title: Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis.
abstract: Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.
authors.affiliation: Division of Environmental Resources, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
authors.forename: Noemia Kazue
authors.initials: NK
authors.lastname: Ishikawa
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Tahara
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Namatame
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
authors.forename: Afgan
authors.initials: A
authors.lastname: Farooq
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
authors.forename: Yukiharu
authors.initials: Y
authors.lastname: Fukushi
mesh_terms: D000890:Anti-Infective Agents / Q000378:metabolism*; D053898:Biosynthetic Pathways; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D055393:Flammulina / Q000378:metabolism*; D012717:Sesquiterpenes / Q000378:metabolism*
chemical_list: D000890:Anti-Infective Agents; D012717:Sesquiterpenes; D003577:Cytochrome P-450 Enzyme System
keywords: 4-quinone; Antimicrobial compound; Flammulina velutipes; cuparene-1; edible mushroom; enokitake