show all | hide all No of entries

Information on EC 1.14.18.1 - tyrosinase and Organism(s) Agaricus bisporus and UniProt Accession O42713

for references in articles please use BRENDA:EC1.14.18.1
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
IUBMB Comments
A type III copper protein found in a broad variety of bacteria, fungi, plants, insects, crustaceans, and mammals, which is involved in the synthesis of betalains and melanin. The enzyme, which is activated upon binding molecular oxygen, can catalyse both a monophenolase reaction cycle (reaction 1) or a diphenolase reaction cycle (reaction 2). During the monophenolase cycle, one of the bound oxygen atoms is transferred to a monophenol (such as L-tyrosine), generating an o-diphenol intermediate, which is subsequently oxidized to an o-quinone and released, along with a water molecule. The enzyme remains in an inactive deoxy state, and is restored to the active oxy state by the binding of a new oxygen molecule. During the diphenolase cycle the enzyme binds an external diphenol molecule (such as L-dopa) and oxidizes it to an o-quinone that is released along with a water molecule, leaving the enzyme in the intermediate met state. The enzyme then binds a second diphenol molecule and repeats the process, ending in a deoxy state . The second reaction is identical to that catalysed by the related enzyme catechol oxidase (EC 1.10.3.1). However, the latter can not catalyse the hydroxylation or monooxygenation of monophenols.
Specify your search results
Select one or more organisms in this record: ?
This record set is specific for:
Agaricus bisporus
UNIPROT: O42713
Word Map
The taxonomic range for the selected organisms is: Agaricus bisporus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Reaction Schemes
hide(Overall reactions are displayed. Show all >>)
2
+
=
2
+
2
Synonyms
AbPPO1, AbPPO4, AbTYR, aurone synthase, catalase-phenol oxidase, catechol oxidase, catecholase, CATPO, chlorogenic acid oxidase, chlorogenic oxidase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
AbPPO1
283726
-
AbPPO4
309210
-
catechol oxidase
catecholase
chlorogenic acid oxidase
-
-
-
-
chlorogenic oxidase
-
-
-
-
cresolase
-
-
-
-
cresolase/monophenolase
984
-
deoxy-tyrosinase
984
-
Diphenol oxidase
-
-
-
-
dopa oxidase
-
-
-
-
met-tyrosinase
984
-
monophenol dihydroxyphenylalanine:oxygen oxidoreductase
-
-
-
-
monophenol monooxidase
-
-
-
-
monophenol monooxygenase
984
-
monophenol oxidase
-
-
-
-
monophenol oxygen oxidoreductase
984
-
monophenol, dihydroxy-L-phenylalanine oxygen oxidoreductase
-
-
-
-
monophenol, o-diphenol:oxygen oxido-reductase
283726
-
monophenol, o-diphenol:oxygen oxidoreductase
monophenol, polyphenol oxidase
984
-
monophenolase
monphenol mono-oxgenase
984
-
mushroom tyrosinase
mushroom tyrosine
984
-
N-acetyl-6-hydroxytryptophan oxidase
-
-
-
-
o-diphenol oxidase
-
-
-
-
o-diphenol oxidoreductase
-
-
-
-
o-diphenol oxygen oxidoreductase
984
-
o-diphenol: O2 oxidoreductase
984
-
o-diphenol: oxidoreductase
984
-
o-diphenol:O2 oxidoreductase
-
-
-
-
o-diphenol:oxygen oxidoreductase
-
-
-
-
o-diphenolase
-
-
-
-
oxygen oxidoreductase
984
-
phenol oxidase
phenolase
-
-
-
-
phenoloxidase
984
-
polyaromatic oxidase
-
-
-
-
polyphenol oxidase
polyphenol oxidase 3
309205
-
polyphenol oxidase 4
309210
UniProt
polyphenolase
-
-
-
-
polyphenoloxidase
984
-
PPO 3
309205
-
PPO2
283726
-
pyrocatechol oxidase
-
-
-
-
tryosinase
984
-
tryrosinase
984
-
tyrosinase
tyrosinase 4
309210
-
tyrosinase diphenolase
984
-
tyrosine-dopa oxidase
-
-
-
-
additional information
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tyrosine + O2 = dopaquinone + H2O
show the reaction diagram
2 L-dopa + O2 = 2 dopaquinone + 2 H2O
show the reaction diagram
mechanism of tyrosinase on monophenols and o-diphenol, overview
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
L-tyrosine,L-dopa:oxygen oxidoreductase
A type III copper protein found in a broad variety of bacteria, fungi, plants, insects, crustaceans, and mammals, which is involved in the synthesis of betalains and melanin. The enzyme, which is activated upon binding molecular oxygen, can catalyse both a monophenolase reaction cycle (reaction 1) or a diphenolase reaction cycle (reaction 2). During the monophenolase cycle, one of the bound oxygen atoms is transferred to a monophenol (such as L-tyrosine), generating an o-diphenol intermediate, which is subsequently oxidized to an o-quinone and released, along with a water molecule. The enzyme remains in an inactive deoxy state, and is restored to the active oxy state by the binding of a new oxygen molecule. During the diphenolase cycle the enzyme binds an external diphenol molecule (such as L-dopa) and oxidizes it to an o-quinone that is released along with a water molecule, leaving the enzyme in the intermediate met state. The enzyme then binds a second diphenol molecule and repeats the process, ending in a deoxy state [7]. The second reaction is identical to that catalysed by the related enzyme catechol oxidase (EC 1.10.3.1). However, the latter can not catalyse the hydroxylation or monooxygenation of monophenols.
CAS REGISTRY NUMBER
COMMENTARY hide
9002-10-2
not distinguished from EC 1.10.3.1
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-catechin hydrate + 1/2 O2
?
show the reaction diagram
-
-
-
?
(-)-epicatechin + 1/2 O2
?
show the reaction diagram
-
-
-
?
caffeic acid + 1/2 O2
caffeoyl quinone + H2O
show the reaction diagram
-
-
-
?
D-dopa + 1/2 O2
D-dopaquinone + H2O
show the reaction diagram
tyrosinase oxidizes L- and D-forms with similar rate
-
-
?
D-tyrosine + O2 + AH2
D-dopa + H2O + A
show the reaction diagram
tyrosinase oxidizes L- and D-forms with similar rate
-
-
?
DL-dopa + 1/2 O2
DL-dopaquinone + H2O
show the reaction diagram
tyrosinase oxidizes L- and D-forms with similar rate
-
-
?
DL-tyrosine + O2 + AH2
DL-dopa + H2O + A
show the reaction diagram
tyrosinase oxidizes L- and D-forms with similar rate
-
-
?
L-dopa + 1/2 O2
L-dopaquinone + H2O
show the reaction diagram
L-Dopa + O2
L-dopaquinone + H2O
show the reaction diagram
-
-
-
?
L-tyrosine + O2
dihydroxyphenylalanine quinone + H2O
show the reaction diagram
-
-
-
?
L-tyrosine + O2 + AH2
L-dopa + H2O + A
show the reaction diagram
tyrosinase oxidizes L- and D-forms with similar rate
-
-
?
p-cresol + O2 + AH2
4-methylpyrocatechol + H2O + A
show the reaction diagram
-
-
-
?
p-tyrosol + O2 + AH2
2-(3,4-dihydroxyphenyl)ethanol + H2O + A
show the reaction diagram
-
-
-
?
phenol + O2 + AH2
catechol + H2O + A
show the reaction diagram
-
-
-
?
pyrocatechol + 1/2 O2
1,2-benzoquinone + H2O
show the reaction diagram
-
-
-
?
pyrogallol + 1/2 O2
?
show the reaction diagram
-
-
-
?
tyramine + O2
4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione + H2O
show the reaction diagram
-
-
-
?
(R)-dopaxanthin + dehydroascorbic acid + O2
(R)-dopaxanthin quinone + L-ascorbic acid + H2O
show the reaction diagram
(R)-tyrosine-betaxanthin + L-DOPA + O2
(R)-dopaxanthin + dopaquinone + H2O
show the reaction diagram
-
i.e. (R)-portulacaxanthin II, the activity of the enzyme is not restricted to betaxanthins derived from (S)-amino acids
(R)-dopaxanthin is a pigment, quantitative product analysis
-
?
1,5-bis(4-hydroxyphenyl)-1,4-pentadiene-3-one + O2
?
show the reaction diagram
-
-
-
-
?
2 2-methyl-L-dopa + O2
2 2-methyldopaquinone + 2 H2O
show the reaction diagram
-
-
-
-
?
2 L-dopa + O2
2 dopaquinone + 2 H2O
show the reaction diagram
2 L-tyrosine + O2
2 L-dopa
show the reaction diagram
-
-
-
-
?
2-methyl-L-tyrosine + O2
2-methyldopaquinone + H2O
show the reaction diagram
-
-
-
-
?
2-methylresorcinol + O2
?
show the reaction diagram
-
acts as enzyme substrate and inhibitor, low activity
-
-
?
3,3',4',5,7-pentahydroxyflavone + 1/2 O2
?
show the reaction diagram
-
quercetin
-
-
?
3,4-dihydroxyphenylacetic acid + 1/2 O2
(3,4-dioxocyclohexa-1,5-dien-1-yl)acetic acid + H2O
show the reaction diagram
-
DHPAA
-
-
?
3,4-dihydroxyphenylalanine + 1/2 O2
dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
3,4-dihydroxyphenylalanine + O2
?
show the reaction diagram
-
-
-
-
?
3,4-dihydroxyphenylpropionic acid + 1/2 O2
3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid + H2O
show the reaction diagram
-
DHPPA
-
-
?
3-hydroxyanthranilic acid + O2
cinnabarinic acid + H2O
show the reaction diagram
-
-
-
?
3-hydroxybenzyl alcohol + O2
?
show the reaction diagram
-
-
-
-
?
3-methoxyphenol + O2
?
show the reaction diagram
-
-
-
-
?
3-[2-(3,4-dihydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-acetylphenyl)triazene + O2
(2E)-3-(4-acetylphenyl)-N-[2-(3,4-dioxocyclohexa-1,5-dien-1-yl)ethyl]-1-methyltriaz-2-ene-1-carboxamide + H2O
show the reaction diagram
-
-
-
-
?
