Oxidized and nitrated oleic acid in biological systems: Analysis by GC-MS/MS and LC-MS/MS, and biological significance

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1811, Issue 11, 2011, Pages 694-705

  Tsikas, Dimitrios ^a   Zoerner, Alexander A ^a   Jordan, Jens ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

Author keywords

Lipids; Nitration; Oxidation; Stable isotope; Tandem mass spectrometry

Indexed keywords

10 NITRO OLEIC ACID; 9 NITRO OLEIC ACID; 9,10 EPOXYOCTADECANOIC ACID; EDETIC ACID; ELECTROPHILE; ISOTOPE; LINOLEIC ACID; OLEIC ACID; TYROSINE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; BLOOD; CATALYST; DERIVATIZATION; ELECTROPHILICITY; ELECTROSPRAY; END STAGE LIVER DISEASE; EPOXIDATION; ERYTHROCYTE; ESTERIFICATION; FATTY ACID ANALYSIS; FATTY ACID BLOOD LEVEL; FATTY ACID DESATURATION; FATTY ACID METABOLISM; FATTY ACID OXIDATION; FATTY ACID SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS; LEUKOCYTE; LIQUID CHROMATOGRAPHY; LIVER CIRRHOSIS; MASS FRAGMENTOGRAPHY; NITRATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REVIEW; TANDEM MASS SPECTROMETRY; URINE;

ANALYTIC SAMPLE PREPARATION METHODS; CHROMATOGRAPHY, LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; NITROSATION; OLEIC ACID; OXIDATION-REDUCTION;

EID: 80255132951     PISSN: 13881981     EISSN: 18792618     Source Type: Journal    
DOI: 10.1016/j.bbalip.2011.06.015     Document Type: Review

References (50)

