An Updated Review of Tyrosinase Inhibitors

Tyrosinase is a multifunctional, glycosylated, and copper-containing oxidase, which catalyzes the first two steps in mammalian melanogenesis and is responsible for enzymatic browning reactions in damaged fruits during post-harvest handling and processing. Neither hyperpigmentation in human skin nor enzymatic browning in fruits are desirable. These phenomena have encouraged researchers to seek new potent tyrosinase inhibitors for use in foods and cosmetics. This article surveys tyrosinase inhibitors newly discovered from natural and synthetic sources. The inhibitory strength is compared with that of a standard inhibitor, kojic acid, and their inhibitory mechanisms are discussed.

[1]  Tian-Shung Wu,et al.  Antityrosinase principles and constituents of the petals of Crocus sativus. , 2004, Journal of natural products.

[2]  C. Tsou.  Kinetics of substrate reaction during irreversible modification of enzyme activity. , 2006, Advances in enzymology and related areas of molecular biology.

[3]  H. Uyama,et al.  Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future , 2005, Cellular and Molecular Life Sciences CMLS.

[4]  I. Kubo,et al.  Flavonols from Heterotheca inuloides: tyrosinase inhibitory activity and structural criteria. , 2000, Bioorganic & medicinal chemistry.

[5]  Y. Akao,et al.  Effects of hydroxystilbene derivatives on tyrosinase activity. , 2003, Biochemical and biophysical research communications.

[6]  K. Park,et al.  Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz , 2008 .

[7]  R. Varón,et al.  A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase. , 2007, Journal of agricultural and food chemistry.

[8]  R. Kondo,et al.  Inhibitory effect of artocarpanone from Artocarpus heterophyllus on melanin biosynthesis. , 2006, Biological & pharmaceutical bulletin.

[9]  Qi Ding,et al.  Quantitative structure–activity relationship studies of mushroom tyrosinase inhibitors , 2008, J. Comput. Aided Mol. Des..

[10]  Kyung-Tae Lee,et al.  Two new flavonol glycosides from Lamium amplexicaule L. and their in vitro free radical scavenging and tyrosinase inhibitory activities. , 2009, Planta medica.

[11]  Mahmud Tareq Hassan Khan,et al.  Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. , 2006, Bioorganic & medicinal chemistry.

[12]  Hyunsu Bae,et al.  Survey and mechanism of skin depigmenting and lightening agents , 2006, Phytotherapy research : PTR.

[13]  S. Kim,et al.  Mulberroside F isolated from the leaves of Morus alba inhibits melanin biosynthesis. , 2002, Biological & pharmaceutical bulletin.

[14]  Hwan-Suck Chung,et al.  Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries , 2007, Phytotherapy research : PTR.

[15]  T. Skotland,et al.  Inactivation of dopamine β-monooxygenase by hydrogen peroxide and by ascorbate , 1980 .

[16]  S. Paskewitz,et al.  Hen egg white lysozyme as an inhibitor of mushroom tyrosinase , 2006, FEBS letters.

[17]  M. Ichihashi,et al.  Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase. , 2007, The Journal of investigative dermatology.

[18]  T. Yokozawa,et al.  Piceatannol inhibits melanogenesis by its antioxidative actions. , 2007, Biological & pharmaceutical bulletin.

[19]  P. Pithayanukul,et al.  Molecular Docking Studies and Anti-Tyrosinase Activity of Thai Mango Seed Kernel Extract , 2009, Molecules.

[20]  Nagasuma Chandra,et al.  Functional interaction of diphenols with polyphenol oxidase , 2007, The FEBS journal.

[21]  T. Masuda,et al.  Tyrosinase Inhibitory Activity of Ethanol Extracts from Medicinal and Edible Plants Cultivated in Okinawa and Identification of a Water-Soluble Inhibitor from the Leaves of Nandina domestica , 2007, Bioscience, biotechnology and biochemistry.

