Cytochrome P450/NADPH-dependent formation of trans epoxides from trans-arachidonic acids

Bioorg Med Chem Lett. 2004 Feb 23;14(4):1019-22. doi: 10.1016/j.bmcl.2003.11.054.

Abstract

Trans-arachidonic acids (trans-AA) are products of cis-trans isomerization of arachidonic acid by nitrogen dioxide radical (NO(2)), and occur in vivo, but their metabolism is unknown. We found that hepatic microsomes oxidized trans-AA via cytochrome P450/NADPH system to epoxides, which were hydrolyzed by epoxide hydrolase to diols (DiHETEs). 14,15-trans-AA produced one erythro diol and three threo diols each having one trans double bond.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Arachidonic Acid / chemistry
  • Arachidonic Acid / isolation & purification
  • Arachidonic Acid / metabolism*
  • Cytochrome P-450 Enzyme System / metabolism*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / metabolism*
  • Microsomes, Liver / enzymology
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • NADP / metabolism*
  • Oxidation-Reduction
  • Rats

Substances

  • Epoxy Compounds
  • Arachidonic Acid
  • NADP
  • Cytochrome P-450 Enzyme System