Document Detail

Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation.
MedLine Citation:
PMID:  15273286     Owner:  NLM     Status:  MEDLINE    
Nitric oxide (*NO) and its reactive metabolites mediate the oxidation, nitration, and nitrosation of DNA bases, amino acids, and lipids. Here, we report the structural characterization and quantitation of two allylic nitro derivatives of linoleic acid (LNO(2)), present as both free and esterified species in human red cell membranes and plasma lipids. The LNO(2) isomers 10-nitro-9-cis, 12-cis-octadecadienoic acid and 12-nitro-9-cis, 12-cis-octadecadienoic acid were synthesized and compared with red cell and plasma LNO(2) species based on chromatographic elution and mass spectral properties. Collision-induced dissociation fragmentation patterns from synthetic LNO(2) isomers were identical to those of the two most prevalent LNO(2) positional isomers found in red cells and plasma. By using [(13)C]LNO(2) as an internal standard, red cell free and esterified LNO(2) content was 50 +/- 17 and 249 +/- 104 nM, respectively. The free and esterified LNO(2) content of plasma was 79 +/- 35 and 550 +/- 275 nM, respectively. Nitrated fatty acids, thus, represent the single largest pool of bioactive oxides of nitrogen in the vasculature, with a net LNO(2) concentration of 477 +/- 128 nM, excluding buffy coat cells. These observations affirm that basal oxidative and nitrating conditions occur in healthy humans to an extent that is sufficient to induce abundant membrane and lipoprotein-fatty acid nitration. Given that LNO(2) is capable of mediating cGMP and non-cGMP-dependent signaling reactions, fatty acid nitration products are species representing the convergence of ()NO and oxygenated lipid cell-signaling pathways.
Paul R S Baker; Francisco J Schopfer; Scott Sweeney; Bruce A Freeman
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.     Date:  2004-07-23
Journal Detail:
Title:  Proceedings of the National Academy of Sciences of the United States of America     Volume:  101     ISSN:  0027-8424     ISO Abbreviation:  Proc. Natl. Acad. Sci. U.S.A.     Publication Date:  2004 Aug 
Date Detail:
Created Date:  2004-08-12     Completed Date:  2004-09-29     Revised Date:  2013-04-18    
Medline Journal Info:
Nlm Unique ID:  7505876     Medline TA:  Proc Natl Acad Sci U S A     Country:  United States    
Other Details:
Languages:  eng     Pagination:  11577-82     Citation Subset:  IM    
Department of Anesthesiology, Center for Free Radical Biology, University of Alabama at Birmingham, Birmingham, AL 35294, USA.
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MeSH Terms
Chromatography, High Pressure Liquid
Erythrocyte Membrane / chemistry*
Fatty Acids, Unsaturated / blood*,  chemical synthesis
Linoleic Acid / blood*,  chemical synthesis,  isolation & purification
Mass Spectrometry
Nitro Compounds / blood*,  chemical synthesis,  isolation & purification
Grant Support
Reg. No./Substance:
0/Fatty Acids, Unsaturated; 0/Nitro Compounds; 2197-37-7/Linoleic Acid
Comment In:
Proc Natl Acad Sci U S A. 2004 Aug 10;101(32):11527-8   [PMID:  15292510 ]

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