[22]  Qing-Xi Chen,et al.  Irreversibly inhibitory kinetics of 3,5-dihydroxyphenyl decanoate on mushroom (Agaricus bisporus) tyrosinase. , 2005, Bioorganic & medicinal chemistry.

[23]  Wen‐yuan Zhu,et al.  The use of botanical extracts as topical skin-lightening agents for the improvement of skin pigmentation disorders. , 2008, The journal of investigative dermatology. Symposium proceedings.

[24]  S. Kim,et al.  Inhibitory effects of 1,3-selenazol-4-one derivatives on mushroom tyrosinase. , 2002, Chemical & pharmaceutical bulletin.

[25]  I. Kubo,et al.  Flavonols from saffron flower: tyrosinase inhibitory activity and inhibition mechanism. , 1999, Journal of agricultural and food chemistry.

[26]  Hang-Ching Lin,et al.  Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa. , 2010, Journal of cosmetic science.

[27]  C. Teng,et al.  Isolation of a Natural Antioxidant, Dehydrozingerone from Zingiber officinale and Synthesis of Its Analogues for Recognition of Effective Antioxidant and Antityrosinase Agents , 2005, Archives of pharmacal research.

[28]  Jun Sik Lee,et al.  Inhibition of melanogenic activity by 4,4'-dihydroxybiphenyl in melanoma cells. , 2006, Biological & pharmaceutical bulletin.

[29]  F. García-Carmona,et al.  Competitive inhibition of mushroom tyrosinase by 4-substituted benzaldehydes. , 2001, Journal of agricultural and food chemistry.

[30]  R. Kondo,et al.  A new stilbene with tyrosinase inhibitory activity from Chlorophora excelsa. , 2003, Chemical & pharmaceutical bulletin.

[31]  E. Solomon,et al.  Substrate analogue binding to the coupled binuclear copper active site in tyrosinase , 1985 .

[32]  H. Chung,et al.  Inhibition of tyrosinase by protocatechuic aldehyde. , 2004, The American journal of Chinese medicine.

[33]  K. Schallreuter,et al.  Regulation of melanogenesis – controversies and new concepts , 2008, Experimental dermatology.

[34]  J. Vaya,et al.  Enhanced substituted resorcinol hydrophobicity augments tyrosinase inhibition potency. , 2007, Journal of medicinal chemistry.

[35]  Qing-Xi Chen,et al.  Inhibitory Effects of Hexylresorcinol and Dodecylresorcinol on Mushroom (Agaricus bisporus) Tyrosinase , 2004, The protein journal.

[36]  Poonsakdi Ploypradith,et al.  Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. , 2006, Bioorganic & medicinal chemistry letters.

[37]  J. Choi,et al.  Tyrosinase inhibitors isolated from the edible brown algaEcklonia stolonifera , 2004, Archives of pharmacal research.

[38]  H. S. Mason.  The chemistry of melanin; mechanism of the oxidation of dihydroxyphenylalanine by tyrosinase. , 1948, The Journal of biological chemistry.

[39]  Qing-Xi Chen,et al.  Inhibitory effects of 4-vinylbenzaldehyde and 4-vinylbenzoic acid on the activity of mushroom tyrosinase , 2005, Journal of enzyme inhibition and medicinal chemistry.

[40]  K. Umezawa,et al.  pH-dependent inhibition of mushroom tyrosinase by N-substituted N-nitrosohydroxylamines , 2008 .

[41]  K. Umezawa,et al.  Synthesis of N-substituted N-nitrosohydroxylamines as inhibitors of mushroom tyrosinase. , 2001, Bioorganic & medicinal chemistry.

[42]  I. Kubo,et al.  Tyrosinase inhibitory activity of the olive oil flavor compounds. , 1999, Journal of agricultural and food chemistry.

[43]  T. Masuda,et al.  Screening for Tyrosinase Inhibitors among Extracts of Seashore Plants and Identification of Potent Inhibitors from Garcinia subelliptica , 2005, Bioscience, biotechnology, and biochemistry.

[44]  E. Camera,et al.  Chemical and instrumental approaches to treat hyperpigmentation. , 2003, Pigment cell research.

