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FOOD CHEMISTRY · 2026 · IF 10.4

Bidirectional regulation of heterocyclic amines by flavonoids: insights from flavonoid amination using dihydromyricetin and baicalein

Jingjing Zhang,Hui Cao,Bing Li,Fuying Wang,Qin Duan,Yaru Li,Jinjin Pei,Hui Wang,Juan Carlos Mejuto,Jesús Simal-Gándara,Haolin Zhang

Heterocyclic amines (HCAs) are carcinogenic contaminants formed during meat thermal processing, and the traditionally recognized inhibitory effects of flavonoids on HCA formation remain controversial. Dihydromyricetin (DMY) and baicalein (BAI) both exhibited dose-dependent bidirectional effects on PhIP formation in a PhIP chemical model. At low concentrations (DMY 125–250 μM, BAI 125–1000 μM), PhIP levels gradually increased to nearly 210% and 300% of control, respectively, mainly driven by amination-related reactions of flavonoid thermal degradation products that promoted phenylacetaldehyde accumulation. At high concentrations (≥2000 μM), PhIP was suppressed to <50% (DMY) and <20% (BAI) of control via potent radical scavenging and phenylacetaldehyde trapping. The bidirectional regulation may be governed by a dynamic balance between amination-driven promotion and the dual inhibitory pathways for PhIP formation. This study explains how flavonoids lead to contradictory effects on HCA formation in cooked meat and provides a mechanistic foundation for their application.

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ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS · 2026 · IF 3.5

Inhibition of xanthine oxidase by orientin, a C-glycosylated flavonoid: Kinetic characterization and molecular simulation

Liwei Jia,Yu Zhong,Baoyue Xu,Qianqian Liu,Xin Meng

Orientin inhibited xanthine oxidase with moderate in vitro potency. • Global kinetic fitting supported a mixed-type inhibition mechanism. • Fluorescence quenching verified direct XO–orientin interaction. • Molecular simulations indicated a stable XO–orientin binding mode. • C-glycosylation altered ADMET-related properties versus luteolin. Xanthine oxidase catalyzes the oxidation of hypoxanthine to xanthine. It further oxidizes xanthine to uric acid, making it an important target for treating hyperuricemia. This study focused on orientin as a model flavonoid for xanthine oxidase inhibition. We examined whether the C-glycosyl group changes its inhibitory potency, binding pattern, and predicted ADMET profile. In vitro enzyme activity was determined to be 364.79 ± 8.21 μM for the half-inhibitory concentration (IC 50 ) of orientin. Kinetic analysis suggested a mixed-type inhibition pattern. Intrinsic fluorescence quenching further supported the interaction between orientin and XO. Molecular docking and molecular dynamics simulations provided structural insight into the binding mode and stability of the orientin–XO complex. ADMET analysis indicates that orientin has promising pharmaceutical properties. These findings provide a basis for future research focusing on structural optimization, metabolic transformation, and in vivo evaluation. Download: Download high-res image (385KB) Download: Download full-size image

CAS / MDL: 28608-75-5
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Microorganisms · 2026 ·Vol. 14 ·期 8 ·1692 · IF 4.7

The Role of Natural Flavonoid Quercetin in Combating Tet(X3)/Tet(X4)-Positive Bacterial Infections

Xiaokun Zhan,Lifeng Zhou,Hanyu Wang,Lihao Wang,Lizhi Tian,Yonglin Zhou,Kuan Gu,Houru Liu

