Antioxidants
·
2026
·Vol. 15
·期 8
·1008
·
IF 8.2
Zhengyan Tan,Pei Xu,Dan Wang,Zongna Han,Huaying Chen,Qianqian Zhu,Yang Yang,Wei Pan,Piao Wang,Rongxiang Chen
This study established an activity-oriented analysis method based on offline two-dimensional liquid chromatography–electrochemical detection (2D-LC-ECD) combined with ultra-high-performance liquid chromatography–Orbitrap-MS/MS (UHPLC-Orbitrap-MS/MS), which was used to comprehensively characterize the antioxidant components ofPolygonum multiflorumThunb. leaves (PML) and screen for differential compounds in samples from different origins. Antioxidant components were screened using 2D-LC-ECD combined with in vitro radical scavenging experiments; structure identification was conducted via UHPLC-Orbitrap-MS/MS, and chemometric analysis alongside quantitative determination of 19 major components was carried out across 31 batches of samples. A total of 43 potential antioxidant compounds were identified from PML, including 11 phenolic acids, 29 flavonoids, 2 stilbene glycosides, and 1 amino acid; phenolic acids and their derivatives, along with flavonoids, were identified as major contributors to antioxidant activity. Hierarchical clustering analysis and principal component analysis both grouped samples into four categories by origin; the orthogonal partial least squares discriminant analysis model (R2X = 0.933, R2Y = 0.941, Q2= 0.846) screened 10 key markers (VIP > 1). The quantitative results showed that polygonacetophenoside had the highest content in PML. In summary, the 2D-LC-ECD coupled with LC-Orbitrap-MS/MS strategy confirmed that phenolic acids and flavonoids are the core material basis for PML’s antioxidant capacity, providing scientific evidence for the industrial development of PML as a natural antioxidant.
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CRYSTAL GROWTH & DESIGN
·
2026
·Vol. 26
·期 16
·6344-6355
·
IF 3.6
Zhu Zuoxuan,Tao Tiantian,Zhou Donghui,Wang Dawei,Wang Dekun,Tang Weiwei,Tan Xiaoyue,Gong Junbo
The pathological crystallization of calcium oxalate monohydrate
(COM) holds paramount significance within the context of human kidney
stone ailment. Previous studies have suggested that polyphenols extracted
from traditional Chinese medicinal herbs effectively inhibit COM crystallization,
whereas the relationship between the molecular structure and their
inhibitory performance remains to be elucidated. In this study, we
examined a library of natural polyphenol plant extracts to investigate
the influence of type, number, spatial arrangement, and length of
functional groups on inhibition performance, thereby addressing a
key gap in the rational design and selection of high-efficacy stone
inhibitors. We combined bulk crystallization assays and microfluidic
growth-kinetics measurements in aqueous solution and artificial urine
with in vitro evaluations of crystal adhesion and
cytotoxicity in human proximal renal tubular epithelial (HK-2) cells,
as well as validation in a murine model, to systematically assess
the efficacy of polyphenolic derivatives in vitro and in vivo . Our results highlight the trihydroxyl
motif and ester functionalities as critical determinants of COM inhibition,
consistent with preferential binding to specific crystal faces and
suppression of crystal growth. Among the polyphenols, methyl gallate
and ethyl gallate markedly reduced crystal–cell adhesion and
crystal-induced cytotoxicity, while ethyl gallate further exhibited
superior in vivo efficacy by reducing renal stone
deposition, inflammation, and tubular injury. Taken together, these
findings identify ethyl gallate as a promising therapeutic lead and
support its further preclinical development for the management of
calcium oxalate kidney stones.
