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

-

-

?

(-)-epicatechin + 1/2 O2

?

-

-

?

(R)-dopaxanthin + dehydroascorbic acid + O2

(R)-dopaxanthin quinone + L-ascorbic acid + H2O

(R)-tyrosine-betaxanthin + L-DOPA + O2

(R)-dopaxanthin + dopaquinone + H2O

-

i.e. (R)-portulacaxanthin II, the activity of the enzyme is not restricted to betaxanthins derived from (S)-amino acids

674114

(R)-dopaxanthin is a pigment, quantitative product analysis

-

?

1,5-bis(4-hydroxyphenyl)-1,4-pentadiene-3-one + O2

?

-

-

?

2 2-methyl-L-dopa + O2

2 2-methyldopaquinone + 2 H2O

-

-

?

2 catechol + O2

2 1,2-benzoquinone + 2 H2O

2 L-dopa + O2

2 dopaquinone + 2 H2O

2 L-tyrosine + O2

2 L-dopa

-

-

?

2-methyl-L-tyrosine + O2

2-methyldopaquinone + H2O

-

-

?

2-methylresorcinol + O2

?

-

acts as enzyme substrate and inhibitor, low activity

-

?

3,3',4',5,7-pentahydroxyflavone + 1/2 O2

?

-

quercetin

689278

-

?

3,4-dihydroxyphenyl propionic acid + O2

2-(3,4-dioxocyclohexa-1,5-dien-1-yl)propionic acid + H2O

-

-

r

3,4-dihydroxyphenylacetic acid + 1/2 O2

(3,4-dioxocyclohexa-1,5-dien-1-yl)acetic acid + H2O

-

DHPAA

-

?

3,4-dihydroxyphenylalanine + 1/2 O2

dopaquinone + H2O

-

-

?

3,4-dihydroxyphenylalanine + O2

?

-

-

?

3,4-dihydroxyphenylpropionic acid + 1/2 O2

3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid + H2O

-

DHPPA

-

?

3-hydroxyanthranilic acid + O2

cinnabarinic acid + H2O

-

-

?

3-hydroxybenzyl alcohol + O2

?

-

-

?

3-methoxyphenol + O2

?

-

-

?

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

-

-

?

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

-

-

?

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

-

-

?

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

-

-

?

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

-

-

?

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

-

-

?

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

-

-

?

4-bromophenol + O2

?

-

-

?

4-chlorocatechol + 1/2 O2

4-chlorocyclohexa-3,5-diene-1,2-dione + H2O

-

-

?

4-chlorophenol + O2

4-chloro-1,2-quinone + H2O

-

-

?

4-ethoxyphenol + O2

?

-

636439 , 675458 , 726870 , 744490

-

?

4-ethylcatechol + 1/2 O2

4-ethylcyclohexa-3,5-diene-1,2-dione + H2O

-

-

?

4-ethylresorcinol + O2

?

-

acts as enzyme substrate and inhibitor

-

?

4-fluorophenol + O2

?

-

-

?

4-hexylresorcinol + O2

?

-

-

?

4-hydroxyanisole + O2

3,4-dihydoxyanisol + H2O

4-hydroxyanisole + O2

?

-

-

?

4-hydroxybenzaldehyde + O2

?

-

-

?

4-hydroxybenzyl alcohol + O2

?

4-hydroxyphenyl acetic acid + O2

?

-

636439 , 675458

-

?

4-hydroxyphenyl propionic acid + O2

3,4-dihydroxyphenyl propionic acid + H2O

-

-

r

4-hydroxyphenyl propionic acid + O2

?

-

-

?

4-iodophenol + O2

?

-

-

?

4-methoxyphenol + O2

?

-

675458 , 744490

-

?

4-methylcatechol + 1/2 O2

4-methyl-1,2-benzoquinone + H2O

4-methylcatechol + O2

4-methyl-o-benzoquinone + H2O

-

-

?

4-Methylphenol + O2

?

-

-

?

4-methylresorcinol + O2

?

-

acts as enzyme substrate and inhibitor

-

?

4-n-butylresorcinol + O2

?

-

-

?

4-nitrocatechol + 1/2 O2

4-nitrocyclohexa-3,5-diene-1,2-dione + H2O

-

-

?

4-tert-butylcatechol + 1/2 O2

4-tert-butylcyclohexa-3,5-diene-1,2-dione + H2O

-

-

?

4-tert-butylcatechol + O2

4-tert-butyl-o-benzoquinone + H2O

-

-

r

4-tert-butylphenol + O2

4-tert-butyl 1,2-benzoquinone + H2O

-

-

?

4-tert-butylphenol + O2

?

-

-

?

4-[(4-methylphenyl)azo]-1,2-benzendiol + 1/2 O2

4-[(E)-(4-methylphenyl)diazenyl]cyclohexa-3,5-diene-1,2-dione + H2O

4-[(4-methylphenyl)azo]-phenol + O2 + AH2

4-[(4-methylbenzo)azo]-1,2-benzendiol + H2O + A

alpha-arbutin + O2

?

-

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

?

caffeic acid + 1/2 O2

caffeoyl quinone + H2O

-

-

?

caffeic acid + O2

caffeoyl quinone + H2O

-

-

?

catechin + O2

?

-

-

?

catechin dimer + O2

?

-

-

?

catechin trimer + O2

?

-

-

?

catechol + 1/2 O2

1,2-benzoquinone + H2O

-

pyrogallol and catechol are best substrates for catalysis and inactivation

-

?

catechol + O2

?

reaction of EC 1.10.3.1

-

?

D-ascorbic acid + O2

?

-

-

r

D-dopa + 1/2 O2

D-dopaquinone + H2O

tyrosinase oxidizes L- and D-forms with similar rate

-

?

D-tyrosine + L-dopa + O2

D-dopa + dopaquinone + H2O

-

-

?

D-tyrosine + O2 + AH2

D-dopa + H2O + A

tyrosinase oxidizes L- and D-forms with similar rate

-

?

deoxyarbutin + O2

?

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

?

-

-

?

DL-dopa + 1/2 O2

DL-dopaquinone + H2O

tyrosinase oxidizes L- and D-forms with similar rate

-

?

DL-tyrosine + O2 + AH2

DL-dopa + H2O + A

tyrosinase oxidizes L- and D-forms with similar rate

-

?

dopa methyl ester + O2

dopaquinone methyl ester + H2O

-

-

r

dopamine + O2

?

dopamine + O2

dopamine quinone + H2O

ellagic acid + O2

?

epicatechin + O2

?

-

-

?

esculetin + 1/2 O2

2H-chromene-2,6,7-trione + H2O

-

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

-

-

?

gamma-L-glutaminyl-3,4-dihydroxybenzene + O2

gamma-L-glutaminyl-3,4-benzoquinone + H2O

-

-

?

gamma-L-glutaminyl-4-hydroxybenzene + O2 + AH2

gamma-L-glutaminyl-3,4-dihydroxybenzene + H2O + A

-

-

?

Gly-Gly-L-Tyr + O2

?

-

-

?

Gly-L-Tyr-Gly + O2

?

-

-

?

hydrocaffeic acid + O2

?

-

-

?

hydroquinone + O2

?

-

744490 , 746222

-

?

hydroxyhydroquinone + O2

2-hydroxy-p-benzoquinone + H2O

-

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

-

individually grafted onto a novel CSG1.0 membrane as a ligand

-

?

L-alpha-methyl tyrosine + O2

L-alpha-methyldopa + H2O

-

-

r

L-alpha-methyldopa + H2O

L-alpha-methyl tyrosine + O2

-

-

r

L-alpha-methyldopa + O2

L-alpha-methyldopaquinone + H2O

-

-

r

L-dopa + 1/2 O2

L-dopachrome + H2O

-

688041 , 689442

-

?

L-dopa + 1/2 O2

L-dopaquinone + H2O

L-DOPA + O2

?

-

-

?

L-DOPA + O2

dopaquinone + H2O

L-Dopa + O2

L-dopaquinone + H2O

L-isoproterenol + O2

1-[1-hydroxy-2-(propan-2-ylamino)ethyl]-3,4-dioxocyclohexa-1,5-diene + H2O

-

-

r

L-Tyr + O2

L-Dopa + H2O

-

diphenolase activity

-

?

L-Tyr-Gly-Gly + O2

?

-

-

?

L-tyrosine + L-dopa + O2

L-dopa + dopaquinone + H2O

L-tyrosine + O2

dihydroxyphenylalanine quinone + H2O

-

-

?

L-tyrosine + O2

dopaquinone + H2O

L-tyrosine + O2

L-DOPA + H2O

L-tyrosine + O2 + AH2

L-3,4-dihydroxyphenylalanine + H2O + A

L-tyrosine + O2 + AH2

L-dopa + H2O + A

L-tyrosine methyl ester + O2

?

-

-

?

methyl gallate + O2

methyl 5-hydroxy-3,4-dioxocyclohexa-1,5-diene-1-carboxylate + H2O

-

-

?

N-acetyl-L-tyrosine + O2

N-acetyl-dopaquinone + H2O

-

-

?

oxyresveratrol + O2

?

p-coumaric acid + O2

caffeic acid + H2O

-

-

?

p-cresol + O2 + AH2

4-methylpyrocatechol + H2O + A

-

-

?

p-tyrosol + O2

2-(3,4-dihydroxyphenyl)ethanol + H2O

-

-

?

p-tyrosol + O2 + AH2

2-(3,4-dihydroxyphenyl)ethanol + H2O + A

-

-

?

phenol + O2

?

phenol + O2

catechol + H2O

-

-

r

phenol + O2 + AH2

catechol + H2O + A

phloretic acid + O2

?

-

-

?

phloretin + O2

?

-

the compound is a substrate and an inhibitor for tyrosinase

-

?

phloridzin + O2

?

-

the compound is a substrate and an inhibitor for tyrosinase

-

?

phloroglucinol + 1/2 O2

?

-

-

?

protocatechuic acid + 1/2 O2

3,4-dioxocyclohexa-1,5-diene-1-carboxylic acid + H2O

-

-

?

protocatechuic aldehyde + 1/2 O2

3,4-dioxocyclohexa-1,5-diene-1-carbaldehyde + H2O

-

-

?

pyrocatechol + 1/2 O2

1,2-benzoquinone + H2O

pyrogallol + 1/2 O2

?

resorcinol + O2

?

-

acts as enzyme substrate and inhibitor

-

?

resveratrol + O2

?

-

-

?

rhododendrol + O2

?

-

-

?

tyramine + O2

4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione + H2O

-

-

?

tyramine + O2

?

tyramine + O2

dopamine + H2O

-

-

r

tyrosine + O2

dopaquinone + H2O

-

744483 , 744486 , 744488 , 744495 , 744511 , 744676 , 744819 , 745130 , 745138 , 745139 , 746193 , 746346 , 746498

-

?

tyrosol + O2

?

-

the compound is a substrate and an inhibitor for tyrosinase

-

?

additional information

?

-

25 entries

2 L-dopa + O2

2 dopaquinone + 2 H2O

2 L-tyrosine + O2

2 L-dopa

-

-

?

dopamine + O2

?

-

744015

-

?

L-DOPA + O2

dopaquinone + H2O

-

713205 , 727168

-

?

L-tyrosine + L-dopa + O2

L-dopa + dopaquinone + H2O

-

-

?

L-tyrosine + O2

dihydroxyphenylalanine quinone + H2O

-

-

?

L-tyrosine + O2

dopaquinone + H2O

L-tyrosine + O2

L-DOPA + H2O

-

-

?

tyrosine + O2

dopaquinone + H2O

-

744483 , 744486 , 744488 , 744495 , 744511 , 744676 , 744819 , 745130 , 745138 , 745139 , 746193 , 746346 , 746498

-

?

additional information

?

-

7 entries

additional information

-

if L-DOPA is an active cofactor, its formation as an intermediate during o-dopaquinone production is controversial

-

copper

Cu2+

13 entries

H2O2

-

the exogenous oxygen molecule is bound as peroxide and bridges the two copper centers, conferring a distinct O2-Cu(II) charge transfer

(+)-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

744491

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

744671

2-butyl-5-hydroxyphenyl 3-(3,4-dihydroxyphenyl)propanoate

-

KI-063, a new tyrosinase inhibitor, strong concentration-dependent inhibitory effect on tyrosinase activity

688592

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-mercaptoethanol

-

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 inhibitor, 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)

689413

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

745095

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

712597

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

711476

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

685462

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

-

711435 , 713205

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

ammonium tetramolybdate

-

anacardic acid

-

competitive inhibition

angelic acid

-

Anisaldehyde

Anisic acid

-

uncompetitive inhibition

anthraglycoside B

-

anthraquinone, isolated from the root of Polygonum cuspidatum

689441

Antrodia camphorata extract

-

basidiomycete, only other effect on tyrosinase activity is prepared from Antrodia camphorata using 75% ethanol extraction

689118

-

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

8 entries

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

712597

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

699039

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

689441

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

-

cyanide

-

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

685668

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

deoxyfuran

-

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)

EDTA

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

-

745139

epigallocatechin gallate

-

exhibits a greater anti-tyrosinase activity than arbutin

erythrodiol

-

pentacyclic triterpene extracted from Rhododendron collettianum

esculetin

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)

689118

-

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

glutathione

-

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

700323

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, structureactivity relationships, overview

-

N-hydroxy-N-(phenylcarbamoyl)acetamide

-

N-phenylthiourea

-

PTU induces a strong inhibition of the tyrosinase activity

N-phenylurea

-

NaCl

-

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

685452

pentagalloyl glucopyranose

-

exhibits potent, dose-dependent inhibitory effect on tyrosinase with respect to L-DOPA with IC50 of 0.04265 mg/ml

700323

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

-

Salicylhydroxamic acid

-

SDS

serotonin

-

SFLLRN

-

Sinapic acid

-

1.6% inhibition at 1 mM

Sodium azide

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

687996

-

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

688592

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

42 entries

-

2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside

2-morpholinoethyl (E)-3-(3,4-dihydroxyphenyl)acrylate

-

a caffeic acid-4-(2-hydroxyethyl) morpholine ester, activates mushroom tyrosinase activity dramatically, the activation of mushroom tyrosinase is noncompetitive

746346

3-hydroxyanthranilic acid

-

higher than 0.005 mM, 600% activation of N-acetyl-tyrosine hydroxylation, activation of 4-tert-butylphenol oxidation, shortens lag time of the enzyme

3-morpholinopropyl (E)-3-(3,4-dihydroxyphenyl)acrylate

-

a caffeic acid-4-(3-hydroxypropyl) morpholine ester, activates mushroom tyrosinase activity dramatically the activation of mushroom tyrosinase is noncompetitive

746346

Aloe-emodin

-

shows mild activating effects on tyrosinase. Isolated from Radix polygoni multiflori, a herb used effectively to prevent graying and treat skin depigmentation diseases in traditional Chinese medicine

