Oxidative changes of lipids monitored by MALDI MS

Chemistry and Physics of Lipids

Volumn 164, Issue 8, 2011, Pages 782-795

  Fuchs, Beate ^a   Bresler, Kristin ^a   Schiller, Jürgen ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Lipids; MALDI MS; Oxidation; Phospholipids; Reactive oxygen species

Indexed keywords

ACYL COENZYME A; FERROUS GLUCONATE; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; LIPID; NITROGEN OXIDE; PEROXYNITRITE; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PLASMALOGEN; REACTIVE OXYGEN METABOLITE; SERINE; SUPEROXIDE;

COLORIMETRY; HUMAN; IN VIVO STUDY; LIPID ANALYSIS; LIPID OXIDATION; LIPID STORAGE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; REVIEW;

HUMANS; LIPID METABOLISM; LIPIDS; OXIDATION-REDUCTION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 80053653285     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2011.09.006     Document Type: Review

References (131)

1. A. Aresta, and C.G. Zambonin Detection of hazelnut oil in extra-virgin olive oil by analysis of polar components by micro-solid phase extraction based on hydrophilic liquid chromatography and MALDI-TOF mass spectrometry J. Mass Spectrom. 45 2010 981 988
2. J. Arnhold, O.M. Panasenko, J. Schiller, Yu.A. Vladimirov, and K. Arnold The action of hypochlorous acid on phosphatidylcholine liposomes in dependence on the content of double bonds. Stoichiometry and NMR analysis Chem. Phys. Lipids 78 1995 55 64
3. J. Arnhold, A.N. Osipov, H. Spalteholz, O.M. Panasenko, and J. Schiller Effects of hypochlorous acid on unsaturated phosphatidylcholines Free Radical Biol. Med. 31 2001 1111 1119 (Pubitemid 33000133)
4. J. Arnhold, A.N. Osipov, H. Spalteholz, O.M. Panasenko, and J. Schiller Formation of lysophospholipids from unsaturated phosphatidylcholines under the influence of hypochlorous acid Biochim. Biophys. Acta 1572 2002 91 100 (Pubitemid 35223060)
5. E. Astigarraga, G. Barreda-Gómez, L. Lombardero, O. Fresnedo, F. Castaño, M.T. Giralt, B. Ochoa, R. Rodríguez-Puertas, and J.A. Fernández Profiling and imaging of lipids on brain and liver tissue by matrix-assisted laser desorption/ionization mass spectrometry using 2-mercaptobenzothiazole as a matrix Anal. Chem. 80 2008 9105 9114
6. - J. Am. Chem. Soc. 73 1951 1842 1843
7. S. Bail, G. Stuebiger, H. Unterweger, G. Buchbauer, and S. Krist Characterization of volatile compounds and triacylglycerol profiles of nut oils using SPME-GC-MS and MALDI-TOF-MS Eur. J. Lipid Sci. Technol. 111 2009 170 182
8. H. Bayir, V.A. Tyurin, Y.Y. Tyurina, R. Viner, V. Ritov, A.A. Amoscato, Q. Zhao, X.J. Zhang, K.L. Janesko-Feldman, H. Alexander, L.V. Basova, R.S. Clark, P.M. Kochanek, and V.E. Kagan Selective early cardiolipin peroxidation after traumatic brain injury: an oxidative lipidomics analysis Ann. Neurol. 62 2007 154 169 (Pubitemid 47546501)
9. M.E. Bégin Effects of polyunsaturated fatty acids and of their oxidation products on cell survival Chem. Phys. Lipids 45 1987 269 313 (Pubitemid 17152338)
10. - free radicals Photochem. Photobiol. 28 1978 645 649
11. - radicals in aqueous solution J. Phys. Chem. Ref. Data 14 1985 1041 1100
12. A. Bischoff, M. Eibisch, B. Fuchs, R. Süß, M. Schürenberg, D. Suckau, and J. Schiller A simple TLC/MALDI method to monitor oxidation products of phosphatidylcholines and -ethanolamines Acta Chromatogr. 23 2011 365 375
