Nitro-fatty acids occur in human plasma in the picomolar range: A targeted nitro-lipidomics GC-MS/MS study

Lipids

Volumn 44, Issue 9, 2009, Pages 855-865

  Tsikas, Dimitrios ^a   Zoerner, Alexander A ^a   Mitschke, Anja ^a   Gutzki, Frank Mathias ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

Author keywords

Fatty acids; GC MS MS; HPLC; Interferences; LC MS MS; Lipidomics; Nitration; Quantification; Stable isotopes; Validation

Indexed keywords

ACETIC ACID ETHYL ESTER; ARACHIDONIC ACID; FATTY ACID; LINOLENIC ACID; OLEIC ACID;

ARTICLE; CONTROLLED STUDY; FATTY ACID ANALYSIS; FATTY ACID BLOOD LEVEL; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOMERISM; LIPIDOMICS; NITRATION; SOLID PHASE EXTRACTION; SOLVENT EXTRACTION; TANDEM MASS SPECTROMETRY;

FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; NITRO COMPOUNDS; SENSITIVITY AND SPECIFICITY; TANDEM MASS SPECTROMETRY;

EID: 70349257172     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-009-3332-4     Document Type: Article

References (30)

1. M Balazy T Iesaki JL Park H Jiang PM Kaminski MS Wolin 2001 Vicinal nitrohydroxyeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid J Pharmacol Exp Ther 299 611 619 11602673 1:CAS:528:DC%2BD3MXnvV2qt74%3D
2. PRS Baker FJ Schopfer S Sweeney BA Freeman 2004 Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation Proc Natl Acad Sci USA 101 11577 11582 15273286 10.1073/pnas.0402587101 1:CAS:528:DC%2BD2cXntVektb0%3D (Pubitemid 39095338)
3. B Kalyanaraman 2004 Nitrated lipids: a class of cell-signaling molecules Proc Natl Acad Sci USA 101 11527 11528 15292510 10.1073/pnas.0404309101 1:CAS:528:DC%2BD2cXntVektL0%3D (Pubitemid 39095328)
4. FJ Schopfer PRS Baker G Giles P ChumLey C Batthyany J Crawford RP Patel N Hogg BP Branchaud JR Lancaster Jr BA Freeman 2005 Fatty acid transduction of nitric oxide signalling J Biol Chem 280 19289 19927 15764811 10.1074/jbc.M414689200 1:CAS:528:DC%2BD2MXjvFersLc%3D (Pubitemid 41379636)
5. PRS Baker Y Lin FJ Schopfer SR Woodcock AL Groeger C Bathyany S Sweeney MH Long KE Iles LMS Baker BP Branchaud YE Chen BA Freeman 2005 Fatty acid transduction of nitric oxide signalling J Biol Chem 280 42464 42475 16227625 10.1074/jbc.M504212200 1:CAS:528:DC%2BD2MXhtlajs7zF (Pubitemid 43023219)
6. ÉS Lima MG Bovini O Augusto HV Barbero HP Souza DSP Abballa 2005 Nitrated lipids decompose to nitric oxide and lipids radicals and cause vasorelaxation Free Radic Biol Med 39 532 539 16043024 10.1016/j.freeradbiomed. 2005.04.005 1:CAS:528:DC%2BD2MXmvVKgu7w%3D (Pubitemid 41021651)
7. T Cui FJ Schopfer J Zhang K Chen T Ichikawa PRS Baker C Bathyany BK Chacko X Feng RP Patel A Agarwal BA Freeman 2005 Nitrated fatty acids: endogenous anti-inflammatory signalling mediators J Biol Chem 281 35686 35698 10.1074/jbc.M603357200
8. SR Woodcock AJV Marwitz P Bruno BP Branchoud 2006 Synthesis of nitrolipids. All four possible diastereomers of nitrooleic acids: (E)- and (Z)-, 9- and 10-nitro-octadec-9-enoic acids Org Lett 8 3931 3934 16928041 10.1021/ol0613463 1:CAS:528:DC%2BD28Xns1Wqur0%3D (Pubitemid 44432823)
9. 2 Free Radic Biol Med 45 269 283 18457679 10.1016/j.freeradbiomed.2008.04.015 1:CAS:528:DC%2BD1cXntlSrsr4%3D
10. A Trostchansky H Rubbo 2008 Nitrated fatty acids: mechanism of formation, chemical characterization, and biological properties Free Radic Biol Med 44 1887 1896 18395528 10.1016/j.freeradbiomed.2008.03.006 1:CAS:528: DC%2BD1cXlslOru7s%3D
11. H Rubbo R Radi 2008 Protein and lipid nitration: role in redox signaling and injury Biochim Biophys Acta 1780 1318 1324 18395525 1:CAS:528: DC%2BD1cXhtVarsbfE
12. BA Freeman PRS Baker FJ Schopfer SR Woodcock A Napoletano M d'Ischia 2008 Nitro-fatty acid formation and signaling J Biol Chem 283 15515 15519 18285326 10.1074/jbc.R800004200 1:CAS:528:DC%2BD1cXmsFektrk%3D
13. D Tsikas A Zoerner A Mitschke Y Homsi FM Gutzki J Jordan 2009 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 2895 2908 10.1016/j.jchromb.2008.12.062 1:CAS:528:DC%2BD1MXps1Whuro%3D
14. V Rudolph FJ Schopfer NKH Khoo TK Rudolph MP Cole S Woodcock G Bonacci AL Groeger F Golin-Bisello CS Chen PRS Baker BA Freeman 2009 Nitro-fatty acid metabolome: saturation, desaturation, β-oxidation, and protein adduction J Biol Chem 284 1461 1473 19015269 10.1074/jbc.M802298200 1:CAS:528: DC%2BD1MXjtFKqtw%3D%3D
