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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2021 · IF 4.556

Copigmentation evidence of phenolic compound: The effect of caffeic and rosmarinic acids addition on the chromatic quality and phenolic composition of Cabernet Sauvignon red wine from the Hexi Corridor region (China)

Bo Zhang,Xue-Qing Wang,Bo Yang,Ning-Ning Li,Jian-Ming Niu,Xiao Shi,Shun-Yu Han

Although phenolic copigments are rarely colored, they can still influence color expression in red wine copigmentation. Here, prefermentative agents, such as caffeic and rosmarinic acids, were added as copigments during Cabernet Sauvignon red winemaking. The evolution of colors and polyphenols was analyzed by tristimulus colorimetry and high-performance liquid chromatography-tandem mass spectrometry during brewing and aging periods. The results showed that the addition of caffeic and rosmarinic copigments was beneficial to obtain more saturated and vivid hue of wines. The changes in color were correlated with a significant increase in anthocyanins concentration. Moreover, the results demonstrated that the addition of the two phenolic copigments increased the concentration of total phenols and enhanced the copigmentation effect, indicating improved chromatic intensity and color stability of wines. Therefore, the addition of caffeic and rosmarinic acids is a simple and useful enological technique to obtain red wines with high color quality and aging potential.

研究领域: 食品科学 · 葡萄与葡萄酒学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2020 ·Vol. 101 ·期 4 ·1579-1588 · IF 2.614

Multiple co-pigments of quercetin and chlorogenic acid blends intensify the color of mulberry anthocyanins: insights from hyperchromicity, kinetics, and molecular modeling investigations

Ibrahim Khalifa,Jing Du,Asad Nawaz,Chunmei Li

BACKGROUND The effect of multiple co-pigments on the color intensification of mulberry anthocyanins (ACs) using spectroscopic techniques in combination with a molecular docking study was studied. The hyperchromicity of ACs co-pigmented with chlorogenic acid (CH) and quercetin (Q) blends was measured and their color stability in liquid and encapsulated particle models was evaluated. RESULTS Multiple co-pigments exhibited higher hyperchromicity, p K H -values, and heat-stability than their individual counterparts. Surflex-docking findings confirmed that stronger binding occurred between multiple ligands and AC than single ones due to their extra -OH, -COOH groups, and delocalization systems. The binding was allowed by increased H-bonding, van der Waals forces, and π - π sites by the extra groups of the multiple co-pigments with AC in aqueous juice and whey particle-based models. CONCLUSION This is the first report of the ternary mixture of phenolic acid-flavonol-anthocyanin which could be used as promising food red-colorants. © 2020 Society of Chemical Industry

CAS / MDL: 327-97-9 117-39-5
研究领域: 食品科学 · 分子生物学
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Food Science & Nutrition · 2020 ·Vol. 8 ·期 7 ·3234-3242 · IF 1.797

Copigmentation effect of three phenolic acids on color and thermal stability of Chinese bayberry anthocyanins

Yanyun Zhu,Hongji Chen,Leyan Lou,Yixin Chen,Xingqian Ye,Jianchu Chen

The copigmentation effects of three phenolic acids (ferulic acid, sinapic acid, and syringic acid) on the color and thermal stability of Chinese bayberry anthocyanins were investigated. The three copigments of ferulic acid, sinapic acid, and syringic acid were found to have significant effects on the color enhancement of bayberry anthocyanins ( p < .05). The maximum absorption wavelength of the anthocyanin aqueous solution exhibited a bathochromic shift, L * decreased, and a * increased with the increase in the molar ratio of copigments. The thermal stability of bayberry anthocyanins was significantly improved after copigmentation. No new anthocyanin derivatives appeared after copigmentation. The thermodynamic parameters (Δ G , Δ H , Δ S ) of the three processes were all negative, indicating the three copigmentations were generally spontaneous and exothermic. The equilibrium constant ( K ) of the sinapic acid group was the greatest among the three phenolic acids, indicating that sinapic acid was more effective in stabilizing the anthocyanins.

研究领域: 食品科学 · 植物化学
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FOOD CHEMISTRY · 2024 · IF 8.5

Intermolecular interactions between malvidin-3-O-glucoside and caffeic acid: Structural and thermodynamic characterization and its effect on real wine color quality

Lulu Wu,Yu Zhang,Shuyue Fan,Mario Prejanò,Tiziana Marino,Nino Russo,Yongsheng Tao,Yunkui Li

The copigmentation effect between malvidin-3- O -glucoside and caffeic acid was comprehensive inquiry on the model wine solution, theoretical simulation and real wine. Thermodynamic parameters were determined by UV/Visible spectroscopy and Isothermal titration calorimetry (ITC). Theoretical data were obtained employing a dispersion-corrected density functional approach. The effects in real wines were investigated by adding the caffeic acid during different fermentation periods. Results shown that the copigmentation reaction between caffeic acid and malvidin-3- O -glucoside is a spontaneous exothermic reaction driven by hydrogen bonding and dispersions forces. Computations show that the polyhydroxyl sugar moiety and phenolic hydroxyl groups are the key active sites. The addition of caffeic acid in post-alcohol fermentation samples evidences an improving color characteristics in the wine.

