Abstract
Tyrosinase is a bifunctional polyphenol oxidase (PPO), catalyzing two oxidative reactions: monophenols to o-quinones (monophenolase activity) and o-diphenols to oquinones (diphenolase activity). As tyrosinase is the rate-limiting enzyme for the melanogenesis process, it is an attractive target for melanogenesis inhibition. Aiming at skin whitening, anticancer, Parkinson’s disease (PD) treatment, antibacterial, fruit and vegetable preservation and other anti-pigmentation effect, medicinal chemists have exploited diverse tyrosinase inhibitors through various approaches. In addition to discovering inhibitors with novel scaffolds, good activity and high safety, researchers also focused on developing strategies for synergistic effects of multiple inhibitors and simultaneously regulating multiple targets to treat cancer or neurodegenerative diseases. This review focused on multiple natural and synthetic tyrosinase inhibitors, which could contribute to preventing fruit and vegetable browning, skin whitening, antibacterial, anticancer, Parkinson's Disease, etc.
Keywords: Tyrosinase inhibitors, fruit and vegetable preservation, skin whitening, anticancer, antibacterial, PD treatment.
[http://dx.doi.org/10.1007/s00775-003-0449-4] [PMID: 12634912]
[http://dx.doi.org/10.1371/journal.pone.0161697] [PMID: 27551823]
[http://dx.doi.org/10.1016/j.ejmech.2019.111892] [PMID: 31810785]
[http://dx.doi.org/10.1016/S0031-9422(97)00186-6] [PMID: 9237394]
[http://dx.doi.org/10.1016/0006-291X(76)91077-9] [PMID: 820338]
[http://dx.doi.org/10.1021/bi200395t] [PMID: 21598903]
[http://dx.doi.org/10.1021/jf020826f] [PMID: 12720364]
[http://dx.doi.org/10.1002/chem.201704410] [PMID: 29052256]
[http://dx.doi.org/10.3390/ijms10062440] [PMID: 19582213]
[http://dx.doi.org/10.1042/bj2740707] [PMID: 1901488]
[http://dx.doi.org/10.1080/14756366.2016.1256882] [PMID: 28097901]
[http://dx.doi.org/10.1007/s00572-002-0162-0] [PMID: 12072980]
[http://dx.doi.org/10.1002/cbic.202000647] [PMID: 33108057]
[http://dx.doi.org/10.1080/10408398.2016.1175416] [PMID: 27172067]
[http://dx.doi.org/10.1002/anie.202008859] [PMID: 32701181]
[http://dx.doi.org/10.1016/j.ica.2017.04.041]
[http://dx.doi.org/10.1517/13543776.2015.1039985] [PMID: 25939410]
[http://dx.doi.org/10.1016/j.biocel.2010.03.023] [PMID: 20381640]
[http://dx.doi.org/10.1152/physrev.00044.2003] [PMID: 15383650]
[http://dx.doi.org/10.1007/s13410-021-00920-0]
[http://dx.doi.org/10.1177/002215540205000201] [PMID: 11799132]
[http://dx.doi.org/10.1096/fj.06-6649rev] [PMID: 17242160]
[http://dx.doi.org/10.4103/0973-1296.139774] [PMID: 25298661]
[http://dx.doi.org/10.1248/cpb.54.281] [PMID: 16508177]
[http://dx.doi.org/10.1111/j.1365-2133.2006.07210.x] [PMID: 16792763]
