Quantitative structure-activity relationship of flavonoids for inhibition of heterocyclic amine mutagenicity

Environmental and Molecular Mutagenesis

Volumn 35, Issue 4, 2000, Pages 279-299

  Hatch, F T ^b   Lightstone, F C ^a   Colvin, M E ^a  

^a LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^b NONE   (United States)

Author keywords

Ames Salmonella assay; Antimutagens; Cooking mutagens; Cytochrome P450; Inhibitory mechanisms; Molecular planarity

Indexed keywords

APIGENIN; BIOCHANIN A; CHALCONE; CHRYSIN; CYTOCHROME P450; DIOSMETIN; ERIODICTYOL; FISETIN; FLAVANONE; FLAVONE; FLAVONOID; FLAVONOL; HESPERETIN; HETEROCYCLIC AMINE; HYDROXYL GROUP; ISORHAMNETIN; KAEMPFEROL; LUTEOLIN; MORIN; MYRICETIN; NARINGENIN; PHLORETIN; QUERCETIN; TANGERETIN;

AMES TEST; ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; COOKING; DATA BASE; DIPOLE; ENZYME ACTIVATION; HEALTH HAZARD; MUTAGENICITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

AMINOQUINOLINES; ANTIMUTAGENIC AGENTS; FLAVONOIDS; HUMANS; MUTAGENS; STRUCTURE-ACTIVITY RELATIONSHIP;

SALMONELLA;

EID: 0033917852     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/1098-2280(2000)35:4<279::AID-EM3>3.0.CO;2-9     Document Type: Article

References (44)

