabe heritable hyperlipidemic rabbits.
    The Journal of clinical investigation, 1995, Volume: 95, Issue:4

    We investigated the effect of cholesterol feeding on plasma cholesterol concentrations, hepatic activities and mRNA levels of HMG-CoA reductase and cholesterol 7 alpha-hydroxylase and hepatic LDL receptor function and mRNA levels in 23 New Zealand White (NZW) and 17 Watanabe heritable hyperlipidemic (WHHL) rabbits. Plasma cholesterol concentrations were 9.9 times greater in WHHL than NZW rabbits and rose significantly in both groups when cholesterol was fed. Baseline liver cholesterol levels were 50% higher but rose only 26% in WHHL as compared with 3.6-fold increase with the cholesterol diet in NZW rabbits. In both rabbit groups, hepatic total HMG-CoA reductase activity was similar and declined > 60% without changing enzyme mRNA levels after cholesterol was fed. In NZW rabbits, cholesterol feeding inhibited LDL receptor function but not mRNA levels. As expected, receptor-mediated LDL binding was reduced in WHHL rabbits. Hepatic cholesterol 7 alpha-hydroxylase activity and mRNA levels were 2.8 and 10.4 times greater in NZW than WHHL rabbits. Unexpectedly, cholesterol 7 alpha-hydroxylase activity was reduced 53% and mRNA levels were reduced 79% in NZW rabbits with 2% cholesterol feeding. These results demonstrate that WHHL as compared with NZW rabbits have markedly elevated plasma and higher liver cholesterol concentrations, less hepatic LDL receptor function, and very low hepatic cholesterol 7 alpha-hydroxylase activity and mRNA levels. Feeding cholesterol to NZW rabbits increased plasma and hepatic concentrations greatly, inhibited LDL receptor-mediated binding, and unexpectedly suppressed cholesterol 7 alpha-hydroxylase activity and mRNA to minimum levels similar to WHHL rabbits. Dietary cholesterol accumulates in the plasma of NZW rabbits, and WHHL rabbits are hypercholesterolemic because reduced LDL receptor function is combined with decreased catabolism of cholesterol to bile acids.

    Topics: Alanine Transaminase; Alkaline Phosphatase; Animals; Bile Acids and Salts; Blotting, Northern; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Cholesterol, Dietary; Dose-Response Relationship, Drug; Hydroxymethylglutaryl CoA Reductases; Hypercholesterolemia; Lipoproteins, LDL; Liver; Protein Binding; Rabbits; Receptors, LDL; RNA, Messenger; Sitosterols

1995
Comparative studies of metabolism of 4-desmethyl, 4-monomethyl and 4,4-dimethyl sterols in Manduca sexta.
    Lipids, 1995, Volume: 30, Issue:1

    To investigate the metabolism and possible deleterious effects of 4-methyl and 4,4-dimethyl steroids in Manduca sexta, the 4,4-dimethyl sterols lanosterol and cycloartenol, the 4-methyl sterol obtusifoliol and the 4,4-dimethyl pentacyclic triterpenoid alpha-amyrin were fed in an artificial agar-based diet at various concentrations. Utilization and metabolism of these four compounds were compared with sitosterol, stigmasterol, brassicasterol, ergosterol and 24-methylenecholesterol, 24-alkyl sterols that are readily dealkylated and converted to cholesterol in Manduca and in most phytophagous insects. None of the 4-methylated compounds significantly inhibited development except at very high dietary concentrations. The delta 24-bonds of lanosterol and cycloartenol were effectively reduced by the Manduca delta 24-sterol reductase enzyme, as is the delta 24-bond of desmosterol which, in most phytophagous insects, is an intermediate in the conversion of sitosterol, stigmasterol and other C28 and C29 phytosterols to cholesterol. On the other hand, the 24-methylene substituent of obtusifoliol was not dealkylated. Each of the 4-desmethyl C28 and C29 sterols was readily converted to cholesterol, and a significant amount of 7-dehydrocholesterol was derived from ergosterol metabolism. The reason for the differences in substrate specificity of these sterols is not clear, but the information may be useful in the development of new, specific, mechanism-based inhibitors of sterol metabolism.

    Topics: Animals; Cholestadienols; Cholesterol; Ergosterol; Manduca; Phytosterols; Sitosterols; Sterols; Stigmasterol

1995
Developmental regulation of sterol biosynthesis in Zea mays.
    Lipids, 1995, Volume: 30, Issue:3

    Sixty-one sterols and pentacyclic triterpenes have been isolated and characterized by chromatographic and spectral methods from Zea mays (corn). Several plant parts were examined; seed, pollen, cultured hypocotyl cells, roots, coleoptiles (sheaths), and blades. By studying reaction pathways and mechanisms on plants fed radiotracers ([2-(14)C]mevalonic acid, [2-(14)C]acetate, and [2-(3)H]acetate), and stable isotopes (D2O), we discovered that hydroxymethylgutaryl CoA reductase is not "the" rate-limiting enzyme of sitosterol production. Additionally, we observed an ontogenetic shift and kinetic isotope effect in sterol biosynthesis that was associated with the C-24 alkylation of the sterol side chain. Blades synthesized mainly 24 alpha-ethyl-sterols, sheaths synthesized mainly 24-methyl-sterols, pollen possessed an interrupted sterol pathway, accumulating 24(28)-methylene-sterols, and germinating seeds were found to lack an active de novo pathway. Shoots, normally synthesizing (Z)-24(28)-ethylidine-cholesterol, after incubation with deuterated water, synthesized the rearranged double-bond isomer, stigmasta-5,23-dien-3 beta-ol. Examination of the mass spectrum and 1H nuclear magnetic resonance spectrum of the deuterated 24-ethyl-sterol indicated the Bloch-Cornforth route originating with acetyl-CoA and passing through mevalonic acid to sterol was not operative at this stage of development. An alternate pathway giving rise to sterols is proposed.

    Topics: Acetates; Alkylation; Carbon Radioisotopes; Chromatography, High Pressure Liquid; Hydroxymethylglutaryl CoA Reductases; Mass Spectrometry; Mevalonic Acid; Models, Biological; Oxidation-Reduction; Phytosterols; Plant Roots; Plant Shoots; Seeds; Sitosterols; Tissue Distribution; Zea mays

1995
The effect of neonatal exposure to diethylstilbestrol, coumestrol, and beta-sitosterol on pituitary responsiveness and sexually dimorphic nucleus volume in the castrated adult rat.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1995, Volume: 208, Issue:1

    The neonatal hormone environment influences the sexually differentiated patterns of development. Estrogens, derived from intracerebral aromatization, promote male pattern development of the central nervous system. The purpose of this study was to determine the effects of neonatal exposure to environmental estrogens on luteinizing hormone (LH) secretion and development of the sexually dimorphic nucleus of the medial preoptic area (SDN-POA) in castrated adult rats. Neonatal rats of both sexes received injections of either corn oil, 0.1 microgram diethylstilbestrol (DES), 3 micrograms beta-sitosterol (B1), 30 micrograms beta-sitosterol (B2), 0.1 microgram coumestrol (C1), 1 microgram coumestrol (C2), or 10 micrograms coumestrol (C3) on Day 1-10 of life and were castrated on Day 21. Right heart catheters were placed on Day 42, and GnRH (50 ng/kg) was administered. Blood was sampled for LH at 0-, 5-, 10-, 15-, and 30-min intervals. All doses of beta-sitosterol and coumestrol elicited increased basal levels of LH in females. In males, B1, B2, C2, and C3 increased basal levels of LH. The GnRH-induced LH increase was prevented in females treated with diethylstilbestrol and 10 micrograms of coumestrol. Males in all treatment groups exhibited GnRH-induced LH surges. The animals were sacrificed by decapitation on Day 49. Volumes of the SDN-POA of the groups were compared. Treatment with the agents did not result in significantly increased SDN volume in females; nor was there a difference in SDN size among the male groups. These data show that exposure to environmental estrogens early in development alters both postpubertal pituitary response to GnRH and basal LH secretion in females and alters only basal LH secretion in males. No significant enlargement (i.e., masculinization) of the SDN-POA was exhibited.

    Topics: Animals; Animals, Newborn; Castration; Coumestrol; Diethylstilbestrol; Female; Gonadotropin-Releasing Hormone; Hypothalamus; Luteinizing Hormone; Male; Pituitary Gland; Rats; Sex Differentiation; Sitosterols

1995
A marked and sustained reduction in LDL sterols by diet and cholestyramine in beta-sitosterolemia.
    Clinical and investigative medicine. Medecine clinique et experimentale, 1995, Volume: 18, Issue:5

    This study examines the therapeutic outcome of a low plant sterol diet and adjunctive drug therapy (cholestyramine) in the long term treatment of beta-sitosterolemia. A diet restricted in plant sterols, cholesterol and fat was implemented in a 48-year-old male beta-sitosterolemic patient. The plant sterols beta-sitosterol, campesterol and stigmasterol, and cholesterol content of the diet were quantitated by a gas chromatography method (GLC) during metabolic ward studies. Food table analysis of dietary sterols, while quantitatively similar to GLC, significantly underestimated the level of plant sterols and therefore overestimated dietary cholesterol intake. The duration of the study was 18 months. The effect of the diet over a period of 6 months on the sterol levels of plasma and individual lipoprotein fractions (VLDL, LDL, HDL) was evaluated. Apolipoproteins A-1 and B-100 levels were measured. The same parameters were assessed over the next 12 months with the adjunctive use of cholestyramine and dietary restrictions. The diet was effective in lowering total, VLDL, and LDL plant sterols by 37%, 59%, and 32% respectively. The low plant sterol diet did not change total plasma, VLDL or LDL cholesterol. With the addition of cholestyramine, total plasma and LDL cholesterol declined by 64 and 76%, respectively, while HDL-cholesterol remained unchanged. LDL plant sterols declined by 77%, while VLDL plant sterol showed no further change. The decline showed no discrimination among the individual plant sterols. One week after cholestyramine therapy, apolipoprotein B fell from 1.03 to 0.11 g/L, while apolipoprotein A rose from 1.29 to 1.79 g/L. These levels subsequently stabilized at 70% below (0.29 g/L) and 42% above (1.81 g/L) that of diet therapy alone. Xanthomas, angina pectoris, and intermittent claudication resolved during the diet and cholestyramine therapy period. Dietary restriction of plant sterols combined with cholestyramine therapy is an effective means of treating beta-sitosterolemia.

    Topics: Adult; Apolipoproteins B; Cholesterol, Dietary; Cholestyramine Resin; Diet; Dietary Fats; Energy Intake; Erythrocytes; Humans; Lipid Metabolism, Inborn Errors; Lipoproteins; Lipoproteins, LDL; Male; Phytosterols; Sitosterols; Sterols

1995
Microbial transformation of beta-sitosterol and stigmasterol into 26-oxygenated derivatives.
    Steroids, 1995, Volume: 60, Issue:9

    The genetically modified Mycobacterium sp. BCS 396 strain has been used to transform sterols with stigmastane side chain in order to obtain 26-oxidized metabolites. beta-Sitosterol (I) was transformed to 4-stigmasten-3-one (II), 26-hydroxy-4-stigmasten-3-one (III), and 3-oxo-4-stigmasten-26-oic acid (IV), while stigmasterol (V) was converted to 4,22-stigmastadien-3-one (VI), 6 beta-hydroxy-4,22-stigmastadien-3-one (VII), 26-hydroxy-4,22-stigmastadien-3-one (VIII), 3-oxo-4,22-stigmastadien-26-oic acid methyl ester (IX), and 3-oxo-1,4,22-stigmastatrien-26-oic acid methyl ester (X) with that strain. In both beta-sitosterol and stigmasterol, 26-oxidation generates the R-configuration on C-25.

    Topics: Mass Spectrometry; Molecular Structure; Mycobacterium; Oxidation-Reduction; Sitosterols; Stigmasterol; Transformation, Bacterial; X-Ray Diffraction

1995
[Chemical constituents of the Sparganium stoloniferum Buch.-Ham].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:8

    Three compounds were obtained for the first time from the rhizome of Sparganium stoloniferum and identified as beta-sitosterol, succinic acid and daucosterol by comparing with the known specimens. Twenty-one fatty acids were separated and identified by GC-MS.

    Topics: Drugs, Chinese Herbal; Fatty Acids; Sitosterols

1995
Evaluation of the use of beta-sitostanol as a nonabsorbable marker for quantifying cholesterol absorption.
    Journal of lipid research, 1995, Volume: 36, Issue:10

    For over a decade investigators have quantified cholesterol absorption by comparison of dietary intake and fecal excretion of isotopic cholesterol with that of beta-sitosterol as a "nonabsorbable" marker. However, beta-sitosterol might not be ideal due to its potential for absorption. We therefore carried out two studies to evaluate a new marker with less potential for absorption, [3H]beta-sitostanol. In the first study (Study I, n = 22), we compared absorption of [3H]beta-sitostanol and [14C]beta-sitosterol in a simultaneous dual-label continuous feeding ("phytosterol absorption") experiment. We observed a consistently higher ratio of [3H]beta-sitostanol/[14C]beta-sitosterol in the stool relative to diet on the first day of fecal collection (6.1% +/- 3.2% loss of [3H]beta-sitosterol, range 3-12%), but thereafter, the ratio in stool was similar to that in diet. In Study II (n = 23), we compared cholesterol absorption directly using [3H]beta-sitosterol and [14C]cholesterol, and, separately, [3H]beta-sitostanol and [14C]cholesterol. We found that mean absorption between the two methods was similar (45% +/- 11% versus 44% +/- 10%, respectively, P difference = 0.40), and the two methods correlated well with one another (r = 0.83) when samples from all available days were used. Variability between the two methods was greater in individuals who absorbed more than 40% of cholesterol. Cholesterol loss on day 2 estimated from use of beta-sitostanol as a nonabsorbable marker was predictive of absorption using ratios from days 4-6 (r = 0.80). These results suggest that, for the majority of subjects, beta-sitosterol is a valid nonabsorbable marker for cholesterol absorption.

    Topics: Adult; Aged; Biomarkers; Cholesterol; Evaluation Studies as Topic; Female; Humans; Intestinal Absorption; Male; Middle Aged; Reference Values; Sitosterols

1995
[Chemical constituents of Euphorbia hylonoma Hand. -Mazz].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:12

    Three compounds have been isolated from the root of Euphorbia hylonoma and identified as 3,3',4-tri-O- methylellagic acid, beta-sitosterol and sucrose by physicochemical and spectroscopic methods. The compound 3,3'4-tri-O-methylellagic acid is discovered in Euphorbia for the first time.

    Topics: Drugs, Chinese Herbal; Ellagic Acid; Sitosterols; Sucrose

1995
[Effect of ginger-processing on beta-sitosterol and total alkaloid contents in Rhizoma Pinelliae].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1995, Volume: 20, Issue:11

    The contents of beta-sitosterol of five processed products of Rhizoma Pinelliae we were determined by TLC. The result showed that the lowest content of beta-sitosterol was found in Rhizoma Pinelliae boiled with ginger juice (0.0180%), and the highest in raw Phizoma Panelliae (0.0572%). The contents of total alkaloid of five processed products of Phizoma Pinelliae were also determined by gravimetry and spectrophotometry with acid dye. The result showed that the highest content of total alkaloid was obtained in Rhizoma Pinelliae boiled with ginger juice and alum, and the lowest in Rhizoma Pinelliae boiled with ginger juice.

    Topics: Alkaloids; Drugs, Chinese Herbal; Hot Temperature; Sitosterols; Technology, Pharmaceutical

1995
Postselective (directed) mutagenesis of fast-growing strain of Mycobacterium vaccae as a method of creating mutants showing changed phenotypic properties.
    Acta microbiologica Polonica, 1994, Volume: 43, Issue:2

    Postselective (directed) mutagenesis was used to create mutants of M. vaccae B3805 showing changed abilities for steroid biotransformations. Three morphological classes of such mutants, differing in colony colour: yellow, white and pink, were selected. Some of them can be helpful in genetic studies of steroid biotransformation. Two mutants were also shown to be hosts for foreign DNA.

    Topics: Biotransformation; DNA, Bacterial; Kinetics; Mutagenesis; Mutation; Mycobacterium; Phenotype; Plasmids; Sitosterols; Steroid Hydroxylases; Steroids

1994
Sterol side-chain cleavage with immobilized Mycobacterium cells in water-immiscible organic solvents.
    Enzyme and microbial technology, 1994, Volume: 16, Issue:8

    The possibility of using whole Mycobacterium sp. cells for the selective degradation of the side-chain of sitosterol in an organic bioconversion medium was investigated. Sterol solubility limits were estimated and free-cell biocompatibility tests were carried out, using a range of water-immiscible solvents. Among these, phthalates exhibited good biocompatibility and sterol-solubilizing capacities. Several organic and inorganic matrices were tested for the immobilization of Mycobacterium sp. cells by surface adhesion. Celite led to the best results, being thus selected for beta-sitosterol side-chain degradation tests in phthalates and in aqueous medium. Cells entrapped in kappa-carrageenan and in polyurethane foams were also used in these tests. The highest degradation activities were obtained with cells immobilized in Celite, with bis(2-ethylhexyl)phthalate as the conversion medium, resulting in molar conversion yields up to 70%, with respect to beta-sitosterol (5 g l-1). Further activity and stability tests revealed that this bioconversion system is markedly temperature dependent.

    Topics: Androstenedione; Biodegradation, Environmental; Biotechnology; Diatomaceous Earth; Microscopy, Electron, Scanning; Mycobacterium; Sitosterols; Solubility; Solvents; Sterols; Temperature; Water

1994
[Chemical constituents of Aralia decaisneana Hance].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1994, Volume: 19, Issue:9

    Six compounds were isolated from the root bark of Aralia decaisneana and elucidated by spectral and chemical analyses as 3-O-[beta-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl- (1-->3)-beta-D-glucuronopyranosyl]-oleanolic acid (Ad-V), chikusetsusaponin IVa (Ad-IX), deglucose chikusetsusaponin IVa (Ad-X), palmitic acid (Ad-VI), beta-sitosterol (Ad-VII) and oleanolic acid (Ad-VIII). Ad-V was obtained from nature for the first time, and the rest were all obtained from this plant for the first time.

    Topics: Drugs, Chinese Herbal; Oleanolic Acid; Saponins; Sitosterols

1994
Effect of inhibitors of cell envelope synthesis on beta-sitosterol side chain degradation by Mycobacterium sp. NRRL MB 3683.
    Journal of basic microbiology, 1994, Volume: 34, Issue:6

    The role of the lipid bilayer and the peptidoglycan of the mycobacterial cell wall in the permeation of beta-sitosterol into the cell and its transformation to androst-1-ene-3,17-dione (AD) and androsta-1,4-diene-3,17-dione (ADD) was studied. Specific inhibitors were used at concentrations affecting the biosynthesis of the assumed target structures, but causing only partial cell growth inhibition or exerting no effect on growth. m-Fluorophenylalanine and DL-norleucine which are known to disorganize the biosynthesis of amphipatic components of the outer layer of the lipid bilayer, used at concentrations 250 micrograms/ml and 400 micrograms/ml, respectively, increased the formation rate of AD+ADD from 0.3 (control) to 0.7 and 0.8 mg products/g dry weight/h. The disorganization of the underlying mycolyl-arabinogalactan structure by the action of the ethambutol at the concentration 40 micrograms/ml, at which the cell growth was apparently not affected, caused the decrease of the product formation from 135 mg/l to 70 mg/l. In the presence of isoniazid (350 micrograms/ml) only trace amounts of AD accumulated during 48 hours of transformation indicating much lower activity than that of the intact cells. The most effective among the tested inhibitors of peptidoglycan synthesis were glycine (15 mg/ml) and vancomycin (150 micrograms/ml) which enhanced the transformation activity of the treated cells nearly three times. Increased transformation rate was also obtained by the action of colistin at concentrations ranging from 10 micrograms/ml to 15 micrograms/ml.

    Topics: Biotransformation; Cell Membrane; Cell Wall; Cycloserine; Ethambutol; Glycine; Isoniazid; Mycobacterium; Norleucine; Penicillins; Peptidoglycan; Phenylalanine; Sitosterols; Vancomycin

1994
Aloe vera, hydrocortisone, and sterol influence on wound tensile strength and anti-inflammation.
    Journal of the American Podiatric Medical Association, 1994, Volume: 84, Issue:12

    Aloe vera at doses of 100 and 300 mg/kg daily for 4 days blocked the wound healing suppression of hydrocortisone acetate up to 100% using the wound tensile strength assay. This response was because of the growth factors present in A. vera masking the wound healing inhibitors such as sterols and certain amino acids. The sterols showed good anti-inflammatory activity (-36%) in reducing the croton oil-induced ear swelling. This activity displayed a dose-response relationship.

    Topics: Aloe; Animals; Cholesterol; Croton Oil; Dose-Response Relationship, Drug; Drug Therapy, Combination; Ear; Hydrocortisone; Labyrinthitis; Male; Mice; Mice, Inbred ICR; Pentacyclic Triterpenes; Phytosterols; Plants, Medicinal; Sitosterols; Tensile Strength; Triterpenes; Wound Healing

1994
[Chemical constituents of flower of David lily].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1994, Volume: 19, Issue:10

    Three compounds were isolated from the flower of Lilium devidii. On the basis of chemical reaction, UV, MS, 1HNMR and 13CNMR spectral data, they were identified as beta-sitosterol, stigmasterol and emodin. These compounds are obtained from the plant for the first time.

    Topics: Drugs, Chinese Herbal; Emodin; Sitosterols; Stigmasterol

1994
[Chemical constituents from fresh leaves of Rehmannia glutinosa Libosch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1994, Volume: 19, Issue:3

    Topics: Drugs, Chinese Herbal; Mannitol; Sitosterols

1994
[Chemical constituents of Artemisia roxbugiana Wall].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1994, Volume: 19, Issue:3

    Topics: Drugs, Chinese Herbal; Sitosterols; Triterpenes

1994
[Chemical constituents of Cynanchum stauntonii (Decne.) Schltr. ex Levl].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1994, Volume: 19, Issue:8

    Topics: Drugs, Chinese Herbal; Fatty Acids; Sitosterols; Triterpenes

1994
[Chemical constituents of Notopterygium incisium Ting. III: Chemical constituents isolated and identified from petroleum ether extracts of N. incisium Ting].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1994, Volume: 19, Issue:2

    Six chemical compounds were isolated from the roots and rhizoma of Notopterygium incisium by column chromatography and preparative thin-layer chromatography, and identified by chemical and spectroscopic analysis as beta-sitosterol, oleic acid, linoleic acid, columbianetin, pregnenolone and ferulic acid. The presence of pregnenolone in the genus Notopterygium has not been reported.

    Topics: Coumaric Acids; Drugs, Chinese Herbal; Fatty Acids, Unsaturated; Pregnenolone; Sitosterols

1994
Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis.
    Metabolism: clinical and experimental, 1994, Volume: 43, Issue:7

    We correlated the activity of the rate-limiting enzyme of cholesterol biosynthesis, 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, with the sterol content and composition of mucosal cells from the ileum of three homozygous sitosterolemic subjects and one control subject. In this inherited disease, whole-body cholesterol biosynthesis is decreased and increased amounts of sitosterol are absorbed from the intestine and deposited in tissues. For comparison, similar measurements were obtained in the ileal mucosa of sitosterol-fed rats where sitosterol accounted for 11% of enterocyte sterols. In the three sitosterolemic homozygotes, sitosterol represented 9% to 11% of the total microsomal sterols in the intestinal mucosa, although normal architecture for both crypts and villi is observed. The mean ileal microsomal HMG-CoA reductase activity in the three homozygotes was less than half of control values. In the ileum of sitosterol-fed rats with increased mucosal sitosterol concentrations, microsomal HMG-CoA reductase activity was not inhibited. These results show that in three sitosterolemic homozygotes, abnormally low HMG-CoA reductase activity was detected in the ileum, as previously demonstrated in mononuclear leukocytes and liver. The failure of the increased tissue sitosterol pool to inhibit HMG-CoA reductase in rat ileum suggests that deficient cholesterol biosynthesis in homozygous sitosterolemia is inherited and is not due to feedback inhibition by tissue sitosterol.

    Topics: Adult; Animals; Cholesterol; Feedback; Female; Homozygote; Humans; Hydroxymethylglutaryl CoA Reductases; Ileum; Intestinal Mucosa; Male; Microsomes; Rats; Rats, Sprague-Dawley; Sitosterols

1994
Quantitative study of local distribution of noncholesterol sterols and cholesterol in gallstones.
    Journal of gastroenterology, 1994, Volume: 29, Issue:3

    Quantitative analysis of the local distribution of four noncholesterol sterols, 24-methylene cholesterol, campesterol, stigmasterol, and beta-sitosterol, and of the local distribution of cholesterol in gallstones was performed by mass spectrometry, with D6-cholesterol as an internal standard. The role played by trace amounts of these four noncholesterol sterols in the formation of gallstones was investigated by comparing the amounts of these sterols in different parts of gallstones. It was found that the amounts of the noncholesterol sterols in the inside part were significant greater than the amounts in the outside part of various structural types of gallstones. However, the distribution of the cholesterol did not show such variation. The amounts of noncholesterol sterols distributed locally suggested that these sterols play a role in the formation of gallstones.

    Topics: Cholelithiasis; Cholesterol; Female; Gas Chromatography-Mass Spectrometry; Humans; Male; Middle Aged; Phytosterols; Sitosterols; Sterols; Stigmasterol

1994
Oxidation of steroidal 5-en-3 beta-ols with Jones reagent in ether.
    Steroids, 1994, Volume: 59, Issue:5

    The two-phase oxidation of steroidal 5-en-3 beta-ol (via 5-en-3-ones) into corresponding 4-en-3,6-diones in diethyl ether with Jones reagent was investigated. It was found that the system Jones reagent/diethyl ether enables short reaction times and easy isolation of the obtained products. The exclusive abstraction of 4 alpha-hydrogen during oxidation, together with molecular mechanics (MM2), and semiempirical (PM3) calculations, suggest that boat conformation of ring A precedes the formation of corresponding radicals (or cations).

    Topics: Cholesterol; Chromates; Dehydroepiandrosterone; Deuterium; Diosgenin; Ether; Indicators and Reagents; Oxidation-Reduction; Pregnenolone; Sitosterols; Steroids; Sulfuric Acids

1994
Inhibition of the myotoxic and hemorrhagic activities of crotalid venoms by Eclipta prostrata (Asteraceae) extracts and constituents.
    Toxicon : official journal of the International Society on Toxinology, 1994, Volume: 32, Issue:5

    The antimyotoxic and antihemorrhagic effects of Eclipta prostrata (EP) and three of its constituents (wedelolactone, WE; stigmaterol, ST; and sitosterol, SI) were investigated. The myotoxicity of crotalid venoms (Bothrops jararaca, Bothrops jararacussu and Lachesis muta), purified myotoxins (bothropstoxin, BthTX; bothropasin; and crotoxin), and polylysine was quantified in vitro by the release rate of creatine kinase (CK) from rat or mouse extensor digitorum muscles, and in vivo by the plasma CK activity in mice. The in vitro myotoxicity of the crotalid venoms and myotoxins was neutralized by simultaneous exposure of the muscles to an aqueous extract of EP or to WE. ST and SI were less effective than WE, but interacted synergistically with it. Both the EP extract and WE failed to neutralize the in vitro myotoxic effects of polylysine. The in vivo myotoxicity of venoms and myotoxins was neutralized by their preincubation with the EP extract or WE. Intravenous administration of the plant extract or WE attenuated the increase in plasma CK activity induced by subsequent intramuscular injections of the crotalid venoms or the myotoxins. EP and WE inhibited the hemorrhagic effect of B. jararaca venom, as well as the phospholipase A2 activity of crotoxin and the proteolytic activity of B. jararaca venom. The data provide direct evidence for antimyotoxic and antihemorrhagic effects of EP and WE against the crotalid venoms responsible for most cases of envenomation by snakebites in Brazil. These effects are interpreted as consequences of antiproteolytic and antiphospholipase A2 activities of EP and its constituents.

    Topics: Animals; Coumarins; Creatine Kinase; Crotalid Venoms; Hemorrhage; Mice; Muscles; Plant Extracts; Rats; Sitosterols; Stigmasterol

1994
Regulation of cholesterol uptake in the rat intestinal cell line.
    Biochimica et biophysica acta, 1994, Jan-03, Volume: 1210, Issue:2

    A new model to study cholesterol absorption in the rat intestinal cells is described. Rat intestine epithelial cells IRD98 were incubated with mixed micelles containing bile acid, phospholipid, cholesterol or its nonabsorbable analogue, sitosterol, and trace amounts of [3H]cholesterol or [14C]sitosterol. Cholesterol and sitosterol uptake was then determined following lipid extraction; specific cholesterol uptake was determined as the difference between cholesterol and sitosterol uptake. Cholesterol, but not sitosterol, uptake was time- and dose-dependent and saturable. Loading of cells with non-lipoprotein cholesterol reduced cholesterol, but not sitosterol, uptake in a dose-dependent manner. In contrast, treatment of cells with an inhibitor of cholesterol synthesis, lovastatin, stimulated cholesterol, but not sitosterol, uptake in a dose-dependent manner. Treatment of cells with palmitic, caproic and oleic acids up-regulated specific cholesterol uptake, while linoleic and stearic acids had an opposite effect. None of the fatty acids affected sitosterol uptake.

    Topics: Animals; Carbon Radioisotopes; Cell Line; Cholesterol; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Intestine, Small; Lovastatin; Models, Biological; Oleic Acid; Oleic Acids; Palmitic Acid; Palmitic Acids; Rats; Sitosterols; Stearic Acids; Time Factors; Tritium

1994
Effect of beta-sitosterol on uterine biochemistry: a comparative study with estradiol and progesterone.
    Biochemistry and molecular biology international, 1993, Volume: 31, Issue:4

    Administration of estradiol/progesterone to ovariectomized animals significantly increased the uterine weight, RNA, DNA and protein concentrations. Similarly, administration of beta-sitosterol alone or in combination with estradiol caused a marked increase in the above parameters and the maximum influence was evident only after median and high dose treatments. However, administration of median/high dose of beta-sitosterol along with progesterone accentuated only the RNA and protein concentrations but exerted an inhibitory effect on sitosterol-induced increment in uterine weight and DNA concentrations.

    Topics: Animals; DNA; Estradiol; Estrogens; Estrogens, Non-Steroidal; Female; Isoflavones; Organ Size; Ovariectomy; Phytoestrogens; Plant Preparations; Progesterone; Proteins; Rats; Rats, Wistar; RNA; Sitosterols; Uterus

1993
[Studies on chemical constituents of Smilax menispermoidea D.C].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:10

    Topics: Diosgenin; Drugs, Chinese Herbal; Sitosterols; Stilbenes

1993
[Studies on the chemical constituents of Arthromeris mairei (Brause) Ching].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:9

    Topics: Chromones; Drugs, Chinese Herbal; Flavonoids; Glycosides; Kaempferols; Quercetin; Sitosterols

1993
Assessment of the estrogenic activity of phytoestrogens isolated from bourbon and beer.
    Alcoholism, clinical and experimental research, 1993, Volume: 17, Issue:6

    Phytoestrogenic substances have previously been isolated and identified in two alcoholic beverages: bourbon and beer. To delineate the relative potencies of the estrogenic substances of plant origin thus far identified in these commonly consumed alcoholic beverages, we evaluated the ability of biochanin A, beta-sitosterol, genistein, and daidzein to bind to cytosolic estrogen receptor binding sites. The in vitro studies demonstrated that each of the contained substances was capable of effectively competing for cytosolic estrogen receptor binding sites of rat liver and uterus. Further, the two phytoestrogenic constituents of bourbon, beta-sitosterol and biochanin A, were less potent than those present in beer. Given the high concentration of beta-sitosterol in bourbon, we chose to evaluate the estrogenicity of beta-sitosterol in vivo using ovariectomized rats. beta-sitosterol was administered either daily or intermittently at 3 doses, based on amounts previously determined to be present in bourbon. The in vivo studies demonstrated that beta-sitosterol is capable of producing a weak estrogenic effect only at the lowest dose (6.2 micrograms/dl) administered intermittently. These responses suggest that beta-sitosterol may be weakly estrogenic at low doses, but is unable to maintain such an effect at higher doses.

