Inhibitory effects of 1,3-thiazine derivatives on melanogenesis
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Abstract Objectives The aim of this study was to identify a novel skin-depigmenting agent from synthetic 1,3-thiazine derivatives. Methods We investigated the inhibitory effects of six kinds of 1,3-thiazine derivative on melanogenesis by examining their effects on tyrosinase activity and melanin biosynthesis in melan-a cells and the zebrafish model. Key findings Of the six compounds, 4-hydroxy-2,6-dimethyl-5,6-dihydro-4H-1,3-thiazine (TZ-6) had the strongest anti-melanogenic effects in cultured melan-a cells (30.4% inhibition at 100 μM). In addition, TZ-6 exhibited an inhibitory effect on mushroom and cellular tyrosinase. Based on the results of Western blotting, TZ-6 reduced the expression of tyrosinase at 100 mM. Additionally, TZ-6 reduced body pigmentation and inhibited tyrosinase activity in the zebrafish model. Conclusions The results have provided useful information for the development of a skin whitening agent.Keywords:
Thiazine
Abstract Objectives The aim of this study was to identify a novel skin-depigmenting agent from synthetic 1,3-thiazine derivatives. Methods We investigated the inhibitory effects of six kinds of 1,3-thiazine derivative on melanogenesis by examining their effects on tyrosinase activity and melanin biosynthesis in melan-a cells and the zebrafish model. Key findings Of the six compounds, 4-hydroxy-2,6-dimethyl-5,6-dihydro-4H-1,3-thiazine (TZ-6) had the strongest anti-melanogenic effects in cultured melan-a cells (30.4% inhibition at 100 μM). In addition, TZ-6 exhibited an inhibitory effect on mushroom and cellular tyrosinase. Based on the results of Western blotting, TZ-6 reduced the expression of tyrosinase at 100 mM. Additionally, TZ-6 reduced body pigmentation and inhibited tyrosinase activity in the zebrafish model. Conclusions The results have provided useful information for the development of a skin whitening agent.
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Depigmentation
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Melanin synthesis is regulated by melanogenic proteins, such as tyrosinase, tyrosinase-related protein 1 (TRP-1) and TRP-2. The effects of Hoelen extract on melanogenesis were investigated in B16Fl murine melanoma cells. Specifically, tyrosinase activity, cell viability and melanin content were assayed, and western blotting and RT-PCR for tyrosinase, TRP-1 and TRP-2 conducted. The results show that Hoelen significantly inhibited melanin synthesis through inhibition of TRP-2 expression, while it did not affect tyrosinase activity or its expression. Taken together, RT-PCR results showed that the depigmentation effect of Hoelen may be due to inhibition of TRP-2 gene transcription. These results suggest that Hoelen may be a useful inhibitor for the attenuation of melanogenesis and hyperpigmentation in skin cells.
Microphthalmia-associated transcription factor
Depigmentation
Skin hyperpigmentation
Skin whitening
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Peroxide-dependent enzymic oxidation of tyrosine to dopachrome and melanin was demonstrated in cell-free melanoma homogenates. Histochemical methods for distinguishing peroxidase activity from aerobic dopa (3,4-dihydroxyphenylalanine) oxidase activity are not reliable with cell-free preparations. Therefore the presence of peroxidase activity in such preparations precludes assay of cresolase activity of mammalian ‘tyrosinase’.
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In this study the effects of 6,6’bieckol isolated from Ishige okamurae as a candidate for skin-whitening agent, we evaluated the inhibitory effect on mushroom tyrosinase and αMSH-induced melanin formation inhibitory effect in B16-F10 mouse melanoma cells.6,6’bieckol exhibited more potent tyrosinase inhibitory effect with IC50 value of 1.16μM than arbutin (IC50 = 243.16 μM) and kojic acid (IC50 = 40.28 μM), used as positive controls. Lineweaver-Burk plots suggest that 6,6’bieckol acts as a non-competitive inhibitors. Furthermore, these compounds were evaluated for their inhibitory effect on αMSH -induced melanin formation in B16-F10 mouse melanoma cells. Treatment with 6,6’bieckol (12.5-200 μM) resulted in a significant inhibition of melanin production in melanoma cells. Collectively, these results suggest that 6,6’bieckol might act as a skin-whitening agent via inhibition of tyrosinase activity and melanin formation in B16-F10 mouse melanoma cells.
