1.14.18.1: tyrosinase
This is an abbreviated version!
For detailed information about tyrosinase, go to the full flat file.
Word Map on EC 1.14.18.1
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1.14.18.1
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melanin
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melanoma
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melanocyte
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melanogenesis
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melanosomes
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cosmetic
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microphthalmia-associated
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hyperpigmentation
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melanogenic
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catechols
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polyphenols
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kojic
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copper
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albinism
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whitening
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hair
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keratinocytes
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albino
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flavonoid
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biosensors
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o-quinone
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amperometric
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phytochemical
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pigmentary
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vitiligo
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tautomerase
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laccase
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abts
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alpha-msh
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melanization
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depigmentation
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hydroquinone
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electrode
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melanocortins
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2,2-diphenyl-1-picrylhydrazyl
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copper-binding
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polyphenoloxidase
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frap
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biotechnology
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agriculture
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pharmacology
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hla-a2
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nutrition
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1,1-diphenyl-2-picrylhydrazyl
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food industry
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hemocyanins
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environmental protection
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l-3,4-dihydroxyphenylalanine
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crest-derived
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drug development
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microphthalmia
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medicine
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agaricus
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butyrylcholinesterase
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melanoma-associated
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copper-containing
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decolor
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bisporus
- 1.14.18.1
- melanin
- melanoma
- melanocyte
-
melanogenesis
- melanosomes
-
cosmetic
-
microphthalmia-associated
- hyperpigmentation
-
melanogenic
- catechols
- polyphenols
-
kojic
- copper
- albinism
-
whitening
- hair
-
keratinocytes
-
albino
- flavonoid
-
biosensors
- o-quinone
-
amperometric
-
phytochemical
-
pigmentary
- vitiligo
-
tautomerase
- laccase
- abts
- alpha-msh
-
melanization
-
depigmentation
- hydroquinone
-
electrode
-
melanocortins
-
2,2-diphenyl-1-picrylhydrazyl
-
copper-binding
- polyphenoloxidase
-
frap
- biotechnology
- agriculture
- pharmacology
-
hla-a2
- nutrition
-
1,1-diphenyl-2-picrylhydrazyl
- food industry
- hemocyanins
- environmental protection
- l-3,4-dihydroxyphenylalanine
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crest-derived
- drug development
- microphthalmia
- medicine
- agaricus
- butyrylcholinesterase
-
melanoma-associated
-
copper-containing
-
decolor
- bisporus
Reaction
2 L-dopa
+
Synonyms
AbPPO1, AbPPO4, AbTYR, aurone synthase, catalase-phenol oxidase, catechol oxidase, catecholase, CATPO, chlorogenic acid oxidase, chlorogenic oxidase, cresolase, cresolase/monophenolase, CsPPO, CZA14Tyr, deoxy-tyrosinase, dihydroxy-L-phenylalanine:oxygen oxidoreductase, Diphenol oxidase, diphenolase, dopa oxidase, EC 1.10.3.1, EC 1.14.17.2, Hc-derived phenoloxidase, Hc-phenoloxidase, HcPO, HdPO, hemocyanin-derived phenoloxidase, jrPPO1, jrTYR, L-DOPA monophenolase, L-DOPA oxidase, L-DOPA:oxygen oxidoreductase, L-tyrosine hydroxylase, MdPPO1, melC2, MelC2 tyrosinase, met-tyrosinase, monophenol dihydroxyphenylalanine:oxygen oxidoreductase, monophenol monooxidase, monophenol monooxygenase, monophenol monoxygenase, monophenol oxidase, monophenol oxygen oxidoreductase, monophenol, 3,4-dihydroxy L-phenylalanine (L-DOPA):oxygen oxidoreductase, monophenol, dihydroxy-L-phenylalanine oxygen oxidoreductase, monophenol, dihydroxy-L-phenylalanine:oxygen oxidoreductase, monophenol, dihydroxyphenylalanine:oxygen oxidoreductase, monophenol, L-Dopa: oxidoreductase, monophenol, L-DOPA: oxygen oxidoreductase, monophenol, o-diphenol: oxygen oxidoreductase, monophenol, o-diphenol:O2 oxidoreductase, monophenol, o-diphenol:oxygen oxido-reductase, monophenol, o-diphenol:oxygen oxidoreductase, monophenol, polyphenol oxidase, monophenol: dioxygen oxidoreductases, hydroxylating, monophenolase, monphenol mono-oxygenase, More, mTyr, murine tyrosinase, mushroom tyrosinase, mushroom tyrosine, N-acetyl-6-hydroxytryptophan oxidase, o-diphenol oxidase, o-diphenol oxidoreductase, o-diphenol oxygen oxidoreductase, o-diphenol: O2 oxidoreductase, o-diphenol: oxidoreductase, o-diphenol:O2 oxidoreductase, o-diphenol:oxygen oxidoreductase, o-diphenolase, OCA1, Orf13, oxygen oxidoreductase, phenol oxidase, phenol oxidases, phenolase, phenoloxidase, PO, polyaromatic oxidase, polyphenol oxidase, polyphenol oxidase 3, polyphenol oxidase 4, polyphenol oxidase B, polyphenolase, polyphenoloxidase, PotPPO, PPO, PPO 3, PPO B, PPO1, PPO2, PPO3, pro-PO III, prophenoloxidase III, pyrocatechol oxidase, SPRTyr, ST94, ST94t, tryosinase, tryrosinase, TY, tyr, TYR1, TYR2, tyrA, TyrBm, tyrosinase, tyrosinase 2, tyrosinase 4, tyrosinase diphenolase, tyrosine-dopa oxidase
ECTree
1.14.18.1 tyrosinaseAdvanced search results
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results (Inhibitors
Inhibitors on EC 1.14.18.1 - tyrosinase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(1E,2E)-3-(2,4-dimethoxyphenyl)-N-hydroxy-1-(pyridin-2-yl)prop-2-en-1-imine
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52.5% inhibition at 50 mM
(2-([4-(4-methoxy-benzyloxy)-benzylidene]-hydrazono)-4-oxothiazolidin-5-ylidene)-acetic acid methyl ester
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(2-[(2-hydroxy-benzylidene)-hydrazono]-4-oxo-thiazolidin-5-ylidene)-acetic acid methyl ester
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(2-[(5-methyl-furan-2-ylmethylene)-hydrazono]-4-oxothiazolidin-5-ylidene)-acetic acid methyl ester
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(2E)-1-(2-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one
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59.2% inhibition at 50 mM
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-3-yl)prop-2-en-1-one
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55.9% inhibition at 50 mM
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-4-yl)prop-2-en-1-one
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48.9% inhibition at 50 mM
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-2-yl)prop-2-en-1-one
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49.5% inhibition at 50 mM
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(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-3-yl)prop-2-en-1-one
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59.2% inhibition at 50 mM