The increased occurrence of tetracycline resistance (conferred by thetet(X3)/tet(X4) resistance genes) poses a major challenge to the clinical treatment of infections using tetracyclines, including tigecycline, which is the “last-resort” therapeutic agent. Thus, there is an urgent need to develop inhibitors targeting Tet(X3)/Tet(X4) to address the crisis of tetracycline resistance. This study revealed that quercetin is an inhibitor of Tet(X3)/Tet(X4), which, when combined with different tetracyclines, can exert synergistic growth-inhibitory effects against Tet(X3)/Tet(X4)-positive bacteria (fractional inhibitory concentration < 0.5). Quercetin + tigecycline significantly decreased the biofilm-forming ability of bacteria. Mechanistic investigations revealed that quercetin inhibits the catalytic activity of Tet(X4) against tetracycline antibiotics by binding to the catalytic active site. In theGalleria mellonellalarval infection model of Tet(X4)-positiveE. coliJ53p47EC or Tet(X4)-negativeE. coliJ53, tigecycline + quercetin enhanced the survival rate, decreased melanization, and suppressed bacterial load. Thus, the findings of this study will enable the development of novel Tet(X3)/Tet(X4)-targeted therapeutic strategies for clinical infections caused by drug-resistantEnterobacteriaceaeandAcinetobacter baumannii, especially Tet(X3)/Tet(X4)-positive pathogens.

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SEPARATION AND PURIFICATION TECHNOLOGY · 2025 · IF 9

Natural product flavonoid of naringenin based thin-film composite polyester membranes preparation for antibiotic separation

Chao Wang,Peijuan Chu,Tengfei He,Cheng Yi,Yue Yao,Lijia Liu,Chunhong Zhang

The application of membrane separation technology in wastewater treatment and pharmaceutical purification has attracted considerable attention. The development of a membrane with effective separation performance and antibacterial properties is of considerable interest for the separation and purification of antibiotics. Here, a thin-film composite (TFC) polyester membrane with effective antibiotic removal and antibacterial properties was fabricated via a facile one-step interfacial polymerization (IP) strategy. Naringenin (Nar), a natural product of flavonoid material derived from the pericarp, was utilized as the aqueous monomer. The suitable reactivity of Nar afforded the resulting membrane with a highly negative charged surface. The rejection performances for the antibiotics cephalothin, cefuroxime sodium, ceftriaxone sodium, and cefoperazone sodium were 96.3 %, 97.7 %, 99.2 %, and 99.8 %, respectively. The pure water permeance was 7.5 L m −2 h −1 bar −1 at a transmembrane pressure of 5 bar. The antibacterial efficacy was greater than 99.0 % against Escherichia coli and Staphylococcus aureus , attributable to the flavonoid structure of Nar. The present work proposed a feasible strategy to prepare TFC membranes with high nanofiltration performance and intrinsic antibacterial efficacy.

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INDUSTRIAL CROPS AND PRODUCTS · 2024 · IF 5.6

Mechanism of deep eutectic solvents based extraction of phenolic and flavonoid compounds from peony petals

Shenglin Wang,Jiahui Wei,Hanwen Ge,Yang Xu,Baoping Zhu,Yuanjun Yang,Ke Zhai,Bin Li,Huanfei Xu

Deep eutectic solvents (DES) have exhibited great potential in the extraction of active ingredients from flowers. In this study, ternary DESs were designed for the extraction of phenolic and flavonoid compounds from peony petals. When the molar ratio of ChCl:EG:U was 1:2:2, and the water content was 30 %, the maximum extraction yields of total phenolic content (TPC) and total flavonoid content (TFC) were achieved, reaching 109.30 mg GAE/g and 56.93 mg RE/g, respectively. Meanwhile, cellulose nanofibers were prepared. The relationship model with extraction yield as the target was established by multivariate analysis. The model indicated that the property parameters of the HBD had a significant impact on the extraction yields of TPC and TFC. At the molecular level, Density functional theory (DFT) was employed to explore the extraction mechanism. The analysis revealed that hydrogen bonding was the main interaction force. The maximum binding energy between DES and rutin was −89.03 kcal/mol. This study provides an efficient extraction solvent and insights into the mechanism of extracting the phenolic and flavonoid compounds from peony petals.

