stigmasterol and spinasterol

α-Spinasterol is a phytosterol found in various edible and non-edible plant sources. The edible plant materials containing α-spinasterol include spinach leaves, cucumber fruits, seeds of pumpkin and watermelon, argan seed oil, cactus pear seed oil and Amaranthus sp. It is a bioavailable nutraceutical, and it can cross the blood-brain barrier. It possesses several important pharmacological properties such as anti-diabetes mellitus, antiinflammation, hypolipidemic, antiulcer, neuroprotection, anti-pain and antitumour activities. For this review, literature search was made focusing on the pharmacological properties of α-spinasterol using PubMed and Google Scholar data bases. Recent studies show the promising antidiabetic properties of α-spinasterol. Its anti-diabetic mechanisms include enhancement of insulin secretion, reduction in insulin resistance, anti-diabetic nephropathy, increase in glucose uptake in muscle cells and inhibition of glucose absorption from intestine. Besides, it is a safe antiinflammatory agent, and its antiinflammatory mechanisms include inhibition of cyclooxygenases, antagonism of TRPV1 receptor and attenuation of proinflammatory cytokines and mediators. It is a promising and safe nutraceutical molecule for human health care. Food supplements, value-added products and nutraceutical formulations can be developed with α-spinasterol for the management of diabetes, chronic inflammatory diseases and improving general health. This review provides all scattered pharmacological studies on α-spinasterol in one place and highlights its immense value for human health care.

Topics: Anti-Inflammatory Agents; Cytokines; Dietary Supplements; Glucose; Humans; Hypoglycemic Agents; Phytosterols; Plant Oils; Prostaglandin-Endoperoxide Synthases; Stigmasterol

Terpenoids from natural plant sources are valuable for their diverse biological activities that have important roles in the medical and agrochemical industries. In this study, we assessed the antioxidant, antifungal, and aphicidal activities of a mixture of spinasterol and 22,23-dihydrospinasterol from the leaves of Citrullus colocynthis. We used 1,1-diphenyl-2-picrylhydrazyl (DPPH) to assess antioxidant activity, and we measured antifungal activity using mycelium growth inhibition assays with three pathogenic fungi, Magnaporthe grisea, Rhizoctonia solani, and Phytophthora infestans. Aphicidal activity against adults of Myzus persicae was determined using in vitro and in vivo assays. Spinasterol and 22,23-dihydrospinasterol exhibited moderate antioxidant activity, even at lower concentrations: 19.98% at 0.78 µg mL

Topics: Antifungal Agents; Antioxidants; Citrullus colocynthis; Plant Leaves; Sitosterols; Stigmasterol; Triterpenes

Hyperpigmentation is considered by many to be a beauty problem and is responsible for photoaging. To treat this skin condition, medicinal cosmetics containing tyrosinase inhibitors are used, resulting in skin whitening. In this study, taraxerol methyl ether (

Topics: Antioxidants; Arbutin; Cell Line, Tumor; Cell Proliferation; Flavonoids; Humans; Hydroxybenzoates; Manilkara; Monophenol Monooxygenase; Neoplasms; Oleanolic Acid; Phytochemicals; Pyrones; Stigmasterol

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.

Topics: Alkynes; Antineoplastic Agents, Phytogenic; Asteraceae; Cell Line, Tumor; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Furaldehyde; Furans; Glucosides; Humans; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Sesquiterpenes; Stigmasterol; Triterpenes

Topics: Apoptosis; Breast Neoplasms; Female; Ganoderma; Gene Expression Regulation, Neoplastic; Humans; MCF-7 Cells; Ovarian Neoplasms; Stigmasterol; Tumor Suppressor Protein p53

Exposures to toxic levels of vanadium and soluble vanadium compounds cause behavioral impairments and neurodegeneration via free radical production. Consequently, natural antioxidant sources have been explored for effective and cheap remedy following toxicity. Grewia carpinifolia has been shown to improve behavioral impairments in vanadium-induced neurotoxicity, however, the active compounds implicated remains unknown. Therefore, this study was conducted to investigate ameliorative effects of bioactive compounds from G. carpinifolia on memory and behavioral impairments in vanadium-induced neurotoxicity.. Sixty BALB/c mice were equally divided into five groups (A-E). A (control); administered distilled water, B (standard); administered α-tocopherol (500 mg/kg) every 72 hr orally with daily dose of sodium metavanadate (3 mg/kg) intraperitoneally, test groups C, and D; received single oral dose of 100 μg β-spinasterol or stigmasterol (bioactive compounds from G. carpinifolia), respectively, along with sodium metavanadate and the model group E, received sodium metavanadate only for seven consecutive days. Memory, locomotion and muscular strength were accessed using Morris water maze, Open field and hanging wire tests. In vivo antioxidant and neuroprotective activities were evaluated by measuring catalase, superoxide dismutase, MDA, H. In Morris water maze, stigmasterol significantly (p ≤ 0.05) decreased escape latency and increased swimming time in target quadrant (28.01 ± 0.02; 98.24 ± 17.38 s), respectively, better than α-tocopherol (52.43 ± 13.25; 80.32 ± 15.21) and β-spinasterol (42.09 ± 14.27; 70.91 ± 19.24) in sodium metavanadate-induced memory loss (112.31 ± 9.35; 42.35 ± 11.05). β-Spinasterol and stigmasterol significantly increased exploration and latency in open field and hanging wire tests respectively. Stigmasterol also increased activities of antioxidant enzymes, decreased oxidative stress markers and lipid peroxidation in mice hippocampal homogenates, and increased MBP expression.. The findings of this study indicate a potential for stigmasterol, a bioactive compound from G. carpinifolia in improving cognitive decline, motor coordination, and ameliorating oxidative stress in vanadium-induced neurotoxicity.

Topics: Animals; Antioxidants; Behavior, Animal; Cognitive Dysfunction; Down-Regulation; Hippocampus; Lipid Peroxidation; Male; Memory Disorders; Mice; Mice, Inbred BALB C; Myelin Basic Protein; Neurotoxicity Syndromes; Oxidative Stress; Stigmasterol; Vanadates

In this study, we designed a novel method of the synthesis of α-spinasterol from commercially available stigmasterol and explored the combinational effect of the α-spinasterol with ceftiofur in vitro against S. pullorum cvcc533, S. pneumoniae CAU0070, E. coli, and S. aureus. α-Spinasterol was obtained by a key reaction of Bamford-Stevens reaction with a desirable yield for five steps. The combination of α-spinasterol and ceftiofur showed stronger synergetic effect against the four pathogenic strains compared with that of stigmasterol and ceftiofur alone. In time-kill analyses, at concentrations above the MICs, ceftiofur in combination with α-spinasterol exhibited time-dependency and concentration-dependency comparing to time dependency with ceftiofur alone. We conclude that the combination usage of α-spinasterol and ceftiofur is an effective and promising strategy against the four pathogenic bacterial strains in vitro.