[45]  Mamoru Koketsu,et al.  Potent inhibitory effects of N-aryl S-alkylthiocarbamate derivatives on the dopa oxidase activity of mushroom tyrosinase. , 2005, Chemical & pharmaceutical bulletin.

[46]  J. Harborne,et al.  Advances in flavonoid research since 1992. , 2000, Phytochemistry.

[47]  Kang-Kang Song,et al.  Inhibitory Effects on Mushroom Tyrosinase by Some Alkylbenzaldehydes , 2003, Journal of enzyme inhibition and medicinal chemistry.

[48]  J. Kawabata,et al.  Inhibitory effects of 5,6,7-trihydroxyflavones on tyrosinase. , 2007, Molecules.

[49]  L. Xie,et al.  Inhibitory effects of cupferron on the monophenolase and diphenolase activity of mushroom tyrosinase. , 2003, The international journal of biochemistry & cell biology.

[50]  Z. Draelos.  Skin lightening preparations and the hydroquinone controversy , 2007, Dermatologic therapy.

[51]  M. Sugumaran.  Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects. , 2002, Pigment cell research.

[52]  Mahmud Tareq Hassan Khan,et al.  Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum , 2007, Phytotherapy research : PTR.

[53]  Ji-Ho Park,et al.  Inhibition of tyrosinase activity by N,N-unsubstituted selenourea derivatives. , 2005, Biological & pharmaceutical bulletin.

[54]  R. Halaban,et al.  Abnormal Acidification of Melanoma Cells Induces Tyrosinase Retention in the Early Secretory Pathway* , 2002, The Journal of Biological Chemistry.

[55]  M. Criton,et al.  Phenylethylamide and phenylmethylamide derivatives as new tyrosinase inhibitors. , 2009, Biological & pharmaceutical bulletin.

[56]  J. Anzai,et al.  Tyrosinase inhibitor from black rice bran. , 2003, Journal of agricultural and food chemistry.

[57]  Se-kwon Kim,et al.  Myrothenones A and B, cyclopentenone derivatives with tyrosinase inhibitory activity from the marine-derived fungus Myrothecium sp. , 2005, Chemical & pharmaceutical bulletin.

[58]  J. Ley,et al.  Hydroxy- or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors. , 2001, Bioorganic & medicinal chemistry.

[59]  T. Sabudak,et al.  Potent tyrosinase inhibitors from Trifolium balansae , 2006, Natural product research.

[60]  Yong Sup Lee,et al.  Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives. , 2009, Bioorganic & medicinal chemistry letters.

[61]  Y. Matoba,et al.  Crystallographic Evidence That the Dinuclear Copper Center of Tyrosinase Is Flexible during Catalysis* , 2006, Journal of Biological Chemistry.

[62]  V. Sharma,et al.  Mushroom tyrosinase: recent prospects. , 2003, Journal of agricultural and food chemistry.

[63]  J. Vaya,et al.  Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. , 2004, Phytochemistry.

[64]  H. Chung,et al.  4-(6-Hydroxy-2-naphthyl)-1,3-bezendiol: a potent, new tyrosinase inhibitor. , 2007, Biological & pharmaceutical bulletin.

[65]  Qing-Xi Chen,et al.  Inhibitory effects of cis- and trans-isomers of 3,5-dihydroxystilbene on the activity of mushroom tyrosinase. , 2006, Biochemical and biophysical research communications.

[66]  H. Kwon,et al.  Downregulation of melanin synthesis by haginin A and its application to in vivo lightening model. , 2008, The Journal of investigative dermatology.

[67]  K. Strothkamp,et al.  Inhibitor binding to the binuclear active site of tyrosinase: temperature, pH, and solvent deuterium isotope effects. , 1994, Biochemistry.

[68]  M. T. Khan,et al.  Tyrosinase inhibitory lignans from the methanol extract of the roots of Vitex negundo Linn. and their structure-activity relationship. , 2006, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[69]  Bin Wu,et al.  New Tyrosinase Inhibitory Sesquiterpenes from Chloranthus henryi , 2008, Chemistry & biodiversity.

