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. 2009 Apr;50 Suppl(Suppl):S219-23.
doi: 10.1194/jlr.R800037-JLR200. Epub 2008 Oct 28.

Isoprostanes

L Jackson Roberts 2nd  1 , Ginger L Milne
Affiliations

Isoprostanes

L Jackson Roberts 2nd et al. J Lipid Res. 2009 Apr.

Abstract

The isoprostanes (IsoPs) are a unique series of prostaglandin-like compounds formed in vivo via a nonenzymatic mechanism involving the free radical-initiated peroxidation of arachidonic acid. This article summarizes our current knowledge of these compounds. Herein, a historical account of their discovery and the mechanism of their formation are described. A specific class of IsoPs, the F2-IsoPs, are stable, robust molecules that can be measured as indices of endogenous oxidant stress. The utility of these molecules as biomarkers and methods by which these compounds can be quantified are discussed. In addition to the F2-IsoPs, isoprostanes with other prostane ring structures as well as oxidation products with furan and dioxolane rings can be generated from arachidonic acid. And, in more recent years, isoprostane-like compounds have been shown to be formed from polyunsaturated fatty acids including eicosapentaenoic acid [C20:5, omega-3], docosahexaenoic acid [C22:6, omega-3], and adrenic acid [C22:4, omega-6]. These findings will be summarized as well.

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Figures

Fig. 1.
Fig. 1.
Pathway of formation of F2-isoprostanes. IsoP, isoprostane.
Fig. 2.
Fig. 2.
Oxidation of arachidonic acid to yield isoprostanes of differing ring structures. IsoK, isoketal.
Fig. 3.
Fig. 3.
Oxidation of arachidonic acid to yield isoprostanes, mono and serial cyclic peroxides, and isofurans.
See this image and copyright information in PMC

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