Dynamics of vitamin E action against LDL oxidation

Free Radical Research

Volumn 28, Issue 6, 1998, Pages 561-572

  Noguchi, Noriko ^a   Niki, Etsuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Antioxidant; Lipid pyroxidation; Low density lipoprotein; Spin label; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; LOW DENSITY LIPOPROTEIN; SCAVENGER;

ATHEROSCLEROSIS; CHEMICAL STRUCTURE; LIPID PEROXIDATION; PATHOGENESIS; REVIEW;

EID: 0031689319     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769809065812     Document Type: Review

References (77)

1. G. Jurgens, H. F. Hoff, G. M. Chisolm III and H. Esterbauer (1987) Modification of human serum low density lipoprotein by oxidation - characterization and pathophysiological implications. Chemistry and Physics of Lipids, 45, 315-336.
2. H. Esterbauer, M. D. Rotheneder, G. Waeg, G. Striegl and G. Jurgens (1990) Biochemical, structural, and functional properties of oxidized low-density lipoprotein. Chemical Research in Toxicology, 3, 77-92.
3. H. Esterbauer, J. Gebicki, H. Puhl and G. Jurgens (1992) The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biology & Medicine, 13, 341-390.
4. H. Esterbauer and G. Jurgens (1993) Mechanistic and genetic aspects of susceptibility of LDL to oxidation. Current Opinion in Lipidology, 4, 114-124.
5. V. W. Bowry, K. U. Ingold and R. Stocker (1992) Vitamin E in human low-density lipoprotein. Biochemical Journal, 288, 341-344.
6. E. Niki and N. Noguchi (1997) Handbook of Synthetic Antioxidants (eds. L. Packer and E. Cadenas) Marcel Dekker, New York, pp. 225-239.
7. T. Kita, Y. Nagano, M. Yokode, K. Ishii, N. Kume, A. Ooshima, H. Yoshida and C. Kawai (1987) Probucol prevents the progression of atherosclerosis in Watanebe heritable hyperlipidemic rabbit, an animal model for familial hypercholesterolemia. Proceedings of the National Academy of Science, USA, 84, 5928-5931.
8. S. H. Zhang, R. L. Reddick, E. Avdievish, L. K. Surles, R. G. Jones and J. B. Reynoids (1997) Paradoxical enhancement of atherosclerosis by probucol treatment in apolipoprotein E-deficient mice. The Journal of Clinical Investigation, 99, 2858-2866.
9. O. Quehenberger, E. Koller, G. Jurgens and H. Esterbauer (1987) Investigation of lipid peroxidation in human low density lipoprotein. Free Radical Research Communications, 3, 233-242.
10. H. Esterbauer, R. J. Schaur and H. Zollner (1987) Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde and related aldehydes. Free Radical Biology & Medicine, 11, 81-128.
11. A. L. Bailey, G. Wortley and S. Southon (1997) Measurement of aldehydes in low density lipoprotein by high performance liquid chromatography. Free Radical Biology & Medicine, 23,1078-1085.
12. R. P. Patel, U. Diczfalusy, S. Dzeletovic, M. T. Wilson and V. M. Darley-Usmar (1996) Formation of oxysterols during oxidation of low density lipoprotein by peroxynitrite, myoglobin, and copper. Journal of Lipid Research, 37, 2361-2371.
13. N. Noguchi, N. Gotoh and E. Niki (1993) Dynamics of the oxidation of low density lipoprotein induced by free radicals. Biochimica et Biophysica Acta, 1168, 348-357.
14. H. Esterbauer, G. Striegl, H Puhl and M. Rotheneder (1989) Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Radical Research Communications, 6, 67-75.
15. B. Frei, M. C. Kim and B. N. Ames (1990) Ubiquinol-10 is an effective lipid-soluble antioxidant at physiological concentrations. Proceedings of the National Academy of Sciences, 87, 4879-4883.