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-4-yl)prop-2-en-1-one
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42.7% inhibition at 50 mM
(2E)-3-(2,4-dimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one
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12.3% inhibition at 50 mM
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
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14% inhibition at 0.1 mM; 2% inhibition at 0.1 mM
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-enamide
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(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]prop-2-enamide
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1% inhibition at 0.1 mM; 4% inhibition at 0.1 mM
(2E)-3-(3,4-dimethoxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
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(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
-
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(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-phenylethyl)prop-2-enamide
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19% inhibition at 0.1 mM
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
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13% inhibition at 0.1 mM; 4% inhibition at 0.1 mM
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]prop-2-enamide
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40% inhibition at 0.1 mM
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
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49% inhibition at 0.1 mM
(2E)-3-(4-hydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide
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strong tyrosinase inhibitory potential
(2E)-3-[4-(dimethylamino)phenyl]-1-(pyridin-2-yl)prop-2-en-1-one
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16.9% inhibition at 50 mM
(2E)-N-benzyl-3-(4-hydroxyphenyl)prop-2-enamide
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strong tyrosinase inhibitory potential
(2E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
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62% inhibition at 0.1 mM
(2E)-N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
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25% inhibition at 0.1 mM
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide
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-
(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
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(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-methoxyphenyl)prop-2-enamide
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(2R,3R)-taxifolin
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isolated from the sprout of Polygonum hydropiper L. (Benitade), inhibited 70% of tyrosinase activity at a concentration of 0.50 mM
(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
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tyrosinase inhibitors from Marrubium velutinum, lignan glucosides
(7S, 8R, 8'R)-(-)-lariciresinol-4,4'-O-bis-beta-D-glucopyranoside
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tyrosinase inhibitors from Marrubium velutinum, lignan glucosides
(7S, 8R, 8'R)-(-)-lariciresinol-4-O-beta-D-glucopyranoside
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tyrosinase inhibitors from Marrubium velutinum, lignan glucosides
(S)-imperanene
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inhibitor in rum distillate wastewater significantly inhibits tyrosinase isolated from HMV-II cells, competitive inhibition. The inhibitory activities in descending order are (S)-imperanene 4-O-beta-D-glucopyranosyl imperanene, 4-O-beta-D-glucopyranosyl-3-methoxy imperanene
(Z)-2-(4-hydroxybenzylidene)-4-hydroxybenzofuran-3(2H)-one
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71% inhibition at 0.1 mM
(Z)-2-(4-hydroxybenzylidene)-6-hydroxybenzofuran-3(2H)-one
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69% inhibition at 0.1 mM
(Z)-4,6-dihydroxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
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11% inhibition at 0.1 mM
1,3-dimethylimidazolium methylsulfate
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69.7% residual activity at 5% (w/v)
1-butyl-3-methylimidazolium methylsulfate
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47.8% residual activity at 5% (w/v)
1-cyclopentyl-1-hydroxy-2-oxohydrazine
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inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-dodecyl-1-hydroxy-2-oxohydrazine
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inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-ethyl-3-methylimidazolium ethyl sulfate
in the presence of 10 or 20% (w/v) 1-ethyl-3-methylimidazolium ethyl sulfate, the activity decreases dramatically and becomes negligible
1-ethyl-3-methylimidazolium methylsulfate
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64.1% residual activity at 5% (w/v)
1-hydroxy-1-naphthalen-1-yl-2-oxohydrazine
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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
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inhibition of the diphenolase activity of mushroom tyrosinase over the pH range of 5.5-8.0 is studied
1-hydroxy-3-phenylurea
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also retains a substantial potency in cell culture by reducing pigment synthesis by 78%
1-pentanoyl-3-(4-methoxyphenyl)thiourea
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noncompetitive inhibition, docking interaction analysis between 1-pentanoyl-3-(4-methoxyphenyl)thiourea and mushroom tyrosinase
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
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most potent inhibitor
2,3,4'-trihydroxy-4-methoxydeoxybenzoin
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displays stable and significant inhibitory effect on tyrosinase activity
2,4-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]benzamide
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39% inhibition at 0.1 mM; 50% inhibition at 0.1 mM
2-(2-hydroxyethoxy)ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
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2-(2-methoxyethoxy)ethyl (2E)-3-(5-hydroxy-4-oxo-4H-pyran-2-yl)prop-2-enoate
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2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl 3,4,5-trihydroxybenzoate
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mixed-type inhibitor
2-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]acetamide
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34% inhibition at 0.1 mM
2-(4-fluorophenyl)-quinazolin-4(3H)-one
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synthesis of the tyrosinase inhibitor, inhibits the diphenolase activity of tyrosinase. Structure analysis by 1H and 13C NMR spectroscopy, Fourier transform infrared spectroscopy (FTIR), and high resolution mass spectrometry. Molecular docking simulation analysis and inhibition mechanism, a mixed-type inhibitor exerting reversible inhibition, overview. The inhibitor does not reduce the amount of the enzyme, but decreases the enzyme activity for the oxidation of L-dopa
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-chlorophenyl)prop-2-enoate
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mixed-type inhibition
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
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reversible, mixed-type inhibition
2-(4-formyl-2-methoxyphenoxy)-2-oxoethyl 2,4-dihydroxybenzoate
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mixed-type inhibition
2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]acetamide
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16% inhibition at 0.1 mM
2-(chloromethyl)-10-(2-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione
-
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2-(chloromethyl)-10-(4-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione
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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
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weak inhibition
2-chlorobenzaldehyde thiosemicarbazone
-
exhibits significant inhibitory potency on both monophenolase activity and diphenolase activity of tyrosinase, reversible noncompetitive inhibitor
2-oxoglutaric acid
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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
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69.8% inhibition at 50 mM
2-[(2,4-dihydroxyphenyl)methylene]-thiosemicarbazone
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most potent tyrosinase inhibitor
2-[2-(2,4-dihydroxyphenyl)ethyl]-5-(D-xylopyranosyloxy)phenyl D-xylopyranoside
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isolated from Chlorophytum arundinaceum (liliaceae)
