Lipidomic analysis of glycerolipid and cholesteryl ester autooxidation products

Molecular Biotechnology

Volumn 42, Issue 2, 2009, Pages 224-268

  Kuksis, Arnis ^a   Suomela, Jukka Pekka ^b   Tarvainen, Marko ^b   Kallio, Heikki ^b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TURKU   (Finland)

Author keywords

Amino acid and glutathione adducts of oxolipids; Cholesteryl esters; Core aldehydes; Fatty acids; Gas and liquid chromatography; Glycerophospholipids; Hydroperoxides; Hydroxides; Isoprostanes; Protein and nucleic acid adducts of oxolipids; Triacylglycerols

Indexed keywords

CHOLESTERYL ESTERS; CORE ALDEHYDES; GLYCEROPHOSPHOLIPIDS; HYDROPEROXIDES; HYDROXIDES; ISOPROSTANES; TRIACYLGLYCEROLS;

ALDEHYDES; AMINATION; AMINES; AMINO ACIDS; ATMOSPHERIC IONIZATION; ATMOSPHERIC PRESSURE; CHROMATOGRAPHIC ANALYSIS; ELECTROSPRAY IONIZATION; ESTERIFICATION; ESTERS; FATTY ACIDS; GAS ABSORPTION; GAS CHROMATOGRAPHY; GLYCEROL; IMPACT IONIZATION; LIQUIDS; MASS SPECTROMETRY; NUCLEIC ACIDS; ORGANIC ACIDS; PARTICLE DETECTORS; THIN LAYER CHROMATOGRAPHY;

LIQUID CHROMATOGRAPHY;

CHOLESTEROL ESTER; GLYCEROLIPID; LIPOPROTEIN; GLYCEROPHOSPHOLIPID; LIPID;

ARTICLE; AUTOOXIDATION; ELECTROSPRAY MASS SPECTROMETRY; GAS CHROMATOGRAPHY; LIPID ANALYSIS; LIPIDOMICS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; CHROMATOGRAPHY; METHODOLOGY; OXIDATION REDUCTION REACTION;

CHOLESTEROL ESTERS; CHROMATOGRAPHY; GLYCEROPHOSPHOLIPIDS; LIPIDS; MASS SPECTROMETRY; OXIDATION-REDUCTION;

EID: 69249229875     PISSN: 10736085     EISSN: None     Source Type: Journal    
DOI: 10.1007/s12033-009-9146-z     Document Type: Article

References (132)

