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

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

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Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, University Montpellier I and II, ENSCM, Faculty of Pharmacy, Montpellier, France.
School of Biological Sciences, The University of Hong Kong, Hong Kong.
INRA, UMR1019, UNH, CRNH Auvergne, Clermont-Ferrand, Clermont Université, Université d'Auvergne, Unité de Nutrition Humaine, Clermont-Ferrand, France.
INSERM U1046, Physiologie & Médecine Expérimentale du Cœur et des Muscles, University Montpellier I and II, Montpellier, France.


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".


Bioactive lipids; Biomarkers; Dihomo-isoprostanes; Isofurans; Neuroprostanes; Phytoprostanes

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