BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
·
2021
·Vol. 85
·期 7
·1697-1705
·
IF 2.043
Chen Jianmin,Ran Mengnan,Wang Meixia,Liu Xinying,Liu Siwan,Yu Yue
The related structure–activity relationships of cinnamic acid and its derivates have not been studied in details yet. Herein, antityrosinase and antioxidant activities of 18 compounds were evaluated. The results demonstrated that the substituents on the phenyl ring of cinnamic acid led to the enhancement of the inhibition on monophenolase and the weakening of the inhibition on diphenolase. Among these tested compounds, 9 was first discovered as a tyrosinase inhibitor in a reversible competitive manner with IC50 value of 68.6 ± 4.2 µm. Docking results demonstrated 9 located into the catalytic center of tyrosinase. Antioxidant assay indicated that only 1 hydroxyl group on the phenyl ring was not enough to possess the radical scavenging activity, and the number of hydroxyl groups may be more important. This study will be helpful in the development of new cinnamic acid derivates as tyrosinase inhibitors and antioxidants with higher efficacy.
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JOURNAL OF CHEMICAL THERMODYNAMICS
·
2020
·
IF 2.888
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.
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JOURNAL OF FOOD PROCESSING AND PRESERVATION
·
2020
·Vol. 45
·期 1
·e15087
·
IF 1.405
Sizhu Tian,Xuwen Li,Shuang Zang,Yongri Jin,Ziwei Zhang,Yong Yu
The phenolic compound contents, antioxidant capacities, and α-amylase and tyrosinase inhibitory activities of 10 wild and 19 cultivated blueberries grown in northeast China were evaluated. The results showed that the α-amylase inhibitory activities of the blueberries represented, by 1/IC 50 , correlated with their total phenolic contents (TPCs). Moreover, the tyrosinase inhibitory activities correlated with the total anthocyanin contents (TACs). High-performance liquid chromatography and electrospray mass spectrometry were conducted to determine and identify seven phenolic acids. The average caffeic acid contents of the cultivated and wild blueberries were 277.37 and 17.71 μg/g, respectively. The total phenolic, anthocyanin, and flavonoid contents were determined. Wild blueberries have higher TPCs, α-amylase inhibitory activities, and antioxidant capacities. Cultivated blueberries have higher TACs and exhibit tyrosinase inhibitory activities similar to those of the wild ones. Practical applications This study revealed that wild blueberries have high α-amylase inhibitory activities and are effective as natural α-amylase inhibitors for the treatment of diabetes. In addition, wild blueberries were found to be rich in phenolics and have high antioxidant capacities. Thus, because of these properties, wild blueberry products with antidiabetic and antioxidant potential can be developed for use in biomedical and pharmaceutical industries.
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Food Science and Human Wellness
·
2020
·
IF 2.455
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.
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MOLECULES
·
2020
·Vol. 25
·期 2
·344
·
IF 3.267
Limin Qu,Ke Song,Qi Zhang,Jie Guo,Juan Huang
Tyrosinase inhibitors with excellent inhibitory activities and lower side effects have promising applications in the fields of medicine, agriculture, food sciences and cosmetics. In this study, a method for simultaneous separation and determination of six target compounds (puerarin, daidzin, genistein, daidzein, genistin, and formononetin) inPuerariae LobataeRadix was established by cloud point extraction (CPE) and concentration combined with high performance liquid chromatography (HPLC). To achieve high extraction yields, an ultrasound-assisted extraction method was developed based on a salt-modified Triton X-100 system. The optimal extraction conditions are: surfactant Triton X-100 concentration 0.07 g/mL, liquid-solid ratio 80:1 (mL/g), NaCl addition amount 0.6 g, equilibrium time 40 min, equilibrium temperature 70 °C. Under the optimal conditions, the total maximum extraction yield of the six target isoflavones reached 8.92 mg/g. Usingl-tyrosine andl-dopa as substrates, the effects of puerarin on the monophenolase and diphenolase activity of tyrosinase activity were investigated by the enzyme kinetics method. The results showed that puerarin inhibited monophenolase activity with an IC50of 0.537 mg/mL and activated diphenolase activity. The inhibition type of puerarin on monophenolase and the activation type of puerarin on diphenolase were analyzed by Lineweaver-Burk plots which show that puerarin showed mixed inhibition on monophenolase and mixed activation on diphenolase. Therefore, puerarin can be used as both a tyrosinase inhibitor and a tyrosinase activator.Keywords:Puerariae LobataeRadix;cloud point extractions;tyrosinase inhibitors;tyrosinase activator;kinetic analysis
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Food & Function
·
2019
·Vol. 10
·期 10
·6915-6926
·
IF 3.241
Sen Guo,Li Liu,Shanshan Zhang,Chuang Yang,Wenping Yue,Haoan Zhao,Chi-Tang Ho,Junfeng Du,Hai Zhang,Naisheng Bai
