JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2026
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IF 6.2
Yanan Zhao,Rui Wang,Ziyang Huang,Siting Ju,Binghua Dong,Hui Teng,Lei Chen
The gut is often referred to as the “second brain” and is highly vulnerable to alcohol exposure. Galangin, a flavonoid extracted from traditional medicinal herbs, Alpinia officinarum Hance, has manifested auspicious clinical application potential. This study aims to explore the regulatory effect of galangin on ferroptosis in an alcohol-related intestinal injury model and its underlying mechanism. In vivo, we confirmed that galangin administration could alleviate alcohol-induced iron metabolism dysfunction and ferroptosis and activate the SESN2/KEAP1/NRF2 signaling pathway in mice colon. In vitro, alcohol-caused disruption of iron homeostasis and ferroptosis could also be significantly reduced by galangin. Using specific small interfering RNA targeting SESN2 (Si-SESN2) or the NRF2 inhibitor ML385 significantly abrogated the protective effect of galangin. Molecular docking and Co-IP results further revealed that galangin activates NRF2 nuclear translocation by promoting KEAP1/SESN2 formation as well as KEAP1/NRF2 dissociation. Collectively, galangin suppressed ferroptosis by activating the SESN2/KEAP1/NRF2 pathway in mice and Caco-2 cells.
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高影响因子
FOOD CHEMISTRY
·
2026
·
IF 10.4
Yitong Wang,Rui Wang,Qiaoying Guo,Xiaoqian Xu,Hui Teng,Lei Chen,Yanan Zhao
Hydrogen bonding and hydrophobic interactions were the major forces involved in the OVA-FUC complex. • The formation of the OVA-FUC complex resulted in enhanced emulsifying properties compared to individual OVA or FUC. • The galangin-loaded emulsion based on the OVA-FUC complex possessed potent antioxidant activity. • Galangin-loaded emulsion potentiates the oxidative stress resistance of Caenorhabditis . The effective delivery of hydrophobic bioactive compounds remains a major challenge in functional food and nutraceutical applications because of their poor aqueous solubility, limited physicochemical stability, and insufficient bioavailability. In this study, ovalbumin-fucoidan (OVA-FUC) complexes were constructed as food-grade stabilizers to develop galangin (GAL)-loaded emulsions with improved stability and antioxidant efficacy. The interaction mechanism, emulsion stability, and antioxidant activity were evaluated using structural characterization, interfacial analysis, storage tests, chemical antioxidant assays, and an ethanol-induced oxidative stress model in Caenorhabditis elegans . Results showed that OVA and FUC formed complexes mainly through hydrogen bonding and hydrophobic interactions. The 1-1 OVA-FUC complex exhibited the most favorable interfacial behavior and produced emulsions with superior storage stability. The GAL-loaded emulsion showed strong ABTS radical-scavenging activity (74.33 ± 7.60%) and effectively reduced ROS, lipofuscin, and MDA levels while increasing glutathione content and improving locomotor activity in C. elegans. These findings reveal that controlled OVA-FUC interactions can optimize interfacial assembly and emulsion stability, offering a practical strategy to improve the functional delivery of hydrophobic antioxidants in food systems. Download: Download high-res image (200KB) Download: Download full-size image
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JOURNAL OF PHYSICAL CHEMISTRY B
·
2026
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IF 3.2
Zheng Li,Mengrong Hu,Siyu Hou,Shufang Gao,Ziyi Wang,Jian Luo
Deprotonated flavonoids typically undergo efficient nonradiative relaxation in solution, rendering them nonemissive. In this study, we successfully activate the fluorescence of such anions by embedding five representative flavonoids─galangin, apigenin, luteolin, kaempferol, and quercetin─into DMSO-doped poly(vinyl alcohol) (PVA/DMSO) films. The unique microenvironment of the composite film provides dual functionalities: intrinsic microbasicity facilitates flavonoid deprotonation, while spatial constraints effectively suppress the nonradiative decay pathways. Consequently, strong visible-light emission is observed for all flavonoids except galangin upon excitation at 440 nm. Time-dependent density functional theory calculations were employed to model the emission energies of various anionic species. By correlating the calculated trends with experimental spectra, we identify the emissive species as anions deprotonated specifically at the C4′–OH position, rationalizing the absence of emission from galangin, which lacks this moiety. This work not only demonstrates a general strategy to unlock the fluorescence of nonemissive anionic chromophores through synergistic matrix control but also establishes PVA/DMSO films as a versatile platform for modulating the photophysics of charged organic molecules.
