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Papers In Press, published online ahead of print July 1, 2003
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Department of Clinical and Toxicological Analyses, University of São Paulo, São Paulo, São Paulo 05508-900
Corresponding Author: dspa{at}usp.br
Nitric oxide (·NO) and ·NO-derived reactive species (e.g. peroxynitrite anion, nitrogen dioxide radical) react with lipids containing unsaturated fatty acids to generate nitrated species. In the present work we synthesized, characterized and detected a nitrated derivative of cholesteryl linoleate (Ch18:2), in human blood plasma and lipoproteins, using a high-pressure liquid chromatography coupled to electrospray ionization tandem mass spectrometry method. It was synthesized by a reaction of Ch18:2 with nitronium tetrafluoroborate, yielding a specie with a mass/charge ratio of (m/z) 711, which is characteristic of the cholesteryl nitrolinoleate (Ch18:2NO2) ammonium adduct. The presence of the nitro group was confirmed by using [15N] nitrite, which gave a product with m/z 712, with the same chromatographic and spectrometric characteristics of those of m/z 711. Furthermore, a C-NO2 structure was also demonstrated in Ch18:2NO2 by infrared analysis (nmax 1549, 1374 cm-1). A stable product with m/z of 711, showing the same chromatographic characteristics and fragmentation pattern as those of synthesized standard, was found in human blood plasma and lipoproteins of normolipidemic subjects. The presence of this novel nitrogen-containing lipid product in human plasma and lipoproteins could represent a potential indicator of the oxidative/nitrative roles that ·NO or its metabolites play during in vivo lipid oxidation, generating a compensatory mechanism of protection in vascular disease.
Revised on June 4, 2003
Accepted on June 16, 2003
Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins: Synthesis, characterization, and detection by HPLC coupled to mass spectrometry
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