3-[2-(3,4-dihydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-ethoxycarbonylphenyl)triazene + O2
ethyl 4-[(1E)-3-[[2-(3,4-dioxocyclohexa-1,5-dien-1-yl)ethyl]carbamoyl]-3-methyltriaz-1-en-1-yl]benzoate + H2O
show the reaction diagram
-
-
-
-
?
3-[2-(3,4-dihydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-tolyl)triazene + O2
(2E)-N-[2-(3,4-dioxocyclohexa-1,5-dien-1-yl)ethyl]-1-methyl-3-(4-methylphenyl)triaz-2-ene-1-carboxamide + H2O
show the reaction diagram
-
-
-
-
?
3-[2-(4-hydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-acetylphenyl)triazene + O2
(2E)-3-(4-acetylphenyl)-1-methyl-N-[2-(4-oxocyclohexa-1,5-dien-1-yl)ethyl]triaz-2-ene-1-carboxamide + H2O
show the reaction diagram
-
-
-
-
?
3-[2-(4-hydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-cyanophenyl)triazene + O2
(2E)-3-(4-cyanophenyl)-1-methyl-N-[2-(4-oxocyclohexa-1,5-dien-1-yl)ethyl]triaz-2-ene-1-carboxamide + H2O
show the reaction diagram
-
-
-
-
?
3-[2-(4-hydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-ethoxycarbonylphenyl)triazene + O2
ethyl 4-[(1E)-3-methyl-3-[[2-(4-oxocyclohexa-1,5-dien-1-yl)ethyl]carbamoyl]triaz-1-en-1-yl]benzoate + H2O
show the reaction diagram
-
-
-
-
?
3-[2-(4-hydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-tolyl)triazene + O2
(2E)-1-methyl-3-(4-methylphenyl)-N-[2-(4-oxocyclohexa-1,5-dien-1-yl)ethyl]triaz-2-ene-1-carboxamide + H2O
show the reaction diagram
-
-
-
-
?
4-bromophenol + O2
?
show the reaction diagram
-
-
-
-
?
4-chlorocatechol + 1/2 O2
4-chlorocyclohexa-3,5-diene-1,2-dione + H2O
show the reaction diagram
-
-
-
-
?
4-chlorophenol + O2
4-chloro-1,2-quinone + H2O
show the reaction diagram
-
-
-
-
?
4-ethoxyphenol + O2
?
show the reaction diagram
-
-
-
-
?
4-ethylcatechol + 1/2 O2
4-ethylcyclohexa-3,5-diene-1,2-dione + H2O
show the reaction diagram
-
-
-
-
?
4-ethylresorcinol + O2
?
show the reaction diagram
-
acts as enzyme substrate and inhibitor
-
-
?
4-fluorophenol + O2
?
show the reaction diagram
-
-
-
-
?
4-hexylresorcinol + O2
?
show the reaction diagram
-
-
-
-
?
4-hydroxyanisole + O2
3,4-dihydoxyanisol + H2O
show the reaction diagram
-
-
-
-
?
4-hydroxyanisole + O2
?
show the reaction diagram
-
-
-
-
?
4-hydroxybenzaldehyde + O2
?
show the reaction diagram
-
-
-
-
?
4-hydroxybenzyl alcohol + O2
?
show the reaction diagram
4-hydroxyphenyl acetic acid + O2
?
show the reaction diagram
-
-
-
-
?
4-hydroxyphenyl propionic acid + O2
?
show the reaction diagram
-
-
-
-
?
4-iodophenol + O2
?
show the reaction diagram
-
-
-
-
?
4-methoxyphenol + O2
?
show the reaction diagram
-
-
-
-
?
4-methylcatechol + 1/2 O2
4-methyl-1,2-benzoquinone + H2O
show the reaction diagram
4-Methylphenol + O2
?
show the reaction diagram
-
-
-
-
?
4-methylresorcinol + O2
?
show the reaction diagram
-
acts as enzyme substrate and inhibitor
-
-
?
4-n-butylresorcinol + O2
?
show the reaction diagram
-
-
-
-
?
4-nitrocatechol + 1/2 O2
4-nitrocyclohexa-3,5-diene-1,2-dione + H2O
show the reaction diagram
-
-
-
-
?
4-tert-butylcatechol + 1/2 O2
4-tert-butylcyclohexa-3,5-diene-1,2-dione + H2O
show the reaction diagram
-
-
-
-
?
4-tert-butylphenol + O2
4-tert-butyl 1,2-benzoquinone + H2O
show the reaction diagram
-
-
-
?
4-tert-butylphenol + O2
?
show the reaction diagram
-
-
-
-
?
4-[(4-methylphenyl)azo]-1,2-benzendiol + 1/2 O2
4-[(E)-(4-methylphenyl)diazenyl]cyclohexa-3,5-diene-1,2-dione + H2O
show the reaction diagram
4-[(4-methylphenyl)azo]-phenol + O2 + AH2
4-[(4-methylbenzo)azo]-1,2-benzendiol + H2O + A
show the reaction diagram
alpha-arbutin + O2
?
show the reaction diagram
-
alpha-arbutin also has a weaker inhibitory effect on the monophenolase activity of the enzyme, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions
-
-
?
beta-arbutin + O2
?
show the reaction diagram
caffeic acid + O2
caffeoyl quinone + H2O
show the reaction diagram
-
-
-
-
?
catechin + O2
?
show the reaction diagram
-
-
-
-
?
catechin dimer + O2
?
show the reaction diagram
-
-
-
-
?
catechin trimer + O2
?
show the reaction diagram
-
-
-
-
?
catechol + 1/2 O2
1,2-benzoquinone + H2O
show the reaction diagram
-
pyrogallol and catechol are best substrates for catalysis and inactivation
-
-
?
catechol + O2
1,2-benzoquinone + H2O
show the reaction diagram
-
-
-
-
?
catechol + O2
?
show the reaction diagram
reaction of EC 1.10.3.1
-
-
?
D-ascorbic acid + O2
?
show the reaction diagram
-
-
-
-
r
D-tyrosine + L-dopa + O2
D-dopa + dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
deoxyarbutin + O2
?
show the reaction diagram
oxytyrosinase is able to hydroxylate deoxyarbutin and finishes the catalytic cycle by oxidizing the formed o-diphenol to quinone, while the enzyme becomes deoxytyrosinase, which evolves to oxytyrosinase in the presence of oxygen. deoxyarbutin can alsio act as enzyme inhibitor. This compound is the only one described that does not release o-diphenol after the hydroxylation step. Oxytyrosinase hydroxylates the deoxyarbutin in ortho position of the phenolic hydroxyl group by means of an aromatic electrophilic substitution. As the oxygen orbitals and the copper atoms are not coplanar, but in axial/equatorial position, the concerted oxidation/reduction cannot occur and the release of a copper atom to bind again in coplanar position, enabling the oxidation/reduction or release of the o-diphenol from the active site to the medium. In the case of deoxyarbutin, the o-diphenol formed is repulsed by the water due to its hydrophobicity, and so can bind correctly and be oxidized to a quinone before being released
-
-
?
DL-2-methyltyrosine + O2
?
show the reaction diagram
-
-
-
-
?
dopamine + O2
?
show the reaction diagram
dopamine + O2
dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
ellagic acid + O2
?
show the reaction diagram
epicatechin + O2
?
show the reaction diagram
-
-
-
-
?
esculetin + 1/2 O2
2H-chromene-2,6,7-trione + H2O
show the reaction diagram
-
demonstration, that esculetin is no inhibitor, but a substrate of mushroom polyphenol oxidase (PPO) and horseradish peroxidase (POD)
-
-
?
gallic acid + 1/2 O2
5-hydroxy-3,4-dioxocyclohexa-1,5-diene-1-carboxylic acid + H2O
show the reaction diagram
-
-
-
-
?
gamma-L-glutaminyl-3,4-dihydroxybenzene + O2
gamma-L-glutaminyl-3,4-benzoquinone + H2O
show the reaction diagram
-
-
-
?
gamma-L-glutaminyl-4-hydroxybenzene + O2 + AH2
gamma-L-glutaminyl-3,4-dihydroxybenzene + H2O + A
show the reaction diagram
-
-
-
?
Gly-Gly-L-Tyr + O2
?
show the reaction diagram
-
-
-
-
?
Gly-L-Tyr-Gly + O2
?
show the reaction diagram
-
-
-
-
?
hydrocaffeic acid + O2
?
show the reaction diagram
-
-
-
-
?
hydroquinone + O2
?
show the reaction diagram
-
-
-
-
?
hydroxyhydroquinone + O2
2-hydroxy-p-benzoquinone + H2O
show the reaction diagram
-
the oxidation of hydroxyhydroquinone by O2 catalyzed by tyrosinase occurs simultaneously with the non-enzymatic oxidation of hydroxyhydroquinone at pH 7.0, the identical isosbestic points indicating that there is a stoichiometric transformation from hydroxyhydroquinone to 2-hydroxy p-benzoquinone, a red p-quinone
-
-
?
L-3,4-dihydroxyphenylalanine + 1/2 O2
L-dopaquinone + H2O
show the reaction diagram
-
individually grafted onto a novel CSG1.0 membrane as a ligand
-
-
?
L-dopa + 1/2 O2
L-dopachrome + H2O
show the reaction diagram
-
-
-
-
?
L-dopa + 1/2 O2
L-dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
L-DOPA + O2
?
show the reaction diagram
-
-
-
-
?
L-DOPA + O2
dopaquinone + H2O
show the reaction diagram
L-Dopa + O2
L-dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
L-Tyr + O2
L-Dopa + H2O
show the reaction diagram
-
diphenolase activity
-
-
?
L-Tyr-Gly-Gly + O2
?
show the reaction diagram
-
-
-
-
?
L-tyrosine + L-dopa + O2
L-dopa + dopaquinone + H2O
show the reaction diagram
L-tyrosine + O2
dopaquinone + H2O
show the reaction diagram
L-tyrosine + O2
L-DOPA + H2O
show the reaction diagram
L-tyrosine + O2 + AH2
L-3,4-dihydroxyphenylalanine + H2O + A
show the reaction diagram
L-tyrosine + O2 + AH2
L-dopa + H2O + A
show the reaction diagram
-
-
-
-
?
L-tyrosine methyl ester + O2
?
show the reaction diagram
-
-
-
-
?
methyl gallate + O2
methyl 5-hydroxy-3,4-dioxocyclohexa-1,5-diene-1-carboxylate + H2O
show the reaction diagram
-
-
-
-
?
