THE RECENT UPDATE OF DEOXYARBUTIN: A SKIN DEPIGMENTATION AGENT WITH TYROSINASE INHIBITION TARGETING
DOI:
https://doi.org/10.22159/ijap.2020v12i3.36957Keywords:
Melanin, Deoxyarbutin, Tyrosinase inhibitor, Skin depigmenting agentAbstract
Melanin is produced through the process of melanogenesis, which serves to protect the skin from the damaging effects of UV radiation. Abnormal accumulation of melanin will aesthetically disturb even interfere with health. One of the clinical manifestations of abnormal accumulation of melanin is the incidence of melasma. Some of the tyrosinase enzyme inhibitor agents most widely used as Hydroquinone, Kojic acid and Arbutin do not give satisfactory results and cause serious side effects. Hydroquinone is known to cause ochronosis exogenous and cytotoxic. Kojic acid is known to cause allergies and mutagenic, while arbutinisis is known to have cytotoxic properties lower than hydroquinone, but less satisfactory depigmentation activity. There was a compound that has been synthesized by removing the hydroxy group of arbutin, known as deoxyarbutin (4-[Tetrahydro-2H-Pyrans-2-yl) oxy] phenol). Deoxyarbutin (dA) shows Ki 10-fold is lower than hydroquinone and 350-fold is lower than arbutin. IC50dA is 17.5+0.5 µmol/l, while the IC50 hydroquinone is 73.7+9.1 µmol/l. In terms of security, dA indicates that cell viability is 95% higher than hydroquinone. However, dA is thermolabile and photolabile. Several studies have shown satisfactory results to improve the stability of dA, that these compounds are considerable potential for further development as a depigmentation agent. The aim of this review is to describe how the potency of dA as a tyrosinase inhibitor interferes melanogenesis process through the latest depigmentation agent, its safety, efficacy and stability.
Downloads
References
Ali SA, Naaz I. Biochemical aspects of mammalian melanocytes and the emerging role of melanocyte stem cells in dermatological therapies. Int J Health Sci 2018;12:69-76.
Mahanty S, Kawali AA, Dakappa SS, Mahendradas P, Kurian M, Kharbanda V, et al. Aqueous humor tyrosinase activity is indicative of iris melanocyte toxicity. Exp Eye Res 2017;162:79-85.
Zhang Y, Helke KL, Coelho SG, Valencia JC, Hearing VJ, Sun S, et al. Essential role of the molecular chaperone gp96 in regulating melanogenesis. Pigment Cell Melanoma Res 2014;27:82-9.
Ando H, Niki Y, Ito M, Akiyama K, Matsui MS, Yarosh DB, et al. Melanosomes are transferred from melanocytes to keratinocytes through the processes of packaging, release, uptake, and dispersion. J Invest Dermatol 2012;132:1222-9.
Cichorek M, Wachulska M, Stasiewicz A, Tymińska A. Skin melanocytes: biology and development. Postepy Dermatologii I Alergologii 2013;30:30-41.
Serre C, Busuttil V, Botto JM. Intrinsic and extrinsic regulation of human skin melanogenesis and pigmentation. Int J Cosmet Sci 2018;40:328-47.
Scott G. Demonstration of melanosome transfer by a shedding microvesicle mechanism. J Invest Dermatol 2012;132:1073-4.
Coelho SG, Yin L, Smuda C, Mahns A, Kolbe L, Hearing VJ. Photobiological implications of melanin photoprotection after UVB-induced tanning of human skin but not UVA-induced tanning. Pigment Cell Melanoma Res 2015;28:210-6.
D'Orazio J, Jarrett S, Amaro Ortiz A, Scott T. UV radiation and the skin. Int J Mol Sci 2013;14:12222-48.
Abdassah M, Aryani R, Surachman E, Muchtaridi M. In vitro assessment of effectiveness and photostability avobenzone in cream formulations by combination ethyl ascorbic acid and alpha tocopherol acetate. J Appl Pharm Sci 2015;5:70-4.
Pillaiyar T, Manickam M, Namasivayam V. Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors. J Enzyme Inhib Med Chem 2017;32:403-25.
