Inhibitory effects of naphthols on the activity of mushroom tyrosinase

Lin, Yuan; Hu, Yonghua; Jia, Yu-Long; Li, Zhi-Cong; Guo, Yun-Ji; Chen, Qing‐Xi; Lin, Hetong

doi:10.1016/j.ijbiomac.2012.04.026

Cited by 18 publications

(8 citation statements)

References 31 publications

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“…Kim et al [10] initially characterized the inhibitory effects of GA against mushroom tyrosinase activity and showed that the 50% inhibition concentration for mushroom tyrosinase activity was 3.5 μM, which is less than that of the commercial tyrosinase inhibitor KA (IC 50 = 59.7 μM). It is known that tyrosinase has both monophenolase and diphenolase activity that can catalyze the hydroxylation of a monophenol and the conversion of O ‐diphenol to the corresponding O ‐quinone [21]. In the present study, we used L ‐tyrosine as a substrate to determine the monophenolase activity and L ‐DOPA to test the diphenolase activity.…”

Section: Discussionmentioning

confidence: 99%

In vitro and in vivo studies disclosed the depigmenting effects of gallic acid: A novel skin lightening agent for hyperpigmentary skin diseases

et al. 2013

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Gallic acid (GA) is a phenolic compound, which has been reported to suppress melanogenesis in melanoma cells. However, the molecular mechanism underlying this inhibitory effect was poorly understood. In this article, we revealed that GA down-regulated melanogenic regulatory genes including tyrosinase, tyrosinase related protein-1 (TRP-1), and dopachrome tatamerase (Dct) expression at transcriptional and translational level. In addition, GA effectively suppressed the microphthalmia-associated transcription factor (MITF) expression by down-regulating the cAMP-mediated PKA/CREB signaling cascades. To delineate the inhibition of MITF by GA, the activation of extracellular signal-regulated protein kinase (ERK) and AKT was investigated. GA caused significant increase of ERK and AKT phosphorylation, while ERK (PD98059) or AKT (LY294002) inhibitor prevents their phosphorylation and increased melanin biosynthesis. In addition, pre-treatment of MITF-siRNA significantly reduced melanin production from 100 to 40%, and even decreased into 10% by combination treatment with GA. Furthermore, UVB-induced hyperpigmentation in the mice skin was significantly rescued by topical application of GA for 4 weeks. Immunohistochemical analyses also confirmed that GA significantly inhibited melanin production followed by the down-regulation of MITF, tyrosinase and their regulatory proteins. In addition, when compared with control zebrafish, GA caused a remarkable inhibition on the endogenous pigmentation in the zebrafish. Results presented in this study strongly suggest that GA is an effective de-pigmenting or skin lightening cosmetics for topical application.

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Section: Discussionmentioning

confidence: 99%

In vitro and in vivo studies disclosed the depigmenting effects of gallic acid: A novel skin lightening agent for hyperpigmentary skin diseases

et al. 2013

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“…Except the inhibitors listed above, other compounds have also been registered for their tyrosinase inhibitory activity by different researchers such as: two Keggin-type polyoxometalates containing glycine as potent inorganic reversible inhibitors 429 , cadmium ions with an IC 50 of 2.92 ± 0.16 mM 48 and rifampicin with an IC 50 = 90 ± 0.6 µM 9 as reversible and noncompetitive inhibitors, ammonium tetrathiotungstate 430 , amoxicillin (IC 50 = 9.0 ± 1.8 mM) 431 , mallotophilippen A and B 432 α-naphthol and β-naphthol 433 , red koji extracts (IC 50 of 5.57 mg/mL) 434 and alpha-hydrazinophloretic acid 435 as competitive inhibitors and rottlerin as a mixed inhibitor 432 . Furthermore, n -alkyl sulfates 436 , sericin extracted from tasar silk fiber waste 437 , 2-hydroxy-3-methylcyclopent-2-enone (IC 50 = 721.91 µg mL −1 ) isolated from ribose-histidine Maillard reaction products 438 , three natural compounds from safflower 439 and mimosine 386 and ethylenediamine 440 are other kinds of tyrosinase inhibitors.…”

Section: Other Tyrosinase Inhibitorsmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

780

471

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Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

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“…The diphenolase activity assay was performed as previously reported. 18 The reaction media (3 mL) for activity assay contained 0.5 mM L-DOPA in 50 mM Na 2 HPO 4 −NaH 2 PO 4 buffer (pH 6.8) and 0.1 mL of different concentrations of inhibitor (dissolved in DMSO previously), with L-DOPA used as the substrate. 0.1 mL of the aqueous solution of mushroom tyrosinase was added to the mixture.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…The vertical axis intercept is 1/V m , the slope is K m /V m , and the horizontal axis intercept is −(1/K m ), so that we can obtain the value of K m and V m . 18 Plant Materials and Treatments. Fruits of longan (Dimocarpus longan Lour.)…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…12−16 Therefore, tyrosinase inhibitors have attracted great attention recently, the numbers of which have already been reported so far. Many tyrosinase inhibitors, such as cardol triene, 15 bibenzyl glycosides, 17 naphthols, 18 chlorobenzaldehyde thiosemicarbazones, 19 benzaldehyde thiosemicarbazones, 20 thymol, 21 mimosine tetrapeptides, 22 hydroxyphenolic acids, and its esters, 23 are composed of compounds that are structurally analogous to phenolic substrate.…”

Section: ■ Introductionmentioning

confidence: 99%

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Inhibitory Effects of Propyl Gallate on Tyrosinase and Its Application in Controlling Pericarp Browning of Harvested Longan Fruits

Lin

et al. 2013

J. Agric. Food Chem.

Self Cite

122

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Tyrosinase (EC 1.14.18.1), also known as polyphenol oxidase (PPO), is a key enzyme in pigment biosynthesis of organisms. The inhibitory effects of propyl gallate on the activity of mushroom tyrosinase and effects of propyl gallate on pericarp browning of harvested longan fruits in relation to phenolic metabolism were investigated. The results showed that propyl gallate could potently inhibit diphenolase activity of tyrosinase. The inhibitor concentration leading to 50% activity lost (IC50) was determined to be 0.685 mM. Kinetic analyses showed that propyl gallate was a reversible and mixed type inhibitor on this enzyme. The inhibition constants (K(IS) and K(I)) were determined to be 2.135 and 0.661 mM, respectively. Furthermore, the results also showed that propyl gallate treatment inhibited activities of PPO and POD in pericarp of harvested longan fruits, and maintained higher contents of total phenol and flavonoid of longan pericarp. Moreover, propyl gallate treatment also delayed the increases of browning index and browning degree in pericarp of harvested longan fruits. Therefore, application of propyl gallate may be a promising method for inhibiting tyrosinase activity, controlling pericarp browning, and extending shelf life of harvested longan fruits.

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Inhibitory effects of naphthols on the activity of mushroom tyrosinase

Cited by 18 publications

References 31 publications

In vitro and in vivo studies disclosed the depigmenting effects of gallic acid: A novel skin lightening agent for hyperpigmentary skin diseases

In vitro and in vivo studies disclosed the depigmenting effects of gallic acid: A novel skin lightening agent for hyperpigmentary skin diseases

A comprehensive review on tyrosinase inhibitors

Inhibitory Effects of Propyl Gallate on Tyrosinase and Its Application in Controlling Pericarp Browning of Harvested Longan Fruits

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