Topics: Anti-Bacterial Agents; Cephalosporins; Drug Synergism; Escherichia coli; Microbial Sensitivity Tests; Molecular Structure; Staphylococcus; Stigmasterol

Sterols play a unique role for the structural and dynamical organization of membranes. The current study reports data on the membrane properties of the phytosterol (3β,5α,22E)-stigmasta-7,22-dien-3-β-ol (α-spinasterol), which represents an important component of argan oil and have not been investigated so far in molecular detail. In particular, the impact of α-spinasterol on the structure and organization of lipid membranes was investigated and compared with those of cholesterol. Various membrane parameters such as the molecular packing of the phospholipid fatty acyl chains, the membrane permeability toward polar molecules, and the formation of lateral membrane domains were studied. The experiments were performed on lipid vesicles using methods of NMR spectroscopy and fluorescence spectroscopy and microscopy. The results show that α-spinasterol resembles the membrane behavior of cholesterol to some degree.

Topics: Cholesterol; Fluorescence; Lipid Bilayers; Magnetic Resonance Spectroscopy; Membranes, Artificial; Permeability; Phospholipids; Plant Oils; Stigmasterol

Postoperative pain is one of the most common manifestations of acute pain and is an important problem faced by patients after surgery. Moreover, neuronal trauma or chemotherapeutic treatment often causes neuropathic pain, which induces disabling and distressing symptoms. At present, treatments of both painful conditions are inadequate. α-Spinasterol, which is well characterized as a transient receptor potential vanilloid 1 antagonist, has anti-inflammatory, antioxidant and antinociceptive effects. Therefore, we investigated its antinociceptive potential on postoperative and neuropathic pain, as well as its effect on COX-1 and COX-2 activities.. Nociceptive responses in a postoperative pain model (surgical incision-induced) or different neuropathic pain models (trauma or chemotherapy-induced) were investigated in mice.. Oral administration of α-spinasterol reduced postoperative pain, when given as a pre- (0.5 h before incision) or post-treatment (0.5 h after incision), and reduced cell infiltration in the injured tissue. α-Spinasterol also reduced the mechanical allodynia induced by partial sciatic nerve ligation and the mechanical and cold allodynia induced by paclitaxel. Moreover, α-spinasterol inhibited COX-1 and COX-2 enzyme activities without altering the body temperature of animals. Importantly, α-spinasterol did not alter spontaneous or forced locomotor activity. Furthermore, it did not cause gastric damage or liver and kidney changes, nor did it alter cell viability in the cerebral cortex and spinal cord slices of mice.. α-Spinasterol is an effective and safe COX inhibitor with antinociceptive effects in postoperative and neuropathic pain models. Therefore, it is an interesting prototype for the development of novel analgesic drugs.

Topics: Acute Pain; Administration, Oral; Analgesics; Animals; Cyclooxygenase 2 Inhibitors; Cyclooxygenase Inhibitors; Disease Models, Animal; Hyperalgesia; Male; Mice; Neuralgia; Pain, Postoperative; Stigmasterol; Time Factors; TRPV Cation Channels

A new compound, methylbergenin (1), was isolated from the whole plants of Ardisia japonica (Thunb.) Bl. (Myrsinaceae), along with eight known compounds: demethoxybergenin (2), bergenin (3), afzelin (4), quercitrin (5), bauerenol (6), bauerenone (7), α-spinasterol (8) and chondrillasterone (9). Compounds 1, 7 and 9 were isolated from A. japonica for the first time. The structure of compound 1 was determined on the basis of NMR (1D and 2D) and mass spectroscopic analysis. The absolute configuration of 1 was assessed by single-crystal X-ray diffraction. Compounds 1, 4, 5, 7 and 9 showed potential inhibitory effects against nitric oxide production in LPS stimulated RAW 264.7 murine macrophages. In addition, Compounds 7 and 9 exhibited cytotoxicity against A549 and HepG-2 cells.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Ardisia; Benzopyrans; Crystallography, X-Ray; Drug Evaluation, Preclinical; Hep G2 Cells; Humans; Lipopolysaccharides; Macrophages; Magnetic Resonance Spectroscopy; Mice; Molecular Structure; Nitric Oxide; Stigmasterol; Triterpenes

Impatiens glandulifera has been imported from Himalaya in Europe and is considered as an invasive alien plant whose spreading arouses increasing interest among scientific literature. Via anti-cancer bioguiding, two new glucosylated steroids, named glanduliferins A and B, were isolated from the dried stem of I. glandulifera plants, together with the well-known α-spinasterol and 2-methoxy-1,4-naphthoquinone, which are also isolated from roots and leaves. They were characterized as 17-(2-hydroxy-2-pentamethylcyclopropyl-ethyl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopents[a]phenathren-3-O-(4-O-acetyl)-α-D-glucopyranoside and 17-(4-ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopents[a]phenathren-3-O-(6-O-acetyl)-β-D-glucopyranoside using various NMR and HRESIMS techniques and chemical methods. In vitro determination of the growth inhibitory activity of the four isolated compounds using the MTT colorimetric assay revealed mean IC50 growth inhibitory value of ~30 μM for glanduliferin A while glanduliferin B and α-spinasterol were poorly active till 100 μM. 2-methoxy-1,4-naphthoquinone revealed to be active in the single micromolar digit range as previously described. Quantitative videomicroscopy analyses of the effects of glanduliferins A and B suggested cytostatic rather than cytotoxic activity in U373 glioblastoma (GBM) cells.

Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Humans; Impatiens; Molecular Structure; Naphthoquinones; Plant Stems; Saponins; Steroids; Stigmasterol

The transient receptor potential vanilloid 1 (TRPV1) receptor has recently gained attention as a new molecular target in the treatment of mental disorders such as depression and anxiety. α-Spinasterol is a plant steroid that acts as a TRPV1 antagonist. The present study was undertaken to evaluate the antidepressant- and anxiolytic-like properties of α-spinasterol in mice. The obtained results showed that α-spinasterol (at doses of 1 and 2mg/kg) exerted anti-immobility effect in mice subjected to the forced swim test. Furthermore, co-administration of an ineffective dose of α-spinasterol (0.5mg/kg) with an ineffective dose of another TRPV1 antagonist - capsazepine (50 μg/mouse) produced a synergistic effect in the forced swim test. This compound was, however, devoid of anxiolytic-like effects in the elevated plus maze (at doses of 0.5-2mg/kg) and the light/dark box test (at a dose of 2mg/kg) in mice. Of note, α-spinasterol did not produce significant changes in body temperature and did not alter spontaneous locomotor activity in mice. The present study adds further support to the thesis that antagonism of the TRPV1 receptors may produce antidepressant effects. α-Spinasterol may represent a new therapeutic approach towards the development of novel antidepressant therapy. However, further detailed studies on the antidepressant potential of α-spinasterol are warranted.

Topics: Animals; Anti-Anxiety Agents; Antidepressive Agents; Anxiety; Body Temperature; Capsaicin; Depression; Male; Mice; Motor Activity; Stigmasterol; TRPV Cation Channels

Spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, were synthesized from commercially available stigmasterol by a four steps reactions. In addition, the effects of these phytosterols on cell growth and mitochondrial activity were evaluated on 158N murine oligodendrocytes, C6 rat glioma cells, and SK-N-BE human neuronal cells with the crystal violet test and the MTT test, respectively. The effects of spinasterol and schottenol were compared with 7-ketocholesterol (7KC) and ferulic acid, which is also present in argan and cactus pear seed oil. Whatever the cells considered, dose dependent cytotoxic effects of 7KC were observed whereas no or slight effects of ferulic acid were found. With spinasterol and schottenol, no or slight effects on cell growth were detected. With spinasterol, reduced mitochondrial activities (30-50%) were found on 158N and C6 cells; no effect was found on SK-N-BE. With schottenol, reduced mitochondrial activity were revealed on 158N (50%) and C6 (10-20%) cells; no effect was found on SK-N-BE. Altogether, these data suggest that spinasterol and schottenol can modulate mitochondrial activity and might therefore influence cell metabolism.