16. Y. Yamamoto, M. Kawamura, K. Tatsuno, S. Yamashita, E. Niki and C Naito (1990) Oxidative Damage and Repair (ed. K. J. A. Davies) Pergamon Press, New York, pp. 287-291.
17. G. W. Burton and K. U. Ingold (1986) Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function. Accounts of Chemical Research, 19, 194-201.
18. E. Niki, T. Saito, A. Kawakami and Y. Kamiya (1984) Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. The Journal of Biological Chemistry, 259, 4177-4182.
19. E. Niki, M. Takahashi and K. Komuro (1986) Antioxidant activity of vitamin E in liposomal membranes. Chemistry Letters, 6, 1573-1576.
20. L. R. C. Barclay (1993) Model biomembranes: quantitative studies of peroxidation, antioxidant action, partitioning, and oxidative stress. Canadian Journal of Chemistry, 17, 1-16.
21. M. Takahashi, J. Tsuchiya and E. Niki (1989) Scavenging of radicals by vitamin E in the membranes as studied by spin labeling. The Journal of American Chemical Society, 111, 6350-6353.
22. N. Gotoh, N. Noguchi, J. Tsuchiya, K. Morita, H. Sakai, H. Shimasaki and E. Niki (1996) Inhibition of oxidation of low density lipoprotein by vitamin E and related compounds. Free Radical Research, 24, 123-134.
23. A. R. Waldeck and R. Stocker (1996) Radical-initiated lipid peroxidation in low density lipoproteins: insights obtained from kinetic modeling. Chemical Research in Toxicology, 9, 954-964.
24. L. R. C. Barclay and K. U. Ingold (1981) Autoxidation of biological molecules. 2. The autoxidation of a model membrane. A comparison of the autoxidation of egg lecithin phosphatidylcholine in water and in chlorobenzene. Journal of American Chemical Society, 103, 6478-6485.
25. E. Niki, A. Kawakami, M. Saito, Y. Yamamoto, J. Tsuchiya and Y. Kamiya (1985) Oxidation of lipids. X. Effect of phytyl side chain of vitamin E on its antioxidant activity. Journal of Biological Chemistry, 260, 2191-2196.
26. J. Cillard, P. Cillard, M. Cormier and L. Girre (1980) Journal of American Oil Chemists Society, 57, 252-255.
27. J. Terao and S. Matsushita (1986) The peroxidizing effect of α-tocopherol on autoxidation of methyl linoleate in bulk phase. Lipids, 21, 255-260.
28. M. Takahashi, Y. Yoshikawa and E. Niki (1989) Oxidation of lipids. XVII. Crossover effect of tocopherols in the spontaneous oxidation of methyl linoleate. Bulletin of Chemical Society of Japan, 62, 1885-1890.
29. M. Matsuo, S.Matsumoto, Y. Iitaka and E. Niki (1989) Radical scavenging reactions of vitamin E and its model compound, 2,2,5,7,8-pentamethyl-6-chromanol, in a tertbutylperoxyl radical-generating system. Journal of American Chemical Society, 111, 7179-7185.
30. S. Nagano, Y Okauchi, S. Urano, U. Nagashma and K. Mukai (1990) Kinetic and ab initio study of the prooxidant effect of vitamin E. Hydrogen abstraction from fatty acid esters and egg yolk lecithin. Journal of American Chemical Society, 112, 8921-8924.
31. S. Nagaoka, K. Sawada, Y. Fukumoto, U. Nagashima, S. Katsumata and K. Mukai (1992) Mechanism of prooxidant reaction of vitamin E. Kinetic, spectroscopes, and ab initio study of proton-transfer reaction. The Journal of Physical Chemistry, 96, 6663-6668.
32. K. Mukai, H. Morimoto, Y. Okauchi and S. Nagaoka (1993) Kinetic study of reactions between tocopheroxyl radicals and fatty acids. Lipids, 28, 753-756.
