Page last updated: 2024-10-24

tyrosinase activity

Definition

Target type: molecularfunction

Catalysis of the reaction: L-tyrosine + O2 = L-DOPAquinone + H2O. This reaction can use both monophenols (such as tyrosine) and catechols (o-diphenols) as substrates. [PMID:4965136, RHEA:18117]

Tyrosinase activity is a crucial enzymatic process that plays a vital role in melanin biosynthesis. This activity is catalyzed by the enzyme tyrosinase, which is a copper-containing enzyme belonging to the type 3 copper protein family. Tyrosinase catalyzes two key reactions in the melanin synthesis pathway:

1. **Hydroxylation of L-tyrosine to L-DOPA:** Tyrosinase acts as a monooxygenase, incorporating molecular oxygen into L-tyrosine to produce L-DOPA (3,4-dihydroxyphenylalanine). This reaction is the rate-limiting step in melanin biosynthesis.

2. **Oxidation of L-DOPA to dopaquinone:** Tyrosinase also acts as an oxidase, oxidizing L-DOPA to dopaquinone. This reaction is crucial as it initiates the polymerization cascade that leads to the formation of melanin pigments.

Dopaquinone is highly reactive and undergoes a series of complex reactions, including auto-oxidation, cyclization, and polymerization, to generate different types of melanin pigments, such as eumelanin (brown-black) and pheomelanin (red-yellow).

Tyrosinase activity is essential for the pigmentation of skin, hair, and eyes. It is also involved in various biological processes, including immune defense, antioxidant activity, and protection against UV radiation. Dysregulation of tyrosinase activity can lead to various pigmentation disorders, such as albinism, vitiligo, and melanoma.

In summary, tyrosinase activity is an enzymatic process that plays a central role in melanin biosynthesis by catalyzing the hydroxylation of L-tyrosine to L-DOPA and the oxidation of L-DOPA to dopaquinone, initiating the polymerization cascade that generates melanin pigments. This activity is crucial for pigmentation and various biological processes.'
"

Proteins (1)

ProteinDefinitionTaxonomy
TyrosinaseA tyrosinase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P14679]Homo sapiens (human)

Compounds (63)

CompoundDefinitionClassesRoles
4-hydroxybenzoic acid4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.monohydroxybenzoic acidalgal metabolite;
plant metabolite
benzaldehydebenzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
benzoic acidaromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.

benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.

Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.
benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
cuminaldehydecuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.benzaldehydesinsecticide;
plant metabolite;
volatile oil component
hydroquinonebenzenediol;
hydroquinones
antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
hexylresorcinolresorcinols
beta-thujaplicinbeta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.

beta-thujaplicin: structure
cyclic ketone;
enol;
monoterpenoid
antibacterial agent;
antifungal agent;
antineoplastic agent;
antiplasmodial drug;
plant metabolite
kojic acid4-pyranones;
enol;
primary alcohol
Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent
resorcinolresorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.

resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951
benzenediol;
phenolic donor;
resorcinols
erythropoietin inhibitor;
sensitiser
levodopaL-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease

Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.
amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid
allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug
salicylaldehydeo-hydroxybenzaldehyde: structure in first sourcehydroxybenzaldehydenematicide;
plant metabolite
xanthonexanthone : The parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9.xanthonesinsecticide
butylphen4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.

butylphen: irritant; structure
phenolsallergen
gamma-thujaplicin2-hydroxy-5-isopropyl- 2,4,6-cycloheptatrienone: a metal chelating agentcyclic ketone
3-hydroxy-1-benzopyran-2-one3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source

hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent.
hydroxycoumarin
2-tert-butylhydroquinone2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.

2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent
hydroquinonesfood antioxidant
4-anisaldehyde4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696

p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.
benzaldehydesbacterial metabolite;
human urinary metabolite;
insect repellent;
plant metabolite
2-hydroxy-4-methoxybenzaldehyde2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)methoxybenzenes;
phenols
1-hydroxy-2(1h)-pyridinone1-hydroxy-2(1H)-pyridinone: structure in first source
2-Methoxyxanthonexanthones
alpha-thujaplicinalpha-thujaplicin: structure in first source
arctiinarctiin: from fruits of Arctium lappa L; RN given refers to (3R-trans)-isomer; RN for cpd without isomeric designation not avail 12/92glycoside;
lignan
glabridinhydroxyisoflavansantiplasmodial drug
moracin mmoracin M: has been isolated from Morus alba L.; structure in first sourcebenzofurans
4-n-butylresorcinol4-n-butylresorcinol: structure in first sourceresorcinols
4-methoxyxanthone4-methoxyxanthone: a vasodilator; structure in first source
mimosineL-mimosine : An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.4-pyridones;
amino acid zwitterion;
non-proteinogenic L-alpha-amino acid
EC 1.14.18.1 (tyrosinase) inhibitor;
plant metabolite
arbutinhydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.beta-D-glucoside;
monosaccharide derivative
Escherichia coli metabolite;
plant metabolite
resveratroltrans-resveratrol : A resveratrol in which the double bond has E configuration.resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
glabreneglabrene: structure in first sourceisoflavonoid
glyasperin Dglyasperin D : A member of the class of hydroxyisoflavans that is (R)-isoflavan substituted by hydroxy groups at positions 2' and 4', methoxy groups at positions 5 and 7 and a prenyl group at position 6. It has been isolated from Glycyrrhiza uralensis.aromatic ether;
hydroxyisoflavans;
methoxyisoflavan
plant metabolite
6-hydroxyindole6-hydroxyindole: structure in first source
trans-4-coumaric acid4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.

hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.

trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.
4-coumaric acidfood component;
mouse metabolite;
plant metabolite
phenylthioureaN-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.

Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.
thioureasEC 1.14.18.1 (tyrosinase) inhibitor
isoeugenoltrans-isoeugenol : The trans-stereoisomer of isoeugenol.isoeugenolplant metabolite
curcumincurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.

Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol
anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger
4-hydroxy-5-methyl-3(2h)-furanone4-hydroxy-5-methyl-3-furanone : A member of the class of furans that is 5-methyl-2,3-dihydrofuran with a hydroxy group at position 4 and a keto group at position 3.cyclic ketone;
enol;
furans
metabolite
quercetin7-hydroxyflavonol;
pentahydroxyflavone
antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
luteolin3'-hydroxyflavonoid;
tetrahydroxyflavone
angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
apigetrinapigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.

apigetrin: structure given in first source
beta-D-glucoside;
dihydroxyflavone;
glycosyloxyflavone;
monosaccharide derivative
antibacterial agent;
metabolite;
non-steroidal anti-inflammatory drug
quercetin 3-o-glucopyranosidequercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells

quercetin 3-O-glucopyranoside: structure in first source
beta-D-glucoside;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone
antineoplastic agent;
antioxidant;
antipruritic drug;
bone density conservation agent;
geroprotector;
histamine antagonist;
osteogenesis regulator;
plant metabolite
kaempferol7-hydroxyflavonol;
flavonols;
tetrahydroxyflavone
antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
hispidolhispidol : A hydroxyaurone that is aurone substituted by hydroxy groups at positions 6 and 4' respectively.hydroxyauroneplant metabolite
7-hydroxycoumarin7-oxycoumarin: derivatives have anti-oxidant properties

umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.
hydroxycoumarinfluorescent probe;
food component;
plant metabolite
euxanthoneeuxanthone : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1 and 7 and an oxo group at position 9. It has been isolated from Cratoxylum cochinchinense.phenols;
xanthones
metabolite;
plant metabolite
trans-2,3',4,5'-tetrahydroxystilbenetrans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrolstilbenoid
linarinlinarin: flavone glycoside isolated from leaves of Linaria japonica MIQ
methyl-p-coumarate4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.

methyl-p-coumarate: structure in first source
4-coumaric acid methyl ester
tilirosidetiliroside: isolated from seeds of Eremocarpus setigeruscinnamate ester;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone
plant metabolite
tilianintilianin: from several medicinal plants including Agastache rugosa and Dracocephalum moldavia
2,4,3',5'-tetramethoxystilbene2,4,3',5'-tetramethoxystilbene: potent inhibitor of human cytochrome P450 1B1; an antihypertensive agent; structure in first source
1-hydroxyxanthone1-hydroxyxanthone: structure in first source
Norartocarpetinflavones
3,4-dihydroxy-xanthone3,4-dihydroxy-xanthone: structure given in first source
hylin
apigenin-7-o-rutinoside
morachalcone amorachalcone A: tyrosinase inhibitor from the wood of Artocarpus heterophyllus; structure in first sourcechalcones
2,4,2',4'-Tetrahydroxychalconechalcones
4-(1-phenylethyl)resorcinol4-(1-phenylethyl)resorcinol: a depigmenting agent for treatment of solar lentigines; structure in first source
3-hydroxyphloretin3-hydroxyphloretin: compound from Formosan apple that reduces tyrosinase activity in human epidermal melanocytes; structure in first sourcechalcones
subamolide asubamolide A: cytotoxic constituent of the stems of Cinnamomum subavenium; structure in first source
feruloyldopamineferuloyldopamine: a dopamine metabolite isolated from tomatoes after infection by Pseudomonas syringae; structure in first source
ascorbic acidAscorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.

L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.

L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.

vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.
ascorbic acid;
vitamin C
coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent