Distributions of hydroperoxide positional isomers generated by oxidation of 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine in liposomes and in methanol solution

Lipids

Volumn 38, Issue 1, 2003, Pages 65-72

  Wang, Xing Hua ^a   Ushio, Hideki ^a   Ohshima, Toshiaki ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; ISOMERS; METHANOL; OXIDATION;

FREE RADICAL OXIDATION;

LIPIDS;

1 PALMITOYL 2 (11 HYDROXY 5,8,12,14 EICOSATETRAENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 (12 HYDROXY 5,8,10,14 EICOSATETRAENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 (13 HYDROXY 9,11 OCTADECADIENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 (15 HYDROXY 5,8,11,13 EICOSATETRAENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 (5 HYDROXY 6,8,11,14 EICOSATETRAENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 (8 HYDROXY 5,9,11,14 EICOSATETRAENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 (9 HYDROXY 5,7,11,14 EICOSATETRAENOYL)GLYCERO 3 PHOSPHOCHOLINE; 1 PALMITOYL 2 ARACHIDONOYLGLYCERO 3 PHOSPHOCHOLINE; 2,2' AZOBIS(2 AMIDINOPROPANE); ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; HYDROGEN; HYDROPEROXIDE; LIPOSOME; METHANOL; PENTAMETHYLCHROMANOL; PHOSPHORYLCHOLINE; UNCLASSIFIED DRUG;

ARTICLE; DERIVATIZATION; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHILICITY; HYDROPHOBICITY; ISOMER; LIPID OXIDATION; MASS SPECTROMETRY;

ANTIOXIDANTS; CELL POLARITY; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FREE RADICALS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN PEROXIDE; ISOMERISM; LIPID PEROXIDATION; LIPOSOMES; METHANOL; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHATIDYLCHOLINES;

EID: 0037225756     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-003-1032-x     Document Type: Article

References (33)

