Genotoxicity of nitrosated red wine and of the nitrosatable phenolic compounds present in wine

Tyramine, quercetin and malvidine-3-glucoside

A. Laires, J. Gaspar, H. Borba, M. Proença, M. Monteiro, J. Rueff

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16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)989-994
Number of pages6
JournalFood and Chemical Toxicology
Volume31
Issue number12
DOIs
Publication statusPublished - 1993

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Tyramine
Wine
Nitrosation
tyramine
genotoxicity
red wines
quercetin
glucosides
wines
phenolic compounds
biogenic amines
flavonoids
phenethylamines
Biogenic Amines
histamine
Flavonoids
Molecules
Phenethylamines
Quercetin
assays

Cite this

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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.",
author = "A. Laires and J. Gaspar and H. Borba and M. Proen{\cc}a and M. Monteiro and J. Rueff",
year = "1993",
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language = "English",
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journal = "Food and Chemical Toxicology",
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publisher = "Elsevier Science B.V., Amsterdam.",
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TY - JOUR

T1 - Genotoxicity of nitrosated red wine and of the nitrosatable phenolic compounds present in wine

T2 - Tyramine, quercetin and malvidine-3-glucoside

AU - Laires, A.

AU - Gaspar, J.

AU - Borba, H.

AU - Proença, M.

AU - Monteiro, M.

AU - Rueff, J.

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

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U2 - 10.1016/0278-6915(93)90008-M

DO - 10.1016/0278-6915(93)90008-M

M3 - Article

VL - 31

SP - 989

EP - 994

JO - Food and Chemical Toxicology

JF - Food and Chemical Toxicology

SN - 0278-6915

IS - 12

ER -