JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2022
·Vol. 103
·期 8
·3896-3906
·
IF 4.125
Xinyue Hong,Xin Song,Xiaqing Wu,Change Yang,Deming Gong,Guowen Zhang
BACKGROUND Gallocatechin gallate (GCG), a catechin of tea polyphenols, possesses inhibitory ability against tyrosinase, but few studies have reported how common processing methods affect it. In this research, the influence of heating and ultrasound treatments on the inhibition of GCG against tyrosinase was explored by ultraviolet–visible absorption, fluorescence spectroscopy, high-performance liquid chromatography and liquid chromatography–tandem mass spectrometry. RESULTS Both heating and ultrasound treatments of GCG alone improved GCG's inhibitory ability against tyrosinase compared with the untreated, and a combination of heating and ultrasound treatment (100 °C, 20 min + 630 W, 20 min) further decreased the relative tyrosinase activity to 26.8%. The treated GCG exhibited a stronger fluorescence quenching effect on tyrosinase, but did not have any influence on the static quenching mechanism. Compared to the untreated GCG, the binding constants of treated GCG by heating, ultrasound and their combination with tyrosinase significantly increased, but the number of binding sites was still approximately one and the main driving force of the treated GCG was still hydrophobic interaction. After treatments of heating, ultrasound and their combination, the composition of GCG solutions was changed. CONCLUSION The enhanced inhibition of treated GCG on tyrosinase may be due to partial conversion of GCG into epigallocatechin-3-gallate (EGCG) and gallic acid (GA), which may cooperate with GCG to better inhibit the enzyme activity. This study has provided some valuable information for the application of catechins against tyrosinase in food processing and cosmetic industry. © 2022 Society of Chemical Industry.
研究领域:
食品科学
·
化妆品化学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2023
·Vol. 103
·期 15
·7381-7392
·
IF 4.1
Qinhao Guan,Lihua Tang,Liangliang Zhang,Lixin Huang,Man Xu,Yuan Wang,Meng Zhang
BACKGROUND Diabetes mellitus poses a substantial threat to public health due to rising morbidity and mortality. α-Glucosidase is one of the key enzymes affecting diabetes. Herein, (−)-epigallocatechin-3-gallate (EGCG) and (−)-epigallocatechin (EGC) were applied to clarify the role of the galloyl moiety of tea polyphenols in the inhibition of glycation and α-glucosidase activity. The structure–activity relationship of the galloyl moiety in EGCG on α-glucosidase was investigated in terms of inhibition kinetics, spectroscopy, atomic force microscopy and molecular docking. A bovine serum protein–fructose model was employed to determine the effect of the galloyl moiety on glycation. RESULTS The results indicated that the introduction of a galloyl moiety enhanced the capacity of EGCG to inhibit glycation and α-glucosidase activity. The IC 50 value of EGC is approximately 2400 times higher than that of EGCG. Furthermore, the galloyl moiety in EGCG altered the microenvironment and secondary structure of α-glucosidase, resulting in a high binding affinity of EGCG to α-glucosidase. The binding constant of EGCG to α-glucosidase at 298 K is approximately 28 times higher than that of EGC. CONCLUSION Overall, the galloyl moiety of EGCG plays a crucial role in inhibiting glycation and α-glucosidase activity, which helps to enhance the molecular understanding of the structure and function of the polyphenol galloyl moiety in the science of food and agriculture. © 2023 Society of Chemical Industry.
研究领域:
食品科学
·
分子生物学
·
药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2021
·
IF 7.514
Jinghui Zhou,Changwei Liu,Shimin Zhao,Ya Liu,Sheng Zhang,Qiang Zhao,Fen Wang,Gang Xu,Jianan Huang,Zhonghua Liu
Theaflavin-3,3ʹ-digallate (TFDG) in black tea possesses several health benefits. However, low TFDG yields limit its application. Herein, tyrosinases from Bacillus megaterium (Bmtyrc) were used to synthesize TFDG. To improve the catalytic efficiency of tyrosinase, a directed evolution strategy and a high-throughput screening method was employed. Compared with the wild type, mutant Bmtyrc-3 (N205D/D166E/D167G/F197W) showed 6.46 and 4.91-folds higher specific activity and 51.97- and 1.95-folds higher Vmax values towards epigallocatechin gallate (EGCG) and epicatechin gallate (ECG), respectively. Moreover, Bmtyrc-3 displayed significantly enhanced catalytic efficiencies, and the space–time yield of TFDG was 35.35 g L -1 d -1 . Bmtyrc-3 presents a broader substrate binding area, caused by a mutation (N205D) encompassing the active site. Changes in the potential of the substrate binding site and hydrogen bonds, and the electrostatic effect on the protein surface resulted in an increased activity of the substrates EGCG and ECG.
