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J. Biol. Chem., Vol. 265, Issue 19, 10865-10871, Jul, 1990
JH Capdevila, A Karara, DJ Waxman, MV Martin, JR Falck and FP Guenguerich
Chiral analysis of the rat liver microsomal arachidonic acid epoxygenase
metabolites shows enantioselective formation of 8,9-, 11,12- , and
14,15-cis-epoxyeicosatrienoic acids in an approximately 2:1, 4:1, and 2:1
ratio of antipodes, respectively. Animal treatment with the cytochrome
P-450 inducer phenobarbital increased the overall enantiofacial selectivity
of the microsomal epoxygenase and caused a concomitant inversion in the
absolute configurations of its metabolites. These effects of phenobarbital
were time-dependent and temporally linked to increases in the concentration
of microsomal cytochrome P-450 enzymes. Reconstitution of the epoxygenase
reaction utilizing several purified cytochrome P-450 demonstrated that the
asymmetry of epoxidation is under cytochrome P-450 enzyme control. These
results established that the chirality of the hepatic arachidonic acid
epoxygenase is under regulatory control and confirm cytochromes P- 450 IIB1
and IIB2 as two of the endogenous epoxygenases induced in vivo by
phenobarbital.
Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase
Department of Medicine (Nephrology Division), Vanderbilt University Medical School, Nashville, Tennessee 37232.
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