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JOURNAL OF MOLECULAR STRUCTURE
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2026
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IF 4.9
Changhai Sun,Mengxin Xiao,Biyue Cui,Shiyuan Sun,Shushuang Shen,Shuting Zhang,Xinran Zhang,Liting Mu
Based on the current state of research, the identification of flavonoid isomers still faces certain difficulties and challenges, and developing liquid chromatography separation conditions requires substantial resources. Therefore, this study constructed a quantitative structure-retention relationship (QSRR) model for anthoxanthins in reverse-phase chromatography by exploring quantitative relationships between chromatographic retention time (t R ) and implicit solvent model solvation free energy and hydrogen bonding energies in the mobile phase. A database was compiled by calculating the molecular descriptors of 1023 hydroxy-substituted flavonoids. When using UHPLC-HRMS technology combined with a database to identify unknown anthoxanthins, this model provides auxiliary identification to enhance the accuracy of the identification results. The model was constructed using 11 modeling compounds and two molecular descriptors to achieve the goal of predict compound retention times. The chromatographic retention time of anthoxanthins exhibited a linear correlation with their solvation free energy in the mobile phase. Furthermore, the feasibility of calculating the hydrogen bonding energies between anthoxanthins and the mobile phase using quantum chemical methods based on electron density was demonstrated. This study provides novel insights into the reverse-phase chromatographic separation of structurally similar compounds, while the constructed database offers extensive data support for isomer research.
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高影响因子
MOLECULES
·
2022
·Vol. 27
·期 23
·8373
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IF 4.927
Xijuan Tu,Fengjie Yu,Qian Jin,Chunping Du,Jiaxu Chen,Ji Yang,Yuchang He,Shaokang Huang,Wenbin Chen
In the present work, a high-throughput field sample preparation method was reported for the simultaneous determination of 5-hydroxymethylfurfural and phenolic compounds in honey. Combining a simple and green homogenous liquid–liquid extraction, matrix-induced sugaring-out, with the use of a 96-deepwell plate and multichannel pipette, the proposed method showed its merits in instrument-free and high-throughput preparation. Due to the high-throughput property, the parameters of the method were rapidly and systematically studied using a constructed 4 × 2 × 4 × 3 array (sample amount × ratio of ACN:H2O × standing time × replicates) in a 96-deepwell plate. Analytical performance was fully validated, and the limits of detection and limits of quantification were in the range of 0.17–1.35 μg/g and 0.51–4.14 μg/g, respectively. Recoveries were between 83.98 and 117.11%, and all the precisions were <5%. Furthermore, the developed method was successfully applied in the outdoor preparation of commercial honey samples and the in-field preparation of raw honey samples in apiary. The current work presented a simple, rapid, and high-throughput method for the field sample preparation of honey and provides a valuable strategy for the design of field and on-site sample preparation.Keywords:field sample preparation;high-throughput;homogenous liquid-liquid extraction;matrix-induced sugaring-out;honey
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JOURNAL OF FOOD SCIENCE
·
2023
·Vol. 88
·期 2
·696-716
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IF 3.9
Chun Xiao Li,Fu Rong Wang,Bing Zhang,Ze Yuan Deng,Hong Yan Li
The impact of phenolic compounds on the human body depended on the type, content, bioavailability, and antioxidant activity. After digestion, different phenolic compounds had different changes of bioavailability and antioxidant activity, which needed to be considered in the application. In this experiment, the structural stability and antioxidant activity of 27 phenolic compounds (phenolic acids, flavonols, flavonoids, and flavanones) were investigated during the in vitro simulated digestion. This experiment eliminated the influence of food matrix, provide a basis for regularity for the changes of phenolic substances in different materials. Results showed that the bioaccessibility of phenolic compounds with different structures varied, and there was a conformational relationship between the structure and stability. After oral digestion, most of the phenolic compounds underwent degradation and the cellular antioxidant activity (CAA) values decreased to a large extent ( p < 0.05). After gastric digestion, the content ( p > 0.05) and CAA values ( p < 0.05) of most phenolic compounds increased. However, after intestinal digestion, the phenolic compounds were degraded to a greater extent, and different structures of phenolic compounds had different changes in CAA values ( p < 0.05). In general, the CAA values of most phenolic compounds after in vitro digestion were lower than the initial value. The 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis (3-ehylbenzthiazoline-6-sulfonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) values of phenolic acids and flavonols decreased after in vitro simulated digestion ( p < 0.05), while the values of DPPH, ABTS, and FRAP of most flavonoids ( p < 0.05) increased. The increased oxygen radical absorption capacity (ORAC) values were found in most phenolic acids, flavonols, and flavonoids ( p < 0.05), and most flavanones showed unremarkable changes in ORAC values ( p > 0.05). In general, the changing trend of chemical-based antioxidant activity was consistent with the content of phenolic compounds.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