    Topics: Alcoholic Beverages; Animals; Beer; Cytosol; Dose-Response Relationship, Drug; Estrogens; Estrogens, Non-Steroidal; Female; Genistein; Isoflavones; Liver; Male; Phytoestrogens; Plant Preparations; Rats; Rats, Wistar; Receptors, Estrogen; Sitosterols; Uterus

1993
Triterpenes and B-sitosterol from piper betle: isolation, antiplatelet and anti-inflammatory effects.
    Biochemical Society transactions, 1993, Volume: 21, Issue:4

    Topics: Adenosine Diphosphate; Animals; Anti-Inflammatory Agents, Non-Steroidal; Arachidonic Acid; Areca; Aspirin; Chromatography, Liquid; Edema; Humans; Plants, Medicinal; Platelet Activating Factor; Platelet Aggregation; Platelet Aggregation Inhibitors; Rats; Sitosterols; Triterpenes

1993
Comparison of intestinal absorption of cholesterol with different plant sterols in man.
    European journal of clinical investigation, 1993, Volume: 23, Issue:12

    Intestinal absorption of cholesterol, campesterol, campestanol, stigmasterol and sitosterol were measured in 10 healthy subjects by an intestinal perfusion technique over a 50 cm segment of the upper jejunum using sitostanol as non-absorbable marker. Cholesterol absorption was highest and averaged 33%., whereas the absorption rate of sitosterol averaged 4.2% and of stigmasterol 4.8%. Higher absorption rates were found for campesterol (9.6%). Campestanol, the 5 alpha saturated derivative of campesterol, showed the highest absorption rate (12.5%) of all plant sterols. A positive correlation between the absorption rate of cholesterol and campesterol was established. In addition, there was a negative correlation between the ratio of sitosterol to cholesterol and the mass of cholesterol absorption. These results are in agreement with previous observations in animal studies, namely, that increasing the length of the side-chain of cholesterol decreases the absorbability of the sterol. Surprisingly, campestanol, the 5 alpha saturated derivate of campesterol, was shown to have higher absorbability compared with its unsaturated compound. This finding is in contrast to previous assumptions, that hydrogenisation of the nucleus double bond of a sterol causes a decrease of absorbability, as has been demonstrated for cholesterol/cholestanol and sitosterol/sitostanol.

    Topics: Cholesterol; Humans; Intestinal Absorption; Male; Perfusion; Phytosterols; Sitosterols

1993
[Comparison of chemical constituents between new and old processed products of rhizoma Typhonii].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:4

    Experimental results showed that the original contents of chemical constituents in the new processed products were higher than those in the old one, while the content of assistant alum in the new products was lower than that of the old one. It is thus confirmed that the new processing technology is reasonable.

    Topics: Amino Acids; Drugs, Chinese Herbal; Hot Temperature; Oleic Acids; Sitosterols; Technology, Pharmaceutical

1993
[Chemical constituents of the fruit of Panax ginseng C. A. Meyer].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:5

    Four compounds were isolated from the fruit of cultivated Panax ginseng and identified as beta-sitosterol,20(R)-protopanaxatriol, daucosterine and 20(R)-ginsenoside-Rg3 on the basis of physicochemical constants and spectral evidences.

    Topics: Fruit; Panax; Plants, Medicinal; Sapogenins; Sitosterols; Triterpenes

1993
[Influence of the blight of Morinda officinalis How on microscopic structure and constituents of the host].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:7

    The results showed that microscopic structure in biennial roots, the contents of B and Mn in nutritive organ and beta-sitosterol content in roots, stems of Morinda officinalis were affected markedly. The total sugar content in the roots and aerial stems was decreased by 5.42%-15.29%.

    Topics: Boron; Carbohydrates; Manganese; Medicine, Chinese Traditional; Plant Diseases; Plants, Medicinal; Sitosterols

1993
[Chemical constituents of fresh bulbs of Fritillaria thunbergii Miq].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:6

    Topics: Alkaloids; Drugs, Chinese Herbal; Sitosterols

1993
[Chemical constituents of Emilia sonchifolia L. DC].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1993, Volume: 18, Issue:2

    Five known compounds were obtained from the whole plant of Emilia sonchifolia. By means of chemical and spectral methods, they were identified to be simiral, beta-sitosterol, stigmasterol, palmitic acid and honey acid.

    Topics: Drugs, Chinese Herbal; Palmitic Acid; Palmitic Acids; Sitosterols; Stigmasterol

1993
A method for the preparation of submicron particles of sparingly water-soluble drugs by precipitation in oil-in-water emulsions. II: Influence of the emulsifier, the solvent, and the drug substance.
    Journal of pharmaceutical sciences, 1993, Volume: 82, Issue:6

    Small particles of two steroids, cholesteryl acetate and beta-sitosterol, were prepared by the following technique. The steroid was dissolved in an organic solvent, which was emulsified in water in the presence of surfactant, thus giving a water-continuous emulsion. As the organic solvent was evaporated, the steroid precipitated. One particle was found to form in each emulsion droplet. Particle sizes down to 25 nm were obtained by this method. Particles were prepared from emulsions containing different organic solvents and surfactants, and the effect on the size and the colloidal stability of the particles was examined. The final particle suspension is relatively stable provided the initial emulsion is stable. Furthermore, there is a close correlation between the initial droplet size and the final particle size. The particle size, therefore, can be varied in the same manner as the size of emulsion droplets; that is, by changing the emulsification process parameters and the amount and choice of surfactant and the oil-to-water ratio. Finally, the particle size depends on the choice of solvent and only slightly on the concentration of drug in the oil phase of the emulsion.

    Topics: Chemical Precipitation; Chemistry, Pharmaceutical; Cholesterol Esters; Drug Carriers; Emulsions; Excipients; Methods; Microscopy, Electron, Scanning; Microspheres; Models, Chemical; Oils; Sitosterols; Solubility; Solvents; Surface-Active Agents; Water

1993
Abscisic acid-lipid interactions: a phospholipid monolayer study.
    Biochimica et biophysica acta, 1993, Aug-15, Volume: 1150, Issue:2

    Lipid monolayer studies were performed on a Langmuir trough in the absence and in the presence of the plant hormone abscisic acid (ABA). The ABA-induced effects on the lipid monolayers can be summarized as follows: (i) ABA as the free acid (pH below 5.3) increased the molecular area and slightly decreased the surface pressure in the collapse points of monolayers made of saturated, unsaturated and of mixed lipids; ABA as the anion showed only minor effects. (ii) The ABA-induced area increase of the lipid monolayers decreased when the surface pressure increased, but some ABA remained in the monolayers made of unsaturated phospholipids even at collapse pressure. (iii) The incorporation of ABA into the monolayers could be inhibited by adding the plant sterol beta-sitosterol to the monolayer forming phospholipids. (iv) There was no substantial difference of ABA action on plant phospholipids as compared with other phospholipids. (v) ABA had a much stronger influence on unsaturated phospholipids than on saturated ones. (vi) ABA decreased the phase-transition temperature of saturated phospholipids. These results, which agree with those obtained from phospholipid vesicle studies, indicate that the physical state of the lipid is important for the ability of ABA penetrating into the lipid monolayer. Finally, a possible relevance of these results is discussed in terms of the action of ABA on guard cell membranes of plants.

    Topics: Abscisic Acid; Hydrogen-Ion Concentration; Membrane Lipids; Phospholipids; Sitosterols; Surface Properties

1993
New model to study cholesterol uptake in the human intestine in vitro.
    Journal of lipid research, 1993, Volume: 34, Issue:2

    A new model to study cholesterol uptake in the human intestine in vitro is described. Human small intestine organ cultures were incubated with mixed micelles containing bile acid, phospholipid, and cholesterol or its nonabsorbable analogue, sitosterol; trace amounts of labeled cholesterol or sitosterol were added to the micelles. After incubation, the lipids were extracted from the cells and cholesterol and sitosterol uptake was evaluated. Specific cholesterol uptake was determined as a difference between cholesterol and sitosterol uptake. Cholesterol, but not sitosterol, uptake was time- and dose-dependent. Rapid and slow phases of cholesterol uptake were observed. Cholesterol uptake was also temperature-dependent. Removal of epithelial cells from human intestine explants reduced cholesterol, but not sitosterol, uptake. Inhibition of acyl CoA:cholesterol acyltransferase by Sandoz compound 58-035 and treatment with monensin reduced cholesterol uptake, but not sitosterol uptake, in a dose-dependent manner. In contrast, treatment of cultures with an inhibitor of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase, lovastatin, stimulated cholesterol, but not sitosterol, uptake in a dose-dependent manner; mevalonic acid reversed the effect of lovastatin. The presented model allows large-scale in vitro studies of different stages of cholesterol absorption in the human intestine.

    Topics: Amides; Bile Acids and Salts; Child; Child, Preschool; Cholesterol; Humans; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Infant; Infant, Newborn; Intestinal Absorption; Kinetics; Lovastatin; Micelles; Models, Biological; Monensin; Organ Culture Techniques; Organosilicon Compounds; Phospholipids; Sitosterols; Sterol O-Acyltransferase

1993
Treatment of severe familial hypercholesterolemia in childhood with sitosterol and sitostanol.
    The Journal of pediatrics, 1993, Volume: 122, Issue:2

    This study was undertaken to compare the ability of two plant sterols to reduce serum levels of lipids and to compare their mechanism of action in nine children with severe familial hypercholesterolemia (total and low-density lipoprotein cholesterol concentrations averaged 9.57 mmol/L (370 mg/dl) and 7.87 mmol/L (301 mg/dl)). After a 3-month strict diet, the children were given sitosterol pastils (2 gm three times a day) for 3 months, followed by a 7-month course of sitostanol (0.5 gm three times a day). Serum lipoprotein levels and serum concentrations of campesterol and sitosterol were determined in all nine children, and the fecal excretion of neutral and acidic sterols were determined in seven children at the end of each therapeutic regimen. Sitosterol reduced low-density lipoprotein cholesterol levels by 20% (p < 0.01); sitostanol reduced low-density lipoprotein cholesterol levels by 33% after 3 months and 29% after 7 months (p < 0.01 compared with diet; p < 0.05 compared with sitosterol). Although sitosterol did not alter serum concentrations of campesterol and sitosterol, a significant reduction did occur during sitostanol therapy (-47% and -51%, respectively; p < 0.01). Fecal excretion of neutral sterols increased from 6.7 mg/kg per day during the control period to 9.7 mg/kg per day during sitosterol administration (p < 0.05), and to 12.6 mg/kg per day during sitostanol administration (p < 0.05 compared with diet and sitosterol periods), indicating an increase in the inhibition of intestinal cholesterol absorption. All children completed the study and no obvious side effects occurred. The data indicate that sitostanol, even with a dose four-fold lower than that of sitosterol, was significantly more effective in reducing elevated levels of low-density lipoprotein cholesterol, and the reduction in serum lipid levels was of the same magnitude as that observed with systemic lipid-lowering drugs. These results suggest that sitostanol, a nonabsorbable plant sterol, could be the drug of choice for treating familial hypercholesterolemia in childhood.

    Topics: Adolescent; Alanine Transaminase; Alkaline Phosphatase; Apolipoproteins B; Carotenoids; Child; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Feces; Female; Heterozygote; Humans; Hyperlipoproteinemia Type II; Male; Phytosterols; Sitosterols; Sterols

1993
[Regulation of cholesterol absorption in human and rat small intestine epithelial cells].
    Biokhimiia (Moscow, Russia), 1993, Volume: 58, Issue:2

    Cholesterol absorption in human small intestine organ culture and rat small intestine epithelial cell culture IRD-98 has been studied using [14C] cholesterol, [3H] cholesterol and [14C] sitosterol. It has been found that cholesterol absorption is a dose- and time-dependent process, while sitosterol absorption is not and makes up to about 25% of the total cholesterol absorption. Cholesterol absorption appeared to be a specific process. The endocytosis inhibitor monensin decreased specific cholesterol absorption by 37%. Cholesterol absorption was examined under different conditions influencing cholesterol metabolism in the cell. Loading of IRD-98 cells with non-lipoprotein cholesterol caused a dose-dependent decrease of cholesterol absorption. The inhibitor of acyl coenzyme A:cholesterol acyl transferase (ACAT), compound Sandoz 58-035, had a similar effect on cholesterol absorption. Lovastatin, an inhibitor of 3-hydroxymethyl-3-glutaryl coenzyme A (HMG-CoA) reductase, stimulated cholesterol absorption in a dose-dependent manner. Loading of cells with cholesterol, lovastatin and Sandoz 58-035 had no effect on sitosterol absorption. The possibility has been demonstrated of using human small intestine organ culture and rat small intestine epithelial cell culture IRD-98 as models for studying cholesterol absorption.

    Topics: Adolescent; Animals; Cells, Cultured; Child; Child, Preschool; Cholesterol; Enzyme Inhibitors; Epithelial Cells; Epithelium; Humans; Infant; Infant, Newborn; Intestinal Absorption; Intestine, Small; Organ Culture Techniques; Rats; Sitosterols

1993
Relation of cholesterol-stimulated Staphylococcus aureus growth to chronic blepharitis.
    Investigative ophthalmology & visual science, 1993, Volume: 34, Issue:7

    Many types of chronic blepharitis have been believed to be primarily microbial in origin; however, it was proposed that differences and changes in lipid composition of meibomian secretion may be the initiating factor in some of these. It was recently reported that there are two subgroups of normals, those whose meibomian secretions contain high levels of cholesterol esters and those whose secretions contain very low levels of these esters. Thus, these subgroups of normals were defined on the basis of detailed lipid analyses of meibomian secretions from individuals showing no clinical signs of chronic blepharitis. All secretions from patients in the various disease groups contain high levels of these esters. Based on previous observations that in some chronic blepharitis disease groups certain Staphylococcus species were capable of hydrolyzing cholesterol esters, the authors tested the hypothesis that the resulting cholesterol might affect growth of Staphylococcus aureus.. Staphylococcus aureus growth stimulation in Mueller-Hinton broth by cholesterol was determined by colony forming units. Growth stimulation by cholesterol and other additives was also determined by the optical density 650 nm method. Statistical analyses included analysis of variance and the Student's t test.. Cholesterol stimulated Staphylococcus aureus growth was significant during the first 24 hr period (20% increase at 25 microM cholesterol, P < 0.02), and for the total 48 hr period (40% increase at 400 microM cholesterol, P < 0.005) when compared to the respective control. Growth stimulation, determined by OD at 650 nm, in the presence of cholesterol was significantly greater (P < 0.02) than that in the presence of either sitosterol or cholestanol when the sterol concentration was 190 microM.. These results suggest that the presence and hydrolysis of cholesterol esters of meibomian secretions may contribute to the proliferation of Staphylococcus spp, especially Staphylococcus aureus, observed in some chronic blepharitis disease groups.

    Topics: Blepharitis; Cholestanol; Cholesterol; Chronic Disease; Colony Count, Microbial; Eye Infections, Bacterial; Fatty Acids; Humans; Hydrolysis; Sitosterols; Staphylococcal Infections; Staphylococcus aureus

1993
Effect of lovastatin on cholesterol absorption in cholesterol-fed rabbits.
    Pharmacology & toxicology, 1993, Volume: 72, Issue:3

    The aim of the present study was to investigate the effect of the hydroxymethylglutaryl (HMG)-CoA reductase inhibitor lovastatin on some aspects of cholesterol metabolism in cholesterol-fed rabbits. The plasma cholesterol concentration was markedly lower in lovastatin-treated rabbits (6 mg/rabbit/day) compared to controls after 36 days of cholesterol-feeding (x +/- S.E.) (19 +/- 4 mmol/l, n = 9 versus 153 +/- 17 mmol/l, n = 7) (P < 0.00001). Intestinal absorption of cholesterol in such rabbits was reduced by 15% in lovastatin-treated rabbits (n = 21) compared to controls (n = 18) (P < 0.025). The results suggest that the hypocholesterolaemic effect of lovastatin in cholesterol-fed rabbits is associated with a decreased intestinal absorption of cholesterol.

    Topics: Animals; Cholesterol; Cholesterol, Dietary; Hypercholesterolemia; Intestinal Absorption; Lovastatin; Male; Rabbits; Sitosterols

1993
[Searching for cytostatic substances in plant tissue of Maytenus molina by in vitro culture. III. Release of substances from active biological fractions from the callus extract of Maytenus wallichiana R. and B].
    Acta poloniae pharmaceutica, 1992, Volume: 49, Issue:1-2

    Chromatographic studies controlled by biological evaluation (Tetrahymena test) showed some colour substances among them tingenone and beta-sitosterol. In order to identify the substances extraction and biologically controlled chromatography was carried out. Two substances were isolated, their properties corresponding with tingenone and beta-sitosterol.

    Topics: Microbial Sensitivity Tests; Plant Extracts; Plants, Medicinal; Sitosterols; Triterpenes

1992
[Chemical constituents of the root of Oplopanax elatus Nakai].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:9

    Topics: Drugs, Chinese Herbal; Glucosides; Phenylpropionates; Sitosterols

1992
[Chemical constituents of Cynanchum thesioides K. Schum].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:12

    Topics: Drugs, Chinese Herbal; Quercetin; Sitosterols; Succinates

1992
[Chemical constituents of Rhodiola kirilowii (Reg.) Reg].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:2

    Three compounds were isolated from the water-soluble part of alcohol extracts of rhizomes of Rhodiola kirilowii. Two of them were identified as salidroside and tyrosol, respectively by chemical and spectral analysis. beta-sitosterol was obtained from the petroleum extracts of the plant.

    Topics: Drugs, Chinese Herbal; Glucosides; Phenols; Phenylethyl Alcohol; Sitosterols

1992
[The antigastroulcerative activity of beta-sitosterol-beta-D-glucoside and its aglycone in rats].
    Hua xi yi ke da xue xue bao = Journal of West China University of Medical Sciences = Huaxi yike daxue xuebao, 1992, Volume: 23, Issue:1

    Beta-sitosterol-beta-D-glucoside and its aglycone (the major constituent of the seed oil of Hippophae rhamnoides L.) were investigated for their antigastroulcerative activity in rats. Two experimental gastric ulcer models were selected: chronic acetic acid-induced ulcers and cold stress-induced ulcers. Both the glucoside and its aglycone showed antiulcerative activity in chronic acetic acid-induced gastric ulcer models, and their effects were at least comparable to the effects of wishupin in combination with cimetidine. The effect of aglycone appears better than the glucoside's. Glucoside also showed visibly antiulcerative effects on cold stress-induced ulcers, but wishupin combined with cimetidine did not have such effects.

    Topics: Acetates; Acetic Acid; Animals; Anti-Ulcer Agents; Female; Male; Rats; Rats, Inbred Strains; Sitosterols; Stomach Ulcer; Stress, Physiological

1992
[Chemical constituents of Isodon albopilosus (C.Y. Wu et H.W. Li) Hara].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:4

    Five compounds have been isolated from the stems and leaves of Isodon albopilosus. On the basis of spectroscopic and chemical data, they were identified as macrocalyxin C, stearic acid, beta-sitosterol, ursolic acid and beta-sitosterol-beta-D-glucoside, respectively.

    Topics: Diterpenes; Drugs, Chinese Herbal; Sitosterols; Stearic Acids

1992
[Constituents of the dry roots of Rehmannia glutinosa Libosch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:5

    From the extract of dry roots of Rehmannia glutimosa, fatty acids, palmitic acid, beta-sitosterol, daucosterol and sulfur (Ss) cyclic compound were isolated and identified. The latter four were isolated for the first time.

    Topics: Drugs, Chinese Herbal; Fatty Acids; Palmitic Acids; Sitosterols

1992
[Effective chemical constituents of Artemisia argyi Levl. et Vant for inhibition of platelet aggregation].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:6

    beta-Sitosterol and eupatilin were isolated and identified from Artemisia argyi. Both of them showed marked inhibition of platelet aggregation.

    Topics: Drugs, Chinese Herbal; Flavonoids; Platelet Aggregation Inhibitors; Sitosterols

1992
[Chemical constituents of Lysionotus].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:7

    Topics: Drugs, Chinese Herbal; Flavones; Flavonoids; Sitosterols

1992
Changes in endogenous lipid excretion in rats fed diets containing non-heated and thermally oxidized olive oils.
    Scandinavian journal of gastroenterology, 1992, Volume: 27, Issue:12

    The objective of this study was to determine the effects of diets containing non-heated and thermally oxidized olive oils on fecal endogenous lipids. Male Wistar rats were fed fat-free diets and diets supplemented with 12% non-heated, heated, and a 1:1 mixture of non-heated/heated olive oils. After a 15-day experimental period two groups of fecal lipids from major endogenous sources were quantitated: neutral sterols and fatty acids associated with intestinal microflora action. Fecal endogenous sterols, particularly cholesterol, were significantly higher when diets contained oil, and excretion increased as the dietary oil alteration increased. Similar results were obtained for endogenous fatty acids. Increments of fecal sterols, dependent on oil alteration, could be explained by impairments in triglyceride hydrolysis and subsequent effect on cholesterol micellar solubilization. Moreover, high concentrations of poorly digestible lipids may have led to intestinal microbial modifications.

    Topics: Animals; Cholestanol; Cholesterol; Dietary Fats, Unsaturated; Fatty Acids; Feces; Hot Temperature; Lipid Metabolism; Male; Olive Oil; Plant Oils; Rats; Rats, Wistar; Sitosterols

1992
[Chemical constituents of Cirsium Japonicum D. C].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1992, Volume: 17, Issue:8

    Topics: Drugs, Chinese Herbal; Flavonoids; Oleanolic Acid; Sitosterols; Stigmasterol; Triterpenes

1992
Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels.
    Clinica chimica acta; international journal of clinical chemistry, 1992, Jun-30, Volume: 208, Issue:3

    Proportions of cholesterol precursors (squalene, delta 8-cholestenol, desmosterol and lathosterol), plant sterols (campesterol and sitosterol) and cholestanol to cholesterol in serum were measured before and serially after liver transplantation in eight patients with primary biliary cirrhosis (PBC) and three with acute liver necrosis. The preoperative proportions of cholestanol were 12 and 3-times higher in the PBC and necrosis groups, respectively, than in a control group of 27 individuals, while those of lathosterol were low in both groups and the campesterol/sitosterol ratio in the PBC group. During the operation the proportions of cholestanol fell sharply and those of lathosterol rose especially in the PBC group. During the postoperative follow-up of 5 weeks the proportions of the non-cholesterol sterols were markedly improved especially in the necrosis group yet those of cholestanol remained high and the campesterol/sitosterol ratios low, particularly in the PBC group. The proportions of lathosterol increased gradually almost to the control limits within the postoperative 5-week period, whereas those of desmosterol decreased. The non-cholesterol sterol values were not related to acute rejections, while significant correlations of cholestanol to liver function tests was found especially at the end of the follow-up.

    Topics: Acute Disease; Adult; Cholestanol; Cholesterol; Female; Humans; Liver Cirrhosis, Biliary; Liver Diseases; Liver Transplantation; Male; Middle Aged; Necrosis; Phytosterols; Protein Precursors; Sitosterols; Squalene

1992
Comparative study of the effects of beta-sitosterol, estradiol and progesterone on selected biochemical parameters of the uterus of ovariectomised rats.
    Journal of ethnopharmacology, 1992, Volume: 36, Issue:1

    A comparative study was made of the effects of beta-sitosterol, estradiol-17 beta and progesterone, individually and in combinations, on certain biochemical parameters important to carbohydrate metabolism in the uteri of adult ovariectomised rats. beta-Sitosterol (SITO), estradiol (E2) and combined treatment (SITO + E2) induced significant increases in glycogen concentration and the activities of glucose-6-phosphate dehydrogenase (G6PDH), phosphohexose isomerase (PHI) and total lactate dehydrogenase (LDH). Progesterone (P) administration however, raised only the uterine PHI and LDH activities. Co-administration of P with beta-sitosterol (P + SITO) suppressed the SITO-induced increase in glycogen concentration and G6PDH activity. On the other hand, combined treatment (P + SITO) augmented total LDH activity.

    Topics: Animals; Carbohydrate Metabolism; Estradiol; Female; Glucose-6-Phosphate Isomerase; Glucosephosphate Dehydrogenase; Glycogen; L-Lactate Dehydrogenase; Ovariectomy; Ovary; Progesterone; Rats; Rats, Inbred Strains; Sitosterols; Sterols; Uterus

1992
Metabolic blocks in the degradation of beta-sitosterol by a plasmid-cured strain of Arthrobacter oxydans.
    Journal of basic microbiology, 1992, Volume: 32, Issue:3

    Plasmid-harbouring, sterol-decomposing organism Arthrobacter oxydans 317 was treated with sodium dodecylsulphate to obtain a plasmid-cured strain A. oxydans 317 A1 incapable of utilizing 4-androstene-3,17-dione (AD). The strain 317 A1 was unable to degrade beta-sitosterol side chain completely to form AD but could carry out partial degradation as shown by the accumulation of 3-oxochol-4-en-24-oic acid as a major metabolite and 27-norcholest-4-en-3,24-dione as a minor metabolite. The strain could form 1,4-androstadiene-3,17-dione (ADD) from 3-oxo-23,24-bisnorchol-1,4-dien-22- oic acid (BNC) to a limited extent. The existence of metabolic blocks in the conversion of 3-oxochol-4-en-24-oic acid to 3-oxo-23,24-bis-norchol-4-en-22-oic acid and further conversion to AD by the plasmid-cured strain 317 A1 was suggested. Neither the formation of ADD from AD nor the conversion of AD and ADD to 9 alpha-hydroxy derivatives leading to steroid ring opening could be done by the plasmid-cured strain but the 17 beta-reduction of AD and ADD and 1(2)-reduction of ADD were not affected by the absence of the plasmid. It was proposed that plasmid determines 1(2)-dehydrogenation and 9 alpha-hydroxylation of steroid ring structure in this organism.

    Topics: Androstadienes; Androstenedione; Arthrobacter; Biodegradation, Environmental; Cholestenones; Plasmids; Sitosterols; Species Specificity

1992
Effects of unsaturated and saturated dietary plant sterols on their serum contents.
    Clinica chimica acta; international journal of clinical chemistry, 1992, Jan-31, Volume: 205, Issue:1-2

    Rapeseed oil fed to 24 hypercholesterolemic patients (50 g/day) reduced serum cholesterol (-8.5%) and cholestanol concentrations but increased those of campesterol and sitosterol. Continuation of rapeseed oil alone or with added sitosterol (625 mg/day) or sitostanol (630 mg/day) had no further effect on serum cholesterol. Rapeseed oil with sitosterol increased further its own proportion to cholesterol in serum but reduced that of campesterol while rapeseed oil with sitostanol reduced the proportions of both sitosterol and campesterol proportionately to the pretreatment values. The changes in the campesterol and sitosterol proportions were negatively and positively related to each other during the sitosterol and sitostanol additions, respectively. Thus, concentrations of unsaturated plant sterols in serum reflect their dietary intakes, saturated plant sterols are virtually not absorbed, plant sterols interfere with absorption of unsaturated structurally different plant sterols and cholestanol, and plant sterol-induced reduction of sterol absorption may be positively related to absorption efficiency of sterols.

    Topics: Adult; Body Weight; Brassica; Cholesterol; Dietary Fats; Female; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Plant Oils; Sitosterols

1992
Selection and characterization of new microorganisms for the manufacture of 9-OH-AD from sterols.
    Journal of basic microbiology, 1992, Volume: 32, Issue:1

    Using a special selection procedure, several mutants of Mycobacterium vaccae were isolated which were capable of converting sterols to 9 alpha-hydroxyandrost-4-ene-3,17-dion (9-OH-AD). Two mutants, Mycobacterium vaccae ZIMET 11052 and 11053, respectively, were further investigated. Strains of the species Mycobacterium fortuitum are mainly used for commercially obtaining 9-OH-AD from sterols. In contrast to the species Mycobacterium fortuitum the species Mycobacterium vaccae has not been reported to contain pathogenic strains. This seems an advantage for industrial application. Mutants with the ability of converting sterols to 9 alpha-hydroxysteroids have a defect in the steroid-1-dehydrogenase activity which is, however, only a partial one. The remaining activity may cause an undesirable degradation of the steroid nucleus. The steroid-1-dehydrogenase activity was tested using an assay developed by ATRAT (1986). We confirmed two apparently distinct steroid-1-dehydrogenases in Mycobacterium fortuitum NRRL B-8119 as reported by WOVCHA et al. (1979). One of them has an activity on androst-4-ene-3,17-dion (AD). The activity is increased by induction with sitosterol. The other one is active on 9-OH-AD. But Mycobacterium vaccae does not possess steroid-1-dehydrogenase activity on 9-OH-AD, and the AD specific steroid-1-dehydrogenase is not effected by sitosterol. The consequence is a high level of protection against steroid nucleus degradation yielding an effective accumulation of 9-OH-AD in fermentations with Mycobacterium vaccae mutants.

    Topics: Androstenedione; Models, Biological; Mutagenesis; Mycobacterium; Oxidoreductases; Sitosterols; Sterols

1992
[Microbial degradation of beta-sitosterol: production of delta 4-androstene-3,17-dione].
    Yao xue xue bao = Acta pharmaceutica Sinica, 1992, Volume: 27, Issue:1

    Degradation of the side chain of beta-sitosterol (Ib) gave delta 4-androstene-3,17-dione (II) and a small amount of delta 1,4-androstene-3,17-dione (III) by Mycobacterium vaccae 209-20. The yield of the product II was 32%.

    Topics: Androstenedione; Mycobacterium; Sitosterols

1992
High serum cholestanol and low campesterol/sitosterol ratio indicate severe liver damage and liver transplantation in primary biliary cirrhosis.
    Transplantation proceedings, 1992, Volume: 24, Issue:1

    Topics: Bilirubin; Biomarkers; Cholesterol; Female; Humans; Liver Cirrhosis, Biliary; Liver Diseases; Liver Transplantation; Male; Phytosterols; Reference Values; Sitosterols

1992
Cholesterol metabolism in distance runners.
    Clinical physiology (Oxford, England), 1992, Volume: 12, Issue:1

    Faecal steroid excretion, including betasitosterol excretion, whole-body cholesterol synthesis, plasma lipids, and lipoprotein concentrations and habitual diet, were determined in 14 male distance runners and 14 sedentary men. The proportion of cholesterol-derived steroids excreted as bile acids, and the quantity of betasitosterol excreted in the faeces were significantly (P less than 0.05) higher in the runners compared with the sedentary men. Faecal betasitosterol excretion and the proportion of cholesterol-derived steroids excreted as bile acids were correlated significantly in the distance runners and the sedentary men (r = 0.774, n = 28, P less than 0.001). These results suggest that greater dietary intake of plant sterols may contribute to the higher proportion of cholesterol-derived steroids excreted as bile acids in distance runners.