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2026
·
IF 8.7
Xuan Chen,Xinmiao Wang,Qian Wang,Chuan Li,Dayong Zhou,Fawen Yin
Inclusion complexes retained stable V-type crystals after frying. • CS-PG and CS-HG reduced oil uptake and improved antioxidant capacity. • Complexes increased resistant starch and inhibited starch hydrolysis. Deep-frying, while widely used for its desirable sensory attributes, poses health concerns due to high oil absorption and lipid oxidation. In this study, we synthesized a series of corn starch-alkyl gallate inclusion complexes with varying acyl chain lengths (C1-C18) and systematically investigated their structure-property relationships during frying, focusing on structural stability, oil absorption, antioxidant capacity, and starch digestibility. XRD, FTIR, and SEM analyses confirmed that all complexes retained a stable V type crystalline structure after frying, with CS-PG (C3) and CS-HG (C16) exhibiting the lowest oil absorption due to their superior crystalline order and compact lamellar organization. However, antioxidant evaluation revealed a distinct chain length dependency: CS-OG (C8) demonstrated the most effective suppression of lipid oxidation, as evidenced by the lowest peroxide value (POV) and thiobarbituric acid reactive substances (TBARS) levels. This divergence highlights a critical performance trade off, wherein intermediate chain lengths optimize antioxidant activity at the oil-starch interface, while shorter and longer chains favor structural integrity and oil barrier properties. Digestibility assays further showed that complexation effectively reduced rapidly digestible starch (RDS) and increased resistant starch (RS) content, with the extent of enzymatic resistance generally improving with chain length. Collectively, these findings demonstrate that the functional performance of starch-alkyl gallate inclusion complexes is governed by alkyl chain length in a property dependent manner. Rather than a single “best” formulation, the optimal chain length varies according to the target application, CS-PG and CS-HG for low oil fried foods, and CS-OG for enhanced oxidative stability. Download: Download high-res image (243KB) Download: Download full-size image
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FOOD CHEMISTRY
·
2026
·
IF 10.4
Xu Guo,Qian Wang,Dong Cai,Xinmiao Wang,Jinghan Yu,Dayong Zhou,Fawen Yin
Antarctic krill phospholipids were complexed with alkyl gallates of varying chain lengths. • Complexation via hydrogen bonding was confirmed by docking, FTIR, UV, and NMR. • Hydrolysis rates increased with chain length; intact ester transport showed inverse trend. • Phospholipid complexes reduced both hydrolysis and transport, confirming sustained release. • Strong hydrolysis-transport correlation identified hydrolysis as rate-limiting for absorption. To investigate the value-added potential of Antarctic krill phospholipids for sustained polyphenol delivery, we prepared phospholipid complexes of alkyl gallates with varying chain lengths (methyl, ethyl, propyl, butyl) and characterized them via molecular docking, spectroscopy, and rheology. A dual-release mechanism is proposed, involving two sequential stages: the putative dissociation of alkyl gallates from the phospholipid matrix, and subsequent enzymatic hydrolysis of the ester bond by intestinal lipases. Using everted rat intestinal sac model with HPLC-UV, we systematically evaluated hydrolysis and transport kinetics. Results showed that alkyl chain length significantly modulated hydrolysis rates (increasing with chain length) and intact ester transport (decreasing with chain length). The uniformly reduced hydrolysis and transport rates upon complexation are consistent with the presence of a dissociation step that may act as a sustained-release reservoir. The kinetic parameters for both hydrolysis and transport showed strong linear correlations with chain length, enabling quantitative prediction of release behavior. Download: Download high-res image (300KB) Download: Download full-size image
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2026
·
IF 4
Xu Guo,Jinghan Yu,Qian Wang,Chuan Li,Weiyuan Niu,Xinmiao Wang,Dayong Zhou,Fawen Yin
BACKGROUND Alkyl gallates (A-GAs) are widely used as antioxidants but suffer from poor oral bioavailability. This study investigates whether complexation with phosphatidylcholine (PC) can enable a controlled two-step release of gallic acid (GA) from A-GAs, and how the acyl chain length of A-GAs modulates this process. RESULTS PC complexes with A-GAs (methyl to stearyl gallates) were prepared by thin-film dispersion. FTIR, UV, and 1 H-NMR confirmed hydrogen bonding between the phenolic hydroxyl of A-GAs and the phosphate group of PC. In an everted rat gut sac model, short-chain A-GAs (C1–C4) and GA showed efficient intestinal permeation. The hydrolysis of A-GAs to GA followed first-order kinetics. As the acyl chain length increased, the hydrolysis rate constant ( k DH ) first increased (methyl: 0.9681 × 10 −5 min −1 ; ethyl: 1.278 × 10 −5 ; propyl: 1.852 × 10 −5 ; butyl: 1.905 × 10 −5 ; octyl: 3.154 × 10 −5 ) and then decreased (dodecyl: 1.699 × 10 −5 ; tetradecyl: 0.9911 × 10 −5 ; hexadecyl: 0.6323 × 10 −5 ; stearyl: 0.4074 × 10 −5 ). Octyl and longer esters were not transported across the intestinal mucosa due to self-association. CONCLUSION PC–A-GA complexes enable a two-step sustained release of GA: release of intact A-GAs, followed by enzymatic hydrolysis to GA. The release kinetics can be tuned by varying the acyl chain length of the A-GA, providing a rational design strategy for improving the oral bioavailability of phenolic compounds. © 2026 Society of Chemical Industry.
