NADPH-dependent microsomal metabolism of 14,15-epoxyeicosatrienoic acid to diepoxides and epoxyalcohols

Jorge H. Capdevila, Paul Mosset, Pendri Yadagiri, Sun Lumin, J. R. Falck

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The arachidonic acid epoxygenase metabolite 14,15-epoxyeicosatrienoic acid is further metabolized by rat liver microsomal fractions to regioisomeric diepoxides and epoxyalcohols. Diepoxides result from epoxidation at the 5,6-, 8,9-, or 11,12-olefins. Hydroxylation leading to epoxyalcohols with a cis, trans-conjugated dienol occurs at carbons 5, 8, 9, or 12. Structural assignments were established by chromatographic and mass spectral comparisons with synthetic standards. The reaction requires NADPH and is inhibited by typical cytochrome P-450 inhibitors. Analysis of the time course of product formation during arachidonic acid oxidation by rat liver microsomal fractions indicated that all four regioisomeric epoxyeicosatrienoic acids can be further metabolized by the enzyme system.

Original languageEnglish (US)
Pages (from-to)122-133
Number of pages12
JournalArchives of Biochemistry and Biophysics
Volume261
Issue number1
DOIs
StatePublished - Feb 15 1988

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NADP
Metabolism
Liver
Rats
Hydroxylation
Epoxidation
Alkenes
Metabolites
Arachidonic Acid
Carbon
Oxidation
Acids
Enzymes
14,15-epoxy-5,8,11-eicosatrienoic acid
arachidonate epoxygenase
Cytochrome P-450 Enzyme Inhibitors

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

NADPH-dependent microsomal metabolism of 14,15-epoxyeicosatrienoic acid to diepoxides and epoxyalcohols. / Capdevila, Jorge H.; Mosset, Paul; Yadagiri, Pendri; Lumin, Sun; Falck, J. R.

In: Archives of Biochemistry and Biophysics, Vol. 261, No. 1, 15.02.1988, p. 122-133.

Research output: Contribution to journalArticle

Capdevila, Jorge H. ; Mosset, Paul ; Yadagiri, Pendri ; Lumin, Sun ; Falck, J. R. / NADPH-dependent microsomal metabolism of 14,15-epoxyeicosatrienoic acid to diepoxides and epoxyalcohols. In: Archives of Biochemistry and Biophysics. 1988 ; Vol. 261, No. 1. pp. 122-133.
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