Stigmasterol is a plant sterol with anti-apoptotic, anti-oxidative and anti-inflammatory effect through multiple mechanisms. In this study, we further assessed whether it exerts protective effect on human brain microvessel endothelial cells (HBMECs) against ischemia-reperfusion injury and explored the underlying mechanisms. HBMECs were used to establish an in vitro oxygen and glucose deprivation/reperfusion (OGD/R) model, while a middle cerebral artery occlusion (MCAO) model of rats were constructed. The interaction between stigmasterol and EPHA2 was detected by surface plasmon resonance (SPR) and cellular thermal shift assay (CETSA). The results showed that 10 μmol·L^-1 stigmasterol significantly protected cell viability, alleviated the loss of tight junction proteins and attenuated the blood-brain barrier (BBB) damage induced by OGD/R in thein vitro model. Subsequent molecular docking showed that stigmasterol might interact with EPHA2 at multiple sites, including T692, a critical gatekeep residue of this receptor. Exogenous ephrin-A1 (an EPHA2 ligand) exacerbated OGD/R-induced EPHA2 phosphorylation at S897, facilitated ZO-1/claudin-5 loss, and promoted BBB leakage in vitro, which were significantly attenuated after stigmasterol treatment. The rat MCAO model confirmed these protective effects in vivo. In summary, these findings suggest that stigmasterol protects HBMECs against ischemia-reperfusion injury by maintaining cell viability, reducing the loss of tight junction proteins, and attenuating the BBB damage. These protective effects are at least meditated by its interaction with EPHA2 and inhibitory effect on EPHA2 phosphorylation.
Humans ; Animals ; Rats ; Stigmasterol ; Phosphorylation ; Endothelial Cells ; Molecular Docking Simulation ; Reperfusion Injury ; Blood-Brain Barrier ; Glucose ; Microvessels ; Oxygen

The present study aimed to study lipid-lowering effect of seven traditional Chinese medicine monomers in zebrafish system. Zebrafish were fed with high fat diet to establish a hyperlipemia model, then fasted and bathed with seven traditional Chinese medicine monomers stigmasterol, triacontanol, chrysophanol, vanillic acid, shikimic acid, polydatin and oleanolic acid respectively. The oil red O staining was used to detect the blood lipids of zebrafish. Serum total cholesterol and triglyceride levels were detected to validate the lipid-lowering effect. The result showed that a zebrafish model of hyperlipemia could be established by feeding larvae zebrafish with high fat diet. Among the seven traditional Chinese medicine monomers, chrysophanol had lipid-lowering effect. Chrysophanol significantly reduced serum total cholesterol and triglyceride levels in adult zebrafish fed with high fat diet. Chrysophanol accelerated peristalsis frequency of zebrafish intestine and the excretion of high fat food. It is concluded that chrysophanol has lipid- lowering effect in zebrafish, and the mechanism of the effect may be due to the roles of chrysophanol in reducing lipid absorption from gastrointestinal tract and accelerating the excretion of food.
Animals ; Anthraquinones ; pharmacology ; Diet, High-Fat ; Fatty Alcohols ; pharmacology ; Glucosides ; pharmacology ; Hyperlipidemias ; drug therapy ; Hypolipidemic Agents ; pharmacology ; Larva ; Lipids ; blood ; Medicine, Chinese Traditional ; Oleanolic Acid ; pharmacology ; Shikimic Acid ; pharmacology ; Stigmasterol ; pharmacology ; Stilbenes ; pharmacology ; Vanillic Acid ; pharmacology ; Zebrafish

This study analyzed the seeds of Zizyphus jujuba var. inermis commonly used as a remedy in traditional Chinese medicine, in order to determine its various biologically active compounds. Through process 3-pentadecylcatechol, ρ-menth-8-ene, and γ-bisabolene were isolated and identified for the first time which are urushiol, monoterpenoidal, and sesquiterpenoidal compounds, respectively. Also, found were another sesquiterpenoidal compounds, vomifoliol, and four steroidal compounds, β-sitosterol, stigmasterol, stigmasta-5,23-dien-3β-ol, and stigmast-4-en-3-one. In addition, fourteen triterpenoidal compounds were isolated and identified. These were lupeol, betulinic acid, betulinaldehyde, alphitolic acid, 3-O-cis-ρ-coumaroyl-alphitolic acid, 3-O-trans-ρ-coumaroylalphitolic acid, 2-O-cis-ρ-coumaroyl-alphitolic acid, 2-O-trans-ρ-coumaroyl-alphitolic acid, zizyberanalic acid, ceanothic acid, oleanolic acid, maslinic acid, 3-O-cis-ρ-coumaroyl-maslinic acid, and 3-O-trans-ρ-coumaroylmaslinic acid. The structures were identified by comparing of the spectroscopic experiments, NMR and MS, and then compared that reported data, respectively. Three extracts of water, methanol, and chloroform from the seeds showed a weak anti-proliferative effect, anti-microbial activity, and anti-oxidant effect, respectively.
Antioxidants ; Chloroform ; Medicine, Chinese Traditional ; Methanol ; Oleanolic Acid ; Stigmasterol ; Water ; Ziziphus*