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ACS Sustainable Chemistry & Engineering
·
2025
·
IF 7.3
Jie Li,Ke Xu,Jiajun Cui,Fei Gao,Hongying Guo,Jiyou Yang,Mengren Li,Zhan Ma,Zijun Wang,Liuping Zhang,Weiwei Huan
Natural trees with uniquely aligned microchannels and water transportation capability bring inspiration to design high-performance biomimetic materials. Herein, a biomimetic aerogel reactor with vertically aligned channels and customized surface modification is developed and acts as a carrier to covalently immobilize tannase for high-efficiency flow biocatalytic conversion of tannins. Attributing to the interconnected cellular structure, aligned channels, high porosity, and hydrophilic property, the biomimetic biocatalysis reactor exhibits mechanical robustness and high liquid flux (2432 L m–2 h–1). Further intergradation with the rapid mass-transfer capability, comfortable microenvironment, and substrate enrichment effect from zwitterionic polymer modification, the biomimetic biocatalysis reactor shows improved pH and thermal stabilities, enzymatic activity, organic solvent tolerance, storage stability, and reusability compared to free enzyme and other substrate-based biocatalysis reactor. Moreover, the high conversion efficiency (99.6%) is achieved by the biomimetic biocatalysis reactor in flow biocatalytic transformation of tannins solely driven by gravity. These results demonstrate the promising strategy for designing a biomimetic enzyme reactor and validate the potential applications of immobilized tannase in biocatalytic engineering fields.
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Foods
·
2022
·Vol. 11
·期 23
·3936
·
IF 5.561
Xinmiao Wang,Qian Wang,Yuanyuan Hu,Fawen Yin,Xiaoyang Liu,Dayong Zhou
Phenolipids such as alkyl gallates (A-GAs) have been approved by the food industry as non-toxic antioxidant additives, which are also regarded as an emerging source of functional food ingredients. However, comprehensive understanding of their digestive absorption is needed. Thus, the models of live mice and anaerobic fermentation were used to clarify the distribution and microbial hydrolysis characteristics of A-GAs in the gastrointestinal tract. HPLC-UV results demonstrated that A-GAs could be hydrolyzed by intestinal lipases and gut microorganisms includingLactobacillusto produce free gallic acid (GA). Through regulating the chain length of the lipid part in A-GAs, the sustained and controllable release of the GA can be easily achieved. Furthermore, A-GAs were also able to reach the colon and the cecum, which would lead to potential gastrointestinal protective effects. Therefore, A-GAs may be applied as possible ingredient for functional foods.Keywords:alkyl gallates;distribution;hydrolysis;gastrointestinal tract;oral administration
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2023
·
IF 4.4
Chengxiang Chu,Xianfeng Wang,Yuanyi Deng,Yi Ma,Chengyue Zou,Mei Yang,Huibo Luo,Danqun Huo,Changjun Hou
A facile and rapid fluorescence sensor array based on Tb (III) and Eu (III) doped Zr (IV) metal–organic frameworks was proposed for Chinese green tea discrimination. According to large porosity of Tb@UiO-66-(COOH) 2 and Eu@UiO-66-(COOH) 2 , phenolic hydroxyl groups of tea polyphenols could coordinate with free carboxylic acid groups and was captured into the pores, which led to the disturbance of electronic structure of ligand and inhibited the energy transfer efficiency from ligand to Tb (III) and Eu (III) center, causing the fluorescence quenching effect. Based on Hierarchy Cluster Analysis and Linear Discrimination Analysis, the fluorescence sensor array was employed for successful tea polyphenols classification through the analysis of different fluorescence quenching effect to tea polyphenols. Green tea samples within different categories and grades were also successfully discriminated using this assay according to tea polyphenols, providing a new method for Chinese green tea identification.
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Food & Function
·
2021
·Vol. 12
·期 21
·10581-10588
·
IF 5.396
Xinmiao Wang,Kefan Chen,Xiumin Zhang,Yuanyuan Hu,Zixu Wang,Fawen Yin,Xiaoyang Liu,Jianghua Zhang,Lei Qin,Dayong Zhou
Phenolipids such as alkyl gallates (A-GAs) have been approved by food industry as non-toxic antioxidant additives. However, their digestion and absorption mechanisms in the intestine have not yet been clarified. In this research, the hydrolysis and transport characteristics of A-GAs with fatty alcohols of various chain lengths (C1:0, C2:0, C3:0, C4:0, C8:0, C12:0 and C16:0) were estimated by the everted-rat-gut-sac model (ERGSM) for the first time. High-performance liquid chromatography measurements proved that measurable peaks corresponding to methyl gallate (G-C1:0), ethyl gallate (G-C2:0), propyl gallate (G-C3:0) and butyl gallate (G-C4:0) were discovered in the serosal fluids, which showed the short-chain alkyl gallates can cross the membrane in the form of esters. Besides, all A-GAs were hydrolyzed to GA in the mucosal solution, which contributed evidently to the transport of GA across the membrane of the small intestine. Meanwhile, the hydrolysis rate of A-GAs and transport rate of GA initially increased and then decreased with the chain length, exhibiting a maximum for octyl gallate (G-C8:0). In general, all A-GAs have the behavior of sustained-release. In consequence, the production of A-GAs should be an effective method to extend action time and further increases biological activities of GA.
