Catabolism of epoxy fatty esters by the purified epoxide hydrolase from mouse and human liver.
Epoxymethylsterate, 9,10- and 12,13-epoxymethyloleates, and a mixture of isomers of epoxymethylarachidonate and diepoxymethylstearate were synthesized, and their metabolic rates were measured using crude and purified cytosolic epoxide hydrolase. Hepatic epoxide hydrolase was purified from human samples and clofibrate-fed mice by affinity chromatography. The major metabolites under these conditions of all the epoxy fatty esters were their vicinal diols whose structures were confirmed by GC-MS. 12,13-Epoxymethyloleate was metabolized faster than 9,10-epoxymethyloleate and other epoxy fatty esters, but all substrates were turned over rapidly. This rapid turnover suggests that epoxy fatty acids may be endogenous substrates for the cytosolic epoxide hydrolase.
Halarnkar
P P
PP
Department of Entomology, University of California, Davis 95616.
Wixtrom
R N
RN
Silva
M H
MH
Hammock
B D
BD
D000818:Animals; D001095:Arachidonic Acids / Q000378:metabolism; D002849:Chromatography, Gas; D004851:Epoxide Hydrolases / Q000302:isolation & purification / Q000378:metabolism*; D004852:Epoxy Compounds / Q000378:metabolism*; D004988:Ethers, Cyclic / Q000378:metabolism*; D005227:Fatty Acids / Q000378:metabolism*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007700:Kinetics; D008099:Liver / Q000201:enzymology*; D008297:Male; D051379:Mice; D009829:Oleic Acids / Q000378:metabolism; D013228:Stearates / Q000378:metabolism
D001095:Arachidonic Acids; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D005227:Fatty Acids; D009829:Oleic Acids; D013228:Stearates; C005576:methyl oleate; D004851:Epoxide Hydrolases