MEDICINAL CHEMISTRY RESEARCH
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2023
·Vol. 32
·期 5
·899-909
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IF 2.6
Ye Zhen,Zhao Tong-Shi-Yao,Li Shan-Bin,Zhou Xian-Li,Luo Qin,Qin Jiang-Ke,Liang Cheng-Qin,Wang Ping,Ge Guang-Bo
Previous in vivo and in vitro studies revealed that esculetin (Fig. 1 ) has anti-hepatitis B virus (anti-HBV) activity as well as a protective effect on liver damage caused by duck hepatitis B virus. We designed and synthesized a series of esculetin derivatives, introduced side chains containing various amino groups into site 7 of the parent structure, and synthesized C-4 and C-8 substituted derivatives with the goal of investigating their anti-HBV activities. In vitro anti-HBV activity was performed against HepG2.2.15 cells by using Enzyme-Linked Immunosorbent Assay(ELISA) kit and cytotoxicity was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay with lamivudine as the positive control. The results demonstrated that several compounds showed moderate anti-HBV activity, while the introduction of morpholine groups could significantly inhibit the expression of hepatitis B e antigen (HBeAg) and the introduction of the 2-methylimidazole group could significantly inhibit the expression of Hepatitis B surface antigen (HBsAg). Among all tested compounds, compound 4a demonstrated the best anti-HBeAg activity (IC 50 = 15.8 ± 4.2 μM), while compound 6d demonstrated the best anti-HBsAg activity (IC 50 = 21.4 ± 2.8 μM). Compounds 6b and 6c showed moderate anti-HBV activity and HBsAg inhibition. Compounds 4b showed moderate anti-HBV activity and an inhibitory effect on HBeAg. In addition, compounds 4a , 4c , 4d , 6b , 6c and 6d showed improved metabolic stability. This study provides useful guidance for the discovery of anti-HBV drugs, which merits further investigation. Graphical Abstract
研究领域:
药理学
·
病毒学
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高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2024
·
IF 2
Cheng Yang,Haijun Yan,Qianhe Huang,Wenge Yang,Yonghong Hu
Esculetin is derived from the leaves of lemons of Rutaceae and the bark of bittersweet ash, belladonna, mandala, and Rehmannia plants. In this research, the solubility of esculetin in ten solvents such as ethyl acetate, isobutyl alcohol, water, methanol, acetonitrile, n-propyl alcohol, isopropyl alcohol, n-butanol, ethanol, and acetone was determined by utilizing static equilibrium-high performance liquid chromatography (HPLC) under standard atmospheric pressure conditions and temperatures in the range of 273.15 to 318.15 K. Among the above ten pure solvents, water displayed the least solubility, while methanol exhibited the highest solubility. At the same temperature (T = 273.15 ∼ 318.15 K), the solubility of esculetin increased with the increase of the molar ratio of soluble solvents. Similarly, when the temperature increases (T = 273.15 ∼ 318.15 K), the solubility of the three binary solvents increases under the condition of a constant molar ratio. The above results suggest that the main factor affecting the solubility of esculetin in the solvent may be the polarization/bipolarity of the solvent. The experimental data was fitted by five thermodynamic models (the Buchowski–Ksiazaczak λh model, the Modified Apelblat model, the Jouyban–Acree model, the SUN model, and the CNIBS/R-K model), and the relative average deviation and root-mean-square deviation of the data were calculated, which proved that the correlation of the solubility data and the five models was relatively good. XRD and DSC were used to detect the crystal form and stability of esculetin during the experiment.
研究领域:
药学
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物理化学
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JOURNAL OF PHYSICAL CHEMISTRY B
·
2017
·
IF 3.177
Yang Wang,Chennong Xiang,Ting Li,Piming Ma,Huiyu Bai,Yi Xie,Mingqing Chen,Weifu Dong
In this article, PVA composites with outstanding thermal stability, UV shielding, and high transparency were fabricated on the basis of traditional Chinese medicine (esculetin). Characterization data have suggested in which the resulting PVA/esculetin (ESC) composites display excellent thermal stability compared to pure PVA and most of the PVA nanocomposites. The pyrolysis mechanism of PVA before and after modification with esculetin varies from chain unzipping degradation followed by chain random scission. The DPPH scavenging activity and FTIR measurements have illustrated that esculetin can scavenge reactive radicals, which leads to improvements in thermal stability and a change in the pyrolysis mechanism of PVA. More importantly, the resulting composites can almost completely block the whole UV region (200–400 nm) without any deterioration of the high transparency of the composites. Therefore, the composites can convert harmful UV light into blue light effectively, which is beneficial for their application as optical materials and devices.