Phytochemical investigation on the leaves of Pileostegia viburnoides Hook.f.et Thoms led to the isolation of twenty-five compounds, and their structures were identified as n-dotriacontane (1), taraxeryl acetate (2), friedelin (3), epifriedelinol (4), canophyllal (5), stigmast-4-en-3-one (6), stigmasterol (7), (24R)-5A-stigmastane-3,6-dione (8), ursolic acid (9), pomolic acid (10), umbelliferone (11), 4-epifriedelin (12), n-octatriacontanol (13), β-amyrin (14), α-amyrin (15), taraxerol (16), nonadecanol (17), friedelane (18), arachic acid (19), protocatechuic acid (20), n-pentatriacontanol (21), hexadecanoic acid (22), vincosamide (23), daucosterol (24), and skimming (25), respectively. To our best knowledge, compounds 1, 2, 12, 13, 17 - 19 and 21-23 were new within Saxifragaceae family. Compounds 15, 16, and 20 were produced from this genus for the first time. Compounds 4, 14 and 25 were first obtained from species P. viburnoides and compounds 3, 5 - 11, and 24 were achieved from the leaves of P. viburnoides for the first time. Furthermore, the anti-neuroinflammatory activity of these isolates was evaluated.
Coumarins ; Humans ; Palmitic Acid ; Saxifragaceae ; Stigmasterol ; Triterpenes

AIM: To investigate the active chloroform fraction of the ethanol extract of Ipomoea carnea flowers on hematological changes in toluene diisocyanate-induced inflammation in Wistar rats. METHOD: Except for the control group, all of the rats were sensitized with intranasal application of 5 μL of 10% toluene diisocyanate (TDI) for 7 days. One week after second sensitization, all of the rats were provoked with 5 μL of 5% TDI to induce airway hypersensitivity. After the last challenge, blood and bronchoalvelor lavage (BAL) fluid were collected and subjected to total and differential leucocytes count. Flash chromatography was performed on the most active chloroform fraction to isolate an individual component. RESULTS: Treatment with the ethanolic extract and its chloroform fraction at an oral dose of 200 mg·kg⁻¹ showed a significant decrease in circulating neutrophil and eosinophil in blood and BAL as compared with standard dexamethasone (DEXA). The structure of the compound obtained from chloroform fraction of Ipomea carnea was elucidated as stigmast-5, 22-dien-3β-ol on the basis of spectral data analysis. CONCLUSION The chloroform fraction was found to be more effective to suppress airway hyper reactivity symptoms, and decreased count of both total and differential inflammatory cells.
Animals ; Asthma ; blood ; chemically induced ; drug therapy ; metabolism ; Bronchoalveolar Lavage Fluid ; Eosinophils ; metabolism ; Female ; Flowers ; chemistry ; Hematology ; Inflammation ; blood ; chemically induced ; drug therapy ; metabolism ; Ipomoea ; chemistry ; Leukocyte Count ; Male ; Molecular Structure ; Neutrophils ; metabolism ; Phytotherapy ; Plant Extracts ; chemistry ; pharmacology ; therapeutic use ; Rats ; Rats, Wistar ; Stigmasterol ; analogs & derivatives ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Toluene 2,4-Diisocyanate

