New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins

Olivares, Concepción; Solano, Francisco

doi:10.1111/j.1755-148x.2009.00636.x

Cited by 263 publications

(205 citation statements)

References 129 publications

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“…4 Dopaquinone is highly reactive and can polymerize spontaneously to form melanin in a series of reaction pathways. 5 Therefore, tyrosinase plays an important role in the pigmentation of skin, 6,7 the browning of fruits and vegetables, 8,9 wound healing, 10 and cuticle formation in insects. 11,12 Tyrosinase is also involved in neuromelanin formation in the brain and neurodegeneration associated with Parkinson's disease.…”

Section: Hydroxylation Of L-tyrosine To L-3-(34-dihydroxyphenyl)-alamentioning

confidence: 99%

Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors

Zhao

Zhang

Dong

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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Two groups of novel hydroxypyridinone derivatives 6(a-e) and 12(a-c),were designed as potential tyrosinase inhibitors, and synthesized using kojic acid as a starting material. The tyrosinase inhibitory activity of these two groups was demonstrated to be potent, especially compounds 6e and 12a, whose IC 50 values for monophenolase activity were 1.95 µM and 2.79 µM, respectively. Both of these values are lower than that of kojic acid (IC 50 = 12.50 µM). Compounds 6e and 12a were investigated for the inhibitory effect on diphenolase activity. The results showed that the inhibitory mechanism of these two compounds was reversible and that the inhibitory type was a competitive-uncompetitive mixed-type. The values of IC 50 of 6e and 12a on the diphenolase activity of tyrosinase were determined to be 8.97 µM and 26.20 µM, respectively. The inhibitory constants (K I and K IS ) of 6e were determined as 17.17 µM and 22.09 µM, respectively; and the K I and K IS values of 12a were 34.41 µM and 79.02 µM, respectively. Compound 6e showed a greater ability to reduce copper and a stronger copper chelating ability than kojic acid.

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Section: Hydroxylation Of L-tyrosine To L-3-(34-dihydroxyphenyl)-alamentioning

confidence: 99%

Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors

Zhao

Zhang

Dong

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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“…36 During the melanogenesis, the key enzyme is tyrosinase, which contains a binuclear copper cluster in the common mushroom (Agaricus bisporus) and in human malignant melanoma. 37 The tyrosinase inhibitory activities of RG and FRC are shown in Figure 1.…”

Section: Inhibitiory Activities Against Tyrosinase and Elastasementioning

confidence: 99%

Fermenting Red Ginseng Enhances Its Safety and Efficacy as a Novel Skin Care Anti-Aging Ingredient: In Vitro and Animal Study

Lee

Kim

Park

et al. 2012

Journal of Medicinal Food

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The objective of this study was to evaluate the anti-aging potential and skin safety of red ginseng (RG) and fermented red ginseng (FRG) using Lactobacillus brevis for use as cosmetic ingredients. Concentrations of uronic acid, polyphenols, and flavonoids, and antioxidant activities were greater in FRG compared to RG. The contents of total ginsenosides were not significantly different. However, the ginsenoside metabolite content was higher in FRG (14,914.3 lg/mL) compared to RG (5697.9 lg/mL). The tyrosinase inhibitory activity (IC50) of FRG was 27.63 lg/mL, and more potent compared with RG (34.14 lg/mL), (P < .05). The elastase inhibitory activity (IC50) of FRG was 117.07 lg/mL also higher compared with RG (157.90 lg/mL). In a primary skin irritation test, 10% RG and 10% FRG were classified as practically nonirritating materials. In a skin sensitization test, the RG group showed a sensitization rate of 100% and its mean evaluation score of irritation was 1.4, whereas the FRG group showed 20% and 0.2%, respectively. By fermentation of RG, FRG has increased contents of ginsenoside metabolites, such as Rg3, Rg5, Rk1, compound K, Rh1, F2, Rg2, and flavonoids content. Therefore, FRG offers increased antiwrinkle efficacy, whitening efficacy, and reduced toxicological potency compared to RG.KEY WORDS: cosmeceutical fermented red ginseng red ginseng skin safety

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“…It is well known that tyrosinase is responsible for the pigmentation of skin [11], the browning of fruits and vegetables [12]. Alterations in melanogenesis may be responsible for part of the clinical and histopathological features unique to malignant melanoma, a cancer with a rapidly increasing incidence [13].…”

mentioning

confidence: 99%

Improved antioxidant and anti-tyrosinase activity of polysaccharide from Sargassum fusiforme by degradation

Chen

Shi

Cui

et al. 2016

International Journal of Biological Macromolecules

100

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2 Highlights The degradation conditions of polysaccharide from S. fusiforme has been optimized. The antioxidant activity of the degraded polysaccharides was greatly improved. The degraded polysaccharides possess superior anti-tyrosinase activity.Abstract: An efficient method for the degradation of polysaccharides isolated from Sargassum fusiforme (PSF) was developed by using ascorbic acid in combination with H2O2. The degradation conditions were optimized using a Box-Behnken response surface design (BBRS). The optimum conditions were established as: concentration of ascorbic acid (VC) and H2O2 17.26 mM, degradation temperature 51 o C and degradation time 1.6 h. The DPPH radical scavenging rate of the degraded polysaccharides from S. fusiforme (DPSF) obtained under the optimal conditions was determined to be 75.22±0.02%, which was well matched with the value (75.21%) predicted by the BBRS model. In vitro antioxidant activity of the polysaccharides was evaluated by determining their radical (hydroxyl radical, superoxide anion radical and DPPH radical) scavenging abilities, and ferric iron reducing power. The inhibitory activity on tyrosinase of DPSF was also evaluated. The results indicate that the degraded polysaccharide has superior antioxidant activity and anti-tyrosinase effect to those of the original polysaccharide.

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New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins

Cited by 263 publications

References 129 publications

Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors

Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors

Fermenting Red Ginseng Enhances Its Safety and Efficacy as a Novel Skin Care Anti-Aging Ingredient: In Vitro and Animal Study

Improved antioxidant and anti-tyrosinase activity of polysaccharide from Sargassum fusiforme by degradation

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