Lipidomic analysis of polyunsaturated fatty acids and their oxygenated metabolites in plasma by solid-phase extraction followed by LC-MS

Analytical and Bioanalytical Chemistry

Volumn 406, Issue 12, 2014, Pages 2827-2839

  Dasilva, Gabriel ^a   Pazos, Manuel ^a   Gallardo, José M ^a   Rodríguez, Isaac ^b   Cela, Rafael ^b   Medina, Isabel ^a  

^a INSTITUTO DE INVESTIGACIONES MARINAS   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Ion trap; Liquid chromatography; Mass spectrometry; Oxygenated lipidmediators; Solid phase extraction; Triple quadrupole

Indexed keywords

CHROMATOGRAPHY; CONTRAST MEDIA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONS; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHASE SEPARATION; POLYUNSATURATED FATTY ACIDS; SUGAR SUBSTITUTES;

FALSE-POSITIVE IDENTIFICATIONS; FRAGMENTATION PATTERNS; ION TRAPS; MULTIPLE REACTION MONITORING; OXIDATION PRODUCTS; OXYGENATED LIPIDMEDIATORS; SOLID-PHASE EXTRACTION; TRIPLE QUADRUPOLE;

EXTRACTION;

UNSATURATED FATTY ACID;

ANIMAL; BLOOD; CHEMICAL STRUCTURE; CHEMISTRY; EVALUATION STUDY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; LIMIT OF DETECTION; METABOLISM; PROCEDURES; RAT; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FATTY ACIDS, UNSATURATED; FEMALE; LIMIT OF DETECTION; MOLECULAR STRUCTURE; RATS; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY;

EID: 84904385859     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-014-7701-3     Document Type: Article

References (42)

