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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2023 · IF 8.2

Exploring the effect of a series of flavonoids on tyrosinase using integrated enzyme kinetics, multispectroscopic, and molecular modelling analyses

Jin Chen,Zhuangwei Zhang,Huihui Li,Hongjin Tang

The control of food browning can be achieved by inhibiting tyrosinase (TY) activity, but current studies on the interaction of flavonoids as potent inhibitors with TY are inadequate. Herein, the effect of a library of flavonoids on TY was investigated using enzyme kinetics , multispectroscopic methods, and molecular modelling. Some flavonoids including 4 , 8 , 10 , 17 , 18 , 28 , 30 , 33 , and 34 exhibited potent TY inhibitory activity, with compound 10 demonstrating reversible inhibition in a mixed-competitive manner. Ultraviolet-visible spectral changes confirmed the formation of flavonoid-TY complexes. Fluorescence quenching analysis suggested effective intrinsic fluorescence quenching by flavonoids through static quenching with the ground-state complex formation. Synchronous fluorescence spectra showed the microenvironment change around the fluorophores induced by flavonoids. ANS-binding fluorescence assay indicated TY's surface hydrophobicity change by flavonoids and highlighted the change in secondary structure conformation, which was further confirmed by Fourier-transform infrared spectra. Molecular modelling results helped visualize the preferred binding conformation at the active site of TY, and demonstrated the important role of hydrophobic interaction and hydrogen bonding in stabilizing the flavonoid-TY complexes. These findings prove that diverse flavonoid structures distinctly impact their binding behavior on TY and contribute to understanding flavonoids' potential as TY inhibitors in controlling food browning.

CAS / MDL: 59-92-7 501-30-4
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Journal of Cosmetic Dermatology · 2023 ·Vol. 23 ·期 1 ·244-255 · IF 2.3

Potent pigmentation inhibitory activity of incensole-enriched frankincense volatile oil-identification, efficacy and mechanism

Xiufang Yan,Xiaoyu Ma,Daoxin Dai,Xiaojuan Yan,Xingyan Han,Xijun Bao,Qiufang Xie

Background Frankincense volatile oil (FVO) has long been considered a side product in pharmaceutical industry since frankincense of large molecular weight is the prime target. However, the volatile oil recycled in the extract process might contain a series of functional actives, serving as promising ingredients in the cosmetic field. Methods Gas chromatography-mass spectrometer was utilized to determine the species and amount of active ingredients in FVO. Subsequently, zebrafish models were used to evaluate pigmentation inhibition, ROS elimination and neutrophil activation. In vitro DPPH test was also conducted to consolidate the anti-oxidation efficacy. Based on the test results, network pharmacology was incorporated, where GO and KEGG enrichment analyses were performed to discover the interrelations between active ingredients. Results About 40 actives molecules were identified, including incensole, acetate incensole, and acetate incensole oxide. The FVO demonstrated great depigmentation activity by suppressing melanin synthesis, as well as providing free radical scavenging and anti-inflammation effect. In network pharmacology analysis, 192 intersected targets were identified. By enrichment analysis and network construction, a series of whitening signal pathways, and hub genes, containing STAT3,MAPK3,MAPK1 were identified. Conclusion The current study quantified the components of FVO, evaluated its efficacy in skin depigmentation, and give pioneering insights on the possible mechanism. The results confirmed that the FVO could serve as whitening agent in topical uses.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2022 · IF 5.999

Ratiometric SERS quantitative analysis of tyrosinase activity based on gold-gold hybrid nanoparticles with Prussian blue as an internal standard

Dechan Lu,Qun Zhang,Zufang Huang,Yudong Lu,Shangyuan Feng,Ruiyun You,Minling Li,Shaoqin Zhang

