Catabolism of epoxy fatty esters by the purified epoxide hydrolase from mouse and human liver

Premjit P. Halarnkar, Roger N. Wixtrom, Marilyn H. Silva, Bruce D. Hammock

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Epoxymethylstearate, 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.

Original languageEnglish (US)
Pages (from-to)226-236
Number of pages11
JournalArchives of Biochemistry and Biophysics
Volume272
Issue number1
DOIs
StatePublished - 1989

Fingerprint

Epoxide Hydrolases
Liver
Esters
Affinity chromatography
Clofibrate
Substrates
Metabolites
Affinity Chromatography
Isomers
Fatty Acids

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Catabolism of epoxy fatty esters by the purified epoxide hydrolase from mouse and human liver. / Halarnkar, Premjit P.; Wixtrom, Roger N.; Silva, Marilyn H.; Hammock, Bruce D.

In: Archives of Biochemistry and Biophysics, Vol. 272, No. 1, 1989, p. 226-236.

Research output: Contribution to journalArticle

Halarnkar, Premjit P. ; Wixtrom, Roger N. ; Silva, Marilyn H. ; Hammock, Bruce D. / Catabolism of epoxy fatty esters by the purified epoxide hydrolase from mouse and human liver. In: Archives of Biochemistry and Biophysics. 1989 ; Vol. 272, No. 1. pp. 226-236.
@article{da1be2bbaf1743babff671c9ceee9f29,
title = "Catabolism of epoxy fatty esters by the purified epoxide hydrolase from mouse and human liver",
abstract = "Epoxymethylstearate, 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.",
author = "Halarnkar, {Premjit P.} and Wixtrom, {Roger N.} and Silva, {Marilyn H.} and Hammock, {Bruce D.}",
year = "1989",
doi = "10.1016/0003-9861(89)90214-2",
language = "English (US)",
volume = "272",
pages = "226--236",
journal = "Archives of Biochemistry and Biophysics",
issn = "0003-9861",
publisher = "Academic Press Inc.",
number = "1",

}

TY - JOUR

T1 - Catabolism of epoxy fatty esters by the purified epoxide hydrolase from mouse and human liver

AU - Halarnkar, Premjit P.

AU - Wixtrom, Roger N.

AU - Silva, Marilyn H.

AU - Hammock, Bruce D.

PY - 1989

Y1 - 1989

N2 - Epoxymethylstearate, 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.

AB - Epoxymethylstearate, 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.

UR - http://www.scopus.com/inward/record.url?scp=0024361188&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0024361188&partnerID=8YFLogxK

U2 - 10.1016/0003-9861(89)90214-2

DO - 10.1016/0003-9861(89)90214-2

M3 - Article

VL - 272

SP - 226

EP - 236

JO - Archives of Biochemistry and Biophysics

JF - Archives of Biochemistry and Biophysics

SN - 0003-9861

IS - 1

ER -