688041

chrysophanol

dithiothreitol

-

small amounts abolish the characteristic lag phase of monohydric phenol oxidation without effect on the maximum rate of reaction or on the total O2 consumption

emodin

gallic acid

-

H2O2

-

the addition of hydrogen peroxide transforms Em to Eox, which is able to hydroxylate alpha/beta-arbutin, although the o-quinone that is originated is unstable

physcion

SDS

activates at 2 mM

additional information

-

2.7

2-Methylresorcinol

-

pH 7.0, 25°C

1.89 - 5.1

3,4-dihydroxyphenyl propionic acid

1.3

3,4-dihydroxyphenylacetic acid

-

0.7

3,4-Dihydroxyphenylpropionic acid

-

0.78

3-hydroxyanthranilic acid

-

10.1

3-Hydroxybenzyl alcohol

-

5.4

3-methoxyphenol

-

0.71

3-[2-(3,4-dihydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-ethoxycarbonylphenyl)triazene

-

in phosphate buffer (pH 7.4), at 37°C

0.31

3-[2-(4-hydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-cyanophenyl)triazene

-

in phosphate buffer (pH 7.4), at 37°C

1.98

4-Bromophenol

-

pH and temperature not specified in the publication

0.6

4-Chlorocatechol

-

1.87

4-Chlorophenol

-

pH and temperature not specified in the publication

0.17

4-ethoxyphenol

0.17

4-Ethylcatechol

-

0.117

4-ethylresorcinol

-

pH 7.0, 25°C

0.41

4-Fluorophenol

-

pH and temperature not specified in the publication

0.08

4-hydroxyanisole

1.14

4-hydroxybenzaldehyde

-

pH and temperature not specified in the publication

1.1

4-Hydroxybenzyl alcohol

-

0.44

4-hydroxyphenyl propionic acid

-

1.91

4-hydroxyphenyl acetic acid

-

636439 , 675458

0.44

4-hydroxyphenyl propionic acid

-

2.02

4-iodophenol

-

pH and temperature not specified in the publication

0.08

4-methoxyphenol

0.1 - 33

4-methylcatechol

0.38

4-Methylphenol

-

pH and temperature not specified in the publication

0.203

4-methylresorcinol

-

pH 7.0, 25°C

0.1

4-nitrocatechol

-

1.45 - 2.8

4-tert-butylcatechol

0.016 - 0.45

4-tert-butylphenol

6.5

alpha-arbutin

-

pH 7.0, 25°C

3

beta-arbutin

1.69

caffeic acid

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.16 - 4.65

catechol

4.28

D-ascorbic acid

-

1.86

D-Tyr

-

0.033

deoxyarbutin

pH and temperature not specified in the publication

1.2

DL-2-methyltyrosine

-

0.25 - 0.46

Dopa

1

dopa methyl ester

-

0.84 - 15.2

dopamine

0.1 - 0.12

ellagic acid

0.63 - 0.9

esculetin

0.18

gallic acid

-

7.8

gamma-L-glutaminyl-3,4-dihydroxybenzene

-

0.3

gamma-L-Glutaminyl-4-hydroxybenzene

-

0.11

Gly-Gly-L-Tyr

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.18

Gly-L-Tyr-Gly

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.91

Hydrocaffeic acid

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.92

hydroquinone

-

pH 7.0, 25°C

0.4

Hydroxyhydroquinone

-

pH and temperature not specified in the publication

1.2

L-alpha-methyl tyrosine

-

6.8

L-alpha-methyldopa

-

2.79

L-ascorbic acid

-

0.17 - 26.1

L-Dopa

12 entries

7.1

L-isoproterenol

-

0.21

L-Tyr

-

0.21

L-Tyr-Gly-Gly

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.18 - 4.1

L-tyrosine

13 entries

0.38

L-tyrosine methyl ester

-

0.12

methyl gallate

-

0.015 - 421

O2

10 entries

0.00865

oxyresveratrol

-

pH 7.0, 25°C

0.06

p-tyrosol

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.33 - 12.5

phenol

0.64

phloretic acid

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

0.07

protocatechuic acid

-

0.15

Protocatechuic aldehyde

-

0.4

pyrocatechol

-

Lineweaver-Burk plot of pyrocatechol oxidation by the mushroom PPO

1.4 - 1.96

pyrogallol

0.46

resorcinol

-

pH 7.0, 25°C

0.51 - 9.53

tyramine

additional information

8 entries

-

9.94

2-Methylresorcinol

-

pH 7.0, 25°C

554 - 632

3,4-dihydroxyphenyl propionic acid

433.1

3,4-dihydroxyphenylacetic acid

-

607.2

3,4-Dihydroxyphenylpropionic acid

-

12.1

3-Hydroxybenzyl alcohol

-

46.8

3-methoxyphenol

-

6

3-[2-(3,4-dihydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-ethoxycarbonylphenyl)triazene

-

in phosphate buffer (pH 7.4), at 37°C

0.6

3-[2-(4-hydroxyphenyl)ethylaminocarbonyl]-3-methyl-1-(4-cyanophenyl)triazene

-

in phosphate buffer (pH 7.4), at 37°C

6.9

4-Bromophenol

-

pH and temperature not specified in the publication

859.2

4-Chlorocatechol

-

4.6

4-Chlorophenol

-

pH and temperature not specified in the publication

132 - 202.2

4-ethoxyphenol

802.3

4-Ethylcatechol

-

6

4-ethylresorcinol

-

pH 7.0, 25°C

10.54

4-Fluorophenol

-

pH and temperature not specified in the publication

184 - 274.9

4-hydroxyanisole

0.19

4-hydroxybenzaldehyde

-

pH and temperature not specified in the publication

20 - 88.2

4-Hydroxybenzyl alcohol

66.7

4-hydroxyphenyl propionic acid

-

44.3

4-hydroxyphenyl acetic acid

-

636439 , 675458

66.7

4-hydroxyphenyl propionic acid

-

2.73

4-iodophenol

-

pH and temperature not specified in the publication

184 - 184.2

4-methoxyphenol

842 - 842.1

4-methylcatechol

14.76

4-Methylphenol

-

pH and temperature not specified in the publication

7.73

4-methylresorcinol

-

pH 7.0, 25°C

0.9

4-nitrocatechol

-

640.1 - 642

4-tert-butylcatechol

5.61

4-tert-butylphenol

-

pH and temperature not specified in the publication

4.43

alpha-arbutin

-

pH 7.0, 25°C

3.7 - 3.77

beta-arbutin

874.1 - 1080

catechol

0.92

D-ascorbic acid

-

8

D-Tyr

-

1.95

deoxyarbutin

pH and temperature not specified in the publication

0.6

DL-2-methyltyrosine

-

35.5

dopa methyl ester

-

439 - 2540

dopamine

551 - 928

esculetin

28.2

gallic acid

-

3

Gly-Gly-L-Tyr

-

in 0.1M sodium phosphate buffer (pH 7.0) at 25°C

3.1

Gly-L-Tyr-Gly

-

in 0.1M sodium phosphate buffer (pH 7.0) at 25°C

101.5

hydroquinone

-

pH 7.0, 25°C

229

Hydroxyhydroquinone

-

pH and temperature not specified in the publication

0.6

L-alpha-methyl tyrosine

-

44.3

L-alpha-methyldopa

-

0.97

L-ascorbic acid

-

107 - 1810

L-Dopa

29.4

L-isoproterenol

-

7.9

L-Tyr

-

4

L-Tyr-Gly-Gly

-

in 0.1M sodium phosphate buffer (pH 7.0) at 25°C

3.77 - 7.9

L-tyrosine

3.4

L-tyrosine methyl ester

-

80.2

methyl gallate

-

5.39

oxyresveratrol

-

pH 7.0, 25°C

11.3 - 14.36

phenol

8.1

protocatechuic acid

-

1.5

Protocatechuic aldehyde

-

1280

pyrogallol

-

18.34

resorcinol

-

pH 7.0, 25°C

15.6 - 25.9

tyramine

3.7

2-Methylresorcinol

-

pH 7.0, 25°C

776.5

4-ethoxyphenol

-

pH 7.0, 25°C

51.3

4-ethylresorcinol

-

pH 7.0, 25°C

2300

4-hydroxyanisole

-

pH 7.0, 25°C

2300

4-methoxyphenol

-

pH 7.0, 25°C

38.1

4-methylresorcinol

-

pH 7.0, 25°C

210

D-ascorbic acid

-

26.5

Gly-Gly-L-Tyr

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

17.1

Gly-L-Tyr-Gly

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

110.3

hydroquinone

-

pH 7.0, 25°C

340

L-ascorbic acid

-

19

L-Tyr-Gly-Gly

-

in 0.1 M sodium phosphate buffer (pH 7.0) at 25°C

33 - 37.6

L-tyrosine

620

oxyresveratrol

-

pH 7.0, 25°C

18.1

phenol

-

pH 7.0, 25°C

39.9

resorcinol

-

pH 7.0, 25°C

12

(2E)-but-2-enoic acid

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

0.91

(2E,4E)-hexa-2,4-dienoic acid

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

0.0003

1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)propane

-

inhibition is competitive and reversible, about 15times more potent than kojic acid

0.0011 - 0.0016

1-pentanoyl-3-(4-methoxyphenyl)thiourea

-

pH 6.8, 25°C

0.041

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-chlorophenyl)prop-2-enoate

-

pH 6.8, 25°C

0.013

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

-

pH 6.8, 25°C

0.065

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 2,4-dihydroxybenzoate

-

pH 6.8, 25°C

0.009

2-(chloromethyl)-10-(2-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione

-

pH 7.2, temperature not specified in the publication

2.4

2-(hydroxymethyl)-7,7-dimethyl-10-phenyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione

-

pH 7.2, temperature not specified in the publication

0.01261

2-acetylamino-1,3,4-thiadiazole-5-sulfonamide

-

pH 6.8, 25°C

744671

0.0012

2-chlorobenzaldehyde thiosemicarbazone

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

1

2-ethyl-3-hydroxy-4H-pyran-4-one

-

pH 7.2, temperature not specified in the publication

7.93

2-oxoglutaric acid

-

pH 7.0, 25°C

0.0051

2-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]phenol

-

pH 6.8, 30°C

0.0025

2-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]phenol

-

pH 6.8, 30°C

0.064

3-hydroxy-1,2-dimethyl-4(1H)-pyridone

-

pH 7.2, temperature not specified in the publication

0.006

4-(2-(hydroxymethyl)-7,7-dimethyl-4,9-dioxo-4,6,7,8,9,10-hexahydropyrano[3,2-b]chromen-10-yl)benzonitrile

-

pH 7.2, temperature not specified in the publication

0.00125

4-chlorobenzaldehyde thiosemicarbazone

-

in 5 0mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

0.06

4-formyl-2-methoxyphenyl (4-phenylpiperazin-1-yl)acetate

-

pH 6.8, 25°C

3.7

4-hydroxyphenyl beta-D-xyloside

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.2

4-hydroxyphenyl beta-xylodioside

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.057

4-hydroxyphenyl beta-xylotetraoside

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.29

4-hydroxyphenyl beta-xylotrioside

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.00029 - 0.00105

4-xylidine-bis(dithiocarbamate) sodium salt

0.00198 - 0.16

5,2',4'-trihydroxy-2'',2''-dimethylchromene-(6,7:5'',6'')-flavanone

0.145

5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid

-

pH 7.2, temperature not specified in the publication

0.148

6-hydroxykaempferol

-

a competitive inhibitor of tyrosinase, L-DOPA as a substrate

0.53 - 0.6

benzoic acid

-

versus different substrates, pH and temperature not specified in the publication

0.0057 - 0.0141

benzyldithiocarbamate sodium salt

0.9 - 1.42

beta-arbutin

0.008 - 0.013

butylxanthate sodium salt

0.11

cefazolin

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

699239

0.0129

cefodizime

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

699239

0.44 - 0.59

Cinnamic acid

-

versus different substrates, pH and temperature not specified in the publication

0.04 - 0.078

deoxyarbutin

0.0014 - 0.0138

ethylxanthate sodium salt

18

gamma-picolyl heptyl amine

-

in 0.1 M phosphate buffer (pH 6.5)

20

gamma-picolyl pentyl amine

-

in 0.1 M phosphate buffer (pH 6.5)

23

gamma-picolyl propyl amine

-

in 0.1 M phosphate buffer (pH 6.5)

0.079

glutamic acid

-

9.16

hesperidin

-

2.51

hexanoic acid

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

0.005 - 0.025

hexylxanthate sodium salt

0.148

histidine

-

0.0043 - 0.0223

kojic acid

0.00039

kuraridinol

-

noncompetitive inhibition

0.000045 - 0.014

kurarinol

0.0041

kurarinone

-

2.82

nobiletin

-

1.54

octanoic acid

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 30°C

0.052

p-Aminobenzoic acid

-

0.005 - 0.011

propylxanthate sodium salt

0.0072 - 0.0218

sodium iso-butylxanthate

0.0061 - 0.0422

sodium iso-pentylxanthate

0.0098 - 0.0129

sodium iso-propylxanthate

0.0074

sophoraflavanone G

-

0.0008 - 0.8

tropolone

0.0015

[4-oxo-2-(pyridin-4-ylmethylene-hydrazono)-thiazolidin-5-ylidene]-acetic acid methyl ester

-

pH 6.8, 25°C, substrate L-DOPA

additional information

16 entries

-

0.035

(+)-gallocatechin-3-O-gallate

Agaricus bisporus

-

competitive inhibition

0.034

(-)-epigallocatechin-3-O-gallate

Agaricus bisporus

-

competitive inhibition

0.25

(1E,4E)-1,5-bis(2-fluoro-4-methoxyphenyl)penta-1,4-dien-3-one

Agaricus bisporus

-

IC50 above 0.25 mM

0.25

(1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one

Agaricus bisporus

-

IC50 above 0.25 mM

0.25

(1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

Agaricus bisporus

-

IC50 above 0.25 mM

0.298

(2-([4-(4-methoxy-benzyloxy)-benzylidene]-hydrazono)-4-oxothiazolidin-5-ylidene)-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.0498

(2-[(5-methyl-furan-2-ylmethylene)-hydrazono]-4-oxothiazolidin-5-ylidene)-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

1

(2E)-3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

0.35

(2E)-3-(3,4-dihydroxyphenyl)-N-(4-hydroxybenzyl)prop-2-enamide

Agaricus bisporus

-

1

(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

0.6

(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-enamide

Agaricus bisporus

-

0.25

(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

Agaricus bisporus

-

0.2781

(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.3218

(2E)-3-(3,4-dimethoxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

1

(2E)-3-(4-chlorophenyl)-N-[2-(4-chlorophenyl)ethyl]prop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

