Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1253706 | Chemistry and Physics of Lipids | 2008 | 11 Pages |
Abstract
Nitration of unsaturated fatty acids is a (patho)physiologically 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 (1), a linoleic acid metabolite, when exposed to nitrating agents of biological relevance. At pH 7.4 and at room temperature, reaction of 1 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 methyl esters and were identified as diastereoisomeric methyl (12S)-10,11-epoxy-12-hydroxy-9-nitromethylheptadecanoates by extensive 1H, 13C, 15N NMR and MS analysis.
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Physical Sciences and Engineering
Chemistry
Chemistry (General)
Authors
Paola Manini, Emanuela Camera, Mauro Picardo, Alessandra Napolitano, Marco d’Ischia,