Non-enzymatic cyclic oxygenated metabolites of adrenic, docosahexaenoic, eicosapentaenoic and α-linolenic acids; bioactivities and potential use as biomarkers

Biochim Biophys Acta. 2015 Apr;1851(4):446-55. doi: 10.1016/j.bbalip.2014.11.004. Epub 2014 Nov 14.


Cyclic oxygenated metabolites are formed in vivo through non-enzymatic free radical reaction of n-6 and n-3 polyunsaturated fatty acids (PUFAs) such as arachidonic (ARA C20:4 n-6), adrenic (AdA 22:4 n-6), α-linolenic (ALA 18:3 n-3), eicosapentaenoic (EPA 20:5 n-3) and docosahexaenoic (DHA 22:6 n-3) acids. These cyclic compounds are known as isoprostanes, neuroprostanes, dihomo-isoprostanes and phytoprostanes. Evidence has emerged for their use as biomarkers of oxidative stress and, more recently, the n-3PUFA-derived compounds have been shown to mediate bioactivities as secondary messengers. Accordingly, this review will focus on the cyclic oxygenated metabolites generated from AdA, ALA, EPA and DHA. This article is part of a Special Issue entitled "Oxygenated metabolism of PUFA: analysis and biological relevance".

Keywords: Bioactive lipids; Biomarkers; Dihomo-isoprostanes; Isofurans; Neuroprostanes; Phytoprostanes.

Publication types

  • Review

MeSH terms

  • Animals
  • Biomarkers / metabolism
  • Docosahexaenoic Acids / metabolism*
  • Eicosapentaenoic Acid / analogs & derivatives
  • Eicosapentaenoic Acid / metabolism*
  • Fatty Acids, Unsaturated / metabolism*
  • Humans
  • Lipid Peroxidation
  • Oxidation-Reduction
  • Oxidative Stress*
  • Signal Transduction
  • alpha-Linolenic Acid / analogs & derivatives
  • alpha-Linolenic Acid / metabolism*


  • Biomarkers
  • Fatty Acids, Unsaturated
  • alpha-Linolenic Acid
  • adrenic acid
  • Docosahexaenoic Acids
  • Eicosapentaenoic Acid