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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Tsikas, Dimitrios Jordan, Jens Zoerner, Alexander A. |
| Description | Author Affiliation: Tsikas D ( Hannover Medical School, Hannover, Germany. tsikas.dimitros@mh-hannover.de) |
| Abstract | Compared to the arachidonic acid (C20:4) cascade, the oleic acid (C18:1) family comprises a handful known metabolites. The pathophysiology of oleic acid and its oxidized and nitrated metabolites, i.e., cis-9,10-epoxyoctadecanoic acid (cis-EpOA) and the two vinylic nitro-oleic acids cis-9-nitro-oleic acid $(9-NO_{2}-OA)$ and cis-10-nitro-oleic acid $(10-NO_{2}-OA),$ is only little investigated and little understood. cis-EpOA, $9-NO_{2}-OA$ and $10-NO_{2}-OA$ have been detected in plasma of healthy and ill human subjects by means of gas chromatography–tandem mass spectrometry (GC–MS/MS) and liquid chromatography–tandem mass spectrometry (LC–MS/MS) techniques in their acid and esterified forms. cis-EpOA is formed from oleic acid by the catalytic action of various cytochrome P450 isozymes. In end-stage liver disease, cis-EpOA plasma concentration is lower than in healthy subjects suggesting liver as the main organ responsible for cis-EpOA synthesis. The origin of $9-NO_{2}-OA$ and $10-NO_{2}-OA$ and of other nitrated oleic acid metabolites is unknown. In vitro models, nitro-oleic acid species can be formed non-enzymatically from oleic acid and nitrogen dioxide. Thus, endogenous nitro-oleic acids could serve as biomarkers of fatty acid nitration by reactive nitrogen species. Synthetic $9-NO_{2}-OA$ and $10-NO_{2}-OA$ at concentrations of three orders of magnitude higher than their endogenous counterparts have interesting pharmacological features and are currently intensely investigated. The present article reviews and discusses currently available analytical methods for the quantitative determination of cis-EpOA, $9-NO_{2}-OA$ and $10-NO_{2}-OA$ in biological samples, notably in human plasma, and the potential biological significance of these oleic acid metabolites. Special emphasis is given to GC–MS/MS and LC–MS/MS methods utilizing the stable-isotope dilution technique. The sensitivity and specificity of the MS/MS approach make electron-capture negative ion chemical ionization (ECNICI) GC–MS/MS and negative electrospray ionization (NESI) LC–MS/MS methodologies indispensable in experimental and clinical settings on oxidative and nitrative oleic acid metabolism. These techniques are particularly suited to delineate the oleic acid cascade. This article is part of a Special Issue entitled Lipodomics and Imaging Mass Spectrometry. |
| ISSN | 00063002 |
| Journal | Biochimica et Biophysica Acta (BBA) - Reviews on Cancer |
| Issue Number | 11 |
| Volume Number | 1811 |
| Language | English |
| Publisher | Elsevier |
| Publisher Date | 2011-11-01 |
| Publisher Place | Netherlands |
| Access Restriction | Open |
| Subject Keyword | Analytic Sample Preparation Methods Gas Chromatography-Mass Spectrometry Oleic Acid Chromatography, Liquid Nitrosation Chemistry Oxidation-Reduction Biochemistry |
| Content Type | Text |
| Resource Type | Article |
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