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International Journal of Electrochemical Science · 2023 · IF 1.5

Identification of Two Hetero-Substituent-Aromatic Isomers of - 4- and 7-Hydroxy Coumarin with the Belousov-Zhabotinsky Oscillator

Muhammad Yasir Nawabi,Waqar Uddin,Gang Hu,Saif Ullah,Zhaohui Fang,Saira Sardar

In this article, we presented an innovative work of distinguishing the two different positional heterosubstituents-aromatic isomers i.e. 4-hydroxycoumarin (4-HC) and 7-hydroxycoumarin (7-HC) on their perturbation effect by a novel analytical Belousov-Zhabotinskii (BZ) oscillator. In such BZ oscillator, the tetra-aza-macrocyclic copper complex ([CuL](ClO4)2) was used in which the ligand L is 5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraeazacyclotetradeca-4,11 diene. Experimental data confirmed that, by discrete injection of these two isomers (4-HC and 7-HC) into the active BZ system with equal concentrations reflected in their inhibition time (t in ), but the tin produced by 4-HC was higher than the tin initiated by 7-HC. The interesting feature is that, with increasing concentrations (9.0 x 10 -5 to 3.6 x 10 4 ) of 4-HC constantly increase the tin and decreased the oscillation number (N) after the regeneration of oscillation. Whereas, the upsurge concentrations of 7-HC didn’t change the tin but reduced the N after regeneration of oscillation. Thus, the two isomers were identified. Based on the mechanistic approach of FKN (Field-Koros-Noyes) model, the reaction perturbation mechanism was discussed. A fleeting description is that both 4-HC and 7-HC isomers were oxidized by BrO 2 intermediate radical (which produce during the course of reaction) into salicylic acid and quinone respectively and the system was temporary freeze (t in ) as well. The products (salicylic acid and quinone) were identified by infra-red and Ultra-Visible spectroscopies.

研究领域: 分析化学 · 物理化学
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PROCESS BIOCHEMISTRY · 2021 · IF 3.757

The synergistic effect of high pressure processing and pectin on the physicochemical stability and antioxidant properties of biopolymer complexes composed of soy protein and coumarin

Bei Jin,Xiaosong Zhou,Yongqi Zhong,Qiyong Li,Siyuan Zhang,Huanping Mo,Jiaru Liang

This study was devoted to explore the synergistic effect of pressure level and pectin addition on the binding and structural properties of soy protein-coumarin (S-C) complexes through multi-spectroscopic approaches to elucidate the protective effect of the complexes on physicochemical stability of coumarin . High pressure processing (HPP) could reinforce the intermolecular hydrogen bonding and hydrophobic interaction between soy protein and coumarin (at a mass ratio of 3:1), resulting in the formation of complexes with smaller particle sizes and more compact structure, the effects were more pronounced as the pressure > 200 MPa. The incorporation of pectin provided a better protection of coumarin against UV and thermal degradation and improved remarkably the physical stability of complex particles during 30 days at 4 °C. In comparison with free coumarin, the coumarin retention of S-P-C (400) was up to 55.3 ± 1.7 % when exposure to UV for 120 min, 61.7 ± 2.9 % under 90 °C heating, and 96 ± 1.5 % after storage. However, the DPPH radical scavenging ability of S-C complexes decreased with HPP treatment and the addition of pectin. The present work revealed that soy protein-pectin-coumarin ternary complexes developed by HPP could be an effective delivery system for bioactive compounds with applications in functional food ingredient.

CAS / MDL: 91-64-5
研究领域: 食品科学 · 生物化学
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Chemosensors · 2021 ·Vol. 9 ·期 3 ·48 · IF 3.398

Highly Selective Recognition of Pyrophosphate by a Novel Coumarin-Iron (III) Complex and the Application in Living Cells

Wei Wang,Hongren Zhao,Bing Zhao,Huimin Liu,Qinglei Liu,Yan Gao

In this paper, a novelNL-Fe3+ensemble was designed as a fluorescent chemosensor for highly selective detection of pyrophosphate (PPi) in DMSO/H2O (2:8/v:v, pH = 7.2) solution and living cells.NLshowed a strong affinity for Fe3+and was accompanied by obvious fluorescence quenching. Upon the addition of PPi to the generatedNL-Fe3+ensemble, the fluorescence and absorption spectra were recovered completely. Spectroscopic investigation showed that the interference provoked by common anions such as adenosine-triphosphate (ATP), adenosine diphosphate (ADP), and phosphates (Pi) can be ignored. The detection limit ofNL-Fe3+to PPi was calculated to be 1.45 × 10−8M. Intracellular imaging showed thatNL-Fe3+has good membrane permeability and could be used for the detection of PPi in living cells. A B3LYP/6-31G(d,p) basis set was used to optimizeNLandNL-Fe3+complex.Keywords:coumarin;Fe(III);pyrophosphate;cells imaging

