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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2020 · IF 4.192

Comparative Study on the Stability and Antioxidant Activity of Six Pyranoanthocyanins Based on Malvidin-3-glucoside

Jianxia Sun,Xinghua Li,Haixia Luo,Lijun Ding,Xinwei Jiang,Xusheng Li,Rui Jiao,Weibin Bai

Pyranoanthocyanins are the important color and functional compounds in red wine. Six common kinds of pyranoanthocyanins were synthesized through the reaction of malvidin-3-O-glucoside (Mv-3-gluc) with acetone, pyruvic acid, p-cumaric acid, caffeic acid, ferulic acid, and sinapid acid, respectively, and their pH (1.0–11.0), SO2 (0–250 ppm), and thermo (50–98 °C) stabilities and antioxidant activities were comparatively studied. Results showed that the six pyranoanthocyanins all exhibited higher pH and SO2 color stability than Mv-3-gluc, especially vitisin-A with a carboxy group on the D ring. The six pyranoanthocyanins also showed much more thermostability than Mv-3-gluc, especially methylpyranomv-3-gluc. The degradation kinetics of Mv-3-gluc and its derivatives all fitted to a first-order reaction. Moreover, pinotin-A with the o-dihydroxyl group on the E ring presented the strongest antioxidant capability, as evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and ferric ion reducing power (FRAP) assays. Additionally, the increase in the number of rings is beneficial to the improvement of the DPPH radical scavenging ability of anthocyanins.

研究领域: 食品科学 · 化学 · 生物学
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Journal of Integrative Agriculture · 2023 · IF 4.8

The protective effect of cyclodextrin on color quality and stability of Cabernet Sauvignon red wine1

Cai-yun LIU,Lu-lu WU,Shu-yue FAN,Yong-sheng TAO,Yun-kui LI

The impact of cyclodextrins (CDs) on wine quality and stability has been seldomly reported. This study systematically assessed the protective effect of post-fermentation addition of CDs on color stability of red wine from the viewpoints of color characteristics, copigmentation and phenolic profiles. The grey relational analysis (GRA) and principal component analysis (PCA) were employed to dissect the key effective determinants related to color quality. The addition of CDs induced a significant hyperchromic effect of 8.19%-25.40%, significant bathochromic effect and enhancement of the color intensity. Furthermore, the evolution of anthocyanin form and the content of monomeric anthocyanins revealed that β -CD is a superior favorable cofactor during wine aging, but for the long-term aging, 2-HP- β -CD and 2-HP- γ -CD are more beneficial in promoting the formation of polymerized anthocyanins and the color stability. This work provides an important reference for the use of CDs to enhance color quality and stability of red wines.

CAS / MDL: 10016-20-3 128446-35-5
研究领域: 食品科学 · 葡萄酒化学 · 分析化学
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AUSTRALIAN JOURNAL OF GRAPE AND WINE RESEARCH · 2019 ·Vol. 25 ·期 3 ·307-315 · IF 2.343

Burdock fructooligosaccharides inhibits postharvest colour development in grape skins by altering phenylpropanoid fluxes from anthocyanin to the resistance-related phenolic substances

Y. Yang,X. Wang,F. Tan,M. Fu,F. Sun

Background and Aims Burdock fructooligosaccharides (BFO) is an elicitor that induces biotic resistance and delays colour development in grapes postharvest. The mechanism of the delayed colour development requires further study. Methods and Results Colour development index; anthocyanin, tannin, flavonol, flavanol, trans -resveratrol and lignin; the trans -resveratrol, lignin and anthocyanin biosynthesis-related transcription factors; and functional gene expression were investigated. In response to BFO induction, upregulation of the v-myb avian myeloblastosis viral oncogene homologue 14 ( MYB14 )-mediated stilbene synthase ( STS ) altered the phenylpropanoid fluxes from anthocyanin to trans -resveratrol; MYBA1 and MYBA2- mediated the downregulation of dihydroflavonol 4-reductase ( DFR ), and flavonoid-3-O-glycosyltransferase ( UFGT ) limited anthocyanin biosynthesis. Downregulation of MYB4- mediated chalcone synthase ( CHS ) and upregulation of cinnamoyl CoA reductase ( CCR ) and cinnamyl alcohol dehydrogenase ( CAD ) altered the phenylpropanoid fluxes from anthocyanin to lignin. Conclusions Burdock fructooligosaccharides inhibits postharvest colour development in grapes by altering the phenylpropanoid fluxes from anthocyanin to resistance-related phenolic substances. Significance of the Study Understanding the mechanism of the effect of BFO on grape colour development may improve our understanding of colour development in grape berries.

