Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids

J R Falck, Sun Lumin, Ian Blair, Elizabeth Dishman, Martha V. Martin, David J. Waxman, F. Peter Guengerich, Jorge H. Capdevila

Research output: Contribution to journalArticle

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Abstract

Incubation of rat liver microsomal fractions with arachidonic acid in the presence of NADPH results in the formation of three novel monohydroxylated fatty acid metabolites. Utilizing chromatographic and mass spectral techniques, these metabolites have been identified as 16-, 17-, and 18-hydroxyeicosatetraenoic acids. The NADPH-dependent microsomal metabolism of arachidonic acid to 16-, 17-, 18-, and 19-hydroxyeicosatetraenoic acids is induced after animal treatment with β-naphthoflavone. Reconstitution of the arachidonic acid oxygenase utilizing individual purified cytochrome P-450 enzymes demonstrates regioselectivity, controlled by the protein catalyst, for the hydroxylation of the sp3 carbon atoms adjacent to the methyl end of the fatty acid.

Original languageEnglish (US)
Pages (from-to)10244-10249
Number of pages6
JournalJournal of Biological Chemistry
Volume265
Issue number18
StatePublished - Jun 25 1990

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Arachidonic Acid
Cytochrome P-450 Enzyme System
Metabolites
NADP
Oxidation
Fatty Acids
Hydroxyeicosatetraenoic Acids
Regioselectivity
Oxygenases
Hydroxylation
Metabolism
Liver
Rats
Animals
Carbon
Atoms
Catalysts
18-hydroxy-5,8,11,14-eicosatetraenoic acid
Proteins

ASJC Scopus subject areas

  • Biochemistry

Cite this

Falck, J. R., Lumin, S., Blair, I., Dishman, E., Martin, M. V., Waxman, D. J., ... Capdevila, J. H. (1990). Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids. Journal of Biological Chemistry, 265(18), 10244-10249.

Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids. / Falck, J R; Lumin, Sun; Blair, Ian; Dishman, Elizabeth; Martin, Martha V.; Waxman, David J.; Guengerich, F. Peter; Capdevila, Jorge H.

In: Journal of Biological Chemistry, Vol. 265, No. 18, 25.06.1990, p. 10244-10249.

Research output: Contribution to journalArticle

Falck, JR, Lumin, S, Blair, I, Dishman, E, Martin, MV, Waxman, DJ, Guengerich, FP & Capdevila, JH 1990, 'Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids', Journal of Biological Chemistry, vol. 265, no. 18, pp. 10244-10249.
Falck, J R ; Lumin, Sun ; Blair, Ian ; Dishman, Elizabeth ; Martin, Martha V. ; Waxman, David J. ; Guengerich, F. Peter ; Capdevila, Jorge H. / Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids. In: Journal of Biological Chemistry. 1990 ; Vol. 265, No. 18. pp. 10244-10249.
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