Topics: Animals; Cell Line; Cell Proliferation; Central Nervous System; Humans; Mice; Mitochondria; Phytosterols; Plant Oils; Pyrus; Rats; Seeds; Sitosterols; Stigmasterol

α-Spinasterol is a plant-derived compound which was reported to act as a selective antagonist for the transient receptor potential vanilloid 1 (TRPV1) receptor. Several studies revealed that the TRPV1 receptors might modulate seizure activity in animal models of seizures and epilepsy. The aim of the present study was to investigate the effect of α-spinasterol on the seizure threshold in three acute models of seizures, i.e., in the intravenous (i.v.) pentylenetetrazole (PTZ) seizure test, in the maximal electroshock seizure threshold (MEST) test and in the model of psychomotor seizures induced by 6 Hz stimulation in mice. Our results revealed significant anticonvulsant effect of α-spinasterol in all the used seizure tests. In the i.v. PTZ test, statistically significant elevation was noted in case of the threshold for myoclonic twitches (doses of 0.1-1 mg/kg) and generalized clonus seizures (doses of 0.5 and 1 mg/kg) but not for tonic seizures. The studied TRPV1 antagonist also increased the threshold for tonic hindlimb extension in the MEST (doses of 0.5 and 1 mg/kg) and 6 Hz psychomotor seizure (doses of 0.1 and 0.5 mg/kg) tests in mice. Furthermore, α-spinasterol did not produce any significant impairment of motor coordination (assessed in the chimney test) and muscular strength (investigated in the grip-strength test) and it did not provoke significant changes in body temperature in mice. Based on the results of our study and the fact that α-spinasterol is characterized by good blood-brain permeability, we postulate further investigation of this compound to precisely evaluate mechanism of its anticonvulsant action and opportunity of its usage in clinical practice.

Topics: Animals; Anticonvulsants; Body Temperature; Disease Models, Animal; Dose-Response Relationship, Drug; Electric Stimulation; Male; Mice; Motor Activity; Muscle Strength; Pentylenetetrazole; Random Allocation; Seizures; Stigmasterol; Treatment Outcome; TRPV Cation Channels

To study the chemical constituents from the active fractions of Kalimeris indica.. The chemical constituents were extracted of different concentrations and isolated by silica gel, Sephadex LH-20 column and preparative HPLC. The chemical structures were further elucidated by the physicochemical characters, MS and NMR spectral data.. Fourteen compounds were isolated and identified as α-spinasterol(1), dibutylphthalate (2), (22E,24R)-5α,8α-epidioxy-ergosta-6,22-dien-3β-ol(3), oleanolic acid(4), coniferyl alcohol(5), umbelliferone(6), syringaresinol(7), 15-oxo-14,16H-strictic acid(8), lariciresinol(9), (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol(10), neoechinulin A(11), pinoresinol(12), 4-allyl-3,5-dimethoxyphenol(13), and 3,4,5-tri-methoxyacetophenone (14).. Except compound 1, the other compounds are isolated from this genus for the first time.

Topics: Asteraceae; Phytochemicals; Stigmasterol

Polygala sabulosa A. W. Bennett is a small herb popularly known as "timutu-pinheirinho" that is widely distributed in southern Brazil and that is used to treat disorders of the bowel and kidney and as a topical anesthetic and expectorant in folk medicine. This study was designed to investigate the anti-inflammatory properties of the hydroalcoholic extract (HEPs), CH2Cl2 fraction and the steroid α-spinasterol obtained from the aerial parts of Polygala sabulosa in a model of acute inflammation induced by intraperitoneal injection of bacterial lipopolysaccharide in mice.. The anti-inflammatory effect of HEPs (3-300 mg/kg, i.g.), CH2Cl2 fraction (0.003-30 mg/kg, i.g.) and steroid α-spinasterol (0.001-1mg/kg, i.p. or 1-10mg/kg, i.g.), were evaluated in mice subjected to the acute inflammation caused by intraperitoneal (i.p.) injection of lipopolysaccharide (LPS, 0.02 µg/kg). The anti-inflammatory activity of the HEPs, CH2Cl2 fraction and steroid were assessed by determining the total numbers of leukocytes and differential cell counts (neutrophils and mononuclear cells) and levels of pro-inflammatory (IL-1β, TNF-α, IL-6) or anti-inflammatory (IL-10) cytokines in peritoneal fluid.. The administration of HEPs (3-300 mg/kg, i.g.) completely inhibited inflammatory cell infiltration (300 mg/kg, i.g.) and it reduced TNF-α (100-300 mg/kg) and IL-1β (100mg/kg) levels in LPS-injected mice. Furthermore, the administration of CH2Cl2 fraction (0.003-30 mg/kg, i.g.) or α-spinasterol (0.001-10mg/kg, by i.p. or i.g.) significantly reduces inflammatory cell infiltration in LPS-injected mice. Moreover, dexamethasone (0.5mg/kg, i.p., used as a positive control) inhibited inflammatory cell infiltration and reduced the levels of TNF-α, IL-1β and IL-6 in LPS-injected mice.. Taken together, these results provide the first experimental evidence demonstrating that HEPs have significant anti-inflammatory effects on LPS-induced inflammation. These effects appear to be, at least in part, due to the presence of α-spinasterol. These findings support the widespread use of Polygala sabulosa in popular medicine and demonstrate that this plant has therapeutic potential for the development of phytomedicines with anti-inflammatory properties.

Topics: Animals; Anti-Inflammatory Agents; Ethanol; Lipopolysaccharides; Methylene Chloride; Mice; Molecular Structure; Peritonitis; Plant Extracts; Polygala; Stigmasterol; Water

The objective of this study was to evaluate the biological activities of the major phytosterols present in argan oil (AO) and in cactus seed oil (CSO) in BV2 microglial cells. Accordingly, we first determined the sterol composition of AO and CSO, showing the presence of Schottenol and Spinasterol as major sterols in AO. While in CSO, in addition to these two sterols, we found mainly another sterol, the Sitosterol. The chemical synthesis of Schottenol and Spinasterol was performed. Our results showed that these two phytosterols, as well as sterol extracts from AO or CSO, are not toxic to microglial BV2 cells. However, treatments by these phytosterols impact the mitochondrial membrane potential. Furthermore, both Schottenol and Spinasterol can modulate the gene expression of two nuclear receptors, liver X receptor (LXR)-α and LXRβ, their target genes ABCA1 and ABCG1. Nonetheless, only Schottenol exhibited a differential activation vis-à-vis the nuclear receptor LXRβ. Thus Schottenol and Spinasterol can be considered as new LXR agonists, which may play protective roles by the modulation of cholesterol metabolism.

