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MICROCHEMICAL JOURNAL · 2022 · IF 5.304

Magnetic molecularly imprinted polymer combined with solid-phase extraction for detection of kojic acid in cosmetic products

Jie Tang,Yueran Ren,Lijun Zhu,Yuncan Chen,Shaomin Liu,Ling Zhu,Rui Yang

In this study, a new magnetic molecularly imprinted polymer Fe 3 O 4 @MIP is prepared via a surface molecularly imprinting technique; it is first applied as a magnetic solid phase extraction (MSPE) adsorbent for the selective and rapid extraction of kojic acid (KA) in cosmetic products. The as-prepared Fe 3 O 4 @MIP is characterized systematically, and is found to exhibit good monodispersity and high magnetic susceptibility in favor of fast separation. The adsorption capacity and equilibrium time of KA on the Fe 3 O 4 @MIP adsorbent are 314.0 mg/g and 30 min, respectively. In addition, the imprinting factor of Fe 3 O 4 @MIP is 2.09 for KA, which indicates that the prepared Fe 3 O 4 @MIP exhibits good selectivity for KA. Under the optimum experimental conditions, the KA in cosmetic products was successfully extracted with Fe 3 O 4 @MIP adsorbent and determined by ultraviolet–visible (UV–vis) spectrophotometry. Validation experiment shows that the developed method presents good linearity (50–500,000 μg/L), satisfactory precision (RSD, 2.5–4.6 %), and high recovery (92.4–104.6 %). The limit of detection (LOD) is 21.4 μg/L, and the enrichment factor is 299. These results suggest that this MSPE method coupled with UV–vis spectrophotometry holds great potential for efficient sample pretreatment and target molecule determination in real samples.

CAS / MDL: 919-30-2 78-10-4
研究领域: 分析化学 · 材料科学
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Food Science and Human Wellness · 2023 · IF 7

Antibacterial mechanism of kojic acid and tea polyphenols against Escherichia coli O157:H7 through transcriptomic analysis

Yilin Lin,Ruifei Wang,Xiaoqing Li,Keren Agyekumwaa Addo,Meimei Fang,Yehui Zhang,Yigang Yu

Escherichia coli O157:H7 is one of the major foodborne pathogenic bacterial that cause infectious diseases in humans. The previous found that a combination of kojic acid and tea polyphenols exhibited better activity against E. coli O157:H7 than using either alone. This study aimed to explore responses underlying the antibacterial mechanisms of kojic acid and tea polyphenols from the gene level. The functional enrichment analysis by comparing kojic acid and tea polyphenols individually or synergistically against E. coli O157:H7 found that acid resistance systems in kojic acid were activated, and the cell membrane and genomic DNA were destructed in the cells, resulting in "oxygen starvation". The oxidative stress response triggered by tea polyphenols inhibited both sulfur uptake and the synthesis of ATP, which affected the bacteria's life metabolic process. Interestingly, we found that kojic acid combined with tea polyphenols hindered the uptake of iron that played an essential role in the synthesis of DNA, respiration, tricarboxylic acid cycle. The results suggested that the iron uptake pathways may represent a novel approach for kojic acid and tea polyphenols synergistically against E. coli O157:H7 and provided a theoretical basis for bacterial pathogen control in the food industry.

CAS / MDL: 501-30-4
研究领域: 微生物学 · 食品科学 · 分子生物学
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Food Science and Human Wellness · 2020 · IF 2.455

Characterization of spoilage bacterial communities in chilled duck meat treated by kojic acid

Wenfu Hou,Qiqi Yue,Wen Liu,Ji Wu,Yang Yi,Hongxun Wang

Chilled duck meat is a popularly consumed meat in China but easily perishes at room/low temperature. Kojic acid is usually used as an antimicrobial. This study investigated the sensory scores, total bacteria number, and total volatile base nitrogen (TVB-N) value of chilled duck meat under kojic acid treatment during storage. The results presented that kojic acid suppressed the growth of spoilage bacteria and prolonged the shelf-life of chilled duck meat by at least two days. In further investigation, the bacterial community composition was explored through high-throughput sequencing. Pseudomonas spp. were the predominant spoilage bacteria after 6-day storage and were significantly suppressed by kojic acid. Besides, Brochothrix showed drug resistance and became the dominant bacteria in the kojic acid treated sample after 6-day storage. In conclusion, kojic acid maintained the sensorial, chemical, and microbial quality of duck meat stored at low temperatures. Meanwhile, kojic acid enriched the bacteria composition and showed strong antimicrobial activity against Pseudomonas spp.

