INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2023
·
IF 8.2
Shuang Xiao,Peng Zhang,Guowen Zhang,Wenwen Li,Haowen Lin,Xing Hu
The activation of toll-like receptor 4 (TLR4) signaling is crucial for initiating and coordinating the immune response against infections, and is proved as a vital target for inflammatory diseases. Herein, TLR4 with sufficient amount and functional activity was generated by heterologous expression and used to investigate the mechanism of apigenin (Api)/chrysin (Chr) inhibition of TLR4 activation. The results demonstrated that Api/Chr exhibited a strong fluorescence quenching effect through a static quenching and a high binding affinity ( K a > 10 5 L·mol −1 ) with TLR4, indicating the potential of Api/Chr as a TLR4 inhibitor. Additionally, the binding of Api/Chr induced a loose and unstable conformation of TLR4 with evidence like the decreased hydrophobicity of the tryptophan microenvironment, decreased α-helix content and increased free sulfhydryl content, resulting in reduced stability of the TLR4. The computer simulations revealed that Api/Chr occupied the myeloid differentiation factor 2 (MD-2) binding region, preventing MD-2 from binding to TLR4. Furthermore, the accuracy of the binding site between Api/Chr and TLR4 was confirmed through genetic mutations . Overall, the mechanism by which Api/Chr inhibited TLR4 activation was elucidated at the macroscopic and molecular levels, providing the worthful information concerning the future therapeutic application of Api/Chr as a natural TLR4 inhibitor.
研究领域:
免疫学
·
药理学
·
分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2014
·
IF 0.697
Man Liu,Ji Zhang,Jian Yang,Bo Yang,Wei Cui
Two routes for the synthesis of the flavones chrysin are described. In the first 1,3,5-trimethoxybenzene was converted to 2-hydroxy-4,6-dimethoxyacetophenone and then by condensation with benzaldehyde to 2′-hydroxy-4′,6′-dimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form chrysin in 53% overall yield. In the second route, 1,3,5-trimethoxybenzene was acylated with cinnamic acid to form the chalcone which was then converted to chrysin in 30.7% overall yield.
✓ 已验证
DOI
高影响因子
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
·
2014
·
IF 3.432
Zhen-Yuan Zhu,Wan-Xiao Wang,Zhen-qian Wang,Li-Jing Chen,Jing-Yi Zhang,Xiao-cui Liu,Shao-ping Wu,Yong-min Zhang
A series of 5,7-disubstituted chrysin , 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation , acetylation , benzoylation , carboxymethylation , and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents . Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC 50 value of 141 μM. Moreover, there is significant up-regulation of G2 in cell cycle of H22.
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2015
·
IF 0.633
Qian Wang,Wei Cui,Jian Yang,Bo Yang
Two novel routes for the synthesis of the flavonoid chrysin are described. In the first, 3,5-dimethoxyphenol (taxicatigenin) was converted to 2-hydroxy-4,6-dimethoxyacetophenone and then by condensation with benzaldehyde to 2′-hydroxy-4′,6′-dimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form chrysin in 50% overall yield. In the second route, taxicatigenin was acylated with cinnamoyl chloride to form a chalcone under special conditions. This was then converted to chrysin in 42% and 56% overall yield, respectively. Several disadvantages of previous syntheses like long reaction time, tedious work-up and low overall yield have been overcome.
✓ 已验证
DOI
高影响因子
Polymers
·
2022
·Vol. 14
·期 12
·2398
·
IF 4.967
Yaohui Wang,Long Li,Gege Cheng,Lanfu Li,Xiuyu Liu,Qin Huang
The separation and extraction of chrysin from active ingredients of natural products are of great significance, but the existing separation and extraction methods have certain drawbacks. Here, chrysin molecularly imprinted nanofiber membranes (MINMs) were prepared by means of electrospinning using chrysin as a template and polyvinyl alcohol and natural renewable resource rosin ester as membrane materials, which were used for the separation of active components in the natural product. The MINM was examined using Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), and thermogravimetric analysis (TGA). The adsorption performance, adsorption kinetics, adsorption selectivity, and reusability of the MINM were investigated in static adsorption experiments. The analysis results show that the MINM was successfully prepared with good morphology and thermal stability. The MINM has a good adsorption capacity for chrysin, showing fast adsorption kinetics, and the maximum adsorption capacity was 127.5 mg·g−1, conforming to the Langmuir isotherm model and pseudo-second-order kinetic model. In addition, the MINM exhibited good selectivity and excellent reusability. Therefore, the MINM proposed in this paper is a promising material for the adsorption and separation of chrysin.Keywords:chrysin;electrospinning;molecular imprinting membrane;adsorption
研究领域:
材料科学
·
天然产物化学
·
分离科学
✓ 已验证
DOI
PubMed
高影响因子
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
·
2017
·
IF 0.809
Shaohua Zhu,Yan Zhang,Peipei Li,Wenzhu Bi,Xiaolan Chen,Yufen Zhao
Display full size
✓ 已验证
DOI
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2020
·
IF 0.593
Ding Liu,Qizhi Zhang,Lang Zhang,Wenmei Yu,Huizhi Long,Jun He,Yunmei Liu
Photodynamic therapy is a promising cancer treatment with the advantages of low toxicity, high efficiency, and noninvasiveness. In this study, 23 novel porphyrin–chrysin derivatives are synthesized using alkyl carbon chains as bridges. We use human gastric cancer cells (MGC-803) and human cervical cancer cells to evaluate the in vitro antitumor activity of all the porphyrin–chrysin derivatives, with 5-fluorouracil (5-Fu) as a positive control. Several of the prepared compounds showed effective photodynamic killing effects, among which 5-hydroxy-2-phenyl-7-(2-(4-(10,15,20-tris(4-hydroxyphenyl)porphyrin-5-yl)phenoxy)ethoxy)-4H-chromen-4-one shows the highest antiproliferation activity on human cervical cancer cells, with a half maximal inhibitory concentration of 26.51 ± 1.15 µM. Flow cytometry analysis showed that human cervical cancer cell apoptosis might be induced by G1 phase arrest.