2-[2-(2,4-dihydroxyphenyl)ethyl]-5-hydroxyphenyl D-xylopyranoside
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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
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2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl 3,5-dihydroxybenzoate
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2-[3-(2,4-dimethoxy-3-methylphenyl)propyl]benzene-1,4-diol
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plant-derived diarylpropane tyrosinase inhibitor
2alpha,3alpha,23-trihydroxyolean-12-en-28-oic acid
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pentacyclic triterpene extracted from Rhododendron collettianum
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-dihydroxy-N-[2-(1H-indol-3-yl)ethyl]benzamide
-
2% inhibition at 0.1 mM; 7% inhibition at 0.1 mM
3,4-dihydroxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide
-
6% inhibition at 0.1 mM; 9% inhibition at 0.1 mM
3,4-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]benzamide
-
43% inhibition at 0.1 mM; 48% inhibition at 0.1 mM
3-(2-aminoethyl)-1H-indol-5-ol
-
15% inhibition at 0.1 mM; 22% inhibition at 0.1 mM
3-(3',4',5'-trihydroxyphenyl)-6,8-dihydroxycoumarin
-
potent, non-competitive tyrosinase inhibitor, 68.3% inhibition at 0.8 mM
3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propanamide
-
94% inhibition at 0.1 mM
3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propanamide
-
28% inhibition at 0.1 mM
3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propanamide
-
96% inhibition at 0.1 mM
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
4,4'-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-(2-(hydroxymethyl)-7,7-dimethyl-4,9-dioxo-4,6,7,8,9,10-hexahydropyrano[3,2-b]chromen-10-yl)benzonitrile
-
-
4-chlorobenzaldehyde thiosemicarbazone
-
exhibits significant inhibitory potency on both monophenolase activity and diphenolase activity of tyrosinase, reversible mixed-type inhibitor
4-formyl-2-methoxyphenyl (4-methylpiperazin-1-yl)acetate
-
reversible, non-competitive inhibition
4-formylphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside
-
-
4-hydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-methoxybenzamide
-
16% inhibition at 0.1 mM; 32% inhibition at 0.1 mM
4-hydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]benzamide
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31% inhibition at 0.1 mM; 9% inhibition at 0.1 mM
4-Hydroxybenzyl alcohol
-
the compound is a substrate and an inhibitor for tyrosinase, 39% inhibition at 1.5 mM
4-hydroxyphenyl beta-xylotetraoside
-
competitive inhibitor, shows 35fold more potent inhibitory activity than beta-arbutin
4-O-beta-D-glucopyranosyl imperanene
-
inhibitor in rum distillate wastewater significantly inhibits tyrosinase isolated from HMV-II cells. The inhibitory activities in descending order are (S)-imperanene, 4-O-beta-D-glucopyranosyl imperanene, 4-O-beta-D-glucopyranosyl-3-methoxy imperanene
4-O-beta-D-glucopyranosyl-3-methoxy imperanene
-
inhibitor in rum distillate wastewater significantly inhibits tyrosinase isolated from HMV-II cells. The inhibitory activities in descending order are (S)-imperanene, 4-O-beta-D-glucopyranosyl imperanene, 4-O-beta-D-glucopyranosyl-3-methoxy imperanene
4-phenyl-2-butanol
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a reversible, potent inhibitor of tyrosinase, mixed-type inhibitor fothe monophenoase activity and noncompetitive-type inhibitor for the diphenolase activity
4-xylidine-bis(dithiocarbamate) sodium salt
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Na-SSC-NH-CH2-C6H4-CH2-NH-CSS-Na, mixed-type inhibition for both, catecholase and cresolase activities
4-[(1E,3E)-3-(hydroxyimino)-3-(pyridin-2-yl)prop-1-en-1-yl]-N,N-dimethylaniline
-
50.6% inhibition at 50 mM
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside
-
-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
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-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4,6-tetrakis-O-(phenylcarbonyl)-beta-D-glucopyranoside
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-
4-[(E)-(carbamothioylhydrazono)methyl]phenyl 2,3,4-tris-O-(phenylcarbonyl)-beta-D-xylopyranoside
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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)-(hydroxyimino)methyl]phenyl 2,3,4,6-tetra-O-acetyl-beta-D-allopyranoside
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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)-(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-[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'-(4-[[tert-butyl(dimethyl)silyl]oxy]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
-
-
5,2',4'-trihydroxy-2'',2''-dimethylchromene-(6,7:5'',6'')-flavanone
-
dalenin, the reversible inhibitor is 52 and 495times more effective as a monophenolase inhibitor than hydroquinone and kojic acid, respectively, non-competitive inhibitor with L-DOPA as substrate, mixed-I type inhibitor with L-tyrosine as substrate
5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-2,2',3,3',4a,8a-hexahydro-4H,4'H-3,8'-bichromene-4,4'-dione
-
-
5,5',7-trihydroxy-2,2'-bis(4-hydroxyphenyl)-4,4'-dioxo-3,3',4,4',4a,8a-hexahydro-2H,2'H-3,8'-bichromen-7'-yl D-glucopyranoside
-
tyrosinase inhibitor isolated from extracts of the seeds of Garcinia kola
5,6,7,4'-tetramethylscutellarein
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols. Methoxylated flavones, like the methylethers of scutellarein, showed 10times lower inhibitory activity than kojic acid
5,6,7,8,4'-pentahydroxyflavone
-
tyrosinase inhibitors from Marrubium cylleneum, flavones/flavonols
5,7,3',4'-taxifolin teramethyl ether
-
assayed together with (2R,3R)-taxifolin
5,7,4'-trimethylscutellarein
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols. Methoxylated flavones, like the methylethers of scutellarein, showed 10times lower inhibitory activity than kojic acid
5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
97.49% inhibition at 0.2 mM
5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)trione
-
14.3% inhibition at 0.2 mM
5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
88.67% inhibition at 0.2 mM
5-(4-(2-butoxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
78.67% inhibition at 0.2 mM
5-(4-(2-butoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
85.88% inhibition at 0.2 mM
5-(4-(2-butoxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
complete inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
95.86% inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
5.27% inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
16.54% inhibition at 0.2 mM
5-(4-(2-hydroxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
22.41% inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
23.12% inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-(2-methoxyethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
complete inhibition at 0.2 mM
5-(4-(4-methoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
12.2% inhibition at 0.2 mM
5-(4-(4-methoxybutoxy)benzyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
9.85% inhibition at 0.2 mM
5-(4-(4-methoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
1.15% inhibition at 0.2 mM
5-(4-(4-methoxyethoxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-hydroxybenzyl)-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-hydroxybenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
-
47.5% inhibition at 0.2 mM
5-(4-hydroxybenzylidene)-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione
-
complete inhibition at 0.2 mM
5-(4-hydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
-
complete inhibition at 0.2 mM
5-ethenyl-5-hydroxy-3-isocyanocyclopent-2-en-1-one
-
inhibitor produced by Trichoderma viride strain H1-7 from a marine environment. Competitive inhibition
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-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-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
8-isoprenyl-5'-geranyl-5,7,2',4'-tetrahydroxy flavanone
-
competitive inhibitor
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
acteoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of acteoside in the presence of CuSO4 (0.05 mM)
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
alyssonoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides
anthraglycoside B
-
anthraquinone, isolated from the root of Polygonum cuspidatum
Antrodia camphorata extract
-
basidiomycete, only other effect on tyrosinase activity is prepared from Antrodia camphorata using 75% ethanol extraction
-
apigenin
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols
apigenin-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
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
baicalein
-
