Singlet oxygen quenching by anthocyanin's flavylium cations

Autores
Rosso, Veridiana V. De; Moran Vieyra, Faustino Eduardo; Mercadante, Adriana Z.; Borsarelli, Claudio Darío
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The quenching of singlet molecular oxygen (1O2) by the flavylium cation form of six widespread anthocyanin derivatives: cyanidin 3-glucoside (CG), cyanidin 3-rutinoside (CR), cyanidin 3-galactoside (CGL), malvidin (M), malvidin 3-glucoside (MG) and malvidin 3,5-diglucoside (MDG) was studied in 1% HCl methanol solution by time-resolved phosphorescence detection (TRPD) of 1O2 and photostationary actinometry using perinaphthenone and methylene blue as sensitizers, respectively. The average value of the total (k0) and chemical (kc) quenching rate constants were ∼ 4×108 M-1 S-1 and 3×106 M-1 S-1, respectively, indicating the good performance of the studied anthocyanins as catalytic quenchers of 1O2. The quenching efficiency was larger for malvidin than for cyanidin derivatives, probably by the extra electron-donating methoxy group in ring B of the malvidin derivatives; and it was also dependent on the number and type of glycosylated substitution. As observed for other phenolic-like derivatives, the quenching of 1O2 by anthocyanins was mediated by a charge-transfer mechanism, which was modulated by the total number of -OR substituents that increases the electron-donating ability of these compounds.
Fil: Rosso, Veridiana V. De. Universidade Estadual de Campinas; Brasil
Fil: Moran Vieyra, Faustino Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Mercadante, Adriana Z.. Universidade Estadual de Campinas; Brasil
Fil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Materia
Anthocyanins
Antioxidant Capacity
Flavylium Cation
Pigments
Singlet Oxygen
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:11336/54522
Acceder
id CONICETDig_c834435d837d744b44a14a4fb7163ca3
oai_identifier_str oai:ri.conicet.gov.ar:11336/54522
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Singlet oxygen quenching by anthocyanin's flavylium cationsRosso, Veridiana V. DeMoran Vieyra, Faustino EduardoMercadante, Adriana Z.Borsarelli, Claudio DaríoAnthocyaninsAntioxidant CapacityFlavylium CationPigmentsSinglet Oxygenhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The quenching of singlet molecular oxygen (1O2) by the flavylium cation form of six widespread anthocyanin derivatives: cyanidin 3-glucoside (CG), cyanidin 3-rutinoside (CR), cyanidin 3-galactoside (CGL), malvidin (M), malvidin 3-glucoside (MG) and malvidin 3,5-diglucoside (MDG) was studied in 1% HCl methanol solution by time-resolved phosphorescence detection (TRPD) of 1O2 and photostationary actinometry using perinaphthenone and methylene blue as sensitizers, respectively. The average value of the total (k0) and chemical (kc) quenching rate constants were ∼ 4×108 M-1 S-1 and 3×106 M-1 S-1, respectively, indicating the good performance of the studied anthocyanins as catalytic quenchers of 1O2. The quenching efficiency was larger for malvidin than for cyanidin derivatives, probably by the extra electron-donating methoxy group in ring B of the malvidin derivatives; and it was also dependent on the number and type of glycosylated substitution. As observed for other phenolic-like derivatives, the quenching of 1O2 by anthocyanins was mediated by a charge-transfer mechanism, which was modulated by the total number of -OR substituents that increases the electron-donating ability of these compounds.Fil: Rosso, Veridiana V. De. Universidade Estadual de Campinas; BrasilFil: Moran Vieyra, Faustino Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Mercadante, Adriana Z.. Universidade Estadual de Campinas; BrasilFil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaTaylor & Francis2008-12info: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/11336/54522Rosso, Veridiana V. De; Moran Vieyra, Faustino Eduardo; Mercadante, Adriana Z.; Borsarelli, Claudio Darío; Singlet oxygen quenching by anthocyanin's flavylium cations; Taylor & Francis; Free Radical Research; 42; 10; 12-2008; 885-8911071-57621029-2470CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1080/10715760802506349info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/abs/10.1080/10715760802506349info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:54:45Zoai:ri.conicet.gov.ar:11336/54522instacron: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:34982025-09-03 09:54:45.753CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Singlet oxygen quenching by anthocyanin's flavylium cations
title Singlet oxygen quenching by anthocyanin's flavylium cations
spellingShingle Singlet oxygen quenching by anthocyanin's flavylium cations
Rosso, Veridiana V. De
Anthocyanins
Antioxidant Capacity
Flavylium Cation
Pigments
Singlet Oxygen
title_short Singlet oxygen quenching by anthocyanin's flavylium cations
title_full Singlet oxygen quenching by anthocyanin's flavylium cations
title_fullStr Singlet oxygen quenching by anthocyanin's flavylium cations
title_full_unstemmed Singlet oxygen quenching by anthocyanin's flavylium cations
title_sort Singlet oxygen quenching by anthocyanin's flavylium cations
dc.creator.none.fl_str_mv Rosso, Veridiana V. De
Moran Vieyra, Faustino Eduardo
Mercadante, Adriana Z.