[70]  Mahmud Tareq Hassan Khan,et al.  Microbial transformation of 17alpha-ethynyl- and 17alpha-ethylsteroids, and tyrosinase inhibitory activity of transformed products. , 2005, Steroids.

[71]  Youngsoo Kim,et al.  Oxyresveratrol and Hydroxystilbene Compounds , 2002, The Journal of Biological Chemistry.

[72]  I. Kubo,et al.  2-Hydroxy-4-methoxybenzaldehyde: A Potent Tyrosinase Inhibitor from African Medicinal Plants , 1999, Planta medica.

[73]  H. Chung,et al.  4,4'-Dihydroxybiphenyl as a new potent tyrosinase inhibitor. , 2005, Biological & pharmaceutical bulletin.

[74]  H. Raper.  THE AEROBIC OXIDASES , 1928 .

[75]  L. Xie,et al.  Inhibitory Effects of Some Flavonoids on the Activity of Mushroom Tyrosinase , 2003, Biochemistry (Moscow).

[76]  M. Iinuma,et al.  Studies of cuticle drugs from natural sources. III. Inhibitory effect of Myrica rubra on melanin biosynthesis. , 1995, Biological & pharmaceutical bulletin.

[77]  Mahmud Tareq Hassan Khan,et al.  Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship. , 2006, Bioorganic & medicinal chemistry.

[78]  Jeong-Hill Park,et al.  Tyrosinase-inhibitory furanocoumarin from Angelica dahurica. , 2004, Biological & pharmaceutical bulletin.

[79]  R. Kondo,et al.  Inhibition of Tyrosinase by Flavonoids, Stilbenes and Related 4-Substituted Resorcinols: Structure-Activity Investigations , 2000, Planta medica.

[80]  C. A. Ramsden,et al.  The mechanism of suicide-inactivation of tyrosinase: a substrate structure investigation. , 2007, The Tohoku journal of experimental medicine.

[81]  K. Mochida,et al.  In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans. , 2004, Journal of agricultural and food chemistry.

[82]  Mahmud Tareq Hassan Khan,et al.  Synthesis of Methyl Ether Analogues of Sildenafil (Viagra®) Possessing Tyrosinase Inhibitory Potential , 2005, Chemistry & biodiversity.

[83]  M. Marshall,et al.  Inhibition mechanism of kojic acid on polyphenol oxidase , 1991 .

[84]  S. Ahn,et al.  Regulation of melanin synthesis by selenium-containing carbohydrates. , 2006, Chemical & pharmaceutical bulletin.

[85]  F. García-Carmona,et al.  L-mimosine a slow-binding inhibitor of mushroom tyrosinase , 1987 .

[86]  Jinhe Kim,et al.  Flavonoids as mushroom tyrosinase inhibitors: a fluorescence quenching study. , 2006, Journal of agricultural and food chemistry.

[87]  S. Waley.  Kinetics of suicide substrates. Practical procedures for determining parameters. , 1985, The Biochemical journal.

[88]  A. Karioti,et al.  Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. , 2007, Bioorganic & medicinal chemistry.

[89]  T. Hwang,et al.  Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use , 2008, Phytotherapy research : PTR.

[90]  C. A. Ramsden,et al.  Evidence consistent with the requirement of cresolase activity for suicide inactivation of tyrosinase. , 2008, The Tohoku journal of experimental medicine.

[91]  A. Rescigno,et al.  Tyrosinase Inhibition: General and Applied Aspects , 2002, Journal of enzyme inhibition and medicinal chemistry.

[92]  V. Kahn,et al.  Inactivation of mushroom tyrosinase by hydrogen peroxide , 1985 .

[93]  J. Choi,et al.  Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis. , 2008, Biological & pharmaceutical bulletin.

[94]  Manzoor Ahmad,et al.  Alkaloids of Aconitum laeve and their anti-inflammatory antioxidant and tyrosinase inhibition activities. , 2005, Phytochemistry.

