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Nino Russo - One of the best experts on this subject based on the ideXlab platform.
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Oenin/Syringic Acid Copigmentation: Insights From a Theoretical Study.
Frontiers in chemistry, 2019Co-Authors: Yunkui Li, Mario Prejano, Marirosa Toscano, Nino RussoAbstract:On the basis of the dispersion-corrected density functional theory, a computational model is proposed to describe the oenin/syringic acid Copigmentation and to explore the non-covalent interaction between the anthocyanin and the copigment in the framework of implicit solvent approach. The predicted binding free energy and visible spectrum shift of this Copigmentation complex are in accordance with the experimental observations. The used model provides a good structural description of oenin/syringic acid complex and suggests that the intermolecular hydrogen bonding, in which the hydroxyl-rich sugar moiety in oenin plays a key role, may be the determinant for the formation and nature of the Copigmentation complex.
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oenin syringic acid Copigmentation insights from a theoretical study
Frontiers in chemistry, 2019Co-Authors: Yunkui Li, Mario Prejano, Marirosa Toscano, Nino RussoAbstract:On the basis of the dispersion-corrected density functional theory, a computational model is proposed to describe the oenin/syringic acid Copigmentation and to explore the non-covalent interaction between the anthocyanin and the copigment in the framework of implicit solvent approach. The predicted binding free energy and visible spectrum shift of this Copigmentation complex are in accordance with the experimental observations. The used model provides a good structural description of oenin/syringic acid complex and suggests that the intermolecular hydrogen bonding, in which the hydroxyl-rich sugar moiety in oenin plays a key role, may be the determinant for the formation and nature of the Copigmentation complex.
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oenin and quercetin Copigmentation highlights from density functional theory
Frontiers in chemistry, 2018Co-Authors: Yunkui Li, Mario Prejano, Marirosa Toscano, Nino RussoAbstract:Making use of anthocyanin Copigmentation, it is possible to effectively improve color quality and stability of red wines and other foods. This can be done by selecting strong copigments, but a 1-fold experimental screening usually entails a high cost and a low efficiency. The aim of this work is to show how a theoretical model based on density functional theory can be useful for an accurate and rapid prediction of Copigmentation ability of a copigment. The present study, concerning the Copigmentation between oenin and quercetin under the framework of implicit solvent, indicates that, in these conditions, the intermolecular hydrogen bonds play an important role in the system stabilization. The dispersion interaction slightly affects the structure, energies and UV-Vis spectral properties of the Copigmentation complex.
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spectrophotometric study of the Copigmentation of malvidin 3 o glucoside with p coumaric vanillic and syringic acids
Food Chemistry, 2013Co-Authors: Naim Malaj, Bruna Clara De Simone, Angelo Domenico Quartarolo, Nino RussoAbstract:Abstract Anthocyanins are a natural source of pigments in plants and their processed food products have become attractive and excellent candidates to replace the synthetic colourants due to their characteristic intense colours and associated health benefits. The intermolecular Copigmentation between anthocyanins and other colourless compounds has been reported to be an important way to enhance and stabilise the colour intensity of aqueous solutions. In the present work we report the equilibrium constant, stoichiometric ratio and the thermodynamic parameters (Δ G °, Δ H ° and Δ S °) related to the intermolecular Copigmentation reactions of the anthocyanin malvidin 3-O-glucoside with one hydroxycinnamic acid ( p -coumaric acid) and two O-methylated hydroxybenzoic acids (vanillic and syringic acid). Different factors which affect their interactions such as copigment concentration, pH and temperature of the medium are examined at two pH levels (pH = 2.50 and 3.65) corresponding to those of the major food mediums where these reactions take place (fruit juices, wine, jams etc.).
Bo Zhang - One of the best experts on this subject based on the ideXlab platform.
