title: Characteristic Steroids from the South China Sea Gorgonian Muricella sibogae and Their Cytotoxicities.
abstract: Twenty-four steroid-based natural products, 9,10-secosteroids (1-10), 1,4-dien-3-one steroids (11-19), and 4-en-3-one steroids (20-24), containing varying side-chains, were isolated from the South China Sea gorgonian Muricella sibogae. The structures of one new 9,10-secosteroid, sibogol D (1), and two new 1,4-dien-3-one steroids, sibogols E and F (11 and 12), were elucidated by extensive spectroscopic analyses and by comparison with the literature data. Cytotoxicities for all the isolates were evaluated against four selected tumor cell lines, HL-60, HCT116, K562, and P388. Compounds 3, 9, and 13 exhibited potent cytotoxic activities against the HL-60 cell line, with IC50 values ranging from 1.27 to 10.05 μM, and compound 3 was also cytotoxic against HCT116 with an IC50 value of 5.8 μM. The bioassay results also indicated a potential relationship between structural patterns and activity. The newly presented series of 1,4-dien-3-one and 4-en-3-one types of steroids relating to the unique 9,10-secosteroids in biogenesis were found in this species for the first time, which is of considerable chemotaxonomic significance.
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China (phone: +86-532-82032323; fax: +86-532-82033054).
authors.forename: Xing-Wang
authors.initials: XW
authors.lastname: Zhang
authors.affiliation: College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, P. R. China.
authors.forename: Xu-Li
authors.initials: XL
authors.lastname: Tang
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China (phone: +86-532-82032323; fax: +86-532-82033054).
authors.forename: Bao-Sheng
authors.initials: BS
authors.lastname: Liu
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China (phone: +86-532-82032323; fax: +86-532-82033054). liguoqiang@ouc.edu.cn.
authors.forename: Ping-Lin
authors.initials: PL
authors.lastname: Li
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China (phone: +86-532-82032323; fax: +86-532-82033054).
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Li
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018922:HL-60 Cells; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D012632:Secosteroids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D012632:Secosteroids
keywords: Chemotaxonomy; Gorgonian; Muricella sibogae; Sibogols D - F; Steroidal diversity