研究领域: 植物学 · 分子生物学
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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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Agriculture-Basel · 2022 ·Vol. 12 ·期 5 ·604 · IF 3.408

Effects of Biodegradable Liquid Film on Cabernet Sauvignon (V. vinifera L.) Grape Quality

Xing Han,Fei Yao,Ying Wang,Xinyao Duan,Zhilei Wang,Yihan Li,Tingting Xue,Xu Liu,Hua Wang,Hua Li

Biodegradable liquid film (BLF) improves soil structure and increases plant freezing tolerance after spraying on the surface of soil and plant. In this study, the effects of BLF on grape composition and volatile compounds in Cabernet sauvignon (Vitis viniferaL.) grapes were determined by spraying BLF during the dormant periods over three years. The aim of the study was to evaluate the potential impact of BLF as an overwintering protection measure on grape fruit quality. In 2020 and 2021, BLF spraying increased reducing sugar content and 100-berry weight, decreased titratable acid content, and improved the maturity factor. Compared with the vines not sprayed with BLF, the content of total phenols and total anthocyanins in grape skins showed an increase over the three-year period, with the largest increases of 31.92% and 48.38%, respectively, and the content of total tannins and total flavan-3-ols increased in 2020 and 2021. BLF treatment also increased the total phenolic content in seeds for all three years, reaching a significant level in 2019, 16.38% higher than control treatment (CK). HPLC analysis showed that BLF treatment affected the content and composition of monomeric anthocyanins in grape skins, especially in 2021, BLF treatment significantly increased the content of nine monomeric anthocyanins, and the proportion of acetylated and coumaroylated anthocyanins. However, GC-MS analysis indicated that BLF had little effect on volatile compounds. These results suggest that BLF can be used as an overwintering protection measure in cold regions to promote the accumulation of sugars and polyphenolics, thereby improving overall grape quality.Keywords:wine grape;biodegradable liquid film;grape composition;anthocyanins

CAS / MDL: 75-05-8 64-18-6
研究领域: 农业 · 酿酒学 · 植物科学
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JOURNAL OF SEPARATION SCIENCE · 2023 ·Vol. 46 ·期 16 ·2300264 · IF 3.1

Insights into the metabolite profiles of Rubus chingii Hu at different developmental stages of fruit

Yu-Jiao Hua,Fen Xie,Kun-jun Mao,Yi-Yuan Luo,Yong-Juan Ding

The fruits of Rubus chingii Hu have high medicinal and nutritional values. However, the metabolite profiles of R. chingii , especially the alterations during different development stages of fruit, have not been comprehensively analyzed, hindering the effective utilization of the unique species. In this study, we comprehensively analyzed the metabolites of R. chingii fruit at four developmental stages using systematic untargeted and targeted liquid chromatography-mass spectrometry metabolomics analysis and identified 682 metabolites. Significant changes were observed in metabolite accumulation and composition in fruits during the different developmental stages. The contents of the index components, kaempferol-3-O-rutinoside and ellagic acid, were the highest in immature fruit. The analysis identified 64 differentially expressed flavonoids and 39 differentially expressed phenolic acids; the accumulation of most of these differentially expressed metabolites decreased with the developmental stages of fruit from immaturity to maturity. These results confirmed that the developmental stages of fruit are a critical factor in determining its secondary metabolite compositions. This study elucidated the metabolic profile of R. chingii fruit at different stages of development to understand the dynamic changes in metabolites.

