The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
New 1-O-Acyl α-L-Rhamnopyranosides and Rhamnosylated Lactones from Streptomyces sp., Inhibitors of 3α-Hydroxysteroid-dehydrogenase (3α-HSD)
JIN-FENG HU, DIRK WUNDERLICH, ISABEL SATTLER, ALBERT HÄRTL, INA PAPASTAVROU, STEPHANIE GROND, SUSANNE GRABLEY, XIAO-ZHANG FENG, RALF THIERICKE
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2000 Volume 53 Issue 9 Pages 944-953

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Abstract

Chemical screening with extracts of Streptomyces sp. (strain GT 61150) resulted in the detection, isolation, and structure elucidation of two new acyl α-L-rhamnopyranosides (1 and 2) and three new rhamnosyllactones A, B1 and B2 (3-5). 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 6-11 inhibit the enzyme 3α-hydroxysteroid-dehydrogenase (3α-HSD).

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The Journal of Antibiotics, Series A

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