Polymer Chemistry
·
2022
·Vol. 13
·期 10
·1437-1445
·
IF 5.364
Yongjie Zhang,Xiaopei Li,Wenqin Zhu,Pibo Liu,Juntao Ren,Shangtao Chen,Yanming Hu,Guangyuan Zhou
Post-modification of polyolefins by cutting-edge C–H activation has recently emerged as an attractive methodology for the incorporation of precise functionalities, thus expanding their applicability and creating value-added materials. In this report, chromone (CM), the core of naturally occurring molecules possessing manifold biological and pharmacological activities, was incorporated into polyethylene (PE) through the recently developed radical-mediated alkane C–H activation approach. The reaction was conducted in the presence of di-tertbutyl peroxide as the oxidant and a small amount of naphthalene as the solvent or under solvent-free conditions. The produced CM-grafted PEs (CM-PEs) exhibited intriguing antioxidative and fluorescence properties as revealed by thermogravimetric analysis (TGA) and fluorescence microscopy. Moreover, CM-PEs were successfully demonstrated to act as a polymer-bound antioxidant, a fluorescence marker for plastic sorting, and a traceable compatibilizer for the PE/polystyrene blend, revealing that CM-PE is a multi-functional material.
研究领域:
材料科学
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高分子化学
·
生物医学工程
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产品关联
DOI
高影响因子
ORGANIC & BIOMOLECULAR CHEMISTRY
·
2022
·Vol. 20
·期 25
·5104-5114
·
IF 3.89
Jin-Rong Lai,Fu-Dan Yin,Qing-Song Guo,Fei Yuan,Bei-Fang Nian,Ming Zhang,Zhi-Bang Wu,Hong-Bin Zhang,E Tang
An Ag-catalysed three-component reaction of alkynyl aryl ketones bearing an ortho-methoxy group, element selenium, and arylboronic acid, providing a facile route to selenofunctionalized chromone products has been developed. This protocol features high efficiency and high regioselectivity, and the use of selenium powder as the selenium source. Mechanistic experiments indicated that the combined oxidative effect of (bis(trifluoroacetoxy)iodo)benzene and oxygen in the air pushes the catalytic redox cycle of the Ag catalyst and the phenylselenium trifluoroacetate formed in situ is the key intermediate of the PIFA-mediated 6-endo-electrophilic cyclization and selenofunctionalization reaction of alkynyl aryl ketones.
研究领域:
有机化学
·
药物化学
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DOI
PubMed
高影响因子
Pharmaceuticals
·
2025
·Vol. 18
·期 4
·510
·
IF 4.8
Mengyuan Yang,Yanan Yuan,Jingfan Wei,Yifei Pei,Yuanfei Niu,Yifan Zhao,Xiangying Kong,Zhijie Zhang
Background/Objectives: Agarwood has a good neuroprotective effect and is often used to relieve anxiety and treat insomnia. This study compared the similarities and differences in the chromone components of two types of agarwood. It further investigated the absorption and brain distribution characteristics of these components in rats and their neuroprotective effects mediated through anti-neuroinflammatory pathways.Methods: This study confirmed, through ITS2 barcoding and chloroplast genome analysis, that both the ordinary and Qi-Nan agarwood are derived fromAquilaria sinensis. A comparative analysis of chromones in ethanol extracts derived from ordinary and Qi-Nan agarwood, as well as those capable of penetrating the blood-brain barrier in vivo, was conducted using UPLC-Q-TOF-MS. Subsequently, an in vitro neuroinflammatory model was established via lipopolysaccharide (LPS)-stimulated BV-2 cells to evaluate the anti-neuroinflammatory activity of differential chromones.Results: UPLC-Q-TOF-MS characterization revealed the chromone components in the two types of agarwood: A total of 81 chromone compounds were identified in the ethanol extracts of ordinary agarwood (OAE) (20 THPECs, 42 FTPECs, and 19 BI), while 41 were identified in the ethanol extracts of Qi-Nan agarwood (QNE) (11 THPECs and 30 FTPECs). Pharmacokinetic analysis in rats showed that 14 components from OAE (eight THPECs and six FTPECs) penetrated the rat serum, and 10 of these 14 components penetrated the blood–brain barrier (BBB). Twelve FTPECs from QNE penetrated the rat serum, all of which penetrated the BBB. The total peak area of the total ion current (TIC) was calculated for the samples, and the TIC of the serum was compared to that of the brain tissue from the same rat to roughly estimate the ratio. The results demonstrated that the capability of FTPECs to traverse the blood–brain barrier is substantially superior to that of THPECs. Correspondingly, only FTPECs were detected using DESI-MS imaging; no THPECs were detected in rat brain tissue, and DESI-MS imaging localized FTPECs to neuroanatomic regions (cerebral cortex, thalamus, and hippocampus). In vitro neuroinflammatory assays revealed the superior anti-inflammatory efficacy of QNE over OAE (IL-6/TNF-α suppression,p< 0.05), correlating with its FTPEC-rich composition.Conclusions: Structure–activity relationships identified FTPECs as potent inhibitors of pro-inflammatory cytokines, exhibiting enhanced BBB penetration (blood–brain relative abundance > 1). These findings establish FTPECs as prioritized candidates for CNS-targeted therapeutics, with QNE’s pharmacological superiority attributed to its FTPEC dominance and optimized BBB transit capacity.
