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

Flavia Aparecida Resende1, Wagner Vilegas, Lourdes Campaner Dos Santos

  • 1Department of Biological Sciences, Faculty of Pharmaceutical Sciences of Araraquara, UNESP-Sao Paulo State University, Araraquara CEP 14801-902, Sao Paulo, Brazil.

Molecules (Basel, Switzerland)
|May 9, 2012
PubMed

Insights

The Ames test revealed that some flavonoids, like quercetin, kaempferol, and galangin, can be mutagenic, especially after metabolic activation. Hydroxylation patterns influence mutagenicity, with fewer hydroxyl groups generally showing less activity.

Area of Science:

  • Biochemistry
  • Toxicology
  • Natural Products Chemistry

Background:

  • Flavonoids are widely distributed plant compounds with diverse biological activities.
  • Understanding their potential genotoxicity is crucial for assessing their safety as therapeutic agents.
  • The relationship between flavonoid structure, specifically hydroxylation patterns, and mutagenicity requires further elucidation.

Purpose of the Study:

  • To investigate the mutagenicity of ten different flavonoids using the Ames test.
  • To establish structure-activity relationship profiles concerning hydroxylation patterns and mutagenicity.
  • To assess the influence of metabolic activation on flavonoid mutagenicity.

Main Methods:

  • Assay of ten flavonoids (quercetin, kaempferol, luteolin, fisetin, chrysin, galangin, flavone, 3-hydroxyflavone, 5-hydroxyflavone, 7-hydroxyflavone) using the Ames test.
  • Utilized Salmonella typhimurium strains TA98, TA100, and TA102.
  • Evaluated mutagenicity with and without metabolic activation (S9 mix).

Main Results:

  • Quercetin exhibited direct mutagenicity, which increased with metabolic activation.
  • Kaempferol and galangin were mutagenic in strain TA98, with kaempferol also showing mutagenicity in other strains after metabolic activation.
  • Flavone (no hydroxyl groups) and monohydroxylated flavonoids showed minimal mutagenicity, primarily in strain TA102 after metabolization. Luteolin and fisetin also showed mutagenicity in TA102.
  • Chrysin (5,7-dihydroxy) was not mutagenic under tested conditions.

Conclusions:

  • Flavonoid mutagenicity is dependent on both the specific compound and metabolic activation.
  • Hydroxylation patterns significantly influence mutagenic potential; fewer hydroxyl groups generally correlate with lower mutagenicity.
  • Certain flavonoids can be biotransformed into more genotoxic products, necessitating careful evaluation before therapeutic use.

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