Microbial transformations of isocupressic acid.
Microbial transformations of the labdane-diterpene isocupressic acid (1) with different microorganisms yielded several oxygenated metabolites that were isolated and characterized by MS and NMR spectroscopic analyses. Nocardia aurantia (ATCC 12674) catalyzed the cleavage of the 13,14-double bond to yield a new nor-labdane metabolite, 2. Cunninghamella elegans (-) (NRRL 1393) gave 7beta-hydroxyisocupressic acid (3) and labda-7,13(E)-diene-6beta,15, 17-triol-19-oic acid (4), and Mucor mucedo (ATCC 20094) gave 2alpha-hydroxyisocupressic acid (5) and labda-8(17),14-diene-2alpha, 13-diol-19-oic acid (6).
Division of Medicinal and Natural Products Chemistry, and Center for Biocatalysis and Bioprocessing, College of Pharmacy, University of Iowa, Iowa City, Iowa 52242, USA.
S J
SJ
Lin
J P
JP
Rosazza
D001711:Biotransformation; D002240:Carbohydrate Sequence; D002264:Carboxylic Acids / Q000378:metabolism*; D003470:Culture Media; D004224:Diterpenes; D005658:Fungi / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009089:Mucor / Q000378:metabolism; D009090:Mucorales / Q000378:metabolism; D009615:Nocardia / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013764:Tetrahydronaphthalenes / Q000378:metabolism*
D002264:Carboxylic Acids; D003470:Culture Media; D004224:Diterpenes; D013764:Tetrahydronaphthalenes; C110793:isocupressic acid