Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 55, Issue 4, Pages 537-540Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.55.537
Keywords
microbial transformation; Streptomyces lavendulea; cembranoid; Sinularia
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5-Episinuleptolide (1) is an abundant norcembranolide diterpene isolated from several species of the soft coral genus Sinularia. Biocatalytic transformation studies of 1 using Streptomyces lavendulea ATCC 8664 resulted in the isolation and characterization of two new metabolites 2 and 3. Compound 2, 6 alpha-hydroxy-5-episinuleptolide was produced via a stereoselective reduction of 1 and was further metabolized into compound 3 which has a 3,8-bicylized cembranoid skeleton. The structures and configurations of the metabolites were determined by spectroscopic and X-ray crystallographic analyses.
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