Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis

Archives of Dermatological Research

Volumn 306, Issue 5, 2014, Pages 475-487

  Park, Jiaa ^a   Park, Joon Heum ^b   Suh, Hwa Jin ^c   Lee, In Chul ^d   Koh, Jaesook ^e   Boo, Yong Chool ^a  

^a Kyungpook National University School of Medicine   (South Korea)

^b Ruby Crown Co Ltd   (South Korea)

^c Gyeongbuk Natural Color Industry Institute   (South Korea)

^d Seowon University   (South Korea)

^e Dermapro Skin Research Center   (South Korea)

Author keywords

Melanin; Oxyresveratrol; Resveratrol; Triacetyl resveratrol; Tyrosinase

Indexed keywords

COSMETIC; MELANIN; MONOPHENOL MONOOXYGENASE; OXYRESVERATROL; PHENOL DERIVATIVE; RESVERATROL; UNCLASSIFIED DRUG; PLANT EXTRACT; PUAG-HAAD; STILBENE DERIVATIVE;

ACETYLATION; ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; CELL LYSATE; CELL VIABILITY; CONTROLLED STUDY; DRUG EFFICACY; DRUG SAFETY; DRUG STABILITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; MELANOCYTE; MELANOGENESIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; ADVERSE EFFECTS; ANIMAL; ANTAGONISTS AND INHIBITORS; BIOLOGICAL MODEL; BIOSYNTHESIS; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; EXPERIMENTAL MELANOMA; FUNCTIONS OF THE SKIN AND ITS APPENDAGES; HEK293 CELL LINE; HYPERPIGMENTATION; SKIN PIGMENTATION; TUMOR CELL LINE; ULTRAVIOLET RADIATION;

ACETYLATION; ANIMALS; CELL LINE, TUMOR; CELL SURVIVAL; HEK293 CELLS; HUMANS; HYPERPIGMENTATION; MELANINS; MELANOMA, EXPERIMENTAL; MICE; MODELS, BIOLOGICAL; MONOPHENOL MONOOXYGENASE; PLANT EXTRACTS; SKIN PHYSIOLOGICAL PHENOMENA; SKIN PIGMENTATION; STILBENES; ULTRAVIOLET RAYS;

EID: 84903739442     PISSN: 03403696     EISSN: 1432069X     Source Type: Journal    
DOI: 10.1007/s00403-014-1440-3     Document Type: Article

References (46)