5,6,7-trihydroxyflavone, high inhibitory effects on tyrosinase. Acts as a cofactor to monophenolase
bayogenin
-
pentacyclic triterpene extracted from Rhododendron collettianum
benzohydroxamic acid
-
is known to inhibit tyrosinase by chelating with copper. Completely independent of pH
benzylacetone
-
a reversible, potent inhibitor of tyrosinase, mixed-type inhibitor
benzyldithiocarbamate sodium salt
-
C6H5-CH2-NH-CSS-Na, noncompetitive inhibition for both, catecholase and cresolase activities
benzylideneacetone
-
a reversible, potent inhibitor of tyrosinase, mixed-type inhibitor
beta-picolyl heptyl amine
-
uncompetitive inhibition of monophenolase and diphenolase activities
beta-picolyl pentyl amine
-
uncompetitive inhibition of monophenolase and diphenolase activities
beta-picolyl propyl amine
-
uncompetitive inhibition of monophenolase and diphenolase activities
betulinic acid
-
pentacyclic triterpene extracted from Rhododendron collettianum
butylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, competitive inhibition for the cresolase activity, competitive inhibition for the catecholase activity
campestrol
-
isolated from Trifolium balansae, NMR structure identification, IC50: 0.00890 mM
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
chrysoeriol
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols
chrysoeriol-7-O-(3'',6''-di-p-coumaroyl)-glucoside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
cistanoside F
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Comparing the activity of tetrasaccharides with cistanoside F
citreorosein
-
anthraquinone, isolated from the root of Polygonum cuspidatum
crenulatoside A
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 23.7%
crude ethanol phase
-
ECPE, inhibitory effect on diphenolase activity of tyrosinase
-
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
daedalin A
-
(2R)-6-hydroxy-2-hydroxymethyl-2-methyl-2H-chromene from mycelial culture of Daedalea dickinsii
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
dihydromorin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
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
dithioerythritol
-
0.05 mM, 82% inhibition of catechol oxidation, 95% inhibition of pyrogallol oxidation and 62% inhibition of dopa oxidation
DMSO
-
low concentrations of DMSO (lower than 3.5 M) lead to reversible mixed-type inhibition of the enzyme, 68.0% residual activity at 1.4 M, 52.6% residual activity at 2.1 M, 36.6% residual activity at 2.8 M, complete inhibition at 5.6 M
echinacoside
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of echinacoside in the presence of CuSO4 (0.05 mM)
epicatechin-(4beta-8, 2beta-O-7)-epicatechin-(4beta-8)-epicatechin
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 34.6%
epigallocatechin gallate
-
exhibits a greater anti-tyrosinase activity than arbutin
erythrodiol
-
pentacyclic triterpene extracted from Rhododendron collettianum
ethylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, uncompetitive inhibition for the cresolase activity, mixed inhibition for the catecholase activity
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
forsythoside B
-
tyrosinase inhibitors from Marrubium velutinum, phenylethanoid glycosides. Bathochromic shift of for sythoside B in the presence of CuSO4 (0.05 mM)
gamma-picolyl heptyl amine
-
uncompetitive inhibition of monophenolase activity and mixed-type inhibition of diphenolase activity
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)
-
glutamic acid
-
individually grafted onto a novel CSG1.0 membrane as a ligand for enzyme purification
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)
H2O2
-
the enzyme becomes inactivated by hydrogen peroxide during catalysis
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
Hexestrol
-
best inhibitors are tropolone, hinokitiol and hexestrol
hexylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, competitive inhibition for the cresolase activity, competitive inhibition for the catecholase activity
hinokitiol
-
best inhibitors are tropolone, hinokitiol and hexestrol
histidine
-
individually grafted onto a novel CSG1.0 membrane as a ligand for enzyme purification
inhibitor peptide
Agaricus hortensis
-
2 natural occuring inhibitors: a 1200 Da peptide that inhibits tyrosinase competitively and second uncharacterized peptide
-
isoartocarpesin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
isoferulate
-
tyrosinase inhibitors from Marrubium cylleneum, phenolic acids
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
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 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
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
kurarinone
-
from the root of Sophora flavescens, exhibits potent antibacterial activity, noncompetitive inhibitor, binds at an allosteric site
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
L-ascorbate
-
significantly inhibits PPO activity, evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
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)
luteolin 4'-O-beta-D-glucopyranoside
-
from Guioa villosa leaf extract, inhibition at 5 mg/ml 14%
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
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
mimosine
-
inhibits monophenolhydroxylase and diphenoloxidase activity, inhibits the activity at concentrations in the microM-range, competitive inhibition
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
N,N-unsubstituted selenourea derivatives
-
55.5% inhibition at 0.2 mM, IC50: 0.17-0.23 mM
-
N-benzylbenzamide derivatives
-
inhibitory potency, structureactivity relationships, overview
-
N-phenylthiourea
-
PTU induces a strong inhibition of the tyrosinase activity
N-[2-(1H-indol-3-yl)ethyl]benzamide
-
0% inhibition at 0.1 mM; 1% inhibition at 0.1 mM
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)propanamide
-
42% inhibition at 0.1 mM
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
-
18% inhibition at 0.1 mM; 23% inhibition at 0.1 mM
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]benzamide
-
22% inhibition at 0.1 mM; 23% inhibition at 0.1 mM
nikotiflorin
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
nobiletin
-
inhibitory effect on tyrosinase diphenolase, from citrus peel crude extracts
NP-40
-
leads to a decrease in the PPO activity, whether p-cresol or catechol is used as the substrate. 50% inhibition is observed in the presence of 68 microM NP-40
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
paeonol
-
effects of paeonol on cell growth of B16F10 melanoma cells are shown. The effect of a high dose of paeonol (200 microM) is better than that of 2 microM hydroquinone (HQ), which acts as a positive agent. Paeonol down-regulates tyrosinase expression at mRNA and protein level. And paeonol inhibits MITF mRNA expression in B16F10 melanoma cells und the phosphorylation of CREB
pentagalloyl glucopyranose
-
exhibits potent, dose-dependent inhibitory effect on tyrosinase with respect to L-DOPA with IC50 of 0.04265 mg/ml
petroleum ether
-
PCPE, inhibitory effect on diphenolase activity of tyrosinase
-
phaselic acid
-
tyrosinase inhibitors from Marrubium velutinum, phenolic acids
physcion
-
anthraquinone, isolated from the root of Polygonum cuspidatum. Most potent tyrosinase inhibition among the four anthraquinones examined, which is comparable to kojic acid
polyvinylpyrrolidone (PVP)-wrapped fullerene derivative
-
inhibitory effect of the water-soluble polymer-wrapped derivative of fullerene, named Radical Sponge. As compared with two major effective cosmetic additives, arbutin and L-ascorbic acid, the polyvinylpyrrolidone (PVP)-wrapped fullerene derivative (Radical Sponge) shows the more marked depigmenting effect in human melanocytes or melanoma cells
-
propylxanthate sodium salt
-
sodium salt of n-alkyl xanthate compound, uncompetitive inhibition for the cresolase activity, mixed inhibition for the catecholase activity
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
sodium cholate
-
in the presence of sodium cholate a decrease in PPO activity is observed when p-cresol is used as the substrate. The inhibition increases with increasing detergent concentration, until a plateau is reached. PPO activity is reduced to 50% of the control
sodium deoxycholate
-
in the presence of sodium deoxycholate, a decrease in PPO activity is observed when p-cresol is used as the substrate. The inhibition increases with increasing detergent concentration, until a plateau is reached. PPO activity is reduced to 50% of the control
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
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
-
tert-butanol
-
the cross-linked enzyme aggregate shows about 50% residual activity after incubation in tert-butanol for about 326 h
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
-
tiliroside
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol acylated glucosides
