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 & 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 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 AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Qian Wang,Xinmiao Wang,Dong Cai,Jinghan Yu,Xuan Chen,Weiyuan Niu,Siya Wang,Xiaoyang Liu,Dayong Zhou,Fawen Yin
Phospholipid complexes of alkyl gallates (A-GAs) including ethyl gallate (EG), propyl gallate (PG), and butyl gallate (BG) were successfully prepared by the thin film dispersion method. HPLC-UV analysis in an everted rat gut sac model indicated that A-GAs can be liberated from phospholipid complexes, which were further hydrolyzed by intestinal lipase to generate free gallic acid (GA). Both A-GAs and GA are able to cross the membrane, and the hydrolysis rate of A-GAs and the transport rate of GA are positively correlated with the alkyl chain length. Especially, compared with the corresponding physical mixtures, the phospholipid complexes exhibit slower sustained-release of A-GAs and GA. Therefore, the formation of phospholipid complexes is an effective approach to prolong the residence time in vivo and additionally enhance the bioactivities of A-GAs and GA. More importantly, through regulating the carbon skeleton lengths, controlled-release of alkyl gallates and gallic acid from phospholipid complexes will be achieved.
研究领域:
药理学
·
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
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
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2025
·
IF 8.5
Xuan Chen,Xinmiao Wang,Qian Wang,Dong Cai,Jinghan Yu,Dayong Zhou,Xiaoyang Liu,Fawen Yin
Corn starch inclusion complexes of alkyl gallates (typical phenololipid representatives), including stearyl gallate, dodecyl gallate, octyl gallate, and hexadecyl gallate, were synthesized by using a heat treatment method. Such inclusion complexes exhibited significantly improved two-step release properties for gallic acid. In other words, gallic acid was generated via the breakdown of alkyl gallates that were released from inclusion complexes in an everted rat intestinal sac model, as determined by HPLC-UV analysis. The produced gallic acid could subsequently pass through intestinal membranes. On the other hand, a glucose oxidase-peroxidase analysis revealed that starch inclusion complexes can slow down starch digestion by increasing the proportion of resistant starch (from 12.2 % to 14.5–30.8 %) and decreasing the proportion of rapidly digestible starch (from 51.2 % to 39.4–49.2 %). Importantly, the two-step release characteristics of gallic acid and the retardation behavior of starch digestion can be easily regulated by modifying the acyl carbon chain length.
研究领域:
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2019
·
IF 5.399
Yinyin Liao,Xiumin Fu,Haiyun Zhou,Wei Rao,Lanting Zeng,Ziyin Yang
Although specialized metabolite distributions in different tea ( Camellia sinensis ) tissues has been studied extensively, little is known about their within-tissue distribution owing to the lack of nondestructive methodology. In this study, desorption electrospray ionization imaging mass spectrometry was used to investigate the within-tissue spatial distributions of specialized metabolites in tea. To overcome the negative effects of the large amount of wax on tea leaves, several sample preparation methods were compared, with a Teflon-imprint method established for tea leaves. Polyphenols are characteristic metabolites in tea leaves. Epicatechin gallate/catechin gallate, epigallocatechin gallate/gallocatechin gallate, and gallic acid were evenly distributed on both sides of the leaves, while epicatechin/catechin, epigallocatechin/gallocatechin, and assamicain A were distributed near the leaf vein. L -Theanine was mainly accumulated in tea roots. L -Theanine and valinol were distributed around the outer root cross-section. The results will advance our understanding of the precise localizations and in-vivo biosyntheses of specialized metabolites in tea.
研究领域:
植物科学
·
分析化学
·
代谢组学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2021
·
IF 6.953
Bingqing Huang,Zhigang Zhang,Nengshui Ding,Bingli Wang,Guoguang Zhang,Peng Fei
In this paper, a method for the enzymatic modification of pectin, in which gallic acid (GA) and propyl gallate (PG) were grafted onto pectin molecules in an aqueous/organic two-phase system catalyzed by lipase, was proposed. The potential reaction mechanism was explored through UV–Vis, FTIR and 1 H NMR spectroscopic methods and density functional theory. Results suggested that the lipase played a dual role during the modification by catalyzing the hydrolysis of methyl ester bonds of pectin in the aqueous phase and the esterification between the 4-OH of GA and PG and the –COOH of pectin in the organic phase. Moreover, the effects of GA and PG on the antioxidant and the antibacterial activities of pectin were evaluated, and results showed that the antioxidant and the antibacterial activities of modified pectin were better than those of native pectin. The effect of modified pectin on the quality of fresh bass ( Lateolabrax maculatus ) was further studied. Results suggested that, compared to control group, the total viable count , histamine level , malondialdehyde content and acid value of bass fillets treated with modified pectin were significantly reduced, whereas the sensory score was significantly increased.
研究领域:
食品科学
·
化学
·
生物化学
·
农业科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2020
·
IF 6.306
Yu-gang Shi,Run-run Zhang,Chen-min Zhu,Ming-feng Xu,Qing Gu,Rammile Ettelaie,Shan Lin,Yi-fan Wang,Xin-yi Leng
The objective of this study was to investigate the antibacterial activity and potential mechanism of alkyl gallates against Escherichia coli and Staphylococcus aureus . Results show that the length of the alkyl chain plays a pivotal role in eliciting the activity and octyl gallate (OG) exerted excellent bactericidal activity through a multiple bactericidal mechanism. OG functions against both bacteria through damaging bacterial cell wall integrity, permeating into cells and then interacting with DNA, as well as disturbing the activity of the respiratory electron transport chain to induce a high-level toxic ROS (hydroxyl radicals) generation and up-regulation of the ROS genes. Also, electrospun nanofibers with OG have unique superiorities for maintaining the freshness of the icefish (4 °C). This research not only provides a more in-depth understanding of the interaction between OG and microorganisms but also highlights the great promise of using OG as a safe multi-functionalized food additive for food preservations.
研究领域:
食品科学
·
微生物学
·
材料科学
✓ 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
JOURNAL OF FLUORESCENCE
·
2022
·Vol. 32
·期 2
·783-789
·
IF 2.525
Xu Lina,Yao Na,Ding Haiyang,Yang Xiaohua,Li Shouhai,Xia Jianling,Li Mei
Selective and sensitive water content measurement in organic solvents is extremely significant for both industrial use and laboratory preparation. Carbon nanodots are promising carbon nanomaterials with unique and novel properties and thus have drawn growing attention. However, the hydrothermal approach for the preparation of carbon dots always uses water as solvent, and consequently, the development of carbon dots from biomass materials for fluorescence detection of water content remains unexplored. Here, carbon dots were prepared from gallic acid via a cheap and facile one-step method. The as-prepared carbon dots present excellent sensitivity and selectivity toward water content and exhibits good linear relationships with water content in range of 0–10%. The carbon dots demonstrated a strong antioxidation capacity and colour-reaction of Fe 3+ like gallic acid. The carbon dots also showed solid-state lighting.
研究领域:
材料科学
·
分析化学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）