Human Skin Lightening Efficacy of Resveratrol and Its Analogs: From in Vitro Studies to Cosmetic Applications
Abstract
:1. Introduction
2. Melanin and Skin Pigmentation Disorders
3. Regulation of Melanin Synthesis
4. Resveratrol: An Antioxidant with Diverse Bioactivities
5. Resveratrol as a Tyrosinase Inhibitor
6. Other Antimelanogenic Mechanisms of Resveratrol and Its Analogs
7. Hypopigmentation Effect of Resveratrol
8. Human Skin Lightening Efficacy of Resveratrol
9. Human Skin Lightening Efficacy of Resveratryl Triacetate (RTA)
10. Human Skin Antiaging Efficacy of Resveratryl Triacetate (RTA)
11. Human Skin Lightening Efficacy of Resveratryl Triglycolate (RTG)
12. Conclusions and Perspectives
Funding
Conflicts of Interest
References
- McLafferty, E.; Hendry, C.; Farley, A. The integumentary system: Anatomy, physiology and function of skin. Nurs. Stand. 2012, 27, 35–42. [Google Scholar] [CrossRef] [PubMed]
- Mayoral, F.A.; Kenner, J.R.; Draelos, Z.D. The skin health and beauty pyramid: A clinically based guide to selecting topical skincare products. J. Drugs Dermatol. 2014, 13, 414–421. [Google Scholar] [PubMed]
- Honigman, R.; Castle, D.J. Aging and cosmetic enhancement. Clin. Interv. Aging 2006, 1, 115–119. [Google Scholar] [CrossRef] [PubMed]
- Ganceviciene, R.; Liakou, A.I.; Theodoridis, A.; Makrantonaki, E.; Zouboulis, C.C. Skin anti-aging strategies. Dermatoendocrinology 2012, 4, 308–319. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Ramos-e-Silva, M.; Celem, L.R.; Ramos-e-Silva, S.; Fucci-da-Costa, A.P. Anti-aging cosmetics: Facts and controversies. Clin. Dermatol. 2013, 31, 750–758. [Google Scholar] [CrossRef] [PubMed]
- Helfrich, Y.R.; Sachs, D.L.; Voorhees, J.J. Overview of skin aging and photoaging. Dermatol. Nurs. 2008, 20, 177–183. [Google Scholar] [PubMed]
- Tsukahara, K.; Sugata, K.; Osanai, O.; Ohuchi, A.; Miyauchi, Y.; Takizawa, M.; Hotta, M.; Kitahara, T. Comparison of age-related changes in facial wrinkles and sagging in the skin of Japanese, Chinese and Thai women. J. Dermatol. Sci. 2007, 47, 19–28. [Google Scholar] [CrossRef] [PubMed]
- Visscher, M.O. Skin Color and Pigmentation in Ethnic Skin. Facial Plast Surg. Clin. N. Am. 2017, 25, 119–125. [Google Scholar] [CrossRef] [PubMed]
- Serre, C.; Busuttil, V.; Botto, J.M. Intrinsic and extrinsic regulation of human skin melanogenesis and pigmentation. Int. J. Cosmet. Sci. 2018, 40, 328–347. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Gunia-Krzyzak, A.; Popiol, J.; Marona, H. Melanogenesis Inhibitors: Strategies for Searching for and Evaluation of Active Compounds. Curr. Med. Chem. 2016, 23, 3548–3574. [Google Scholar] [CrossRef] [PubMed]
- Rauf, A.; Imran, M.; Suleria, H.A.R.; Ahmad, B.; Peters, D.G.; Mubarak, M.S. A comprehensive review of the health perspectives of resveratrol. Food Funct. 2017, 8, 4284–4305. [Google Scholar] [CrossRef] [PubMed]
- Pandey, K.B.; Rizvi, S.I. Plant polyphenols as dietary antioxidants in human health and disease. Oxidat. Med. Cell. Longev. 2009, 2, 270–278. [Google Scholar] [CrossRef] [PubMed]
- Lee, T.H.; Seo, J.O.; Baek, S.H.; Kim, S.Y. Inhibitory effects of resveratrol on melanin synthesis in ultraviolet B-induced pigmentation in Guinea pig skin. Biomol. Ther. 2014, 22, 35–40. [Google Scholar] [CrossRef] [PubMed]
- Wu, Y.; Jia, L.L.; Zheng, Y.N.; Xu, X.G.; Luo, Y.J.; Wang, B.; Chen, J.Z.; Gao, X.H.; Chen, H.D.; Matsui, M.; et al. Resveratrate protects human skin from damage due to repetitive ultraviolet irradiation. J. Eur. Acad. Dermatol. Venereol. 2013, 27, 345–350. [Google Scholar] [CrossRef] [PubMed]
- Ryu, J.H.; Seok, J.K.; An, S.M.; Baek, J.H.; Koh, J.S.; Boo, Y.C. A study of the human skin-whitening effects of resveratryl triacetate. Arch. Dermatol. Res. 2015, 307, 239–247. [Google Scholar] [CrossRef] [PubMed]
- Boo, Y.C. Clinical evaluation of skin whitening effect of a cream containing resveratryl triacetate. Fragr. J. Korea 2016, 2016, 72–79. [Google Scholar]
- Jo, D.J.; Seok, J.K.; Kim, S.Y.; Park, W.; Baek, J.H.; Kim, Y.M.; Boo, Y.C. Human skin-depigmenting effects of resveratryl triglycolate, a hybrid compound of resveratrol and glycolic acid. Int. J. Cosmet. Sci. 2018, 40, 256–262. [Google Scholar] [CrossRef]
- Schiaffino, M.V. Signaling pathways in melanosome biogenesis and pathology. Int. J. Biochem. Cell Biol. 2010, 42, 1094–1104. [Google Scholar] [CrossRef] [Green Version]
