Microbial transformation of 5-episinuleptolide.
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, 6alpha-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.
Kamel
Haidy Nasr
HN
Department of Pharmacognosy and National Center for Natural Products Research, RIPS, School of Pharmacy, University of Mississippi, MS 38677, USA. knkamel@olemiss.edu
Fronczek
Frank Rolf
FR
Khalifa
Sherief Ibrahim
SI
Slattery
Marc
M
D001711:Biotransformation; D004224:Diterpenes / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012015:Reference Standards; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013302:Streptomyces / Q000378:metabolism*
C520059:5-episinuleptolide; D004224:Diterpenes