Repair of iron-induced DNA oxidation by the flavonoid myricetin in primary rat hepatocyte cultures

Free Radical Biology and Medicine

Volumn 26, Issue 11-12, 1999, Pages 1457-1466

  Abalea, Valérie ^a   Cillard, Josiane ^a   Dubos, Marie Pierre ^a   Sergent, Odile ^a   Cillard, Pierre ^a   Morel, Isabelle ^a  

^a INSERM   (France)

Author keywords

DNA damage; DNA repair; Flavonoid; Free radicals; Hepatocyte culture; Myricetin

Indexed keywords

CELL DNA; FLAVONOID; IRON; MYRICETIN;

ANIMAL CELL; ARTICLE; CELL PROTECTION; CONTROLLED STUDY; DNA DAMAGE; DNA REPAIR; GENOTOXICITY; LIVER CELL CULTURE; LIVER CELL DAMAGE; MALE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; RAT;

ANIMALS; CELLS, CULTURED; DNA DAMAGE; DNA REPAIR; FLAVONOIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; IRON; L-LACTATE DEHYDROGENASE; LIPID PEROXIDATION; LIVER; MALE; MALONDIALDEHYDE; MUTAGENICITY TESTS; OXIDATION-REDUCTION; OXIDATIVE STRESS; RATS; RATS, SPRAGUE-DAWLEY;

ANIMALIA;

EID: 0033004488     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(99)00010-6     Document Type: Article

References (71)