CAS / MDL: 331-39-5
研究领域: 食品科学 · 化学
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FOOD RESEARCH INTERNATIONAL · 2024 · IF 7

Mannoproteins modulate olfactrory perception and copigmentation of organoleptic-active-components in wines: Effects and potential molecular mechanisms

Zhengbo Guo,Hanyue Dong,Junxia Lin,Yongyuerun Hu,Dabing Ren,Lunzhao Yi,Siyu Li

In this research, accelerated aroma release experiments and malvidin-3- O -glucoside copigmentation experiments in model red wine solutions were designed to investigate the abilities and molecular mechanisms of mannoproteins in modulating olfactory/chromatic properties of red wines. Results indicate that under orthonasal condition, mannoprotein MP2 was promising aroma modulator due to its predictable behaviors in expelling and retaining the aroma compounds during different periods. Low field nuclear magnetic resonance and molecular dynamic simulation proved that the modulation ability of MP2 should be explained by its transitionary interacting preferences with water/aroma compound molecules. Retronasal results show that the release of aroma compounds and olfactory perceptions were irregular and difficult to predict, probably due to the complexity of the retronasal condition. All mannoproteins protected malvidin-3- O -glucoside and quercetin via the formation of binary/ternary complexes, and quercetin was found prior to be protected than malvidin-3- O -glucoside. Principal mannoprotein A0A6C1DV26 might be the critical malvidin-3- O -glucoside protector. With the presence of quercetin, principal mannoproteins B3LQU1/B5VL26 in mannoprotein MP1 might exhibit intramolecular and/or intermolecular mechanisms that strengthened the hyperchromic effect, thus enhanced the copigmentation.

CAS / MDL: 9000-90-2
研究领域: 食品科学 · 分子生物学
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FOOD CHEMISTRY · 2018 · IF 4.946

Effects of high hydrostatic pressure-assisted organic acids on the copigmentation of Vitis amurensis Rupr anthocyanins

Yang He,Liankui Wen,Hansong Yu,Fei Zheng,Zhitong Wang,Xuanwei Xu,Hao Zhang,Yong Cao,Bixiang Wang,Baiji Chu,Jianyu Hao

Natural anthocyanins are safer and nutritious as compared to synthetic pigments; however, their stability is poor. They can produce spontaneous copigmentation with organic acids, leading to the improvement of colour stability, albeit slowly. Box–Behnken experimental design was used to elucidate the mechanism of copigmentation between Vitis amurensis Rupr anthocyanins (0.1 mg/mL) and organic acids (0.87 mg/mL, ferulic acid: d -gluconic acid:caffeic acid:vanillic acid = 1.5:2.5:2.5:0.5, w/w/w/w) promoted by high hydrostatic pressure (HHP; 300 MPa, 2 min). The copigmentation effect and antioxidant activity of anthocyanins were also evaluated. The structure of anthocyanins was analysed using ultraviolet–visible spectroscopy, Fourier-transform infrared spectroscopy, high-performance liquid chromatography, and mass spectrometry. The results of HHP copigmentation showed that the following anthocyanins were newly formed—delphinidin-3- O -catechol, petunidin-3- O -catechol, delphinidin-4-vinyl-catechol, petunidin-3- O -guaiacol, malvidin-4-vinyl-guaiacol, cyanidin-3- O -(6″- O -caffeoyl)-glucoside, peonidin-3- O -(6″- O -caffeoyl)-glucoside, delphinidin-3- O -(6″- O -caffeoyl)-glucoside, malvidin-3- O -glucoside-4-vinyl-guaiacol, and malvidin-3- O -(6″- O -feruloyl)-glucoside—owing to appropriate modifications that increased the copigmentation rate (R = 42.12%), photo-thermal stability (R > 45%), and potential antioxidant activities expressed in vivo ( p  < 0.01 vs. Model Group).

研究领域: 食品科学 · 化学 · 植物学
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FOOD RESEARCH INTERNATIONAL · 2025 · IF 8

Effect of bovine serum albumin and Copigments on the stability of Haskap berry anthocyanin extracts at neutral pH

Lianghao Wang,Jiayuan Luo,Xu Zhang,Yihong Bao,Junwei Huo

Haskap berry anthocyanin extract (HAE), a high-value and high-potential natural pigment, is prone to degradation by external factors such as heat and light. To improve the chemical and color stability of HAE, the binary and ternary composite system of HAE, BSA and copigments was compared for the protection of anthocyanin in the heat and light treatments at neutral pH. Compared to the binary composite system of HAE with BSA and ferulic acid (FA), the select HAE-BSA-FA ternary composite system decreased the total anthocyanin degradation rate (TADR) to 65.26 % and 70.06 % after heat and light treatments, and the color difference value (ΔE) to 43.59 % and 71.64 %, the bioaccessibility index (BAI) at the conclusion of gastric digestion and intestinal digestion increased 17.52 % and 44.57 %, which had a better protective effect on the thermal, light and in vitro digestion stability of HAE. Results of fluorescence spectroscopy, circular binning, FTIR spectroscopy, SDS-PAGE, and particle size analysis indicated that the stability of HAE was promoted by non-covalent binding with BSA and FA, such as hydrogen bonding, electrostatic force. HAE, BSA, and FA are complexed by hydrophobic interactions, and the secondary structure of BSA was changed in the process.