1. C Wolf PJ Quinn 2008 Lipidomics: Practical aspects and applications Progress in Lipid Research 47 15 36 1:CAS:528:DC%2BD2sXhsVSmurbP
2. Kuksis, A., Suomela, J.-P., Tarvainen, M., & Kallio, H. (2008). The use of lipidomics for analysis of Glycerolipid and cholesteryl ester oxidation by GC, LC and on-line Ms. In D. Armstrong (Ed.), Methods in molecular biology. Totowa, NJ : The Humana Press Inc. (in press).
3. B Karten H Boechzelt PM Abuja M Mittelbach K Oettl W Sattler 1998 Femtomole analysis of 9-oxononanoyl cholesterol by high performance liquid chromatography Journal of Lipid Research 39 1508 1519 1:CAS:528: DyaK1cXkslOqurg%3D
4. J Terao I Acano S Matsushita 1985 Preparation of hydroperoxy and hydroxy derivatives of rat liver phosphatidylcholine and phosphatidylethanolamine Lipids 20 312 317 10.1007/BF02534264 10.1007/BF02534264 1:CAS:528:DyaL2MXks1OrsLw%3D (Pubitemid 15086429)
5. TG Traylor H Kiefer 1966 Di-t-Butyl hyponitrite. A convenient source of t-butoxy radicals Tetrahedron Letters 49 6163 6168
6. EA Podrez E Poliakov Z Shen R Zhang Y Deng M Sun PJ Finton L Shan B Gugiu PL Fox HF Hoff RG Salomon SL Hazen 2002 Identification of a novel family of oxidized phospholipids that serve as ligands for the macrophage scavenger receptor CD36 The Journal of Biological Chemistry 277 38503 38516 10.1074/jbc.M203318200 10.1074/jbc.M203318200 1:CAS:528:DC%2BD38Xns1Cnsbk%3D (Pubitemid 35154709)
7. W Zhang M Sun RG Salomon 2006 Preparative singlet oxygenattion of linoleate provides doubly allylic dihydroperoxides: Putative intermediates in the generation of biologically active aldehydes in vivo Journal of Organic Chemistry 71 5607 5615 10.1021/jo0605795 1:CAS:528:DC%2BD28XmtVShsL8%3D (Pubitemid 44117006)
8. X Han RW Gross 2003 Global analyses of cellular lipodomes directly from crude extracts of biological samples by ESI mass spectrometry: A bridge to lipidomics Journal of Lipid Research 44 1071 1079 10.1194/jlr.R300004-JLR200 10.1194/jlr.R300004-JLR200 1:CAS:528:DC%2BD3sXltFarsr0%3D (Pubitemid 37279625)
9. U Garscha T Nilsson EH Oliw 2008 Enantiomeric separation and analysis of unsaturated hydroperoxy fatty acids by chiral column chromatography-mass spectrometry Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 872 90 98 10.1016/j.jchromb.2008.07.013 10.1016/j.jchromb.2008.07.013 1:CAS:528:DC%2BD1cXhtVensbvO
10. +) ion spray-mass spectrometry of peroxidation products of cholesterol linoleate and cholesterol arachidonate: High performance liquid chromatography-mass spectrometry analysis of peroxide products from polyunsaturated lipid autoxidation Journal of the American Chemical Society 122 8042 8055 10.1021/ja001180f 10.1021/ja001180f 1:CAS:528:DC%2BD3cXltlahtLg%3D (Pubitemid 30659426)
11. 2)for lipid analysis Frontiers in Bioscience 13 100 120 10.2741/2663 10.2741/2663 1:CAS:528:DC%2BD1cXhs1Chs7w%3D (Pubitemid 351594765)
12. Fless, G. M. (1991). General properties of ultracentrifugation and considerations for lipoprotein isolation. In E. G. Perkins (Ed.), Analysis of fats, oils and lipoproteins (pp. 512-527). Champaign: AOCS Press.
13. BH Chung JP Segrest MJ Ray JD Brunzell JE Hokanson RM Krauss K Baudrie JT Cone 1986 Single vertical spin-density gradient ultracentrifugation Methods in Enzymology 128 181 209 10.1016/0076-6879(86)28068-4 10.1016/0076-6879(86)28068-4 1:CAS:528:DyaL28Xls1ygsLk%3D
14. B Frei JM Gaziano 1993 Content of antioxidants, preformed lipid hydroperoxides, and cholesterol as predictors of the susceptibility of human LDL to metal ion-dependent and ion-independent oxidation Journal of Lipid Research 34 21350 22145
15. J Terao I Asano S Matsushita 1884 High performance liquid chromatographic determination of phospholipid peroxidation products of rat liver after carbon-tetrachloride administration Archives of Biochemistry and Biophysics 235 326 333 10.1016/0003-9861(84)90205-4 10.1016/0003-9861(84)90205-4
16. 3-isoprostanes) in vivo from eicosapentaenoic acid The Journal of Biological Chemistry 283 12043 12055 10.1074/jbc.M800122200 10.1074/jbc. M800122200 1:CAS:528:DC%2BD1cXltVyrsL4%3D
17. J Adachi N Yoshioka M Sato K Nakagawa Y Yamamoto Y Ueno 2005 Detection of phosphatidylcholine oxidation products in rat heart using quadrupole time-of-flight mass spectrometry Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 823 37 43 10.1016/j.jchromb. 2005.03.035 10.1016/j.jchromb.2005.03.035 1:CAS:528:DC%2BD2MXmvVWmurs%3D (Pubitemid 41073987)
18. MY Golovko EJ Murphy 2008 An improved LC-MS/MS procedure for brain prostanoid analysis using brain fixation with head-focused microwave irradiation and liquid-liquid extraction Journal of Lipid Research 49 893 902 10.1194/jlr.D700030-JLR200 10.1194/jlr.D700030-JLR200 1:CAS:528: DC%2BD1cXjvFegsbw%3D
19. AM Gutierrez GR Reboredo SM Mosca A Catala 2008 An allometric study of fatty acids and sensitivity to lipid peroxidation of brain microsomes and mitochondria isolated from different bird species Comparative Biochemistry and Physiology. Part A 150 359 365 10.1016/j.cbpa.2008.04.597 10.1016/j.cbpa.2008. 04.597 1:CAS:528:DC%2BD1cXnt1aqs7k%3D
