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Molecules 2012, 17(5), 5255-5268; doi:10.3390/molecules17055255

Mutagenicity of Flavonoids Assayed by Bacterial Reverse Mutation (Ames) Test

1
Department of Biological Sciences, Faculty of Pharmaceutical Sciences of Araraquara, UNESP-Sao Paulo State University, Araraquara CEP 14801-902, Sao Paulo, Brazil
2
Experimental Campus of Sao Vicente, UNESP-Sao Paulo State University, Sao Vicente CEP 11350-000, Sao Paulo, Brazil
3
Department of Organic Chemistry, Institute of Chemistry, UNESP-Sao Paulo State University, Araraquara CEP 14800-900, Sao Paulo, Brazil
*
Author to whom correspondence should be addressed.
Received: 13 April 2012 / Revised: 25 April 2012 / Accepted: 27 April 2012 / Published: 7 May 2012
(This article belongs to the collection Bioactive Compounds)
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Abstract

The mutagenicity of ten flavonoids was assayed by the Ames test, in Salmonella typhimurium strains TA98, TA100 and TA102, with the aim of establishing hydroxylation pattern-mutagenicity relationship profiles. The compounds assessed were: quercetin, kaempferol, luteolin, fisetin, chrysin, galangin, flavone, 3-hydroxyflavone, 5-hydroxyflavone and 7-hydroxyflavone. In the Ames assay, quercetin acted directly and its mutagenicity increased with metabolic activation. In the presence of S9 mix, kaempferol and galangin were mutagenic in the TA98 strain and kaempferol showed signs of mutagenicity in the other strains. The absence of hydroxyl groups, as in flavone, only signs of mutagenicity were shown in strain TA102, after metabolization and, among monohydroxylated flavones (3-hydroxyflavone, 5-hydroxyflavone and 7-hydroxyflavone), the presence of hydroxyl groups only resulted in minor changes. Luteolin and fisetin also showed signs of mutagenicity in strain TA102. Finally, chrysin, which has only two hydroxy groups, at the 5-OH and 7-OH positions, also did not induce mutagenic activity in any of the bacterial strains used, under either activation condition. All the flavonoids were tested at concentrations varying from 2.6 to 30.7 nmol/plate for galangin and 12.1 to 225.0 nmol/plate for other flavonoids. In light of the above, it is necessary to clarify the conditions and the mechanisms that mediate the biological effects of flavonoids before treating them as therapeutical agents, since some compounds can be biotransformed into more genotoxic products; as is the case for galangin, kaempferol and quercetin.
Keywords: mutagenicity; Ames test; flavonoids mutagenicity; Ames test; flavonoids
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Resende, F.A.; Vilegas, W.; dos Santos, L.C.; Varanda, E.A. Mutagenicity of Flavonoids Assayed by Bacterial Reverse Mutation (Ames) Test. Molecules 2012, 17, 5255-5268.

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