24-ethyl-4-cholesten-3-one and gamma-sitosterol

Chemical examination of Chinese mangrove

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

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

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

14C-labeled C29- and C27-steroids were injected in rats, which were killed after 14 days. Phytosterols (C29) were excreted mainly as such, whereas C27-steroids were recovered essentially as water soluble metabolites. The total 14C-excretion was lower from 3-oxo, delta 4-steroids (5 alpha-stanol precursors) than from 3 beta-hydroxy,delta 5-steroids. 14C-Phytosterols were accumulated more than C27-steroids in liver, serum (mainly in HDL) and especially in adrenal glands and ovaries. In relation to serum, particularly the 5 alpha-stanols were enriched in the adrenal glands and ovaries. No striking lysosomal accumulation of any of the steroids was found.

Topics: Animals; Arteriosclerosis; Blood Proteins; Cricetinae; Female; Injections, Intraperitoneal; Lipid Metabolism, Inborn Errors; Liver; Rats; Rats, Inbred Strains; Sitosterols; Subcellular Fractions; Tissue Distribution