- Cardinali, G.; Ceccarelli, S.; Kovacs, D.; Aspite, N.; Lotti, L.V.; Torrisi, M.R.; Picardo, M. Keratinocyte growth factor promotes melanosome transfer to keratinocytes. J. Investig. Dermatol. 2005, 125, 1190–1199. [Google Scholar] [CrossRef]
- Yamaguchi, Y.; Beer, J.Z.; Hearing, V.J. Melanin mediated apoptosis of epidermal cells damaged by ultraviolet radiation: Factors influencing the incidence of skin cancer. Arch. Dermatol. Res. 2008, 300 (Suppl. 1), 43–50. [Google Scholar] [CrossRef]
- Slominski, A.T.; Zmijewski, M.A.; Skobowiat, C.; Zbytek, B.; Slominski, R.M.; Steketee, J.D. Sensing the environment: Regulation of local and global homeostasis by the skin’s neuroendocrine system. Adv. Anat. Embryol. Cell Biol. 2012, 212, 1–115. [Google Scholar]
- Costin, G.E.; Hearing, V.J. Human skin pigmentation: Melanocytes modulate skin color in response to stress. Faseb J. 2007, 21, 976–994. [Google Scholar] [CrossRef] [PubMed]
- Tadokoro, T.; Yamaguchi, Y.; Batzer, J.; Coelho, S.G.; Zmudzka, B.Z.; Miller, S.A.; Wolber, R.; Beer, J.Z.; Hearing, V.J. Mechanisms of skin tanning in different racial/ethnic groups in response to ultraviolet radiation. J. Investig. Dermatol. 2005, 124, 1326–1332. [Google Scholar] [CrossRef] [PubMed]
- Haltaufderhyde, K.D.; Oancea, E. Genome-wide transcriptome analysis of human epidermal melanocytes. Genomics 2014, 104, 482–489. [Google Scholar] [CrossRef] [PubMed]
- Soejima, M.; Koda, Y. Population differences of two coding SNPs in pigmentation-related genes SLC24A5 and SLC45A2. Int. J. Leg. Med. 2007, 121, 36–39. [Google Scholar] [CrossRef] [PubMed]
- Ginger, R.S.; Askew, S.E.; Ogborne, R.M.; Wilson, S.; Ferdinando, D.; Dadd, T.; Smith, A.M.; Kazi, S.; Szerencsei, R.T.; Winkfein, R.J.; et al. SLC24A5 encodes a trans-Golgi network protein with potassium-dependent sodium-calcium exchange activity that regulates human epidermal melanogenesis. J. Biol. Chem. 2008, 283, 5486–5495. [Google Scholar] [CrossRef] [PubMed]
- Cook, A.L.; Chen, W.; Thurber, A.E.; Smit, D.J.; Smith, A.G.; Bladen, T.G.; Brown, D.L.; Duffy, D.L.; Pastorino, L.; Bianchi-Scarra, G.; et al. Analysis of cultured human melanocytes based on polymorphisms within the SLC45A2/MATP, SLC24A5/NCKX5, and OCA2/P loci. J. Investig. Dermatol. 2009, 129, 392–405. [Google Scholar] [CrossRef]
- Slominski, A.; Tobin, D.J.; Shibahara, S.; Wortsman, J. Melanin pigmentation in mammalian skin and its hormonal regulation. Physiol. Rev. 2004, 84, 1155–1228. [Google Scholar] [CrossRef]
- Fistarol, S.K.; Itin, P.H. Disorders of pigmentation. J. Dtsch. Dermatol. Ges. 2010, 8, 187–201. [Google Scholar] [CrossRef]
- Olivares, C.; Solano, F. New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins. Pigment Cell Melanoma Res. 2009, 22, 750–760. [Google Scholar] [CrossRef]
- Simon, J.D.; Peles, D.; Wakamatsu, K.; Ito, S. Current challenges in understanding melanogenesis: Bridging chemistry, biological control, morphology, and function. Pigment Cell Melanoma Res. 2009, 22, 563–579. [Google Scholar] [CrossRef] [PubMed]
- Steinhoff, M.; Stander, S.; Seeliger, S.; Ansel, J.C.; Schmelz, M.; Luger, T. Modern aspects of cutaneous neurogenic inflammation. Arch. Dermatol. 2003, 139, 1479–1488. [Google Scholar] [CrossRef] [PubMed]
- Busca, R.; Ballotti, R. Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res. 2000, 13, 60–69. [Google Scholar] [CrossRef] [PubMed]
- Tachibana, M. MITF: A stream flowing for pigment cells. Pigment Cell Res. 2000, 13, 230–240. [Google Scholar] [CrossRef] [PubMed]
- Ebanks, J.P.; Wickett, R.R.; Boissy, R.E. Mechanisms regulating skin pigmentation: The rise and fall of complexion coloration. Int. J. Mol. Sci. 2009, 10, 4066–4087. [Google Scholar] [CrossRef] [PubMed]
- Xu, W.; Gong, L.; Haddad, M.M.; Bischof, O.; Campisi, J.; Yeh, E.T.; Medrano, E.E. Regulation of microphthalmia-associated transcription factor MITF protein levels by association with the ubiquitin-conjugating enzyme hUBC9. Exp. Cell Res. 2000, 255, 135–143. [Google Scholar] [CrossRef] [PubMed]
- Pillaiyar, T.; Manickam, M.; Jung, S.H. Recent development of signaling pathways inhibitors of melanogenesis. Cell. Signal. 2017, 40, 99–115. [Google Scholar] [CrossRef] [PubMed]
- D’Mello, S.A.; Finlay, G.J.; Baguley, B.C.; Askarian-Amiri, M.E. Signaling Pathways in Melanogenesis. Int. J. Mol. Sci. 2016, 17, 1144. [Google Scholar] [CrossRef] [PubMed]
- Maymone, M.B.C.; Neamah, H.H.; Secemsky, E.A.; Vashi, N.A. Correlating the Dermatology Life Quality Index and Skin Discoloration Impact Evaluation Questionnaire tools in disorders of hyperpigmentation. J. Dermatol. 2018, 45, 361–362. [Google Scholar] [CrossRef]