Morus species, commonly known as mulberry, is widely distributed in China. The mulberry tree is a high-value plant in agriculture. Morus australis is one of the major Morus species growing in Northern China. However, the biological properties of the main constituents of M. australis roots were not well studied. In the present study, through extensive chromatographic and spectral analysis, 12 phenolic compounds were isolated and identified from the M. australis roots. Compounds 1, 2, 8, 9 and 12 were isolated from M. australis roots for the first time. Antitumor activities of these polyphenols were studied on the A549 cell line. Compounds 1, 5 and 6 exhibited cytotoxicity on A549 cells and induced apoptosis in A549 cells via the intrinsic mitochondrial pathway. They also mediated inhibition of autophagic flux contributed cell death via the PI3k/Akt/mTOR pathway. In order to explore more potential bioactivities of these isolates, α-glucosidase, acetylcholinesterase and tyrosinase inhibitory activities were studied, and the results demonstrated that the inhibitory activity of these polyphenols on enzymes was not defined by their basic structural skeletons, but by the substituted position.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
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2019
·
IF 2.931
Jianmin Chen,Qinglian Li,Yaling Ye,Ziyao Huang,Zhipeng Ruan,Nan Jin
Tyrosinase is the rate-limiting enzyme for controlling the production of melanin in the human body, and overproduction of melanin can lead to a variety of skin disorders. In this paper, the inhibitory kinetics of phloretin on tyrosinase and their binding mechanism were determined using spectroscopy, molecular docking, antioxidant assays and chromatography. The spectroscopic results indicate that phloretin reversibly inhibits tyrosinase in a mix-type manner through a multiphase kinetic process with the IC 50 of 169.36 μmol/L. It is shown that phloretin has a strong ability to quench the intrinsic fluorescence of tyrosinase mainly through a static quenching procedure, suggesting that a stable phloretin-tyrosinase complex is generated. Molecular docking results suggest that the dominant conformation of phloretin binds to the gate of the active site of tyrosinase. Moreover, the antioxidant assays demonstrate that phloretin has powerful antioxidant capacity and has the ability to reduce o -dopaquinone to l -dopa just like ascorbic acid . Interestingly, the results of spectroscopy and chromatography indicate that phloretin is a substrate of tyrosinase but also an inhibitor. The possible inhibitory mechanism is proposed, which will be helpful to design and search for tyrosinase inhibitors.
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MICROCHIMICA ACTA
·
2019
·Vol. 186
·期 5
·1-7
·
IF 5.479
Deng Hao-Hua,Lin Xiu-Ling,He Shao-Bin,Wu Gang-Wei,Wu Wei-Hua,Yang Yu,Lin Zhen,Peng Hua-Ping,Xia Xing-Hua,Chen Wei
It is found that catechol inhibits the oxidase-mimicking activity of chitosan-protected platinum nanoparticles (Chit-PtNPs) by competing with the substrate for the active site of the Ch-PtNPs. The inhibition mechanism of catechol is different from that of ascorbic acid in that it neither reacts with O 2 •- nor reduces the oxidized 3,3′,5,5′-tetramethylbenzidine (TMB). Tyrosinase (TYRase) catalyzes the oxidation of catechol, thus restoring the activity of oxidase-mimicking Chit-PtNPs. By combining the Chit-PtNP, catechol, and TYRase interactions with the oxidation of TMB to form a yellow diamine (maximal absorbance at 450 nm), a colorimetric analytical method was developed for TYRase determination and inhibitor screening. The assay works in the 0.5 to 2.5 U·mL −1 TYRase activity range, and the limit of detection is 0.5 U·mL −1 . In our perception, this new assay represents a powerful approach for determination of TYRase activity in biological samples.
Schematic representation of a colorimetric method for tyrosinase (TYRase) detection and inhibitor screening. It is based on the fact that catechol can inhibit the oxidase-like activity of chitosan-stabilized platinum nanoparticles (Ch-PtNPs) by competing with the substrate for the active sites and TYRase can catalyze the oxidation of catechol.
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Analytical Methods
·
2019
·Vol. 11
·期 11
·1500-1507
·
IF 2.378
Sha Sha Li,Bo Yin,Hong Lin Zhai,Shao Hua Lu,Jia Ying Mi
Although UV-Vis spectroscopy has been applied in many fields, it still encounters some challenges in multi-component mixture analysis due to severe spectral overlapping and different interferences. In this paper, a Tchebichef curve moment (TM) approach has been developed and proposed for the quantitative analysis of five skin-whitening agents in several cosmetic products with different substrates based on conventional UV-Vis determination for the first time. First, the TMs were calculated from the raw UV-Vis spectra of mixed standard samples, and employed to establish linear quantitative models by stepwise regression. Then, the obtained models were applied to the analysis of real samples. The leave-one-out correlation coefficients (Rloo-cv) of the established models were more than 0.9948 within the linear ranges. The proposed approach was evaluated using intra- and inter-day precision (less than 5.98%) and recovery (ranging from 88.3 ± 2.8% to 109.2 ± 2.3%). The LODs and LOQs were less than 0.13 mg L−1 and 0.45 mg L−1, respectively. Compared with the classical methods, the proposed approach is not only more accurate, reliable and robust in the quality control analysis of cosmetic products, but also can extend effectively the application of conventional UV-Vis determination.
