New 1-O-Acyl α-L-Rhamnopyranosides and Rhamnosylated Lactones from Streptomyces sp., Inhibitors of 3α-Hydroxysteroid-dehydrogenase (3α-HSD)

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 s...

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Veröffentlicht in:	Journal of antibiotics 2000/09/25, Vol.53(9), pp.944-953
Hauptverfasser:	HU, JIN-FENG, WUNDERLICH, DIRK, SATTLER, ISABEL, HÄRTL, ALBERT, PAPASTAVROU, INA, GROND, STEPHANIE, GRABLEY, SUSANNE, FENG, XIAO-ZHANG, THIERICKE, RALF
Format:	Artikel
Sprache:	eng
Schlagworte:	1-Acyl ^a-L-rhamnopyranosides 1-O-acyl ^a-L-rhamnopyranosides 3^a-Hydroxysteroid dehydrogenase 3a-Hydroxysteroid dehydrogenase Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology Biological and medical sciences Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Fundamental and applied biological sciences. Psychology Furans - chemistry Furans - isolation & purification Furans - pharmacology General aspects Glycosides - chemistry Glycosides - isolation & purification Glycosides - pharmacology Hydroxysteroid Dehydrogenases - antagonists & inhibitors lactones Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Magnetic Resonance Spectroscopy Microbiology Streptomyces Streptomyces - chemistry Streptomyces - metabolism Structure-Activity Relationship
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Zusammenfassung:	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).
ISSN:	0021-8820 1881-1469
DOI:	10.7164/antibiotics.53.944