N-acetyl-L-tyrosine + O2
N-acetyl-dopaquinone + H2O
show the reaction diagram
-
-
-
?
oxyresveratrol + O2
?
show the reaction diagram
p-coumaric acid + O2
caffeic acid + H2O
show the reaction diagram
-
-
-
-
?
p-tyrosol + O2
2-(3,4-dihydroxyphenyl)ethanol + H2O
show the reaction diagram
-
-
-
-
?
phenol + O2
?
show the reaction diagram
phenol + O2 + AH2
catechol + H2O + A
show the reaction diagram
-
-
-
-
?
phloretic acid + O2
?
show the reaction diagram
-
-
-
-
?
phloretin + O2
?
show the reaction diagram
-
the compound is a substrate and an inhibitor for tyrosinase
-
-
?
phloridzin + O2
?
show the reaction diagram
-
the compound is a substrate and an inhibitor for tyrosinase
-
-
?
phloroglucinol + 1/2 O2
?
show the reaction diagram
-
-
-
-
?
protocatechuic acid + 1/2 O2
3,4-dioxocyclohexa-1,5-diene-1-carboxylic acid + H2O
show the reaction diagram
-
-
-
-
?
protocatechuic aldehyde + 1/2 O2
3,4-dioxocyclohexa-1,5-diene-1-carbaldehyde + H2O
show the reaction diagram
-
-
-
-
?
pyrocatechol + 1/2 O2
1,2-benzoquinone + H2O
show the reaction diagram
-
-
-
-
?
pyrogallol + 1/2 O2
?
show the reaction diagram
resorcinol + O2
?
show the reaction diagram
-
acts as enzyme substrate and inhibitor
-
-
?
resveratrol + O2
?
show the reaction diagram
-
-
-
-
?
rhododendrol + O2
?
show the reaction diagram
-
-
-
-
?
tyramine + O2
?
show the reaction diagram
tyrosine + O2
dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
tyrosol + O2
?
show the reaction diagram
-
the compound is a substrate and an inhibitor for tyrosinase
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-tyrosine + O2
dihydroxyphenylalanine quinone + H2O
show the reaction diagram
-
-
-
?
2 L-dopa + O2
2 dopaquinone + 2 H2O
show the reaction diagram
2 L-tyrosine + O2
2 L-dopa
show the reaction diagram
-
-
-
-
?
dopamine + O2
?
show the reaction diagram
-
-
-
-
?
L-DOPA + O2
dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
L-tyrosine + L-dopa + O2
L-dopa + dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
L-tyrosine + O2
dopaquinone + H2O
show the reaction diagram
L-tyrosine + O2
L-DOPA + H2O
show the reaction diagram
-
-
-
-
?
tyrosine + O2
dopaquinone + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
if L-DOPA is an active cofactor, its formation as an intermediate during o-dopaquinone production is controversial
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
copper
H2O2
-
the exogenous oxygen molecule is bound as peroxide and bridges the two copper centers, conferring a distinct O2-Cu(II) charge transfer
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
-
4-hexylresorcinol
-
ammonium tetramolybdate
-
Salicylhydroxamic acid
-
(+)-gallocatechin-3-O-gallate
-
GCG, tyrosinase inhibitor
(+)haemanthamine
-
-
(-)-epicatechin-3-O-gallate
-
ECG, tyrosinase inhibitor
(-)-epigallocatechin
-
competitive, IC50: 0.035 mM
(-)-epigallocatechin-3-O-gallate
(1E,2E)-3-(2,4-dimethoxyphenyl)-N-hydroxy-1-(pyridin-2-yl)prop-2-en-1-imine
-
52.5% inhibition at 50 mM
(1E,4E)-1,5-bis(2-fluoro-4-methoxyphenyl)penta-1,4-dien-3-one
-
-
(1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one
-
-
(1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
-
-
(2-([4-(4-methoxy-benzyloxy)-benzylidene]-hydrazono)-4-oxothiazolidin-5-ylidene)-acetic acid methyl ester
-
-
(2-[(2-hydroxy-benzylidene)-hydrazono]-4-oxo-thiazolidin-5-ylidene)-acetic acid methyl ester
-
-
(2-[(5-methyl-furan-2-ylmethylene)-hydrazono]-4-oxothiazolidin-5-ylidene)-acetic acid methyl ester
-
-
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one
-
59.2% inhibition at 50 mM
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-3-yl)prop-2-en-1-one
-
55.9% inhibition at 50 mM
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-4-yl)prop-2-en-1-one
-
48.9% inhibition at 50 mM
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-2-yl)prop-2-en-1-one
-
49.5% inhibition at 50 mM
-
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-3-yl)prop-2-en-1-one
-
59.2% inhibition at 50 mM
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-4-yl)prop-2-en-1-one
-
42.7% inhibition at 50 mM
(2E)-3-(2,4-dimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one
-
12.3% inhibition at 50 mM
(2E)-3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-(4-hydroxybenzyl)prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dimethoxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-chlorophenyl)-N-[2-(4-chlorophenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-hydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide
-
strong tyrosinase inhibitory potential
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
-
-
(2E)-3-(4-methoxyphenyl)-N-(1-phenylethyl)prop-2-enamide
-
-
(2E)-3-(4-methoxyphenyl)-N-(2-phenylethyl)prop-2-enamide
-
-
(2E)-3-(4-methoxyphenyl)prop-2-enoic acid
-
-
(2E)-3-phenyl-N-(1-phenylethyl)prop-2-enamide
-
-
(2E)-3-phenyl-N-(2-phenylethyl)prop-2-enamide
-
-
(2E)-3-phenylprop-2-enoic acid
-
-
(2E)-3-[4-(dimethylamino)phenyl]-1-(pyridin-2-yl)prop-2-en-1-one
-
16.9% inhibition at 50 mM
(2E)-but-2-enoic acid
-
non-competitive inhibition
(2E)-N-(3,4-dihydroxybenzyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide
-
-
(2E)-N-(4-chlorobenzyl)-3-phenylprop-2-enamide
-
-
(2E)-N-benzyl-3-(3,4-dihydroxyphenyl)prop-2-enamide
-
-
(2E)-N-benzyl-3-(4-hydroxyphenyl)prop-2-enamide
-
strong tyrosinase inhibitory potential
(2E)-N-benzyl-3-(4-methoxyphenyl)prop-2-enamide
-
-
(2E)-N-benzyl-3-phenylprop-2-enamide
-
-
(2E)-N-[2-(4-chlorophenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
-
-
(2E)-N-[2-(4-chlorophenyl)ethyl]-3-phenylprop-2-enamide
-
-
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide
-
-
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
-
-
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
-
-
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-methoxyphenyl)prop-2-enamide
-
-
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-phenylprop-2-enamide
-
-
(2E,4E)-hexa-2,4-dienoic acid
-
non-competitive inhibition
(2E,6E)-2,6-bis[(4-chlorophenyl)methylidene]cyclohexanone
-
-
(2E,6E)-2,6-bis[(4-hydroxyphenyl)methylidene]cyclohexanone
-
-
(2R,3R)-taxifolin
-
isolated from the sprout of Polygonum hydropiper L. (Benitade), inhibited 70% of tyrosinase activity at a concentration of 0.50 mM
(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-(4-methoxyphenyl)prop-2-enoic acid
-
-
(2Z)-3-phenylprop-2-enoic acid
-
-
(4-oxo-2-[(1H-pyrrol-2-ylmethylene)-hydrazono]-thiazolidin-5-ylidene)-acetic acid methyl ester
-
-
(4-oxo-2-[(3-phenyl-allylidene)-hydrazono]-thiazolidin-5-ylidene)-acetic acid methyl ester
-
-
(7S, 8R, 8'R)-(-)-lariciresinol-4'-O-beta-D-glucopyranoside
-
tyrosinase inhibitors from Marrubium velutinum, lignan glucosides
(7S, 8R, 8'R)-(-)-lariciresinol-4,4'-O-bis-beta-D-glucopyranoside
-
tyrosinase inhibitors from Marrubium velutinum, lignan glucosides
(7S, 8R, 8'R)-(-)-lariciresinol-4-O-beta-D-glucopyranoside
-
tyrosinase inhibitors from Marrubium velutinum, lignan glucosides
(R)-HTCCA
-
-
(S)-HTCCA
-
-
1,10-bis(1,10-carboxyethyl) ether
-
-
1,3-dimethylimidazolium methylsulfate
-
69.7% residual activity at 5% (w/v)
1,5-bis(4-hydroxyphenyl)-1,4-pentadiene-3-one
-
-
1-(1,4-diacetylphenyl)dithiosemicarbazide
-
-
1-(1-(2,4,6-trihydroxyphenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(2,4-dihydroxyphenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(4-bromophenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(4-fluorophenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(4-hydroxyphenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(4-isopropylphenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(4-methoxyphenyl)ethylidene)thiosemicarbazide
-
-
1-(1-(4-methoxyphenyl)propan-2-ylidene)-thiosemicarbazide
-
-
1-(1-(4-methoxyphenyl)propan-2-ylidene)thiosemicarbazide
-
-
1-(1-(pyrazin-2-yl)ethylidene)thiosemicarbazide
-
-
1-(1-(pyridin-3-yl)ethylidene)thiosemicarbazide
-
-
1-(1-(thiophen-2-yl)ethylidene)thiosemicarbazide
-
-
1-(1-p-tolylethylidene)thiosemicarbazide
-
-
1-(1-phenylethylidene)thiosemicarbazide
-
-
1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)propane
-
tyrosinase inhibitor with strong depigmenting effects, found in the medicinal plant Dianella ensifolia. Synthetic and plant derived versions of the enzyme inhibit mushroom tyrosinase with similar potencies
1-(2,4-dimethoxyphenyl)-3-hydroxyurea
-
-
1-(2,5-dimethyl-1H-pyrrol-1-yl)thiourea
-
-
1-(2-hydroxy-1,2-diphenylethylidene)thiosemicarbazide
-
-
1-(2-oxo-1,2-diphenylethylidene)thiosemicarbazide
-
-
1-(3-methylbutylidene)thiosemicarbazide
-
-
1-(3-oxocyclohexylidene)thiosemicarbazide
-
-
1-(3-phenylallylidene)thiosemicarbazide
-
-
1-(4-(4-hydroxyphenyl)butan-2-ylidene)-thiosemicarbazide
-
-
1-(4-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide
-
-
1-(4-bromophenyl)-3-hydroxyurea
-
-
1-(4-butoxyphenyl)-3-hydroxyurea
-
-
1-(4-fluorophenyl)-ethanone
-
-
1-(4-methoxyphenyl)-ethanone
-
-
1-(4-methylpent-3-en-2-ylidene) thiosemicarbazide
-
-
1-(but-2-enylidene)thiosemicarbazide
-
-
1-(butan-2-ylidene)thiosemicarbazide
-
-
1-(propan-2-ylidene)thiosemicarbazide
1-(thiophen-2-yl)-ethanone
-
-
1-butyl-3-methylimidazolium methylsulfate
-
47.8% residual activity at 5% (w/v)
1-cyclohexylidenethiosemicarbazide
-
-
1-cyclopentyl-1-hydroxy-2-oxohydrazine
-
inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-cyclopentylidenethiosemicarbazide
-
-
1-dodecyl-1-hydroxy-2-oxohydrazine
-
inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-ethyl-3-methylimidazolium methylsulfate
-
64.1% residual activity at 5% (w/v)
1-ethylidenethiosemicarbazide
-
-
1-hydroxy-1,3-dimethyl-3-phenylurea
-
-
1-hydroxy-1-methyl-3-(4-nitrophenyl)urea
-
-
1-hydroxy-1-methyl-3-phenylurea
-
-
1-hydroxy-1-naphthalen-1-yl-2-oxohydrazine
-
inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-hydroxy-2-oxo-1-phenylhydrazine
-
inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-hydroxy-3-(4-hydroxyphenyl)urea
-
-
1-hydroxy-3-(4-methoxyphenyl)urea
-
-
1-hydroxy-3-(4-nitrophenyl)urea
-
-
1-hydroxy-3-phenylthiourea
-
-
1-hydroxy-3-phenylurea
-
also retains a substantial potency in cell culture by reducing pigment synthesis by 78%
1-hydroxy-3-[4-(trifluoromethyl)phenyl]urea
-
-
1-methoxy-3-(4-nitrophenyl)thiourea
-
-
1-methoxy-3-naphthalen-2-ylthiourea
-
-
1-methoxy-3-phenylurea
-
-
1-methylethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
1-pentanoyl-3-(2,3-dichlorophenyl)thiourea
-
-
1-pentanoyl-3-(2,4,6-trimethylphenyl)thiourea
-
-
1-pentanoyl-3-(2,4-dinitrophenyl)thiourea
-
-
1-pentanoyl-3-(2,6-dibromo-4-fluorophenyl)thiourea
-
-
1-pentanoyl-3-(3-nitrophenyl)thiourea
-
-
1-pentanoyl-3-(4-bromo-2-fluorophenyl)thiourea
-
-
1-pentanoyl-3-(4-bromophenyl)thiourea
-
-
1-pentanoyl-3-(4-chlorophenyl)thiourea
-
-
1-pentanoyl-3-(4-methoxyphenyl)thiourea
-
noncompetitive inhibition, docking interaction analysis between 1-pentanoyl-3-(4-methoxyphenyl)thiourea and mushroom tyrosinase
1-pentanoyl-3-(4-nitrophenyl)thiourea
-
-
1-propylidenethiosemicarbazide
-
-
1-[1-(4-methoxyphenyl)ethylidene]thiosemicarbazide
-
-
1-[4-(benzyloxy)phenyl]-3-hydroxyurea
-
-
1-[[tert-butyl(dimethyl)silyl]oxy]-3-phenylurea
-
-
2'-(3,4-dihydroxyphenyl)-3',5,5',7,7'-pentahydroxy-2-(4-hydroxyphenyl)-2,2',3,3',4a,8a-hexahydro-4H,4'H-3,8'-bichromene-4,4'-dione
-
most potent inhibitor
2,2':4',2''-ter-1,3,4-oxadiazole-5,5',5''(4H,4''H)-trithione
-
-
2,2':4',2''-ter-1,3,4-thiadiazole-5,5',5''(4H,4''H)-trithione
-
-
2,3,4'-trihydroxy-4-methoxydeoxybenzoin
-
displays stable and significant inhibitory effect on tyrosinase activity
2,3,4,4'-tetrahydroxydeoxybenzoin
-
-
2,3,4-trihydroxy-3',4'-dimethoxydeoxybenzoin
-
-
2,3,4-trihydroxy-4'-methoxydeoxybenzoin
-
-
2,4,4',6-tetrahydroxydeoxybenzoin
-
-
2,4,4'-trihydroxydeoxybenzoin
-
-
2,4,5-trihydroxy-4'-methoxydeoxybenzoin
-
-
2,4,6-trihydroxy-4'-methoxydeoxybenzoin
-
-
2,4-dichlorocinnamic acid
-
-
2,4-dihydroxy-3',4'-dimethoxydeoxybenzoin
-
-
2,4-dihydroxy-4'-methoxydeoxybenzoin
-
-
2,4-dihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide
-
IC50: 0.550 mM
2,4-dihydroxy-N-(4-hydroxybenzyl)benzamide
-
IC50: 1.820 mM
2-(2-furanylmethylene)-thiosemicarbazone
-
-
2-(2-hydroxyethoxy)ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
2-(2-methoxyethoxy)ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl 3,4,5-trihydroxybenzoate
-
mixed-type inhibitor
2-(4-fluorophenyl)-quinazolin-4(3H)-one
-
synthesis of the tyrosinase inhibitor, inhibits the diphenolase activity of tyrosinase. Structure analysis by 1H and 13C NMR spectroscopy, Fourier transform infrared spectroscopy (FTIR), and high resolution mass spectrometry. Molecular docking simulation analysis and inhibition mechanism, a mixed-type inhibitor exerting reversible inhibition, overview. The inhibitor does not reduce the amount of the enzyme, but decreases the enzyme activity for the oxidation of L-dopa
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-chlorophenyl)prop-2-enoate
-
mixed-type inhibition
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
-
reversible, mixed-type inhibition
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 2,4-dihydroxybenzoate
-
mixed-type inhibition
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 3,4-dihydroxybenzoate
-
-
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 3,5-dihydroxybenzoate
-
-
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 4-hydroxybenzoate
-
-
2-(chloromethyl)-10-(2-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione
-
-
2-(chloromethyl)-10-(4-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione
-
i.e. DHPC04, binding mode of R-DHPC04 and S-DHPC04 on the catalytic site of the enzyme, interactions between DHPC04 and residues His243 and Asn260
2-(hydroxymethyl)-7,7-dimethyl-10-phenyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione
-
weak inhibition
2-(phenylmethylene)-thiosemicarbazone
-
-
2-acetylamino-1,3,4-thiadiazole-5-sulfonamide
-
acetazolamide or ACZ, in vitro, in vivo studies, and in silico docking studies. Inhibition kinetics, noncompetitive inhibition. Molecular dynamics simulations, overview
2-butyl-5-hydroxyphenyl 3-(3,4-dihydroxyphenyl)propanoate
-
KI-063, a new tyrosinase inhibitor, strong concentration-dependent inhibitory effect on tyrosinase activity
2-chlorobenzaldehyde thiosemicarbazone
-
exhibits significant inhibitory potency on both monophenolase activity and diphenolase activity of tyrosinase, reversible noncompetitive inhibitor
2-chlorocinnamic acid
-
-
2-cyano-4-hydroxycinnamic acid
-
-
2-ethyl-3-hydroxy-4H-pyran-4-one
-
-
2-hydroxy-4-methoxybenzoic acid
-
-
2-hydroxy-4-methylbenzoic acid
-
-
2-hydroxy-5-methoxybenzoic acid
-
-
2-hydroxy-5-methylbenzoic acid
-
-
2-Hydroxybenzaldehyde
-
-
2-hydroxybenzoic acid
-
-
2-hydroxyethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
2-methoxyethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
2-Methylbenzaldehyde
-
-
2-Methylbenzoic acid
-
-
2-Methylresorcinol
-
acts as enzyme substrate and inhibitor
2-oxoglutaric acid
-
AKG, a reversible inhibitor of tyrosinase, inhibition kinetics integrated with molecular dynamics simulations reveal a complex induced parabolic slope mixed-type inhibition. AKG significantly inhibits the L-dopa oxidation of tyrosinase in a dose-dependent manner, complete inactivation at about 25 mM. Enzyme residues His85, His259, Asn260, Phe264, Met280, Gly281, and Val283 interact with the inhibitor
2-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]phenol
-
77.5% inhibition at 50 mM, reversible competitive inhibition
2-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]phenol
-
80.6% inhibition at 50 mM, reversible competitive inhibition
2-[(1E,2E)-N-hydroxy-3-(pyridin-4-yl)prop-2-enimidoyl]phenol
-
69.8% inhibition at 50 mM
2-[(2,3,4-trihydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(2,4-dihydroxyphenyl)methylene]-thiosemicarbazone
-
most potent tyrosinase inhibitor
2-[(2,5-dihydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(2,5-dimethoxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(2-hydroxy-4-bromophenyl)methylene]thiosemicarbazone
-
-
2-[(2-hydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3,4,5-trihydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3,4,5-trimethoxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3,4-dihydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3,5-dihydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3-hydroxy-4-methoxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3-hydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(3-methoxy-4-hydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(4-bromophenyl)methylene]-thiosemicarbazone
-
-
2-[(4-hydroxyphenyl)methylene]-thiosemicarbazone
-
-
2-[(4-methoxyphenyl)methylene]-thiosemicarbazone
-
-
2-[2-(2,4-dihydroxyphenyl)ethyl]-5-(D-xylopyranosyloxy)phenyl D-xylopyranoside
-
isolated from Chlorophytum arundinaceum (liliaceae)
2-[2-(2,4-dihydroxyphenyl)ethyl]-5-hydroxyphenyl D-xylopyranoside
-
isolated from Chlorophytum arundinaceum (liliaceae)
2-[2-(2-hydroxyethoxy)ethoxy]ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
2-[2-(2-methoxyethoxy)ethoxy]ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(2,4-dihydroxyphenyl)prop-2-enoate
non-competitive inhibitor, binding to the enzyme's binuclear active site is irreversible. The 2-hydroxy group in the compound interacts with amino acid HIS85 which is present in active binding site
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-chlorophenyl)prop-2-enoate
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
mixed-type inhibition
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-phenylprop-2-enoate
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 2,4-dihydroxybenzoate
mixed-type inhibition
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,4,5-trihydroxybenzoate
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,4-dihydroxybenzoate
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,5-dihydroxybenzoate
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3-hydroxybenzoate
-
2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 4-hydroxybenzoate
-
2-[3-(2,4-dimethoxy-3-methylphenyl)propyl]benzene-1,4-diol
-
plant-derived diarylpropane tyrosinase inhibitor
2alpha,3alpha,23-trihydroxyolean-12-en-28-oic acid
-
pentacyclic triterpene extracted from Rhododendron collettianum
3'',4''-dihydroglabridin
-
100% inhibition at 0.33 mg/ml
3',5,5',7,7'-pentahydroxy-2,2'-bis(4-hydroxyphenyl)-2,2',3,3',4a,8a-hexahydro-4H,4'H-3,8'-bichromene-4,4'-dione
-
-
3,4,5-trihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide
-
IC50: 0.555 mM
3,4,5-trihydroxy-N-(4-hydroxybenzyl)benzamide
-
IC50: 1.180 mM
3,4-dihydroxy-4'-methoxydeoxybenzoin
-
-
3,4-dihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide
-
IC50: 0.280 mM
3,4-dihydroxy-N-(4-hydroxybenzyl)benzamide
-
IC50: 2.0 mM
3,4-dihydroxybenzaldehyde-O-ethyloxime
-
-
3,4-dihydroxycinnamic acid
-
noncompetitive inhibition
3,4-dimethoxycinnamic acid
-
2.5% inhibition at 0.33 mM
3,4-dimethoxydihydrocinnamic acid
-
20.2% inhibition at 1 mM
3,5-dihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide
-
IC50: 0.705 mM
3,5-dihydroxy-N-(4-hydroxybenzyl)benzamide
-
IC50: 0.710 mM
3,7,3',4'-taxifolin tetraacetate
-
assayed together with (2R,3R)-taxifolin
3-(3',4',5'-trihydroxyphenyl)-6,8-dihydroxycoumarin
-
potent, non-competitive tyrosinase inhibitior, 68.3% inhibition at 0.8 mM
3-(3-hydroxyphenyl)-2H-chromen-2-one
-
19.3% inhibition at 0.8 mM
3-(4-bromophenyl)-1-hydroxy-1-methylurea
-
-
3-hydroxy-1,2-dimethyl-4(1H)-pyridone
-
-
3-hydroxy-1-methyl-1-phenylurea
-
-
3-Hydroxybenzaldehyde
-
-
3-hydroxycinnamic acid
-
-
3-hydroxycoumarin
-
-
3-hydroxyphloretin
-
constituents from the formosan apple (Malus doumeri var. formosana), exhibits a dose-dependent inhibitory effect on mushroom tyrosinase activity, competitive inhibitor. Enzyme kinetics study of 3-hydroxyphloretin as inhibitor with various concentrations of the L-tyrosine substrate (15.625, 31.25, 62.5, 125, 250, 500 microM)
3-methoxy-1-methyl-1-phenylurea
-
-
3-Methoxybenzaldehyde
-
-
3-methylbenzaldehyde
-
-
3-methylbenzoic acid
-
-
3-methylcrotonic acid
-
-
3-O-[2,6-di-O-alpha-L-rhamnopyranosyl-beta-D-galactopyranosyl]-quercetin
-
from Guioa villosa leaf extract
3-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]naphthalen-2-ol
-
58.2% inhibition at 50 mM
3-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]naphthalen-2-ol
-
62.6% inhibition at 50 mM
3-[(1E,2E)-N-hydroxy-3-(pyridin-4-yl)prop-2-enimidoyl]naphthalen-2-ol
-
57.5% inhibition at 50 mM
3beta, 23, 24-trihydroxyolean-12-en-28-oic acid
-
pentacyclic triterpene extracted from Rhododendron collettianum
4'-hydroxy-[1,1'-biphenyl]-2-carboxylic acid
-
-
4'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
-
-
4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid
-
binding mode, modeling
4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid
-
-
4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid
-
-
4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid
-
binding mode, modeling
4,4'-diamino-3-(4-hydroxyphenyl)-1'H-1,3'-bi-1,2,4-triazole-5,5'(4H,4'H)-dithione
-
-
4,4'-diamino-3-(pyridin-4-yl)-1'H-1,3'-bi-1,2,4-triazole-5,5'(4H,4'H)-dithione
-
-
4,4'-ethane-1,2-diyldibenzene-1,3-diol
-
-
4-(1-methylethyl)benzaldehyde
-
-
4-(1-methylethyl)benzoic acid
-
-
4-(2-(hydroxymethyl)-7,7-dimethyl-4,9-dioxo-4,6,7,8,9,10-hexahydropyrano[3,2-b]chromen-10-yl)benzonitrile
-
-
4-(benzyloxy)-N'-(hydrazinylcarbonyl)benzohydrazide
-
-
4-(hexyloxy)benzoic acid
-
-
4-(pentyloxy)benzoic acid
-
-
4-Aminobenzoic acid
-
a noncompetitive inhibitor
4-butoxybenzoic acid
-
-
4-butylbenzaldehyde
-
-
4-butylbenzoic acid
-
-
4-chlorobenzaldehyde thiosemicarbazone
-
exhibits significant inhibitory potency on both monophenolase activity and diphenolase activity of tyrosinase, reversible mixed-type inhibitor
4-chlorosalicylic acid
-
-
4-coumaric acid
-
74.4% inhibition at 0.33 mM
4-ethenylbenzaldehyde
-
-
4-ethenylbenzoic acid
-
-
4-ethoxybenzoic acid
-
-
4-Ethylbenzaldehyde
-
-
4-ethylbenzoic acid
-
-
4-ethylresorcinol
-
acts as enzyme substrate and inhibitor
4-formyl-2-methoxyphenyl (4-methylpiperazin-1-yl)acetate
-
reversible, non-competitive inhibition
4-formyl-2-methoxyphenyl (4-phenylpiperazin-1-yl)acetate
-
-
4-formyl-2-methoxyphenyl chloroacetate
-
-
4-formylphenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
-
-
4-formylphenyl 2,3,4-tri-O-acetyl-beta-D-allopyranoside
-
-
4-formylphenyl 2,3,4-tri-O-benzyl-beta-D-ribopyranoside
-
-
4-formylphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside
-
-
4-formylphenyl 2,3-O-(1-methylethylidene)-beta-D-allopyranoside
-
-
4-formylphenyl 4,6-O-(phenylmethylidene)-beta-D-gulopyranoside
-
-
4-formylphenyl 6-O-(dimethoxyphosphoryl)-beta-D-allopyranoside
-
-
4-formylphenyl 6-O-trityl-beta-D-allopyranoside
-
-
4-formylphenyl beta-D-allopyranoside
-
-
4-formylphenyl beta-D-glucopyranoside
-
-
4-formylphenyl beta-D-ribopyranoside
-
-
4-formylphenyl-O-beta-D-allopyranoside
-
-
4-heptylbenzaldehyde
-
-
4-heptylbenzoic acid
-
-
4-hexylbenzaldehyde
-
-
4-hexylbenzoic acid
-
-
4-hexylresorcinol
-
-
4-hydroxy-3-methoxycinnamic acid
-
noncompetitive inhibition
4-hydroxyanisole
-
can also act as enzyme substrate
4-hydroxybenzaldehyde
4-hydroxybenzoic acid
-
-
4-Hydroxybenzyl alcohol
-
the compound is a substrate and an inhibitor for tyrosinase, 39% inhibition at 1.5 mM
4-hydroxycinnamic acid
-
competitive inhibition of tyrosinase by 4-hydroxycinnamic acid is a slow, reversible reaction with fractional remaining activity, has no effects on the proliferation of normal liver L02 cells, delays the mushroom browning. Molecular docking analysis and kinetic modeling, structure-function analysis, detailed overview
4-Hydroxycoumarin
-
weak inhibition
4-hydroxyphenyl beta-D-xyloside
-
-
4-hydroxyphenyl beta-xylodioside
-
competitive inhibitor
4-hydroxyphenyl beta-xylotetraoside
-
competitive inhibitor, shows 35fold more potent inhibitory activity than beta-arbutin
4-hydroxyphenyl beta-xylotrioside
-
competitive inhibitor
4-methoxybenzaldehyde
-
-
4-methoxybenzoic acid
-
-
4-methoxycinnamic acid
4-methylbenzaldehyde
-
-
4-methylbenzoic acid
-
-
4-methylresorcinol
-
acts as enzyme substrate and inhibitor
4-n-butylresorcinol
-
-
4-octylbenzaldehyde
-
-
4-octylbenzoic acid
-
-
4-pentylbenzaldehyde
-
-
4-pentylbenzoic acid
-
-
4-phenyl-2-butanol
-
a reversible, potent inhibitor of tyrosinase, mixed-type inhibitor fothe monophenoase activity and noncompetitive-type inhibitor for the diphenolase activity
4-propoxybenzoic acid
-
-
4-propylbenzaldehyde
-
-
4-propylbenzoic acid
-
-
4-tert-butylbenzaldehyde
-
-
4-tert-butylbenzoic acid
-
-
4-xylidine-bis(dithiocarbamate) sodium salt
-
Na-SSC-NH-CH2-C6H4-CH2-NH-CSS-Na, mixed-type inhibition for both, catecholase and cresolase activities
4-[(1E,3E)-3-(hydroxyimino)-3-(pyridin-2-yl)prop-1-en-1-yl]-N,N-dimethylaniline
-
50.6% inhibition at 50 mM
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl beta-D-allopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl beta-D-glucopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside
-
reversible and competitive-type inhibitor
4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl beta-D-allopyranoside
-
-
4-[(E)-(hydroxyimino)methyl]phenyl beta-D-glucopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl beta-D-allopyranoside
-
-
4-[(E)-(methoxyimino)methyl]phenyl beta-D-glucopyranoside
-
-
4-[2-(2,4-dihydroxyphenyl)ethyl]-3-hydroxyphenyl D-xylopyranoside
-
isolated from Chlorophytum arundinaceum (liliaceae)
4-[3-(2-hydroxy-5-methoxyphenyl)propyl]benzene-1,3-diol
-
plant-derived diarylpropane tyrosinase inhibitor
4-[[hydroxy(nitroso)amino]methyl]benzene-1,3-diol
-
inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
4-[[hydroxy(nitroso)amino]methyl]phenol
-
inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
5'-(3-hydroxyphenyl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-(4-hydroxyphenyl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-(4-hydroxyphenyl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione
-
-
5'-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione
-
-
5'-(diphenylmethyl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-(diphenylmethyl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione
-
-
5'-(naphthalen-1-yl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-(pyridin-4-yl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-(pyridin-4-yl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione
-
-
5'-benzyl-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-cyclohexyl-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-phenyl-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-phenyl-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione
-
-
5'-[(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)methyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)methyl]-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione
-
-
5'-[3-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-[3-(benzyloxy)phenyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5'-[4-(benzyloxy)phenyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione
-
-
5,2',4'-trihydroxy-2'',2''-dimethylchromene-(6,7:5'',6'')-flavanone
-
dalenin, the reversible inhibitor is 52 and 495times more effective as a monophenolase inhibitor than hydroquinone and kojic acid, respectively, non-competitive inhibitor with L-DOPA as substrate, mixed-I type inhibitor with L-tyrosine as substrate
5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-2,2',3,3',4a,8a-hexahydro-4H,4'H-3,8'-bichromene-4,4'-dione
-
-
5,5',7-trihydroxy-2,2'-bis(4-hydroxyphenyl)-4,4'-dioxo-3,3',4,4',4a,8a-hexahydro-2H,2'H-3,8'-bichromen-7'-yl D-glucopyranoside
-
tyrosinase inhibitor isolated from extracts of the seeds of Garcinia kola
5,6,7,4'-tetramethylscutellarein
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols. Methoxylated flavones, like the methylethers of scutellarein, showed 10times lower inhibitory activity than kojic acid