33. K. U. Ingold, V. W. Bowry, R. Stocker and C. Walling (1993) Autooxidation of lipids and antioxidation by α-tocopherol and ubiquinol in homogeneous solution and in aqueous dispersions of lipids: unrecognized consequences of lipid particle size as exemplified by oxidation of human low density lipoprotein. Proceedings of the National Academy of Science, USA, 90, 45-49.
34. V. W. Bowry and R. Stocker (1993) Tocopherol-mediated peroxidation. The prooxidant effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. The Journal of American Chemical Society, 115, 6029-6044.
35. J. Neuzil and R. Stocker (1994) Free and albumin-bound bilirubin are efficient co-antioxidants for α-tocopherol, inhibiting plasma and low density lipoprotein lipid peroxidation. The Journal Biological Chemistry, 269, 16712-16719.
36. V. W. Bowry, D. Mohr, J. Cleary and R. Stocker (1995) Prevention of tocopherol-mediated peroxidation in ubiquinol-10-free human low density lipoprotein. The Journal of Biological Chemistry, 270, 5756-5763.
37. S. R. Thomas, J. Neuzil and R. Stocker (1996) Cosupplementation with coenzyme Q prevents the prooxidant effect of α-tocopherol and increases the resistance of LDL to transition metal-dependent oxidation initiation. Arteriosclerosis, Thrombosis, and Vascular Biology, 16, 687-696.
38. J. M. Upston, J. Neuzil, and R. Stocker (1996) Oxidation of LDL by recombinant human 15-lipoxygenase: evidence for α-tocopherol-dependent oxidation of esterified core and surface lipids. Journal of Lipid Research, 37, 2650-2661.
39. J. Neuzil, S. R. Thomas and R. Stocker (1997) Requirement for, promotion, or inhibition by α-tocopherol of radical-induced initiation of plasma lipoprotein lipid peroxidation. Free Radical Biology & Medicine, 22, 57-71.
40. P. M. Abuja and H. Esterbauer (1995) Simulation of lipid peroxidation in low-density lipoprotein by a basic "skeleton" of reactions. Chemical Research in Toxicology, 8, 753-763.
41. P. M. Abuja, R. Albertini and H. Esterbauer (1997) Simulation of the induction of oxidation of low-density lipoprotein by high copper concentrations; Evidence for a nonconstant rate of initiation. Chemical Research in Toxicology, 10, 644-651.
42. N. Hogg, C. Rice-Evans, V. M. Darley-Usmar, M.T. Wilson, G. Paganga and L. Bourne (1994) The role of lipid hydroperoxides in the myoglobin dependent oxidation of LDL. Archives of Biochemistry and Biophysics, 313, 313-318.
43. C. E. Thomas and R. L. Jackson (1991) Lipid hydroperoxide involvement in copper-dependent and -independent oxidation of low density lipoproteins. Journal of Pharmacological Experimental Therapy, 256, 1182-1188.
44. V. J. O'Leary, V. M. Darley-Usmar, L. J. Russell and D. Stone (1992) Pro-oxidant effects of lipoxygenasederived peroxides on the copper-initiated oxidation of low-density lipoprotein. Biochemical Journal, 282, 631-634.
45. A. Lass, J. Belkner, H. Esterbauer and H. Kuhn (1996) Lipoxygenase treatment renders low density lipoprotein susceptible to copper catalyzed oxidation. Biochemical Journal, 314, 577-585.
46. J. P. Thomas, B. Kalyanaraman and A. W. Girotti (1994) Involvement of pre-existing lipid hydroperoxides in copper stimulated oxidation of low density lipoprotein. Archives of Biochemistry and Biophysics, 315, 244-254.
47. S. M. Lynch and B. Frei (1995) Implications for metal ion-dependent oxidative modification of LDL. Journal of Biological Chemistry, 270, 5158-5163.