13. M.J. Burkitt A critical overview of the chemistry of copper-dependent low density lipoprotein oxidation: roles of lipid hydroperoxides, alpha-tocopherol, thiols, and ceruloplasmin Arch. Biochem. Biophys. 394 2001 117 135 (Pubitemid 32948291)
14. C.D. Calvano, A. Aresta, F. Palmisano, and C.G. Zambonin A laser desorption ionization time-of-flight mass spectrometry investigation into triacylglycerols oxidation during thermal stressing of edible oils Anal. Bioanal. Chem. 389 2007 2075 2084 (Pubitemid 350198025)
15. C.D. Calvano, I.D. van der Werf, F. Palmisano, and L. Sabbatini Fingerprinting of egg and oil binders in painted artworks by matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis of lipid oxidation by-products Anal. Bioanal. Chem. 400 2011 2229 2240
16. B.P. Chapagain, and Z. Wiesman MALDI-TOF/MS fingerprinting of triacylglycerols (TAGs) in olive oils produced in the Israeli Negev desert J. Agric. Food Chem. 57 2009 1135 1142
17. M. Carini, G. Aldini, and R.M. Facino Mass spectrometry for detection of 4-hydroxy-trans-2-nonenal (HNE) adducts with peptides and proteins Mass Spectrom. Rev. 23 2004 281 305
18. S.C. Cheng, M.Z. Huang, and J. Shiea Thin layer chromatography/mass spectrometry J. Chromatogr. A 1218 2011 2700 2711
19. W.W. Christie Lipid Analysis 2003 The Oily Press Lipid Library Bridgwater, UK
20. D.P. Clifford, and J.E. Repine Hydrogen peroxide mediated killing of bacteria Mol. Cell. Biochem. 49 1982 143 149 (Pubitemid 13142647)
21. 31P NMR spectroscopy in the quality control and authentication of extra-virgin olive oil: a review of recent progress Magn. Reson. Chem. 45 2007 367 377
22. P.C. Dedon, and S.R. Tannenbaum Reactive nitrogen species in the chemical biology of inflammation Arch. Biochem. Biophys. 423 2004 12 22 (Pubitemid 38202218)
23. S.I. Dikalov, and R.P. Mason Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals: reassignment to alkoxyl radical adducts Free Radical Biol. Med. 30 2001 187 197 (Pubitemid 32121796)
24. M.R. Domingues, A. Reis, and P. Domingues Mass spectrometry analysis of oxidized phospholipids Chem. Phys. Lipids 156 2008 1 12
25. K. Dreisewerd The desorption process in MALDI Chem. Rev. 103 2003 395 426
26. J.D. Dunn, and J. Allison The detection of multiply charged dyes using matrix-assisted laser desorption/ionization mass spectrometry for the forensic examination of pen ink dyes directly from paper J. Forensic Sci. 52 2007 1205 1211 (Pubitemid 47342402)
27. M. Eibisch, B. Fuchs, J. Schiller, R. Süß, and K. Teuber Analysis of phospholipid mixtures from biological tissues by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry (MALDI-TOF MS): a laboratory experiment J. Chem. Educ. 88 2011 503 507
28. M. Fitzl, R. Süß, K. Arnold, and J. Schiller Nitrite reduces the effects of HOCl on unsaturated phosphatidylcholines - a MALDI-TOF MS study Chem. Phys. Lipids 140 2006 11 17
29. J. Flemmig, H. Spalteholz, K. Schubert, S. Meier, and J. Arnhold Modification of phosphatidylserine by hypochlorous acid Chem. Phys. Lipids 161 2009 44 50
30. D.A. Ford Lipid oxidation by hypochlorous acid: chlorinated lipids in atherosclerosis and myocardial ischemia Clin. Lipidol. 5 2010 835 852