1. An SM, Kim HJ, Kim JE, Boo YC (2008) Flavonoids, taxifolin and luteolin attenuate cellular melanogenesis despite increasing tyrosinase protein levels. Phytother Res 22:1200-1207
2. An SM, Lee SI, Choi SW, Moon SW, Boo YC (2008) p-Coumaric acid, a constituent of Sasa quelpaertensis Nakai, inhibits cellular melanogenesis stimulated by alpha-melanocyte stimulating hormone. Br J Dermatol 159:292-299 (Pubitemid 352009845)
3. An SM, Koh JS, Boo YC (2009) Inhibition of melanogenesis by tyrosinase siRNA in human melanocytes. BMB Rep 42:178-183
4. An SM, Koh JS, Boo YC (2010) p-Coumaric acid not only inhibits human tyrosinase activity in vitro but also melanogenesis in cells exposed to UVB. Phytother Res 24:1175-1180
5. Busca R, Ballotti R (2000) Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res 13:60-69 (Pubitemid 30324886)
6. Cabanes J, Chazarra S, Garcia-Carmona F (1994) Kojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase. J Pharm Pharmacol 46:982-985
7. Caddeo C, Teskac K, Sinico C, Kristl J (2008) Effect of resveratrol incorporated in liposomes on proliferation and UV-B protection of cells. Int J Pharm 363:183-191
8. Cardinali G, Ceccarelli S, Kovacs D, Aspite N, Lotti LV, Torrisi MR, Picardo M (2005) Keratinocyte growth factor promotes melanosome transfer to keratinocytes. J Invest Dermatol 125:1190-1199
9. Chang TS (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440-2475
10. Costin GE, Hearing VJ (2007) Human skin pigmentation: melanocytes modulate skin color in response to stress. Faseb J 21:976-994
11. Ebanks JP, Wickett RR, Boissy RE (2009) Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration. Int J Mol Sci 10:4066-4087
12. Epstein JH (1983) Photocarcinogenesis, skin cancer, and aging. J Am Acad Dermatol 9:487-502
13. Hsieh TC, Huang YC, Wu JM (2011) Control of prostate cell growth, DNA damage and repair and gene expression by resveratrol analogues, in vitro. Carcinogenesis 32:93-101
14. Kim HJ, An SM, Boo YC (2008) A dual mechanism of 4-hydroxy-5-methyl-3[2H] -furanone inhibiting cellular melanogenesis. J Cosmet Sci 59:117-125
15. Kim M, An SM, Koh JS, Jang DI, Boo YC (2011) Use of nonmelanocytic HEK293 cells stably expressing human tyrosinase for the screening of anti-melanogenic agents. J Cosmet Sci 62:515-523
16. Kim M, Park J, Song K, Kim HG, Koh JS, Boo YC (2012) Screening of plant extracts for human tyrosinase inhibiting effects. Int J Cosmet Sci 34:202-208
17. Kim YJ, Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62:1707-1723
18. Kim YM, Yun J, Lee CK, Lee H, Min KR, Kim Y (2002) Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. J Biol Chem 277:16340-16344 (Pubitemid 34967923)
19. Kwon BS, Haq AK, Pomerantz SH, Halaban R (1987) Isolation and sequence of a cDNA clone for human tyrosinase that maps at the mouse c-albino locus. Proc Natl Acad Sci USA 84:7473-7477 (Pubitemid 18035714)
20. Lebonvallet N, Jeanmaire C, Danoux L, Sibille P, Pauly G, Misery L (2010) The evolution and use of skin explants: potential and limitations for dermatological research. Eur J Dermatol 20:671-684
21. Lee KT, Lee KS, Jeong JH, Jo BK, Heo MY, Kim HP (2003) Inhibitory effects of Ramulus mori extracts on melanogenesis. J Cosmet Sci 54:133-142
22. Lin CB, Babiarz L, Liebel F, Roydon Price E, Kizoulis M, Gendimenico GJ, Fisher DE, Seiberg M (2002) Modulation of microphthalmia-associated transcription factor gene expression alters skin pigmentation. J Invest Dermatol 119:1330-1340 (Pubitemid 36005617)
23. Maeda K, Fukuda M (1996) Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 276:765-769 (Pubitemid 126660519)
24. Newton RA, Cook AL, Roberts DW, Leonard JH, Sturm RA (2007) Post-transcriptional regulation of melanin biosynthetic enzymes by cAMP and resveratrol in human melanocytes. J Invest Dermatol 127:2216-2227 (Pubitemid 47258483)