研究领域:
生物技术
·
生物化学
·
酶学
·
食品科学
✓ 已验证
DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2019
·
IF 8.355
Xiaohong Hu,Jia Wen,Haibo Zhang,Qian Wang,Caiya Yan,Lang Xing
The most important thing to do with hexavalent chromium (Cr(VI)) removal in wastewater through adsorption-reduction method is to find an adsorbent that has both strong adsorbability and reducibility. Herein, an eco-friendly material ZIF-8-EGCG, which was a combination of epicatechin gallate (EGCG) and ZIF-8, was synthesized to treat Cr(VI)-containing wastewater. At room temperature, the maximum adsorption amount of Cr(VI) reached 136.96 mg·g −1 , and the Cr(VI) reduction rate (96%) was much better than that of the original ZIF-8 (37%). Such outcome was among the best in the existing studies using MOFs to treat Cr(VI). In addition, the characterization results showed that the surface of ZIF-8-EGCG was electronegative. The material was irregular sphere with pore size of 7.12 nm and BET surface area of 113.02 m 2 ·g −1 . The well-fitted Langmuir adsorption isotherm and pseudo first/second-order kinetics model suggested that the adsorption of Cr(VI) on ZIF-8-EGCG was governed by both physical and chemical processes. Stability results revealed that the overall stability of ZIF-8-EGCG due to the etched structure was slightly inferior to ZIF-8, especially at higher temperatures (>35 °C). Simultaneously, the reaction between ZIF-8-EGCG and Cr(VI) was a spontaneous, exothermic, entropic decrease process.
研究领域:
环境科学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2022
·
IF 8.025
Wangli Dai,Chen Yan,Yicheng Ding,Wenjie Wang,Saiqi Gu,Zheng Xu,Xuxia Zhou,Yuting Ding
The objective of this study was to investigate the potential application of chitosan coatings incorporating epigallocatechin gallate (EGCG) for preserving fillets of bighead carp during chilled storage. The fillets were coated with acetic acid and glycerol, chitosan, and chitosan-EGCG, respectively, and the changes in their physicochemical, microbiological, and sensory characteristics during storage at 4 °C were determined. Notably, total volatile basic nitrogen, thiobarbituric-acid-reactive substances, and K value of chitosan-EGCG coated fillets sampled on day 15 were 48.04 %, 60.19 %, and 32.91 % lower than untreated fillets, respectively. Microbial enumeration suggested that the inclusion of EGCG significantly improved the inhibitory effect of pure chitosan coating on the proliferation of microorganisms. Furthermore, the chitosan-EGCG coated fillets also performed the best in terms of color, texture, and sensory analysis, and extended the shelf-life of the fillets for at least 6 days. A principal component analysis further confirmed the preserving effect of the chitosan-EGCG coating. Mantel test results suggested that the fillets' organoleptic characteristics strongly correlated with physicochemical and microbiological indicators. Overall, this work provides an effective protocol for food quality control and the extension of shelf life during chilled storage, and it clarifies the relationships between organoleptic characteristics and physicochemical and microbiological indexes.
研究领域:
食品科学
·
生物化学
✓ 已验证
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Dong Cai,Xinmiao Wang,Qian Wang,Peiyong Tong,Weiyuan Niu,Xu Guo,Jinghan Yu,Xuan Chen,Xiaoyang Liu,Dayong Zhou,Fawen Yin
The freeze-drying approach was used to create inclusion complexes utilizing alkyl gallates and β-cyclodextrin, namely dodecyl gallate, octyl gallate, butyl gallate, and ethyl gallate, which are exemplary examples of phenolic esters. The everted-rat-gut-sac model demonstrated that the inclusion complexes released alkyl gallates, which were subsequently hydrolyzed to generate free gallic acid, as evidenced by HPLC-UV analysis. Both gallic acid and short-chain alkyl gallates were capable of permeating the small intestinal membrane. The transport rate of gallic acid (or alkyl gallates) exhibited an initial rise followed by a drop when the carbon-chain lengths varied. The inclusion complex groups exhibited a superior sustained-release effect compared to the comparable alkyl gallates groups, thus possibly leading to higher bioavailability and stronger bioactivity. Moreover, altering the length of the carbon chain will allow for the effortless achievement of regulated release of phenolic compounds and short-chain phenolic esters from such β-cyclodextrin inclusion complexes.
