Mutagenicity of flavonoids assayed by bacterial reverse mutation (Ames) test

Molecules

Volumn 17, Issue 5, 2012, Pages 5255-5268

  Resende, Flavia Aparecida ^a   Vilegas, Wagner ^a   Dos Santos, Lourdes Campaner ^a   Varanda, Eliana Aparecida ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

Ames test; Flavonoids; Mutagenicity

Indexed keywords

FLAVONOID; GALANGIN; KAEMPFEROL; KAEMPFEROL DERIVATIVE; MUTAGENIC AGENT; QUERCETIN;

ARTICLE; BIOASSAY; BIOTRANSFORMATION; DRUG EFFECT; GENETICS; HYDROXYLATION; METABOLISM; MUTAGEN TESTING; MUTATION; SALMONELLA TYPHIMURIUM; STRUCTURE ACTIVITY RELATION;

BIOLOGICAL ASSAY; BIOTRANSFORMATION; FLAVONOIDS; HYDROXYLATION; KAEMPFEROLS; MUTAGENICITY TESTS; MUTAGENS; MUTATION; QUERCETIN; SALMONELLA TYPHIMURIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861517020     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17055255     Document Type: Article

References (31)

1. Chebil, L.; Anthoni, J.; Humeau, C.; Gerardin, C.; Engasser, J.M.; Ghoul, M. Enzymatic acylation of flavonoids: Effect of the nature of the substrate, origin of lipase, and operating conditions on conversion yield and regioselectivity. J. Agric. Food Chem. 2007, 55, 9496-9502.
2. Williams, C.A.; Grayer, R.J. Anthocyanins and other flavonoids. Nat. Prod. Rep. 2004, 21, 539-573.
3. Wang, Y.; Chen, S.; Yu, O. Metabolic engineering of flavonoids in plants and microorganisms. Appl. Microbiol. Biotechnol. 2011, 91, 949-956.
4. Taylor, L.P.; Grotewold, E. Flavonoids as developmental regulators. Curr. Opin. Plant Biol. 2005, 8, 317-323.
5. Peer, W.A.; Murphy, A.S. Flavonoids and auxin transport: Modulators or regulators? Trends Plant Sci. 2007, 12, 556-563.
6. Buer, C.S.; Imin, N.; Djordjevic, M.A. Flavonoids: New roles for old molecules. J. Integr. Plant Biol. 2010, 52, 98-111.
7. Spencer, J.P.E.; Vauzour, D.; Rendeiro, C. Flavonoids and cognition: The molecular mechanisms underlying their behavioural effects. Arch. Biochem. Biophys. 2009, 492, 1-9.
8. Havsteen, B.H. The biochemistry and medical significance of the flavonoids. Pharmacol. Ther. 2002, 96, 67-202.
9. Benigni, R.; Bossa, C. Structure alerts for carcinogenicity, and the Salmonella assay system: A novel insight through the chemical relational databases technology. Mutat. Res. 2008, 659, 248-261.
10. Boersma, M.G.; Vervoort, J.; Szymusiak, H.; Lemanska, K.; Tyrakowska, B.; Cenas, N.; Segura-Aguilar, J.; Rietjens, I.M.C.M. Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide. Chem. Res. Toxicol. 2000, 13, 185-191.
11. Cushnie, T.P.; Lamb, A.J. Antimicrobial activity of flavonoids. Int. J. Antimicrob. Agents 2005, 26, 343-356.
12. Duarte Silva, I.; Gaspar, J.; Gomes da Costa, G.; Rodrigues, A.S.; Laires, A.; Rueff, J. Chemical features of flavonols affecting their genotoxicity. Potential implications in their use as therapeutical agents. Chem. Biol. Interact. 2000, 124, 29-51.
13. Mazzatorta, P.; Tran, L.A.; Schilter, B.; Grigorov, M. Integration of structure-activity relationship and artificial intelligence systems to improve in silico prediction of Ames test mutagenicity. J. Chem. Inf. Model. 2007, 47, 34-38.
14. Snijman, P.W.; Swanevelder, S.; Elizabeth Joubert, E.; Green, I.R.; Gelderblom, W.C.A. The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): Some dose-response effects on mutagen activation-flavonoid interactions. Mutat. Res. 2007, 631, 111-123.