Tyrosinase (TYR) is a polyphenol oxidase that regulates melanin biosynthesis . Abnormal levels of TYR have been confirmed closely associated with melanoma cancer and other diseases, making the establishment of highly sensitive and accurate quantitative detection of TYR is thus essential for fundamental research and clinical applications. Herein, we proposed a new strategy that combines surface-enhanced Raman scattering (SERS) with Dopamine (DA) and Prussian blue (PB) functionalized gold-gold hybrid nanoparticles for TYR detection. DA is oxidized to dopaquinone with the presence of TYR, leading to the consumption of DA in the reaction solution and the corresponding decrease in DA characteristic peak intensity at 1480 cm −1 . Our SERS quantitative assay of TYR with “on-off” sensing strategy yields an excellent limit of detection (LOD) of 3 × 10 −3 U mL −1 in a linear range of 10 −3 to 100 U mL −1 . In particular, the intensity ratio of 1480 cm −1 to 2121 cm −1 allows us to achieve remarkably reliable quantitative detection of TYR, with the 2121 cm −1 peak intensity of the standard internal (IS) molecule PB being used to correct SERS signal fluctuations. Furthermore, our proposed assay has been successfully demonstrated to quantify TYR spiked in human serum samples, with excellent percentage recovery of 90.0–110.6 %. The potential of our ratiometric SERS strategy for the performance evaluation of TYR inhibitors has also been verified. Our work is therefore expected to provide a new route for accurate and reliable monitoring of TYR activity in the complex biological environment.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF FOOD QUALITY · 2022 · IF 3.2

Phytochemical Characterization and Antioxidant and Enzyme Inhibitory Activities of Different Parts of Prinsepia utilis Royle

Yue Zheng,Lei Zhao,Junjie Yi

The objective of this study was to evaluate the phenolic composition and antioxidant and enzyme inhibitory activities of the flowers, leaves, and stems of Prinsepia utilis Royle. In the work, their total phenol content and flavonoid content were determined. In addition, the scavenging effects of DPPH and ABTS free radicals and ferric reducing antioxidant power were measured. The results showed the flowers had the highest total phenol and flavonoid content, followed by the leaves and stems. A total of 11 phenolic substances were identified and quantified using UHPLC-ESI-HRMS/MS, of which rutin was the dominant phenolic compound in all samples. All three samples had good antioxidant activity and dose dependently inhibited the activity of α-glucosidase, pancreatic lipase, and tyrosinase. In summary, the ethanol extracts of the flowers have the best antioxidant and enzyme inhibitory ability among three samples. The outcome could provide support for the development and utilization of P. utilis.

CAS / MDL: 501-30-4
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2022 ·Vol. 414 ·期 6 ·2265-2273 · IF 4.478

Fast screening of tyrosinase inhibitors from traditional Chinese medicinal plants by ligand fishing in combination with in situ fluorescent assay

Zhao Yan,Hu Jin-Jie,Bai Xiao-Lin,Liu Hao-Peng,Qi Xu-Wei,Liao Xun

A simple and rapid method for screening of tyrosinase (TYR) inhibitors present in traditional Chinese medicines (TCMs) was developed by combining ligand fishing and the fluorescent enzymatic assay based on dopamine-functionalized carbon quantum dots (CQDs-Dopa). Ligands of the enzyme present in the TCM extractions were firstly adsorbed on the enzyme-modified magnetic beads, and then the beads were magnetically separated and subjected directly to the CQDs-Dopa-based fluorescent assay. Finally, compounds were desorbed from the “active” beads and identified with ultra-performance liquid chromatography-triple quadrupole mass spectrometry. A known natural TYR inhibitor quercetin was selected to assess the feasibility and quantification performance of this method, and good linearity in the range of 0.01–0.16 mM ( R 2  = 0.992) with a low detection limit of 0.004 mM was obtained. This method was then applied to screen TYR inhibitors present in Scutellaria baicalensis and Sophora flavescens . Six TYR inhibitors including baicalin ( 1 ), baicalein ( 2 ), wogonin ( 3 ), oroxylin A ( 4 ), kurarinone ( 5 ), and sophoraflavanone G ( 6 ) were found, among which 1 – 4 were firstly discovered in this work. This is the first report on the in situ assessment of the target compounds obtained by ligand fishing in the form of a mixture, which exhibited the combined advantages of specific extraction ability of ligand fishing and the high sensitivity of CQDs-based fluorescent assay, showing great potential for fast screening of enzyme inhibitors from TCMs. Graphical abstract

CAS / MDL: 491-67-8 501-30-4
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NATURAL PRODUCT RESEARCH · 2023 · IF 2.2

Three new lanostane triterpenoids and two new amides from Alternaria sp. with NLRP3 inflammasome inhibitory activity

De-Wen Bi,Jian- Feng,Wen-Hui Pang,Peng-Yun Yang,Yao-Jun Xu,Muhammad Aurang Zeb,Meng-Ru Wang,Xing-Jie Zhang,Xiao-Li Li,Rui-Han Zhang,Wei-Guang Wang,Wei-Lie Xiao

Three new lanostane triterpenoids (1-3) along with two new amides fatty compounds (4-5) were isolated from the ethyl acetate extract of a culture of the endophytic fungus Alternaria sp. gx-2. Their structures were identified by 1D and 2D NMR spectral data and HRESIMS. Compounds 1-12 were evaluated for their anti-inflammatory and tyrosinase inhibition activities. The isolated compounds did not show inhibitory activities at a concentration of 100 μM against tyrosinase, while under the concentration of 10 μM, the release of lactate dehydrogenase (LDH) inhibition rate of compound 1 was 54.45%, indicating that compound 1 had moderate anti-inflammatory activity on the activation of NLRP3 inflammasome.