0.35

(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.03

(2E)-3-(4-hydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide

Agaricus bisporus

-

0.5

(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

1

(2E)-3-(4-methoxyphenyl)-N-(1-phenylethyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

1

(2E)-3-(4-methoxyphenyl)-N-(2-phenylethyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

0.42

(2E)-3-(4-methoxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

0.1

(2E)-3-phenyl-N-(1-phenylethyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 0.1 mM

0.1

(2E)-3-phenyl-N-(2-phenylethyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 0.1 mM

2.1

(2E)-3-phenylprop-2-enoic acid

Agaricus bisporus

-

12.05 - 20

(2E)-but-2-enoic acid

0.35

(2E)-N-(3,4-dihydroxybenzyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide

Agaricus bisporus

-

0.1

(2E)-N-(4-chlorobenzyl)-3-phenylprop-2-enamide

Agaricus bisporus

-

IC50 above 0.1 mM

0.25

(2E)-N-benzyl-3-(3,4-dihydroxyphenyl)prop-2-enamide

Agaricus bisporus

-

0.028

(2E)-N-benzyl-3-(4-hydroxyphenyl)prop-2-enamide

Agaricus bisporus

-

1

(2E)-N-benzyl-3-(4-methoxyphenyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

0.1

(2E)-N-benzyl-3-phenylprop-2-enamide

Agaricus bisporus

-

IC50 above 0.1 mM

0.1

(2E)-N-[2-(4-chlorophenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

Agaricus bisporus

-

IC50 above 0.1 mM

1

(2E)-N-[2-(4-chlorophenyl)ethyl]-3-phenylprop-2-enamide

Agaricus bisporus

-

IC50 above 1 mM

0.0054

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.008

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.008

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.0238

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-methoxyphenyl)prop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.0404

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-phenylprop-2-enamide

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.9 - 4.95

(2E,4E)-hexa-2,4-dienoic acid

0.25

(2E,6E)-2,6-bis[(4-chlorophenyl)methylidene]cyclohexanone

Agaricus bisporus

-

IC50 above 0.25 mM

0.25

(2E,6E)-2,6-bis[(4-hydroxyphenyl)methylidene]cyclohexanone

Agaricus bisporus

-

IC50 above 0.25 mM

0.24

(2R,3R)-taxifolin

Agaricus bisporus

-

0.35

(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.35

(2Z)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.1152

(2Z)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.35

(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.35

(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.1213

(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.35

(2Z)-3-(4-methoxyphenyl)prop-2-enoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.35

(2Z)-3-phenylprop-2-enoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.0501

(4-oxo-2-[(1H-pyrrol-2-ylmethylene)-hydrazono]-thiazolidin-5-ylidene)-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.208

(4-oxo-2-[(3-phenyl-allylidene)-hydrazono]-thiazolidin-5-ylidene)-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.07905

1,5-bis(4-hydroxyphenyl)-1,4-pentadiene-3-one

Agaricus bisporus

-

0.00015

1-(1,4-diacetylphenyl)dithiosemicarbazide

Agaricus bisporus

-

0.022

1-(1-(2,4,6-trihydroxyphenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00058

1-(1-(2,4-dihydroxyphenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00052

1-(1-(4-bromophenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00017

1-(1-(4-fluorophenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00031

1-(1-(4-hydroxyphenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.001

1-(1-(4-isopropylphenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00011

1-(1-(4-methoxyphenyl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00042

1-(1-(4-methoxyphenyl)propan-2-ylidene)-thiosemicarbazide

Agaricus bisporus

-

0.00042

1-(1-(4-methoxyphenyl)propan-2-ylidene)thiosemicarbazide

Agaricus bisporus

-

0.00088

1-(1-(pyrazin-2-yl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00082

1-(1-(pyridin-3-yl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00014

1-(1-(thiophen-2-yl)ethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00027

1-(1-p-tolylethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00034

1-(1-phenylethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00024

1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)propane

Agaricus bisporus

-

0.00085

1-(2,5-dimethyl-1H-pyrrol-1-yl)thiourea

Agaricus bisporus

-

0.0555

1-(2-hydroxy-1,2-diphenylethylidene)thiosemicarbazide

Agaricus bisporus

-

0.1

1-(2-oxo-1,2-diphenylethylidene)thiosemicarbazide

Agaricus bisporus

-

0.00062

1-(3-methylbutylidene)thiosemicarbazide

Agaricus bisporus

-

0.0151

1-(3-oxocyclohexylidene)thiosemicarbazide

Agaricus bisporus

-

0.0027

1-(3-phenylallylidene)thiosemicarbazide

Agaricus bisporus

-

0.00054

1-(4-(4-hydroxyphenyl)butan-2-ylidene)-thiosemicarbazide

Agaricus bisporus

-

0.00054

1-(4-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide

Agaricus bisporus

-

0.0027

1-(4-bromophenyl)-3-hydroxyurea

Agaricus bisporus

-

0.99

1-(4-fluorophenyl)-ethanone

Agaricus bisporus

-

2

1-(4-methoxyphenyl)-ethanone

Agaricus bisporus

-

0.0115

1-(4-methylpent-3-en-2-ylidene) thiosemicarbazide

Agaricus bisporus

-

0.001

1-(but-2-enylidene)thiosemicarbazide

Agaricus bisporus

-

0.00028

1-(butan-2-ylidene)thiosemicarbazide

Agaricus bisporus

-

0.000086 - 0.00011

1-(propan-2-ylidene)thiosemicarbazide

0.15

1-(thiophen-2-yl)-ethanone

Agaricus bisporus

-

0.00095

1-cyclohexylidenethiosemicarbazide

Agaricus bisporus

-

0.000075 - 0.0006

1-cyclopentyl-1-hydroxy-2-oxohydrazine

0.00017

1-cyclopentylidenethiosemicarbazide

Agaricus bisporus

-

0.00026 - 0.0022

1-dodecyl-1-hydroxy-2-oxohydrazine

0.00023

1-ethylidenethiosemicarbazide

Agaricus bisporus

-

0.77

1-hydroxy-1-methyl-3-(4-nitrophenyl)urea

Agaricus bisporus

-

0.0062 - 0.046

1-hydroxy-1-naphthalen-1-yl-2-oxohydrazine

0.00013 - 0.0011

1-hydroxy-2-oxo-1-phenylhydrazine

0.041

1-hydroxy-3-(4-hydroxyphenyl)urea

Agaricus bisporus

-

0.032

1-hydroxy-3-(4-methoxyphenyl)urea

Agaricus bisporus

-

0.0026

1-hydroxy-3-(4-nitrophenyl)urea

Agaricus bisporus

-

0.00029

1-hydroxy-3-phenylurea

Agaricus bisporus

-

0.0043

1-hydroxy-3-[4-(trifluoromethyl)phenyl]urea

Agaricus bisporus

-

0.026

1-methoxy-3-naphthalen-2-ylthiourea

Agaricus bisporus

-

0.0803

1-methylethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.0078

1-pentanoyl-3-(2,3-dichlorophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0197

1-pentanoyl-3-(2,4,6-trimethylphenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0101

1-pentanoyl-3-(2,4-dinitrophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0195

1-pentanoyl-3-(2,6-dibromo-4-fluorophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0166

1-pentanoyl-3-(3-nitrophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0065

1-pentanoyl-3-(4-bromo-2-fluorophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0034

1-pentanoyl-3-(4-bromophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0023

1-pentanoyl-3-(4-chlorophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0016

1-pentanoyl-3-(4-methoxyphenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.008

1-pentanoyl-3-(4-nitrophenyl)thiourea

Agaricus bisporus

-

pH 6.8, 25°C

0.0002

1-propylidenethiosemicarbazide

Agaricus bisporus

-

0.000086

1-[1-(4-methoxyphenyl)ethylidene]thiosemicarbazide

Agaricus bisporus

-

0.0063

1-[4-(benzyloxy)phenyl]-3-hydroxyurea

Agaricus bisporus

-

0.07

1-[[tert-butyl(dimethyl)silyl]oxy]-3-phenylurea

Agaricus bisporus

-

0.582

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

Agaricus bisporus

-

0.0694

2,2':4',2''-ter-1,3,4-oxadiazole-5,5',5''(4H,4''H)-trithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.0029

2,2':4',2''-ter-1,3,4-thiadiazole-5,5',5''(4H,4''H)-trithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.0431 - 0.0461

2,3,4'-trihydroxy-4-methoxydeoxybenzoin

0.3 - 0.5

2,3,4,4'-tetrahydroxydeoxybenzoin

0.2033 - 0.3

2,3,4-trihydroxy-4'-methoxydeoxybenzoin

0.2613 - 0.3

2,4,4',6-tetrahydroxydeoxybenzoin

0.1359 - 0.1785

2,4,4'-trihydroxydeoxybenzoin

0.08435 - 0.1974

2,4,5-trihydroxy-4'-methoxydeoxybenzoin

0.07105 - 0.2302

2,4,6-trihydroxy-4'-methoxydeoxybenzoin

0.1121 - 0.2397

2,4-dihydroxy-3',4'-dimethoxydeoxybenzoin

0.0788 - 0.1814

2,4-dihydroxy-4'-methoxydeoxybenzoin

0.55

2,4-dihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 0.550 mM

1.82

2,4-dihydroxy-N-(4-hydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 1.820 mM

0.00045

2-(2-furanylmethylene)-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.0265

2-(2-hydroxyethoxy)ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.0591

2-(2-methoxyethoxy)ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.16

2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl 3,4,5-trihydroxybenzoate

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8) for 10 min at 25°C

0.12

2-(4-fluorophenyl)-quinazolin-4(3H)-one

Agaricus bisporus

-

pH and temperature not specified in the publication

744491

0.0309

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-chlorophenyl)prop-2-enoate

Agaricus bisporus

-

pH 6.8, 25°C

0.0161

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Agaricus bisporus

-

pH 6.8, 25°C

0.0426

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 2,4-dihydroxybenzoate

Agaricus bisporus

-

pH 6.8, 25°C

0.1569

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 3,4-dihydroxybenzoate

Agaricus bisporus

-

pH 6.8, 25°C

0.0598

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 3,5-dihydroxybenzoate

Agaricus bisporus

-

pH 6.8, 25°C

0.2012

2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 4-hydroxybenzoate

Agaricus bisporus

-

pH 6.8, 25°C

0.00193

2-(phenylmethylene)-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00122 - 0.0154

2-chlorobenzaldehyde thiosemicarbazone

2.28

2-hydroxy-4-methoxybenzoic acid

Agaricus bisporus

-

1.65

2-hydroxy-4-methylbenzoic acid

Agaricus bisporus

-

7.9

2-hydroxy-5-methoxybenzoic acid

Agaricus bisporus

-

2.15

2-hydroxy-5-methylbenzoic acid

Agaricus bisporus

-

2.85

2-Hydroxybenzaldehyde

Agaricus bisporus

-

4.3

2-hydroxybenzoic acid

Agaricus bisporus

-

0.0749

2-hydroxyethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.0004

2-hydroxytropone

Agaricus bisporus

-

0.0981

2-methoxyethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

2.6

2-Methylbenzaldehyde

Agaricus bisporus

-

2.56

2-Methylbenzoic acid

Agaricus bisporus

-

0.717 - 1.415

2-Methylresorcinol

15

2-oxoglutaric acid

Agaricus bisporus

-

pH 7.0, 25°C

0.0153

2-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]phenol

Agaricus bisporus

-

pH 6.8, 30°C

0.0127

2-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]phenol

Agaricus bisporus

-

pH 6.8, 30°C

0.2

2-[(2,3,4-trihydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00018

2-[(2,4-dihydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.0065

2-[(2,5-dihydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.0875

2-[(2,5-dimethoxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00033

2-[(2-hydroxy-4-bromophenyl)methylene]thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00038

2-[(2-hydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.1152

2-[(3,4,5-trihydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.1455

2-[(3,4,5-trimethoxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.0422

2-[(3,4-dihydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.0336

2-[(3,5-dihydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00488

2-[(3-hydroxy-4-methoxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.0039

2-[(3-hydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00568

2-[(3-methoxy-4-hydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00028

2-[(4-bromophenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00041

2-[(4-hydroxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00148

2-[(4-methoxyphenyl)methylene]-thiosemicarbazone

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

0.00073

2-[2-(2,4-dihydroxyphenyl)ethyl]-5-(D-xylopyranosyloxy)phenyl D-xylopyranoside

Agaricus bisporus

-

0.0016

2-[2-(2,4-dihydroxyphenyl)ethyl]-5-hydroxyphenyl D-xylopyranoside

Agaricus bisporus

-

5times more potent than that of kojic acid

0.0792

2-[2-(2-hydroxyethoxy)ethoxy]ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.0676

2-[2-(2-methoxyethoxy)ethoxy]ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.0000167

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(2,4-dihydroxyphenyl)prop-2-enoate

Agaricus bisporus

pH 6.8, 25°C

0.0067

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-chlorophenyl)prop-2-enoate

Agaricus bisporus

pH 6.8, 25°C

0.0065

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Agaricus bisporus

pH 6.8, 25°C

0.0077

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-phenylprop-2-enoate

Agaricus bisporus

pH 6.8, 25°C

0.0067

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 2,4-dihydroxybenzoate

Agaricus bisporus

pH 6.8, 25°C

0.0652

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,4,5-trihydroxybenzoate

Agaricus bisporus

pH 6.8, 25°C

0.0159

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,4-dihydroxybenzoate

Agaricus bisporus

pH 6.8, 25°C

0.0938

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,5-dihydroxybenzoate

Agaricus bisporus

pH 6.8, 25°C

0.0149

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3-hydroxybenzoate

Agaricus bisporus

pH 6.8, 25°C

0.0149

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 4-hydroxybenzoate

Agaricus bisporus

pH 6.8, 25°C

0.001

2-[3-(2,4-dimethoxy-3-methylphenyl)propyl]benzene-1,4-diol

Agaricus bisporus

-

0.00112

2alpha,3alpha,23-trihydroxyolean-12-en-28-oic acid

Agaricus bisporus

-

0.0114

3'',4''-dihydroglabridin

Agaricus bisporus

-

in 20 mM phosphate buffer (pH 6.8), at 25°C

0.555

3,4,5-trihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 0.555 mM

1.18

3,4,5-trihydroxy-N-(4-hydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 1.180 mM

0.168 - 0.3

3,4-dihydroxy-4'-methoxydeoxybenzoin

0.28

3,4-dihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 0.280 mM

2

3,4-dihydroxy-N-(4-hydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 2.0 mM

0.0003

3,4-dihydroxybenzaldehyde-O-ethyloxime

Agaricus bisporus

-

0.97

3,4-dihydroxycinnamic acid

Agaricus bisporus

-

1

3,4-dimethoxycinnamic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

1

3,4-dimethoxydihydrocinnamic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.705