To investigate the chemical constituents of Chamaecyparis obtusa var. breviramea f. crippsii, various column chromatography and spectroscopic methods were used for the isolation and elucidation of compounds. One new monoterpenoid glucoside, (4S)-4-isopropylcyclohex-l-enecarboxylic acid 4-O-beta-D-glucopyranoside (1), together with five known compounds, (4R)-p-menth-l-ene-7, 8-diol 7-O-beta-D-glucopyranoside (2), skimmin (3), 7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2H-1-benzopyran-2-one (4), stigmast-4-en-3-one (5) and 1, 4-benzenedicarboxylic acid 1-butyl-4-(2-methylpropyl) ester (6) were isolated and identified from the twigs of this plant. All compounds were isolated from this plant for the first time. The methanol extract of this plant showed cytotoxicity on cancer cell lines A549, BGC-823, Du145 and MDA-MB-231 with IC50 values of 0.94, 1.07, 0.95 and 0.96 microg x mL(-1), respectively. Yet, compounds 1, 2 and 3 showed no cytotoxicity on cancer cell lines HeLa, BGC-823 and A549.
Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Chamaecyparis ; chemistry ; Coumarins ; chemistry ; isolation & purification ; pharmacology ; Glucosides ; chemistry ; isolation & purification ; pharmacology ; Humans ; Molecular Structure ; Monoterpenes ; chemistry ; isolation & purification ; pharmacology ; Plant Leaves ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Stigmasterol ; analogs & derivatives ; chemistry ; isolation & purification ; pharmacology

OBJECTIVETo study the chemical constituents of Oxytropis microphylla.

METHODThe 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).

RESULTEight 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).

CONCLUSIONAll 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.

Chromatography, High Pressure Liquid ; Flavanones ; chemistry ; Flavonoids ; chemistry ; Kaempferols ; chemistry ; Lactones ; chemistry ; Oxytropis ; chemistry ; Sesquiterpenes ; chemistry ; Sitosterols ; chemistry ; Spectrometry, Mass, Electrospray Ionization ; Stigmasterol ; chemistry ; Triterpenes ; chemistry

OBJECTIVETo study the constituents of the whole herbs of Vernonia cinerea. by bio-activity guided isolation with PC-12 model.

METHODThe constituents were separated by column chromatography and the structures were elucidated by spectroscopic methods.

RESULTFour compounds were identified to be (+)-lirioresinol B (1), stigmasterol (2), stigmasterol-3-O-beta-D-glucoside (3), 4-sulfo-benzocyclobutene (4), and their NGF inducing activity were also investigated.

CONCLUSIONCompounds 1, 3, 4 were isolated from this genus for the first time, and compound 4 was identified as a new natural product. Compounds 1, 3, 4 showed cytotoxicity on PC-12, and compounds 2, 3, 4 showed inhibition activity. Compound 4 showed a specific effect on the survival of TrkA fibroblasts, and resulted in the inducing NGF activity.

Animals ; Drugs, Chinese Herbal ; chemistry ; Glucosides ; chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; PC12 Cells ; Polycyclic Compounds ; chemistry ; pharmacology ; Rats ; Stigmasterol ; analogs & derivatives ; chemistry ; Vernonia ; chemistry

OBJECTIVETo study the chemical constituents of Dendobium crystallinum.

METHODCompounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography. Their structures were identified by physicochemical properties and spectral analyses.

RESULTNine compounds were obtained and identified as: 4, 4'-dihydroxy-3, 5-dimethoxybi-benzyl (1), gigantol (2), naringenin (3) , p-hydroxybenzoic acid (4), n-tetracosyl trans-p-cou-marate (5), n-octacosy trans-p-coumarate (6), n-hexacosyl trans-ferulate (7), stigmasterol (8), daucosterol (9).

CONCLUSIONAll these compounds were obtained from this plant for the first time, compounds 1 and 4 were isolated firstly from the genus.

Bibenzyls ; Chromatography ; Dendrobium ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Flavanones ; chemistry ; Guaiacol ; analogs & derivatives ; chemistry ; Magnetic Resonance Spectroscopy ; Parabens ; chemistry ; Sitosterols ; chemistry ; Stigmasterol ; chemistry

OBJECTIVETo investigate the chemical constituents from the root of Psammosilene tunicoides.

METHODColumn 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.

RESULTSeven 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.

CONCLUSIONCompounds 2-7 were obtained from genus Psammosilene for the first time.

Caryophyllaceae ; chemistry ; Cerebrosides ; chemistry ; isolation & purification ; Isoflavones ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Spectrometry, Mass, Electrospray Ionization ; Stigmasterol ; analogs & derivatives ; chemistry ; isolation & purification