1. Yamamoto, Y., Niki, E., Kamiya, Y., and Shimasaki, H. (1984) Oxidation of Phosphatidylcholines in Homogeneous Solution and in Water Dispersion, Biochim. Biophys. Acta 795, 332-340.
2. Cosgrove, J.P., Church, D.F., and Pryor, W.A. (1987) The Kinetics of the Autoxidation of Polyunsaturated Fatty Acids, Lipids 22, 299-304.
3. Yamamoto, Y., Niki, E., and Kamiya, Y. (1982) Quantitative Determination of the Oxidation of Methyl Linoleate and Methyl Linolenate, Bull. Chem. Soc. Jpn. 55, 1548-1550.
4. Bruna, E., Petei, E., Beijean-Leymarie, M., Huynh, S., and Nouvelot, A. (1989) Specific Susceptibility of Docosahexaenoic Acid and Eicosapentaenoic Acid to Peroxidation in Aqueous Solution, Lipids 24, 970-975.
5. Miyashita, K., Nara, E., and Ota, T. (1993) Oxidative Stability of Polyunsaturated Fatty Acids in an Aqueous Solution, Biosci. Biotechnol. Biochem. 57, 1638-1640.
6. Yazu, K., Yamamoto, Y., Ukegawa, K., and Niki, E. (1996) Mechanism of Lower Oxidizability of Eicosapentaenoate than Linolenate in Aqueous Micelles, Lipids 31, 337-340.
7. Yazu, K., Yamamoto, Y., Niki, E., Miki, K., and Ukegawa, K. (1998) Mechanism of Lower Oxidizability of Eicosapentaenoate than Linoleate in Aqueous Micelles. II. Effect of Antioxidants, Lipids 33, 597-600.
8. Coxon, D.T., Price, K.R., and Chan, H.W.-S. (1981) Formation, Isolation and Structure Determination of Methyl Linolenate Diperoxides, Chem. Phys. Lipids 28, 365-378.
9. Neff, W.E., Frankel, E.N., and Weisleder, D. (1981) High-Pressure Liquid Chromatography of Autoxidized Lipids: II. Hydroperoxy-Cyclic Peroxides and Other Secondary Products from Methyl Linolenate, Lipids 16, 439-448.
10. O'Connor, D.E., Michelich, E.D., and Coleman, M.C. (1984) Stereochemical Course of the Autoxidative Cyclization of Lipid Hydroperoxides to Prostaglandin-Like Bicyclo-endoperoxides, J. Am. Chem. Soc. 106, 3577-3584.
11. Frankel, E.N., Neff, W.E., Rohwedder, W.K., Khambay, B.P.S., Garwood, R.F., and Weedon, B.C.L. (1977) Analysis of Autoxidized Fats by Gas Chromatography-Mass Spectrometry: I. Methyl Oleate, Lipids 12, 901-907.
12. Frankel, E.N., Garwood, R.F., Khambay, B.P.S., Moss, G., and Weedon, B.C.L. (1984) Stereochemistry of Olefins and Fatty Acid Oxidation. III. The Allylic Hydroperoxides from the Autoxidation of Methyl Oleate, J. Chem. Soc. Perkin Trans. 1, 2233-2240.
13. 13C NMR Spectrometry, Methods Enzymol. 186, 380-387.
14. Porter, N.A., Mills, K.A., and Carter, R.A. (1994) A Mechanistic Study of Oleate Autoxidation: Competing Peroxy H-Atom Abstraction and Rearrangement, J. Am. Chem. Soc. 116, 6690-6696.
15. Wang, X.-H., Ohshima, T., Ushio, T., and Koizumi, C. (1999) Proportion of Geometrical Hydroperoxide Isomers Generated by Radical Oxidation of Methyl Linoleate in Homogeneous Solution and in Aqueous Emulsion, Lipids 34, 675-679.
16. Selke, E., Frankel, E.N., and Neff, W.E. (1978) Thermal Decomposition of Methyl Oleate Hydroperoxides and Identification of Volatile Components by Gas Chromatography-Mass Spectrometry, Lipids 13, 511-513.
17. Frankel, E.N., Neff, W.E., Selke, E., and Weisleder, D. (1982) Photosensitized Oxidation of Methyl Linoleate. Secondary and Volatile Thermal Decomposition Products, Lipids 17, 11-18.
18. Frankel, E.N., Neff, W.E., Selke, E., and Brooks, D.D. (1987) Thermal and Metal Catalyzed Decomposition of Methyl Linolenates, Lipids 22, 322-327.
19. Milne, G.L., and Porter N.A. (2001) Separation and Identification of Phospholipid Peroxidation Products, Lipids 36, 1265-1275.
20. Chapman, R.A., and Mackay, K. (1949) The Estimation of Peroxides in Fats and Oils by the Ferric Thiocyanate Method, J. Am. Oil Chem. Soc. 26, 360-363.
21. Box, G.E.P., Hunter, W.G., and Hunter, J.S. (1978) Statistics for Experimenters, pp. 21-56, John Wiley & Sons, New York.
22. 14C Tracer and Product Studies, Biochim. Biophys. Acta 1237, 77-85.
23. Fukuzawa, K., Ikebata, W., Shibata, A., and Kumadaki, I. (1992) Location of Dynamics of α-Tocopherol in Model Phospholipid Membranes with Different Charges, Chem. Phys. Lipids 63, 69-75.
24. Kelley, E.E., Buettner, G.R., and Burns, C.P. (1995) Relative α-Tocopherol Deficiency in Cultured Cells: Free Radical-Mediated Lipid Peroxidation, Lipid Oxidizability, and Cellular Polyunsaturated Fatty Acid Content, Arch. Biochem. Biophys. 319, 102-109.
25. Hopia, A., Huang, S.-W., and Frankel, E.N. (1996) Effect of α-Tocopherol and Trolox on the Decomposition of Methyl Linoleate Hydroperoxides, Lipids 31, 357-365.
26. Yamauchi, R., Yagi, Y., and Kato, K. (1996) Oxidation of α-Tocopherol During the Peroxidation of Dilinoleylphosphatidylcholine in Liposomes, Biosci. Biotech. Biochem. 60, 616-620.
27. Yamauchi, R., Hara, Y., Murase; H., and Kato, K. (2000) Analysis of the Addition Products of α-Tocopherol with Phosphatidylcholine-Proxy Radicals by High-Performance Liquid Chromatography with Chemiluminescenct Detection, Lipids 35, 1405-1410.
28. Litman, B.J., Lewis, E.N., and Levin, I.W. (1991) Packing Characteristics of Highly Unsaturated Bilayer Lipids: Raman Spectroscopic Studies of Multilamellar Phosphatidylcholine Dispersion, Biochemistry 30, 313-319.
29. Rich, M.R. (1993) Conformational Analysis of Arachidonic and Related Fatty Acids Using Molecular Dynamics Simulations, Biochim. Biophys. Acta 1178, 87-96.
30. Khaselev, N., and Murphy, R.C. (2000) Peroxidation of Arachidonate Containing Plasmenyl Glycerophosphocholine: Facile Oxidation of Esterified Arachidonate at Carbon-5, Free Radic. Biol. Med. 29, 620-632.
31. Murphy, R.C. (2001) Free-Radical-Induced Oxidation of Arachidonoyl Plasmalogen Phospholipids: Antioxidant Mechanism and Precursor Pathway for Bioactive Eicosanoids, Chem. Res. Toxicol. 14, 463-472.
32. Peers, K.E., and Coxon, D.T. (1983) Controlled Synthesis of Monohydroperoxides by α-Tocopherol Inhibited Autoxidation of Polyunsaturated Lipids, Chem. Phys. Lipids 32, 49-56.
33. Yamagata, S., Murakami, H., Terao, J., and Matsushita, S. (1983) Nonenzymatic Oxidation Products of Methyl Arachidonate, Agric. Biol. Chem. 47, 2791-2799.