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J Biol Chem, Vol. 274, Issue 3, 1313-1319, January 15, 1999

Identification and Measurement of Endogenous -Oxidation Metabolites of 8-epi-Prostaglandin F2

Chiara Chiabrando, Anna Valagussa, Claudia Rivalta, Thierry Durand, Alexandre Guy, Ettore Zuccato, Pia Villa^**, Jean-Claude Rossi, and Roberto Fanelli

From the  Department of Environmental Health Sciences of the ^** Istituto di Ricerche Farmacologiche "Mario Negri," Via Eritrea 62, 20157 Milano, Italy and the  Faculty of Pharmacy, UPRES A CNRS 5074, UM I, F-34060 Montpellier, France

F₂-isoprostanes are prostaglandin-like compounds derived from nonenzymatic free radical-catalyzed peroxidation of arachidonic acid. 8-epi-Prostaglandin (PG) F₂, a major component of the F₂-isoprostane family, can be conveniently measured in urine to assess noninvasively lipid peroxidation in vivo. Measurement of major metabolites of endogenous 8-epi-PGF₂, in addition to the parent compound, may be useful to better define its formation in vivo. 2,3-Dinor-5,6-dihydro-8-epi-PGF₂ is the only identified metabolite of 8-epi-PGF₂ in man, but its endogenous levels are unknown. In addition to this metabolite, we have identified another major endogenous metabolite, 2,3-dinor-8-epi-PGF₂, in human and rat urine. The identity of these compounds, present at the pg/ml level in urine, was proven by a number of complementary approaches, based on: (a) immunoaffinity chromatography for selective extraction; (b) gas chromatography-mass spectrometry for structural analysis; (c) in vitro metabolism in isolated rat hepatocytes; and (d) chemical synthesis of the enantiomer of 2,3-dinor-5,6-dihydro-8-epi-PGF₂ as a reference standard. In humans, the urinary excretion rate of both dinor metabolites is comparable with that of 8-epi-PGF₂. Both metabolites increase in parallel with the parent compound in cigarette smokers, and they are not reduced during cyclooxygenase inhibition. Another -oxidation product, 2,3,4,5-tetranor-8-epi-PGF₂, was identified as a major product of rat hepatocyte metabolism. In conclusion, at least two major -oxidation products of 8-epi-PGF₂ are present in urine, which may be considered as additional analytical targets to evaluate 8-epi-PGF₂ formation and degradation in vivo.

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Copyright © 1999 by The American Society for Biochemistry and Molecular Biology, Inc.

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