stigmasterol and ergosterol-5-8-peroxide

Compounds from the hexane, dichloromethane and acetone extracts of Heritiera littoralis bark were investigated for their nitric oxide (NO) inhibitory effects using RAW264.7 macrophage cells. The result indicated that ergosterol peroxide (13) exhibited the highest activity against NO release with an IC(50) value of 2.5 microM, followed by 6-alpha-hydroxystigmast-4-en-3-one (11, IC(50)=9.5 microM) and stigmast-4-en-3-one (9, IC(50)=15.9 microM), whereas other compounds showed moderate and mild effects (25.4- > 100 microM). Ergosterol peroxide (13) and 6-alpha-hydroxystigmast-4-en-3-one (11) were also tested against prostaglandin E(2) (PGE(2)) and tumor necrosis factor alpha (TNF-alpha) releases. It was found that ergosterol peroxide (13) possessed marked activity against PGE(2) release with an IC(50) value of 28.7 microM, while 6-alpha-hydroxystigmast-4-en-3-one (11) was 86.7 microM. However, these two compounds were inactive towards TNF-alpha release (IC(50) > 100 microM). The mechanism in transcriptional level of ergosterol peroxide (13) was found to down regulate mRNA expressions of iNOS and COX-2 in dose-dependent manners.

Topics: Animals; Anti-Inflammatory Agents; Cell Line; Cyclooxygenase 2; Dinoprostone; Dose-Response Relationship, Drug; Down-Regulation; Ergosterol; Gene Expression Regulation; Inhibitory Concentration 50; Macrophages; Malvaceae; Mice; Nitric Oxide; Nitric Oxide Synthase Type II; Plant Bark; Plant Extracts; RNA, Messenger; Stigmasterol

An activity-guided fractionation method was used to isolate anticancer components from Nuruk (Rhizopus oryzae KSD-815:KSD-815). Dried powder of KSD-815 was extracted with 80% methanol and partitioned successively using nhexane, ethyl acetate, n-butanol, and water. The n-hexane and n-butanol fractions showed a strong antimigratory effect on human cancer cells. Both of these fractions were subjected to separation and purification procedures using silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies to afford four purified compounds. These were identified as ergosterol peroxide (1), stigmast- 5-en-3beta,7beta-diol (2), ergosta-7,22-dien-3beta,5alpha,6beta,9alpha-tetraol (3), and daucosterol (4), respectively, by spectroscopic methods such as nuclear magnetic resonance spectrometry, mass spectrometry, and infrared spectroscopy, and comparison with those in the literature. Compounds 1-4 were isolated from KSD-815 for the first time. Compounds 1 and 4 inhibited the migration of MDA-MB-231 cells at concentrations lower than 20 micronM.

Topics: Breast Neoplasms; Cell Line, Tumor; Cell Movement; Edible Grain; Ergosterol; Female; Food Microbiology; Humans; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Rhizopus; Sitosterols; Spectrophotometry, Infrared; Sterols; Stigmasterol

A new stigmasterol, (24S)-stigmast-5-en-7beta-ethoxy-3beta-ol (2) together with three known sterols have been isolated from the ethanolic extract of the pericarp of Sphaerophysa salsula (Pall.) DC, and their structures elucidated mainly on the basis of the spectral data and comparison with the literature.

Topics: China; Chromatography, Gel; Ergosterol; Fabaceae; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Phytosterols; Plant Extracts; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Infrared; Stigmasterol