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Copigmentation evidence of oenin with phenolic compounds a comparative study of spectrographic thermodynamic and theoretical data
Food Chemistry, 2020Co-Authors: Bo Zhang, Pan Pan Zhou, Qiang Wang, Ningning LiAbstract:Abstract The Copigmentation effects of polyphenol with different structures vary greatly. Therefore, the aim of this study is to investigate possible interactions in red wine model solutions between oenin and three phenolic compounds: danshensu, caffeic acid and rosmarinic acid. Our results show that the Copigmentation of rosmarinic acid is the strongest among the compounds tested. The colourimetric parameters indicate that colour intensity becomes enhanced with increasing concentration of these copigments, leading to darker and more vivid bluish colours. Thermodynamic and quantum chemical investigations are performed to interpret the absorption properties in the visible range. Fluorescence spectroscopy confirms the interaction between caffeic acid and oenin, while FTIR spectroscopic results further suggest a role for hydrogen bonds in the overall process. To our knowledge, this is the first experimentally corroborated direct evidence of hydrogen bonds in Copigmentation.
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the effect of prefermentative addition of gallic acid and ellagic acid on the red wine color Copigmentation and phenolic profiles during wine aging
Food Research International, 2017Co-Authors: Xinke Zhang, Fei He, Bo Zhang, Malcolm J Reeves, Xu Zhao, Chang Qing DuanAbstract:Abstract Though non-anthocyanin phenolics normally do not have red color, they affect the red color expression in the Copigmentation of red wines. In this study, the influence of prefermentative addition of 300 mg/L gallic acid and ellagic acid, as cofactors, on aging dry red wines had been systematically evaluated at the industrial scales from the perspectives of color, phenolic profiles and Copigmentation effects of anthocyanins. Red wines made with these two compounds exhibited better color properties than the control, having better CIELAB chromatic parameters. Additionally, significantly higher levels of detectable anthocyanins and copigmented anthocyanin ratio had been observed. Wines with ellagic acid showed better chromatic properties and phenolic profiles than wines with gallic acid, as shown in previous theoretical results. Anti-Copigmentation phenomenon was noticed and elucidated. These practical results confirmed that ellagic acid was the better cofactor, and would give more additional guidance for the production of high quality wine. Chemical compounds Malvidin-3-O-glucoside (PubChem CID: 443,652); Petunidin-3-O-glucoside (PubChem CID: 443,651); Delphinidin-3-O-glucoside (PubChem CID: 443,650); Peonidin-3-O-glucoside (PubChem CID: 443,654); Ellagic acid (PubChem CID: 5,281,855); Gallic acid (PubChem CID: 370); Quercetin (PubChem CID: 443,654); Caffeic acid (PubChem CID: 689,043); (+)-catechin (PubChem CID: 9064); Vanillic acid (PubChem CID: 8468).
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The color expression of Copigmentation between malvidin-3-O-glucoside and three phenolic aldehydes in model solutions: The effects of pH and molar ratio
Food Chemistry, 2016Co-Authors: Bo Zhang, Pan Pan Zhou, Fei He, Yue Liu, Chang Qing DuanAbstract:Copigmentation was investigated in model solutions between the anthocyanin malvidin-3-O-glucoside and three phenolic aldehydes (vanillic, syringic and coniferyl aldehydes) as a function of the pH and the pigment/copigment molar ratio. Tristimulus colorimetry was applied to evaluate the chromatic variations induced by Copigmentation process. The results indicated that the greatest magnitude of Copigmentation was obtained at pH 3.0 and molar ratio of 1:100, being significantly higher with coniferyl aldehyde, followed by syringic and vanillic aldehydes. The equilibrium constant (K) and Gibbs free energies (ΔG°) determined here show a spontaneous exothermic reaction. Theoretical calculations (ΔGbinding, ΔE) specified the relative arrangement of the pigment and copigment molecules within the complexes. In addition, an atoms in molecules (AIM) analysis was used to explore the main driving forces contributing to the formation of Copigmentation complexes.