研究领域:
药理学
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神经科学
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植物化学
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产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2016
·Vol. 21
·期 5
·555
·
IF 2.465
Zhongxiu Zhang,Xiaohui Wang,Wanqing Yang,Juan Wang,Cong Su,Xiao Liu,Jun Li,Yunfang Zhao,Shepo Shi,Pengfei Tu
Five 2-(2-phenylethyl)chromones including a new one, (5S,6R,7S,8R)-5,8-dichloro-6,7-dihydroxy-2-phenylethyl-5,6,7,8-tetrahydro-4H-chromen-4-one (1), and four known ones (2–5), were isolated from 150 mM NaCl-elicitedAquilaria sinensiscell suspension cultures. In addition, three feruloyl amides (6–8), six nucleosides (9–14), (+)-syringaresinol (15), indole-3-carboxaldehyde (16), and two glycosides (17–18) were also obtained. The structures were unambiguously identified by analysis of their UV, IR, NMR, and HRESIMS data. The absolute configuration of the new 2-(2-phenylethyl)chromone (1) was established by a dimolybdenum tetraacetate-induced circular dichroism experiment. Compared to un-elicited cell lines, the appearance of 2-(2-phenylethyl)chromones in NaCl-treated cells occurred on the 3rd and 5th days of their treatment. 2-(2-Phenylethyl)chromones, feruloyl amides, nucleosides, and lignins have been reported to be closely related to plant defense; therefore, the identification of these compounds from NaCl-elicitedA. sinensiscell suspension cultures would be useful for further exploring the mechanism of agarwood formation.Keywords:2-(2-phenylethyl)chromone;induced circular dichroism;Aquilaria sinensis;agarwood;cell suspension cultures;sodium chloride elicitation
研究领域:
植物学
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天然产物化学
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药用植物研究
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产品关联
DOI
PubMed
高影响因子
PHYTOCHEMISTRY
·
2024
·
IF 3.2
Xiaojie Fan,Jiaxin Guo,Dongyan Feng,Dahong Li,Huiming Hua
Plants of the Garcinia genus were rich in structurally diverse and naturally bioactive components, while limited studies have been reported for Garcinia pedunculata Roxb. and G. nujiangensis C. Y. Wu & Y. H. Li. Four previously undescribed compounds including three chromones , garpedunchromones A-C ( 1 – 3 ), and one biflavonoid , nujiangbiflavone A ( 14 ), along with fifteen known analogs ( 4 – 13 , 15 – 19 ) were isolated from G. pedunculata and G. nujiangensis . The structures of the isolated compounds were determined based on their HRESIMS data, extensive NMR spectroscopic analyses , and ECD calculations. The chromone derivatives were isolated from Garcinia for the first time. Compound 14 was a rare biflavonoid with C-3─C-6″ linkage. The biological evaluation of these isolates against NO production was conducted in the LPS-induced RAW 264.7 cells, resulting in the identification of a series of potent NO inhibitors, of which garpedunchromone B ( 2 ) was the most active with an IC 50 value of 18.11 ± 0.96 μM. In the network pharmacology studies, the potential targets of compounds and inflammation were obtained from PharmMapper and GeneCards database. GO and KEGG enrichment analysis revealed that the overlapped targets were closely related to the major pathogenic processes linked to inflammation. Garpedunchromone B and proteins binding sites were being predicted.
研究领域:
植物化学
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药理学
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天然产物研究
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产品关联
DOI
PubMed
高影响因子
FITOTERAPIA
·
2024
·
IF 2.5
Yuan Wei,Wen-Hua Dong,Wei Li,Jun Zeng,Hui-Qin Chen,Sheng-Zhuo Huang,Li Yang,Wen-Li Mei,Ya-Li Wang,Zhi-Yong Guo,Hao-Fu Dai,Hao Wang
Six new dimeric 2-(2-phenylethyl)chromones ( 1 – 6 ) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1 – 6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8′′) of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC 50 value of 27.71 ± 2.60 μM, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC 50 value of 35.40 ± 1.04 μM.
