Polyoxygenated sterols from the Formosan soft coral Sinularia gibberosa.
Chemical investigation on the dichloromethane-soluble fraction from the EtOH extract of Sinularia gibberosa Tixier-Durivault has led to the isolation of three new polyoxygenated sterols, gibberoketosterols B (1) and C (2) and gibberoepoxysterol (3), along with two known steroids, gibberoketosterol (4) and 24-methylenecholest-5-en-3beta-ol (5). These cholestane-type sterols possessing a 22,24(28)-conjugated diene (1 and 2) in the side chain or a 5alpha,6alpha-epoxide in the B-ring (3) were isolated for the first time from marine sources. Compound 4 showed significant inhibition against the up-regulation of the pro-inflammatory iNOS and COX-2 proteins of LPS-stimulated RAW264.7 macrophage cells, while 1 was found to be inactive. The cytotoxicity of 1-4 toward a limited panel of cancer cell lines is also reported.
Ahmed
Atallah F
AF
Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, Republic of China.
Hsieh
Ya-Ting
YT
Wen
Zhi-Hong
ZH
Wu
Yang-Chang
YC
Sheu
Jyh-Horng
JH
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D015394:Molecular Structure; D052247:Nitric Oxide Synthase Type II / Q000187:drug effects; D013261:Sterols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013624:Taiwan; D014407:Tumor Cells, Cultured
D052246:Cyclooxygenase 2 Inhibitors; D008070:Lipopolysaccharides; D013261:Sterols; C514317:gibberoepoxysterol; C514315:gibberoketosterol B; C514316:gibberoketosterol C; D052247:Nitric Oxide Synthase Type II