J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
QUICK SEARCH:   [advanced]


     

Originally published In Press as doi:10.1194/jlr.M200467-JLR200 on July 1, 2003

This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow All Versions of this Article:
M200467-JLR200v1
44/9/1660    most recent
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Right arrow Citation Map
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Lima, E. S.
Right arrow Articles by Abdalla, D. S. P.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Lima, E. S.
Right arrow Articles by Abdalla, D. S. P.
Social Bookmarking
Add to CiteULike   Add to Complore   Add to Connotea   Add to Del.icio.us   Add to Digg   Add to Reddit   Add to Technorati  
What's this?
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{dagger} and Dulcineia S. P. Abdalla1,*

* Departamento de Análises Clínicas e Toxicológicas, Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil
{dagger} 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 (Vmax 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{alpha},2{alpha} (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


Add to CiteULike CiteULike   Add to Complore Complore   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us   Add to Digg Digg   Add to Reddit Reddit   Add to Technorati Technorati    What's this?


This article has been cited by other articles:


Home page
 J. Biol. Chem.Home page
S. Miersch, M. G. Espey, R. Chaube, A. Akarca, R. Tweten, S. Ananvoranich, and B. Mutus
Plasma Membrane Cholesterol Content Affects Nitric Oxide Diffusion Dynamics and Signaling
J. Biol. Chem., July 4, 2008; 283(27): 18513 - 18521.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
L. M. S. Baker, P. R. S. Baker, F. Golin-Bisello, F. J. Schopfer, M. Fink, S. R. Woodcock, B. P. Branchaud, R. Radi, and B. A. Freeman
Nitro-fatty Acid Reaction with Glutathione and Cysteine: KINETIC ANALYSIS OF THIOL ALKYLATION BY A MICHAEL ADDITION REACTION
J. Biol. Chem., October 19, 2007; 282(42): 31085 - 31093.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
T. Cui, F. J. Schopfer, J. Zhang, K. Chen, T. Ichikawa, P. R. S. Baker, C. Batthyany, B. K. Chacko, X. Feng, R. P. Patel, et al.
Nitrated Fatty Acids: Endogenous Anti-inflammatory Signaling Mediators
J. Biol. Chem., November 24, 2006; 281(47): 35686 - 35698.
[Abstract] [Full Text] [PDF]

Home page
 Proc. Natl. Acad. Sci. USAHome page
M. M. Wright, F. J. Schopfer, P. R. S. Baker, V. Vidyasagar, P. Powell, P. Chumley, K. E. Iles, B. A. Freeman, and A. Agarwal
Fatty acid transduction of nitric oxide signaling: Nitrolinoleic acid potently activates endothelial heme oxygenase 1 expression.
PNAS, March 14, 2006; 103(11): 4299 - 4304.
[Abstract] [Full Text] [PDF]

Home page
 Proc. Natl. Acad. Sci. USAHome page
P. R. S. Baker, F. J. Schopfer, S. Sweeney, and B. A. Freeman
From the Cover: Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation
PNAS, August 10, 2004; 101(32): 11577 - 11582.
[Abstract] [Full Text] [PDF]


HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
 All ASBMB Journals   Journal of Biological Chemistry 
 Molecular and Cellular Proteomics   ASBMB Today 
Copyright © 2003 by the American Society for Biochemistry and Molecular Biology.