Structural requirements for mutagenicity of flavonoids upon nitrosation. A structure-activity study.
A wealth of promutagens can damage DNA provided metabolic/chemical reactions take place before an ultimate mutagen is formed. Nitrosation reactions are amongst those chemical reactions which may take place to render some chemical classes of promutagens as ultimate mutagens. Flavonoids are amongst chemicals which can be rendered mutagenic upon nitrosation. In this study, 22 flavonoids were tested in the Ames assay for their mutagenicity upon nitrosation and the respective structural requirements for nitrosation-dependent mutagenicity were established. Nitrosatable chemicals present in the diet may play a role in the aetiology of gastric cancer and flavonoids are amongst the common molecules present in a variety of food items. Flavonoids such as quercetin and catechin were predicted to be non-mutagenic upon nitrosation by the CASE methodology and were shown in this study to be strong nitrosatable mutagens.
D004249:DNA Damage; D004305:Dose-Response Relationship, Drug; D005419:Flavonoids / Q000737:chemistry / Q000633:toxicity*; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D009603:Nitroso Compounds; D011355:Prodrugs / Q000737:chemistry / Q000633:toxicity*; D011794:Quercetin / Q000633:toxicity; D012431:Rutin / Q000633:toxicity; D012486:Salmonella typhimurium / Q000187:drug effects*; D013329:Structure-Activity Relationship
D005419:Flavonoids; D009153:Mutagens; D009603:Nitroso Compounds; D011355:Prodrugs; D012431:Rutin; D011794:Quercetin