- Jow, T.; Hantash, B.M. Hydroquinone-induced depigmentation: Case report and review of the literature. Dermatitis 2014, 25, e1–e5. [Google Scholar] [CrossRef]
- Hu, Z.M.; Zhou, Q.; Lei, T.C.; Ding, S.F.; Xu, S.Z. Effects of hydroquinone and its glucoside derivatives on melanogenesis and antioxidation: Biosafety as skin whitening agents. J. Dermatol. Sci. 2009, 55, 179–184. [Google Scholar] [CrossRef] [PubMed]
- Desmedt, B.; Courselle, P.; De Beer, J.O.; Rogiers, V.; Grosber, M.; Deconinck, E.; De Paepe, K. Overview of skin whitening agents with an insight into the illegal cosmetic market in Europe. J. Eur. Acad. Dermatol. Venereol. 2016, 30, 943–950. [Google Scholar] [CrossRef] [PubMed]
- Pillaiyar, T.; Manickam, M.; Namasivayam, V. Skin whitening agents: Medicinal chemistry perspective of tyrosinase inhibitors. J. Enzym. Inhib. Med. Chem. 2017, 32, 403–425. [Google Scholar] [CrossRef] [PubMed]
- Zolghadri, S.; Bahrami, A.; Hassan Khan, M.T.; Munoz-Munoz, J.; Garcia-Molina, F.; Garcia-Canovas, F.; Saboury, A.A. A comprehensive review on tyrosinase inhibitors. J. Enzym. Inhib. Med. Chem. 2019, 34, 279–309. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Nassiri-Asl, M.; Hosseinzadeh, H. Review of the pharmacological effects of Vitis vinifera (Grape) and its bioactive compounds. Phytother. Res. 2009, 23, 1197–1204. [Google Scholar] [CrossRef] [PubMed]
- Koushki, M.; Amiri-Dashatan, N.; Ahmadi, N.; Abbaszadeh, H.A.; Rezaei-Tavirani, M. Resveratrol: A miraculous natural compound for diseases treatment. Food Sci. Nutr. 2018, 6, 2473–2490. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Gu, J.; Hu, W.; Zhang, D.D. Resveratrol, a polyphenol phytoalexin, protects against doxorubicin-induced cardiotoxicity. J. Cell Mol. Med. 2015, 19, 2324–2328. [Google Scholar] [CrossRef] [PubMed]
- Pervaiz, S. Chemotherapeutic potential of the chemopreventive phytoalexin resveratrol. Drug Resist. Updates 2004, 7, 333–344. [Google Scholar] [CrossRef] [PubMed]
- Kovacic, P.; Somanathan, R. Multifaceted approach to resveratrol bioactivity: Focus on antioxidant action, cell signaling and safety. Oxid. Med. Cell. Longev. 2010, 3, 86–100. [Google Scholar] [CrossRef] [PubMed]
- Mahal, H.S.; Mukherjee, T. Scavenging of reactive oxygen radicals by resveratrol: Antioxidant effect. Res. Chem. Intermed. 2006, 32, 59–71. [Google Scholar] [CrossRef]
- Holthoff, J.H.; Woodling, K.A.; Doerge, D.R.; Burns, S.T.; Hinson, J.A.; Mayeux, P.R. Resveratrol, a dietary polyphenolic phytoalexin, is a functional scavenger of peroxynitrite. Biochem. Pharmacol. 2010, 80, 1260–1265. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Yang, H.; Tang, C.Y.; Luo, C.; He, H.X.; Zhou, Y.D.; Yu, W.H. Resveratrol Attenuates the Cytotoxicity Induced by Amyloid-beta(1-42) in PC12 Cells by Upregulating Heme Oxygenase-1 via the PI3K/Akt/Nrf2 Pathway. Neurochem. Res. 2018, 43, 297–305. [Google Scholar]
- Ungvari, Z.; Bagi, Z.; Feher, A.; Recchia, F.A.; Sonntag, W.E.; Pearson, K.; de Cabo, R.; Csiszar, A. Resveratrol confers endothelial protection via activation of the antioxidant transcription factor Nrf2. Am. J. Physiol. Heart Circ. Physiol. 2010, 299, H18–H24. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Li, X.N.; Ma, L.Y.; Ji, H.; Qin, Y.H.; Jin, S.S.; Xu, L.X. Resveratrol protects against oxidative stress by activating the Keap-1/Nrf2 antioxidant defense system in obese-asthmatic rats. Exp. Ther. Med. 2018, 16, 4339–4348. [Google Scholar] [CrossRef] [PubMed]
- Soeur, J.; Eilstein, J.; Lereaux, G.; Jones, C.; Marrot, L. Skin resistance to oxidative stress induced by resveratrol: From Nrf2 activation to GSH biosynthesis. Free Radic Biol. Med. 2015, 78, 213–223. [Google Scholar] [CrossRef]
- Baxter, R.A. Anti-aging properties of resveratrol: Review and report of a potent new antioxidant skin care formulation. J. Cosmet. Dermatol. 2008, 7, 2–7. [Google Scholar] [CrossRef]
- Farris, P.; Krutmann, J.; Li, Y.H.; McDaniel, D.; Krol, Y. Resveratrol: A unique antioxidant offering a multi-mechanistic approach for treating aging skin. J. Drugs Dermatol. 2013, 12, 1389–1394. [Google Scholar]
- Na, J.I.; Shin, J.W.; Choi, H.R.; Kwon, S.H.; Park, K.C. Resveratrol as a Multifunctional Topical Hypopigmenting Agent. Int. J. Mol. Sci. 2019, 20, 956. [Google Scholar] [CrossRef]