    Topics: Adult; Bile Acids and Salts; Cholesterol; Diet; Exercise; Feces; Humans; Male; Middle Aged; Running; Sitosterols; Steroids; Sterols

1992
Plasma non-cholesterol sterols in patients with non-insulin dependent diabetes mellitus.
    Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme, 1992, Volume: 24, Issue:4

    Plasma plant sterol concentrations (an index of cholesterol absorption efficiency) and plasma lathosterol concentration (an index of cholesterol synthesis rate) were measured in 52 patients with non-insulin dependent diabetes mellitus (NIDDM) and 36 non-diabetic controls. Plasma plant sterol concentrations were significantly (P less than 0.01) lower in diabetic patients (campesterol: men -36%, women -48%; betasitosterol: men -35%, women -42%). Fasting serum insulin levels were inversely correlated with plasma plant sterol concentrations in diabetic patients (campesterol: r = -0.347, P = 0.012; betasitosterol: r = -0.345, P = 0.012) and in non-diabetic men (campesterol: r = -0.578, P = 0.039; betasitosterol: r = -0.702, P = 0.008). Serum insulin levels were also correlated significantly with plasma lathosterol concentration in diabetic patients (r = 0.295, P = 0.034). The results of this study suggest that absorption of plant sterols and possibly cholesterol from the diet may be reduced in hyperinsulinemic diabetics.

    Topics: Adult; Aged; Cholesterol; Diabetes Mellitus, Type 2; Female; Humans; Insulin; Male; Middle Aged; Phytosterols; Sitosterols

1992
Pravastatin and lovastatin similarly reduce serum cholesterol and its precursor levels in familial hypercholesterolaemia.
    European journal of clinical pharmacology, 1992, Volume: 42, Issue:2

    The hypocholesterolaemic effect of pravastatin 40 mg and lovastatin 40 mg daily has been compared in patients with familial hypercholesterolaemia (FH). Administration of the two drugs was separated by a three-month washout period. The reduction in total serum cholesterol after 1,2 and 4 weeks of treatment was similar after pravastatin (-23%, -32% and -32%) and lovastatin (-23%, -30% and -31%). The serum concentrations of LDL cholesterol were similarly reduced, whilst triglycerides, other lipoproteins, cholestanol and squalene were not altered. The reductions in the serum levels of the cholesterol precursor sterols, delta 8-cholesterol, desmosterol and lathosterol were not significantly different after either drug. The lack of difference suggests that cholesterol synthesis was equally inhibited by the two agents. In addition, the serum content of the plant sterols campesterol and sitosterol tended to be equally increased. The comparability of the increases suggests that the absorption and biliary elimination of the two sterols were equally affected by the two statins. Thus, no difference was found between the effects of pravastatin and lovastatin on the serum levels and metabolic precursors of cholesterol in FH during four weeks of treatment.

    Topics: Adult; Aged; Cholesterol; Cholesterol, LDL; Desmosterol; Female; Humans; Hyperlipoproteinemia Type II; Isomerism; Lovastatin; Male; Middle Aged; Phytosterols; Pravastatin; Sitosterols; Triglycerides

1992
Long-term treatment of severe familial hypercholesterolemia in children: effect of sitosterol and bezafibrate.
    Pediatrics, 1992, Volume: 89, Issue:1

    Seven prepubertal children (age range 5.3 to 10.8 years) with severe heterozygous familial hypercholesterolemia (serum cholesterol concentration 416 +/- 85 mg/dL and low-density lipoprotein [LDL] cholesterol concentration 360 +/- 90 mg/dL) were first treated by dietary intervention, second by sitosterol (3 x 2 g/d), and third by bezafibrate (2 x 200 mg/d). Each treatment period lasted 3 months. Subsequently, a treatment combining half the dose of sitosterol and bezafibrate was administered for the following 24 months. Diet alone reduced total and LDL cholesterol values by 4.5% (not significant) and 6.6% (P less than .05), respectively. Sitosterol lowered total and LDL cholesterol values by 17% (P less than .05) when compared with diet alone. Compared with sitosterol, bezafibrate produced a more pronounced effect on total and LDL cholesterol values (-18% and -28%, P less than .05), and high-density lipoprotein cholesterol concentration increased significantly from 48 mg/dL to 55 mg/dL. Combined treatment with half the dose each of sitosterol and bezafibrate was as effective as the higher dose of bezafibrate, and reduction averaged almost 40% and 50% for total and LDL cholesterol values; this lipid-lowering effect persisted for the next 24 months. Laboratory safety parameters and physical examination revealed no obvious side effects. This study indicates that the combination of sitosterol (3 x 1 g/d) plus bezafibrate (1 x 200 mg/d) is an alternate, acceptable, safe, and effective therapeutic approach for treatment of severe hypercholesterolemia in children with high-risk familial hypercholesterolemia.

    Topics: Apolipoprotein A-I; Bezafibrate; Child; Cholesterol, HDL; Cholesterol, LDL; Drug Administration Schedule; Drug Therapy, Combination; Female; Follow-Up Studies; Humans; Hyperlipoproteinemia Type II; Male; Sitosterols; Triglycerides

1992
A butyrolactone lignan disaccharide from Flacourtia ramontchi.
    Phytochemistry, 1991, Volume: 30, Issue:3

    beta-Sitosterol, beta-sitosterol-beta-D-glucopyranoside and a butyrolactone lignan disaccharide, ramontoside, were isolated from the heartwood of Flacourtia ramontchi. The structure of ramontoside was determined as diphyllin-4-O-[beta-D-glucopyranosyl(1---4)]-beta- 2,3-di-O-methyl-D-xylopyranoside by hydrolysis and spectral data.

    Topics: Acetylation; Carbohydrate Sequence; Dioxolanes; Glycosides; Hydrolysis; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Molecular Structure; Plants, Medicinal; Sitosterols

1991
Plasma noncholesterol sterols in male distance runners and sedentary men.
    European journal of applied physiology and occupational physiology, 1991, Volume: 63, Issue:2

    Plasma lathosterol concentration is taken to be an index of the rate of cholesterol synthesis and plasma concentrations of plant sterols just as campesterol and betasitosterol are taken to be indeces of cholesterol absorption efficiency. These noncholesterol sterols were measured in plasma from 14 male distance runners and 10 sedentary men. Plasma lathosterol concentration was 30% lower (P less than 0.02) and plasma betasitosterol concentration was 33% higher (P less than 0.02) in the runners compared to the sedentary men. Plasma concentrations of lathosterol and plant sterols were inversely and significantly (P less than 0.05) correlated in both the runners and the sedentary men. Plasma plant sterol concentrations were correlated positively and significantly (P less than 0.01) with plasma high density lipoprotein cholesterol (HDL-C) concentrations in the runners and sedentary men combined. These findings suggest that more efficient cholesterol absorption may lead to higher plasma plant sterol concentrations and may contribute to lower cholesterol synthesis rates, reduced concentrations of plasma lathosterol and higher plasma HDL-C concentration in distance runners.

    Topics: Adult; Apolipoproteins; Cholesterol; Humans; Lipids; Lipoproteins; Male; Phytosterols; Running; Sitosterols; Triglycerides

1991
[Chemical constituents of Morinda officinalis How].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1991, Volume: 16, Issue:11

    This paper reports the identification of four compounds isolated from the cortex of Morinda officinalis growing in Guangdong Province. These compounds are beta-sitosterol (I), 2-methyl-anthraquinone(II), rubiadin-1-methyl ether(III) and 24-ethylcholesterol(VI). Compounds II and VI are isolated from Morinda Genus for the first time.

    Topics: Anthraquinones; Drugs, Chinese Herbal; Sitosterols

1991
[Chemical constituents of Swertia tetraptera Maxim. var. xinglongensis Ji Ma et R. N. Zhao].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1991, Volume: 16, Issue:9

    Five natural products were isolated from S. tetraptera var. xinglongensis of which four were proved to be oleanolic acid, 1,3-dihydroxy-4,7-dimethoxyxanthone, 1-hydroxy-2,3,5-trimethoxyxanthone and beta-sitosterol. 1,3-dihydroxy-4,7-dimethoxyxanthone has been obtained for the first time from the genus Swertia.

    Topics: Drugs, Chinese Herbal; Oleanolic Acid; Sitosterols; Xanthenes; Xanthones

1991
Antifertility effects of beta-sitosterol in male albino rats.
    Journal of ethnopharmacology, 1991, Volume: 35, Issue:2

    The effects of beta-sitosterol on fertility, epididymal sperm counts and testicular and accessory reproductive organ weights were evaluated in male albino rats. The effects were studied at two dosages (0.5 and 5 mg/kg per day rat subcutaneously) for 16, 32 and 48 days. The antifertility effect of beta-sitosterol was pronounced only at the high dose level, but there was a significant decrease in testicular weight and sperm concentrations after long-term treatment with the low dose of beta-sitosterol. The weights of all accessory sex tissues except caput epididymis increased following low dose sitosterol treatment. High dose treatment reduced the sperm concentrations as well as the weights of testis and accessory sex tissues in a time-dependent manner. Withdrawal of treatment for 30 days restored only the weights of accessory sex tissues to near normal conditions.

    Topics: Animals; Female; Fertility; Genitalia, Male; Male; Organ Size; Pseudopregnancy; Rats; Rats, Inbred Strains; Sitosterols; Sperm Count

1991
[Chemical constituents of Aconitum coreanum (Levl.) raipaics].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1991, Volume: 16, Issue:12

    Topics: Alkaloids; Drugs, Chinese Herbal; Fatty Acids; Sitosterols

1991
Sources of plant sterol contaminants encountered in low level steroid analysis.
    Journal of chromatography, 1991, Dec-06, Volume: 572, Issue:1-2

    During development of an analytical method to characterize ligands to new members of the steroid hormone receptor superfamily, a persistant contaminant profile was observed during gas chromatographic analysis of reagent blanks. Mass spectrometric analysis identified three of the contaminant peaks as cholesterol and the plant sterols stigmasterol and sitosterol. Laboratory articles made of natural rubber, i.e. pipette fillers and latex gloves, were found to be the source of these and other compounds in the reagent blank profile.

    Topics: Cholesterol; Chromatography, Gas; Mass Spectrometry; Plants; Sitosterols; Steroids; Stigmasterol

1991
[Quality of Schisandra incarnata Stapf].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1991, Volume: 16, Issue:4

    In the western part of Hubei province we have collected a medicinal plant by the local name of "North Wuweizi". It has been identified as Schisandra incarnata. A tetrahydrofuran lignan chicanine has been isolated from the kernel of the plant. Pharmacological experiments show that S. incarnata possesses activities of lowering sGPT levels as well as prolonging the sleeping time induced by phenobarbital.

    Topics: Alanine Transaminase; Animals; Drugs, Chinese Herbal; Male; Mice; Sitosterols; Sleep

1991
Transformation of sitosterol to androsta-1, 4-diene-3, 17-dione by immobilized Mycobacterium cells.
    Indian journal of biochemistry & biophysics, 1991, Volume: 28, Issue:2

    Transformation of sitosterol to androsta-1, 4-diene-3, 17-dione was studied with Mycobacterium cells entrapped in various polymeric matrices. Of the three supports viz. alginate, carageenan, agarose and polyacrylamide, studied, the polyacrylamide immobilized cells showed optimum catalytic stability and reusability.

    Topics: Androstadienes; Biotransformation; Kinetics; Mycobacterium; Sitosterols

1991
The hypercholesterolemic effect of dietary coconut fat versus corn oil in hypo- or hyperresponsive rabbits is not exerted through influencing cholesterol absorption.
    Lipids, 1991, Volume: 26, Issue:5

    In two inbred strains of rabbits with high or low response of plasma cholesterol to dietary saturated versus polyunsaturated fatty acids, the efficiency of intestinal cholesterol absorption was measured. The feeding of a cholesterol-free purified diet containing saturated fatty acids in the form of coconut fat, when compared with a diet containing corn oil as polyunsaturated fatty acids, did not influence the efficiency of cholesterol absorption in the two rabbit strains. Irrespective of the dietary fat source, the hyperresponsive rabbits absorbed cholesterol more efficiently. It is concluded that the hypercholesterolemic effect of dietary coconut fat versus corn oil is not exerted by influencing cholesterol absorption.

    Topics: Animals; Body Weight; Cholesterol; Cholesterol, Dietary; Coconut Oil; Cocos; Corn Oil; Dietary Fats; Feeding Behavior; Hypercholesterolemia; Intestinal Absorption; Liver; Male; Plant Oils; Rabbits; Sitosterols; Species Specificity

1991
Sterol and triterpene derivatives from plants inhibit the effects of a tumor promoter, and sitosterol and betulinic acid inhibit tumor formation in mouse skin two-stage carcinogenesis.
    Oncology, 1991, Volume: 48, Issue:1

    A single topical application of 1 microgram of 12-O-tetradecanoylphorbol- 13-acetate (TPA) to the ears of mice was shown to induce edema, and this TPA-induced inflammation was inhibited by 4-methylsterol and triterpene derivatives. The ED50 of these compounds against TPA-induced inflammation was 0.1-3 mumol. Phytosterols had only slight inhibitory effects. Furthermore, application of 5 micrograms TPA to mouse skin rapidly caused accumulation of ornithine decarboxylase (ODC). Similarly, sitosterol and lupane-type triterpene derivatives markedly inhibited this TPA-induced ODC accumulation. In addition, 5 mumol betulinic acid markedly inhibited the promoting effect of 2.5 micrograms TPA applied twice weekly on skin tumor formation in mice initiated with 50 micrograms of 7,12-dimethylbenz[a]anthracene, and 5 mumol of sitosterol caused slight suppression. Thus, the inhibitory effects of sterol and triterpene derivatives on TPA-induced inflammation roughly parallelled their inhibitory activities against tumor promotion.

    Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Antineoplastic Agents, Phytogenic; Betulinic Acid; Female; Mice; Mice, Inbred ICR; Ornithine Decarboxylase; Pentacyclic Triterpenes; Phytosterols; Sitosterols; Skin Neoplasms; Tetradecanoylphorbol Acetate; Triterpenes

1991
[Chemical constituents of anticancer plant Nyssa sinensis Oliv].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1991, Volume: 16, Issue:7

    Topics: Antineoplastic Agents, Phytogenic; Drugs, Chinese Herbal; Palmitates; Salicylates; Sitosterols

1991
Incorporation of liposomal phytosterols into human cells in culture: a potential in vitro model for investigating pathological effects of phytosterolemia.
    Biochemical medicine and metabolic biology, 1991, Volume: 46, Issue:1

    A potential in vitro cell culture model was developed for studies concerning the pathological effect of phytosterolemia in which liposomal phytosterols were incorporated into human skin fibroblasts and hepatoblastoma (HepG2) cells. After incubation with phytosterols, fibroblasts and HepG2 cells contained a significant amount (20-27%) of phytosterols (campesterol and beta-sitosterol). Phytosterol accumulation caused a significant reduction in the cholesterol content of cells. Labeled sitosterol and cholesterol showed similar uptake with lower esterification of sitosterol when compared to cholesterol. Labeled sitosterol incorporated into LDL was esterified to a greater extent than sitosterol added as straight liposome. About 23% of the labeled sitosterol was converted into acidic products and 5.6% was present as 5 alpha-stanols in HepG2 cells.

    Topics: Cells, Cultured; Cholesterol; Fibroblasts; Humans; Liposomes; Models, Biological; Phytosterols; Sitosterols; Skin; Tumor Cells, Cultured

1991
[Xanthomas of the Achilles tendon as the cardinal symptom of sitolsterolemia].
    Deutsche medizinische Wochenschrift (1946), 1991, Mar-01, Volume: 116, Issue:9

    The circumference of both Achilles tendons had gradually increased over the years in a now 32-year-old man (diameter of the left tendon 4.5 cm, of the right one 3.5 cm). This finally led to exercise-related pain in both tendons. Biopsy revealed benign deposition of xanthomata. Serum total cholesterol concentration was 261 mg/dl. Determination of various sitosterol fragments in serum gave a beta-sitosterol level of 43 mg/dl (normal range 0.3-1.7 mg/dl), characteristic of sitosterolaemia, which is an autosomal recessive disease causing intestinal hyperabsorption of a range of plant steroids closely related to cholesterol. On a diet low in plant steroids and treatment with cholestyramine (up to 32 g daily) the beta-sitosterol concentration fell, but only to 35 mg/dl, because of poor patient compliance. The patient died suddenly from coronary artery stenosis seven months after the diagnosis of sitosterolaemia.

    Topics: Achilles Tendon; Adult; Biopsy; Chronic Disease; Combined Modality Therapy; Diagnosis, Differential; Humans; Male; Muscular Diseases; Sitosterols; Xanthomatosis

1991
Lathosterol level in plasma is elevated in type III hyperlipoproteinemia, but not in non-type III subjects with apolipoprotein E2/2 phenotype, nor in type IIa or IIb hyperlipoproteinemia.
    Metabolism: clinical and experimental, 1991, Volume: 40, Issue:3

    We measured the serum lathosterol level, a reflection of the rate of whole body cholesterol synthesis, in 15 patients with manifest type III hyperlipoproteinemia (HLP), in 20 subjects with apolipoprotein (apo) E2/2 phenotype, but without type III HLP, in 21 patients with type IIA and 10 patients with type IIB HLP. A group of 100 subjects with apo E3/3 phenotype served as reference. Using ANCOVA, lathosterol was adjusted for serum cholesterol and triglyceride concentrations, since these parameters were found to independently correlate with lathosterol. The adjusted means (+/- SEM), in mumol/L, in these groups were 12.9 +/- 1.1, 8.2 +/- 1.1, 4.8 +/- 0.9, 9.8 +/- 1.4, and 7.8 +/- 0.4, respectively. Type III HLP patients had significantly higher lathosterol levels than all other groups except type IIB HLP. In addition, lathosterol was significantly lower in type IIA patients than in all other groups. The serum levels of plant sterols, used as a reflection of cholesterol absorption, did not differ among the various groups after adjustment for serum cholesterol. These findings suggest that an overproduction of cholesterol is one factor discriminating E2/2 homozygotes with type III HLP from those without the disease.

    Topics: Analysis of Variance; Apolipoprotein E2; Apolipoproteins E; Cholesterol; Humans; Hyperlipoproteinemia Type II; Hyperlipoproteinemia Type III; Isomerism; Phenotype; Phytosterols; Sitosterols

1991
High cholestanol and low campesterol-to-sitosterol ratio in serum of patients with primary biliary cirrhosis before liver transplantation.
    Hepatology (Baltimore, Md.), 1991, Volume: 13, Issue:4

    Serum levels of cholesterol precursors (squalene, delta 8-cholestanol, desmosterol and lathosterol), plant sterols (campesterol and sitosterol), cholestanol and cholestanol/noncholesterol sterol ratios were related to liver damage and liver transplantation indications in healthy controls (n = 26) and in 31 patients with primary biliary cirrhosis divided into group I (S-bilirubin less than 21 mumol/L; n = 14), group II (S-bilirubin 21 to 108 mumol/L; n = 7) and group III (elected for liver transplantation; S-bilirubin 109 to 520 mumol/L; n = 10). The mean serum respective lathosterol levels in controls and in group I were three and two times higher than those in groups II and III, respectively. The plant sterol contents were higher in group II than in groups I and III and the campesterol/sitosterol ratios were lowest in group III. The serum cholestanol levels were high even in group I (i.e., in patients without icterus) and increased progressively to group III, up to 6 and 13 times those in group I and the control group, respectively. The cholestanol/noncholesterol sterol ratios increased progressively from the controls to groups I, II and III. The serum cholestanol levels were positively related to serum bilirubin levels in all primary biliary cirrhosis patients (n = 31, r = 0.906) and to the plant sterol levels in the control group and group I, but significantly negatively in group III. The cholestanol vs. precursor sterol correlations were negative in most cases.(ABSTRACT TRUNCATED AT 250 WORDS)

    Topics: Cholestanol; Cholesterol; Female; Humans; Liver Cirrhosis, Biliary; Liver Function Tests; Liver Transplantation; Male; Phytosterols; Sitosterols; Sterols

1991
Effects of lovastatin on biliary lipid secretion and bile acid metabolism in humans.
    Journal of lipid research, 1991, Volume: 32, Issue:1

    Lovastatin, an inhibitor of HMG-CoA reductase, lowers cholesterol saturation of bile. To determine the mechanism of this effect and further define the role of cholesterol synthesis in regulation of biliary lipid metabolism, we studied ten human volunteers in a control period and again after 5-6 weeks on lovastatin, 40 mg b.i.d. Mean sterol production from acetate in mononuclear leukocytes fell from 1.18 to 0.84 pmol/min per 10(6) cells on lovastatin (P less than 0.02). Concomitantly there was reduction in mean biliary secretion of cholesterol from 143 to 96 mumol/h (P less than 0.02). On lovastatin, mean pool size of bile acids by the Lindstedt method fell from 3193 to 2917 mumol (one-sided P = 0.05) and mean pool size by the one-sample method fell from 5158 to 4091 mumol (P less than 0.002). Lovastatin had no effect on mean fractional turnover rate of either cholic acid (0.77 vs. 0.74 day-1) or chenodeoxycholic acid (0.51 vs. 0.54 day-1). Mean total bile acid synthesis was lower on lovastatin (1443 vs. 1240 mumol/day), but the difference did not quite achieve statistical significance. In humans, inhibition of cholesterol synthesis by lovastatin lowers biliary cholesterol saturation by reducing cholesterol secretion into bile. Bile acid pool size, and perhaps bile acid synthesis, are also reduced by this inhibition.

    Topics: Adult; Aged; Bile Acids and Salts; Biliary Tract; Chenodeoxycholic Acid; Cholesterol; Cholic Acid; Cholic Acids; Humans; Lipid Metabolism; Lovastatin; Male; Middle Aged; Sitosterols

1991
Two novel methods used in the biodegradation of bile acids and plant sterols.
    Biochemical Society transactions, 1991, Volume: 19, Issue:1

    Topics: Bile Acids and Salts; Biodegradation, Environmental; Deoxycholic Acid; Gram-Negative Bacteria; Hot Temperature; Microscopy, Electron, Scanning; Plants; Pseudomonas; Sitosterols; Sterols

1991
Quantitation of beta-sitosterol in bourbon.
    Alcoholism, clinical and experimental research, 1991, Volume: 15, Issue:2

    Four phytoestrogens have previously been isolated and identified in alcoholic beverages. Before studies to evaluate the degree of estrogenicity of these substances can be performed, it is necessary to determine appropriate doses to be administered to experimental animals. Because beta-sitosterol is the most plentiful, being present in bourbon at microgram/dl quantities, we have chosen to begin our quantitation work with this compound. The variability of the amount of beta-sitosterol contained in various brands of bourbon and in different lots of the same brand of bourbon have been assessed using combined gas chromatography/mass spectrometry (GC/MS) for quantitation following a simplified procedure to extract compounds of interest from bourbon.

    Topics: Alcoholic Beverages; Gas Chromatography-Mass Spectrometry; Humans; Sitosterols

1991
Simplified gas chromatographic method for the simultaneous determination of phytosterols and cholesterol.
    Journal of chromatography, 1991, Jan-18, Volume: 563, Issue:1

    Topics: Cholesterol; Chromatography, Gas; Food, Fortified; Humans; Phytosterols; Sitosterols; Stigmasterol

1991
High levels of plant sterols and cholesterol precursors in cerebrotendinous xanthomatosis.
    Journal of lipid research, 1991, Volume: 32, Issue:2

    We measured the cholestanol, cholesterol precursor (lathosterol), and plant sterol (campesterol and sitosterol) concentrations of serum and bile in 11 patients with cerebrotendinous xanthomatosis. The mean values of serum cholestanol, lathosterol, campesterol, and sitosterol were, respectively, 8.4-, 2.5-, 2.7-, and 1.4-times higher in the patients than in normal control subjects (n = 26). Cholestanol (6.7-fold) and campesterol (3.7-fold) levels in bile (n = 4) were also elevated in the patients. There was no significant difference of serum sterol levels between patients with coronary artery disease and those without it. Chenodeoxycholic acid treatment for periods ranging from 6 months to 3 years and 4 months lowered serum lathosterol (57.7% reduction) and campesterol (57.8%) levels in parallel with cholestanol (70.8%) level, but the sitosterol level (19.7%) decreased less. Thus, increased levels of cholesterol precursor (lathosterol), plant sterols (campesterol and sitosterol), and cholestanol were found in the serum and bile in cerebrotendinous xanthomatosis. Chenodeoxycholic acid treatment effectively reduced the levels of these sterols, except for sitosterol.

    Topics: Adult; Bile; Chenodeoxycholic Acid; Cholestanol; Cholesterol; Chromatography, High Pressure Liquid; Coronary Disease; Female; Humans; Male; Middle Aged; Phytosterols; Sitosterols; Xanthomatosis

1991
Hypocholesterolemic activity of beta-sitosterol in cholesterol fed sea quail.
    Artery, 1991, Volume: 18, Issue:3

    Male SEA quail were fed a 0.5% cholesterol supplemented diet, to which was added 0%, 1%, and 2% beta-sitosterol, for a period of seven days. Dietarily administered beta-sitosterol reduced total serum cholesterol levels by 62% and 72% at the 1% and 2% treatment doses, respectively. This hypocholesterolemic activity of sitosterol in cholesterol fed SEA quail was anticipated on the basis of the numerous earlier studies demonstrating similar activity in cholesterol fed chickens. Beta-sitosterol was tested in SEA quail to experimentally confirm its expected serum cholesterol lowering effects and to expand further the utility of the SEA quail model in cholesterol and atherosclerosis research.

    Topics: Animals; Anticholesteremic Agents; Cholesterol; Coturnix; Diet, Atherogenic; Intestinal Absorption; Male; Sitosterols

1991
[On the skinning of radix Adenophorae].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1991, Volume: 16, Issue:1

    Traditional experience calls for the skinning of Radix Adenophorae. Depending on the chemical compositions, this paper presents a comparative study on the skin, the radix with skin and the skinned radix. The experimental results show that the contents of beta-sitosterol, saponins, amino acids and trace elements are highest in the radix with skin, and that the radix with skin and the skinned radix are similar in the contents of polysaccharides.

    Topics: Amino Acids; Drugs, Chinese Herbal; Plants, Medicinal; Saponins; Sitosterols; Technology, Pharmaceutical; Trace Elements

1991
[New triterpenoidal sapogenins from the roots of Glycyrrhiza yunnanensis].
    Yao xue xue bao = Acta pharmaceutica Sinica, 1990, Volume: 25, Issue:7

    Two new pentacyclic triterpenoidal sapogenins of oleanane type, namely glyyunnansapogenin A (I) and glyyunnansapogenin B (II), together with a known compound beta-sitosterol were isolated and characterized from the roots of Glycyrrhiza yunnanensis Cheng f. et L. K. Tai, family Leguminosae, collected in Yunnan Province, China. I was obtained as its methyl ester (Ia), mp 276-277 degrees C, which formed a diacetate (Ic), mp 244-245 degrees C. II, mp 287-289 degrees C, gave a triacetate (IIb), mp 286-287 degrees C and a monomethyl ester (IIa), mp 272-275 degrees C, which further formed a triacetate (IIc), mp 187-189 degrees C and a diacetate (IId), mp 243-245 degrees C after treatment with acetic anhydride and pyridine over night at room temperature. The structures of I and II were established by spectral analyses of IR, 1H NMR, 13CNMR, MS, CD and ORD. Glyyunnansapogenin A (I) was proved to be 3 beta, 24-dihydroxy-16-oxo-olean-12-en-29-oic acid and glyyunnansapogenin B (II) 3 beta, 21 alpha, 24-trihydroxy-olean-12-en-30-oic acid respectively.

    Topics: Chemical Phenomena; Chemistry; Glycyrrhiza; Plants, Medicinal; Sapogenins; Sitosterols; Triterpenes

1990
[Diterpenoid constituents in bulbs of Fritillaria anhuiensis S.C. Chen et S.F. Yin].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1990, Volume: 15, Issue:3

    The bulb of Fritillaria anhuiensis, a substitute for the traditional Chinese medicine Beimu, has been used as antibechic and expectorant. From the either soluble part of the bulb, four constituents were isolated and identified by spectral analysis (IR, MS, 1HNMR, 13CNMR) as beta-sitosterol, daucosterol, ent-kaur-15-en-17-ol and ent-kauran-16 beta, 17-diol.

    Topics: Diterpenes; Drugs, Chinese Herbal; Sitosterols

1990
[Chemical constituents of Adenophora stricta Miq].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1990, Volume: 15, Issue:8

    Four compounds were isolated from the roots of Adenophora stricta. On the basis of spectrometric analysis and physicochemical constants, they were identified as beta-sitosterol, beta-sitosterol-O-beta-D-glucopyranoside, taraxerone and octacasanoic acid respectively. Taraxerone and octacasanoic acid were isolated from the plants of Adenophora for the first time.

    Topics: Drugs, Chinese Herbal; Fatty Acids; Oleanolic Acid; Sitosterols

1990
[Chemical constituents in the stem of Premna crassa Hand. -Mazz].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1990, Volume: 15, Issue:8

    In this paper four compounds isolated from the stem of Premna crassa are described. Their structures have been identified as friedelin, epifriedelanol, stearic acid and beta-sitosterol respectively by comparing their chemical and spectroscopic data with those of the authentic samples.

    Topics: Drugs, Chinese Herbal; Oleanolic Acid; Sitosterols; Stearic Acids; Triterpenes

1990
The antiatherogenic effects of components isolated from pollen typhae.
    Thrombosis research, 1990, Mar-15, Volume: 57, Issue:6

    Based on the results of previous investigations that pollen Typhae, a Traditional Chinese Medicine, Had antiatherogenic effects, several components were isolated successively from the drug and their effects on porcine aortic endothelial cell (EC) and smooth muscle cell (SMC) cultures as well as on platelet aggregation were examined. 12 components isolated from Pollen Typhae have been identified on their chemical structures and biological effects. 4 of them showed different evident antiatherogenic effects. 1) Isorhamnetin-3-O-rhamnosyl-glucoside could stimulate EC to produce tPA and PGI2; 2) Quercetin-3-O-neohesperidose could protect EC from injury by fibrin, as well as raise tPA activity; 3) beta-Sitosterol palmitate could inhibit SMC proliferation and 4) beta-Sitosterol glucoside showed an inhibitory effect on platelet aggregation. These results would provide some information for the search of new drugs in the treatment and prevention of atherosclerosis.

    Topics: Animals; Cell Division; Disaccharides; Drugs, Chinese Herbal; Endothelium, Vascular; Epoprostenol; Fibrin; Flavonols; Hesperidin; Muscle, Smooth, Vascular; Platelet Aggregation; Platelet Aggregation Inhibitors; Pollen; Quercetin; Sitosterols; Swine; Tissue Plasminogen Activator

1990
Effects of steroid molecules on the dynamical structure of dioleoylphosphatidylcholine and digalactosyldiacylglycerol bilayers.
    Biochimica et biophysica acta, 1990, Feb-28, Volume: 1022, Issue:2

    The ESR spectra of cholestane spin labels (CSL) in dioleoylphosphatidylcholine (DOPC) bilayers containing 20 wt% of cholesterol, 7-dehydrocholesterol, beta-sitosterol, stigmasterol and lanosterol exhibit a marked similarity, thus indicating that these steroids induced the same effects on the lipid bilayer over the temperature range 21-55 degrees C. The incorporation of these steroids into the DOPC bilayers enhances the orientational order of the CSL molecules at every temperature studied, but only induces a pronounced slow-down in their rotational motions at temperatures above 35 degrees C. Similar results were obtained in DOPC/ergosterol multilamellar liposomes, but the changes are now less pronounced than in the other five DOPC/steroid systems. In contrast, the addition of stigmasterol to digalactosyldiacylglycerol (DGDG) bilayers appears to increase the order parameter mean value of P2, without affecting the diffusion coefficients. Furthermore, the incorporation of 7-dehydrocholesterol to DGDG bilayers causes a large enhancement in the orientational order, but has only a small effect on D perpendicular of the CSL molecules. Importantly, this latter effect appears to be independent of temperature. The marked changes in the rates of the rotational motion brought about by the addition of steroids, contrasts with the lack of a significant effect of unsaturation on the bilayer dynamics reported by us previously (Korstanje et al. (1989), Biochim. Biophys. Acta 980, 225-233, and 982, 196-204).

