Reduction in free-radical-induced DNA strand breaks and base damage through fast chemical repair by flavonoids

Free Radical Research

Volumn 33, Issue 1, 2000, Pages 91-103

  Anderson, Robert F ^a   Amarasinghe, Chanchala ^a   Fisher, Louisa J ^a   Mak, Wai B ^a   Packer, John E ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Antioxidants; Base damage; DNA strand breaks; Electron transfer; Flavonoids; Pulse radiolysis

Indexed keywords

ANTIOXIDANT; APIGENIN; CATECHIN; DNA; EPICATECHIN; FIESTIN; FLAVANOL DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; FREE RADICAL; HYDROXYL RADICAL; KAEMPFEROL; LUTEOLIN; QUERCETIN; UNCLASSIFIED DRUG;

ARTICLE; DNA DAMAGE; DNA REPAIR; DNA STRAND BREAKAGE; DRUG STRUCTURE; ELECTRON TRANSPORT; IN VITRO STUDY; IRRADIATION; PULSE RADIOLYSIS;

EID: 0034079428     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760000300651     Document Type: Article

References (69)

1. M.G.L. Hertog, E.J.M. Feskens, P.C.H. Hollman, M.B. Katan and D. Kromhout (1493) Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet, 342, 1007-1011.
2. M.G.L. Hertog, D. Kromhout, C. Aravanis, H. Blackburn, R. Buzina, F.S.G. Fidanza, A. Jansen, A. Menotti, S. Nedeljkovic, M. Pekkarinen, B.S. Simic, H. Toshima, E.J.M. Feskens, P.C.H. Hollman and M.B. Katan (1995) Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Archives of Internal Medicine, 155, 381-386.
3. P. Knekt, R. Jarvinen, A. Reunanen and J. Maattela (1996) Flavonoid intake and coronary mortality in Finland: a cohort study. British Medical Journal, 312, 478-481.
4. A.B. Miller (1990) Diet and cancer. Reviews of Oncology, 3, 87-95.
5. K.A. Steinmetz and D. Potter (1991) Vegetables and fruit and cancer. Cancer Causes Control, 2, 325-357.
6. E. Negri, C. La Vecchia, S. Franceschi, B. D'Avanzo and F. Parazzini (1991) Vegetable and fruit consumption and cancer risk. International Journal of Cancer, 48, 350-354.
7. J. Kahnau (1976) The flavonoids: a class of semi-essential food components: their role in human nutrition. World Review of Nutrition anid Diet, 24, 117-120.
8. J.A. Conquer, G. Maiani, E. Azzini, A. Raguzzini and B.J. Holub (1998) Supplementation with quercetin markedly increases plasma quercetin concentration without effect on selected risk factors for heart disease in healthy subjects. Journal of Nutrition, 128, 593-597.
9. G. Paganga and C.A. Rice-Evans (1997) The identification of flavonoids as glycosides in human plasma. FEBS Letters, 401, 78-82.
10. P.C.H. Hollman, M.G.L. Hertog and MB. Katan (1996) Role of dietary flavonoids in protection against cancer and coronary heart disease. Biochemical Society Transactions, 24, 785-789.
11. M.G.L. Hertog and P.C.H. Hollman (1996) Potential health effects of the dietary flavonol quercetin. European Journal of Clinical Nutrition, 50, 63-71.
12. P.L.T.M.K. Janssen, R.P. Mensink, F.J.J. Cox, J.L. Harryvan, R. Hoevenier, P.C.H. Hollman and M.B. Katan (1998) Effects of the flavonoids quercetin and apigenin on hemostasis in healthy volunteers: results from an in vitro and a dietary supplement study. American Journal of Clinical Nutrition, 67, 255-262.
13. S.C. Sahu and M.C. Washington (1991) Effects of anti-oxidants on quercetin induced nuclear DNA damage and lipid peroxidation. Cancer Letters, 60, 259-264.
14. S.J. Duthie, W. Johnson and V.L. Dobson (1997) The effect of dietary flavonoids on DNA damage (strand breaks and oxidised pyrimidines) and growth in human cells. Mutation Research, 390, 141-151.
