| Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation. | |
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MedLine Citation:
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PMID: 15273286 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Paul R S Baker; Francisco J Schopfer; Scott Sweeney; Bruce A Freeman |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. Date: 2004-07-23 |
Journal Detail:
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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:
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Created Date: 2004-08-12 Completed Date: 2004-09-29 Revised Date: 2013-04-18 |
Medline Journal Info:
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Nlm Unique ID: 7505876 Medline TA: Proc Natl Acad Sci U S A Country: United States |
Other Details:
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Languages: eng Pagination: 11577-82 Citation Subset: IM |
Affiliation:
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Department of Anesthesiology, Center for Free Radical Biology, University of Alabama at Birmingham, Birmingham, AL 35294, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chromatography, High Pressure Liquid Erythrocyte Membrane / chemistry* Fatty Acids, Unsaturated / blood*, chemical synthesis Humans Isomerism Linoleic Acid / blood*, chemical synthesis, isolation & purification Mass Spectrometry Nitro Compounds / blood*, chemical synthesis, isolation & purification |
| Grant Support | |
ID/Acronym/Agency:
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R01HL58115/HL/NHLBI NIH HHS; R01HL64937/HL/NHLBI NIH HHS; T32HL07457/HL/NHLBI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Fatty Acids, Unsaturated; 0/Nitro Compounds; 2197-37-7/Linoleic Acid |
| Comments/Corrections | |
Comment In:
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Proc Natl Acad Sci U S A. 2004 Aug 10;101(32):11527-8
[PMID:
15292510
]
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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