20. MA Kiebisch X Han H Cheng A Lunceford CF Clarke H Moon JH Chung TN Seyfried 2008 Lipidomic analysis and electron transport chain activities in C57BL/6J mouse brain mitochondria Journal of Neurochemistry 106 299 312 10.1111/j.1471-4159.2008.05383.x 10.1111/j.1471-4159.2008.05383.x 1:CAS:528:DC%2BD1cXot1Ogsb4%3D (Pubitemid 351840212)
21. T Nakamura DL Bratton RC Murphy 1997 Analysis of epoxyeicosatrienoic and monohydroxyeicosatetraenoic acid esterified to phospholipids in human red blood cells by electrospray tandem mass spectrometry Journal of Mass Spectrometry 32 888 896 10.1002/(SICI)1096-9888(199708)32:8<888::AID-JMS548>3.0.CO;2-W 10.1002/(SICI)1096-9888(199708)32:8<888::AID-JMS548>3.0.CO;2-W 1:CAS:528:DyaK2sXlsFWnsrg%3D (Pubitemid 27331429)
22. RF Spaide WC Ho-Spaide RW Browne D Armstrong 1999 Characterization of peroxidized lipids in Bruch's membrane Retina 19 141 147 10.1097/00006982- 199903000-00009 10.1097/00006982-199903000-00009 1:STN:280:DyaK1M3ivVahuw%3D%3D
23. A Kuksis A Ravandi M Schneider 2005 Covalent binding of acetone to aminophospholipids in vitro and in vivo Annals of the New York Academy of Sciences 1043 417 439 10.1196/annals.1333.049 10.1196/annals.1333.049 1:CAS:528:DC%2BD2MXpvVKqt7o%3D (Pubitemid 41123931)
24. J Folch M Lees GHS Stanley 1957 A simple method for the isolation and purification of total lipids from animal tissues The Journal of Biological Chemistry 226 497 509 1:STN:280:DyaG2s%2FnsFCjtw%3D%3D
25. EG Bligh WJ Dyer 1959 A rapid method of total lipid extraction and purification Canadian Journal of Biochemistry and Physiology 37 911 917 1:CAS:528:DyaG1MXhtVSgt70%3D
26. A Hara NS Radin 1978 Lipid extraction of tissues with low toxicity solvent Analytical Biochemistry 90 420 426 10.1016/0003-2697(78)90046-5 10.1016/0003-2697(78)90046-5 1:CAS:528:DyaE1cXmtFWmsL0%3D
27. V Matyash G Liebisch TV Kurzchalia A Shevchenko D Schwudke 2008 Lipid extraction by methyl-tert-butyl ether for high-throughput lipidomics Journal of Lipid Research 49 1137 1146 10.1194/jlr.D700041-JLR200 1:CAS:528: DC%2BD1cXltFSltLY%3D
28. ML Lenz H Hughes JR Mitchell DP Via JR Guyton AA Taylor AM Gotto Jr CV Smith 1990 Lipid hydroperoxy and hydroxy derivatives in copper-catalyzed oxidation of low density lipoprotein Journal of Lipid Research 31 1043 1050 1:CAS:528:DyaK3cXlsV2rtL8%3D
29. D Schmitt Z Shen SM Colles W Wu RG Saloman Y Chen GM Chisolm SL Hazen 1999 Leukocytes utilize myeloperoxidase-generated nitrating intermediates as physiological catalysts for the generation of biologically active oxidized lipids and sterols in serum Biochemistry 38 16904 16915 10.1021/bi991623w 10.1021/bi991623w 1:CAS:528:DyaK1MXnslSltr4%3D (Pubitemid 30013697)
30. SH Lee MV Williams IA Blair 2005 Targeted chiral lipidomics analysis Prostaglandins & Other Lipid Mediators 77 141 157 10.1016/j.prostaglandins. 2004.01.009 10.1016/j.prostaglandins.2004.01.009 1:CAS:528:DC%2BD2MXnslylu7s%3D (Pubitemid 41133423)
31. H Kamido A Kuksis L Marai JJ Myher H Peng 1992 Preparation, chromatography, and mass spectrometry of cholesteryl ester and glycerolipid-bound aldehydes Lipids 27 645 650 10.1007/BF02536126 10.1007/BF02536126 1:CAS:528:DyaK3sXnt1Ci
32. A Buldt U Karst 1997 1-Methyl-1-(2, 4-dinitrophenyl)hydrazine as a new reagent for HPLC determination of aldehydes Analytical Chemistry 69 3617 3622 10.1021/ac970146p 10.1021/ac970146p
33. 1 and specific detection of prostaglandin A's and 190 hydroxylated prostaglandin A's in human semen Biomedical Mass Spectrometry 9 531 535 10.1002/bms.1200050905 10.1002/bms.1200050905
34. T White S Bursten D Federighi RA Lewis E Nudelman 1998 High resolution separation and quantification of neutral lipid and phospholipid species in mammalian cells and sera by multi-one-dimensional thin-layer chromatography Analytical Biochemistry 258 109 117 10.1006/abio.1997.2545 10.1006/abio.1997. 2545 1:CAS:528:DyaK1cXitlKhs7o%3D (Pubitemid 28163151)
35. K Kishimoto R Urade T Ogawa T Moriyama 2001 Nondestructive quantification of neutral lipids by thin-layer chromatography and laser-fluorescent scanning: Suitable methods for "lipidome" analysis Biochemical and Biophysical Research Communications 281 657 662 10.1006/bbrc.2001.4404 10.1006/bbrc.2001. 4404 1:CAS:528:DC%2BD3MXhsFOgt7g%3D (Pubitemid 32917851)
36. B Fuchs J Schiller R Suss M Schurenberg D Suckau 2007 A direct and simple method of coupling matrix-assisted laser desorption and ionization time-of-flight mass spectrometry (MALDI-TOF MS) to thin-layer chromatography (TLC) for the analysis of phospholipids from egg yolk Analytical and Bioanalytical Chemistry 389 827 834 10.1007/s00216-007-1488-4 10.1007/s00216-007-1488-4 1:CAS:528:DC%2BD2sXhtVOmtLbE (Pubitemid 47462452)
37. A Rohlfing J Muthing G Pohlentz U Distler J Peter-Katalinic S Berkenkamp K Dreisewed 2007 IR-MALDI-MS analysis of HPTLC-separated phospholipid mixtures directly from the TLC plate Analytical Chemistry 79 5793 5808 10.1021/ac070633x 10.1021/ac070633x 1:CAS:528:DC%2BD2sXmslyrurk%3D (Pubitemid 47229831)
38. BL Peterson BS Cummings 2006 A review of chromatographic methods for the assessment of phospholipids in biological samples Biomedical Chromatography 20 227 243 10.1002/bmc.563 10.1002/bmc.563 1:CAS:528:DC%2BD28XjtlKmu7g%3D