研究领域: 生物化学 · 分析化学 · 细胞生物学
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MACROMOLECULAR RAPID COMMUNICATIONS · 2012 ·Vol. 34 ·期 3 ·274-279 · IF 4.596

Photo-controlled Hierarchical Assembly and Fusion of Coumarin-containing Polydiacetylene Vesicles

Jingguo Li,Hao Jiang,Wenlong Hu,Hongyan Xia,Gang Zou,Qijin Zhang

Herein, we synthesize a coumarin-substituted diacetylene monomer (CODA) and report the novel photo-controlled reversible assembly and disassembly behavior of the polymerized CODA (PCODA) vesicles. The photo-triggered dimerization and cleavage reactions of the coumarin groups within the surface of the adjacent PCODA vesicles can be utilized as the driving force to induce assembly and disassembly of PCODA vesicles. Moreover, the boundary of PCODA vesicles in the aggregates becomes more obscure when the irradiation time exceeds 30 min. Fusion occurs upon close docking of target membranes, driven by sufficient dimerization of the coumarin groups within the surface of PCODA vesicles.

CAS / MDL: 93-35-6
研究领域: 材料科学 · 生物化学 · 纳米医学
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FISH & SHELLFISH IMMUNOLOGY · 2018 · IF 3.185

Synthesis and antiviral activity of a new coumarin derivative against spring viraemia of carp virus

Yu-Feng Shen,Lei Liu,Chen-Zhang Feng,Yang Hu,Cheng Chen,Gao-Xue Wang,Bin Zhu

Coumarin as a lead structure have received a considerable attention in the last three decades for the discovery of antiviral agents. Our previous study indicated that imidazole coumarins possessed antiviral activities against SVCV . Based on the structure-activity relationship in that study, a new imidazole coumarin derivative, 7-(4-benzimidazole-butoxy)-coumarin (BBC), was designed, synthesized and its anti-SVCV activity was evaluated. By comparing inhibitory concentration at half-maximal activity (IC 50 ), we found that BBC (IC 50  = 0.56 mg/L) possessed a higher antiviral activity than those imidazole coumarins in our previous study. Besides, BBC can significantly inhibit cell death and reduce cellular morphological damage induced by SVCV. Our further data indicated that intraperitoneal injection of BBC increased the survival rate of zebrafish by 17.5%, decreased viral titer in fish body and inhibited SVCV glycoprotein expression in kidney and spleen . In uninfected zebrafish, the expression levels of ifnγ , ifnφ1 , ifnφ2 and rig1 genes were up-regulated after BBC treatment, which indicated that BBC could activate interferon response. In addition, data of the antioxidant enzymes activities and results of the antioxidant enzymes-related genes expressions suggested BBC could reduce SVCV-induced oxidative damage in infected zebrafish. Altogether, BBC is expected to be a therapeutic agent against SVCV infection in the field of aquaculture.

CAS / MDL: 93-35-6
研究领域: 水产养殖 · 病毒学 · 药理学
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Journal of Food Measurement and Characterization · 2021 ·Vol. 15 ·期 6 ·5439-5444 · IF 2.431

Analysis of coumarin in food and plant tissue without extraction based on voltammetry of microparticles

Fu Li,Chen Fei,Zhao Shichao,Yu Jinhong,Karimi-Maleh Hassan,Lin Cheng-Te

The detection of coumarins in real samples often requires a complex extraction process, which makes the analytical technique unable to meet the actual detection needs. In this work, we proposed a novel analytical technique based on the electrochemical reduction behavior of coumarins. This technique does not require complex pretreatment of the real sample, such as extraction and filtration. The sample particles were directly immobilized on the surface of the electrode after co-mixing with graphene. After a simple pre-reduction process, the amount of coumarin in the real sample can be evaluated by voltammetry. We have analyzed the feasibility of this technique by using cakes, fruits and different organ tissues of Glehnia littoralis . The results showed that this new analytical technique successfully achieved the rapid detection of coumarin content in real samples. The amount of coumarin in apples was 0.045 mg/g. The amount of coumarin in the roots, leaves and fruits of Glehnia littoralis was 0.037 mg/g, 0.011 mg/g and 0.079 mg/g, respectively.