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2022
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IF 4.831
Xiangrong Li,Linyu Han,Zhizhi Song,Ruonan Xu,Lixia Wang
Transferrin is the indispensable component in the body fluids and has been explored as a potential drug carrier for target drugs to cancer cells. Flavonols are widely distributed in plants and shown a wide range of biological activities. In the present study, the interaction between flavonols (including galangin, kaempferol, quercetin, and myricetin) and transferrin under physiological conditions was investigated by using experimental as well as computational approaches. Fluorescence data reveal that the fluorescence quenching mechanism of transferrin by flavonols is static quenching. Transferrin has moderate affinity with flavonols, and the binding constants ( K a ) are 10 3 -10 4 L/mol. In addition, there are two different binding sites for the interaction between kaempferol and transferrin. Thermodynamic parameter analysis shows that the interaction of flavonols and transferrin is synergistically driven by enthalpy and entropy. Hydrophobic interaction, electrostatic force and hydrogen bonds are the main force types. Synchronous fluorescence spectroscopy shows that flavonols decrease the hydrophobicity of the microenvironment around tryptophan (Trp) and have no effect on the microenvironment around tyrosine (Tyr). UV–vis and CD spectra show that the interaction between transferrin and flavonols leads to the loosening and unfolding of transferrin backbone. The increase of β-sheet is accompanied by the decrease of α-helix and β-turn. The specific binding sites of flavonols to transferrin are confirmed by molecular docking. Molecular dynamic simulation suggests that the transferrin-flavonols docked complex is stable throughout the simulation trajectory.
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Food & Function
·
2022
·Vol. 13
·期 9
·5061-5074
·
IF 6.317
Jie Zhao,Lin Huang,Renjie Li,Zhuangwei Zhang,Jin Chen,Hongjin Tang
Gliadin, as a main component of wheat storage protein, is used as a drug encapsulation and delivery system owing to its specific characteristics. Flavonoids are regarded as active natural products with a variety of pharmacological effects. In this study, an integrated method including UV-vis, fluorescence, and FT-IR spectroscopy and molecular modelling was applied to explore the structure–affinity relationship and the interaction nature between a library of flavonoids and gliadin. The characteristic UV-vis spectral changes of gliadin mediated by flavonoids with absorption bands at 218 and 278 nm demonstrated the existence of an interaction depending on generating the ground-state complexes. Fluorescence quenching results showed that the intrinsic fluorescence of gliadin could be effectively quenched by flavonoids coupled with the formation of flavonoid–gliadin complexes through the static quenching mechanism. The structure–affinity relationship revealed the critical structural elements associated with the binding affinity on gliadin and underlined the favorable substituents at the specific positions of flavonoid skeletons leading to a stronger binding potency. From the analysis of synchronous fluorescence spectra, flavonoids could cause the conformation change of gliadin and impact the microenvironment around TYR and TRP residues. Moreover, the ANS fluorescent probe assay suggested that these flavonoids also influenced the surface hydrophobicity of glaidin based on the further exposure or blocking of hydrophobic domains. Molecular modelling was subsequently performed and illustrated the proposed binding conformation of flavonoids on gliadin. Combined with the FT-IR spectra, these results further confirmed the important role of hydrophobic interactions and hydrogen bonds in their binding process.
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FOOD CHEMISTRY
·
2022
·
IF 9.231
Jie Zhao,Lin Huang,Renjie Li,Zhuangwei Zhang,Jin Chen,Hongjin Tang
Bovine serum albumin (BSA) has the potential application of establishing a delivery system for flavonoids. However, the effect of copper on the binding of flavonoids with BSA is unclear. Therefore, the binding of six flavonoids with BSA containing Cu 2+ was investigated using UV–vis, fluorescence, and molecular docking. The UV–vis spectral changes demonstrated the formation of flavonoid-Cu 2+ complexes. The fluorescence quenching results suggested that the chelation of Cu 2+ increased the binding affinity of galangin and baicalin to the BSA but decreased the binding capacity of chrysin, baicalein, luteolin, and vitexin. Synchronous fluorescence data revealed that Cu 2+ could influence the secondary structure conformation of BSA binding with flavonoids, which was further confirmed by ANS-binding fluorescence, circular dichroism, and molecular docking. These findings demonstrate that the complexation of Cu 2+ significantly affects the binding of flavonoids with BSA, which provides the theoretical basis for the development of natural product-metal complex functional foods.