39. L Mondello PQ Tranchida P Dugo G Dugo 2008 Comprehensive two-dimensional gas chromatography-mass spectrometry: A review Mass Spectrometry Reviews 27 101 124 10.1002/mas.20158 10.1002/mas.20158 1:CAS:528:DC%2BD1cXktVKkur8%3D (Pubitemid 351315897)
40. Y Chen JD Morrow LJ Roberts II 1999 Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway The Journal of Biological Chemistry 274 10863 10868 10.1074/jbc.274.16.10863 10.1074/jbc.274.16.10863 1:CAS:528:DyaK1MXis1Gnu7k%3D (Pubitemid 29191068)
41. 4-neuroprostanes) in vivo from docosahexaenoic acid The Journal of Biological Chemistry 277 36076 36084 10.1074/jbc.M205638200 10.1074/jbc.M205638200 1:CAS:528: DC%2BD38XnsVCjsL0%3D
42. H Yin ES Musiek L Gao NA Porter JD Morrow 2005 Regiochemistry of neuroprostanes generated from the peroxidation of docosahexaenoic acid in vitro and in vivo The Journal of Biological Chemistry 280 26600 26611 10.1074/jbc.M503088200 10.1074/jbc.M503088200 1:CAS:528:DC%2BD2MXlvFylsr4%3D (Pubitemid 41022258)
43. 4- neuroprostanes) derived from docosahexaenoic acid in vivo in humans by a stable isotope dilution mass spectrometric assay Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 799 95 102 10.1016/j.jchromb.2003.10.036 10.1016/j.jchromb.2003.10.036 1:CAS:528: DC%2BD3sXptlOjurc%3D (Pubitemid 37500867)
44. 3-isoprostanes) in vivo from eicosapentaenoic acid The Journal of Biological Chemistry 281 14092 14099 10.1074/jbc.M601035200 10.1074/jbc.M601035200 1:CAS:528:DC%2BD28XksFeis7k%3D (Pubitemid 43848336)
45. RW Browne D Armstrong 2000 HPLC analysis of lipid-derived polyunsaturated fatty acid peroxidation products in oxidatively modified plasma Clinical Chemistry 46 829 836 1:CAS:528:DC%2BD3cXkt1ejtbo%3D
46. Browne, R. W., & Armstrong, D. (1998). Separation of hydroxyl and hydroperoxy polyunsaturated fatty acids by high pressure liquid chromatography. In D. Armstrong (Ed.), Methods in molecular biology, free radicals, antioxidant protocols (pp. 147-155). Totowa: Humana Press.
47. 2: A family of icosanoids produced in vivo in humans Proceedings of the National Academy of Sciences of the United States of America 89 304 308 10.1073/pnas.85.2.304 10.1073/pnas.85.2.304
48. SH Lee IA Blair 2007 Targeted chiral lipidomics analysis by liquid chromatography electron capture atmospheric pressure chemical ionization mass spectrometry (LC-ECAPCI/MS) Methods in Enzymology 433 159 174 10.1016/S0076-6879(07)33009-7 10.1016/S0076-6879(07)33009-7 1:CAS:528: DC%2BD1cXhsVOqtr8%3D
49. M Masoodi A Nicolaou 2006 Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry Rapid Communications in Mass Spectrometry 20 3023 3029 10.1002/rcm.2697 10.1002/rcm.2697 1:CAS:528:DC%2BD28XhtFCgtb3J (Pubitemid 44569781)
50. M Masoodi AA Mir NA Petasis CN Serhan A Nicolaou 2008 Simultaneous lipidomic analysis of three families of bioactive lipid mediators leukotrienes, resolvins, protectins and related hydroxyl-fatty acids by liquid chromatography/electrospray ionization tandem mass spectrometry Rapid Communications in Mass Spectrometry 22 75 83 10.1002/rcm.3331 10.1002/rcm.3331 1:CAS:528:DC%2BD1cXitVSmtb0%3D (Pubitemid 351156118)
51. R Mashima K Onodera Y Yamamoto 2000 Regioisomeric distribution of cholesteryl linoleate hydroperoxides and hydroxides in plasma from healthy humans provides evidence for free radical-mediated lipid peroxidation in vivo Journal of Lipid Research 41 109 115 1:CAS:528:DC%2BD3cXltFOitQ%3D%3D (Pubitemid 30051848)
52. DW Thomas FJGM Van Kuijk EA Dratz RJ Stephens 1991 Quantitative determination of hydroxyl fatty acids as an indicator of in vivo lipid peroxidation: Gas chromatography-mass spectrometry methods Analytical Biochemistry 198 104 111 10.1016/0003-2697(91)90513-S 10.1016/0003-2697(91) 90513-S 1:CAS:528:DyaK3MXmslGit78%3D
53. DW Thomas FJGM Van Kuijk RJ Stephens 1992 Quantitative determination of hydroxyl fatty acids as an indicator of in vivo lipid peroxidation products of arachidonic and docosapentaenoic acids in rat liver after exposure to carbon tetrachloride Analytical Biochemistry 206 353 358 10.1016/0003-2697(92)90377-J 10.1016/0003-2697(92)90377-J 1:CAS:528:DyaK38XmsVKlt7k%3D
54. S Mawatari K Murakami 1998 Analysis of membrane phospholipid peroxidation by isocratic high performance liquid chromatography with ultraviolet detection Analytical Biochemistry 264 118 123 10.1006/abio.1998.2830 10.1006/abio.1998. 2830 1:CAS:528:DyaK1cXntFWgtL4%3D (Pubitemid 28493878)
55. CN Serhan CB Clish J Brannon SP Colgan N Chiang K Gronert 2000 Novel functional sets of lipoid derived mediators with anti-inflammatory actions generated from ω-3-fatty acids via cyclooxygenase 2-nonsteroid anti-inflammatory drugs and transcellular processing The Journal of Experimental Medicine 192 1197 1204 10.1084/jem.192.8.1197 10.1084/jem.192.8.1197 1:CAS:528:DC%2BD3cXnsVaqsrc%3D (Pubitemid 30786697)
56. JA Lawson H Li J Rokach M Adiyaman S-W Hwang SP Khanapure GA FitzGerald 1998 Identification of two major F2 isoprostanes, 8, 12-iso- and 5-epi-8, 12-iso-isoprostanes F2-VI, in human urine The Journal of Biological Chemistry 273 29295 29301 10.1074/jbc.273.45.29295 10.1074/jbc.273.45.29295 1:CAS:528:DyaK1cXntlKqsLw%3D (Pubitemid 28509927)