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Skin whitening
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The purpose of this study was to investigate whitening agent from a natural substance using in vivo model zebrafish. Tyrosinase is a key enzyme in melanogensis which was used for screening of whitening agent with tyrosinase inhibition assay and melanocyte cell melanin biosynthesis inhibition assay. However, pigmentation mechanisms were very a complicated procedure in human dermis. In this study, we used zebrafish embryo as an animal model for confirmed phenotype-based screening of melanin synthesis with natural sources. Zebrafish has most of same organs and tissues that can be seen in human. Especially, pigments were located in the epidermal layer on the surface of organism. In order to examine the whitening effects involved in pigment cell signaling, we treated zebrafish embryos with 10 kinds of methanol extracts of medicinal herbs. Among those medicinal herbs tested, 50 μg/mL of MeOH extract of Forsythia suspensa was decreased the pigmentation on zebrafish larva. After solvent partitioning with MeOH extract of F. suspense , chloroform and ethyl acetate fractions showed the depigmentation effect on zebrafish. In contrast the tyrosinase inhibition effect of F. suspense has not shown. Those results suggest that different approaches to obtain depigmentation process, and confirm the new protocols to evaluate mleanogenesis using in vivo zebrafish model.
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Melanocyte
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Effects of hot-water extract from Sasa quelpaertensis leaf (HWES) on melanogenesis were investigated in B16/F10 mouse melanoma cells. HWES inhibited cellular tyrosinase activity and melanin biosynthesis in a dose-dependent manner. Western blotting analysis showed that HWES dose-dependently inhibited tyrosinase and tyrosinase related protein-1 expression. Also, HWES suppressed sustained ERK activation in a concentration-dependent manner, suggesting that HWES inhibits the melanin biosynthesis through the suppressive effect against pathway involving sustained ERK activation.
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The present study investigates the potent skin whitening ability of ethanol extract from the brown alga, Padina boryana (PBE) which was collected in the shores of Fulhadhoo Island, the Maldives, and its specific pathways of action. The effect of PBE which contains a rich amount of polyphenols was evaluated using B16F10 murine melanoma cells and provides insight to the underlying mechanisms with reference to the inhibition of melanin formation. Melanin synthesis and cellular tyrosinase inhibition were assessed in the α-MSH-stimulated melanocytes. Melanogenic pathway-related protein expressions were investigated via Western blotting. ERK 42/44 was particularly examined considering its involvement in the melanogenic pathway. Further, RT-qPCR techniques were involved in gene expression analysis. PBE dose-dependently inhibited the cellular melanin synthesis and tyrosinase levels. Western blotting revealed the potential of PBE to downregulate microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 and protein-2 (TRP-1 and TRP-2). Moreover, results explained the phosphorylation of ERK was sustained via PBE and hence declined the ultimate melanin synthesis. Gene expression analysis reinforced the results obtained. The study provides substantial evidence to express the potential of PBE to inhibit B16F10 melanoma cell melanin synthesis. Concisely, results suggest the ability of PBE to be involved in medicinal and cosmeceutical applications.
Microphthalmia-associated transcription factor
Skin whitening
Cosmeceuticals
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본 연구는 B16F10 melanoma 세포를 사용하여 도인승기탕의 70% EtOH와 물 추출물의 멜라닌 생합성, tyrosinase 활성, western blotting으로 측정하였다. 도인승기탕 추출물은 농도 의존적으로 멜라닌 생합성과 tyrosinase활성을 저해하였다. 그 결과 도인승기탕 70% 에탄올 추출물이 멜라닌 합성을 40%, tyrosinase는 51% 저해효과를 나타내었다. Western blot을 이용하여 B16F10 melanoma 세포 내에 tyrosinase, TRP-1, TRP-2, MITF의 발현을 억제하는 효과를 관찰하였다. 이상의 결과에 따라 도인승기탕의 70% 에탄올 추출물은 미백 소재로서 가능성을 가지는 것으로 나타났다. This study involved observation of the inhibitory effect of 70% EtOH and water extracts from Doinseunggitang on melanin synthesis, tyrosinase activity, and western blotting using B16F10 melanoma cells. Doinseunggitang extracts inhibited melanin synthesis and tyrosinase activity in a dependent manner. As a result, it was found that Doinseunggitang 70% EtOH extracts inhibit melanin synthesis and tyrosinase activity, respectively, by 40% and 51%. In addition, western blotting analysis showed that 70% EtOH extracts inhibited tyrosinase, MITF, TRP-1, and TRP-2 expression. These results show that 70% ethanol extracts of Doinseunggitang could be developed as a skin whitening material in cosmetics.
Microphthalmia-associated transcription factor
Skin whitening
Northern blot
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