Zaidi KU, Ali AS, Ali SA, Naaz I. Microbial tyrosinases: promising enzymes for pharmaceutical, food bioprocessing, and environmental industry. Biochem Res Int 2014. p. 16. https://doi.org/10.1155/2014/854687
Bang E, Noh SG, Ha S, Jung HJ, Kim DH, Lee AK, et al. Evaluation of the novel synthetic tyrosinase inhibitor (Z)-3-(3-bromo-4-hydroxybenzylidene) thiochroman-4-one (MHY1498) in vitro and in silico. Molecules (Basel, Switzerland) 2018;23:3307.
Singh BK, Park SH, Lee HB, Goo YA, Kim HS, Cho SH, et al. Kojic acid peptide: a new compound with anti-tyrosinase potential. Annals Dermatol 2016;28:555-61.
Slominski A, Zmijewski MA, Pawelek J. L-tyrosine and L-dihydroxyphenylalanine as hormone-like regulators of melanocyte functions. Pigment Cell Melanoma Res 2012;25:14-27.
Pająk M, Pałka K, Winnicka E, Kańska M. The chemo-enzymatic synthesis of labeled l-amino acids and some of their derivatives. J Radioanal Nucl Chem 2018;317:643-66.
Araji S, Grammer TA, Gertzen R, Anderson SD, Mikulic Petkovsek M, Veberic R, et al. Novel roles for the polyphenol oxidase enzyme in secondary metabolism and the regulation of cell death in walnut. Plant Physiol 2014;164:1191-203.
Sugumaran M. Reactivities of quinone methides versus o-quinones in catecholamine metabolism and eumelanin biosynthesis. Int J Mol Sci 2016;17:1576.
Klopcic I, Sollner Dolenc M. Chemicals and drugs forming reactive quinone and quinone imine metabolites. Chem Res Toxicol 2018;32. Doi: 10.1021/acs.chemrestox.8b00213
Videira IFdS, Moura DFL, Magina S. Mechanisms regulating melanogenesis. An Bras Dermatol 2013;88:76-83.
Vandecasteele SJ, De Ceulaer J, Wittouck E. Tigecycline induced hyperpigmentation of the skin. Open Forum Infect Dis 2016;3:33-9.
Yamaguchi Y, Hearing VJ. Physiological factors that regulate skin pigmentation. BioFactors (Oxford, England) 2009;35:193-9.
Vandecasteele SJ, De Ceulaer J, Wittouck E. Tigecycline induced hyperpigmentation of the skin. Open Forum Infect Dis 2016;3:ofw033-ofw033.
D'Mello SAN, Finlay GJ, Baguley BC, Askarian-Amiri ME. Signaling pathways in melanogenesis. Int J Mol Sci 2016;17:1144.
Wang Y, Hao MM, Sun Y, Wang LF, Wang H, Zhang YJ, et al. Synergistic promotion on tyrosinase inhibition by antioxidants. Molecules (Basel, Switzerland) 2018;23:106.
Alam MB, Bajpai VK, Lee J, Zhao P, Byeon JH, Ra JS, et al. Inhibition of melanogenesis by jineol from scolopendra subspinipes mutilans via MAP-Kinase mediated MITF downregulation and the proteasomal degradation of tyrosinase. Sci Reports 2017;7:45858.
Cho BR, Jun HJ, Thach TT, Wu C, Lee SJ. Betaine reduces cellular melanin content via suppression of microphthalmia-associated transcription factor in B16-F1 murine melanocytes. Food Sci Biotechnol 2017;26:1391-7.
Chen WC, Tseng TS, Hsiao NW, Lin YL, Wen ZH, Tsai CC, et al. Discovery of highly potent tyrosinase inhibitor, T1, with significant anti-melanogenesis ability by zebrafish in vivo assay and computational molecular modeling. Sci Rep 2015;5:7995.
Rizwana K, Naveed A. Evaluation of depegmenting and antierythemic effects of cosmetic emulgels containing raspberry fruit extract on human cheek skin. Int J Pharm Pharm Sci 2016;9:236-8.
