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MOLECULES · 2018 ·Vol. 23 ·期 7 ·1788 · IF 3.098

Protection of Anthocyanin from Myrica rubra against Cerebral Ischemia-Reperfusion Injury via Modulation of the TLR4/NF-κB and NLRP3 Pathways

Hong-Xin Cui,Ji-Hong Chen,Jing-Wan Li,Fang-Rong Cheng,Ke Yuan

Myrica rubra(MR) is rich in anthocyanins, and it has good anti-cancer, anti-aging, antioxidant, and antiviral effects. The proportion of disability and death caused by ischemic stroke gradually increased, becoming a major disease that is harmful to human health. However, research on effects of anthocyanin from MR on cerebral ischemia-reperfusion (I/R) injury is rare. In this study, we prepared eight purified anthocyanin extracts (PAEs) from different types of MR, and examined the amounts of total anthocyanin (TA) and cyanidin-3-O-glucoside (C-3-G). After one week of PAE treatment, the cerebral infarction volume, disease damage, and contents of nitric oxide and malondialdehyde were reduced, while the level of superoxide dismutase was increased in I/R mice. Altogether, our results show that Boqi1MR contained the most TA (22.07%) and C-3-G (21.28%), and that PAE isolated from Dongkui MR can protect the brain from I/R injury in mice, with the mechanism possibly related to the Toll-like receptor 4 (TLR4)/ nuclear factor-κB (NF-κB) and NOD-like receptor pyrin domain-containing 3 protein (NLRP3) pathways.Keywords:Myrica rubra;anthocyanins;cyanidin-3-O-glucoside;cerebral ischemia-reperfusion;TLR4/NF-κB;NLRP3

CAS / MDL: 67-56-1 298-96-4
研究领域: 药理学 · 神经科学 · 分子生物学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2024 · IF 6

Study on the interaction mechanism and physicochemical properties of luteolin and its glucoside compounds with β-lactoglobulin

Zihao Chen,Min Fu,Jun Chen,Guowen Zhang,Ti Li,Qin Geng,Taotao Dai

Molecular docking simulations and multispectral approaches were used to study the non-covalent interactions between β-lactoglobulin (β-LG) and chosen luteolin (Lu), isoorientin (Iso), and cynaroside (Cyn). The fluorescence quenching results demonstrated that Lu, Iso, and Cyn spontaneously formed stable complexes with β-LG through static quenching. Thermodynamic parameters and molecular docking simulations demonstrated that hydrogen bonds were the primary forces driving the interactions between the protein and flavonoids. The binding constants followed the order: β-LG-Lu (2.87 × 10⁴ L/mol) > β-LG-Iso (1.83 × 10⁴ L/mol) > β-LG-Cyn (1.52 × 10⁴ L/mol). Additionally, the C-glycosylated flavonoid (Iso) showed a higher propensity to form hydrogen bonds with β-LG compared to the O-glycosylated flavonoid (Cyn). The results of circular dichroism indicated that the β-LG structure became looser with the introduction of Lu, Iso, and Cyn. Furthermore, the assembly of β-LG-flavonoid complexes decreased the surface hydrophobicity and oil-water interfacial tension of β-LG, improved its foaming and emulsifying capabilities, and protected the antioxidant properties of the flavonoids to a certain extent. This study investigated the interaction mechanisms between flavonoids with different glycosyl types and β-LG, providing insights for the incorporation of suitable flavonoids into dairy products, and offering theoretical perspectives on preserving the antioxidant properties of flavonoids.

研究领域: 食品科学 · 分子生物学
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FOOD CHEMISTRY · 2021 · IF 7.514

Effect of advanced/hybrid oxidation process involving ultrasonication and ultraviolet radiation (sonophotolysis) on anthocyanin stability: Degradation kinetics and mechanism

