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

Luís Cruz; Nuno Basílio; Johan Mendoza; Nuno Mateus; Victor de Freitas; Maun H. Tawara; Juan Correa; Eduardo Fernandez-Megia

doi:10.1002/chem.201901912

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

Luís Cruz, Nuno Basílio, Johan Mendoza, Nuno Mateus, Victor de Freitas, Maun H. Tawara, Juan Correa, Eduardo Fernandez-Megia

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Abstract

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 pK_h 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.

Original language	English
Pages (from-to)	11696-11706
Number of pages	11
Journal	Chemistry - A European Journal
Volume	25
Issue number	50
DOIs	https://doi.org/10.1002/chem.201901912
Publication status	Published - 6 Sept 2019

Keywords

anthocyanins
association constants
gallic acid-based dendrimers
NMR spectroscopy
UV/Vis spectroscopy

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asap paperAccepted author manuscript, 3.22 MBLicence: CC BY-NC

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

abstract = "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.",

keywords = "anthocyanins, association constants, gallic acid-based dendrimers, NMR spectroscopy, UV/Vis spectroscopy",

author = "Lu{\'i}s Cruz and Nuno Bas{\'i}lio and Johan Mendoza and Nuno Mateus and {de Freitas}, Victor and Tawara, {Maun H.} and Juan Correa and Eduardo Fernandez-Megia",

note = "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).",

year = "2019",

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language = "English",

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T1 - Impact of a Water-Soluble Gallic Acid-Based Dendrimer on the Color-Stabilizing Mechanisms of Anthocyanins

AU - Cruz, Luís

AU - Basílio, Nuno

AU - Mendoza, Johan

AU - Mateus, Nuno

AU - de Freitas, Victor

AU - Tawara, Maun H.

AU - Correa, Juan

AU - Fernandez-Megia, Eduardo

N1 - 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).

PY - 2019/9/6

Y1 - 2019/9/6

N2 - 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.

AB - 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.

KW - anthocyanins

KW - association constants

KW - gallic acid-based dendrimers

KW - NMR spectroscopy

KW - UV/Vis spectroscopy

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U2 - 10.1002/chem.201901912

DO - 10.1002/chem.201901912

M3 - Article

C2 - 31264754

AN - SCOPUS:85070784208

SN - 0947-6539

VL - 25

SP - 11696

EP - 11706

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 50

ER -

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

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Keywords

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