Atypical antioxidant activity of non-phenolic amino-coumarins

Autores
Zúñiga Núñez, Daniel; Barrias, Pablo; Cárdenas Jirón, Gloria; Ureta Zañartu, M. Soledad; Lopez Alarcón, Camilo; Moran Vieyra, Faustino Eduardo; Borsarelli, Claudio Darío; Alarcón, Emilio; Aspee, Alexis
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Coumarin compounds have been described as anti-inflammatories, and chemotherapeutic agents as well as antioxidants. However, the origin of the antioxidant activity of non phenolic coumarins remains obscure. In the present report, we demonstrate that non-phenolic 7-dialkyl-aminocoumarins may also have significant antioxidant properties against free radicals derived from 2,2′-azobis(2-amidinopropane) dihydrochloride under aerobic conditions. This atypical behaviour is due to the presence of traces of very reactive hydroxycinnamic acid-type compounds. Changing functional groups at the C-3 and C-4 positions shifts the reactivity of the compounds from peroxyl to alkoxyl free radicals. Kinetic and theoretical studies based on Density Functional Theory support the formation of reactive hydroxycinnamic acid and directly link the antioxidant behaviour of the compounds to hydrogen atom transfer.
Fil: Zúñiga Núñez, Daniel. Universidad de Santiago de Chile; Chile
Fil: Barrias, Pablo. Universidad de Santiago de Chile; Chile
Fil: Cárdenas Jirón, Gloria. Universidad de Santiago de Chile; Chile
Fil: Ureta Zañartu, M. Soledad. Universidad de Santiago de Chile; Chile
Fil: Lopez Alarcón, Camilo. Pontificia Universidad Católica de Chile; Chile
Fil: Moran Vieyra, Faustino Eduardo. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina
Fil: Borsarelli, Claudio Darío. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina
Fil: Alarcón, Emilio. University of Ottawa; Canadá
Fil: Aspee, Alexis. University of Ottawa; Canadá
Materia
COUMARINS
ANTIOXIDANT
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/149456
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Atypical antioxidant activity of non-phenolic amino-coumarinsZúñiga Núñez, DanielBarrias, PabloCárdenas Jirón, GloriaUreta Zañartu, M. SoledadLopez Alarcón, CamiloMoran Vieyra, Faustino EduardoBorsarelli, Claudio DaríoAlarcón, EmilioAspee, AlexisCOUMARINSANTIOXIDANThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Coumarin compounds have been described as anti-inflammatories, and chemotherapeutic agents as well as antioxidants. However, the origin of the antioxidant activity of non phenolic coumarins remains obscure. In the present report, we demonstrate that non-phenolic 7-dialkyl-aminocoumarins may also have significant antioxidant properties against free radicals derived from 2,2′-azobis(2-amidinopropane) dihydrochloride under aerobic conditions. This atypical behaviour is due to the presence of traces of very reactive hydroxycinnamic acid-type compounds. Changing functional groups at the C-3 and C-4 positions shifts the reactivity of the compounds from peroxyl to alkoxyl free radicals. Kinetic and theoretical studies based on Density Functional Theory support the formation of reactive hydroxycinnamic acid and directly link the antioxidant behaviour of the compounds to hydrogen atom transfer.Fil: Zúñiga Núñez, Daniel. Universidad de Santiago de Chile; ChileFil: Barrias, Pablo. Universidad de Santiago de Chile; ChileFil: Cárdenas Jirón, Gloria. Universidad de Santiago de Chile; ChileFil: Ureta Zañartu, M. Soledad. Universidad de Santiago de Chile; ChileFil: Lopez Alarcón, Camilo. Pontificia Universidad Católica de Chile; ChileFil: Moran Vieyra, Faustino Eduardo. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; ArgentinaFil: Borsarelli, Claudio Darío. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; ArgentinaFil: Alarcón, Emilio. University of Ottawa; CanadáFil: Aspee, Alexis. University of Ottawa; CanadáRoyal Society of Chemistry2018-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/149456Zúñiga Núñez, Daniel; Barrias, Pablo; Cárdenas Jirón, Gloria; Ureta Zañartu, M. Soledad; Lopez Alarcón, Camilo; et al.; Atypical antioxidant activity of non-phenolic amino-coumarins; Royal Society of Chemistry; RSC Advances; 8; 4; 1-2018; 1927-19332046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/ 10.1039/c7ra12000ainfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2018/RA/C7RA12000Ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:16:36Zoai:ri.conicet.gov.ar:11336/149456instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:16:36.743CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Atypical antioxidant activity of non-phenolic amino-coumarins
title Atypical antioxidant activity of non-phenolic amino-coumarins