研究领域:
植物化学
·
药理学
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产品关联
DOI
PubMed
高影响因子
Marine Drugs
·
2015
·Vol. 13
·期 8
·5219-5236
·
IF 2.853
Ming-Wen Xia,Cheng-Bin Cui,Chang-Wei Li,Chang-Jing Wu,Ji-Xing Peng,De-Hai Li
Three new and rare chromones, named epiremisporine B (2), epiremisporine B1 (3) and isoconiochaetone C (4), along with three known remisporine B (1), coniochaetone A (5) and methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6) were isolated from a mutant from the diethyl sulfate (DES) mutagenesis of a marine-derivedPenicillium purpurogenumG59. The structures of2–4including the absolute configurations were determined by spectroscopic methods, especially by NMR analysis and electronic circular dichroism (ECD) experiments in conjunction with calculations. The absolute configuration of the known remisporine B (1) was determined for the first time. Compounds2and3have a rare feature that has only been reported in one example so far. The compounds1–6were evaluated for their cytotoxicity against several human cancer cell lines. The present work explored the great potential of our previous DES mutagenesis strategy for activating silent fungal pathways, which has accelerated the discovery of new bioactive compounds.Keywords:chromone derivatives;remisporine;epiremisporine;isoconiochaetone;ECD;marine-derived fungus;Penicillium purpurogenumG59;DES mutagenesis
研究领域:
微生物学
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药物化学
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生物合成
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DOI
PubMed
高影响因子
RSC Advances
·
2017
·Vol. 7
·期 34
·21028-21035
·
IF 3.108
Yuyu Liu,Xiaohui Wang,Ting Mo,Yaru Yan,Yuelin Song,Yunfang Zhao,Jun Li,Shepo Shi,Xiao Liu,Pengfei Tu
Recently, owing to the important pharmaceutical properties of malonylated glycosides, their chemoenzymatic synthesis using malonyltransferase has received significant attention. In the present study, a new malonyltransferase, NbMaT1, was identified from Nicotiana benthamiana. Extensive enzymatic assays revealed its significant substrate tolerance based on HPLC-UV and HR-MS analyses. Moreover, 16 of the tested glycosides including flavone glycosides, flavonol glycosides, dihydroflavone glycosides, isoflavone glycosides, coumarin glycosides, and phenylethyl chromone glycosides with various sugar moieties (such as glucose, xylose, and galactose) substituted at different positions of their skeleton could be accepted by NbMaT1 to conduct the corresponding malonylation. Among these, enzymatic malonylation of phenylethyl chromone glycosides as well as xylosides and galactosides has rarely been reported earlier. Furthermore, one-pot synthesis using the known malonyl-CoA synthetase MatB and NbMaT1 as well as an unnatural fusion protein MatB–NbMaT1 was designed, which allowed malonic acid to be directly used in the malonylation reaction without the addition of expensive malonyl-CoA. Moreover, a remarkably improved conversion rate was observed for all the tested substrates, with both commercial and industrial application values. The malonylated product of the bioactive flavonoid diglycoside icariin was prepared and NMR spectroscopy revealed that the malonyl group was specifically transferred onto the 6-OH group of the glucose moiety. NbMaT1 was expected to be a universal and effective tool for chemoenzymatic synthesis of diverse bioactive-malonylated glycoside derivatives for drug discovery.
研究领域:
生物化学
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药理学
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植物生物技术
·
酶学
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DOI
高影响因子
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
·
2023
·
IF 5.6
Changjun Zhang,Yujia Zhang,Yangjing Lv,Jianan Guo,Bianbian Gao,Yi Lu,Anjie Zang,Xi Zhu,Tao Zhou,Yuanyuan Xie
Based on the multitarget-directed ligands (MTDLs) strategy, a series of chromone-hydroxypyridinone hybrids were designed, synthesised, and evaluated as potential multimodal anti-AD ligands. Prospective iron-chelating effects and favourable monoamine oxidase B (MAO-B) inhibitory activities were observed for most of the compounds. Pharmacological assays led to the identification of compound 17d, which exhibited favourable iron-chelating potential (pFe3+ = 18.52) and selective hMAO-B inhibitory activity (IC50 = 67.02 ± 4.3 nM, SI = 11). Docking simulation showed that 17d occupied both the substrate and the entrance cavity of MAO-B, and established several key interactions with the pocket residues. Moreover, 17d was determined to cross the blood–brain barrier (BBB), and can significantly ameliorate scopolamine-induced cognitive impairment in AD mice. Despite its undesired pharmacokinetic property, 17d remains a promising multifaceted agent that is worth further investigation.