研究领域:
材料科学
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中药化学
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光化学
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PubMed
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
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2023
·Vol. 24
·期 2
·1593
·
IF 5.6
Ji Ma,Yang Deng,Tingting Yang,Maoru Li,Jing Shang
Non-alcoholic fatty liver disease (NAFLD), defined in recent years as metabolic-associated fatty liver disease (MAFLD), is one of the most common liver diseases in the world, with no drugs on market. Esculetin (ESC) is an active compound discovered in a variety of natural products that modulates a wide range of metabolic diseases and is a potential drug for the treatment of NAFLD. In this study, we used an HCD-induced NAFLD larval zebrafish model in vivo and an FFA-induced BRL-3A hepatocyte model in vitro to evaluate the anti-NAFLD effect of ESC. Lipid lowering, anti-oxidation and anti-inflammation effects were revealed on ESC and related gene changes were observed. This study provides a reference for further study and development of ESC as a potential anti-NAFLD/MAFLD drug.Keywords:esculetin;non-alcoholic fatty liver disease;lipid-lowering;antioxidant
研究领域:
药理学
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肝病学
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分子生物学
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高影响因子
PLANT DISEASE
·
2021
·Vol. 105
·期 6
·
IF 4.438
Bi Wang,Pirui Li,Shu Xu,Lanying Liu,Yannan Xu,Xu Feng,Xingzeng Zhao,Yu Chen
Esculetin is an important plant-derived natural product that has multiple bioactivities and applications. Phytophthora capsici is a notorious plant pathogen capable of infecting a broad range of hosts. In this study, we evaluated the antifungal activity of esculetin against P. capsici . The baseline sensitivity of P. capsici to esculetin was established using 108 isolates collected from various geographical regions in the Jiangsu and Shandong Provinces of China. The median effective concentration (EC 50 ) values for esculetin ranged from 2.08 to 16.46 μg/ml (mean, 6.87 ± 2.70 μg/ml) and were normally distributed. Furthermore, both zoospore production and germination were strongly inhibited by esculetin. Importantly, esculetin exhibited protective as well as curative activities against P. capsici on tomato and was capable of restricting the early infection of P. capsici on Nicotiana benthamiana . We found that the esculetin treatment led to cell membrane damage of P. capsici , as revealed by morphological observations and measurements of relative conductivity and malondialdehyde (MDA). Finally, our results also suggested that esculetin may adversely affect P. capsici by inhibiting its DNA and protein synthesis. These findings will contribute to the broader evaluation of the use of esculetin to control diseases caused by P. capsici and toward a better understanding of its mode of action as a potential fungicide.
研究领域:
植物病理学
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天然产物化学
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分子生物学
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International Journal of Electrochemical Science
·
2023
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IF 1.5
Yuanyuan Yao,Xiaomei Zhang,Na Li,Xuming Liang,Yangping Wen,Hui Zhang,Yilong Chen,Dajian Yang,Jingkun Xu
A novel simple, sensitive and selective electrochemical sensor was successfully prepared for the determination of esculetin in Cortex Fraxini based on the carboxylic acid-functionalized single-walled carbon nanotubes-Nafion–Au nanosol nanocomposite modified glassy carbon electrode (c-SWCNTs-NF–AuNs/GCE). Scanning electron microscopy, energy dispersive X-ray spectroscopy, electrochemical impedance spectroscopy and cyclic voltammetry were carried out to characterize the properties of c-SWCNTs-NF–AuNs nanocomposite. Owing to the synergistic effects of large surface area, superior electrical conductivity, and large amount of chemically active sites of c-SWCNTs, together with the good biocompatibility and high conductivity of AuNs, the c-SWCNTs-NF– AuNs/GCE exhibited a good electrocatalytic activity to esculetin with wide linear range of 0.004–55 μM and low detection limit of 0.12 nM. Additionally, the modified electrode was employed for analysis of esculetin in Cortex Fraxini with satisfactory results.
研究领域:
分析化学
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药物分析
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TALANTA
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2016
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IF 4.035
Huichao Li,Lu Wang,Kai Sheng,Lina Zou,Baoxian Ye
The nanocomposites of titanium dioxide nanoparticles decorated poly(diallyldimethylammonium chloride)-functionalized graphene (TiO 2 -PDDA-Gr) were successfully synthesized via a facile and green strategy. The prepared nanocomposites were characterized by X-ray diffraction (XRD), UV–visible spectrophotometry (UV–vis), Fourier Transform infrared spectroscopy (FT-IR) and transmission electron microscopy (TEM). By combining the merits of the PDDA-Gr and TiO 2 NPs, a highly sensitive electrochemical sensor was erected to detect esculetin based on the TiO 2 -PDDA-Gr nanocomposites. Under the optimized conditions, a lower detection limit of 4×10 −9 mol L −1 (S/N=3) and a wide linear detection range from 1×10 −8 to 3.5×10 −6 mol L −1 were achieved by differential pulse voltammetry (DPV). Additionally, the proposed electroanalytical methodology was applied in Chinese herb Viola yedoensis Makino and Cortex Fraxini with satisfactory results, showing that fabricated sensor has potential to be applied.