1. Hertog M.G.L., Hollman P.C.H., Katan M.B., Krombout D. Estimation of daily intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutr. Cancer. 20:1993;21-29.
2. Serafini M., Ghiselli A., Ferro-Luzzi A. Red wine, tea, and antioxidants. Lancet. 344:1994;626. [abstract].
3. Morel I., Lescoat G., Cogrel P., Sergent O., Pasdeloup N., Brissot P., Cillard P., Cillard J. Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem. Pharmacol. 45:1993;13-19.
4. Pietrangelo A., Borella F., Casalgrandi G., Montosi G., Ceccarelli D., Gallesi D., Giovannini F., Gasparetto A., Masini A. Antioxidant activity of silybin in vivo during long-term iron overload in rats. Gastroenterology. 109:1995;1941-1949.
5. Paganga G., Al-Hashim H., Khodr H., Scott B.C., Aruoma O.I., Hider R.C., Halliwell B., Rice-Evans C.A. Mechanisms of antioxidant activities of quercetin and catechin. Redox Report. 2:1996;359-364.
6. Salah N., Miller N.J., Paganga G., Tijburg L., Bolwell G.P., Rice-Evans C.A. Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain breaking antioxidants. Arch. Biochem. Biophys. 322:1995;339-346.
7. Hanasaki Y., Ogawa S., Fukui S. The correlation between active oxygen scavenging and antioxidative effects of flavonoids. Free Radic. Biol. Med. 16:1994;845-850.
8. Husain S.R., Cillard J., Cillard P. Hydroxyl radical scavenging activity of flavonoids. Phytochemistry. 26:1987;2489-2491.
9. Morel I., Lescoat G., Cillard P., Cillard J. Role of flavonoids and iron chelation in antioxidant action. Packer L. Meth. in enzymol. Vol. 234. 1994;437-443 Academic Press, New York.
10. Turlin B., Juguet F., Moirand R., Lequilleuc D., Loreal O., Campion J.P., Launois B., Ramée M.P., Deugnier Y. Increased liver iron stores in patients with hepatocellular carcinoma developed on a non cirrhotic liver. Hepatology. 22:1995;446-450.
11. Morel I., Lescoat G., Cillard J., Pasdeloup N., Brissot P., Cillard P. Kinetic evaluation of free malondialdehyde and enzyme leakage as indices of iron damage in rat hepatocyte cultures. Biochem. Pharmacol. 39:1990;1647-1655.
12. Morel I., Hamon-Bouer C., Abalea V., Cillard P., Cillard J. Comparison of oxidative damage of DNA and lipids in normal and tumor rat hepatocyte cultures treated with ferric nitrilotriacetate. Cancer Lett . 119:1997;31-36.
13. Morel I., Abalea V., Sergent O., Cillard P., Cillard J. Involvement of phenoxyl radical intermediates in lipid antioxidant action of myricetin in iron-treated rat hepatocyte culture. Biochem. Pharmacol. 55:1998;1399-1404.
14. Elangovan V., Sekar N., Govindasamy S. Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis. Cancer Lett. 25:1994;107-113.
15. Webster R.P., Gawde M.D., Bhattacharya R.K. Protective effect of rutin, a flavonol glycoside, on the carcinogen-induced DNA damage and repair enzymes in rat. Cancer Lett. 109:1996;185-191.
16. Mizuta M., Kanamori H. Time-course of mutagenicity due to flavonols in a pickled vegetable. Mutat. Res. 122:1983;287-291.
17. Rueff J., Laires A., Gaspar J., Rodrigues A. Mutagenic activity in the wine-making process correlations with rutin and quercetin levels . Mutagenesis. 5:1990;393-396.
18. Rueff J., Laires A., Borba H., Chaveca T., Gomes M.I., Halpern M. Genetic toxicology of flavonoids the role of metabolic conditions in the induction of reverse mutation, SOS functions and sister-chromatid exchanges . Mutagenesis. 1:1986;179-183.
19. Pamucku A.M., Yalciner S., Hatcher J.F., Bryan G.T. Quercetin, a rat intestinal and bladder carcinogen present in bracken fern (Pteridium aquilinium). Cancer Res. 40:1980;3468-3472.
20. Van der Hoeven J., Bruggeman I.M., Debets F.M.H. Genotoxicity of quercetin in cultured mammalian cells. Mutat. Res. 136:1984;9-21.
21. Alldrick A.J., Lake B.G., Rowland I.R. Modification of in vivo heterocyclic amine genotoxicity by dietary flavonoids. Mutagenesis. 4:1989;365-370.
22. Hirono I., Ueno I., Hosaka S., Takanashi H., Matsushima T., Sugimura T., Natori S. Carcinogenicity examination of quercetin and rutin in ACI rats. Cancer Lett. 13:1981;15-21.
23. Ahmed M.S., Ramesh V., Nagaraja V., Parish J.H., Hadi S.M. Mode of binding of quercetin to DNA. Mutagenesis. 9:1994;193-197.