[http://dx.doi.org/10.1186/1472-6882-12-106] [PMID: 22827920]
[http://dx.doi.org/10.3233/JPD-171263] [PMID: 29991141]
[http://dx.doi.org/10.1080/14756366.2018.1545767] [PMID: 30734608]
[http://dx.doi.org/10.1111/j.1541-4337.2012.00191.x]
[PMID: 27437876]
[http://dx.doi.org/10.1016/j.ijbiomac.2016.01.070] [PMID: 26812105]
[http://dx.doi.org/10.1016/j.foodchem.2014.11.157] [PMID: 25577083]
[http://dx.doi.org/10.1016/j.bioorg.2016.01.001] [PMID: 26773755]
[http://dx.doi.org/10.1046/j.1467-2494.2000.00019.x] [PMID: 18503477]
[http://dx.doi.org/10.1016/j.ijpharm.2008.07.024] [PMID: 18718515]
[PMID: 24301240]
[http://dx.doi.org/10.1046/j.1523-1747.2002.19615.x] [PMID: 12485436]
[http://dx.doi.org/10.1038/sj.jid.5700840] [PMID: 17460731]
[http://dx.doi.org/10.1155/2013/645257]
[http://dx.doi.org/10.1016/j.carres.2018.11.006] [PMID: 30471509]
[http://dx.doi.org/10.1016/j.foodchem.2019.125310] [PMID: 31473456]
[http://dx.doi.org/10.1016/j.bioorg.2018.10.069] [PMID: 30428420]
[http://dx.doi.org/10.1016/j.ejmech.2017.09.059] [PMID: 29040952]
[http://dx.doi.org/10.1016/j.bmc.2020.115497] [PMID: 32312487]
[http://dx.doi.org/10.1016/j.ejmech.2021.113401] [PMID: 33831779]
[http://dx.doi.org/10.1016/j.ejmech.2019.07.034] [PMID: 31336310]
[http://dx.doi.org/10.1016/j.bmc.2011.11.030] [PMID: 22189272]
[http://dx.doi.org/10.4062/biomolther.2013.081] [PMID: 24596619]
[http://dx.doi.org/10.1016/j.bcp.2019.04.015] [PMID: 30991050]
[http://dx.doi.org/10.1038/srep07995] [PMID: 25613357]
[http://dx.doi.org/10.1016/j.jff.2019.01.044]
[http://dx.doi.org/10.1016/j.foodres.2017.07.010] [PMID: 28873682]
[http://dx.doi.org/10.1002/ardp.201500298] [PMID: 26575580]
[http://dx.doi.org/10.1007/s00403-016-1644-9] [PMID: 27059716]
[http://dx.doi.org/10.1016/j.bmcl.2016.12.027] [PMID: 28011217]
[http://dx.doi.org/10.1016/j.jbiosc.2016.06.002] [PMID: 27353860]
[PMID: 27081457]
[http://dx.doi.org/10.1002/bkcs.10772]
[http://dx.doi.org/10.1080/14756366.2019.1609467] [PMID: 31072148]
[http://dx.doi.org/10.1016/j.bioorg.2019.102950] [PMID: 31075740]
[http://dx.doi.org/10.1016/j.bmcl.2016.05.006] [PMID: 27185329]
[http://dx.doi.org/10.1080/09168451.2018.1445518] [PMID: 29521165]
[http://dx.doi.org/10.1111/exd.13863] [PMID: 30554432]
[http://dx.doi.org/10.2147/DDDT.S131538] [PMID: 28352157]
[http://dx.doi.org/10.1016/j.csbj.2019.07.017] [PMID: 31921392]
[http://dx.doi.org/10.1016/j.bioorg.2019.103445] [PMID: 31826809]
[http://dx.doi.org/10.1007/s00044-014-0929-9]
[http://dx.doi.org/10.1016/j.jprot.2007.12.013] [PMID: 18272228]
[http://dx.doi.org/10.1080/mmy.39.4.353.357] [PMID: 11556765]
[http://dx.doi.org/10.1046/j.1462-5814.2003.00268.x] [PMID: 12675679]
[http://dx.doi.org/10.18388/abp.2006_3314] [PMID: 16951740]
[http://dx.doi.org/10.1016/j.ejmech.2004.06.013] [PMID: 15464616]
