scholarly journals Inhibitory and Acceleratory Effects ofInonotus obliquuson Tyrosinase Activity and Melanin Formation in B16 Melanoma Cells

2014 ◽  
Vol 2014 ◽  
pp. 1-11 ◽  
Author(s):  
Zheng-Fei Yan ◽  
Yang Yang ◽  
Feng-Hua Tian ◽  
Xin-Xin Mao ◽  
Yu Li ◽  
...  
Keyword(s):  
Nicotinic Acid ◽  
Therapeutic Agent ◽  
Kojic Acid ◽  
Ethyl Acetate Extract ◽  
Tyrosinase Activity ◽  
Mushroom Tyrosinase ◽  
Melanin Content ◽  
Inonotus Obliquus ◽  
Nmr Data ◽  
Tyrosinase Inhibitors

The aim of the present study is to preliminarily investigate the antimelanogenesis effect ofInonotus obliquusextracts by cell-free mushroom tyrosinase assay. It was found that petroleum ether and n-butanol extracts might contain unknown potential tyrosinase inhibitors, while its ethyl acetate extract might contain some unknown accelerators. Six compounds were isolated and their structures were identified by interpretation of NMR data and nicotinic acid was first discovered inInonotus obliquus. In cells testing, betulin and trametenolic acid decreased tyrosinase activity and melanin content, while inotodiol and lanosterol significantly increased tyrosinase activity and melanin content, showing anAC⁡50of 9.74 and 8.43 μM, respectively. Nicotinie acid, 3β,22,25-trihydroxy-lanosta-8-ene, had a little or no effect on tyrosinase. Betulin exhibited a mode of noncompetitive inhibition with aKI=KISof 0.4 μM on tyrosinase activity showing an IC50of 5.13 μM and being more effective than kojic acid (6.43 μM), and trametenolic acid exhibited a mode of mixed inhibition with aKIof 0.9 μM,KISof 0.5 μM, and anIC50of 7.25 μM. We proposed betulin and trametenolic acid as a new candidate of potent tyrosinase inhibitors and inotodiol and lanosterol as accelerators that could be used as therapeutic agent.

scholarly journals Novel Anti-Melanogenic Compounds, (Z)-5-(Substituted Benzylidene)-4-thioxothiazolidin-2-one Derivatives: In Vitro and In Silico Insights

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4963
Author(s):  
Heejeong Choi ◽  
Il Young Ryu ◽  
Inkyu Choi ◽  
Sultan Ullah ◽  
Hee Jin Jung ◽  
...  
Keyword(s):  
Active Site ◽  
Kojic Acid ◽  
Docking Simulation ◽  
Tyrosinase Activity ◽  
In Vitro Assays ◽  
Mushroom Tyrosinase ◽  
Tyrosinase Inhibitors ◽  
Melanin Contents ◽  
Human Tyrosinase

To confirm that the β-phenyl-α,β-unsaturated thiocarbonyl (PUSTC) scaffold, similar to the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, acts as a core inhibitory structure for tyrosinase, twelve (Z)-5-(substituted benzylidene)-4-thioxothiazolidin-2-one ((Z)-BTTZ) derivatives were designed and synthesized. Seven of the twelve derivatives showed stronger inhibitory activity than kojic acid against mushroom tyrosinase. Compound 2b (IC50 = 0.47 ± 0.97 µM) exerted a 141-fold higher inhibitory potency than kojic acid. Kinetic studies’ results confirmed that compounds 2b and 2f are competitive tyrosinase inhibitors, which was supported by high binding affinities with the active site of tyrosinase by docking simulation. Docking results using a human tyrosinase homology model indicated that 2b and 2f might potently inhibit human tyrosinase. In vitro assays of 2b and 2f were conducted using B16F10 melanoma cells. Compounds 2b and 2f significantly and concentration-dependently inhibited intracellular melanin contents, and the anti-melanogenic effects of 2b at 10 µM and 2f at 25 µM were considerably greater than the inhibitory effect of kojic acid at 25 µM. Compounds 2b and 2f similarly inhibited cellular tyrosinase activity and melanin contents, indicating that the anti-melanogenic effects of both were due to tyrosinase inhibition. A strong binding affinity with the active site of tyrosinase and potent inhibitions of mushroom tyrosinase, cellular tyrosinase activity, and melanin generation in B16F10 cells indicates the PUSTC scaffold offers an attractive platform for the development of novel tyrosinase inhibitors.

