Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid

44 Páginas.-- 8 Figuras.-- 3 Tablas.-- 3Figuras y 1 tabla suplementarias

Detalles Bibliográficos
Autores: Zamora, Rosario, Navarro, José Luis, Hidalgo, Francisco J.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/176201
Acceso en línea:http://hdl.handle.net/10261/176201
Access Level:acceso abierto
Palabra clave:2-Phenylethylamine
Biogenic amines
Lipid hydroperoxides
Lipid oxidation
Maillard reaction
Phenolics
Reactive carbonyls
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spelling Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic AcidZamora, RosarioNavarro, José LuisHidalgo, Francisco J.2-PhenylethylamineBiogenic aminesLipid hydroperoxidesLipid oxidationMaillard reactionPhenolicsReactive carbonyls44 Páginas.-- 8 Figuras.-- 3 Tablas.-- 3Figuras y 1 tabla suplementariasLipid hydroperoxides have been shown to produce amino acid decarboxylations. Because thermal decomposition of lipid hydroperoxides produces free radicals and reactive carbonyls, and phenolic compounds have been shown to scavenger both of them, phenolics are expected to inhibit these reactions and this protection should depend on the structures of the involved phenolics. In this study, the effect of a wide array of phenolics and their mixtures on 2-phenylethylamine formation by phenylalanine degradation in the presence of the 13-hydroperoxide of linoleic acid (LOOH) was studied. LOOH increased considerably the formation of the amine, and phenolics mostly exhibiting an inhibitory role that depended on their structure. Thus, 1,3-diphenols decreased the formation of 2-phenylethylamine because of their carbonyl trapping abilities. In contrast, the inhibition of 1,2- and 1,4-diphenols was lower because they could not trap the reactive carbonyls produced by LOOH decomposition. In addition, their free radical scavenging was likely accompanied by the formation of quinones, which acted as reactive carbonyls. The function of all other phenolics could be calculated by adding the individual functions of the different diphenols present in their structures. In fact, experimental values obtained for both mixtures of phenolics and complex phenolics correlated well with the calculated values obtained from their constituting diphenols. All of these results suggest that, when the reaction mechanisms are known, it is possible to predict the behavior of complex phenolics on the basis of their structure.This study was supported in part by the European Union (FEDER funds) and the Plan Nacional de I + D of the Ministerio de Economía y Competitividad of Spain (project AGL2015-68186-R).Peer reviewedAmerican Chemical SocietyEuropean CommissionMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201920192018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/176201reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/AGL2015-68186-Rhttp://dx.doi.org/10.1021/acs.jafc.8b05569Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1762012026-05-22T06:33:51Z
dc.title.none.fl_str_mv Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
title Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
spellingShingle Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
Zamora, Rosario
2-Phenylethylamine
Biogenic amines
Lipid hydroperoxides
Lipid oxidation
Maillard reaction
Phenolics
Reactive carbonyls
title_short Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
title_full Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
title_fullStr Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
title_full_unstemmed Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
title_sort Structure–Activity Relationship (SAR) of Phenolics for the Inhibition of 2-Phenylethylamine Formation in Model Systems Involving Phenylalanine and the 13-Hydroperoxide of Linoleic Acid
dc.creator.none.fl_str_mv Zamora, Rosario
Navarro, José Luis
Hidalgo, Francisco J.
author Zamora, Rosario
author_facet Zamora, Rosario
Navarro, José Luis
Hidalgo, Francisco J.
author_role author
author2 Navarro, José Luis
Hidalgo, Francisco J.
author2_role author
author
dc.contributor.none.fl_str_mv European Commission
Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv 2-Phenylethylamine
Biogenic amines
Lipid hydroperoxides
Lipid oxidation
Maillard reaction
Phenolics
Reactive carbonyls
topic 2-Phenylethylamine
Biogenic amines
Lipid hydroperoxides
Lipid oxidation
Maillard reaction
Phenolics
Reactive carbonyls
description 44 Páginas.-- 8 Figuras.-- 3 Tablas.-- 3Figuras y 1 tabla suplementarias
publishDate 2018
dc.date.none.fl_str_mv 2018
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/176201
url http://hdl.handle.net/10261/176201
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/AGL2015-68186-R
http://dx.doi.org/10.1021/acs.jafc.8b05569
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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