CAS / MDL: 91-64-5
研究领域: 分析化学 · 食品科学 · 植物学
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ANALYTICA CHIMICA ACTA · 2016 · IF 4.712

A quick response fluorescent probe based on coumarin and quinone for glutathione and its application in living cells

Xi Dai,Zhi-Fang Du,Li-Hong Wang,Jun-Ying Miao,Bao-Xiang Zhao

We have designed and synthesized a simple but effective fluorescent probe for sensing glutathione (GSH) by PET process based on coumarin and quinone , which worked as fluorophore and reaction site, respectively. The probe could discriminate GSH from cysteine and homocysteine within 1 min in PBS-buffered solution. The sensing mechanism was confirmed by density functional theory (DFT), viscosity test, fluorescence spectrum analysis and HRMS , respectively. The probe has a low limit of detection (0.1 μM) and finally been used in cell imaging successfully.

研究领域: 生物化学 · 分析化学
✓ 已验证 DOI PubMed 高影响因子
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ACS Applied Materials & Interfaces · 2018 · IF 8.097

Coumarin-Based Oxime Esters: Photobleachable and Versatile Unimolecular Initiators for Acrylate and Thiol-Based Click Photopolymerization under Visible Light-Emitting Diode Light Irradiation

Zhiquan Li,Xiucheng Zou,Guigang Zhu,Xiaoya Liu,Ren Liu

Developing efficient unimolecular visible light-emitting diode (LED) light photoinitiators (PIs) with photobleaching capability, which are essential for various biomedical applications and photopolymerization of thick materials, remains a great challenge. Herein, we demonstrate the synthesis of a series of novel PIs, containing coumarin moieties as chromophores and oxime ester groups as initiation functionalities and explore their structure–activity relationship. The investigated oxime esters can effectively induce acrylates and thiol-based click photopolymerization under 450 nm visible LED light irradiation. The initiator O-3 exhibited excellent photobleaching capability and enabled photopolymerization of thick materials (∼4.8 mm). The efficient unimolecular photobleachable initiators show great potential in dental materials and 3D printings.

CAS / MDL: 68-12-2 7446-08-4
研究领域: 材料科学 · 化学 · 生物医学工程
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2024 · IF 4.3

Dual detection of Hg2+ and Pb2+ by a coumarin-functionalized Schiff base in environmental and biosystems

Brian Musikavanhu,Tingting Pan,Quanhong Ma,Yongdi Liang,Zhaoli Xue,Lei Feng,Long Zhao

Fluorescent chemosensors are often preferred for tracking toxic ions because of their non-destructive measurement and ease of use in environmental real samples and biosystems. Exploring high selectivity, great sensitivity, and biocompatible fluorophores with facile, accessible and dual-responsive features is currently highly demanding. A coumarin-based naphthol hydrazone Schiff base chemosensor, NaChro , is designed and synthesized in a two-step process to detect toxic metal ions with strong emission. Fluorescence spectra analysis demonstrates that the probe binds to Hg 2+ and Pb 2+ ions with a 1:1 and a 2:1 stoichiometry, respectively, with high sensitivity, short response time and minimal interference from other metal ions. The observed reversible turn-on reaction was attributed to the inhibition of C = N isomerization and excited-state intramolecular proton transfer (ESIPT) processes once the ions were introduced. The practical applications of NaChro are successfully addressed in paper strips, various water samples, HeLa cells and Zebrafish, demonstrating that the probe can detect and track Hg 2+ and Pb 2+ ions in environmental samples and biosystems.

研究领域: 环境科学 · 生物化学 · 分析化学
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CHEMICAL RESEARCH IN CHINESE UNIVERSITIES · 2014 ·Vol. 30 ·期 3 ·362-367 · IF 1.119

Coumarin modified rhodamine derivative: Fluorescent chemosensor selectively recognizing Al3+ and Ca2+

Cao Li,Jia Chunman,Zhang Qi,Chen Da,Zhang Chunyan,Qian Yaao

A fluorescent probe with a coumarin moiety bound to rhodamine 6G hydrazide( 1 ) was synthesized. Its sensing behavior toward various metal ions was investigated with fluorescence methods. Compound 1 displays different fluorescence emission responses to Al 3+ and Ca 2+ at the same excitation wavelength in the visible light region, while no changes occur after the addition of other metal ions. The binding ratios of the complexs of 1 -Al 3+ and 1 -Ca 2+ are both 2:1 according to the Job plot and high resolution mass spectrometer(HRMS) experiments. Moreover, emission spectrum of 1 -Ca 2+ complex and absorption spectrum of the rhodamine dyes overlap largely. When Al 3+ was added to the 1 -Ca 2+ system, calcium in complex 1 -Ca 2+ can be displaced by Al 3+ , resulting in the output of another ratiometric sensing signal, which demonstrates that the 1 -Ca 2+ complex can be served as a new and effective fluorescence resonance energy transfer(FRET) donor for rhodamine derivatives.