Xiaohan Wu,Qianwei Lin,Tarun Belwal,Hao Huang,Ligen Zou,Weide Lv,Zisheng Luo

The hybrid oxidation effect of ultrasonics (US) and ultraviolet light (UV-A) on Cyanidin-3-O-glucoside (C3G) stability were examined. For comparison, sonolysis and photolysis experiments were also conducted. The results showed that under hybrid sonophotolysis and sonolysis treatment, C3G degradation undergoes zero-order kinetics, while under photolysis, first-order degradation kinetic prevailed. The degradation rate increases with the increase in US power, with the lowest, was recorded as 0.70 μg/ml/h (14 W/L) and 0.77 μg/ml/h (28 W/L), and highest as 0.80 μg/ml/h (42 W/L). Similarly, the degradation ability of UV photolysis at 400 μW/cm 2 was weak, which increased with increasing UV power (600 μW/cm 2 ) . Overall the sonophotolysis degradation rate was significantly higher than that of the individual effect. With the addition of gallic acid (GA), the degradation of C3G was found lower under sonophotolysis; thus, it could be used as a natural protective agent for C3G during food processing.

CAS / MDL: 5949-29-1 149-91-7
研究领域: 食品科学 · 化学工程 · 分析化学
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MOLECULES · 2021 ·Vol. 26 ·期 6 ·1721 · IF 4.412

Interaction of Soy Protein Isolate Hydrolysates with Cyanidin-3-O-Glucoside and Its Effect on the In Vitro Antioxidant Capacity of the Complexes under Neutral Condition

Yaru Wu,Zhucheng Yin,Xuejiao Qie,Yao Chen,Maomao Zeng,Zhaojun Wang,Fang Qin,Jie Chen,Zhiyong He

The interaction of soy protein isolate (SPI) and its hydrolysates (SPIHs) with cyanidin-3-O-glucoside (C3G) at pH 7.0 were investigated to clarify the changes in the antioxidant capacity of their complexes. The results of intrinsic fluorescence revealed that C3G binds to SPI/SPIHs mainly through hydrophobic interaction, and the binding affinity of SPI was stronger than that of SPIHs. Circular dichroism and Fourier-transform infrared spectroscopy analyses revealed that the interaction with C3G did not significantly change the secondary structures of SPI/SPIHs, while the surface hydrophobicity and average particle size of proteins decreased. Furthermore, the SPI/SPIHs-C3G interaction induced an antagonistic effect on the antioxidant capacity (ABTS and DPPH) of the complex system, with the masking effect on the ABTS scavenging capacity of the SPIHs-C3G complexes being lower than that of the SPI-C3G complexes. This study contributes to the design and development of functional beverages that are rich in hydrolysates and anthocyanins.Keywords:soy protein isolate;hydrolysate;cyanidin-3-O-glucoside;noncovalent interaction;antioxidant capacity

研究领域: 食品科学 · 营养学 · 生物化学
✓ 已验证 DOI PubMed 高影响因子
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Food & Function · 2023 ·Vol. 14 ·期 14 ·6707-6717 · IF 6.1

Modulation effect of black rice dietary fiber on the metabolism and fermentation of cyanidin-3-glucoside in an in vitro human colonic model

Shuai Zhang,Mei Deng,Ruifen Zhang,Xuchao Jia,Fei Huang,Dong Zhao,Lihong Dong,Jianwei Chi,Zhida Sun,Qin Ma,Mingwei Zhang

Black rice (Oryza sativa L.) is a great source of anthocyanins and dietary fiber and possesses various health-promoting properties. The modulating effect of insoluble dietary fiber (IDF) from black rice on the fermentation of cyanidin-3-O-glucoside (Cy3G) in an in vitro human colonic model, together with the possible microbiota-mediated mechanisms, was investigated. The combined Cy3G and IDF fermentation can promote the biotransformation of Cy3G into phenolic compounds such as cyanidin and protocatechuic acid with stronger antioxidant activities and increase the total production of SCFAs during the fermentation of Cy3G. 16S rRNA sequencing analysis revealed that the addition of IDF modulated the microbiota structure and bloomed Bacteroidota and Prevotellaceae-related genera, which were positively correlated with metabolites of Cy3G, thus potentially regulating the microbial metabolism of Cy3G. The work is of great significance for elucidating the material basis of the health benefits of black rice.