31. J.H. Forman, and A.B. Fisher R.A. Greenwald, CRC Handbook of Methods for Oxygen Radical Research 1985 CRC Press Boca Raton 359 364
32. E.N. Frankel Lipid Oxidation 2005 The Oily Press Bridgwater
33. G.O. Frühwirth, A. Loidl, and A. Hermetter Oxidized phospholipids: from molecular properties to disease Biochim. Biophys. Acta 1772 2007 718 736 (Pubitemid 46891216)
34. B. Fuchs, C. Schober, G. Richter, R. Süss, and J. Schiller MALDI-TOF MS of phosphatidylethanolamines: different adducts cause different post source decay (PSD) fragment ion spectra J. Biochem. Biophys. Methods 70 2007 689 692 (Pubitemid 46669700)
35. B. Fuchs, K. Müller, F. Göritz, S. Blottner, and J. Schiller Characteristic oxidation products of choline plasmalogens are detectable in cattle and roe deer spermatozoa by MALDI-TOF mass spectrometry Lipids 42 2007 991 998 (Pubitemid 350127313)
36. B. Fuchs, and J. Schiller Application of MALDI-TOF mass spectrometry in lipidomics Eur. J. Lipid Sci. Technol. 111 2009 83 98
37. B. Fuchs, and J. Schiller Recent developments of useful MALDI matrices for the mass spectrometric characterization of apolar compounds Curr. Org. Chem. 13 2009 1664 1681
38. B. Fuchs, J. Schiller, R. Süß, A. Nimptsch, M. Schürenberg, and D. Suckau Capabilities and disadvantages of combined matrix-assisted laserdesorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and high-performance thin-layer chromatography (HPTLC): analysis of egg yolk lipids J. Planar Chromatogr. 22 2009 35 42
39. B. Fuchs, R. Süß, and J. Schiller An update of MALDI-TOF mass spectrometry in lipid research Prog. Lipid Res. 49 2010 450 475
40. B. Fuchs, R. Süss, K. Teuber, M. Eibisch, and J. Schiller Lipid analysis by thin-layer chromatography - a review of the current state J. Chromatogr. A 1218 2011 2754 2774
41. G.P. Gellermann, T.R. Appel, P. Davies, and S. Diekmann Paired helical filaments contain small amounts of cholesterol, phosphatidylcholine and sphingolipids Biol. Chem. 387 2006 1267 1274 (Pubitemid 44402074)
42. J. Gidden, R. Liyanage, B. Durham, and J.O. Lay Jr. Reducing fragmentation observed in the matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of triacylglycerols in vegetable oils Rapid Commun. Mass Spectrom. 21 2007 1951 1957 (Pubitemid 46999244)
43. X. Guo, and E. Lankmayr Multidimensional approaches in LC and MS for phospholipid bioanalysis Bioanalysis 2 2010 1109 1123
44. B.M. Ham, J.T. Jacob, and R.B. Cole MALDI-TOF MS of phosphorylated lipids in biological fluids using immobilized metal affinity chromatography and a solid ionic crystal matrix Anal. Chem. 77 2005 4439 4447 (Pubitemid 41542263)
45. X. Han, and R.W. Gross Shotgun lipidomics: electrospray ionization mass spectrometric analysis and quantitation of cellular lipidomes directly from crude extracts of biological samples Mass Spectrom. Rev. 24 2005 367 412 (Pubitemid 40665798)
46. M. Hamberg, and B. Samuelsson Oxygenation of unsaturated fatty acids by the vesicular gland of sheep J. Biol. Chem. 242 1967 5344 5354
47. A.S. Henick, M.F. Benca, and J.H. Mitchell Estimating carbonyl compounds in rancid fats and foods J. Am. Oil Chem. Soc. 31 1954 88 91
48. Herrero, M., Simó, C., García-Cañas, V., Ibáñez, E., Cifuentes, A. Foodomics: MS-based strategies in modern food science and nutrition. Mass Spectrom. Rev., in press.