    Topics: Chemical Phenomena; Chemistry, Physical; Cholestanes; Cholesterol; Dehydrocholesterols; Electron Spin Resonance Spectroscopy; Galactolipids; Glycolipids; Lanosterol; Lipid Bilayers; Liposomes; Phosphatidylcholines; Sitosterols; Spin Labels; Steroids; Stigmasterol; Structure-Activity Relationship; Temperature

1990
Effect of lipid composition on the transfer of sterols mediated by non-specific lipid transfer protein (sterol carrier protein2).
    Biochimica et biophysica acta, 1990, Sep-18, Volume: 1046, Issue:2

    The rate of non-specific lipid transfer protein (nsLTP)-mediated exchange is independent of structure for dissimilar sterols: cholesterol, lanosterol, sitosterol and vitamin D-3. Conversely, the nsLTP-mediated exchange of cholesterol is markedly affected by the phospholipid composition of the donor liposome. Negatively charged phosphatidylglycerols strikingly increase cholesterol exchange in the presence of nsLTP while not altering the exchange in the absence of nsLTP. The presence of unsaturated acyl chains in the phospholipid enhances exchange. Sphingomyelin drastically decreases cholesterol exchange, as does di-O-alkylphosphatidylcholine. Decreased exchange produced by these substitutions can be reversed by addition of phosphatidylcholine. The presence of an acyl group and a negative charge in the phospholipid are critical for the nsLTP-mediated transfer of cholesterol. In addition to these studies on composition of the donor membrane, the charge on the membrane also appears critical. Maximal exchange rates accompany optimization of potential interaction of negatively charged surface and the basic nsLTP. The nsLTP also mediates an approximately equal rate of exchange of cholesterol and phosphatidylcholine. However, approaching equilibrium, only half of the phospholipid can be exchanged while there is exchange of about 90% of cholesterol. Thus, it appears that only the phospholipid in an outer membrane layer may be available whereas cholesterol is fully available. Therefore, in contrast to a 'carrier' model we suggest that nsLTP facilitates exchange by binding to the membranes, and binding is highly dependent upon lipid composition. Once bound, the protein functions as a bridge between membranes, thus, facilitating exchange.

    Topics: Biological Transport; Carrier Proteins; Cholecalciferol; Cholesterol; Lanosterol; Lipids; Liposomes; Phosphatidylcholines; Phosphatidylglycerols; Phospholipids; Plant Proteins; Sitosterols; Sphingomyelins; Sterols

1990
[Chemical constituents of the seed oil of Astragalus complanatus R. Brown].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1990, Volume: 15, Issue:4

    beta-sitosterol and fatty acids were obtained from the oil of seeds of Astragalus complanatus. The fatty acids were separated and their molecular weights determined by GC-MS. Fourteen of them were identified as heptenoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, octadecenoic acid, octadecanoic acid, octadecadienoic acid, linolenic acid, eicosanoic acid, eicosenoic acid and docosanoic acid, etc.

    Topics: Drugs, Chinese Herbal; Fabaceae; Fatty Acids; Fatty Acids, Unsaturated; Plants, Medicinal; Seeds; Sitosterols

1990
[Beta-sitosterol in the treatment of hypercholesterolemia].
    Casopis lekaru ceskych, 1990, Oct-19, Volume: 129, Issue:42

    A group of 28 patients with primary hyperlipoproteinaemia [19X lipoprotein (LP) type IIA, 8X type IIB and 1X a normolipidaemic patient with concurrent hyperapoB lipoproteinaemia] were given for a period of three weeks a dietetic preparation containing phytosterols - 12 g/day. This led to a significant drop of total cholesterol and LDL-cholesterol in plasma. The cholesterol concentration in HDL and both its fractions increased, the differences however were not significant. The triglyceride levels did not change. There was a significant drop of the apolipoprotein B (apo-B) concentration in LDL, the apo-A-I in plasma did not change. There was a significant drop of atherogenic indexes TC/HDL-C, LDL-C/HDL-C and apo-B/-A-I. During investigation of the LCAT activity the authors observed a significant rise of the fractional esterification rate associated with a highly significant drop of the free cholesterol concentration in plasma as a result of treatment. Discrimination analysis of parameters of the lipoprotein metabolism and the patients' body weight before treatment helps to assess a function by means of which it is possible in 92.3% of the subjects to predict the success of treatment before the administration of beta-sitosterol.

    Topics: Female; Humans; Hypercholesterolemia; Lipids; Male; Middle Aged; Sitosterols

1990
[Chemical studies on the constituents of Daphne koreane Nakai].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1990, Volume: 15, Issue:10

    In this paper three compounds isolated from Daphne koreane are described. Their structures have been identified as beta-sitosterol, naringenin and 7,8-dimethoxycoumarin on the basis of spectral data and chemical reactions.

    Topics: Anti-Ulcer Agents; Coumarins; Drugs, Chinese Herbal; Flavanones; Flavonoids; Sitosterols

1990
[A case of sitosterolemia with spastic gait due to intradural-extramedullary xanthoma].
    Rinsho shinkeigaku = Clinical neurology, 1990, Volume: 30, Issue:10

    A forty-eight-year-old woman with a 30 years history of tendinous xanthomatosis developed spastic gait and mild urinary incontinence. Myelography, metrizamide-enhanced CT and magnetic resonance image revealed multiple intradural-extramedullary tumors extending from C1 to Th7. The gait disturbance entirely disappeared by the removal of the tumors. Morphological examination of the tumors showed xanthogranulomatosis. The analysis of her sera and tumors revealed increased amount of plant sterols, especially beta-sitosterol and the diagnosis was made as beta-sitosterolemia. Tendinous xanthoma and beta-sitosterolemia were seen in 2 of 6 her brothers but none showed neurological symptoms. This is the first case of sitosterolemia with neurological complication i.e., spinal cord compression due to extramedullary sitosterolemia xanthomas.

    Topics: Female; Gait; Granuloma; Humans; Middle Aged; Movement Disorders; Sitosterols; Spinal Cord Compression; Spinal Cord Diseases; Urinary Incontinence; Xanthomatosis

1990
Serum plant sterols and cholesterol precursors reflect cholesterol absorption and synthesis in volunteers of a randomly selected male population.
    American journal of epidemiology, 1990, Volume: 131, Issue:1

    To investigate the regulation of serum levels of cholesterol precursor sterols and plant sterols, these noncholesterol sterols, fatty acids, and various parameters of cholesterol metabolism were analyzed in 63 volunteers from a randomly selected Finnish male population sample of 100 subjects, aged 50 years, who had normal dietary habits. Serum levels of cholesterol precursors, desmosterol and lathosterol (in terms of micrograms/mg cholesterol), were negatively related to both the fractional and absolute absorption of dietary cholesterol and serum high density lipoprotein (HDL) cholesterol, and positively related to overall cholesterol synthesis and serum very low density lipoprotein (VLDL) cholesterol. Serum levels of the plant sterols, campesterol and sitosterol, exhibited positive correlations with the polyunsaturated/saturated fatty acid ratio of dietary fat, the linoleic acid contents of plasma and dietary lipids, the amount of dietary plant sterols (as indicated by fecal output), fractional and absolute absorption of dietary cholesterol, and HDL cholesterol, but were inversely related to the overall cholesterol synthesis and VLDL cholesterol. Stepwise multiple regression analysis revealed that the serum level of campesterol was associated with fractional cholesterol absorption, dietary plant sterols, and biliary cholesterol secretion, and that of sitosterol with dietary plant sterols, cholesterol synthesis, fractional cholesterol absorption, and biliary cholesterol secretion. Thus, the serum non-cholesterol sterols are significant indicators of cholesterol absorption and synthesis even under basal conditions and, since gas liquid chromatographic determination of these sterols is quite simple, their measurement may be valuable for monitoring cholesterol metabolism in large-scale epidemiologic studies.

    Topics: Absorption; Cholesterol; Cholesterol, Dietary; Cholesterol, HDL; Cholesterol, LDL; Desmosterol; Dietary Fats; Fatty Acids; Humans; Isomerism; Male; Middle Aged; Phytosterols; Random Allocation; Sitosterols

1990
Thrombin-induced inositol phosphate production by platelets from rats with diet-induced or genetically determined hypercholesterolemia.
    The Journal of laboratory and clinical medicine, 1990, Volume: 115, Issue:2

    Platelets from rats with diet-induced or genetically determined hypercholesterolemia are hypersensitive to thrombin through a pathway that is independent of the effects of released ADP or formation of thromboxane A2. We examined production of inositol phosphates by platelets from these hypercholesterolemic rats to determine whether the enhanced responsiveness to thrombin is associated with increased production of inositol trisphosphate (IP3). The opportunity to study rats with hypercholesterolemia determined genetically or induced by diet makes it possible to determine whether any differences in inositol phosphate production are caused by hypercholesterolemia alone rather than to any other effect of the diet used to induce hypercholesterolemia. Platelets were prelabeled with [3H]inositol so that increases in inositol phosphates (IP, IP2, and IP3) upon stimulation with thrombin could be assessed by measuring the amount of label in these compounds. Platelets were preincubated with CP/CPK, to inhibit effects of released ADP, and aspirin, to inhibit formation of thromboxane A2/endoperoxides. In platelets from rats with either form of hypercholesterolemia, the percentage increase in labeling of IP3 was significantly greater 30 seconds after stimulation with low concentrations of thrombin than in platelets from control rats. Increased IP3 formation in platelets from hypercholesterolemic rats indicates that there is increased activity of a pathway(s) leading to IP3 formation and that this may be a mechanism responsible for the thrombin-induced hypersensitivity of these platelets.

    Topics: Animals; Aspirin; Blood Platelets; Cholesterol, Dietary; Creatine Kinase; Hypercholesterolemia; Inositol; Inositol Phosphates; Kinetics; Male; Phosphocreatine; Platelet Aggregation; Rats; Rats, Inbred Strains; Sitosterols; Thrombin

1990
Rat toxicity studies with beta-sitosterol.
    Journal of ethnopharmacology, 1990, Volume: 28, Issue:2

    Chronic administration of beta-sitosterol subcutaneously to rats for 60 days was well tolerated and there was no clear cut evidence of any gross or microscopic lesions either in the liver or kidney. Liver and kidney function tests were assessed by determining the blood/serum parameters like haemoglobin, blood glucose, serum protein, serum bilirubin, serum cholesterol, serum GPT and serum GOT. All the parameters were in the normal range except serum protein and serum cholesterol. Serum cholesterol was the only variable which depleted markedly in both sexes in a dose-dependent manner suggesting intrinsic hypocholesterolemic effect of the sterol.

    Topics: Alanine Transaminase; Animals; Aspartate Aminotransferases; Bilirubin; Blood Glucose; Body Weight; Cholesterol; Dose-Response Relationship, Drug; Drug Administration Schedule; Female; Hemoglobins; Kidney; Liver; Male; Organ Size; Rats; Rats, Inbred Strains; Sex Characteristics; Sitosterols

1990
Formation of C21 bile acids from plant sterols in the rat.
    The Journal of biological chemistry, 1990, May-15, Volume: 265, Issue:14

    Formation of bile acids from sitosterol in bile-fistulated female Wistar rats was studied with use of 4-14C-labeled sitosterol and sitosterol labeled with 3H in specific positions. The major part (about 75%) of the 14C radioactivity recovered as bile acids in bile after intravenous administration of [4-14C]sitosterol was found to be considerably more polar than cholic acid, and only trace amounts of radioactivity had chromatographic properties similar to those of cholic acid and chenodeoxycholic acid. It was shown that polar metabolites were formed by intermediate oxidation of the 3 beta-hydroxyl group (loss of 3H from 3 alpha-3H-labeled sitosterol) and that the most polar fraction did not contain a hydroxyl group at C7 (retention of 3H in 7 alpha,7 beta-3H2-labeled sitosterol). Furthermore, the polar metabolites had lost at least the terminal 6 or 7 carbon atoms of the side chain (loss of 3H from 22,23-3H2- and 24,28-3H2-labeled sitosterol). Experiments with 3H-labeled 7 alpha-hydroxysitosterol and 4-14C-labeled 26-hydroxysitosterol showed that none of these compounds was an efficient precursor to the polar metabolites. By analysis of purified most polar products of [4-14C] sitosterol by radio-gas chromatography and the same products of 7 alpha,7 beta-[2H2]sitosterol by combined gas chromatography-mass spectrometry, two major metabolites could be identified as C21 bile acids. One metabolite had three hydroxyl groups (3 alpha, 15, and unknown), and one had two hydroxyl groups (3 alpha, 15) and one keto group. Considerably less C21 bile acids were formed from [4-14C]sitosterol in male than in female Wistar rats. The C21 bile acids formed in male rats did not contain a 15-hydroxyl group. Conversion of a [4-14C]sitosterol into C21 bile acids did also occur in adrenalectomized and ovariectomized rats, indicating that endocrine tissues are not involved. Experiments with isolated perfused liver gave direct evidence that the overall conversion of sitosterol into C21 bile acids occurs in this organ. Intravenously injected 7 alpha,7 beta-3H-labeled campesterol gave a product pattern identical to that of 4-14C-labeled sitosterol. Possible mechanisms for hepatic conversion of sitosterol and campesterol into C21 bile acids are discussed.

    Topics: 3-alpha-Hydroxysteroid Dehydrogenase (B-Specific); 3-Hydroxysteroid Dehydrogenases; Animals; Bile; Bile Acids and Salts; Carbon Radioisotopes; Cholesterol; Chromatography, Gas; Chromatography, High Pressure Liquid; Female; Hydroxylation; Liver; Male; Mass Spectrometry; NAD; Oxidation-Reduction; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Tritium

1990
Pharmacokinetics and bioavailability of beta-sitosterol in the beagle dog.
    Arzneimittel-Forschung, 1990, Volume: 40, Issue:4

    Tritium-labelled beta-sitosterol (BSS) 10 mg was administered to 6 beagle dogs in a 3-way crossover study: 1. i.v. solution, 2. p.o. powdered BSS, and 3. BSS embedded in a polyethyleneglycol (PEG) melt. The concentration-time profiles for both routes of administration were best described by a two-compartment open model with a fast distribution phase, having a t1/2 alpha of about 3 h, and a terminal disposition phase having a t1/2 beta of about 129 h. The volume of distribution of the central compartment corresponds to the total body fluid (Vc = 0.56 l/kg), and the apparent volume of distribution is about equal to the total body weight (V d/beta = 0.92 l/kg). The mean residence time is about 185 h. The absolute bioavailability upon p.o. administration is about 9%. The PEG embedment of BSS does not increase the extent of absorption; however, the rate of absorption is significantly increased.

    Topics: Administration, Oral; Animals; Biological Availability; Dogs; Injections, Intravenous; Sitosterols

1990
Increased plasma plant sterol levels in heterozygotes with sitosterolemia and xanthomatosis.
    Journal of lipid research, 1990, Volume: 31, Issue:5

    Plasma sterol levels in a family of sitosterolemia and xanthomatosis were determined by a high performance liquid chromatography. Three affected siblings manifested marked xanthomatosis including subcutaneous soft tissues and generalized atherosclerosis. Two other siblings as well as children of the patients did not show such clinical symptoms and signs. Plasma levels of cholesterol, sitosterol, campesterol, and cholestanol in three affected subjects were 190 +/- 18.5, 25.9 +/- 11.6, 16.1 +/- 7.8, 1.84 +/- 0.92 mg/dl (mean +/- SD), respectively. Four daughters of the affected subjects, who should be considered as obligatory heterozygotes, showed moderately increased levels of these sterols (195 +/- 41.7, 1.33 +/- 0.44, 1.56 +/- 0.69, 0.80 +/- 0.28 mg/dl), which were significantly higher than those of normal subjects. Treatment with cholestyramine had little effect on the increased plasma plant sterol levels, but markedly decreased plasma cholestanol concentrations in two affected siblings. This report presents the clinical features of the patients with sitosterolemia and xanthomatosis and also demonstrates that heterozygotes with this disorder have increased plasma levels of plant sterols as well as cholestanol, and suggests that this rare disease might be inherited as an autosomal co-dominant trait in certain cases. The data also indicate that cholestyramine administration was not effective in this family for treatment of sitosterolemia.

    Topics: Adult; Child; Cholestyramine Resin; Chromatography, High Pressure Liquid; Female; Heterozygote; Humans; Lipids; Male; Middle Aged; Pedigree; Phytosterols; Sitosterols; Xanthomatosis

1990
[Studies on the chemical constituents of the stems and leaves of Illicium dunnianum Tutch].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1989, Volume: 14, Issue:1

    Four chemical constituents were isolated from the stems and leaves of Illicium dunnianum: beta-sitosterol (I), 1-triacontanal (II), quercitrin (III) and shikimic acid (IV), and identified on the basis of spectral analysis. Pharmacological experiments have shown that shikimic acid possesses analgesic activities.

    Topics: Analgesics; Drugs, Chinese Herbal; Fatty Alcohols; Quercetin; Shikimic Acid; Sitosterols

1989
[Studies on the chemical constituents of Arisaema fargesii Buchett].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1989, Volume: 14, Issue:8

    Heptatriacontane, benzoic acid, succinic acid, palmitic acid, stearic acid, beta-sitosterol, stigmasterol, daucosterol, D-mannitol, D-glucose, sucrose and choline chloride were isolated from the roots of Arisaema fargesii collected from Gansu Province. Their structures were elucidated by spectroscopic methods and a few chemical transformations. The twelve compounds have not been reported before as constituents of Arisaema fargesii.

    Topics: Antineoplastic Agents, Phytogenic; Drugs, Chinese Herbal; Sitosterols; Succinates; Succinic Acid

1989
The mechanism of the hypocholesterolaemic effect of activated charcoal.
    European journal of clinical investigation, 1989, Volume: 19, Issue:3

    The hypocholesterolaemic mechanism of activated charcoal was studied in seven patients with primary hypercholesterolaemia. The reduction of serum cholesterol was correlated with the serum concentrations of cholesterol precursors and of two plant sterols. Activated charcoal, 8 g t.i.d. for 4 weeks, reduced serum concentration of total cholesterol by 27% (P less than 0.01). The effect was accompanied by a moderate elevation (P less than 0.05) in serum squalene and desmosterol concentrations and by a marked increase (up to 300-700%) in serum lathosterol and delta 8 lathosterol concentrations. The levels of two plant sterols, campesterol and beta-sitosterol, were unchanged or only slightly decreased by the use of activated charcoal. The decrease of serum cholesterol concentration had significant negative correlations with serum lathosterol and delta 8 lathosterol, and significant positive correlations with serum cholestanol and beta-sitosterol. These observations suggest an increased cholesterol synthesis upon treatment with activated charcoal, probably caused by the interference with the enterohepatic circulation of bile acids.

    Topics: Anticholesteremic Agents; Charcoal; Cholesterol; Desmosterol; Female; Humans; Hypercholesterolemia; Male; Middle Aged; Phytosterols; Sitosterols

1989
[Chemical studies on the constituents of radix Ophiopogonis].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1989, Volume: 14, Issue:6

    In this paper four compounds isolated from Radix Ophiopogonis are described. Their structures have been identified as beta-sitosterol (I), 6-aldehydo-7-methoxy-isoophiopogonanone B (II), beta-sitosterol-beta-D-glucopyranoside (III) and 1-borneol-beta-D-apisyl-beta-D-glucopyranoside (IV) on the basis of spectral data and hydrolytic reaction.

    Topics: Camphanes; Drugs, Chinese Herbal; Glucosides; Isoflavones; Saponins; Sitosterols

1989
Effects of sitosterol and sitostanol on micellar solubility of cholesterol.
    Journal of nutritional science and vitaminology, 1989, Volume: 35, Issue:4

    The influence of sitosterol and sitostanol on the solubility of cholesterol in mixed bile salt micelles in vitro and in vivo was investigated to examine the mechanism by which sitostanol inhibits cholesterol absorption more than does sitosterol. Both sitosterol and sitostanol decreased micellar solubility of cholesterol to a similar extent, when determined with the turbidity. Also, these sterols reduced the concentration of cholesterol in micelles, both in vitro and in vivo. The extent of the reduction of micellar solubility of cholesterol by these sterols was almost the same in vitro, whereas sitostanol tended to reduce the solubility more effectively than sitosterol in vivo. Thus, the interference with cholesterol solubilization in vivo may be responsible for effective inhibition of cholesterol absorption by sitostanol. Since the effect of sitostanol was not observed in vitro, there is a possibility that another factor(s) not included in the in vitro system might affect the action of sitostanol on micellar solubility of cholesterol in vivo.

    Topics: Animals; Cholesterol; Intestinal Absorption; Male; Micelles; Rats; Sitosterols; Solubility; Spectrophotometry; Ultracentrifugation

1989
Effects of cholestyramine and squalene feeding on hepatic and serum plant sterols in the rat.
    Lipids, 1989, Volume: 24, Issue:8

    Hepatic and serum phytosterol concentrations were compared in the rat under basal conditions and during activated cholesterol and bile acid production due to squalene and cholestyramine feeding. Both treatments consistently decreased hepatic and serum levels of sitosterol and campesterol and, unlike esterified cholesterol, esterified plant sterols were not increased in liver during squalene feeding. Serum levels of phytosterols were decreased quite proportionately to those in the liver. The hepatic levels of sitosterol and campesterol closely correlated with each other, but not with cholesterol levels. The percentage esterification of both phytosterols was lower than that of cholesterol. The results indicate that activation of hepatic sterol production leads to depletion of hepatic plant sterols. It is suggested that poor esterification of plant sterols may contribute to this decrease.

    Topics: Animals; Cholesterol; Cholestyramine Resin; Esterification; Liver; Male; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Squalene

1989
Increased sitosterol absorption, decreased removal, and expanded body pools compensate for reduced cholesterol synthesis in sitosterolemia with xanthomatosis.
    Journal of lipid research, 1989, Volume: 30, Issue:9

    We measured the turnover and absorption of sitosterol and cholesterol, along with plasma sterol and lipoprotein concentrations, in one control and two subjects with sitosterolemia with xanthomatosis. All individuals consumed the same diet which contained approximately 500 mg/day of cholesterol and 250 mg/day of sitosterol. Sterol absorption was measured by the plasma dual-isotope ratio method and turnover by plasma isotope-kinetic analysis. In two sitosterolemic subjects, 28% and 63% of the sitosterol and 69% and 49% of the cholesterol were absorbed, respectively, compared to 4% of the sitosterol and 44% of the cholesterol in the control. As expected, plasma sitosterol specific activities decayed much more rapidly than cholesterol in the control subject. In contrast, plasma sitosterol and cholesterol specific activity-time curves were similar and decayed more slowly in the sitosterolemic subjects. In the control subject, the total sitotterol pool was 290 mg and was linearly related to low absorption (18 mg/day); whereas the total sitosterol pool was 17 times (4800 mg) and 13 times (3500 mg) larger, respectively, in the sitosterolemic subjects and was expanded out of proportion to increased absorption because of decreased removal. Daily cholesterol turnover and synthesis were markedly reduced in the sitosterolemic subjects. In four sitosterolemic subjects, plasma concentrations of total sterols, low density lipoproteins, and apolipoprotein B were increased, while those of high density lipoproteins and apolipoprotein A-I were low to normal. The low density lipoproteins were very similar to those of normal control subjects in density distribution, peak flotation rate, sterol-to-protein (apolipoprotein B) ratio, particle size, and morphology. These results demonstrate in patients with sitosterolemia with xanthomatosis that: 1) the absorption of sitosterol and cholesterol is enhanced; 2) tissue recognition between cholesterol and sitosterol is lost; 3) total exchangeable sitosterol pools are expanded out of proportion to absorption because of decreased excretion; 4) plasma sterol and lipoprotein concentrations favor tissue deposition; and 5) cholesterol synthesis is diminished. We postulate that the changes in sitosterol metabolism (increased absorption, loss of tissue sterol structural recognition, expanded pools, and hepatic retention) are a response to reduced cholesterol synthesis in these subject.

    Topics: Absorption; Adolescent; Adult; Arteriosclerosis; Cholesterol; Female; Humans; Lipoproteins; Male; Sitosterols; Sterols; Xanthomatosis

1989
[Studies on the chemical constituents of the roots of Aralia continentalis Kitag].
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 1989, Volume: 14, Issue:7

    Seven compounds were isolated from the roots of Aralia continentalis. Four of these compounds were identified as ent-kaur-16-en-19-oic acid, beta-sitosterol glucoside (daucosterol), beta-sitosterol and 16 alpha-hydroxy-(-)-kauran-19-oic acid. It is the first time that 16 alpha-hydroxy-(-)-karan-19-oic acid and beta-sitosterol glucoside were isolated from this plant.

    Topics: Diterpenes; Drugs, Chinese Herbal; Sitosterols

1989
Cultivation and preliminary phytochemical analysis of the Psychotria bacteriophila callus tissue.
    Acta poloniae pharmaceutica, 1989, Volume: 46, Issue:4

    Topics: Culture Media; Culture Techniques; Plants, Medicinal; Sitosterols; Tissue Extracts

1989
The effect of beta-sitosterol on spore germination and germ-tube elongation of Aspergillus niger and Botryodiplodia theobromae.
    International journal of food microbiology, 1989, Volume: 8, Issue:1

    The effect of beta-sitosterol on spore germination and prevention of elongation of germ-tube of Aspergillus niger and Botryodiplodia theobromae was studied. The antifungal activity of the compound showed a percentage inhibition, of the fungal spore germination, of about 40% at a concentration of 50 micrograms/ml while inhibition on the elongation of germ-tubes was as high as 65% at the same concentration. The ED50 for inhibition of germ-tube elongation in A. niger was about 31 micrograms/ml. The role of the compound in disease resistance is discussed.

    Topics: Aspergillus niger; Food Microbiology; Mitosporic Fungi; Plant Diseases; Sitosterols; Spores, Fungal

1989
Origin of intestinal lymph cholesterol in rats: contribution from luminal absorption, mucosal synthesis and filtration from plasma.
    Lymphology, 1989, Volume: 22, Issue:1

    Measurement of cholesterol transport from plasma to intestinal lymph based on i.v. labeling with radioactive beta-sitosterol was validated by the simultaneous i.v. administration of 4-14C-beta-sitosterol and of 1,2-3H-cholesterol to two rats with bile duct, intestinal lymph, duodenum and jugular vein cannulations. In 11 other rats undergoing intestinal lymph duct cannulation, each potential source of lymph cholesterol was determined 2-3 weeks after i.v. pulse administration of 1,2-3H-beta-sitosterol and 4-14C-cholesterol. For this purpose, lymph fat, after an intragastric infusion of cottonseed oil (1900mg), was used as a marker for total cholesterol mass transported into intestinal lymph. In these two experimental groups of rats, namely, in the absence and in the presence of supplemental dietary cholesterol, filtration of cholesterol from plasma to lymph and absorption of cholesterol derived from bile did not change in the presence of exogenous cholesterol. In other words, absorption of cholesterol based on the amount of cholesterol in intestinal lymph by direct measurement was comparable to the level obtained by the isotopic procedure based upon lowering of the lymph/plasma ratio of 4-14C-cholesterol specific activity (d.p.m./mg of cholesterol). Plasma cholesterol appearing in intestinal lymph was transported mainly in lymph lipoproteins at a density below 1.006 (i.e., chylomicrons). Esterification was not necessary for luminal cholesterol absorption under these experimental conditions.

    Topics: Animals; Biological Transport; Carbon Radioisotopes; Cholesterol; Chylomicrons; Intestinal Absorption; Intestinal Mucosa; Lymph; Male; Rats; Rats, Inbred Strains; Sitosterols; Tritium

1989
Effect of sitosterol on the rate-limiting enzymes in cholesterol synthesis and degradation.
    Lipids, 1989, Volume: 24, Issue:1

    Attempts were made to develop an animal model for phytosterolemia. Infusion of Intralipid containing 0.2% sitosterol in rats gave circulating levels of sitosterol of about 2.5 mmol/l, which is similar to or higher than those present in patients with untreated phytosterolemia. In addition, the infusions gave serum levels of cholesterol nearly twice those obtained in rats infused with Intralipid alone or Intralipid containing 0.2% cholesterol. The hepatic HMG-CoA reductase activity was unaffected or slightly increased by the sitosterol infusions (not statistically significant). The cholesterol 7 alpha-hydroxylase activity was slightly depressed (ca. 30%). In the case of 7 alpha-hydroxylation of endogenous cholesterol, the depression reached statistical significance (p less than 0.05). The microsomal content of sitosterol in the sitosterol-infused rats was about 30% of that of microsomal cholesterol. The effect of sitosterol on 7 alpha-hydroxylation of cholesterol was investigated by incubations of acetone powder of rat liver microsomes with mixtures of cholesterol and sitosterol. Sitosterol mixed with cholesterol to a composition similar to that found in the above microsomal fraction had a depressing effect on 7 alpha-hydroxylation of cholesterol. This degree of depression was of the same magnitude as that found in the sitosterol infusion experiments. The possibility is discussed that the hypercholesterolemia obtained in the beta-sitosterol-infused rats is due to the inhibitory effect of sitosterol on the cholesterol 7 alpha-hydroxylase.

    Topics: Animals; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Disease Models, Animal; Hydroxymethylglutaryl CoA Reductases; Hypercholesterolemia; Male; Microsomes, Liver; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Steroid Hydroxylases

1989
[Sterols from Gynostemma pentafillum].
    Bollettino della Societa italiana di biologia sperimentale, 1989, Volume: 65, Issue:4

    The sterol fraction of Gynostemma pentafillum contains beta-sito sterol and isofucosterol. The identification of these compounds has been carried out through NMR and MS data.

    Topics: Phytosterols; Plants; Sitosterols; Stigmasterol

1989
Fatty acid desaturase activities are modulated by phytosterol incorporation in microsomes.
    Biochimica et biophysica acta, 1989, Sep-25, Volume: 1005, Issue:2

    The effect of phytosterol-rich diets (3% beta-sitosterol + 2% campesterol) on rat liver microsomal fatty acid desaturases, membrane dynamics and lipid composition was investigated. After a 21 day period, phytosterol was incorporated into microsomes and the membrane fluidity decreased. There were no changes in either the phospholipid composition or in the total sterol content. However, the phytosterol/cholesterol ratio increased. In the animals fed phytosterols, the delta 5-, delta 6- and delta 9-fatty acid desaturases were significantly more active than in control animals. The changes in the lipid fatty acid composition were consistent with those of the desaturase activities. Hence, it is suggested that: (1) dietary phytosterol modulates desaturase activities; (2) phytosterols make the membrane more rigid but do not induce changes in the relative phospholipid composition; (3) delta 9-, delta 5- and delta 6-desaturase activities increase when the membrane becomes more rigid without changes in the phospholipid composition.

    Topics: Animals; Cholesterol; Diet; Fatty Acid Desaturases; Fluorescence; Male; Microsomes, Liver; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols

1989
Contribution of plasma protein and lipoproteins to intestinal lymph: comparison of long-chain with medium-chain triglyceride duodenal infusion.
    Lymphology, 1989, Volume: 22, Issue:1

    In rats with intestinal lymph-fistula and electrolyte and protein losses continuously replaced by I.V. infusion, the plasma to lymph filtration of total protein, albumin, and cholesterol was similar after duodenal infusion of either long-chain (LCT) or medium-chain (MCT) triglyceride. Filtration of cholesterol into intestinal lacteals was also measured after pulsed I.V. administration of 14C-beta-sitosterol as an indirect marker for passage of lipoproteins into the lymph system. During intraduodenal administration of LCT and constant I.V. infusion of 125I-apo high density lipoprotein (HDL), intact plasma HDL appeared in lymph and contributed apo-LP to chylomicron formation. Nevertheless, most lymph apo-LP originated from local mucosal synthesis.

