title: Differences in the hydroxylation pattern of flavonoids alter their chemoprotective effect against direct- and indirect-acting mutagens.
abstract: The antimutagenicity of ten flavonoids, differing in their hydroxylation patterns against direct-acting and indirect-acting mutagens, namely 4-nitro-o-phenylenediamine, sodium azide, mitomycin C, benzo[a]pyrene, aflatoxin B1 and 2-aminofluorene, were compared with the aim of investigating how the hydroxyl groups in their structures govern the biological activity of flavonoids, by the Ames test, with Salmonella typhimurium strains TA98, TA100 and TA102. The flavonoids tested were: quercetin, kaempferol, luteolin, fisetin, chrysin, galangin, flavone, 3-hydroxyflavone, 5-hydroxyflavone and 7-hydroxyflavone. In these tests, all compounds were shown to be antimutagenic in more than one strain and various mechanisms of action were demonstrated. The results suggested that the number and position of hydroxyl groups may increase or decrease the protective effect, depending on the type and concentration of flavonoids and mutagen used. These studies contribute to clarifying the mechanisms by which these flavonoids act in protecting DNA from damage. This is required before they can be widely used.
authors.affiliation: UNESP-São Paulo State University, Faculty of Pharmaceutical Sciences of Araraquara, Department of Biological Sciences, CEP 14801-902 Araraquara, São Paulo, Brazil. Electronic address: flaviabiomed@yahoo.com.br.
authors.forename: Flávia A
authors.initials: FA
authors.lastname: Resende
authors.affiliation: UNESP-São Paulo State University, Faculty of Pharmaceutical Sciences of Araraquara, Department of Biological Sciences, CEP 14801-902 Araraquara, São Paulo, Brazil.
authors.forename: Carolina P
authors.initials: CP
authors.lastname: da Silva Almeida
authors.affiliation: UNESP-São Paulo State University, Experimental Campus of the Paulista Coast, CEP 11330-900 São Vicente, São Paulo, Brazil.
authors.forename: Wagner
authors.initials: W
authors.lastname: Vilegas
authors.affiliation: UNESP-São Paulo State University, Faculty of Pharmaceutical Sciences of Araraquara, Department of Biological Sciences, CEP 14801-902 Araraquara, São Paulo, Brazil.
authors.forename: Eliana A
authors.initials: EA
authors.lastname: Varanda
mesh_terms: D016587:Antimutagenic Agents / Q000737:chemistry* / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D006900:Hydroxylation; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics
chemical_list: D016587:Antimutagenic Agents; D005419:Flavonoids; D009153:Mutagens
keywords: Ames test; Antimutagenicity; Flavonoids