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Copigmentation between malvidin 3 o glucoside and hydroxycinnamic acids in red wine model solutions investigations with experimental and theoretical methods
Food Research International, 2015Co-Authors: Pan Pan Zhou, Fei He, Bo Zhang, Chang Qing DuanAbstract:Abstract The Copigmentation effect between malvidin-3-O-glucoside and three hydroxycinnamic acids (p-coumaric, caffeic and ferulic acids) on the color expression was assessed in red wine model solutions. The colorimetric parameters indicated that the increasing concentration of these copigments could enhance the color intensity of the wine-like solutions (hyperchromic effect and bathochromic shift), and displayed the darker and more vivid bluish chromatic properties. The equilibrium constant (K), stoichiometric ratio (n) and thermodynamic parameters (∆ G°, ∆ H°, ∆ S°) were determined by the spectrophotometric methods, showing the generally spontaneous exothermic character of the process. In addition, quantum chemical investigations were performed to interpret the absorption differences. The results showed that the ferulic acid was the more powerful copigment compared with the other two hydroxycinnamic counterparts, indicating that the Copigmentation was not only correlated to the concentration of the copigments but also strongly dependent on their molecular structures. AIM analysis was also used to explore the driving forces contributing to the Copigmentation, which suggested that the hydrogen bond and van der Waals interactions were the main driving forces for the three pigment–copigment complexes.
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Copigmentation of malvidin 3 o glucoside with five hydroxybenzoic acids in red wine model solutions experimental and theoretical investigations
Food Chemistry, 2015Co-Authors: Bo Zhang, Pan Pan Zhou, Fei He, Chang Qing DuanAbstract:In the present research, the Copigmentations of malvidin-3-O-glucoside with five hydroxybenzoic cofactors (p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, and syringic acid) were investigated. The influence of the concentration of these cofactors and the reaction temperature was examined. The equilibrium constant (K), stoichiometric ratio (n) and the thermodynamic parameters (Delta G degrees, Delta H degrees, Delta SO degrees) related to the Copigmentation were also reported here. Theoretical calculations were performed to identify the relative arrangement between the pigment and cofactors in the Copigmentation complexes. Besides, the comparison of the relative binding free energies (Delta Delta G(binding)) derived from the theoretical calculations and experimental data were made, and the binding strength of these Copigmentation complexes was discussed with the interaction energies (Delta E). AIM analysis was also used to explore the main driving forces contributing to the Copigmentation. In the comparison of the five studied cofactors, syringic acid had a stronger Copigmentation effect than the other four phenolic acids investigated. (C) 2014 Elsevier Ltd. All rights reserved.
Chang Qing Duan - One of the best experts on this subject based on the ideXlab platform.
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the effect of prefermentative addition of gallic acid and ellagic acid on the red wine color Copigmentation and phenolic profiles during wine aging
Food Research International, 2017Co-Authors: Xinke Zhang, Fei He, Bo Zhang, Malcolm J Reeves, Xu Zhao, Chang Qing DuanAbstract:Abstract Though non-anthocyanin phenolics normally do not have red color, they affect the red color expression in the Copigmentation of red wines. In this study, the influence of prefermentative addition of 300 mg/L gallic acid and ellagic acid, as cofactors, on aging dry red wines had been systematically evaluated at the industrial scales from the perspectives of color, phenolic profiles and Copigmentation effects of anthocyanins. Red wines made with these two compounds exhibited better color properties than the control, having better CIELAB chromatic parameters. Additionally, significantly higher levels of detectable anthocyanins and copigmented anthocyanin ratio had been observed. Wines with ellagic acid showed better chromatic properties and phenolic profiles than wines with gallic acid, as shown in previous theoretical results. Anti-Copigmentation phenomenon was noticed and elucidated. These practical results confirmed that ellagic acid was the better cofactor, and would give more additional guidance for the production of high quality wine. Chemical compounds Malvidin-3-O-glucoside (PubChem CID: 443,652); Petunidin-3-O-glucoside (PubChem CID: 443,651); Delphinidin-3-O-glucoside (PubChem CID: 443,650); Peonidin-3-O-glucoside (PubChem CID: 443,654); Ellagic acid (PubChem CID: 5,281,855); Gallic acid (PubChem CID: 370); Quercetin (PubChem CID: 443,654); Caffeic acid (PubChem CID: 689,043); (+)-catechin (PubChem CID: 9064); Vanillic acid (PubChem CID: 8468).