研究领域: 营养学 · 微生物学 · 食品科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF VIROLOGY · 2025 · IF 3.8

Self-assembled cyanidin-3-O-glucoside nanoparticles alleviate inflammation and ferroptosis induced by PRRSV infection

Xiaohan Chen,Yipeng Pang,Fructueux Modeste Amona,Zilu Liu,Fang Wang,Yuan Liang,Jiachen Yang,Wanhan Zhang,Xingtang Fang,Xi Chen

Porcine reproductive and respiratory syndrome virus (PRRSV) is a highly contagious pathogen that causes substantial economic losses in the global swine industry, primarily by impairing reproductive performance and respiratory health. However, current therapeutic approaches remain limited in effectively controlling PRRSV infection. Here, we present self-assembled cyanidin-3-O-glucoside (C3G)-based nanoparticles (C3G-Cs-SeNPs) as a promising antiviral agent against PRRSV infection. These nanoparticles demonstrated excellent stability and biocompatibility, with minimal cytotoxicity in Marc-145 cells. C3G-Cs-SeNPs significantly reduced ROS levels in PRRSV-infected cells, enhancing the antioxidant capacity and mitigating oxidative stress. In addition, they effectively inhibited key stages of the PRRSV lifecycle, including viral internalization and replication, leading to a marked decrease in viral proliferation. Moreover, C3G-Cs-SeNPs alleviated ferroptosis by restoring redox homeostasis through enhanced antioxidant enzyme activity. Mechanistically, these nanoparticles potentially activate the SIRT1/Nrf2/HO-1 signaling pathway, which plays a critical role in regulating inflammation and ferroptosis in PRRSV-infected cells. These findings suggest that C3G-Cs-SeNPs could serve as a novel therapeutic approach to modulate inflammation, ferroptosis, and viral replication in respiratory viral infections. Our study highlights the therapeutic potential of C3G-Cs-SeNPs in combating PRRSV infection, with important implications for viral infection management and respiratory disease treatment.

CAS / MDL: 7084-24-4
研究领域: 病毒学 · 纳米技术 · 免疫学 · 抗病毒治疗 · 氧化应激研究
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2020 · IF 6.306

Enzymatic acylation of cyanidin-3-glucoside with fatty acid methyl esters improves stability and antioxidant activity

Pingling Zhang,Shuang Liu,Zhengang Zhao,Lijun You,Mark D. Harrison,Zhanying Zhang

Cyanidin-3-glucoside is a major anthocyanin in legumes, black rice, and purple potato, and has anti-inflammatory and antioxidant properties. In the present study, the effect of acylation on cyanidin-3-glucoside lipophilicity, stability, and antioxidant capacity was investigated. Cyanidin-3-glucoside was enzymatically acylated through transesterification with fatty acid esters to produce three monoacylated cyanidin-3-glucoside esters, cyanidin-3-(6″- n- octanoyl)-glucoside, cyanidin-3-(6″-lauroyl)-glucoside, and cyanidin-3-(6″-myristoyl)-glucoside. Cyanidin-3-(6″- n- octanoyl)-glucoside had the highest thermostability and photostability of the three cyanidin-3-glucoside esters. While the in vitro antioxidant activity of cyanidin-3-(6″- n- octanoyl)-glucoside was 7.5%–14.3% lower than that of cyanidin-3-glucoside ( p  < 0.05), its cellular antioxidant activity increased by 33.3% ( p  < 0.05). Further, while cyanidin-3-(6″-lauroyl)-glucoside had lower stability and in vitro antioxidant activity than that of cyanidin-3-(6″- n- octanoyl)-glucoside, its cellular antioxidant capacity was 125.9% and 69.4% higher than cyanidin-3-glucoside and cyanidin-3-(6″- n- octanoyl)-glucoside, respectively ( p  < 0.05). This study demonstrated that transesterification can be used to improve the stability and in vivo antioxidant activity of cyanidin-3-glucoside.

研究领域: 食品科学 · 化学 · 生物化学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Analytical Methods · 2017 ·Vol. 9 ·期 17 ·2535-2545 · IF 1.9

Development and validation of green chromatography for the determination of anthocyanins in haskap berry, mulberry and blackberry