[95]  Mahmud Tareq Hassan Khan,et al.  Tetraketones: a new class of tyrosinase inhibitors. , 2006, Bioorganic & medicinal chemistry.

[96]  J. Hwang,et al.  Depigmenting activity and low cytotoxicity of alkoxy benzoates or alkoxy cinnamte in cultured melanocytes. , 2003, Chemical & pharmaceutical bulletin.

[97]  J N Rodríguez-López,et al.  Tyrosinase: a comprehensive review of its mechanism. , 1995, Biochimica et biophysica acta.

[98]  Te-Sheng Chang.  8-Hydroxydaidzein is unstable in alkaline solutions. , 2010, Journal of cosmetic science.

[99]  Y. Kubota,et al.  The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation. , 1998, Pigment cell research.

[100]  J. Espín,et al.  Effect of captopril on mushroom tyrosinase activity in vitro. , 2001, Biochimica et biophysica acta.

[101]  K. Umezawa,et al.  Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines. , 2003, Bioorganic chemistry.

[102]  I. Kubo,et al.  Inactivation Kinetics of Mushroom Tyrosinase by Cetylpyridinium Chloride , 2003, Journal of protein chemistry.

[103]  Yong Sup Lee,et al.  Identification of tyrosinase inhibitors from Glycyrrhiza uralensis. , 2005, Planta medica.

[104]  C. Lee,et al.  Inhibitory effects of calycosin isolated from the root of Astragalus membranaceus on melanin biosynthesis. , 2009, Biological & pharmaceutical bulletin.

[105]  J. Park,et al.  A sphingolipid and tyrosinase inhibitors from the fruiting body ofphellinus linteus , 2004, Archives of pharmacal research.

[106]  F. Solano,et al.  Molecular anatomy of tyrosinase and its related proteins: beyond the histidine-bound metal catalytic center. , 2002, Pigment cell research.

[107]  C. Cespedes,et al.  Tyrosinase Inhibitors from Galls of Rhus javanica Leaves and Their Effects on Insects , 2003, Zeitschrift für Naturforschung C - A Journal of Biosciences.

[108]  I. Kubo,et al.  Tyrosinase Inhibitors from Cumin , 1998 .

[109]  K. Park,et al.  Tyrosinase inhibitory polyphenols from roots of Morus lhou. , 2009, Journal of agricultural and food chemistry.

[110]  J. Espín,et al.  Slow-binding inhibition of mushroom (Agaricus bisporus) tyrosinase isoforms by tropolone. , 1999, Journal of agricultural and food chemistry.

[111]  Isao Kubo,et al.  Molecular design of antibrowning agents: antioxidative tyrosinase inhibitors , 2003 .

[112]  D. Chung,et al.  Inhibitory effect of dalbergioidin isolated from the trunk of Lespedeza cyrtobotrya on melanin biosynthesis. , 2008, Journal of Microbiology and Biotechnology.

[113]  I. Kubo,et al.  Molecular design of antibrowning agents. , 2000, Journal of agricultural and food chemistry.

[114]  Y. Boo,et al.  Flavonoids, taxifolin and luteolin attenuate cellular melanogenesis despite increasing tyrosinase protein levels , 2008, Phytotherapy research : PTR.

[115]  Mingfu Wang,et al.  Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agent. , 2008, Molecular nutrition & food research.

[116]  I. Kubo,et al.  2-hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor. , 2004, Bioorganic & medicinal chemistry letters.

[117]  M. Noda,et al.  Identification and kinetic study of tyrosinase inhibitors found in sake lees. , 2006, Journal of agricultural and food chemistry.

[118]  M. R. Shah,et al.  Tyrosinase-inhibitory long-chain esters from Amberboa ramosa. , 2005, Chemical & pharmaceutical bulletin.

[119]  A. Rescigno,et al.  Umbelliferone and esculetin: inhibitors or substrates for polyphenol oxidases? , 2008, Biological & pharmaceutical bulletin.