49. H. Hidaka, N. Hanyu, M. Sugano, K. Kawasaki, K. Yamauchi, and T. Katsuyama Analysis of human serum lipoprotein lipid composition using MALDI-TOF mass spectrometry Ann. Clin. Lab. Sci. 37 2007 213 221 (Pubitemid 47311337)
50. F. Hillenkamp, and J. Peter-Katalinić MALDI MS - A Practical Guide to Instrumentation, Methods and Application 2007 Wiley-VCH Weinheim
51. W. Hou, H. Zhou, F. Elisma, S.A. Bennett, and D. Figeys Technological developments in lipidomics Brief Funct. Genomic Proteomic 7 2008 395 409
52. L. Huang, M.C. Yappert, J.J. Miller, and D. Borchman Thyroxine ameliorates oxidative stress by inducing lipid compositional changes in human lens epithelial cells Invest. Ophthalmol. Vis. Sci. 48 2007 3698 3704 (Pubitemid 351261107)
53. L. Huang, R. Estrada, M.C. Yappert, and D. Borchman Oxidation-induced changes in human lens epithelial cells. 1. Phospholipids Free Radical Biol. Med. 41 2006 1425 1432 (Pubitemid 44466726)
54. E.D. Inutan, B. Wang, and S. Trimpin Commercial intermediate pressure MALDI ion mobility spectrometry mass spectrometer capable of producing highly charged laserspray ionization ions Anal. Chem. 83 2011 678 684
55. T.W. Jaskolla, W.D. Lehmann, and M. Karas 4-Chloro-alpha-cyanocinnamic acid is an advanced, rationally designed MALDI matrix Proc. Natl. Acad. Sci. U. S. A. 105 2008 12200 12205
56. T. Jaskolla, B. Fuchs, M. Karas, and J. Schiller The new matrix 4-chloro-alpha cyanocinnamic acid allows the detection of phosphatidylethanolamine chloramines by MALDI-TOF mass spectrometry J. Am. Soc. Mass Spectrom. 20 2009 867 874
57. A. Jerlich, A.R. Pitt, R.J. Schaur, and C.M. Spickett Pathways of phospholipid oxidation by HOCl in human LDL detected by LC-MS Free Radical Biol. Med. 28 2000 673 682 (Pubitemid 30171280)
58. Y. Kawai, H. Kiyokawa, Y. Kimura, Y. Kato, K. Tsuchiya, and J. Terao Hypochlorous acid-derived modification of phospholipids: characterization of aminophospholipids as regulatory molecules for lipid peroxidation Biochemistry 45 2006 14201 14211 (Pubitemid 44846209)
59. R.S. Kim, and F.S. LaBella Comparison of analytical methods for monitoring autoxidation profiles of authentic lipids J. Lipid Res. 28 1987 1110 1117
60. W.H. Koppenol The centennial of the Fenton reaction Free Radical Biol. Med. 15 1993 645 651 (Pubitemid 23353414)
61. W.H. Koppenol The Haber-Weiss cycle - 70 years later Redox Rep. 6 2001 229 234 (Pubitemid 32962823)
62. R. Knochenmuss, and R. Zenobi MALDI ionization: the role of in-plume processes Chem. Rev. 103 2003 441 452
63. S. Krist, G. Stuebiger, S. Bail, and H. Unterweger Detection of adulteration of poppy seed oil with sunflower oil based on volatiles and triacylglycerol composition J. Agric. Food Chem. 54 2006 6385 6389 (Pubitemid 44367606)
64. B. Lassgue, and K.K. Griendling NADPH oxidases: functions and pathologies in the vasculature Arterioscler. Thromb. Vasc. Biol. 30 2010 653 661
65. J. Lessig, J. Schiller, J. Arnhold, and B. Fuchs Hypochlorous acid-mediated generation of glycerophosphocholine from unsaturated plasmalogen glycerophosphocholine lipids J. Lipid Res. 48 2007 1316 1324 (Pubitemid 47312033)
66. J. Lessig, and B. Fuchs Plasmalogens in biological systems: their role in oxidative processes in biological membranes, their contribution to pathological processes and aging and plasmalogen analysis Curr. Med. Chem. 16 2009 2021 2041
