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

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.

journal_name

Chem Phys Lipids

authors

Manini P,Camera E,Picardo M,Napolitano A,d'Ischia M

doi

10.1016/j.chemphyslip.2007.09.007

subject

Has Abstract

pub_date

2008-01-01 00:00:00

pages

51-61

issue

1

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(07)00428-8

journal_volume

151

pub_type

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