Metabolic products of microorganisms. 261. Obscurolides, a novel class of phosphodiesterase inhibitors from streptomyces. I. Production, isolation, structural elucidation and biological activity of obscurolides A1 to A4.
A novel class of butyrolactones, named obscurolides, was isolated from the culture filtrate of Streptomyces viridochromogenes by chemical screening methods. The structural elucidation of the obscurolides A1 to A4 (1 approximately 4) is described. The carboxy group of the 4-aminobenzoic acid moiety of obscurolide A1 (1) is reduced in the other compounds. The isolated natural products have been proved to be diastereomeric mixtures by a partial racemization at C-7 which belongs to an allylic alcohol system. The obscurolides showed a weak inhibitory activity against calcium/calmodulin-dependent and independent phosphodiesterases from bovine.
Hoff
H
H
Biologisches Institut, Universität Tübingen, Germany.
Drautz
H
H
Fiedler
H P
HP
Zähner
H
H
Schultz
J E
JE
Keller-Schierlein
W
W
Philipps
S
S
Ritzau
M
M
Zeeck
A
A
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D001921:Brain / Q000201:enzymology; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D000242:Cyclic AMP / Q000378:metabolism; D005285:Fermentation; D006868:Hydrolysis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D009206:Myocardium / Q000201:enzymology; D010726:Phosphodiesterase Inhibitors / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013302:Streptomyces / Q000378:metabolism
D010726:Phosphodiesterase Inhibitors; C076471:obscurolide A1; C076472:obscurolide A2; C076473:obscurolide A3; C076474:obscurolide A4; D000242:Cyclic AMP; D015107:4-Butyrolactone