5,6,7,8,4'-pentahydroxyflavone
-
tyrosinase inhibitors from Marrubium cylleneum, flavones/flavonols
5,7,3',4'-taxifolin teramethyl ether
-
assayed together with (2R,3R)-taxifolin
5,7,4'-trimethylscutellarein
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols. Methoxylated flavones, like the methylethers of scutellarein, showed 10times lower inhibitory activity than kojic acid
5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
97.49% inhibition at 0.2 mM
5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)trione
-
14.3% inhibition at 0.2 mM
5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
88.67% inhibition at 0.2 mM
5-(4-(2-butoxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
78.67% inhibition at 0.2 mM
5-(4-(2-butoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
85.88% inhibition at 0.2 mM
5-(4-(2-butoxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
complete inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
95.86% inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
5.27% inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
16.54% inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
22.41% inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
23.12% inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
complete inhibition at 0.2 mM
5-(4-(4-methoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
12.2% inhibition at 0.2 mM
5-(4-(4-methoxybutoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
9.85% inhibition at 0.2 mM
5-(4-(4-methoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
1.15% inhibition at 0.2 mM
5-(4-(4-methoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-hydroxybenzyl)-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-hydroxybenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
47.5% inhibition at 0.2 mM
5-(4-hydroxybenzylidene)-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-hydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
complete inhibition at 0.2 mM
5-ethenyl-5-hydroxy-3-isocyanocyclopent-2-en-1-one
-
inhibitor produced by Trichoderma viride strain H1-7 from a marine environment. Competitive inhibition
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
-
-
5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid
-
-
5-hydroxymethyl-2-furfural
-
noncompetitive inhibition
6'-glucosyl-martynoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of 6'-glucosyl-martynoside in the presence of CuSO4 (0.05 mM)
6-hydroxy-2H-pyran-3-carbaldehyde
-
a new tyrosinase inhibitor from Crinum yemense, testing for tyrosinase inhibiting activity, based on structural similarity to kojic acid. It shows a concentration-dependant reduction in tyrosinase activity similar to kojic acid in an in vitro assay, more potent than kojic acid
6-hydroxy-3-(4'-hydroxyphenyl)coumarin
-
26.7% inhibition at 0.8 mM
6-hydroxy-kaempferol-3-O-rutinoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
6-hydroxyapigenin
-
5,6,7-trihydroxyflavone, high inhibitory effects on tyrosinase. Acts as a cofactor to monophenolase
6-hydroxycoumarin
-
weak inhibition
6-hydroxygalangin
-
5,6,7-trihydroxyflavone, high inhibitory effects on tyrosinase. Acts as a cofactor to monophenolase
6-hydroxykaempferol
-
5,6,7-trihydroxyflavone, high inhibitory effects on tyrosinase. Acts as a cofactor to monophenolase. competitive inhibitor
7-(2,4-dihydroxyphenyl)-4-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro(3,2-g)chromen-5-one
-
artocarpfuranol, isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
7-hydroxy-3-(4-hydroxyphenyl)-2H-chromen-2-one
-
9.6% inhibition at 0.8 mM
7-hydroxycoumarin
-
-
8-isoprenyl-5'-geranyl-5,7,2',4'-tetrahydroxy flavanone
-
competitive inhibitor
8-O-methyltianmushanol
-
-
9-hydroxy-4-methoxypsoralen
-
noncompetitive inhibition
Ac-KSRFR
-
N-acetyl-pentapeptide Ac-P2, mixed-type inhibition
Ac-KSSFR
-
N-acetyl-pentapeptide Ac-P3, mixed-type inhibition
Ac-RSRFK
-
N-acetyl-pentapeptide Ac-P1, mixed-type inhibition
Ac-RSRFS
-
N-acetyl-pentapeptide Ac-P4, mixed-type inhibition
acetone
-
increasing solvent concentration up to 80% (v/v) yields a gradual reduction in the activity of the soluble and cross-linked enzyme forms, the cross-linked enzyme aggregate shows about 40% residual activity after incubation in acetone for about 34 h
acetophenone
-
-
acteoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of acteoside in the presence of CuSO4 (0.05 mM)
afzelechin
-
-
Agaritine
-
uncompetitive inhibition
albafuran A
-
-
aloesin
alpha-arbutin
-
inhibition of monophenolase activity, the inhibitory activity of beta-arbutin is higher compared to alpha-arbutin, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions
alpha-cyano-4-hydroxycinnamic acid
-
-
alpha-picolyl heptyl amine
-
-
alpha-picolyl nonyl amine
-
-
alpha-picolyl pentyl amine
-
-
alpha-picolyl propyl amine
-
-
alyssonoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
anacardic acid
-
competitive inhibition
angelic acid
-
-
Anisaldehyde
Anisic acid
-
uncompetitive inhibition
anthraglycoside B
-
anthraquinone, isolated from the root of Polygonum cuspidatum
Antrodia camphorata extract
-
basidiomycete, only other effect on tyrosinase activity is prepared from Antrodia camphorata using 75% ethanol extraction
-
apigenin
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols
apigenin 4'-O-beta-D-glucopyranoside
-
from Guioa villosa leaf extract
apigenin-7-O-(3'',6''-di-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
apigenin-7-O-(6''-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium cylleneum, flavone/flavonol acylated glucosides
arbutin
arbutine
-
clinically used tyrosinase inhibitor
arjungenin
-
pentacyclic triterpene extracted from Rhododendron collettianum
arjunilic acid
-
pentacyclic triterpene extracted from Rhododendron collettianum, most potent inhibitor, have potential to be used for the treatment of hyperpigmentation associated with the high production of melanocytes
artocarpanone
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
artocarpesin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
artocarpetin
-
isolated from the wood of Artocarpus heterophyllus
artocarpin
-
isolated from the wood of Artocarpus heterophyllus
ascorbic acid
azelaic acid
baicalein
-
5,6,7-trihydroxyflavone, high inhibitory effects on tyrosinase. Acts as a cofactor to monophenolase
Barbituric acid
-
5.95% inhibition at 0.2 mM
bayogenin
-
pentacyclic triterpene extracted from Rhododendron collettianum
benzaldehyde
-
-
benzohydroxamic acid
-
is known to inhibit tyrosinase by chelating with copper. Completely independent of pH
benzoic acid
benzylacetone
-
a reversible, potent inhibitor of tyrosinase, mixed-type inhibitor
benzyldithiocarbamate sodium salt
-
C6H5-CH2-NH-CSS-Na, noncompetitive inhibition for both, catecholase and cresolase activities
benzylideneacetone
-
a reversible, potent inhibitor of tyrosinase, mixed-type inhibitor
beta-arbutin
beta-picolyl heptyl amine
-
uncompetitive inhibition of monophenolase and diphenolase activities
beta-picolyl nonyl amine
-
-
beta-picolyl pentyl amine
-
uncompetitive inhibition of monophenolase and diphenolase activities
beta-picolyl propyl amine
-
uncompetitive inhibition of monophenolase and diphenolase activities
betulin
-
from Guioa villosa leaf extract
betulinic acid
-
pentacyclic triterpene extracted from Rhododendron collettianum
Bromoacetate
-
noncompetitive inhibition in a dose-dependent manner
brosimone I
-
isolated from the wood of Artocarpus heterophyllus
broussonin C
-
competitive inhibition
bufobutanoic acid
-
-
butylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, competitive inhibition for the cresolase activity, competitive inhibition for the catecholase activity
caffeic acid
campestrol
-
isolated from Trifolium balansae, NMR structure identification, IC50: 0.00890 mM
captopril
-
-
carpachromene
-
isolated from the wood of Artocarpus heterophyllus
catechin
catechol
cefazolin
cefodizime
chloroform
-
the cross-linked enzyme aggregate shows about 30% residual activity after incubation in chloroform for about 3 h
chlorogenic acid
-
tyrosinase inhibitors from Marrubium velutinum, phenolic acids
choline acetate
-
27.9% residual activity at 5% (w/v)
choline dihydrophosphate
-
27.4% residual activity at 5% (w/v)
choline methylsulfonate
-
39.7% residual activity at 5% (w/v)
choline nitrate
-
54.6% residual activity at 5% (w/v)
chrysoeriol
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols
chrysoeriol 4'-O-beta-D-glucopyranoside
-
from Guioa villosa leaf extract
chrysoeriol-7-O-(3'',6''-di-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
cinnamaldehyde
-
-
Cinnamic acid
cistanoside F
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Comparing the activity of tetrasaccharides with cistanoside F
citreorosein
-
anthraquinone, isolated from the root of Polygonum cuspidatum
crenulatoside A
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 23.7%
crenulatoside B
-
from Guioa villosa leaf extract
crenulatoside C
-
from Guioa villosa leaf extract
crenulatoside D
-
from Guioa villosa leaf extract
crotonic acid
-
-
crude ethanol phase
-
ECPE, inhibitory effect on diphenolase activity of tyrosinase
-
cudraflavone B
-
isolated from the wood of Artocarpus heterophyllus
cumic acid
-
noncompetitive inhibition
cuminaldehyde
Cupferron
-
-
cyanomaclurin
