title: 9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa.
abstract: Nine new 9,11-secosterols (1-9), containing the same 3β,6α,11-trihydroxy-9,11-seco-5α-cholest-7-en-9-one steroidal nucleus, whereas possessing an array of structurally diverse side chains, along with fourteen known 9,11-secosterol compounds (10-23), were isolated from the South China Sea gorgonian coral Subergorgia suberosa, of which 3/4, 5/6, 7/8, and the known compounds 11/12, 20/21 were five pairs of inseparable C-24 epimers. Their structures were established by the extensive analyses of 1D and 2D NMR spectra, high-resolution chemical ionization mass spectrometry (HRCIMS), and by the comparison with literature data. Cytotoxic effect of these metabolites against the growth of HeLa cell lines was evaluated. The result showed that the inhibitory effect of compounds 1-23 varied considerably depending on the nature of the side chain in spite of sharing the same steroidal nucleus. Compound 19, featuring both the absence of hydroxyl group and the presence of double bond in the stigmasterol side chain, exhibited the most potent cytotoxicity with IC50 being 15.1 μM. The preliminary structure activity relationship studies identified some important structural features considerably influencing the biological effect deserved, providing valuable information for chemists and pharmacologists to design and synthesize more effective antitumor agents bearing the 9,11-secosteroid framework.
authors: College of Pharmacy, Jinan University, Guangzhou 510632, PR China; National Engineering Research Centre of Navel Orange, Gannan Normal University, Ganzhou 341000, PR China.
authors: Jun
authors: J
authors: Zhang
authors: Division of Life Science, School of Science, The Hong Kong University of Science and Technology, Hong Kong Special Administrative Region.
authors: Ling-Li
authors: LL
authors: Liu
authors: National Engineering Research Centre of Navel Orange, Gannan Normal University, Ganzhou 341000, PR China.
authors: Ba-Lian
authors: BL
authors: Zhong
authors: Department of Chemistry, Jinan University, Guangzhou 510632, PR China.
authors: Xiao-Jian
authors: XJ
authors: Liao
authors: College of Pharmacy, Jinan University, Guangzhou 510632, PR China; Department of Chemistry, Jinan University, Guangzhou 510632, PR China. Electronic address: txush@jnu.edu.cn.
authors: Shi-Hai
authors: SH
authors: Xu
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D012632:Secosteroids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D003603:Cytotoxins; D012632:Secosteroids
keywords: 9,11-Secosterol; Cytotoxicity; Gorgonian coral; Subergorgia suberosa