Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis

Jo, Hyeju; Choi, Minho; Sim, Joo Yong; Liu, Siyuan; Lee, Young Hee; Kim, Youngsoo; Seo, Seung‐Yong; Zhou, Yuanyuan; Lee, Kiho; Kim, Wun-Jae; Hong, Jin Tae; Lee, Heesoon

doi:10.1016/j.bmcl.2017.06.011

Cited by 23 publications

(19 citation statements)

References 33 publications

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“…They bind to the receptors MC1R and EDNRB on the membrane surface of melanocytes, which stimulates intracellular signaling pathways for melanin biosynthesis 5, 14. We asked whether the in vivo outcomes of DACE could be translated into facultative melanogenesis in melanocytes, since DACE inhibits α-MSH-induced melanin pigmentation in B16-F0 cells 26. Upon exposure to α-MSH alone, human epidermal melanocyte (HEM) or melanoma cell lines such as B16-F0 and MNT1 markedly increased intracellular and extracellular levels of melanin pigments (Figure 2A-C).…”

Section: Resultsmentioning

confidence: 99%

“…Diacetylcaffeic acid cyclohexyl ester (DACE, Figure 1A) inhibits melanin production in α-MSH-activated B16-F0 cells and its efficacy is decreased when cyclohexyl ester moiety is replaced by amide groups with a phenyl, piperazine or pyrazole ring 26. In the current study, we evaluated the antimelanogenic activity of DACE in vivo and elucidated its mechanism of action.…”

Section: Introductionmentioning

confidence: 99%

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Nuclear Entry of CRTC1 as Druggable Target of Acquired Pigmentary Disorder

Yun¹,

Hong²,

Lee³

et al. 2019

Theranostics

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Rationale: SOX10 (SRY-related HMG-box 10) and MITF-M (microphthalmia-associated transcription factor M) restrict the expression of melanogenic genes, such as TYR (tyrosinase), in melanocytes. DACE (diacetylcaffeic acid cyclohexyl ester) inhibits melanin production in α-MSH (α-melanocyte stimulating hormone)-activated B16-F0 melanoma cells. In this study, we evaluated the antimelanogenic activity of DACE in vivo and elucidated the molecular basis of its action. Methods: We employed melanocyte cultures and hyperpigmented skin samples for pigmentation assays, and applied chromatin immunoprecipitation, immunoblotting, RT-PCR or siRNA-based knockdown for mechanistic analyses. Results: Topical treatment with DACE mitigated UV-B-induced hyperpigmentation in the skin with attenuated expression of MITF-M and TYR. DACE also inhibited melanin production in α-MSH- or ET-1 (endothelin 1)-activated melanocyte cultures. As a mechanism, DACE blocked the nuclear import of CRTC1 (CREB-regulated co-activator 1) in melanocytes. DACE resultantly inhibited SOX10 induction, and suppressed the transcriptional abilities of CREB/CRTC1 heterodimer and SOX10 at MITF-M promoter, thereby ameliorating facultative melanogenesis. Furthermore, this study unveiled new issues in melanocyte biology that i) KPNA1 (Impα5) escorted CRTC1 as a cargo across the nuclear envelope, ii) SOX10 was inducible in the melanogenic process, and iii) CRTC1 could direct SOX10 induction at the transcription level. Conclusion: We propose the targeting of CRTC1 as a unique strategy in the treatment of acquired pigmentary disorders.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nuclear Entry of CRTC1 as Druggable Target of Acquired Pigmentary Disorder

Yun¹,

Hong²,

Lee³

et al. 2019

Theranostics

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“…Furthermore, the results of KEGG analysis revealed many potential genes from the melanogenesis pathway. At present, many candidate genes in the melanogenesis pathway have already been shown to be related to coat color, including melanocortin 1 receptor (MC1R) (e.g., San-Jose et al, 2017), melanocyte-stimulating hormone (MSH) (e.g., Jo et al, 2017), and microphthalmia-associated transcription factor (MITF) (e.g., Irizarry and Bryden, 2016;Wang et al, 2017;Xia et al, 2017). Here, a series of DEMs whose targets are involved in the melanogenesis pathway were identified (Table 1), including Frizzled-7 (FZD7) and Frizzled-6 (FZD6), which are found in a variety of cancer cells and related to signal transduction (Cao et al, 2017;Liu et al, 2017;Yang et al, 2011;Corda et al, 2017).…”

Section: Resultsmentioning

confidence: 99%

Identification and characterization of microRNAs in white and black coated yak

Basang

Luo

et al. 2018

IJAR

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In this study, we used high-throughput technology to provide the first transcriptome dataset for differentially expressed miRNA in mixed pools of dermis tissue from black- and white-coated yak to research the possible molecular mechanisms of yak coat pigmentation. In this study, 92,636,002 and 95,917,842 clear reads were generated through Illumina paired-end sequencing. A total of 78 differentially expressed miRNAs (DEMs) were identified, including 59 upregulated and 19 downregulated miRNAs in the mixed pools of white-coated yak compared with the mixed pools of black-coated yak. In addition, 3634 genes were predicted as putative targets of DEMs. These DEGs related to 59 GO categories and were enriched in 216 Kyoto Encyclopedia of Genes and Genomes (KEGG) pathways, including melanogenesis and the Wnt signaling pathway. The results of the current study indicated that the coat color of the yak involved the transcriptional regulation process of miRNAs. These results provide helpful data to understand the molecular mechanisms of yak coat pigmentation.

