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Journal of Lipid Research, Vol. 44, 1660-1666, September 2003
Copyright © 2003 by American Society for Biochemistry and Molecular Biology

Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins

Emersom S. Lima^*, Paolo Di Mascio and Dulcineia S. P. Abdalla^1,*

^* Departamento de Análises Clínicas e Toxicológicas, Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil
Faculdade de Ciências Farmacêuticas, and Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

¹ To whom correspondence should be addressed. e-mail: 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 species with 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 (V_max 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.

Abbreviations: Ch18:2, cholesteryl linoleate (cholesteryl 9,12-octadecadienoate); Ch18:2NO₂, cholesteryl nitrolinoleate; [³H]-Ch18:2, [1,2 (n)-³H]cholesteryl linoleate; IR, infrared; LC-ESI/MS/MS, liquid chromatography/electrospray ionization tandem mass spectrometry; LONO, nitritelinoleate; LONO₂, nitratelinoleate; ^•NO₂, nitrogen dioxide radical

Supplementary key words nitration • cholesteryl linoleate • lipoproteins • mass spectrometry

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