研究领域:
药剂学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Qian Wang,Weiyuan Niu,Xinmiao Wang,Jinghan Yu,Xuan Chen,Dong Cai,Fawen Yin,Xiaoyang Liu,Dayong Zhou
Ethanol evaporation method was applied to synthesize phospholipid complexes from phosphatidylcholine (PC) and short-chain alkyl gallates (A-GAs, a typical representative of lipophenols) including butyl-, propyl- and ethyl gallates. 1 H NMR, UV and FTIR showed that A-GAs were interacted with PC through weak physical interaction. Through the analysis of concentrations of A-GAs and gallic acid (GA) by an everted rat gut sac model coupled with HPLC-UV detection, phospholipid complexes were found to gradually release A-GAs. These liberated A-GAs were further hydrolyzed by intestinal lipases to release GA. Both of GA and A-GAs could cross intestinal membrane. Especially, the transmembrane A-GAs could also be hydrolyzed to produce GA. Undoubtedly, the dual release of phenol compounds from phospholipid complexes of short-chain lipophenols will be effective to extend the in vivo residence period of phenol compounds. More importantly, such behavior is easily adjusted by changing the acyl chain lengths of lipophenols in phospholipid complexes.
研究领域:
生物化学
·
药物递送系统
·
食品科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Frontiers in Pharmacology
·
2024
·
IF 4.4
Zou Caomin,Chen Qianru,Li Jiasheng,Meng Jiang
Moutan Cortex (MC) has been used in treating inflammation-associated diseases and conditions in China and other Southeast Asian countries. However, the active components of its anti-inflammatory effect are still unclear. The study aimed to screen and identify potential cyclooxygenase-2 (COX-2) inhibitors in MC extract. The effect of MC on COX-2 was determined in vitro by COX-2 inhibitory assays, followed by bio-affinity ultrafiltration in combination with ultra-performance liquid chromatography-mass spectrometry (BAUF-UPLC-MS). To verify the reliability of the constructed approach, celecoxib was applied as the positive control, in contrast to adenosine which served as the negative control in this study. The bioactivity of the MC components was validated in vitro by COX-2 inhibitor assay and RAW264.7 cells. Their in vivo anti-inflammatory activity was also evaluated using LPS-induced zebrafish inflammation models. Finally, molecular docking was hired to further explore the internal interactions between the components and COX-2 residues. The MC extract showed an evident COX-2-inhibitory effect in a concentration-dependent manner. A total of 11 potential COX-2 inhibitors were eventually identified in MC extract. The COX-2 inhibitory activity of five components, namely, gallic acid (GA), methyl gallate (MG), galloylpaeoniflorin (GP), 1,2,3,6-Tetra-O-galloyl-β-D-glucose (TGG), and 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (PGG), were validated through both in vitro assays and experiments using zebrafish models. Besides, the molecular docking analysis revealed that the potential inhibitors in MC could effectively inhibit COX-2 by interacting with specific residues, similar to the mechanism of action exhibited by celecoxib. In conclusion, BAUF-UPLC-MS combining the molecular docking is an efficient approach to discover enzyme inhibitors from traditional herbs and understand the mechanism of action.
研究领域:
药理学
·
分析化学
·
生物化学
·
中药学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2022
·
IF 9.231
Rui Cui,Shengnan Ji,Minquan Xia,Xing Fu,Xi Huang
Ovomucoid (OVM) is a critical anti-nutritional factor in egg, which may reduce nutrient utilization. In this study, the effects of polyphenols on the trypsin inhibitory activity (TIA) of OVM were investigated by exploring the structural changes and interaction mechanisms. The results found that TIA decreased to 62.34% and 90.41% as epigallocatechin gallate (EGCG) and gallic acid (GA) were added individually. EGCG and GA interacted with OVM via static quenching and hydrophobic interaction. They induced a transition of OVM conformation from disorder to order. Infrared and fluorescence quenching analysis showed that the interaction between EGCG or GA and OVM was spontaneous, and hydrophobic interaction was the predominant force. The mechanism suggested that polyphenols affect the protein conformation by spontaneously binding to OVM in hydrophobic interactions, and lowering the TIA through reduced hydrophobicity. In summary, EGCG may be a promising OVM trypsin activity inactivator, which could also guarantee safety of egg products.
