Oxidative metabolism of ambrox and sclareolide by Botrytis cinerea.
Ambrox (1), a perfumery diterpene, was oxidatively metabolised by a plant pathogenic fungus Botrytis cinerea in a xenobiotic fashion to afford a major product, i.e., 1beta-hydroxy-8-epiambrox (13) (60%) along with three minor metabolites 3beta-hydroxyambrox (2), sclareolide (5) and 3beta-hydroxysclareolide (7). Sclareolide (5), a cytotoxic diterpenoidal lactone was fermented with the same fungus to yield 3beta-hydroxysclareolide (7) (59%) as a major metabolite together with two minor metabolites characterised as 1-ketosclareolide (15), and 3beta,14-dihydroxysclareolide (16).
Farooq
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A
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
Tahara
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S
D020171:Botrytis / Q000378:metabolism*; D004224:Diterpenes / Q000737:chemistry / Q000378:metabolism*; D005285:Fermentation; D005663:Furans / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D010944:Plants / Q000382:microbiology
D004224:Diterpenes; D005663:Furans; D009281:Naphthalenes; C109395:sclareolide; C413580:ambrox