Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins

Detalhes bibliográficos
Autor(a) principal: Cruz, Luís
Data de Publicação: 2019
Outros Autores: Basílio, Nuno, Mendoza, Johan, Mateus, Nuno, de Freitas, Victor, Tawara, Maun H., Correa, Juan, Fernandez-Megia, Eduardo
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/96164
Resumo: project grant (PTDC/OCE-ETA/31250/2017) with financial support from FCT/MCTES through national funds and co-financed by FEDER, under the Partnership Agreement PT2020 (UID/QUI/50006/2019-POCI/01/0145/FEDER/007265). Financial support was also obtained from the Spanish Ministry of Science, Innovation and Universities (CTQ2015-69021-R and RTI2018-102212-B-I00), the Xunta de Galicia (GRC2014/040, ED431C 2018/30, and Centro Singular de Investigacion de Galicia Accreditation 2016-2019, ED431G/09) and the European Union (European Regional Development Fund-ERDF).
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spelling Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyaninsanthocyaninsassociation constantsgallic acid-based dendrimersNMR spectroscopyUV/Vis spectroscopyCatalysisOrganic Chemistryproject grant (PTDC/OCE-ETA/31250/2017) with financial support from FCT/MCTES through national funds and co-financed by FEDER, under the Partnership Agreement PT2020 (UID/QUI/50006/2019-POCI/01/0145/FEDER/007265). Financial support was also obtained from the Spanish Ministry of Science, Innovation and Universities (CTQ2015-69021-R and RTI2018-102212-B-I00), the Xunta de Galicia (GRC2014/040, ED431C 2018/30, and Centro Singular de Investigacion de Galicia Accreditation 2016-2019, ED431G/09) and the European Union (European Regional Development Fund-ERDF).The interaction of two anthocyanins with a water-soluble polyanionic dendrimer was studied through UV/Vis, stopped-flow, and NMR spectroscopy. Cyanidin-3-glucoside (cy3glc) revealed a stronger interaction than malvidin-3-glucoside (mv3glc) at pH 1 according to their apparent association constants. A higher color increased was also obtained for cy3glc at pH 3.5 as a result of this stronger interaction. A high-frequency chemical shift of the cy3glc aromatic protons suggest the formation of ionic pairs. The interaction parameters (K≈700 m−1, n≈295) indicated the binding of approximately two anthocyanin molecules by each sulfate group. The equilibrium and rate constants of cy3glc in the presence of dendrimer showed an increased stability of the flavylium cation and a higher protection of this species from hydration (pK′a and pKh increased almost one pH unit). The tuning and color stabilization of anthocyanins by using this dendrimer allow novel applications as colorimetric sensors for food packaging.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNCruz, LuísBasílio, NunoMendoza, JohanMateus, Nunode Freitas, VictorTawara, Maun H.Correa, JuanFernandez-Megia, Eduardo2022-03-31T00:31:40Z2019-09-062019-09-06T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article11application/pdfhttp://hdl.handle.net/10362/96164eng0947-6539PURE: 16262404https://doi.org/10.1002/chem.201901912info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T04:43:52Zoai:run.unl.pt:10362/96164Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:38:29.372461Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
title Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
spellingShingle Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
Cruz, Luís
anthocyanins
association constants
gallic acid-based dendrimers
NMR spectroscopy
UV/Vis spectroscopy
Catalysis
Organic Chemistry
title_short Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
title_full Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
title_fullStr Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
title_full_unstemmed Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
title_sort Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins
author Cruz, Luís
author_facet Cruz, Luís
Basílio, Nuno
Mendoza, Johan
Mateus, Nuno
de Freitas, Victor
Tawara, Maun H.
Correa, Juan
Fernandez-Megia, Eduardo
author_role author
author2 Basílio, Nuno
Mendoza, Johan
Mateus, Nuno
de Freitas, Victor
Tawara, Maun H.
Correa, Juan
Fernandez-Megia, Eduardo
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Cruz, Luís
Basílio, Nuno
Mendoza, Johan
Mateus, Nuno
de Freitas, Victor
Tawara, Maun H.
Correa, Juan
Fernandez-Megia, Eduardo
dc.subject.por.fl_str_mv anthocyanins
association constants
gallic acid-based dendrimers
NMR spectroscopy
UV/Vis spectroscopy
Catalysis
Organic Chemistry
topic anthocyanins
association constants
gallic acid-based dendrimers
NMR spectroscopy
UV/Vis spectroscopy
Catalysis
Organic Chemistry
description project grant (PTDC/OCE-ETA/31250/2017) with financial support from FCT/MCTES through national funds and co-financed by FEDER, under the Partnership Agreement PT2020 (UID/QUI/50006/2019-POCI/01/0145/FEDER/007265). Financial support was also obtained from the Spanish Ministry of Science, Innovation and Universities (CTQ2015-69021-R and RTI2018-102212-B-I00), the Xunta de Galicia (GRC2014/040, ED431C 2018/30, and Centro Singular de Investigacion de Galicia Accreditation 2016-2019, ED431G/09) and the European Union (European Regional Development Fund-ERDF).
publishDate 2019
dc.date.none.fl_str_mv 2019-09-06
2019-09-06T00:00:00Z
2022-03-31T00:31:40Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/96164
url http://hdl.handle.net/10362/96164
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0947-6539
PURE: 16262404
https://doi.org/10.1002/chem.201901912
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11
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dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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