Acta Pharmaceutica Sinica B
·
2018
·
IF 6.014
Shuzhen Ren,Mingyu Liu,Chao Hong,Guowen Li,Jiabin Sun,Jianying Wang,Lei Zhang,Yan Xie
Pharmaceutical cocrystals are a promising technology that can be used to improve the solubility of poor aqueous compounds. The objective of this study was to systematically investigate the solubility of myricetin (MYR) cocrystals, including their kinetic solubility, thermodynamic solubility, and intrinsic dissolution rate (IDR). The effects of pH, surfactant, ion concentration, and coformers on the cocrystal solubility were evaluated. Furthermore, single crystal structures of MYR, myricetin–isonicotinamide (MYR–INM) and myricetin–caffeine (MYR–CAF) cocrystals were analyzed to discuss the possible reasons for the enhancement of cocrystal solubility from the perspective of the spatial structure. The results indicated that the kinetic solubility of MYR cocrystals was modulated by pH and cocrystal coformer (CCF) ionization in buffer solution, while it primarily depended on the CCF solubility in pure water. In addition, the solubility of MYR cocrystals was increased in a concentration dependent fashion by the surfactant or ion concentration. The thermodynamic solubility of MYR–INM (1:3) cocrystals decreased with the increases of the pH value of the dissolution media. The IDR of MYR cocrystals was faster than that of MYR in the same medium and extremely fast in pH 4.5 buffer. The improved solubility of MYR cocrystals was probably related to the alternate arrangements of MYR and INM/CAF molecules and increased intermolecular distance. The present study provides some references to investigate the solubility behavior of pharmaceutical cocrystals.
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2025
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IF 8.5
Shakeel Zeb,Zhiwei Ding,Abdul Haleem,Rongpeng Yu,Yingli Zhao,Zhanchao Liu,Yan Liu
Myricetin has a significant role in pharmacology, specifically in traditional Chinese medicine. The most intriguing pharmacological action of myricetin consists of its multi-pathway anticancer effects. Therefore, rapid and selective isolation of myricetin from garlic and apple juices has notable pharmacological benefits. Chitosan-graphene oxide-based biomacroporous cryogel are highly efficient and environmentally friendly materials for adsorption. The current study involved the synthesis of chitosan-graphene oxide-based biomacroporous cryogel sorbent for the selective recovery of myricetin. The characterization investigation utilizing SEM, XRD, EDS and FTIR demonstrated the successful synthesis of a chitosan-graphene oxide-based biomacroporous cryogel. Additionally, XPS effectively revealed the interaction of functional groups on the biomacroporous cryogel sorbent with myricetin. The maximum adsorption capacity for myricetin, under optimized conditions, was 167 mg g −1 in 60 min. The equilibrium adsorption capacity was achieved at neutral pH with optimal parameters, and the Freundlich isotherm model was followed. The pseudo-second-order model presented better descriptions of the adsorption process. In addition, the chitosan-graphene oxide-based biomacroporous cryogel exhibited remarkable selectivity: due to involvement of two primary factors: the number of hydroxyl-groups and the fact that the extra hydroxyl group at position 5′ in ring B allows for a more noticeable transfer of the unshared electron pair from oxygen to the π system of the B ring. The adsorption of myricetin decreases to 2 % after three consecutive cycles, indicating the significant reusability of chitosan-graphene oxide-based biomacroporous cryogel. Additionally, the chitosan-graphene oxide based-biomacroporous cryogel that was produced has been utilized after one month and shown a comprehensive shelf-life. Typical adsorption mechanisms include hydrogen bonding and demonstrates significant potential for the efficient and specific isolation of myricetin in complex mixtures. Furthermore, the chitosan-graphene oxide-based biomacroporous cryogel demonstrated a significant rise in recovery of myricetin flavonoid in real samples of garlic and apple juices, rising from 99.66 % to 114.29 %.
