Terpenoids produced by actinomycetes: isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088

被引：0
作者：
Masato Shirai
Masaaki Okuda
Keiichiro Motohashi
Masaya Imoto
Kazuo Furihata
Yoshihide Matsuo
Atsuko Katsuta
Yoshikazu Shizuri
Haruo Seto
机构：
[1] Faculty of Applied Bioscience,Department of Applied Biology and Chemistry
[2] Tokyo University of Agriculture,undefined
[3] Faculty of Science and Technology,undefined
[4] Keio University,undefined
[5] Graduate School of Agricultural and Life Sciences,undefined
[6] University of Tokyo,undefined
[7] Marine Biotechnology Institute Co. Ltd.,undefined
[8] Marine Biosciences,undefined
[9] Kamaishi Research Laboratory,undefined
[10] Kitasato University,undefined
[11] 6Current address: Suntory Holdings Limited,undefined
[12] R&D Planning Division,undefined
[13] Wakayamadai,undefined
[14] Shimamoto-cho,undefined
[15] Mishima-gun,undefined
[16] Osaka,undefined
[17] 618-8503,undefined
[18] Japan.,undefined
来源：
The Journal of Antibiotics | 2010年 / 63卷
关键词：
androgen receptor binding inhibitor; biosynthesis; cyperusol C; gifhornenolone; terpenoid;
D O I：
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中图分类号：
学科分类号：
摘要：
New terpenoids named gifhornenolones A (1) and B (2) were isolated from the culture broth of Verrucosispora gifhornensis YM28-088, and their structures were established as hydroxylated isopimaradiene derivatives on the basis of extensive NMR and MS spectral analyses. In addition, a known sesquiterpene compound cyperusol C (3) was isolated. The absolute configuration of 1 was determined by nuclear Overhauser effect spectroscopy (NOESY) and CD spectra as 4R, 5S, 9R, 10S, 13R, and that of 2 was determined by NOESY experiments as 3R, 4R, 5R, 9R, 10S, 13R. Labeling experiments with [1-13C]glucose and [U-13C6]glucose confirmed that the MEP (2-C-methyl-D-erythritol-4-phosphate) pathway was used for the biosynthesis of terpenoids in this organism. 1 showed potent inhibitory activity to the androgen receptor with an IC50 of 2.8 μg ml−1.
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页码：245 / 250
页数：5
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