-
isolated from the wood of Artocarpus heterophyllus
cycloartocarpesin
-
isolated from the wood of Artocarpus heterophyllus
cycloartocarpin
-
isolated from the wood of Artocarpus heterophyllus
cyclomorusin
-
exhibits competitive inhibition characteristics. Flavone displaying tyrosinase inhibitory activity, isolated from the stem barks of Morus lhou. Inhibitory potency of this flavonoid toward monophenolase activity of mushroom tyrosinase is investigated
D-ascorbic acid
-
met-tyrosinase is stable in anaerobic conditions but, in the presence of D-ascorbic acid undergoes an inactivation
D-ascorbic acid-6-p-hydroxybenzoic acid ester
-
irreversible inhibitor
daedalin A
-
(2R)-6-hydroxy-2-hydroxymethyl-2-methyl-2H-chromene from mycelial culture of Daedalea dickinsii
davanol
-
competitive, IC50: 0.017 mM
decahydro-2-naphthyl gallate
-
-
deoxyarbutin
competitive, a potent inhibitor of tyrosinase that can also act as substrate of the enzyme, shows membrane breaking and toxicity towards melanosomes, induces hydroxyl free radicals. Inhibition mechanism, overview
dihydro-4-coumaric acid
-
19.6% inhibition at 1 mM
dihydro-4-methoxycinnamic acid
-
46.4% inhibition at 1 mM
dihydrocaffeic acid
-
2.7% inhibition at 1 mM
dihydrocinnamic acid
-
40.5% inhibition at 1 mM
dihydroferulic acid
-
17.9% inhibition at 1 mM
dihydroisoferulic acid
-
60.6% inhibition at 0.33 mM
dihydromorin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
dihydrosinapic acid
-
22.6% inhibition at 1 mM
dioxane
-
increasing solvent concentration up to 80% (v/v) yields a gradual reduction in the activity of the soluble and cross-linked enzyme forms, the cross-linked enzyme aggregate shows about 40% residual activity after incubation in dioxane for about 62 h
DL-dithiothreitol
-
very slight inhibition at 300 pmol/unit of enzyme
dopastin
-
-
echinacoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of echinacoside in the presence of CuSO4 (0.05 mM)
ellagic acid
-
-
emodin
-
anthraquinone, isolated from the root of Polygonum cuspidatum
epiafzelechin
-
-
epicatechin
-
-
epicatechin-(4beta-8, 2beta-O-7)-epicatechin-(4beta-8)-epicatechin
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 34.6%
epigallocatechin
-
-
epigallocatechin gallate
-
exhibits a greater anti-tyrosinase activity than arbutin
erythrodiol
-
pentacyclic triterpene extracted from Rhododendron collettianum
esculetin
-
6,7-dihydroxycoumarin, weak inhibition
ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
ethylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, uncompetitive inhibition for the cresolase activity, mixed inhibition for the catecholase activity
farnesic acid
-
-
ferulic acid
flemichin D
-
competitive inhibition
fleminchalcone A
-
i.e. 1-(5-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chroman-8-yl)-3-(4-methoxyphenyl)-propan-1-one, competitive inhibition
fleminchalcone B
-
i.e. 1-(3,5-dihydroxy-2,2-dimethylchroman-6-yl)-3-(4-methoxyphenyl)propan-1-one, competitive inhibition
fleminchalcone C
-
i.e. 1-(5-hydroxy-8-(2-hydroxypropan-2-yl)-2,2-dimethyl-7,8-dihydro-2H-furo[2,3-h]chromen-6-yl)-3-(4-methoxyphenyl)propan-1-one, competitive inhibition
fluorodeoxyarbutin
-
forsythoside B
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of for sythoside B in the presence of CuSO4 (0.05 mM)
galangin
-
and its flavonoid mixture from Alpinia officinarum
gallic acid
gallocatechin
-
-
gamma-picolyl heptyl amine
-
uncompetitive inhibition of monophenolase activity and mixed-type inhibition of diphenolase activity
gamma-picolyl nonyl amine
-
-
gamma-picolyl pentyl amine
-
uncompetitive inhibition of monophenolase activity and mixed-type inhibition of diphenolase activity
gamma-picolyl propyl amine
-
uncompetitive inhibition of monophenolase activity and mixed-type inhibition of diphenolase activity
Ganoderma lucidum extract
-
basidiomycete, also known as Lingzhi in the herbal medicine community, exhibits significant inhibition of tyrosinase activity. No difference in inhibitory effects on tyrosinase activity is observed by Ganoderma lucidum extracts obtained by the three different extraction methods (75%, 50% ethanol, and distilled water extraction)
-
geranial
-
-
geranic acid
-
in lemongrass (Cymbopogon citratus)
geranic acid ethyl amide
-
-
geranic acid ethyl ester
-
-
geranic acid ethylene glycol ester
-
-
geraniol
-
-
geranyl gallate
-
-
glabrene
-
-
glabridin
glabridine
-
tyrosinase inhibitor
glutamic acid
-
individually grafted onto a novel CSG1.0 membrane as a ligand for enzyme purification
glyasperin C
-
tyrosinase inhibitor
glycolic acid
-
tyrosinase inhibitor
Guanidine-HCl
-
treatment with guanidine-HCl at increasing concentrations (0-800 mM) results in a reduced activity for both enzyme forms, but aggregation as cross-linked enzyme aggregate improves tyrosinase stability at higher concentrations (above 314 mM)
hesperidin
-
inhibitory effect on tyrosinase diphenolase, from citrus peel crude extracts
hexane
-
the cross-linked enzyme aggregate shows about 20% residual activity after incubation in hexane for about 24 h
hexanoic acid
-
mixed-type inhibition
hexylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, competitive inhibition for the cresolase activity, competitive inhibition for the catecholase activity
histidine
-
individually grafted onto a novel CSG1.0 membrane as a ligand for enzyme purification
hydroquinone
hydroxyanisole
-
tyrosinase inhibitor
isoartocarpesin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
isoferulate
-
tyrosinase inhibitors from Marrubium cylleneum, phenolic acids
isoferulic acid
-
77.8% inhibition at 0.33 mM
isoliquiritigenin
-
-
isorhamnetin-3-O-(6''-OAc)-glucoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
isorhamnetin-3-O-glucoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
isorhamnetin-3-O-rutinoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
isorhamnetin-7-O-(6''-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
isovaleric acid
-
-
kaempferol
kaempferol 3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside
-
IC50 of 0.1806 mg/ml
kaempferol 3-O-[beta-D-glucopyranosyl-(1->4)][alpha-L-rhamnopyranosyl-(1->6)]-beta-D-glucopyranoside
-
IC50 of 0.1935 mg/ml
kaempferol-3-O-(6''-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum, flavone/flavonol acylated glucosides
kaempferol-3-O-glucoside
-
tyrosinase inhibitors from Marrubium cylleneum, flavone/flavonol glucosides
kazinol C
-
competitive inhibition
kazinol D
-
-
kazinol F
-
competitive inhibition
kazinol S
-
competitive inhibition, i.e. 5'-(2-methylbut-3-en-2-yl)-6''-(3-methylbut-2-enyl)-5''-(2,3-epoxy-3-methylbytyl)-2',4',3'',4''-tetrahydroxy diphenylpropane
kazinol T
-
i.e. 5'-(2-methylbut-3-en-2-yl)-6''-(3-methylbut-2-enyl)-4'',5''-[(2-(1-hydroxy-1-methylethyl)]-dihydrofuranyl)-2',4',3''-trihydroxy diphenylpropane
KFEKKFEK
-
-
khonklonginol H
-
competitive inhibition
kojic acid
kolaflavonone
-
-
kuraridinol
-
prenylated flavonoid from Sophora flavescens, isolated from the EtOAc fraction, inhibitory effects on tyrosinase and melanin synthesis. Inhibitory activity 20times more potent than that of the positive control, kojic acid. Kuraridinol is a chalcone compound belonging to the prenylated flavonoids
kurarinol
kurarinone
-
from the root of Sophora flavescens, exhibits potent antibacterial activity, noncompetitive inhibitor, binds at an allosteric site
kuwanon A
-
-
kuwanon C
-
exhibits competitive inhibition characteristics. Flavone displaying tyrosinase inhibitory activity, isolated from the stem barks of Morus lhou. Inhibitory potency of this flavonoid toward monophenolase activity of mushroom tyrosinase is investigated
kuwanon E
-
competitive inhibitor
kuwanon U
-
-
L-ascorbic acid
-
met-tyrosinase is stable in anaerobic conditions but, in the presence of L-ascorbic acid undergoes an inactivation
L-cysteine
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
L-mimosine
L-Pro-L-Leu-Gly
-
-
ladanein
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols. Methoxylated flavones, like the methylethers of scutellarein, showed 10times lower inhibitory activity than kojic acid
lamiophlomiside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
lavandulifolioside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of lavandulifolioside in the presence of CuSO4 (0.05 mM)
leucosceptoside A
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of leucosceptoside A in the presence of CuSO4 (0.05 mM)
lupeol
-
from Guioa villosa leaf extract
lupinifolin
-
competitive inhibition
luteolin
-
-
luteolin 4'-O-beta-D-glucopyranoside
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 14%
Luteolin 7-O-glucoside
-
-
luteolin-7-O-glucoside
-
tyrosinase inhibitors from Marrubium cylleneum, flavone/flavonol glucosides
macroporus adsorption resin
-
FGRE, inhibitory effect on diphenolase activity of tyrosinase
-
martynoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
maslinic acid
-
pentacyclic triterpene extracted from Rhododendron collettianum
mauritianin
-
from Guioa villosa leaf extract
Methacrylic acid
-
-
methanol
-
the soluble enzyme retains 7.8% of its original activity, as compared to 31% by the cross-linked enzyme aggregates, after being incubated in the presence of 40% (v/v) methanol
Methimazole
-
-
methyl (Z)-2-((E)-2-(((E)-(5-bromothiophen-2-yl)methylene)hydrazono)-4-oxothiazolidin-5-ylidene)acetate