研究领域: 植物化学 · 食品科学 · 分析化学
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Cell Reports · 2025 · IF 6.9

SlWRKY14 integrates carotenoid and flavonoid biosynthetic pathways to regulate coloration and quality of tomato fruits

Yuanyuan Li,Fanliang Meng,Huiwan You,Zhiyong Shao,Chenyu Xu,Yuening Li,Songwen Li,Lihong Liu,Qiaomei Wang

Carotenoids and flavonoids are two principal classes of secondary metabolites in tomato fruit, jointly contributing to pigmentation and nutritional quality. Here, we identified SlWRKY14 as a novel regulator of both these two pathways. slwrky14 lines result in redder fruits enriched in carotenoids, whereas fruit-specific overexpression lines produce orange-yellow fruits with reduced carotenoids but elevated flavonoids. SlWRKY14 directly binds to the promoter of carotenoid biosynthetic genes ( SlDXS1 and SlPSY1 ) and represses their transcription by recruiting histone deacetylase SlHDA1, which functions in decreased histone acetylation to inhibit gene expression. Further genetic evidence verifies the role of the SlWRKY14-SlHDA1 module in suppressing carotenoid accumulation. In contrast, SlWRKY14 activates the flavonoid biosynthetic gene SlPALA to promote flavonoid accumulation. Our findings demonstrate SlWRKY14 as a regulatory node of carotenoid and flavonoid biosynthesis, providing a strategy for coloration regulation and quality improvement without penalty of yield in tomato.

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Plants-Basel · 2025 ·Vol. 14 ·期 1 ·133 · IF 4.1

WRKY Transcription Factors Modulate the Flavonoid Pathway of Rhododendron chrysanthum Pall. Under UV-B Stress

Wang Yu,Xiangru Zhou,Jinhao Meng,Hongwei Xu,Xiaofu Zhou

The depletion of the ozone layer has resulted in elevated ultraviolet-B (UV-B) radiation levels, posing a significant risk to terrestrial plant growth.Rhododendron chrysanthumPall. (R. chrysanthum), adapted to high-altitude and high-irradiation environments, has developed unique adaptive mechanisms. This study exposedR. chrysanthumto UV-B radiation for two days, with an 8 h daily treatment, utilizing metabolomic and transcriptomic analyses to explore the role of WRKY transcription factors in the plant’s UV-B stress response and their regulation of flavonoid synthesis. UV-B stress resulted in a significant decrease in rETR and Ik and a significant increase in 1-qP. These chlorophyll fluorescence parameters indicate that UV-B stress impaired photosynthesis inR. chrysanthum. Faced with the detrimental impact of UV-B radiation,R. chrysanthumis capable of mitigating its effects by modulating its flavonoid biosynthetic pathways to adapt positively to the stress. This study revealed changes in the expression of 113 flavonoid-related metabolites and 42 associated genes, with WRKY transcription factors showing significant correlation with these alterations. WRKY transcription factors can influence the expression of key enzyme genes in the flavonoid metabolic pathway, thereby affecting metabolite production. A theoretical reference for investigating plant stress physiology is provided in this work, which also offers insights into the stress responses of alpine plants under adverse conditions.

CAS / MDL: 64-18-6
研究领域: 植物学 · 分子生物学 · 环境科学
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ADVANCED FUNCTIONAL MATERIALS · 2024 · IF 18.5

Donor–Acceptor Type Solvatochromic Flavonoid Materials Fluorphores for Polarity Sensing and Real-Time Temperature Monitoring

