Hydroxylation and glucoside conjugation in the microbial metabolism of the diterpene sclareol.
1. The microbial metabolism of sclareol (1), a labdane diterpene ditertiary alcohol, was studied. Preliminary screening identified a number of microorganisms capable of metabolizing sclareol. 2. Preparative scale fermentation of growing cultures of Bacillus cereus UI-1477 resulted in the production of seven metabolites which have been characterized as 3 beta-hydroxysclareol (2), 2 alpha-hydroxysclareol (3), 18-hydroxysclareol (4), 2 alpha,18-dihydroxysclareol (6), 8 alpha,13 beta-dihydroxy-labd-14-en-3 beta-O-beta-D-glucoside (5), 8 alpha,13 beta-dihydroxy-labd-14-en-18-O-beta-D-glucoside (7), and 8 alpha,13 beta-dihydroxy-labd-14-en-2 alpha-O-beta-D-glucoside (10) by chemical, enzymic, and spectral data, especially 2D-n.m.r. techniques and thermospray liquid chromatography-mass spectrometry analysis.
Kouzi
S A
SA
Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University 38677.
McChesney
J D
JD
D001409:Bacillus cereus / Q000378:metabolism; D001711:Biotransformation; D004224:Diterpenes / Q000737:chemistry / Q000378:metabolism* / Q000493:pharmacokinetics; D005285:Fermentation; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism; D006001:Glycoconjugates / Q000737:chemistry / Q000378:metabolism; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004224:Diterpenes; D005960:Glucosides; D006001:Glycoconjugates; C070760:sclareol