1. Adamson RH, Farb A, Virmani R, Snyderwine EG, Thorgeirsson SS, Takayama S, Sugimura T, Dalgard DW, Thorgeirsson UP. 1995. Studies on the carcinogenic and myocardial effects of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in nonhuman primates. In: Adamson RH, Gustafsson J-A, Ito N, Nagao M, Sugimura T, Wakabayashi K, Yamazoe Y, editors. Heterocyclic amines in cooked foods: possible human carcinogens. (Proc. 23rd Intl Symp Princess Takamatsu Cancer Res Fund) Princeton NJ: Princeton Scientific Publishing Co. Inc. pp 260-267.
2. Anderson D, Dobrzyńska MM, Yu T-W. 1997. Modulating effects of silymarin and myricetin on food mutagens and doxorubicin in assays with different endpoints. J Environ Pathol Toxicol Oncol 16:313-327.
3. Anderson D, Dobrzyńska MM, Başaran M, Basaran A, Yu T-W. 1998. Flavonoids modulate Comet assay responses to food mutagens in human lymphocytes and sperm. Mutat Res 402:269-277.
4. Beyeler S, Testa B, Perrissoud D. 1988. Flavonoids as inhibitors of rat liver monooxygenase activities. Biochem Pharmacol 37:1971-1979.
5. Birt DF and Bresnick E. 1991. Chemoprevention by nonnutrient components of vegetables and fruits. In Alfin-Slater RB, Kritchevsky D, editors. Cancer and nutrition, Volume 7 of Human nutrition: a comprehensive treatise, New York: Plenum Press. pp 221-260.
6. Cody V. 1988. Crystal and molecular structures of flavonoids. In: Cody V, Middleton E Jr, and Harborne JB. editors. Plant flavonoids in biology and medicine II: biochemical, cellular, and medicinal properties. New York: Liss. pp 29-44.
7. Colvin MC, Hatch FT, Felton JS. 1998. Chemical and biological factors affecting mutagen potency. Mutat Res 400:479-492.
8. Dai R, Zhai S, Wei X, Pincus MR, Vestal RE, Friedman FK. 1998. Inhibition of human cytochrome P450 1A2 by flavones: a molecular modeling study. J. Protein Chem 17:643-650.
9. De Flora S. 1998. Mechanisms of inhibitors of mutagenesis and carcinogenesis. Mutat Res 402:151-158.
10. DeMarini DM. 1998. Dietary interventions of human carcinogenesis. Mutat Res 400:457-465.
11. Dragsted LO, Strube M, Larsen JC. 1993. Cancer-protective factors in fruits and vegetables: biochemical and biological background. Pharmacol Toxicol 72(Suppl 1):116-135.
12. Edenharder R, von Petersdorff I, and Rauscher R. 1993. Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res 287:261-274.
13. Edenharder R, Rauscher R, Platt KL. 1997. The inhibition by flavonoids of 2-amino-3-methylimidazo[4,5-f]quinoline metabolic activation to a mutagen: a structure-activity relationship study. Mutat Res 379:21-32.
14. Felton JS, Wu R, Knize MG, Thompson LH, Hatch FT. 1995. Heterocyclic amine mutagenicity/carcinogenicity; Influence of repair, metabolism, and structure. In: Adamson RH, Gustafsson J-A, Ito N, Nagao M, Sugimura T, Wakabayashi K, Yamazoe Y, editors. Heterocyclic amines in cooked foods: possible human carcinogens (Proc. 23rd Intl Symp Princess Takamatsu Cancer Res Fund) Princeton NJ: Princeton Scientific Publishing Co. Inc. pp 50-58.
15. Felton JS, Malfatti MA, Knize MG, Salmon CP, Hopmans EC, Wu RW. 1997. Health risks of heterocyclic amines. Mutat Res 376:37-41.
16. Ferriola PC, Cody V, Middleton E. 1989. Protein kinase inhibition by plant flavonoids: kinetic mechanisms and structure-activity relationships. Biochem Pharmacol 38:1617-1624.
17. Fleming I, 1976. Frontier orbitals and organic chemical reactions. New York: Wiley. p 37.
18. Glusker JP, Rossi M. 1986. Molecular aspects of chemical carcinogens and bioflavonoids. In: Cody V, Middleton E Jr, Harborne JB, editors. Plant flavonoids in biology and medicine: biochemical, pharmacological, and structure-activity relationships. New York: Liss. pp 395-410.
19. Hansch C, Leo A. 1979. Substituent constants for correlation analysis in chemistry and biology. New York: Wiley. 339 p.
20. Hatch FT, Colvin ME, Seidl ET. 1996. Structural and quantum chemical factors affecting mutagenic potency of aminoimidazo-azaarenes. Environ Mol Mutagen 27:314-330.
21. Hatch FT, Colvin ME. 1997. Quantitative structure-activity (QSAR) relationships of mutagenic aromatic and heterocyclic amines. Mutat Res 376:87-96.
22. Heo MY, Yu KS, Kim KH, Kim HP, Au WW. 1992. Anticlastogenic effects of flavonoids against mutagen-induced micronuclei in mice. Mutat Res 284:243-249.