scholarly journals Thiopurine Drugs Repositioned as Tyrosinase Inhibitors

2017 ◽  
Author(s):  
Joonhyuck Choi ◽  
You-Mie Lee ◽  
Jun-Goo Jee
Keyword(s):  
Kojic Acid ◽  
Enzyme Assays ◽  
Mushroom Tyrosinase ◽  
Melanin Content ◽  
B16f10 Melanoma ◽  
Chemical Similarity ◽  
Melanin Biosynthesis ◽  
Cell Lysate ◽  
The Us ◽  
Tyrosinase Inhibitors

In this study, we repositioned thiopurine drugs used for the treatment of acute leukaemia as new tyrosinase inhibitors. Tyrosinase catalyses two distinct and successive oxidations in melanin biosynthesis: the conversions of tyrosine to dihydroxyphenylalanine (DOPA) and DOPA to dopaquinone. Continuous efforts are underway to discover small molecule inhibitors of tyrosinase for therapeutic, cosmetic, and agricultural purposes. Structure-based virtual screening has predicted inhibitor candidates for mushroom tyrosinase from drugs approved by the US Food and Drug Administration (FDA). Enzyme assays have confirmed the thiopurine leukaemia drug, thioguanine, as a tyrosinase inhibitor. Two other thiopurine drugs, mercaptopurine and azathioprine, were also evaluated for their tyrosinase inhibitory activity; mercaptopurine caused stronger inhibition than thioguanine did, whereas azathioprine was a poor inhibitor. The inhibitory constants of thioguanine and mercaptopurine were calculated as 52 and 16 µM, respectively, and the value of mercaptopurine was comparable to that of the well-known inhibitor kojic acid (13 µM). The cell lysate and melanin content assay in B16F10 melanoma cells confirmed that the compounds inhibited mammalian tyrosinase. In particular, 50 µM thioguanine reduced the melanin content by 57% without cytotoxicity. Furthermore, the thiopurine drugs shared little chemical similarity with the known tyrosinase inhibitors.

scholarly journals Synthesis of Novel Compounds as New Potent Tyrosinase Inhibitors

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Hooshang Hamidian
Keyword(s):  
Kojic Acid ◽  
Azo Compounds ◽  
The Novel ◽  
Mushroom Tyrosinase ◽  
Reference Standard ◽  
Tyrosinase Inhibition ◽  
H Nmr ◽  
Ft Ir ◽  
Tyrosinase Inhibitors ◽  
C Nmr

In the present paper, we report the synthesis and pharmacological evaluation of a new series of azo compounds with different groups (1-naphthol, 2-naphthol, andN,N-dimethylaniline) and trifluoromethoxy and fluoro substituents in the scaffold. All synthesized compounds (5a–5f) showed the most potent mushroom tyrosinase inhibition (IC50values in the range of 4.39 ± 0.76–1.71 ± 0.49 µM), comparable to the kojic acid, as reference standard inhibitor. All the novel compounds were characterized by FT-IR,1H NMR,13C NMR, and elemental analysis.

scholarly journals The Organogermanium Compound THGP Suppresses Melanin Synthesis via Complex Formation with L-DOPA on Mushroom Tyrosinase and in B16 4A5 Melanoma Cells

2019 ◽  
Vol 20 (19) ◽  
pp. 4785
Author(s):  
Junya Azumi ◽  
Tomoya Takeda ◽  
Yasuhiro Shimada ◽  
Hisashi Aso ◽  
Takashi Nakamura
Keyword(s):  
Gene Expression ◽  
Kojic Acid ◽  
Biological Activities ◽  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Melanin Synthesis ◽  
Mushroom Tyrosinase ◽  
Melanin Production ◽  
Organogermanium Compound ◽  
Or Gene

