Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures

The formation of 2-phenylethylamine and phenylacetaldehyde in mixtures of phenylalanine, a lipid oxidation product, and a second amino acid was studied to determine the role of the second amino acid in the degradation of phenylalanine produced by lipid-derived reactive carbonyls. The presence of the...

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Detalhes bibliográficos
Autores: Hidalgo, Francisco J., León, María Mercedes, Zamora, Rosario
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/147630
Acesso em linha:http://hdl.handle.net/10261/147630
Access Level:acceso abierto
Palavra-chave:Lipid oxidation
Biogenic amines
Carbonyl-amine reactions
Amino acid degradation
Strecker degradation
Maillard reaction
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spelling Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixturesHidalgo, Francisco J.León, María MercedesZamora, RosarioLipid oxidationBiogenic aminesCarbonyl-amine reactionsAmino acid degradationStrecker degradationMaillard reactionThe formation of 2-phenylethylamine and phenylacetaldehyde in mixtures of phenylalanine, a lipid oxidation product, and a second amino acid was studied to determine the role of the second amino acid in the degradation of phenylalanine produced by lipid-derived reactive carbonyls. The presence of the second amino acid usually increased the formation of the amine and reduced the formation of the Strecker aldehyde. The reasons for this behaviour seem to be related to the α-amino group and the other functional groups (mainly amino or similar groups) present in the side-chain of the amino acid. These groups are suggested to modify the lipid-derived reactive carbonyl but not the reaction mechanism because the E of formation of both 2-phenylethylamine and phenylacetaldehyde remained unchanged in all studied systems. All these results suggest that the amine/aldehyde ratio obtained by amino acid degradation can be modified by adding free amino acids during food formulation.We are indebted to José L. Navarro for technical assistance. 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 (projects AGL2012-35627 and AGL2015-68186-R).Peer ReviewedElsevierMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2017201720162017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/147630reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)InglésSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1476302026-05-22T06:33:51Z
dc.title.none.fl_str_mv Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
title Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
spellingShingle Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
Hidalgo, Francisco J.
Lipid oxidation
Biogenic amines
Carbonyl-amine reactions
Amino acid degradation
Strecker degradation
Maillard reaction
title_short Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
title_full Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
title_fullStr Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
title_full_unstemmed Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
title_sort Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures
dc.creator.none.fl_str_mv Hidalgo, Francisco J.
León, María Mercedes
Zamora, Rosario
author Hidalgo, Francisco J.
author_facet Hidalgo, Francisco J.
León, María Mercedes
Zamora, Rosario
author_role author
author2 León, María Mercedes
Zamora, Rosario
author2_role author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Lipid oxidation
Biogenic amines
Carbonyl-amine reactions
Amino acid degradation
Strecker degradation
Maillard reaction
topic Lipid oxidation
Biogenic amines
Carbonyl-amine reactions
Amino acid degradation
Strecker degradation
Maillard reaction
description The formation of 2-phenylethylamine and phenylacetaldehyde in mixtures of phenylalanine, a lipid oxidation product, and a second amino acid was studied to determine the role of the second amino acid in the degradation of phenylalanine produced by lipid-derived reactive carbonyls. The presence of the second amino acid usually increased the formation of the amine and reduced the formation of the Strecker aldehyde. The reasons for this behaviour seem to be related to the α-amino group and the other functional groups (mainly amino or similar groups) present in the side-chain of the amino acid. These groups are suggested to modify the lipid-derived reactive carbonyl but not the reaction mechanism because the E of formation of both 2-phenylethylamine and phenylacetaldehyde remained unchanged in all studied systems. All these results suggest that the amine/aldehyde ratio obtained by amino acid degradation can be modified by adding free amino acids during food formulation.
publishDate 2016
dc.date.none.fl_str_mv 2016
2017
2017
2017
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/10261/147630
url http://hdl.handle.net/10261/147630
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 15.811543

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