1. M. Massaro, and R. De Caterina Vasculoprotective effects of oleic acid: epidemiological background and direct vascular antiatherogenic properties Nutr. Metab. Cardiovasc. Dis. 12 2002 42 51 (Pubitemid 135712747)
2. P. Yaqoob Monounsaturated fatty acids and immune function Eur. J. Clin. Nutr. 56 2002 S9 S13
3. R.M. Laethem, M. Balazy, and D.R. Koop Epoxidation of C18 unsaturated fatty acids by cytochromes P4502C2 and P4502CAA Drug Metab. Dispos. 24 1996 664 668
4. D. Tsikas, M. Sawa, G. Brunner, F.M. Gutzki, H.H. Meyer, and J.C. Frölich Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes J. Chromatogr. B 784 2003 351 365 (Pubitemid 36044018)
5. G.A. Ulsaker, and G. Teien Gas chromatographic-mass spectrometric identification of 9,10-epoxystearate in human blood Analyst 108 1983 521 524 (Pubitemid 13097466)
6. P. Fahlstadius cis-9,10-Epoxystearic acid in human leukocytes: isolation andquantitative determination Lipids 23 1988 1015 1018 (Pubitemid 18267402)
7. D. Tsikas, A. Mitschke, F.M. Gutzki, H.H. Meyer, and J.C. Frölich Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). II. Quantitative determination of cis-EODA in human plasma by GC-tandem MS J. Chromatogr. B 804 2004 403 412 (Pubitemid 38481717)
8. T. Thum, S. Batkai, P.G. Malinski, T. Becker, I. Mevius, J. Klempnauer, H.H. Meyer, J.C. Frölich, J. Borlak, and D. Tsikas Measurement and diagnostic use of hepatic cytochrome P450 metabolism of oleic acid in liver disease Liver Int. 30 2010 1181 1188
9. IARC (International Agency for Research on Cancer). cis-9,10-Epoxystearic acid 11 (1976) 115-223.
10. I. Chu, D.C. Villeneuve, V. Secours, and A. Viau Absorption, distribution and metabolism of epoxystearic acid in the rat Bull. Environ. Contam. Toxicol. 22 1979 462 466 (Pubitemid 9246077)
11. T. Watabe, Y. Ueno, and J. Imazumi Conversion of oleic acid into threo-dihydroxystearic acid by rat liver microsomes Biochem. Pharmacol. 20 1971 912 913
12. R. Sharma, S. Gupta, S.S. Singhal, G.A. Ansari, and Y.C. Awasthi Glutathione S-transferase-catalysed conjugation of 9,10-epoxystearic acid with glutathione J. Biochem. Toxicol. 6 1991 147 153
13. D. Tsikas, and G. Brunner Analysis of glutathione conjugates by HPLC. II. Ion-exchange chromatography and fluorescence detection Fresenius J. Anal. Chem. 343 1992 330 334
14. M. Balazy, T. Iesaki, J.L. Park, H. Jiang, P.M. Kaminski, and M.S. Wolin Vicinal nitrohydroxyeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid J. Pharmacol. Exp. Ther. 299 2001 611 619 (Pubitemid 32979674)
15. P.R.S. Baker, F.J. Schopfer, S. Sweeney, and B.A. Freeman Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation Proc. Natl Acad. Sci. U. S. A. 101 2004 11577 11582 (Pubitemid 39095338)
16. B. Kalyanaraman Nitrated lipids: a class of cell-signaling molecules Proc. Natl Acad. Sci. U. S. A. 101 2004 11527 11528
17. F.J. Schopfer, P.R.S. Baker, G. Giles, P. ChumLey, C. Batthyany, J. Crawford, R.P. Patel, N. Hogg, B.P. Branchaud, J.R. Lancaster Jr., and B.A. Freeman Fatty acid transduction of nitric oxide signalling J. Biol. Chem. 280 2005 19289 19927
18. P.R.S. Baker, Y. Lin, F.J. Schopfer, S.R. Woodcock, A.L. Groeger, C. Bathyany, S. Sweeney, M.H. Long, K.E. Iles, L.M.S. Baker, B.P. Branchaud, Y.E. Chen, and B.A. Freeman Fatty acid transduction of nitric oxide signalling J. Biol. Chem. 280 2005 42464 42475
19. É.S. Lima, M.G. Bovini, O. Augusto, H.V. Barbero, H.P. Souza, and D.S.P. Abballa Nitrated lipids decompose to nitric oxide and lipids radicals and cause vasorelaxation Free Radic. Biol. Med. 39 2005 532 539 (Pubitemid 41021651)
20. T. Cui, F.J. Schopfer, J. Zhang, K. Chen, T. Ichikawa, P.R.S. Baker, C. Bathyany, B.K. Chacko, X. Feng, R.P. Patel, A. Agarwal, and B.A. Freeman Nitrated fatty acids: endogenous anti-inflammatory signalling mediators J. Biol. Chem. 281 2005 35686 35698
21. S.R. Woodcock, A.J.V. Marwitz, P. Bruno, and B.P. Branchoud Synthesis of nitrolipids. All four possible diastereomers of nitrooleic acids: (E)- and (Z)-, 9- and 10-nitro-octadec-9-enoic acids Org. Lett. 8 2006 3931 3934 (Pubitemid 44432823)
22. 2 Free Radic. Biol. Med. 45 2008 269 283
23. A. Trostchansky, and H. Rubbo Nitrated fatty acids: mechanism of formation, chemical charcterization, and biological properties Free Radic. Biol. Med. 44 2008 1887 1896
24. H. Rubbo, and R. Radi Protein and lipid nitration: role in redox signaling and injury Biochim. Biophys. Acta 1780 2008 1318 1324
25. B.A. Freeman, P.R.S. Baker, F.J. Schopfer, S.R. Woodcock, A. Napoletano, and M. d'Ischia Nitro-fatty acid formation and signaling J. Biol. Chem. 283 2008 15515 15519
26. F.J. Schopfer, C. Batthyany, P.R.S. Baker, G. Bonacci, M.P. Cole, V. Rudolph, A. Groeger, T.K. Rudolph, S. Nadtochiy, P.S. Brookes, and B.A. Freeman Detection and quantification of protein adduction by electrophilic fatty acids: mitochondrial generation of fatty acid nitroalkene derivatives Free Radic. Biol. Med. 4 2009 1250 1259