3,5-dihydroxy-N-(3,4,5-trihydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 0.705 mM

0.71

3,5-dihydroxy-N-(4-hydroxybenzyl)benzamide

Agaricus bisporus

-

IC50: 0.710 mM

0.27

3-(3',4',5'-trihydroxyphenyl)-6,8-dihydroxycoumarin

Agaricus bisporus

-

in 0.067 M phosphoric acid buffer (pH 6.8), at 25°C

3.68

3-(3-hydroxyphenyl)-2H-chromen-2-one

Agaricus bisporus

-

in 0.067 M phosphoric acid buffer (pH 6.8), at 25°C

0.035

3-cymene

Agaricus bisporus

-

competitive, IC50: 0.035 mM

0.016

3-hydroxy-1-methyl-1-phenylurea

Agaricus bisporus

-

3.7

3-Hydroxybenzaldehyde

Agaricus bisporus

-

1

3-hydroxycinnamic acid

Agaricus bisporus

-

IC50 above 1 mM

0.0634

3-hydroxyphloretin

Agaricus bisporus

-

exhibits a dose-dependent inhibitory effect on mushroom tyrosinase activity, 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)

689413

1.8

3-Methoxybenzaldehyde

Agaricus bisporus

-

0.45

3-methylbenzaldehyde

Agaricus bisporus

-

0.58

3-methylbenzoic acid

Agaricus bisporus

-

1.7

3-methylcrotonic acid

Agaricus bisporus

-

0.01102

3beta, 23, 24-trihydroxyolean-12-en-28-oic acid

Agaricus bisporus

-

0.1

4'-hydroxy-[1,1'-biphenyl]-2-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.01059

4'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.0147

4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.1

4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid

Agaricus bisporus

-

above, pH 6.5, 30°C

0.0153

4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.0153

4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.0024

4,4'-diamino-3-(4-hydroxyphenyl)-1'H-1,3'-bi-1,2,4-triazole-5,5'(4H,4'H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00101

4,4'-diamino-3-(pyridin-4-yl)-1'H-1,3'-bi-1,2,4-triazole-5,5'(4H,4'H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00037

4,4'-ethane-1,2-diyldibenzene-1,3-diol

Agaricus bisporus

-

0.075

4-(1-methylethyl)benzaldehyde

Agaricus bisporus

-

0.225

4-(1-methylethyl)benzoic acid

Agaricus bisporus

-

0.049

4-(benzyloxy)-N'-(hydrazinylcarbonyl)benzohydrazide

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

1.15

4-(hexyloxy)benzoic acid

Agaricus bisporus

-

1.4

4-(pentyloxy)benzoic acid

Agaricus bisporus

-

1.65

4-butoxybenzoic acid

Agaricus bisporus

-

0.038

4-butylbenzaldehyde

Agaricus bisporus

-

0.165

4-butylbenzoic acid

Agaricus bisporus

-

0.00182 - 0.0067

4-chlorobenzaldehyde thiosemicarbazone

0.1156

4-coumaric acid

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.023

4-ethenylbenzaldehyde

Agaricus bisporus

-

0.33

4-ethenylbenzoic acid

Agaricus bisporus

-

1.1

4-ethoxybenzoic acid

Agaricus bisporus

-

0.095

4-Ethylbenzaldehyde

Agaricus bisporus

-

0.29

4-ethylbenzoic acid

Agaricus bisporus

-

0.0019 - 0.00931

4-ethylresorcinol

0.0216

4-formyl-2-methoxyphenyl (4-methylpiperazin-1-yl)acetate

Agaricus bisporus

-

pH 6.8, 25°C

0.1014

4-formyl-2-methoxyphenyl (4-phenylpiperazin-1-yl)acetate

Agaricus bisporus

-

pH 6.8, 25°C

0.0789

4-formyl-2-methoxyphenyl chloroacetate

Agaricus bisporus

-

pH 6.8, 25°C

3

4-formylphenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Agaricus bisporus

-

3

4-formylphenyl 2,3,4-tri-O-acetyl-beta-D-allopyranoside

Agaricus bisporus

-

3

4-formylphenyl 2,3,4-tri-O-benzyl-beta-D-ribopyranoside

Agaricus bisporus

-

3

4-formylphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside

Agaricus bisporus

-

0.62

4-formylphenyl 2,3-O-(1-methylethylidene)-beta-D-allopyranoside

Agaricus bisporus

-

0.052

4-formylphenyl 4,6-O-(phenylmethylidene)-beta-D-gulopyranoside

Agaricus bisporus

-

0.43

4-formylphenyl 6-O-(dimethoxyphosphoryl)-beta-D-allopyranoside

Agaricus bisporus

-

3

4-formylphenyl 6-O-trityl-beta-D-allopyranoside

Agaricus bisporus

-

2.54

4-formylphenyl beta-D-allopyranoside

Agaricus bisporus

-

0.94

4-formylphenyl beta-D-glucopyranoside

Agaricus bisporus

-

0.28

4-formylphenyl beta-D-ribopyranoside

Agaricus bisporus

-

2.54

4-formylphenyl-O-beta-D-allopyranoside

Agaricus bisporus

-

0.0088

4-heptylbenzaldehyde

Agaricus bisporus

-

0.095

4-heptylbenzoic acid

Agaricus bisporus

-

0.008

4-hexylbenzaldehyde

Agaricus bisporus

-

0.11

4-hexylbenzoic acid

Agaricus bisporus

-

0.0025 - 0.018

4-hexylresorcinol

0.97

4-hydroxy-3-methoxycinnamic acid

Agaricus bisporus

-

1.12 - 1.22

4-hydroxybenzaldehyde

1.3

4-hydroxybenzoic acid

Agaricus bisporus

-

3

4-hydroxyphenyl beta-D-xyloside

Agaricus bisporus

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.74

4-hydroxyphenyl beta-xylodioside

Agaricus bisporus

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.18

4-hydroxyphenyl beta-xylotetraoside

Agaricus bisporus

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.48

4-hydroxyphenyl beta-xylotrioside

Agaricus bisporus

-

in 100 mM sodium phosphate buffer (pH 6.8), at 25°C

0.35

4-methoxybenzaldehyde

Agaricus bisporus

-

0.42

4-methoxybenzoic acid

Agaricus bisporus

-

0.41 - 0.8617

4-methoxycinnamic acid

0.12

4-methylbenzaldehyde

Agaricus bisporus

-

0.35

4-methylbenzoic acid

Agaricus bisporus

-

0.0011

4-methylresorcinol

Agaricus bisporus

-

pH 7.0, 25°C, inhibition of the diphenolase activity of mushroom tyrosinase

0.01

4-octylbenzaldehyde

Agaricus bisporus

-

0.082

4-octylbenzoic acid

Agaricus bisporus

-

0.0135

4-pentylbenzaldehyde

Agaricus bisporus

-

0.12

4-pentylbenzoic acid

Agaricus bisporus

-

0.8 - 1.1

4-phenyl-2-butanol

1.85

4-propoxybenzoic acid

Agaricus bisporus

-

0.075

4-propylbenzaldehyde

Agaricus bisporus

-

0.235

4-propylbenzoic acid

Agaricus bisporus

-

0.038

4-tert-butylbenzaldehyde

Agaricus bisporus

-

0.215

4-tert-butylbenzoic acid

Agaricus bisporus

-

0.00341

4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside

Agaricus bisporus

-

0.00041

4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside

Agaricus bisporus

-

0.00031

4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Agaricus bisporus

-

0.0528

4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside

Agaricus bisporus

-

0.0365

4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside

Agaricus bisporus

-

0.00065

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

Agaricus bisporus

-

0.00361

4-[(E)-(carbamothioylhydrazono)methyl]phenyl beta-D-allopyranoside

Agaricus bisporus

-

0.00296

4-[(E)-(carbamothioylhydrazono)methyl]phenyl beta-D-glucopyranoside

Agaricus bisporus

-

0.2

4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(hydroxyimino)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

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

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(hydroxyimino)methyl]phenyl beta-D-allopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(hydroxyimino)methyl]phenyl beta-D-glucopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

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

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl beta-D-allopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.2

4-[(E)-(methoxyimino)methyl]phenyl beta-D-glucopyranoside

Agaricus bisporus

-

IC50 above 0.2 mM

0.00043

4-[2-(2,4-dihydroxyphenyl)ethyl]-3-hydroxyphenyl D-xylopyranoside

Agaricus bisporus

-

0.024

4-[3-(2-hydroxy-5-methoxyphenyl)propyl]benzene-1,3-diol

Agaricus bisporus

-

0.0027 - 0.0238

4-[[hydroxy(nitroso)amino]methyl]benzene-1,3-diol

0.0011 - 0.0137

4-[[hydroxy(nitroso)amino]methyl]phenol

0.0185

5'-(3-hydroxyphenyl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00177

5'-(4-hydroxyphenyl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00019

5'-(4-hydroxyphenyl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00053

5'-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00676

5'-(diphenylmethyl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.0052

5'-(diphenylmethyl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.0336

5'-(naphthalen-1-yl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.0142

5'-(pyridin-4-yl)-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00247

5'-(pyridin-4-yl)-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00367

5'-benzyl-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00494

5'-cyclohexyl-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00647

5'-phenyl-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00131

5'-phenyl-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00442

5'-[(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)methyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00049

5'-[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)methyl]-2,3'-bi-1,3,4-thiadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.0019

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

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00364

5'-[3-(benzyloxy)phenyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00135

5'-[4-(benzyloxy)phenyl]-2,3'-bi-1,3,4-oxadiazole-2',5(4H)-dithione

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.00026 - 0.01861

5,2',4'-trihydroxy-2'',2''-dimethylchromene-(6,7:5'',6'')-flavanone

0.1325

5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.0342

5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.1374

5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.1793

5-(4-(2-butoxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.1074

5-(4-(2-butoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.04545

5-(4-(2-butoxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.1559

5-(4-(2-hydroxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(2-hydroxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(2-hydroxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(2-hydroxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.1128

5-(4-(2-methoxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(2-methoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.02843

5-(4-(2-methoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.07542

5-(4-(2-methoxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(4-methoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(4-methoxybutoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-(4-methoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.0778

5-(4-(4-methoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.07002

5-(4-hydroxybenzyl)-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.2

5-(4-hydroxybenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

IC50 above 0.2 mM, in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.01449

5-(4-hydroxybenzylidene)-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.01398

5-(4-hydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Agaricus bisporus

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

0.0514 - 0.0516

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

0.98

5-hydroxymethyl-2-furfural

Agaricus bisporus

-

0.0422

6-hydroxy-2H-pyran-3-carbaldehyde

Agaricus bisporus

-

1.567

6-hydroxy-3-(4'-hydroxyphenyl)coumarin

Agaricus bisporus

-

in 0.067 M phosphoric acid buffer (pH 6.8), at 25°C

0.193

6-hydroxyapigenin

Agaricus bisporus

-

0.182

6-hydroxygalangin

Agaricus bisporus

-

0.124

6-hydroxykaempferol

Agaricus bisporus

-

0.1

7-hydroxy-3-(4-hydroxyphenyl)-2H-chromen-2-one

Agaricus bisporus

-

IC50 above 0.1 mM, in 0.067 M phosphoric acid buffer (pH 6.8), at 25°C

0.0442 - 0.2

8-isoprenyl-5'-geranyl-5,7,2',4'-tetrahydroxy flavanone

0.312

8-O-methyltianmushanol

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 37°C

0.2

9-hydroxy-4-methoxypsoralen

Agaricus bisporus

-

0.00078

Ac-KSRFR

Agaricus bisporus

-

pH 6.8, 25°C

0.00081

Ac-KSSFR

Agaricus bisporus

-

pH 6.8, 25°C

0.00075

Ac-RSRFK

Agaricus bisporus

-

pH 6.8, 25°C

0.00029

Ac-RSRFS

Agaricus bisporus

-

pH 6.8, 25°C

0.85

acetophenone

Agaricus bisporus

-

0.03

Agaritine

Agaricus bisporus

-

0.0985 - 0.2

albafuran A

0.1

aloesin

Agaricus bisporus

-

12

alpha-picolyl heptyl amine

Agaricus bisporus

-

IC50 above 12 mM, in 0.1 M phosphate buffer (pH 6.5)

12

alpha-picolyl pentyl amine

Agaricus bisporus

-

IC50 above 12 mM, in 0.1 M phosphate buffer (pH 6.5)

12

alpha-picolyl propyl amine

Agaricus bisporus

-

IC50 above 12 mM, in 0.1 M phosphate buffer (pH 6.5)

0.0075 - 0.028

ammonium tetramolybdate

0.0001

anacardic acid

Agaricus bisporus

-

0.38

Anisaldehyde

Agaricus bisporus

-

0.68

Anisic acid

Agaricus bisporus

-

0.04 - 548

arbutin

10 entries

0.006577

arjungenin

Agaricus bisporus

-

0.001

arjunilic acid

Agaricus bisporus

-

0.001545

artocarpanone

Agaricus bisporus

-

0.0005254

artocarpesin

Agaricus bisporus

-

0.2009

artocarpetin

Agaricus bisporus

-

0.04793

artocarpfuranol

Agaricus bisporus

-

0.273

baicalein

Agaricus bisporus

-

0.0011

bayogenin

Agaricus bisporus

-

0.8

benzaldehyde

Agaricus bisporus

-

1

benzoic acid

Agaricus bisporus

-

0.6 - 2.8

benzylacetone

1.5 - 2

benzylideneacetone

6.3

beta-arbutin

Agaricus bisporus

-

9.5

beta-picolyl heptyl amine

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.5)

12

beta-picolyl pentyl amine

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.5)

12

beta-picolyl propyl amine

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.5)

1.44

betulin

Agaricus bisporus

-

0.00214

betulinic acid

Agaricus bisporus

-

25

Bromoacetate

Agaricus bisporus

-

699039

0.06028

brosimone I

Agaricus bisporus

-

0.00043 - 0.00057

broussonin C

0.35

bufobutanoic acid

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.4 - 1

caffeic acid

0.0089

campestrol

Agaricus bisporus

-

isolated from Trifolium balansae, NMR structure identification, IC50: 0.00890 mM

0.09438

carpachromene

Agaricus bisporus

-

0.02 - 7

cefazolin

0.13 - 0.21

cefodizime

1

Cinnamic acid

0.1666

cudraflavone B

Agaricus bisporus

-

0.26

cumic acid

Agaricus bisporus

-

0.05

cuminaldehyde

Agaricus bisporus

-

0.06873

cyanomaclurin

Agaricus bisporus

-

0.092

cyclomorusin

Agaricus bisporus

-

for monophenolase activity

0.58

D-ascorbic acid-6-p-hydroxybenzoic acid ester

Agaricus bisporus

-

in 50 mM phosphate buffer (pH 6.8) for 10 min at 25°C

0.194

daedalin A

Agaricus bisporus

-

685668

0.017

davanol

Agaricus bisporus

-

competitive, IC50: 0.017 mM

1

dihydro-4-coumaric acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

1

dihydro-4-methoxycinnamic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

1

dihydrocaffeic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

1

dihydrocinnamic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

1

dihydroferulic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.1957

dihydroisoferulic acid

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.01035

dihydromorin

Agaricus bisporus

-

1

dihydrosinapic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.034

dillapiole

Agaricus bisporus

-

competitive, IC50: 0.034 mM

0.0655

epigallocatechin gallate

Agaricus bisporus

-

0.00312

erythrodiol

Agaricus bisporus

-

0.21 - 0.225

esculetin

0.0363

ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.11

farnesic acid

Agaricus bisporus

-

1

ferulic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.00179 - 0.00748

flemichin D

0.00101 - 0.0195

fleminchalcone A

0.0184 - 0.0326

fleminchalcone B

0.00128 - 0.00522

fleminchalcone C

6.8

gamma-picolyl heptyl amine

Agaricus bisporus

-

4.2

gamma-picolyl pentyl amine

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.5)