24. Duarte Silva I., Gaspar J., Rodrigues A., Gomes da Costa G., Laires A., Rueff J. Mechanism of myricetin mutagenicity in V79 cells involvement of radical species . Teratogen. Carcino. Mut. 16:1996;253-268.
25. Bryan S.E., Vizard D.L., Beary D.A., LaBiche R.A., Hardy K.J. Partitioning of zinc and copper within subnuclear nucleoprotein particles. Nucleic Acids Res. 9:1981;5811-5823.
26. Fazal F., Rahman A., Greensill J., Ainley K., Hadi S.M., Parish J.H. Strand scission in DNA by quercetin and Cu (II) identification of free radical intermediates and biological consequences of scission . Carcinogenesis. 11:1990;2005-2008.
27. Sahu S.C., Gray G.C. Interactions of flavonoids, trace metals, and oxygen nuclear DNA damage and lipid peroxidation induced by myricetin . Cancer Lett. 70:1993;73-79.
28. Sahu S.C., Gray G.C. Kaempferol-induced nuclear DNA damage and lipid peroxidation. Cancer Lett. 85:1994;159-164.
29. Wiseman H., Halliwell B. Damage to DNA by reactive oxygen and nitrogen species role in inflammatory disease and progression to cancer . Biochem. J. 313:1996;17-29.
30. Halliwell B., Aruoma O.I. DNA damage by oxygen-derived species. Its mechanism and measurement in mammalian systems. FEBS Lett. 281:1991;9-19.
31. Douki T., Delatour T., Bianchini F., Cadet J. Observation and prevention of an artefactual formation of oxidized DNA bases and nucleosides in the GC-EIMS method. Carcinogenesis. 17:1996;347-353.
32. Dizdaroglu M. Chemical determination of free radical-induced damage to DNA. Free Radic. Biol. Med. 10:1991;225-242.
33. Breimer L.H. Molecular mechanisms of oxygen radical carcinogenesis and mutagenesis. The role of DNA base damage. Mol Carcinogen. 3:1990;188-197.
34. Cheng K.C., Cahill D.S., Kasai H., Nishimura S., Loeb L.A. 8-hydroxyguanine an abundant form of oxidative DNA damage, cause G:T and A:C substitutions. J Biol Chem. 267:1992;166-172.
35. McBride T.J., Preston B.D., Loeb L.A. Mutagenic spectrum resulting from DNA damage by oxygen radicals. Biochemistry. 30:1991;207-213.
36. Satoh M.S., Lindahl T. Enzymatic repair of oxidative DNA damage. Cancer Res. 54:(Suppl.):1994;1899S-1901S.
37. Park J.Y.K., Shinenaga M.K., Ames B.N. Induction of cytochrome P450A1 by 2,3,7,8-tetrachlorodibenzo-p-dioxin or indolo(2,3-b)carbazole is associated with oxidative DNA damage. Proc. Natl. Acad. Sci. USA. 309:1996;193-198.
38. Abalea V., Cillard J., Dubos M.P., Anger J.P., Cillard P., Morel I. Iron-induced oxidative DNA damage and its repair in primary rat hepatocyte culture. Carcinogenesis. 19:1998;1053-1059.
39. Guguen C., Guillouzo A., Boisnard M., Le Cam A., Bourel M. Etude ultrastructurale de monocouches d'hépatocytes de rat adulte cultivés en présence d'hémisuccinate d'hydrocortisone. Biol. Gastroenterol. 8:1975;223-231.
40. Guguen-Guillouzo C., Guillouzo A. Modulation of functional activities in cultures rat hepatocytes. Mol. Cell. Biol. 53:1983;35-56.
41. White G.P., Jacobs A. Iron uptake by chang liver cells from transferrin, NTA and citrate complexes. The effect of iron-loading and chelation with desferrioxamine. Biochim. Biophys. Acta. 543:1978;217-225.
42. Bradford M.M. A rapid and sensitive method for quantification of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem. 72:1976;248-254.
43. Labarca C., Paigen K. A simple, rapid and sensitive DNA assay procedure. Anal. Biochem. 102:1980;344-352.
44. Dizdaroglu M. Chemistry of free radical damage to DNA and nucleoproteins. Halliwell B., Aruoma O.I. DNA and free radicals. 1993;19-39 Ellis Horwood Ltd, England.
45. Radicella J.P., Dherin C., Desmaze C., Fox M.S., Boiteux S. Cloning and characterisation of hOGG1, a human homolog of the OGG1 gene of saccharomyces cerevisae. Proc. Natl. Acad. Sci. USA. 94:1997;8010-8015.
46. Krokan H.E., Standal R., Slupphaug G. DNA glycosylases in the base excision repair in DNA. Biochem. J. 325:1997;1-16.
47. Fornace A.J., Alamo I., Hollander M.C. DNA damage-inducible transcripts in mammalian cells. Proc. Natl. Acad. Sci. USA. 85:1988;8800-8804.
