Vitamin E: Application of the Principles of Physical Organic Chemistry to the Exploration of Its Structure and Function

Accounts of Chemical Research

Volumn 19, Issue 7, 1986, Pages 194-201

  Burton, G W ^a   Ingold, K U ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845374568     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00127a001     Document Type: Article

References (68)

1. For a review of homogeneous liquid phase autoxidation see: Howard, J. A. In Free Radicals, Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, pp 3-62.
2. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095-5099.
3. For a review of peroxyl radical chemistry see: Ingold, K. U. Acc. Chefn. Res. 1969, 2, 1-9.
4. For a review of antioxidation see: Ingold, K. U. Chem. Rev. 1961, 61, 563-589.
5. For a 1980 state-of-the-art report see: Vitamin, E. A. Comprehensive Treatise; Machlin, L. J., Ed.; Marcel Dekker: New York, 1980.
6. For reviews of phenolic antioxidants see: Ingold, K. U. Spec. Publ.-Chem. Soc. 1971, 24, 285-293; Mahoney, L. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 547-555.
7. Horswill, E. C.; Howard, J. A.; Ingold, K. U. Can. J. Chem. 1966, 44, 985-991.
8. Boozer, C. E.; Hammond, G. S.; Hamilton, C. E.; Sen, J. N. J. Am. Chem. Soc. 1955, 77, 3233-3237.
9. Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472–6477.
10. See also: (a) Howard, J. A.; Ingold, K. U. Can. J. Chem. 1962, 40, 1851-1864; (b) 1963, 41, 1744-1751; (c) 1963, 41, 2800-2806; (d) 1964, 42, 1044–1056.
11. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1965, 43, 2729–2736.
12. Century, B.; Horwitt, M. K. Fed. Proc., Fed. Am. Soc. Exp. Biol. 1965, 24, 906–911.
13. Chipault, J. R. In Autoxidation and Antioxidants; Lundberg, W. O., Ed.; Interscience: New York, 1982; Vol. 2, Chapter 12, pp 477–542.
14. Green, J.; Diplock, A. T.; Bunyan, J.; McHale, D.; Muthy, I. R. Br. J. Nutr. 1967, 21, 69–101. Green, J.; Bunyan, J. Nutr. Abstr. Rev. 1969, 39, 321–345. Green, J. Ann. N.Y. Acad. Sci. 1972, 203, 29–43.
15. Burton, G. W.; Doba, T.; Gabe, E.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053–7065.
16. Burton, G. W.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1983, 105, 5950–5951.
17. Gilchrist, J. L. G.; Burton, G. W.; Ingold, K. U. Chem. Phys. 1985, 95, 473–481.
18. Doba, T.; Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1983, 105, 6505–6506.
19. Mahoney, L. R.; Korcek, S.; Hoffman, S.; Willermet, P. A. Ind. Eng. Chem. Prod. Res. Dev. 1978, 17, 250–255. Willermet, P. A.; Mahoney, L. R.; Haas, C. M. Tech. Prepr.-Am. Soc. Lubr. Eng. 1978, 78-AM-1B-1; ASLE Trans. 1979, 22, 301–306. Mahoney, L. R.; Otto, K.; Korcek, S.; Johnson, M. D. Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 11–15.
20. Plasma is the clear yellow liquid which constitutes about 60% by volume of blood and is obtained as the supernatant after centrifugation of the RBC. The latter make up ca. 40% by volume of blood.
