Cytochrome P450-derived linoleic acid metabolites EpOMEs and DiHOMEs: a review of recent studies

J Nutr Biochem. 2020 Dec:86:108484. doi: 10.1016/j.jnutbio.2020.108484. Epub 2020 Aug 20.

Abstract

Linoleic acid (LA) is the most abundant polyunsaturated fatty acid found in the Western diet. Cytochrome P450-derived LA metabolites 9,10-epoxyoctadecenoic acid (9,10-EpOME), 12,13-epoxyoctadecenoic acid (12,13-EpOME), 9,10-dihydroxy-12Z-octadecenoic acid (9,10-DiHOME) and 12,13-dihydroxy-9Z-octadecenoic acid (12,13-DiHOME) have been studied for their association with various disease states and biological functions. Previous studies of the EpOMEs and DiHOMEs have focused on their roles in cytotoxic processes, primarily in the inhibition of the neutrophil respiratory burst. More recent research has suggested the DiHOMEs may be important lipid mediators in pain perception, altered immune response and brown adipose tissue activation by cold and exercise. The purpose of this review is to summarize the current understanding of the physiological and pathophysiological roles and modes of action of the EpOMEs and DiHOMEs in health and disease.

Keywords: 12,13-DiHOME; Cytochrome P450; Isoleukotoxin; Leukotoxin; Linoleic acid; Soluble epoxide hydrolase.

Publication types

  • Research Support, N.I.H., Extramural
  • Review

MeSH terms

  • Adipose Tissue, Brown / metabolism
  • Analgesics / pharmacology
  • Animals
  • Cytochrome P-450 Enzyme System / metabolism
  • Endocrine System / drug effects
  • Epoxide Hydrolases / metabolism
  • Exotoxins / chemistry
  • Humans
  • Immune System / drug effects
  • Inflammation
  • Linoleic Acid / metabolism*
  • Lipids / chemistry
  • Lung / drug effects
  • Mice
  • Neutrophils / metabolism
  • Oleic Acids / metabolism*
  • Oxidation-Reduction
  • Pain Management
  • Respiratory Burst
  • Stearic Acids / metabolism*

Substances

  • 12,13-dihydroxyoctadecenoic acid
  • 12,13-epoxy-11-hydroxy-9-octadecenoic acid
  • 9,10-dihydroxy-12-octadecenoic acid
  • Analgesics
  • Exotoxins
  • Lipids
  • Oleic Acids
  • Stearic Acids
  • leukotoxin
  • 9,10-epoxystearic acid
  • Cytochrome P-450 Enzyme System
  • Linoleic Acid
  • Epoxide Hydrolases