- Rabe, J.H.; Mamelak, A.J.; McElgunn, P.J.; Morison, W.L.; Sauder, D.N. Photoaging: Mechanisms and repair. J. Am. Acad. Dermatol. 2006, 55, 1–19. [Google Scholar] [CrossRef]
- Fisher, G.J.; Kang, S.; Varani, J.; Bata-Csorgo, Z.; Wan, Y.; Datta, S.; Voorhees, J.J. Mechanisms of photoaging and chronological skin aging. Arch. Dermatol. 2002, 138, 1462–1470. [Google Scholar] [CrossRef]
- Sardy, M. Role of matrix metalloproteinases in skin ageing. Connect. Tissue Res. 2009, 50, 132–138. [Google Scholar] [CrossRef] [PubMed]
- Dong, K.K.; Damaghi, N.; Picart, S.D.; Markova, N.G.; Obayashi, K.; Okano, Y.; Masaki, H.; Grether-Beck, S.; Krutmann, J.; Smiles, K.A.; et al. UV-induced DNA damage initiates release of MMP-1 in human skin. Exp. Dermatol. 2008, 17, 1037–1044. [Google Scholar] [CrossRef] [PubMed]
- Kim, J.; Oh, J.; Averilla, J.N.; Kim, H.J.; Kim, J.S.; Kim, J.S. Grape Peel Extract and Resveratrol Inhibit Wrinkle Formation in Mice Model Through Activation of Nrf2/HO-1 Signaling Pathway. J. Food Sci. 2019, 84, 1600–1608. [Google Scholar] [CrossRef] [PubMed]
- Gracia-Sancho, J.; Villarreal, G., Jr.; Zhang, Y.; Garcia-Cardena, G. Activation of SIRT1 by resveratrol induces KLF2 expression conferring an endothelial vasoprotective phenotype. Cardiovasc. Res. 2010, 85, 514–519. [Google Scholar] [CrossRef] [PubMed]
- Gertz, M.; Giang, T.T.N.; Fischer, F.; Suenkel, B.; Schlicker, C.; Franzel, B.; Tomaschewski, J.; Aladini, F.; Becker, C.; Wolters, D.; et al. A Molecular Mechanism for Direct Sirtuin Activation by Resveratrol. PLoS ONE 2012, 7, e49761. [Google Scholar] [CrossRef] [PubMed]
- Tian, J.; Chen, J.W.; Gao, J.S.; Li, L.; Xie, X. Resveratrol inhibits TNF-alpha-induced IL-1beta, MMP-3 production in human rheumatoid arthritis fibroblast-like synoviocytes via modulation of PI3kinase/Akt pathway. Rheumatol. Int. 2013, 33, 1829–1835. [Google Scholar] [CrossRef] [PubMed]
- Zhu, X.; Liu, Q.; Wang, M.; Liang, M.; Yang, X.; Xu, X.; Zou, H.; Qiu, J. Activation of Sirt1 by resveratrol inhibits TNF-alpha induced inflammation in fibroblasts. PLoS ONE 2011, 6, e27081. [Google Scholar] [CrossRef] [PubMed]
- Subedi, L.; Lee, T.H.; Wahedi, H.M.; Baek, S.H.; Kim, S.Y. Resveratrol-Enriched Rice Attenuates UVB-ROS-Induced Skin Aging via Downregulation of Inflammatory Cascades. Oxid. Med. Cell. Longev. 2017, 2017, 8379539. [Google Scholar] [CrossRef]
- Abbas, H.; Kamel, R. Potential role of resveratrol-loaded elastic sorbitan monostearate nanovesicles for the prevention of UV-induced skin damage. J. Liposome Res. 2019, 1–9. [Google Scholar] [CrossRef]
- Choi, M.A.; Seok, J.K.; Lee, J.-W.; Lee, S.Y.; Kim, Y.M.; Boo, Y.C. Effects of Resveratrol and Resveratryl Triacetate on The Inflammatory Responses of Human Epidermal Keratinocytes Exposed to Airborne Particulate Matter PM10. J. Soc. Cosmet. Sci. Korea 2018, 44, 249–258. [Google Scholar]
- Pandey, A.K.; Bhattacharya, P.; Shukla, S.C.; Paul, S.; Patnaik, R. Resveratrol inhibits matrix metalloproteinases to attenuate neuronal damage in cerebral ischemia: A molecular docking study exploring possible neuroprotection. Neural. Regen. Res. 2015, 10, 568–575. [Google Scholar] [CrossRef] [PubMed]
- Kim, Y.M.; Yun, J.; Lee, C.K.; Lee, H.; Min, K.R.; Kim, Y. Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. J. Biol. Chem. 2002, 277, 16340–16344. [Google Scholar] [CrossRef] [PubMed]
- Shin, N.H.; Ryu, S.Y.; Choi, E.J.; Kang, S.H.; Chang, I.M.; Min, K.R.; Kim, Y. Oxyresveratrol as the potent inhibitor on dopa oxidase activity of mushroom tyrosinase. Biochem. Biophys. Res. Commun. 1998, 243, 801–803. [Google Scholar] [CrossRef] [PubMed]
- Zheng, Z.P.; Tan, H.Y.; Wang, M. Tyrosinase inhibition constituents from the roots of Morus australis. Fitoterapia 2012, 83, 1008–1013. [Google Scholar] [CrossRef] [PubMed]
- Yokozawa, T.; Kim, Y.J. Piceatannol inhibits melanogenesis by its antioxidative actions. Biol. Pharm. Bull. 2007, 30, 2007–2011. [Google Scholar] [CrossRef] [PubMed]
- Lee, H.S.; Kim, D.H.; Hong, J.E.; Lee, J.Y.; Kim, E.J. Oxyresveratrol suppresses lipopolysaccharide-induced inflammatory responses in murine macrophages. Hum. Exp. Toxicol. 2015, 34, 808–818. [Google Scholar] [CrossRef] [PubMed]
- Choi, H.Y.; Lee, J.H.; Jegal, K.H.; Cho, I.J.; Kim, Y.W.; Kim, S.C. Oxyresveratrol abrogates oxidative stress by activating ERK-Nrf2 pathway in the liver. Chem. Biol. Interact. 2016, 245, 110–121. [Google Scholar] [CrossRef] [PubMed]