15. S.R. Husain, J. Cillard and P. Cillard (1987) Hydroxyl radical scavenging activity of flavonoids. Phytochemistry, 26, 2489-2491.
16. W. Bohrs and M. Saran (1987) Radical scavenging by flavonoid antioxidants. Free Radical Research Communications, 2, 289-294.
17. A.I. Huguet, S. Manwz and M.J. Alcaranz (1989) Superoxide scavenging properties of flavonoids in a non-enzymic system. Zeitshrift für Naturforschung, 45c, 19-24.
18. U. Takahama (1985) Inhibition of lipoxygenase-dependent lipid peroxidation by quercetin: mechanism of antioxidative function. Phytochemistry, 24, 1443-1446.
19. C.V. De Whalley, S.M. Rankin, J.R.S. Hoult, W. Jessup and D.S. Leake (1990) Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages. Biochemical Pharmacology, 39, 1743-1750.
20. E.S. Fiala, R.S. Sodium, M. Bhattacharya and H. Li (1996) (-)-Epigallocatechin gallate, a polyphenolic tea antioxidant, inhibits peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Experientia, 52, 922-926.
21. T.P.A. Devasagayam, M. Subramaian, B.B. Singh, R. Ramanathan and N.P. Das (1995) Protection of plasmid pBR322 DNA by flavonoids against single-strand breaks induced by singlet molecular oxygen. Journal of Photochemistry and Photobiology B, 30, 97-103.
22. M. Noroozi, W.J. Angerson and M.E.J. Lean (1998) Effects of flavonoids and vitamin C on oxidative DNA damage to human lymphocytes. American Journal of Clinical Nutrition, 67, 1210-1218.
23. H. Verhagen, H.E. Poulsen, S. Loft, G. van Poppel, M.I. Willems and P.J. van Bladeren (1995) Reduction of oxidative DNA-damage in humans by Brussels sprouts. Carcinogenesis, 16, 969-970.
24. B. Ames and L.S. Gold (1991) Endogenous mutagens and the causes of aging and cancer. Mutation Research, 250, 3-16.
25. R. Olinski, T. Zastawny, J. Budzbon, J. Skokowski, W. Zegarski and M. Dizdaroglu (1992) DNA base modifications in chromatin of human cancerous tissues. FEBS Letters, 309, 193-198.
26. M.A. Siddiqi and E. Bothe (1987) Single-and double-strand break formation in DNA irradiated in aqueous solution: dependence on dose and OH radical scavenger concentration. Radiation Research, 112, 449-463.
27. J.F. Ward (1991) Mechanisms of radiation action on DNA in model systems - their relevance to cellular DNA. In Early Effects of Radiation on DNA, Vol. 54 (Eds., E.M. Fielden and P. O'Neill), Springer-Verlag, New York, pp. 1-16.
28. C. von Sonntag (1987) The Chemical Basis of Radiation Biology, Taylor & Francis Ltd., London.
29. A.P. Breen and J.A. Murphy (1995) Reactions of oxyl radicals with DNA, Free Radicals in Biology and Medicine, 18, 1033-1077.
30. R.L. Willson, P. Wardman and K.-D. Asmus (1974) Interaction of dGMP radical with cysteamine and promethazine as possible model of DNA repair. Nature, 252, 323-324.
31. L.P. Candeias and S. Steenken (1989) Structure and acid-base properties of one-electron-oxidized deoxyguanosine, guanosine, and 1-methylguanosine. Journal of the American Chemical Society, 111, 1094-1099.
32. L.P. Candeias and S. Steenken (1993) Electron transfer in di(deoxy)nucleoside phosphate in aqueous solution: rapid migration of oxidative damage (via adenine) to guanine, Journal of the American Chemical Society, 115, 2437-2440.
33. S.V. Jovanovic and M.G. Simic (1986) One-electron redox potentials of purines and pyrimidines. Journal of Physical Chemistry, 90, 974-978.
34. S. Steenken and S.V. Jovanovic (1997) How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. Journal of the American Chemical Society, 119, 617-618.