67. J. Lessig, and B. Fuchs HOCl-mediated glycerophosphocholine and glycerophosphoethanolamine generation from plasmalogens in phospholipid mixtures Lipids 45 2010 37 51
68. E.S. Lima, P. Di Mascio, and D.S. Abdalla Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins J. Lipid Res. 44 2003 1660 1666 (Pubitemid 37185876)
69. E. Malle, G. Marsche, J. Arnhold, and M.J. Davies Modification of low-density lipoprotein by myeloperoxidase-derived oxidants and reagent hypochlorous acid Biochim. Biophys. Acta 1761 2006 392 415 (Pubitemid 43776460)
70. K.M. McAvey, B. Guan, C.A. Fortier, M.A. Tarr, and R.B. Cole Laser-induced oxidation of cholesterol observed during MALDI-TOF mass spectrometry J. Am. Soc. Mass Spectrom. 22 2011 659 669
71. J.C. Morris The acid ionization constant of HOCl from 5 to 35 J. Phys. Chem. 195 1966 133 140
72. M.C. Moya Moreno, D. Mendoza Olivares, F.J. Amézquita López, J.V. Gimeno Adelantado, and F. Bosch Reig Analytical evaluation of polyunsaturated fatty acids degradation during thermal oxidation of edible oils by Fourier transform infrared spectroscopy Talanta 50 1999 269 275
73. M.C. Moya Moreno, D. Mendoza Olivares, F.J. Amézquita López, J.V. Gimeno Adelantado, and F. Bosch Reig Determination of unsaturation grade and trans isomers generated during thermal oxidation of edible oils and fats by FTIR J. Mol. Struct. 482-483 1999 551 556 (Pubitemid 29299556)
74. R.C. Murphy Free-radical-induced oxidation of arachidonoyl plasmalogen phospholipids: antioxidant mechanism and precursor pathway for bioactive eicosanoids Chem. Res. Toxicol. 14 2001 463 472 (Pubitemid 32480012)
75. R.C. Murphy, J.A. Hankin, and R.M. Barkley Imaging of lipid species by MALDI mass spectrometry J. Lipid Res. 50 Suppl 2009 S317 S322
76. C. Nusshold, M. Kollroser, H. Köfeler, G. Rechberger, H. Reicher, A. Ullenm, E. Bernhart, S. Waltl, I. Kratzer, A. Hermetter, H. Hackl, Z. Trajanoski, A. Hrzenjak, E. Malle, and W. Sattler Hypochlorite modification of sphingomyelin generates chlorinated lipid species that induce apoptosis and proteome alterations in dopaminergic PC12 neurons in vitro Free Radical Biol. Med. 48 2010 1588 1600
77. E.M. Oborina, and M.C. Yappert Effect of sphingomyelin versus dipalmitoylphosphatidylcholine on the extent of lipid oxidation Chem. Phys. Lipids 123 2003 223 232 (Pubitemid 36419534)
78. n Lipids 33 1998 843 852 (Pubitemid 28460150)
79. B.W. Patterson Methods for measuring lipid metabolism in vivo Curr. Opin. Clin. Nutr. Metab. Care 5 2002 475 479 (Pubitemid 40684641)
80. D.I. Pattison, C.L. Hawkins, and M.J. Davies Hypochlorous acid-mediated oxidation of lipid components and antioxidants present in low-density lipoproteins: absolute rate constants, product analysis, and computational modeling Chem. Res. Toxicol. 16 2003 439 449 (Pubitemid 36514501)
81. D.I. Pattison, and M.J. Davies Reactions of myeloperoxidase-derived oxidants with biological substrates: gaining chemical insight into human inflammatory diseases Curr. Med. Chem. 13 2006 3271 3290 (Pubitemid 44669775)
82. G.M. Patton, and S.J. Robins Separation and quantitation of phospholipid classes by HPLC Methods Mol. Biol. 110 1998 193 215
