Nitration of unsatd. fatty acids is a (patho)physiol. important pathway of lipid modification induced by nitric oxide-derived species. We report herein on the unexpected chain rearrangement undergone by (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid (I), a linoleic acid metabolite, when exposed to nitrating agents of biol. relevance. At pH 7.4 and at room temp., reaction of I with peroxynitrite (ONOO-) as well as Fe2+-EDTA/H2O2/NO2- and horseradish peroxidase/H2O2/NO2- led to the formation of two nitration products, which could be isolated as the Me esters and were identified as diastereoisomeric Me (12S)-10,11-epoxy-12-hydroxy-9-(nitromethyl)heptadecanoates by extensive 1H, 13C, 15N NMR and MS anal.

Biomimetic nitration of the linoleic acid metabolite 13-hydroxyoctadecadienoic acid: isolation and spectral characterization of novel chain-rearranged epoxy nitro derivatives.

MANINI, PAOLA;NAPOLITANO, ALESSANDRA;D'ISCHIA, MARCO
2008

Abstract

Nitration of unsatd. fatty acids is a (patho)physiol. important pathway of lipid modification induced by nitric oxide-derived species. We report herein on the unexpected chain rearrangement undergone by (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid (I), a linoleic acid metabolite, when exposed to nitrating agents of biol. relevance. At pH 7.4 and at room temp., reaction of I with peroxynitrite (ONOO-) as well as Fe2+-EDTA/H2O2/NO2- and horseradish peroxidase/H2O2/NO2- led to the formation of two nitration products, which could be isolated as the Me esters and were identified as diastereoisomeric Me (12S)-10,11-epoxy-12-hydroxy-9-(nitromethyl)heptadecanoates by extensive 1H, 13C, 15N NMR and MS anal.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/305564
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