Biotransformation of (+)-fenchone by Salmonella typhimurium OY1002/2A6 expressing human CYP2A6 and NADPH-P450 reductase

J Oleo Sci. 2013;62(5):293-6. doi: 10.5650/jos.62.293.

Abstract

In this study, biotransformation of (+)-fenchone (compound 1) by Salmonella typhimurium OY1002/2A6 expressing human CYP2A6 and NADPH-P450 reductase yielded two oxidized metabolites, namely, (+)-(1S,6R)-6-endo-hydroxyfenchone (compound 2) and (+)-(1S,6S)-6-exo-hydroxyfenchone (compound 3). The conversion rate of compound 1 to compound 2 and 3 was 2.4% and 5.2%, respectively. This is the first study that succeeded in metabolizing compound 1 to obtain large amounts of metabolite 2 and 3 by using S. typhimurium OY1002/2A6 expressing human CYP2A6 and NADPH-P450 reductase.

MeSH terms

  • Aryl Hydrocarbon Hydroxylases / biosynthesis*
  • Aryl Hydrocarbon Hydroxylases / genetics
  • Biotransformation
  • Camphanes
  • Cytochrome P-450 CYP2A6
  • Humans
  • NADPH-Ferrihemoprotein Reductase / biosynthesis*
  • NADPH-Ferrihemoprotein Reductase / genetics
  • Norbornanes / metabolism*
  • Salmonella typhimurium / enzymology*
  • Salmonella typhimurium / genetics

Substances

  • Camphanes
  • Norbornanes
  • fenchone
  • Aryl Hydrocarbon Hydroxylases
  • CYP2A6 protein, human
  • Cytochrome P-450 CYP2A6
  • NADPH-Ferrihemoprotein Reductase