57. JA Lawson J Rokach GA FitzGerald 1999 Isoprostanes: Formation, analysis and use as indices of lipid peroxidation in vivo The Journal of Biological Chemistry 274 24441 24444 10.1074/jbc.274.35.24441 10.1074/jbc.274.35.24441 1:CAS:528:DyaK1MXls1ynsrg%3D (Pubitemid 29404634)
58. 2-Isoprostane metabolites: A novel extraction and LC-MS methodology Lipids 43 925 936 10.1007/s11745-008-3222-1 10.1007/s11745-008-3222-1 1:CAS:528:DC%2BD1cXhtFWltbrP
59. 2-isoprostanes to plaque instability in human carotid atherosclerosis The Journal of Clinical Investigation 103 421 427 10.1172/JCI3985 10.1172/JCI3985 1:CAS:528: DyaK1MXovVKmuw%3D%3D
60. WE Neff E Selke TL Mounts W Rinsch EN Frankel MAM Zeitoun 1992 Effect of triacylglycerol composition and structures on oxidative stability of oils from selected soybean germplasm Journal of the American Oil Chemists' Society 69 111 118 10.1007/BF02540559 10.1007/BF02540559 1:CAS:528:DyaK38XksVKqtbc%3D
61. WE Neff WC Byrdwell 1998 Characterization of model triacylglycerol (triolein, trilinolein, and trilinolenin) autoxidation products via high-performance liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometery Journal of Chromatography. A 818 169 186 10.1016/S0021-9673(98)00553-6 10.1016/S0021-9673(98)00553-6 1:CAS:528: DyaK1cXlsFeqt78%3D (Pubitemid 28401416)
62. th Nordic lipid symposium, Lipidforum (pp. 230-238). Bergen, Norway.
63. O Sjovall A Kuksis L Marai JJ Myher 1997 Elution factors of synthetic oxotriacylglycerols as an aid in identification of peroxidized natural triacylglycerols by reverse-phase high-performance liquid chromatography with electrospray mass spectrometry Lipids 32 1211 1218 10.1007/s11745-997-0155-4 10.1007/s11745-997-0155-4 1:CAS:528:DyaK2sXnsFaisbg%3D
64. O Sjovall A Kuksis H Kallio 2001 Analysis of molecular species of peroxide adducts of triacylglycerols following treatment of corn oil with tert-butyl hydroperoxide Lipids 36 1347 1356 10.1007/s11745-001-0851-0 10.1007/s11745-001-0851-0 1:CAS:528:DC%2BD38XovVSjtg%3D%3D
65. 2+ Lipids 37 81 94 10.1007/s11745-002-0867-5 10.1007/s11745-002-0867-5 1:CAS:528:DC%2BD38XhsVKnt7w%3D
66. O Sjovall A Kuksis H Kallio 2003 Tentative identification and quantification of TAG core aldehydes as dinitrophenylhydrazones in autoxidized sunflower seed oil using reversed phase HPLC with electrospray ionization MS Lipids 38 1179 1190 10.1007/s11745-003-1177-7 10.1007/s11745-003-1177-7 (Pubitemid 38018575)
67. T Kusaka S Ishihara M Sakaida A Mifune Y Nakano K Tsuda M Ikeda H Nakano 1996 Composition analysis of normal plant triacylglycerols and hydroperoxidized rac-1-stearoyl-2-oleoyl-3-linoleoyl-sn-glycerols by liquid chromatography- atmospheric pressure chemical ionization mass spectrometry Journal of Chromatography A 730 1 7 10.1016/0021-9673(95)00996-5 10.1016/0021-9673(95) 00996-5 1:CAS:528:DyaK28XivFOhtLg%3D (Pubitemid 26141919)
68. C Bauer-Plank L Steenhorst-Slikkerveer 2000 Analysis of triacylglyceride hydroperoxides in vegetable oils by nonaqueous reversed-phase high-performance liquid chromatography with ultraviolet detection Journal of the American Oil Chemists' Society 77 477 482 10.1007/s11746-000-0076-7 1:CAS:528: DC%2BD3cXjsVKgt7k%3D (Pubitemid 30862690)
69. L Steenhorst-Slikkerveer A Louter HG Janssen C Bauer-Plank 2000 Analysis of nonvolatile lipid oxidation products in vegetable oils by normal-phase high performance liquid chromatography with mass spectrometric detection Journal of the American Oil Chemists' Society 77 837 845 10.1007/s11746-000-0134-1 1:CAS:528:DC%2BD3cXmtFyhsrc%3D
70. K Hartvigsen A Ravandi R Harkewicz H Kamido K Bukhave G Holmer A Kuksis 2000 1-O-Alkyl-2-(ω-oxo)acyl-sn-glycerols from shark oil and human milk fat are potential precursors of PAF mimics and GHB Lipids 41 679 693 10.1007/s11745-006-5019-4 10.1007/s11745-006-5019-4
71. K Kanazawa H Ashida 1998 Catabolic fate of dietary trilinoleoylglycerol hydroperoxides in rat gastrointestines Biochimica et Biophysica Acta 1393 336 348 1:CAS:528:DyaK1cXls1OltLk%3D
72. K Kanazawa H Ashida 1998 Dietary hydroperoxides of linoleic acid decompose to aldehydes in stomach before being absorbed unto the body Biochimica et Biophysica Acta 1393 349 361 1:CAS:528:DyaK1cXls1OltLY%3D
73. Tarvainen, M., Suomela, J.-P., Kallio, H., Ahotupa, M., & Kuksis, A. (2008). Critical lipid oxidation products in an artificial digestion model. In Abstracts 99th annual AOCS meeting and expo (p. 20, Abstract no. 14). Seattle, Washington.
74. I Staprans JH Rapp X-M Pan KY Kim KR Feingold 1994 Oxidized lipids in the diet are a source of oxidized lipid in chylomicrons of human serum Arteriosclerosis and Thrombosis 14 1900 1905 1:CAS:528:DyaK2MXislOktb8%3D
75. I Staprans JH Rapp X-M Pan KR Feingold 1996 Oxidized lipids in the diet are incorporated by the liver into very low density lipoprotein in rats Journal of Lipid Research 37 420 430 1:CAS:528:DyaK28XhsFCls7k%3D