- Leu, Y.L.; Hwang, T.L.; Hu, J.W.; Fang, J.Y. Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use. Phytother. Res. 2008, 22, 552–556. [Google Scholar] [CrossRef] [PubMed]
- Yanagihara, M.; Yoshimatsu, M.; Inoue, A.; Kanno, T.; Tatefuji, T.; Hashimoto, K. Inhibitory effect of gnetin C, a resveratrol dimer from melinjo (Gnetum gnemon), on tyrosinase activity and melanin biosynthesis. Biol. Pharm. Bull. 2012, 35, 993–996. [Google Scholar] [CrossRef] [PubMed]
- Lin, Y.S.; Chen, H.J.; Huang, J.P.; Lee, P.C.; Tsai, C.R.; Hsu, T.F.; Huang, W.Y. Kinetics of Tyrosinase Inhibitory Activity Using Vitis vinifera Leaf Extracts. Biomed. Res. Int. 2017, 2017. [Google Scholar] [CrossRef] [PubMed]
- Kwon, B.S.; Haq, A.K.; Pomerantz, S.H.; Halaban, R. Isolation and sequence of a cDNA clone for human tyrosinase that maps at the mouse c-albino locus. Proc. Natl. Acad. Sci. USA 1987, 84, 7473–7477. [Google Scholar] [CrossRef] [PubMed]
- Wichers, H.J.; Recourt, K.; Hendriks, M.; Ebbelaar, C.E.; Biancone, G.; Hoeberichts, F.A.; Mooibroek, H.; Soler-Rivas, C. Cloning, expression and characterisation of two tyrosinase cDNAs from Agaricus bisporus. Appl. Microbiol. Biotechnol. 2003, 61, 336–341. [Google Scholar] [CrossRef] [PubMed]
- Takara, K.; Iwasaki, H.; Ujihara, K.; Wada, K. Human tyrosinase inhibitor in rum distillate wastewater. J. Oleo Sci. 2008, 57, 191–196. [Google Scholar] [CrossRef] [PubMed]
- An, S.M.; Koh, J.S.; Boo, Y.C. p-coumaric acid not only inhibits human tyrosinase activity in vitro but also melanogenesis in cells exposed to UVB. Phytother. Res. 2010, 24, 1175–1180. [Google Scholar] [PubMed]
- Kim, M.; An, S.M.; Koh, J.S.; Jang, D.I.; Boo, Y.C. Use of non-melanocytic HEK293 cells stably expressing human tyrosinase for the screening of anti-melanogenic agents. J. Cosmet. Sci. 2011, 62, 515–523. [Google Scholar] [PubMed]
- Kim, M.; Park, J.; Song, K.; Kim, H.G.; Koh, J.S.; Boo, Y.C. Screening of plant extracts for human tyrosinase inhibiting effects. Int. J. Cosmet. Sci. 2012, 34, 202–208. [Google Scholar] [CrossRef] [PubMed]
- Park, J.; Boo, Y.C. Isolation of resveratrol from vitis viniferae caulis and its potent inhibition of human tyrosinase. Evid. Based Complement. Altern. Med. 2013, 2013, 645257. [Google Scholar] [CrossRef]
- Kwak, J.Y.; Seok, J.K.; Suh, H.J.; Choi, Y.H.; Hong, S.S.; Kim, D.S.; Boo, Y.C. Antimelanogenic effects of luteolin 7-sulfate isolated from Phyllospadix iwatensis Makino. Br. J. Dermatol. 2016, 175, 501–511. [Google Scholar] [CrossRef]
- Boo, Y.C. p-Coumaric Acid as An Active Ingredient in Cosmetics: A Review Focusing on its Antimelanogenic Effects. Antioxidants 2019, 8, 275. [Google Scholar] [CrossRef]
- Bernard, P.; Berthon, J.Y. Resveratrol: An original mechanism on tyrosinase inhibition. Int. J. Cosmet. Sci. 2000, 22, 219–226. [Google Scholar] [CrossRef]
- Gonzalvez, A.G.; Gonzalez Urena, A.; Lewis, R.J.; van der Zwan, G. Spectroscopy and kinetics of tyrosinase catalyzed trans-resveratrol oxidation. J. Phys. Chem. B 2012, 116, 2553–2560. [Google Scholar] [CrossRef] [PubMed]
- Satooka, H.; Kubo, I. Resveratrol as a kcat type inhibitor for tyrosinase: Potentiated melanogenesis inhibitor. Bioorg. Med. Chem. 2012, 20, 1090–1099. [Google Scholar] [CrossRef] [PubMed]
- Ito, S.; Fujiki, Y.; Matsui, N.; Ojika, M.; Wakamatsu, K. Tyrosinase-catalyzed oxidation of resveratrol produces a highly reactive ortho-quinone: Implications for melanocyte toxicity. Pigment. Cell Melanoma Res. 2019. [Google Scholar] [CrossRef] [PubMed]
- Ortiz-Ruiz, C.V.; Ballesta de Los Santos, M.; Berna, J.; Fenoll, J.; Garcia-Ruiz, P.A.; Tudela, J.; Garcia-Canovas, F. Kinetic characterization of oxyresveratrol as a tyrosinase substrate. Iubmb Life 2015, 67, 828–836. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Okura, M.; Yamashita, T.; Ishii-Osai, Y.; Yoshikawa, M.; Sumikawa, Y.; Wakamatsu, K.; Ito, S. Effects of rhododendrol and its metabolic products on melanocytic cell growth. J. Dermatol. Sci. 2015, 80, 142–149. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Park, J.; Park, J.H.; Suh, H.J.; Lee, I.C.; Koh, J.; Boo, Y.C. Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis. Arch. Dermatol. Res. 2014, 306, 475–487. [Google Scholar] [CrossRef] [PubMed]
- Kim, S.Y.; Park, K.C.; Kwon, S.B.; Kim, D.S. Hypopigmentary effects of 4-n-butylresorcinol and resveratrol in combination. Pharmazie 2012, 67, 542–546. [Google Scholar] [PubMed]
