The effect of self-aggregation on the determination of the kinetic and thermodynamic constants of the network of chemical reactions in 3-glucoside anthocyanins

Leydet, Yoann; Gavara, Raquel; Petrov, Vesselin; Diniz, Ana; Parola, A. Jorge; Piña, Fernando

doi:10.1016/j.phytochem.2012.06.022

Cited by 93 publications

(101 citation statements)

References 33 publications

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“…Our previous study reported that the greatest self‐association was malvidin‐3‐ O ‐glucoside, followed by peonidin‐3‐ O ‐glucoside and delphinidin‐3‐ O ‐glucoside (Han and Xu ). The steric structures of aggregates might be yielded differently during self‐association due to the differences on B rings of these anthocyanins, which might further lead to their color differences (Leydet and others ). In addition, the self‐aggregates probably induced a significant displacement of the anthocyanin equilibrium towards colored forms (González‐Manzano and others ).…”

Section: Resultsmentioning

confidence: 99%

Contribution of Monomeric Anthocyanins to the Color of Young Red Wine: Statistical and Experimental Approaches

Han

2015

Journal of Food Science

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Monomeric anthocyanin contributions to young red wine color were investigated using partial least square regression (PLSR) and aqueous alcohol solutions in this study. Results showed that the correlation between the anthocyanin concentration and the solution color fitted in a quadratic regression rather than linear or cubic regression. Malvidin-3-O-glucoside was estimated to show the highest contribution to young red wine color according to its concentration in wine, whereas peonidin-3-O-glucoside in its concentration contributed the least. The PLSR suggested that delphinidin-3-O-glucoside and peonidin-3-O-glucoside under the same concentration resulted in a stronger color of young red wine compared with malvidin-3-O-glucoside. These estimates were further confirmed by their color in aqueous alcohol solutions. These results suggested that delphinidin-3-O-glucoside and peonidin-3-O-glucoside were primary anthocyanins to enhance young red wine color by increasing their concentrations. This study could provide an alternative approach to improve young red wine color by adjusting anthocyanin composition and concentration.

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Section: Resultsmentioning

confidence: 99%

Contribution of Monomeric Anthocyanins to the Color of Young Red Wine: Statistical and Experimental Approaches

Han

2015

Journal of Food Science

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“…Because of their nearly planar structure and the strong tendency for aggregation into dimers and higher aggregates, they are particularly attractive candidates for ILCs. Additionally, flavylium salts possess unique structural features, that is, the ionic moiety is located in the center of the mesogenic core rather than as peripheral headgroup and the molecular shape is unsymmetrical.…”

Section: Introductionmentioning

confidence: 99%

Flavylium Salts: A Blooming Core for Bioinspired Ionic Liquid Crystals

Forschner

Knelles

Bader

et al. 2019

Chemistry A European J

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Thermotropic ionic liquid crystals based on the flavylium scaffold have been synthesized and studied for their structure‐properties relationship for the first time. The mesogens were probed by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X‐ray diffraction (XRD). Low numbers of alkoxy side chains resulted in smectic (SmA) and lamello‐columnar (LamCol) phases, whereas higher substituted flavylium salts showed Colro as well as ordered and disordered columnar (Colho, Colhd) mesophases. Mesophase width ranged from 13 K to 220 K, giving access to room temperature liquid crystals. The optical properties of the synthesized compounds were probed towards absorption and emission properties. Strong absorption with maxima between 444 and 507 nm was observed, and some chromophores were highly emissive with quantum yields up to 99 %. Ultimately, mesogenic and dye properties were examined by temperature‐dependent emissive experiments in the solid state.

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“…Self-association of anthocyanins has been investigated by UV-visible spectroscopy, circular dichroism and NMR [21,22,23]. At high concentration (>0.1 mM), anthocyanins typically form left-handed aggregates, which results in relatively modest modifications in the visible spectra (band broadening with a slight decrease of absorption at λ max ).…”

Section: Resultsmentioning

confidence: 99%

“…One study was reported with the pyranoanthocyanin formed by addition of 8-vinylcatechin (itself a product of the aromatic electrophilic substitution of acetaldehyde with catechin) and malvidin 3- O - β - d -(6- O - p -coumaroyl)glucoside. At pH = 1.3, the AH + form of this PA was shown to form a noncovalent dimer with a binding constant Kd of 3 × 10 3 M −1 [11], which is only circa twice higher than for the parent anthocyanin (estimated in the presence of 30% DMSO and thus probably lower than its value in aqueous solution) [23]. Although the AH + forms of PAs do not seem much more prone to self-association than the parent anthocyanins, under mildly acidic conditions, AH + ···A or A···A self-association is likely to be stronger due to the decrease in electrostatic repulsion.…”

Section: Resultsmentioning

confidence: 99%

p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions

Vallverdú‐Queralt

Biler

Meudec

et al. 2016

IJMS

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The physicochemical properties of the wine pigments catechyl-pyranomalvidin-3-O-glucoside (PA1) and guaiacyl-pyranomalvidin-3-O-glucoside (PA2) are extensively revisited using ultraviolet (UV)-visible spectroscopy, dynamic light scattering (DLS) and quantum chemistry density functional theory (DFT) calculations. In mildly acidic aqueous solution, each cationic pigment undergoes regioselective deprotonation to form a single neutral quinonoid base and water addition appears negligible. Above pH = 4, both PA1 and PA2 become prone to aggregation, which is manifested by the slow build-up of broad absorption bands at longer wavelengths (λ ≥ 600 nm), followed in the case of PA2 by precipitation. Some phenolic copigments are able to inhibit aggregation of pyranoanthocyanins (PAs), although at large copigment/PA molar ratios. Thus, chlorogenic acid can dissociate PA1 aggregates while catechin is inactive. With PA2, both chlorogenic acid and catechin are able to prevent precipitation but not self-association. Calculations confirmed that the noncovalent dimerization of PAs is stronger with the neutral base than with the cation and also stronger than π–π stacking of PAs to chlorogenic acid (copigmentation). For each type of complex, the most stable conformation could be obtained. Finally, PA1 can also bind hard metal ions such as Al3+ and Fe3+ and the corresponding chelates are less prone to self-association.

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The effect of self-aggregation on the determination of the kinetic and thermodynamic constants of the network of chemical reactions in 3-glucoside anthocyanins

Cited by 93 publications

References 33 publications

Contribution of Monomeric Anthocyanins to the Color of Young Red Wine: Statistical and Experimental Approaches

Contribution of Monomeric Anthocyanins to the Color of Young Red Wine: Statistical and Experimental Approaches

Flavylium Salts: A Blooming Core for Bioinspired Ionic Liquid Crystals

p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions

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