[http://dx.doi.org/10.4314/tjpr.v15i3.10]
[http://dx.doi.org/10.1155/2013/251754]
[http://dx.doi.org/10.1080/10408398.2019.1653822] [PMID: 31456411]
[http://dx.doi.org/10.1007/s00217-012-1669-z]
[http://dx.doi.org/10.1007/s11164-013-1192-2]
[http://dx.doi.org/10.1016/j.micpath.2016.08.004] [PMID: 27497894]
[PMID: 21284262]
[http://dx.doi.org/10.1016/j.soncn.2013.06.002] [PMID: 23958214]
[http://dx.doi.org/10.1016/j.ejmech.2020.112531] [PMID: 32712436]
[http://dx.doi.org/10.3389/fnut.2016.00048] [PMID: 27843913]
[http://dx.doi.org/10.1016/j.critrevonc.2016.12.003] [PMID: 28109401]
[http://dx.doi.org/10.1042/CBI20110103] [PMID: 21542806]
[http://dx.doi.org/10.1016/j.pdpdt.2011.09.003] [PMID: 22594986]
[http://dx.doi.org/10.1016/j.bmcl.2016.03.108] [PMID: 27080182]
[http://dx.doi.org/10.3390/ijms21134732] [PMID: 32630811]
[http://dx.doi.org/10.1021/acs.jafc.0c07379] [PMID: 33821640]
[http://dx.doi.org/10.1016/j.foodchem.2020.127030] [PMID: 32535311]
[http://dx.doi.org/10.1016/j.ijbiomac.2019.06.120] [PMID: 31233796]
[http://dx.doi.org/10.1016/j.ejmech.2019.05.006] [PMID: 31082763]
[http://dx.doi.org/10.1038/334345a0] [PMID: 2899295]
[http://dx.doi.org/10.1016/S1474-4422(09)70238-8] [PMID: 19909913]
[http://dx.doi.org/10.1002/mds.25187] [PMID: 23589357]
[http://dx.doi.org/10.1016/j.expneurol.2015.11.004] [PMID: 26571193]
[http://dx.doi.org/10.1016/j.jns.2011.06.048] [PMID: 21774947]
[http://dx.doi.org/10.2174/1570159X14666151120123025] [PMID: 26585523]
[http://dx.doi.org/10.1016/j.bmcl.2017.07.075] [PMID: 28869077]
[http://dx.doi.org/10.1038/s41467-019-08858-y] [PMID: 30846695]
[PMID: 32772550]
[http://dx.doi.org/10.1002/mds.27776] [PMID: 31251435]
[http://dx.doi.org/10.2174/1568026614666140610121253] [PMID: 24917394]
[http://dx.doi.org/10.1074/jbc.M509785200] [PMID: 16436386]
[http://dx.doi.org/10.1016/j.mam.2011.10.006] [PMID: 22020111]
[http://dx.doi.org/10.1016/S1382-6689(01)00083-7] [PMID: 21782577]
[http://dx.doi.org/10.1007/s00044-012-0419-x]
[http://dx.doi.org/10.1016/j.bmcl.2018.11.030] [PMID: 30470490]
[http://dx.doi.org/10.1021/acschemneuro.1c00560] [PMID: 34882402]
[http://dx.doi.org/10.1021/jf011230f] [PMID: 11879010]
[http://dx.doi.org/10.1016/j.bmc.2016.07.060] [PMID: 27507110]
[http://dx.doi.org/10.1016/j.bmcl.2011.12.144] [PMID: 22300660]
[http://dx.doi.org/10.1002/bkcs.10931]
[http://dx.doi.org/10.1016/j.ijbiomac.2016.11.027] [PMID: 27840215]
[http://dx.doi.org/10.3390/molecules22020281] [PMID: 28208818]
[http://dx.doi.org/10.1016/j.bmcl.2019.126722] [PMID: 31732410]
[http://dx.doi.org/10.1016/j.bioorg.2019.103316] [PMID: 31585271]
[http://dx.doi.org/10.1016/j.ijbiomac.2019.05.201] [PMID: 31150673]
[http://dx.doi.org/10.1016/j.bmc.2018.10.014] [PMID: 30366788]