研究领域:
食品科学
·
生物化学
·
营养学
✓ 已验证
DOI
PubMed
高影响因子
Food & Function
·
2025
·
IF 5.4
Xuan Chen,Xinmiao Wang,Qian Wang,Dong Cai,Jinghan Yu,Beiwei Zhu,Dayong Zhou,Fawen Yin
The heat treatment method was used to synthesize starch inclusion complexes from starch and short-chain alkyl gallates (a typical representative of phenololipids), such as butyl gallate, propyl gallate, ethyl gallate and methyl gallate. In an everted rat gut sac model, HPLC-UV analysis revealed that the released alkyl gallates from inclusion complexes were degraded to produce gallic acid. Gallic acids (0.009455–0.014160 nmol min−1) and alkyl gallates (0.2695–0.9441 nmol min−1) were both able to pass through intestinal membranes. After transmembrane transfer, alkyl gallates could also be hydrolyzed to produce gallic acid (1.947 × 10−5–2.290 × 10−5 min−1). It was evident that such an inclusion complex demonstrated superior dual sustained-release characteristics for phenolic compounds. Meanwhile, starch inclusion complexes can also slow down starch digestion by raising resistant starch (from 12.2% to 27.2–46.0%) and lowering rapidly digestible starch (from 51.2% to 22.2–51.2%), according to a glucose oxidase–peroxidase analysis. The delayed digestion behavior of starch in inclusion complexes is very beneficial for blood glucose control. Thus, our work effectively established a theoretical foundation for modifying the dual sustained-release behavior of phenolic compounds and the retardation of starch digestion by adjusting the carbon-chain length in starch inclusion complexes.
研究领域:
食品科学
·
营养学
·
药理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF CONTROLLED RELEASE
·
2025
·
IF 11.5
Jiahao Wang,Renjie Zhang,Hongying Xie,Yuexin Yang,Hao Chen,Quankui Lin
In cataract, oxidative stress plays an important role. It breaks the balance of the antioxidant defense system by destroying biological macromolecules such as proteins, lipids and nucleic acids in the lens, induces lens opacity, and then leads to the formation of cataract. The antioxidant properties of epigallocatechin gallate (EGCG) are well-established, particularly its ability to scavenge ROS and modulate cellular pathways. However, its therapeutic potential is limited by poor stability and bioavailability. To overcome these challenges, the work is designed to form a metal-phenolic network (MPN) system by coordinating EGCG with zinc ions. MPNs offer distinct advantages for ocular drug delivery, including enhanced structural stability, improved cellular uptake, and the ability to simultaneously target multiple oxidative stress pathways. By doing so, an antioxidant nanoparticle is formed to slow down the turbidity process of the lens induced by oxidative stress and thus prevent the occurrence of cataract. The particle size, zeta potential, ultraviolet absorption spectrum, FTIR, surface morphology and element distribution of EGCG-Zn were determined. In vitro, EGCG-Zn has good biosafety, cell uptake performance and anti-cell damage performance. In addition, from a mechanistic analysis, the particles can scavenge free radicals and reduce the production of intracellular ROS. Similarly, EGCG-Zn can well prevent the damage of reactive oxygen species to intracellular lysosomes, mitochondria, cytoskeleton, DNA synthesis and cell senescence. In the UV-B-induced cataract animal model in rats, EGCG-Zn has good in vivo safety. The transparency of the lens in the experimental group using EGCG-Zn is significantly lower than that in the untreated model group. In conclusion, EGCG-Zn nanoparticles are expected to become an important means in the field of cataract treatment, bringing hope for restoring clear vision to many cataract patients.
研究领域:
眼科
·
药剂学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2022
·Vol. 27
·期 21
·7301
·
IF 4.927
Shanshan Wang,Hua Wang,Fujie Yan,Jie Wang,Songbai Liu
In this study, a novel galloyl phytol antioxidant was developed by incorporating the branched phytol chain with gallic acid through mild Steglich esterification. The evaluation of the radical scavenging activity, lipid oxidation in a liposomal model, and glycerol trioleate revealed its superior antioxidant activities in both dispersed and bulk oils. Then, the antioxidant capacity enhancement of galloyl phytol was further explored using thermal gravimetry/differential thermal analysis (TG/DTA), transmission electron microscopy (TEM), and molecular modeling. The EC50 values of GP, GPa, and GE were 0.256, 0.262, and 0.263 mM, respectively, which exhibited comparable DPPH scavenging activities. These investigations unveiled that the branched aliphatic chain enforced the coiled molecular conformation and the unsaturated double bond in the phytol portion further fixed the coiled conformation, which contributed to a diminished aggregation tendency and enhanced antioxidant activities in dispersed and bulk oils. The remarkable antioxidant performance of galloyl phytol suggested intriguing and non-toxic natural antioxidant applications in the food industry, such as effectively inhibiting the oxidation of oil and improvement of the quality and shelf life of the oil, which would contribute to the use of tea resources and extending the tea industry chain.Keywords:gallic acid;phytol;galloyl phytol;antioxidant activity;Steglich esterification
研究领域:
食品科学
·
化学
·
药学
✓ 已验证
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）