CAS / MDL: 501-30-4 9002-10-2
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CHEMISTRY & BIODIVERSITY · 2021 ·Vol. 19 ·期 1 ·e202100740 · IF 2.408

Highly Potent Inhibition of Tyrosinase by Mulberrosides and the Inhibitory Mechanism in Vitro

Xiang Liu,Jinqiu Rao,Kai Wang,Meijun Wang,Tie Yao,Feng Qiu

Many stilbene glycosides can alleviate skin hyperpigmentation due to their inhibitory effect on tyrosinase. Mulberrosides in Morus alba L. are stilbene glycosides. In the present study, the inhibition of tyrosinase by five mulberrosides (S1–5), isolated from Morus alba L. was investigated and compared, and the inhibitory mechanism was explored. These five mulberrosides exhibited obvious inhibitory effects on tyrosinase only in a concentration-dependent manner, without time-dependence, indicating that they are reversible inhibitors of tyrosinase. S2, S1 and S5 inhibited tyrosinase activity with IC 50 values of 28.93, 75.94 and 151.72 μM, respectively, and were more active than kojic acid (IC 50 =169.13 μM). Kinetic studies revealed that S1, S2 and S4 were competitive inhibitors, while S3 and S5 were mixed inhibitors. Analysis of the fluorescent spectra showed that mulberrosides S1, S2 and S4 quenched the intrinsic fluorescence intensity of tyrosinase. A molecular docking study indicated that the interaction of tyrosinase with mulberrosides was reflected by compound scores as follows: S2>S5>S1>S3/S4>kojic acid, and hydroxy groups in the side chain of mulberrosides may play a crucial role in the binding of the enzyme. Our results suggest that mulberrosides in Morus alba L. could be further developed as whitening agents for enhanced performance against hyperpigmentation. Graphical

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ELECTROPHORESIS · 2016 · IF 2.482

Screening of tyrosinase inhibitors by capillary electrophoresis with immobilized enzyme microreactor and molecular docking

Mengxia Cheng,Zilin Chen

A new method for screening tyrosinase inhibitors from traditional Chinese medicines (TCMs) was successfully developed by capillary electrophoresis with reliable online immobilized enzyme microreactor (IMER). In addition, molecular docking study has been used for supporting inhibition interaction between enzyme and inhibitors. The IMER of tyrosinase was constructed at the outlet of the capillary by using glutaraldehyde as cross-linker. The parameters including enzyme reaction, separation of the substrate and product, and the performance of immobilized tyrosinase were investigated systematically. Because of using short-end injection procedure, the product and substrate were effectively separated within 2 min. The immobilized tyrosinase could remain 80% active for 30 days at 4°C. The Michaelis–Menten constant of tyrosinase was determined as 1.78 mM. Kojic acid, a known tyrosinase inhibitor, was used as a model compound for the validation of the inhibitors screening method. The half-maximal inhibitory concentration of kojic acid was 5.55 μM. The method was successfully applied for screening tyrosinase inhibitors from 15 compounds of TCM. Four compounds including quercetin, kaempferol, bavachinin, and bakuchiol were found having inhibitory potentials. The results obtained in this work were supported by molecular docking study.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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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
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MATERIALS RESEARCH BULLETIN · 2021 · IF 4.641

Aggregation-induced emission of lead halide perovskites modulated by dispersed/aggregated gold nanoparticles for application in the detection of dopamine

Fei Qu,QianQian Fa,Tian Yin,Dafeng Jiang,Xian-en Zhao

A new kind of lead halide perovskites (LHPs) with aggregation induced emission (AIE) feature is developed. These LHPs are nonemissive when they disperse in good solvent (DMF), but show high brightness when they aggregate in water. The morphology of LHPs changes from nanometer-sized irregular shape to micrometer-sized needle-like, and then to stick-like with increasing water fraction. However, their AIE is quenched by only a few pM of dispersed gold nanoparticles (AuNPs). Dopamine (DA) induces aggregation of AuNPs, resulting in AIE recovery of LHPs. A good linear range of DA is obtained from 0.5 to 50 μM with the limit of detection (LOD) 0.12 μM. In the catalysis of tyrosinase (TYR), DA is oxidized to dopaquinone, resulting in the fluorescence quenching of LHPs again. Therefore, this system is further used for monitoring TYR activity and evaluating inhibitor of TYR. Finally, this method is successfully applied to detecting DA in urine samples.

