Inhibition of 2,2'-azobis(2,4-dimethylvaleronitrile)-induced lipid peroxidation by sesaminols

Lipids

Volumn 33, Issue 10, 1998, Pages 1031-1036

  Kang, Myung Hwa ^a   Katsuzaki, Hirotaka ^b   Osawa, Toshihiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBIS(2,4 DIMETHYLVALERONITRILE); SESAME SEED OIL; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID PEROXIDATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

SESAMUM INDICUM;

EID: 0031737970     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-998-0302-y     Document Type: Article

References (38)

1. Budowski, P., and Markley, K.S. (1951) The Chemical and Physiological Properties of Sesame Oil, Chem. Rev. 48, 125-151.
2. Lyon, C.K. (1972) Sesame: Current Knowledge of Composition and Use, J. Am. Oil Chem. Soc. 49, 245-249.
3. Fukuda, Y., Nagata, T., Osawa, T., and Namiki, M. (1986) Contribution of Lignan Analogues to Antioxidant Activity of Refined Unroasted Sesame Seed Oil, J. Am. Oil Chem. Soc. 63, 1027-1031.
4. Nagata, M., Osawa, T., Namiki, M., Fukuda, Y., and Ozaki, T. (1987) Stereochemical Structures of Antioxidant Bisepoxylignans, Sesaminol and Its Isomers, Transformed from Sesamolin, Agric. Biol. Chem. 51, 1285-1289.
5. Haslam, E. (1970) The Stereochemistry of Sesamolin, J. Chem. Soc. 5, 2332-2334.
6. Kang, M-H., Naito, M., Tsujihara, N., and Osawa, T. (1998) Sesamolin Inhibits Lipid Peroxidation in Rat Liver and Kidney, J. Nutr. 128, 1018-1022.
7. Ozer, N.K., Boscoboinik, D., and Azzi, A. (1995) New Roles of Low-Density Lipoproteins and Vitamin E in the Pathogenesis of Atherosclerosis, Biochem. Molecular Biol. Internat. 35, 117-124.
8. Gugliucci, A., and Stahl, A.J.C. (1995) Low Density Lipoprotein Oxidation is Inhibited by Extracts of Ilex paraguariensis, Biochem. Molecular Biol. Internat. 35, 47-56.
9. Osawa, T., Kumon, H., Fukuda, Y., Namiki, M., and Kawakishi, S. (1990) Antimutagenic Heat Stable Antioxidants, in Mutagens and Carcinogens in the Diet (Pariza, M.W., Aeschbacher, H.U., Felton, J.S., and Sato, S., eds.) pp. 223-228, Wiley-Liss, New York.
10. Osawa, T., Nagata, M., Namiki, M., and Fukuda, Y. (1985) Sesamolinol, a Novel Antioxidant Isolated from Sesame Seeds, Agric. Biol. Chem. 49, 3351-3352.
11. Osawa, T., Namiki, M., and Kawakishi, S. (1990) Role of Dietary Antioxidants in Protection Against Oxidative Damage, Basic Life Sci., 139-153.
12. Osawa, T. (1992) Phenolic Antioxidants in Dietary Plants as Antimutagens, in Phenolic Compounds in Food and Health (Ho, C-T., Lee, C.Y., and Hung, M.T., eds.) pp. 135-149, American Chemical Society, Washington, DC.
13. Osawa, T., Yoshida, S., Yamashita, K., and Ochi, H. (1995) Protective Role of Dietary Antioxidants in Oxidative Stress, in Oxidative Stress and Aging (Cutler, R.G., Packer, L., Bertram, J., and Mori, A., eds.) pp. 367-377, Birkhauser-Verlag, Basel.
14. Fukuda, Y., Osawa, T., Namiki, M., and Ozaki, T. (1985) Studies on Antioxidant Substances in Sesame Seed, Agric. Biol. Chem. 49, 301-306.
15. Tashiro, T., Fukuda, Y., Osawa, T., and Namiki, M. (1990) Oil and Minor Components of Sesame (Sesamum indicum L.) Strains, J. Am. Oil Chem. Soc. 67, 508-511.
16. Matsuo, M., Matsumoto, S., Iitaka, Y., and Niki, E. (1989) Radical-Scavenging Reactions of Vitamin E and Its Model Compound, 2,2,5,7,8-Pentamethylchroman-6-ol, in a tert-Butylperoxyl Radical-Generating System, J. Am. Chem. Soc. 111, 7179-7185.
17. Yamauchi, R., Matsui, T., Satake, Y., Kato, K., and Ueno, Y. (1989) Reaction Products of α-Tocopherol with a Free Radical Initiator, 2,2′-Azobis(2,4-dimethylvaleronitrile), Lipids 24, 204-209.
