Detection of cholesteryl ester hydroperoxide isomers using gas chromatography-mass spectrometry combined with thin-layer chromatography blotting

Analytical Biochemistry

Volumn 360, Issue 1, 2007, Pages 130-137

  Kawai, Yoshichika ^a   Miyoshi, Mariko ^a   Moon, Jae Hak ^a   Terao, Junji ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Cholesteryl ester; Gas chromatography mass spectrometry; Lipid hydroperoxides; Oxidized LDL; Thin layer chromatography blotting

Indexed keywords

ESTERS; FLUORESCENCE; IONIZATION OF GASES; ISOMERS; MASS SPECTROMETRY; OXIDATION; PLANTS (BOTANY); THIN LAYER CHROMATOGRAPHY;

CHOLESTERYL ESTER HYDROPEROXIDES; CHOLESTERYL ESTERS; CHROMATOGRAPHIC TECHNIQUES; ELECTRON IONIZATION MASS SPECTROMETRY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LIPID HYDROPEROXIDES; LOW DENSITY LIPOPROTEINS; OXIDIZED LDL;

GAS CHROMATOGRAPHY;

CHOLESTEROL ESTER; CHOLESTERYL ESTER HYDROPEROXIDE; CHOLESTERYL LINOLEATE HYDROPEROXIDE; DIPHENYL 1 PYRENYLPHOSPHINE; ETHER DERIVATIVE; FLUORESCENT DYE; HYDROPEROXIDE DERIVATIVE; LOW DENSITY LIPOPROTEIN; OXIDIZED LOW DENSITY LIPOPROTEIN; PHOSPHINE DERIVATIVE; SILANE DERIVATIVE; STEARIC ACID DERIVATIVE;

ANALYTIC METHOD; ARTICLE; ATHEROSCLEROSIS; DERIVATIZATION; ELECTRON IONIZATION MASS SPECTROMETRY; EXTRACTION; FLUORESCENCE; GAS CHROMATOGRAPHY; HYDROGENATION; ISOMER; LIPID PEROXIDATION; MASS SPECTROMETRY; METHYLATION; OXIDATION; PATHOGENESIS; PRIORITY JOURNAL; SILYLATION; THIN LAYER CHROMATOGRAPHY;

EID: 33845465416     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2006.09.028     Document Type: Article

References (31)