15. Macgregor, J.T. Mutagenic and carcinogenic effects of flavonoids. In Plant Flavonoids in Biology and Medicine: Biochemical Pharmacological and Structure-Activity Relationships; Cody, V., Middlenton, E., Harbone, J.B., Eds.; Alan R. Liss: New York, NY, USA, 1986; pp. 411-424.
16. Skibola, C.F.; Smith, M.T. Potential health impacts of excessive flavonoid intake. Free Radic. Biol. Med. 2000, 29, 375-383.
17. Sahu, R.K.; Basu, R.; Sharma, A. Genetic toxicological testing of some plant flavonoids by the micronucleus test. Mutat. Res. 1981, 89, 69-74.
18. Das, A.; Wang, J.H.; Lien, E.J. Carcinogenicity, mutagenicity and cancer preventing activities of flavonoids: A structure-system activity relationship (SSAR) analysis. Prog. Drug Res. 1994, 42, 133-167.
19. Rietjens, I.M.C.M.; Boersma, M.G.; van der Woude, H.; Jeurissen, S.M.F.; Schutte, M.E.; Alink, G.M. Flavonoids and alkenylbenzenes: Mechanisms of mutagenic action and carcinogenic risk. Mutat. Res. 2005, 574, 124-138.
20. Hou, D.X.; Kumamoto, T. Flavonoids as protein kinase inhibitors for cancer chemoprevention: Direct binding and molecular modeling. Antioxid. Redox Signal. 2010, 13, 691-719.
21. Brown, J.P.; Dietrich, P.S. Mutagenicity of plant flavonoids in the Salmonella/mammalian microsome test. Activation of flavonol glycosides by mixed glycosides from rat fecal bacteria and other sources. Mutat. Res. 1979, 66, 223-240.
22. Duarte Silva, I.; Rodrigues, A.S.; Gaspar, J.; Laires, A.; Rueff, J. Metabolism of galangin by rat cytochromes P450: Relevance to the genotoxicity of galangin. Mutat. Res. 1997, 393, 247-257.
23. van der Woude, H.; Alink, G.M.; van Rossum, B.E.J.; Walle, K.; van Steeg, H.; Walle, T.; Rietjens, I.M.C.M. Formation of transient covalent protein and DNA adducts by quercetin in cells with and without oxidative enzyme activity. Chem. Res. Toxicol. 2005, 18, 1907-1916.
24. Harwood, M.; Danielewska-Nikiel, B.; Borzelleca, J.F.; Flamm, G.W.; Williams, G.M.; Lines, T.C. A critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic/carcinogenic properties. Food Chem. Toxicol. 2007, 45, 2179-2205.
25. Boots, A.W.; Haenen, G.R.; Bast, A. Health effects of quercetin: From antioxidant to nutraceutical. Eur. J. Pharmacol. 2008, 585, 325-337.
26. Boots, A.W.; Li, H.; Schins, R.P.; Duffin, R.; Heemskerk, J.W.; Bast, A.; Haenen, G.R. The quercetin paradox. Toxicol. Appl. Pharmacol. 2007, 222, 89-96.
27. Maron, D.M.; Ames, B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 1983, 113, 173-215.
28. Myers, L.N.; Adams, N.; Kier, T.K.; Rao, B.; Shaw, B.; Williams, L. Microcomputer software for data management and statistical analyses of the Ames/Salmonella. In Statistical Methods in Toxicological Research; Krewski, D., Ed.; Gordon and Brech: New York, NY, USA, 1991; pp. 265-279.
29. Bernstein, L.; Kaldor, J.; Mccann, J.; Pike, M.C. An empirical approach to the statistical analysis of mutagenesis data from the Salmonella test. Mutat. Res. 1982, 97, 267-281.
30. Santos, F.V.; Colus, I.M.S.; Silva, M.A.; Vilegas, W.; Varanda, E.A. Assessment of DNA damage induced by extracts and fractions of Strychnos pseudoquina, a Brazilian medicinal plant with antiulcerogenic activity. Food Chem. Toxicol. 2006, 44, 1585-1589.
31. McGeorge, L.S.; Louis, J.B.; Altrerholt, T.B.; Mcgarrity, G.J. Mutagenicity analysis of industrial effluents: Results and consideration for integration into water pollution control programs. In Short Term Bioassays in the Analysis of Complex Environmental Mixtures; Waters, M.D., Claxton, L., Lewtas, J., Nesnow, S., Sandhu, S.S., Strauss, G., Eds.; Plenum: New York, NY, USA, 1985; Volume 4, pp. 247-267