27. P.R.S. Baker, F.J. Schopfer, V.B. O'Donnell, and B.A. Freeman Convergence of nitric oxide and lipid signaling: anti-inflammatory nitro-fatty acids Free Radic. Biol. Med. 46 2009 989 1003
28. A. Trostchansky, J.M. Souza, A. Ferreira, M. Ferrari, F. Blancko, M. Trujillo, D. Castro, H. Cerecetto, R.P. Baker, V.B. O'Donnell, and H. Rubbo Synthesis, isomer characterization, and anti-inflammatory properties of nitroarachidonate Biochemistry 46 2007 4645 4653 (Pubitemid 46625519)
29. L. Chen, C.A. Bosworth, T. Pico, J.F. Collawn, K. Varga, Z. Gaao, J.P. Clancy, J.A. Fortenberry, J.R. Lancaster Jr., and S. Matalon DETANO and nitrated lipids increase chloride secretion across lung airway cells Am. J. Respir. Cell Mol. 39 2008 150 162
30. K.E. Iles, M.M. Wright, M.P. Cole, N.E. Welty, L.B. Ware, M.A. Matthay, F.J. Schopfer, P.R.S. Baker, A. Agarwal, and B.A. Freeman Fatty acids transduction of nitric acid signalling: nitrolinoleic acid mediates protective effects through regulation of the ERK pathway Free Radic. Biol. Med. 46 2009 866 875
31. T.E. Taylor-Clark, S. Ghatta, W. Bettner, and B.J. Undem Nitrooleic acid, an endogenous product of nitrative stress, activates nociceptive sensory nerves via the direct activation of TRPA1 Mol. Pharmacol. 75 2009 820 829
32. V. Rudolph, F.J. Schopfer, N.K.H. Khoo, T.K. Rudolph, M.P. Cole, S. Woodcock, G. Bonacci, A.L. Groeger, F. Golin-Bisello, C.S. Chen, P.R.S. Baker, and B.A. Freeman Nitro-fatty acid metabolome: saturation, desaturation, β-oxidation, and protein adduction J. Biol. Chem. 284 2009 1461 1473
33. D. Tsikas A critical review and discussion of analytical methods in the l-arginine/nitric oxide (NO) area of basic and clinical research Anal. Biochem. 379 2008 139 163
34. D. Tsikas, A. Zoerner, A. Mitschke, Y. Homsi, F.M. Gutzki, and J. Jordan Specific GC-MS/MS stable-isotope dilution methodology for free 9- and 10-nitro-oleic acid in human plasma challenges previous LC-MS/MS reports J. Chromatogr. B 877 2009 2895 2908
35. D. Tsikas, A.A. Zoerner, A. Mitschke, and F.M. Gutzki Nitro-fatty acids occur in human plasma in the picomolar range: a targeted nitro-lipidomics GC-MS/MS study Lipids 44 2009 855 865
36. G.A. Ulsaker, and G. Teien Gas chromatographic mass specrometric identification of four triene monoepoxides of arachidonic acid in human plasma Analyst 115 1990 259 262 (Pubitemid 20157488)
37. G.A. Ulsaker, and G. Teien Identification of 9,10-epoxyoctadecanoic acid in human urine using gas chromatography-mass spectrometry Biomed. Chromatogr. 9 1995 183 187
38. A. Sevanian, J.F. Mead, and R.A. Stein Epoxides as products of lipid autoxidation in rat lungs Lipids 14 1979 634 643 (Pubitemid 9244376)
39. 2 and epoxide hydrolase Lipids 16 1981 781 789
40. E. Blée, and F. Schuber Efficient epoxidation of unsaturated fatty acids by a hydroperoxide-dependent oxygenase J. Biol. Chem. 265 1990 12887 12894
41. N. Chacos, J.R. Folck, C. Wixtrom, and J. Capdevila Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid Biochem. Biophys. Res. Commun. 104 1982 916 922 (Pubitemid 12108300)
42. H.W. Knoche Incorporation of oxygen-18 into the oxirane ring of cis-9,10-epoxyoctadecanoic acid Lipids 6 1971 581 583
43. M. Hamberg, and G. Hamberg Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.) Arch. Biochem. Biophys. 283 1990 409 416
44. D. Tsikas Identifying and quantifying contaminants contributing to endogenous analytes in gas chromatography-mass spectrometry Anal. Chem. 82 2010 7835 7841
45. D. Tsikas Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to assess in vivo synthesis of prostaglandins, thromboxane, leukotrienes, isoprostanes and related compounds in humans J. Chromatogr. B 717 1998 201 245 (Pubitemid 28464601)
46. R.C. Murphy, R.M. Barkley, K.Z. Berry, J. Hankin, K. Harrison, C. Johnson, J. Krank, A. McAnoy, C. Uhlson, and S. Zarin Electrospray ionization and tandem mass spectrometry of eicosanoids Anal. Biochem. 346 2005 1 42 (Pubitemid 41456623)
47. 2 α. Possible methodological, mechanistic and clinical implications J. Chromatogr. B 794 2003 237 255 (Pubitemid 37107351)
48. D. Tsikas, and K. Caidahl Recent methodological advances in the mass spectrometric analysis of free and protein-associated 3-nitrotyrosine in human plasma J. Chromatogr. B 814 2005 1 9 (Pubitemid 40017929)
49. H. Ryberg, and K. Caidahl Chromatographic and mass spectrometric methods for quantitative determination of 3-nitrotyrosine in biological samples and their application to human samples J. Chromatogr. B 851 2007 160 171 (Pubitemid 46720146)
50. D. Tsikas Analytical methods for 3-nitrotyrosine quantification in biological samples: the unique role of tandem mass spectrometry Amino Acids 2011 10.1007/s00726-010-0604-5