5.8

gamma-picolyl propyl amine

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.5)

1.62

geranial

Agaricus bisporus

-

0.01858

glabridin

Agaricus bisporus

-

in 20 mM phosphate buffer (pH 6.8), at 25°C

16.08

hesperidin

Agaricus bisporus

-

3.35 - 13.2

hexanoic acid

0.01348 - 1.09

hydroquinone

0.0006628

isoartocarpesin

Agaricus bisporus

-

0.1149

isoferulic acid

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.23 - 0.262

kaempferol

0.0155 - 0.0228

kazinol C

0.1647 - 0.2

kazinol D

0.00096 - 0.0017

kazinol F

0.0179 - 0.0269

kazinol S

0.1031 - 0.2

kazinol T

3.6

KFEKKFEK

Agaricus bisporus

-

in 0.67 mM potassium phosphate buffer (pH 6.8), at 37°C

0.00496 - 0.0204

khonklonginol H

0.0074 - 0.68

kojic acid

29 entries

0.88

kuraridinol

Agaricus bisporus

-

potent tyrosinase inhibitory activity

0.0001 - 8.6

kurarinol

0.0022

kurarinone

Agaricus bisporus

-

0.1318 - 0.2

kuwanon A

0.135

kuwanon C

Agaricus bisporus

-

for monophenolase activity

0.0475 - 0.2

kuwanon E

0.2

kuwanon U

0.00368

L-mimosine

2.73

L-Pro-L-Leu-Gly

Agaricus bisporus

-

in 0.67 mM potassium phosphate buffer (pH 6.8), at 37°C

2.24

lupeol

Agaricus bisporus

-

0.0112 - 0.0841

lupinifolin

0.0017

maslinic acid

Agaricus bisporus

-

0.04 - 0.047

Methimazole

0.349

methyl (Z)-2-((E)-2-(((E)-(5-bromothiophen-2-yl)methylene)hydrazono)-4-oxothiazolidin-5-ylidene)acetate

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.101

methyl (Z)-2-((E)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)-4-oxothiazolidin-5-ylidene)acetate

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.002345

methyl arjunolate

Agaricus bisporus

-

0.0074 - 0.0646

moracin M

0.1603 - 0.2

moracin N

0.0825 - 0.2

moracinoside M

2.32

morin

Agaricus bisporus

-

competitive, IC50: 2.320 mM

0.088

mormin

Agaricus bisporus

-

for monophenolase activity

0.25

morusin

Agaricus bisporus

-

for monophenolase activity

0.2

morusinol

0.027

N',N'''-benzene-1,4-diylbis(1-hydroxyurea)

Agaricus bisporus

-

0.1772

N'-(hydrazinylcarbonyl)-4-hydroxybenzohydrazide

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.996

N'-(hydrazinylcarbonyl)naphthalene-2-carbohydrazide

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 25°C

0.17 - 0.23

N,N-unsubstituted selenourea derivatives

Agaricus bisporus

-

55.5% inhibition at 0.2 mM, IC50: 0.17-0.23 mM

-

0.029

N-(2,4-dihydroxybenzyl)-2,4-dihydroxybenzamide

Agaricus bisporus

-

IC50: 0.029 mM

0.017

N-(2,4-dihydroxybenzyl)-3,4,5-trihydroxybenzamide

Agaricus bisporus

-

IC50: 0.017 mM

0.011

N-(2,4-dihydroxybenzyl)-3,4-dihydroxybenzamide

Agaricus bisporus

-

IC50: 0.011 mM

0.0022

N-(2,4-dihydroxybenzyl)-3,5-dihydroxybenzamide

Agaricus bisporus

-

IC50: 0.0022 mM

1.66

N-benzyl-2,4-dihydroxybenzamide

Agaricus bisporus

-

IC50: 1.660 mM

0.78

N-benzyl-3,4,5-trihydroxybenzamide

Agaricus bisporus

-

IC50: 0.780 mM

2

N-benzyl-3,4-dihydroxybenzamide

Agaricus bisporus

-

IC50: 2.0 mM

0.7

N-benzyl-3,5-dihydroxybenzamide

Agaricus bisporus

-

IC50: 0.700 mM

1.99

N-benzylamide

Agaricus bisporus

-

IC50: 1.990 mM

0.17

N-hydroxy-N-(phenylcarbamoyl)acetamide

Agaricus bisporus

-

0.0018

N-phenylthiourea

Agaricus bisporus

-

0.1274 - 0.2

neocyclomorusin

1.49

nobiletin

Agaricus bisporus

-

0.0012 - 0.4647

norartocarpetin

2.15 - 3.06

octanoic acid

0.4

octyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate

Agaricus bisporus

-

in 0.1 M phosphate buffer (pH 6.8), at 37°C

0.001 - 0.0012

oxyresveratrol

0.2 - 3.65

p-coumaric acid

0.3506

p-hydroxybenzyl alcohol

Agaricus bisporus

-

685452

0.17

Phenylthiourea

Agaricus bisporus

-

IC50: 0.17 mM

0.346

procyanidin B1

Agaricus bisporus

-

0.07

quercetin

Agaricus bisporus

-

competitive, IC50: 0.070 mM

0.123

RADSRADC

Agaricus bisporus

-

in 0.67 mM potassium phosphate buffer (pH 6.8), at 37°C

0.652 - 1.125

resorcinol

0.0008 - 0.0012

Salicylhydroxamic acid

0.35

serotonin

Agaricus bisporus

-

IC50 above 0.35 mM, in 0.1 M phosphate buffer (pH 7.0), at 37°C

8

SFLLRN

Agaricus bisporus

-

in 0.67 mM potassium phosphate buffer (pH 6.8), at 37°C

1

Sinapic acid

Agaricus bisporus

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

0.0047

sophoraflavanone G

Agaricus bisporus

-

1.13

soyacerebroside I

Agaricus bisporus

-

0.0005733 - 0.0265

steppogenin

0.00239

stigmast-5-ene-3beta,26-diol

Agaricus bisporus

-

isolated from Trifolium balansae, NMR structure identification, IC50: 0.00239 mM

0.00525

stigmast-5-ene-3beta-ol

Agaricus bisporus

-

isolated from Trifolium balansae, NMR structure identification, IC50: 0.00525 mM

2

Thiosemicarbazide

0.358

tianmushanol

Agaricus bisporus

-

in 50 mM Na-phosphate buffer (pH 6.8), at 37°C

0.85

trans-cinnamaldehyde

Agaricus bisporus

-

0.14 - 2.3

trans-geranic acid

506.8

trifolirhizin

Agaricus bisporus

-

moderate inhibitory activity

0.0004 - 0.0017

tropolone

0.42

umbelliferone

Agaricus bisporus

-

in 0.067 M phosphoric acid buffer (pH 6.8), at 25°C

0.04

YRSRKYSSWY

Agaricus bisporus

-

in 0.67 mM potassium phosphate buffer (pH 6.8), at 37°C

0.00697

[1,1''-biphenyl]-3-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.1

[1,1'-biphenyl]-2-carboxylic acid

Agaricus bisporus

-

above, pH 6.5, 30°C

0.06324

[1,1'-biphenyl]-4-carboxylic acid

Agaricus bisporus

-

pH 6.5, 30°C

0.0753

[2-(furan-2-ylmethylene-hydrazono)-4-oxo-thiazolidin-5-ylidene]-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.142

[2-[(4-benzyloxy-benzylidene)-hydrazono]-4-oxo-thiazolidin-5-ylidene]-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

0.0032

[4-oxo-2-(pyridin-4-ylmethylene-hydrazono)-thiazolidin-5-ylidene]-acetic acid methyl ester

Agaricus bisporus

-

pH 6.8, 25°C, substrate L-DOPA

additional information

7 entries

-

1.22

purified recombinant enzyme, substrate L-tyrosine, pH 6.8, 25°C

1530

-

1700

Sigma mushroom tyrosinase (SMT, crude powder, lot 105k7026) (units/mg of powder), WMT and SMT show different levels of tyrosinase activity per milligram of powder

3000

-

mushroom tyrosinase 3000/mg

3320

-

3400

-

3900

498

Worthington mushroom tyrosinase (WMT, crude powder, lot 33H6588Q) (units/mg of powder), WMT and SMT show different levels of tyrosinase activity per milligram of powder

52.19

-

purified native enzyme, pH 7.0, 35°C

5360

-

64.2

-

tyrosine hydroxylation

6800

-

8300

-

mushroom tyrosinase 8300 U/mg

additional information

4

-

5.3

-

PPO activity shows two pH optima, at 5.3 and 7.0 at 25°C when pyrogallol is used as the substrate

6

6 - 7

pH-optimum

6.5

6.8

7

7.2

-

assay at

744015 , 744676 , 745819

7.4

-

assay at

744014 , 744819 , 749419

4 - 10

-

activity range, profile overview

4.5 - 7

-

assay at pH 4.5.and 7.0

4.5 - 9

-

the activity of mushrom tyrosinase is studied in this pH range

5 - 10

the proteolytically activated mushroom tyrosinase shows over 50% of its maximal activity in the range of pH 5-10 and accepts a wide range of substrates including mono- and diphenols, flavonols and chalcones

5.5 - 8

-

inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied. The observed inhibitory activity at pH 6.8. and 5.8 is approximately 10times and 100times greater than at pH 7.8

20

25

30

-

assay at

744014 , 744015 , 744511 , 745095 , 746346

30 - 40

-

cross-linked enzyme aggregate

35

-

37

-

enzyme assay at

40

-

45

-

optimal reaction temperature for the enzyme in aqueous solution

50

-

optimal reaction temperature of the enzyme in 1-butyl-3-methylimidazolium hexafluorophosphate should be higher than 50°C, which is higher than the one for the enzyme in chloroform (20°C) and in aqueous solution (45°C)

55

-

soluble enzyme

20 - 50

-

25 - 70

-

determination of the temperature stability of mushroom PPO

30 - 65

-

activity range, profile overview

4.75

-

commercial preparation

-

-

tyrosinase 4

-

-

1249974 A+, 2355842 A+

intracellular

-

5622

1250788 A++, 1250788 A+

membrane

-

membrane-bound

-

-

evolution

-

tyrosinases are widespread in nature and act on a range of substrates

744483

malfunction

-

excessive accumulation of melanin, due to the overexpression of the enzyme, leads to skin disorders such as age spots, freckles and malignant melanoma

metabolism

physiological function

12 entries

additional information

Q00024 pBLAST

PPO1_AGABI

568

0

63898

Swiss-Prot

other Location (Reliability: 4)

O42713 pBLAST

PPO2_AGABI

556

0

63927

Swiss-Prot

other Location (Reliability: 5)

C7FF04 pBLAST

PPO3_AGABI

576

0

66267

Swiss-Prot

other Location (Reliability: 2)

C7FF05 pBLAST

PPO4_AGABI

611

0

68318

Swiss-Prot

other Location (Reliability: 3)

110000

dynamic light scattering

112800

-

118600 - 119500

-

beta-tyrosinase, sedimentation equilibrium

636414

118800

-

gamma-tyrosinase, sedimentation equilibrium

120000

128000

-

13400

134000

-

2 * 134000 + 2 * 43000, alpha2beta2 subunit composition

14000

2 * 45000 + 2 * 14000, SDS-PAGE

30000

-

4 * 30000, SDS-PAGE

43000

45000

?

dimer

-

heterotetramer

tetramer

additional information

proteolytic modification

the latent recombinant tyrosinase 4 enzyme can be activated by limited proteolysis with proteinase K, which cleaves the polypeptide chain after K382, only one The latent enzyme can amino acid before the main in-vivo activation site. Activation by proteinase K is more efficient compared to activation by trypsin

crystal structure analysis

-

744483

hanging drop vapor diffusion method, using 10% (w/v) PEG 4000, 100 mM sodium acetate buffer pH 4.6 and 5 mM HoCl3

purified recombinant detagged latent tyrosinase, X-ray diffraction structure determination and analysis. In contrast to the crystals obtained with the enzyme isolated from the natural source which contains two different chains in the asymmetric unit (one latent and one active protein) and does only form in the presence of sodium hexatungstotellurate(VI) (Na6[TeW6O24] x 22 H2O), the recombinant enzyme forms crystals containing exclusively the latent tyrosinase. The latent chain of AbPPO4 isolated from Agaricus bisporu, PDB ID 4OUA, chain B, is aligned with the heterologously produced protein, PDB ID 5M6B, chain B

additional information

5 - 10

in the pH-range from pH 5-10 the enzyme retains more than 50% of its activity

746472

5 - 8

-

the soluble enzyme shows half-lives of about 11 min, 35 min, and 3 min at pH 5.0-5.5, pH 6.0, and pH 6.5-8.0, respectively. The cross-linked enzyme aggregates show half-lives of about 11 min, 35 min, and 1 min at pH 5.0-5.5, pH 6.0, and pH 6.5-8.0, respectively

712534

30 - 65

-

purified native enzyme, about 35% of tyrosinase activity is still present at 55°C, but activity is lost at 65°C

35

-

the enzyme is not very heat stable, and its activity decreases when incubated at the temperatures higher than 35°C

40 - 60

-

the soluble enzyme shows half-lives of about 120 min, 30 min, and 10 min at 40, 50, and 60°C, respectively. The cross-linked enzyme aggregates show half-lives of about 320 min, 120 min, and 30 min at 40, 50, and 60°C, respectively

4°C, purified recombinant detagged enzyme, after 1 year of storage in 10 mM HEPES, pH 7.5, the enzyme is still active

PPO is relatively stable at -15°C for 44 days.

