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

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 elu...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2013-03, Vol.23 (5), p.1334-1337
Main Authors: Liang, Lin-Fu, Wang, Xu-Jie, Zhang, Hai-Yan, Liu, Hai-Li, Li, Jia, Lan, Le-Fu, Zhang, Wen, Guo, Yue-Wei
Format: Article
Language:English
Subjects:
Animals
Anthozoa - chemistry
Antibacterial
antibacterial properties
bioassays
blood serum
Cell Line, Tumor
corals
Humans
Hydroxylation
Microbial Sensitivity Tests
Molecular Structure
Neuroprotective
neuroprotective effect
oleanolic acid
PTP1B
Sinularia
Sinularia depressa
Soft coral
spectroscopy
Staphylococcus aureus
Stereoisomerism
Steroid
steroids
Steroids - chemistry
Steroids - isolation & purification
Steroids - pharmacology
Structure-Activity Relationship
structure-activity relationships
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Summary: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-β25–35- 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.12.087