Anqi Liu,Qipeng Zhang,Lei Pan,Fan Yang,Dan Lin,Changlong Jiang

Electron donor–acceptor (D–A) molecules are emerging tools for designing sensitive luminogens, attracting significant research attention. However, due to poor quantum yields under certain conditions, current D–A fluorophores often suffer from fluorescence quenching in practical applications. Developing new D–A dyes and functional composites is crucial for expanding their applications. Here, a novel donor–acceptor type flavonoid dye molecule, namely “AFL”, exhibiting both polarity-dependent fluorescence emission wavelength shift and viscosity-dependent intensity change, for polarity measurement and temperature sensing is designed and synthesized. Because the intramolecular charge transfer (ICT) can be enhanced by a decrease of excited state energy caused in high-polarity organic solvents, AFL undergoes fluorescence emission wavelength shift that shows fluorescence color response to solvents of different polarities and hence differentiates between them. Moreover, the actual temperature can be monitored by the as-designed AFL@tetradecanoic acid (AFL@TA) sensor. By combining with TA, viscosity sensitively changes upon the temperature change of insoluble composites, thus realizing the fluorescence intensity response to temperature. Remarkable recyclable performance and satisfactory mechanical properties are integrated. This study provides a promising approach to developing a new D–A fluorescent probe and furnishes perspectives on the potential of such D–A type flavonoid material in stimuli-responsive systems with a focus on visualization sensing technology.

研究领域: 化学 · 材料科学 · 生物传感技术
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MOLECULES · 2025 ·Vol. 30 ·期 5 ·980 · IF 4.6

Substrate Selectivities of GH78 α-L-Rhamnosidases from Human Gut Bacteria on Dietary Flavonoid Glycosides

Bin-Chun Li,Bingbing Wu,Xueting Hou,Guo-Bin Ding

α-L-rhamnosidases play a key role in the metabolism and biodegradation of dietary flavonoid glycosides. We have developed a novel microplate spectrophotometric method to rapidly evaluate the conversion rates and substrate selectivities of mesophilic α-L-rhamnosidases towards citrus flavanone diglycosides by combining with a high-active and thermophilic β-D-glucosidase based on UV-visible spectral differences between citrus flavanone diglycosides and the corresponding aglycones under alkaline conditions. Furthermore, catalytic activities and enzyme kinetics of four α-L-rhamnosidases from human gut bacteria on various dietary flavonoid glycosides with different glycosidic bonds from various subclasses have been explored by HPLC. The α-L-rhamnosidase BtRha78A specifically removed the rhamnose group from the flavones, flavanones and flavonols diglycosides with the α-1,6 glycosidic bonds. Moreover, BtRha78A displayed higher catalytic activities on the rutinose group at 7-OH of the aglycones than at 3-OH. HFM-RhaA preferred to catalyze the flavones, flavanones and dihydrochalcones diglycosides with the α-1,2 glycosidic linkages at the 7-OH. However, this enzyme also showed high catalytic activity on the flavonol diglycoside rutin with the α-1,6 glycosidic bonds at the 3-OH. HFM-RhaC exhibited certain hydrolytic abilities towards all flavonoid diglycosides, and displayed higher activities on the flavonoid diglycosides with the α-1,6 glycosidic bonds. HFM-Rha78 weakly hydrolyzed the flavones, flavanones and dihydrochalcones diglycosides with the α-1,2 glycosidic bonds, and the flavonols diglycosides with α-1,6 glycosidic bonds. All four α-L-rhamnosidases from human gut bacteria did not exhibit catalytic activity towards the flavonoid glycosides with the α-1 glycosidic bonds. It was revealed that the α-L-rhamnosidases from human gut bacteria possessed diverse substrate selectivity on dietary flavonoid diglycosides. The structural basis for the specificity of BtRha78A on the flavonoid diglycosides with α-1,6 glycosidic bonds and the preference of HFM-RhaA on the flavonoid diglycosides with α-1,2 glycosidic bonds have been analyzed by molecular docking.

CAS / MDL:
研究领域: 生物化学 · 微生物学 · 营养学
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Journal of Functional Foods · 2015 · IF 3.574

Total phenolic, flavonoid and antioxidant activity of 23 edible flowers subjected to in vitro digestion

Guan-Lin Chen,Song-Gen Chen,Ying-Qing Xie,Fu Chen,Ying-Ying Zhao,Chun-Xia Luo,Yong-Qing Gao