研究领域:
肿瘤学
·
药理学
·
化学合成
✓ 已验证
产品关联
DOI
高影响因子
NATURAL PRODUCT RESEARCH
·
2019
·
IF 1.999
Yang Li,Qizhi Zhang,Jun He,Wenmei Yu,Jie Xiao,Yu Guo,Xiaoming Zhu,Yunmei Liu
A series of chrysin amino acid derivatives were synthesized to evaluate for their antiproliferative activities against several cancer cell lines. Among the compounds tested, N-(2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)octanoyl)-L-leucine methyl ester(5d) presented a good anti-proliferative activity in MDA-MB-231 and MCF-7 cells. Flow cytometry analysis showed that 5d induced apoptosis and prolonged cell cycle progression in MDA-MB-231 and MCF-7 cells. Western blot analysis showed that 5d significantly inhibited Akt phosphorylation (Ser473) in MDA-MB-231 and MCF-7 cells. In addition, 5d treatment markedly downregulated Bcl-2 and upregulated Bax in a dose-dependent manner. In vitro caspase activation assay showed that 5d induced apoptosis of MDA-MB-231 cells by enhancing caspase 3/7 activity. The regulatory effect of 5d on apoptosis of MDA-MB-231 and MCF-7 cells may be induced by mitochondrial apoptosis pathway. This study is of great significance for designing and developing more effective chrysin amino acid derivatives.
研究领域:
药理学
·
肿瘤学
·
细胞生物学
✓ 已验证
DOI
PubMed
高影响因子
BIOFOULING
·
2026
·
IF 2.5
Xue Wang,Chengxi Li
Candida albicans (C. albicans) biofilms exhibit markedly enhanced tolerance to conventional antifungal agents, necessitating the identification of novel therapeutic alternatives. Chrysin, a naturally occurring flavonoid distributed in propolis and Passiflora species, possesses well-documented antioxidant and anti-inflammatory properties. However, its activity against C. albicans biofilms remains uncharacterized. This study comprehensively evaluated the antibiofilm efficacy of chrysin in vitro and in vivo. The sessile minimum inhibitory concentration causing 50% inhibition (SMIC50) of chrysin against C. albicans SC5314 was 128 μg/mL. Chrysin suppressed biofilm metabolic activity, reduced biomass, and decreased cell viability in a concentration-dependent manner, as demonstrated by XTT reduction assay, crystal violet staining, and live/dead fluorescence staining. Scanning electron microscopy (SEM) revealed progressive dismantling of hyphal networks and disruption of biofilm architecture. Chrysin significantly elevated intracellular reactive oxygen species (ROS) levels and induced mitochondrial membrane potential (MMP) depolarization in a dose-dependent manner, indicating that oxidative stress induction is a key antifungal mechanism. In a murine oral candidiasis model, chrysin reduced fungal burden and tongue lesion scores in a concentration-dependent manner, with the 256 μg/mL group achieving outcomes comparable to fluconazole. Chrysin also attenuated pro-inflammatory cytokines interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α), while increasing interleukin-10 (IL-10). Biosafety assessment demonstrated cell viability above 80% in human oral keratinocytes (HOK) and above 85% in mouse fibroblasts (L929) at concentrations up to 512 μg/mL, with no observable organ toxicity in vivo. Collectively, these findings establish chrysin as a potent, mechanistically defined, and safe natural antifungal candidate with promising translational potential for the management of C. albicans biofilm-associated infections.
