Microbial transformation of cedrol
1993
Maatooq, G. | El-Sharkawy, S. | Afifi, M.S. | Rosazza, J.P.N.
(+)-Cedrol (1) was biotransformed by cultures of Steptomyces griseus ATCC 10137 and Bacillus cereus UI 1477 (NRRL B-14591). Metabolites isolated by solvent extraction and chromatography over Si gel and reversed-phase RP-C18 columns and by preparative tlc, were examined by ms and 1H- and 13C-nmr spectroscopy. B. cereus afforded 2S-hydroxycedrol (2) as the only metabolite. The metabolite 2 is apparently formed when cedrol is properly oriented at the cytochrome P-452 hydroxylase of B. cereus. S. griseus afforded 3S-hydroxycedrol (3), 4R-hydroxycedrol (4), 4-oxocedrol (5), 10S-hydroxycedrol (7), 4-oxo-3S-hydroxycedrol (8), 3R,4S-dihydroxycedrol (9), 10S,11S-dihydroxycedrol (10), and 11-oxo-10S-hydroxycedrol (11), 4R,10S-dihydroxycedrol (12), and 3S,10S-dihydroxycedrol (13). Metabolites 5 and 8-13 are new oxygenated cedrol derivatives.
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