stigmasterol and gamma-sitosterol

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Chemical examination of Chinese mangrove

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Topics: Animals; Cholesterol; Chromatography, High Pressure Liquid; Phytosterols; Rats; Reproducibility of Results; Sitosterols; Stigmasterol; Tandem Mass Spectrometry; Zea mays

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Topics: Drugs, Chinese Herbal; Isoflavones; Sitosterols; Stigmasterol

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

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

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

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

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

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

Topics: Drugs, Chinese Herbal; Flavonoids; Oleanolic Acid; Sitosterols; Stigmasterol; Triterpenes

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

Topics: Cholesterol; Chromatography, Gas; Food, Fortified; Humans; Phytosterols; Sitosterols; Stigmasterol

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

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

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

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

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

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

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

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

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

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

Topics: Cholesterol; Chromatography, Gas; Phytosterols; Plants; Sitosterols; Stigmasterol

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

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

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

Topics: Cholesterol; Phytosterols; Plants, Medicinal; Sitosterols; Stigmasterol

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

Topics: Animals; Cholesterol; Cholesterol Esters; Female; Intestinal Absorption; Intestine, Small; Male; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Stigmasterol

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

Topics: Chemistry, Pharmaceutical; Cholesterol; Chromatography; Phytosterols; Research; Sitosterols; Sterols; Stigmasterol

Topics: Cholesterol; Glucosides; Glycosides; Humans; Nicotiana; Phytosterols; Sitosterols; Smoke; Smoking; Sterols; Stigmasterol