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来自链霉菌属的新型1-O-酰基-α-L-鼠李吡喃糖苷和鼠李糖基化内酯,3α-羟基类固醇脱氢酶(3α-HSD)抑制剂。

New 1-O-acyl alpha-L-rhamnopyranosides and rhamnosylated lactones from Streptomyces sp., inhibitors of 3 alpha-hydroxysteroid-dehydrogenase (3alpha-HSD).

作者信息

Hu J F, Wunderlich D, Sattler I, Härtl A, Papastavrou I, Grond S, Grabley S, Feng X Z, Thiericke R

机构信息

Hans-Knöll-Institute for Natural Products Research, Jena, Germany.

出版信息

J Antibiot (Tokyo). 2000 Sep;53(9):944-53. doi: 10.7164/antibiotics.53.944.

DOI:10.7164/antibiotics.53.944
PMID:11099228
Abstract

Chemical screening with extracts of Streptomyces sp. (strain GT 61150) resulted in the detection, isolation, and structure elucidation of two new acyl alpha-L-rhamnopyranosides (1 and 2) and three new rhamnosyllactones A, B1 and B2 (3 approximately 5). Rhamnosyllactones B1 and B2 were obtained as a 5:1 mixture. The structures were confirmed by spectroscopic analysis, especially 2D-NMR techniques. The rhamnosyltransferase of our strain is able to connect the sugar moiety to heteroaromatic carboxylic acids and enols. The metabolites 1 and 4/5 as well as previously reported acylrhamnosides 6 approximately 11 inhibit the enzyme 3alpha-hydroxysteroid-dehydrogenase (3alpha-HSD).

摘要

用链霉菌属(菌株GT 61150)提取物进行化学筛选,结果检测、分离并阐明了两种新的酰基α-L-鼠李吡喃糖苷(1和2)以及三种新的鼠李糖基内酯A、B1和B2(3至5)。鼠李糖基内酯B1和B2以5:1的混合物形式获得。结构通过光谱分析得以确认,尤其是二维核磁共振技术。我们菌株的鼠李糖基转移酶能够将糖部分连接到杂芳族羧酸和烯醇上。代谢产物1和4/5以及先前报道的酰基鼠李糖苷6至11可抑制3α-羟基类固醇脱氢酶(3α-HSD)。

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