trifolirhizin
-
prenylated flavonoid from Sophora flavescens, isolated from the EtOAc fraction, inhibitory effects on tyrosinase and melanin synthesis
Tween 80
-
leads to a decrease in the PPO activity, whether p-cresol or catechol is used as the substrate. 60% inhibition is observed in the presence of 32-60 microM Tween 80
tyrosol
-
the compound is a substrate and an inhibitor for tyrosinase, 18% inhibition at 1.5 mM
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
[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
[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
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide
-
67% inhibition at 0.1 mM
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
-
100% inhibition at 0.1 mM
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
-
15% inhibition at 0.1 mM; 30% inhibition at 0.1 mM
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
-
-
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
-
55% inhibition at 0.1 mM; 73% inhibition at 0.1 mM
(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-hydroxy-3-methoxyphenyl)prop-2-enamide
-
29% inhibition at 0.1 mM; 48% inhibition at 0.1 mM
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-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)propane
-
tyrosinase inhibitor with strong depigmenting effects, found in the medicinal plant Dianella ensifolia. 22times more potent than kojic acid
1-Phenyl-2-thiourea
-
the phenoloxidase activity of HdPO is most sensitive to 1-phenyl-2-thiourea, complete inhibition at 5 mM
2,4,6-cycloheptatriene-1-one
Mushroom
-
copper chelator, trivial name tropolone, mixed inhibition, 90% reversible by dialysis, approx. 70% recovery by addition of CuSO4
2,4,6-cycloheptatriene-1-one
-
1 mM, 91% inhibition of catecholase activity
2-acetylamino-1,3,4-thiadiazole-5-sulfonamide
-
acetazolamide or ACZ, in vitro, in vivo studies, and in silico docking studies. Inhibition kinetics, noncompetitive inhibition. Molecular dynamics simulations, overview
2-acetylamino-1,3,4-thiadiazole-5-sulfonamide
-
acetazolamide or ACZ, in vitro, in vivo studies, and in silico docking studies, His244, Asn260 and His85 are the major interacting residues in the binding site of the protein. Inhibition kinetics, acetazolamide is a noncompetitive inhibitor without cytotoxic effect. Molecular dynamics simulations, overview
2-acetylamino-1,3,4-thiadiazole-5-sulfonamide
-
acetazolamideor ACZ, in vitro, in vivo, and in silico studies, inhibition kinetics. Acetazolamide is a a noncompetitive inhibitor without cytotoxic effect showing inhibition of tyrosinase expression in L-DOPA-induced melanoma. Molecular dynamics simulations, overview
2-butyl-5-hydroxyphenyl 3-(3,4-dihydroxyphenyl)propanoate
-
KI-063, a new tyrosinase inhibitor, strong concentration-dependent inhibitory effect on tyrosinase activity
2-mercaptoethanol
-
evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
3-hydroxyphloretin
-
constituents from the formosan apple (Malus doumeri var. formosana), exhibits a dose-dependent inhibitory effect on mushroom tyrosinase activity, competitive inhibitor. Enzyme kinetics study of 3-hydroxyphloretin as inhibitor with various concentrations of the L-tyrosine substrate (15.625, 31.25, 62.5, 125, 250, 500 microM)
3-hydroxyphloretin
-
constituents from the formosan apple (Malus doumeri var. formosana), inhibition 73%, shows substantial cellular tyrosinase inhibitory activity at a concentration of 100 microM
4-hydroxycinnamic acid
-
competitive inhibition of tyrosinase by 4-hydroxycinnamic acid is a slow, reversible reaction with fractional remaining activity, has no effects on the proliferation of normal liver L02 cells, delays the mushroom browning. Molecular docking analysis and kinetic modeling, structure-function analysis, detailed overview
4-methoxycinnamic acid
-
tyrosinase inhibitory activity of 4-methoxycinnamic acid is ever reported, selected as comparing substance
5-hydroxy-2-(hydroxymethyl)-2H-pyran-4-one
-
1.12 mM, 50% inhibition of recombinant enzyme
5-hydroxy-2-(hydroxymethyl)-2H-pyran-4-one
-
trivial name kojic acid, 1 mM, complete inhibition of L-dopa oxidation, 94% inhibition of tyrosinase activity
5-hydroxy-2-(hydroxymethyl)-2H-pyran-4-one
-
1 mM, 50% inhibition of L-dopa oxidation
arbutin
exhibits little inhibitory effect on TyrA with 25.6% inhibition at 10 mM
arbutin
-
tyrosinase inhibitory activity of arbutin is ever reported, selected as comparing substance
arbutin
-
a glycosylated benzoquinone, ascorbic acid reduces melanin formation via reduction of dopaquinone
arbutin
-
as compared with two major effective cosmetic additives, arbutin and L-ascorbic acid, the polyvinylpyrrolidone (PVP)-wrapped fullerene derivative (Radical Sponge) shows the more marked depigmenting effect in human melanocytes or melanoma cells
arbutin
a glycosylated benzoquinone, ascorbic acid reduces melanin formation via reduction of dopaquinone
ascorbic acid
-
inhibition of tyrosinase-catalyzed enzymatic browning by trapping the dopaquinone intermediate with cysteine or ascorbic acid, overview
ascorbic acid
-
the phenoloxidase activity of HdPO is most sensitive to ascorbic acid, 93% inhibition at 10 mM
ascorbic acid
-
exhibits less tyrosinase-inhibitory activity than 3-hydroxyphloretin or catechol
ascorbic acid
-
in descending order of inhibition potency: p-hydroxybenzoic acid > glutathione = ascorbic acid > L-cysteine > EDTA > citric acid
ascorbic acid
-
strong inhibitor, 78% inhibition at 1 mM, 88% inhibition at 10 mM
ascorbic acid
-
50% and 78% inhibition at 1 mM for the cv. Narince samples from 2006 and 2007, respectively
benzoic acid
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
benzoic acid
-
is known to inhibit tyrosinase by chelating with copper. Acts in a similar manner to 1-hydroxy-2-oxo-1-phenylhydrazine
benzoic acid
-
competitive inhibition, 45% inhibition of diphenolase activity at 0.7 mM, 42% inhibition of monophenolase activity at 0.7 mM
beta-(N-3-hydroxypyridone-4)-alpha-aminopropionic acid
Mushroom
-
0.1 mM, 50% inhibition; copper chelator, trivial name L-mimosine
beta-(N-3-hydroxypyridone-4)-alpha-aminopropionic acid
-
copper chelator, trivial name L-mimosine
beta-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
CaCl2
-
evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
catechol
-
constituents from the formosan apple (Malus doumeri var. formosana)
catechol
-
constituents from the formosan apple (Malus doumeri var. formosana), inhibition 78%, shows substantial cellular tyrosinase inhibitory activity at a concentration of 100 microM
cefazolin
-
reversible, competitive inhibition of both monophenolase and diphenolase activities of tyrosinase
cefodizime
-
reversible, mixed-type inhibition of both monophenolase and diphenolase activities of tyrosinase
Cinnamic acid
-
competitive inhibition, 48% inhibition of diphenolase activity at 1.0 mM, 50% inhibition of monophenolase activity at 1.0 mM
Citric acid
-
in descending order of inhibition potency: p-hydroxybenzoic acid > glutathione = ascorbic acid > L-cysteine > EDTA > citric acid
Cl-
-
enzyme added to substrate L-dopa, that is mixed with various concentrations of NaCl in 0.05 M sodium phosphate buffer, pH 7.0. When the NaCl concentration reaches to 600 mM, almost all the enzyme activity is abolished. Cl- induced inhibition of human tyrosinase, Cl- inhibits tyrosinase in a slope-parabolic competitive manner. TXM13 originated tyrosinase and the overexpressed human tyrosinase in HEK293 cells are inhibited. The inhibition by Cl- is reversible
Cl-
-
200 mM, 13% inhibition at pH 6.0, 85% inhibition at pH 5.0, 96% inhibition at pH 4.0
CN-
-
0.2 mM, 70% inhibition of catechol oxidation, 63% inhibition of pyrogallol oxidation, 50% inhibition of dopa oxidation
CN-
-
0.2 mM, 50% inhibition of isoenzyme I, 0.13 mM, 50% inhibition of isoenzyme III
cysteine
-
inhibition of tyrosinase-catalyzed enzymatic browning by trapping the dopaquinone intermediate with cysteine or ascorbic acid, overview
cysteine
-
the phenoloxidase activity of HdPO is most sensitive to cysteine, complete inhibition at 10 mM
diethyldithiocarbamate
-
strongly inhibited by diethyldithiocarbamate, 90.2% inhibition at 20 mM
diethyldithiocarbamate
-
2 mM, complete inhibition, 1 mM Cu2+ restores activity to original level
diethyldithiocarbamate
-
0.5 mM, 50% inhibition of isoenzyme I, 0.19 mM, 50% inhibition of isoenzyme III
diethyldithiocarbamate
-
0.05 mM, 97% inhibition of tyrosinase activity, 83% inhibition of catecholase activity
diethyldithiocarbamate
-
1 mM, 34% inhibition of isoenzyme A, 95% inhibition of isoenzyme B
diethyldithiocarbamate
-
1 mM, complete inhibition of L-dopa oxidation, 21% inhibition of tyrosinase activity
diethyldithiocarbamate
-
1 mM, complete inhibition of L-dopa oxidation
diethyldithiocarbamate
-
competitive vs. tyrosine, addition of Cu2+ restores activity