    Topics: Animals; Blood Proteins; Carbon Radioisotopes; Cholesterol; Duodenum; Infusions, Intravenous; Intestinal Mucosa; Lipoproteins; Lymph; Male; Rats; Rats, Inbred Strains; Sitosterols; Triglycerides

1989
[Studies on the chemical constituents of Aconitum szechenyianum Gay].
    Yao xue xue bao = Acta pharmaceutica Sinica, 1989, Volume: 24, Issue:1

    Five constituents were isolated from Aconitum szechenyianum Gay. The structures of these compounds were identified as beta-sitosterol (I), aconitine (II), 3-acetylaconitine (III), songorine (IV) and a new compound whose structure was elucidated to be szechenyine (V) on the basis of UV, IR, 1HNMR, 13CNMR and Mass spectra.

    Topics: Acetylcarnitine; Aconitine; Aconitum; Alkaloids; Chemical Phenomena; Chemistry; Drugs, Chinese Herbal; Sitosterols

1989
Effects of cholesteryl esters on the accessibility of LH/hCG receptors and membrane lipid fluidity in rat testes.
    Biochimica et biophysica acta, 1989, Mar-13, Volume: 979, Issue:3

    Incubation of rat testicular membranes with cholesteryl hemisuccinate resulted in an increase in both membrane lipid microviscosity and 125I-labelled hCG specific binding. The purpose of this investigation was to establish which functional groups of cholesteryl hemisuccinate are important for the stimulatory effects. The data obtained showed that only esters of cholesterol with dicarboxylic acids, not those of monocarboxylic acids, increase the accessibility of LH/hCG receptors and membrane rigidity. Experiments with cholesteryl sulfates showed that there are polar groups on C3 carbon of cholesterol having no stimulatory effect on receptors, although an increase in membrane rigidity occurred. The side-chain of cholesterol is important for the stimulatory action. Androstenolone hemisuccinate was ineffective in this respect. On the other hand, partially modified side-chains (hemisuccinates of beta-sitosterol and stigmasterol) did not result in a marked reduction of the stimulatory action. The carboxyl group of cholesteryl hemisuccinate must be 'free': its esterification abolishes the stimulatory effect of cholesteryl hemisuccinate on both the LH/hCG receptor and membrane microviscosity. These results suggest that an intact carboxyl group of ester and the side-chain of cholesterol are indispensable for the stimulatory effect of cholesteryl hemisuccinate on the accessibility of LH/hCG receptors.

    Topics: Animals; Cell Membrane; Cholesterol Esters; Chorionic Gonadotropin; Male; Membrane Fluidity; Molecular Structure; Rats; Rats, Inbred Strains; Receptors, LH; Sitosterols; Stigmasterol; Structure-Activity Relationship; Testis; Viscosity

1989
Influence of beta-sitosterol on the fibrinolytic potential in rabbits.
    Folia haematologica (Leipzig, Germany : 1928), 1988, Volume: 115, Issue:1-2

    Long-term treatment of rabbits with beta-sitosterol (40 mg/kg over 3 months) caused an increased fibrinolytic activity in blood, an increased fibrinolytic capacity and an enhanced plasminogen activator activity in tissue of lungs and kidneys. The 3-months lasting beta-sitosterol administration did not influence the content of plasminogen activator inhibitor, plasminogen, alpha 2-antiplasmin, antithrombin III and fibrinogen.

    Topics: Animals; Female; Fibrinolysis; Kidney; Ligation; Lung; Male; Plasminogen Activators; Plasminogen Inactivators; Rabbits; Sitosterols; Time Factors

1988
Inhibition of cholesterol absorption in rats by plant sterols.
    Journal of lipid research, 1988, Volume: 29, Issue:12

    The extent and site(s) of inhibition of cholesterol absorption by plant sterols, sitosterol and fucosterol, were studied in rats. The intragastric administration of a single emulsified lipid meal containing 25 mg [3H]cholesterol and 25 mg of either sitosterol or fucosterol inhibited the lymphatic absorption of cholesterol by 57% and 41%, respectively, in 24 hr. Less than 2% of each plant sterol was absorbed in the 24-hr period. In contrast, neither plant sterol (50 microM) inhibited cholesterol absorption when co-administered with equimolar amounts of cholesterol in phospholipid-bile salt micelles nor was either absorbed from the micellar solution. A series of in vitro studies was conducted to identify the site(s) of plant sterol inhibition of cholesterol absorption and to account for the difference in inhibitory effectiveness of sitosterol and fucosterol. A comparison of the micellar solubility of each sterol alone and in equimolar binary mixtures (to 2.0 mM) revealed that the solubility of individual sterols decreased in the following order: cholesterol, fucosterol, sitosterol, and that in binary mixtures cholesterol solubility was decreased by sitosterol and, to a lesser extent, by fucosterol relative to its solubility alone. A comparison between micellar-solubilized cholesterol and either sitosterol or fucosterol for binding to isolated brush border membranes, intestinal mucin, or for esterification by either cholesterol esterase or acyl coenzyme A:cholesterol acyltransferase revealed moderate to no competition. The data suggest that plant sterols displace cholesterol from bile salt (taurocholate) micelles and that sitosterol is more effective than fucosterol in this capacity.

    Topics: Absorption; Animals; Anticholesteremic Agents; Binding, Competitive; Cholesterol; Esterification; Gastric Mucins; In Vitro Techniques; Intestinal Absorption; Lymphatic System; Male; Micelles; Microvilli; Mucous Membrane; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Solubility; Sterol Esterase; Stigmasterol

1988
Polyterpenoids as cholesterol and tetrahymanol surrogates in the ciliate Tetrahymena pyriformis.
    Biochimica et biophysica acta, 1988, May-22, Volume: 960, Issue:2

    The tetracyclic sterol precursors, cyclolaudenol, cycloartenol and lanosterol, inhibit efficiently the tetrahymanol biosynthesis in the ciliate Tetrahymena pyriformis, as reported earlier for cholesterol and other sterols. The prokaryotic bacteriohopanetetrols have little effect, and diplopterol, another hopanoid, as well as the carotenoid, canthaxanthin, have no effect. In the presence of triparanol, a hypocholesterolemic drug inhibiting the squalene cyclase of T. pyriformis and modifying the fatty acid metabolism, the cells do not grow further, but growth can be restored by the addition to the culture medium of suitable polyterpenoids. Thus, growth in presence of triparanol (13 microM) is almost normal after addition of a sterol such as sitosterol and cyclolaudenol, and longer lag times and lower absorbances than those of untreated cultures are observed in presence of cyclartenol, lanosterol, euphenol (a lanosterol isomer), bacteriohopanetetrols and three carotenoids. No growth at all is observed in the presence of tetrahymanol and diplopterol, although these triterpenoids are the normal reinforcers of the ciliate, probably because of a poor bioavailability. Thus, structurally different polyterpenoids are (at least partially) functionally equivalent and capable of replacing tetrahymanol or sterols and might act as membrane reinforcers in T. pyriformis cells.

    Topics: Animals; Cholesterol; Lanosterol; Phytosterols; Polymers; Sitosterols; Squalene; Tetrahymena pyriformis; Triparanol; Triterpenes

1988
Competitive inhibition of bile acid synthesis by endogenous cholestanol and sitosterol in sitosterolemia with xanthomatosis. Effect on cholesterol 7 alpha-hydroxylase.
    The Journal of clinical investigation, 1988, Volume: 82, Issue:6

    The 7 alpha-hydroxylation of two cholesterol analogues, sitosterol and cholestanol, and their effect on the 7 alpha-hydroxylation of cholesterol were measured in rat and human hepatic microsomes. In untreated rat liver microsomes, the 7 alpha-hydroxylation of cholesterol was higher than that of cholestanol (1.4-fold) and sitosterol (30-fold). After removal of endogenous sterols from the microsomes by acetone treatment, the 7 alpha-hydroxylation of cholesterol was similar to that of cholestanol and only fourfold higher than that of sitosterol. Cholestanol and sitosterol competitively inhibited cholesterol 7 alpha-hydroxylase in both rat and human liver microsomes, with cholestanol the more potent inhibitor. Patients with sitosterolemia with xanthomatosis, who have elevated microsomal cholestanol and sitosterol, showed reduced cholesterol 7 alpha-hydroxylase activity relative to the activity in control subjects (13.9 and 14.7 vs. 20.3 +/- 0.9 pmol/nmol P-450 per min, P less than 0.01). Enzyme activity in these patients was 40% higher when measured in microsomes from which competing sterols had been removed. Ileal bypass surgery in one sitosterolemic patient decreased plasma cholestanol and sitosterol concentrations and resulted in a 30% increase in hepatic microsomal cholesterol 7 alpha-hydroxylase activity. Cholesterol 7 alpha-hydroxylase appears to have a specific apolar binding site for the side chain of cholesterol and is affected by the presence of cholestanol and sitosterol in the microsomal substrate pool. Reduced bile acid synthesis in sitosterolemia with xanthomatosis may be related to the inhibition of cholesterol 7 alpha-hydroxylase activity by endogenous cholesterol analogues.

    Topics: Adolescent; Adult; Animals; Bile Acids and Salts; Cholestanol; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Female; Humans; Kinetics; Male; Microsomes, Liver; Middle Aged; Rats; Sitosterols; Steroid Hydroxylases; Substrate Specificity; Xanthomatosis

1988
Effects of MK-733, an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A reductase, on absorption and excretion of [3H]cholesterol in rabbits.
    Biochimica et biophysica acta, 1988, Nov-04, Volume: 963, Issue:1

    Effects of MK-733 on the absorption and excretion of cholesterol in rabbits were examined using [3H]cholesterol. The animals were divided into six groups; three groups were fed a normal diet, and the other groups a cholesterol diet. MK-733 was administered orally as a single dose of 10 mg/kg on day 8, or multiple doses of 10 mg/kg once a day for 14 days. On the 8th day, [3H]cholesterol was given orally to each animal. In the groups fed a normal diet, single and consecutive administration of MK-733 did not affect the absorption and excretion of [3H]cholesterol. In the cholesterol-fed groups, however, single administration of MK-733 decreased the serum 3H radioactivity slightly, but did not affect the fecal excretion of [3H]cholesterol. However, the consecutive treatment with MK-733 clearly reduced the serum 3H radioactivity. The cumulative excretion of the fecal radioactivity of [3H]cholesterol in the MK-733 group (multiple) was higher than that in the control group. From these results, it is concluded that MK-733 inhibits the absorption of cholesterol from the gastrointestinal wall in cholesterol-fed rabbits.

    Topics: Administration, Oral; Animals; Cholesterol; Cholesterol, Dietary; Feces; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Lovastatin; Male; Rabbits; Simvastatin; Sitosterols

1988
Thrombin binding to platelets from hypercholesterolaemic rats.
    Atherosclerosis, 1988, Volume: 73, Issue:2-3

    Platelets from rats made hypercholesterolaemic with a diet enriched with milk fat and cholesterol and containing taurocholate to promote hypercholesterolaemia aggregated more extensively to a low concentration of thrombin than platelets from rats given a milk fat-enriched diet containing sitosterol. Total and specific binding of thrombin to platelets from hypercholesterolaemic rats was significantly greater than in controls when expressed per mg platelet protein, per mumol platelet cholesterol, or per unit relative surface area. Total and specific binding of thrombin per platelet were not different between the groups. However, platelets from hypercholesterolaemic rats had less protein and cholesterol, were smaller and had less surface area than control platelets; platelet cholesterol content expressed per mg platelet protein was not different. Thus, the increase in thrombin-binding to the smaller platelets from hypercholesterolaemic rats during the first 10 s after its addition may be responsible, at least in part, for the hypersensitivity of these platelets to thrombin.

    Topics: Animals; Blood Platelets; Cholesterol; Cholesterol, Dietary; Dietary Fats; Hypercholesterolemia; Male; Milk; Protein Binding; Rats; Rats, Inbred Strains; Sitosterols; Taurocholic Acid; Thrombin

1988
The selective uptake of cholesterol by the rat tapeworm Hymenolepis diminuta (Cestoda).
    Comparative biochemistry and physiology. B, Comparative biochemistry, 1988, Volume: 91, Issue:1

    1. The sterols of Hymenolepis diminuta are almost exclusively cholesterol or similar C-27 sterols; the free sterols of its environment (the lumen of the rat intestine) are cholesterol and various phytosterols. 2. During incubation of tapeworms with mixed micelles of taurocholate, glyceryl monooleate, and equimolar [3H]cholesterol and [14C]beta-sitosterol, the uptake of cholesterol is 40 times more rapid than the uptake of sitosterol. 3. Following uptake, the desorption of labeled sitosterol is six times more rapid than that of cholesterol. 4. We did not detect the esterification of absorbed sterols or the conversion of absorbed sitosterol of cholesterol. 5. The highly selective uptake of cholesterol and the moderately selective desorption of phytosterols can account for the selective accumulation of C-27 sterol by the tapeworm.

    Topics: Animals; Biological Transport, Active; Cholesterol; Hymenolepis; Micelles; Sitosterols; Sterols

1988
Regulation of plasma plant sterol levels in patients with gut resections.
    Scandinavian journal of clinical and laboratory investigation, 1988, Volume: 48, Issue:7

    The role of cholesterol and bile acid malabsorption in the regulation of plasma plant sterol levels was studied in 30 patients with an ileal resection (seven without any malabsorption, eight with bile acid malabsorption alone and 15 with bile acid, fat and cholesterol malabsorption) and nine with jejunoileal bypass (modest bile acid, and severe cholesterol and fat malabsorption). In contrast to cholesterol, plant sterols are not synthesized by the body, and so the plasma levels are regulated by their intestinal absorption and biliary secretion. In fact, the plant sterol, especially campesterol, levels were low in patients with cholesterol and fat malabsorption. Cholesterol absorption efficiency was a significant determinant of the plant sterol levels, suggesting that it reflects overall sterol absorption efficiency and that the plasma plant sterol levels, in turn, reflect cholesterol absorption. Bile acid malabsorption, though it appeared to promote biliary plant sterol secretion, had little direct effect on the plasma plant sterol contents. The results indicate that plasma campesterol levels can be used to evaluate cholesterol absorption efficiency in general and may reveal clinically significant steatorrhoea in patients with gut exclusion.

    Topics: Adult; Aged; Cholesterol; Humans; Ileum; Intestinal Absorption; Jejunoileal Bypass; Lipids; Malabsorption Syndromes; Middle Aged; Phytosterols; Sitosterols

1988
Studies on the mechanism of high intestinal absorption of cholesterol and campesterol in high-responding rhesus monkeys.
    Atherosclerosis, 1988, Volume: 72, Issue:2-3

    To understand better the mechanism of higher absorption of cholesterol and campesterol in high-responding than in low-responding rhesus monkeys, we measured the concentrations of the two sterols in the micellar fraction isolated from small intestinal content, and also determined their rates of esterification by cholesterol esterase prepared from the small intestinal mucosa. The results show that the concentrations of both cholesterol and campesterol in the micellar fraction were significantly higher in the high- than in low- and intermediate-responding rhesus monkeys. Also the rates of esterification of both sterols are higher in the proximal segment of the small intestine in high-responders than the other two groups. We conclude that the two necessary steps in the process of sterol absorption, namely, the amounts of sterols solubilized in micelles and their esterification within mucosal cells which are higher in high- than in low-responders are responsible for the higher absorption of the sterols in the high-responding rhesus monkeys.

    Topics: Animals; Cholesterol; Cholesterol, Dietary; Fatty Acids; Intestinal Absorption; Intestine, Small; Macaca; Macaca mulatta; Male; Micelles; Phytosterols; Sitosterols; Sterol Esterase

1988
Discrimination between cholesterol and sitosterol for absorption in rats.
    Journal of lipid research, 1988, Volume: 29, Issue:12

    The intestinal absorption of cholesterol and sitosterol was compared in rats. The intragastric administration of a single emulsified lipid meal containing either 50 mg of [4-14C]cholesterol or [4-14C]sitosterol resulted in the lymphatic absorption of 18.2% and 0.42% of each sterol, respectively, in 6 hr. This difference was unaltered when the mucosal sterol load was equalized by reducing the cholesterol to 1 mg in the emulsified lipid meal while maintaining the same sitosterol load or when the physical state in the lumen was equalized by infusion of a micellar solution containing both sterols into bile-diverted intestine. Lymphatic cholesterol was 90% esterified compared to 12% for sitosterol. Both sterols were associated predominantly (greater than 70%) with the chylomicron fraction. Eighty percent of the chylomicron cholesterol was recovered as ester with the core lipids, while 77% of the sitosterol was recovered as free sterol with the chylomicron coat. In mucosal homogenates at 6 hr, sitosterol recovery was one-eleventh that of cholesterol. When [3H]cholesterol (10 mg) and [14C]sitosterol (10 mg) were co-administered in an emulsified intragastric lipid meal, sitosterol associated with the brush border isolated 2 hr later was one-fifth that of cholesterol. Similar differences were seen when brush border membranes were incubated in vitro with micellar solutions containing either 50 microM [3H]cholesterol or [14C]sitosterol and the relative uptake of each sterol was unaffected by micellar phospholipid type (egg yolk phospholipids, phosphatidylcholine, or phosphatidylethanolamine).(ABSTRACT TRUNCATED AT 250 WORDS)

    Topics: Animals; Binding, Competitive; Cholesterol; Esterification; In Vitro Techniques; Intestinal Absorption; Lymphatic System; Male; Micelles; Microvilli; Mucous Membrane; Rats; Sitosterols

1988
Redistribution of cholesterol and beta-sitosterol between intralipid and rat plasma lipoproteins and red blood cells in vivo.
    Biochemistry and cell biology = Biochimie et biologie cellulaire, 1988, Volume: 66, Issue:12

    Male Wistar rats were injected intravenously with 2 mL of Intralipid containing 7.5 x 10(5) counts per minute (cpm) [14C]cholesterol and 7.5 x 10(5) cpm beta-[3H]sitosterol. Blood was withdrawn immediately and at 5, 10, 20, 60, 120, and 1440 min after injection from different animals. Plasma and red cells were separated and washed by conventional centrifugation, while lipoprotein density classes corresponding to chylomicrons, very low (VLDL), low (LDL), and high density lipoproteins (HDL) were isolated by ultracentrifugation. Total lipid and sterol compositions were determined by thin-layer chromatography in combination with gas-liquid chromatography, whereas radioactivity was measured by scintillation counting. The ratio of [14C]cholesterol/beta-[3H]sitosterol rose from 1 to 3.65 in the plasma VLDL fraction, whereas that in the LDL and HDL fractions were equilibrated at about 2, following an initial transient increase in favour of cholesterol. The appearance and disappearance of the radioactivity from LDL and HDL fractions exhibited precursor-product relationship owing probably to the conversion of the Intralipid into an intermediate lipoprotein-X-like particle, which possesses a density similar to that of LDL. The radioactive cholesterol and beta-sitosterol were incorporated into the red blood cell membranes at nearly similar initial rates, while at later times the incorporation of cholesterol was much preferred.

    Topics: Animals; Cholesterol; Erythrocytes; Fat Emulsions, Intravenous; Lipids; Lipoproteins; Male; Microscopy, Electron; Rats; Rats, Inbred Strains; Sitosterols; Sterols

1988
[Isolation and identification of isoflavones in the root of Caragana intermedia Kuang].
    Zhong yao tong bao (Beijing, China : 1981), 1988, Volume: 13, Issue:12

    Topics: Drugs, Chinese Herbal; Fabaceae; Flavonoids; Isoflavones; Plants, Medicinal; Sitosterols

1988
[The chemical constituents of Ardisia crenata Sims].
    Zhong yao tong bao (Beijing, China : 1981), 1988, Volume: 13, Issue:12

    Topics: Anti-Ulcer Agents; Benzopyrans; Benzoquinones; Drugs, Chinese Herbal; Flavonoids; Isoflavones; Quinones; Sitosterols; Triterpenes

1988
Schistosoma mansoni: sterol and phospholipid composition of cercariae, schistosomula, and adults.
    Experimental parasitology, 1988, Volume: 65, Issue:2

    The sterol and phospholipid composition of cercariae, schistosomula, and adult Schistosoma mansoni was analyzed by gas-liquid chromatography and high-performance liquid chromatography (HPLC). Cercariae and schistosomula contained cholesterol, desmosterol, campesterol, stigmasterol, and beta-sitosterol while adults contained only cholesterol. In all stages cholesterol comprised greater than 50% of the total sterols, and in cercariae and schistosomula desmosterol comprised 38 and 21% of the total sterols, respectively. The other three sterols, campesterol, stigmasterol, and beta-sitosterol, made up approximately 10% of the total. The same five sterols found in cercariae and schistosomula were present in the hepatopancreas of uninfected snails but with a much higher desmosterol concentration in the parasite, 38%, than in the snail, 2%. As in cercariae and schistosomula the three minor sterols comprised approximately 10%. Thus, the sterol composition of cercariae and schistosomula was similar but not identical to that of the snail host. Phosphatidylcholine was the major phospholipid of all three stages (50%) as determined by two HPLC procedures. The remaining phospholipids consisted of phosphatidylethanolamine, phosphatidylserine, and phosphatidylinositol. In addition, in adults there were small quantities of sphingomyelin and lysophosphatidylcholine. The percentage of each phospholipid was similar among stages with the exception of a slight increase in phosphatidylserine in adults compared to cercariae and schistosomula. These results show that a characteristic lipid composition is found in cercariae, schistosomula, and adults.

    Topics: Animals; Cholesterol; Chromatography, Gas; Chromatography, High Pressure Liquid; Desmosterol; Phosphatidylcholines; Phosphatidylethanolamines; Phosphatidylinositols; Phosphatidylserines; Phospholipids; Phytosterols; Schistosoma mansoni; Sitosterols; Sterols; Stigmasterol

1988
Serum plant sterols and lathosterol related to cholesterol absorption in coeliac disease.
    Clinica chimica acta; international journal of clinical chemistry, 1988, May-31, Volume: 174, Issue:2

    The concentrations of the plant sterols, campesterol and beta-sitosterol in serum, normally correlate with the efficiency of cholesterol absorption, whereas the concentration of lathosterol, a cholesterol precursor sterol, closely parallels changes in cholesterol synthesis. In this study we explored whether the plant sterol concentrations in serum in coeliac disease are determined by cholesterol absorption and whether they alone or with the serum lathosterol concentration, could be used for screening the activity of coeliac disease. In six patients the plant sterol concentrations in serum were significantly lower than in 17 control subjects, the reduction being more marked for campesterol than for beta-sitosterol: the serum lathosterol concentration was significantly higher than in the control subjects. The opposite changes in serum plant sterols and lathosterol were recorded in patients on a gluten-free diet. The plant sterol concentrations in serum (nmol/mg of cholesterol) were positively correlated with each other, and with the percentage absorption of cholesterol and with xylose absorption; they were negatively correlated with faecal fat, but not with faecal plant sterols. Thus, the low plant sterol concentrations in serum in coeliac disease were attributable to their impaired absorption, which in turn was closely associated with the absorption of cholesterol. The serum campesterol concentration clearly distinguished the untreated patients from the controls, whereas the use of serum beta-sitosterol, and the serum ratios of lathosterol/plant sterol resulted in some overlapping with the controls. It is suggested that the plant sterols in serum might be worth of determining when screening patients for coeliac disease and especially when testing their adherence to the gluten-free diet.

    Topics: Celiac Disease; Cholesterol; Cholesterol, Dietary; Glutens; Humans; Phytosterols; Sitosterols

1988
Sitosterolaemia and heterozygous familial hypercholesterolaemia in a three year old girl: case report.
    The New Zealand medical journal, 1988, Jun-22, Volume: 101, Issue:848

    A case of a 3 1/2 year old female child is described in which symptomless cutaneous xanthomatosis led to the diagnosis of sitosterolaemia in the presence of a defect of low-density lipoprotein uptake by cultured fibroblasts. The condition responded to treatment by cholestyramine with normalisation of the blood lipid levels. Normal growth and development continued for three years of observation.

    Topics: Child, Preschool; Female; Heterozygote; Humans; Hyperlipoproteinemia Type II; Lipoproteins; Sitosterols

1988
Inhaled tobacco sterols: uptake by the lungs and disposition to selected organs of rats.
    The Journal of laboratory and clinical medicine, 1988, Volume: 112, Issue:2

    Tobacco sterols (cholesterol, beta-sitosterol, campesterol, and stigmasterol) are present in tobacco smoke and appear in plasma of mammals exposed to cigarette smoke. Because tobacco sterols may be important in the pathogenesis of smoking-induced lung and vascular diseases, we studied the pattern of deposition of cigarette sterols in the lungs and appearance of cigarette sterols in plasma and body organs of rats. After exposure to twenty 5 ml "puffs" of smoke from tobacco labeled with [4-14C]cholesterol or beta-[4-14C]sitosterol, rats were killed just after exposure (day 0) and on days 2, 5, 8, 11, 15, and 30, and the lungs and selected body organs analyzed for activity. We found that cigarette sterols are associated with particulates in cigarette smoke, deposited mostly in distal airspaces and parenchyma of the lungs, and appear in plasma and several body organs for more than 30 days after this single exposure to cigarette smoke. Bronchoalveolar lavage fluid contained relatively small amounts of radiolabel for only the first few days, suggesting that most of the sterols were rapidly incorporated in lung parenchyma. Because disorders of sterol metabolism have been implicated in a variety of diseases including atherosclerosis and cancer, the significance of tobacco sterols to human smoking-induced diseases deserves further study.

    Topics: Animals; Bronchoalveolar Lavage Fluid; Cholesterol; Esophagus; Gastric Mucosa; Kidney; Liver; Lung; Male; Nicotiana; Phytosterols; Plants, Toxic; Rats; Rats, Inbred Strains; Sitosterols; Smoke; Spleen; Sterols; Stigmasterol; Tissue Distribution

1988
Interaction of the polyene antibiotic filipin with model and natural membranes containing plant sterols.
    Biochimica et biophysica acta, 1988, Aug-18, Volume: 943, Issue:2

    The interaction of the polyene antibiotic, filipin, with individual or mixed plant sterols (stigmasterol, sitosterol, campesterol and 24-methylpollinastanol) incorporated into large unilamellar vesicles (LUV) of soybean phosphatidylcholine (PC) as well as the filipin interaction with purified membrane fractions from maize roots containing these sterols was investigated by ultraviolet (UV) absorption and and circular dichroism (CD) spectroscopy. With both types of membrane preparation, dramatic changes in the UV absorption and CD spectra of the antibiotic were evidenced. When LUV containing stigmasterol, sitosterol and/or campesterol were incubated with low filipin concentrations (i.e., for filipin/sterol molar ratios (rst) lower than 1), CD signal characteristic of the formation of filipin-sterol complexes were observed. At higher rst values, the filipin-sterol interaction was shown to be in competition with a filipin-phospholipid interaction. With 24-methylpollinastanol-containing LUV, the filipin-phospholipid interaction was detected even at rst values lower than 1, which suggests a lower affinity of filipin for this sterol and emphasizes the structural differences between delta 5-sterols and 9 beta,19-cyclopropylsterols. With sterol-free soybean PC LUV, a filipin-phospholipid interaction could also be evidenced. With maize root cell membranes containing either delta 5-sterols or 9 beta,19-cyclopropylsterols, CD spectra similar to those obtained in the presence of LUV having these sterols as components were observed. Thus, the protein component of the membranes does not appear to be an important feature.

    Topics: Cell Membrane; Cholestanols; Cholesterol; Circular Dichroism; Filipin; Liposomes; Phytosterols; Plants; Polyenes; Sitosterols; Spectrophotometry, Ultraviolet; Stigmasterol; Zea mays

1988
[Chemical constituents of Rabdosia japonica var. glaucocalyx].
    Zhong yao tong bao (Beijing, China : 1981), 1987, Volume: 12, Issue:5

    Topics: Antineoplastic Agents, Phytogenic; Diterpenes, Kaurane; Drugs, Chinese Herbal; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

1987
Xanthogranulomatosis in an adult: lipid analysis of xanthomas and plasma.
    Journal of the American Academy of Dermatology, 1987, Volume: 16, Issue:1 Pt 2

    Xanthomatosis in the absence of hyperlipidemia is unusual but has been associated with compositional abnormalities of lipoprotein particles. An adult who developed juvenile xanthogranulomatosis in association with oral contraceptive ingestion is reported. Plasma lipids and lipoprotein electrophoresis were normal, as in a few other patients reported with this disorder. However, analysis of cutaneous xanthoma and plasma by thin-layer and gas-liquid chromatography revealed that cholesterol was the principal lipid in xanthoma and that there were no unusual sterols in plasma or tissue. Possible mechanisms of xanthoma formation are discussed. Thus juvenile xanthogranulomatosis should be considered in adults with normolipemic xanthomatosis.. This article reports the case of a 23-year-old woman with juvenile xanthogranulomatosis, an unusual normolipemic xanthomatosis most often seen in young children. Chromatographic techniques were used to analyze this patient's plasma and xanthomatous tissue for beta-sitosterol, cholestanol, and other sterols that might be present in unusual quantities. The woman had normal fasting levels of plasma cholesterol and triglyceride. The lipoprotein electrophoresis was also normal, and levels of unusual sterols, such as cholestanol and beta-sitosterol, were not increased in plasma or in the xanthomas. Analysis of xanthoma tissue revealed that the predominant lipid was cholesterol. The only medication this patient reported using was a combination oral contraceptive (OC) containing 1 mg of norethindrone and 0.035 mg of ethinyl estradiol. OC use was initiated 1 month before the onset of cutaneous symptoms. The patient refused to discontinue OC use. Since it was not possible to withdraw the drug and observe the patient for regression of the lesions, a causal association of juvenile xanthogranulomatosis with OC use can not be asserted. This case suggests that juvenile xanthogranulomatosis should be considered in adults with normolipemic xanthomatosis. Possible mechanisms for cutaneous xanthoma formation include a defect in local lipid synthesis, an abnormality in local tissue uptake and degradation of lipoproteins that may or may not be coupled with an abnormality in circulating lipoproteins, or local invasion of histiocytes that then accumulate large amounts of cholesterol because of an intrinsic cellular abnormality.

    Topics: Adult; Biopsy; Cholestanols; Cholesterol; Contraceptives, Oral, Synthetic; Female; Humans; Lipids; Sitosterols; Xanthogranuloma, Juvenile

1987
Prophylaxis of alimentary hypercholesterolemia.
    Atherosclerosis, 1987, Volume: 68, Issue:3

    Topics: Animals; Cholesterol, Dietary; Humans; Hypercholesterolemia; Sitosterols

1987
Separation and identification of phytoestrogenic compounds isolated from bourbon.
    Alcohol and alcoholism (Oxford, Oxfordshire). Supplement, 1987, Volume: 1

    There is considerable evidence that several plant metabolites have estrogenic properties. Given that many alcoholic beverages are made from plants which have been shown to possess estrogenic activity, we considered the possibility that alcoholic beverages may contain estrogenically active substances. To evaluate this hypothesis we first extracted and then used gas chromatography/mass spectrometry to identify two phytoestrogens, biochanin A and beta-sitosterol in the bourbon extracts. Based on these findings we suggest that the feminization observed in chronic male alcoholics with liver disease may reflect, at least in part, the presence of biologically active phytoestrogens in the alcoholic beverages they consume.

    Topics: Alcoholic Beverages; Chemical Phenomena; Chemistry; Estrogens; Estrogens, Non-Steroidal; Gas Chromatography-Mass Spectrometry; Genistein; Isoflavones; Phytoestrogens; Plant Preparations; Sitosterols

1987
[Isolation and identification of the lipophilic constituents from the root of Euphorbia fischeriana Steud].
    Zhong yao tong bao (Beijing, China : 1981), 1987, Volume: 12, Issue:8

    Topics: Drugs, Chinese Herbal; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Triterpenes

1987
[Active constituents of Rabdosia henryi (Hemsl.) Hara].
    Zhong yao tong bao (Beijing, China : 1981), 1987, Volume: 12, Issue:10

    Topics: Chemical Phenomena; Chemistry; Diterpenes; Medicine, Chinese Traditional; Oleanolic Acid; Plants, Medicinal; Sapogenins; Sitosterols

1987
Effects of ketoconazole on cholesterol synthesis and precursor concentrations in the rat liver.
    Lipids, 1987, Volume: 22, Issue:12

    Ketoconazole, an antimycotic agent, given to rats for a week as 0.05% food addition had no effect on the hepatic concentrations of free and esterified cholesterol or on the activity of acyl coenzyme. A: cholesterol-acyltransferase (ACAT). However, the levels of free methylated cholesterol precursors, especially lanosterols, less markedly delta 8,24 and delta 8-dimethyl sterols and monomethyl sterols, were increased after only one day's treatment, while those of esterified methyl sterols were increased inconsistently, and those of free and esterified delta 8-lathosterol, lathosterol and desmosterol were not affected at all. Cholestyramine treatment had no significant effect on ACAT in spite of a decrease in the hepatic content of esterified cholesterol and caused a marked increase in the free cholesterol precursor levels, especially in those of lathosterols. Cholestyramine given to ketoconazole-treated rats increased the hepatic levels of delta 8 and delta 7-lathosterols but not desmosterol or methylated cholesterol precursors. Ketoconazole increased and cholestyramine markedly decreased plant sterols, sitosterol and campesterol in the liver. In serum, the contents of both lanosterols and lathosterol were increased but that of cholesterol tended to be decreased by ketoconazole (-19%). The results indicate that ketoconazole impairs demethylation processes at C-14 and to some extent at C-4 in the rat liver, resulting in lowered serum cholesterol level.

    Topics: Animals; Cholesterol; Cholestyramine Resin; Ketoconazole; Kinetics; Liver; Male; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Sterol O-Acyltransferase

1987
Distribution and partitioning of cholesterol and beta-sitosterol in micellar bile salt solutions.
    The American journal of physiology, 1987, Volume: 253, Issue:3 Pt 1

    The distribution of cholesterol and beta-sitosterol in micellar bile salt solutions was studied using an ultrafiltration technique to separate micellar aggregates from monomers present in the intermicellar aqueous phase. The partitioning and the rates of influx across the brush-border membrane of these two sterols from micellar solutions were determined using polyethylene discs and everted jejunal sacs, respectively. Micellar solubilities of cholesterol and beta-sitosterol were not significantly different, whereas the monomer concentration of beta-sitosterol in the intermicellar aqueous phase was significantly lower than that of cholesterol [0.21 +/- 0.02 microM for beta-sitosterol and 25.0 +/- 2.71 (SE) microM for cholesterol, P less than 0.001]. There was no difference in the partitioning nor was there a difference in the rates of influx between cholesterol and beta-sitosterol from micellar solutions containing a similar amount of the two sterols. It is concluded that monomer concentration of beta-sitosterol in the intermicellar aqueous phase is extremely low compared with that of cholesterol, but their partitioning and rates of influx across the membrane are similar. This is primarily attributable to a much higher membrane/monomer partition coefficient of beta-sitosterol than cholesterol and to a direct interaction between micelle and membrane.

    Topics: Animals; Bile Acids and Salts; Cholesterol; In Vitro Techniques; Jejunum; Male; Micelles; Microvilli; Rats; Sitosterols; Solutions

1987
Intestinal cholesterol absorption in the chyluria model.
    Journal of lipid research, 1987, Volume: 28, Issue:10

    Isotopic methods for the measurement of dietary cholesterol absorption were compared with the lymph cholesterol balance procedure in filarial chyluria patients. After a single intravenous injection of radioactive cholesterol, absorption was found to be 746 +/- 136 mg/day by method I, which is based upon the fecal endogenous neutral steroid mass measurement, and 471 +/- 135 mg/day by the simultaneously measured lymph/plasma ratio of cholesterol specific activity (dpm/mg). The corresponding value, determined as the difference between lymph cholesterol transport on a cholesterol-containing diet (1500 mg) and on a cholesterol-free diet, was 622 mg/day. When radioactive cholesterol (1487 mg/day) was fed daily to a second patient, absorption determined by isotopic fecal recovery (353 mg/day) matched that obtained by the lymph balance procedure (326 mg/day). Transudation of plasma cholesterol into the intestinal lymph, estimated by the single intravenous injection of radioactive beta-sitosterol, was independent of both the luminal content of plant sterols and the absorption of dietary cholesterol. The absorption of endogenous cholesterol was calculated by: 1) subtracting the cholesterol originating from plasma (transudation) together with the absorbed dietary cholesterol found in lymph from the total mass of cholesterol transported in lymph, and 2) the lymph balance method, i.e., after interrupting the endogenous cholesterol mucosal uptake by beta-sitosterol feeding (9 g/day) while on a cholesterol-free diet. Endogenous cholesterol was preferentially absorbed compared to dietary cholesterol, but there was no competition for absorption. The major portion of dietary cholesterol found in lymph was esterified, but esterification was not a prerequisite for absorption.

    Topics: Adult; Aged; Cholesterol, Dietary; Chyle; Esters; Female; Humans; Intestinal Absorption; Lymph; Male; Middle Aged; Models, Biological; Sitosterols; Urine

1987
[Prostaglandin E2 in prostatitis and prostatic adenoma].
    Urologia internationalis, 1986, Volume: 41, Issue:2

    The measurement of prostaglandin E2 (PGE2) concentrations in the serum and prostatic fluid of healthy men, patients with prostatic hyperplasia and of patients with prostatitis was attempted and correlated to the state of disease, respectively. PGE2-concentrations with prostatic fluid of healthy men were found to be significantly lower than in patients with prostatitis. Corresponding to the course of treatment concentrations normalized, being favorably influenced by sitosterin as an adjuvant medication. Compared to healthy men, PGF2 concentrations in the prostatic fluid of patients with hyperplasia of the prostate incline to lower levels.

    Topics: Adult; Chronic Disease; Dinoprostone; Follow-Up Studies; Humans; Male; Middle Aged; Prostaglandins E; Prostate; Prostatic Hyperplasia; Prostatitis; Radioimmunoassay; Sitosterols

1986
[Chemical constituents of Typha angustata and Typha angustifolia].
    Zhong yao tong bao (Beijing, China : 1981), 1986, Volume: 11, Issue:12

    Topics: Animals; Guinea Pigs; Medicine, Chinese Traditional; Medicine, East Asian Traditional; Mice; Plant Extracts; Plants, Medicinal; Sitosterols; Species Specificity

1986
[Chemical constituents of Melastoma polyanthum].
    Zhong yao tong bao (Beijing, China : 1981), 1986, Volume: 11, Issue:12

    Topics: Benzopyrans; Ellagic Acid; Medicine, Chinese Traditional; Plants, Medicinal; Sitosterols

1986
Fucosterol decreases angiotensin converting enzyme levels with reduction of glucocorticoid receptors in endothelial cells.
    Biochemical and biophysical research communications, 1986, Aug-29, Volume: 139, Issue:1

    The modulation of angiotensin converting enzyme (ACE) levels was studied using fucosterol, one of phytosterols, in cultured bovine carotid endothelial cells. Addition of fucosterol to the culture medium resulted in the decrease of ACE activity of endothelial cells; however, fucosterol did not directly inhibit ACE activity. Dexamethasone elevated the levels of ACE in normal cells, but this effect was not seen in the fucosterol-treated cells. Receptor assays showed that the amount of glucocorticoid receptors in fucosterol-treated cells decreased to an undetectable level. These results indicate that fucosterol lowers the ACE levels on the endothelial cells by inhibiting the synthesis of glucocorticoid receptors involved in the regulation of ACE levels.

    Topics: Cells, Cultured; Dexamethasone; Endothelium; Peptidyl-Dipeptidase A; Phytosterols; Receptors, Glucocorticoid; Sitosterols; Stigmasterol

1986
Fecal bile acids and neutral sterols in rats with spontaneous colon cancer.
    International journal of cancer, 1986, Apr-15, Volume: 37, Issue:4

    Fecal bile acids and neutral sterols of spontaneous colon cancer-bearing Wistar-Furth strain rats were examined and compared with those of control rats of the same strain by gas chromatography and gas chromatography-mass spectrometry. The amount of total fecal bile acids and the percentage of fecal lithocholic acid were almost similar in both groups, but the percentage of fecal deoxycholic acid was significantly higher in the colon cancer group than in the controls. The amount of total fecal neutral sterols and the percentage of fecal coprostanol were also markedly higher in the colon cancer group than in the controls. The percentage of cholesterol and the amount of beta-sitosterol were, however, almost similar in the two groups. These results indicate that fecal deoxycholic acid and fecal coprostanol are notably higher in rats with colon cancer than in controls.

    Topics: Animals; Bile Acids and Salts; Cholestanol; Cholesterol; Colonic Neoplasms; Feces; Rats; Rats, Inbred WF; Sitosterols; Sterols

1986
Metabolism of 24-ethyl-4-cholesten-3-one and 24-ethyl-5-cholesten-3 beta-ol (sitosterol) after intraperitoneal injection in the rat.
    Scandinavian journal of clinical and laboratory investigation. Supplementum, 1986, Volume: 184

    14C-labeled C29- and C27-steroids were injected in rats, which were killed after 14 days. Phytosterols (C29) were excreted mainly as such, whereas C27-steroids were recovered essentially as water soluble metabolites. The total 14C-excretion was lower from 3-oxo, delta 4-steroids (5 alpha-stanol precursors) than from 3 beta-hydroxy,delta 5-steroids. 14C-Phytosterols were accumulated more than C27-steroids in liver, serum (mainly in HDL) and especially in adrenal glands and ovaries. In relation to serum, particularly the 5 alpha-stanols were enriched in the adrenal glands and ovaries. No striking lysosomal accumulation of any of the steroids was found.

    Topics: Animals; Arteriosclerosis; Blood Proteins; Cricetinae; Female; Injections, Intraperitoneal; Lipid Metabolism, Inborn Errors; Liver; Rats; Rats, Inbred Strains; Sitosterols; Subcellular Fractions; Tissue Distribution

1986
Visible fibrinolysis by endothelial cells: effect of vitamins and sterols.
    Bioscience reports, 1986, Volume: 6, Issue:12

    We have succeeded in corroborating the enhancing effect of vitamin A, vitamin C, sitosterol and fucosterol on the fibrinolytic activity of endothelial cells. The assay system consisted of an in situ dissolution of a fibrin layer coated onto a culture dish, over which endothelial cells were grown in a culture medium containing 10% serum. The dissolution was enhanced by the addition of these vitamins and phytosterols to the culture medium.

    Topics: Animals; Ascorbic Acid; Cattle; Cells, Cultured; Endothelium; Fibrin; Fibrinolysis; Phytosterols; Sitosterols; Stigmasterol; Vitamin A

1986
Absorption of cholesterol and beta-sitosterol from cigarette smoke in Macaca mulatta.
    Atherosclerosis, 1986, Volume: 60, Issue:1

    When smoke from single cigarettes containing [4-14C]cholesterol or beta-[4-14C]sitosterol was delivered to the lungs of Rhesus macaques, plasma contained radiolabeled sterols up to 50 days later. Since cholesterol, as well as plant sterols (campesterol, stigmasterol and beta-sitosterol), are normally present in cigarette smoke, our observations suggest that protracted absorption of sterols occurs after cigarette smoking.

    Topics: Animals; Carbon Radioisotopes; Cholesterol; Female; Intestinal Absorption; Lung; Macaca mulatta; Nicotiana; Plants, Toxic; Sitosterols; Smoke

1986
Abnormal metabolism of shellfish sterols in a patient with sitosterolemia and xanthomatosis.
    The Journal of clinical investigation, 1986, Volume: 77, Issue:6

    Sitosterolemia and xanthomatosis together are a disease characterized by premature cardiovascular disease, and by elevated plasma concentrations of total sterols and of plant sterols, especially sitosterol which is hyperabsorbed. In order to determine whether this abnormal metabolism also involved other sterols, a patient with sitosterolemia was fed a diet high in shellfish that contain significant quantities of noncholesterol sterols, some of which are less well absorbed than cholesterol in humans. Compared with control subjects (n = 8), the sitosterolemic subject had an increased absorption of 22-dehydrocholesterol (71.5% vs. 43.8 +/- 11.4%, mean +/- SD), C-26 sterol (80.6% vs. 49.3 +/- 11.4%), brassicasterol (51.8% vs. 4.8 +/- 4.2%), and 24-methylene cholesterol (60.5% vs. 16.0 +/- 8.3%). This enhanced absorption was associated with an increased plasma total shellfish sterol level (13.1 mg/dl vs. 1.9 +/- 0.7 mg/dl in normals). In the sitosterolemic subject, as in normals, the shellfish sterols were not preferentially concentrated in any lipoprotein class, and 50-65% of these sterols were in the esterified form in plasma. Bile acids and neutral sterols were quantitated in bile obtained by duodenal aspiration. The bile acid composition did not differ significantly in the sitosterolemic subject compared with the normal controls. The sitosterolemic subject, though, was unable to concentrate normally the neutral shellfish sterols in bile. The normal controls concentrated the shellfish sterols in bile 6.3 +/- 1.7-fold relative to the plasma shellfish sterol concentration whereas the study subject was only able to concentrate them 2.1-fold. We propose that sitosterolemia and xanthomatosis occur from a generalized abnormality in the usual ability of the gut mucosa and other tissues of the body to discriminate among many different sterols. This has important implications for the understanding of the pathophysiology of this disease and for therapeutic recommendations.

    Topics: Adult; Bile Acids and Salts; Cholestyramine Resin; Chromatography, Gas; Female; Humans; Hysterectomy; Intestinal Absorption; Lipids; Lipoproteins; Neomycin; Plants; Shellfish; Sitosterols; Xanthomatosis

1986
Investigation of the role of micellar phospholipid in the preferential uptake of cholesterol over sitosterol by dispersed rat jejunal villus cells.
    Biochemistry and cell biology = Biochimie et biologie cellulaire, 1986, Volume: 64, Issue:8

    The uptake of radioactive cholesterol and sitosterol by rat jejunal villus cells was examined using mixed micellar solutions containing sodium taurocholate, equimolar mixtures of the two sterols, and a variety of phospholipid types. The addition of phospholipid to the incubation solutions reduced the cellular absorption of both sterols and gave rise to uptake kinetics that were linear with time. In the presence of egg yolk phospholipid, uptake of the sterols by villus cells occurred with a modest preference for cholesterol over sitosterol. The ratio of accumulated cholesterol/sitosterol increased from 1.0 initially to 1.23 +/- 0.04 (n = 18) after a 30-min incubation at 37 degrees C. The selectivity displayed in the villus cells increased significantly as egg phosphatidylethanolamine was added to the egg phosphatidylcholine (PC) preparation in micellar solution. It was markedly decreased when dipalmitoyl PC or the primarily saturated egg yolk sphingomyelin were incorporated into the micelles. In every case examined, phospholipid was taken up by the cells concurrently with the sterols. The selectivity between cholesterol and sitosterol was maintained when the donor species were multilamellar vesicles composed of egg PC and the sterols, but not when the donor particles were albumin-stabilized sterol dispersions or taurocholate solutions in the absence of PC. The results show that the selective absorption of cholesterol over the plant sterol occurs only in the presence of unsaturated phospholipid. The phospholipid may act by influencing the permeability of the cellular membranes to the two sterols or the rate of sterol desorption from the phospholipid-containing micellar or liposomal carriers.(ABSTRACT TRUNCATED AT 250 WORDS)

    Topics: 1,2-Dipalmitoylphosphatidylcholine; Animals; Cholesterol; Colloids; Jejunum; Kinetics; Micelles; Phosphatidylcholines; Phosphatidylethanolamines; Phospholipids; Rats; Sitosterols; Sphingomyelins

1986
[Antitussive constituents of Verbena officinalis].
    Zhong yao tong bao (Beijing, China : 1981), 1985, Volume: 10, Issue:10

    Topics: Antitussive Agents; Glucosides; Glycosides; Iridoid Glycosides; Iridoids; Medicine, Chinese Traditional; Medicine, East Asian Traditional; Plant Extracts; Plants, Medicinal; Sitosterols; Tracheitis

1985
Modulation of yeast plasma membrane composition of a yeast sterol auxotroph as a function of exogenous sterol.
    Archives of biochemistry and biophysics, 1985, Aug-01, Volume: 240, Issue:2

    Plasma membranes isolated from a yeast sterol auxotroph (RD5-R) grown on 1, 5, and 15 micrograms ml-1 exogenous concentrations of sterol showed no discontinuity in plots of steady-state fluorescence anisotropy. Liposomes constructed from phospholipid and sterol extracted from RD5-R grown on different sterols indicated that exogenously supplied sterol modulated cellular phospholipids such that lipid-phase transitions were avoided. Liposomes derived from sterol and phospholipid extracted from the same culture exhibited no lipid-phase transitions. However, when phospholipid extracted from a culture grown on a specific sterol was mixed with sterol extracted from a heterologous culture grown on a different sterol to form liposomes, discontinuities were detected in the anisotropy measurements of the liposomes produced. Quantitative analyses revealed that the exogenously supplied sterol coordinately regulated specific phospholipid species, fatty acid composition, and sterol to phospholipid ratios in yeast auxotrophs.

    Topics: Cell Membrane; Cholesterol; Ergosterol; Fatty Acids; Fluorescence Polarization; Liposomes; Mathematics; Phospholipids; Saccharomyces cerevisiae; Sitosterols; Sterols; Stigmasterol

1985
Cholesterol absorption and turnover in hypercholesterolemic dogs.
    Journal of lipid research, 1985, Volume: 26, Issue:3

    Cholesterol absorption was measured in chronically hypercholesterolemic dogs by four methods: the fecal recovery method of Borgström (1969, J. Lipid Res. 10: 331-337), the dual isotope method of Zilversmit and Hughes (1974, J. Lipid Res. 15: 465-473), the recovery of cholesterol in thoracic duct lymph collected continuously for 16 hr after a meal, and the recovery of isotopic cholesterol from the liver and plasma 24 hr after the animals consumed an isotope-containing meal. The four methods showed excellent agreement and indicated that dogs fed a cholesterol-rich synthetic diet absorb 5.2 +/- 0.5 g (mean +/- SD) of cholesterol per day and that cholesterol absorption is reasonably constant from week to week in these animals. Separate estimates of cholesterol excretion indicated that these dogs excreted 4.7 +/- 0.5 g of cholesterol per day, and thus were at or near the steady-state with regard to cholesterol input-output. These data, taken together with a previous report (1981, J. Lipid Res. 22: 598-609), indicate that the canine liver can clear up to 300 mg of chylomicron cholesterol/hr, and support the concept that chylomicron remnants do not contribute significantly to the hypercholesterolemia in these animals.

    Topics: Animals; Bile; Cholesterol; Cholesterol, Dietary; Chylomicrons; Dogs; Feces; Female; Hypercholesterolemia; Intestinal Absorption; Liver; Lymph; Male; Micelles; Sitosterols; Solubility

1985
Evaluation of the contribution of dietary cholesterol to hypercholesterolemia in diabetic rats and of sitosterol as a recovery standard for cholesterol absorption.
    Journal of lipid research, 1985, Volume: 26, Issue:1

    The contribution of dietary cholesterol to hypercholesterolemia in diabetic rats fed chow ad libitum was evaluated. Diabetes was induced with streptozotocin, and the intake, absorption, and subsequent tissue distribution of dietary cholesterol were measured. Absorption was measured as the difference between [3H]cholesterol intake and fecal 3H-labeled neutral sterol excretion, using both [14C]sitosterol (added to diet) and [14C]cholesterol (added to feces) as recovery markers. [3H]Cholesterol absorption was underestimated by 1-3% using [14C]sitosterol as a recovery standard, due to the 7-8% absorption of sitosterol. After 3 weeks of diabetes, rats were hyperphagic, thereby increasing dietary cholesterol intake 2-fold. [3H]Cholesterol absorption was significantly increased from 69% in controls to 78% in diabetics, whereas [14C]sitosterol absorption was unaffected. With increased dietary cholesterol intake and decreased whole body cholesterol synthesis (Diabetes. 1983. 32: 811-819), influx from diet equaled for exceeded influx from synthesis. The amounts of 3H-labeled neutral sterol recovered from the small intestine, periphery, and plasma were increased 3- to 4-fold in the diabetic rats. Furthermore, the degree of hypercholesterolemia in diabetic rats was directly related to the fraction of plasma cholesterol derived from the diet. We conclude that the 2.3-fold increase in absorbed dietary cholesterol resulting from hyperphagia and, to a lesser extent, from increased fractional absorption, contributes to the hypercholesterolemia of diabetic rats fed chow ad libitum.

    Topics: Animals; Cholesterol; Cholesterol, Dietary; Circadian Rhythm; Diabetes Mellitus, Experimental; Eating; Feces; Hypercholesterolemia; Intestinal Absorption; Male; Rats; Rats, Inbred Strains; Reference Standards; Sitosterols; Tissue Distribution

1985
The degradation of beta-sitosterol by Pseudomonas sp. NCIB 10590 under aerobic conditions.
    Journal of steroid biochemistry, 1985, Volume: 23, Issue:3

    The bacterial degradation of beta-sitosterol by Pseudomonas sp NCIB 10590 has been studied. Major biotransformation products included 24-ethylcholest-4-en-3-one, androsta-1,4-diene-3,17-dione, 3-oxochol-4-en-3-one-24-oic acid and 3-oxopregn-4-en-3-one-20-carboxylic acid. Minor products identified were 26-hydroxy-24-ethylcholest-4-en-3-one, androst-4-ene-3,17-dione, 3-oxo-24-ethylcholest-4-en-26-oic acid, 3-oxochola-1,4-dien-3-one-24-oic acid, 3-oxopregna-1,4-dien-3-one-20 carboxylic acid and 9 alpha-hydroxyandrosta-1,4-diene-3,17-dione. Studies with selected inhibitors have enabled the elucidation of a comprehensive pathway of beta-sitosterol degradation by bacteria.

    Topics: 1-Propanol; Aerobiosis; Biotransformation; Chemical Phenomena; Chemistry; Fermentation; Pseudomonas; Sitosterols

1985
[Metabolites of Eupatorium cannabinum].
    Bollettino della Societa italiana di biologia sperimentale, 1985, Aug-30, Volume: 61, Issue:8

    Topics: Cholesterol; Chromatography, Gas; Phytosterols; Plants; Sitosterols; Stigmasterol

1985
Corn oil and its minor constituents as inhibitors of DMBA-induced chromosomal breaks in vivo.
    Mutation research, 1984, Volume: 136, Issue:3

    Inhibitory effects of corn oil and its constituents have been studied against 7,12-dimethylbenz[a]anthracene (DMBA)-induced chromosomal breaks in B6C3F1 female mice using the in vivo bone-marrow micronucleus assay. We tested propyl gallate, alpha-tocopherol and beta-sitosterol as constituents of corn oil. In addition, sunflower oil was tested also to check whether corn oil differs from any other vegetable oil. Corn oil, propyl gallate, beta-sitosterol or sunflower oil were injected i.p. to mice for 2 days at 24-h intervals, prior to injecting DMBA i.p. alpha-Tocopherol was mixed in powdered food and the mice were fed on it for 4 days before receiving DMBA. Bone-marrow samples were collected at various 24-h intervals. About 50-70% reduction in number of micronucleated polychromatic erythrocytes (MNPCE)/500 PCEs were observed in all the treatments wherever corn oil was used. Significant inhibitory effects were noted in treatments with alpha-tocopherol and beta-sitosterol. Sunflower oil also showed an inhibitory effect, similar to that with corn oil.

    Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Benz(a)Anthracenes; Bone Marrow; Cell Nucleus; Chromosome Aberrations; Corn Oil; Dietary Fats; Female; Mice; Mice, Inbred Strains; Mutagenicity Tests; Oils; Plant Oils; Propyl Gallate; Sitosterols; Sunflower Oil; Vitamin A

1984
Effects of azasteroids on growth and development of the free-living stages of Nippostrongylus brasiliensis and Nematospiroides dubius.
    Comparative biochemistry and physiology. B, Comparative biochemistry, 1984, Volume: 78, Issue:4

    25-Azasteroids were evaluated for their effects on the growth and development of the free-living stages of Nippostrongylus brasiliensis and Nematospiroides dubius. Increasing the concentration of 25-azasteroids in axenic cultures of either species resulted in a decrease in the percentage and mean length of larvae that developed to the third stage. Morphologic abnormalities of inhibited larvae were similar to those shown by larvae cultured in sterol-deficient medium. Addition of cholesterol to the culture medium reversed the inhibitive effects of azasteroid. Azasteroid completely inhibited growth and development of N. brasiliensis when the only sterol present in the culture medium was sitosterol. These results suggest similar pathways of sterol metabolism and similar mechanisms of action by azasteroids in the nematodes and insects that have been studied.

    Topics: Animals; Azasteroids; Cholesterol; Culture Media; Drug Synergism; Larva; Male; Nematoda; Nippostrongylus; Rats; Sitosterols; Steroids, Heterocyclic

1984
Diet, nutrition intake, and metabolism in populations at high and low risk for colon cancer. Dietary cholesterol, beta-sitosterol, and stigmasterol.
    The American journal of clinical nutrition, 1984, Volume: 40, Issue:4 Suppl

    Cholesterol and fat are implicated as dietary factors enhancing the risk for colon carcinogenesis. Plant sterols such as beta-sitosterol when added to diets of experimental animals treated with colon carcinogens reduce tumor yields and counteract the proliferative changes associated with carcinogenesis. The question of whether the diet of human populations at low risk for colon cancer is mirrored in their sterol composition is addressed in this study. Four study groups consisting of 18 Seventh-day Adventist (SDA) pure vegetarians, 50 SDA lacto-ovo vegetarians, 50 SDA nonvegetarians, and 50 general population nonvegetarians were selected from the greater Los Angeles basin, and 3-day composite diets were analyzed for their sterol composition. The most significant index of dietary sterol status is the ratio, beta-sitosterol + stigmasterol/cholesterol (plant sterol/cholesterol ratio). The values for the four groups ranged from 0.49 to 16.0 (general population nonvegetarians = 0.49; SDA-nonvegetarians = 0.98; SDA lacto-ovo vegetarians = 3.26; SDA pure vegetarians = 16.0). The data also show that the absolute amounts of cholesterol consumed as a factor by itself might not be as significant as its relationship to total plant sterols in the diet.

    Topics: Adult; Age Factors; Cholesterol, Dietary; Colonic Neoplasms; Diet; Diet, Vegetarian; Energy Intake; Female; Humans; Male; Middle Aged; Phytosterols; Sex Factors; Sitosterols; Stigmasterol

1984
[Effect of beta-sitosterol incorporated into liposomes on several indicators of lipid metabolism in experimental hypercholesteremia in rats].
    Voprosy meditsinskoi khimii, 1984, Volume: 30, Issue:6

    Alterations in lipid content of microvilli membranes, affecting their physical structure, as well as in lipoproteins of rat small intestinal mucosa and of blood plasma were studied in experimental hypercholesterolemia after treatment with crystalline and liposomal preparations of beta-sitosterol. The liposomal preparation of beta-sitosterol exhibited distinctly higher hypocholesterolemic activity as compared with the crystalline sterol. Possible role of structural and functional alterations in enterocyte membranes and in intestinal lipoproteins during absorption of cholesterol as well as inhibition of the processes by means of beta-sitosterol are discussed.

    Topics: Animals; Hypercholesterolemia; Intestinal Absorption; Intestinal Mucosa; Intestine, Small; Lipid Metabolism; Lipids; Liposomes; Membranes; Microvilli; Phospholipids; Rats; Sitosterols

1984
[Sterols in Stevia rebaudiana Bertoni].
    Bollettino della Societa italiana di biologia sperimentale, 1984, Dec-30, Volume: 60, Issue:12

    The sterol fraction of Stevia rebaudiana Bertoni contains, essentially, the following sterols: stigmasterol (45,8%), beta-sitosterol (39,4%) and campesterol (13,1%). The individual components were separated, after acetylation, by HPLC with absolute methanol as eluant. The identification of the compounds has been carried out through NMR and MS, while the corresponding percentages have been desumed from the GLC data.

    Topics: Cholesterol; Phytosterols; Plants, Medicinal; Sitosterols; Stigmasterol

1984
Sterols from Equisetum arvense.
    Bollettino della Societa italiana di biologia sperimentale, 1984, Dec-30, Volume: 60, Issue:12

    The sterol fraction of Equisetum arvense L. contains, essentially, the following sterols: beta-sitosterol (60.0%), campesterol (32.9%), isofucosterol (5.9%) and cholesterol (trace amounts). The identification of the compounds has been carried out through NMR and MS, while the corresponding percentage have been desumed from the GLC and HPLC data.

    Topics: Cholesterol; Chromatography, Gas; Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Phytosterols; Plants, Medicinal; Sitosterols; Stigmasterol

1984
Sitosterol-stimulative production of plasminogen activator in cultured endothelial cells from bovine carotid artery.
    Thrombosis research, 1984, Feb-15, Volume: 33, Issue:4

    The endothelial cell is a rich source of plasminogen activator that is associated with fibrinolytic activity in blood vessel. Addition of sitosterol to the culture medium of endothelial cells from bovine carotid artery gave rise to a marked increment in the activity of plasminogen activator. Removal of sitosterol from the culture medium resulted in a decrease of plasminogen activator activity back to normal levels. Enhancement of plasminogen activator activity in cultured endothelial cells was not observed by cholesterol, 5-androsten-3 beta-ol and others.

    Topics: Animals; Carotid Arteries; Cattle; Cells, Cultured; Endothelium; Fibrinolysis; Plasminogen Activators; Sitosterols; Steroids; Stimulation, Chemical

1984
Role of hydrophilic bile acids and of sterols on cholelithiasis in the hamster.
    Journal of lipid research, 1984, Volume: 25, Issue:6

    The effect of various dietary additions such as cholesterol, beta-sitosterol, bile acids, and bile acid analogs on gallstone formation was studied in the hamster. Gallstones were formed in 50% of the animals fed a high glucose, fat-free diet. Administration of 0.2% cholesterol or 1% beta-sitosterol had no effect on the incidence of gallstones. Ursodeoxycholic acid (0.5%) and its analog ursodeoxy-oxazoline [2-(3 alpha, 7 beta-dihydroxy-24-nor-5 beta-cholanyl)-4,4-dimethyl-2- oxazoline] were ineffective in preventing gallstones. Hyodeoxycholic acid and hyodeoxy-oxazoline [2-(3 alpha,6 alpha-dihydroxy-24-nor-5 beta-cholanyl)-4,4-dimethyl-2- oxazoline] at the same dosage effectively prevented gallstones, while the trihydroxy bile acid, hyocholic acid, was not effective. Of all the dietary regimens tested, only hyodeoxycholic acid significantly lowered serum cholesterol. The lithogenic diet produced a five-fold increase in hepatic HMG-CoA reductase activity; this activity was not affected by dietary cholesterol or beta-sitosterol. Hyodeoxycholic acid and hyocholic acid feeding increased the reductase activity by an additional 50% while the other bile acids had no effect. beta-Sitosterol doubled the cholesterol 7 alpha-hydroxylase activity whereas hyodeoxy-oxazoline lowered it. Hyodeoxycholic acid-fed animals had significantly lower cholesterol absorption than the animals on the lithogenic diet alone. Biliary cholesterol content increased dramatically in the animals fed the lithogenic diet and was increased still further by ursodeoxycholic acid, hyodeoxycholic acid, and hyodeoxy-oxazoline. These data show that hyodeoxycholic acid and hyodeoxy-oxazoline do not prevent gallstones by inhibiting hepatic cholesterol synthesis or biliary cholesterol secretion.