21. Burton, G. W.; Joyce, A.; Ingold, K. U. Lancet 1982, 2, 327.
22. Burton, G. W.; Joyce, A.; Ingold, K. U. Arch. Biochem. Biophys. 1983, 221, 281–290.
23. Dodge, J. T.; Mitchell, C.; Hanahan, D. J. Arch. Biochem. Biophys. 1963, 100, 119–130.
24. Burton, G. W.; Ingold, K. U.; Thompson, K. E. Lipids 1981,16, 946.
25. Folch, J.; Ascoli, I.; Lees, M.; Meath, J. A.; Lebaron, F. N. J. Biol. Chem. 1951, 191, 833–841. Folch, J.; Lees, M.; Stanley, G. H. S. J. Biol. Chem. 1957, 226, 497–509.
26. These observations date back at least to: Donnan, S. K. J. Biol. Chem. 1950, 182, 415–419.
27. Shuster, C. W. Proc. Soc. Exp. Biol. Med. 1958, 90, 423–426.
28. Ahmed, S. M.; Slater, T. F. In Recent Advances in Lipid Peroxidation and Tissue Injury; Slater, T. F.; Garner, A., Eds.; Brunel University Printing Services: Uxbridge, U.K., 1981; pp 177–194.
29. Burlakova, E. B.; Molochkina, E. M.; Palmina, N. P. Adv. Enzyme Regul. 1980,18, 163–179.
30. Player, T. J. In Free Radicals, Lipid Peroxidation and Cancer; McBrien, D. C. H.; Slater, T. F.; Eds.; Academic: London, 1982; pp 173-195.
31. Burton, G. W.; Cheeseman, K. H.; Ingold, K. U.; Slater, T. F. Biochem. Soc. Trans. 1983, 11, 261–262.
32. Slater, T. F.; Benedetto, C.; Burton, G. W.; Cheeseman, K. H.; Ingold, K. U.; Nodes, J. T. In Icosanoids and Cancer, Thaler-Dao, H., Paulet, A. C., Paoletti, R. Eds.; Raven: New York, 1984; pp 21–29.
33. Cheeseman, K. H.; Burton, G. W.; Ingold, K. U.; Slater, T. F. Toxicol. Pathol. 1984, 12, 235–239.
34. Cheeseman, K. H.; Collins, M.; Proudfoot, K.; Slater, T. F.; Burton, G. W.; Webb, A. C.; Ingold, K. U. Biochem. J. 1986,235, 507–514.
35. Cheeseman, K. H.; Collins, M.; Maddix, S.; Milia, A.; Proudfoot, K.; Slater, T. F.; Burton, G. W.; Webb, A.; Ingold, K. U. FEBS Lett., submitted for publication.
36. Singer, S. J.; Nicolson, G. L. Science 1972, 175, 720-731; Stryer, L. Biochemistry; Freeman: San Francisco, 1975; Chapter 10, pp 227–252.
37. Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 7792-7794.
38. Porter, N. A.; Weber, B. A.; Weenen, H.; Khan, J. A. J. Am. Chem. Soc. 1980, 102, 5597–5601. Weenen, H.; Porter, N. A. J. Biol. Chem. 1982, 104, 5216–5221.
39. Barclay, L. R. C.; Locke, S. J.; MacNeil, J. M. Can. J. Chem. 1983, 61, 1288-1290; 1985, 63, 366–374.
40. Barclay, L. R. C.; Locke, S. J.; MacNeil, J. M.; VanKessel, J.; Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 2479–2481.
41. Barclay, L. R. C.; MacNeil, J. M.; VanKessel, J.; Forrest, B. J.; Porter, N. A.; Lehman, L. S.; Smith, K. J.; Ellington, J. C., Jr. J. Am. Chem. Soc. 1984, 106, 6740–6747.
42. Yamamoto, Y.; Niki, E.; Kamiya, Y. Bull. Chem. Soc. Jpn. 1982, 55, 1548–1550. Yamamoto, Y.; Niki, E.; Kamiya, Y.; Shimasaki, H. Biochim. Biophys. Acta 1984, 795, 332–340.