Topics: Animals; ATP Binding Cassette Transporter 1; ATP Binding Cassette Transporter, Subfamily G, Member 1; ATP-Binding Cassette Transporters; Cell Line; Gene Expression Regulation; Lipoproteins; Liver X Receptors; Membrane Potential, Mitochondrial; Mice; Microglia; Opuntia; Orphan Nuclear Receptors; Plant Oils; Seeds; Sitosterols; Sterols; Stigmasterol

Spinasterol, a biologically active compound, exhibits a number of pharmacological activities, including antitumor, antiulcerogenic and anticarcinogenic activity, and originates from the aerial parts of Aster scaber Thunb (Asteraceae). The present study investigated whether α-spinasterol isolated from Melandrium firmum Rohrbach could prevent benign prostatic hyperplasia (BPH) induced by testosterone propionate (TP) in rats. Male Wistar rats were randomly divided into four groups of eight rats following castration. A negative control group received subcutaneous injections of corn oil. Treatments were administered orally 1 h prior to TP injection. All the rats were sacrificed at the scheduled termination time and their prostates were removed, cleaned and weighed. The prostate size ratio (prostate weight/rat body weight) was then calculated. Additional histopathological examinations were conducted, and the levels of TP and dihydrotestosterone (DHT) in the serum and prostate were measured. TP significantly increased the prostate size ratio (P<0.01), and DHT and testosterone levels in the serum and prostate. The TP-induced increase was significantly inhibited in α-spinasterol-treated rats when compared with the negative controls (P<0.05). In addition, histopathological examination demonstrated that α-spinasterol treatment suppressed TP-induced prostatic hyperplasia. It is concluded that α-spinasterol can prevent TP-induced prostatic hyperplasia and may be beneficial in the management of BPH.

Topics: Animals; Dihydrotestosterone; Disease Models, Animal; Male; Organ Size; Plant Extracts; Prostate; Prostatic Hyperplasia; Rats; Stigmasterol; Testosterone

Polygala cyparissias, used in folk medicine as an anaesthetic, has already demonstrated antinociceptive activity against acute pain. In this study, we investigated the antihyperalgesic activity of the P. cyparissias methanol extract (PCME) from which the following compounds were isolated: α-spinasterol (PC1), 1,3-dihydroxy-7-methoxyxanthone (PC2), 1,7-dihydroxy-2,3-methylenedioxyxanthone (PC3) and 1,3,6,8-tetrahydroxy-2,7-dimethoxyxanthone (PC4). The antihyperalgesic effect was evaluated using experimental models of persistent pain induced by carrageenan, lipopolysaccharide (LPS), Freund's Complete Adjuvant (CFA), PGE(2) or epinephrine. The partial ligation of the sciatic nerve (PLSN) model was also used. In inflammatory hyperalgesia induced by carrageenan, LPS, CFA or PGE(2), the inhibition values obtained with the PCME treatment were 68 ± 3%, 89 ± 5%, 43 ± 3% and 40 ± 4%, respectively. In epinephrine-induced hyperalgesia, the extract was effective, reducing 99 ± 11% of response frequency, while in PLSN, 54 ± 4% of inhibition was obtained. These results allow to suggest that the antihyperalgesic activity of PCME is, at least in part, related to its capability to inhibit the hypersensitization induced by pro-inflammatory mediators, such as LPS, carrageenan and CFA, without interfering with locomotor activity or motor performance. Furthermore, compounds PC1, PC3 and PC4 inhibited the carrageenan-induced hyperalgesia with inhibition of 42 ± 6%, 48 ± 5% and 64 ± 4%, respectively. In summary, our data demonstrate that PCME has relevant antihyperalgesic activity and that the isolated PC1, PC3 and PC4 seem to be responsible, at least in part, for this important effect.

Topics: Analgesics; Animals; Carrageenan; Disease Models, Animal; Drug Evaluation, Preclinical; Epinephrine; Female; Freund's Adjuvant; Hyperalgesia; Inflammation; Lipopolysaccharides; Medicine, Traditional; Methanol; Mice; Neuralgia; Pain; Plant Extracts; Polygala; Sciatic Nerve; Stigmasterol; Xanthones

Extracts from the leaves of Stewartia koreana are known to exhibit strong anti-inflammatory activity. Investigation of bioactive compounds from S. koreana has led to the isolation of 3-O-β-d-glucopyanosylspinasterol (spinasterol-Glc), a spinasterol glycoside. In the present study, we examined the effects of spinasterol-Glc on production of nitric oxide (NO) and proinflammatory cytokines in LPS-treated RAW264.7 macrophage cells and in mouse models. Our results showed that spinasterol-Glc inhibited the production of NO and proinflammatory cytokines such as TNF-α, IL-6 and IL-1β in dose-dependent manners in LPS-treated RAW264.7 cells. Spinasterol-Glc inhibited the expression of iNOS and the proinflammatory cytokine genes. Spinasterol-Glc also inhibited phosphorylation of IκB-α and IKKα/β as well as translocation of NF-κB to the nucleus. We demonstrated that spinasterol-Glc reduced transcription of the NF-κB minimal promoter and NF-κB DNA binding activity. Administration of the spinasterol-Glc significantly decreased the plasma levels of these inflammatory mediators including TNF-α, IL-6 and IL-1β in LPS-injected mice and improved survival of septic mice with lethal endotoxemia. These results suggest that spinasterol-Glc has effective inhibitory effects on production of inflammatory mediators via inhibition of MAP kinases/NF-κB activities, and can be used as a potential anti-inflammatory agent for the prevention and treatment of inflammatory diseases.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Base Sequence; Cell Line; Cytokines; Down-Regulation; Glycosides; I-kappa B Kinase; I-kappa B Proteins; Inflammation Mediators; Lipopolysaccharides; Macrophage Activation; Male; MAP Kinase Signaling System; Medicine, Korean Traditional; Mice; Mice, Inbred C57BL; NF-kappa B; NF-KappaB Inhibitor alpha; Nitric Oxide; Nitric Oxide Synthase Type II; RNA, Messenger; Stigmasterol; Theaceae

The transient receptor potential vanilloid 1 (TRPV1) receptor is relevant to the perception of noxious information and has been studied as a therapeutic target for the development of new analgesics. The goal of this study was to perform in vivo and in vitro screens to identify novel, efficacious, and safe TRPV1 antagonists isolated from leaves of the medicinal plant Vernonia tweedieana Baker. All of the fractions and the hydroalcoholic extract produced antinociception in mice during the capsaicin test, but the dichloromethane fraction also had antioedematogenic effect. Among the compounds isolated from the dichloromethane fraction, only α-spinasterol reduced the nociception and edema induced by capsaicin injection. Moreover, α-spinasterol demonstrated good oral absorption and high penetration into the brain and spinal cord of mice. α-Spinasterol was able to displace [3H]resiniferatoxin binding and diminish calcium influx mediated by capsaicin. Oral administration of the dichloromethane fraction and α-spinasterol also produced antinociceptive effect in the noxious heat-induced nociception test; however, they did not change the mechanical threshold of naive mice. The treatment with α-spinasterol did not produce antinociceptive effect in mice systemically pretreated with resiniferatoxin. In addition, α-spinasterol and the dichloromethane fraction reduced the edema, mechanical, and heat hyperalgesia elicited by complete Freund's adjuvant paw injection. The dichloromethane fraction and α-spinasterol did not affect body temperature or locomotor activity. In conclusion, α-spinasterol is a novel efficacious and safe antagonist of the TRPV1 receptor with antinociceptive effect.