CAS / MDL: 121-34-6
研究领域: 食品科学 · 生物化学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2025 · IF 6.6

Influence of phenolic co-pigments on the stability of major anthocyanin in blueberry wine and color changes during storage

Meijuan Qiu,Shaoyi Chen,Hongxiang Zhou

Addressing the issue of color loss owing to the degradation of anthocyanins during storage in blueberry wine, we compared the stabilizing effect of phenolics on anthocyanins. Initially, the influences of phenolic co-pigments (catechin, epicatechin, gallic acid, sringic acid, and caffeic acid) on the main monomeric anthocyanin (malvidin-3-O-galactoside) in blueberry wine were evaluated in a model wine solution. Gallic acid showed the highest binding strength (binding constant K  = 24.41 mol/L) and excellent thermal (half-life t 1/2  = 15.20 h) and light stability (half-life t 1/2  = 38.66 h) in the model wine solution, whereas epicatechin distinguished itself in oxidative stability (half-life t 1/2  = 11.37 h). In the subsequent storage, the blueberry wine containing epicatechin or gallic acid as co-pigments displayed markedly improved color stability, evidenced by intensified color enhancement and darker displacement, reduced color change, and maintenance of elevated levels of total phenolics, total flavonoids, and anthocyanins. This work may provide theoretical and practical guidance for stabilizing wine color during the storage of fermented fruit wines such as blueberry wine.

研究领域: 食品化学 · 食品科学 · 酿造学 · 植物化学
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FOOD HYDROCOLLOIDS · 2025 · IF 12.4

Copigmentation effect and mechanism of α-cyclodextrin on wine color quality and stability: combining dynamics, thermodynamics, structural characterization and quantum mechanics

Caiyun Liu,Lulu Wu,Zengshuai Zhang,Ziying Li,Mario Prejanò,Tiziana Marino,Yongsheng Tao,Yunkui Li

This study was aimed to explore the effect of α-cyclodextrin (α-CD) on color quality and stability of red wines, and to dissect the mechanism of copigmentation at molecular level. Firstly, α-CD was added to real wine before fermentation and aging dynamics were monitored. This study found that α-CD enhanced visual quality by strengthening anthocyanins maceration during fermentation, yet α-CD improved color stability by promoting formation of color-stable polymeric anthocyanins during aging. Secondly, the thermodynamics and dose-effect relationships in model wines revealed that binding between α-CD and malvidin-3- O -glucoside (Mvd-G) was a spontaneous exothermic reaction driven by enthalpy, with an optimal molar ratio of 1:5. Finally, structural characterization of host-guest complex and electronic effects of intermolecular interactions revealed that Mvd-G successfully formed host-guest complex with α-CD through hydrogen bonding and dispersion. The hydroxyl group and glucoside in the anthocyanin C ring, as well as the primary hydroxyl group of the α-CD were the key structures for forming hydrogen bonds. The results of this study provided an experimental and theoretical basis for the applications of α-CD as copigment to enhance the color quality and stability.

研究领域: 食品科学 · 化学 · 葡萄酒技术 · 分子生物学 · 量子力学
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FOOD CHEMISTRY · 2024 · IF 8.5

A double-layer film based on the strategy of tannic acid-anthocyanin co-pigmentation and tannic-crosslinked-gelatin/−reduced Ag nanoparticles for beef preservation and monitoring

Rui Li,Haoyu Feng,Shancan Wang,Di Zhuang,Youhong Wen,Jie Zhu

A double-layer film was developed with tannic acid (TA) co-pigmented purple potato anthocyanin extract (PAE)-agar as the inner layer, and K-carrageenan-oregano essential oil Pickering emulsion (OPE)/silver nanoparticles (TA-AgNPs) as the outer layer. Molecular docking and FT-IR results elucidated that intermolecular hydrogen bond was the main interaction between components in the agar-carrageenan matrix, with TA and PAE contributing to intensified anthocyanin color through π-π stacking. The incorporation of OPE/TA-AgNPs enhanced the film's hydrophobicity (WCA > 100 ° ) and UV–vis barrier (close to 0% at 200-320 nm, effectively impeding UVA, UVB, and UVC) properties and exhibited outstanding antioxidant (DPPH scavenging rate > 88%) and antimicrobial activities. This film showed a significant color change in the pH range of 2–12 (from pink to yellow) and a considerable sensitivity to volatile amines within 2 min. The films effectively alleviated beef spoilage (extending the shelf life of beef for 1d) and reflected the freshness of beef during storage. Additionally, the digital color information of the film was obtained by a smartphone combined with RGB values analysis to quantify the freshness of beef rapidly. Therefore, this study expands the application of food packaging films with freshness preservation and monitoring in the field of animal-derived food.

CAS / MDL: 11114-20-8
研究领域: 食品科学 · 材料科学 · 生物技术 · 包装工程
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