spellingShingle Atypical antioxidant activity of non-phenolic amino-coumarins
Zúñiga Núñez, Daniel
COUMARINS
ANTIOXIDANT
title_short Atypical antioxidant activity of non-phenolic amino-coumarins
title_full Atypical antioxidant activity of non-phenolic amino-coumarins
title_fullStr Atypical antioxidant activity of non-phenolic amino-coumarins
title_full_unstemmed Atypical antioxidant activity of non-phenolic amino-coumarins
title_sort Atypical antioxidant activity of non-phenolic amino-coumarins
dc.creator.none.fl_str_mv Zúñiga Núñez, Daniel
Barrias, Pablo
Cárdenas Jirón, Gloria
Ureta Zañartu, M. Soledad
Lopez Alarcón, Camilo
Moran Vieyra, Faustino Eduardo
Borsarelli, Claudio Darío
Alarcón, Emilio
Aspee, Alexis
author Zúñiga Núñez, Daniel
author_facet Zúñiga Núñez, Daniel
Barrias, Pablo
Cárdenas Jirón, Gloria
Ureta Zañartu, M. Soledad
Lopez Alarcón, Camilo
Moran Vieyra, Faustino Eduardo
Borsarelli, Claudio Darío
Alarcón, Emilio
Aspee, Alexis
author_role author
author2 Barrias, Pablo
Cárdenas Jirón, Gloria
Ureta Zañartu, M. Soledad
Lopez Alarcón, Camilo
Moran Vieyra, Faustino Eduardo
Borsarelli, Claudio Darío
Alarcón, Emilio
Aspee, Alexis
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv COUMARINS
ANTIOXIDANT
topic COUMARINS
ANTIOXIDANT
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Coumarin compounds have been described as anti-inflammatories, and chemotherapeutic agents as well as antioxidants. However, the origin of the antioxidant activity of non phenolic coumarins remains obscure. In the present report, we demonstrate that non-phenolic 7-dialkyl-aminocoumarins may also have significant antioxidant properties against free radicals derived from 2,2′-azobis(2-amidinopropane) dihydrochloride under aerobic conditions. This atypical behaviour is due to the presence of traces of very reactive hydroxycinnamic acid-type compounds. Changing functional groups at the C-3 and C-4 positions shifts the reactivity of the compounds from peroxyl to alkoxyl free radicals. Kinetic and theoretical studies based on Density Functional Theory support the formation of reactive hydroxycinnamic acid and directly link the antioxidant behaviour of the compounds to hydrogen atom transfer.
Fil: Zúñiga Núñez, Daniel. Universidad de Santiago de Chile; Chile
Fil: Barrias, Pablo. Universidad de Santiago de Chile; Chile
Fil: Cárdenas Jirón, Gloria. Universidad de Santiago de Chile; Chile
Fil: Ureta Zañartu, M. Soledad. Universidad de Santiago de Chile; Chile
Fil: Lopez Alarcón, Camilo. Pontificia Universidad Católica de Chile; Chile
Fil: Moran Vieyra, Faustino Eduardo. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina
Fil: Borsarelli, Claudio Darío. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina
Fil: Alarcón, Emilio. University of Ottawa; Canadá
Fil: Aspee, Alexis. University of Ottawa; Canadá
description Coumarin compounds have been described as anti-inflammatories, and chemotherapeutic agents as well as antioxidants. However, the origin of the antioxidant activity of non phenolic coumarins remains obscure. In the present report, we demonstrate that non-phenolic 7-dialkyl-aminocoumarins may also have significant antioxidant properties against free radicals derived from 2,2′-azobis(2-amidinopropane) dihydrochloride under aerobic conditions. This atypical behaviour is due to the presence of traces of very reactive hydroxycinnamic acid-type compounds. Changing functional groups at the C-3 and C-4 positions shifts the reactivity of the compounds from peroxyl to alkoxyl free radicals. Kinetic and theoretical studies based on Density Functional Theory support the formation of reactive hydroxycinnamic acid and directly link the antioxidant behaviour of the compounds to hydrogen atom transfer.
publishDate 2018
dc.date.none.fl_str_mv 2018-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/149456
Zúñiga Núñez, Daniel; Barrias, Pablo; Cárdenas Jirón, Gloria; Ureta Zañartu, M. Soledad; Lopez Alarcón, Camilo; et al.; Atypical antioxidant activity of non-phenolic amino-coumarins; Royal Society of Chemistry; RSC Advances; 8; 4; 1-2018; 1927-1933
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/149456
identifier_str_mv Zúñiga Núñez, Daniel; Barrias, Pablo; Cárdenas Jirón, Gloria; Ureta Zañartu, M. Soledad; Lopez Alarcón, Camilo; et al.; Atypical antioxidant activity of non-phenolic amino-coumarins; Royal Society of Chemistry; RSC Advances; 8; 4; 1-2018; 1927-1933
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/ 10.1039/c7ra12000a
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2018/RA/C7RA12000A
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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