Microbial transformation of 17α-ethynyl- and 17α-ethylsteroids, and tyrosinase inhibitory activity of transformed products

被引：28

作者：

Choudhary, AL ^{[1
]}

Sultan, S ^{[1
]}

Khan, MTH ^{[1
]}

Rahman, AU ^{[1
]}

机构：

[1] Univ Karachi, HEJ Res Inst Chem, Int Ctr Chem Sci, Karachi 75270, Pakistan

来源：

STEROIDS | 2005年 / 70卷 / 12期

关键词：

17; alpha-ethynyl-17; beta-hydroxyandrost-4-en-3-one; alpha-ethyl-17; microbial transfortnation; Cephalosporium aphidicola; Cunninghamella elegans; tyrosinase inhibition;

D O I：

10.1016/j.steroids.2005.05.002

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：

The microbial transformation of the 17 alpha-ethynyl-17 beta-hydroxyandrost-4-en-3-one (1) (ethisterone) and 17 alpha-ethyl-17 beta-hydroxyandrost4-en-3-one (2) by the fungi Cephalosporium aphidicola and Cunninghamella elegans were investigated. Incubation of compound 1 with C. aphidicola afforded oxidized derivative, 17 alpha-ethynyl-17 beta-hydroxyandrosta-1,4-dien-3-one (3), while with C elegans afforded a new hydroxy derivative, 17 alpha-ethynyl-11 alpha, 17 beta-dihydroxyandrost-4-en-3-one (4). On the other hand, the incubation of compound 2 with the fungus C aphidicola afforded 17 alpha-ethyl-17 beta-hydroxyandrosta-1,4-dien-3-one (5). Two new hydroxylated derivatives, 17 alpha-ethyl-11 alpha,17 beta-dihydroxyandrost-4-en-3-one (6) and 17 alpha-ethyl-6 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one (7) were obtained from the incubation of compound 2 with C. elegans. Compounds 1-6 exhibited tyrosinase inhibitory activity, with compound 6 being the most potent member (IC50 = 1.72 mu M). (c) 2005 Elsevier Inc. All rights reserved.

引用

页码：798 / 802

页数：5

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