Rhododendrol glycosides as stereospecific tyrosinase inhibitors

Iwadate, Takehiro; Nihei, Keiji

doi:10.1016/j.bmc.2015.09.014

Cited by 16 publications

(4 citation statements)

References 41 publications

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“…Rather low IC50 values have been determined also for resveratrol derivatives such as (E)-2,3-bis(4-hydroxyphenyl)acrylonitrile (IC50 = 5.06 μM) [169] and dihydrooxyresveratrol glucosides [170] (Figure 19). As to other natural phenol-inspired synthetic compounds [157][158][159][160][161], the best results have been reported for a carvacrol derivative containing a 3,5-dihydroxyphenyl moiety (IC 50 = 0.0167 µM) [159] ( Figure 19). Good inhibition properties have been exhibited also by some rhododendrol glycosides (IC 50 = 0.56-9.15 µM) [160] and eugenol derivatives (IC 50 ca.…”

Section: Synthetic Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

“…As to other natural phenol-inspired synthetic compounds [157][158][159][160][161], the best results have been reported for a carvacrol derivative containing a 3,5-dihydroxyphenyl moiety (IC 50 = 0.0167 µM) [159] ( Figure 19). Good inhibition properties have been exhibited also by some rhododendrol glycosides (IC 50 = 0.56-9.15 µM) [160] and eugenol derivatives (IC 50 ca. 8 µM) [161] (Figure 19).…”

Section: Synthetic Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

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Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed.

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Section: Synthetic Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

Section: Synthetic Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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“…Between diverse approaches to abnormal melanogenesis, and suppress excessive, tyrosinase inhibition studies have been the most studied. [ 47,48 ]…”

Section: Discussionmentioning

confidence: 99%

Evaluation of in vitro inhibitory effects of some natural compounds on tyrosinase activity and molecular docking study: Antimelanogenesis potential

Taslimi

2020

J Biochem & Molecular Tox

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Tyrosinase enzyme is a functional oxidase that is extensively divided in nature. It is the main enzyme in melanin synthesis and is also involved in designating the color of mammalian hair and skin. Additionally, it is accountable for the unfavorable enzymatic browning that happens in plant‐derived foods, limiting the shelf‐life of new‐cut crops with the resultant economic harm. Recently, there has been a remarkable concern to study the inhibitory activity of the tyrosinase enzyme and some inhibitory molecules isolated from natural sources. For tyrosinase enzyme, afzelin, narcissoside, justiciresinol, thalassiolin B, carpachromene, neobavaisoflavone, and kojic acid (as standard) as natural phenols have IC50 values in the range of 2.37‐7.90 µM. Theoretical methods, such as gaussian software program and molecular modeling, were used to compare the biological and chemical activity values of molecules. To compare the biochemical and chemical activity values of molecules, chemical activities with quantum chemical parameters, and biological activities against tyrosinase with the ID of 5M8L molecules were investigated.

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“…Over the past decade, many efforts have been spent on searching for new and effective tyrosinase inhibitors, and a tremendously large number of naturally occurring and synthetic tyrosinase inhibitors have been reported. [22][23][24][25][26][27][28][29][30][31][32][33][34][35] Unfortunately, only few of them can be used in practice due to the lack of their individual activities or safety concerns. Therefore, more efforts are urgently needed to search and develop new, potent and safe tyrosinase inhibitors with improved therapeutic profiles.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Biological Evaluation and Inhibition Mechanism of 3-/4-Alkoxy Phenylethylidenethiosemicarbazides as New, Potent and Safe Tyrosinase Inhibitors

Song

Mai

Shi

et al. 2020

CHEMICAL & PHARMACEUTICAL BULLETIN

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Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethylidenethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC 50 value below 1 µM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000 µmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure-activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.

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Rhododendrol glycosides as stereospecific tyrosinase inhibitors

Cited by 16 publications

References 41 publications

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Evaluation of in vitro inhibitory effects of some natural compounds on tyrosinase activity and molecular docking study: Antimelanogenesis potential

Design, Synthesis, Biological Evaluation and Inhibition Mechanism of 3-/4-Alkoxy Phenylethylidenethiosemicarbazides as New, Potent and Safe Tyrosinase Inhibitors

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