25. Olivares C, Solano F (2009) New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins. Pigment Cell Melanoma Res 22:750-760
26. Park J, Boo YC (2013) Isolation of resveratrol from vitis viniferae caulis and its potent inhibition of human tyrosinase. Evid Based Complement Alternat Med 2013:645257
27. Park SH, Kim DS, Park SH, Shin JW, Youn SW, Park KC (2008) Inhibitory effect of p-coumaric acid by Rhodiola sachalinensis on melanin synthesis in B16F10 cells. Pharmazie 63:290-295
28. Petrovski G, Gurusamy N, Das DK (2011) Resveratrol in cardiovascular health and disease. Ann N Y Acad Sci 1215:22-33
29. Satooka H, Kubo I (2012) Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor. Bioorg Med Chem 20:1090-1099
30. Schiaffino MV (2010) Signaling pathways in melanosome biogenesis and pathology. Int J Biochem Cell Biol 42:1094-1104
31. Schwahn DJ, Xu W, Herrin AB, Bales ES, Medrano EE (2001) Tyrosine levels regulate the melanogenic response to alpha-melanocyte-stimulating hormone in human melanocytes: implications for pigmentation and proliferation. Pigment Cell Res 14:32-39 (Pubitemid 32228353)
32. Seo YK, Kim SJ, Boo YC, Baek JH, Lee SH, Koh JS (2011) Effects of p-coumaric acid on erythema and pigmentation of human skin exposed to ultraviolet radiation. Clin Exp Dermatol 36:260-266
33. Silva F, Figueiras A, Gallardo E, Nerin C, Domingues FC (2014) Strategies to improve the solubility and stability of stilbene antioxidants: a comparative study between cyclodextrins and bile acids. Food Chem 145:115-125
34. Slominski A, Tobin DJ, Shibahara S, Wortsman J (2004) Melanin pigmentation in mammalian skin and its hormonal regulation. Physiol Rev 84:1155-1228 (Pubitemid 39287950)
35. Solano F, Briganti S, Picardo M, Ghanem G (2006) Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res 19:550-571 (Pubitemid 44674109)
36. Song K, An SM, Kim M, Koh JS, Boo YC (2011) Comparison of the antimelanogenic effects of p-coumaric acid and its methyl ester and their skin permeabilities. J Dermatol Sci 63:17-22
37. Spielmann H (2010) The EU commission's draft report on alternative (Non-animal) methods for cosmetics testing: current status and future prospects-2010: a missed opportunity. Altern Lab Anim 38:339-343
38. Steinhoff M, Stander S, Seeliger S, Ansel JC, Schmelz M, Luger T (2003) Modern aspects of cutaneous neurogenic inflammation. Arch Dermatol 139:1479-1488 (Pubitemid 37433137)
39. Tachibana M (2000) MITF: a stream flowing for pigment cells. Pigment Cell Res 13:230-240
40. Takara K, Iwasaki H, Ujihara K, Wada K (2008) Human tyrosinase inhibitor in rum distillate wastewater. J Oleo Sci 57:191-196
41. Takeyama R, Takekoshi S, Nagata H, Osamura RY, Kawana S (2004) Quercetin-induced melanogenesis in a reconstituted three-dimensional human epidermal model. J Mol Histol 35:157-165 (Pubitemid 40585326)
42. Wichers HJ, Recourt K, Hendriks M, Ebbelaar CE, Biancone G, Hoeberichts FA, Mooibroek H, Soler-Rivas C (2003) Cloning, expression and characterisation of two tyrosinase cDNAs from Agaricus bisporus. Appl Microbiol Biotechnol 61:336-341 (Pubitemid 36683529)
43. Wu JM, Hsieh TC (2011) Resveratrol: a cardioprotective substance. Ann N Y Acad Sci 1215:16-21
44. Yanagihara M, Yoshimatsu M, Inoue A, Kanno T, Tatefuji T, Hashimoto K (2012) Inhibitory effect of gnetin C, a resveratrol dimer from melinjo (Gnetum gnemon), on tyrosinase activity and melanin biosynthesis. Biol Pharm Bull 35:993-996
45. Yasumoto K, Yokoyama K, Takahashi K, Tomita Y, Shibahara S (1997) Functional analysis of microphthalmia-associated transcription factor in pigment cell-specific transcription of the human tyrosinase family genes. J Biol Chem 272:503-509 (Pubitemid 27021187)
46. Yoon TJ, Lei TC, Yamaguchi Y, Batzer J, Wolber R, Hearing VJ (2003) Reconstituted 3-dimensional human skin of various ethnic origins as an in vitro model for studies of pigmentation. Anal Biochem 318:260-269 (Pubitemid 36694118)