CRYSTAL GROWTH & DESIGN
·
2023
·
IF 3.8
Fan-Zhi Bu,Yue-Ming Yu,Min Zhang,Cui-Wei Yan,Zhi-Yong Wu,Yan-Tuan Li
To achieve new breakthroughs in the development of synergistic antiviral medication cocrystals of acyclovir (AYL) with phenolic acids, a cocrystallization-driven strategy for optimizing the physicochemical properties and increasing the antiviral efficacy is proposed. This method emphasizes the structural features and medicinal value together with the dominant properties of gallic acid (GLA) to promote both solubility and permeability of AYL by cocrystallizing GLA into AYL’s lattice; meanwhile, the antiviral ability of ALY can be greatly increased by activating the antiviral potential of GLA and utilizing the synergistic antiviral activity of both in cocrystal formation. Guided by this idea, the first AYL-phenolic acid cocrystal, AYL-GLA-2H2O, is orientationally constructed and fully characterized. The accurate cocrystal structure revealed by single-crystal X-ray diffraction indicates that the entry of GLA into the AYL lattice has disrupted the homodimer of AYL itself, leading to the formation of a hydrophobic heterodimer between AYL and GLA molecules, coupled with an aqueous tetramer, thus endowing the cocrystal with both hydrophilic and hydrophobic characteristics. Such structural feature induces a concurrent enhancement in dissolubility and permeability of the cocrystal compared with the parent medicine. These observations can be strongly supported by density functional theory-based theoretical investigations involving molecular electrostatic potential, Hirshfeld surface, frontier molecular orbital, and Gibbs solvation free energy. Interestingly, the perfected AYL’s properties along with the stimulated antiviral activity of GLA enable the two ingredients in the cocrystal to display synergistic antiviral activity against the herpes simplex virus with a cooperativity index of less than 1, contributing to enhancing the antiviral ability. Thus, this contribution not only highlights the effectiveness of combining theory with experiment to solve AYL’s issues via the cocrystallization-driven method but fills in the gaps from previous studies on AYL-phenolic acid cocrystals with synergistic antiviral effects.
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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.
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FOOD CHEMISTRY
·
2024
·
IF 8.5
Xinmiao Wang,Qian Wang,Dong Cai,Jinghan Yu,Xuan Chen,Xu Guo,Peiyong Tong,Xiaoyang Liu,Fawen Yin,Dayong Zhou
HPLC-UV analysis was used to evaluate the enzymatic degradation characteristics of tyrosol acyl esters (TYr-Es) and alkyl gallates (A-GAs). Among various hydrolytic enzymes, TYr-Es can be hydrolyzed by pancrelipase, while A-GAs cannot be hydrolyzed by pancrelipase. Interestingly, carboxylesterase-1b (CES-1b), carboxylesterase-1c (CES-1c) and carboxylesterase-2 (CES-2) are able to hydrolyze TYr-Es and A-GAs, and thus to liberate tyrosol (TYr) and gallic acid (GA). By contrast, the degrees of hydrolysis (DHs) of TYr-Es and A-GAs by CES-1b and CES-1c were significantly higher than those by CES-2. Meanwhile, the DHs of TYr-Es were much higher than those of A-GAs. Especially, the DHs firstly increased and then decreased with the increasing alkyl chain length. Besides, DHs positively correlated with the unsaturation degree at the same chain length. Through regulating carbon length, unsaturation degree and the ester bond structure, controlled-release of phenolic compounds and fatty acids (or fatty alcohols) from phenolic esters will be easily achieved.
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高影响因子
FOOD RESEARCH INTERNATIONAL
·
2024
·
IF 7
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.