48. N. Noguchi, N. Gotoh and E. Niki (1994) Effects of ebselen and probucol on oxidative modification of lipids and protein of low density lipoprotein induced by free radicals. Biochimica et Biophysica Acta, 1213, 176-182.
49. M. Maiorino, A. Roveri and F. Ursini (1992) Antioxidant effect of ebselen (PZ 51): Peroxidase mimetic activity on phospholipid and cholesterol hydroperoxides vs free radical scavenger activity. Archives of Biochemistry and Biophysics, 295, 404-409.
50. Y. Yoshida, J. Tsuchiya and E. Niki (1994) Interaction of α-tocopherol with copper and its effect on lipid peroxidation. Biochimica et Biophysica Acta, 1200, 85-92.
51. M. Maiorino, A. Zamburlini, A. Roveri and F. Ursini (1993) Prooxidant role of vitamin E in copper induced lipid peroxidation. FEBS Letters, 330, 174-176.
52. M. Iwatsuki, E. Niki, D. Stone and V. M. Darley-Usmar (1995) α-Tocopherol mediated peroxidation in the copper (II) and metmyoglobin induced oxidation of human LDL: the influence of lipid hydroperoxides. FEBS Letters, 360, 271-276.
53. E. Niki, A. Kawakami, Y. Yamamoto and Y. Kamiya (1985) Oxidation of lipids. VIII. Synergistic inhibition of oxidation of phosphatidylcholine liposome in aqueous dispersion by vitamin E and vitamin C. Bulletin of Chemical Society of Japan, 58, 1971-1975.
54. T. Doba, G. W. Burton and K. U. Ingold (1985) Antioxidant and co-antioxidant activity of vitamin C, The effect of vitamin C, either alone or in the presence of vitamin E or a water soluble vitamin E analogue upon the peroxidation of aqueous multilamellar phospholipid liposomes. Biochimica et Biophysica Acta, 835, 298-303.
55. V. E. Kagan, E. A. Serbinova, T. Forte, G. Scita and L. Packer (1992) Recycling of vitamin E in human low density lipoproteins. Journal of Lipid Research, 33, 385-397.
56. B. Kalyanaraman, V. M. Darley-Usmar, J. Wood, J. Joseph and S. Parthasarathy (1992) Synergistic interaction between the probucol phenoxyl radical and ascorbic acid in inhibiting the oxidation of low density lipoprotein. The Journal of Biological Chemistry, 267, 6789-6795.
57. M. Takahashi, J. Tsuchiva, E. Niki and S. Urano (1988) Action of vitamin E as antioxidant in phospholipid liposomal membranes as studied by spin label technique. Journal of Nutritional Science and Vitaminology, 34, 25-34.
58. N. Noguchi, Y. Okimoto, J. Tsuchiya, O. Cynshi, T. Kodama and E. Niki (1997) Inhibition of oxidation of low-density lipoprotein by a novel antioxidant BO-653 prepared by theoretical design. Archives of Biochemistry and Biophysics, 347, 141-147.
59. Y. Yamamoto, E. Komuro and E. Niki (1990) Antioxidant activity of ubiquinol in solution and phosphatidylcholine liposome. Journal of Nutritional Science and Vitaminology, 36, 505-511.
60. K. Mukai, S. Kikuchi and S. Urano (1990) Stopped-flow kinetic study of the regeneration reaction of tocopheroxyl radical by reduced ubiquinone-10 in solution. Biochimica et Biophysica Acta, 1035, 77-82.
61. E. Niki, N. Noguchi and N. Gotoh (1993) Inhibition of oxidative modification of low density lipoprotein by antioxidants. Journal of Nutritional Science and Vitaminology, 39, S1-S8.
62. D. C. Liebler, J. A. Burr, L. Philips and A. J. L. Ham (1996) Gas chromatography-mass spectrometry analysis of vitamin E and its oxidation products. Analytical Biochemistry, 236, 27-34.