35. P. O'Neill (1983) Pulse radiolytic study of the interaction of thiols and ascorbate with OH adducts of dGMP and dG: implications for DNA repair processes. Radiation Research, 96, 198-210.
36. P. O'Neill and P.W. Chapman (1985) Potential repair of free radical adducts on deoxy-GMP and deoxyguanosine by series of reductants: a pulse radiolysis study. International Journal of Radiation Biology, 47, 71-81.
37. S.V. Jovanovic and M.G. Simic (1989) The DNA guanyl radical: kinetics and mechanisms of generation and repair. Biochimica et Biophysica Acta, 1008, 39-44.
38. W. Li, R. Zheng, B. Su, Z. Jia, H. Li, Y. Jiang, S. Yao and N. Lin (1996) Repair of dGMP hydroxyl radical adducts by verbascoside via electrontransfer: a pulse radiolysis study. International Journal of Radiation Biology, 69, 481-486.
39. S. Steenken and P. Neta (1982) One-electron redox potentials of phenols. Hydroxy-and aminophenols and related compounds of biological interest. Journal of Physical Chemistry, 86, 3661-3667.
40. S.V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic and M.G. Simic (1994) Flavonoids as antioxidants. Journal of the American Chemical Society, 116, 4846-4851.
41. R.E. Krisch, P.M. Tan and M.B. Flick (1985) A sensitive SV40 viral probe assay for DNA strand breaks and their biological repair in higher cells: techniques and preliminary results. Radiation Research, 101, 356-372.
42. B. Epe, M. Pflaum, M. Haring, J. Hegler and H. Rudiger (1993) Use of repair endonucleases to characterize DNA damage induced by reactive oxygen species in cellular and cell-free systems. Toxicology Letters, 67, 57-72.
43. J.R. Milligan, J.Y-.Y. Ng, C.C.L. Wu, J.A. Aguilera, J.F. Ward, Y.W. Kow, S.S. Wallace and R.P. Cunningham (1996) Methylperoxyl radicals as intermediates in the damage to DNA irradiated in aqueous dimethyl sulfoxide with gamma rays. Radiation Research, 146, 436-443.
44. G.K. Kuipers and M.V.M. Lafleur (1998) Characterization of DNA damage induced by gamma-radiation-derived water radicals, using DNA repair enzymes. International Journal of Radiation Biology, 74, 511-519.
45. G.V. Buxton, C.L. Greenstock, W.P. Helman and A.B. Ross (1988) Critical review of rate constants of hydrated electrons, hydrogen atoms and hydroxyl radicals (•OH/•O) in aqueous solution. Journal of Physical Chemistry Reference Data, 17, 513-886.
46. S.S. Wallace (1998) Enzymatic processing of radiation-induced free radical damage in DNA. Radiation Research, 150, S60-S69.
47. H.E. Krokan, R. Standal and G. Slupphaug (1997) DNA glycosylases in the base excision repair of DNA. Biochemical Journal, 325, 1-16.
48. R.F. Anderson, W.A. Denny, W. Li, J.E. Packer, M. Tercel and W.R. Wilson (1997) Pulse radiolysis studies on the fragmentation of arylmethyl quaternary nitrogen mustards by one-electron reduction in aqueous solution. Journal of Physical Chemistry, 101, 9704-9709.
49. M. Erben-Russ, W. Bors and M. Saran (1987) Reactions of linoleic acid peroxyl radicals with phenolic antioxidants: a pulse radiolysis study. International Journal of Radiation Biology, 52, 393-414.
50. P.S. Hodgkins, M.P. Fairman and P. O'Neill (1996) Rejoining of gamma-radiation-induced single-strand breaks in plasmid DNA by human cell extracts: dependence on the concentration of the hvdroxyl radical scavenger, tris. Radiation Research, 145, 24-30.
51. K.U. Ingold (1968) Inhibition of autoxidation. Advances in Chemistry Series, 75, 296-305.
52. S.V. Jovanovic, S. Steenken and M.G. Simic (1990) One-electron reduction potentials of 5-indoxyl radicals. A pulse radiolysis and laser photolysis study. Journal of Physical Chemistry, 94, 3583-3588.