Topics: Analgesics; Animals; Binding, Competitive; Body Temperature; Calcium; Capsaicin; Chromatography, High Pressure Liquid; Diterpenes; Edema; Freund's Adjuvant; Hot Temperature; Male; Mice; Nociceptors; Pain; Pain Measurement; Plant Extracts; Plant Leaves; Stigmasterol; Tissue Distribution; TRPV Cation Channels; Vernonia

To study the triterpenoids constituents from Wisteria sinensis Sweet Caulis.. The compounds were beta-solated and purified with silica gel and Sephadex LH-20 column chromatography from the petroleum ether extract. Their structures were determined on the basis of physicochemical properties and spectroscopic analysis.. They were identified as beta-sitosterol palmitate (1), alpha-spinasterol (2), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3beta-ol (3), (22E, 24R)-ergosta-5, 7, 22-trien-3beta-ol (4), (22E, 24R) -ergosta-7, 22-dien-3beta-ol (5), 11alpha, 12alpha-oxidotaraxerol (6), lupeol (7), betulinic acid (8), 22-oxo-3beta, 24-dihydroxyolean-12-ene (9), 2alpha, 3beta, 23-trihydroxyolean-12-ene (10), soyasapogenol E (11), 3alpha, 21beta-dihydroxy-olean-12-ene (12).. Compounds 1 - 12 are isolated from this plant for the first time.

Topics: Ethanol; Molecular Structure; Plant Stems; Sitosterols; Stigmasterol; Triterpenes; Wisteria

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

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

Methanol extract of Koreana stewartia leaves (SKE) stimulated collagen production in ultraviolet-B (UVB)-irradiated human fibroblast cells. An active compound was isolated from SKE by successive partitioning and chromatography, and the chemical structure was determined to be 3-O-β-D-glucopyranosylspinasterol (spinasterol-Glc) by spectroscopic characterization. Spinasterol-Glc increased collagen production in the supernatant of UVB-irradiated dermal fibroblast cell cultures in a dose-dependent manner. The effects of spinasteol-Glc on expression of procollagen and matrix metalloproteinase-1 (MMP-1) were further evaluated. We found that the compound stimulated collagen production in UVB-treated fibroblasts than in vehicle-treated control cells by about 3-fold. In addition, we also demonstrate that the compound increased the mRNA and protein levels of procollagen in UVB-treated fibroblast cells, while it inhibited expression of MMP-1. These results indicate that spinasterol-Glc protects fibroblast cells from the adverse effects of UV radiation via stimulation of procollagen synthesis as well as inhibition of MMP-1 expression. Spinasterol-Glc may be useful in the future development of therapeutic and cosmetic applications.

Topics: Base Sequence; Blotting, Western; Cells, Cultured; DNA Primers; Fibroblasts; Humans; Matrix Metalloproteinase 1; Procollagen; Skin; Spectrometry, Mass, Fast Atom Bombardment; Stigmasterol; Theaceae

To study the chemical constituents of Codonopsis lanceolata.. Chemical constituents were separated with the column chromatographic, and their structures were identified by chemical and spectroscopic methods.. Six compounds were isolated and identified as syringin (1), shikimic acid (2), friedelin (3), alpha-spinasterol (4), stigmasterol (5), stigmasta-7-dien-3beta-ol (6).. Compounds 3-6 are isolated from this plant for the first time.

Topics: Codonopsis; Glucosides; Magnetic Resonance Spectroscopy; Phenylpropionates; Plant Roots; Plants, Medicinal; Shikimic Acid; Stigmasterol; Triterpenes

Phytochemical investigation of the petroleum ether extract fraction of Polyalthia cerasoides seeds led to the isolation of two phytosterols (alpha-spinasterol and spinasterol) and a clerodane di-terpenoid. The structures of these compounds were elucidated using IR, (1)H-NMR, (13)C-NMR and Mass spectral analysis. Further, these compounds were tested for antiproliferative action against CACO-2 cell line and apoptotic action was determined by nuclear staining and DNA fragmentation analysis. The results showed that the compounds exhibited antiproliferative action at various concentrations with an IC(50) value of 28.6+/-4.34nM/ml, 57.7+/-6.81nM/ml and 60.0+/-7.10nM/ml for clerodane diterpenoid, spinasterol and alpha-Spinasterol respectively. Furthermore, the isolated compounds were screened for antimutagenic effect against methylmethane sulfonate (MMS) induced mutation. Phytosterols showed protective effect, whereas clerodane diterpenoid was less effective to MMS induced chromosomal aberrations. Our research contributes to the characterization of phytochemical constituents and to understand the ability of these compounds to antiproliferative and antimutagenic responses from the seed extracts.

Topics: Antimutagenic Agents; Antineoplastic Agents, Phytogenic; Apoptosis; Caco-2 Cells; Cell Proliferation; Chromosome Breakage; Colonic Neoplasms; Diterpenes, Clerodane; Humans; Inhibitory Concentration 50; Magnetic Resonance Spectroscopy; Methyl Methanesulfonate; Mutagens; Mutation; Phytotherapy; Plant Extracts; Polyalthia; Seeds; Stigmasterol

The present study evaluates the gastroprotective properties of acetone extract, chloroform, and methanol fractions, alpha-spinasterol (1); 1,3-dihydroxy-7-methoxyxanthone (2); and 1,7-dihydroxy-2,3-methylenedioxyxanthone (3) obtained from Polygala cyparissias (Polygalaceae). Gastroprotective assays were performed in mice using ethanol/HCl and nonsteroidal anti-inflammatory drug (NSAID)/bethanechol-induced ulcer models. Chloroformic fraction showed no interesting results. On the other hand, in the ethanol/HCl-induced ulcer model, the treatment using doses of 50, 125, and 250 mg/kg promoted ulcer inhibition of 45.19+/-12.93%, 62.99+/-3.49%, and 67.40+/-4.75% for acetone extract and 43.70+/-5.12%, 64.56+/-5.64%, and 74.49+/-6.13% for methanol fraction. In the model of NSAID/bethanechol-induced ulcer, the ulcer inhibitions in the same doses were 28.12+/-12.45%, 60.16+/-6.58%, and 77.86+/-7.18% for the acetone extract and 46.09+/-6.92%, 67.45+/-4.36%, and 75.00+/-2.92% for the methanol fraction. In view of the antiulcer potential of the acetone extract and its high yield and xanthone content, it was submitted to chromatographic procedures, giving compounds 1-3, which were also evaluated in the ethanol-induced ulcer model. The results showed that at a dose of 50 mg/kg, these compounds reduced the percentage of ulcer by around 71.26+/-9.40%, 81.10+/-5.75%, and 86.22+/-3.42%, for compounds 1, 2, and 3, respectively. The antiulcerogenic activity of P. cyparissias may be attributed, at least in part, to these compounds.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Anti-Ulcer Agents; Bethanechol; Dose-Response Relationship, Drug; Ethanol; Hydrochloric Acid; Mice; Phytotherapy; Plant Extracts; Polygalaceae; Stigmasterol; Stomach Ulcer; Xanthones