- Wang, Y.; Hao, M.M.; Sun, Y.; Wang, L.F.; Wang, H.; Zhang, Y.J.; Li, H.Y.; Zhuang, P.W.; Yang, Z. Synergistic Promotion on Tyrosinase Inhibition by Antioxidants. Molecules 2018, 23, 106. [Google Scholar] [CrossRef]
- Ogas, T.; Kondratyuk, T.P.; Pezzuto, J.M. Resveratrol analogs: Promising chemopreventive agents. Ann. N. Y. Acad. Sci. 2013, 1290, 21–29. [Google Scholar] [CrossRef]
- Pezzuto, J.M.; Kondratyuk, T.P.; Ogas, T. Resveratrol derivatives: A patent review (2009–2012). Expert Opin. Ther. Pat. 2013, 23, 1529–1546. [Google Scholar] [CrossRef]
- Choi, J.; Bae, S.J.; Ha, Y.M.; No, J.K.; Lee, E.K.; Lee, J.S.; Song, S.; Lee, H.; Suh, H.; Yu, B.P.; et al. A newly synthesized, potent tyrosinase inhibitor: 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol. Bioorg. Med. Chem. Lett. 2010, 20, 4882–4884. [Google Scholar] [CrossRef] [PubMed]
- Franco, D.C.; de Carvalho, G.S.; Rocha, P.R.; da Silva Teixeira, R.; da Silva, A.D.; Raposo, N.R. Inhibitory effects of resveratrol analogs on mushroom tyrosinase activity. Molecules 2012, 17, 11816–11825. [Google Scholar] [CrossRef] [PubMed]
- Liu, Q.; Kim, C.; Jo, Y.H.; Kim, S.B.; Hwang, B.Y.; Lee, M.K. Synthesis and Biological Evaluation of Resveratrol Derivatives as Melanogenesis Inhibitors. Molecules 2015, 20, 16933–16945. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Zhu, Y.; Pan, W.H.; Ku, C.F.; Zhang, H.J.; Tsang, S.W. Design, synthesis and evaluation of novel dihydrostilbene derivatives as potential anti-melanogenic skin-protecting agents. Eur. J. Med. Chem. 2018, 143, 1254–1260. [Google Scholar] [CrossRef]
- Fais, A.; Corda, M.; Era, B.; Fadda, M.B.; Matos, M.J.; Quezada, E.; Santana, L.; Picciau, C.; Podda, G.; Delogu, G. Tyrosinase inhibitor activity of coumarin-resveratrol hybrids. Molecules 2009, 14, 2514–2520. [Google Scholar] [CrossRef] [PubMed]
- Park, S.; Seok, J.K.; Kwak, J.Y.; Choi, Y.H.; Hong, S.S.; Suh, H.J.; Park, W.; Boo, Y.C. Anti-melanogenic effects of resveratryl triglycolate, a novel hybrid compound derived by esterification of resveratrol with glycolic acid. Arch. Dermatol. Res. 2016, 308, 325–334. [Google Scholar] [CrossRef] [PubMed]
- Yoon, H.S.; Hyun, C.G.; Lee, N.H.; Park, S.S.; Shin, D.B. Comparative Depigmentation Effects of Resveratrol and Its Two Methyl Analogues in alpha-Melanocyte Stimulating Hormone-Triggered B16/F10 Murine Melanoma Cells. Prev. Nutr. Food Sci. 2016, 21, 155–159. [Google Scholar] [CrossRef]
- Hoek, K.S.; Schlegel, N.C.; Eichhoff, O.M.; Widmer, D.S.; Praetorius, C.; Einarsson, S.O.; Valgeirsdottir, S.; Bergsteinsdottir, K.; Schepsky, A.; Dummer, R.; et al. Novel MITF targets identified using a two-step DNA microarray strategy. Pigment. Cell Melanoma Res. 2008, 21, 665–676. [Google Scholar] [CrossRef]
- Lin, C.B.; Babiarz, L.; Liebel, F.; Roydon Price, E.; Kizoulis, M.; Gendimenico, G.J.; Fisher, D.E.; Seiberg, M. Modulation of microphthalmia-associated transcription factor gene expression alters skin pigmentation. J. Investig. Dermatol. 2002, 119, 1330–1340. [Google Scholar] [CrossRef]
- Hori, Y.S.; Kuno, A.; Hosoda, R.; Horio, Y. Regulation of FOXOs and p53 by SIRT1 modulators under oxidative stress. PLoS ONE 2013, 8, e73875. [Google Scholar] [CrossRef]
- Kwon, S.H.; Choi, H.R.; Kang, Y.A.; Park, K.C. Depigmenting Effect of Resveratrol Is Dependent on FOXO3a Activation without SIRT1 Activation. Int. J. Mol. Sci. 2017, 18, 1213. [Google Scholar] [CrossRef] [PubMed]
- Delmas, D.; Solary, E.; Latruffe, N. Resveratrol, a phytochemical inducer of multiple cell death pathways: Apoptosis, autophagy and mitotic catastrophe. Curr. Med. Chem. 2011, 18, 1100–1121. [Google Scholar] [CrossRef] [PubMed]
- Khandia, R.; Dadar, M.; Munjal, A.; Dhama, K.; Karthik, K.; Tiwari, R.; Yatoo, M.I.; Iqbal, H.M.N.; Singh, K.P.; Joshi, S.K.; et al. A Comprehensive Review of Autophagy and Its Various Roles in Infectious, Non-Infectious, and Lifestyle Diseases: Current Knowledge and Prospects for Disease Prevention, Novel Drug Design, and Therapy. Cells 2019, 8, 674. [Google Scholar] [CrossRef] [PubMed]
- Kim, E.S.; Chang, H.; Choi, H.; Shin, J.H.; Park, S.J.; Jo, Y.K.; Choi, E.S.; Baek, S.Y.; Kim, B.G.; Chang, J.W.; et al. Autophagy induced by resveratrol suppresses alpha-MSH-induced melanogenesis. Exp. Dermatol. 2014, 23, 204–206. [Google Scholar] [CrossRef] [PubMed]
- White, R.; Hanson, G.C.; Hu, F. Tyrosinase maturation and pigment expression in B16 melanoma: Relation to theophylline treatment and intracellular cyclic AMP. J. Cell. Physiol. 1979, 99, 441–450. [Google Scholar] [CrossRef] [PubMed]