The organogermanium compound 3-(trihydroxygermyl)propanoic acid (THGP) has various biological activities. We previously reported that THGP forms a complex with cis-diol structures. L-3,4-Dihydroxyphenylalanine (L-DOPA), a precursor of melanin, contains a cis-diol structure in its catechol skeleton, and excessive melanin production causes skin darkening and staining. Thus, the cosmetic field is investigating substances that suppress melanin production. In this study, we investigated whether THGP inhibits melanin synthesis via the formation of a complex with L-DOPA using mushroom tyrosinase and B16 4A5 melanoma cells. The ability of THGP to interact with L-DOPA was analyzed by 1H-NMR, and the influence of THGP and/or kojic acid on melanin synthesis was investigated. We also examined the effect of THGP on cytotoxicity, tyrosinase activity, and gene expression and found that THGP interacted with L-DOPA, a precursor of melanin with a cis-diol structure. The results also showed that THGP inhibited melanin synthesis, exerted a synergistic effect with kojic acid, and did not affect tyrosinase activity or gene expression. These results suggest that THGP is a useful substrate that functions as an inhibitor of melanogenesis and that its effect is enhanced by combination with kojic acid.

scholarly journals ANTI-TYROSINASE ACTIVITY FROM VARIOUS SOLVENTS OF PEANUT SHELL (ARACHIS HYPOGAEA L.) EXTRACTS IN VITRO

2019 ◽  
pp. 150-152
Author(s):  
RISHA FILLAH FITHRIA ◽  
MELLA DWI KRISDIANA ◽  
ETIKA MUSLIMAH ◽  
SARIF MUSYAFA ◽  
NINING SUGIHARTINI
Keyword(s):  
Ethyl Acetate ◽  
Kojic Acid ◽  
Ethyl Acetate Extract ◽  
Ethanol Extract ◽  
Tyrosinase Activity ◽  
Peanut Shell ◽  
Microplate Reader ◽  
Tyrosinase Enzyme ◽  
Better Than

Objective: This study aimed to determine in vitro anti-tyrosinase activity from various solvents of peanut shell extracts and to find out if the activityis better than kojic acid which is a conventional compound used as anti-hyperpigmentation agent.Methods: Extraction was done by maceration method with various solvents of ethyl acetate, n-hexane, and 70% ethanol. Extracts were made into theseries concentration of 25, 50, and 75 μg/ml. Kojic acid with concentration of 50 μg/ml used as positive control and 5% dimethyl sulfoxide used asnegative control. Tyrosinase enzyme will react with L-3,4-dihydroxyphenylalanine substrate to produce dopachrome compound. The absorbance ofdopachrome read by microplate reader at λ = 492 nm. If the absorbance read by the microplate reader is low, means that the inhibition power of thepeanut shell extract against the tyrosinase enzyme is high. Anti-tyrosinase activity seen by the percentage inhibition value. The percentage inhibitionvalue was analyzed with Kruskal–Wallis test followed by Mann–Whitney U-test; all tests were carried out with a confidence level of 95%.Results: The mean of percentage inhibition value of n-hexane extract ranged from 12.44 ± 1.66% to 39.82 ± 1.33%, 70% of ethanol extract rangedfrom 39.98 ± 0.85% to 70.19 ± 1.98%, and ethyl acetate extract ranged from 17.85 ± 0.78% to 60.30 ± 0.97%. Kojic acid has mean percentageinhibition value of 78.19 ± 1.97%. IC50 of ethanol, ethyl acetate, and n-hexane extracts was, respectively, 40.53 μg/ml, 63.49 μg/ml, and 91.95 μg/ml.Ethanol extract contains flavonoid, tannin, and saponin. Ethyl acetate extract contains flavonoid.Conclusion: All various solvents of peanut shell extracts have anti-tyrosinase activity but not better than kojic acid. Ethanol extract with concentrationof 75 μg/ml has the greatest anti-tyrosinase activity.