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Insects · 2021 ·Vol. 12 ·期 6 ·510 · IF 2.769

Collaborative Response of the Host and Symbiotic Lignocellulytic System to Non-Lethal Toxic Stress in Coptotermes formosanus Skiraki

Wenhui Zeng,Bingrong Liu,Wenjing Wu,Shijun Zhang,Yong Chen,Zhiqiang Li

Simple SummaryCoptotermes formosanusShiraki is a wood feeding lower termite and is widely distributed in many areas. The dynamic adjustment of theC. formosanusdigestive system to unfavorable survival environments was investigated via non-lethal toxic feeding. The toxic stress did not change the dominant role of microbial lignocellulases in cellulose degradation ofC. formosanus. The core symbiotic community was stable in abundance during the tolerance to the toxic treatment. However, a large number of low abundance taxa were significantly enriched by the low toxic feeding. These rare bacterial lineages likely contribute to toxic stress tolerance of termite. Above all, these findings add important new knowledge to our understanding of environmental adaptation of the lignocellulose hydrolysis system in termites.AbstractDisturbing the lignocellulose digestive system of termites is considered to be a promising approach for termite control. The research on the tolerance mechanism of the termite lignocellulose digestive system to harmful environment conditions is limited. In this study, we keepCoptotermes formosanusSkiraki under a non-lethal toxic condition by feeding the termites with filter paper containing the kojic acid (a low toxic insecticide). The effects of low toxic stress on the activities and gene expressions of host/symbiotic originated lignocellulases, and on the symbiotic microbial community structure ofC. formosanuswere explored. Our result showed that the low toxic stress would lead to the synchronous decrease of cellulase and hemicellulase activities, and supplementary increase of corresponding gene expressions. The symbiotic community maintained its role as the main force in the lignocellulolytic system ofC. formosanus. Meanwhile, a large number of rare taxa were significantly enriched by kojic acid treatment. These numerically inconspicuous bacterial populations might be responsible for the functions similar to phenoloxidase or insecticide detoxification and enableC. formosanusto tolerate the harmful environment. Overall, our data suggested that the digestive adaptation ofC. formosanusto physiotoxic feeding is closely related to the triple collaboration of termites–flagellates–bacteria.Keywords:lignocellulolytic system;non-lethal stress;symbiont;termite;toxic tolerance

CAS / MDL: 501-30-4
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BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY · 2021 ·Vol. 69 ·期 3 ·951-962 · IF 2.431

Evaluation of antityrosinase activity and mechanism, antioxidation, and UV filter properties of theaflavin

Jianmin Chen,Mengnan Ran,Meixia Wang,Xinying Liu,Siwan Liu,Zhipeng Ruan,Nan Jin

Tyrosinase is a key metalloenzyme for the biosynthesis of melanin that plays a critical role in the prevention of skin damage caused by ultraviolet (UV) radiation. However, the overproduction of melanin may cause a variety of skin diseases. Due to the toxicity and inefficiency of existing tyrosinase inhibitors, it is urgent to identify safe and potent alternatives from natural sources. Theaflavin, a single-component extracted from black tea, has been found to possess a variety of pharmacological activities. Herein, the inhibition kinetics of theaflavin on tyrosinase and inhibitory mechanism were determined using spectroscopy, molecular docking, and zebrafish model. The results showed that theaflavin inhibited the diphenolase activity of tyrosinase in a reversible mixed type manner with IC 50 of 229.75 μmol/L and hindered the synthesis of melanin in zebrafish. This may be due to the formation of eight hydrogen bonds and hydrophobic effects between theaflavin and tyrosinase according to the results of molecular docking. To study the possible effects on the prevention of free radical-mediated skin cancer and photoaging caused by UV radiation, the antioxidation and UV filter properties of theaflavin were further verified. This study demonstrates that theaflavin is a potential multifunctional compound that can be used in cosmetic and medicinal products.

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