Lee YS, Park JH, Kim MH, Seo SH, Kim HJ. Synthesis of tyrosinase inhibitory kojic acid derivative. Arch Pharm (Weinheim) 2006;339:111-4.
Saeedi M, Eslamifar M, Khezri K. Kojic acid applications in cosmetic and pharmaceutical preparations. Biomed Pharmacother 2019;110:582-93.
Lajis AFB, Hamid M, Ariff AB. Depigmenting effect of Kojic acid esters in hyperpigmented B16F1 melanoma cells. J Biomed Biotechnol 2012. Doi:10.1155/2012/952452
Burnett CL, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler DC, et al. Final report of the safety assessment of kojic acid as used in cosmetics. Int J Toxicol 2010;29:244S-273S.
Chang TS. Natural melanogenesis inhibitors are acting through the down-regulation of tyrosinase activity. Materials 2012;5:1661-85.
Chawla S, deLong MA, Visscher MO, Wickett RR, Manga P, Boissy RE. Mechanism of tyrosinase inhibition by deoxy arbutin and its second-generation derivatives. Br J Dermatol 2008;159:1267-74.
Tada M, Kohno M, Niwano Y. Alleviation effect of arbutin on oxidative stress generated through tyrosinase reaction with L-tyrosine and L-DOPA. BMC Biochem 2014;15:23-3.
Garcia Jimenez A, Teruel Puche JA, Berna J, Rodriguez Lopez JN, Tudela J, Garcia Canovas F. Action of tyrosinase on alpha and beta-arbutin: a kinetic study. PloS One 2017;12:e0177330-e0177330.
Lee SY, Baek N, Nam TG. Natural, semisynthetic and synthetic tyrosinase inhibitors. J Enzyme Inhibition Med Chem 2016;31:1-13.
Ni-Komatsu L, Tong C, Chen G, Brindzei N, Orlow SJ. Identification of quinolines that inhibit melanogenesis by altering tyrosinase family trafficking. Mol Pharmacol 2008;74:1576-86.
Palumbo A, d'Ischia M, Misuraca G, Prota G. Mechanism of inhibition of melanogenesis by hydroquinone. Biochim Biophys Acta 1991;1073:85-90.
Al-Saleh I, Elkhatib R, Al-Rouqi R, Al-Enazi S, Shinwari N. The dangers of skin-lightening creams. Toxicol Environ Chem 2012;94:195-219.
Westerhof W, Kooyers TJ. Hydroquinone and its analogues in dermatology-a potential health risk. J Cosmet Dermatol 2005;4:55-9.
Hutt AM, Kalf GF. Inhibition of human DNA topoisomerase II by hydroquinone and p-benzoquinone, reactive metabolites of benzene. Environ Health Perspect 1996;104 Suppl 6:1265-9.
DeCaprio AP. The toxicology of hydroquinone--relevance to occupational and environmental exposure. Crit Rev Toxicol 1999;29:283-330.
McGregor D. Hydroquinone: an evaluation of the human risks from its carcinogenic and mutagenic properties. Crit Rev Toxicol 2007;37:887-914.
Loizzo MR, Tundis R, Menichini F. Natural and synthetic tyrosinase inhibitors as antibrowning agents: an update. Compr Rev Food Sci Food Saf 2012;11:378-98.
Chen CY, Kuo PL, Chen YH, Huang JC, Ho ML, Lin RJ, et al. Tyrosinase inhibition, free radical scavenging, antimicroorganism and anticancer proliferation activities of Sapindus mukorossi extracts. J Taiwan Institute Chem Eng 2010;41:129-35.
Nisakorn S, Anongnuch T, Ampa J, Krisada K. Anti-tyrosinase and cytotoxicity activities of curcumin-metal complexes. Int J Pharm Pharm Sci 1970;6:270-3.
Ruksiriwanich W, Sringarm K, Jantrawut P. Stability enhancement of celastrus paniculatus seed oil by loading in niosomes. Asian J Pharm Clin Res 2014;7:186-91.
