Anthocyanin interactions with DNA: Intercalation, topoisomerase I inhibition and oxidative reactions

Journal of Food Biochemistry

Volumn 32, Issue 5, 2008, Pages 576-596

  Webb, Michael R ^a,b   Min, Kyungmi ^a   Ebeler, Susan E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 52349112273     PISSN: 01458884     EISSN: 17454514     Source Type: Journal    
DOI: 10.1111/j.1745-4514.2008.00181.x     Document Type: Article

References (38)

1. ACQUAVIVA, R., RUSSO, A., GALVANO, F., GALVANO, G., BARCELLONA, M.L., LI VOLTI, G. VANELLA, A. 2003. Cyanidin and cyanidin 3-O-β-D-glucoside as DNA cleavage protectors and antioxidants. Cell. Biol. Toxicol. 19, 243 252.
2. AHMAD, A., FARHAN ASAD, S., SINGH, S. HADI, S.M. 2000. DNA breakage by resveratrol and Cu(II): Reaction mechanism and bacteriophage inactivation. Cancer Lett. 154, 29 37.
3. BORKOWSKI, T., SZYMUSIAK, H., GLISZCZYÉSKA-SWIGLO, A., RIETJENS, I.M.C.M. TYRAKOWSKA B. 2005. Radical scavenging capacity of wine anthocyanins is strongly pH-dependent. J. Agric. Food Chem. 53, 5526 5534.
4. BOULTON, R. 2001. The copigmentation of anthocyanins and its role in the color of red wine: A critical review. Am. J. Enol. Viticult. 52, 67 87.
5. BROUILLARD, R. DUBOIS, J.E. 1977. Mechanism of the structural transformations of anthocyanins in acidic media. J. Am. Chem. Soc. 99, 1359 1364.
6. BROUILLARD, R., WIGAND, M.C., DANGLES, O. CHEMINAT, A. 1991. pH and solvent effects on the copigmentation reaction of malvin with polyphenols, purine and pyrimidine derivatives. J. Chem. Soc. Perkin Trans. 2 8, 1235 1241.
7. CHOI, J., CHOI, Y., JEONG, Y., LEE, M., KWON, H. KANG, Y. 2004. Flavones inhibit tumor TNF-alpha-induced nuclear transactivation of NF-kappa B and expression of cell adhesion molecules in human vascular endothelial cells. FASEB J. 18, #792.5.
8. EDENHARDER, R. TANG, X. 1997. Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by flavonoids, coumarins, quinones and other phenolic compounds. Food Chem. Toxicol. 35, 357 372.
9. GALATI, G., SABZEVARI, O., WILSON, J.X. O'BRIEN, P.J. 2002. Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology 177, 91 104.
10. GASIOROWSKI, K., BROKOS, B., KULMA, A., OGORZALEK, A. SKORKOWSKA, K. 2001. Impact of four antimutagens on apoptosis in genotoxically damaged lymphocytes in vitro. Cell. Mol. Biol. Lett. 6, 649 675.
11. HABERMEYER, M., FRITZ, J., BARTHELMES, H.U., CHRISTENSEN, M.O., LARSEN, M.K., BOEGE, F. MARKO, D. 2005. Anthocyanidins modulate the activity of human DNA topoisomerases I and II and affect cellular DNA integrity. Chem. Res. Toxicol. 18, 1395 1404.
12. HASLAM, E. 1998. Practical Polyphenolics from Structure to Molecular Recognition and Physiological Action, Cambridge University Press, Cambridge, UK.
13. HOUBIERS, C., LIMA, J.C., MACANITA, A.L. SANTOS, H. 1998. Color stabilization of malvidin 3-glucoside: Self-aggregation of the flavylium cation and copigmentation with the Z-chalcone form. J. Phys. Chem. B 102, 3578 3585.
14. KAMEI, H., KOJIMA, T., HASEGAWA, M., KOIDE, T., UMEDA, T., YUKAWA, T. TERABE, K. 1995. Suppression of tumor cell growth by anthocyanins in vitro. Cancer Invest. 13, 590 594.
15. KATSUBE, N., IWASHITA, K., TSUSHIDA, T., YAMAKI, K. KOBORI, M. 2003. Induction of apoptosis in cancer cells by Bilberry (Vaccinium myrtillus) and the anthocyanins. J. Agric. Food Chem. 51, 68 75.
16. KOIDE, T., KAMEI, H., HASHIMOTO, Y., KOJIMA, T., TERABE, K. UMEDA, T. 1997. Influence of flavonoids on cell cycle phase as analyzed by flow-cytometry. Cancer Biother. Radiopharm. 12, 111 115.
17. MATSUMOTO, H., INABA, H., KISHI, M., TOMINAGA, S., HIRAYAMA, M. TSUDA, T. 2001. Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J. Agric. Food Chem. 49, 1546 1551.
18. MAZZA, G. BROUILLARD, R. 1987. Color stability and structural transformations of cyanidin-3,5-diglucoside and four 3-deoxyanthocyanins in aqueous solutions. J. Agric. Food Chem. 35, 422 426.