-
-
methyl (Z)-2-((E)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)-4-oxothiazolidin-5-ylidene)acetate
-
-
methyl arjunolate
-
pentacyclic triterpene extracted from Rhododendron collettianum
methyl gallate
-
shows a concentration-dependent inhibitory activity against tyrosinase with IC50 of 0.0625 mg/ml
monobenzyl hydroquinone
-
benoquin, PBP, tyrosinase inhibitor
moracin M
-
competitive inhibitor
moracin N
-
competitive inhibitor
moracinoside M
-
competitive inhibitor
morin
-
competitive, IC50: 2.320 mM
mormin
-
exhibits competitive inhibition characteristics. Characterized as a new flavone possesing a 3-hydroxymethyl-2-butenyl at C-3. Flavone displaying tyrosinase inhibitory activity, isolated from the stem barks of Morus lhou. Inhibitory potency of this flavonoid toward monophenolase activity of mushroom tyrosinase is investigated
morusin
-
Flavone displaying tyrosinase inhibitory activity, isolated from the stem barks of Morus lhou. Inhibitory potency of this flavonoid toward monophenolase activity of mushroom tyrosinase is investigated
morusinol
-
-
N',N'''-benzene-1,4-diylbis(1-hydroxyurea)
-
-
N'-(hydrazinylcarbonyl)-4-hydroxybenzohydrazide
-
-
N'-(hydrazinylcarbonyl)naphthalene-2-carbohydrazide
-
-
N,N-unsubstituted selenourea derivatives
-
55.5% inhibition at 0.2 mM, IC50: 0.17-0.23 mM
-
N-(2,4-dihydroxybenzyl)-2,4-dihydroxybenzamide
-
IC50: 0.029 mM
N-(2,4-dihydroxybenzyl)-3,4,5-trihydroxybenzamide
-
IC50: 0.017 mM
N-(2,4-dihydroxybenzyl)-3,4-dihydroxybenzamide
-
IC50: 0.011 mM
N-(2,4-dihydroxybenzyl)-3,5-dihydroxybenzamide
-
IC50: 0.0022 mM
N-benzyl-2,4-dihydroxybenzamide
-
IC50: 1.660 mM
N-benzyl-3,4,5-trihydroxybenzamide
-
IC50: 0.780 mM
N-benzyl-3,4-dihydroxybenzamide
-
IC50: 2.0 mM
N-benzyl-3,5-dihydroxybenzamide
-
IC50: 0.700 mM
N-benzylamide
-
IC50: 1.990 mM
N-benzylbenzamide derivatives
-
inhibitory potency, structure–activity relationships, overview
-
N-hydroxy-N-(phenylcarbamoyl)acetamide
-
-
N-phenylthiourea
-
PTU induces a strong inhibition of the tyrosinase activity
N-phenylurea
-
-
NaN3
-
treatment with NaN3 at increasing concentrations (0-4 mM) results in a reduced activity for both soluble and cross-linked enzyme forms, but aggregation as cross-linked enzyme aggregates improves tyrosinase stability at higher concentrations (above 0.4 mM)
neocyclomorusin
-
competitive inhibitor
nikotiflorin
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
nobiletin
-
inhibitory effect on tyrosinase diphenolase, from citrus peel crude extracts
norartocarpetin
octanoic acid
-
mixed-type inhibition
octyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
-
-
oxyresveratrol
p-Aminobenzoic acid
-
individually grafted onto a novel CSG1.0 membrane as a ligand. This study indicates the p-aminobenzoic acid (ABA) grafted chitosan membrane (CSG-ABA) exhibits the best sorption capacity on tyrosinase
p-coumaric acid
p-hydroxybenzyl alcohol
-
4HBA, inhibitory effect on tyrosinase activity and melanogenesis. As the concentration of p-hydroxybenzyl alcohol increases, the enzyme activity rapidly decreases. Results indicate that the tyrosinase binds to the p-hydroxybenzyl alcohol and induces the enzyme conformation changes, and then causes total loss of the enzyme
pentagalloyl glucopyranose
-
exhibits potent, dose-dependent inhibitory effect on tyrosinase with respect to L-DOPA with IC50 of 0.04265 mg/ml
petroleum ether
-
PCPE, inhibitory effect on diphenolase activity of tyrosinase
-
phaselic acid
-
tyrosinase inhibitors from Marrubium velutinum, phenolic acids
phenylacetic acid
-
-
phenylethylamide
-
-
-
Phenylthiourea
-
IC50: 0.17 mM
phloretin
-
the compound is a substrate and an inhibitor for tyrosinase, 63% inhibition at 0.2 mM
phloridzin
-
the compound is a substrate and an inhibitor for tyrosinase, 53% inhibition at 0.15 mM
phloridzin dihydrate
-
-
phloroglucinol
-
enzyme-inhibitor interaction measurement by SPR
physcion
-
anthraquinone, isolated from the root of Polygonum cuspidatum. Most potent tyrosinase inhibition among the four anthraquinones examined, which is comparable to kojic acid
procyanidin
-
-
procyanidin B1
-
-
prodelphindin
-
-
propelargonidin
-
-
propylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, uncompetitive inhibition for the cresolase activity, mixed inhibition for the catecholase activity
pyrogallol
-
enzyme-inhibitor interaction measurement by SPR
quercetin
quercetin 3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside
-
IC50 of 0.1297 mg/ml
quercetin 3-O-[beta-D-glucopyranosyl-(1->4)][alpha-L-rhamnopyranosyl-(1->6)]-beta-D-glucopyranoside
-
IC50 of 0.1462 mg/ml
quercetin-3-O-(6''-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium cylleneum, flavone/flavonol acylated glucosides
RADSRADC
-
-
resorcinol
-
acts as enzyme substrate and inhibitor
resveratrol
-
can also act as enzyme substrate
rutin
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
saffron
-
enzyme-inhibitor interaction measurement by SPR
-
SDS
-
a sharp decrease in the activity of the soluble enzyme is noted from 0 to 17 mM SDS
serotonin
-
-
Sinapic acid
-
1.6% inhibition at 1 mM
Sodium azide
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
Sodium fluoride
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
sodium iso-butylxanthate
-
-
sodium iso-pentylxanthate
-
-
sodium iso-propylxanthate
-
-
sophoraflavanone G
-
from the root of Sophora flavescens, exhibits potent antibacterial activity, noncompetitive inhibitor
soyacerebroside I
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 86.3%
stachydrine
-
tyrosinase inhibitors from Marrubium cylleneum, lignan glucosides
stachysoside D
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
steppogenin
stigmast-5-ene-3beta,26-diol
-
isolated from Trifolium balansae, NMR structure identification, IC50: 0.00239 mM
stigmast-5-ene-3beta-ol
-
isolated from Trifolium balansae, NMR structure identification, IC50: 0.00525 mM
Streptomyces hiroshimensis strain TI-C3 with anti-tyrosinase activity
-
bacterial strain TI-C3, isolated and verified to display 498 U/ml of anti-tyrosinase acitivity. The anti-tyrosinase activity of the strain TI-C3 is improved to 905 U/ml under cultivation, usong glucose and malt extract as the sole carbon and nitrogen sources
-
Tannic acid
-
enzyme-inhibitor interaction measurement by SPR
terrein
-
examine the effects of a combination of 2-butyl-5-hydroxyphenyl 3-(3,4-dihydroxyphenyl)propanoate with terrein, an agent that down-regulates microphthalmia-associated transcription factor
tert-butanol
-
the cross-linked enzyme aggregate shows about 50% residual activity after incubation in tert-butanol for about 326 h
tetrabutylammonium acetate
-
24.1% residual activity at 5% (w/v)
tetrabutylammonium methylsulfonate
-
45.3% residual activity at 5% (w/v)
tetramethylammonium acetate
-
30% residual activity at 5% (w/v)
Thai honey
-
different types of Thai honey on pathogenic bacteria causing skin diseases, tyrosinase enzyme and generating free radicals, antibacterial and antioxidant activities of Thai honey, overview. Honey from longan flower gives the highest activity on multiresistent Staphylococcus aureus (MRSA isolate 49) when compared to the other types of honey, with a minimum inhibitory concentration of 12.5% v/v and minimum bactericidal concentration of 25% v/v. The antioxidant activity of the honey obtained from coffee pollen is the highest with highest level of phenolic and flavonoid compounds. Honey from coffee flower shows inhibition of tyrosinase by 63.46%. The highest activity of tyrosinase inhibition from manuka honey is also very high
-
Thiobarbituric acid
-
8.21% inhibition at 0.2 mM
thiodeoxyarbutin
-
Thiosemicarbazide
-
-
tianmushanol
-
-
tiglic acid
-
-
tiliroside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
trans-cinnamaldehyde
-
competitive inhibition
trans-geranic acid
-
-
tributylammonium dihydrophosphate
-
27.5% residual activity at 5% (w/v)
triethylammonium dihydrophosphate
-
23.4% residual activity at 5% (w/v)
trifolirhizin
-
prenylated flavonoid from Sophora flavescens, isolated from the EtOAc fraction, inhibitory effects on tyrosinase and melanin synthesis
trimethylammonium dihydrophosphate
-
12% residual activity at 5% (w/v)
trimethylammonium methylsulfonate
-
40.9% residual activity at 5% (w/v)
tropolone
tyrosol
-
the compound is a substrate and an inhibitor for tyrosinase, 18% inhibition at 1.5 mM
umbelliferone
-
-
Vanillin
-
-
velutinoside I
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
velutinoside II
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of velutinoside II in the presence of CuSO4 (0.05 mM)
velutinoside III
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
velutinoside IV
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
YRSRKYSSWY
-
-
[1,1''-biphenyl]-3-carboxylic acid
-
little availability of the carboxylic acid group in 2-phenylbenzooic acid to chelate with cupric ions in the active site
[1,1'-biphenyl]-2-carboxylic acid
-
-
[1,1'-biphenyl]-4-carboxylic acid
-
-
[2-(furan-2-ylmethylene-hydrazono)-4-oxo-thiazolidin-5-ylidene]-acetic acid methyl ester
-
-
[2-[(4-benzyloxy-benzylidene)-hydrazono]-4-oxo-thiazolidin-5-ylidene]-acetic acid methyl ester
-
-
[4-oxo-2-(pyridin-4-ylmethylene-hydrazono)-thiazolidin-5-ylidene]-acetic acid methyl ester
-
non-competitive inhibition
additional information
-