✓ 已验证
DOI
PubMed
高影响因子
Chinese Herbal Medicines
·
2018
·
IF 0
Ding Liu,Yan-peng Li,Hong-xiu Shen,Yang Li,Jun He,Qi-zhi Zhang,Yun-mei Liu
Objective To design and synthesize a series of chrysin derivatives and evaluate the antitumor activities with MTT assay , so as to investigate molecular structure-activity relationship with molecular docking . Methods Target products were synthesized with high yield by substitution reaction, hydrolysis reaction, esterification reaction, and saponification reaction in sequence, and activities of all compounds were evaluated with human gastric carcinoma cell lines MGC-803 and human breast carcinoma cell lines MCF-7 through standard MTT assay. Molecular docking results were calculated with Surflex Geom X programme of Sybyl X-2.0 version workstation. Results 7- O -amino acids chrysin derivatives 6a – 6l were synthesized and their inhibitory effects were evaluated by comparing the material chrysin with positive control drug 5-fluorouracil (5-FU). Among these derivatives, compound 5b (IC 50 = 24.50 ± 2.26 µmol/L), 5k (IC 50 = 24.30 ± 2.19 µmol/L), and 6f (IC 50 = 24.61 ± 2.01 µmol/L) showed better inhibitory activities against MGC-803 cell lines, and compound 5g (IC 50 = 13.15 ± 1.73 µmol/L) and 5j (IC 50 = 12.34 ± 1.25 µmol/L) showed better inhibitory activities against MCF-7 cell lines than chrysin and 5-FU. Molecular docking scores showed a credible consistency compared with MTT results. Conclusion Compounds 5b, 5d, 5g, 5j, 5k , and 6f showed good antiproliferative effects on specific tumor cells, and compound 5g should be researched further when according to molecular docking.
研究领域:
药理学
·
肿瘤学
·
药物化学
✓ 已验证
产品关联
DOI
JOURNAL OF PHARMACY AND PHARMACOLOGY
·
2021
·Vol. 74
·期 2
·216-226
·
IF 3.765
Huang Rui,Zhao Zizuo,Jiang Xujie,Li Weiwei,Zhang Lidan,Wang Bin,Tie Hongtao
ObjectivesThe chrysin has properties of low aqueous solubility, bioavailability and absorption, and its effect on hepatic ischaemia-reperfusion (HIR) remains unclear. Thus, we prepared a liposomal chrysin (LC) and explored its effect and potential mechanism on HIR.MethodsA thin-film dispersion method was used to prepare LC, and a mouse HIR model was used. Mice were pre-treated with LC (100 mg/kg) or placebo by gavage feeding at 16.5 h, 8.5 h, 0.5 h before modelling.ResultsThe average particle sizes, polydispersity index, zeta potential, encapsulation efficiency and drug loading of LC were 129 ± 13.53 nm, 0.265 ± 0.021, −34.46 ± 4.14 mV, 95.03 ± 2.17%, 16.4 ± 0.8%. The concentration of chrysin in plasma and liver tissue by LC administration increased 2.54 times and 1.45 times. LC pre-treatment reduced HIR-induced liver injury and inhibited cell apoptosis. Besides, LC pre-treatment decreased reactive oxygen species and malondialdehyde and inhibited the inflammation response indicated by lower IL-6, TNF-α, infiltration of neutrophils. Further, LC pre-treatment significantly decreased NLRP3 activation, evidenced by reduced cleaved caspase-3, NLRP3, ASC, cleaved caspase-1 and IL-1β expression.ConclusionsLC has good biocompatibility, and it could attenuate HIR-induced injury. Its mechanism was associated with NLRP3 inflammasome inhibition, and LC might be an effective drug for treating and preventing HIR-induced injury.
研究领域:
药理学
·
肝病学
·
炎症研究
·
药物递送系统
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Polymers
·
2022
·Vol. 14
·期 14
·2771
·
IF 4.967
Long Li,Lanfu Li,Gege Cheng,Sentao Wei,Yaohui Wang,Qin Huang,Wei Wu,Xiuyu Liu,Guoning Chen
Chrysin is a natural bioactive molecule with various groups, and it has been a challenge to separate and enrich chrysin from natural products. Molecularly imprinted polymers have been widely used in the extraction of natural products, but the number and type of functional monomers limits the separation effect. The synergistic action of multiple functional monomers can improve the separation effect. In this paper, molecularly imprinted polymers (Bi-MIPs) were prepared using methacrylic acid and acrylamide as binary functional monomers for the separation and enrichment of chrysin. The Bi-MIPs were characterized using thermogravimetric analyzer (TGA), Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscope (SEM). The performances of Bi-MIPs were assessed, which included adsorption isotherms, selective recognition and adsorption kinetics. The experimental results show that Bi-MIPs are shaped as a uniform sphere with an abundant pocket structure on its surface. The adsorption of chrysin on the Bi-MIPs followed a pseudo-second-order and adapted Langmuir–Freundlich isotherm models. The adsorption performance of the Bi-MIPs was determined at different temperatures, and the Bi-MIPs showed excellent adsorption performance at 30 °C. The initial decomposition temperature of the Bi-MIPs was 220 °C. After five times of adsorption and desorption, the adsorption performance of the Bi-MIPs decreased by only 7%. In contrast with single functional monomer molecularly imprinted polymers (Si-MIPs), the Bi-MIPs showed excellent specificity, with an imprinting factor of 1.54. The Bi-MIPs are promising materials in the separation and enrichment of chrysin for their high adsorption capacity, low cost and being environmentally friendly.Keywords:chrysin;molecular imprinting;adsorption performance;binary functional monomers
研究领域:
分析化学
·
材料科学
✓ 已验证
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）