Senol FS, Orhan I, Yilmaz G, Cicek M, Sener B. Acetylcholinesterase, butyrylcholinesterase, and tyrosinase inhibition studies and antioxidant activities of 33 scutellaria L. taxa from turkey. Food Chem Toxicol 2010;48:781-8.
Wangthong S, Palaga T, Rengpipat S, Wanichwecharungruang SP, Chanchaisak P, Heinrich M. Biological activities and safety of thanaka (Hesperethusa crenulata) stem bark. J Ethnopharmacol 2010;132:466-72.
Joy D, Kumar K, Kumar B, Silvipriya K. Collagen from squid and its biological activity. Int J Curr Pharm Res 2017;9:24-6.
Nordlund JJ, Grimes PE, Ortonne JP. The safety of hydroquinone. J Eur Acad Dermatol Venereol 2006;20:781-7.
Migas P, Krauze Baranowska M. The significance of arbutin and its derivatives in therapy and cosmetics. Phytochem Lett 2015;13:35-40.
Noh JM, Kwak SY, Kim DH, Lee YS. Kojic acid-tripeptide amide as a new tyrosinase inhibitor. Biopolymers 2007;88:300-7.
Saruno R, Kato F, Ikeno T. Kojic Acid, a tyrosinase inhibitor from aspergillus albus. Agric Biol Chem 1979;43:1337-8.
Hashemi SM, Emami S. Kojic acid-derived tyrosinase inhibitors: synthesis and bioactivity. Pharm Biomed Res 2015;1:1-17.
Azami F, Tazikeh Lemeski E, Mahmood Janlou MA. Kojic acid effect on the inhibitory potency of tyrosinase. J Chem Health Risks 2017;7. Doi:10.22034/JCHR.2017.544176
Nakagawa M, Kawai K, Kawai K. Contact allergy to kojic acid in skin care products. Contact Dermatitis 1995;32:9-13.
Ando H, Matsui MS, Ichihashi M. Quasi-drugs developed in Japan for the prevention or treatment of hyperpigmentary disorders. Int J Mol Sci 2010;11:2566-75.
Mann T, Gerwat W, Batzer J, Eggers K, Scherner C, Wenck H, et al. Inhibition of human tyrosinase requires molecular motifs distinctively different from mushroom tyrosinase. J Invest Dermatol 2018;138:1601-8.
Sugimoto K, Nishimura T, Nomura K, Sugimoto K, Kuriki T. Inhibitory effects of alpha-arbutin on melanin synthesis in cultured human melanoma cells and a three-dimensional human skin model. Biol Pharm Bull 2004;27:510-4.
Hamed SH, Sriwiriyanont P, deLong MA, Visscher MO, Wickett RR, Boissy RE. Comparative efficacy and safety of deoxyarbutin, a new tyrosinase-inhibiting agent. J Cosmet Sci 2006;57:291-308.
Boissy RE, Visscher M, DeLong MA. DeoxyArbutin: a novel reversible tyrosinase inhibitor with effective in vivo skin lightening potency. Exp Dermatol 2005;14:601-8.
Chandrashekar B, Chaithra S, Lakshmi NN. Effectiveness and safety of a novel topical depigmenting agent in epidermal pigmentation: an open-label, non-comparative study. Int J Res Dermatol 2018;4:489-94.
Liu CQ, Deng L, Zhang P, Zhang SR, Liu L, Xu T, et al. Screening of high alpha-arbutin producing strains and production of alpha-arbutin by fermentation. World J Microbiol Biotechnol 2013;29:1391-8.
Seo DH, Jung JH, Lee JE, Jeon EJ, Kim W, Park CS. Biotechnological production of arbutins (alpha-and beta-arbutins), skin-lightening agents, and their derivatives. Appl Microbiol Biotechnol 2012;95:1417-25.
Lim YJ, Lee EH, Kang TH, Ha SK, Oh MS, Kim SM, et al. Inhibitory effects of arbutin on melanin biosynthesis of alpha-melanocyte stimulating hormone-induced hyperpigmentation in cultured brownish guinea pig skin tissues. Arch Pharm Res 2009;32:367-73.
