New insights into the oxidative electrochemistry of vitamin E

Accounts of Chemical Research

Volumn 40, Issue 4, 2007, Pages 251-257

  Webster, Richard D ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ACETONITRILE DERIVATIVE; ALPHA TOCOPHEROL; ANTIOXIDANT; CATION; DICHLOROMETHANE; FERROCENE; FERROUS ION; NITRIC OXIDE; PHENOL DERIVATIVE; PHENOXYL RADICAL; PROTON; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; SPECTROSCOPY;

ACETONITRILES; ANTIOXIDANTS; CATIONS; ELECTROCHEMISTRY; ELECTRON TRANSPORT; FERROUS COMPOUNDS; METHYLENE CHLORIDE; MOLECULAR STRUCTURE; NITRIC OXIDE; OXIDATION-REDUCTION; PHENOLS; PROTONS; SOLVENTS; SPECTRUM ANALYSIS; VITAMIN E;

EID: 34248372502     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar068182a     Document Type: Article

References (45)

1. Burton, G. W.; Ingold, K. U. Vitamin E: Application of the Principles of Physical Organic Chemistry to the Exploration of Its Structure and Function. Acc. Chem. Res. 1986, 19, 194-201.
2. Finkel, T.; Holbrook, N. J. Oxidants, Oxidative Stress and the Biology of Ageing. Nature 2000, 408, 239-247.
3. Wang, X.; Quinn, P. J. The Location and Function of Vitamin E in Membranes. Mol. Membr. Biol. 2000, 17, 143-156.
4. Niki, E.; Noguchi, N. Dynamics of Antioxidant Action of Vitamin E. Acc. Chem. Res. 2004, 37, 45-51.
5. Traber, M. G.; Arai, H. Molecular Mechanisms of Vitamin E Transport. Annu. Rev. Nutr. 1999, 19, 343-355.
6. Ricciarelli, R.; Zingg, J.-M.; Azzi, A. The 80th Anniversary of Vitamin E: Beyond Its Antioxidant Properties. Biol. Chem. 2002, 383, 457-465.
7. Boscoboinik, D.; Szewczyk, A.; Hensey, C.; Azzi, A. Inhibition of Cell-Proliferation by α-Tocopherol - Role of Protein-Kinase-C. J. Biol. Chem. 1991, 266, 6188-6194.
8. Tasinato, A.; Boscoboinik, D.; Bartoli, G. M.; Maroni, P. Azzi, A. d-α-Tocopherol Inhibition of Vascular Smooth Muscle Cell Proliferation Occurs at Physiological Concentrations, Correlates With Protein Kinase C Inhibition, and Is Independent of Its Antioxidant Properties. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 12190-12194.
9. Min, K. C.; Kovall, R. A.; Hendrickson, W. A. Crystal Structure of Human α-Tocopherol Transfer Protein Bound to Its Ligand: Implications for Ataxia with Vitamin E Deficiency. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 14713-14718.
10. Hosomi, A.; Arita, M.; Sato, Y.; Kiyose, C.; Ueda, T.; Igarashi, O.; Arai, H.; Inoue, K. Affinity for α-Tocopherol Transfer Protein as a Determinant of the Biological Activities of Vitamin E Analogs. FEBS Lett. 1997, 409, 105-108.
11. Melton, L. The Antioxidant Myth. New Sci. 2006, 2563, 40-43.
12. Svanholm, U.; Bechgaard, K.; Parker, V. D. Electrochemistry in Media of Intermediate Acidity. VIII. Reversible Oxidation Products of the α-Tocopherol Model Compound. Cation Radical, Cation, and Dication. J. Am. Chem. Soc. 1974, 96, 2409-2413.
13. Nanni, E. J., Jr.; Stallings, M. D.; Sawyer, D. T. Does Superoxide Ion Oxidize Catechol, α-Tocopherol, and Ascorbic Acid by Direct Electron Transfer? J. Am. Chem. Soc. 1980, 102, 4481-4485.
14. Webster, R. D. Voltammetric Studies on the α-Tocopherol Anion and α-Tocopheroxyl (Vitamin E) Radical in Acetonitrile. Electrochem. Commun. 1999, 1, 581-584.
15. Williams, L. L.; Webster, R. D. Electrochemically Controlled Chemically Reversible Transformation of α-Tocopherol (Vitamin E) into Its Phenoxonium Cation. J. Am. Chem. Soc. 2004, 126, 12441-12450.
16. Lee, S. B.; Lin, C. Y.; Gill, P. M. W.; Webster, R. D. Transformation of α-Tocopherol (Vitamin E) and Related Chromanol Model Compounds into Their Phenoxonium Ions by Chemical Oxidation with the Nitrosonium Cation. J. Org. Chem. 2005, 70, 10466-10473.
17. Wilson, G. J.; Lin, C. Y.; Webster, R. D. Significant Differences in the Electrochemical Behavior of the α-, β-, γ-, and δ-Tocopherols (Vitamin E). J. Phys. Chem. B 2006, 110, 11540-11548.
18. - Anions. J. Am. Chem. Soc. 2006, 128, 9332-9333.
19. Groves, J. T.; Boxer, S. G. Micropattern Formation in Supported Lipid Membranes. Acc. Chem. Res. 2002, 35, 149-157.
20. Dimroth, K.; Umbach, W.; Thomas, H. Stabile Phenoxy-Kationen aus Arylierten Phenolen. Chem. Ber. 1967, 100, 132-141.
21. Speiser, B.; Rieker, A. Electrochemical Oxidations. Part 1. Phenoxy Cations in the Anodic Oxidation of Phenolic Compounds. J. Chem. Res. (S) 1977, 314-315.