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“…Cellular oxidants of B16 cells were determined by using the dichloro-dihydro-fluorescein diacetate (DCFH-DA) method based on a previous study [6]. Briefly, B16 cells were plated into 96 well plates at a density of 3.0 × 10 4 cells/well and incubated for 24 h. Cells were treated with non-toxic concentrations of the sample and incubated for 24 h. The cells were washed with PBS, pH 7.4, and incubated with 10 µM DCFH-DA (Merck, Kenilworth, NJ, USA) solution for 3 h. The cellular oxidants were determined by fluorescence intensity at 485/535 nm.…”

Section: Cellular Oxidantsmentioning

confidence: 99%

“…In this study, novel effective natural products for hyperpigmentation treatment were elucidated. Several phenolic acids have been identified as having anti-melanogenic properties via the inhibition of tyrosinase, a key enzyme for melanogenesis [4][5][6][7]. In addition, the antioxidant activity of natural compounds was also considered for the protection and treatment of hyperpigmentation [8,9].…”

Section: Introductionmentioning

confidence: 99%

Germinated Riceberry Rice Enhanced Protocatechuic Acid and Vanillic Acid to Suppress Melanogenesis through Cellular Oxidant-Related Tyrosinase Activity in B16 Cells

2020

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The anti-melanogenic bioactivities of phytophenolic compounds have been well recognized. Riceberry rice contains a rich source of phenolic compounds that act as melanin inhibitors through their antioxidant and anti-tyrosinase properties. Germination has been shown to be an effective process to improve targeted phenolic compounds. In this study, germinated riceberry rice extract was tested for antioxidant activity. Total phenolic content was determined while the tyrosinase inhibitory effect was screened by the in vitro mushroom tyrosinase assay. Cytotoxicity of germinated riceberry rice extract was investigated in B16 cells before evaluating its activities on cellular tyrosinase, melanogenesis, melanin excretion, morphological appearance, and cellular oxidants. Germinated riceberry rice extract showed increased potency of antioxidants and was also twice as effective for mushroom tyrosinase inhibition when compared with ungerminated riceberry rice extract. In B16 cells, the extract inhibited cellular tyrosinase, melanogenesis, and cellular oxidants in a dose-dependent manner when compared with untreated cells. Germinated riceberry rice extract also displayed an effect on B16 cells morphology by reducing the number of melanin-containing cells and their dendriticity. Additionally, the germination of riceberry rice dominantly enhanced two phenolic acids, protocatechuic acid and vanillic acid, which have the potential for antioxidant-associated hyperpigmentation control. Thus, the restricted germination of riceberry rice tended to promote protocatechuic acid and vanillic acid, which dominantly displayed antioxidants and tyrosinase-related melanogenic inhibition.Antioxidants 2020, 9, 247 2 of 12 acid, chlorogenic acid, syringic acid, p-coumaric acid, and ferulic acid [10,11] that act as tyrosinase inhibitors. Previously, a suitable germination process promoted both the quantitative and qualitative aspects of these valuable phenolic compounds [12][13][14][15]. In this study, riceberry rice was enhanced for anti-melanogenesis by the germination process. Germinated riceberry rice extract could be further developed as a novel agent for hyperpigmentation control. Materials and Methods Rice GerminationRiceberry rice was obtained from Phayao province, Thailand. A hundred grams of rice were soaked in reverse osmosis water, pH 7.2-7.4 for 1 h. Soaked riceberry rice was germinated in a polyethylene tray (22 × 22 × 5 cm) at room temperature in the dark for 6 h. Subsequently, germinated riceberry rice was lyophilized and then ultracentrifugally powdered. The riceberry rice powder was then sieved through 345 µm and stored at −20 • C until extraction.

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Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis

Cited by 23 publications

References 33 publications

Nuclear Entry of CRTC1 as Druggable Target of Acquired Pigmentary Disorder

Nuclear Entry of CRTC1 as Druggable Target of Acquired Pigmentary Disorder

Identification and characterization of microRNAs in white and black coated yak

Germinated Riceberry Rice Enhanced Protocatechuic Acid and Vanillic Acid to Suppress Melanogenesis through Cellular Oxidant-Related Tyrosinase Activity in B16 Cells

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