title: Genotoxicity of nitrosated red wine and of the nitrosatable phenolic compounds present in wine: tyramine, quercetin and malvidine-3-glucoside.
abstract: Phenolic compounds and biogenic amines are known to be present in some foodstuffs which become directly genotoxic after nitrosation in vitro. Red wine has previously been shown to be genotoxic and this activity has been attributed mainly to flavonoids. Besides flavonoids, red wine contains a multiplicity of compounds, including biogenic amines. Using the Ames assay and the SOS chromotest, this study has shown that red wine and some of the nitrosatable molecules present in wine become directly genotoxic on nitrosation in vitro: these include the phenolic molecules tyramine, quercetin and malvidine-3-glucoside, whereas phenylethylamine and histamine were negative on nitrosation. Interestingly, quercetin had been predicted to be negative after nitrosation, using the CASE methodology. The concentrations of these three positive nitrosatable compounds in wine were determined by HPLC. Comparison of these concentrations and their respective levels of genotoxicity suggests that the genotoxicity after nitrosation is probably attributable to other molecules. It is also possible that synergistic effects may occur between various nitrosatable compounds in wine.
authors.affiliation: Department of Genetics, Faculty of Medical Sciences UNL, Lisbon, Portugal.
authors.forename: A
authors.initials: A
authors.lastname: Laires
authors.forename: J
authors.initials: J
authors.lastname: Gaspar
authors.forename: H
authors.initials: H
authors.lastname: Borba
authors.forename: M
authors.initials: M
authors.lastname: Proença
authors.forename: M
authors.initials: M
authors.lastname: Monteiro
authors.forename: J
authors.initials: J
authors.lastname: Rueff
mesh_terms: D000872:Anthocyanins / Q000032:analysis / Q000378:metabolism / Q000633:toxicity*; D002851:Chromatography, High Pressure Liquid; D004305:Dose-Response Relationship, Drug; D009152:Mutagenicity Tests; D009153:Mutagens / Q000032:analysis / Q000378:metabolism / Q000633:toxicity*; D009573:Nitrites / Q000494:pharmacology; D015538:Nitrosation; D011794:Quercetin / Q000032:analysis / Q000378:metabolism / Q000633:toxicity*; D014439:Tyramine / Q000032:analysis / Q000378:metabolism / Q000633:toxicity*; D014920:Wine / Q000032:analysis / Q000633:toxicity*
chemical_list: D000872:Anthocyanins; D009153:Mutagens; D009573:Nitrites; D011794:Quercetin; D014439:Tyramine