43. Perly, B.; Smith, I. C. P.; Hughes, L.; Burton, G. W.; Ingold, K. U. Biochim. Biophys. Acta 1985, 819, 131–135.
44. Barclay, L. R. C.; Locke, S. J.; MacNeil, J. M.; VanKessel, J. Can. J. Chem. 1985, 63, 2633–2638.
45. Fessenden, R. W.; Hitachi, A.; Nagarajan, V. J. Phys. Chem. 1984, 88, 107–110. (47) Golumbic, C.; Mattill, H. A. J. Am. Chem. Soc. 1941, 63, 1279–1280.
46. Tappel, A. L. Geriatrics 1968, 23, 97–105.
47. Packer, J. E.; Slater, T. F.; Willson, R. A. Nature 1979, 278, 737–738.
48. Niki, E.; Tsuchiya, J.; Tanimura, R.; Kamiya, Y. Chem. Lett. 1982, 789–792.
49. Niki, E.; Saito, T.; Kamiya, Y. Chem. Lett. 1983, 631–632. Niki, E.; Saito, T.; Kawakami, A.; Kamiya, Y. J. Biol. Chem. 1984, 259, 4177–4182.
50. Yamamoto, Y.; Haga, S.; Niki, E.; Kamiya, Y. Bull. Chem. Soc. Jpn. 1984, 57, 1260-1264. Pryor, W. A.; Kaufman, M. J.; Church, D. F. J. Org. Chem. 1985, 50, 281–283.
51. Doba, T.; Burton, G. W.; Ingold, K. U. Biochim. Biophys. Acta 1985, 835, 298–303.
52. Niki, E.; Kawakami, A.; Yamamoto, Y.; Kamiya, Y. Bull. Chem. Soc. Jpn. 1985, 58, 1971-1975.
53. Ames, B. N.; Cathcart, R.; Schwiers, E.; Hochstein, P. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6858–6862. See also: Matsushita, S.; Ibuki, F.; Aoki, A. Arch. Biochem. Biophys. 1963, 102, 446–451. Proctor, P. Nature (London) 1970, 228, 868–869.
54. (a) Niki, E.; Yamamoto, Y.; Kamiya, Y. Chem. Lett. 1985, 1267–1270. (b) Niki, E.; Saito, M.; Yoshikawa, Y.; Yamamoto, Y.; Kamiya, Y. Bull. Chem. Soc. Jpn. 1986, 59, 471–477.
55. Wayner, D. D. M., unpublished result from this laboratory.
56. Wayner, D. D. M.; Burton, G. W.; Ingold, K. U.; Locke, S. FEBS Lett. 1985, 187, 33–37.
57. 58 and now obtain somewhat lower TRAC values.
58. Niki, E.; Kawakami, A.; Saito, M.; Yamamoto, Y.; Tsuchiya, J.; Kamiya, Y. J. Biol. Chem. 1985, 260, 2191–2196.
59. Weiser, H.; Vecchi, M. Int. J. Vit. Nutr. Res. 1982, 52, 351–370.
60. Burton, G. W.; Foster, D. O.; Perly, B.; Slater, T. F.; Smith, I. C. P.; Ingold, K. U. Philos. Trans. R. Soc. London B 1985, B311, 565–578.
61. Ingold, K. U.; Burton, G. W.; Foster, D. O.; Hughes, L.; Lindsay, D. A.; Webb, A. Lipids, submitted for publication.
62. Burton, G. W.; Webb, A.; Ingold, K. U. Lipids 1985, 20, 29–39.
63. Bligh, E. G.; Dyer, W. J. Can. J. Biochem. Physiol. 1959, 37, 911–917.
64. “Recommended Dietary Allowances”, 9th ed; National Academy Science: Washington, DC, 1980, p 64.
65. Silber, R.; Winter, R.; Kayden, H. J. J. Clin. Invest. 1969, 48 2089–2095. Poukka, R. K. H.; Bieri, J. G. Lipids, 1970, 5, 757–761 Bjornson, L. K.; Gniewkowski, C.; Kayden, H. J. J. Lipid Res. 1975, 16 39-53.
66. Machlin, L. J.; Gabriel, E.; Brin, M. J. Nutr. 1982, 112, 1437-1440.
67. Ingold, K. U.; Burton, G. W.; Foster, D. O.; Zuker, M.; Hughes, L.; Lusztyk, E.; Slaby, M. FEBS Lett., submitted for publication.
68. 66We have now synthesized and are currently measuring the bioactivities of RRR-6 and SRR-6.