19. MISTRY, T.V., CAI, Y., LILLEY, T.H. HASLAM, E. 1991. Polyphenol interactions. Part 5. Anthocyanin co-pigmentation. J. Chem. Soc. Perkin Trans. 2 8, 1287 1296.
20. NETTO, L.E.S. STADTMAN, E.R. 1996. The iron-catalyzed oxidation of dithiothreitol is a biphasic process: Hydrogen peroxide is involved in the initiation of a free radical chain of reactions. Arch. Biochem. Biophys. 333, 233 242.
21. POOL-ZOBEL, B.L., BUB, A., SCHRÖDER, N. RECHKEMMER, G. 1999. Anthocyanins are potent antioxidants in model systems but do not reduce endogenous oxidative DNA damage in human colon cells. Eur. J. Nutr. 38, 227 234.
22. POPP, R. SCHIMMER, O. 1991. Induction of sister-chromatid exchanges (SCE), polyploidy, and micronuclei by plant flavonoids in human lymphocyte cultures. A comparative study of 19 flavonoids. Mutat. Res. 246, 205 213.
23. QUINEY, C., DAUZONNE, D., KERN, C., FOURNERON, J.-D., IZARD, J.-C., MOHAMMAD, R.M., KOLB, J.-P. BILLARD, C. 2004. Flavones and polyphenols inhibit the NO pathway during apoptosis of leukemia B-cells. Leuk. Res. 28 (8 851 861.
24. RAMIREZ-TURTOSA, C., ANDERSEN, Ø.M., GARDNER, P.T., MORRICE, P.C., WOOD, S.G., DUTHIE, S.J., COLLINS, A.R. DUTHIE, G.G. 2001. Anthocyanin-rich extract decreases indices of lipid peroxidation and DNA damage in vitamin E-depleted rats. Free Radic. Biol. Med. 31 (9 1033 1037.
25. RUSSO, A., ACQUAVIVA, R., CAMPISI, A., SORRENTI, V., DI GIACOMO, C., VIRGATA, G., BARCELLONA, M.L. VANELLA, A. 2000. Bioflavonoids as antiradicals, antioxidants and DNA cleavage protectors. Cell. Biol. Toxicol. 16, 91 98.
26. SAKANO, K., OIKAWA, S., HIRAKU, Y. KAWANISHI, S. 2004. Oxidative DNA damage induced by a melatonin metabolite, 6-hydroxymelatonin, via a unique non-o-quinone type of redox cycle. Biochem. Pharmacol. 68, 1869 1878.
27. SARMA, A.D. SHARMA, R. 1999. Anthocyanin-DNA copigmentation complex: Mutual protection against oxidative damage. Phytochemistry 52, 1313 1318.
28. SATUÉ-GRACIA, M.T., HEINONEN, M. FRANKEL, E.N. 1997. Anthocyanins as antioxidants on human low density lipoprotein and lecithin-liposome systems. J. Agric. Food Chem. 45, 3362 3367.
29. SINGLETON, V.L. 1987. Oxygen with phenols and related reactions in musts, wines, and model systems: Observations and practical implications. Am. J. Enol. Viticult. 38, 69 77.
30. SUDA, I., OKI, T., MASUDA, M., NISHIBA, Y., FURUTA, S., MATSUGANO, K., SUGITA, K. TERAHARA, N. 2002. Direct absorption of acylated anthocyanins in purple-fleshed sweet potato into rats. J. Agric. Food Chem. 50 (6 1672 1676.
31. TSUDA, T., HORIO, F. OSAWA, T. 2000. The role of anthocyanins as an antioxidant under oxidative stress in rats. Biofactors 13, 133 139.
32. U.S. DEPARTMENT OF AGRICULTURE, AGRICULTURAL RESEARCH SERVICE. 2007. USDA Database for the Flavonoid Content of Selected Foods. Release 2.1. U.S. Department of Agriculture-2006, http://www.ars.usda.gov/services/docs.htm?docid= 6231 (accessed June 6, 2008).
33. WANG, J.C. 2002. Cellular roles of DNA topoisomerases: A molecular perspective. Nat. Rev. Mol. Cell Biol. 3, 430 440.
34. WANG, H., CAO, G. PRIOR, R.L. 1997. The oxygen radical absorbing capacity of anthocyanins. J. Agric. Food Chem. 45, 304 309.
35. WEBB, M.R. EBELER, S.E. 2003. A gel electrophoresis assay for the simultaneous determination of topoisomerase I inhibition and DNA intercalation. Anal. Biochem. 321, 22 30.
36. WEBB, M.R. EBELER, S.E. 2004. Comparative analysis of topoisomerase IB inhibition and DNA intercalation by flavonoids and similar compounds: Structural determinates of activity. Biochem. J. 384, 527 541.
37. WILLIAMS, R.J., SPENCER, J.P.E. RICE-EVANS, C. 2004. Flavonoids: Antioxidants or signaling molecules? Free Radic. Biol. Med. 36 (7 838 849.
38. WU, X., BEECHER, G.R., HOLDEN, J.M., HAYTOWITZ, D.B., GEBHARDT, S.E. PRIOR, R.L. 2006. Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J. Agric. Food Chem. 54, 4069 4075.