1. Frankel EN (1998) Lipid oxidation. The Oily Press LTD,West Ferry, Dundee, Scotland
2. Mathews CK, Van Holde KE, Ahern KG (2003) In: Capella I (ed) Biochemistry, 3rd edn. Addison Wesley, Oregon
3. Masoodi M, Mir AA, Petasis NA, Serhan CN, Nicolaou A (2008) Simultaneous lipidomic analysis of three families of bioactive lipid mediators leukotrienes, resolvins, protectins and related hydroxyfatty acids by liquid chromatography/electrospray ionisation tandem mass spectrometry. Rapid Commun Mass Spectrom 22(2):75-83. doi:10.1002/rcm.3331
4. Nithipatikom K, DiCamelli R, Kohler S, Gumina R, Falck J, Campbell W, Gross G (2001) Determination of cytochrome P450 metabolites of arachidonic acid in coronary venous plasma during ischemia and reperfusion in dogs. Anal Biochem 292(1):115-124. doi:10.1006/abio.2001.5044
5. Yin H, Brooks JD, Gao L, Porter NA, Morrow JD (2007) Identification of novel autoxidation products of the omega-3 fatty acid eicosapentaenoic acid in vitro and in vivo. J Biol Chem 282(41): 29890-29901. doi:10.1074/jbc.M703108200
6. Kamal-Eldin A, Yanishlieva N (2002) N-3 fatty acids for human nutrition: stability considerations. Eur J Lipid Sci Technol 104(12): 825-836. doi:10.1002/1438-9312(200212)104:123.0.CO;2-N
7. Gao L, Yin H, Milne G, Porter N, Morrow J (2006) Formation of Fring isoprostane-like compounds (F-3-isoprostanes) in vivo from eicosapentaenoic acid. J Biol Chem 281(20):14092-14099. doi:10.1074/jbc.M601035200
8. Massey KA, NicolaouA(2011) Lipidomics of polyunsaturated-fattyacid- derived oxygenated metabolites. Biochem Soc Trans 39(5): 1240-1246. doi:10.1042/BST0391240
9. SunY, OHSF, Uddin J,Yang R,Gotlinger K, Campbell E, Colgan SP, Petasis NA, Serhan CN (2007) Resolvin D1 and its aspirin-triggered 17R epimer-stereochemical assignments, anti-inflammatory properties, and enzymatic inactivation. J Biol Chem 282(13):9323-9334. doi:10.1074/jbc.M609212200
10. Min L, Li Y, Yu B, Huwei L (2014) Analytical methods in lipidomics and their applications. Anal Chem 86(1):161
11. Davi G, Alessandrini P, Mezzetti A, Minotti G, Bucciarelli T, Costantini F, Cipollone F, Bon G, Ciabattoni G, Patrono C (1997) In vivo formation of 8-epi-prostaglandin F-2 alpha is increased in hypercholesterolemia. Arterioscler Thromb Vasc Biol 17(11):3230-3235
12. Pratico D, Iuliano L, Basili S, Ferro D, Camastra C, Cordova C, FitzGerald G, Violi F (1998) Enhanced lipid peroxidation in hepatic cirrhosis. J Invest Med 46(2):51-57
13. Stein C, Tanner S, Awad J, Roberts L, Morrow J (1996) Evidence of free radical-mediated injury (isoprostane overproduction) in scleroderma. Arthritis Rheum 39(7):1146-1150. doi:10.1002/art.1780390711
14. Delanty N, Reilly M, Pratico D, Lawson J, McCarthy J, Wood A, Ohnishi S, Fitzgerald D, FitzGerald G (1997) 8-Epi PGF(2 alpha) generation during coronary reperfusion-A potential quantitative marker of oxidant stress in vivo. Circulation 95(11):2492-2499
15. Gopaul N, Anggard E, Mallet A, Betteridge D, Wolff S, Nourooz-Zadeh J (1995) Plasma 8-epi-Pgf(2-Alpha) levels are elevated in individuals with non-insulin-dependent diabetes mellitus. FEBS Lett 368(2):225-229. doi:10.1016/0014-5793(95)00649-T
16. Cavalca V, Minardi F, Scurati S, Guidugli F, Squellerio I, Veglia F, Dainese L, Guarino A, Tremoli E, Caruso D (2010) Simultaneous quantification of 8-iso-prostaglandin-F-2 alpha and 11-dehydro thromboxane B-2 in human urine by liquid chromatographytandem mass spectrometry. Anal Biochem 397(2):168-174. doi:10.1016/j.ab.2009.10.014
17. Walter M, Blumberg J, Dolnikowski G, Handelman G (2000) Streamlined F-2-isoprostane analysis in plasma and urine with high-performance liquid chromatography and gas chromatography/ mass spectroscopy. Anal Biochem 280(1):73-79. doi:10.1006/abio.1999.4476
18. Waddington E, Sienuarine K, Puddey I, Croft K (2001) Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography. Anal Biochem 292(2):234-244. doi:10.1006/abio.2001.5075
19. Kelly L, Grehan B, Della Chiesa A, OMara SM, Downer E, Sahyoun G, Massey KA, Nicolaou A, Lynch MA (2011) The polyunsaturated fatty acids, EPA and DPA exert a protective effect in the hippocampus of the aged rat. Neurobiol Aging 32(12):2318.e1-2318.e15. doi:10.1016/j.neurobiolaging.2010.04.001
20. Serhan CN, GotlingerK, Hong S, LuY, Siegelman J, Baer T, Yang R, Colgan SP, Petasis NA (2006) Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: assignments of dihydroxy-containing docosatrienes. J Immunol 176(3): 1848-1859
21. Arita M, Bianchini F, Aliberti J, Sher A, Chiang N, Hong S, Yang R, Petasis NA, Serhan CN (2005) Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1. J Exp Med 201(5):713-722. doi:10.1084/jem.20042031
22. Lee CH (2012) Resolvins as new fascinating drug candidates for inflammatory diseases. Arch Pharm Res 35(1):3-7. doi:10.1007/ s12272-012-0121-z