研究领域: 化学传感器 · 荧光共振能量转移
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Biomass Conversion and Biorefinery · 2023 · IF 4

Large-scale isolation of scopoletin from Nicotiana tabacum

Chen Yujiao,Chen Min,Zhang Wuhua,Zhang Shishan,Su Xiankun,Zhao Taijun,Chen Yidan,Su Xiaowei,Zeng Jingwen,Cao Jun,Liu Zhengbo,Zhong Li,Wang Guixue

Nicotiana tabacum leaves are mainly used in the production of cigarettes and cigars all over the world, and a large amount of waste materials will be produced in the process. High-value scopoletin can be extracted and separated from waste materials, but there are some problems, such as low purity of products and inability of large-scale production. In this study, we established an efficient and stable method for producing high-purity scopoletin from waste tobacco by containing acetone reflux extracting with dynamic axial compression-high performance liquid chromatography (DAC-HPLC) separating. In particular, the extraction system makes the scopoletin fully extracted through continuous reflux, the DAC-HPLC system makes the high-purity scopoletin repeatedly obtained, and the DAC-HPLC system was first used for scopoletin. Finally, related to the waste tobacco power, the yield of scopoletin is 1.9%, and its HPLC purity is 99.94%. Additionally, a preparation method for the colorless needle crystal of scopoletin was established. Meanwhile, it has a strong antioxidant activity by testing the scavenging activity of the DPPH free radical and the Fe 3+ reducing power. And its spatial structure was identified by an X-ray diffractometer, which laid a good foundation for in-depth study of scopoletin. Graphical Abstract

CAS / MDL: 7705-08-0
研究领域: 植物化学 · 药物化学 · 环境科学
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JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS · 2014 · IF 2.829

Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC–MS/MS) with selected reaction monitoring

Feng Chen,Hai-Long Li,Yin-Feng Tan,Yong-Hui Li,Wei-Yong Lai,Wei-Wei Guan,Jun-Qing Zhang,Yuan-Sheng Zhao,Zhen-Miao Qin

Alpinia oxyphylla (Yizhi) capsularfruits are commonly used in traditional medicine. Pharmacological studies have demonstrated that A. oxyphylla capsularfruits have some beneficial roles. Besides volatile oil, sesquiterpenes, diarylheptanoids and flavonoids are main bioactive constituents occurring in the Yizhi capsularfruits. The representative constituents include tectochrysin, izalpinin, chrysin, apigenin-4′,7-dimethylether, kaempferide, yakuchinone A, yakuchinone B, oxyphyllacinol and nootkatone. Their content levels in the fruit and its pharmaceutical preparations have been reported by our group. The nine phytochemicals are also the major components present in the Yizhi alcoholic extracts, which have anti-diarrheal activities. However, the fates of these constituents in the body after oral or intravenous administration remain largely unknown. In the present study, we focus on these phytochemicals albeit other concomitant compounds. The chemicals and their metabolites in rat plasma were identified using liquid chromatography/tandem mass spectrometry with selected reaction monitoring mode after orally administered Yizhi extract to rats. Rat plasma samples were treated by methanol precipitation, acidic or enzymatic hydrolysis. This target analysis study revealed that: (1) low or trace plasma levels of parent chemicals were measured after p.o. administration of Yizhi extract, Suoquan capsules and pills to rats; (2) flavonoids and diarylheptanoids formed mainly monoglucuronide metabolites; however, diglucuronide metabolites for chrysin, izalpinin and kaempferide were also detected; (3) metabolic reduction of Yizhi diarylheptanoids occurred in rats. Yakuchinone B was reduced to yakuchinone A and then to oxyphyllacinol in a stepwise manner and subsequently glucuronidated by UDP-glucuronosyl transferase. Further research is needed to characterize the UDP-glucuronosyl transferase and reductase involved in the biotransformation of Yizhi chemicals.

研究领域: 药理学 · 分析化学
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