diethyldithiocarbamate
Vibrio tyrosinaticus
-
10 mM, 80% inactivation, activity is restored by incubation with 0.01 mM Cu2+, Mn2+, Cd2+ or Fe2+
EDTA
-
below 2 mM, 66% inhibition at 0.5 mM, 28% inhibition at 1 mM, no inhibition at 2 mM
EDTA
-
sodium salt of ethylenediaminetetraacetic acid, uncompetitive inhibition
EDTA
-
in descending order of inhibition potency: p-hydroxybenzoic acid > glutathione = ascorbic acid > L-cysteine > EDTA > citric acid
EDTA
-
evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
ellagic acid
-
exhibits less tyrosinase-inhibitory activity than 3-hydroxyphloretin or catechol
ferulic acid
-
tyrosinase inhibitors from Marrubium cylleneum, phenolic acids
gallic acid
-
significantly inhibited tyrosinase. Isolated from Radix polygoni multiflori, a herb used effectively to prevent graying and treat skin depigmentation diseases in traditional Chinese medicine
gallic acid
-
shows a concentration-dependent inhibitory activity against tyrosinase with IC50 of 0.644 mg/ml
gallic acid
-
significantly inhibited tyrosinase. Isolated from Radix polygoni multiflori, a herb used effectively to prevent graying and to treat skin depigmentation diseases in traditional Chinese medicine
glutathione
-
in descending order of inhibition potency: p-hydroxybenzoic acid > glutathione = ascorbic acid > L-cysteine > EDTA > citric acid
guanidine hydrochloride
-
up to 30% inhibition of the cresolase activity is observed upon addition of up to 10 mM guanidine hydrochloride, the inhibition remained at the same level in up to 16 mM guanidine hydrochloride. On the other hand, up to 55% inhibition of the catecholase activity is observed in 17 mM guanidine hydrochloride, a further increase in guanidine hydrochloride to 90 mM led to as much as 75% inhibition of the catecholase activity
Hg2+
-
Hg2+ causes an inhibition in the range of 13% and 72% at 1 and 10 mM, respectively
hydroquinone
shows membrane breaking and toxicity towards melanosomes, and induces hydroxyl free radicals
hydroquinone
-
exhibits less tyrosinase-inhibitory activity than 3-hydroxyphloretin or catechol, very toxic to HEMn cell
kojic acid
-
is known to inhibit tyrosinase by chelating with copper. Shows only slight pH-dependence of tyrosinase inhibition
kojic acid
-
mixed-type inhibition, inhibition study of tyrosinase by pressure-mediated (electrophoretically-mediated) microanalysis, method development and validation, overview
kojic acid
IC50: 0.048 mM for ST94 and ST94t; IC50: 0.048 mM for ST94 and ST94t
kurarinol
-
prenylated flavonoid from Sophora flavescens, isolated from the EtOAc fraction, inhibitory effects on tyrosinase and melanin synthesis. Kurarinol is a prenylated flavanone and an effective inhibitor of alpha-glucosidase, beta-amylase, and cGMP phosphodiesterase-5, and also inhibits diacylglycerol acyltransferase activity
kurarinol
-
from the root of Sophora flavescens, shows no antibacterial activity, competitive inhibitor. Is 50times more potent than lavandulylated flavanones sophoraflavanone G and kurarinone
L-ascorbic acid
-
met-tyrosinase is stable in anaerobic conditions but, in the presence of L-ascorbic acid undergoes an inactivation
L-ascorbic acid
-
1 mM, complete inhibition of purified enzyme, 20% inhibition of crude enzyme
L-ascorbic acid
-
as compared with two major effective cosmetic additives, arbutin and L-ascorbic acid, the polyvinylpyrrolidone (PVP)-wrapped fullerene derivative (Radical Sponge) shows the more marked depigmenting effect in human melanocytes or melanoma cells
L-cysteine
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
L-cysteine
-
in descending order of inhibition potency: p-hydroxybenzoic acid > glutathione = ascorbic acid > L-cysteine > EDTA > citric acid
L-cysteine
-
significantly inhibits PPO activity, evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
L-cysteine
-
52% and 76% inhibition at 1 mM for the cv. Narince samples from 2006 and 2007, respectively
Metabisulfite
-
0.1 mM, 99% inhibition, 1 mM Cu2+ restores activity to original level
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
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)
norartocarpetin
-
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. Norartocarpetin shows a time-dependent inhibition against oxidation of l-tyrosine. It also operated under the enzyme isomerization model
norartocarpetin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
oxyresveratrol
-
a stilbenoid and reversible, non-competitive, and strong inhibitor of tyrosinase, is proposed as skin-whitening and anti-browning agent, can also act as enzyme substrate
p-coumaric acid
-
tyrosinase inhibitors from Marrubium cylleneum, phenolic acids
p-hydroxybenzoic acid
-
in descending order of inhibition potency: p-hydroxybenzoic acid > glutathione = ascorbic acid > L-cysteine > EDTA > citric 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
p-hydroxybenzyl alcohol
-
p-hydroxybenzyl alcohol, inhibitory effect on tyrosinase activity and melanogenesis. p-hydroxybenzyl alcohol exhibits an inhibitory effect on melanogenesis in mouse melanocytes at noncytotoxic concentrations. The results indicate that no significant difference is observed in tyrosinase gene expression between the p-hydroxybenzyl alcohol-treated and non-treated cells. Thus, it is concluded that no repression of tyrosinase gene is induced by p-hydroxybenzyl alcohol
Phenylthiourea
IC50: 0.00017 mM for ST94, 0.00018 mM for ST94t; IC50: 0.00017 mM for ST94, 0.00018 mM for ST94t
Phenylthiourea
-
PTU, copper-chelating reagent, inhibits monophenolhydroxylase and diphenoloxidase activity, inhibits the activity strongly even at concentrations in the nM-range, noncompetitive inhibitor, inhibition with PTU is reversible
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
quercetin
-
tyrosinase inhibitors from Marrubium cylleneum, flavones/flavonols
quercetin
-
decreases the rate of bioreduction to a greater degree in tyrosinase overexpressing clones
quinone isomerase
-
part of a complex consisting of phenoloxidase, quinone isomerase and quinone methide isomerase
-
quinone isomerase
-
part of a complex consisting of phenoloxidase, quinone isomerase and quinone methide isomerase
-
rutin
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
SDS
-
a sharp decrease in the activity of the soluble enzyme is noted from 0 to 17 mM SDS
Sodium azide
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
Sodium azide
-
evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
Sodium diethyl dithiocarbamate
-
SDDC, significantly inhibits PPO activity, evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate. Inhibitors such as sodium diethyl dithiocarbamate and thiourea, which combine with the copper moiety in the enzyme, are generally potent inhibitors of PPO. The inhibitors are copper-chelating agents and they suppress browning activities in which copper is directly involved in the oxidation of phenolic compounds
Sodium fluoride
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
Sodium metabisulfite
-
evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate
Sodium metabisulfite
-
for all ripening stages sodium metabisulfite inhibits PPO activity
Sodium metabisulfite
-
uncompetitive inhibition, 70.5% inhibition at 10 mM
Sodium metabisulfite
-
complete inhibition at 1 mM; effective inhibitor, complete inhibition at 1 mM
Sodium metabisulfite
-
49% and 74% inhibition at 1 mM for the cv. Narince samples from 2006 and 2007, respectively
sodium sulfite
-
the phenoloxidase activity of HdPO is much sensitive to sodium sulfite, 72.1% inhibition at 10 mM
steppogenin
-
isolated from the wood of Artocarpus heterophyllus, strong mushroom tyrosinase inhibitory activity
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
terrein
-
examines 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. Cells co-treated with 2-butyl-5-hydroxyphenyl 3-(3,4-dihydroxyphenyl)propanoate and terrein show much less pigmentation than cells treated with 2-butyl-5-hydroxyphenyl 3-(3,4-dihydroxyphenyl)propanoate or terrein alone
Thiourea
-
the phenoloxidase activity of HdPO is much sensitive to thiourea, 83.7% inhibition at 10 mM
Thiourea
-
evaluated for effectiveness as an inhibitor of PPO activity, using catechol as the substrate. Inhibitors such as sodium diethyl dithiocarbamate and thiourea, which combine with the copper moiety in the enzyme, are generally potent inhibitors of PPO. The inhibitors are copper-chelating agents and they suppress browning activities in which copper is directly involved in the oxidation of phenolic compounds
Triton X-100
-
leads to a decrease in the PPO activity, whether p-cresol or catechol is used as the substrate. With p-cresol as the substrate, up to 80% inhibition is observed in the presence of 30 microM Triton X-100
tropolone
-
is known to inhibit tyrosinase by chelating with copper. Shows only slight pH-dependence of tyrosinase inhibition
