One-electron oxidation of quercetin and quercetin derivatives in protic and non protic media

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 1999, Pages 1387-1395

  Dangles, Olivier ^a   Fargeix, Guillaume ^a   Dufour, Claire ^b  

^a UNIVERSITÉ LYON 1   (France)

^b CEMAGREF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001383541     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901460h     Document Type: Article

References (48)

1. The Flavonoids, Advances in Research since 1986, Ed. J. B. Harborne, Chapman and Hall, London. 1994.
2. E. Middleton Jr. and C. Kandaswami, in The Flavonoids, Advances in Research since 1986, Ed. J. B. Harborne, Chapman and Hall, London, 1994, p. 619.
3. (a) A. T. Diplock, in Free Radical Damage and its Control, New Comprehensive Biochemistry, Vol. 28, Ed. C. A. Rice-Evans and R. H. Burdon, Eisevier, Amsterdam, 1994, p. 113;
4. (b) R. A. Larson, Naturally Occurring Antioxidants, Lewis Publishers, CRC Press LLC, Boca Raton, 1997.
5. (a) C. A. Rice-Evans, in Free Radical Damage and its Control. New Comprehensive Biochemistry, Vol. 28. Ed. C. A. Rice-Evans and R. H. Burdon, Elsevier, Amsterdam, 1994, p. 131;
6. (b) H. Sies, Angew. Chem., Int. Ed. Engl., 1986, 25, 1058.
7. (a) Flavonoids in Health and Disease, Ed. C. A. Rice-Evans and L. Packer, M. Dekker, New York, 1997;
8. (b) P. Cos, L. Ying, M. Calomme, J. P. Hu, K. Cimanga, B. Van Poel, L. Pieters, A. J. Vlietinck and D. Vanden Berghe, J. Nat. Prod., 1998, 61, 71;
9. (c) N. Salah, N. J. Miller, G. Paganga, L. Tijburg, G. P. Bolwell and C. Rice-Evans, Arch. Biochem. Biophys., 1995, 322, 339;
10. (d) C. Rice-Evans, N. J. Miller and G. Paganga, Free Radical Biol. Med., 1996, 20, 933;
11. (e) G. Cao, E. Sofic and R. L. Prior, Free Radical Biol. Med., 1997, 22, 749;
12. (f) J. R. S. Hoult, M. A. Moroney and M. Paya, Methods Enzymol., 1994, 234, 443;
13. (g) I. Morel. G. Lescoat, P. Cillard and J. Cillard, Methods Enzymol., 1994, 234, 437;
14. (h) W. F. Hodnick, D. L. Duval and R. S. Pardini, Biochem. Pharmacol., 1994, 47, 573;
15. (i) N. Cotelle, J.-L. Bernier, J.-P. Catteau, J. Pommery, J.-C. Wallet and E. M. Gaydou, Free Radical Biol. Med., 1996, 20, 35;
16. (j) J. A. Vinson, J. Jang, Y. A. Dabbagh, M. M. Serry and S. Cai, J. Agric. Food Chem., 1995, 43, 2798.
17. (a) M. G. L. Hertog, E. J. M. Feskens, P. C. H. Hollman, M. B. Katan and D. Kromhout, The Lancet, 1993, 342, 1007;
18. (b) D. S. Leake, in Photochemistry of Fruit and Vegetables, Ed. F. A. Tomas-Barberan and R. J. Robins, Clarendon Press, Oxford, 1997, p. 287.
19. (a) S. Steenken and P. Neta, J. Phys. Chem., 1982, 86, 3661;
20. (b) W. Bors and M. Saran, Free Radical Res. Commun., 1987, 2, 289;
21. (c) W. Bors, W. Heller, C. Michel and M. Saran, Methods Enzymol., 1990, 186, 343;
22. (d) W. Bors, C. Michel and M. Saran, Methods Enzymol., 1994, 234, 420;
23. (e) S. V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic and M. G. Simic, J Am. Chem. Soc., 1994, 116, 4846;
24. (f) S. V. Jovanovic, S. Steenken, Y. Hara and M. G. Simic, J. Chem. Soc., Perkin Trans. 2, 1996, 2497;
25. (g) W. Bors and M. Saran, Free Radical Res Commun., 1987, 2, 289.
26. (a) M. G. Peters, Angew. Chem., Int. Ed. Engl., 1989, 28, 555;
27. (b) Y. J. Abul-Hajj, K. Tabakovic and I. Tabakovic, J. Am. Chem. Soc., 1995, 117, 6144.
28. (a) L. Valgimigli, J. T. Banks, K. U. Ingold and J. Lusztyk, J. Am. Chem. Soc., 1995, 117, 9966;
29. (b) C. Sanchez-Moreno, J. A. Larrauri and F. Saura-Calixto, J. Sci. Food Agric., 1998, 76, 270;
30. (c) T. Yoshida, K. Mori, T. Hatano, T. Okumura, I. Uehara, K. Komagoe, Y. Fujita and T. Okuda, Chem. Pharm. Bull. 1989, 37, 1919.
31. O. Dangles, C. Dufour and S. Bret, J. Chem. Soc., Perkin Trans. 2, 1999, 737.
32. (a) M. Utaka and A. Takeda, J. Chem. Soc., Chem. Commun., 1985, 1824;
33. (b) M. A. Smith, R. A. Webb and L. J. Cline, J. Org. Chem., 1965, 30, 995.
34. P. Hapiot, A. Neudeck, J. Pinson, H. Fulcrand, P. Neta and C. Rolando, J. Electroanal. Chem., 1996, 405, 169.
35. C. Tournaire, M. Hocquaux, I. Beck, E. Oliveros and M.-T. Maurette, Tetrahedron, 1994, 50, 9303.
36. S. Berger, P. Hertl and A. Rieker, in The Chemistry of the Quinonoid Compounds (Part 1), Ed. S. Patai and Z. Rappoport, J. Wiley and Sons, Chichester, 1988, p. 29.
37. H. Geiger, in The Flavonoids, Advances in Research since 1986, Ed. J. B. Harborne, Chapman and Hall, London, 1994, p. 95.
38. J. A. Kuhnle, J. J. Windle and A. C. Waiss, J. Chem. Soc. (B), 1969, 613.
39. W. F. Hodnick, F. S. Kung, W. J. Roettger, C. W. Bohmont and R. S. Pardini, Biochem. Pharmacol., 1986, 35, 2345.
40. (a) P. Ashworth and W. T. Dixon. J. Chem. Soc., Perkin Trans. 2, 1972, 1130;
41. (b) J. A. Pedersen, J. Chem. Soc., Perkin Trans. 2, 1973, 424.
42. M. J. Nilges, H. M. Swartz and P. A. Riley, J. Biol. Chem., 1984, 259. 2446.
43. A. Nishinaga, T. Tojo, H. Tomita and T. Matsuura, J. Chem. Soc., Perkin Trans, 1, 1979, 2511.
44. Y. Yoshioka, S. Yamanaka, S. Yamada, T. Kawakami, M. Nishino, K. Yamaguchi and A. Nishinaga, Bull. Chem. Soc. Jpn., 1996, 69, 2701.
45. P. K. Agrawal and H.-J. Schneider, Tetrahedron Lett., 1983, 24, 177.
46. G. M. Escandar and L. F. Sala, Can. J. Chem., 1991, 69, 1994.
47. V. W. Bowry and K. U. Ingold, J. Org. Chem., 1995, 60, 5456.
48. Carbon-13 NMR of Flavonoids, Ed. P. K. Agrawal, Studies in Organic Chemistry, Vol. 39, Elsevier, Amsterdam, 1989.