    Topics: Animals; Bile; Bile Acids and Salts; Cholanes; Cholelithiasis; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Cholic Acids; Cricetinae; Deoxycholic Acid; Diet; Hydroxymethylglutaryl CoA Reductases; Liver; Male; Mesocricetus; Phospholipids; Sitosterols; Sterols; Ursodeoxycholic Acid

1984
Synthesis of the putative metabolites of plant sterols: (24R)- and (24S)-24-methyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrols and 24-ethyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24 xi-tetrol.
    Journal of lipid research, 1984, Volume: 25, Issue:8

    This report describes the synthesis of (24R)- and (24S)-24-methyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrols and 24-ethyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24 xi-tetrol starting from cholic acid. The bile alcohols epimeric at C-24 were resolved by analytical and preparative thin-layer chromatography and characterized by gas-liquid chromatography and mass spectrometry. These epimeric bile alcohols may be useful for studying the transformation of beta-sitosterol to cholic acid.

    Topics: Animals; Cholestanols; Humans; Phytosterols; Sitosterols

1984
Serum lipoproteins and lecithin: cholesterol acyltransferase (LCAT) activity in hypercholesterolemic subjects given beta-sitosterol.
    International journal of clinical pharmacology, therapy, and toxicology, 1984, Volume: 22, Issue:4

    We studied the effect on the serum LCAT activity and apolipoproteins in ten subjects with primary hypercholesterolemia after treatment with beta-sitosterol. The 2-month administration of beta-sitosterol resulted in an increase of the fractional as well as of the molar esterification rate of the LCAT. These alterations were associated with a decrease of the levels of total, esterified, and unesterified cholesterol, whereas the levels of HDL-cholesterol and the apolipoproteins A-I and B were not affected. We conclude that beta-sitosterol primarily lowers cholesterol-rich lipoproteins with a lower density range than LDL via an accelerated esterification rate of the LCAT enzyme.

    Topics: Adult; Aged; Apolipoproteins; Cholesterol; Cholesterol, HDL; Esterification; Female; Humans; Hyperlipoproteinemia Type II; Lipoproteins; Lipoproteins, HDL; Male; Middle Aged; Phosphatidylcholine-Sterol O-Acyltransferase; Sitosterols; Triglycerides

1984
Changes in biliary and fecal bile acids in mice after treatments with diosgenin and beta-sitosterol.
    Journal of lipid research, 1984, Volume: 25, Issue:3

    Diosgenin and beta-sitosterol (1% in diet) were administered to CRJ:CD-1 male mice for 15 days, in order to examine the changes in bile acid metabolism. There were some differences between diosgenin and beta-sitosterol in their effects on diet intake, liver weight, and plasma cholesterol level. However, both phytosterols caused no statistically significant changes in body weight gain, decreased cholesterol absorption to about one-third that observed in control mice, decreased liver cholesterol level, increased fecal excretion of cholesterol, and decreased fecal excretion of bile acids. Most of the increase in fecal excretion of cholesterol occurred 2 days after the start of feeding of phytosterols and gradually declined thereafter, but the levels on day 15 were nevertheless higher than those in the control mice. The fecal excretion of bile acids decreased progressively after the treatment with phytosterols. The decrease of bile acid derived from chenodeoxycholic acid was more predominant than the decrease of those derived from cholic acid, resulting in an increase of the cholic acid/chenodeoxycholic acid ratio. The biliary cholesterol, phospholipid, and bile acid mole % ratios and the lithogenic index were not changed, but the percentages of cholic acid and its related bile acids (the cholic acid group) to the total bile acids increased and those of the chenodeoxycholic acid group decreased after the treatments. The pool size of bile acids decreased in the mice given diosgenin but not in those given beta-sitosterol. Distribution of bile acids between the gallbladder and intestine was not altered by either phytosterol.(ABSTRACT TRUNCATED AT 250 WORDS)

    Topics: Animals; Bile; Bile Acids and Salts; Body Weight; Cholesterol; Diet; Diosgenin; Feces; Kinetics; Liver; Male; Mice; Mice, Inbred Strains; Sapogenins; Sitosterols

1984
[Prostatic adenoma. Indication for therapy using sitosterine-containing phytopharmacologic agents].
    Die Medizinische Welt, 1983, May-27, Volume: 34, Issue:21

    Topics: Adult; Child; Costs and Cost Analysis; Diet; Food Analysis; Humans; Hypercholesterolemia; Infant; Male; Prostatic Hyperplasia; Sitosterols

1983
Interrelationship between serum and fecal sterols.
    Japanese journal of medicine, 1983, Volume: 22, Issue:1

    Seven healthy volunteers and 3 hospitalized patients were given the same diet for 6 days. The mean intake of cholesterol was 359 mg/day. There was a large difference in the fecal amount of cholesterol and coprostanol among the subjects. The ratio of coprostanol/cholesterol ranged from 0.01 to 4.27. The subjects whose feces contained smaller amount of coprostanol excreted larger amounts of beta-sitosterol and crude fiber, suggesting that the various activities of intestinal flora were lower than the other subjects. The difference in the activity of intestinal flora to convert cholesterol into coprostanol was ascertained by incubating the feces anaerobically with egg yolk in vitro. It was also demonstrated that cholesterol was synthesized de novo and the amount corresponded to 0.1-0.6 g/day. The amounts of sterols in the feces of the other 17 hospitalized patients were also determined and there was an inverse relationship between the serum cholesterol and coprostanol/cholesterol ratio in the feces. These results suggested that the conversion of cholesterol into coprostanol by the intestinal flora might have an important role in the regulation of serum cholesterol level.

    Topics: Adult; Aged; Cholestanol; Cholesterol; Cholesterol, Dietary; Dietary Fiber; Feces; Humans; Intestines; Middle Aged; Sitosterols

1983
In vitro evaluation of Saudi Arabian toothbrush tree (Salvadora persica).
    Odonto-stomatologie tropicale = Tropical dental journal, 1983, Volume: 6, Issue:3

    Topics: Cells, Cultured; Humans; Medicine, Traditional; Oral Hygiene; Periodontium; Plants, Medicinal; Sitosterols

1983
Some aspects of mechanism of inhibition of cholesterol absorption by beta-sitosterol.
    Biochimica et biophysica acta, 1983, Aug-10, Volume: 732, Issue:3

    Mixed bile salt micelle solubilized either cholesterol or beta-sitosterol to a comparable extent. When added simultaneously, beta-sitosterol restricted the micellar solubility of cholesterol. beta-Sitosterol also reduced the cholesterol content in the aqueous (micellar) phase of the intestinal contents of rats, the extent of reduction being comparable with that observed in vitro. The intestinal uptake of cholesterol in vivo was equivalent to the micellar incorporation of cholesterol both in vitro and in vivo. beta-Sitosterol had no inhibitory effect on cholesterol absorption from the micellar solution in jejunal loops in situ, whereas the rate of beta-sitosterol uptake was only about one-fifth that of cholesterol. The intestinal uptake of beta-sitosterol intubated into the stomach of rats was about one-fifth that of cholesterol. The intestinal brush-border membrane discriminated these sterols. These results suggest that the restriction of the micellar solubility of cholesterol, rather than the inhibition of uptake from brush-border membrane, is the major determinant for the interference of beta-sitosterol with cholesterol absorption.

    Topics: Animals; Carbon Radioisotopes; Cholesterol; Intestinal Absorption; Intestinal Mucosa; Jejunum; Kinetics; Male; Micelles; Rats; Rats, Inbred Strains; Sitosterols

1983
Evaluation of an isotope ratio method for measuring biliary cholesterol secretion.
    Journal of lipid research, 1983, Volume: 24, Issue:7

    We have evaluated an isotope ratio method for measuring biliary cholesterol secretion. Secretion was measured in eight nonhuman primates by analysis of radioactivity of feces and plasma 4 weeks after intravenous administration of a single dose of [3H]cholesterol. For the test, [14C]cholesterol was fed in known amounts daily for 10 days. The ratio of isotopes in feces (14C/3H) was equivalent to the ratio of total radioactivity that entered the intestine from diet and bile. Assuming biliary cholesterol specific activity equals plasma cholesterol specific activity, the mass of cholesterol secreted daily in the bile could be calculated. In paired experiments in four animals we were able to directly compare biliary secretion by the new method with mass measurement by intraduodenal intubation (Grundy, S. M., and A. L. Metzger. 1972. Gastroenterology. 52: 2100-1216). The two methods correlated well in these four animals (r = 0.97). We further noted that bile secretion by the new method (eight animals) and by the mass method (four animals) correlated well with body weight (r = 0.94 for weight vs secretion by the isotope ratio method; r = 0.97 for weight vs secretion by the mass ratio method). Ranges of body weight and secretion for the eight animals were 4.2-13.1 kg and 3.6-11.4 mg/hr, respectively. The slopes of the two regression lines for body weight vs. secretion measured by the two methods did not differ significantly from one another (F(1.8) = 1.42; 0.25 less than P less than 0.50).(ABSTRACT TRUNCATED AT 250 WORDS)

    Topics: Animals; Biliary Tract; Carbon Radioisotopes; Chlorocebus aethiops; Cholesterol; Macaca; Macaca mulatta; Sitosterols; Tritium

1983
Sterol constituents of Tamus communis L.
    Journal of ethnopharmacology, 1983, Volume: 8, Issue:3

    Topics: Cholesterol; Phytosterols; Plants, Medicinal; Sitosterols; Stigmasterol

1983
[Significance of nonsaponifiable constituents of dietary fats on the bioactivity of vitamin E].
    Zeitschrift fur Ernahrungswissenschaft, 1983, Volume: 22, Issue:4

    In experiments with male Wistar rats the influence of the non-saponifiable constituents of dietary fats: dl-alpha-tocopherol (60 ppm), dl-gamma-tocopherol (480 ppm), ubiquinone (96 ppm) and beta-sitosterol (3035 ppm) on the tocopherol status was investigated, considering the fatty acid composition of the tested fats. For a test period of eight weeks the animals were fed isoenergetic diets containing three types of dietary fats: corn oil (60% PUFA), a kind of "stripped corn oil" (60% PUFA) and butter (nearly 5% PUFA). Independent of the PUFA-content of the diet, the tocopherol supplementations were able to stabilize the erythrocyte membrane; the calculated hemolysis rates were about 2%. The absence of tocopherols in the diets ("stripped corn oil", butter) caused an increase of the hemolysis rate up to 70% after two weeks. The original amounts of tocopherols in corn oil tended to minimize the hemolysis. Ubiquinone and beta-sitosterol did not reduce the hemolysis rates when they were applied without tocopherols. With respect to creatine-phosphokinase activity, creatine and creatinine excretion the results were similar. Plasma and erythrocyte levels of alpha- and gamma-tocopherol were determined in all groups and discussed in connection with the other examined parameters of tocopherol status. The ultimate result of this experiment is that the content of tocopherols in dietary fats is not always adequate to keep vitamin E status normal, especially if polyunsaturated fatty acid content is high in the diet. Reflecting the vitamin E adequacy of dietary fats, not only alpha-tocopherol but also gamma-tocopherol should be much more considered than previously.

    Topics: Animals; Butter; Dietary Fats; Dose-Response Relationship, Drug; Fatty Acids, Unsaturated; Hemolysis; Male; Rats; Rats, Inbred Strains; Sitosterols; Structure-Activity Relationship; Triglycerides; Ubiquinone; Vitamin E; Zea mays

1983
A facile synthesis of [3 alpha-3 H]beta -sitosterol.
    Steroids, 1983, Volume: 42, Issue:6

    Direct oxidation of the parent sterol using CrO3 provided (24R)-24-ethyl-5-cholesten-3-one which on treatment with NaBT4 gave [3 alpha-3 H] (24R)-24-ethyl-5-cholesten-3 beta-ol. Purification at each stage afforded samples which were compared spectrally with the corresponding cholesterol series compounds.

    Topics: Chromatography, Gas; Chromatography, Thin Layer; Isotope Labeling; Oxidation-Reduction; Sitosterols; Tritium

1983
beta-sitosterol: esterification by intestinal acylcoenzyme A: cholesterol acyltransferase (ACAT) and its effect on cholesterol esterification.
    Journal of lipid research, 1983, Volume: 24, Issue:4

    Rabbits were fed either 10% coconut oil, 10% coconut oil and 1% beta-sitosterol, 10% coconut oil and 1% cholesterol, or 10% coconut oil and 1% beta-sitosterol plus 1% cholesterol for 4 weeks. Microsomal membranes from intestines of animals fed the 1% beta-sitosterol diet had 48% less cholesterol and were enriched twofold in beta-sitosterol compared to membranes from animals fed the coconut oil diet alone. Acylcoenzyme A:cholesterol acyltransferase (ACAT) activity in jejunum and ileum was decreased significantly in animals fed the plant sterol alone. In membranes from animals fed 1% beta-sitosterol and 1% cholesterol, beta-sitosterol content increased 50% whereas cholesterol was modestly decreased compared to their controls fed only cholesterol. Intestinal ACAT was unchanged in the animals fed both sterols when compared to their controls. beta-Sitosterol esterification was determined by incubating intestinal microsomal membranes with either [(14)C]beta-sitosterol-albumin emulsion or [(14)C]beta-sitosterol:dipalmitoyl phosphatidylcholine (DPPC) liposomes to radiolabel the endogenous sterol pool. Oleoyl-CoA was then added. The CoA-dependent esterification rate of beta-sitosterol was very slow compared to that of cholesterol using both techniques. An increased amount of endogenous microsomal beta-sitosterol, which occurs in animals fed 1% beta-sitosterol, did not interfere with the stimulation of ACAT activity secondary to cholesterol enrichment of the membranes. Enriching microsomal membranes three- to five-fold with beta-sitosterol did not affect ACAT activity. Freshly isolated intestinal cells were incubated for 1 hour with [(3)H]oleic acid and beta-sitosterol:DPPC or 25-hydroxycholesterol:DPPC. Incorporation of oleic acid into cholesteryl esters did not change in the presence of beta-sitosterol but increased fourfold after the addition of 25-hydroxycholesterol. We conclude that the CoA-dependent esterification rate of cholesterol is at least 60 times greater than that of beta-sitosterol. Membrane beta-sitosterol does not interfere with nor compete with cholesterol esterification. Inadequate esterification of this plant sterol may play a role in the poor absorption of beta-sitosterol by the gut.-Field, F. J., and S. N. Mathur. beta-Sitosterol: esterification by intestinal acylcoenzyme A:cholesterol acyltransferase (ACAT) and its effect on cholesterol esterification.

    Topics: Acyl Coenzyme A; Acyltransferases; Animals; Catalysis; Cholesterol Esters; Dietary Fats; In Vitro Techniques; Intestine, Small; Male; Microsomes; Rabbits; Sitosterols; Sterol O-Acyltransferase

1983
Comparison of cholesterol and beta-sitosterol: effects on jejunal fluid secretion induced by oleate, and absorption from mixed micellar solutions.
    Gut, 1983, Volume: 24, Issue:7

    Jejunal fluid secretion induced by perfusion with oleic acid can be reduced by the addition of cholesterol. The present study was performed to test the specificity of this effect by comparing the effects of cholesterol with that of a plant sterol, beta-sitosterol during perfusion of the jejunum in healthy volunteers. In addition, we compared the solubilities of cholesterol and beta-sitosterol in micellar solutions and their jejunal absorption rates. One millimolar beta-sitosterol was as effective as 1 mM cholesterol in reducing jejunal fluid secretion induced by 6 mM oleate (n = 7). In mixed micellar solutions consisting of 10 mM taurocholate and 6 mM oleate, solubility of beta-sitosterol is about one third of cholesterol solubility. When cholesterol was gradually replaced by beta-sitosterol in the incubation mixture, beta-sitosterol reduced cholesterol solubility to a greater extent than would be expected from an equimolar replacement of cholesterol by beta-sitosterol. Absorption of beta-sitosterol was limited by its solubility in mixed micellar solutions and both sterols were absorbed at equal rates as long as their solubility limits were not exceeded (n = 5).

    Topics: Cholesterol; Humans; Intestinal Absorption; Intestinal Secretions; Jejunum; Male; Micelles; Oleic Acid; Oleic Acids; Perfusion; Sitosterols; Solubility

1983
Precursor of 27-nor-5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 24,25-pentol in man.
    Journal of steroid biochemistry, 1983, Volume: 18, Issue:6

    Cholesterol was shown to be the precursor of 27-nor-5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 24,25-pentol which is the major bile alcohol in human urine. 4-[14C]-Labelled cholesterol and beta-sitosterol were administered to patients with primary biliary cirrhosis. Urine was extracted with Amberlite XAD-2 and sterol glucuronides and bile acid conjugates were isolated by ion exchange chromatography on Lipidex-DEAP. Following hydrolysis and further purification on Lipidex-DEAP, the C26 bile alcohol and methyl esters of cholic and chenodeoxycholic acids were isolated by HPLC. The specific radioactivity of the C26-pentol was the same as that of cholic acid after administration of [14C]-cholesterol. In contrast, little if any radioactivity could be detected in the C26-pentol after administration of labelled beta-sitosterol.

    Topics: Bile Acids and Salts; Carbon Radioisotopes; Cholestanols; Cholesterol; Chromatography, High Pressure Liquid; Female; Humans; Liver Cirrhosis, Biliary; Methylation; Middle Aged; Sitosterols

1983
Effects of spinasterol and sitosterol on plasma and liver cholesterol levels and biliary and fecal sterol and bile acid excretions in mice.
    Japanese journal of pharmacology, 1983, Volume: 33, Issue:1

    Effects of spinasterol and sitosterol on plasma and liver cholesterol levels and biliary and fecal sterol and bile acid excretions were examined with male mice. Both phytosterols were added to the diet at a 1% concentration and fed to mice for 15 days. Spinasterol increased the fecal cholesterol excretion and decreased the plasma and liver cholesterol levels, the bile acid pool size and the fecal bile acid excretion, especially those derived from chenodeoxycholic acid. Fecal coprostanol excretion remained unchanged. These changes were similar to those produced by sitosterol. These data led to the conclusions 1) that spinasterol, as well as sitosterol, inhibits cholesterol absorption, resulting in decreases of the plasma and liver cholesterol levels and 2) that when cholesterol absorption is inhibited, the synthesis of bile acids, especially that of chenodeoxycholic acid, decreases, suggesting that the dietary cholesterol is preferentially metabolized to chenodeoxycholic acid in mice.

    Topics: Animals; Bile; Bile Acids and Salts; Body Weight; Cholesterol; Feces; Liver; Male; Mice; Phospholipids; Phytosterols; Sitosterols; Sterols; Stigmasterol

1983
[Conservative therapy of prostatic adenoma as well as prostatitis with beta-sitosterol prostate capsules].
    Die Medizinische Welt, 1982, Dec-03, Volume: 33, Issue:48

    Topics: Adult; Aged; Capsules; Double-Blind Method; Humans; Male; Middle Aged; Prostatic Hyperplasia; Prostatitis; Sitosterols

1982
Fecal cholesterol excretion studies in type II hypercholesterolemic patients treated with the soybean protein diet.
    Atherosclerosis, 1982, Volume: 43, Issue:2-3

    The fecal steroid elimination profile was studied in 7 type II hyperlipoproteinemic patients given a low-lipid diet with textured soybean proteins, in order to define the mechanism of the hypocholesterolemic activity of this new dietary regimen. Four of the patients followed a 3- + 3-week cross-over protocol, comparing the soybean diet with a reference low-lipid diet with animal proteins. In these, fecal neutral steroids and bile acids were analyzed by chromatography during the two dietary periods. In spite of the clear hypocholesterolemic effect, no significant differences in steroid output were noted between the two dietary periods. In the 3 remaining patients, a chromatographic + isotopic method (by injecting 14C-labelled cholesterol i.v. 4-6 weeks prior to the dietary study) was employed. Again, no marked changes were noted in the fecal neutral steroid and bile acid outputs and the slope of the decay curve of the plasma cholesterol-specific activity was not changed by the experimental diet, in spite of the remarkable decrease in plasma cholesterol. The reported results do not provide a definitive contribution to the mode of action of the soybean protein diet. They suggest, however, that it is not an effect mediated by undigestible dietary components. The possibility of a cholesterol redistribution from plasma to tissue pools should be considered.

    Topics: Bile Acids and Salts; Cholesterol; Cholesterol, Dietary; Dietary Fats; Feces; Female; Glycine max; Humans; Hyperlipoproteinemia Type II; Male; Plant Proteins, Dietary; Sitosterols

1982
Combined inhibitors of carcinogenesis: effect on azoxymethane-induced intestinal cancer in rats.
    Journal of the National Cancer Institute, 1982, Volume: 69, Issue:1

    Outbred male Sprague-Dawley CD rats were fed a complete semisynthetic diet and were given supplemental low doses (2 ppm) of selenium as H2SeO3 in their drinking water or 50 mg 13-cis-retinoic acid (13-cis-RA) and 2 g beta-sitosterol/kg diet either singly, in combinations of two, or in combinations of all three. Intestinal tumors were induced with eight weekly sc injections of 8 mg azoxymethane (AOM)/kg body weight, and inhibition of tumor formation was determined by tumor counts after 26 weeks. Noncarcinogen controls for each dietary group received eight injections of sterile water. Tumor inhibition was statistically significant in 2 groups of animals: Dietary control animals had a tumor frequency of 5.07 tumors/rat, rats receiving selenium- plus 13-cis-RA supplementation had a tumor frequency of 3.77, and those being given the combination of all three inhibitors had 2.75 tumors/rat. Analysis of fecal steroids from 3 AOM groups (dietary controls, the beta-sitosterol plus 13-cis-RA-supplemented group, and the group receiving all three additives) after 4 months of supplementation showed that the addition of beta-sitosterol to the diet had no effect on acidic or neutral steroids, regardless of the observed difference in tumor frequency. These results suggest that subpharmacologic doses of inhibitors, particularly those that inhibit the process by different mechanisms, while ineffective alone, may provide significant inhibition of tumorigenesis when used in combination.

    Topics: Animals; Azo Compounds; Azoxymethane; Body Weight; Drinking; Eating; Intestinal Neoplasms; Male; Rats; Rats, Inbred Strains; Selenium; Sitosterols; Tretinoin

1982
[Lowering lipids rapidly and permanently with etofibrate].
    Medizinische Klinik, 1982, Jan-29, Volume: 77, Issue:3

    Topics: Cholestyramine Resin; Clofibrate; Clofibric Acid; Dextrothyroxine; Humans; Hyperlipoproteinemias; Lipoproteins, HDL; Liver; Nicotinic Acids; Sitosterols

1982
Effects of beta-sitosterol on the concentrations of serum and liver cholesterol and serum apolipoproteins in rats fed butter fat.
    Journal of nutritional science and vitaminology, 1982, Volume: 28, Issue:2

    Male rats were fed on semipurified cholesterol-free diets containing butter fat with or without supplementary beta-sitosterol. The expected rise of serum cholesterol caused by butter fat, as compared with safflower oil, was not able to be demonstrated, and hence the hypocholesterolemic effect of beta-sitosterol as well. However, the plant sterol effectively lowered the liver cholesterol level. Similar responses were also observed in mice. The distribution of cholesterol in serum lipoproteins remained unchanged among different dietary regimens. Butter fat increased the concentration of serum apoA-I in relation to safflower oil. There was possibly a trend toward higher serum apoA-I with supplementation of beta-sitosterol in a butter-fat diet. The effect of the plant sterol on serum apoB was rather variable. The observation strongly suggests that alteration in cholesterol metabolism in these rodents may not satisfactorily be estimated by the serum cholesterol parameter alone when diets free of cholesterol are fed. The concentration of hepatic cholesterol and serum apolipoproteins seems a more apposite measure for this purpose.

    Topics: Animals; Apolipoproteins; Cholesterol; Cholesterol, HDL; Dietary Fats; Lipoproteins, HDL; Liver; Male; Mice; Phospholipids; Rats; Rats, Inbred Strains; Sitosterols; Triglycerides

1982
Effects of plant sterols on cholesterol concentration in the rat small intestine.
    Experientia, 1982, Sep-15, Volume: 38, Issue:9

    Topics: Animals; Cholesterol; Cholesterol Esters; Female; Intestinal Absorption; Intestine, Small; Male; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Stigmasterol

1982
Effect of feeding beta-sitosterol alone or in combination with cholestyramine during early life on subsequent response to cholesterol challenge in adult life in guinea-pigs.
    The British journal of nutrition, 1982, Volume: 48, Issue:3

    The effect of feeding 20 g beta-sitosterol/kg alone or in combination with cholestyramine (20 g/kg) during neonatal life of guinea-pigs on their subsequent response to a dietary cholesterol challenge in adult life was examined. 2. beta-Sitosterol pretreated animals showed higher plasma cholesterol values following 2 weeks on a cholesterol challenge (2-5 g/kg) diet, but did not differ significantly from control values for the remainder of the cholesterol challenge period. 3. Guinea-pigs pretreated with beta-sitosterol plus cholestyramine, on the other hand, showed a marked increase in plasma cholesterol levels over those of controls during the cholesterol challenge period, and this "hyper-responder" behaviour was maintained throughout the study period. 4. Despite the increase in plasma cholesterol, beta-sitosterol plus cholestyramine pretreated animals excreted significantly (P less than 0.05) greater amounts of bile acids and total sterols. 5. These findings demonstrate that neonatal pretreatment with beta-sitosterol plus cholestyramine has detrimental effects on the handling of a cholesterol challenge in adult life, and does not achieve the beneficial effect previously noted with pretreatment with cholestyramine alone.

    Topics: Animals; Animals, Newborn; Bile Acids and Salts; Body Weight; Cholesterol; Cholesterol, Dietary; Cholestyramine Resin; Diet; Feces; Guinea Pigs; Male; Sitosterols; Sterols

1982
Differential uptake of cholesterol and plant sterols by rat erythrocytes in vitro.
    Lipids, 1982, Volume: 17, Issue:10

    The in vitro uptake of radioactively labeled cholesterol and the plant sterol beta-sitosterol has been examined in rat erythrocytes. From mixed micellar solutions containing egg yolk phospholipid and sodium taurocholate, the erythrocytes showed a nonlinear uptake of the two sterols. The uptake leveled off after about 45 min with the attainment of a 1:1 total sterol-to-phospholipid ratio within the cell membrane, as determined on a mass basis. From solutions containing egg yolk phospholipid, or purified egg yolk phosphatidylcholine, a preference for cholesterol over the plant sterol was observed, increasing with time from a cholesterol/beta-sitosterol uptake ratio of unity (the media ratio) to a maximum of 2 after a 60-min incubation. Correction of the data for nonspecifically bound sterol increased the ratio to a maximum of 5 at the 30-min time point. The increase in the cholesterol/beta-sitosterol uptake ratio with time, following an initial nonspecific association, showed that penetration of the plasma membrane by the sterol was required for the selectivity to be expressed. The presence of lysophosphatidylcholine or bovine serum albumin did not exert any noticeable influence over the extent or selectivity of absorption. Replacement of the egg yolk phospholipid with synthetic dipalmitoyl-phosphatidylcholine led to a loss of the sterol selectivity. No evidence was found to support a selective extraction of sterol from the erythrocyte membrane to account for the observed effects, nor was there any sign of a mass accumulation of phospholipid during the incubation. It is suggested that the media phospholipid influences the membrane permeability toward cholesterol and beta-sitosterol.

    Topics: Animals; Biological Transport; Cholesterol; Erythrocytes; Hemolysis; Kinetics; Male; Micelles; Plants; Rats; Rats, Inbred Strains; Sitosterols

1982
Lowering plasma cholesterol with beta-sitosterol and diet.
    Lancet (London, England), 1981, May-23, Volume: 1, Issue:8230

    Topics: Adolescent; Adult; Cholesterol; Female; Humans; Hyperlipoproteinemia Type II; Sitosterols

1981
[Measurement of urinary flow in general practice. Efficacy of beta-sitosterine].
    ZFA. Zeitschrift fur Allgemeinmedizin, 1981, Oct-10, Volume: 57, Issue:28

    Topics: Humans; Male; Plant Extracts; Prostatic Hyperplasia; Rheology; Sitosterols; Urination Disorders; Urodynamics

1981
[Urination disorders caused by prostatic hyperplasia. Effect of Bazoton, Harzol and Prosta-capsules].
    MMW, Munchener medizinische Wochenschrift, 1981, Oct-30, Volume: 123, Issue:44

    Topics: Adenoma; Humans; Male; Plant Extracts; Prostatic Hyperplasia; Sitosterols; Urination Disorders; Urodynamics

1981
A unique patient with coexisting cerebrotendinous xanthomatosis and beta-sitosterolemia.
    The American journal of medicine, 1981, Volume: 71, Issue:2

    An adult Chinese man presented with tendinous and tuberous xanthomatosis and severe atheromatous changes in the coronary arteries. In addition, he had chronic hemolytic anemia, with spherostomatocytic erythrocytes. Cerebrotendinous xanthomatosis was diagnosed on the basis of increased cholestanol levels in his plasma, red cells and xanthoma, changes in bile acid composition due to the defective synthesis of chenodeoxycholic acid. Coexisting beta-sitosterolemia was confirmed by the finding of large amounts of the plant sterols such as beta-sitosterol and campesterol. This is the first report of these two rare lipid storage disorders in the same patient.

    Topics: Adult; Anemia, Hemolytic; Chenodeoxycholic Acid; Cholestanols; Cholesterol; Coronary Disease; Humans; Lipidoses; Phytosterols; Sitosterols; Spherocytes; Xanthomatosis

1981
Unsaponifiable matter and fatty acid composition of pea oil.
    Zeitschrift fur Ernahrungswissenschaft, 1981, Volume: 20, Issue:2

    14 compounds were detected in the unsaponifiable matter of pea oil by gas liquid chromatography (GLC) and 8 of them were identified as hydrocarbons C30, C32, squalene, alpha-tocopherol, cholesterol, campesterol, stigmasterol and beta-sitosterol. The predominant unsaponifiable fraction was beta-sitosterol whereas the others were found in variable amounts. Two sterols were isolated by column chromatography. One of them was characterised as beta-sitosterol by measuring the melting point, [a]D, and infrared spectra and those of its acetate. However, the other sterol was unidentified. The fatty acid contents in pea oil were determined quantitatively by GLC. They were present in variable amounts, whereas linoleic acid was the major one.

    Topics: Chromatography, Gas; Egypt; Fabaceae; Fatty Acids; Linoleic Acids; Oils; Phytosterols; Plants, Medicinal; Sitosterols

1981
A new aspect on the mechanism of intestinal cholesterol absorption in rat.
    Journal of nutritional science and vitaminology, 1981, Volume: 27, Issue:3

    In order to study the mechanism of intestinal cholesterol absorption, the relationship between the amount of cholesterol administered and the rate of absorption was investigated by the dual isotope plasma ratio method in vivo and the ligated-loop method in situ. The energy requirement of cholesterol absorption was also observed by means of the ligated-loop method. The results obtained are summarized below. 1) Tri-phase absorption was observed by the dual isotope plasma ratio method. When less than 300 microgram of cholesterol was administered, absorption increased linearly, with the coefficient of absorption being more than 80%. When the amount administered was between 300 and 500 microgram, the absorption was constant. With the administration of more than 500 microgram, absorption increased linearly, but the coefficient of absorption decreased to approximately 55%. 2) With the ligated-loop method, a second saturation profile was obtained when between 250 and 400 microgram of cholesterol was administered to a segment. When 50 to 250 microgram of cholesterol were administered, absorption increased in proportion to the increase in cholesterol dosage. 3) The mucosal uptake of cholesterol decreased to 40-60% of the control with the addition of metabolic inhibitors such as NaN3, KCN, 2,4-DNP and ouabain, whereas the uptake of palmitate showed no significant decrease. In addition, the uptake of cholesterol decreased remarkably to 25% of the control with the lowering of body temperature from 37 degrees C to 27 C. These results suggest the existence of an active transport system which has a limited capacity for cholesterol absorption and which requires energy for its operation in the physiological state.