23. Masoodi M, Eiden M, Koulman A, Spaner D, Volmer DA (2010) Comprehensive lipidomics analysis of bioactive lipids in complex regulatory networks. Anal Chem 82(19):8176-8185. doi:10.1021/ ac1015563
24. Masoodi M, Nicolaou A (2006) Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 20(20): 3023-3029. doi:10.1002/rcm.2697
25. Kretschmer A, Giera M, Wijtmans M, de Vries L, Lingeman H, Irth H, Niessen WMA (2011) Derivatization of carboxylic acids with 4-APEBA for detection by positive-ion LC-ESI-MS(/MS) applied for the analysis of prostanoids and NSAID in urine. J Chromatogr B 879(17-18):1393-1401. doi:10.1016/j.jchromb.2010. 11.028
26. Zhang H, Ilyasova D, Sztaray J, Young SP, Wang F, Millington DS (2010) Quantification of the oxidative damage biomarker 2,3-dinor-8-isoprostaglandin-F- 2 alpha in human urine using liquid chromatography-tandem mass spectrometry. Anal Biochem 399(2): 302-304. doi:10.1016/j.ab.2009.12.024
27. Yang J, Schmelzer K, Georgi K, Hammock BD (2009) Quantitative profiling method for oxylipin metabolome by liquid chromatography electrospray ionization tandem mass spectrometry. Anal Chem 81(19):8085-8093. doi:10.1021/ac901282n
28. Medina S, Dominguez-Perles R, Gil JI, Ferreres F, Garcia-Viguera C, Martinez-Sanz JM, Gil-Izquierdo A (2012) A ultra-pressure liquid chromatography/triple quadrupole tandem mass spectrometry method for the analysis of 13 eicosanoids in human urine and quantitative 24 hour values in healthy volunteers in a controlled constant diet. Rapid Commun Mass Spectrom 26(10):1249-1257. doi:10.1002/ rcm.6224
29. Deems R, Buczynski MW, Bowers-Gentry R, Harkewicz R, Dennis EA (2007) Detection and quantitation of eicosanoids via high performance liquid chromatography-electrospray ionization-mass spectrometry. Lipidomics Bioact Lipids Mass-Spectrom-Based Lipid Anal 432:59-82. doi:10.1016/S0076-6879(07) 32003-X
30. Taylor AW, Bruno RS, Traber MG (2008)Women and smokers have elevated urinary F(2)-isoprostane metabolites: a novel extraction and LC-MS methodology. Lipids 43(10):925-936. doi:10.1007/s11745-008-3222-1
31. Nourooz-Zadeh J (2008) Key issues in F-2-isoprostane analysis. Biochem Soc Trans 36(Pt 5):1060-1065. doi:10.1042/BST0361060
32. Levandi T, Pussa T, Vaher M, Toomik P, Kaljurand M (2009) Oxidation products of free polyunsaturated fatty acids in wheat varieties. Eur J Lipid Sci Technol 111(7):715-722. doi:10.1002/ejlt.200800286
33. Maskrey BH, ODonnell VB (2008) Analysis of eicosanoids and related lipid mediators using mass spectrometry. Biochem Soc Trans 36(Pt 5):1055-1059. doi:10.1042/BST0361055
34. Kortz L, Geyer R, Ludwig U, Planert M, Bruegel M, Leichtle A, Fiedler GM, Thiery J, Ceglarek U (2009) Simultaneous eicosanoid profiling and identification by liquid chromatography and hybrid triple quadrupole-linear ion trap mass spectrometry for metabolomic studies in human plasma. Laboratoriumsmedizin-J Lab Med 33(6): 341-348. doi:10.1515/JLM.2009.057
35. Dickinson J, Murphy R (2002) Mass spectrometric analysis of leukotriene A(4) and other chemically reactive metabolites of arachidonic acid. J Am Soc Mass Spectrom 13(10):1227-1234. doi:10.1016/S1044-0305(02)00456-7
36. Li M, Feng B, Liang Y, Zhang W, Bai Y, Tang W, Wang T, Liu H (2013) Lipid profiling of human plasma from peritoneal dialysis patients using an improved 2D (NP/RP) LC-QToF MS method. Anal Bioanal Chem 405(21):6629-6638. doi:10.1007/s00216-013-7109-5
37. Massey KA, Nicolaou A (2013) Lipidomics of oxidized polyunsaturated fatty acids. Free Radic Biol Med 59:45-55. doi:10.1016/j. freeradbiomed.2012.08.565
38. Margalit A, Duffin K, Isakson P (1996) Rapid quantitation of a large scope of eicosanoids in two models of inflammation: development of an electrospray and tandem mass spectrometry method and application to biological studies. Anal Biochem 235(1):73-81. doi:10.1006/ abio.1996.0093
39. Ferreiro-Vera C, Mata-Granados JM, Priego-Capote F, Quesada-Gomez JM, Luque de Castro MD (2011) Automated targeting analysis of eicosanoid inflammation biomarkers in human serum and in the exometabolome of stem cells by SPE-LC-MS/MS. Anal Bioanal Chem 399(3):1093-1103. doi:10.1007/s00216-010-4400-6
40. Durn JH, Marshall KM, Farrar D, ODonovan P, Scally AJ, Woodward DF, Nicolaou A (2010) Lipidomic analysis reveals prostanoid profiles in human term pregnant myometrium. Prostaglandins Leukot Essent Fat Acids 82(1):21-26. doi:10.1016/j.plefa.2009.11.002
41. McDaniel JC, Massey K, Nicolaou A (2011) Fish oil supplementation alters levels of lipid mediators of inflammation in microenvironment of acute human wounds.Wound Repair Regen 19(2):189-200. doi:10.1111/j.1524-475X.2010.00659.x
42. Jessome L, Volmer D (2006) Ion suppression: a major concern in mass spectrometry. Lc Gc N Am 24(5):498