First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa

被引：15

作者：

Boonananwong, Suthinee ^{[1
]}

Kongkathip, Boonsong ^{[1
]}

Kongkathip, Ngampony ^{[1
]}

机构：

[1] Kasetsart Univ, Nat Prod & Organ Synth Res Unit, Dept Chem, Fac Sci, Bangkok 10900, Thailand

来源：

STEROIDS | 2008年 / 73卷 / 11期

关键词：

steroid synthesis; biological activity; anticancer activity; polyoxygenated cholestanes;

D O I：

10.1016/j.steroids.2008.04.013

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Using tigogenin as starting material, (20S)-20-hydroxycholestane-3,6-dione (1), (16S, 20S)-16,20-dihydroxycholestan-3-one (2), (20S)-20-hydroxycholest-1-ene-3,16-dione (3) and (20S)-20-hydroxycholest-4-ene-3,16-dione (4), natural polyoxygenated Steroids from the gorgonian, Leptogorgia sarmentosa, were synthesized in four steps. Antitumor activity against three tumor cell lines (breast cancer, MCF7, lung cancer NCI and oral cancer KB) was evaluated. Two compounds (3 and 4) showed strong activity against NCI (IC50 6.16 and 10.51 mu M) and moderate activity against MCF7 and KB, the IC50 being in the range 30.6S-47.22 mu M. Compound 2 showed moderate activity against NCI (IC50 42.68 mu M) but was inactive against MCF7 and KB whereas compound 1 showed no activity against all tested cells. (c) 2008 Elsevier Inc. All rights reserved.

引用

页码：1123 / 1127

页数：5

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