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FOOD AND CHEMICAL TOXICOLOGY
·
2021
·
IF 6.025
Yajing Fang,Fuqiang Liang,Mengmeng Xia,Weiwei Cao,Siyi Pan,Ting Wu,Xiaoyun Xu
This study was aimed to investigate the inhibitory activity of flavonoids on P-glycoprotein (P-gp). Effects of 39 flavonoids on the cellular uptake (CU) of rhodamine123 (Rho) and daunomycin (DNR) were investigated in both parental KB and P-gp overexpressed KB/MDR cells. The inhibition mechanism of selected flavonoids was further investigated by measuring the ATPase activity and expression level of P-gp. Twelve flavonoids improved the uptake of Rho (↑Rho F ) and nineteen flavonoids increased the uptake of DNR (↑DNR F ) in KB/MDR cells with nine flavonoids overlapped. Structure-activity relationship (SAR) indicated that 8-OCH 3 , and 2′-OH have a negative effect on Rho and DNR transport. Whereas 5-OH, 5-OCH 3 , 6-OH, 7-OCH 3 , 3′-OH, and 4′-OH, are essential for inhibition of flavonoids on P-gp and reversing the resistance of Rho and DNR. Eleven selected flavonoids significantly induced the basal P-gp-ATPase activity but much lower than that induced by verapamil . Tangeretin , galangin , kaempferol , quercetin , and morin significantly reversed the ATPase activity stimulated by verapamil. Six of eleven flavonoids significantly decreased P-gp expression, whereas three flavonoids slightly increased P-gp expression. These results provide valuable information that flavonoids can effectively reverse multidrug resistance of P-gp-mediated transport of nutraceutical and drugs by co-administration.
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BIOLOGICAL & PHARMACEUTICAL BULLETIN
·
2020
·
IF 1.863
Yuanguo Xiong,Hao Lu,Hanlin Xu
Hepatic fibrosis (HF) is a common disease, with currently no available treatment. Galangin, a natural flavonoid extracted from Alpinia officinaruim Hance, has multiple effects demonstrated in previous studies. The aim of the present study was to explore the anti-fibrogenic effect of galangin in vitro, and research its potential molecular mechanisms. LX-2 cells were chosen as an in vitro HF model, and were treated with galangin in different concentrations. Cell viability was analyzed using Cell Counting Kit-8 (CCK-8) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, cell apoptosis was measured using flow cytometry, and the anti-fibrogenic effect of galangin was determined using quantitative reverse transcription polymerase chain reaction (RT-qPCR), immunofluorescence, and western blotting. The results show that the proliferation of LX-2 cells was efficiently inhibited by galangin, and apoptosis was induced in a dose-dependent manner. Both the mRNA and protein expression of α-SMA and collagen I were markedly downregulated. Galangin also inhibited the PI3K/Akt and Wnt/β-catenin signaling pathways and increased the Bax/Bcl-2 ratio. The results of this study suggest that galangin has an anti-fibrogenic effect and may represent a promising agent in the treatment of hepatic fibrosis.
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高影响因子
FOOD CHEMISTRY
·
2020
·
IF 6.306
Jie Zhao,Lin Huang,Chunyong Sun,Dongsheng Zhao,Hongjin Tang
In this study, some flavonoids were screened as potent xanthine oxidase (XO) inhibitors in vitro . Flavonoid 9 was demonstrated to exhibit the inhibitory activity through a ping-pong mechanism. Further structure-activity relationship revealed that different structural elements had greatly influenced the inhibition effect on XO and underlined the requirement of hydroxyl groups at C5 and C4′ of flavonoid type I. Moreover, some bioactive flavonoids could efficiently quench the intrinsic fluorescence of XO by either static or static-dynamic mixed mechanism. The synchronous fluorescence, ANS-binding fluorescence, Fourier transform infrared spectra and circular dichroism suggested that active flavonoids could bind to the active center of XO, prevent the entrance of substrate, and induce the rearrangement and conformation change of its secondary structures, ultimately resulting in the significant inhibition effect. Additionally, molecular docking further confirmed these conclusions and highlighted the great importance of hydrophobic interactions and hydrogen bonds for the formation of stable complex conformation.
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