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高影响因子
Foods
·
2026
·Vol. 15
·期 16
·2795
·
IF 6
Chang Liu,Mingze Xu,Yi Luan,Khubaib Ali,Rui Sun,Qingling Wang,Shixue Wu,Yixue Shi,Mangang Wu
Soybean oil-based pre-emulsions stabilized by myofibrillar protein (MP), Arabic gum (AG), or gallic acid-grafted Arabic gum (GA-AG) were used to partially (50%) or fully (100%) replace pork back fat in Western-style emulsified sausages. The present study investigated the effects of such replacement on the initial quality attributes and lipid oxidation stability of sausages during storage. Compared with sausages formulated with pure pork back fat, pre-emulsion substitution significantly reduced cooking loss and improved textural characteristics, especially hardness and springiness. Incorporating AG into the soybean oil pre-emulsion further enhanced the cooking yield of the products, while GA-AG retained AG’s stabilizing efficacy without compromising sensory acceptability. Sensory evaluation results demonstrated that 50% fat replacement achieved an optimal balance between textural performance and overall sensory preference. During refrigerated storage, the thiobarbituric acid reactive substance (TBARS) values increased in all sausage formulations. In contrast, sausages formulated with the GA-AG-stabilized soybean oil pre-emulsion exhibited the most potent inhibitory effect on lipid oxidation. After 312 h of storage, the TBARS values of the GA-AG groups were merely 32.8% of those of the single MP-treated groups. These findings suggest that the MP/GA-AG-stabilized soybean oil pre-emulsion system effectively improves the processing properties and oxidative stability of low-animal-fat emulsified sausages.
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FOOD CHEMISTRY
·
2026
·
IF 10.4
Qiuya Ji,Kai Ye,Ran Meng,Sijie Wu,Ran Feng,Bao Zhang
To address the conflicting challenges of fat reduction, texture fidelity, and co-delivery of hydrophilic and hydrophobic bioactive compounds, this study explored an innovative O 1 /W/O 2 -microstructured bigel system, WGB(O 1 /W/O 2 ). The system was stabilized through whey protein aggregates rapidly adsorbing at dual interfaces as an amphiphilic mediator, along with hydrogen bonding formation with guar gum in hydrogel matrix. The extended multilayered structure enabled WGB(O 1 /W/O 2 ) demonstrated favorable cream cheese simulation performance in appearance, viscoelastic properties, melting behavior, and texture characteristics. Sequential degradation of each phase during digestion (O 2 -W-O 1 ) increased the intestinal release of PTS and GA by up to 3.3-fold and 1.8-fold, respectively, over conventional bigels (O/W or bicontinuous). Among the bigels, cream cheese texture similarity ranked O 1 /W/O 2 > bicontinuous>O/W. The delivery efficiency for hydrophobic PTS followed O 1 /W/O 2 > O/W > bicontinuous, while that for hydrophilic GA followed O 1 /W/O 2 > bicontinuous>O/W. This study highlights broad application prospects of WGB(O 1 /W/O 2 ) for fat-reduced and nutrient-enhanced dual-functional foods, while advances understanding of bigel microstructure evolution-properties relationships.
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RSC Advances
·
2019
·Vol. 9
·期 9
·5142-5150
·
IF 3.049
Zaizhi Liu,Yanlong Qi,Mengling Gui,Chunte Feng,Xun Wang,Yang Lei
A Brønsted acid ionic liquid, 3-methyl-1-(4-sulfonylbutyl) imidazolium hydrogensulfate ([HO3S(CH2)4mim]HSO4), was used for the first time for the preparation of a sulfonated carbon catalyst. The catalyst was prepared from the residue obtained after recovery of the essential oil from the leaves of Cinnamomum longepaniculatum. The sulfonated carbon catalyst with an amorphous structure attained high acidic efficiency at a sulfonation temperature of 200 °C for 2 h of sulfonation time, and was characterised. SEM morphologies revealed that the carbon catalyst consisted of uniform carbon microspores. FTIR analysis, elemental analysis, and X-ray photoelectron spectroscopy revealed that the sulfonic acid group was successfully introduced on the surface of the sulfonated carbon catalyst. The result of TG analysis showed that the obtained sulfonated carbon catalyst has high thermal stability. Good acid and catalytic activity of the obtained sulfonated carbon catalyst were observed for the preparation of ellagic acid and gallic acid, which is comparable to those of diluted sulfuric acid and a sulfonated carbon catalyst that had been prepared with concentrated sulfuric acid. The excellent reusability of the sulfonated carbon catalyst was also confirmed by repeated experimental trials. In summary, the sulfonated catalyst derived from the residue obtained after recovery of essential oil from the leaves of C. longepaniculatum is an economic, eco-benign and promising substitute for traditional mineral acid catalysts for acidic catalysis in industrial applications.
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高影响因子
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