ETHNOPHARMACOLOGYCAL RELEVANCE: The tea from the leaves of Baccharis illinita DC (Asteraceae family) is commonly used by the population as anti-inflammatory (including topically), protective gastric and anti-infectious. However, no studies have been done with this species to confirm its topical anti-inflammatory action.. This study evaluated he topical effects of crude extract of leaves (CE) and its active constituents in 12-O-tetradecanoylphorbol acetate (TPA)-induced ear oedema.. CE and compounds effects were tested in commonly used models of TPA-, arachidonic acid (AA)- and capsaicin-ear oedema. Polymorphonuclear (PMN) cell migration was evaluated by mieloperoxidase and analyzed histologically.. CE (0.1-1 mg/ear) caused a dose-related inhibition of TPA-induced ear oedema and PMN influx similarly to that produced by topical application of the steroidal anti-inflammatory drug dexamethasone. The active constituents of the AcOEt fraction kaurenoic acid, alpha-spinasterol, oleanolic acid and baurenol also inhibited TPA-induced ear edema. Histological analysis of the ear of CE-treated animals confirmed the reduction of edema and of PMN infiltration. Both CE and the nosteroidal anti-inflammatory drug indomethacin inhibited the AA-induced ear oedema, but did not change capsaicin-induced oedema.. These results indicate that the CE and the active constituents have a topical anti-inflammatory effect and the possible mechanisms for the pharmacological effects are discussed.

Topics: Administration, Topical; Animals; Anti-Inflammatory Agents; Arachidonic Acid; Baccharis; Capsaicin; Dermatitis, Contact; Disease Models, Animal; Diterpenes; Dose-Response Relationship, Drug; Ear; Edema; Male; Mice; Neutrophil Infiltration; Oleanolic Acid; Plant Leaves; Plant Preparations; Stigmasterol; Tetradecanoylphorbol Acetate

Arnica (Heterotheca inuloides) is a widely used medicinal plant in México; it has been recognized as anti-inflammatory, analgesic, cytotoxic, scavenger of superoxide anion and also as a preventive of lipid peroxidation. In vivo studies have demonstrated a hepatoprotective action of the methanolic extract of this plant as well as of quercetin, one of its main components, and the evidence obtained pointed out to an antioxidant mechanism. In this work, we focused on the free radical scavenging capacity of acetonic and methanolic extracts of H. inuloides in comparison with reference compounds. The two extracts were 2-12 times more effective (IC50, microg/mL) than the reference compounds to cope with the following radicals or molecules tested: 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(+)), 2,2-diphenyl-1-picrylhydrazyl (DPPH), peroxynitrite (ONOO(-)), superoxide (O2(-)), singlet oxygen ((1)O(2)), hypochlorous acid (HOCl), hydrogen peroxide (H2O2), hydroxyl (OH). Additionally, five secondary metabolites isolated from the methanolic extract displayed potent concentration-dependent antioxidant effects against reactive oxygen species produced in vitro (IC50 values in the range of 0.018-4.31mg/mL). d-Chiro-inositol showed the higher antioxidant effect against O2(-), H2O2 and OH while spinasterol and quercetin were the most active against (1)O(2) and ONOO(-), respectively. The antioxidant properties of the extracts and metabolites tested partially support the wide use of this plant in traditional medicine.

Topics: Antioxidants; Asteraceae; Dose-Response Relationship, Drug; Hydrogen Peroxide; Inhibitory Concentration 50; Medicine, Traditional; Mexico; Plant Extracts; Quercetin; Reactive Oxygen Species; Stigmasterol

Spinasterol, which is isolated from the aerial parts of Aster scaber Thunb. (Asteraceae), is involved in various biological activities. In this study, we report the efficacy of spinasterol in effectively modulating the regulation of antioxidative and anti-inflammatory activity through the upregulation of heme oxygenase (HO)-1 in murine hippocampal HT22 cells and BV2 microglia. We showed that spinasterol increased the cellular resistance of HT22 cells to oxidative injury caused by the glutamate-induced cytotoxicity by extracellular signal-regulated kinase (ERK) pathway-dependent expression of HO-1. Furthermore, spinasterol suppressed the lipopolysaccharide (LPS)-induced expression of pro-inflammatory enzymes and inflammatory mediators in BV2 microglia. Spinasterol also suppressed the production of nitric oxide (NO), prostaglandin E2 (PGE₂), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β) through extracellular signal-regulated kinase (ERK) pathway-dependent expression of HO-1. These results suggest that spinasterol has a therapeutic potential against neurodegenerative diseases that are caused by oxidative stress and neuroinflammation.

Topics: Animals; Anti-Inflammatory Agents; Blotting, Western; Cell Culture Techniques; Cell Line; Cell Survival; Cytoprotection; Dinoprostone; Enzyme Induction; Heme Oxygenase-1; Hippocampus; Interleukin-1; Mice; Microglia; Molecular Structure; Oxidative Stress; Reactive Oxygen Species; Stigmasterol; Tumor Necrosis Factor-alpha

The present study assessed the possible antinociceptive action of the hydroalcoholic extract, fractions and pure compounds obtained from the aerial parts of Baccharis illinita DC (Asteraceae) in behavioural models of chemical nociception in mice. The hydroalcoholic extract and fractions (hexane and aqueous but not EtOAc fraction) obtained from B. illinita (30-1000 mg/kg orally) produced a dose-related inhibition of the acetic acid-induced nociceptive response. However, the hexane fraction was more potent than the hydroalcoholic extract and the aqueous fraction. The hexane fraction derivatives baurenol, alpha-spinasterol and oleanolic acid (0.00001-10 mg/kg intraperitoneally) also caused potent inhibition of acetic acid-induced pain. The hexane fraction (300-1000 mg/kg orally) produced inhibition of both phases of formalin-induced pain. Moreover, the hexane fraction (30-600 mg/kg orally) also caused a dose-dependent inhibition of glutamate-induced pain. Nevertheless, the hexane fraction only at the dose of 300 mg/kg orally, produced partial inhibition of the paw oedema caused by carrageenan. Furthermore, the hexane fraction (300 mg/kg orally) caused inhibition of the nociceptive response induced by intrathecal injection of N-methyl-d-aspartic acid, alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid, tumour necrosis factor-alpha and interleukin-1beta. In contrast, the hexane fraction did not affect the biting response induced by the metabotropic or ionotropic glutamatergic receptor agonist (+/-)-1-aminocyclopentane-trans-1,3-dicarboxylic acid and kainate, respectively. In addition, the antinociception caused by the hexane fraction (300 mg/kg orally) in the acetic acid test was not affected by intraperitoneal treatment of mice with naloxone (a non-selective opioid receptor antagonist). The precise mechanism responsible for the antinociceptive effect of the hexane fraction remains unclear, but appears to be partly associated with an inhibition of glutamatergic transmission and an inhibition of pathways dependent on pro-inflammatory cytokines. Finally, baurenol, alpha-spinasterol and oleanolic acid have an important role in the antinociceptive effects of the hexane fraction. Moreover, the antinociceptive action demonstrated in the present study supports the ethnomedical uses of this plant.

