Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone

Autores
Montenegro, Mariana Angélica; Nazareno, Mónica Azucena; Borsarelli, Claudio Darío
Año de publicación
2007
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The kinetic of the O2(1g)-photosensitized oxidation of the flavanone naringin (7–rhamnoglucosyl-4’,5-dihydroxyflavanone, FL) and its chalcone isomer (4’–rhamnoglucosyl-2’,6’,4-trihydroxychalcone, CH) in neutral and 1 mM NaOH ethanol solutions was studied using Rose Bengal as photosensitizer. The rate constants for the chemical quenching of O2(1g) by the flavonoids (kr) were determined using either UV-Vis absorption spectroscopy or HPLC techniques, and for the total (physical + chemical) quenching (kt) were determined using time-resolved phosphorescence detection of O2(1g) at 1270 nm. A larger reactivity towards O2(1g) of CH than for FL in neutral ethanol solutions was observed, due to the extra conjugated double bond in CH. However, in alkaline media the reactivity of both isomers was larger than in neutral conditions. This behaviour was associated to the increment of electron density by the formation of a carbanion in FL and to the presence of the extended conjugated -system in the CH isomer by deprotonation of phenolic groups . In all cases, the formation of 4-hydroxybenzoic acid as ending product was detected by HPLC. Based on reported mechanisms of O2(1g)-mediated oxidation of flavonoids, the formation of 7-rhamnoglucosyl-5,4’-dihydroxyflavonol as primary photo-oxidation product was proposed. The reactivity towards O2(1g) of the aglycone of naringin (5,7,4’-trihydroxyflavanone or naringenin, NG) in alkaline conditions was lower than for the parent naringin, due to incapability of NG to form a carbanion species. These results are expected to have significance in biosynthesis, antioxidant properties and stability of naturally occurring flavonoids.
Fil: Montenegro, Mariana Angélica. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Nazareno, Mónica Azucena. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina
Fil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina
Materia
PHOTOOXIDATIONS
FLAVONOIDS
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:11336/244103
Acceder
id CONICETDig_25397324ec527a57557bcfa9809347dc
oai_identifier_str oai:ri.conicet.gov.ar:11336/244103
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its ChalconeMontenegro, Mariana AngélicaNazareno, Mónica AzucenaBorsarelli, Claudio DaríoPHOTOOXIDATIONSFLAVONOIDSSINGLET OXYGENhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The kinetic of the O2(1g)-photosensitized oxidation of the flavanone naringin (7–rhamnoglucosyl-4’,5-dihydroxyflavanone, FL) and its chalcone isomer (4’–rhamnoglucosyl-2’,6’,4-trihydroxychalcone, CH) in neutral and 1 mM NaOH ethanol solutions was studied using Rose Bengal as photosensitizer. The rate constants for the chemical quenching of O2(1g) by the flavonoids (kr) were determined using either UV-Vis absorption spectroscopy or HPLC techniques, and for the total (physical + chemical) quenching (kt) were determined using time-resolved phosphorescence detection of O2(1g) at 1270 nm. A larger reactivity towards O2(1g) of CH than for FL in neutral ethanol solutions was observed, due to the extra conjugated double bond in CH. However, in alkaline media the reactivity of both isomers was larger than in neutral conditions. This behaviour was associated to the increment of electron density by the formation of a carbanion in FL and to the presence of the extended conjugated -system in the CH isomer by deprotonation of phenolic groups . In all cases, the formation of 4-hydroxybenzoic acid as ending product was detected by HPLC. Based on reported mechanisms of O2(1g)-mediated oxidation of flavonoids, the formation of 7-rhamnoglucosyl-5,4’-dihydroxyflavonol as primary photo-oxidation product was proposed. The reactivity towards O2(1g) of the aglycone of naringin (5,7,4’-trihydroxyflavanone or naringenin, NG) in alkaline conditions was lower than for the parent naringin, due to incapability of NG to form a carbanion species. These results are expected to have significance in biosynthesis, antioxidant properties and stability of naturally occurring flavonoids.Fil: Montenegro, Mariana Angélica. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Nazareno, Mónica Azucena. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; ArgentinaFil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; ArgentinaElsevier Science SA2007-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/244103Montenegro, Mariana Angélica; Nazareno, Mónica Azucena; Borsarelli, Claudio Darío; Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 186; 1; 2-2007; 47-561010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603006003984info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2006.07.013info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:53:53Zoai:ri.conicet.gov.ar:11336/244103instacron: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:34982025-10-15 14:53:54.269CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
title Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
spellingShingle Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
Montenegro, Mariana Angélica
PHOTOOXIDATIONS
FLAVONOIDS
SINGLET OXYGEN
title_short Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