[http://dx.doi.org/10.1016/j.ejmech.2018.10.025] [PMID: 30347330]
[http://dx.doi.org/10.1016/j.bioorg.2019.03.001] [PMID: 30856375]
[http://dx.doi.org/10.1039/C8MD00099A] [PMID: 30108974]
[http://dx.doi.org/10.1007/s00044-017-1861-6]
[http://dx.doi.org/10.2174/1381612043382710] [PMID: 15579073]
[http://dx.doi.org/10.1021/bc060285q] [PMID: 17432826]
[http://dx.doi.org/10.1016/j.bmcl.2017.04.039] [PMID: 28476568]
[http://dx.doi.org/10.1016/j.bmcl.2005.10.013] [PMID: 16275073]
[http://dx.doi.org/10.1016/j.bmc.2017.01.037] [PMID: 28189394]
[http://dx.doi.org/10.1016/j.bioorg.2017.08.002] [PMID: 28837887]
[http://dx.doi.org/10.2174/138955710791572442] [PMID: 20402635]
[http://dx.doi.org/10.1016/j.bmc.2017.04.027] [PMID: 28478865]
[http://dx.doi.org/10.1002/ardp.201700363] [PMID: 29611624]
[http://dx.doi.org/10.1111/cbdd.12527] [PMID: 25643871]
[PMID: 26798851]
[http://dx.doi.org/10.1111/cbdd.12577] [PMID: 25916324]
[http://dx.doi.org/10.1371/journal.pone.0138578] [PMID: 26422245]
[http://dx.doi.org/10.1016/j.molstruc.2018.08.033]
[http://dx.doi.org/10.1016/j.ejmech.2018.09.031] [PMID: 30243151]
[http://dx.doi.org/10.1016/j.ejmech.2016.10.030] [PMID: 27810600]
[http://dx.doi.org/10.1016/j.ejmech.2019.06.019] [PMID: 31202126]
[http://dx.doi.org/10.1111/cbdd.13001] [PMID: 28390091]
[http://dx.doi.org/10.1002/ardp.201600224] [PMID: 27681014]
[http://dx.doi.org/10.1016/j.bmc.2016.07.068] [PMID: 27527415]
[http://dx.doi.org/10.1016/j.bbagen.2012.05.003] [PMID: 22609875]
[http://dx.doi.org/10.3390/molecules18066620] [PMID: 23743888]
[http://dx.doi.org/10.1021/cc000002f] [PMID: 10827923]
[PMID: 25826148]
[http://dx.doi.org/10.1016/j.bioorg.2019.103270] [PMID: 31539749]
[http://dx.doi.org/10.1039/C3OB42309C] [PMID: 24448828]
[http://dx.doi.org/10.1021/jm500561a] [PMID: 25025991]
[http://dx.doi.org/10.1021/jo00087a020]
[http://dx.doi.org/10.1016/j.jdermsci.2017.11.004] [PMID: 29191393]
[http://dx.doi.org/10.1023/A:1027445410426]
[http://dx.doi.org/10.1016/j.ijbiomac.2019.04.156] [PMID: 31026526]
[http://dx.doi.org/10.1007/s12010-020-03295-w] [PMID: 32212107]
[http://dx.doi.org/10.1016/j.ejmech.2009.12.058] [PMID: 20116901]
[http://dx.doi.org/10.1021/jm011116o] [PMID: 12086495]
[http://dx.doi.org/10.1039/C5RA25446A]
[http://dx.doi.org/10.1016/S0960-894X(02)00025-2] [PMID: 11859003]
[http://dx.doi.org/10.1016/j.drudis.2018.11.016] [PMID: 30481556]
[http://dx.doi.org/10.1146/annurev.biochem.78.091707.100215] [PMID: 19489722]
[PMID: 30536636]
[http://dx.doi.org/10.3762/bjoc.13.219] [PMID: 29114326]
[http://dx.doi.org/10.1002/cbdv.201900167] [PMID: 31145516]
[http://dx.doi.org/10.1016/j.bmc.2010.04.021] [PMID: 20452224]
[http://dx.doi.org/10.1016/j.foodchem.2015.05.124] [PMID: 26213029]
