Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems

[EN] Enzymatic browning is one of the main problems faced by the food industry due to the enzyme polyphenol oxidase (PPO) provoking an undesirable color change in the presence of oxygen. Here, we report the evaluation of 10 different azamacrocyclic compounds with diverse morphologies as potential in...

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Autores: Muñoz-Pina, Sara, Ros-Lis, José Vicente, Delgado-Pinar, Estefanía, Martínez-Camarena, Álvaro, Verdejo, B., García-España, Enrique, Argüelles Foix, Angel Luís|||0000-0001-5320-7011, Andrés Grau, Ana María|||0000-0002-6132-3167
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/161034
Acceso en línea:https://riunet.upv.es/handle/10251/161034
Access Level:acceso abierto
Palabra clave:PPO
Inhibition
Macrocyclic polyamines
Enzymatic activity
QUIMICA ORGANICA
TECNOLOGIA DE ALIMENTOS
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repository_id_str
spelling Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food SystemsMuñoz-Pina, SaraRos-Lis, José VicenteDelgado-Pinar, EstefaníaMartínez-Camarena, ÁlvaroVerdejo, B.García-España, EnriqueArgüelles Foix, Angel Luís|||0000-0001-5320-7011Andrés Grau, Ana María|||0000-0002-6132-3167PPOInhibitionMacrocyclic polyaminesEnzymatic activityQUIMICA ORGANICATECNOLOGIA DE ALIMENTOS[EN] Enzymatic browning is one of the main problems faced by the food industry due to the enzyme polyphenol oxidase (PPO) provoking an undesirable color change in the presence of oxygen. Here, we report the evaluation of 10 different azamacrocyclic compounds with diverse morphologies as potential inhibitors against the activity of PPO, both in model and real systems. An initial screening of 10 ligands shows that all azamacrocyclic compounds inhibit to some extent the enzymatic browning, but the molecular structure plays a crucial role on the power of inhibition. Kinetic studies of the most active ligand (L2) reveal a S-parabolic I-parabolic noncompetitive inhibition mechanism and a remarkable inhibition at micromolar concentration (IC50 = 10 mu M). Furthermore, L2 action has been proven on apple juice to significantly reduce the enzymatic browning.Financial support by the Spanish Ministerio de Ciencia, Innovacion y Universidades (project RTI2018-100910-B-C44), Ministerio de Economia y Competitividad (projects CTQ2016-78499-C6-1-R, Unidad de Excelencia MDM 2015-0038 and CTQ2017-90852-REDC), and Generalitat Valenciana (Project PROMETEOII2015-002) is gratefully acknowledged.American Chemical SocietyDepartamento de Tecnología de AlimentosInstituto Universitario de Ingeniería de Alimentos (FoodUPV)Escuela Técnica Superior de Ingeniería Agronómica y del Medio NaturalGeneralitat ValencianaMinisterio de Economía y CompetitividadAgencia Estatal de InvestigaciónRepositorio Institucional de la Universitat Politècnica de València Riunet20202020-07-29journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://riunet.upv.es/handle/10251/161034reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 RTI2018-100910-B-C44 DISEÑO Y APLICACIONES SELECCIONADAS DE NANOMATERIALES POROSOS MULTIFUNCIONALES CON POROSIDAD MEJORADAMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 CTQ2016-78499-C6-1-R DISEÑO, SINTESIS Y NANOFORMULACION DE PEQUEÑAS MOLECULAS Y COMPLEJOS METALICOS CON ACTIVIDAD FRENTE A KINETOPLASTIDOS. BUSQUEDA DE DIANAS TERAPEUTICAS Y MECANISMOS DE ACCIONMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 MDM-2015-0038Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 CTQ2017-90852-REDC APLICACION DE LA QUIMICA SUPRAMOLECULAR AL DISEÑO, SINTESIS Y ESTUDIO DE COMPUESTOS BIOACTIVOS DE ACCION ANTIINFLAMATORIA, ANTITUMORAL O ANTIPARASITARIAGeneralitat Valenciana https://doi.org/10.13039/501100003359 PROMETEOII%2F2015%2F002open accesshttp://purl.org/coar/access_right/c_abf2Reserva de todos los derechoshttp://rightsstatements.org/vocab/InC/1.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/1610342026-06-13T07:49:27Z
dc.title.none.fl_str_mv Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
title Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