研究领域:
材料科学
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分析化学
·
药物分析
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MICROCHEMICAL JOURNAL
·
2026
·
IF 5.2
Si-hui Yang,Shuai-nan Zhang,Xu-zhao Li
Iniferter-mediated surface imprinting precisely controls uniform 13 nm polymer shells. • Ultrahigh adsorption capacity of 70.92 mg/g, over threefold higher than reported MIPs. • 4-VP functional monomer ensures high selectivity via hydrogen bonding (IF = 2.08). • Rapid adsorption reaches equilibrium within 2 h, following pseudo-second-order kinetics. • Excellent reusability, retaining 85.9% capacity after five adsorption-desorption cycles. As a coumarin compound with important biological activity, esculetin (ESC) is widely found in complex matrices such as herbal medicines. Due to its low content and severe matrix interference, efficient and highly selective enrichment is essential prior to analytical detection and practical application. In this study, surface molecularly imprinted nanomicrospheres (SMIMs), a type of molecularly imprinted polymer (MIP) with specific recognition ability for ESC, were successfully prepared based on surface molecular imprinting technology combined with initiation–transfer–termination polymerization, using ESC as the template molecule, 4-vinylpyridine (4-VP) as the functional monomer, and ethylene glycol dimethacrylate (EGDMA) as the cross-linking agent. The morphology, structure, and properties of the polymers were systematically characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDS), dynamic light scattering (DLS), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and Brunauer-Emmett-Teller (BET) surface area analysis. The results showed that the prepared imprinted polymers were spherical nanoparticles with uniform particle size, good dispersion, and well-developed surface pores. The adsorption experiments showed that the adsorption capacity of the SMIMs for ESC was significantly higher than that of the non-imprinted polymers (NIMs). The adsorption process followed the pseudo-second-order kinetic model and the Langmuir isotherm model. The maximum adsorption capacity reached 70.92 mg/g at 298 K, indicating excellent specific recognition performance. Analysis of real samples demonstrated that SMIMs can be successfully applied for the selective enrichment of esculetin in Herba Lysimachiae, with its content significantly increasing from 247.37 μg/kg to 645.96 μg/kg. The analytical method exhibited high accuracy (recoveries of 92.15%–104.21%) and good reproducibility (RSD < 5.0%). More importantly, the near-100% matrix effect (97.05%–104.24%) demonstrates the excellent anti-interference capability of the material when dealing with complex natural product matrices, thereby ensuring the reliability of the analytical results. This study provides new materials and methodological support for the specific enrichment and highly sensitive detection of trace bioactive components in herbs. Download: Download high-res image (123KB) Download: Download full-size image
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MATERIALS & DESIGN
·
2026
·
IF 8.2
Fengbo Yu,Ying Zhu,Xingjun Fan,Chonghuan Lin,Guifang Liu,Jingdan Cao,Qiang Wang
A pH-responsive core–shell nanogel gave fourfold enhanced skin retention of esculetin. • It matched steroid efficacy and restored barrier proteins, a dual-action therapy. • A safe, scalable platform for natural compounds as topical anti-inflammatory agents. To address the need for topical therapies with enhanced skin penetration and retention for infantile atopic dermatitis (AD), we screened esculetin (Esc), an active monomer from traditional Chinese medicine, in a cellular AD model. Esc demonstrated pronounced anti-inflammatory activity. Subsequently, a self-assembled nanogel delivery system, Esc@(HAP/PSI)-gel, was engineered using hydroxyapatite (HAP) and polysuccinimide (PSI) for sustained release. The optimized nanoparticles were spherical (Average diameter: 156 nm, zeta potential: −15.7 mV) with pH-responsive drug release. Compared with Esc-gel, Esc@(HAP/PSI)-gel significantly enhanced skin permeation and drug retention without inducing irritation. In AD mice, Esc@(HAP/PSI)-gel alleviated skin lesions, reduced ear swelling, lowered the spleen index, attenuated epidermal/dermal thickening, suppressed inflammatory cell infiltration, and modulated key cytokines (IL-6, TNF-α, IgE) more effectively than Esc-gel. Hence, the HAP/PSI-based nanogel delivery system enables the efficient and sustained delivery of Esc, enhances transdermal absorption, and demonstrates considerable therapeutic potential for AD. Download: Download high-res image (259KB) Download: Download full-size image
