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Antimelanogenic Effect of Purpurogallin in Murine Melanoma Cells
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 Title & Authors
Antimelanogenic Effect of Purpurogallin in Murine Melanoma Cells
Kim, Han-Hyuk; Kim, Tae Hoon;
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 Abstract
Melanin is one of the most important factors affecting skin color. Melanogenesis is the bioprocess of melanin production by melanocytes in the skin and hair follicles and is mediated by several enzymes, such as tyrosinase, tyrosinase related protein (TRP)-1, and TRP-2. Convenient enzymatic transformation of the simple phenol pyrogallol with polyphenol oxidase originating from pear to an oxidative product, purpurogallin, was efficient. The structure of the pyrogallol oxidation product was identified on the basis of spectroscopic methods. The biotransformation product purpurogallin showed significant inhibitory effects against both melanin synthesis and tyrosinase activity in a dose-dependent manner in B16 melanoma cells. In addition, purpurogallin significantly attenuated melanin production by inhibiting TRP-1, and TRP-2 expression through modulation of their corresponding transcription factors, and microphthalamia- associated transcription factor in B16 cells. Consequently, purpurogallin derived from convenient enzymatic transformation of pyrogallol might be a beneficial material for reducing skin hyperpigmentation.
 Keywords
biotransformation;polyphenol oxidase;antimelanogenesis;oxidation product;
 Language
Korean
 Cited by
 References
1.
Agar N, Young AR. 2005. Melanogenesis: a photoprotective response to DNA damage?. Mutat Res 571: 121-132. crossref(new window)

2.
Sanchez-Ferrer A, Rodriguez-Lopez JN, Garcia-Canovas F, Garcia-Carmona F. 1995. Tyrosinase: a comprehensive review of its mechanism. Biochim Biphys Acta 1247: 1-11. crossref(new window)

3.
Hearing VJ. 1999. Biochemical control of melanogenesis and melanosomal organization. J Investig Dermatol Symp Proc 4: 24-28. crossref(new window)

4.
del Marmol V, Beermann F. 1996. Tyrosinase and related proteins in mammalian pigmentation. FEBS Lett 381: 165-168. crossref(new window)

5.
Chakraborty AK, Funasaka Y, Komoto M, Ichihashi M. 1998. Effect of arbutin on melanogenic proteins in human melanocytes. Pigment Cell Res 11: 206-212. crossref(new window)

6.
Curto EV, Kwong C, Hermersdorfer H, Glatt H, Santis C, Virador V, Hearing VJ Jr, Dooley TP. 1992. Inhibitors of mammalian melanocytes tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem Pharmacol 57: 663-672.

7.
Desmedt B, Rogiers V, Courselle P, De Beer JO, De Paepe K, Deconinck E. 2013. Development and validation of a fast chromatographic method for screening and quantification of legal and illegal skin whitening agents. J Pharm Biomed Anal 83: 82-88. crossref(new window)

8.
Li Y, Shibahara A, Matsuo Y, Tanaka T, Kouno I. 2010. Reaction of the black tea pigment theaflavin during enzymatic oxidation of tea catechins. J Nat Prod 73: 33-39. crossref(new window)

9.
Bae JS, Kim TH. 2012. Enzymatic transformation of caffeic acid with enhanced cyclooxygenase-2 inhibitory activity. Bioorg Med Chem Lett 22: 793-796. crossref(new window)

10.
Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. 1987. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res 47: 936-942.

11.
Martinez-Esparza M, Jimenez-Cervantes C, Solano F, Lozano JA, Garcia-Borron JC. 1998. Mechanism of melanogenesis inhibition by tumor necrosis factor-$\alpha$ in B16/F10 mouse melanoma cells. Eur J Biochem 255: 139-146. crossref(new window)

12.
Sies H. 2010. Polyphenols and health: update and perspectives. Arch Biochem Biophys 501: 2-5. crossref(new window)

13.
Yasuda T, Inaba A, Ohmori M, Endo T, Kubo S, Ohsawa K. 2000. Urinary metabolites of gallic acid in rats and their radical-scavenging effects on 1,1-diphenyl-2-picrylhydrazyl radical. J Nat Prod 63: 1444-1446. crossref(new window)

14.
Nonaka GI, Hashimoto F, Nishioka I. 1986. Tannins and related compounds. XXXVI. Isolation and structures of theaflagallins, new red pigments from black tea. Chem Pharm Bull 34: 61-65. crossref(new window)

15.
Park JG, Kramer BS, Steinberg SM, Carmichael J, Collins JM, Minna JD, Gazdar AF. 1987. Chemosensitivity testing of human colorectal carcinoma cell lines using a tetrazolim-based colorimetric assay. Cancer Res 47: 5875-5879.

16.
Kwak JH, Seo UK, Han YH. 2001. Inhibitory effect of mugwort extracts on tyrosinase activity. Korean J Biotechnol Bioeng 16: 220-223.

17.
Huang HC, Chou YC, Wu CY, Chang TM. 2013. [8]-Gingerol inhibits melanogenesis in murine melanoma cells through down-regulation of the MAPK and PKA signal pathways. Biochem Biophys Res Commun 438: 375-381. crossref(new window)

18.
Busca R, Ballotti R. 2000. Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res 13: 60-69. crossref(new window)

19.
Sassone-Corsi P. 1998. Coupling gene expression to cAMP signalling: role of CREB and CREM. Int J Biochem Cell Biol 30: 27-38. crossref(new window)

20.
Li Y, Shibahara A, Matsuo Y, Tanaka T, Kouno I. 2010. Reaction of the black tea pigment theaflavin during enzymatic oxidation of tea catechins. J Nat Prod 73: 33-39. crossref(new window)

21.
Tanaka T, Miyata Y, Tamaya K, Kusano R, Matsuno R, Tamaru S, Tanaka K, Matsui T, Maeda M, Kouno I. 2009. Increase of theaflavin gallates and thearubigins by acceleration of catechin oxidation in a new fermented tea product obtained by the tea-rolling processing of loquat (Eriobotrya japonica) and green tea leaves. J Agric Food Chem 57: 5816-5822. crossref(new window)

22.
Miyata Y, Tamaru S, Tanaka T, Tamaya K, Matsui T, Nagata Y, Tanaka K. 2013. Theaflavins and theasinensin A derived from fermented tea have antiherperglycemic and hypotriacylglycerolemic effects in KK-A(y) mice and Sprague-Dawley rats. J Agric Food Chem 61: 9366-9372. crossref(new window)