-

-

-

685018 , 685668 , 688028 , 698391

a 2fold purification in monophenolase and diphenolase activities is achieved by ammonium sulfate fractionation

-

alpha-, beta-, gamma- and delta tyrosinase, ammonium sulfate, hydroxylapatite

-

636414

ammonium sulfate, DEAE-Sepharose, Phenyl-Sepharose, hydroxyapatite

-

636449

by Duckworth and Coleman's procedure, but with two additional chromatographic steps

-

enzyme is extracted into 100 ml phosphate buffer (50 mM, pH 6.0) and crudely purified from fresh mushrooms (50 g) and then adsorbed onto celite (2 g) and dried in a vacuum oven

-

native enzyme 16.36fold by ammonium sulfate fractionation, dialysis, gel filtration, and anion exchange chromatography

-

partial purification of tyrosinase

recombinant GST-tagged enzyme from Escherichia coli by glutathione affinity chromatography, followed by tag cleavage through specific protease HRV 3 C

Superdex S-200 filtration

Agaricus bisporus possesses genes coding for six different tyrosinases (AbPPO1-AbPPO6), full-length gene AbPPO4 (1-565) DNA and amino acid sequence determination and analysis, recombinant expression of N-terminally GST-tagged tyrosinase 4 from gene AbPPO4 containing 23 mutations in Escherichia coli as latent enzyme

biotechnology

-

prepared CSG1.0 possesses macropores which permit fluid to pass through, and micropores in the skeleton of macropores which increase the specific surface area for ligands to immobilize on. These hybrid membranes could be used to immobilize ligands for affinity sorption. Advanced application of the hybrid membranes can be developed for application in tissue engineering, enzyme immobilization, catalysts support, fuel cells, etc.

drug development

11 entries

environmental protection

-

the integration of cyanide hydratase and tyrosinase open up new possibilities for the bioremediation of wastewaters with complex pollution. Almost full degradation of free cyanide in the model and the real coking wastewaters is achieved by using a recombinant cyanide hydratase in the first step. The removal of cyanide, a strong inhibitor of tyrosinase, enables an effective degradation of phenols by this enzyme in the second step. Phenol is completely removed from a real coking wastewater within 20 h and cresols are removed by 66% under the same conditions

749419

food industry

-

inhibitors have good potential as antibrowning agents to be applied in real food systems

medicine

-

tyrosinase purified from Agaricus bisporus is a potential source for medical applications

pharmacology

additional information

-

tyrosinase is an important enzyme in the food industry because during the processing of fruits and vegetables any wounding may cause cell disruption and lead to quinone formation, the enzymatic browning implies a considerable economic loss in the commercial production of fruits and vegetables, the appearance of food and beverages may be affected, as may the taste and its nutritional value, often decreasing the quality of the final product

674114

636414

Nelson, R.M.; Mason, H.S.

Tyrosinase (mushroom)

Methods Enzymol.

17A

626-632

1970

Agaricus bisporus

-

636415

Vanneste, W.H.; Zuberb hler, A.

Copper-containing oxygenases

Mol. Mech. Oxygen Activ. (Hayaishi, O., ed.) Academic Press, New York

New York

371-404

1974

Agaricus bisporus, Mammalia, Mushroom

-

636423

Strothkamp, K.; Jolly, R.; Mason, H.S.

Quaternary structure of mushroom tyrosinase

Biochem. Biophys. Res. Commun.

70

519-524

1976

Agaricus bisporus

820338

636427

Naish-Byfield, S.; Cooksey, C.J.; Riley, P.A.

Oxidation of monohydric phenol substrates by tyrosinase: effect of dithiothreitol on kinetics

Biochem. J.

304

155-162

1994

Agaricus bisporus

-

Rescigno, A.; Sanjust, E.; Soddu, G.; Rinaldi, A.C.; Sollai, F.; Curreli, N.; Rinaldi, A.

Effect of 3-hydroxyanthranilic acid on mushroom tyrosinase activity

Biochim. Biophys. Acta

1384

268-276

1998

Agaricus bisporus

9659387

Espin, J.C.; Jolivet, S.; Wichers, H.J.

Kinetic Study of the Oxidation of g-L-Glutaminyl-4-hydroxybenzene Catalyzed by Mushroom (Agaricus bisporus) Tyrosinase

J. Agric. Food Chem.

47

3495-3502

1999

Agaricus bisporus

10552675

Espin, J.C.; Varon, R.; Fenoll, L.G.; Gilabert, M.A.; Garcia-Ruiz, P.A.; Tudela, J.; Garcia-Canovas, F.

Kinetic characterization of the substrate specificity and mechanism of mushroom tyrosinase

Eur. J. Biochem.

267

1270-1279

2000

BRENDA: Agaricus bisporus

Textmining: Electron

10691963

636449

Shi, Y.L.; Benzie, I.F.F.; Buswell, J.A.

Role of tyrosinase in the genoprotective effect of the edible mushroom, Agaricus bisporus

Life Sci.

70

1595-1608

2002

BRENDA: Agaricus bisporus

Textmining: Homo sapiens

11991248

Ha, S.K.; Koketsu, M.; Lee, K.; Choi, S.Y.; Park, J.H.; Ishihara, H.; Kim, S.Y.

Inhibition of tyrosinase activity by N,N-unsubstituted selenourea derivatives

Biol. Pharm. Bull.

28

838�840

2005

Agaricus bisporus

15863889

Cho, S.J.; Roh, J.S.; Sun, W.S.; Kim, S.H.; Park, K.D.

N-Benzylbenzamides: A new class of potent tyrosinase inhibitors

Bioorg. Med. Chem. Lett.

16

2682-2684

2006

Agaricus bisporus

16513349

Kim, Y.J.; Uyama, H.

Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future

Cell. Mol. Life Sci.

62

1707-1723

2005

BRENDA: Agaricus bisporus, Beta vulgaris, Homo sapiens, Neurospora crassa, Streptomyces glaucescens

Textmining: Melasma

15968468

674114

Gandia-Herrero, F.; Escribano, J.; Garcia-Carmona, F.

Characterization of the activity of tyrosinase on betaxanthins derived from (R)-amino acids

J. Agric. Food Chem.

53

9207-9212

2005

Agaricus bisporus

16277424

Garcia-Molina, F.; Penalver, M.J.; Fenoll, L.G.; Rodriguez-Lopez, J.N.; Varon, R.; Gracia-Canovas, F.; Tudela, J.

Kinetic study of monophenol and o-diphenol binding to oxytyrosinase

J. Mol. Catal. B

32

185-192

2005

Agaricus bisporus, Neurospora crassa, Streptomyces antibioticus, Streptomyces glaucescens

-

Sabudak, T.; Khan, M.T.H.; Choudhury, M.I.; Oksuz, S.

Potent tyrosinase inhibitors from Trifolium balansae

Nat. Prod. Res.

20

665-670

2006

BRENDA: Agaricus bisporus

Textmining: Trifolium balansae

16901809

Saboury, A.A.; Alijanianzadeh, M.; Mansoori-Torshizi, H.

The role of alkyl chain length in the inhibitory effect n-alkyl xanthates on mushroom tyrosinase activities

Acta Biochim. Pol.

54

183-191

2007

Agaricus bisporus

17369881

Munoz-Munoz, J.L.; Garcia-Molina, F.; Garcia-Ruiz, P.A.; Molina-Alarcon, M.; Tudela, J.; Garcia-Canovas, F.; Rodriguez-Lopez, J.N.

Phenolic substrates and suicide inactivation of tyrosinase: kinetics and mechanism

Biochem. J.

416

431-440

2008

Agaricus bisporus

18647136

685452

Liu, S.H.; Pan, I.H.; Chu, I.M.

Inhibitory effect of p-hydroxybenzyl alcohol on tyrosinase activity and melanogenesis

Biol. Pharm. Bull.

30

1135-1139

2007

Agaricus bisporus, Mus musculus

17541167

Miyazawa, M.; Tamura, N.

Inhibitory compound of tyrosinase activity from the sprout of Polygonum hydropiper L. (Benitade)

Biol. Pharm. Bull.

30

595-597

2007

BRENDA: Agaricus bisporus

Textmining: Persicaria hydropiper

17329865

Hyun, S.K.; Lee, W.H.; Jeong, d.a..M.; Kim, Y.; Choi, J.S.

Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis

Biol. Pharm. Bull.

31

154-158

2008

BRENDA: Agaricus bisporus

Textmining: Sophora flavescens, Sophora

18175961

685462

Tsuchiya, T.; Yamada, K.; Minoura, K.; Miyamoto, K.; Usami, Y.; Kobayashi, T.; Hamada-Sato, N.; Imada, C.; Tsujibo, H.

Purification and determination of the chemical structure of the tyrosinase inhibitor produced by Trichoderma viride strain H1-7 from a marine environment

Biol. Pharm. Bull.

31

1618-1620

2008

BRENDA: Agaricus bisporus

Textmining: Trichoderma viride, Homo sapiens, Metazoa, Trichoderma koningii

18670100

Karioti, A.; Protopappa, A.; Megoulas, N.; Skaltsa, H.

Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum

Bioorg. Med. Chem.

15

2708-2714

2007

BRENDA: Agaricus bisporus

Textmining: Marrubium cylleneum, Marrubium velutinum, Metazoa

17287127

Liu, J.; Yi, W.; Wan, Y.; Ma, L.; Song, H.

1-(1-Arylethylidene)thiosemicarbazide derivatives: a new class of tyrosinase inhibitors

Bioorg. Med. Chem.

16

1096-1102

2008

Agaricus bisporus

18326070

Criton, M.; Le Mellay-Hamon, V.

Analogues of N-hydroxy-N-phenylthiourea and N-hydroxy-N-phenylurea as inhibitors of tyrosinase and melanin formation

Bioorg. Med. Chem. Lett.

18

3607-3610

2008

Agaricus bisporus

18501598

Oozeki, H.; Tajima, R.; Nihei, K.I.

Molecular design of potent tyrosinase inhibitors having the bibenzyl skeleton

Bioorg. Med. Chem. Lett.

18

5252-5254

2008

BRENDA: Agaricus bisporus

Textmining: Chlorophytum arundinaceum

18782667

685668

Morimura, K.; Yamazaki, C.; Hattori, Y.; Makabe, H.; Kamo, T.; Hirota, M.

A tyrosinase inhibitor, Daedalin A, from mycelial culture of Daedalea dickinsii

Biosci. Biotechnol. Biochem.

71

2837-2840

2007

BRENDA: Agaricus bisporus

Textmining: Daedalea dickinsii

17986791

Munoz-Munoz, J.L.; Garcia-Molina, F.; Varon, R.; Rodriguez-Lopez, J.N.; Garcia-Canovas, F.; Tudela, J.

Kinetic characterization of the oxidation of esculetin by polyphenol oxidase and peroxidase

Biosci. Biotechnol. Biochem.

71

390-396

2007

BRENDA: Agaricus bisporus

Textmining: Armoracia rusticana

17284853

Yang, Z.; Yue, Y.J.; Xing, M.

Tyrosinase activity in ionic liquids

Biotechnol. Lett.

30

153-158

2008

Agaricus bisporus

17823775

Nesterov, A.; Zhao, J.; Minter, D.; Hertel, C.; Ma, W.; Abeysinghe, P.; Hong, M.; Jia, Q.

1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)propane, a novel tyrosinase inhibitor with strong depigmenting effects

Chem. Pharm. Bull.

56

1292-1296

2008

BRENDA: Agaricus bisporus, Mus musculus

Textmining: Homo sapiens, Dianella ensifolia, plant

18758104

Liu, J.; Cao, R.; Yi, W.; Ma, C.; Wan, Y.; Zhou, B.; Ma, L.; Song, H.

A class of potent tyrosinase inhibitors: Alkylidenethiosemicarbazide compounds

Eur. J. Med. Chem.

44

1773-1778

2009

Agaricus bisporus

18524420

Gouzi, H.; Benmansour, A.

Partial purification and characterization of polyphenol oxidase extracted from Agaricus bisporus (J.E.Lange) Imbach

Int. J. Chem. React. Eng.

5

A76

2007

Agaricus bisporus

-

Flurkey, A.; Cooksey, J.; Reddy, A.; Spoonmore, K.; Rescigno, A.; Inlow, J.; Flurkey, W.H.

Enzyme, protein, carbohydrate, and phenolic contaminants in commercial tyrosinase preparations: potential problems affecting tyrosinase activity and inhibition studies

J. Agric. Food Chem.

56

4760-4768

2008

Agaricus bisporus (O42713), Agaricus bisporus

18500813

Masuda, T.; Odaka, Y.; Ogawa, N.; Nakamoto, K.; Kuninaga, H.

Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus)

J. Agric. Food Chem.

56

597-601

2008

Agaricus bisporus

18081247

Selinheimo, E.; NiEidhin, D.; Steffensen, C.; Nielsen, J.; Lomascolo, A.; Halaouli, S.; Record, E.; OBeirne, D.; Buchert, J.; Kruus, K.

Comparison of the characteristics of fungal and plant tyrosinases

J. Biotechnol.

130

471-480

2007

Malus domestica, Trametes sanguinea, Trichoderma reesei, Agaricus bisporus (O42713), Solanum tuberosum (Q41428)

17602775

Okunji, C.; Komarnytsky, S.; Fear, G.; Poulev, A.; Ribnicky, D.M.; Awachie, P.I.; Ito, Y.; Raskin, I.

Preparative isolation and identification of tyrosinase inhibitors from the seeds of Garcinia kola by high-speed counter-current chromatography

J. Chromatogr. A

1151

45-50

2007

BRENDA: Agaricus bisporus

Textmining: Garcinia kola

17367799

687996

Chang, T.S.; Tseng, M.; Ding, H.Y.; Shou-Ku Tai, S.

Isolation and characterization of Streptomyces hiroshimensis strain TI-C3 with anti-tyrosinase activity

J. Cosmet. Sci.

59

33-40

2008

Agaricus bisporus

18350233

Alijanianzadeh, M.; Saboury, A.A.; Mansuri-Torshizi, H.; Haghbeen, K.; Moosavi-Movahedi, A.A.

The inhibitory effect of some new synthesized xanthates on mushroom tyrosinase activities

J. Enzyme Inhib. Med. Chem.

22

239-246

2007

Agaricus bisporus

17518352

688028

Garcia Molina, F.; Munoz, J.L.; Varon, R.; Rodriguez Lopez, J.N.; Garcia Canovas, F.; Tudela, J.

Effect of tetrahydropteridines on the monophenolase and diphenolase activities of tyrosinase

J. Enzyme Inhib. Med. Chem.

22

383-394

2007

Agaricus bisporus

17847704

688030

Lu, Y.H.; Lin-Tao, Y.H.; Wang, Z.T.; Wei, D.Z.; Xiang, H.B.