CAS / MDL: 501-30-4
研究领域: 食品科学 · 微生物学 · 生物技术
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ARABIAN JOURNAL FOR SCIENCE AND ENGINEERING · 2019 ·Vol. 45 ·期 1 ·29-40 · IF 1.518

Antimicrobial Polymer with Enhanced Activity and Reduced Toxicity upon Grafting to Chitosan Oligosaccharide

Liu Xiaoli,Xie Wancui,Yang Xihong,Zhan Xiaobei,Xia Wenshui

The aim of this work was to develop a novel, nontoxic, bioactive antimicrobial material based on a natural polymer, chitosan oligosaccharides (COS), a natural pyrone compound, kojic acid (KA), and piperazine. The COS-based polymer (COS-O-MB) has been synthesized by selective partial alkylation reaction to graft kojic acid, KA, and piperazine onto the COS molecular chain. Then, physicochemical properties and bioactivity of the COS-O-MBs were evaluated and it was characterized by FT-IR, NMR spectroscopy, Mw, PID, antimicrobial activity, hemolysis assay, biocompatibility, animal toxicity, and antimicrobial action mode studies. The results revealed that the alkylation reaction took place at the C-6 position of COS, and the as-prepared COS-O-MB significantly enhanced the antimicrobial activity and biocompatibility and reduced the hemolytic activity in vitro in comparison with that of the free COS and KA. Meanwhile, the antimicrobial action mode studies proved that COS-O-MB can pass through the anionic microbial membrane, destroy the cytomembrane integrity, and potentially affect protein denaturation, demonstrating that exposure to COS-O-MB results in the death of microbial cells. But importantly, COS-O-MB is not toxic to human cells. Hence, low hemolytic activity to human red blood cells, and nontoxic nature to female mice of SLAC KM strain, made this novel polymer material a promising and effective compound for food and pharmaceutical industries.

CAS / MDL: 127-08-2 148411-57-8
研究领域: 生物材料学 · 微生物学 · 药理学
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JOURNAL OF THE ELECTROCHEMICAL SOCIETY · 2022 ·Vol. 169 ·期 3 ·037529 · IF 4.386

Blocking the Cu (II) Ions Mediated Catalytical Ability for Construction of Ratiometric Fluorescence Sensing Platform Based on Glutathione-Stabilized Copper Nanoclusters

Bei-Bei Tao,Ning-Ning Wu,Hong-Ding Zhang,Hai-Bo Wang

It is of great importance to integrate two kinds of fluorescent probes in one system to construct ratiometric sensing platform. Inspired by the efficient overlapped spectrum of glutathione-stabilized copper nanoclusters (GSH-CuNCs) and 2, 3-diaminophenazine (DAP), a novel and label-free ratiometric fluorescent sensor has been developed for Cu2+ and kojic acid (KA) detection on the basis of in situ converting o-phenylenediamine (OPD) into DAP by the catalytic oxidation ability of Cu2+. The Cu2+ catalytically generated DAP was served as an energy acceptor to inhibit the fluorescence emission of GSH-CuNCs (energy donor). As a result, the sensitivity and accuracy of the strategy were greatly improved due to the dual-emission reverse change ratiometric profile. The sensing system showed high sensitivity toward Cu2+ in a range of 0.1–50 μM and with a limit of detection of 20 nM. Furthermore, based on the specific coordination interaction between Cu2+ and KA, the ratiometric sensor displayed the range of detection of KA from 0.2 μM to 300 μM with a limit of detection of 50 nM. Thus, the ratiometric method paved a new way for the effective quantification of Cu2+ and KA in real samples, which were closely concerned with human health.

研究领域: 分析化学 · 生物医学
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ANALYTICAL BIOCHEMISTRY · 2017 · IF 2.334

Kinetics and inhibition study of tyrosinase by pressure mediated microanalysis

Dong-Mei Liu,Jun-Li Yang,Wei Ha,Juan Chen,Yan-Ping Shi

In the present study, pressure mediated microanalysis (PMMA), a fast, convenient and efficient capillary electrophoresis (CE) method was developed for studying enzyme kinetics of tyrosinase and inhibition kinetics of kojic acid , a model inhibitor of tyrosinase. The enzymatic reaction conditions and CE conditions were optimized in order to obtain high enzyme activity and short analysis time. By PMMA, only the product could be detected at 475 nm, and no voltage was applied to separate the product from the reaction mixture thus greatly simplifying the optimization procedure. The spectrophotometric assay and electrophoretically mediated microanalysis (EMMA) were also performed to validate the developed method. With the present method, the Michaelis-Menten constant ( K m ) was calculated to be 1.347 mM for tyrosinase. The inhibition constant of kojic acid to free tyrosinase ( K I ) and kojic acid to tyrosinase/L-DOPA complex ( K IS ) were calculated to be 36.64 and 74.35 μM, respectively, and the half-maximal inhibitory concentration (IC 50 ) was determined to be 46.64 μM for kojic acid. The developed method is fast and convenient for studying enzyme kinetics, inhibition kinetics and further screening enzyme inhibitors .

