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J Biol Chem, Vol. 273, Issue 45, 29295-29301, November 6, 1998

Identification of Two Major F₂ Isoprostanes, 8,12-Iso- and 5-epi-8,12-Iso-isoprostane F₂-VI, in Human Urine

John A. Lawson, Hongwei Li, Joshua Rokach^§, Mustafa Adiyaman^§, Seong-Woo Hwang^§, Subhash P. Khanapure^§, and Garret A. FitzGerald

From the  Center for Experimental Therapeutics, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6100 and the ^§ Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, Melbourne, Florida

Isoprostanes (iPs) are nonenzymatic, free radical-derived compounds isomeric with enzymatically formed eicosanoids such as prostaglandins, leukotrienes, and thromboxanes. One group formed by the auto-oxidation of arachidonic acid, the F₂-iPs, consists of four classes of isomers of prostaglandin F₂ (PGF₂). They are relatively abundant in human urine. This fact, along with their chemical stability and excellent characteristics for quantitation by gas chromatography/mass spectrometry, has made them attractive indices of oxidative stress in humans. We developed a specific assay using gas chromatography/mass spectrometry for the first identified F₂-iP, iPF₂-III (previously called 8-iso-PGF₂ or 8-epi-PGF₂), which demonstrated the utility of monitoring a specific isomer. Recently, we described an assay for another isomer, iPF₂-VI, which is present in urine in greater concentration than iPF₂-III and which is particularly amenable to quantitation. We now describe the identification in human urine of two more isomers, 8,12-iso-iPF₂-VI and 5-epi-8,12-iso-iPF₂-VI, using high performance liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry. These compounds are each present in ~5-fold greater concentrations than iPF₂-VI (~20-fold greater than iPF₂-III). They share the unique chemical characteristics of class VI compounds, which make them attractive targets for quantitation by gas chromatography/mass spectrometry and immunoassay development.

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Copyright © 1998 by The American Society for Biochemistry and Molecular Biology, Inc.

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