53. J.J. van Hemmen and W.J.A. Meuling (1975) Inactivation of biologically active DNA by γ-ray-induced superoxide radicals and their dismutation products singlet oxygen and hydrogen peroxide. Biochimica et Biophysica Acta, 402, 133-141.
54. C. von Sonntag (1994) Topics in free radical-mediated DNA damage: purines and damage amplification-superoxic reactions-bleomycin, the incomplete radiomimetic. International Journal of Radiation Biology, 66, 485-490.
55. L. Denison, A. Haigh, G. D'Cunha and R.F. Martin (1992) DNA ligands as radioprotectors: molecular studies with Hoechst 33342 and Hoechst 33258. International Journal of Radiation Biology, 61, 69-81.
56. R.F. Martin and L. Denison (1992) DNA ligands as radiomodifiers: studies with minor-groove binding bibenzimidazoles. International Journal of Radiation Biology and Physics, 23, 579.
57. A. Adhikary, E. Bothe, V. Jain and C. von Sonntag (1997) Inhibition of radiation-induced DNA strand breaks by Hoechst 33258: OH-radical scavenging and DNA radical quenching. Radioprotection, 32, Cl-89-Cl-90.
58. R.F. Martin and R.F. Anderson (1998) Pulse radiolysis studies indicate that electron transfer is involved in the radioprotection by Hoechst 33342 and methylproamine. International Journal of Radiation Oncology Biology and Physics, 42, 827-831.
59. A. Rahman, Shahabuddin, S.M. Hadi and J.H. Parish (1990) Complexes involving quercetin, DNA and Cu(II). Carcinogenesis, 11, 2001-2003.
60. R. Solimani (1996) Quercetin and DNA in solution: analysis of the dynamics of their interaction with a linear dichroism study. International Journal of Biological Macromolecules, 18, 287-295.
61. M.H.L. Green, J.E. Lowe, A.P.W. Waugh, K.E. Aldridge, J. Cole and C.F. Arlett (1994) Effect of diet and vitamin C on DNA strand breakage in freshly-isolated human white blood cells. Mutation Research, 316, 91-102.
62. C. Rice-Evans and N.J. Miller (1994) Total antioxidant status in plasma and body fluids. Methods in Enzymology, 234, 279-293.
63. T.M. Satue-Gracia, M. Heinonenen and E.N. Frankel (1997) Anthocyanins as antioxidants on human low-density lipoprotein and lecithin-liposome systems. Journal of Agricultural and Food Chemistry, 45, 3362-3367.
64. T. Lapidot, S. Harel, B. Akiri, R. Granit and J. Kanner (1949) pH-dependent forms of red wine anthocyanins as antioxidants. Journal of Agricultural and Food Chemistry, 47, 67-70.
65. The Alpha-Tocopherol, Beta Carotene Cancer Prevention Study Group (1995) The effect of vitamin E and beta ca rotene on the incidence of lung cancer and other cancers in mate smokers. New England Journal of Medicine, 330, 1029-1035.
66. P.C.H. Hollman, J.H.M. de Vries, S.D. van Leeuwen, N.J.B. Mengelers and M.B. Katan (1995) Absorption of dietary quercetin glycosides and quercetin in healthy ilcostomy volunteers. American Journal of Clinical Nutrition, 62B 1276-1282.
67. R. Gugler, M. Leschik and H.J. Dengler (1975) Disposition of quercetin in man after single oral and intravenous doses. European Journal of Clinical Pharmacology, 9, 229-234.
68. A. Crozier, E. Jensen, M.E.J. Lean and M.S. McDonald (1997) Quantitative analysis of flavonoids by reversed -phase high-performance liquid chromatography. Journal of Chromatography, 761, 315-321.
69. C. Manach, C. Morand, V. Crespy, C. Demigne, O. Texier, F. Regerat and C. Remesy (1998) Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Letters, 426, 331-336.