    Topics: Animals; Biological Transport, Active; Body Temperature; Cholesterol; Dose-Response Relationship, Drug; Intestinal Absorption; Intestinal Mucosa; Jejunum; Palmitic Acid; Palmitic Acids; Rats; Sitosterols

1981
Antihypercholesterolemic activity of beta-sitostanol in rabbits.
    Journal of nutritional science and vitaminology, 1981, Volume: 27, Issue:3

    The antihypercholesterolemic activity of beta-sitosterol and beta-sitostanol was compared in male rabbits given a cholesterol-supplemented diet. beta-Sitosterol and beta-sitostanol were fed to these rabbits at the 0.5% level with cholesterol (0.5% and 0.2% in experiments I and II, respectively). The serum cholesterol level tended to be lower in rabbits fed beta-sitostanol than in the animals fed beta-sitosterol even in experiment I. The beta-sitostanol exhibited a significantly greater hypocholesterolemic activity in experiment II, LDL-cholesterol being decreased markedly. The liver cholesterol decreased in both groups of rabbits to a similar extent. beta-Sitostanol prevented more effectively the formation of dietary cholesterol-induced atheroma in the abdominal aorta than beta-sitosterol. It is most likely, together with the data reported previously on rats, that the hypocholesterolemic activity of beta-sitostanol results from the significantly greater inhibitory effect on the intestinal absorption of cholesterol than that of beta-sitosterol.

    Topics: Animals; Anticholesteremic Agents; Arteriosclerosis; Cholesterol; Cholesterol, Dietary; Lipids; Lipoproteins; Liver; Male; Rabbits; Sitosterols; Sterols

1981
Microbiological transformations of beta-sitosterol and stigmasterol by a soil pseudomonad.
    Experientia, 1980, May-15, Volume: 36, Issue:5

    Fermentation of beta-sitosterol by a soil pseudomonad resulted in the formation of 4-stigmasten-3-one, 4-stigmasten-3-one-6 beta-ol and 5-stigmasten-3 beta, 7 alpha-diol. In case of stigmasterol the metabolites isolated and characterized were 4,22-stigmastadien-3-one, 4,22-stigmastadien-3-one-6 beta-ol and 5,22-stigmastadien-3 beta, 7 alpha-diol.

    Topics: Isomerism; Optical Rotation; Phytosterols; Pseudomonas; Sitosterols; Stigmasterol

1980
[Effect of cholic acid and chenodesoxycholic acid on biliary secretion in mice. Effect of the addition of beta-sitosterol].
    Canadian journal of physiology and pharmacology, 1980, Volume: 58, Issue:9

    Five groups of 20 mice received for 4 months one of the following diets: T, standard diet (T); a, T + cholic acid (0.2%); b, T + cholic acid (0.2%) + beta-sitosterol (2%); c, T + chenodeoxycholic acid (0.2%); d, T + chenodeoxycholic acid (0.2%) + beta-sitosterol (2%). After this time, the cholesterol intestinal absorption and the biliary secretion of lipids were measured. The biliary secretion of cholesterol, the total hepatic cholesterol (23 mg/g liver dry weight), and the intestinal absorption of cholesterol (90% administered dose) were higher in mice fed with cholic acid than in mice fed with chenodeoxycholic acid (hepatic cholesterol, 9.6 mg/g liver dry weight; absorption, 65% administered dose). The addition of beta-sitosterol to the diet supplemented with cholic acid decreased the cholesterol intestinal absorption and the biliary secretion of cholesterol so that both became similar to that obtained with chenodeoxycholic acid. These results indicate that in mice, as in man, cholic acid elicits a higher cholesterol biliary secretion than chenodeoxycholic acid. In this experimental model, the distinct effect on the biliary cholesterol of these two bile salts is due to their specific effects on the intestinal absorption of cholesterol.

    Topics: Animals; Bile; Chenodeoxycholic Acid; Cholesterol; Cholic Acids; Diet; Female; Intestinal Absorption; Liver; Mice; Sitosterols

1980
Adverse effects of phytoestrogens-7. Effect of beta-sitosterol treatment on follicular development, ovarian structure and uterus in the immature female sheep.
    Cellular and molecular biology, including cyto-enzymology, 1980, Volume: 26, Issue:3

    Topics: Animals; Female; Ovarian Follicle; Ovary; Sheep; Sitosterols; Uterus

1980
Mechanism of dealkylation of clionasterol in the insect Tenebrio molitor.
    The Biochemical journal, 1978, Aug-15, Volume: 174, Issue:2

    1. 25-3H- and 26-14C-labelled (24S)-24-ethylcholest-5-en-3beta-ol (clionasterol) were synthesized from (24S)-24-ethylcholesta-5,25-dien-3beta-ol. 2. These labelled substrates were mixed and administered, together with the hypocholesterolemic agent, triparanol citrate, to Tenebrio molitor larvae. 3. The 3H label from the clionasterol substrate was retained in both the desmosterol and the cholesterol isolated from the larvae. 4. Location of this 3H label in the desmosterol showed that dealkylation of the clionasterol involved 3H migration from C-25 to C-24. A possible mechanism for dealkylation is presented.

    Topics: Animals; Cholesterol; Dealkylation; Desmosterol; Larva; Sitosterols; Tenebrio

1978
UNIQUE STEROL IN THE ECOLOGY AND NUTRITION OF DROSOPHILA PACHEA.
    Science (New York, N.Y.), 1965, Aug-13, Volume: 149, Issue:3685

    Drosophila pachea, which breeds only in the stems of senita cactus (Lophocereus schottii) throughout the Sonoran Desert, requires the cactus as a dietary supplement when reared on laboratory media. Delta(7)-Stigmasten-3beta-ol, isolated from the cactus or synthesized, can replace the cactus in the diet of flies reared nonaseptically or axenically. Delta(7)-Cholesten-3beta-ol and Delta(5, 7)-cholestadien-3beta-ol could be substituted for the cactus sterol; Delta(5, 7)-stigmastadien-3beta-ol produced infertile females. Cholesterol, 4alpha-methyl-Delta(7)-cholesten-3beta3-ol, beta-sitosterol, stigmasterol, ergosterol, and Delta(7)-ergosten- 3beta-ol did not support larval growth.

    Topics: Animals; Biochemical Phenomena; Biochemistry; Cholesterol; Diet; Diptera; Drosophila; Ecology; Ergosterol; Female; Larva; Metabolism; Nutritional Status; Research; Sitosterols; Sterols

1965
STUDIES ON THE PLANT STEROLS AND TRIPERPENES. II. SEPARATION OF STIGMASTEROL, BETA-SITOSTEROL AND CAMPESTEROL, AND ABOUT SO-CALLED "GAMMA-SITOSTEROL".
    Chemical & pharmaceutical bulletin, 1965, Volume: 13

    Topics: Chemistry, Pharmaceutical; Cholesterol; Chromatography; Phytosterols; Research; Sitosterols; Sterols; Stigmasterol

1965
THE UTILIZATION AND FATE OF BETA-SITOSTEROL IN THE LARVA OF THE HOUSEFLY, MUSCA DOMESTICA L.
    Journal of insect physiology, 1965, Volume: 11

    Topics: Animals; Houseflies; Larva; Metabolism; Research; Sitosterols; Sterols

1965
THE EFFECT OF CORN OIL ON FECAL SITOSTEROL AND CHOLESTEROL IN MAN.
    Nutrition reviews, 1964, Volume: 22

    Topics: Cholesterol; Corn Oil; Humans; Sitosterols

1964
THE DIFFERENTIAL-PHOTOMETRIC ESTIMATION OF COPROSTANOL IN THE PRESENCE OF CHOLESTEROL, SITOSTEROL, AND OTHER 3-BETA-HYDROXYSTEROLS.
    Canadian journal of biochemistry, 1964, Volume: 42

    Topics: Cholestanol; Cholesterol; Feces; Photometry; Research; Sitosterols; Sterols

1964
DIFFERENTIAL-PHOTOMETRIC ESTIMATION OF CHOLESTEROL AND SITOSTEROL IN THE PRESENCE OF CERTAIN OTHER 3-BETA-HYDROXYSTEROLS.
    Canadian journal of biochemistry, 1964, Volume: 42

    Topics: Cholesterol; Edible Grain; Feces; Oils; Photometry; Research; Sitosterols; Sterols; Zea mays

1964
MAGNITUDE OF THE HYPOCHOLESTEROLEMIC EFFECT OF DIETARY SITOSTEROL IN MAN.
    The Journal of nutrition, 1964, Volume: 83

    Topics: Biomedical Research; Butter; Cholesterol; Diet; Dietary Fats; Humans; Sitosterols; Sterols

1964
[ACTION OF BETA-SITOSTEROL ON CHOLESTEROLEMIA AND THE LIPIDOGRAM IN ARTERIOSCLEROSIS. LONG TERM RESULTS].
    Bruxelles medical, 1964, Dec-27, Volume: 44

    Topics: Anticholesteremic Agents; Arteriosclerosis; Cholesterol; Geriatrics; Humans; Lipids; Lipoproteins; Sitosterols; Sterols

1964
[ACHIEVEMENTS IN THE FIELD OF SYNTHESIS OF BETA-SITOSTEROL DERIVATIVES AND STEROIDS].
    Farmatsevtychnyi zhurnal, 1964, Volume: 19

    Topics: Achievement; Chemistry, Pharmaceutical; Pharmacy; Research; Sitosterols; Steroids; Sterols

1964
Isolation of beta-sitosterol, beta-stosteryl-D-glucoside, and palmitic acid from coastal Bermuda grass and orchard grass.
    Journal of pharmaceutical sciences, 1963, Volume: 52

    Topics: Cynodon; Dactylis; Glucosides; Glycosides; Palmitic Acid; Poaceae; Sitosterols; Sterols

1963
Identification of the D-glucosides of stigmasterol, sitosterol and campesterol in tobacco and cigarette smoke.
    The Biochemical journal, 1963, Volume: 87

    Topics: Cholesterol; Glucosides; Glycosides; Humans; Nicotiana; Phytosterols; Sitosterols; Smoke; Smoking; Sterols; Stigmasterol

1963
EFFECT OF BETA-SITOSTEROL ON CHOLESTEROL AND LIPID METABOLISM IN THE RAT.
    Nature, 1963, Nov-09, Volume: 200

    Topics: Biochemical Phenomena; Biochemistry; Carbon Isotopes; Cholesterol; Hypercholesterolemia; Lipid Metabolism; Rats; Research; Sitosterols; Sterols

1963
[ISOLATION OF BETA-SITOSTEROL-BETA-DGLUCOSIDE FROM THE LEAVES OF LYCIUM CHINENSE MILL].
    Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 1963, Volume: 83

    Topics: Chemistry, Pharmaceutical; Glycosides; Lycium; Pharmacy; Plant Leaves; Plants, Medicinal; Research; Sitosterols; Sterols

1963
[EFFECTS OF BETA-SITOSTEROL ON THE BLOOD LEVEL OF CHOLESTEROL, LIPIDS AND POLYUNSATURATED FATTY ACIDS (CLINICAL STUDY)].
    Archivio di patologia e clinica medica, 1963, Volume: 40

    Topics: Arteriosclerosis; Blood Chemical Analysis; Cholesterol; Fatty Acids; Fatty Acids, Unsaturated; Geriatrics; Humans; Lipids; Pharmacology; Sitosterols; Sterols

1963
The biosynthesis of beta-amyrin and beta-sitosterol in germinating seeds of Pisum sativum.
    Biochemistry, 1962, May-25, Volume: 1

    Topics: Lipid Metabolism; Oleanolic Acid; Pisum sativum; Seeds; Sitosterols; Sterols

1962
The effects of sitosterol, nicotinic acid and triparanol on fat tolerance.
    The American journal of clinical nutrition, 1962, Volume: 10

    Topics: Anticholesteremic Agents; Fats; Lipid Metabolism; Niacin; Nicotinic Acids; Sitosterols; Sterols; Triparanol

1962
[Longterm treatment of human hypercholesterolemia by beta-sitosterol].
    Revue francaise de gerontologie, 1962, Volume: 8(Special)

    Topics: Arteriosclerosis; Cholesterol; Humans; Hypercholesterolemia; Sitosterols; Sterols

1962
[Research on the efficacy of antiatherosclerotic preparations. I. The control of serum lipids by a multivitamin-hormone preparation and beta-sitosterin].
    Medizinische Klinik, 1962, Jan-05, Volume: 57

    Topics: Arteriosclerosis; Cholesterol; Estradiol; Hormones; Humans; Sitosterols; Sterols; Testosterone; Triiodothyronine; Vitamins

1962
Biosynthesis of beta-sitosterol and pentacyclic triterpenes of Salvia officinalis.
    The Journal of biological chemistry, 1962, Volume: 237

    Topics: Pentacyclic Triterpenes; Plants; Salvia officinalis; Sitosterols; Sterols; Terpenes

1962
Biosynthesis of sclareol, beta-sitosterol, and oleanolic acid from mevalonic acid-2-C-14.
    The Journal of biological chemistry, 1962, Volume: 237

    Topics: Diterpenes; Fatty Acids; Mevalonic Acid; Oleanolic Acid; Plants; Sitosterols; Sterols; Terpenes

1962
Biosynthesis of 14C-sclareol and beta-sitosterol from 2-14C-mevalonic acid.
    Nature, 1961, Jan-14, Volume: 189

    Topics: Diterpenes; Fatty Acids; Lipid Metabolism; Mevalonic Acid; Sitosterols; Sterols; Terpenes

1961
Isolation of a beta-sitosterol complex from Salvia sclarea.
    Journal of pharmaceutical sciences, 1961, Volume: 50

    Topics: Plants; Salvia; Sitosterols; Sterols

1961
[Effect of beta-sitosterol on the blood lipid level in patients with coronary atherosclerosis].
    Terapevticheskii arkhiv, 1961, Volume: 33

    Topics: Cardiotonic Agents; Coronary Artery Disease; Coronary Disease; Humans; Lipids; Sitosterols; Sterols

1961
The effect of linoleic and linolenic acid, estradiol valerate and beta sitosterol upon experimentally induced hypercholesterolemia and the development of lipid changes in the aorta of dogs.
    The American journal of the medical sciences, 1961, Volume: 241

    Topics: alpha-Linolenic Acid; Animals; Aorta; Arachidonic Acid; Arteriosclerosis; Cholesterol; Dogs; Estradiol; Hypercholesterolemia; Lipid Metabolism; Lipids; Sitosterols; Sterols

1961
[On the effect of sitosterol on cholesterol metabolism in homothermals].
    Arzneimittel-Forschung, 1961, Volume: 11

    Topics: Cholesterol; Humans; Sitosterols; Sterols

1961
[Studies in the field of beta-sitosterol and non-steroid androgens].
    Meditsinskaia promyshlennost' SSSR, 1961, Volume: 11

    Topics: Androgens; Humans; Sitosterols; Sterols

1961
Metabolism of beta-sitosterol and other lipids in the presence of acetate-2-14C by blowfly larvae.
    Nature, 1960, Dec-17, Volume: 188

    Topics: Acetates; Animals; Diptera; Larva; Lipid Metabolism; Lipids; Sitosterols; Steroids

1960
Effect of beta-sitosterol on regression of hyperlipemia and increased plasma coagulability in the chicken.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1960, Volume: 104

    Topics: Animals; Blood Coagulation; Chickens; Humans; Hyperlipidemias; Lipids; Sitosterols; Sterols

1960
Radiochemical purity of beta-sitosterols tritiated by catalytic exchange and by the Wilzbach procedure.
    Archives of biochemistry and biophysics, 1960, Volume: 89

    Topics: Catalysis; Radiopharmaceuticals; Sitosterols; Sterols

1960
The metabolism of H3-beta-sitosterol in the guinea pig: its conversion to urinary cortisol.
    The Journal of biological chemistry, 1960, Volume: 235

    Topics: Guinea Pigs; Hydrocortisone; Lipid Metabolism; Sitosterols; Sterols

1960
EFFECT of thiouracil and sitosterol on diet-induced hypercholesterolemia and lipomatous arterial lesions in the rat.
    Nutrition reviews, 1960, Volume: 18

    Topics: Animals; Arteriosclerosis; Diet; Humans; Hypercholesterolemia; Rats; Sitosterols; Steroids; Thiouracil

1960
TREATMENT of hypercholesterolemic patients with niacin, sitosterol and safflower oil.
    Nutrition reviews, 1960, Volume: 18

    Topics: Arachidonic Acid; Humans; Niacin; Nicotinic Acids; Safflower Oil; Sitosterols

1960
Observations on an effect of beta sitosterol on "stypven clotting time".
    Medical bulletin (Ann Arbor, Mich.), 1960, Volume: 26

    Topics: Blood Coagulation; Cholesterol; Hematologic Tests; Sitosterols; Sterols

1960
[Experimental animal studies on the problem of absorption of beta-sitosterol].
    Arzneimittel-Forschung, 1960, Volume: 10

    Topics: Animals; Humans; Sitosterols; Sterols

1960
Effect of taurine, glycine and beta-sitosterols on serum and tissue cholesterol in the rat and rabbit.
    Circulation research, 1959, Volume: 7, Issue:2

    Topics: Animals; Bile Acids and Salts; Cholesterol; Glycine; Glycine Agents; Lipid Metabolism; Rabbits; Rats; Salts; Sitosterols; Steroids; Taurine

1959
Absorption of H3-beta-sitosterol in the lymph fistula rat.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1959, Volume: 100, Issue:1

    Topics: Animals; Fistula; Lipid Metabolism; Lymph; Lymphatic Diseases; Rats; Sitosterols; Steroids

1959
Comparative lymphatic absorption of beta-sitosterol and cholesterol by the rat.
    Archives of biochemistry and biophysics, 1959, Volume: 82, Issue:1

    Topics: Animals; Cholesterol; Lipid Metabolism; Lymphatic System; Rats; Sitosterols; Steroids

1959
Effect of beta-sitosterol on serum cholesterol concentration in the rat.
    The American journal of physiology, 1959, Volume: 197, Issue:1

    Topics: Animals; Cholesterol; Rats; Sitosterols; Steroids

1959
Hypercholesteremia: treatment with sitosterol and a low cholesterol diet.
    American practitioner and digest of treatment, 1959, Volume: 10, Issue:7

    Topics: Cholesterol; Diet; Humans; Hypercholesterolemia; Sitosterols; Steroids

1959
Effects of thiouracil and sitosterol on diet-induced hypercholesterolemia and lipomatous arterial lesions in the rat.
    American heart journal, 1959, Volume: 58, Issue:2

    Topics: Animals; Arteries; Arteriosclerosis; Cholesterol; Diet; Fats; Humans; Hypercholesterolemia; Rats; Sitosterols; Steroids; Thiouracil

1959
Comparison of the treatment of hypercholesteremia with nicotinic acid, sitosterol, and safflower oil.
    American heart journal, 1959, Volume: 58

    Topics: Arachidonic Acid; Cholesterol; Humans; Hypercholesterolemia; Niacin; Nicotinic Acids; Safflower Oil; Sitosterols; Sterols

1959
The effect of sitosterol on radioactive fat absorption patterns.
    The American journal of cardiology, 1959, Volume: 4

    Topics: Biological Transport; Coronary Disease; Fats; Heart; Humans; Metabolic Diseases; Sitosterols; Sterols

1959
[The intestinal resorption of radiocarbon-labeled cholesterol 4 in the rat, and the influence of sitosterol].
    Revue de l'atherosclerose, 1959, Volume: 1

    Topics: Animals; Biological Phenomena; Cholesterol; Intestines; Lipid Metabolism; Rats; Sitosterols; Sterols

1959
Effects of cholesterol and beta-sitosterol in the gerbil.
    The American journal of physiology, 1959, Volume: 197

    Topics: Animals; Cholesterol; Gerbillinae; Humans; Sitosterols; Sterols

1959
Formation of mixed crystals of cholesterol and sitosterol in vitro and in rabbit intestine.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1959, Volume: 102

    Topics: Animals; Cholesterol; In Vitro Techniques; Intestines; Rabbits; Sitosterols; Sterols

1959
Regression studies with safflower oil and sitosterol in rabbit atherosclerosis.
    Circulation research, 1959, Volume: 7

    Topics: Animals; Arachidonic Acid; Atherosclerosis; Rabbits; Safflower Oil; Sitosterols; Sterols

1959
Dietary and pharmaceutical approaches to atherosclerosis; special reference to beta-sitosterol.
    Texas state journal of medicine, 1958, Volume: 54, Issue:1

    Topics: Arteriosclerosis; Atherosclerosis; Diet; Sitosterols; Steroids

1958
Influence of H3-beta-sitosterol on sterol excretion.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1958, Volume: 97, Issue:2

    Topics: Biological Transport; Humans; Sitosterols; Steroids; Sterols

1958
Effect of beta-sitosterol on serum cholesterol and lipoprotein levels of patients ingesting a low-fat diet.
    The American journal of the medical sciences, 1958, Volume: 235, Issue:4

    Topics: Arteriosclerosis; Cholesterol; Diet; Diet, Fat-Restricted; Fats; Humans; Lipoproteins; Sitosterols; Steroids

1958
Sitosterol feeding: chronic animal and clinical toxicology and tissue analysis.
    Circulation research, 1958, Volume: 6, Issue:3

    Topics: Animals; Humans; Sitosterols; Steroids

1958
Response of serum lipids and lipoproteins o man to beta-sitosterol and safflower oil; a longterm study.
    Circulation, 1958, Volume: 17, Issue:5

    Topics: Arachidonic Acid; Humans; Lipids; Lipoproteins; Longitudinal Studies; Male; Safflower Oil; Sitosterols; Steroids

1958
Isolation of beta-sitosterol-D-glucoside from groundnut phospholipids.
    Nature, 1958, Apr-12, Volume: 181, Issue:4615

    Topics: Arachis; Glucosides; Glycosides; Humans; Phospholipids; Sitosterols

1958
[Intestinal absorption of cholesterol-4-C14 in the rat and the influence of sitosterol].
    Comptes rendus hebdomadaires des seances de l'Academie des sciences, 1958, May-12, Volume: 246, Issue:19

    Topics: Animals; Cholesterol; Intestinal Absorption; Intestines; Leadership; Lipid Metabolism; Rats; Sitosterols; Steroids

1958
Combined beta-sitosterol and linoleic acid regimen for cholesterolfed rabbits.
    Journal of gerontology, 1958, Volume: 13, Issue:2

    Topics: Animals; Cholesterol; Lagomorpha; Linoleic Acid; Rabbits; Sitosterols; Steroids

1958
The result of treatment of hypercholesterolemia associated with atherosclerosis with sitosterol and safflower oil derivatives.
    The Journal of the Louisiana State Medical Society : official organ of the Louisiana State Medical Society, 1958, Volume: 110, Issue:8

    Topics: Arachidonic Acid; Arteriosclerosis; Atherosclerosis; Cholesterol; Humans; Hypercholesterolemia; Safflower Oil; Sitosterols; Steroids

1958
[Effects of sitosterol & phenylethylacetamide (hyposterol) on hypercholesterolemia].
    Nederlands tijdschrift voor geneeskunde, 1958, Jun-14, Volume: 102, Issue:24

    Topics: Amides; Anesthetics, Local; Humans; Hypercholesterolemia; Sitosterols; Steroids

1958
Effects of the esterification of supplemental cholesterol and sitosterol in the diet.
    The Journal of nutrition, 1958, Jun-10, Volume: 65, Issue:2

    Topics: Cholesterol; Diet; Esterification; Lipid Metabolism; Liver; Sitosterols; Steroids

1958
Fate of beta-sitosterol in housefly larvae.
    Nature, 1958, Sep-13, Volume: 182, Issue:4637

    Topics: Animals; Biochemical Phenomena; Diptera; Houseflies; Larva; Lipid Metabolism; Sitosterols; Steroids

1958
Liver cholesterol mobilization in mice as effected by dietary beta-sitosterol and cholic acid.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1958, Volume: 99, Issue:2

    Topics: Animals; Bile Acids and Salts; Cholesterol; Cholic Acid; Lipid Metabolism; Liver; Mice; Salts; Sitosterols; Steroids

1958
[The inhibiting effect of beta-sitosterol on the intestinal absorption of cholesterol].
    Bollettino della Societa italiana di biologia sperimentale, 1958, Oct-31, Volume: 34, Issue:20

    Topics: Cholesterol; Intestinal Absorption; Intestines; Lipid Metabolism; Sitosterols; Steroids

1958
The influence of sitosterol upon psoriasis vulgaris; observations on electrophoretic pattern.
    Dermatologica, 1958, Volume: 117, Issue:5

    Topics: Cholesterol; Electrophoresis; Humans; Leadership; Psoriasis; Sitosterols; Steroids

1958
Clinical experiences with beta sitosterol, a new anti-cholesterolemic agent.
    Northwest medicine, 1957, Volume: 56, Issue:1

    Topics: Arteriosclerosis; Sitosterols; Steroids

1957
The effect of beta-sitosterol on cholesterol-induced atheroma in rabbits with high blood pressure.
    British journal of experimental pathology, 1957, Volume: 38, Issue:1

    Topics: Animals; Arteriosclerosis; Cholesterol; Hypertension; Plaque, Atherosclerotic; Rabbits; Sitosterols; Steroids

1957
Effect of dihydrocholesterol and beta-sitosterol on cholesterol atherosclerosis in rabbits.
    Circulation research, 1957, Volume: 5, Issue:2

    Topics: Animals; Arteriosclerosis; Atherosclerosis; Cholestanol; Cholesterol; Rabbits; Sitosterols; Steroids

1957
Effect of sitosterol on the concentration of serum lipids in patients with coronary atherosclerosis.
    Circulation, 1957, Volume: 16, Issue:5

    Topics: Coronary Artery Disease; Coronary Disease; Heart; Humans; Lipids; Sitosterols; Steroids

1957
[Sitosterol therapy of hypercholesterolemia].
    Ugeskrift for laeger, 1957, Sep-12, Volume: 119, Issue:37

    Topics: Cholesterol; Humans; Hypercholesterolemia; Sitosterols; Steroids

1957
The effect of beta-sitosterol upon intestinal absorption of cholesterol in the rat.
    Circulation research, 1956, Volume: 4, Issue:2

    Topics: Animals; Cholesterol; Intestinal Absorption; Intestines; Lipid Metabolism; Rats; Sitosterols; Steroids

1956
Sitosterol administration in normal and hypercholesteremic subjects; the effect in man of sitosterol therapy on serum lipids and lipoproteins.
    A.M.A. archives of internal medicine, 1956, Volume: 97, Issue:6

    Topics: Blood; Cholesterol; Humans; Hypercholesterolemia; Lipids; Lipoproteins; Male; Sitosterols; Steroids

1956
Effects of beta-sitosterol on regression of cholesterol atherosclerosis in rabbits.
    Circulation research, 1956, Volume: 4, Issue:4

    Topics: Animals; Arteriosclerosis; Atherosclerosis; Cholesterol; Rabbits; Sitosterols; Steroids

1956
[Study of the benzene extract of the leaves of little periwinkle: Vinca minor, presence of ursolic acid, ornol, beta-sitosterol and triacontane].
    Annales pharmaceutiques francaises, 1956, Volume: 14, Issue:5

    Topics: Benzene; Plant Extracts; Plant Leaves; Sitosterols; Triterpenes; Ursolic Acid; Vinca

1956
The serum cholesterol and other lipids after administration of sitosterol.
    British heart journal, 1955, Volume: 17, Issue:3

    Topics: Blood; Cholesterol; Dietary Fats, Unsaturated; Humans; Lipids; Plant Oils; Sitosterols; Steroids; Triticum

1955
The effect of sitosterol administration upon the serum cholesterol level and lipoprotein pattern.
    The American journal of the medical sciences, 1955, Volume: 230, Issue:6

    Topics: Blood; Cholesterol; Humans; Lipoproteins; Sitosterols; Steroids; Triticum

1955
Effects of Beta-sitosterol and ferric chloride on accumulation of cholesterol in mouse liver.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1955, Volume: 90, Issue:1

    Topics: Animals; Chlorides; Cholesterol; Ferric Compounds; Iron; Lipid Metabolism; Liver; Mice; Sitosterols; Steroids

1955
SYMPOSIUM on sitosterol.
    Transactions of the New York Academy of Sciences, 1955, Volume: 18, Issue:2

    Topics: Sitosterols; Steroids

1955
Symposium on sitosterol. I. The effects of sitosterol ingestion on serum cholesterol concentration.
    Transactions of the New York Academy of Sciences, 1955, Volume: 18, Issue:2

    Topics: Blood; Cholesterol; Eating; Humans; Sitosterols; Steroids

1955
Symposium on sitosterol. II. Clinical experience with sitosterols.
    Transactions of the New York Academy of Sciences, 1955, Volume: 18, Issue:2

    Topics: Blood; Cholesterol; Humans; Sitosterols; Steroids

1955
Symposium on sitosterol. III. The physical chemistry of cholesterol and beta-sitosterol related to the intestinal absorption of cholesterol.
    Transactions of the New York Academy of Sciences, 1955, Volume: 18, Issue:2

    Topics: Chemistry, Physical; Cholesterol; Humans; Intestinal Absorption; Intestines; Lipid Metabolism; Sitosterols; Steroids

1955
Symposium on sitosterol. IV. Absorbability of beta-sitosterol.
    Transactions of the New York Academy of Sciences, 1955, Volume: 18, Issue:2

    Topics: Humans; Lipid Metabolism; Sitosterols; Steroids

1955
Effects of lipotropes and sitosterol on the level of blood lipids and the clinical course of angina pectoris.
    Journal of the American Geriatrics Society, 1955, Volume: 3, Issue:6

    Topics: Aged; Angina Pectoris; Blood; Cholesterol; Choline; Humans; Inositol; Lipids; Sitosterols

1955
The effects of sitosterol on serum lipids.
    The American journal of medicine, 1955, Volume: 19, Issue:1

    Topics: Blood; Humans; Lipids; Sitosterols; Steroids

1955
Effect of varying the intake of dietary fat and the ingestion of sitosterol on lipid and lipoprotein fractions of human serum.
    Metabolism: clinical and experimental, 1955, Volume: 4, Issue:4

    Topics: Blood; Dietary Fats; Dietary Fats, Unsaturated; Eating; Fats; Humans; Lipids; Lipoproteins; Sitosterols; Steroids; Triticum

1955
Absorption of cholesterol-4-C14 in rats fed mixed soybean sterols and beta-sitosterol.
    Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 1953, Volume: 83, Issue:3

    Topics: Animals; Cholesterol; Glycine max; Lipid Metabolism; Rats; Sitosterols; Sterols

1953
Beta-Sitosteryl D-glucoside and beta-sitosterol from commercially dried grapefruit pulp.
    Archives of biochemistry and biophysics, 1953, Volume: 47, Issue:2

    Topics: Citrus; Citrus paradisi; Fruit; Glucosides; Glycosides; Humans; Sitosterols; Steroids

1953