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Microbiological transformation of manoyl oxide derivatives by Mucor plumbeus

AuthorsFraga, Braulio M. CSIC; González, Pedro; Guillermo, Ricardo; Hernández, Melchor G.
Issue Date1998
PublisherAmerican Chemical Society
CitationJournal of Natural Products 61(10): pp. 1237-1241 (1998)
AbstractBiotransformations of jhanol (18-hydroxymanoyl oxide( (2). jhanidiol (1$,18-dihydroxymanoyl oxide (3), and 1-oxo-jhanol (1-oxo-18-hydroxymanoyl oxide) (4) by the fungus Mucor plumbeus have bee studied. In the incubation of 2 there exists a preference for hydroxylation at C-2(a)(8) and C-6($)(9-11) and, to a lesser degree, at C-1(a)(7), C-11(a)(6), and C-11($)(5 and 10). In the second substrate (3), the presence of a 1$-hydroxyl group inhibits 6$- or 11-hydroxylation. Epoxidation of the vinyl group constitutes the main reaction, with the positions 2a (14) and 3$ (15) being hydroxylated. In the incubation of 4, there was a preference for 6$-hydroxylation (21) or epoxidation of the vinyl group (22). Other hydroxylations observed were at the 2a (19), 2$ (20), 3a (23), 3$ (24), and 11$ (18) positions.
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