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ACS Nano
·
2024
·
IF 15.8
Lei Liu,Zhifang Ma,Qiaoyi Han,Wei Meng,Haozheng Wang,Xinghua Guan,Qiang Shi
Restoration of blood-brain barrier (BBB) dysfunction, which drives worse outcomes of ischemic stroke, is a potential target for therapeutic opportunities, whereas a sealed BBB blocks the therapeutics entrance into the brain, making the BBB protection strategy paradoxical. Post ischemic stroke, hypoxia/hypoglycemia provokes the up-regulation of transmembrane glucose transporters and iron transporters due to multiple metabolic disorders, especially in brain endothelial cells. Herein, we develop a myricetin oligomer-derived nanostructure doped with Ce to bypass the BBB which is cointermediated by glucose transporters and iron transporters such as glucose transporters 1 (GLUT1), sodium/glucose cotransporters 1 (SGLT1), and transferrin(Tf) reporter (TfR). Moreover, it exhibits BBB restoration capacity by regulating the expression of tight junctions (TJs) through the activation of protective autophagy. The myricetin oligomers scaffold not only acts as targeting moiety but is the prominent active entity that inherits all diverse pharmacological activities of myricetin. The suppression of oxidative damage, M1 microglia activation, and inflammatory factors makes it a multitasking nanoagent with a single component as the scaffold, targeting domain and curative components.
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2024
·
IF 7.7
Yuanyong Yao,Ao Ma,Huang Qi,Jiarong Chen,Jiangzhou Yan,Lihong Chen,Jiaxing Ye,Meng Zhang,Hai Yang,Shixue Chen
To gain an in-depth understanding of the process of myricetin (MY) inhibiting the generation of • O 2 − from Xanthine Oxidase (XOD) at a novel perspective, the inhibiting pathway is necessary to be re-elaborated through inhibitory type, thermodynamic analysis and molecular simulation. The results demonstrated that MY is indeed a potent inhibiting agent for • O 2 − producing from XOD, with the maximum value of 33.78 % in the inhibition of • O 2 − . Furthermore, the deprotonated form (De-MY) of MY was examined to be an effective agent for interacting with XOD, with the measurement of • O 2 − in productions from MY, XOD@MY and XAN-XOD@MY, as comparing to the XAN-XOD@ALL. On the inhibition kinetics, De-MY was witnessed to be on a mixed-type inhibition, with more competitive inhibition. In the thermodynamic analysis, the Stern-Volmer plots for De-MY obtained at 298 K, 303 K and 308 K, were polynomial-fitted to form curves approaching the X axis via the fluorescence quenching of XOD, which was against the reported with good linearity. It indicated that the interaction between De-MY and XOD occurred at the range of MY concentrations from 0 to 0.025 (×10 −5 mol L −1 ), is dominated by a static quenching procedure, ascribing to the appearance of accessible interaction with corresponding f values less than 1. As well, via combining the synchronous fluorescence data, Molecular dynamics simulations showed that MY binding to the Trp 283, ARG-60 and Tyr 58 with H-binding interactions is an available access to block the transfer of free electrons from FADH 2 to O 2 . Therefore, in this work, successfully re-elaborating the inhibition mechanism of • O 2 − generating from XOD by MY is benefited for MY in the future applications.
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JOURNAL OF FOOD COMPOSITION AND ANALYSIS
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2025
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IF 4.6
Wenhao Wang,Guoying Tan,Qinggui Lei,Jing Chen,Zhengming Qian
A rapid and environmentally friendly quantification method for myricetin and dihydromyricetin in vine tea was developed using direct infusion–tandem mass spectrometry (DI–MS/MS). These compounds are vital functional components known for their anti-inflammatory and antioxidant properties, making them significant for health promotion. DI–MS/MS enhances analytical efficiency by eliminating the need for chromatographic separation, significantly reducing analysis time and solvent consumption compared to previous methods like liquid chromatography–tandem mass spectrometry. This method was validated for accuracy, precision, and stability, ensuring reliable results across various samples. By providing a more sustainable and rapid method for the quality control of vine tea products, this method contributes significantly to the industrial development of vine tea as a functional food product, thereby supporting consumer safety and health benefits in the growing market for herbal teas and natural health products.