18. Liebler, D.C., Baker, P.F., and Kaysen, K.L. (1990) Oxidation of Vitamin E: Evidence for Competing Autoxidation and Peroxyl Radical Trapping Reactions of the Tocopheroxyl Radical, J. Am. Chem. Soc. 112, 6995-7000.
19. Sugiyama, Y., Kawakishi, S., and Osawa, T. (1996) Involvement of the β-Diketone Moiety in the Antioxidative Mechanism of Tetrahydrocurcumin, Biochem. Pharmacol. 52, 519-525.
20. Tsuda, T., Ohshima, K., Kawakishi, S., and Osawa, T. (1996) Oxidation Products of Cyanidin 3-O-β-D-Glucoside with a Free Radical Initiator, Lipids 31, 1259-1263.
21. Niki, E., Yamamoto, Y., Komuro, E., and Sato, K. (1991) Membrane Damage Due to Lipid Oxidation, Am. J. Clin. Nutr. 53, 201s-205s.
22. Philpot, J. (1963) The Estimation and Identification of Organic Peroxides, Radiation Res. Suppl. 3, 55-70.
23. Jacob, H.S., and Samuel, E.L. (1968) Degradation of Membrane Phospholipids and Thiols in Peroxide Hemolysis: Studies in Vitamin E Deficiency, Blood 32, 549-568.
24. Chiu, D., Lubin, B., and Shohet, S.B. (1982), Peroxidative Reactions in Red Cell Biology, in Free Radicals in Biology (Pryor, W.A., ed.) Vol. V, pp. 115-160, Academic Press, New York.
25. Steinberg, D. (1997) Low Density Lipoprotein Oxidation and Its Pathobiological Significance, J. Biol. Chem. 272, 20963-20966.
26. Esterbauer, H., Dieber-Rotheneder, M., Waeg, G., Striegl, G., and Jurgens, G. (1992) Biochemical, Structural, and Functional Properties of Oxidized Low Density Lipoprotein, Chem. Res. Toxicol. 3, 77-92.
27. Dieber-Rotheneder, M., Puhl, H., Waeg, G., Striegl, G., and Esterbauer, H. (1991) Effect of Oral Supplementation with D-α-Tocopherol on the Vitamin E Content of Human Low Density Lipoproteins and Resistance to Oxidation, J. Lipid Res. 32, 1325-1332.
28. Regnstrom, J., Walldius, G., Carlson, L.A., and Nilsson, J. (1990) Effect of Probucol Treatment on the Susceptibility of Low Density Lipoprotein Isolated from Hypercholesterolemic Patients to Become Oxidatively Modified in vitro, Atherosclerosis 82, 43-51.
29. Bjorkhem, I., Henriksson-Freyschuss, A., Breuer, O., Diczfalusy, U., Berglund, L., and Henriksson, P. (1991) The Antioxidant Butylated Hydroxytoluene Protects Against Atherosclerosis, Arterioscler. Thromb. 11, 14-22.
30. Mathiesen, L., Wang, S., Halvorsen, B., Karl, E., and Sund, R.B. (1996) Inhibition of Lipid Peroxidation in Low Density Lipoprotein by the Flavonoid Myrigalone B and Ascorbic Acid, Biochem. Pharmacol. 51, 1719-1725.
31. Osawa, T., Ide, A., Su, J.D., and Namiki, M. (1987) Inhibition of Lipid Peroxidation by Ellagic Acid, J. Agric. Food Chem. 35, 808-812.
32. Osawa, T., Sugiyama, Y., Inayoshi, M., and Kawakishi, S. (1995) Antioxidant Activity of Tetrahydrocurcuminoids, Biosci. Biotech. Biochem. 59, 1609-1612.
33. Goodhue, C.T., and Risley, H.A. (1965) Reactions of Vitamin E with Peroxides. II. Reaction of Benzoyl Peroxide with d-α-Tocopherol in Alcohols, Biochemistry 4, 854-858.
34. Pryor, W.A. (1976) The Role of Free Radical Reactions in Biological Systems, in Free Radicals in Biology (Pryor, W.A. ed.) Vol. I, pp. 1-43, Academic Press, New York.
35. Urano, S., Yamanoi, S., Hattori, Y., and Matsuo, M. (1976) Radical Scavenging Reactions of α-Tocopherol II. The Reaction with Some Alkyl Radicals, Lipids 12, 105-108.
36. Urano, S., and Matsuo, M. (1976) A Radical Scavenging Reaction of α-Tocopherol with Methyl Radical, Lipids 11, 380-383.
37. Gardner, H.W., Eskins, K., Grams, G.W., and Inglett, G.E. (1972) Radical Addition of Linoleic Hydroperoxides to α-Tocopherol or the Analogous Hydroxychroman, Lipids 7, 324-334.
38. Namiki, M. (1995) The Chemistry and Physiological Functions of Sesame, Food Rev. Internat. 11, 281-329.