title_full Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
title_fullStr Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
title_full_unstemmed Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
title_sort Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone
dc.creator.none.fl_str_mv Montenegro, Mariana Angélica
Nazareno, Mónica Azucena
Borsarelli, Claudio Darío
author Montenegro, Mariana Angélica
author_facet Montenegro, Mariana Angélica
Nazareno, Mónica Azucena
Borsarelli, Claudio Darío
author_role author
author2 Nazareno, Mónica Azucena
Borsarelli, Claudio Darío
author2_role author
author
dc.subject.none.fl_str_mv PHOTOOXIDATIONS
FLAVONOIDS
SINGLET OXYGEN
topic PHOTOOXIDATIONS
FLAVONOIDS
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 kinetic of the O2(1g)-photosensitized oxidation of the flavanone naringin (7–rhamnoglucosyl-4’,5-dihydroxyflavanone, FL) and its chalcone isomer (4’–rhamnoglucosyl-2’,6’,4-trihydroxychalcone, CH) in neutral and 1 mM NaOH ethanol solutions was studied using Rose Bengal as photosensitizer. The rate constants for the chemical quenching of O2(1g) by the flavonoids (kr) were determined using either UV-Vis absorption spectroscopy or HPLC techniques, and for the total (physical + chemical) quenching (kt) were determined using time-resolved phosphorescence detection of O2(1g) at 1270 nm. A larger reactivity towards O2(1g) of CH than for FL in neutral ethanol solutions was observed, due to the extra conjugated double bond in CH. However, in alkaline media the reactivity of both isomers was larger than in neutral conditions. This behaviour was associated to the increment of electron density by the formation of a carbanion in FL and to the presence of the extended conjugated -system in the CH isomer by deprotonation of phenolic groups . In all cases, the formation of 4-hydroxybenzoic acid as ending product was detected by HPLC. Based on reported mechanisms of O2(1g)-mediated oxidation of flavonoids, the formation of 7-rhamnoglucosyl-5,4’-dihydroxyflavonol as primary photo-oxidation product was proposed. The reactivity towards O2(1g) of the aglycone of naringin (5,7,4’-trihydroxyflavanone or naringenin, NG) in alkaline conditions was lower than for the parent naringin, due to incapability of NG to form a carbanion species. These results are expected to have significance in biosynthesis, antioxidant properties and stability of naturally occurring flavonoids.
Fil: Montenegro, Mariana Angélica. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Nazareno, Mónica Azucena. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina
Fil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina
description The kinetic of the O2(1g)-photosensitized oxidation of the flavanone naringin (7–rhamnoglucosyl-4’,5-dihydroxyflavanone, FL) and its chalcone isomer (4’–rhamnoglucosyl-2’,6’,4-trihydroxychalcone, CH) in neutral and 1 mM NaOH ethanol solutions was studied using Rose Bengal as photosensitizer. The rate constants for the chemical quenching of O2(1g) by the flavonoids (kr) were determined using either UV-Vis absorption spectroscopy or HPLC techniques, and for the total (physical + chemical) quenching (kt) were determined using time-resolved phosphorescence detection of O2(1g) at 1270 nm. A larger reactivity towards O2(1g) of CH than for FL in neutral ethanol solutions was observed, due to the extra conjugated double bond in CH. However, in alkaline media the reactivity of both isomers was larger than in neutral conditions. This behaviour was associated to the increment of electron density by the formation of a carbanion in FL and to the presence of the extended conjugated -system in the CH isomer by deprotonation of phenolic groups . In all cases, the formation of 4-hydroxybenzoic acid as ending product was detected by HPLC. Based on reported mechanisms of O2(1g)-mediated oxidation of flavonoids, the formation of 7-rhamnoglucosyl-5,4’-dihydroxyflavonol as primary photo-oxidation product was proposed. The reactivity towards O2(1g) of the aglycone of naringin (5,7,4’-trihydroxyflavanone or naringenin, NG) in alkaline conditions was lower than for the parent naringin, due to incapability of NG to form a carbanion species. These results are expected to have significance in biosynthesis, antioxidant properties and stability of naturally occurring flavonoids.
publishDate 2007
dc.date.none.fl_str_mv 2007-02
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/11336/244103
Montenegro, Mariana Angélica; Nazareno, Mónica Azucena; Borsarelli, Claudio Darío; Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 186; 1; 2-2007; 47-56
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/244103
identifier_str_mv Montenegro, Mariana Angélica; Nazareno, Mónica Azucena; Borsarelli, Claudio Darío; Kinetic of the Photosensitized Oxygenation of the Flavanone Naringin and its Chalcone; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 186; 1; 2-2007; 47-56
1010-6030
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603006003984
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2006.07.013
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
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science SA
publisher.none.fl_str_mv Elsevier Science SA
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_ 1846083070334074880
score 13.22299

Publicaciones similares