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JOURNAL OF FOOD BIOCHEMISTRY
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2019
·Vol. 44
·期 1
·e13088
·
IF 1.358
Xiao Tian,Sen Guo,Shanshan Zhang,Peisheng Li,Tianyi Wang,Chi-Tang Ho,Min-Hsiung Pan,Naisheng Bai
The seeds of tree peony ( Paeonia ostii ) are promulgated as emerging edible oil crops. However, biological properties of principal constituents of peony seeds were not well studied. Fifteen main constituents including suffruticosols A and B, trans -ε-viniferin, ampelopsin E, resveratrol, trans -resveratrol-4′- O -β- d -glucopyranoside, paeoniflorin, luteolin, luteolin-4′- O -β- d -glucopyranoside, apigenin, kaempferol, oleanic acid, betulinic acid, hederagenin, and caffeic acid were isolated and identified. Their cytotoxicity against human tumor cell lines (COLO205, HT-29, HepG2, AGS, and HL-60) were evaluated. Among them, trans -ε-viniferin showed the most potent cytotoxicity against HL-60 cells (IC 50 5.6 μM); ampelopsin E exhibited the most obvious antiproliferative properties on COLO205 (IC 50 78.1 μM) and HT-29 (IC 50 4.2 μM) cells, and betulinic acid showed the strongest growth inhibitory effects on HepG2 (IC 50 6.6 μM) and AGS (IC 50 5.4 μM) cells. Three enzymes (tyronsinase, α-glucosidase, and acetylcholinesterase) inhibitory activities of 12 compounds were also screened. Stilbene compounds, especially suffruticosols A and B, showed a significant inhibitory activity on all three enzymes. Practical applications The cytotoxicity of 15 main constituents from peony seeds against COLO205, HT-29, HepG2, AGS, and HL-60 cells were evaluated. Among them, trans -ε-viniferin showed the most potent cytotoxicity against HL-60 cells (IC50 5.6 μM); ampelopsin E exhibited the most obvious antiproliferative properties on COLO205 (IC50 78.1 μM) and HT-29 (IC50 4.2 μM) cells, and betulinic acid showed the strongest growth inhibitory effects on HepG2 (IC50 6.6 μM) and AGS (IC50 5.4 μM) cells. Collectively, these results suggested that Paeonia ostii seed (POS) extracts are potential candidates for anticancer agents.
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ANALYTICAL CHEMISTRY
·
2018
·
IF 6.042
Jiahui Zhao,Shuang Wang,Shasha Lu,Xingfu Bao,Jian Sun,Xiurong Yang
An enzyme cascade-triggered reaction with novel signal generation mechanism is beneficial for the development and insight of the enzyme cascade, which is extensively used for signal transduction in potential applications. Inspired by the fluorogenic and chromogenic reaction between dopamine and resorcinol, and the specific catalytic properties of alkaline phosphatase (ALP) and tyrosinase, we designed and synthesized an unconventional substrate of ALP, named p-aminoethyl-phenyl phosphate disodium salt (PAPP). As expected, the ALP and tyrosinase-incubated PAPP solution exhibited pale yellow with intense blue fluorescence upon addition of resorcinol, owing to the ALP-catalyzed transformation of PAPP into an intermediate tyramine, and the tyrosinase-catalyzed hydroxylation of tyramine to dopamine, as well as the specific reaction between dopamine and resorcinol. Therefore, an enzyme cascade system has been developed herein based on the ALP and tyrosinase coupled enzymes-triggered fluorogenic and chromogenic reaction. According to the direct relationship between the activity of ALP/tyrosinase and absorbance/fluorescence intensity of the resultant solution, the proposed enzyme cascade-triggered reaction was utilized for assaying ALP and tyrosinase activity with fluorometric and colorimetric dual-readout signals. Furthermore, such enzyme cascade catalysis process was integrated into the ALP-based cascade enzyme-linked immunosorbent assay with dual-readout signals, resulting in the sensitive detection of cardiac troponin I in diluted serum.
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ANALYTICAL CHEMISTRY
·
2018
·
IF 6.042
Chenyue Zhan,Jiatian Cheng,Bowen Li,Shuailing Huang,Fang Zeng,Shuizhu Wu
Melanoma is a type of highly malignant and metastatic skin cancer, and early detection of melanoma by analyzing the level of its biomarker may decrease the likelihood of mortality. In this study, a fluorescent probe called NBR-AP for detecting tyrosinase (a biomarker of melanoma) has been created by incorporating a hydroxyphenylurea group (as a substrate for the enzyme) onto a fluorescent dye phenoxazine derivative (as an activatable signal reporter). This probe can be activated to generate fluorescence through a tyrosinase-mediated oxidation followed by hydrolysis of the urea linkage. The probe is able to detect the endogenous tyrosinase level in live cells and in zebrafish sensitively and selectively. Moreover, by imaging the tyrosinase activity, NBR-AP has been successfully applied to diagnose the melanoma and its metastasis in xenogeneic mouse models established via subcutaneous injection of B16F10 cells.
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