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The color expression of Copigmentation between malvidin-3-O-glucoside and three phenolic aldehydes in model solutions: The effects of pH and molar ratio
Food Chemistry, 2016Co-Authors: Bo Zhang, Pan Pan Zhou, Fei He, Yue Liu, Chang Qing DuanAbstract:Copigmentation was investigated in model solutions between the anthocyanin malvidin-3-O-glucoside and three phenolic aldehydes (vanillic, syringic and coniferyl aldehydes) as a function of the pH and the pigment/copigment molar ratio. Tristimulus colorimetry was applied to evaluate the chromatic variations induced by Copigmentation process. The results indicated that the greatest magnitude of Copigmentation was obtained at pH 3.0 and molar ratio of 1:100, being significantly higher with coniferyl aldehyde, followed by syringic and vanillic aldehydes. The equilibrium constant (K) and Gibbs free energies (ΔG°) determined here show a spontaneous exothermic reaction. Theoretical calculations (ΔGbinding, ΔE) specified the relative arrangement of the pigment and copigment molecules within the complexes. In addition, an atoms in molecules (AIM) analysis was used to explore the main driving forces contributing to the formation of Copigmentation complexes.
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Copigmentation between malvidin 3 o glucoside and hydroxycinnamic acids in red wine model solutions investigations with experimental and theoretical methods
Food Research International, 2015Co-Authors: Pan Pan Zhou, Fei He, Bo Zhang, Chang Qing DuanAbstract:Abstract The Copigmentation effect between malvidin-3-O-glucoside and three hydroxycinnamic acids (p-coumaric, caffeic and ferulic acids) on the color expression was assessed in red wine model solutions. The colorimetric parameters indicated that the increasing concentration of these copigments could enhance the color intensity of the wine-like solutions (hyperchromic effect and bathochromic shift), and displayed the darker and more vivid bluish chromatic properties. The equilibrium constant (K), stoichiometric ratio (n) and thermodynamic parameters (∆ G°, ∆ H°, ∆ S°) were determined by the spectrophotometric methods, showing the generally spontaneous exothermic character of the process. In addition, quantum chemical investigations were performed to interpret the absorption differences. The results showed that the ferulic acid was the more powerful copigment compared with the other two hydroxycinnamic counterparts, indicating that the Copigmentation was not only correlated to the concentration of the copigments but also strongly dependent on their molecular structures. AIM analysis was also used to explore the driving forces contributing to the Copigmentation, which suggested that the hydrogen bond and van der Waals interactions were the main driving forces for the three pigment–copigment complexes.
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Copigmentation of malvidin 3 o glucoside with five hydroxybenzoic acids in red wine model solutions experimental and theoretical investigations
Food Chemistry, 2015Co-Authors: Bo Zhang, Pan Pan Zhou, Fei He, Chang Qing DuanAbstract:In the present research, the Copigmentations of malvidin-3-O-glucoside with five hydroxybenzoic cofactors (p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, and syringic acid) were investigated. The influence of the concentration of these cofactors and the reaction temperature was examined. The equilibrium constant (K), stoichiometric ratio (n) and the thermodynamic parameters (Delta G degrees, Delta H degrees, Delta SO degrees) related to the Copigmentation were also reported here. Theoretical calculations were performed to identify the relative arrangement between the pigment and cofactors in the Copigmentation complexes. Besides, the comparison of the relative binding free energies (Delta Delta G(binding)) derived from the theoretical calculations and experimental data were made, and the binding strength of these Copigmentation complexes was discussed with the interaction energies (Delta E). AIM analysis was also used to explore the main driving forces contributing to the Copigmentation. In the comparison of the five studied cofactors, syringic acid had a stronger Copigmentation effect than the other four phenolic acids investigated. (C) 2014 Elsevier Ltd. All rights reserved.
Francisco José Heredia - One of the best experts on this subject based on the ideXlab platform.