Topics: Analgesics; Animals; Baccharis; Cytokines; Disease Models, Animal; Dose-Response Relationship, Drug; Female; Mice; Oleanolic Acid; Pain; Pain Measurement; Plant Components, Aerial; Plant Extracts; Receptors, Glutamate; Solvents; Stigmasterol; Triterpenes

To Study liposoluble constituents of Teurium labiosum.. The constituents were isolated and purified by silica gel column and Sephadex LH-20 chromatography. Their structures were elucidated by physicochemical properties and spectral analysis.. Six compounds were obtained and identified as stearic acid (I), alpha-spinasterol (II), Methyl phaeophorbide a (III), friedelino (IV), lupeol (V) and stigmasta-5,22-dien-3beta-ol (VI).. All these compounds are obtained from this plant for the first time.

Topics: Alcohols; Lamiaceae; Magnetic Resonance Spectroscopy; Oleanolic Acid; Pentacyclic Triterpenes; Plants, Medicinal; Solvents; Stearic Acids; Stigmasterol; Triterpenes

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

Several studies have provided new insights into the role of sphingolipid/sterol-rich domains so-called lipid rafts of the plasma membrane (PM) from mammalian cells, and more recently from leaves, cell cultures, and seedlings of higher plants. Here we show that lipid raft domains, defined as Triton X-100-insoluble membranes, can also be prepared from Medicago truncatula root PMs. These domains have been extensively characterized by ultrastructural studies as well as by analysis of their content in lipids and proteins. M. truncatula lipid domains are shown to be enriched in sphingolipids and Delta(7)-sterols, with spinasterol as the major compound, but also in steryl glycosides and acyl-steryl glycosides. A large number of proteins (i.e. 270) have been identified. Among them, receptor kinases and proteins related to signaling, cellular trafficking, and cell wall functioning were well represented whereas those involved in transport and metabolism were poorly represented. Evidence is also given for the presence of a complete PM redox system in the lipid rafts.

Topics: Cell Fractionation; Medicago truncatula; Membrane Lipids; Membrane Microdomains; Oxidation-Reduction; Plant Proteins; Plant Roots; Proteomics; Solubility; Stigmasterol

To investigate the chemical constituents from the root of Psammosilene tunicoides.. Column chromatographic methods were used to isolate the chemical constituents of this plant. ESI-MS, EI-MS and NMR methods were employed for their structural elucidation.. Seven compounds were isolated and identified as goyaprosaponin (1), Soya-cerebroside (2), tectoridin (3), alpha-spinasterol (4), tetracosanoic acid (5), beta-sitosterol (6), daucosterol (7) respectively.. Compounds 2-7 were obtained from genus Psammosilene for the first time.

Topics: Caryophyllaceae; Cerebrosides; Isoflavones; Magnetic Resonance Spectroscopy; Plant Roots; Plants, Medicinal; Spectrometry, Mass, Electrospray Ionization; Stigmasterol

We have investigated the possible antinociceptive action of the extract, fractions and pure compounds obtained from the whole plant Polygala sabulosa A. W. Bennett (Polygalaceae) in acetic acid-induced visceral pain in mice. Intraperitoneal injection of animals with the hydroalcoholic extract and fractions (CH(2)Cl(2), EtOAc, n-BuOH, aqueous fraction) (1-100 mg kg(-1)) caused a dose-related and significant inhibition of the acetic acid-induced visceral nociceptive response. The CH(2)Cl(2), EtOAc and n-BuOH fractions were more potent than the hydroalcoholic extract and aqueous fraction. The isolated compounds dihydrostyryl-2-pyrones (1, 2, 3), styryl-2-pyrone (7), alpha-spinasterol (9), scopoletin (10) and two esters of the coumarin (scopoletin) obtained semisynthetically, acetylscopoletin (10a) and benzoylscopoletin (10b) (0.001-10 mg kg(-1)), exhibited significant and dose-related antinociceptive effects against acetic acid-induced visceral pain. The results distinguished, for the first time, the extract, fractions and pure compounds obtained from P. sabulosa that produced marked antinociception against the acetic acid-induced visceral nociceptive response, supporting the ethnomedical use of P. sabulosa.

Topics: Abdominal Pain; Acetic Acid; Analgesics; Animals; Coumarins; Male; Mice; Pain Measurement; Plant Extracts; Polygala; Pyrones; Stigmasterol

To investigate the chemical constituents of the rhizome of Curcuma phaeocaulis Val.. The constituents were isolated by column chromatography and their structures elucidated by chemical properties and spectroscopic analysis.. Five compunds have been isolated and identified as isocurcumenol, curcumenol, alpha-spinasterol, curcumin, and beta-sitosterin-3-O-glucoside.. alpha-Spinasterol and alpha-stediol were isolated from Curcuma phaeocaulis Val. for the first time.

Topics: Curcuma; Curcumin; Molecular Structure; Plants, Medicinal; Rhizome; Sesquiterpenes; Stigmasterol

We purified phytoestrogens from Pueraria root (Pueraria mirifica from Thailand and Pueraria lobata from Korea), which is used as a rejuvenating folk medicine in Thailand and China. Dried, powdered plant material was extracted with 100% ethanol and further separated by concentration, filtration, and thin layer silica gel chromatography. Using the fractions obtained during separation, we first investigated their cytotoxicity in several cancer cell lines from various tissues. The ethanol-extracted components (PE1, PE4) had significant antiproliferative effects on breast cancer cell lines, including MCF-7, ZR-75-1, MDA-MB-231, SK-BR-3, and Hs578T. Second, we compared these results with the cytotoxic effects of known flavonoids, sterols, and coumarins from Pueraria root. The known compounds were not as effective, and occurred in a different polarity region on HPLC. Third, further separation resulted in the isolation of eight different components (Sub PE-A to -H). One of these, PE-D, affected the growth of some breast cancer cell lines (MCF-7, MDA- MB-231) in a dose- and time-dependent manner, as well as the growth of ovarian (2774) and cervical cancer cells (HeLa). Finally, a transfection assay showed that this component had an estrogenic effect similar to 17beta - estradiol, which activates both estrogen receptor alpha (ERalpha) and ERbeta. The NMR analysis determined that spinasterol (stigmasta-7, 22-dien-3beta-ol) is an active cytotoxic component of Pueraria root.

Topics: Antineoplastic Agents; Chromatography, High Pressure Liquid; Estrogen Receptor alpha; Estrogen Receptor beta; Female; Humans; Plant Preparations; Plant Roots; Pueraria; Stigmasterol; Transfection; Tumor Cells, Cultured

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 from the rhizome of Impatiens pritzellii var. hupehensis.. The rhizome were extracted with methanol, isolated and purified by column chromatography on silica gel. All the compounds were identified on the basis of spectral analysis (including IR, MS, NMR) and physico-chemical characters.. Five compounds were identified as a-spinasterol (I), alpha-spinasteryl-7, 22-dien-3-O-beta-D-glucopyranoside (II), stigmast-7, 22-dien-3-one (III), stearic acid (IV), hentriantane (V).. Compound I is isolated from this plant for the first time, Compound II, III, IV, V are isolated from genus Balsaminaceae for the first time.

Topics: Impatiens; Plants, Medicinal; Rhizome; Stearic Acids; Stigmasterol

From the roots of Securidaca inappendiculata, one new sterol glycoside securisteroside (1) has been isolated, along with two known sterols, spinasterol (2) and 3-O-beta-D-glucopyranosyl-spinasterol (3). The new sterol was characterized by chemical and spectrometric methods, including EIMS, FABMS and one- and two-dimensional NMR experiments.