76. J-P Suomela M Ahotupa O Sjovall J-P Kurvinen H Kallio 2004 Diet and lipoprotein oxidation: Analysis of oxidized triacylglycerols in pig lipoproteins Lipids 39 639 647 10.1007/s11745-004-1277-4 10.1007/s11745-004-1277-4 1:CAS:528:DC%2BD2cXhtVSjur%2FE (Pubitemid 39488882)
77. J-P Suomela M Ahotupa H Kallio 2005 Triacylglycerol oxidation in pig lipoproteins after a diet rich in oxidized sunflower seed oil Lipids 40 437 444 10.1007/s11745-005-1402-4 10.1007/s11745-005-1402-4 1:CAS:528: DC%2BD2MXmtVart7Y%3D (Pubitemid 40911443)
78. GL Milne NA Porter 2001 Separation and identification of phospholipid peroxidation products Lipids 36 1265 1275 10.1007/s11745-001-0841-2 10.1007/s11745-001-0841-2 1:CAS:528:DC%2BD38Xht1OqsA%3D%3D
79. GL Milne JR Seal CM Havrilla M Wijtmans NA Porter 2005 Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins Journal of Lipid Research 46 307 319 10.1194/jlr.M400311-JLR200 10.1194/jlr.M400311-JLR200 1:CAS:528: DC%2BD2MXhvFGkurY%3D (Pubitemid 40271095)
80. 2-isoprostanes) in plasma and low density lipoprotein exposed to oxidative stress in vitro The Journal of Clinical Investigation 93 998 1004 10.1172/JCI117107 10.1172/JCI117107 1:CAS:528:DyaK2cXitV2gsrY%3D
81. 2: Preferential hydrolysis of acute phase HDL Journal of Lipid Research 39 2150 2160 1:CAS:528:DyaK1cXnsFems7g%3D
82. Z Ahmed A Ravandi GF Maguire A Kuksis PW Connelly 2003 Formation of apolipoprotein A-I-phosphatidylcholine core aldehyde Schiff base adducts promote uptake by THP-1 macrophages Cardiovascular Research 58 712 720 10.1016/S0008-6363(03)00257-8 10.1016/S0008-6363(03)00257-8 1:CAS:528: DC%2BD3sXksVOrt7g%3D (Pubitemid 36694458)
83. H Kamido A Kuksis L Marai JJ Myher 1995 Lipid ester-bound aldehydes among copper-catalyzed peroxidation products of human plasma lipoproteins Journal of Lipid Research 36 1876 1886 1:CAS:528:DyaK2MXot1Orsrs%3D
84. H Hughes CV Smith JO Tsokos-Kuhn JR Mitchell 1986 Quantitation of lipid peroxidation products by gas chromatography-mass spectrometry Analytical Biochemistry 152 107 112 10.1016/0003-2697(86)90127-2 10.1016/0003-2697(86) 90127-2 1:CAS:528:DyaL28XkvVarug%3D%3D
85. 2-isoprostane regioisomers formed in vivo in the rat Free Radical Biology and Medicine 23 943 954 10.1016/S0891-5849(97) 00133-0 10.1016/S0891-5849(97)00133-0 1:CAS:528:DyaK2sXmtVOmsrY%3D (Pubitemid 27402620)
86. 4-neuroprostanes Free Radical Biology and Medicine 34 1631 1635 10.1016/S0891-5849(03)00215-6 10.1016/S0891-5849(03)00215-6 1:CAS:528:DC%2BD3sXkt1yltLs%3D (Pubitemid 36638723)
87. S Pachmann MJ Mueller 1998 Evidence for the formation of dinor-isoprostanes E1 from α-linolenic acid in plants The Journal of Biological Chemistry 273 32650 32655 10.1074/jbc.273.49.32650 10.1074/jbc.273.49.32650 (Pubitemid 28557647)
88. Z Ou A Ogamo L Guo Y Konda 1995 Identification and quantification of choline glycerophospholipids that contain alddehyde residues by fluorometric high performance liquid chromatography Analytical Biochemistry 227 289 294 10.1006/abio.1995.1283 10.1006/abio.1995.1283 1:CAS:528:DyaK2MXmt1Wis7w%3D
89. Z Ou A Ogamo Y Kawai Y Nakagawa 1996 Quantification of choline glycerophospholipids that contain carboxylate residues by fluorometric-high performance liquid chromatography Journal of Chromatography A 724 131 136 10.1016/0021-9673(95)00967-1 10.1016/0021-9673(95)00967-1 1:CAS:528: DyaK28XitVWlsL8%3D (Pubitemid 26070047)
90. Y Kawai A Ogamo Y Nakagawa 1999 Formation of the aldehydic choline glycerophospholipids in human red blood cell membrane peroxidized with an azo inititator Journal of Biochemistry 126 115 120 1:CAS:528:DyaK1MXmtlagtL8%3D Tokyo
91. Y Kawai A Saito N Shibata M Kobayashi S Yamada T Osawa K Uchida 2002 Covalent binding of oxidized cholesteryl esters to protein The Journal of Biological Chemistry 278 21040 21049 10.1074/jbc.M212426200 10.1074/jbc. M212426200 1:CAS:528:DC%2BD3sXkt1Witrk%3D
92. E Waddington K Sienuarine I Puddey K Croft 2001 Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high performance liquid chromatography Analytical Biochemistry 292 234 244 10.1006/abio.2001.5075 10.1006/abio.2001.5075 1:CAS:528: DC%2BD3MXjsVyqt7w%3D (Pubitemid 32458090)
93. 2-isoprostanes in the lipid subfractions of atherosclerotic plaque and in vitro oxidized low density lipoprotein Redox Report 7 179 184 10.1179/135100002125000433 10.1179/135100002125000433 1:CAS:528:DC%2BD38Xmt1aht7s%3D (Pubitemid 34700443)
94. KR Kozak SW Rowlinson LJ Marnett 2000 Oxygenation of the endocannabinoid, 2-arachidoyglycerol, to glyceryl prostaglandins by cycloxygenase-1 The Journal of Biological Chemistry 275 33744 33749 10.1074/jbc.M007088200 10.1074/jbc.M007088200 1:CAS:528:DC%2BD3cXnvVyjsbc%3D (Pubitemid 30808595)
95. KR Kozak BC Crews JD Morrow L-H Wang YH Ma R Weinander P-J Jakobsson LJ Marnett 2002 Metabolism of the endocannabinoids, 2-arachidonoylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides The Journal of Biological Chemistry 277 44877 44885 10.1074/jbc.M206788200 10.1074/jbc.M206788200 1:CAS:528:DC%2BD38Xosl2msbo%3D (Pubitemid 36159083)
96. 2-Dihomo-isoprostanes arise from free radical attack on adrenic acid Journal of Lipid Research 249 995 1005 10.1194/jlr.M700503-JLR200 10.1194/jlr.M700503-JLR200 1:CAS:528:DC%2BD1cXltFSlt70%3D