[120]  G. Vielhaber,et al.  4‐(1‐Phenylethyl)1,3‐Benzenediol: A New, Highly Efficient Lightening Agent , 2007 .

[121]  Hoi-Seon Lee.  Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. , 2002, Journal of agricultural and food chemistry.

[122]  M. Rendon,et al.  Review of skin-lightening agents. , 2006, Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.].

[123]  Mei Hong,et al.  Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase. , 2002, Pigment cell research.

[124]  Kenji Matsumoto,et al.  Gnetol as a Potent Tyrosinase Inhibitor from Genus Gnetum , 2003, Bioscience, biotechnology, and biochemistry.

[125]  H. Matsuda,et al.  Inhibitory effects of Citrus hassaku extract and its flavanone glycosides on melanogenesis. , 2009, Biological & pharmaceutical bulletin.

[126]  D. Wei,et al.  Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts , 2007, Journal of enzyme inhibition and medicinal chemistry.

[127]  C. A. Ramsden,et al.  Evidence of the Indirect Formation of the Catecholic Intermediate Substrate Responsible for the Autoactivation Kinetics of Tyrosinase* , 1997, The Journal of Biological Chemistry.

[128]  E. Jaenicke,et al.  A three-dimensional model of mammalian tyrosinase active site accounting for loss of function mutations. , 2007, Pigment cell research.

[129]  H. Ding,et al.  Mushroom tyrosinase inhibitory effects of isoflavones isolated from soygerm koji fermented with Aspergillus oryzae BCRC 32288 , 2007 .

[130]  Mahmud Tareq Hassan Khan,et al.  Microbial transformation of 17α-ethynyl- and 17α-ethylsteroids, and tyrosinase inhibitory activity of transformed products , 2005, Steroids.

[131]  R. Varón,et al.  Experimental methods for kinetic study of suicide substrates. , 1989, Journal of enzyme inhibition.

[132]  J. Vaya,et al.  Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety. , 2005, Bioorganic & medicinal chemistry.

[133]  Xiao-ru Wang,et al.  Isolation and identification of flavonoids in licorice and a study of their inhibitory effects on tyrosinase. , 2005, Journal of agricultural and food chemistry.

[134]  G. Hong,et al.  Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors. , 2007, Bioorganic & medicinal chemistry.

[135]  Li Zhang,et al.  3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors. , 2007, Bioorganic & medicinal chemistry.

[136]  M. Chung,et al.  Aloesin inhibits hyperpigmentation induced by UV radiation , 2002, Clinical and experimental dermatology.

[137]  F. García-Carmona,et al.  Kojic Acid, a Cosmetic Skin Whitening Agent, is a Slow‐binding Inhibitor of Catecholase Activity of Tyrosinase , 1994, The Journal of pharmacy and pharmacology.

[138]  Te-Sheng Chang.  Two potent suicide substrates of mushroom tyrosinase: 7,8,4'-trihydroxyisoflavone and 5,7,8,4'-tetrahydroxyisoflavone. , 2007, Journal of agricultural and food chemistry.

[139]  Mahmud Tareq Hassan Khan,et al.  Tyrosinase inhibition studies of cycloartane and cucurbitane glycosides and their structure-activity relationships. , 2006, Bioorganic & medicinal chemistry.

[140]  Bin Wu,et al.  Complex sesquiterpenoids with tyrosinase inhibitory activity from the leaves of Chloranthus tianmushanensis. , 2008, Journal of natural products.

[141]  T. Masuda,et al.  Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus). , 2008, Journal of agricultural and food chemistry.

[142]  E. Solomon,et al.  SUBSTRATE ANALOG BINDING TO THE COUPLED BINUCLEAR COPPER ACTIVE SITE IN TYROSINASE , 2002 .

[143]  I. Kubo,et al.  Tyrosinase inhibitory p‐Coumaric acid from Ginseng leaves , 1999, Phytotherapy research : PTR.

[144]  S. H. Kang,et al.  Oxyresveratrol as the potent inhibitor on dopa oxidase activity of mushroom tyrosinase. , 1998, Biochemical and biophysical research communications.