Anti-Melanogenic Activity of p-Chlorophenyl Benzyl Ether in α-MSH-Induced Mouse Melanoma B16F10 Cells

2019 ◽  
Vol 819 ◽  
pp. 118-123
Author(s):  
Wassana Riam-Amatakun ◽  
Panupan Limpachayaporn ◽  
Jhoan Rhea L. Pizon ◽  
Praneet Opanasopit ◽  
Nopparat Nuntharatanapon
Keyword(s):  
Kojic Acid ◽  
Positive Association ◽  
Inhibitory Effect ◽  
Tyrosinase Activity ◽  
Dependent Manner ◽  
Benzyl Ether ◽  
Melanin Content ◽  
Synthetic Compound ◽  
Melanin Biosynthesis ◽  
B16f10 Cells

Melanin is cutaneous pigment which level of its production determines skin complexion. Overproduction of melanin, frequently promoted by UV rays, results in darkening of the skin. Inhibition of tyrosinase activity, a core component in melanin biosynthesis, is one of the mechanisms of depigmenting agents. Hydroquinone and kojic acid are the examples of well-known whitening agents widely used in both pharmaceutical and cosmetic products. However, their adverse effect issues still needed to be overcome. A recent study showed that p-chlorophenyl benzyl ether (Cl-benz), a new synthetic compound, more strongly inhibited mushroom tyrosinase than kojic acid. In the current study, cytotoxicity, anti-melanogenic activity and anti-tyrosinase activity of Cl-benz were performed in mouse B16F10 melanoma cells compared to kojic acid. After 24 h of treatment on B16F10 cells, the cytotoxicity was not observed with Cl-benz and kojic acid. However, after incubation for 48 h, kojic acid at a concentration of 500 μM reduced cell viability less than 50%, whereas Cl-benz-treated cells showed negligible cytotoxicity. For cell-based assay, Cl-benz exhibited inhibitory effect similar to kojic acid. Melanin production in B16F10 cells was suppressed by Cl-benz in a dose dependent manner. One hundred micrograms of Cl-benz decreased melanin content in α-MSH by 66%. Moreover, the percentage of cellular tyrosinase activity of Cl-benz showed positive association with its corresponding melanin content. These results revealed that Cl-benz could inhibit melanogenesis via the mechanism of cellular tyrosinase inhibition. Accordingly, Cl-benz has potential to become a novel skin whitening agent in terms of efficacy and safety.

Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors

2020 ◽  
Vol 201 ◽  
pp. 112480
Author(s):  
Morteza Ashooriha ◽  
Mehdi Khoshneviszadeh ◽  
Mahsima Khoshneviszadeh ◽  
Alireza Rafiei ◽  
Mostafa Kardan ◽  
...  
Keyword(s):  
Natural Product ◽  
Kojic Acid ◽  
Mushroom Tyrosinase ◽  
Tyrosinase Inhibitors

scholarly journals Electrochemical Screening and Evaluation of Lamiaceae Plant Species from South Africa with Potential Tyrosinase Activity

Sensors ◽  
2019 ◽  
Vol 19 (5) ◽  
pp. 1035 ◽  
Author(s):  
Ninon Etsassala ◽  
Tesfaye Waryo ◽  
Olugbenga Popoola ◽  
Adewale Adeloye ◽  
Emmanuel Iwuoha ◽  
...  
Keyword(s):  
South Africa ◽  
South African ◽  
Kojic Acid ◽  
Screening Method ◽  
Tyrosinase Activity ◽  
Minimum Concentration ◽  
Methanolic Extracts ◽  
Fast Screening ◽  
African Flora ◽  
Tyrosinase Inhibitors

South Africa is a country with a wide variety of plants that may contain excellent anti-tyrosinase inhibitors. With wide applications in cosmetics, pharmaceuticals and food products, tyrosinase inhibitors have received very special attention in the recent past as a way of preventing the overproduction of melanin in epidermal layers which often over time brings detrimental effects on human skin. In this present study, a fast screening method using a cyclic voltammetry technique was applied in the evaluation of methanolic extracts of twenty-five species of plants from the Lamiaceae family for anti-tyrosinase activity. Among these plants, those that showed a fast current inhibition rate at a minimum concentration when compared to a kojic acid standard were classified as having the greatest anti-tyrosinase activity. These include Salvia chamelaeagnea, S. dolomitica, Plectranthus ecklonii, P. namaensis, and P. zuluensis. The results presented herein focused in particular on providng firsthand information for further extensive research and exploration of natural product materials with anti-tyrosinase activity from South African flora for use in cosmetics, skin care and medicinal treatments.