- Halaban, R.; Pomerantz, S.H.; Marshall, S.; Lambert, D.T.; Lerner, A.B. Regulation of tyrosinase in human melanocytes grown in culture. J. Cell Biol. 1983, 97, 480–488. [Google Scholar] [CrossRef]
- Newton, R.A.; Cook, A.L.; Roberts, D.W.; Leonard, J.H.; Sturm, R.A. Post-transcriptional regulation of melanin biosynthetic enzymes by cAMP and resveratrol in human melanocytes. J. Investig. Dermatol. 2007, 127, 2216–2227. [Google Scholar] [CrossRef]
- Lei, M.J.; Dong, Y.; Sun, C.X.; Zhang, X.H. Resveratrol inhibits proliferation, promotes differentiation and melanogenesis in HT-144 melanoma cells through inhibition of MEK/ERK kinase pathway. Microb. Pathog. 2017, 111, 410–413. [Google Scholar] [CrossRef]
- Lee, T.H.; Seo, J.O.; Do, M.H.; Ji, E.; Baek, S.H.; Kim, S.Y. Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue. Biomol. Ther. 2014, 22, 431–437. [Google Scholar] [CrossRef] [Green Version]
- Lee, T.H.; Kang, J.H.; Seo, J.O.; Baek, S.H.; Moh, S.H.; Chae, J.K.; Park, Y.U.; Ko, Y.T.; Kim, S.Y. Anti-Melanogenic Potentials of Nanoparticles from Calli of Resveratrol-Enriched Rice against UVB-Induced Hyperpigmentation in Guinea Pig Skin. Biomol. Ther. 2016, 24, 85–93. [Google Scholar] [CrossRef] [Green Version]
- Choi, G.W.; Jeong, H.J.; Sek, J.K.; Baek, J.H.; Kim, Y.M.; Boo, Y.C. Skin Anti-aging Effects of a Cream Containing Resveratryl Triacetate (RTA). J. Soc. Cosmet. Sci. Korea 2018, 44, 161–170. [Google Scholar]
- Pierard, G.E. EEMCO guidance for the assessment of skin colour. J. Eur. Acad. Dermatol. Venereol. 1998, 10, 1–11. [Google Scholar] [CrossRef]
- Silva, F.; Figueiras, A.; Gallardo, E.; Nerin, C.; Domingues, F.C. Strategies to improve the solubility and stability of stilbene antioxidants: A comparative study between cyclodextrins and bile acids. Food Chem. 2014, 145, 115–125. [Google Scholar] [CrossRef] [PubMed]
- Zupancic, S.; Lavric, Z.; Kristl, J. Stability and solubility of trans-resveratrol are strongly influenced by pH and temperature. Eur. J. Pharm. Biopharm. 2015, 93, 196–204. [Google Scholar] [CrossRef] [PubMed]
- Jensen, J.S.; Wertz, C.F.; O’Neill, V.A. Preformulation stability of trans-resveratrol and trans-resveratrol glucoside (Piceid). J. Agric. Food Chem. 2010, 58, 1685–1690. [Google Scholar] [CrossRef] [PubMed]
- Hsieh, T.C.; Huang, Y.C.; Wu, J.M. Control of prostate cell growth, DNA damage and repair and gene expression by resveratrol analogues, in vitro. Carcinogenesis 2011, 32, 93–101. [Google Scholar] [CrossRef] [PubMed]
- Wattanakrai, P.; Suwanachote, S.; Kulkollakarn, S.; Rajatanavin, N. The study of human skin irritation of a novel herbal skin care product and ingredients by human single closed patch testing. J. Med. Assoc. Thai. 2007, 90, 1116–1122. [Google Scholar] [PubMed]
- Loffler, H.; Pirker, C.; Aramaki, J.; Frosch, P.J.; Happle, R.; Effendy, I. Evaluation of skin susceptibility to irritancy by routine patch testing with sodium lauryl sulfate. Eur. J. Dermatol. 2001, 11, 416–419. [Google Scholar] [PubMed]
- Frosch, P.J.; Kligman, A.M. The soap chamber test. A new method for assessing the irritancy of soaps. J. Am. Acad. Dermatol. 1979, 1, 35–41. [Google Scholar] [CrossRef]
- An, S.M.; Ham, H.; Choi, E.J.; Shin, M.K.; An, S.S.; Kim, H.O.; Koh, J.S. Primary irritation index and safety zone of cosmetics: Retrospective analysis of skin patch tests in 7440 Korean women during 12 years. Int. J. Cosmet. Sci. 2014, 36, 62–67. [Google Scholar] [CrossRef]
- Makino, E.T.; Mehta, R.C.; Banga, A.; Jain, P.; Sigler, M.L.; Sonti, S. Evaluation of a hydroquinone-free skin brightening product using in vitro inhibition of melanogenesis and clinical reduction of ultraviolet-induced hyperpigmentation. J. Drugs Dermatol. 2013, 12, s16–s20. [Google Scholar] [PubMed]
- Watanabe, F.; Hashizume, E.; Chan, G.P.; Kamimura, A. Skin-whitening and skin-condition-improving effects of topical oxidized glutathione: A double-blind and placebo-controlled clinical trial in healthy women. Clin. Cosmet. Investig. Dermatol. 2014, 7, 267–274. [Google Scholar] [CrossRef] [PubMed]
- Seo, Y.K.; Kim, S.J.; Boo, Y.C.; Baek, J.H.; Lee, S.H.; Koh, J.S. Effects of p-coumaric acid on erythema and pigmentation of human skin exposed to ultraviolet radiation. Clin. Exp. Dermatol. 2011, 36, 260–266. [Google Scholar] [CrossRef] [PubMed]