[145]  Youngeup Jin,et al.  Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase. , 2007, Bioorganic & medicinal chemistry letters.

[146]  Hiromi Oozeki,et al.  Molecular design of potent tyrosinase inhibitors having the bibenzyl skeleton. , 2008, Bioorganic & medicinal chemistry letters.

[147]  Kang-Kang Song,et al.  Inhibitory effects of salicylic acid family compounds on the diphenolase activity of mushroom tyrosinase , 2006 .

[148]  I. Chu,et al.  Inhibitory effect of p-hydroxybenzyl alcohol on tyrosinase activity and melanogenesis. , 2007, Biological & pharmaceutical bulletin.

[149]  Mahmud Tareq Hassan Khan,et al.  Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. , 2005, Bioorganic & medicinal chemistry.

[150]  X. Yao,et al.  Biphenyl glycosides from the fruit of Pyracantha fortuneana. , 2006, Journal of natural products.

[151]  Francisco Solano,et al.  Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. , 2006, Pigment cell research.

[152]  K. P. Devkota,et al.  Tyrosinase inhibitory and antileishmanial constituents from the rhizomes of Paris polyphylla , 2007, Natural product research.

[153]  S. Rhee,et al.  Inhibition of tyrosinase by green tea components. , 1999, Life sciences.

[154]  B. Krebs,et al.  The crystal structure of catechol oxidase: new insight into the function of type-3 copper proteins. , 2002, Accounts of chemical research.

[155]  Marc Criton,et al.  Analogues of N-hydroxy-N'-phenylthiourea and N-hydroxy-N'-phenylurea as inhibitors of tyrosinase and melanin formation. , 2008, Bioorganic & medicinal chemistry letters.

[156]  M. Miyazawa,et al.  Inhibitory compound of tyrosinase activity from the sprout of Polygonum hydropiper L. (Benitade). , 2007, Biological & pharmaceutical bulletin.

[157]  Ali Akbar Saboury,et al.  Substrate share in the suicide inactivation of mushroom tyrosinase. , 2004, Biochimica et biophysica acta.

[158]  M. Litaudon,et al.  Tyrosinase inhibitors and sesquiterpene diglycosides from Guioa villosa. , 2008, Planta medica.

[159]  Hang-Ching Lin,et al.  Identifying 6,7,4′-Trihydroxyisoflavone as a Potent Tyrosinase Inhibitor , 2005, Bioscience, biotechnology, and biochemistry.

[160]  R. Ben-arie,et al.  Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots. , 2003, Journal of agricultural and food chemistry.

[161]  Y. Murata,et al.  Mushroom Tyrosinase Inhibitory Activity of Esculetin Isolated from Seeds of Euphorbia lathyris L. , 2003, Bioscience, biotechnology, and biochemistry.

[162]  Xiaobing Huang,et al.  Inhibitory effects of fluorobenzaldehydes on the activity of mushroom tyrosinase , 2006, Journal of enzyme inhibition and medicinal chemistry.

[163]  Heyao Wang,et al.  Inhibitory effect of 2,4,2',4'-tetrahydroxy-3-(3-methyl-2-butenyl)-chalcone on tyrosinase activity and melanin biosynthesis. , 2009, Biological & pharmaceutical bulletin.

[164]  C. Lee,et al.  Synthetic tyrosyl gallate derivatives as potent melanin formation inhibitors. , 2007, Bioorganic & medicinal chemistry letters.

[165]  Hyun Pyo Kim,et al.  Tyrosinase inhibitory prenylated flavonoids from Sophora flavescens. , 2003, Biological & pharmaceutical bulletin.

[166]  U. Farooq,et al.  Tyrosinase inhibitors from Rhododendron collettianum and their structure-activity relationship (SAR) studies. , 2004, Chemical & pharmaceutical bulletin.

[167]  D. Hebert,et al.  Tyrosinase Maturation through the Mammalian Secretory Pathway: Bringing Color to Life , 2022 .