Topics: Magnetic Resonance Spectroscopy; Mass Spectrometry; Plant Roots; Securidaca; Stigmasterol

To study the constituents of the root of Gypsophila oldhamiana Miq.. Silica gel column chromatographic technique was used for the isolation and purification of compounds. The structures were elucidated on the basis of spectral data and chemical evidences.. Five compounds were obtained and identified as the beta-D-glucoside of alpha-spinasterol (I), tetracosyl caffeate (II), sucrose (III), beta-sitosterol (IV) and daucosterol (V).. Compound II is a new compound. Compound I was isolated from this plant for the first time.

Topics: Caffeic Acids; Caryophyllaceae; Molecular Conformation; Molecular Structure; Plant Roots; Plants, Medicinal; Stigmasterol; Sucrose

The chemical investigation of the hexane extract of the stem bark of Gordonia ceylanica afforded 3beta-acetoxy-11alpha(2',3'-epoxyferulyloxy)-olean-13(18)-ene as a new natural product and alpha-spinasterol for the first time from Gordonia.

Topics: Chromatography, Liquid; Chromatography, Thin Layer; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Bark; Plant Stems; Plants, Medicinal; Spectrophotometry, Infrared; Spectrum Analysis; Sri Lanka; Stigmasterol; Theaceae; Triterpenes

Spinasterol, an antimutagen, was isolated from squash flowers by solvent partitioning and repeated vacuum liquid chromatography. Spinasterol was then tested for its anticarcinogenic potential by using the mouse skin tumor assay. There was a 90% skin tumor incidence for the positive control group (DMBA + croton oil + acetone). At a concentration of 15.0 microg/0.2 ml acetone, spinasterol decreased the incidence of skin tumors by 55.6% and decreased the number of tumors by 65.0% when applied immediately after croton oil. Hence, spinasterol showed antitumorigenic potential. It is not a co-carcinogen nor a co-tumor promoter as there was no increase in the incidence of skin tumors after spinasterol application. Teratogenesis Carcinog. Mutagen. 20:99-105, 2000.

Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Anticarcinogenic Agents; Carcinogens; Chloroform; Chromatography, Liquid; Cocarcinogenesis; Croton Oil; Cucurbitaceae; Drug Screening Assays, Antitumor; Methanol; Mice; Molecular Structure; Skin Neoplasms; Solvents; Stigmasterol; Time Factors

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

Five compounds were isolated from the aerial part of Conyza blinii. On the basis of physicochemical properties and spectroscopic analysis, they were identified as alpha-spinasterol, 5, 8-dihydroxy-7, 3', 4'-trimethoxyflavone, caffeic acid, quercetin and syringic acid. All these compounds were isolated from the plant of C. blinii for the first time.

Topics: Asteraceae; Caffeic Acids; Drugs, Chinese Herbal; Plant Shoots; Plants, Medicinal; Quercetin; Stigmasterol

Most work reporting the sterol composition of living organisms has not been done quantitatively, although good quantitative data are available for fatty acids and many other cellular components using an internal-standard method that compensates for errors during gas chromatographic analysis. In this paper, we report on the use of 7-stigmastenyl acetate as an internal standard for sterol analysis in two species of phytoplankton and oysters produced with two different diets. This internal-standard method provides an internal standard for this entire process of analysis, not just the gas chromatographic analysis. When analyzing 50-microgram samples of cholesterol acetate after hydrolysis and acetylation, about 30% of the sample was lost, resulting in a 30% error using the older external-standard method. Using the internal-standard method, the analysis error was less than 2%. Losses of sterol during analysis apparently are greater with plant and animal samples than with pure sterol standards. This internal-standard method was shown to be extremely useful, especially for samples with less than 500 micrograms of sterol. Finally, the standard error in sterol analysis is much lower when the internal-standard method is used, allowing statistical distinctions that are not possible otherwise. Use of 7-stigmastenyl acetate as an internal standard offers several advantages over the use of cholestane.

Topics: Animals; Cholesterol; Cholesterol Esters; Ostreidae; Phytoplankton; Reference Standards; Sterols; Stigmasterol

Seven compounds were isolated from Aster poliothamnus. By means of spectral evidences and crystal analysis, their structures were elucidated as beta-sitosterol, beta-amyrin, daucosterol, spinasterol, stigmasterol, dammara-20, 24-dien-3 beta-ol and epifriedlinol.

Topics: Asteraceae; Molecular Conformation; Plants, Medicinal; Stigmasterol; Triterpenes

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

The antigenotoxic constituent of squash flowers was isolated by solvent partitioning and repeated vacuum liquid chromatography. The micronucleus test, an in vivo method, was used to monitor the antigenotoxicity of the various fractions during the isolation process. Isolate SQFwB2D from the chloroform extract of squash flowers is the most antigenotoxic isolate. It decreased the mutagenicity of tetracycline by 64.7% at a dosage of 100 mg/kg mouse. Statistical analysis using Kruskall Wallis one-way analysis of variance by Ranks showed that SQFw2D is different from the control group (tetracycline + corn oil) at alpha = 0.001. GC-MSD of isolate SQFwB2D shows 2 peaks at Rt = 19.860 (SQFwB2D-1) and 20.242 min (SQFwB2D-2) with relative peak heights of 16:1, respectively. Spectral analyses show that SQFwB2D-1 is 24 alpha-ethyl-5 alpha-cholesta-7,trans-22-dien-3 beta-ol or spinasterol.

Topics: Animals; Antimutagenic Agents; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mice; Micronucleus Tests; Spectrophotometry, Infrared; Stigmasterol; Vegetables

Topics: Anti-Inflammatory Agents; Diterpenes; Drugs, Chinese Herbal; Plant Roots; Plants, Medicinal; Stigmasterol

Ten compounds were isolated from Codono psis pilosula var. volubilis. Six of them were characterized as friedelin, taraxerol, alpha-spinasterol, alpha-spinasterol-beta-D-glucopyranoside, n-butyl-alpha-D-fructofuranoside and n-butyl-beta-D-fructopyranoside.

Topics: Drugs, Chinese Herbal; Fructose; Stigmasterol

A new bergenin derivative isolated from the root of Ardisia crenata was determined to be 11-o-syringylbergenin by spectral methods. Other compounds were identified as spinasterol, series fatty acids, beta-sitosterol-beta-D-glucoside, norbergenin and sucrose respectively. The last three were obtained for the first time from the genus of Ardisia.

Topics: Benzopyrans; Chemical Phenomena; Chemistry; Drugs, Chinese Herbal; Sitosterols; Stigmasterol; Sucrose

Topics: Medicine, Chinese Traditional; Medicine, East Asian Traditional; Nitrates; Phytosterols; Plants, Medicinal; Potassium Compounds; Stigmasterol; Succinates; Succinic Acid

Topics: Animals; Anti-Inflammatory Agents; Capillary Permeability; Edema; Female; Foot Diseases; Male; Mice; Phytosterols; Rats; 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: Plant Extracts; Plants, Medicinal; Sitosterols; Stigmasterol

Topics: Chemistry Techniques, Analytical; Glucosides; Glycosides; Medicago sativa; Palmitic Acid; Research; Sterols; Stigmasterol

Topics: Bile Acids and Salts; Humans; Steroids; Stigmasterol