Gillbro JM, Olsson MJ. The melanogenesis and mechanisms of skin-lightening agents--existing and new approaches. Int J Cosmet Sci 2011;33:210-21.
Numata T, Tobita R, Tsuboi R, Okubo Y. Contact dermatitis caused by arbutin contained in skin-whitening cosmetics. Contact Dermatitis 2016;75:187-8.
Oiso N, Tatebayashi M, Hoshiyama Y, Kawada A, Allergic contact dermatitis caused by arbutin and dipotassium glycyrrhizate in skin-lightening products. Contact Dermatitis 2017;77:51-3.
Matsuo Y, Ito A, Masui Y, Ito M. A case of allergic contact dermatitis caused by arbutin. Contact Dermatitis 2015;72:404-5.
Matsuo Y, Ito A, Masui Y, Ito M. A case of allergic contact dermatitis caused by arbutin. Contact Dermatitis 2015;72:404-5.
Martin C, Portet C, Bantz P, Brun JP, Ruperti A, Mallet MN, et al. [Pharmacokinetics and tissue penetration of single-dose netilmicin used for antibiotic prophylaxis during colo-rectal surgery]. Pathol Biol (Paris) 1991;39:507-10.
Yang CH, Chang NF, Chen YS, Lee SM, Lin PJ, Lin CC. Comparative study on the photostability of arbutin and deoxy arbutin: sensitivity to ultraviolet radiation and enhanced photostability by the water-soluble sunscreen, benzophenone-4. Biosci Biotechnol Biochem 2013;77:1127-30.
Sauriasari R, Azizah N, Basah K. Tyrosinase inhibition, 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, and phytochemical screening of fractions and ethanol extract from leaves and stem bark of matoa (Pometia pinnata). Asian J Pharm Clin Res 2017;10:85-9.
Hirobe T. Keratinocytes regulate the function of melanocytes. Dermatol Sinica 2014;32:200-4.
Nishimura EK. Melanocyte stem cells: a melanocyte reservoir in hair follicles for hair and skin pigmentation. Pigment Cell Melanoma Res 2011;24:401-10.
Tachibana M. Sound needs sound melanocytes to be heard. Pigment Cell Res 1999;12:344-54.
Steel KP, Barkway C. Another role for melanocytes: their importance for normal stria vascularis development in the mammalian inner ear. Development 1989;107:453-63.
Vashi NA, Kundu RV. Facial hyperpigmentation: causes and treatment. Br J Dermatol 2013;169 Suppl 3:41-56.
Bae Harboe YSC, Park HY. Tyrosinase: a central regulatory protein for cutaneous pigmentation. J Investigative Dermatol 2012;132:2678-80.
Uchida R, Ishikawa S, Tomoda H. Inhibition of tyrosinase activity and melanine pigmentation by 2-hydroxytyrosol. Acta Pharm Sinica B 2014;4:141-5.
Ito S, A chemist's view of melanogenesis. Pigment Cell Res 2003;16:230-6.
Kobayashi T, Urabe K, Winder A, Jimenez Cervantes C, Imokawa G, Brewington T, et al. Tyrosinase related protein 1 (TRP1) functions as a DHICA oxidase in melanin biosynthesis. EMBO J 1994;13:5818-25.
Chen H, Weng QY, Fisher DE. UV signaling pathways within the skin. J Invest Dermatol 2014;134:2080-5.
Li PH, Liu LH, Chang CC, Gao R, Leung CH, Ma DL, et al. Silencing stem cell factor gene in fibroblasts to regulate paracrine factor productions and enhance c-kit expression in melanocytes on melanogenesis. Int J Mol Sci 2018;19:1475.
Hsiao JJ, Fisher DE. The roles of microphthalmia-associated transcription factor and pigmentation in melanoma. Arch Biochem Biophys Suppl 2014;563:28-34.
Taylor AW. Alpha-melanocyte stimulating hormone (alpha-MSH) is a post-caspase suppressor of apoptosis in RAW 264.7 macrophages. PLoS One 2013;8:e74488.