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Improving the color and aging aptitude of Syrah wines in warm climate by wood–grape mix maceration
European Food Research and Technology, 2017Co-Authors: María Jesús Cejudo-bastante, Francisco J. Rivero-granados, Francisco José HerediaAbstract:© 2016, Springer-Verlag Berlin Heidelberg. The amelioration of aging aptitude of Syrah red wines from warm climate regions by adding oak wood chips to the grape maceration/fermentation has been developed. Our attention was focused on the tristimulus colorimetry, differential colorimetry and phenolic composition. This technique was applied with an eye toward improving color stabilization of wines in a warm climate region where common loss of color normally occurs. On the basis of the results, a color enhancement (by an increment of chroma, Cab*) and significantly (p < 0.05) higher amounts of total polyphenols, anthocyanins, flavan-3-ols and esters of hydroxycinnamic acids were observed in Syrah red wines, favoring a significantly (p < 0.05) higher percentage of Copigmentation and, hence, color stabilization. Finally, it could be affirmed that the joint addition of oak wood chips (during both fermentation and aging) induced visually perceptible color differences (ΔEab* > 3), mainly quantitative (Δ 2 L and Δ 2 C), from the early months of storage.
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Pre-fermentative addition of an enzymatic grape seed hydrolysate in warm climate winemaking. Effect on the differential colorimetry, Copigmentation and polyphenolic profiles
Food Chemistry, 2016Co-Authors: María Jesús Cejudo-bastante, M. José Jara-palacios, Julián Carlos Rivas-gonzalo, Bruno Rodríguez-morgado, Juan Parrado, Francisco José HerediaAbstract:The effect of adding an enzymatic hydrolysate of grape seeds (EH-GS) during Syrah wine fermentation in a warm climate has been evaluated. We focused on the polyphenolic composition as well as the application of differential and tristimulus colorimetry to colour data. This is the first attempt at using this oenological alternative to avoid common colour losses of red wines elaborated in a warm climate. The addition of 250 g (simple dose, SW) of EH-GS to 120 kg of fermentation material promoted a significant (p < 0.05) increase in the polyphenolic content of stored wines, especially in benzoic acid, hydroxycinnamic acid derivative, flavonol and anthocyanin levels. This increase could promote a higher Copigmentation percentage and maximum colour stabilization (C∗ab) without significantly changing the wine tonality. Unexpectedly, the use of a double quantity (DW) of EH-GS resulted in significantly less chroma than for control wines (CW), demonstrating visually perceptible colour changes (ΔE∗ab> 3 CIELAB units).
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Optimisation of an oak chips-grape mix maceration process. Influence of chip dose and maceration time
Food Chemistry, 2016Co-Authors: Belén Gordillo, Berta Baca-bocanegra, Ignacio García Estévez, Natalia Quijada-morín, Francisco José Heredia, FRANCISCO JOSÉ RODRIGUEZ PULIDO, M. Lourdes González-miret, María Teresa Escribano-bailónAbstract:Oak chips-related phenolics are able to modify the composition of red wine and modulate the colour stability. In this study, the effect of two maceration techniques, traditional and oak chips-grape mix process, on the phenolic composition and colour of Syrah red wines from warm climate was studied. Two doses of oak chips (3 and 6 g/L) at two maceration times (5 and 10 days) during fermentation was considered. Changes on phenolic composition (HPLC-DAD-MS), Copigmentation/polymerisation (spectrophotometry), and colour (Tristimulus and Differential Colorimetry) were assessed by multivariate statistical techniques. The addition of oak chips at shorter maceration times enhanced phenolic extraction, colour and its stabilisation in comparison to the traditional maceration. On contrast, increasing chip dose in extended maceration time resulted in wines with lighter and less stable colour. Results open the possibility of optimise alternative technological applications to traditional grape maceration for avoiding the common loss of colour of wines from warm climate.