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POSTHARVEST BIOLOGY AND TECHNOLOGY
·
2023
·
IF 7
Lin-Jun Wang,Qiu-Han Bai,Qiu-Xia Pan,Yi-Feng Wu,Ting-Ting Shao,Yi-Wen Guo,Wen-Shuang Wei,Yi-Ting Wen,Wei-Ming Chai
The anti-tyrosinase mechanism of esculetin has been systematically investigated by various spectroscopic techniques and molecular simulation. And the outcomes confirmed that esculetin was a competitive and excellent tyrosinase inhibitor ( IC 50 =43 ± 0.5 µmol L −1 ). The binding of esculetin to tyrosinase affected the hydrophobic microenvironment of the enzyme and altered its conformation. Thermodynamic analysis and molecular docking demonstrated that the binding was driven by hydrophobic interaction and hydrogen bonding. Circular dichroism and molecular dynamic analysis revealed that esculetin induced the structural stretching of tyrosinase and slightly impacted the microenvironment of amino acid residues. Cell assays further demonstrated that esculetin inhibited intracellular tyrosinase activity and melanin production but showed no significant effect on cell proliferation . Additionally, studies on browning inhibition indicated that esculetin delayed the browning of fresh-cut apples by suppressing phenolic metabolism, strengthening antioxidant systems, and reducing membrane-lipid peroxidation. The above discoveries offered new viewpoints for understanding the suppressive mechanism of esculetin on tyrosinase and browning, as well as scientific evidence for its potential application in food preservation and medicine.
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SEPARATION SCIENCE AND TECHNOLOGY
·
2026
·
IF 2.5
Jialong Yuan,Xu Zhang,Congcong Zhao,Fengjiao Bai,Hao Yan,Jin Li,Zhenyu Zuo
A novel molecularly imprinted polymer(Esc-SMIPs) with specific selectivity for esculetin (Esc), was synthesized in this work. Dehydroabietic acid [2-(acryloyloxy) ethyl] ester (DAAEE) and 4-vinylpyridine (4-VP) were utilized as bifunctional monomers, and porous cellulose microspheres derived from traditional Chinese medicine residue were employed as the carrier. The polymer was characterized by FT-IR, SEM, BET, TEM, and TGA. Experimental results demonstrated that the Esc – SMIPs prepared by these bifunctional monomers exhibit higher adsorption capacity (37.12 mg/g) and a superior imprinting factor (2.55) compared with the SMIPs derived from other monomers (PS, AA, 4 - VP, AM and DAAEE). In addition, Esc – SMIPs were applied as the solid – phase extraction filler for the selective identification and separation of Esc from Cortex fraxini extract. The concentration of Esc in the eluent (70% ethanol) was found to be significantly higher than that in the Cortex fraxini extract. The recovery rates of spiked samples for Esc were in the range of 98.06% − 101.93%, with relative standard deviation (RSD) values below 1.86%. When compared with macroporous adsorption resin D101 or Esc – SNIPs, excellent targeted enrichment and high separation efficiency for Esc are possessed by Esc – SMIPs.
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Antioxidants
·
2026
·Vol. 15
·期 5
·652
·
IF 8.2
Haoyang Dai,Qinqin Zhang,Pei Chen,Suiqing Chen
The pathogenesis of acute liver injury (ALI) involves the loss of hepatic detoxification function, massive death of liver parenchymal cells within a short period, and excessive inflammatory responses. Studies have shown that Esculetin (Esc) possesses potent anti-inflammatory, antioxidant, and anti-tumor properties. In this study, we investigate whether Esc has a protective effect against ALI in mice and its potential mechanism. Esculetin markedly decreased ROS, MitoSOX, and apoptosis levels in AML12 cells and restored MMP. H&E staining demonstrated that Esc alleviated hepatic histopathological injury, and its intervention reduced serum ALT and AST levels. Moreover, Esc diminished ROS and apoptosis levels in the liver. Hepatic proteomic profiling identified the AMPK signaling pathway. Esc reduced the protein levels of p-AMPK/AMPK, PGC-1α, p-SIRT1/SIRT1, and BAX and upregulated the levels of Bcl-2 in liver tissue. Concomitantly, we added inhibitor Compound C (CC) to the AML12 cells to assess whether Esc acted through the AMPK pathway. The results showed that CC exacerbated the degree of liver injury, whereas Esc was able to reverse these phenomena, thus exerting an anti-liver injury effect. These findings provide mechanistic insights into the protective effects of Esc against ALI and support its potential as a therapeutic candidate for ALI.
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