83. B.L. Peterson, and B.S. Cummings A review of chromatographic methods for the assessment of phospholipids in biological samples Biomed. Chromatogr. 20 2006 227 243
84. G. Picariello, A. Paduano, R. Sacchi, and F. Addeo MALDI-TOF mass spectrometry profiling of polar and nonpolar fractions in heated vegetable oils J. Agric. Food Chem. 57 2009 5391 5400
85. G. Picariello, R. Romano, and F. Addeo Nitrocellulose film substrate minimizes fragmentation in matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis of triacylglycerols Anal. Chem. 82 2010 5783 5791
86. J. Prousek Fenton chemistry in biology and medicine Pure Appl. Chem. 79 2007 2325 2338
87. M. Pulfer, and R.C. Murphy Electrospray mass spectrometry of phospholipids Mass Spectrom. Rev. 22 2003 332 364
88. M.J. Raftery Detection and characterization of N-alpha-chloramines by electrospray tandem mass spectrometry Anal. Biochem. 366 2007 218 227 (Pubitemid 46898215)
89. M.R. Ramírez, M. Estévez, D. Morcuende, and R. Cava Effect of the type of frying culinary fat on volatile compounds isolated in fried pork loin chops by using SPME-GC-MS J. Agric. Food Chem. 52 2004 7637 7643
90. A. Reis, P. Domingues, A.J. Ferrer-Correia, and M.R. Domingues Fragmentation study of short-chain products derived from oxidation of diacylphosphatidylcholines by electrospray tandem mass spectrometry: identification of novel short-chain products Rapid Commun. Mass Spectrom. 18 2004 2849 2858 (Pubitemid 39576827)
91. G. Richter, C. Schober, R. Süss, B. Fuchs, M. Müller, and J. Schiller The reaction between phosphatidylethanolamines and HOCl investigated by TLC: fading of the dye primuline is induced by dichloramines J. Chromatogr. B 867 2008 233 237
92. G. Richter, C. Schober, R. Süss, B. Fuchs, C. Birkemeyer, and J. Schiller Comparison of the positive and negative ion electrospray ionization and matrix-assisted laser desorption ionization-time-of-flight mass spectra of the reaction products of phosphatidylethanolamines and hypochlorous acid Anal. Biochem. 376 2008 157 159
93. S.A. Saraiva, E.C. Cabral, M.N. Eberlin, and R.R. Catharino Amazonian vegetable oils and fats: fast typification and quality control via triacylglycerol (TAG) profiles from dry matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry fingerprinting J. Agric. Food Chem. 57 2009 4030 4034
94. L.M. Sayre, D. Lin, Q. Yuan, X. Zhu, and X. Tang Protein adducts generated from products of lipid oxidation: focus on HNE and ONE Drug Metab. Rev. 38 2006 651 675 (Pubitemid 44903261)
95. 31P-NMR J. Lipid Res. 42 2001 1501 1508 (Pubitemid 34007682)
96. 31P NMR spectroscopy Eur. Food Res. Technol. 215 2002 282 286
97. J. Schiller, R. Süß, M. Petković, G. Hanke, A. Vogel, and K. Arnold Effects of thermal stressing on saturated vegetable oils and isolated triacylglycerols - product analysis by MALDI-TOF mass spectrometry, NMR and IR spectroscopy Eur. J. Lipid Sci. Technol. 104 2002 496 505
98. J. Schiller, B. Fuchs, J. Arnhold, and K. Arnold Contribution of reactive oxygen species to cartilage degradation in rheumatic diseases: molecular pathways, diagnosis and potential therapeutic strategies Curr. Med. Chem. 10 2003 2123 2145 (Pubitemid 37139067)
