Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin

Autores
Montaña, Maria Paulina; Massad, Walter Alfredo; Criado, Susana Noemi; Biasutti, Maria Alicia; Garcia, Norman Andino
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Kinetic and mechanistic aspects on the stability of the flavones (FL) quercetin (Que), morin (Mor) and rutin (Rut), in methanolic solution and in the presence of reactive oxygen species (ROS) generated by visible light-promoted riboflavin (Rf, vitamin B2) photoirradiation were studied. The system was chosen as a model for the evaluation of the in vivo protective effect of biological targets by the flavones. The overall picture includes the vitamin as an endogenous natural photosensitizer. A systematic study on the effect of ROS on FL photostability shows that under work conditions Que is oxidized by singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2̇-) and hydrogen peroxide; Mor is degraded by O2(1Δg) and O 2̇- whereas Rut only reacts with O2( 1Δg). Que and Rut, with an extremely poor overall rate constant, are mainly physical quenchers of O2( 1Δg). Mor, with O2(1Δ g)-interception ability slightly lower than the recognized synthetic antioxidant trolox (Tx), behaves as a typical sacrificial scavenger provided that ca 80% of the collisions with O2(1Δ g) cause its own degradation, whereas this parameter reaches around 50% in the case of Tx.
Fil: Montaña, Maria Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Biasutti, Maria Alicia. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Materia
Quercetin
Morin Rutin
Photoooxidation
Photodegradation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/131225
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/131225
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutinMontaña, Maria PaulinaMassad, Walter AlfredoCriado, Susana NoemiBiasutti, Maria AliciaGarcia, Norman AndinoQuercetinMorin RutinPhotoooxidationPhotodegradationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Kinetic and mechanistic aspects on the stability of the flavones (FL) quercetin (Que), morin (Mor) and rutin (Rut), in methanolic solution and in the presence of reactive oxygen species (ROS) generated by visible light-promoted riboflavin (Rf, vitamin B2) photoirradiation were studied. The system was chosen as a model for the evaluation of the in vivo protective effect of biological targets by the flavones. The overall picture includes the vitamin as an endogenous natural photosensitizer. A systematic study on the effect of ROS on FL photostability shows that under work conditions Que is oxidized by singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2̇-) and hydrogen peroxide; Mor is degraded by O2(1Δg) and O 2̇- whereas Rut only reacts with O2( 1Δg). Que and Rut, with an extremely poor overall rate constant, are mainly physical quenchers of O2( 1Δg). Mor, with O2(1Δ g)-interception ability slightly lower than the recognized synthetic antioxidant trolox (Tx), behaves as a typical sacrificial scavenger provided that ca 80% of the collisions with O2(1Δ g) cause its own degradation, whereas this parameter reaches around 50% in the case of Tx.Fil: Montaña, Maria Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; ArgentinaFil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Biasutti, Maria Alicia. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaWiley Blackwell Publishing, Inc2010-07-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/131225Montaña, Maria Paulina; Massad, Walter Alfredo; Criado, Susana Noemi; Biasutti, Maria Alicia; Garcia, Norman Andino; Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 86; 4; 7-7-2010; 827-8340031-8655CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1111/j.1751-1097.2010.00754.xinfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1111/j.1751-1097.2010.00754.xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:50:17Zoai:ri.conicet.gov.ar:11336/131225instacron: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 09:50:18.211CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
title Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
spellingShingle Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
Montaña, Maria Paulina
Quercetin
Morin Rutin
Photoooxidation
Photodegradation
title_short Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
title_full Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
title_fullStr Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
title_full_unstemmed Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
title_sort Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin
dc.creator.none.fl_str_mv Montaña, Maria Paulina
Massad, Walter Alfredo
Criado, Susana Noemi
Biasutti, Maria Alicia
Garcia, Norman Andino
author Montaña, Maria Paulina
author_facet Montaña, Maria Paulina
Massad, Walter Alfredo
Criado, Susana Noemi
Biasutti, Maria Alicia
Garcia, Norman Andino
author_role author
author2 Massad, Walter Alfredo
Criado, Susana Noemi
Biasutti, Maria Alicia
Garcia, Norman Andino
author2_role author
author
author
author
dc.subject.none.fl_str_mv Quercetin
Morin Rutin
Photoooxidation
Photodegradation
topic Quercetin
Morin Rutin
Photoooxidation
Photodegradation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Kinetic and mechanistic aspects on the stability of the flavones (FL) quercetin (Que), morin (Mor) and rutin (Rut), in methanolic solution and in the presence of reactive oxygen species (ROS) generated by visible light-promoted riboflavin (Rf, vitamin B2) photoirradiation were studied. The system was chosen as a model for the evaluation of the in vivo protective effect of biological targets by the flavones. The overall picture includes the vitamin as an endogenous natural photosensitizer. A systematic study on the effect of ROS on FL photostability shows that under work conditions Que is oxidized by singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2̇-) and hydrogen peroxide; Mor is degraded by O2(1Δg) and O 2̇- whereas Rut only reacts with O2( 1Δg). Que and Rut, with an extremely poor overall rate constant, are mainly physical quenchers of O2( 1Δg). Mor, with O2(1Δ g)-interception ability slightly lower than the recognized synthetic antioxidant trolox (Tx), behaves as a typical sacrificial scavenger provided that ca 80% of the collisions with O2(1Δ g) cause its own degradation, whereas this parameter reaches around 50% in the case of Tx.
Fil: Montaña, Maria Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Biasutti, Maria Alicia. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
description Kinetic and mechanistic aspects on the stability of the flavones (FL) quercetin (Que), morin (Mor) and rutin (Rut), in methanolic solution and in the presence of reactive oxygen species (ROS) generated by visible light-promoted riboflavin (Rf, vitamin B2) photoirradiation were studied. The system was chosen as a model for the evaluation of the in vivo protective effect of biological targets by the flavones. The overall picture includes the vitamin as an endogenous natural photosensitizer. A systematic study on the effect of ROS on FL photostability shows that under work conditions Que is oxidized by singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2̇-) and hydrogen peroxide; Mor is degraded by O2(1Δg) and O 2̇- whereas Rut only reacts with O2( 1Δg). Que and Rut, with an extremely poor overall rate constant, are mainly physical quenchers of O2( 1Δg). Mor, with O2(1Δ g)-interception ability slightly lower than the recognized synthetic antioxidant trolox (Tx), behaves as a typical sacrificial scavenger provided that ca 80% of the collisions with O2(1Δ g) cause its own degradation, whereas this parameter reaches around 50% in the case of Tx.
publishDate 2010
dc.date.none.fl_str_mv 2010-07-07
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/11336/131225
Montaña, Maria Paulina; Massad, Walter Alfredo; Criado, Susana Noemi; Biasutti, Maria Alicia; Garcia, Norman Andino; Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 86; 4; 7-7-2010; 827-834
0031-8655
CONICET Digital
CONICET
url http://hdl.handle.net/11336/131225
identifier_str_mv Montaña, Maria Paulina; Massad, Walter Alfredo; Criado, Susana Noemi; Biasutti, Maria Alicia; Garcia, Norman Andino; Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: A kinetic and mechanistic study on quercetin, morin and rutin; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 86; 4; 7-7-2010; 827-834
0031-8655
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1111/j.1751-1097.2010.00754.x
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1111/j.1751-1097.2010.00754.x
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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 13.069144

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