J. Lipid Res.
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A more recent version of this article appeared on August 1, 2004

Papers In Press, published online ahead of print May 16, 2004
J. Lipid Res., doi:10.1194/jlr.M300463-JLR200
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Submitted on November 5, 2003
Revised on April 8, 2004
Accepted on May 4, 2004

Human CYP4F3 are the main catalysts in the oxidation of fatty acid epoxides

Valérie Le Quere, Emmanuelle Plee-Gautier, Philippe Potin, Stéphanie Madec, and Jean-Pierre Salaun

Faculté de Médecine, Université de Bretagne Occidentale, BREST 29285

Corresponding Author: jp.salaun{at}univ-brest.fr

CYP4F isoforms are involved in the oxidation of important cellular mediators such as leukotriene B4 (LTB4)1 and prostaglandins. The proinflammatory agent LTB4 and cytotoxic leukotoxins were associated with several inflammatory diseases. We report on the hydroxylation of Z9,10-epoxyoctadecanoic, Z9,10-epoxyoctadec-Z12-enoic, Z12,13-epoxyoctadec-Z9-enoic acids and that of monoepoxides from arachidonic acid (EET) as a mechanism for regulation of leukotoxin and EET activity. The three C18-epoxides were converted to 18-hydroxy-C18-epoxides by human hepatic microsomes with apparent Km within 27.6 and 175 µM. Among P450 recombinants, CYP4F2 and 4F3B catalyzed mainly the -hydroxylation of C18-epoxides with Vmax within 0.84 to 15.0 min-1, whereas the Vmax displayed by CYP4F3A, the isoform found in leukocytes, ranged from 3.0 to 21.2 min-1. A rate of omega-hydroxylation by CYP4A11 was experimentally found within 0.3 and 2.7 min-1. CYP4F2 and CYP4F3 exhibited preference for omega-hydroxylation of 8,9-EET, whereas human liver microsomes preferred 11,12-EET followed by 8,9-EET. Moreover, conjugated diols from both C18-epoxides and EETs were omega-hydroxylated by liver microsomes and by CYP4F2 and CYP4F3. These data support the hypothesis that the human CYP4F subfamily is involved in the omega-hydroxylation of fatty acid epoxides. These findings demonstrated that another pathway besides conversion to diols exists for fatty acid epoxides inactivation.


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