PMID: 8443245Feb 24, 1993Paper

bis-Allylic hydroxylation of linoleic acid and arachidonic acid by human hepatic monooxygenases

Biochimica Et Biophysica Acta
E H Oliw

Abstract

[14C]Linoleic acid was incubated with human liver microsomes and NADPH and biosynthesis of allylic hydroxy fatty acids was investigated. 11-Hydroxy-9Z,12Z-octadecadienoic acid (11-HODE), 9-hydroxy-10E,12Z-octadecadienoic acid (9-HODE), 13-hydroxy-9Z,11E-octadecadienoic acid (13-HODE) and 14-hydroxy-9Z,12Z-octadecadienoic acid were identified. 9-HODE and 13-HODE were formed with stereoselectivity (80% R) provided that 11-HODE was prevented from decomposing to 9(R,S)-HODE and 13(R,S)-HODE by extractive isolation at pH 5-6. Human hepatic microsomes metabolized [14C]arachidonic acid to many products, including 13-HETE and small amounts of 15-HETE (> 90% R), 11-HETE (59% R) and 12-HETE (> 90% R). Hepatic microsomes of untreated rats metabolized [14C]linoleic acid to 11-HODE as a major product, but significant formation of 11-HODE by purified cytochrome P-450 (P450) (CYP1A1, CYP2B1, CYP2B4, CYP2E1, CYP3A6 and CYP4A1) in a reconstituted system could not be detected, indicating that 11-HODE might be formed by other and constitutive P450 isozymes.

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Citations

Aug 30, 2000·Prostaglandins & Other Lipid Mediators·J H Capdevila, J R Falck
Nov 16, 2002·Prostaglandins & Other Lipid Mediators·Jorge H Capdevila, John R Falck
Nov 27, 1999·Molecular Aspects of Medicine·J A Hasler
Jun 17, 1998·Proceedings of the National Academy of Sciences of the United States of America·W E BoeglinA R Brash
Mar 1, 1996·Kidney International·A M AlkhunaiziR W Schrier
Jan 18, 2005·Biochemical and Biophysical Research Communications·Mia Sandberg LundbladAnders Rane
Jul 12, 2005·Prostaglandins, Leukotrienes, and Essential Fatty Acids·J Clària, A Planagumà
Aug 4, 2015·Prostaglandins, Leukotrienes, and Essential Fatty Acids·Zhi-Xin Yuan, Stanley I Rapoport
Dec 20, 2020·Biochimica Et Biophysica Acta. Molecular and Cell Biology of Lipids·Zhichao ZhangAmeer Y Taha
Jan 10, 2020·Biochimica Et Biophysica Acta. Molecular and Cell Biology of Lipids·David FuchsCraig E Wheelock
Dec 18, 2020·Frontiers in Endocrinology·Ali A HajeyahValerie B O'Donnell
Nov 24, 1999·The American Journal of Physiology·E TitosJ Clària
Feb 1, 1995·The Journal of Investigative Dermatology·A N BaerF A Green

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