Jun Sang,Qun Ma,Cui-qin Li

This study was aimed at developing and validating a green HPLC-DAD method to determine anthocyanins using ethanol and an alpha-hydroxy acid aqueous solution as a mobile phase. The effects of alpha-hydroxy acids on the chromatographic behaviors of cyanidin-3-O-glucoside, the most predominant anthocyanin in nature, in a C18 column were investigated. Among seven selected alpha-hydroxy acids, tartaric acid exhibited potential for improving the chromatographic separation of cyanidin-3-O-glucoside. Cyanidin-3-O-glucoside was the main anthocyanin in haskap berry, mulberry, and blackberry, and the three berries were selected for further method development and validation. The optimized mobile phase was a mixture of ethanol and a 0.25 mol L−1 tartaric acid aqueous solution at the 20 : 80 (v/v) ratio. The retention time of cyanidin-3-O-glucoside was less than 1.8 min, and an optimum separation of anthocyanins was achieved in 4 min. The developed method was validated in terms of linearity, limits of detection and quantification, precision, repeatability, stability, and recovery. The calibration curve revealed good linearity (R2 = 0.9999), and the limits of detection and quantification were 0.038 mg L−1 and 0.125 mg L−1, respectively. The relative standard deviations of intra- and inter-day precision, repeatability, and stability were less than 5%. The recoveries of cyanidin-3-O-glucoside from the berry samples were between 99% and 101%, a satisfactory level. Additionally, the optimized mobile phase had a negligible effect on the C18 column stability. Therefore, the developed method was safe, rapid, and valid for anthocyanin analysis.

研究领域: 分析化学 · 食品科学 · 植物科学
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FOOD CHEMISTRY · 2022 · IF 9.231

Formation of hydroxyphenyl-pyranoanthocyanins derived from cyanidin-3-O-glucoside and effects of high-pressure processing on the transformation efficiency

Yingyu Zeng,Xusheng Li,Kailan Yuan,Bo Chen,Wenbao Zhang,Chao Wang,Jianxia Sun,Hosahalli S. Ramaswamy,Weibin Bai

Hydroxyphenyl-pyranoanthocyanins (PACNs), derived from anthocyanins (ACNs) reacted with hydroxycinnamic acids, have higher practical application value because of better physicochemical stability than their precursors. However, the slow formation rate restricted their broader applications. In the present study, cyanidin-3- O -glucoside (C3G) was chosen to react with four kinds of hydroxycinnamic acids in a model solution. Changes of color and the production of hydroxyphenyl-PACNs were monitored. The formation of derivatives was time-dependent, and the orange-yellow changing trend was correlated with the formation of PACNs and the consumption of C3G. In addition, high-pressure processing (HPP) as a widely-used non-thermal processing method in the food industry was conducted to investigate its impact on hydroxyphenyl-PACNs formation. The results showed that HPP significantly improves the yield of two types of hydroxyphenyl-PACNs (C3G-4-vinylcatechol and C3G-4-vinylphenol) and the retention of total residual pigments during 56 days of storage. Therefore, HPP contributed to color-protecting and the transformation of hydroxyphenyl-PACNs.

CAS / MDL: 9005-38-3
研究领域: 食品科学 · 化学 · 生物技术
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ENVIRONMENTAL POLLUTION · 2021 · IF 8.071

Canidin-3-glucoside prevents nano-plastics induced toxicity via activating autophagy and promoting discharge

Wen Chen,Qiang Chu,Xiang Ye,Yuhao Sun,Yangyang Liu,Ruoyi Jia,Yonglu Li,Pengcheng Tu,Qiong Tang,Ting Yu,Chuan Chen,Xiaodong Zheng

Increasing attention has been brought to microplastics pollution recently, while emerging evidences indicate that nano-plastics degraded from microplastics are more of research significance owing to stronger toxicity. However, there is little study focused on the prevention of nano-plastics induced toxicity until now. Canidin-3-glucoside (C3G), a natural anthocyanin proved to possess multiple functions like antioxidant and intestinal tissue protection. Thus, we proposed whether C3G could act as a molecular weapon against nano-plastics induced toxicity. In Caco2 cell and Caenorhabditis elegans ( C. elegans ) models, we found that polystyrene (PS) nano-plastics exposure resulted in physiological toxicity and oxidative damage, which could be restored by C3G. More significantly in Caco2 cells, we observed that autophagy was activated via Sirt1-Foxo1 signaling pathway to attenuate PS induced toxicity after C3G intervention and further verified by adding autophagy inhibitor 3-Methyladenine (3-MA). Meanwhile, PS co-localization with lysosomes was observed, indicating the encapsulation and degradation of PS. In C. elegans , by detecting LGG-1/LC3 expression in GFP-targeted LGG-1 report gene (LGG-1:GFP) labeled transgenic DA2123 strain, the co-localization of LGG-1:GFP with PS was found as well, means that autophagy is involved in C3G’s beneficial effects. Furthermore, we were surprised to find that C3G could promote the discharge of PS from N2 nematodes, which reduces PS toxicity more directly.