23. Hernaez J, Xu M, Dashwood R. 1997. Effects of tea and chlorophyllin on the mutagenicity of N-hydroxy-IQ: Studies of enzytne inhibition, molecular complex formation, and degradation/scavenging of the active metabolites. Environ Mol Mutagen 30:468-474.
24. Kier LB. 1985. A shape index from molecular graphs. Quant Struct Act Relat 4:109-116.
25. Knize MG, Salmon CP, Mehta SS, Felton JS. 1997. Analysis of cooked muscle meats for heterocyclic aromatic amine carcinogens. Mutat Res 376:129-134.
26. Lee H, Tsai S-J. 1991. Effect of emodin on cooked-food mutagen activation. Food Chem Toxic 29:765-770.
27. Lee H, Wang H-W, Su H-Y, Hao N.J. 1994. The structure-activity relationships of flavonoids as inhibitors of cytochrome P-450 enzymes in rat liver microsomes and the mutagenicity of 2-amino-3-methy-limidazo[4,5-f]quinoline. Mutagenesis 9:101-106.
28. Lewis DFV. 1992. Computer modeling of cytochromes P-450 and their substrates: a rational approach to the prediction of carcinogenicity. Front Biotransform 7:90-136.
29. Lewis DFV, Ioannides C, Parke DV. 1989. Molecular orbital studies of oxygen activation and mechanisms of cytochromes P450-mediated oxidative metabolism of xenobiotics. Chem Biol Interact 70:263-280.
30. Lewis DFV, Ioannides C, Walker R, Parke DV. 1995. Quantitative structure-activity relationships and COMPACT analysis of a series of food mutagens. Food Addit Contam 12:715-723.
31. Malaveille C, Hautefeuille A, Pignatelli B, Talaska G, Vineis P, Bartsch H. 1998. Antimutagenic dietary phenolics as antigenotoxic substances in urothelium of smokers. Mutat Res 402:219-224.
32. MacGregor JT. 1986a. Mutagenic and carcinogenic effects of flavonoids. In: Cody V, Middleton E Jr, Harborne JB, editors. Plant flavonoids in biology and medicine: biochemical, pharmacological, and structure-activity relationships. New York: Liss. pp 411-424.
33. MacGregor JT. 1986b. Genetic toxicology of dietary flavonoids. In: Knudsen I, editor. Genetic toxicology of the diet. New York: AR Liss. Inc. pp 33-43.
34. Ohgaki H, Takayama S, Sugimura T. 1991. Short review of the carcinogenicities of mutagens in food pyrolysates. In: Hayatsu H, editor. Mutagens in food: detection and prevention. Boca Raton FL: CRC Press. pp 219-228.
35. Reed AE, Weinstock RB, Weinhold F. 1985. Natural population analysis. J Chem Physics 83:735-746.
36. Rice-Evans CA, Miller N.J. 1997. Structure-antioxidant activity relationships of flavonoids and isoflavonoids. In: Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York: Marcel Dekker. pp 199-219.
37. Rossi M, Cantrell JS, Farber AJ, Dyott T, Carrell HL, Glusker JP. 1980. Molecular structures of 5,6- and 7,8-benzoflavones, inhibitors of aryl hydrocarbon hydroxylase. Cancer Res 40:2774-2784.
38. Stavric B and Matula TI. 1992. Flavonoids in foods: Their significance for nutrition and health. In: Ong ASH, Packer L, editors. Lipid-soluble antioxidants: biochemistry and clinical applications. Basel: Birkhauser Verlag, pp 274-294.
39. Stavric B, Matula TI, Klassen R, Downie RH, Wood RJ. 1992. Effect of flavonoids on mutagenicity and bioavailability of xenobiotics in foods. In: Huang M-T, Ho C-T, Lee CY. 1992. Phenolic compounds in food and their effects on health II. ACS Symposium Series No. 507. Washington DC: American Chemical Society, pp 239-249.
40. Van Acker SABE, Bast A, van der Vingh WJF. 1997. Structural aspects of antioxidant activity of flavonoids. In: Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York: Marcel Dekker. pp 221-251.
41. Vinter JG, Davis A, Saunders MR. 1987. Strategic approaches to drug design. 1. An integrated software framework for molecular modelling. J Computer-Aided Molecular Design 1:31-51.
42. Wood AW, Smith DS, Chang RL, Huang M-T, and Conney AH. 1986. Effects of flavonoids on the metabolism of xenobiotics. In: Cody V, Middleton E, Jr. Harborne JB. editors. Plant flavonoids in biology and medicine: biochemical, pharmacological, and structure-activity relationships. New York: AR Liss Inc. pp 195-210.
43. World Cancer Research Fund/American Institute for Cancer Research. 1997. Food, nutrition and the prevention of cancer: a global perspective. Washington DC: American Institute for Cancer Research, p 426.
44. Yang CS, Smith TJ, Hong J-Y. 1994. Cytochrome P450 enzymes as targets for chemoprevention against chemical carcinogenesis and toxicity: opportunities and limitations. Cancer Res 54:1982s-1986s.