97. 4-neuroprostanes from excitotoxicity and innate immune response in vivo by α- or γ-tocopherol Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 827 88 93 10.1016/j.jchromb.2005.03.037 10.1016/j.jchromb.2005.03.037 1:CAS:528:DC%2BD2MXhtFOmsbnL (Pubitemid 41551601)
98. 2-isoprostanes in human atherosclerotic lesions The Journal of Clinical Investigation 100 2028 2034 10.1172/JCI119735 10.1172/JCI119735 1:CAS:528:DyaK2sXmslKkurw%3D
99. A Ravandi S Babaei R Leung JC Monge G Hoppe H Hoff H Kamido A Kuksis 2004 Phospholipids and oxophospholipids in atherosclerotic plaques at different stages of plaque development Lipids 39 97 109 1:CAS:528:DC%2BD2cXjs1Gltrw%3D
100. H Kamido K Nonanka A Kuksis L Marai A Ravandi 1996 Identification of lipid ester core aldehydes and hydroperoxides in human atherosclerotic lesions. American Heart Association 69th Annual Meeting, New Orleans, LA Circulation 94 1 1707
101. JA Kenar CM Havrilla NA Porter JR Guyton SA Brown KF Klemp E Selinger 1996 Identification and quantification of the regioisomeric cholesteryl linoleate hydroperoxides in oxidized human low density lipoprotein and high density lipoprotein Chemical Research in Toxicology 9 737 744 10.1021/tx9600098 10.1021/tx9600098 1:CAS:528:DyaK28XivVyis78%3D (Pubitemid 26181624)
102. H Yin JD Morrow NA Porter 2004 Identification of a novel class of endoperoxides from arachidonate autoxidation The Journal of Biological Chemistry 279 3766 3776 10.1074/jbc.M307137200 10.1074/jbc.M307137200 1:CAS:528:DC%2BD2cXmtlCrug%3D%3D (Pubitemid 38140621)
103. K Akasaka H Ohrui H Meguro 1993 Simultaneous determination of hydroperoxides of phosphatidylcholine, cholesteryl esters and triacylglycerols by column-switching high performance liquid chromatography with a post-column detection system Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 622 153 159 1:STN:280:DyaK2c3gtFaksg%3D%3D
104. K Akasaka H Ohta Y Hanada H Ohrui 1999 Simultaneous determination of lipid hydroperoxides of HPLC-post column systems Bioscience, Biotechnology, and Biochemistry 63 1506 1508 10.1271/bbb.63.1506 10.1271/bbb.63.1506 1:CAS:528:DyaK1MXmtVWntrk%3D
105. SP Hui T Murai T Yoshimura H Chiba H Nagasaka T Kurosawa 2005 Improved HPLC assay for lipid peroxides in human plasma using the internal standard of hydroperoxide Lipids 40 515 522 10.1007/s11745-005-1412-2 10.1007/s11745-005- 1412-2 1:CAS:528:DC%2BD2MXmtVartLY%3D (Pubitemid 40911452)
106. H Kamido A Kuksis L Marai JJ Myher 1992 Identification of cholesterol-bound aldehydes in copper-oxidized low density lipoprotein FEBS Letters 304 269 272 10.1016/0014-5793(92)80635-T 10.1016/0014-5793(92)80635-T 1:CAS:528:DyaK38XltVKlt74%3D
107. G Hoppe A Ravandi D Herrera A Kuksis HF Hoff 1997 Oxidation products of cholesteryl linoleate are resistant to hydrolysis in macrophages, form complexes with proteins, and are present in human atherosclerotic lesions Journal of Lipid Research 38 1347 1360 1:CAS:528:DyaK2sXltFCjsL0%3D
108. 2-isoprostanes in biological fluids and tissues as measure of oxidant stress Methods in Enzymology 300 3 12 10.1016/S0076-6879(99)00106-8 10.1016/S0076-6879(99)00106-8 1:CAS:528:DyaK1MXltVGh
109. B Karten H Boechzelt PM Abuja M Mittelbach W Sattler 1999 Macrophage-enhanced formation of cholesteryl ester-core aldehydes during oxidation of low density lipoprotein Journal of Lipid Research 40 1240 1253 1:CAS:528:DyaK1MXksVKiuro%3D
110. R Harkewicz K Hartvigsen F Almazan EA Dennis JL Witztum YI Miller 2008 Cholesteryl ester hydroperoxides are biologically active components of minimally oxidized low density lipoprotein The Journal of Biological Chemistry 283 10241 10251 10.1074/jbc.M709006200 10.1074/jbc.M709006200 1:CAS:528: DC%2BD1cXksFags78%3D
111. JM Upston AC Terentis K Morris JF Keaney R Stocker 2002 Oxidized lipid accumulates in the presence of α-tocopherol in atherosclerosis The Biochemical Journal 363 753 760 10.1042/0264-6021:3630753 10.1042/0264-6021: 3630753 1:CAS:528:DC%2BD38XjvFemsL4%3D (Pubitemid 34526396)
112. JM Upston J Neuzil PK Witting R Alleva R Stocker 1997 Oxidation of free fatty acids in low density lipoprotein by 15-lipoxygenase stimulates nonenzymic, α-tocopherol-mediated peroxidation of cholesteryl esters The Journal of Biological Chemistry 272 30067 30074 10.1074/jbc.272.48.30067 10.1074/jbc.272.48.30067 1:CAS:528:DyaK2sXnslGhtL4%3D (Pubitemid 27512202)
113. C. Suarna R. T. Dea P. T. Southwell-Keeley D. E. Moore R. Stocker 1997 Separation and characterization of cholesteryl oxo-and hydroxy-linoleate isolated from human atherosclerotic plaques Free Radical Research 27 397 408 10.3109/10715769709065779 10.3109/10715769709065779 1:CAS:528:DyaK2sXnvFWktb8%3D
114. C Suarna RT Dean J May R Stocker 1995 Human atherosclerotic plaque contains both oxidized lipids and relatively large amounts of α-tocopherol and ascorbate Arteriosclerosis, Thrombosis, and Vascular Biology 15 1616 1624 1:STN:280:DyaK28%2FhtFGrtQ%3D%3D
115. P Friedman S Horkko D Steinberg JL Witztum EA Dennis 2002 Correlation of antiphospholipid antibody recognition with the structure of synthetic oxidized phospholipids The Journal of Biological Chemistry 277 7010 7020 10.1074/jbc.M108860200 10.1074/jbc.M108860200 1:CAS:528:DC%2BD38XitV2mtbg%3D (Pubitemid 34953088)