Rouzaud F, Kadekaro AL, Abdel Malek ZA, Hearing VJ. MC1R and the response of melanocytes to ultraviolet radiation. Mutat Res 2005;571:133-52.
Stamos JL, Weis WI. The β-catenin destruction complex. Cold Spring Harbor Perspect Biol 2013;5:a007898-a007898.
Monga SPS. Role and regulation of β-catenin signaling during physiological liver growth. Gene Expression 2014;16:51-62.
Huang HC, Chang SJ, Wu CY, Ke HJ, Chang TM. [6]-Shogaol inhibits α-MSH-induced melanogenesis through the acceleration of ERK and PI3K/Akt-mediated MITF degradation. BioMed Res Int 2014. Doi:10.1155/2014/842569
Böhm M, Grässel S. Role of proopiomelanocortin-derived peptides and their receptors in the osteoarticular system: from basic to translational research. Endocrine Rev 2012;33:623-51.
Xie X, Xie S, Yao H, Ye X, Yu Z, Su W. Green and catalyst-free synthesis of deoxyarbutin in continuous-flow. Reaction Chem Eng 2019;4:927-31.
Shashni B, Sharma K, Singh R, Sakharkar KR, Dhillon SK, Nagasaki Y, et al. Coffee component hydroxyl hydroquinone (HHQ) as a putative ligand for PPAR gamma and implications in breast cancer. BMC Genomics 2013;14 Suppl 5:S6-S6.
Miao F, Shi Y, Fan ZF, Jiang S, Xu SZ, Lei TC. Deoxyarbutin possesses a potent skin-lightening capacity with no discernible cytotoxicity against melanosomes. PloS One 2016;11:e0165338-e0165338.
Ma L, Xu Y, Wei Z, Xin G, Xing Z, Niu H, et al. Deoxyarbutin displays antitumour activity against melanoma in vitro and in vivo through a p38-mediated mitochondria associated apoptotic pathway. Sci Rep 2017;7:7197.
Dalgard FJ, Gieler U, Tomas Aragones L, Lien L, Poot F, Jemec GBE, et al. The psychological burden of skin diseases: a cross-sectional multicenter study among dermatological out-patients in 13 European countries. J Invest Dermatol 2015;135:984-91.
Chang NF, Chen YS, Lin YJ, Tai TH, Chen AN, Huang CH, et al. Study of hydroquinone mediated cytotoxicity and hypopigmentation effects from UVB-irradiated arbutin and deoxyarbutin. Int J Mol Sci 2017;18:969.
Yang CH, Chang NF, Chen YS, Lee SM, Lin PJ, Lin CC. Comparative study on the photostability of arbutin and deoxy arbutin: sensitivity to ultraviolet radiation and enhanced photostability by the water-soluble sunscreen, benzophenone-4. Biosci Biotechnol Biochem 2013;77:1127-30.
Lin CC, Yang CH, Chang NF, Wu PS, Chen YS, Lee SM, et al. Study on the stability of deoxyarbutin in an anhydrous emulsion systemy. Int J Mol Sci 2011;12:5946-54.
Yang CH, Chen YS, Lai JS, Hong WWL, Lin CC. Determination of the thermodegradation of deoxyArbutin in aqueous solution by high performance liquid chromatography. Int J Mol Sci 2010;11:3977-87.
Muchtaridi M, Ida M, Ahmad F. Method development and validation for analysis of deoxyarbutinin anhydrous emulsion system using high-performance liquid chromatography. Int J Appl Pharm 2019;11:172-5.
Garcia Jimenez A, Teruel Puche JA, Garcia Ruiz PA, Saura Sanmartin A, Berna J, Garcia Canovas F, et al. Structural and kinetic considerations on the catalysis of deoxyarbutin by tyrosinase. PloS One 2017;12:e0187845-e0187845.
Tofani RP, Sumirtapura YC, Darijanto ST. Formulation, characterisation, and in vitro skin diffusion of nanostructured lipid carriers for deoxyarbutin compared to a nanoemulsion and conventional cream. Sci Pharm 2016;84:634-45.
Published
How to Cite
Issue
Section