63. K. Mukai, S. Itoh and H. Morimoto (1992) Stopped-flow kinetic study of vitamin E regeneration reaction with biological hydroquinones (reduced forms of ubiquinone, vitamin K, and tocopherolquinone) in solution. Journal of Biological Chemistry, 267, 22277-22281.
64. K. Mukai, H. Morimoto, S. Kikuchi and S. Nagaoka (1993) Kinetic study of free-radical-scavenging action of biological hydroquinones (reduced forms of ubiquinoe, vitamin K and tocopherol quinone) in solution. Biochimica et Biophysics Acta, 1157, 313-317.
65. J. Neuzil, P. K. Witting and R. Stocker (1997) α-Tocopheryl hydroquinone is an efficient multifunctional inhibitor of radical-initiated oxidation of low density lipoprotein lipids. Proceedings of the National Academy of Science, USA, 94, 7885-7890.
66. F. Bohm, R. Edge, E. J. Land, D. J. McGarvey and T. G. Truscott (1997) Carotenoids enhance vitamin E antioxidant efficiency. The Journal of American Chemical Society, 119, 621-622.
67. H. Tsuchihashi, M. Kigoshi, M. Iwatsuki and E. Niki (1995) Action of β-carotene as an antioxidant against lipid peroxidation. Archives of Biochemistry and Biophysics, 323, 137-147.
68. E. Niki (1987) Antioxidants in relation to lipid peroxidation. Chemistry and Physics of Lipids, 44, 227-253.
69. K. F. Gey, P. Puska, P. Jordan and U. K. Moser (1991) Inverse correlation between plasma vitamin E and mortality from ischemic heart disease in cross-cultural epidemiology. American Journal of Clinical Nutrition, 53, 326S-334S
70. M. J. Stampfer, C. H. Hennekens, J. E. Manson, G. A. Colditz, B Rosner and W. C. Willett (1993) Vitamin E consumption and the risk of coronary disease in women. New England Journal of Medicine, 328, 1444-1449.
71. E. B. Rimm, M. J. Stampfer, A. Ascherio, E. Giovannucci, G. A. Colditz and W. C. Willett (1993) Vitamin E consumption and the risk of coronary heart disease in men. New England Journal of Medicine, 328, 1450-1456.
72. N. G. Stephens, A. Parsons, P. W. Schofield, F. Ketty, K. Cheeseman and M. J. Mitchinson (1996) Randomised controlled trial of vitamin E in patients with coronary disease: Cambridge Heart Antioxidant Study (CHAOS). Lancet, 347, 781-786.
73. P. Knekt (1993) Vitamin E in Health and Disease (eds. L. Packer and J. Juchs) Marcel Dekker, New York, pp. 513-527.
74. M. Sano, C. Ernesto, R. G. Thomas, M. R. Klauber, K. Schafer, M. Grundman, P. Woodbury, J. Growdon, C. W. Cotman, E. Pfeiffer, L. S. Schneider and L. J. Thal (1997) A controlled trial of selegiline, alpha-tocopherol or both as treatment for Alzheimer's disease. New English Journal of Medicine, 336, 1216-1222.
75. S. N. Meydani, M. Meydani, J. B. Blumberg, L. S. Laka, G. Siber, R. Loszweski, C. Thompson, M.C. Pedrosa, R. D. Diamond and B. D. Stollar (1997) Vitamin E supplementation and in vivo immune response in healthy elderly subjects. JAMA 277, 1380-1386.
76. B. D. Szewczyka and A. Azzi (1991) Alpha-tocopherol (vitamin E) regulates vascular smooth muscle cell proliferation and protein kinase C activity. Archives of Biochemistry & Biophysics, 286, 264-269.
77. N. K. Ozer, D. Boscoboinik and A. Azzi (1995) New roles of low density lipoproteins and vitamin E in the pathogenesis of atherosclerosis. Biochemistry & Molecular Biology International, 35, 117-124.