Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II)

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 397, Issue 2, 1998, Pages 191-201

  Yamashita, Naruto ^a   Murata, Mariko ^a   Inoue, Sumiko ^b   Hiraku, Yusuke ^b   Yoshinaga, Takeo ^b   Kawanishi, Shosuke ^a  

^a MIE UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

2,5 Dimethyl 4 hydroxy 3(2 H) furanone; Active oxygen species; Copper; DNA damage; Fragrant compound; Mutagenicity

Indexed keywords

COPPER ION; FURANONE DERIVATIVE; PROTEIN P53; SUPEROXIDE;

ARTICLE; DNA DAMAGE; FOOD PROCESSING; HUMAN; MUTAGENESIS; MUTAGENICITY; OXIDATIVE STRESS; PRIORITY JOURNAL; TUMOR SUPPRESSOR GENE;

ANIMALS; CATTLE; COPPER; DEOXYGUANOSINE; DNA DAMAGE; DNA FRAGMENTATION; FREE RADICAL SCAVENGERS; FURANS; GLUCOSIDES; HUMANS; MUTAGENS; OXIDATION-REDUCTION; PHOSPHORUS RADIOISOTOPES; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPEROXIDES;

LETHRINIDAE;

EID: 0032472894     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(97)00210-8     Document Type: Article

References (33)

1. Hayase F., Kim S.B., Kato H. Maillard reaction products formed from D-glucose and glycine and the formation mechanisms of amides as major components. Agric. Biol. Chem. 49:1985;2337-2341.
2. Hiramoto K., Sekiguchi K., Aso-o R., Ayuha K., Ni-iyama H., Kato T., Kikugawa K. DNA strand breaks induced through active oxygen radicals by fragrant component 4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone in Maillard reaction of hexose/amino acid. Food Chem. Toxicol. 33:1995;803-814.
3. Hiramoto K., Sekiguchi K., Ayuha K., Aso-o R., Moriya N., Kato T., Kikugawa K. DNA breaking activity and mutagenicity of soy sauce; characterization of the active components and identification of 4-hydroxy-5-methyl-3(2H)-furanone. Mutation Res. 359:1996;119-132.
4. Hiramoto K., Aso-o R., Ayuha K., Ni-iyama H., Hikage S., Kato T., Kikugawa K. DNA strand break by 2,5-dimethyl-4-hydroxy-3(2H)-furanone, a fragrant in various foodstuffs. Mutation Res. 359:1996;17-24.
5. Hemming J., Holmbom B., Reunanen M., Kronberg L. Determination of the strong mutagen 3-chloro-4-(dichloromethyl)-2(5H)-furanone in chlorinated drinking and humic water. Chemosphere. 15:1986;549-556.
6. P. Chumakov, EMBL Data Library, accession number X54156, 1990.
7. Kawanishi S., Inoue S., Sano S. Mechanism of DNA cleavage induced by sodium chromate (VI) in the presence of hydrogen peroxide. J. Biol. Chem. 261:1986;5952-5958.
8. Maxam A.M., Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65:1980;499-560.
9. Kasai H., Crain P.F., Kuchino Y., Nishimura S., Ootsuyama A., Tanooka H. Formation of 8-hydroxy-guanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis. 7:1986;1849-1851.
10. Ito K., Inoue S., Yamamoto K., Kawanishi S. 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′sequences in double-stranded DNA by UV radiation with riboflavin. J. Biol. Chem. 268:1993;13221-13227.
11. Porra R.J., Klein O., Dornemann D., Senger H. A simple method for the rapid determination of 4,5-dioxovaleric acid in the presence of 2-oxoglutarate and other 2-oxocarboxylic acids. Physiol. Chem. 361:1980;187-190.
12. Van Gelder B.F., Slater E.C. The extinction coefficient of cytochrome c. Biochim. Biophys. Acta. 58:1962;593-595.
13. Rahman A., Shahabuddin S., Hadi M., Ainley K. Strand scission in DNA induced by quercetin and Cu(II), role of Cu(I) and oxygen free radicals. Carcinogenesis. 10:1989;1833-1839.
14. 2 formation. Carcinogenesis. 13:1992;1497-1502.
15. Blair D., Diehl H. Bathophenanthrolinedisulphonic acid and bathocuproinedisulphonic acid, water soluble reagents for iron and copper. Talanta. 7:1961;163-174.
16. Loft S., Poulsen H.E. Cancer risk and oxidative DNA damage in man. J. Mol. Med. 74:1996;297-312.
17. Guyton K.Z., Kensler T.W. Oxidative mechanisms in carcinogenesis. Br. Med. Bull. 49:1993;523-544.
18. Breen A.P., Murphy J.A. Reactions of oxyl radicals with DNA. Free Radic. Biol. Med. 18:1995;1033-1077.
19. Shibutani S., Takeshita M., Grollman A.P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature. 349:1991;431-434.
20. 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;1895s-1898s.
21. S. Kawanishi, S. Oikawa, S. Inoue, Role of metal in oxidative DNA damage by non-mutagenic carcinogen, in: B. Sarkar (Ed.), Genetic Response to Metals, Marcel Dekker, New York, 1995, pp. 131-151.
22. Ito K., Yamamoto K., Kawanishi S. Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines; non-Fenton-type hydroxyl radical formation. Biochemistry. 31:1992;3069-3075.
23. Kawanishi S., Yamamoto K. Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper (II) or manganese (III). Biochemistry. 30:1991;11606-11613.
24. Devasagayam T.P., Steenken S., Obendorf M.S., Schulz W.A., Sies H. Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry. 30:1991;6283-6289.
25. van den Ouweland G.A.M., Peer H.G. Components contributing to beef flavor. Volatile compounds produced by the reaction of 4-hydroxy-5-methyl-3(2)-furanone and its thio analog with hydrogen sulfide. J. Agric. Food Chem. 23:1975;501-505.
26. Shu C.K., Mookherjee B.D., Ho C.T. Volatile components of the thermal degradation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone. J. Agric. Food Chem. 33:1985;446-448.
27. Celander D.W., Cech T.R. Iron(II)-ethylenediaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides; similar reactivity toward single- and double-stranded forms. Biochemistry. 29:1990;1355-1361.
28. Geierstanger B.H., Kagawa T.F., Chen S.L., Quigley G.J., Ho P.S. Base-specific binding of copper(II) to Z-DNA. J. Biol. Chem. 266:1991;20185-20191.
29. Dijkwel P.A., Wenink P.W. Structural integrity of the nuclear matrix; different effects of thiol agents and metal chelators. J. Cell. Sci. 84:1986;53-67.
30. Friedman M., Wilson R.E., Ziderman I.I. Mutagen formation in heated wheat gluten, carbohydrates, and gluten/carbohydrate blends. J. Agric. Food Chem. 38:1990;1019-1028.
31. Wakabayashi K., Nagao M., Ochiai M., Fujita Y., Tahira T., Nakayasu M., Ogaki H., Takayama S., Sugimura T. Recently identified nitrite-reactive compounds in food; occurrence and biological properties of the nitrosated products. IARC Sci. Publ. 84:1987;287-291.
32. Nunomura N., Sasaki M., Yokotsuka T. Shoyu (soy sauce) components; acidic fractions and the characteristic flavor component. Agric. Biol. Chem. 44:1980;239-351.
33. Parodi S., Flora S.D., Cavanna M., Pino A., Robbiano L., Bennicelli C., Brambilla G. DNA-damaging activity in vivo and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity. Cancer Res. 41:1981;1469-1482.