22. Vigalok, A.; Rybtchinski, B.; Gozin, Y.; Koblenz, T. S.; Ben-David, Y.; Rozenberg, H.; Milstein, D. Metal-Stabilized Phenoxonium Cation. J. Am. Chem. Soc. 2003, 125, 15692-15693.
23. Hammerich, O.; Svensmark, B. Oxygen-Containing Compounds. In Organic Electrochemistry, 3rd ed.; Lund, H., Baizer, M. M., Eds.; Marcel Dekker: New York, 1991; Chapter 16.
24. Rudolph, M.; Reddy, D. P.; Feldberg, S. W. A Simulator for Cyclic Voltammetric Responses. Anal. Chem. 1994, 66, 589A-600A.
25. Bowry, V. W.; Ingold, K. U. Extraordinary Kinetic Behavior of the α-Tocopheroxyl (Vitamin E) Radical. J. Org. Chem. 1995, 60, 5456-5467.
26. Bolza, F.; Treloar, F. E. Conductivity of Trifluoroacetic Acid in 1,2-Dichloroethane. J. Chem. Eng. Data 1972, 17, 197-199.
27. Evans, D. H.; Jimenez, P. J.; Kelly, M. J. Reversible Dimerization of Phenoxyl Radicals Formed by Anodic Oxidation of Phenolates. J. Electroanal. Chem. 1984, 163, 145-157.
28. Webster, R. D. In Situ Electrochemical-ATR-FTIR Spectroscopic Studies on Solution Phase 2,4,6-Tri-Substituted Phenoxyl Radicals. Electrochem. Commun. 2003, 5, 6-11.
29. Parkhurst, R. M.; Skinner, W. A. Chromans and Tocopherols. In Chemistry of Heterocyclic Compounds; Ellis, G. P., Lockhart, I. M., Eds.; Wiley: New York, 1981; Vol. 36, Chapter 3.
30. Rosenau, T.; Habicher, W. D. Novel Tocopherol Compounds I. Bromination of α-Tocopherol - Reaction Mechanism and Synthetic Applications. Tetrahedron 1995, 51, 7919-7926.
31. Rosenau, T.; Potthast, A.; Elder, T.; Kosma, P. Stabilization and First Direct Spectroscopic Evidence of the o-Quinone Methide Derived from Vitamin E. Org. Lett. 2002, 4, 4285-4288.
32. Edge, R.; Land, E. J.; McGarvey, D.; Mulroy, L.; Truscott, T. G. Relative One-Electron Reduction Potentials of Carotenoid Radical Cations and the Interactions of Carotenoids with the Vitamin E Radical Cation. J. Am. Chem. Soc. 1998, 120, 4087-4090.
33. Packer, J. E.; Slater, T. F.; Willson, R. L. Direct Observation of a Free Radical Interaction between Vitamin E and Vitamin C. Nature 1979, 278, 737-738.
34. 2 Oxidation of α-Tocopherol and Its Model Compound in Solution. Chem. Phys. Lipids 1981, 29, 129-135.
35. Matsuo, M.; Matsumoto, S.; Ozawa, T. Electron Spin Resonance Spectra and Hyperfine Coupling Constants of the α-Tocopheroxyl and 2,2,5,7,8-Pentamethylchroman-6-oxyl Radicals Derived from Vitamin E and Its Model and Deuterated Model Compounds. Org. Magn. Reson. 1983, 21, 261-264.
36. Mukai, K.; Tsuzuki, N.; Ishizu, K.; Ouchi, S.; Fukuzawa, K. Electron Spin Resonance and Electron Nuclear Double Resonance Studies of Cation Radicals Derived From Tocopherol Model Compounds. Chem. Phys. Lipids 1984, 35, 199-208.
37. Lehtovuori, P.; Joela, H. Radical Cations of Vitamin E. Phys. Chem. Chem. Phys. 2002, 4, 1928-1933.
38. Parker, A. W.; Bisby, R. H. Time-Resolved Resonance Raman Spectroscopy of α-Tocopheroxyl and Related Radicals in Solvent, Micellar and Membrane Systems. J. Chem. Soc., Faraday Trans. 1993, 89, 2873-2878.
39. Costentin, C.; Robert, M.; Savéant, J.-M. Electron Transfer and Bond Breaking: Recent Advances. Chem. Phys. 2006, 324, 40-56.
40. Costentin, C.; Robert, M.; Savéant, J.-M. Electrochemical and Homogeneous Proton-Coupled Electron Transfers: Concerted Pathways in the One-Electron Oxidation of a Phenol Coupled with an Intramolecular Amine-Driven Proton Transfer. J. Am. Chem. Soc. 2006, 128, 4552-4553.
41. Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. Concerted Proton-Electron Transfer in the Oxidation of Hydrogen-Bonded Phenols. J. Am. Chem. Soc. 2006, 128, 6075-6088.
42. Chevion, S.; Roberts, M. A.; Chevion, M. The Use of Cyclic Voltammetry for the Evaluation of Antioxidant Capacity. Free Radical Biol. Med. 2000, 28, 860-870.
43. Kilmartin, P. A.; Zou, H.; Waterhouse, A. L. A Cyclic Voltammetry Method Suitable for Characterizing Antioxidant Properties of Wine and Wine Phenolics. J. Agric. Food. Chem. 2001, 49, 1957-1965.
44. Rieker, A.; Beisswenger, R.; Regier, K. Synthesis via Anodically Produced Phenoxenium Ions. Applications in the Field of Peptides and Carbohydrates. Tetrahedron 1991, 47, 645-654.
45. Infante, J. P. A Function for the Vitamin E Metabolite α-Tocopherol Quinone as an Essential Enzyme Cofactor for the Mitochondrial Fatty Acid Desaturases. FEBS Lett. 1999, 446, 1-5.