In order to provide new information on the antioxidant activities before and after in vitro digestion of the selected flowers for consumers, nutritionists, and food policy makers, total phenolic and flavonoid contents and antioxidant capacities of 23 edible flowers were evaluated. In addition, some bioactive components in the flowers were also identified and quantified by ultra performance liquid chromatography (UPLC). The correlations between 2, 2-diphenyl-1-picrylhydrazylradical scavenging activity assay (DPPH), Ferric reducing antioxidant power assay (FRAP), and ABTS •+ radical cation scavenging activity assay (ABTS) values and total flavonoid contents and total phenolic contents were also evaluated. Three flowers, Osmanthus fragrans (Thunb.) Lour, Paeonia lactiflora Pall, and Rosa rugosa Thunb (purple) showed the strongest antioxidant activities before or after the digestion, which implied that these flowers are important natural sources for the prevention of oxidative stress diseases.

研究领域: 食品科学 · 营养学 · 药理学 · 植物科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2013 · IF 1.977

Simultaneous kinetic spectrometric determination of three flavonoid antioxidants in fruit with the aid of chemometrics

Ruiling Sun,Yong Wang,Yongnian Ni,Serge Kokot

A simple, inexpensive and sensitive kinetic spectrophotometric method was developed for the simultaneous determination of three anti-carcinogenic flavonoids: catechin, quercetin and naringenin, in fruit samples. A yellow chelate product was produced in the presence neocuproine and Cu(I) – a reduction product of the reaction between the flavonoids with Cu(II), and this enabled the quantitative measurements with UV–vis spectrophotometry. The overlapping spectra obtained, were resolved with chemometrics calibration models, and the best performing method was the fast independent component analysis (fast-ICA/PCR (Principal component regression)); the limits of detection were 0.075, 0.057 and 0.063   mg   L −1 for catechin, quercetin and naringenin, respectively. The novel method was found to outperform significantly the common HPLC procedure.

CAS / MDL: 7758-99-8
研究领域: 分析化学 · 食品科学 · 植物化学
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SEED SCIENCE RESEARCH · 2021 ·Vol. 31 ·期 2 ·136-148 · IF 2.25

Investigation of flavonoid expression and metabolite content patterns during seed formation of Artemisia sphaerocephala Krasch.

Chengshuai Li,Lijing Zhang,Decao Niu,Shuzhen Nan,Xiumei Miao,Xiaowei Hu,Hua Fu

Flavonoids are a group of phenolic secondary metabolites in plants that have important physiological, ecological and economic value. In this study, using the desert plant Artemisia sphaerocephala Krasch. as the sample material, the content and components of the total flavonoids in its seeds at seven different developmental stages were determined. In addition, the genes involved in flavonoid metabolism were identified by full-length transcriptome sequencing (third-generation sequencing technology based on PacBio RS II). Their expression levels were analysed by RNA-seq short reading sequencing, to reveal the patterns and regulation mechanisms of flavonoid accumulation during seed development. The key results were as follows: the content of total flavonoids in mature seeds was 15.05 mg g−1, including five subclasses: flavonols, chalcones, flavones, flavanones and proanthocyanidins, among which flavonols accounted for 45.78%. The period of rapid accumulation of flavonoids was 40–70 d following anthesis. The high expression of phenylalanine ammonia-lyase (PAL), 4-coumarate-CoA ligase (4CL) and UDP-glucose:flavonoids 3-o-glucosyltransferase (UF3GT) promoted the accumulation of total flavonoids, while the high expression of flavonoids 3′-hydroxylase (F3′H) and flavonols synthase (FLS) made flavanols the main component. Transcription factors such as the MYB-bHLH-WDR (MBW) complex and Selenium-binding protein (SBP) directly regulated the structural genes of flavonoid metabolism, while C2H2-type zinc finger (C2H2), Zinc-finger transcription factor (GATA), Dehydration-responsive element binding (DREB), Global Transcription factor Group E protein (GTE), Trihelix DNA-binding factors (Trihelix) and Phytochrome-interacting factor (PIF) indirectly promoted the synthesis of flavonoids through hormones such as brassinoidsteroids (BRs) and abscisic acid (ABA). These results provided valuable resources for the application of related genes in genetics and breeding.

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