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY
·
2026
·
IF 4.1
Xie Yuxin,Ding Zhiwei,Zeb Shakeel,Xiang Liangyin,Yu Rongpeng,Liu Zhanchao,Jiang Yinhua,Liu Yan
A novel surface molecularly imprinted electrochemical sensor for myricetin detection was developed. This sensor employs deep eutectic solvent (DES) as a green multifunctional electrolyte to suppress template oxidation, improve solubility, and assist the electropolymerization of a dual-monomer ( p -aminobenzoic acid, p -ABA; pyrrole, Py). The sensor with DES as the electrolyte exhibited a 1.3-fold higher response current than the aqueous system, owing to enhanced myricetin solubility and reduced template oxidation. Meanwhile, it was incorporated with a well-dispersed few-layer MXene to construct an optimal sensitized interface. The dual-monomer system is capable of two types of interactions with myricetin: p -ABA forms hydrogen bonds with its hydroxyl group, while Py undergoes π–π stacking with the aromatic a-ring. This synergistic binding generates an imprinted cavity with high specificity. The amount of sorbent, pH, and voltammetric parameters were all optimized during the experiment. Differential pulse voltammetry (DPV) showed that the sensor exhibited acceptable stability, a wide linear detection range of 2.0–160 µmol/L, and a low limit of detection (LOD) of 0.5 µmol/L (signal-to-noise ratio [S/N] = 3), with an imprinting factor of 3.4. The electrochemical investigation of myricetin in real fruit juice samples showed potential for the proposed sensor, which could have applications in food safety. Graphical abstract Deep eutectic solvent-assisted dual-monomer molecularly imprinted polymer (MIP) sensor for selective voltammetric determination of myricetin (MYR) with enhanced molecular recognition. A novel molecularly imprinted electrochemical sensor for myricetin detection is fabricated by immobilizing a dual-monomer surface molecularly imprinted polymer (SMIP) layer coupled with few-layer MXene on a glassy carbon electrode (GCE). The sensor was prepared using deep eutectic solvent (DES) as the electrolyte to maintain the stability of the target molecular structure and to facilitate interactions such as hydrogen bonding and π–π stacking, thereby enhancing the selectivity of the sensor. The developed analytical approach provides valuable insights for the design and development of other electrochemical sensing systems.
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JOURNAL OF CHEMICAL NEUROANATOMY
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2024
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IF 2.7
Linli Guo,Yanan Zhao,Zhengqiao Kong,Ruihua Liu,Ping Liu
Alzheimer's disease (AD) is a degenerative neurological disorder with unclear pathogenesis. Single-target drugs have very limited efficacy in treating AD, but synthetic multi-target drugs have poor efficacy and safety. Therefore, finding suitable natural multi-target drugs against AD is of great interest for research studies. We chose two flavonols, myricetin and morin, for the relevant study. In this study, we used microinjection of Aβ 1-42 oligomers into the CA1 region of rat hippocampus, combined with gavage of Aluminum chloride hexahydrate (AlCl 3 ·6H 2 O) solution to establish AD rat models, and myricetin and morin were selected as intervening drugs to explore the protective effects against neurological impairment. Experimental results showed that myricetin or morin could reduce the production of Aβ, Tubulin-associated unit (Tau), and Phosphorylated tubulin-associated unit (p-Tau), down-regulate the expression of relevant inflammatory factors, reduce hippocampal cell apoptosis in rats. There was a significant increase in the activity of adenosine triphosphatase, catalase, total superoxide dismutase, and the content of glutathione in the brain tissue. However, the content of malondialdehyde, inducible nitric oxide synthase, and the activity of acetylcholinesterase were decreased in the brain tissue. These two flavonols can regulate the imbalance of monoamine and amino acid neurotransmitter levels. In conclusion, Myricetin or morin can effectively improve learning and memory dysfunction in AD rats induced by Aβ 1-42 /Al 3+ through anti-oxidative stress and anti-apoptotic features.
