Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis

Bioorg Med Chem Lett. 2009 Oct 1;19(19):5640-3. doi: 10.1016/j.bmcl.2009.08.026. Epub 2009 Aug 8.

Abstract

We previously revealed that Orf8 and Orf6, which were identified in the brassicicene C biosynthetic gene cluster in Alternaria brassicicola strain ATCC96836, were fusicoccadiene (FD) synthase and 16-O-methyltransferase, respectively. In the present Letter, the early biosynthetic steps after the formation of FD were investigated. Plasmids carrying the FD synthase gene, one (or two) of five cytochrome P450 genes (orf1, orf2, orf5, orf7, and orf11) identified in the cluster and a cytochrome P450 reductase gene cloned from strain ATCC96836 were constructed and introduced into Saccharomyces cerevisiae. Based on the structures of the compounds produced by the transformants, Orf1 is suggested to be an 8beta-hydroxylation enzyme that yields FD 8beta-ol (4), followed by 16-hydroxylation by Orf7 to produce FD 8beta16-diol (5).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / genetics
  • Cytochrome P-450 Enzyme System / genetics*
  • Cytochrome P-450 Enzyme System / metabolism
  • Diterpenes / chemistry
  • Diterpenes / metabolism*
  • Hydroxylation
  • Multigene Family
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism

Substances

  • Diterpenes
  • Recombinant Proteins
  • brassicicene C
  • Cytochrome P-450 Enzyme System