tropolone
IC50: 0.0021 mM for ST94, 0.0022 mM for ST94t; IC50: 0.0021 mM for ST94, 0.0022 mM for ST94t
tropolone
-
substrate analogue, best inhibitors are tropolone, hinokitiol and hexestrol
Tween 20
-
leads to a decrease in the PPO activity, whether p-cresol or catechol is used as the substrate. 50% inhibition is observed in the presence of 40-65 microM Tween 20
Urea
-
30% inhibition of cresolase activity is reached with 17 mM urea. No further inhibition is observed for up to 100 mM urea. When the catecholase activity is assayed in the presence of urea, up to 60% inhibition is observed in 0.5 mM urea, a further increase in urea concentration resulted in more inhibition
Zn2+
-
binding structure in the active site, modeling, overview. Replacing the Cu2+ with Zn2+ ions can be performed in TyrBm without structural consequences, while the presence of Zn2+ ions inhibits the activity of tyrosinase on both monophenols and diphenols
additional information
-
melan-a cell viability after application of N,N-unsubstituted selenourea derivatives and kojic acid, overview
-
additional information
-
structure, application and importance of inhibitors, overview
-
additional information
-
no inhibition by phythyl-1-hexanoate and pentacosanol, both isolated and identified from Trifolium balansae
-
additional information
-
suicide inactivation of tyrosinase acting on o-diphenols. A kinetic study of the suicide inactivation of tyrosinase during its action on a variety of substrates is described, and a mechanism is proposed to explain the experimental kinetic results and to throw light on the suicide inactivation step of mushroom tyrosinase
-
additional information
-
compounds from Sophora flavescens are further tested for their inhibitory effects on melanogenesis in B16 melanoma cells. MeOH extract fraction, CH2Cl2 fraction, EtOAc fraction and, n-BuOH fraction from Sophora flavescens inhibit L-tyrosine oxidation catalyzed by tyrosinase in concentration dependent manner. EtOAc fraction has more potent inhibitory activity than the other fractions
-
additional information
-
flavonoids and phenylethanoid glycosides show moderate inhibitory activity against tyrosinase (almost 2-3times weaker than kojic acid). In general at lower concentrations activity descends as flavonols > flavones > acylated monoglycosides > monoglycosides > diglycosides
-
additional information
-
the main active moiety interacting with the center of tyrosinase would be thiosemicarbazo group, the inhibitory activity is closely related with thiosemicarbazide moieties and the groups attached on the aromatic ring. The proposed structure of the formed complexes between tyrosinase and synthesized compounds is shown
-
additional information
-
NHOH moiety is important for tyrosinase inhibition
-
additional information
-
it is shown, that tyrosinase is not inhibited by an excess of monophenol or by reductants such as 6BH4, 6.7 di-CH3BH4 and AH2, when the experimental measurements are made in the true steady-state
-
additional information
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extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening. Three different extracts (acetone, methanol and dichloromethane) of Sideroxylon inerme L. are evaluated for their inhibitory effect in vitro on the monophenolase and diphenolase activated forms of tyrosinase, using a colorimetric procedure
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antibrowning effects of Artocarpus heterophyllus extracts on fresh-cut apple slices tested
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extracts of Antrodia camphorata prepared by 50% extraction and distilled water, and all extracts prepared from Agaricus brasiliensis and Cordyceps militaris show less than 25% inhibition in the reaction mixtures contained 1 mg/ml extracts. No significant inhibitory effect on tyrosinase activity is observed when 0.1 mg/ml extracts are used in the reaction mixture
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the ranking of the inhibitory potency is physcion > citreorosein = anthraglycoside B = emodin
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not inhibited by glabridin diacetate, glabridin dihexanoate, glabridin didecanoate, glabridin dipalmitate, and glabridin distearate
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5-(4-(2-butoxyethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)-trione is not active against tyrosinase
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ellagic acid is not an inhibitor of polyphenol oxidase
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histidine chemical modification of tyrosinase conspicuously inactivates enzyme activity
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atractylenolide III, isofuranodiene, glechomanolide, and chloranthalactone A exhibit no inhibition against tyrosinase
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the alcoholic extract from seed kernels of Thai mango (Mangifera indica L. cultivar Fahlun) exhibits potent, dose-dependent inhibitory effect on tyrosinase with respect to L-DOPA with IC50 of 0.09863 mg/ml
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the enzyme exhibits a lag period when employed in vitro and it is slowly inactivated by catechol substrates and is rapidly inactivated by resorcinols
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true inhibitors of tyrosinase diminish the rate of action of the enzyme when it acts on either of its physiological substrates, L-tyrosine (monophenolase activity) or L-dopa (diphenolase activity)
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design, synthesis (by incorporating heterocyclic piperazine ring), and inhibitory activity of vanillin derivatives against tyrosinase, molecular docking analysis using the tyrosinase structure PDB ID 2ZWE, overview
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structural mechanism of resorcinol inhibitors, overview
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additional information
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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, pharmacophore modeling and molecular docking studies using mushroom tyrosinase structure, PDB ID 2Y9X, as template, overview. Two-dimensional quantitative structure-activity relationship modeling. Inhibition of the diphenolase activity. The thiazolidinone derivatives are synthesized by condensation of substituted thiosemicarbazones with dimethyl acetylenedicarboxylate 4. The thiosemicarbazones are synthesized as intermediates by acid catalyzed condensation of thiosemicarbazide with a range of substituted aromatic aldehydes
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both 4'-hydroxylation and methoxylation of 4-phenylbenzoic acid increase the inhibitory activity of phenylbenzoic acid isomers against mushroom tyrosinase, molecular inhibition mechanism involving the copper ions of the enzyme, overview. Arg268 fixes the angle of the aromatic ring of Phe264, and Val248 and is supposed to interact with the inhibitors as a hydrophobic manner. 4'-Hydroxylation but not methoxylation of 2-phenylbenzoic acid appears inhibitory activity. The interactions of Asn260 and Phe264 in the active site with the adequate-angled biphenyl group are involved in the inhibitory activities of the modified phenylbenzoic acid isomers by parallel and T-shaped Pi-Pi interactions, respectively
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inhibitory kinetics of azachalcones and their oximes on mushroom tyrosinase, solid-state-based mechanochemical synthesis process, and analysis of the inhibition mechanism, overview. The 2'-OH group substituted on ring A is an important design element in achieving enhanced tyrosinase inhibition. The presence of a pyridinyl skeleton results in an improved tyrosinase effect. The pyridinyl N-atom of substituted azachalcone derivatives can possibly get protonated at physiological pH or might be available to coordinate the Cu-atoms existing in the tyrosinase active site
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inhibition of tyrosinase by 4H-chromene analogues, synthesis, kinetic studies, and computational analysis, overview. Dihydropyrano[3,2-b] chromenediones (DHPCs), which are considered 4H-chromenes, are an important class of fused oxygenated heterocycles that are synthesized via a one-pot three-component reaction of kojic acid, an aldehyde and a 1,3-dione. Molecular docking and molecular modeling using the enzyme crystal structure, PDB ID 2Y9X, as template
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automated docking calculations for inhibitor docking to the enzyme structure model, molecular dynamics, overview. Intermolecular interactions and effectiveness of specific inhibition
