Bioactive polyhydroxylated steroids from the Hainan soft coral Sinularia depressa Tixier-Durivault

Lin-Fu Liang; Xu-Jie Wang; Hai-Yan Zhang; Hai-Li Liu; Jia Li; Le-Fu Lan; Wen Zhang; Yue-Wei Guo

doi:10.1016/j.bmcl.2012.12.087

Bioactive polyhydroxylated steroids from the Hainan soft coral Sinularia depressa Tixier-Durivault

Bioorg Med Chem Lett. 2013 Mar 1;23(5):1334-7. doi: 10.1016/j.bmcl.2012.12.087. Epub 2013 Jan 4.

Authors

Lin-Fu Liang¹, Xu-Jie Wang, Hai-Yan Zhang, Hai-Li Liu, Jia Li, Le-Fu Lan, Wen Zhang, Yue-Wei Guo

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhang Jiang Hi-Tech Park, Shanghai 201203, PR China.

PMID: 23357636
DOI: 10.1016/j.bmcl.2012.12.087

Abstract

Two new steroids, (2β,3β,4α,5α,8β)-4-methylergost-24(28)-ene-2,3,8-triol (1) and (3β,7α)-24-methyl-7-hydroperoxycholest-5,24(28)-diene-3-ol (2), together with 13 known analogues (3-15) were isolated from the soft coral Sinularia depressa Tixier-Durivault. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. In the bioassay in vitro, compounds 3a, 4, and 14 exhibited potent PTP1B inhibitory activity, being similar as that of positive control oleanolic acid. Compound 14 also displayed a notable neuroprotective activity against both amyloid-β(25-35)- and serum deprivation-induced injuries in SH-SY5Y cells while compound 11 showed a considerable antibacterial activity against Staphylococcus aureus. Preliminary structure-activity relationships of these steroids were discussed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anthozoa / chemistry*
Cell Line, Tumor
Humans
Hydroxylation
Microbial Sensitivity Tests
Molecular Structure
Stereoisomerism
Steroids / chemistry*
Steroids / isolation & purification
Steroids / pharmacology*
Structure-Activity Relationship

Substances

Steroids