1. Steinberg D., Parthasarathy S., Carew T.E., Khoo J.C., and Witztum J.L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320 (1989) 915-924
2. Steinberg D. Role of oxidized LDL and antioxidants in atherosclerosis. Adv. Exp. Med. Biol. 369 (1995) 39-48
3. Van Heek M., Schmitt D., Toren P., Cathcart M.K., and DiCorleto P.E. Cholesteryl hydroperoxyoctadecadienoate from oxidized low density lipoprotein inactivates platelet-derived growth factor. J. Biol. Chem. 273 (1998) 19405-19410
4. Kawai Y., Saito A., Shibata N., Kobayashi M., Yamada S., Osawa T., and Uchida K. Covalent binding of oxidized cholesteryl esters to prote. Implications for Oxidative Modification of Low Density Lipoprotein and Atherosclerosis. J. Biol. Chem. 278 (2003) 21040-21049
5. Yamamoto Y., Brodsky M.H., Baker J.C., and Ames B.N. Anal. Biochem. 160 (1987) 7-13
6. Miyazawa T., Yasuda K., and Fujimoto K. Chemiluminescence-high performance liquid chromatography of phosphatidylcholine hydroperoxide. Anal. Lett. 20 (1987) 915-925
7. Terao J., Shibata S.S., and Matsushita S. Selective quantification of arachidonic acid hydroperoxides and their hydroxy derivatives in reverse-phase high performance liquid chromatography. Anal. Biochem. 169 (1988) 415-423
8. Gebicki J.M., and Guille J. Spectrophotometric and high-performance chromatographic assays of hydroperoxides by the iodometric technique. Anal. Biochem. 176 (1989) 360-364
9. Mullertz A., Schmedes A., and Hølmer G. Separation and detection of phospholipid hydroperoxides in the low nanomolar range by a high performance liquid chromatography/ironthiocyanate assay. Lipids 25 (1990) 415-418
10. Akasaka K., Ohrui H., and Meguro H. An aromatic phosphine reagent for the HPLC-fluorescence determination of hydroperoxides-determination of phosphatidylcholine hydroperoxides in human plasma. Anal. Lett. 21 (1988) 965
11. Akasaka K., Ohata A., Ohrui H., and Meguro H. Automatic determination of hydroperoxides of phosphatidylcholine and phosphatidylethanolamine in human plasma. J. Chromatogr.B 665 (1995) 37-43
12. Taki T., Handa K., and Ishikawa D. Blotting of glycolipids and phospholipids from a high-performance thin-layer chromatogram to a polyvinylidene difluoride membrane. Anal. Biochem. 221 (1994) 312-316
13. Taki T., and Ishikawa D. TLC blotting: application to microscale analysis of lipids and as a new approach to lipid-protein interaction. Anal. Biochem. 251 (1997) 135-143
14. Terao J., Miyoshi M., and Miyamoto S. Thin-layer chromatography blotting for the fluorescence detection of phospholipid hydroperoxides and cholesteryl ester hydroperoxides. J. Chromatogr. B Biomed. Sci. Appl. 765 (2001) 199-203
15. Arai H., Terao J., Abdalla D.S., Suzuki T., and Takama K. Coulometric detection in high-performance liquid chromatographic analysis of cholesteryl ester hydroperoxides. Free Radical Biol. Med. 20 (1996) 365-371
16. Bligh E.G., and Dyer W.J. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37 (1959) 911-917
17. Esterbauer H., Dieber-Rotheneder M., Waeg G., Striegl G., and Jurgens G. Biochemical, structural, and functional properties of oxidized low-density lipoprotein. Chem. Res. Toxicol. 3 (1990) 77-92
18. Lehmann W.D., Stephan M., and Furstenberger G. Profiling assay for lipoxygenase products of linoleic and arachidonic acid by gas chromatography-mass spectrometry. Anal. Biochem. 204 (1992) 158-170
19. 2 is used as oxidant. Biochim. Biophys. Acta 1392 (1998) 23-40
20. Spiteller P., Kern W., Reiner J., and Spiteller G. Aldehydic lipid peroxidation products derived from linoleic acid. Biochim. Biophys. Acta 1531 (2001) 188-208
21. Kühn H., Belkner J., Wiesner R., Schewe T., Lankin V.Z., and Tikhaze A.K. Structure elucidation of oxygenated lipids in human atherosclerotic lesions. Eicosanoids 5 (1992) 17-22
22. Kühn H., Belkner J., Zaiss S., Fahrenklemper T., and Wohl-feil S. Involvement of 15-lipoxygenase in early stages of atherogenesis. J. Exp. Med. 179 (1994) 1903-1911
23. Ylä-Herttuala S., Rosenfeld M.E., Parthasarathy S., Sigal E., Sarkioja T., Witztum J.L., and Steinberg D. Gene expression in macrophage-rich human atherosclerotic lesions. 15-lipoxygenase and acetyl low density lipoprotein receptor messenger RNA colocalize with oxidation specific lipid-protein adducts. J. Clin. Invest. 87 (1991) 1146-1152
24. Frankel E.N. Chemistry of free radical and singlet oxidation of lipids. Prog. Lipid Res. 23 (1984) 97-221
25. Terao J., and Matsushita S. Products formed by photosensitized oxidation of unsaturated fatty acid esters. J. Am. Oil Chem. Soc. 54 (1977) 234-239
26. Terao J., and Matsushita S. The isomeric compositions of monohydroperoxides produced by oxidation of unsaturated fatty acid esters with singlet oxygen. J. Food Process. Preserv. 3 (1979) 329-337
27. Frankel E.N., Neff W.E., Rohwedder W.K., Khambay B.P., Garwood R.F., and Weedon B.C. Analysis of autoxidized fats by gas chromatography: I Methyl linoleate. Lipids 12 (1977) 908-913
28. Frankel E.N. Volatile lipid oxidation products. Prog. Lipid Res. 22 (1982) 1-33
29. Howard J.A., and Ingold K.U. Absolute rate constants for hydrocarbon autoxidation. VI. Alkylaromatic and olefinic hydrocarbons. Can. J. Chem. 45 (1967) 793
30. Bando N., Hayashi H., Wakamatsu S., Inakuma T., Miyoshi M., Nagao A., Yamauchi R., and Terao J. Participation of singlet oxygen in ultraviolet-A-induced lipid peroxidation in mouse skin and its inhibition by dietary β-carotene: an ex vivo study. Free Radical Biol. Med. 37 (2004) 1854-1863
31. Akasaka K., Ijichi S., Watanabe K., Ohrui H., and Meguro H. High-performance liquid chromatography and post-column derivatization with diphenyl-1-pyrenylphosphine for fluorimetric determination of triacylglycerol hydroperoxides. J. Chromatogr. 596 (1992) 197-202