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Bioactive 9,11‐Secosteroids from Gorgonian Subergorgia suberosa Collected from the South China Sea
Author(s) -
Liu Min,
Shao ChangLun,
Chen Min,
Qi Jun,
Wang Yu,
Fang YuChun,
Wang ChangYun
Publication year - 2014
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201400021
Subject(s) - gorgonian , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , chemistry , steroid , terpenoid , biology , biochemistry , coral , ecology , hormone
Five new 9,11‐secosteroids 1, 2 , and 4 – 6 , and seven known analogs, 3 and 7 – 12 , with the same steroid skeleton, (5 αH ) ‐ 3 β ,6 α ,11‐trihydroxy‐9,11‐secocholest‐7‐en‐9‐one, were isolated from the South China Sea gorgonian Subergorgia suberosa. Among them, 2 / 3 and 4 / 5 are C(24) ‐epimeric mixtures, and 6 / 7 is an ( E )/( Z ) mixture of (C(24)C(28)). Their structures and relative configurations were elucidated by using comprehensive spectroscopic methods including NOESY spectra. The absolute configuration of the steroidal nucleus was established by the modified Mosher method applied to 10 and on the basis of a common biogenesis for all of these compounds. All isolated compounds, 1 – 12 , and five synthetic acetylated derivatives, 12a – 12e , were evaluated for their cytotoxicities in vitro. Compounds 4 / 5, 11, 12 , and 12b – 12d showed cytotoxic activities against K562 cell line with the IC 50 values ranging from 1.09 to 8.12 μ M .