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design, synthesis, kinetic mechanism, and molecular docking studies of 1-pentanoyl-3-arylthioureas as inhibitors of mushroom tyrosinase and free radical scavengers, structure activity relationships, overview
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inhibition mechanism of mono- and diphenolase activities, overview
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inhibitor screening using surface plasmon resonance (SPR), two-state modeling. Structural changes of the mushroom tyrosinase in the presence of inhibitors are analyzed by circular dichroism spectroscopy
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hydroxycoumarin derivatives as enzyme inhibitors, molecular docking study, structure-activity relationships, overview
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avocado proanthocyanidins, from Persea americana fruits, are a source of tyrosinase inhibitors, they are reversible and competitive inhibitors, structure-activity relationships, and inhibition mechanism, overview. Ligand structure analysis by mass spectroscopy
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the inhibition of tyrosinase by analogues of kojic acid, main interactions occurring between inhibitors-tyrosinase complexes and influence of divalent cation (Cu2+) in enzymatic inhibition are analysed using molecular docking, molecular dynamic simulations and linear interaction energy (LIE) method, using the three-dimensional structure of enzyme AbTYR in complex with inhibitor tropolone, PDB 2Y9X, overview. No inhibition by 3-hydroxy-2-methyl-4-pyrone. Tyrosinase displays various inhibition patterns
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additional information
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proanthocyanidins extracted from Rhododendron pulchrum fresh leaves, collected from the campus of Jiangxi Normal University (Nanchang, China) in June 2011, are a source of tyrosinase inhibitors, structure, activity, and mechanism, mass spectrometric analysis, overview. Inhibition of monophenolase and diphenolase activity of mushroom tyosinase. Molecular docking of tyrosinase with the ligands using the structure of the oxy tyrosinase from Streptomyces castaneoglobisporus as the initial model for docking simulations
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the compounds with resorcinol structure can also act as substrates, react with tyrosinase producing reactive quinones
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carvacrol derivatives as mushroom tyrosinase inhibitors, synthesis, kinetics mechanism and molecular docking studies using crystal structure of mushroom tyrosinase, PDB ID 2Y9X, overview
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synthesis of caffeic acid ester morpholines and inhibitory effect on tyrosinase
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mushroom tyrosinase and melanogenesis inhibition by N-acetyl-pentapeptides, inhibition kinetics, overview. The compounds inhibits melanogenesis and reduce the melanin content, e.g. in murine B16F10 cells
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structure, application and importance of inhibitors, overview
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a significant reduction in phenoloxidase activity is observed from the 6 h embryo stage to the day 11 larvae
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over the same ranges of concentrations (0-30 microM for Triton X-100, 0-65 microM for Tween 20 and for Tween 80, and 0-83 microM for NP-40), no effect is observed on PPO activity when catechol is used as the substrate
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tyrosinase activity is inhibited by an unknown epidermal protein
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in vitro and in vivo inhibitory potency of natural compounds, inhibition of melanogenesis, overview; no inhibition by N-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide at 0.1 mM
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melanin plays a crucial protective role against skin photocarcinogenesis, however, the production of abnormal melanin pigmentation is a serious esthetic problem in humans, melanin biosynthesis can be inhibited by avoiding UV exposure, the inhibition of tyrosinase, the inhibition of melanocyte metabolism and proliferation, or the removal of melanin with corneal ablation, overview, structure, application and importance of inhibitors, overview
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inhibitory potency of different aurones, no inhibition by apigenin, (Z)-2-benzylidene-6-hydroxybenzofuran-3(2H)-one, (Z)-2-(4-ethylbenzylidene)-6-hydroxybenzofuran-3(2H)-one, (Z)-benzylidene-4,6-dihydroxybenzofuran-3(2H)-one, (Z)-4,6-dihydroxy-2-(4-ethylbenzylidene)benzofuran-3(2H)-one, (Z)-4,6-dihydroxy-2-(2-ethylbenzylidene)benzofuran-3(2H)-one, (Z)-4,6-dihydroxy-2-(2-hydroxybenzylidene)benzofuran-3(2H)-one, (Z)-4,6-dihydroxy-2-(4-ethyloxybenzylidene)benzofuran-3(2H)-one, (Z)-2-(4-tert-butylbenzylidene)-4,6-dihydroxybenzofuran-3(2H)-one, (Z)-4,6-dihydroxy-2-(4-propylbenzylidene)benzofuran-3(2H)-one, and (Z)-4,6-dihydroxy-2-(4-hydroxy-3-methoxybenzylidene)benzofuran-3(2H)-one, overview, cytotoxic effects on melanocytes depend on the skin color type of the origin, overview
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additional information
automated docking calculations for inhibitor docking to the enzyme structure model, molecular dynamics, overview. Intermolecular interactions and effectiveness of specific inhibition. Residues N81, N260, H263, and M280 are involved in the binding of inhibitors to mushroom tyrosinase. E195 and H208 are important residues in bacterial tyrosinase, while E230, S245, N249, H252, V262, and S265 bind to inhibitors and are important in forming Pi interaction in human tyrosinase
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additional information
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automated docking calculations for inhibitor docking to the enzyme structure model, molecular dynamics, overview. Intermolecular interactions and effectiveness of specific inhibition. Residues N81, N260, H263, and M280 are involved in the binding of inhibitors to mushroom tyrosinase. E195 and H208 are important residues in bacterial tyrosinase, while E230, S245, N249, H252, V262, and S265 bind to inhibitors and are important in forming Pi interaction in human tyrosinase
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results indicate that the inhibition mechanisms of thiol groups are different from those of halide salts
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no inhibition by Li+. The Cu2+, the active centre of PPO, can be chelated by EDTA and ascorbic acid or replaced by other metal ions such as Ca2+, Zn2+ and Co2+, which cause the inactivation of PPO
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structure, application and importance of inhibitors, overview
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the inhibition of enzyme activity as a function of pH, temperature, and ascorbic acid is studied. The enzymatic activity increases with temperature (within the range studied) and is completely inhibited at pH values below 3.0 regardless of temperature. In alkaline conditions, the inhibitory pH level depends on temperature, at 8°C it is observed at pH above 9.0, whereas at 25°C, inhibition occurrs at pH values above 11.0. In any case, the browning reaction does not occur in the presence of ascorbic acid, and, theoretically, prevent browning in bruised olives
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enzyme-inhibitor binding structure and inhibition mechanism, overview
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pH-dependent inhibition of the enzyme
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natural occurring compounds like cyclodextrins (two different types of cyclodextrins (OH-beta-CDs and gamma-CDs) tested on enzymatic diphenolic oxidation), which are used in food technology and in pharmacology, can release the inhibitory effect of the inhibitors
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structure, application and importance of inhibitors, overview
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the enzyme is strongly inhibited by the reducing agents
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the enzyme is strongly inhibited by the reducing agents
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not inhibited by 1 mM arbutin, or 0.2 mM Cu2+, Fe3+, Zn2+, Mg2+ and Ca2+
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no inhibition by citric acid. The mode of action of inhibitors differs from each other. Ascorbic acid and metabisulfite are reducing agents, which can either reduce o-quinones to colourless diphenols or react irreversibly with o-quinones to form stable colourless
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