99. J. Schiller, K. Müller, R. Süss, J. Arnhold, C. Gey, A. Herrmann, J. Lessig, K. Arnold, and P. Müller Analysis of the lipid composition of bull spermatozoa by MALDI-TOF mass spectrometry - a cautionary note Chem. Phys. Lipids 126 2003 85 94 (Pubitemid 37297968)
100. J. Schiller, R. Süß, B. Fuchs, M. Müller, M. Petković, O. Zschörnig, and H. Waschipky The suitability of different DHB isomers as matrices for the MALDI-TOF MS analysis of phospholipids: Which isomer for what purpose? Eur. Biophys. J. 36 2007 517 527 (Pubitemid 46626207)
101. 2 but not by hypochlorous acid Bioorg. Chem. 37 2009 202 210
102. M. Setou, and N. Kurabe Mass microscopy: high-resolution imaging mass spectrometry J. Electron Microsc. 60 2011 47 56
103. O. Shadyro, I. Yurkova, M. Kisel, O. Brede, and J. Arnhold Formation of phosphatidic acid, ceramide, and diglyceride on radiolysis of lipids: identification by MALDI-TOF mass spectrometry Free Radical Biol. Med. 36 2004 1612 1624 (Pubitemid 38746567)
104. O.I. Shadyro, I.L. Yurkova, M.A. Kisel, O. Brede, and J. Arnhold Radiation-induced fragmentation of cardiolipin in a model membrane Int. J. Radiat. Biol. 80 2004 239 245 (Pubitemid 38586333)
105. T. Shibamoto Analytical methods for trace levels of reactive carbonyl compounds formed in lipid peroxidation systems J. Pharm. Biomed. Anal. 41 2006 12 25
106. R. Shroff, and A. Svatos 1,8-Bis(dimethylamino)naphthalene: a novel superbasic matrix for matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of fatty acids Rapid Commun. Mass Spectrom. 23 2009 2380 2382
107. 13C nuclear magnetic resonance techniques to the characterization of lipid oxidation products in autoxidized linoleoyl/linolenoylglycerols Lipids 34 1999 741 756 (Pubitemid 29381844)
108. H. Spalteholz, K. Wenske, O.M. Panasenko, J. Schiller, and J. Arnhold Evaluation of products upon the reaction of hypohalous acid with unsaturated phosphatidylcholines Chem. Phys. Lipids 129 2004 85 96 (Pubitemid 38293252)
109. L.J. Sparvero, A.A. Amoscato, P.M. Kochanek, B.R. Pitt, V.E. Kagan, and H. Bayir Mass-spectrometry based oxidative lipidomics and lipid imaging: applications in traumatic brain injury J. Neurochem. 115 2010 1322 1336
110. 31P NMR spectroscopy in food analysis. 1. Quantitative determination of the mono- and diglyceride composition of olive oils J. Agric. Food Chem. 48 2000 802 805 (Pubitemid 30194008)
111. G. Stübiger, E. Pittenauer, and G. Allmaier MALDI seamless postsource decay fragment ion analysis of sodiated and lithiated phospholipids Anal. Chem. 80 2008 1664 1678 (Pubitemid 351429572)
112. G. Stübiger, O. Belgacem, P. Rehulka, W. Bicker, B.R. Binder, and V. Bochkov Analysis of oxidized phospholipids by MALDI mass spectrometry using 6-aza-2-thiothymine together with matrix additives and disposable target surfaces Anal. Chem. 82 2010 5502 5510
113. G. Stübiger, G. Sobal, K. Widhalm, O. Belgacem, and K. Pock Influence of HSA and IgG on LDL oxidation studied by size-exclusion chromatography and phospholipid profiling using MALDI tandem-mass spectrometry Chem. Phys. Lipids 164 2011 563 572
114. G. Sun, K. Yang, Z. Zhao, S. Guan, X. Han, and R.W. Gross Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of cellular glycerophospholipids enabled by multiplexed solvent dependent analyte-matrix interactions Anal. Chem. 80 2008 7576 7585