[http://dx.doi.org/10.1016/j.ejmech.2016.03.073] [PMID: 27061981]
[http://dx.doi.org/10.1039/C7DT01801K] [PMID: 28920989]
[http://dx.doi.org/10.1016/j.ejmech.2008.12.002] [PMID: 19128861]
[http://dx.doi.org/10.1016/j.ejmech.2009.12.016] [PMID: 20056520]
[http://dx.doi.org/10.1016/S0022-1139(02)00330-5]
[http://dx.doi.org/10.1016/j.carres.2007.11.024] [PMID: 18083151]
[http://dx.doi.org/10.1016/j.bmc.2016.03.013] [PMID: 26972919]
[http://dx.doi.org/10.1016/S1471-4922(03)00005-9] [PMID: 12643993]
[http://dx.doi.org/10.1016/j.bioorg.2019.103063] [PMID: 31220666]
[http://dx.doi.org/10.3390/molecules14010519] [PMID: 19169199]
[http://dx.doi.org/10.1016/j.ejmech.2017.08.033] [PMID: 28865277]
[http://dx.doi.org/10.1016/j.bioorg.2018.09.003] [PMID: 30248509]
[http://dx.doi.org/10.1016/j.foodchem.2016.10.140] [PMID: 27979126]
[http://dx.doi.org/10.1248/cpb.c19-00949] [PMID: 32238654]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.048] [PMID: 20716467]
[http://dx.doi.org/10.1002/jhet.3760]
[http://dx.doi.org/10.1016/j.bmc.2005.04.046] [PMID: 15905094]
[http://dx.doi.org/10.1016/j.ejmech.2007.01.003] [PMID: 17321639]
[http://dx.doi.org/10.3797/scipharm.1109-14] [PMID: 22145104]
[http://dx.doi.org/10.1021/jm9900927] [PMID: 10447958]
[http://dx.doi.org/10.1111/j.1747-0285.2006.00399.x] [PMID: 16882318]
[PMID: 9442556]
[http://dx.doi.org/10.3390/12081910] [PMID: 17960096]
[http://dx.doi.org/10.4103/0250-474X.41448] [PMID: 20046705]
[http://dx.doi.org/10.1016/j.bmc.2010.01.021] [PMID: 20138770]
[http://dx.doi.org/10.1016/j.ejmech.2017.04.021] [PMID: 28433680]
[http://dx.doi.org/10.1016/j.ijbiomac.2017.11.147] [PMID: 29180052]
[http://dx.doi.org/10.1016/j.bmc.2017.09.009] [PMID: 28988751]
[http://dx.doi.org/10.1016/j.bioorg.2019.01.036] [PMID: 30772647]
[http://dx.doi.org/10.1021/jm801343r] [PMID: 19296651]
[http://dx.doi.org/10.1016/j.bmcl.2009.01.090] [PMID: 19217781]
[http://dx.doi.org/10.1016/S0968-0896(00)00160-7] [PMID: 11026546]
[http://dx.doi.org/10.1016/j.ejmech.2007.03.033] [PMID: 17531354]
[http://dx.doi.org/10.1097/00001813-199701000-00012] [PMID: 9147617]
[http://dx.doi.org/10.1016/j.bioorg.2016.09.007] [PMID: 27669118]
[http://dx.doi.org/10.1007/s11418-017-1148-8] [PMID: 29264846]
[http://dx.doi.org/10.1016/j.bbagen.2012.03.018] [PMID: 22498140]
[http://dx.doi.org/10.1039/c0md00234h]
[http://dx.doi.org/10.1016/j.bbagen.2011.03.001] [PMID: 21397665]
[http://dx.doi.org/10.1016/j.ejmech.2012.01.019] [PMID: 22301213]
[http://dx.doi.org/10.1039/C4MD00171K]
[http://dx.doi.org/10.1007/s12272-013-0184-5] [PMID: 23812774]
[PMID: 26347064]
[http://dx.doi.org/10.1016/j.bmc.2018.05.047] [PMID: 29907470]
[http://dx.doi.org/10.1080/14756366.2019.1654468] [PMID: 31456445]
[http://dx.doi.org/10.1016/S0006-2952(98)00340-2] [PMID: 10037452]