spellingShingle Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
Muñoz-Pina, Sara
PPO
Inhibition
Macrocyclic polyamines
Enzymatic activity
QUIMICA ORGANICA
TECNOLOGIA DE ALIMENTOS
title_short Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
title_full Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
title_fullStr Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
title_full_unstemmed Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
title_sort Inhibitory Effect of Azamacrocyclic Ligands on Polyphenol Oxidase in Model and Food Systems
dc.creator.none.fl_str_mv Muñoz-Pina, Sara
Ros-Lis, José Vicente
Delgado-Pinar, Estefanía
Martínez-Camarena, Álvaro
Verdejo, B.
García-España, Enrique
Argüelles Foix, Angel Luís|||0000-0001-5320-7011
Andrés Grau, Ana María|||0000-0002-6132-3167
author Muñoz-Pina, Sara
author_facet Muñoz-Pina, Sara
Ros-Lis, José Vicente
Delgado-Pinar, Estefanía
Martínez-Camarena, Álvaro
Verdejo, B.
García-España, Enrique
Argüelles Foix, Angel Luís|||0000-0001-5320-7011
Andrés Grau, Ana María|||0000-0002-6132-3167
author_role author
author2 Ros-Lis, José Vicente
Delgado-Pinar, Estefanía
Martínez-Camarena, Álvaro
Verdejo, B.
García-España, Enrique
Argüelles Foix, Angel Luís|||0000-0001-5320-7011
Andrés Grau, Ana María|||0000-0002-6132-3167
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Tecnología de Alimentos
Instituto Universitario de Ingeniería de Alimentos (FoodUPV)
Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural
Generalitat Valenciana
Ministerio de Economía y Competitividad
Agencia Estatal de Investigación
Repositorio Institucional de la Universitat Politècnica de València Riunet
dc.subject.none.fl_str_mv PPO
Inhibition
Macrocyclic polyamines
Enzymatic activity
QUIMICA ORGANICA
TECNOLOGIA DE ALIMENTOS
topic PPO
Inhibition
Macrocyclic polyamines
Enzymatic activity
QUIMICA ORGANICA
TECNOLOGIA DE ALIMENTOS
description [EN] Enzymatic browning is one of the main problems faced by the food industry due to the enzyme polyphenol oxidase (PPO) provoking an undesirable color change in the presence of oxygen. Here, we report the evaluation of 10 different azamacrocyclic compounds with diverse morphologies as potential inhibitors against the activity of PPO, both in model and real systems. An initial screening of 10 ligands shows that all azamacrocyclic compounds inhibit to some extent the enzymatic browning, but the molecular structure plays a crucial role on the power of inhibition. Kinetic studies of the most active ligand (L2) reveal a S-parabolic I-parabolic noncompetitive inhibition mechanism and a remarkable inhibition at micromolar concentration (IC50 = 10 mu M). Furthermore, L2 action has been proven on apple juice to significantly reduce the enzymatic browning.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020-07-29
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://riunet.upv.es/handle/10251/161034
url https://riunet.upv.es/handle/10251/161034
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 RTI2018-100910-B-C44 DISEÑO Y APLICACIONES SELECCIONADAS DE NANOMATERIALES POROSOS MULTIFUNCIONALES CON POROSIDAD MEJORADA
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 CTQ2016-78499-C6-1-R DISEÑO, SINTESIS Y NANOFORMULACION DE PEQUEÑAS MOLECULAS Y COMPLEJOS METALICOS CON ACTIVIDAD FRENTE A KINETOPLASTIDOS. BUSQUEDA DE DIANAS TERAPEUTICAS Y MECANISMOS DE ACCION
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 MDM-2015-0038
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 CTQ2017-90852-REDC APLICACION DE LA QUIMICA SUPRAMOLECULAR AL DISEÑO, SINTESIS Y ESTUDIO DE COMPUESTOS BIOACTIVOS DE ACCION ANTIINFLAMATORIA, ANTITUMORAL O ANTIPARASITARIA
Generalitat Valenciana https://doi.org/10.13039/501100003359 PROMETEOII%2F2015%2F002
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
instname:Universitat Politècnica de València (UPV)
instname_str Universitat Politècnica de València (UPV)
reponame_str RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
collection RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301629

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