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COMPOSITES COMMUNICATIONS
·
2020
·
IF 4.915
Yuchao Wu,Mingen Fei,Tingting Chen,Renhui Qiu,Wendi Liu
The development of highly biobased and robust thermosetting matrices using renewable feedstocks has become an interesting topic in the field of composites. A series of palm oil (PO)-based thermosets were prepared from a PO vinyl monomer and natural phenolic (NP) cross-linkers. The PO fatty acid-ethyl acrylamide (POFA-EA) was synthesized via a facile transesterification of PO with N -(2-hydroxyethyl)acrylamide (HEAA). NPs including eugenol, methyl gallate, and tannic acid were used to generate aromatic rings-containing cross-linkers via a solvent-free and ultrasonic-assisted esterification. The mechanical properties and processibility of the developed PO resins were closely associated with the chemical structures and unsaturation degrees of the incorporated NP cross-linkers. Besides, the thermosets were further used as the matrices for bamboo fibers-reinforced biocomposites . The resulting biocomposites showed comparable mechanical properties and T g s toward those of petroleum-based counterparts. The biocomposites are anticipated to be fully decomposed because the PO matrices could be degraded in a mild alkali condition. This study provides insights to develop high performance and recyclable PO-based thermosets and their biocomposites.
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FOOD RESEARCH INTERNATIONAL
·
2026
·
IF 8.8
Qian Wang,Weiyuan Niu,Xiangbo Zeng,Xinmiao Wang,Dayong Zhou,Fawen Yin
BG-PC and HG-PC exhibit the strongest antioxidant activity in walnut oil. • A reverse-micelle interfacial localization mechanism is proposed to explain chain-length-dependent antioxidant activity. • This offers a design strategy for lipid antioxidants. Phospholipid complexes of gallic acid and alkyl gallates (C1–C16) were synthesized and applied to walnut oil to investigate their antioxidant efficacy and underlying mechanisms. They exhibited significantly enhanced antioxidant efficacy over the monomers or physical mixtures during thermal oxidation (60 °C). Our systematic structure–activity relationship study revealed that complexes with intermediate (C4) and longest (C16) alkyl chains exhibited the highest antioxidant efficacy, as evidenced by reduced oxidation products and degradation of polyunsaturated fatty acids. Critical micelle concentration, cryo-TEM, CLSM, and SAXS analysis collectively indicated that the complexes self-assembled into reverse micelles in oil. Based on this, a spatial distribution mechanism was proposed: The alkyl chain length appeared to achieve complementary antioxidant protection at interfacial and lipid regions by influencing the preferential positioning of complexes within these structures. Similar trends were observed in oil-in-water emulsions. These findings provide mechanistic insights into the rational design of phospholipid-based antioxidant systems for lipid-rich foods. Download: Download high-res image (226KB) Download: Download full-size image
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LANGMUIR
·
2023
·
IF 3.9
Yonggan Ju,Jingxian Hua,Hong Niu,Hongling Chen
Bubbles or foams appear in many industrial processes, bringing inconvenience; yet, efficient capture or removal of them is still challenging. In this study, we report the synthesis and properties of multibranched molecule defoamers based on methyl gallate derivatives (Mb-GDs), which adopt methyl gallate (M-G) as the parent structure, by incorporating alkyl groups from alkyl isocyanates (A-I) with different chain lengths (C12 and C18) to replace R–OH in the M-G structure and further by linking two Mb-GDs into one Gemini-type multibranched derivative (Gt-Mb-GD) by transesterification to construct a defoamer material with a larger spatial volume. The surface properties and interfacial activity of molecular defoamers in aqueous solutions were studied, and the structure–property relationships of the multibranched gallate molecule defoamers based on Mb-GDs and Gt-Mb-GDs were further investigated by comparing the defoaming and antifoaming performance in four typical surfactant foams and foaming solutions with two kinds of commercial defoamers. The foam experiments indicated that the defoamers with a longer branched chain length (C18) showed more effectiveness in defoaming and antifoaming for four surfactant foams or foaming solutions, even at very low dosages, which were far stronger than the commercial high-carbon alcohol defoamer with a linear structure and comparable to branched silicone-based emulsion-type defoamers. Compared with Mb-GD defoamers, Gt-Mb-GD defoamers with a larger branched structure showed a higher defoaming performance. The study found the great potential of materials with multibranched structures for practical applications as the core components of high-performance defoamers.
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危险品化学品经营许可证（带存储）