Mechanism and inhibitory effect of galangin and its flavonoid mixture from Alpinia officinarum on mushroom tyrosinase and B16 murine melanoma cells

J. Enzyme Inhib. Med. Chem.

22

433-438

2007

BRENDA: Agaricus bisporus

Textmining: Mus musculus, Alpinia officinarum

17847709

Zhang, C.; Lu, Y.; Tao, L.; Tao, X.; Su, X.; Wei, D.

Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts

J. Enzyme Inhib. Med. Chem.

22

91-98

2007

BRENDA: Agaricus bisporus

Textmining: Citrus, Mus musculus

17373553

Shiino, M.; Watanabe, Y.; Umezawa, K.

pH-dependent inhibition of mushroom tyrosinase by N-substituted N-nitrosohydroxylamines

J. Enzyme Inhib. Med. Chem.

23

16-20

2008

Agaricus bisporus

18341247

688041

Guan, S.; Su, W.; Wang, N.; Li, P.; Wang, Y.

Effects of radix polygoni multiflori components on tyrosinase activity and melanogenesis

J. Enzyme Inhib. Med. Chem.

23

252-255

2008

BRENDA: Agaricus bisporus, Mus musculus

Textmining: Radix

18343911

Ryu, Y.B.; Ha, T.J.; Curtis-Long, M.J.; Ryu, H.W.; Gal, S.W.; Park, K.H.

Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz

J. Enzyme Inhib. Med. Chem.

23

922-930

2008

BRENDA: Agaricus bisporus

Textmining: Morus lhou, plant

18608767

Momtaz, S.; Mapunya, B.M.; Houghton, P.J.; Edgerly, C.; Hussein, A.; Naidoo, S.; Lall, N.

Tyrosinase inhibition by extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening

J. Ethnopharmacol.

119

507-512

2008

BRENDA: Agaricus bisporus

Textmining: Sideroxylon inerme, Sideroxylon

18573327

Chao, A.

Preparation of porous chitosan/GPTMS hybrid membrane and its application in affinity sorption for tyrosinase purification with Agaricus bisporus

J. Membr. Sci.

311

306-318

2008

Agaricus bisporus

-

688592

Kim, D.S.; Lee, S.; Lee, H.K.; Park, S.H.; Ryoo, I.J.; Yoo, I.D.; Kwon, S.B.; Baek, K.J.; Na, J.I.; Park, K.C.

The hypopigmentary action of KI-063 (a new tyrosinase inhibitor) combined with terrein

J. Pharm. Pharmacol.

60

343-348

2008

Agaricus bisporus, Mus musculus

18284814

Zheng, Z.P.; Cheng, K.W.; To, J.T.; Li, H.; Wang, M.

Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agent

Mol. Nutr. Food Res.

52

1530-1538

2008

BRENDA: Agaricus bisporus

Textmining: Artocarpus heterophyllus, Malus domestica

18683821

Gao, H.; Nishida, J.; Saito, S.; Kawabata, J.

Inhibitory effects of 5,6,7-trihydroxyflavones on tyrosinase

Molecules

12

86-97

2007

Agaricus bisporus

17693955

689118

Chien, C.C.; Tsai, M.L.; Chen, C.C.; Chang, S.J.; Tseng, C.H.

Effects on tyrosinase activity by the extracts of Ganoderma lucidum and related mushrooms

Mycopathologia

166

117-120

2008

BRENDA: Agaricus bisporus

Textmining: Ganoderma lucidum, Basidiomycota, Ganoderma, Cordyceps, Agaricus brasiliensis, Taiwanofungus camphoratus

18459064

689278

Thangasamy, T.; Sittadjody, S.; Lanza-Jacoby, S.; Wachsberger, P.R.; Limesand, K.H.; Burd, R.

Quercetin selectively inhibits bioreduction and enhances apoptosis in melanoma cells that overexpress tyrosinase

Nutr. Cancer

59

258-268

2007

Agaricus bisporus

18001220

Abdel-Halim, O.B.; Marzouk, A.M.; Mothana, R.; Awadh, N.

A new tyrosinase inhibitor from Crinum yemense as potential treatment for hyperpigmentation

Pharmazie

63

405-407

2008

BRENDA: Agaricus bisporus

Textmining: Crinum yemense

18557429

689413

Lin, Y.P.; Hsu, F.L.; Chen, C.S.; Chern, J.W.; Lee, M.H.

Constituents from the Formosan apple reduce tyrosinase activity in human epidermal melanocytes

Phytochemistry

68

1189-1199

2007

BRENDA: Agaricus bisporus, Homo sapiens

Textmining: Malus domestica, plant

17379263

Ryu, Y.B.; Westwood, I.M.; Kang, N.S.; Kim, H.Y.; Kim, J.H.; Moon, Y.H.; Park, K.H.

Kurarinol, tyrosinase inhibitor isolated from the root of Sophora flavescens

Phytomedicine

15

612-618

2008

BRENDA: Agaricus bisporus

Textmining: Sophora flavescens, Firmicutes, Streptomyces bikiniensis

17951038

Ullah, F.; Hussain, H.; Hussain, J.; Bukhari, I.A.; Khan, M.T.; Choudhary, M.I.; Gilani, A.H.; Ahmad, V.U.

Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum

Phytother. Res.

21

1076-1081

2007

BRENDA: Agaricus bisporus

Textmining: Rhododendron

17661331

Parvez, S.; Kang, M.; Chung, H.S.; Bae, H.

Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries

Phytother. Res.

21

805-816

2007

BRENDA: Agaricus bisporus, Beta vulgaris, Neurospora crassa, Streptomyces glaucescens

Textmining: Metazoa

17605157

689441

Leu, Y.L.; Hwang, T.L.; Hu, J.W.; Fang, J.Y.

Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use

Phytother. Res.

22

552-556

2008

BRENDA: Agaricus bisporus

Textmining: Polygonum cuspidatum

18338768

689442

Guan, S.; Su, W.; Wang, N.; Li, P.; Wang, Y.

A potent tyrosinase activator from Radix Polygoni multiflori and its melanogenesis stimulatory effect in B16 melanoma cells

Phytother. Res.

22

660-663

2008

BRENDA: Agaricus bisporus, Mus musculus

Textmining: Radix

18389468

Magid, A.A.; Voutquenne-Nazabadioko, L.; Bontemps, G.; Litaudon, M.; Lavaud, C.

Tyrosinase inhibitors and sesquiterpene diglycosides from Guioa villosa

Planta Med.

74

55-60

2008

BRENDA: Agaricus bisporus

Textmining: Guioa villosa

18203056

Jirawattanapong, W.; Saifah, E.; Patarapanich, C.

Synthesis of glabridin derivatives as tyrosinase inhibitors

Arch. Pharm. Res.

32

647-654

2009

BRENDA: Agaricus bisporus

Textmining: Sus scrofa

19471877

Munoz-Munoz, J.L.; Garcia-Molina, F.; Garcia-Ruiz, P.A.; Varon, R.; Tudela, J.; Garcia-Canovas, F.; Rodriguez-Lopez, J.N.

Stereospecific inactivation of tyrosinase by L- and D-ascorbic acid

Biochim. Biophys. Acta

1794

244-253

2009

Agaricus bisporus

19010454

Le Mellay-Hamon, V.; Criton, M.

Phenylethylamide and phenylmethylamide derivatives as new tyrosinase inhibitors

Biol. Pharm. Bull.

32

301-303

2009

Agaricus bisporus

19182394

Yi, W.; Cao, R.; Wen, H.; Yan, Q.; Zhou, B.; Wan, Y.; Ma, L.; Song, H.

Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors

Bioorg. Med. Chem. Lett.

18

6490-6493

2008

Agaricus bisporus

18996693

Kang, S.S.; Kim, H.J.; Jin, C.; Lee, Y.S.

Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives

Bioorg. Med. Chem. Lett.

19

188-191

2009

BRENDA: Agaricus bisporus

Textmining: Melasma

19022667

Yi, W.; Cao, R.; Wen, H.; Yan, Q.; Zhou, B.; Ma, L.; Song, H.

Discovery of 4-functionalized phenyl-O-beta-D-glycosides as a new class of mushroom tyrosinase inhibitors

Bioorg. Med. Chem. Lett.

19

6157-6160

2009

Agaricus bisporus

19800229

Baek, Y.S.; Ryu, Y.B.; Curtis-Long, M.J.; Ha, T.J.; Rengasamy, R.; Yang, M.S.; Park, K.H.

Tyrosinase inhibitory effects of 1,3-diphenylpropanes from Broussonetia kazinoki

Bioorg. Med. Chem.

17

35-41

2009

BRENDA: Agaricus bisporus

Textmining: Broussonetia kazinoki

19046886

Ng, L.T.; Ko, H.H.; Lu, T.M.

Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins

Bioorg. Med. Chem.

17

4360-4366

2009

Agaricus bisporus

19481947

Chiku, K.; Dohi, H.; Saito, A.; Ebise, H.; Kouzai, Y.; Shinoyama, H.; Nishida, Y.; Ando, A.

Enzymatic synthesis of 4-hydroxyphenyl beta-D-oligoxylosides and their notable tyrosinase inhibitory activity

Biosci. Biotechnol. Biochem.

73

1123-1128

2009

BRENDA: Agaricus bisporus

Textmining: Escherichia coli, Bacillus sp. (in: Bacteria)

19420707

Yi, W.; Cao, R.H.; Chen, Z.Y.; Yu, L.; Ma, L.; Song, H.C.

Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted phenylmethylenethiosemicarbazones as tyrosinase inhibitors

Chem. Pharm. Bull.

57

1273-1277

2009

Agaricus bisporus

19881280

Selinheimo, E.; Gasparetti, C.; Mattinen, M.; Steffensen, C.; Buchert, J.; Kruus, K.

Comparison of substrate specificity of tyrosinases from Trichoderma reesei and Agaricus bisporus

Enzyme Microb. Technol.

44

1-10

2009

Agaricus bisporus, Trichoderma reesei

-

Lee, K.H.; Ab Aziz, F.H.; Syahida, A.; Abas, F.; Shaari, K.; Israf, D.A.; Lajis, N.H.

Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities

Eur. J. Med. Chem.

44

3195-3200

2009

Agaricus bisporus

19359068

Perry, M.J.; Mendes, E.; Simplicio, A.L.; Coelho, A.; Soares, R.V.; Iley, J.; Moreira, R.; Francisco, A.P.

Dopamine- and tyramine-based derivatives of triazenes: activation by tyrosinase and implications for prodrug design

Eur. J. Med. Chem.

44

3228-3234

2009

BRENDA: Agaricus bisporus

Textmining: Homo sapiens

19386398

Yan, Q.; Cao, R.; Yi, W.; Chen, Z.; Wen, H.; Ma, L.; Song, H.

Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities

Eur. J. Med. Chem.

44

4235-4243

2009

BRENDA: Agaricus bisporus

Textmining: Staphylococcus aureus

19552984

Yi, W.; Wu, X.; Cao, R.; Song, H.; Ma, L.

Biological evaluations of novel vitamin C esters as mushroom tyrosinase inhibitors and antioxidants

Food Chem.

117

381-386

2009

Agaricus bisporus

100522135

698391

Munoz-Munoz, J.L.; Garcia-Molina, F.; Garcia-Molina, M.; Tudela, J.; Garcia-Canovas, F.; Rodriguez-Lopez, J.N.

Ellagic acid: characterization as substrate of polyphenol oxidase

IUBMB Life

61

171-177

2009

Agaricus bisporus

18925653

Jeong, S.H.; Ryu, Y.B.; Curtis-Long, M.J.; Ryu, H.W.; Baek, Y.S.; Kang, J.E.; Lee, W.S.; Park, K.H.

Tyrosinase inhibitory polyphenols from roots of Morus lhou

J. Agric. Food Chem.

57

1195-1203

2009

BRENDA: Agaricus bisporus

Textmining: Morus lhou

19166303

Bandyopadhyay, P.; Jha, S.; Imran Ali, S.K.

Picolyl alkyl amines as novel tyrosinase inhibitors: Influence of hydrophobicity and substitution

J. Agric. Food Chem.

57

9780-9786

2009

Agaricus bisporus

19803525

699039

Gou, L.; Lu, Z.R.; Park, D.; Sang, H.; Shi, L.; Seong, J.; Bhak, J.; Park, Y.; Ren, Z.; Zou, F.

The effect of histidine residue modification on tyrosinase activity and conformation: Inhibition kinetics and computational prediction

J. Biomol. Struct. Dyn.

26

395-401

2008

Agaricus bisporus

18808205

Xue, C.B.; Luo, W.C.; Ding, Q.; Liu, S.Z.; Gao, X.X.

Quantitative structure-activity relationship studies of mushroom tyrosinase inhibitors

J. Comput. Aided Mol. Des.

22

299-309

2008

BRENDA: Agaricus bisporus

Textmining: Hexapoda, Metazoa, Indicator

18256890

699239

Zhuang, J.X.; Li, W.G.; Qiu, L.; Zhong, X.; Zhou, J.J.; Chen, Q.X.

Inhibitory effects of Cefazolin and Cefodizime on the activity of mushroom tyrosinase

J. Enzyme Inhib. Med. Chem.

24

251-256

2009

Agaricus bisporus

18830875

Abu Ubeid, A.; Zhao, L.; Wang, Y.; Hantash, B.M.

Short-sequence oligopeptides with inhibitory activity against mushroom and human tyrosinase

J. Invest. Dermatol.

129

2242-2249

2009

Agaricus bisporus, Homo sapiens

19440221

Wu, B.; Chen, J.; Qu, H.; Cheng, Y.

Complex sesquiterpenoids with tyrosinase inhibitory activity from the leaves of Chloranthus tianmushanensis

J. Nat. Prod.

71

877-880

2008

BRENDA: Agaricus bisporus

Textmining: Chloranthus

18357995

Antonella Fai, A.F.; Corda, M.; Era, B.; Fadda, M.; Matos, M.; Quezada, E.; Santana, L.; Picciau, C.; Podda, G.; Delogu, G.

Tyrosinase inhibitor activity of coumarin-resveratrol hybrids

Molecules

14

2514-2520

2009

Agaricus bisporus

19633620

700323

Nithitanakool, S.; Pithayanukul, P.; Bavovada, R.; Saparpakorn, P.

Molecular docking studies and anti-tyrosinase activity of Thai mango seed kernel extract

Molecules

14

257-265

2009

BRENDA: Agaricus bisporus

Textmining: Mangifera indica

19136913

Nugroho, A.; Choi, J.K.; Park, J.H.; Lee, K.T.; Cha, B.C.; Park, H.J.

Two new flavonol glycosides from Lamium amplexicaule L. and their in vitro free radical scavenging and tyrosinase inhibitory activities

Planta Med.

75

364-366

2009

BRENDA: Agaricus bisporus

Textmining: Lamium amplexicaule

19148861

Ismaya, W.T.; Rozeboom, H.J.; Schurink, M.; Boeriu, C.G.; Wichers, H.; Dijkstra, B.W.