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SEPARATION AND PURIFICATION TECHNOLOGY
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2026
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IF 9.1
Rongpeng Yu,Qinya Huang,Wanyi Wang,Liangyin Xiang,Shakeel Zeb,Zhanchao Liu,Zheng Chuanbo,Yan Liu
This study explores the synthesis and application of a 2D block -shaped covalent organic framework(COF) and its integration into a surface molecularly imprinted polymers(SMIPs) for the selective adsorption of Myricetin(Myr) from food samples. The COF was synthesized using a binary deep eutectic solvent(DES1) composed of choline chloride and glycerol, while the molecularly imprinted polymers(MIPs) were polymerized on the surface of the COF utilizing a ternary deep eutectic solvent(DES2), consisting of choline chloride, acrylamide, and ethylene glycol. After optimizing the proportion of DESs, the resulting 50%-DES applied to COF(DC)-MIP exhibited a high adsorption capacity of 40.04 mg/g within 0.5 h at pH 6.0. The adsorption process, characterized by Langmuir isotherms and pseudo-second-order kinetics, was exothermic. The XPS and UV–Vis spectra confirm the adsorption mechanisms, indicating that Myr adsorption onto the COF-based MIP was predominantly driven by hydrogen bonding and π-π stacking interactions. Due to the COF serving as the matrix material, which enhances the structural stability and solvent resistance of the polymer, the 50%-DC-MIP demonstrated excellent recyclability, maintaining consistent performance over five cycles. Because of excellent selectivity, the 50%-DC-MIP was effectively employed to grape juice, bayberry juice and green tea resulting in satisfactory recoveries of 94.67% to 102.25%, 93.75% to 108.33% and 97.33% to 101.15%, respectively. These findings highlight the potential of COF-based MIPs for the selective extraction and detection of bioactive compounds like Myricetin in complex food samples, aligning with green chemistry principles by utilizing DES as environmentally friendly solvents.
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MOLECULES
·
2022
·Vol. 27
·期 23
·8140
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IF 4.927
Jianchun Zhao,Wenmin Yuan,Shixiao Wang,Hongwei Zhang,Dan Chen,Xiaochen Niu,Xiaochun Liu,Li Liu,Jiangming Gao
M10, a novel myricetin derivative, is an anti-inflammatory agent designed for treatment of colitis. Here, we aim to investigate its pharmacokinetic behavior and tissue distribution in a mouse model with colitis. Pharmacokinetics and tissue distribution of M10 and its metabolite myricetin were compared in normal mice and in dextran-sodium-sulfate (DSS)-induced colitis mice. The role of fecal microbiota was also analyzed during metabolism of M10 in vitro. After oral administration, M10 was very low in the plasma of both normal and diseased mice. However, both M10 and myricetin were mainly distributed in the gastrointestinal tract, including the stomach, colon and small intestine, in physiological and pathological conditions. Significantly, M10 and myricetin were found in higher levels in gastrointestinal tracts with inflamed tissues than in normal tissues of mice. An in vitro assay revealed that 80% of M10 was metabolized to myricetin via fecal microbiota. After oral administration, M10 was not absorbed into circulation but mainly distributed in the inflamed submucosal tissues of colitic mice, where it was metabolized into myricetin to prevent colitis development.Keywords:M10;myricetin;pharmacokinetics;tissue distribution;ulcerative colitis
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ACS Biomaterials Science & Engineering
·
2023
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IF 5.8
Lei Liu,Zhifang Ma,Qiaoyi Han,Wei Meng,Hongbo Ye,Tianci Zhang,Yu Xia,Zehong Xiang,Yue Ke,Xinghua Guan,Qiang Shi,Fazly I. Ataullakhanov,Mikhail Panteleev
The brain and liver are more susceptible to ischemia and reperfusion (IR) injury (IRI), which triggers the reactive oxygen species (ROS) burst and inflammatory cascade and results in severe neuronal damage or hepatic injury. Moreover, the damaged endothelial barrier contributes to proinflammatory activity and limits the delivery of therapeutic agents such as some macromolecules and nanomedicine despite the integrity being disrupted after IRI. Herein, we constructed a phenylboronic-decorated chitosan-based nanoplatform to deliver myricetin, a multifunctional polyphenol molecule for the treatment of cerebral and hepatic ischemia. The chitosan-based nanostructures are widely studied cationic carriers for endothelium penetration such as the blood–brain barrier (BBB) and sinusoidal endothelial barrier (SEB). The phenylboronic ester was chosen as the ROS-responsive bridging segment for conjugation and selective release of myricetin molecules, which meanwhile scavenged the overexpressed ROS in the inflammatory environment. The released myricetin molecules fulfill a variety of roles including antioxidation through multiple phenolic hydroxyl groups, inhibition of the inflammatory cascade by regulation of the macrophage polarization from M1 to M2, and endothelial injury repairment. Taken together, our present study provides valuable insight into the development of efficient antioxidant and anti-inflammatory platforms for potential application against ischemic disease.