研究领域: 生物化学 · 酶学
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JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY · 2020 · IF 4.673

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

L. Ravithej Singh,Yu-Lin Chen,Yuan-Yuan Xie,Wei Xia,Xing-Wen Gong,Robert C. Hider,Tao Zhou

In an attempt to synthesise new tyrosinase inhibitors, we designed and synthesised a series of chalcone-hydroxypyridinone hybrids as potential tyrosinase inhibitors adopting strategic modifications of kojic acid. All the newly synthesised compounds were characterised by NMR and mass spectrometry. Initial screening of the target compounds demonstrated that compounds 1a, 1d, and 1n had relatively strong inhibitory activities against tyrosinase monophenolase, with IC50 values of 3.07 ± 0.85, 2.25 ± 0.8 and 2.75 ± 1.19 μM, respectively. The inhibitory activity against monophenolase was 6- to 8-fold higher than that of kojic acid. Compounds 1a, 1d, and 1n also showed inhibition of diphenolase, with IC50 values of 17.05 ± 0.07, 11.70 ± 0.03 and 19.3 ± 0.28 μM, respectively. The inhibition kinetics of diphenolase indicates that compounds 1a and 1d induce reversible inhibition on tyrosinase. Finally, we found that copper coordination should be one of the important inhibitory mechanism of these compounds in tyrosinase.

研究领域: 药物化学 · 生物化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2021 · IF 7.46

Plasmonic photothermal biosensor for visual detection of tyrosinase and dopamine based on manganese dioxide nanosheets-mediated etching of gold nanorods

Jin Li,Yun-Yun Wei,Xiao-Peng Liu,Zhang-Run Xu

As a crucial enzyme involved in melanogenesis, tyrosinase plays an important role in the diagnosis of melanoma. Herein, a novel and simple photothermal quantitative method based on manganese dioxide nanosheets-mediated etching of gold nanorods was established for tyrosinase activity assay with a simple household thermometer as the readout. Gold nanorods were etched by manganese dioxide nanosheets in acid condition at room temperature with a fast and stable etching efficiency. With the etching of gold nanorods, the photothermal conversion efficiency decreased gradually with the change of the aspect ratio of gold nanorods, leading to the decrease of the temperature increment of the solution by degrees. The gold nanorods have an unparalleled photothermal conversion efficiency, and the increment of temperature caused by the photothermal effect of gold nanorods has a span as wide as nearly 17 °C within one minute of laser irradiation . A household thermometer, instead of a spectrometer or any other professional and costly instruments, was used as a signal reader to achieve the visual quantitative detection, which makes this method possible for point-of-care testing. The photothermal platform was used successfully for the determination of tyrosinase and its substrate dopamine with wider linear ranges from 1.0 to 70 U/mL and 2.0–150 μM and detection limits as low as 0.34 U/mL and 0.92 μM, respectively. Moreover, the inhibition efficiency of kojic acid on tyrosinase activity was investigated, proving the photothermal quantitative method will be a potential platform for screening inhibitors of tyrosinase.

研究领域: 生物化学 · 分析化学 · 纳米技术 · 癌症诊断
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2020 · IF 2.888

Kojic acid in fourteen mono-solvents: Solubility data, Hansen solubility parameter and thermodynamic properties

Renren Sun,Haixia He,Yameng Wan,Liyuan Li,Jiao Sha,Gaoliang Jiang,Yu Li,Tao Li,Baozeng Ren

In this research, solubility of kojic acid in fourteen mono-solvents was obtained by laser monitoring approach at various temperatures under 0.1 MPa. The mole solubility of kojic acid exhibited a positive relation with temperature. Moreover, the solubility sequence of kojic acid at 298.15 K is: dimethyl sulfoxide (DMSO) > N-methylpyrrolidone (NMP) > N, N-dimethylacetamide (DMAC) > N, N-dimethylformamide (DMF) > 2-methoxyethanol > 2-ethoxyethanol > acetic acid > methanol > 1,4-dioxane > ethanol > water > n-propanol > acetone > ethyl acetate. The Hansen solubility parameter (HSP) and solvents polarity were applied to explore this solubility behaviour. The experimental solubility data was correlated with five thermodynamic models including two-Suffix Margules, NRTL-SAC, NRTL, modified Apelblat equation and UNIQUAC model, and the calculated results indicated that all of models had great fitting effects with the measured solubility data. Furthermore, the solution thermodynamic properties (Δ dis G o , Δ dis H o , Δ dis S o ) of kojic acid in investigated solvents were calculated by van’t Hoff equation. The positive values of Δ dis H o and Δ dis S o indicated that the dissolution process of kojic acid in all the measured solvents was endothermic and entropy-driven.