研究领域: 植物学 · 代谢组学
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FOOD RESEARCH INTERNATIONAL · 2024 · IF 7

Gallic acid improves color quality and stability of red wine via physico-chemical interaction and chemical transformation as revealed by thermodynamics, real wine dynamics and benchmark quantum mechanical calculations

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

The aim of this study was to explore the copigmentation effect of gallic acid on red wine color and to dissect its mechanism at the molecular level. Three-dimensional studies, e.g., in model wine, in real wine and in silico, and multiple indicators, e.g., color, spectrum, thermodynamics and phenolic dynamics, were employed. The results showed that gallic acid significantly enhanced the color quality and stability of red wine. Physico-chemical interactions and chemical transformations should be the most likely mechanism, and physico-chemical interactions are also a prerequisite for chemical transformations. QM calculations of the physico-chemical interactions proved that the binding between gallic acid and malvidin-3- O -glucoside is a spontaneous exothermic reaction driven by hydrogen bonding and dispersion forces. The sugar moiety of malvidin-3- O -glucoside and the phenolic hydroxyl groups of gallic acid affect the formation of hydrogen bonds, while the dispersion interaction was related to the stacking of the molecular skeleton.

CAS / MDL: 149-91-7
研究领域: 食品科学 · 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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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2016 · IF 2.857

The Modulatory Effect of Anthocyanins from Purple Sweet Potato on Human Intestinal Microbiota in Vitro

Xin Zhang,Yang Yang,Zufang Wu,Peifang Weng

In order to investigate the modulatory effect of purple sweet potato anthocyanins (PSPAs) on human intestinal microbiota, PSPAs were prepared by column chromatography and their influence on intestinal microbiota was analyzed by monitoring the bacterial populations and analyzing short-chain fatty acid (SCFA) concentrations at different time points. The numbers (log10 cell/mL) of Bifidobacterium and Lactobacillus/Enterococcus spp., Bacteroides-Prevotella, Clostridium histolyticum, and total bacteria after 24 h of culture in anaerobic fermentation broth containing PSPAs were 8.44 ± 0.02, 8.30 ± 0.01, 7.80 ± 0.03, 7.60 ± 0.03, and 9.00 ± 0.02, respectively, compared with 8.21 ± 0.03, 8.12 ± 0.02, 7.95 ± 0.02, 7.77 ± 0.02, and 9.01 ± 0.03, respectively, in the controls. The results showed that PSPAs induced the proliferation of Bifidobacterium and Lactobacillus/Enterococcus spp., inhibited the growth of Bacteroides-Prevotella and Clostridium histolyticum, and did not affect the total bacteria number. Total SCFA concentrations in the cultures with PSPAs were significantly higher than in the controls (P < 0.05). Moreover, during the fermentation, the PSPAs were partially fragmented to phenolic acids, which may exert a better effect on intestinal microecology, suggesting that PSPAs may have prebiotic-like activity by generating SCFAs and modulating the intestinal microbiota, contributing to improvements in human health.

研究领域: 食品科学 · 微生物学 · 营养学
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FOOD RESEARCH INTERNATIONAL · 2019 · IF 3.579

Compositional characterization study on high -molecular -mass polymeric polyphenols in red wines by chemical degradation