研究领域:
药理学
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神经科学
·
药物化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF MOLECULAR STRUCTURE
·
2025
·
IF 4.7
Yingqi Qiu,Chenhao Zhao,Jiahao Lu,Pin Cheng,Aiqun Wu,Haiou Jiang,Liqun Shen
The Vilsmeier reagent was prepared from N, N-dimethylformamide and POCl₃. Cyclization with 2-hydroxyacetophenone derivatives followed by Pinnick oxidation afforded 3-carboxychromone intermediates. Subsequent condensation with dehydroabietylamine yielded eight target dehydroabietylamine-chromone derivatives 1-8 . In vitro antitumor assays demonstrated that compound 3 exhibited potent inhibitory activity against HeLa, B16F10, and HepG2 cell lines with IC₅₀ values of 2.07 ± 0.18, 4.46 ± 0.23, and 3.04 ± 0.12 μM, respectively. DAPI staining and fluorescence microscopy confirmed that compound 3 induces early apoptosis and causes cell cycle arrest at the G2/M phase. Molecular electrostatic potential (MEP) and frontier molecular orbital (FMO) analyses revealed electronic distributions and reactive sites, while docking studies indicated strong binding affinities of compound 3 toward AKT1 and SRC proteins (-9.20 and -7.76 kcal/mol). Network pharmacology and molecular dynamics simulations further validated the stability of protein complexes, profiling to evaluate pharmacokinetic properties. These findings establish a foundation for developing dehydroabietylamine-chromone hybrids as promising antitumor agents.
研究领域:
药物化学
·
药理学
·
肿瘤学
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计算生物学
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有机合成
·
生物信息学
✓ 已验证
DOI
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
·
2024
·
IF 1.3
Cai-Yun Tian,Qing-Rui Yang,Ling-Xuan Fan,Yu-Mei Yang,Bo-Wen Gao,Jian-Bo Yang
Zhachong-13 pills (ZC-13), as a traditional prescription of Mongolian medicine, are often used in the clinical practice of Mongolian hospitals for the treatment of stroke and rheumatic arthritis. In this experiment, UHPLC-Q-Exactive Orbitrap MS was used to explore the chemical composition of ZC-13. The results showed that 315 compounds were identified or inferred, including 56 alkaloids, 77 2-(2-phenylethyl)chromones, 61 flavonoids, 31 tannins, 8 coumarins, 16 lignans, 21 terpenoids, 5 amino acids, 19 organic acids, and 21 other components. In addition, the pharmacological activities related to anti-cerebral ischemia of these components were summarized. This result laid a foundation for further study on the pharmacodynamic material basis of ZC-13 and provided a scientific basis for the formulation of ZC-13 quality specifications.
研究领域:
药理学
·
分析化学
·
传统医学
·
药物化学
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产品关联
DOI
PubMed
高影响因子
TALANTA
·
2024
·
IF 5.6
Renjie Li,Haizhe Zhang,Weiqi Leng,Zhipeng Liu,Jiangtao Shi
At present, excessive Fe 3+ in daily water has become a threat to human health. Among the conventional detection methods for Fe 3+ , fluorescent probes have been applied on a large scale due to their simplicity and efficiency. However, the currently available fluorescent probes are difficult to synthesize, costly and environmentally unfriendly, limiting their applications. In this work, a fluorescent extract of Pterocarpus wood was successfully obtained, and the structure of some coumarin-based molecules in this extract was determined by 2D-NMR. Subsequently, the intensity of this fluorescence was optimized using response surface methodology (RSM), resulting in a high-intensity fluorescent probe. The probe was sensitive to the concentrations of Fe 3+ and MnO 4 − , and could efficiently detects Fe 3+ in the range of 2.7 μM–8.0 μM, with LOD and LOQ reaching 1.06 μM and 3.20 μM, respectively. Moreover, based on the strong complexation property of EDTA on Fe 3+ , this work designed the "switch-on" fluorescent probes . The experiment shows that both static and dynamic quenching exist in this system. The mechanism of complexation and oxidation of fluorescent molecules by the quencher is interpreted in the quenching reaction. In addition, the fluorescent probe has a high yield and low cost, it also performs well in actual water sample tests. This method is expected to be developed as a new way on Fe 3+ detection.
研究领域:
分析化学
·
环境科学
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材料科学
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）