115. Y.E. Sun, W.D. Wang, H.W. Chen, and C. Li Autoxidation of unsaturated lipids in food emulsion Crit. Rev. Food Sci. Nutr. 51 2011 453 466
116. J.C. Touchstone Thin-layer chromatographic procedures for lipid separation J. Chromatogr. B 671 1995 169 195
117. M. Uchiama, and M. Mihara Determination of malonaldehyde precursor in tissues by thiobarbituric acid test Anal. Biochem. 86 1978 271 278 (Pubitemid 9050395)
118. J.J. van den Berg, C.C. Winterbourn, and F.A. Kuypers Hypochlorous acid-mediated modification of cholesterol and phospholipid: analysis of reaction products by gas chromatography-mass spectrometry J. Lipid Res. 34 1993 2005 2012 (Pubitemid 23324974)
119. J.D. van den Berg, N.D. Vermist, L. Carlyle, M. Holcapek, and J.J. Boon Effects of traditional processing methods of linseed oil on the composition of its triacylglycerols J. Sep. Sci. 27 2004 181 199 (Pubitemid 38268246)
120. O.F. van den Brink, J.J. Boon, P.B. O'Connor, M.C. Duursma, and R.M. Heeren Matrix-assisted laser desorption/ionization Fourier transform mass spectrometric analysis of oxygenated triglycerides and phosphatidylcholines in egg tempera paint dosimeters used for environmental monitoring of museum display conditions J. Mass Spectrom. 36 2001 479 492 (Pubitemid 32536860)
121. M.L. Vestal Modern MALDI time-of-flight mass spectrometry J. Mass Spectrom. 44 2009 303 317
122. C. von Sonntag, and H.-P. Schuchmann The elucidation of peroxyl radical reactions in aqueous solution with the help of radiation-chemical methods Angew. Chem. Int. Ed. 30 1991 1229 1253
123. B.A. Wagner, G.R. Buettner, and C.P. Burns Free radical-mediated lipid peroxidation in cells: oxidizability is a function of cell lipid bis-allylic hydrogen content Biochemistry 33 1994 4449 4453 (Pubitemid 24145090)
124. C.C. Winterbourn, M.C. Vissers, and A.J. Kettle Myeloperoxidase Curr. Opin. Hematol. 7 2000 53 58 (Pubitemid 30007688)
125. J. Wu, K. Teuber, M. Eibisch, B. Fuchs, and J. Schiller Chlorinated and brominated phosphatidylcholines are generated under the influence of the Fenton reagent at low pH - a MALDI-TOF MS study Chem. Phys. Lipids 164 2011 1 8
126. M.A. Yorek G. Cevc, Phospholipids Handbook 1993 Marcel Dekker, Inc. New York 745 766
127. H. Yoshida, and R. Kisugi Mechanisms of LDL oxidation Clin. Chim. Acta 411 2010 1875 1882
128. I. Yurkova, M. Kisel, J. Arnhold, and O. Shadyro Free-radical fragmentation of galactocerebrosides: a MALDI-TOF mass spectrometry study Chem. Phys. Lipids 134 2005 41 49 (Pubitemid 40327008)
129. D. Ziech, R. Franco, A.G. Georgakilas, S. Georgakila, V. Malamou-Mitsi, O. Schoneveld, A. Pappa, and M.I. Panayiotidis The role of reactive oxygen species and oxidative stress in environmental carcinogenesis and biomarker development Chem. Biol. Interact. 188 2010 334 339
130. O. Zschörnig, C. Bergmeier, R. Süß, K. Arnold, and J. Schiller Human low-density lipoprotein oxidation: hypochlorous acid leads to the generation of lysophospholipids under acidic conditions Lett. Org. Chem. 1 2004 381 390
131. N.J. Zuidam, H.K. Gouw, Y. Barenholz, and D.J. Crommelin Physical (in)stability of liposomes upon chemical hydrolysis: the role of lysophospholipids and fatty acids Biochim. Biophys. Acta 1240 1995 101 110