Mechanism of lower oxidizability of eicosapentaenoate than linoleate in aqueous micelles

Lipids

Volumn 31, Issue 3, 1996, Pages 337-340

  Yazu, Kazumasa ^a   Yamamoto, Yorihiro ^b   Ukegawa, Koji ^a   Niki, Etsuo ^b  

^a NATL INST FOR RSRC AND ENVIRON   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBIS(2 AMIDINOPROPANE); CHLOROBENZENE; HEXANE; ICOSAPENTAENOIC ACID; LINOLEIC ACID; METHANOL; TRITON X 100;

AEROBIC METABOLISM; ARTICLE; ENZYME SUBSTRATE; LIPID ANALYSIS; LIPID METABOLISM; LIPID OXIDATION; MICELLE; PHOTOOXIDATION;

AMIDINES; AZO COMPOUNDS; CHLOROBENZENES; EICOSAPENTAENOIC ACID; ESTERS; FATTY ACIDS, UNSATURATED; KINETICS; LINOLEIC ACID; LINOLEIC ACIDS; MICELLES; MODELS, CHEMICAL; NITRILES; OCTOXYNOL; OXIDATION-REDUCTION; PEROXIDES;

EID: 0029865971     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02529881     Document Type: Article

References (14)

1. Howard, J.A., and Ingold, K.U. (1967) Absolute Rate Constants for Hydrocarbon Autoxidation. VI. Alkyl Aromatic and Olefinic Hydrocarbons, Can. J. Chem. 45, 793-802.
2. 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.
3. 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.
4. Cosgrove, J. P., Church, D. F., and Pryor, W. A. (1987) The Kinetics of the Autoxidation of Polyunsaturated Fatty Acids, Lipids 22, 299-304.
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. Bruna, E., Petit, E., Bejiean-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.
7. Boozer, C.E., Hammond, G.S., Hamilton, C.E., and Sen, J.N. (1955) The Stoichiometry and Fate of Inhibitors in Benzene and Chlorobenzene, J. Am. Chem. Soc. 77, 3233-3237.
8. Yazu, K., Ukegawa, K., Nakayama, T., Yamamoto, Y , and Niki, E. (1992) Autoxidation of Phosphatidylethanolamine and Phosphatidylcholine in Organic Solvents, J. Jpn. Oil Chem. Soc. (YUKAGAKU) 41, 582-585.
9. Barclay, L.R.C., Locke, S.J., MacNeil, J.M., and VanKessel, J. (1985) Quantitative Studies of the Autoxidation of Linoleate Monomers Sequestered in Phosphatidylcholine Bilayers. Absolute Rate Constants in Bilayers, Can. J. Chem. 63, 2633-2638.
10. Porter, N.A., Lehman, L.S., Weber, B.A., and Smith, K.J. (1981) Unified Mechanism for Polyunsaturated Fatty Acid Autoxidation. Competition of Peroxy Radical Hydrogen Atom Abstraction, β-Scission, and Cyclization, J. Am. Chem. Soc. 103, 6447-6455.
11. Porter, N. A., and Funk, M.O. (1975) Peroxy Radical Cyclization as a Model for Prostaglandin Biosynthesis. J. Org. Chem. 40, 3614-3615.
12. Pryor, W.A., and Stanley, J.P. (1975) A Suggested Mechanism for the Production of Malonaldehyde During the Autoxidation of Polyunsaturated Fatty Acids. Nonenzymatic Production of Prostaglandin Endoperoxides During Autoxidation, J. Org. Chem. 40, 3615-3617.
13. Barclay, L.R.C, and Ingold, K.U. (1981) The Autoxidation of a Model Membrane. A Comparison of the Autoxidation of Egg Lecithin Phosphatidylcholine in Water and in Chlorobenzene, J. Am. Chem. Soc. 103, 6478-6485.
14. Barclay, L.R.C., Baskin, K.A., Locke, S.J., and Schaefer, T.A. (1987) Benzophenone-Photosensitized Autoxidations of Linoleate in Solution and Sodium Dodecyl Sulfate Micelles. Can. J. Chem. 65, 2529-2540.