New 1-O-acyl alpha-L-rhamnopyranosides and rhamnosylated lactones from Streptomyces sp., inhibitors of 3 alpha-hydroxysteroid-dehydrogenase (3alpha-HSD).
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).
Hu
J F
JF
Hans-Knöll-Institute for Natural Products Research, Jena, Germany.
Wunderlich
D
D
Sattler
I
I
Härtl
A
A
Papastavrou
I
I
Grond
S
S
Grabley
S
S
Feng
X Z
XZ
Thiericke
R
R
D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006913:Hydroxysteroid Dehydrogenases / Q000037:antagonists & inhibitors*; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
C417122:2-(1-propen-1-yl)-4-hydroxymethyl-3-furanylcarbonyl-rhamnopyranoside; D004791:Enzyme Inhibitors; D005663:Furans; D006027:Glycosides; D007783:Lactones; C417124:rhamnosyllactone A; C417123:rhamnosyllactone B1; D006913:Hydroxysteroid Dehydrogenases