title: Tumor cell growth inhibitory activity and structure-activity relationship of polyoxygenated steroids from the gorgonian Menella kanisa.
abstract: Fourteen new polyoxygenated steroids (6, 9, 14-18, 20-23, 25-27) having carbon skeletons of cholestane, ergostane, and 24-norcholestane, were isolated together with thirteen known analogues (1-5, 7, 8, 10-13, 19, 24) from the South China Sea gorgonian Menella kanisa. The structures of the new compounds were elucidated by detailed analysis of spectroscopic data and comparisons with reported data. This is the first report of chemical investigation on the title gorgonian. Compounds 12 and 13 were reported for the first time from natural sources. These compounds exhibited different levels of growth inhibition activity against A549 and MG-63 cell lines in bioassay in vitro. Preliminary structure-activity analysis revealed an important role of side chain in the activity. A substitution of a 5α-hydroxy or an oxidation of 6β-hydroxy to a ketone carbonyl group may decrease the activity whereas the contribution of the 1-ketone group remains uncertain.
authors.affiliation: Research Center for Marine Drugs and Department of Pharmacology, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, PR China.
authors.forename: Pan
authors.initials: P
authors.lastname: Wang
authors.forename: Hua
authors.initials: H
authors.lastname: Tang
authors.forename: Bao-Shu
authors.initials: BS
authors.lastname: Liu
authors.forename: Tie-Jun
authors.initials: TJ
authors.lastname: Li
authors.forename: Peng
authors.initials: P
authors.lastname: Sun
authors.forename: Wen
authors.initials: W
authors.lastname: Zhu
authors.forename: Yan-Ping
authors.initials: YP
authors.lastname: Luo
authors.forename: Wen
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents
keywords: Menella kanisa; Polyoxygenated steroids; Structure elucidation; Structure–activity relationship; Tumor cell growth inhibition