116. A Ravandi A Kuksis JJ Myher L Marai 1995 Determination of lipid ester ozonides and core aldehydes by high performance liquid chromatography with on-line mass spectrometry Journal of Biochemical and Biophysical Methods 30 271 285 10.1016/0165-022X(95)00015-7 10.1016/0165-022X(95)00015-7 1:CAS:528:DyaK2MXpslKhtbs%3D
117. A Ravandi A Kuksis N Shaikh G Jackowski 1997 Preparation of Schiff base adducts of phosphatidylcholine core aldehydes and aminophospholipids, amino acids, and myoglobin Lipids 32 989 1001 10.1007/s11745-997-0129-6 10.1007/s11745-997-0129-6 1:CAS:528:DyaK2sXmvVSks7s%3D (Pubitemid 27398495)
118. J Alary L Debrauwer Y Fernandez J-P Cravedi D Rao G Bories 1998 1,4-Dihydroxynonene of exogenous 4-hydroxy-2-nonenal is a physiological component of rat and human urine Chemical Research in Toxicology 11 130 135 10.1021/tx970139w 10.1021/tx970139w 1:CAS:528:DyaK1cXht1Kqtbk%3D (Pubitemid 28128444)
119. F Gueraud F Crouzet J Alary D Rao L Debrauwer F Laurent J-P Cravedi 2005 Enantioselective metabolism of (R)- and (S)-4-hydroxy-2-nonenal in rat BioFactors 24 97 104 10.1002/biof.5520240111 1:CAS:528:DC%2BD2MXht1Gjt77O
120. HC Kuiper CL Miranda JD Sowell JF Stevens 2008 Mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites are in vivo markers of oxidative stress The Journal of Biological Chemistry 283 17131 17138 10.1074/jbc.M802797200 10.1074/jbc.M802797200 1:CAS:528:DC%2BD1cXntFSnt70%3D
121. H Itabe H Yamamoto M ASuzuki Y Kawai Y Nakagawa A Suzuki T Imanaka T Takano 1996 Oxidized phosphatidylcholines that modify proteins The Journal of Biological Chemistry 271 33208 33217 10.1074/jbc.271.52.33208 10.1074/jbc.271.52.33208 1:CAS:528:DyaK2sXitFarsg%3D%3D (Pubitemid 27010127)
122. S Horkko DA Bird E Miller H Itabe N Leitinger G Subbanagounder JA Berliner P Friedman EA Dennis LK Curtiss W Palinski JL Witztum 1999 Monoclonal autoantibodies specific for oxidized phospholipids or oxidized phospholipid-protein adducts inhibit macrophage uptake of oxidized low-density lipoproteins The Journal of Clinical Investigation 103 117 128 10.1172/JCI4533 10.1172/JCI4533 1:CAS:528:DyaK1MXjsl2lsw%3D%3D
123. J-P Kurvinen A Kuksis A Ravandi O Sjovall H Kallio 1999 Rapid complexing of oxoacylglycerols with amino acids, peptides and aminophospholipids Lipids 34 299 305 10.1007/s11745-999-0367-7 10.1007/s11745-999-0367-7 1:CAS:528: DyaK1MXisVelt7s%3D
124. BG Gugiu K Mouillesseaux C Duong T Herzog A Hekimian L Koroniak TM Vondriska AD Watson 2008 Protein targets of oxidized phospholipids in endothelial cells Journal of Lipid Research 49 510 520 10.1194/jlr.M700264- JLR200 10.1194/jlr.M700264-JLR200 1:CAS:528:DC%2BD1cXit12is7g%3D
125. CJ Brame RG Salomon JD Morrow LJ Roberts 1999 Identification of extremely reactive γ-ketoaldehydes (isolevuloglandins) as products of the isoprostane pathway and characterization of their lysyl protein adducts The Journal of Biological Chemistry 274 13139 10.1074/jbc.274.19.13139 10.1074/jbc.274.19.13139 1:CAS:528:DyaK1MXjtFOls7w%3D (Pubitemid 29220438)
126. N Bernoud-Hubac SS Davies O Boutaud TJ Montine LJ Roberts II 2001 Formation of highly reactive γ-ketoaldehydes (neuroketals) as products of the neuroprostane pathway The Journal of Biological Chemistry 276 30964 30970 10.1074/jbc.M103768200 10.1074/jbc.M103768200 1:CAS:528:DC%2BD3MXmsVaquro%3D
127. XM Li RG Salomon J Qin SL Hazen 2007 Conformation of an endogenous ligand in a membrane bilayer for the macrophage scavenger receptor CD36 Biochemistry 46 5009 5017 10.1021/bi700163y 10.1021/bi700163y 1:CAS:528:DC%2BD2sXjslWhtL8%3D (Pubitemid 46682999)
128. NS Kar MZ Ashraf M Valiyaveettil EA Podzer 2008 Mapping and characterization of the binding site for specific lipoprotein of scavenger receptor CD36 The Journal of Biological Chemistry 283 8765 8771 10.1074/jbc.M709195200 10.1074/jbc.M709195200 1:CAS:528:DC%2BD1cXjsFCgt7Y%3D
129. MZ Ashraf NS Kar X Chen J Choi RG Salomon M Febbraio 2008 Specific oxidized phospholipids inhibit scavenger receptor BI-mediated selective uptake of cholesteryl esters The Journal of Biological Chemistry 283 10408 10414 10.1074/jbc.M710474200 10.1074/jbc.M710474200 1:CAS:528:DC%2BD1cXksFagsLk%3D
130. T Douki F Odin S Caillat A Favier J Cadet 2004 Predominance of the 1, N2-propano 2'-deoxyguanosine adduct among 4-hydroxy-2-nonenal-induced DNA lesions Free Radical Biology and Medicine 37 62 70 10.1016/j.freeradbiomed.2004. 04.013 10.1016/j.freeradbiomed.2004.04.013 1:CAS:528:DC%2BD2cXkslWktr0%3D (Pubitemid 38746651)
131. SH Lee JA Arora T Oe IA Blair 2005 4-Hydroperoxy-2-nonenal-induced formation of 1, N2-etheno-2'-deoxyguanosine adducts Chemical Research in Toxicology 18 780 786 10.1021/tx0497088 10.1021/tx0497088 1:CAS:528: DC%2BD2MXislWltbc%3D (Pubitemid 40563293)
132. P Zhu SH Lee S Wehrli IA Blair 2006 Characterization of a lipid hydroperoxide-derived RNA adduct in rat intestinal epithelial cells Chemical Research in Toxicology 19 809 817 10.1021/tx0600189 10.1021/tx0600189 1:CAS:528:DC%2BD28XktlCjsL4%3D (Pubitemid 43939060)