Borsarelli, Claudio Darío
author Rosso, Veridiana V. De
author_facet Rosso, Veridiana V. De
Moran Vieyra, Faustino Eduardo
Mercadante, Adriana Z.
Borsarelli, Claudio Darío
author_role author
author2 Moran Vieyra, Faustino Eduardo
Mercadante, Adriana Z.
Borsarelli, Claudio Darío
author2_role author
author
author
dc.subject.none.fl_str_mv Anthocyanins
Antioxidant Capacity
Flavylium Cation
Pigments
Singlet Oxygen
topic Anthocyanins
Antioxidant Capacity
Flavylium Cation
Pigments
Singlet Oxygen
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The quenching of singlet molecular oxygen (1O2) by the flavylium cation form of six widespread anthocyanin derivatives: cyanidin 3-glucoside (CG), cyanidin 3-rutinoside (CR), cyanidin 3-galactoside (CGL), malvidin (M), malvidin 3-glucoside (MG) and malvidin 3,5-diglucoside (MDG) was studied in 1% HCl methanol solution by time-resolved phosphorescence detection (TRPD) of 1O2 and photostationary actinometry using perinaphthenone and methylene blue as sensitizers, respectively. The average value of the total (k0) and chemical (kc) quenching rate constants were ∼ 4×108 M-1 S-1 and 3×106 M-1 S-1, respectively, indicating the good performance of the studied anthocyanins as catalytic quenchers of 1O2. The quenching efficiency was larger for malvidin than for cyanidin derivatives, probably by the extra electron-donating methoxy group in ring B of the malvidin derivatives; and it was also dependent on the number and type of glycosylated substitution. As observed for other phenolic-like derivatives, the quenching of 1O2 by anthocyanins was mediated by a charge-transfer mechanism, which was modulated by the total number of -OR substituents that increases the electron-donating ability of these compounds.
Fil: Rosso, Veridiana V. De. Universidade Estadual de Campinas; Brasil
Fil: Moran Vieyra, Faustino Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Mercadante, Adriana Z.. Universidade Estadual de Campinas; Brasil
Fil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
description The quenching of singlet molecular oxygen (1O2) by the flavylium cation form of six widespread anthocyanin derivatives: cyanidin 3-glucoside (CG), cyanidin 3-rutinoside (CR), cyanidin 3-galactoside (CGL), malvidin (M), malvidin 3-glucoside (MG) and malvidin 3,5-diglucoside (MDG) was studied in 1% HCl methanol solution by time-resolved phosphorescence detection (TRPD) of 1O2 and photostationary actinometry using perinaphthenone and methylene blue as sensitizers, respectively. The average value of the total (k0) and chemical (kc) quenching rate constants were ∼ 4×108 M-1 S-1 and 3×106 M-1 S-1, respectively, indicating the good performance of the studied anthocyanins as catalytic quenchers of 1O2. The quenching efficiency was larger for malvidin than for cyanidin derivatives, probably by the extra electron-donating methoxy group in ring B of the malvidin derivatives; and it was also dependent on the number and type of glycosylated substitution. As observed for other phenolic-like derivatives, the quenching of 1O2 by anthocyanins was mediated by a charge-transfer mechanism, which was modulated by the total number of -OR substituents that increases the electron-donating ability of these compounds.
publishDate 2008
dc.date.none.fl_str_mv 2008-12
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/11336/54522
Rosso, Veridiana V. De; Moran Vieyra, Faustino Eduardo; Mercadante, Adriana Z.; Borsarelli, Claudio Darío; Singlet oxygen quenching by anthocyanin's flavylium cations; Taylor & Francis; Free Radical Research; 42; 10; 12-2008; 885-891
1071-5762
1029-2470
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54522
identifier_str_mv Rosso, Veridiana V. De; Moran Vieyra, Faustino Eduardo; Mercadante, Adriana Z.; Borsarelli, Claudio Darío; Singlet oxygen quenching by anthocyanin's flavylium cations; Taylor & Francis; Free Radical Research; 42; 10; 12-2008; 885-891
1071-5762
1029-2470
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1080/10715760802506349
info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/abs/10.1080/10715760802506349
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
application/pdf
dc.publisher.none.fl_str_mv Taylor & Francis
publisher.none.fl_str_mv Taylor & Francis
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
_version_ 1842269305040797696
score 13.13397

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