Mutagenic products are promoted in the nitrosation of tyramine

[EN] Tyramine is a biogenic compound derived from the decarboxylation of the amino acid tyrosine, and is therefore present at important concentrations in a broad range of raw and fermented foods. Owing to its chemical properties, tyramine can react with nitrite, a common food additive, in the acidic...

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Autores: González Jiménez, Mario, Arenas Valgañón, Jorge, García Santos, María Pilar, Calle Martín, Emilio, Casado, Julio
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/154897
Acceso en línea:http://hdl.handle.net/10366/154897
Access Level:acceso abierto
Palabra clave:Monoamines
Nitrosation reactions
Nitroso compounds
Tyramine
2210 Química Física
2210.03 Cinética Química
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spelling Mutagenic products are promoted in the nitrosation of tyramineGonzález Jiménez, MarioArenas Valgañón, JorgeGarcía Santos, María PilarCalle Martín, EmilioCasado, JulioMonoaminesNitrosation reactionsNitroso compoundsTyramine2210 Química Física2210.03 Cinética Química[EN] Tyramine is a biogenic compound derived from the decarboxylation of the amino acid tyrosine, and is therefore present at important concentrations in a broad range of raw and fermented foods. Owing to its chemical properties, tyramine can react with nitrite, a common food additive, in the acidic medium of stomach to form N- and C-nitroso compounds. Since toxicology studies have shown that the product of C-nitrosation of tyramine is mutagenic, in the present article tyramine nitrosation mechanisms have been characterized in order to discern which of them are favoured under conditions similar to those in the human stomach lumen. To determine the kinetic course of nitrosation reactions, a systematic study of the nitrosation of ethylbenzene, phenethylamine, and tyramine was carried out, using UV–visible absorption spectroscopy. The results show that, under conditions mimicking those of the stomach lumen, the most favoured reaction in tyramine is C-nitrosation, which generates mutagenic products.Ministerio de Economía y Competitividad and the European Regional Development Fund (Project CTQ2010-18999). M.G.J. disfrutó una beca de Doctorado del Ministerio de Economía y Competitividad. J.A.V. disfrutó una beca de Doctorado de la Junta de Castilla y León.Elsevier202420242017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10366/154897reponame:GREDOS. Repositorio Institucional de la Universidad de Salamancainstname:Universidad de Salamanca (USAL)InglésCTQ2010-18999Attribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:gredos.usal.es:10366/1548972026-06-07T06:28:51Z
dc.title.none.fl_str_mv Mutagenic products are promoted in the nitrosation of tyramine
title Mutagenic products are promoted in the nitrosation of tyramine
spellingShingle Mutagenic products are promoted in the nitrosation of tyramine
González Jiménez, Mario
Monoamines
Nitrosation reactions
Nitroso compounds
Tyramine
2210 Química Física
2210.03 Cinética Química
title_short Mutagenic products are promoted in the nitrosation of tyramine
title_full Mutagenic products are promoted in the nitrosation of tyramine
title_fullStr Mutagenic products are promoted in the nitrosation of tyramine
title_full_unstemmed Mutagenic products are promoted in the nitrosation of tyramine
title_sort Mutagenic products are promoted in the nitrosation of tyramine
dc.creator.none.fl_str_mv González Jiménez, Mario
Arenas Valgañón, Jorge
García Santos, María Pilar
Calle Martín, Emilio
Casado, Julio
author González Jiménez, Mario
author_facet González Jiménez, Mario
Arenas Valgañón, Jorge
García Santos, María Pilar
Calle Martín, Emilio
Casado, Julio
author_role author
author2 Arenas Valgañón, Jorge
García Santos, María Pilar
Calle Martín, Emilio
Casado, Julio
author2_role author
author
author
author
dc.subject.none.fl_str_mv Monoamines
Nitrosation reactions
Nitroso compounds
Tyramine
2210 Química Física
2210.03 Cinética Química
topic Monoamines
Nitrosation reactions
Nitroso compounds
Tyramine
2210 Química Física
2210.03 Cinética Química
description [EN] Tyramine is a biogenic compound derived from the decarboxylation of the amino acid tyrosine, and is therefore present at important concentrations in a broad range of raw and fermented foods. Owing to its chemical properties, tyramine can react with nitrite, a common food additive, in the acidic medium of stomach to form N- and C-nitroso compounds. Since toxicology studies have shown that the product of C-nitrosation of tyramine is mutagenic, in the present article tyramine nitrosation mechanisms have been characterized in order to discern which of them are favoured under conditions similar to those in the human stomach lumen. To determine the kinetic course of nitrosation reactions, a systematic study of the nitrosation of ethylbenzene, phenethylamine, and tyramine was carried out, using UV–visible absorption spectroscopy. The results show that, under conditions mimicking those of the stomach lumen, the most favoured reaction in tyramine is C-nitrosation, which generates mutagenic products.
publishDate 2017
dc.date.none.fl_str_mv 2017
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10366/154897
url http://hdl.handle.net/10366/154897
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv CTQ2010-18999
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:GREDOS. Repositorio Institucional de la Universidad de Salamanca
instname:Universidad de Salamanca (USAL)
instname_str Universidad de Salamanca (USAL)
reponame_str GREDOS. Repositorio Institucional de la Universidad de Salamanca
collection GREDOS. Repositorio Institucional de la Universidad de Salamanca
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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