- Wilkes, M.; Wright, C.Y.; du Plessis, J.L.; Reeder, A. Fitzpatrick Skin Type, Individual Typology Angle, and Melanin Index in an African Population: Steps Toward Universally Applicable Skin Photosensitivity Assessments. Jama Dermatol. 2015, 151, 902–903. [Google Scholar] [CrossRef] [PubMed]
- Friedman, P.M.; Skover, G.R.; Payonk, G.; Kauvar, A.N.; Geronemus, R.G. 3D in-vivo optical skin imaging for topographical quantitative assessment of non-ablative laser technology. Dermatol. Surg. 2002, 28, 199–204. [Google Scholar] [PubMed]
- Saito, N.; Nishijima, T.; Fujimura, T.; Moriwaki, S.; Takema, Y. Development of a new evaluation method for cheek sagging using a Moire 3D analysis system. Ski. Res. Technol. 2008, 14, 287–292. [Google Scholar] [CrossRef] [PubMed]
- Ryu, H.S.; Joo, Y.H.; Kim, S.O.; Park, K.C.; Youn, S.W. Influence of age and regional differences on skin elasticity as measured by the Cutometer. Ski. Res. Technol. 2008, 14, 354–358. [Google Scholar] [CrossRef]
- Hahn, H.J.; Jung, H.J.; Schrammek-Drusios, M.C.; Lee, S.N.; Kim, J.H.; Kwon, S.B.; An, I.S.; An, S.; Ahn, K.J. Instrumental evaluation of anti-aging effects of cosmetic formulations containing palmitoyl peptides, Silybum marianum seed oil, vitamin E and other functional ingredients on aged human skin. Exp. Ther. Med. 2016, 12, 1171–1176. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Taub, A.; Bucay, V.; Keller, G.; Williams, J.; Mehregan, D. Multi-Center, Double-Blind, Vehicle-Controlled Clinical Trial of an Alpha and Beta Defensin-Containing Anti-Aging Skin Care Regimen With Clinical, Histopathologic, Immunohistochemical, Photographic, and Ultrasound Evaluation. J. Drugs Dermatol. 2018, 17, 426–441. [Google Scholar]
- Tagami, H.; Ohi, M.; Iwatsuki, K.; Kanamaru, Y.; Yamada, M.; Ichijo, B. Evaluation of the skin surface hydration in vivo by electrical measurement. J. Investig. Dermatol. 1980, 75, 500–507. [Google Scholar] [CrossRef]
- de Villiers, M.M.; Narsai, K.; van der Watt, J.G. Physicochemical Stability of Compounded Creams Containing a-Hydroxy Acids. Int. J. Pharm. Compd. 2000, 4, 72–75. [Google Scholar] [PubMed]
- Sharad, J. Glycolic acid peel therapy—A current review. Clin. Cosmet. Investig. Dermatol. 2013, 6, 281–288. [Google Scholar] [CrossRef] [PubMed]
- Jung, H.; Chung, H.; Chang, S.E.; Kang, D.H.; Oh, E.S. FK506 regulates pigmentation by maturing the melanosome and facilitating their transfer to keratinocytes. Pigment Cell Melanoma Res. 2016, 29, 199–209. [Google Scholar] [CrossRef] [PubMed]
- Greatens, A.; Hakozaki, T.; Koshoffer, A.; Epstein, H.; Schwemberger, S.; Babcock, G.; Bissett, D.; Takiwaki, H.; Arase, S.; Wickett, R.R.; et al. Effective inhibition of melanosome transfer to keratinocytes by lectins and niacinamide is reversible. Exp. Dermatol. 2005, 14, 498–508. [Google Scholar] [CrossRef] [PubMed]
- Seiberg, M.; Paine, C.; Sharlow, E.; Andrade-Gordon, P.; Costanzo, M.; Eisinger, M.; Shapiro, S.S. Inhibition of melanosome transfer results in skin lightening. J. Investig. Dermatol. 2000, 115, 162–167. [Google Scholar] [CrossRef]
Literature | Tests | Models | Treatments | Assessments |
---|---|---|---|---|
Lin et al., 2002 [109] | Yucatan swine | Natural pigmentation | 1% Resveratrol | Visual Evaluation |
UV-induced tanning | ||||
Lee et al., 2014 [13] | Guinea pigs | UV-induced tanning | 1% Resveratrol | Instrumental methods |
Visual Evaluation | ||||
Wu et al., 2013 [14] | Humans | UV-induced tanning | 1% Resveratrol | Instrumental methods |
Ryu et al., 2015 [15] | Humans | UV-induced tanning | 0.4% RTA | Instrumental methods |
Natural pigmentation | ||||
Boo, 2016 [16] | Humans | UV-induced tanning | 0.8% RTA | Instrumental methods |
Visual Evaluation | ||||
Ryu et al., 2018 [121] | Humans | Natural pigmentation | 0.8% RTA | Instrumental methods |
Ryu et al., 2018 [17] | Humans | UV-induced tanning | 0.4% RTG | Instrumental methods |
Visual Evaluation |
© 2019 by the author. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Boo, Y.C. Human Skin Lightening Efficacy of Resveratrol and Its Analogs: From in Vitro Studies to Cosmetic Applications. Antioxidants 2019, 8, 332. https://doi.org/10.3390/antiox8090332
Boo YC. Human Skin Lightening Efficacy of Resveratrol and Its Analogs: From in Vitro Studies to Cosmetic Applications. Antioxidants. 2019; 8(9):332. https://doi.org/10.3390/antiox8090332
Chicago/Turabian StyleBoo, Yong Chool. 2019. "Human Skin Lightening Efficacy of Resveratrol and Its Analogs: From in Vitro Studies to Cosmetic Applications" Antioxidants 8, no. 9: 332. https://doi.org/10.3390/antiox8090332