Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis

• Main Author: Ishikawa,Noemia Kazue
• Publication Date: 2013
• Other Authors: Tahara,Satoshi, Namatame,Tomohiro, Farooq,Afgan, Fukushi,Yukiharu
• Format: Article
• Language: eng
• Source: Brazilian Journal of Microbiology
• Download full: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822013000400037
• topic: Antimicrobial compound; cuparene-1,4-quinone; edible mushroom; enokitake; Flammulina velutipes

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.