CAS / MDL: 501-30-4
研究领域: 化学 · 物理化学 · 热力学
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FOOD CONTROL · 2022 · IF 6.652

Kojic acid induces resistance against Colletotrichum brevisporum and enhances antioxidant properties of postharvest papaya

Yan-Xia Wang,Su-Yan Wang,Trust Beta,Mahdi Shahriar,Pedro Laborda,Daniela D. Herrera-Balandrano

Once harvested, papaya fruit is prone to rapid deterioration and spoilage by microorganisms leading to food loss. The current study aimed to evaluate the effect of kojic acid (KA) treatments (2 mM and 5 mM) on the resistance of postharvest papaya against Colletotrichum brevisporum , a hazardous fungal pathogen. The results indicated that KA treatment decreased the lesion length in papayas by 30% after 7 days of storage. In addition, KA promoted the activity of both superoxide dismutase (SOD) and catalase (CAT) enzymes. Consequently, a decrease in malondialdehyde (MDA), hydrogen peroxide (H 2 O 2 ) and nitric oxide (NO) contents was also observed. Furthermore, the application of KA enhanced the antioxidant activity and expression levels of several genes related to antioxidant properties and defense response in papaya. In this regard, the effects of KA on C. brevisporum -infected postharvest papaya were studied for the first time, revealing the ability of KA to induce disease resistance and enhance the antioxidant properties in postharvest papaya.

研究领域: 植物病理学 · 采后生理学 · 食品科学 · 分子生物学
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Chemical Biology & Drug Design · 2015 ·Vol. 86 ·期 5 ·1087-1092 · IF 2.485

Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors

Wenlin Xie,Jingai Zhang,Xiaojing Ma,Wenqian Yang,Ying Zhou,Xufu Tang,Yan Zou,Hui Li,Jingjing He,Shimin Xie,Yunhui Zhao,Fengping Liu

A series of 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole derivatives were synthesized by nucleophilic substitution reaction of 5-hydroxy-2-chloromethyl -4H-pyran-4-one with 5-substituted-3-mercapto-4-amino-1,2,4-triazole, and their inhibitory effects on mushroom tyrosinase were evaluated. The results indicated that most of the synthesized compounds exhibited significant inhibitory activity. Specifically, 5-(4-chlorophenyl)-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole ( 6j ) exhibited the most potent tyrosinase inhibitory activity with IC 50 value of 4.50 ± 0.34 μ m . The kinetic studies of the compound ( 6j ) demonstrated that the inhibitory effects of the compound on the tyrosinase were belonging to competitive inhibitors. Meanwhile, the structure–activity relationship was also discussed.

研究领域: 药物化学 · 生物化学
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CROP PROTECTION · 2026 · IF 3.3

A pH-responsive, kojic acid-based amphiphilic polymer as a nanocarrier for targeted herbicide delivery

Yuying Xie,Yangchun Ge,Zhuochao Shen,Yupeng Qiu,Haohua Zhang,Changmeng Sun,Jiangkuan Tang,Bingke Li,Junran Xu,Ping Liang,Yubang Tao,Shengtian Wang,Xuqiang Peng,Zhongyu Li

Hydrophobic herbicides often suffer from poor solubility and low bioavailability in crop protection applications, which hinders the sufficient uptake of active ingredients by target weeds and severely limits their effectiveness in safeguarding crop growth. To enhance the delivery efficiency and targeting capability of such herbicides, this study developed a pH-responsive amphiphilic polymer nanocarrier using the natural product kojic acid and triethylene glycol divinyl ether as raw materials for loading diuron. This carrier can self-assemble in aqueous media to form stable core-shell nanoparticles with a critical micelle concentration of 6.92 × 10 −3  mg/mL and an average particle size of 181.4 nm after drug loading. In a simulated acidic rhizosphere environment of Echinochloa crus-galli , the drug-loaded nanoparticles exhibited distinct pH-responsive release behavior while maintaining good physical stability. Biological experiments further confirmed that this delivery system significantly enhances the herbicidal activity of diuron against Echinochloa crus-galli , providing new insights and a material foundation for the development of efficient and intelligent herbicide delivery systems.

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