48. Klungland A., Lindahl T. Second pathway for completion of human DNA base excision-repair reconstitution with purified proteins and requirement for Dnase IV(FEN1) . EMBO J. 16:1997;3341-3348.
49. Bennett R., Wilson D.M., Wong D., Demple B. Interaction of human apurinic endonuclease and DNA polymerase β in the base excision repair pathway. Proc. Natl. Acad. Sci. USA. 94:1997;7166-7169.
50. Lepley D.M., Li B., Birt D.F., Pelling J.C. The chemoprotective flavonoid apigenin induced G2/M arrest in keratinocytes. Carcinogenesis. 7:1996;2367-2375.
51. Williamson G., Plumb G.W., Uda Y., Price K.R., Rhodes M.J. Dietary quercetin glycosides antioxidant activity and induction of anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells . Carcinogenesis. 17:1996;2385-2387.
52. Kuchino Y., Mori F., Kasai H., Inoue H., Iwai S., Miura K., Ohtsuka E., Nishimura S. Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and adjacent residues. Nature. 327:1987;77-79.
53. Pavlov Y.I., Minnick D.T., Izuta S., Kunkel T.A. DNA replication fidelity with 8-oxodeoxyguanosine triphosphate. Biochemistry. 33:1994;4695-4701.
54. Kasai H., Nishimura S. Formation of 8-hydroxydeoxyguanosine in DNA by oxygen radicals and its biological significance. Sies H. Oxidative stress. 1991;99-116 Academic Press, London.
55. Luo Y., Henle E.S., Linn S. Oxidative damage to DNA constituents by iron-mediated fenton reactions. The deoxycytidine family. J. Biol. Chem. 271:1996;21167-21176.
56. Ravanat J-L, Gremaud E., Markovic J., Turesky R.J. Detection of 8-oxoguanine in cellular DNA using 2,6-diamino-8-oxopurine as an internal standard for high-performance liquid chromatography with electrochemical detection. Anal. Biochem. 260:1998;30-37.
57. Toyokuni S., Mori T., Dizdaroglu M. DNA base modification in renal chromatin of wistar rats treated with a renal carcinogen, ferric nitrilotriacetate. Int. J. Cancer. 57:1994;123-128.
58. Le Page F., Margot A., Grollman A.P., Sarasin A., Gentil A. Mutagenicity of a unique 8-oxoguanine in a human Ha-ras sequence in mammalian cells. Carcinogenesis. 16:1995;2779-2784.
59. Purmal A.A., Wah Kow Y., Wallace S.S. Major oxidative products of cytosine, 5-hydroxycytosine and 5-hydroxyuracil, exhibit sequence context-dependent mispairing in vitro. Nucleic Acids Res. 22:1994;72-78.
60. Kamiya H., Kasai H. Effects of sequence contexts on misincorporation of nucleotides opposite 2-hydroxyadenine. FEBS Lett. 391:1996;113-116.
61. Duthie S.E., Johnson W., Dodson V.L. The effect of dietary flavonoids on DNA damage (strand breaks and oxidised pyrimidines) and growth in human cells. Mutat. Res. 390:1997;141-151.
62. Constantinou A., Mehta R., Runyan C. Flavonoids as DNA topoisomerase antagonists and poisons structure-activity relationships . J Natural Products. 58:1995;217-225.
63. Lee S.J., Choi J.H., Son K.H., Chang H.W., Kang S.S., Kim H.P. Suppression of mouse lymphocyte proliferation in vitro by naturally occurring bioflavonoids. Life Sci. 57:1995;551-558.
64. Sato F., Matsukawa Y., Nishino H., Sakai T. Apigenin induces morphological differentiation and G2-M arrest inrat neuronal cells. Biochem. Biophys. Res. Commun. 204:1994;578-594.
65. Cao J., Xu Y., Chien J., Klaunig J.E. Chemopreventive effects of green and black tea on pulmonary and hepatic carcinogenesis. Fund. Appl. Toxicol. 29:1996;244-250.
66. Li Y., Trush M.A. Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. 54:1994;1895-1898.
67. Sahu S.C., Gray G.C. Lipid peroxidation and DNA damage induced by morin and naringenin in isolated rat liver nuclei. Food Chem. Toxicol. 35:1997;443-447.
68. Laughton M.J., Halliwell B., Evans P.J., Hoult J.R.S. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Biochem. Pharmacol. 38:1989;2859-2865.
69. Stadler R.H., Markovic J., Turesky R.J. In vitro anti- and pro-oxidative effects of natural polyphenols. Biol. Trace Elem. Res. 47:1995;299-305.
70. Block G. The data support a role for antioxidants in reducing cancer risk. Nutr. Rev. 50:1992;207-213.
71. Knekt P., Jarvinen R., Seppanen R., Hellovaara M., Teppo L., Pukkala E., Aromaa A. Dietary flavonoids and the risk of lung cancer and other malignant neoplasms. Am. J. Epidemiol. 146:1997;223-230.