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Food & Function
·
2025
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IF 5.4
Yilong Liu,Ruoqi Wang,Jinren Zhou,Qiang Lyu,Xiaoyong Zhao,Xiaochun Yang,Kunsong Chen,Zhiwei Gao,Xian Li
Atherosclerosis poses a significant threat to global health. This study aimed to investigate the effects of myricetin (MYR) on high-fat diet (HFD)-induced atherosclerosis in ApoE−/− mice. Our findings demonstrated that MYR treatment significantly reduced the formation of atherosclerotic plaques, particularly at a high dose of 100 mg kg−1 day−1. Additionally, MYR markedly attenuated lipid metabolism disorders in ApoE−/− mice by decreasing body weight, improving serum lipid profiles, and reducing lipid deposition. Analysis of 16S rRNA sequencing revealed that MYR treatment enhanced the abundance of probiotic g_Lachnospiraceae_NK4A136, while it reduced that of obesity-associated genera, including Rikenellaceae_RC9_gut_group and Alistipes. Metabolomic analysis and RT-qPCR tests indicated that MYR upregulated hepatic bile acid biosynthesis, evidenced by increased total bile acid levels and enhanced expression of key enzymes CYP7A1 and CYP8B1, particularly through the classical biosynthetic pathway. Spearman's correlation analysis revealed strong associations between the regulated bile acids and these aforementioned bacteria. Therefore, our results demonstrated that MYR exerts an anti-atherosclerotic effect by modulating the gut-liver axis.
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BIOORGANIC CHEMISTRY
·
2026
·
IF 5.1
Yuanyong Yao,Jiaxing Ye,Lihong Chen,Ao Ma,Xinyan Pang,Shiming Song,Meng Zhang,Shixue Chen,Hai Yang
Xanthine oxidase (XOD) is a critical biomarker associated with various pathological conditions, and recent advances have enhanced the understanding of its inhibition mechanisms. Binary inhibitor combinations, which exhibit synergistic inhibition of XOD, have attracted increasing attention. However, their underlying molecular mechanisms remain poorly elucidated. In this study, the myricetin–allopurinol (MY@ALL, 1:1) combination is identified as a promising binary inhibitor system targeting XOD. At lower concentrations, the interaction between MY@ALL and XOD likely proceeds via a static quenching mechanism, leading to the formation of a stable ground-state MY@ALL@XOD complex with a pronounced quenching effect. At higher concentrations, a mixed (both static and dynamic) quenching mechanism is observed, resulting in a weaker quenching effect. Furthermore, MY@ALL demonstrates lower binding affinity toward XOD than myricetin alone, accompanied by reduced accessibility. The binding of MY@ALL to XOD to form the MY@ALL@XOD complex is spontaneous and endothermic at low concentrations, contrasting with the exothermic nature of myricetin binding. Additionally, MY@ALL induces a smaller increase in XOD protein hydrophobicity, potentially due to more effective modulation of α-helix and β-turn structural elements. This attenuated increase in hydrophobicity may account for the reduced accessibility of the inhibitor to the enzyme. Kinetic analyses reveal that MY@ALL exhibits mixed-type inhibition, with shifting dominance between non-competitive and competitive modes under different conditions. Molecular docking and thermodynamic simulations further confirm and predict that MY@ALL binds to two distinct sites on XOD. Collectively, this work provides novel insights into the molecular basis of synergistic inhibition by efficient binary inhibitor combinations.
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