Crystallization and preliminary X-ray crystallographic analysis of tyrosinase from the mushroom Agaricus bisporus

Acta Crystallogr. Sect. F

67

575-578

2011

Agaricus bisporus (O42713), Agaricus bisporus

21543865

Guo, Y.J.; Pan, Z.Z.; Chen, C.Q.; Hu, Y.H.; Liu, F.J.; Shi, Y.; Yan, J.H.; Chen, Q.X.

Inhibitory effects of fatty acids on the activity of mushroom tyrosinase

Appl. Biochem. Biotechnol.

162

1564-1573

2010

Agaricus bisporus

20544305

Takahashi, T.; Miyazawa, M.

Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition

Bioorg. Med. Chem. Lett.

21

1983-1986

2011

Agaricus bisporus

21377874

Ghani, U.; Ullah, N.

New potent inhibitors of tyrosinase: novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site

Bioorg. Med. Chem.

18

4042-4048

2010

BRENDA: Agaricus bisporus

Textmining: Solanum tuberosum

20452224

711476

Chiari, M.E.; Vera, D.M.; Palacios, S.M.; Carpinella, M.C.

Tyrosinase inhibitory activity of a 6-isoprenoid-substituted flavanone isolated from Dalea elegans

Bioorg. Med. Chem.

19

3474-3482

2011

BRENDA: Agaricus bisporus

Textmining: Dalea, Developayella elegans, plant

21561780

Li, Z.C.; Chen, L.H.; Yu, X.J.; Hu, Y.H.; Song, K.K.; Zhou, X.W.; Chen, Q.X.

Inhibition kinetics of chlorobenzaldehyde thiosemicarbazones on mushroom tyrosinase

J. Agric. Food Chem.

58

12537-12540

2010

Agaricus bisporus

21062043

Xu, D.Y.; Yang, Y.; Yang, Z.

Activity and stability of cross-linked tyrosinase aggregates in aqueous and nonaqueous media

J. Biotechnol.

152

30-36

2011

Agaricus bisporus

21262284

712597

Amin, E.; Saboury, A.; Mansuri-Torshizi, H.; Moosavi-Movahedi, A.

Potent inhibitory effects of benzyl and p-xylidine-bis dithiocarbamate sodium salts on activities of mushroom tyrosinase

J. Enzyme Inhib. Med. Chem.

25

272-281

2010

Agaricus bisporus

19663663

Takahashi, T.; Miyazawa, M.

Tyrosinase inhibitory activities of cinnamic acid analogues

Pharmazie

65

913-918

2010

Agaricus bisporus

21284262

Munoz-Munoz, J.L.; Berna, J.; Garcia-Molina, M.d.e.l..M.; Garcia-Molina, F.; Garcia-Ruiz, P.A.; Varon, R.; Rodriguez-Lopez, J.N.; Garcia-Canovas, F.

Hydroxylation of p-substituted phenols by tyrosinase: further insight into the mechanism of tyrosinase activity

Biochem. Biophys. Res. Commun.

424

228-233

2012

BRENDA: Agaricus bisporus

Textmining: Transformation

22732412

Wang, Y.; Curtis-Long, M.; Lee, B.; Yuk, H.; Kim, D.; Tan, X.; Park, K.

Inhibition of tyrosinase activity by polyphenol compounds from Flemingia philippinensis roots

Bioorg. Med. Chem.

22

1115-1120

2014

BRENDA: Agaricus bisporus

Textmining: Flemingia philippinensis, plant

24412339

743960

Lai, X.; Soler-Lopez, M.; Ismaya, W.; Wichers, H.; Dijkstra, B.

Crystal structure of recombinant tyrosinase-binding protein MtaL at 1.35% resolution

Acta Crystallogr. Sect. F

72

244-250

2016

Agaricus bisporus (C7FF04), Agaricus bisporus

26919530

744014

Liu, D.M.; Yang, J.L.; Ha, W.; Chen, J.; Shi, Y.P.

Kinetics and inhibition study of tyrosinase by pressure mediated microanalysis

Anal. Biochem.

525

54-59

2017

Agaricus bisporus

28257907

744015

Hu, J.J.; Bai, X.L.; Liu, Y.M.; Liao, X.

Functionalized carbon quantum dots with dopamine for tyrosinase activity analysis

Anal. Chim. Acta

995

99-105

2017

BRENDA: Agaricus bisporus

Textmining: Electron

29126486

Jantakee, K.; Tragoolpua, Y.

Activities of different types of Thai honey on pathogenic bacteria causing skin diseases, tyrosinase enzyme and generating free radicals

Biol. Res.

48

4-4

2015

BRENDA: Agaricus bisporus

Textmining: Bacteria, Apoidea

25654191

744483

Ramsden, C.A.; Riley, P.A.

Tyrosinase the four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation

Bioorg. Med. Chem.

22

2388-2395

2014

Agaricus bisporus

24656803

Ortiz-Ruiz, C.V.; Berna, J.; Garcia-Molina, M.d.e.l. .M.; Tudela, J.; Tomas, V.; Garcia-Canovas, F.

Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates

Bioorg. Med. Chem.

23

3738-3746

2015

Agaricus bisporus

25913862

Ashraf, Z.; Rafiq, M.; Seo, S.Y.; Babar, M.M.; Zaidi, N.U.

Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase

Bioorg. Med. Chem.

23

5870-5880

2015

BRENDA: Agaricus bisporus

Textmining: Transformation

26204890

Garcia-Jimenez, A.; Teruel-Puche, J.A.; Berna, J.; Rodriguez-Lopez, J.N.; Tudela, J.; Garcia-Ruiz, P.A.; Garcia-Canovas, F.

Characterization of the action of tyrosinase on resorcinols

Bioorg. Med. Chem.

24

4434-4443

2016

Agaricus bisporus

27480027

744491

Wang, R.; Chai, W.M.; Yang, Q.; Wei, M.K.; Peng, Y.

2-(4-Fluorophenyl)-quinazolin-4(3H)-one as a novel tyrosinase inhibitor Synthesis, inhibitory activity, and mechanism

Bioorg. Med. Chem.

24

4620-4625

2016

Agaricus bisporus

27527415

Channar, P.A.; Saeed, A.; Larik, F.A.; Rafiq, M.; Ashraf, Z.; Jabeen, F.; Fattah, T.A.

Synthesis, computational studies and enzyme inhibitory kinetics of substituted methyl[(2-(4-dimethylamino-benzylidene)-hydrazono)-4-oxo-thiazolidin-5-ylidene]acetates as mushroom tyrosinase inhibitors

Bioorg. Med. Chem.

25

5929-5938

2017

Agaricus bisporus

28988751

Oyama, T.; Yoshimori, A.; Takahashi, S.; Yamamoto, T.; Sato, A.; Kamiya, T.; Abe, H.; Abe, T.; Tanuma, S.I.

Structural insight into the active site of mushroom tyrosinase using phenylbenzoic acid derivatives

Bioorg. Med. Chem. Lett.

27

2868-2872

2017

Agaricus bisporus

28495084

Radhakrishnan, S.K.; Shimmon, R.G.; Conn, C.; Baker, A.T.

Inhibitory kinetics of azachalcones and their oximes on mushroom tyrosinase a facile solid-state synthesis

Chem. Biodivers.

13

531-538

2016

Agaricus bisporus

27061023

744671

Abbas, Q.; Raza, H.; Hassan, M.; Phull, A.R.; Kim, S.J.; Seo, S.Y.

Acetazolamide inhibits the level of tyrosinase and melanin an enzyme kinetic, in vitro, in vivo, and in silico studies

Chem. Biodivers.

14

e1700117

2017

Agaricus bisporus, Danio rerio, Homo sapiens

28557244

Brasil, E.M.; Canavieira, L.M.; Cardoso, E.T.C.; Silva, E.O.; Lameira, J.; Nascimento, J.L.M.; Eifler-Lima, V.L.; Macchi, B.M.; Sriram, D.; Bernhardt, P.V.; Silva, J.R.A.; Williams, C.M.; Alves, C.N.

Inhibition of tyrosinase by 4H-chromene analogs Synthesis, kinetic studies, and computational analysis

Chem. Biol. Drug Des.

90

804-810

2017

Agaricus bisporus

28390091

Zaidi, K.U.; Ali, A.S.; Ali, S.A.

Purification and characterization of melanogenic enzyme tyrosinase from button mushroom

Enzyme Res.

2014

120739

2014

BRENDA: Agaricus bisporus

Textmining: Homo sapiens, Dialysis

25197562

744819

Nokinsee, D.; Shank, L.; Lee, V.S.; Nimmanpipug, P.

Estimation of inhibitory effect against tyrosinase activity through homology modeling and molecular docking

Enzyme Res.

2015

262364

2015

Agaricus bisporus, Homo sapiens (P14679), Homo sapiens

26788364

Larik, F.A.; Saeed, A.; Channar, P.A.; Muqadar, U.; Abbas, Q.; Hassan, M.; Seo, S.Y.; Bolte, M.

Design, synthesis, kinetic mechanism and molecular docking studies of novel 1-pentanoyl-3-arylthioureas as inhibitors of mushroom tyrosinase and free radical scavengers

Eur. J. Med. Chem.

141

273-281

2017

Agaricus bisporus

29040952

Gou, L.; Lee, J.; Hao, H.; Park, Y.D.; Zhan, Y.; Lue, Z.R.

The effect of oxaloacetic acid on tyrosinase activity and structure Integration of inhibition kinetics with docking simulation

Int. J. Biol. Macromol.

101

59-66

2017

Agaricus bisporus

28322963

745095

Hu, Y.H.; Chen, Q.X.; Cui, Y.; Gao, H.J.; Xu, L.; Yu, X.Y.; Wang, Y.; Yan, C.L.; Wang, Q.

4-Hydroxy cinnamic acid as mushroom preservation anti-tyrosinase activity kinetics and application

Int. J. Biol. Macromol.

86

489-495

2016

Agaricus bisporus

26812105

del Mar Garcia-Molina, M.; Munoz-Munoz, J.L.; Berna, J.; Garcia-Ruiz, P.A.; Rodriguez-Lopez, J.N.; Garcia-Canovas, F.

Catalysis and inactivation of tyrosinase in its action on hydroxyhydroquinone

IUBMB Life

66

122-127

2014

Agaricus bisporus

24578277

Ortiz-Ruiz, C.V.; Maria-Solano, M.A.; Garcia-Molina, M.d.e.l. .M.; Varon, R.; Tudela, J.; Tomas, V.; Garcia-Canovas, F.

Kinetic characterization of substrate-analogous inhibitors of tyrosinase

IUBMB Life

67

757-767

2015

Agaricus bisporus

26399372

Ortiz-Ruiz, C.V.; Ballesta de Los Santos, M.; Berna, J.; Fenoll, J.; Garcia-Ruiz, P.A.; Tudela, J.; Garcia-Canovas, F.

Kinetic characterization of oxyresveratrol as a tyrosinase substrate

IUBMB Life

67

828-836

2015

Agaricus bisporus

26450473

Patil, S.; Sistla, S.; Jadhav, J.

Screening of inhibitors for mushroom tyrosinase using surface plasmon resonance

J. Agric. Food Chem.

62

11594-11601

2014

Agaricus bisporus

25402844

Asthana, S.; Zucca, P.; Vargiu, A.V.; Sanjust, E.; Ruggerone, P.; Rescigno, A.

Structure-activity relationship study of hydroxycoumarins and mushroom tyrosinase

J. Agric. Food Chem.

63

7236-7244

2015

Agaricus bisporus

26263396

745139

Chai, W.M.; Wei, M.K.; Wang, R.; Deng, R.G.; Zou, Z.R.; Peng, Y.Y.

Avocado proanthocyanidins as a source of tyrosinase inhibitors structure characterization, inhibitory activity, and mechanism

J. Agric. Food Chem.

63

7381-7387

2015

BRENDA: Agaricus bisporus

Textmining: Persea americana

26259028

Liu, X.; Jia, Y.L.; Chen, J.W.; Liang, G.; Guo, H.Y.; Hu, Y.H.; Shi, Y.; Zhou, H.T.; Chen, Q.X.

Inhibition effects of benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on the activity of mushroom tyrosinase

J. Biosci. Bioeng.

119

275-279

2015

Agaricus bisporus

25441446

Lima, C.R.; Silva, J.R.; de Tassia Carvalho Cardoso, E.; Silva, E.O.; Lameira, J.; do Nascimento, J.L.; do Socorro Barros Brasil, D.; Alves, C.N.

Combined kinetic studies and computational analysis on kojic acid analogous as tyrosinase inhibitors

Molecules

19

9591-9605

2014

BRENDA: Agaricus bisporus

Textmining: Metazoa, Mammalia

25004069

Chai, W.M.; Wang, R.; Wei, M.K.; Zou, Z.R.; Deng, R.G.; Liu, W.S.; Peng, Y.Y.

Proanthocyanidins extracted from Rhododendron pulchrum leaves as source of tyrosinase inhibitors structure, activity, and mechanism

PLoS ONE

10

e0145483

2015

BRENDA: Agaricus bisporus

Textmining: Rhododendron x pulchrum, Rhaponticum pulchrum

26713623

Garcia-Jimenez, A.; Teruel-Puche, J.A.; Berna, J.; Rodriguez-Lopez, J.N.; Tudela, J.; Garcia-Canovas, F.

Action of tyrosinase on alpha and beta-arbutin A kinetic study

PLoS ONE

12

e0177330

2017

Agaricus bisporus

28493937

Ashraf, Z.; Rafiq, M.; Nadeem, H.; Hassan, M.; Afzal, S.; Waseem, M.; Afzal, K.; Latip, J.

Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies

PLoS ONE

12

e0178069

2017

Agaricus bisporus (C7FF04)

28542395

Garcia-Jimenez, A.; Teruel-Puche, J.A.; Garcia-Ruiz, P.A.; Saura-Sanmartin, A.; Berna, J.; Garcia-Canovas, F.; Rodriguez-Lopez, J.N.

Structural and kinetic considerations on the catalysis of deoxyarbutin by tyrosinase

PLoS ONE

12

e0187845

2017

Agaricus bisporus (C7FF04)

29136639

746346

Zheng, J.; Zhang, R.; Chen, Y.; Ye, X.; Chen, Q.; Shen, D.; Wang, Q.

Synthesis of caffeic acid ester morpholines and their activation effects on tyrosinase

Process Biochem.

62

91-98

2017

Agaricus bisporus, Homo sapiens (P14679)

-

Pretzler, M.; Bijelic, A.; Rompel, A.

Heterologous expression and characterization of functional mushroom tyrosinase (AbPPO4)

Sci. Rep.

7

1810

2017

BRENDA: Agaricus bisporus (C7FF05), Agaricus bisporus

Textmining: Escherichia coli

28500345