Plants as a Promising Reservoir of Tyrosinase Inhibitors

2020 ◽  
Vol 17 ◽  
Author(s):  
Rabia Riaz ◽  
Paolo Zucca ◽  
Antonio Rescigno ◽  
Stefania Peddio ◽  
Rahman Shah Zaib Saleem ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Secondary Metabolites ◽  
Biosynthetic Pathway ◽  
Kojic Acid ◽  
Structure Optimization ◽  
Tyrosinase Activity ◽  
Plant Origin ◽  
Current Review ◽  
Tyrosinase Inhibitors ◽  
Mechanistic Investigations

Abstract:: The process of melanogenesis, that takes place in the melanocytes of the epidermis, leads to hyperpigmentation. The biosynthetic pathway for production of melanin involves the enzyme tyrosinase that has been an attractive target for cosmaceutical research. Numerous synthetic, semisynthetic and natural, especially plant-based, inhibitors of tyrosinase have been reported in the literature. In plants, the secondary metabolites like flavonoids, chalcones, stilbenes, tannins, hydroquinone and kojic acid, etc... have been shown to possess the anti-tyrosinase activity. In the current review, we have covered the progress in this sphere that would be useful for not only further mechanistic investigations but also for the optimization of the structure of the metabolites for improved activity and selectivity. Thus the review presents a comprehensive report on tyrosinase inhibitors of plant origin reported in the extract form or as isolated compounds. Huge gap has been found between research and industry due to inconsistent pursual of the potent plant based extracts. There is a need to completely evaluate the extracts for structure optimization using molecular docking and evaluation of the safety inorder to benefit the industry with non toxic biological friendly products through invivo and exvivo optimization.

scholarly journals Urea-Extracted Sericin is Potentially Better Than Kojic Acid in the Inhibition of Melanogenesis Through Increased ROS Generation

2020 ◽  
Author(s):  
Sarocha Cherdchom ◽  
Amornpun Sereemasoun ◽  
Pornanong Aramwit
Keyword(s):  
Kojic Acid ◽  
Therapeutic Potential ◽  
Chemical Properties ◽  
Extraction Methods ◽  
Inhibitory Effect ◽  
Biological Properties ◽  
Tyrosinase Activity ◽  
The Other ◽  
Ros Generation ◽  
Melanin Content

Abstract Background: Hyperpigmentation is a skin disorder, which is caused by an excess production of melanin. The reduction in melanin content without causing undesirable effects is required for the treatment of hyperpigmentation. Sericin is increasingly used as a hyperpigmentation treatment because of its antityrosinase activity. However, the various methods of sericin extraction have an effect on the composition and biological properties. The purpose of this study was to investigate the antioxidant and anti-melanogenic properties of sericin using different extraction methods including acid, base, heat, and urea extraction. Methods: The chemical properties of extracted sericin were assessed in terms of amino acid components, thermal behavior, and UV-vis absorption. The inhibitory effects of sericin on melanogenesis were explored by determining the melanin content and cellular tyrosinase activity in B16F10 cells.Results: Sericin from urea extraction provided different properties when compared with the other extraction methods. Our results indicate that urea-extracted sericin reduced the melanin content and cellular tyrosinase activity more effectively than the other extraction methods. Interestingly, the potential anti-melanogenic activity was more effective than kojic acid, a depigmenting agent used to treat hyperpigmentation.Conclusions: Our results present the potential inhibitory effect of urea-extracted sericin on melanogenesis. Our results support the therapeutic potential of urea-extracted sericin in the treatment of hyperpigmentation and its complications.

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