[http://dx.doi.org/10.1007/s00044-018-2267-9]
[http://dx.doi.org/10.1016/j.freeradbiomed.2015.10.397] [PMID: 26459033]
[http://dx.doi.org/10.1371/journal.pone.0167699] [PMID: 27936080]
[http://dx.doi.org/10.1039/C6FO00636A] [PMID: 27491891]
[http://dx.doi.org/10.1186/1752-153X-7-19] [PMID: 23363809]
[http://dx.doi.org/10.1186/s13065-020-00679-1] [PMID: 32280949]
[http://dx.doi.org/10.1016/j.cellimm.2012.12.007] [PMID: 23399843]
[http://dx.doi.org/10.1016/j.ejmech.2008.05.008] [PMID: 18597896]
[http://dx.doi.org/10.1016/j.ejphar.2011.08.052] [PMID: 21937012]
[http://dx.doi.org/10.1017/S0007114515003086] [PMID: 26346559]
[http://dx.doi.org/10.1007/s10753-015-0243-9] [PMID: 26329367]
[http://dx.doi.org/10.1016/j.bmc.2019.04.016] [PMID: 31000406]
[http://dx.doi.org/10.1080/09168451.2016.1240606] [PMID: 27756183]
[http://dx.doi.org/10.1016/j.bmcl.2018.11.029] [PMID: 30470492]
[http://dx.doi.org/10.1039/C5RA19551A]
[http://dx.doi.org/10.1016/j.ijbiomac.2017.04.058] [PMID: 28414110]
[http://dx.doi.org/10.1038/jid.2009.124] [PMID: 19440221]
[http://dx.doi.org/10.1016/j.peptides.2006.11.023] [PMID: 17241698]
[http://dx.doi.org/10.1021/ci500370x] [PMID: 25317506]
[http://dx.doi.org/10.1016/j.jbiosc.2015.10.010] [PMID: 26589783]
[http://dx.doi.org/10.1080/14756366.2019.1661401] [PMID: 31496313]
[http://dx.doi.org/10.1021/acs.jmedchem.8b00737] [PMID: 30011202]
[http://dx.doi.org/10.7717/peerj.4206] [PMID: 29383286]
[http://dx.doi.org/10.1002/minf.201900054] [PMID: 31508903]
[http://dx.doi.org/10.1002/jccs.201800119]
[http://dx.doi.org/10.1016/j.molstruc.2017.08.034]
[http://dx.doi.org/10.1515/znc-2016-0095] [PMID: 27442367]
[http://dx.doi.org/10.1016/j.foodchem.2019.05.184] [PMID: 31253292]
[http://dx.doi.org/10.1016/S0169-328X(96)00308-7] [PMID: 9105685]
[http://dx.doi.org/10.1016/j.bmc.2010.12.007] [PMID: 21236688]
[http://dx.doi.org/10.1016/j.ejmech.2019.111862] [PMID: 31735576]
[http://dx.doi.org/10.1016/j.ejmech.2017.03.062] [PMID: 28371641]
[http://dx.doi.org/10.1080/14756366.2019.1707196] [PMID: 31899985]
[http://dx.doi.org/10.1080/17460441.2017.1253677] [PMID: 27783541]
[http://dx.doi.org/10.1038/nrd2467] [PMID: 18167490]
[http://dx.doi.org/10.1021/acs.jmedchem.6b00492] [PMID: 27144971]
[http://dx.doi.org/10.1080/17460441.2020.1743676] [PMID: 32208982]
[http://dx.doi.org/10.3390/metabo8020025] [PMID: 29561812]
[http://dx.doi.org/10.1021/cr200176r] [PMID: 22607219]
[http://dx.doi.org/10.1080/14756366.2020.1765166] [PMID: 32401067]
[http://dx.doi.org/10.1016/j.bioorg.2018.06.005] [PMID: 29940340]
[http://dx.doi.org/10.1080/14756366.2016.1238362] [PMID: 27778522]
[http://dx.doi.org/10.1080/07391102.2014.893203] [PMID: 24601849]
[http://dx.doi.org/10.1034/j.1600-0749.2003.00029.x] [PMID: 12622786]