15. Hu C, van der Heijden R, Wang M, van der Greef J, Hankemeier T, Xu G (2009) Analytical strategies in lipidomics and applications in disease biomarker discovery. J Chromatogr B 877:2836-2846
16. TM Annesley 2003 Ion suppression in mass spectrometry Clin Chem 49 1041 1044 12816898 10.1373/49.7.1041 1:CAS:528:DC%2BD3sXltFeisLg%3D (Pubitemid 36751088)
17. BK Matuszewski 2006 Standard line slopes as a measure of a relative matrix effect in quantitative HPLC-MS bioanalysis J Chromatogr B 820 293 300 10.1016/j.jchromb.2005.11.009 (Pubitemid 43075465)
18. Tsikas D, Dehnert S, Urban K, Surdacki A, Meyer HH (2009) GC-MS analysis of S-nitrosothiols after conversion to S-nitroso-N-acetylcysteine ethyl ester and in-injector nitrosation of ethyl acetate. J Chromatogr B. doi: 10.1016/j.jchromb.2009.06.032
19. N Christeff F Homo-Delarche N Thobie S Durant M Dardenne EA Nunez 1994 Free fatty acid profiles in the non-obese diabetic (NOD) mouse: basal serum levels and effects of endocrine manipulation Prostaglandins Leukot Essent Fatty Acids 51 125 131 7972266 10.1016/0952-3278(94)90088-4 1:CAS:528: DyaK2cXltlWnt7k%3D (Pubitemid 24240590)
20. WS Jobgen SC Jobgen H Li CJ Meininger G Wu 2007 Analysis of nitrite and nitrate in biological samples using high-performance liquid chromatography J Chromatogr B 851 71 82 10.1016/j.jchromb.2006.07.018 1:CAS:528: DC%2BD2sXlt1aktbY%3D (Pubitemid 46720130)
21. D Giustarini A Milzani I Dalle-Donne R Rossi 2007 Detection of S-nitrosothiols in biological fluids: a comparison among the most widely applied methodologies J Chromatogr B 851 124 139 10.1016/j.jchromb.2006.09.031 1:CAS:528:DC%2BD2sXlt1akt7Y%3D (Pubitemid 46720138)
22. D Tsikas K Caidahl 2005 Recent methodological advances in the mass spectrometric analysis of free and protein-associated 3-nitrotyrosine in human plasma J Chromatogr B 814 1 9 10.1016/j.jchromb.2004.10.003 1:CAS:528: DC%2BD2cXhtVyksrvF (Pubitemid 40017929)
23. H Ryberg K Caidahl 2007 Chromatographic and mass spectrometric methods for quantitative determination of 3-nitrosotyrosine in biological samples and their application to human samples J Chromatogr B 851 160 171 10.1016/j.jchromb.2007.02.001 1:CAS:528:DC%2BD2sXlt1aktL8%3D (Pubitemid 46720146)
24. D Tsikas 2008 A critical review and discussion of analytical methods in the l-arginine/nitric oxide (NO) area of basic and clinical research Anal Biochem 379 139 163 18510938 10.1016/j.ab.2008.04.018 1:CAS:528: DC%2BD1cXnvVKjt7k%3D
25. FJ Schopfer C Batthyany PRS Baker G Bonacci MP Cole V Rudolph A Groeger TK Rudolph S Nadtochiy PS Brookes BA Freeman 2009 Detection and quantification of protein adduction by electrophilic fatty acids: mitochondrial generation of fatty acid nitroalkene derivatives Free Radic Biol Med 46 1250 1259 19353781 10.1016/j.freeradbiomed.2008.12.025 1:CAS:528:DC%2BD1MXkt1Shs7c%3D
26. PRS Baker FJ Schopfer VB O'Donnell BA Freeman 2009 Convergence of nitric oxide and lipid signaling: anti-inflammatory nitro-fatty acids Free Radic Biol Med 46 989 1003 19200454 10.1016/j.freeradbiomed.2008.11.021 1:CAS:528:DC%2BD1MXkt1Shuro%3D
27. A Trostchansky JM Souza A Ferreira M Ferrari F Blancko M Trujillo D Castro H Cerecetto RP Baker VB O'Donnell H Rubbo 2007 Synthesis, isomer characterization, and anti-inflammatory properties of nitroarachidonate Biochemistry 46 4645 4653 17373826 10.1021/bi602652j 1:CAS:528: DC%2BD2sXjt1Wisb0%3D (Pubitemid 46625519)
28. L Chen CA Bosworth T Pico JF Collawn K Varga Z Gaao JP Clancy JA Fortenberry JR Lancaster Jr S Matalon 2008 DETANO and nitrated lipids increase chloride secretion across lung airway cells Am J Respir Cell Mol Biol 39 150 162 18314534 10.1165/rcmb.2008-0005OC 1:CAS:528:DC%2BD1cXpsFOnt78%3D
29. KE Iles MM Wright MP Cole NE Welty LB Ware MA Matthay FJ Schopfer PRS Baker A Agarwal BA Freeman 2009 Fatty acids transduction of nitric acid signalling: nitrolinoleic acid mediates protective effects through regulation of the ERK pathway Free Radic Biol Med 46 866 875 19133325 10.1016/j. freeradbiomed.2008.12.001 1:CAS:528:DC%2BD1MXivVKgtb8%3D
30. TE Taylor-Clark S Ghatta W Bettner BJ Undem 2009 Nitrooleic acid, an endogenous product of nitrative stress, activates nociceptive sensory nerves via the direct activation of TRPA1 Mol Pharmacol 75 820 829 19171673 10.1124/mol.108.054445 1:CAS:528:DC%2BD1MXktVSlurs%3D