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EC Tree
IUBMB Comments A cytochrome P-450 (heme-thiolate) protein found in plants, where it is part of the biosynthesis pathway of the red naphthoquinone pigment shikonin.
The enzyme appears in viruses and cellular organisms
Synonyms
CYP76B74 , geranylhydroquinone,NADPH:oxygen oxidoreductase (3''-hydroxylating), GHQ 3''-hydroxylase,
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geranylhydroquinone,NADPH:oxygen oxidoreductase (3''-hydroxylating)
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CYP76B74
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GHQ 3''-hydroxylase
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geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2 = 3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
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geranylhydroquinone,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (3''-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein found in plants, where it is part of the biosynthesis pathway of the red naphthoquinone pigment shikonin.
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geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
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geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
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likely to be involved in shikonin and dihydroechinofuran biosynthesis
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geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
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hydroxylation takes place specifically at position 3'', i.e. at the methyl group involved in the cyclization reaction. The reaction velocity obtained with 3-geranyl-4-hydroxybenzoic acid is more than 100 times lower than that obtained with geranylhydro-quinone
proton/proton correlation spectroscopic and proton/proton long-range correlation spectroscopic studies confirm that hydroxylation takes place specifically at position 3''
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geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
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geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2
3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
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likely to be involved in shikonin and dihydroechinofuran biosynthesis
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NADPH
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required, could not be replaced by NADH, FAD or FMN. The optimal concentration of NADPH for this reaction is between 1 and 5 mM
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Ancymidol
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1 mM, 38% inhibition
CO
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inhibitory effect of CO is reversed by illumination
cytochrome c
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0.01 mM, 96% inhibition
ketoconazole
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1 mM, 62% inhibition
Metyrapone
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1 mM, 14% inhibition
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cytochrome P-450
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involved in activity
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0.0015 - 0.023
geranylhydroquinone
0.0015
geranylhydroquinone
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pH 7.4, 30°C, microsomal fraction
0.023
geranylhydroquinone
pH 7.5, 28°C
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7.4
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activity in K-phosphate buffer at pH 7.4 is only 40% of that observed in Tris-HCl buffer
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6.7 - 8.3
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50% of maximal activiyt at pH 6.7 and pH 8.3. Tris-Cl buffer
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UniProt
brenda
Sieb. et Zucc.
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brenda
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brenda
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brenda
hairy root
brenda
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brenda
protein is anchored to the endoplasmic reticulum membrane
brenda
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brenda
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physiological function
In CYP76B74 RNA interference hairy roots, shikonin derivative accumulation decreases dramatically. CYP76B74 belongs to the CYP76B subfamily and catalyzes the key hydroxylation step in shikonin biosynthesis with high efficiency
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A0A6M3TY96_LITER
496
0
55950
TrEMBL
Secretory Pathway (Reliability: 4 )
A0A6M3TXH1_LITER
496
1
56056
TrEMBL
Secretory Pathway (Reliability: 5 )
A0A3Q9R4N5_9BORA
496
0
55741
TrEMBL
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addition of glycerol (20%, v/v) to the microsomal fraction before freezing results in the loss of 80% of the activity
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stable against freezing
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-70°C, 1 month, microsomal protein retains 82% of the original activity
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Yamamoto. H.; Inoue, K.; Li, S.M.; Heide, L.
Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures
Planta
210
312-317
2000
Lithospermum erythrorhizon
brenda
Wang, S.; Wang, R.; Liu, T.; Lv, C.; Liang, J.; Kang, C.; Zhou, L.; Guo, J.; Cui, G.; Zhang, Y.; Werck-Reichhart, D.; Guo, L.; Huang, L.
CYP76B74 catalyzes the 3''-hydroxylation of geranylhydroquinone in shikonin biosynthesis
Plant Physiol.
179
402-414
2019
Arnebia euchroma (A0A3Q9R4N5), Arnebia euchroma
brenda
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1.14.14.174 geranylhydroquinone 3''-hydroxylase
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