研究领域: 环境科学 · 毒理学 · 细胞生物学 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2022 · IF 8.025

Improving the physicochemical stability of Pickering emulsion stabilized by glycosylated whey protein isolate/cyanidin-3-glucoside to deliver curcumin

Xiaoya Tao,Cheng Chen,Yaochang Li,Xinguang Qin,Haizhi Zhang,Yuanyuan Hu,Zhengqi Liu,Xiaoming Guo,Gang Liu

Protein-polysaccharide-polyphenol delivery systems function as a promising tool to deliver bioactive ingredients aiming to improve their solubility and bioavailability. In this study, whey protein isolate (WPI), short-chain inulin (SCI), and cyanidin-3-glucoside (C3G) were first used to stabilize Pickering emulsions. The physicochemical properties and stability of curcumin encapsulated or not in Pickering emulsions were explored. Results showed that glycosylation and C3G reduced surface and interfacial tension on protein surfaces and inhibited the aggregation of emulsion droplets, thereby reducing the emulsion's particle size. WPI-SCI/C3G stabilized Pickering emulsion had the best stability. The CLSM results showed that the WPI-SCI and WPI-SCI/C3G stabilized emulsions were uniformly dispersed, suggesting that glycosylation and the interaction between protein and C3G enhanced the adsorption capacity of the interfacial protein and improved the stability of the Pickering emulsion. The retention rates of curcumin-loaded WPI-SCI- (67.34 %) and WPI-SCI/C3G- (77.07 %) stabilized Pickering emulsions on day 8 of storage were higher than those in WPI- (33.97 %) and WPI/C3G- (37.02 %) stabilized emulsions, and the degradation half-life was also extended from 7 days to >15 days. These findings provide a theoretical basis for the application of WPI Pickering emulsion and indicate a useful means for the delivery of bioactive components.

CAS / MDL: 3326-32-7 7385-67-3
研究领域: 食品科学 · 胶体化学 · 药学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2020 · IF 5.774

Degradation behavior of polyphenols in model aqueous extraction system based on mechanical and sonochemical effects induced by ultrasound

Pengxu Wang,Chuanxiang Cheng,Yaqin Ma,Meng Jia

In this study, the temporal and spatial variation of mechanical effects (ME) and sonochemical effects (SE), the degradation behavior of polyphenols as well as the correlation coefficients were comprehensively analyzed. The ME and SE showed inverse dependence along with the axial direction of transducer. Higher irradiation distance (50 mm) enhanced the ME but inhibited the generation of hydroxyl radicals (8.29 μmol/L). Rutin and cyanidin-3-glucoside, compared with thermal degradation (70°C, 6.41%, and 11.45%), were more susceptible to free radical degradation due to the boost of SE at low temperature (10°C, 20.23%, and 34.41%). The concentration of hydroxyl radicals at 70°C (18.38 μmol/L) was about 5.77 times lower than that at 10°C (3.22 μmol/L). No significant differences in the ME were observed for a wide range of temperatures (10–70°C). The impacts of increasing duty cycle on further promoting the ME and SE were limited. The concentration of hydroxyl radicals (0–23.37 μmol/L) increased linearly with sonication time (0–45 min) and the degradation of caffeic acid only occurred on a time scale (25 min). The free radical scavenger can minimize the degradation of polyphenols by inhibiting the hydroxyl radicals (23.37 μmol/L without t-BuOH; 12.17 μmol/L with t-BuOH). The above results showed that the degradation of polyphenols attacked by hydroxyl radicals presented a dose-response relationship. The correlation between the hydroxyl radicals and polyphenols as well as the mechanical effects and extraction yield indicated that the stability of polyphenols exposed to ultrasonic field depended on the structure-radical scavenging activity relationship and the extraction may be accompanied by the degradation.

CAS / MDL: 7681-11-0 153-18-4
研究领域: 化学 · 食品科学 · 超声技术
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