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Color-Copigmentation study by tristimulus colorimetry (CIELAB) in red wines obtained from Tempranillo and Graciano varieties
Food Research International, 2013Co-Authors: Matilde García-marino, María Teresa Escribano-bailón, M. Luisa Escudero-gilete, Francisco José Heredia, Julián Carlos Rivas-gonzaloAbstract:A study of the changes of Copigmentation phenomenon in wines elaborated from different varieties has been undertaken. Colorimetric measurement of Tempranillo (T) and Graciano (G) monovarietal wines, and two 80:20 blend wines: M, (grape blending T and G, co-maceration) and W (wine blending T and G, co-vinification) was performed by spectrophotometry. Significant differences (p
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comprehensive colorimetric study of anthocyanic Copigmentation in model solutions effects of ph and molar ratio
Journal of Agricultural and Food Chemistry, 2012Co-Authors: Belén Gordillo, Francisco J Rodriguezpulido, Luisa M Escuderogilete, Lourdes M Gonzalezmiret, Francisco José HerediaAbstract:New colorimetric variables have been defined in the uniform CIELAB color space to assess the quantitative and qualitative color changes induced by Copigmentation and their incidence on visual perception. The Copigmentation process was assayed in model solutions between malvidin 3-glucoside and three phenolic compounds (catechin, epicatechin, and caffeic acid) as a function of the pH and the pigment/copigment molar ratio. Along the pH variation, the greatest magnitude of Copigmentation was obtained at pH 3.0, being significantly higher with epicatechin and caffeic acid. At high acidic pH, the main contribution of Copigmentation to the total color was qualitative, whereas between pH 2.0 and 4.0, the main colorimetric contribution was quantitative. The contribution of epicatechin and caffeic acid to the color changes was more marked for the quantitative characteristics. On contrast, particularly at higher pH values, the qualitative contribution was more important in catechin copigmented solutions. Increasing...
Isidro Hermosin Gutierrez - One of the best experts on this subject based on the ideXlab platform.
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phenolic composition and magnitude of Copigmentation in young and shortly aged red wines made from the cultivars cabernet sauvignon cencibel and syrah
Food Chemistry, 2005Co-Authors: Isidro Hermosin Gutierrez, Eva Sanchezpalomo Lorenzo, Almudena Vicario EspinosaAbstract:Abstract Young and shortly aged red wines made from single cultivar grapes grown in the warm climate region of La Mancha (Spain), were examined for their phenolic composition and effects of Copigmentation on wine colour. In addition to anthocyanins, flavonol and hydroxycinnamic acid profiles allowed the varietal differentiation of these wines. Characteristic flavonols found were principally glycosides, the main ones, being: myricetin 3-glucoside, quercetin 3-glucoside, and quercetin 3-glucuronide. The fraction of red colour due to copigmented anthocyanins ranged from 32% to 43% at the end of the alcoholic fermentation, and this decreased to 20–34% after 3 months of ageing, when a decrease in both monomeric anthocyanin and flavonol concentrations was also observed . Cencibel wines showed the greatest loss in flavonols after 3 months, but these were apparently replaced, in the Copigmentation complexes, by other abundant cofactors, such as hydroxycinnamic acids and (−)-epicatechin. Thereafter, Cencibel wines showed proportionally the lowest decrease in this Copigmentation effect at this ageing time. After 9 months, the losses of monomeric anthocyanins and cofactors still continued, and only Syrah wines showed a little enhancement of the red colour intensity. At this ageing time, the amounts of monomeric anthocyanins were sufficient for the formation of Copigmentation complexes, but the molar ratio of cofactors to anthocyanins was possibly too low for detecting significant effects on colour, especially in Cabernet Sauvignon and Cencibel wines. A second observed effect of Copigmentation was the bathochromic shift to bluish hues for Cencibel and Syrah wines, and it only was maintained in the latter wine during all the ageing times checked.
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influence of ethanol content on the extent of Copigmentation in a cencibel young red wine
Journal of Agricultural and Food Chemistry, 2003Co-Authors: Isidro Hermosin GutierrezAbstract:The effect of ethanol content on the Copigmentation of a Cencibel young red wine was studied, by means of ethanol elimination and reconstitution of the initial volume with different ethanol proportions. The reference wine (14.0% ethanol, 0.40 g/L volatile acidity) showed a bathochromic shift of 4 nm and a color enhancement (AColor) of 41%, lower than that found for the reconstituted wine with the same ethanol content (53%). This discrepancy could be attributable to the loss of acetic acid during the ethanol elimination step. ΔColor was 95% for the reconstituted wine without ethanol and decreased until 18% for the reconstituted wine with 22% ethanol. Copigmentation was important for reconstituted wines with ethanol contents typical for table red wine, showing ΔColor between 53 and 57%. An increase in ethanol content in reconstituted wines was accompanied by an increase in the pH value. Perceivable changes in color (ΔE* > 1) followed every increase in ethanol content.