Biotransformation of ent-13-epi-manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi

Phytochemistry. 2004 Jan;65(1):107-15. doi: 10.1016/j.phytochem.2003.09.017.

Abstract

Biotransformation of ent-3beta,12alpha-dihydroxy-13-epi-manoyl oxide with Fusarium moniliforme gave the regioselective oxidation of the hydroxyl group at C-3 and the ent-7beta-hydroxylation. The action of Gliocladium roseum in the 3,12-diketoderivative originated monohydroxylations at C-1 and C-7, both by the ent-beta face, while Rhizopus nigricans produced hydroxylation at C-7 or C-18, epoxidation of the double bond, reduction of the keto group at C-3, and combined actions as biohydroxylation at C-2/epoxidation of the double bond and hydroxylation at C-7/reduction of the keto group at C-3. In the ent-3-hydroxy-12-keto epimers, G. roseum originated monohydroxylations at C-1 and C-7 and R. nigricans originated the oxidation at C-3 as a major transformation, epoxidation of double bond and hydroxylation at C-2. Finally, in the ent-3beta-hydroxy epimer R. nigricans also originated minor hydroxylations at C-1, C-6, C-7 and C-20 and F. moniliforme produced an hydroxylation at C-7 and a dihydroxylation at C-7/C-11.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Epoxy Compounds / chemistry
  • Fusarium / metabolism*
  • Gliocladium / metabolism*
  • Hydroxylation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Rhizopus / metabolism*
  • Stereoisomerism
  • Terpenes / chemistry*
  • Terpenes / metabolism*

Substances

  • Epoxy Compounds
  • Terpenes
  • ent-13-epi-manoyl oxide