Hao Suo,Ruochen Tian,Jing Li,Shuting Zhang,Yan Cui,Lingxi Li,Baoshan Sun

High-molecular-mass polymeric polyphenols (HPPCs) is the major group of polyphenols in red wine. However, owing to the diversity and structural complexity, its compositional characterization remains a difficulty. In this study, purified high-molecular-mass polymeric polyphenols (PHPPCs) was isolated by solid phase extraction combined with semi-preparative HPLC from red wine. Different chemical degradation methods (NaOH, HCl and benzyl mercaptan degradation) were used to decompose the PHPPCs into low molecular weight fragments. The chemical structures of the degradation fragments were verified by HPLC/UPLC−DAD and HPLC-FT-ICR-MS. The results showed that three proanthocyanidins, five proanthocyanidins benzylthioether, quercetin and fifteen anthocyanins were detected by degradation in the presence of benzyl mercaptan. Nine bound phenolic acids were found by NaOH degradation and twelve bound amino acids were proved by HCl. Among these different fragments detected,delphinidin-3-O-glucoside pyruvic adduct, four acylated anthocyanins, four hydroxyphenyl pyranoanthocyanins, quercetin, protocatechuic acid, vanillic acid, and cinnamic acid were first found in the PHPPCs. For the first time amino acids as constitutive units of polymeric polyphenols in red wines were verified. Based on the degradation fragments, the possible compositional characterization of HPPCs in red wine was postulated.

CAS / MDL: 100-53-8
研究领域: 食品科学 · 分析化学 · 植物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Ultrahigh Pressure Facilitates the Acylation of Malvidin and Chlorogenic Acid to Increase the Stability and Protective Effect of Malvidin Derivatives on H2O2-Induced ARPE-19 Cells

Xinyao Liu,Sheng Li,Zhitong Wang,Xinyuan Wang,Yang He,Liankui Wen

We explored the effects of ultrahigh-pressure technology and chlorogenic acid on the color stability and structure–activity relationship of malvidin (MV). Experimental conditions were optimized through single-factor experiments and response surface analysis at a pressure of 300 MPa, mass ratio of MV to chlorogenic acid of 1:3.64 (w/w), and time of 5 min. Compared with MV, MV derivatives showed higher stability and in vitro antioxidant activity. X-ray diffraction analysis, UV–vis spectroscopy, Fourier transform infrared spectroscopy, high-performance liquid chromatography, and mass spectrometry were conducted to determine the structures of MV derivatives for the first time. Ultrahigh pressure facilitated acylation of chlorogenic acid and MV and produced four new MV derivatives. Analysis of the effect of malvidin-3-O-6-(acrylic acid-(2-hydroxy, 4-carboxy-cyclohexanol) ester)-guaiacol (Mv3ACEC) on ARPE-19 cells exposed to H2O2 by RNA transcriptome sequencing showed that Mv3ACEC simultaneously inhibited various inflammatory and apoptotic signal transduction pathways, exerted a synergistic effect, and partly inhibited cell apoptosis through the MAPK signaling pathway. Therefore, the results show that ultrahigh pressure will cause acylation of chlorogenic acid and MV to produce four new MV derivatives, and MV derivatives protect ARPE-19 cells from H2O2-induced oxidative stress.

CAS / MDL: 327-97-9
研究领域: 食品科学 · 生物化学 · 细胞生物学
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FOOD CHEMISTRY · 2018 · IF 4.946

Effects of low power ultrasonic treatment on the transformation of cyanidin-3-O-glucoside to methylpyranocyanidin-3-O-glucoside and its stability evaluation

Jianxia Sun,Haixia Luo,Xinghua Li,Xusheng Li,Yeyu Lu,Weibin Bai

Pyranoanthocyanins are anthocyanin derivatives that are formed during fermentation and oxygenation processes in aged wine. They play a critical role in assessing the aging of wine based on its colour quality. Naturally, the formation process of pyranoanthocyanins is fairly slow. In this respect, the present work studies the role and efficiency of ultrasonic treatment in accelerating the formation of methylpyranocyanidin-3- O -glucoside and investigates the spectral characteristics as well as the stability of this derivative toward heat, bisulfite bleaching and pH variation in a simulation system. Our results showed that the yield of methylpyranocyanidin-3- O -glucoside can be increased by 32.5% by ultrasonic treatment at 100 W for 40 min, and excessive treatment (≥60 min) does not have a positive effect on the yield. Moreover, this derivative exhibits a better stability toward heat, pH variation and bisulfite bleaching than its precursor cyanidin-3- O -glucoside.

研究领域: 食品科学 · 化学
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