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Literature summary extracted from

  • Yamamoto. H.; Inoue, K.; Li, S.M.; Heide, L.
    Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures (2000), Planta, 210, 312-317.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.14.14.174 cytochrome P-450 involved in activity Lithospermum erythrorhizon

General Stability

EC Number General Stability Organism
1.14.14.174 addition of glycerol (20%, v/v) to the microsomal fraction before freezing results in the loss of 80% of the activity Lithospermum erythrorhizon
1.14.14.174 stable against freezing Lithospermum erythrorhizon

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.174 Ancymidol 1 mM, 38% inhibition Lithospermum erythrorhizon
1.14.14.174 CO inhibitory effect of CO is reversed by illumination Lithospermum erythrorhizon
1.14.14.174 cytochrome c 0.01 mM, 96% inhibition Lithospermum erythrorhizon
1.14.14.174 ketoconazole 1 mM, 62% inhibition Lithospermum erythrorhizon
1.14.14.174 Metyrapone 1 mM, 14% inhibition Lithospermum erythrorhizon

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.14.174 0.0015
-
 geranylhydroquinone pH 7.4, 30°C, microsomal fraction Lithospermum erythrorhizon

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.14.174 microsome
-
 Lithospermum erythrorhizon
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.174 geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2 Lithospermum erythrorhizon likely to be involved in shikonin and dihydroechinofuran biosynthesis 3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.174 Lithospermum erythrorhizon
-
 Sieb. et Zucc.
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.14.174 cell suspension culture
-
 Lithospermum erythrorhizon
-

Storage Stability

EC Number Storage Stability Organism
1.14.14.174 -70°C, 1 month, microsomal protein retains 82% of the original activity Lithospermum erythrorhizon

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.174 geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2 likely to be involved in shikonin and dihydroechinofuran biosynthesis Lithospermum erythrorhizon 3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.174 geranylhydroquinone + [reduced NADPH-hemoprotein reductase] + O2 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 Lithospermum erythrorhizon 3''-hydroxygeranylhydroquinone + [oxidized NADPH-hemoprotein reductase] + H2O proton/proton correlation spectroscopic and proton/proton long-range correlation spectroscopic studies confirm that hydroxylation takes place specifically at position 3'' ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.174 GHQ 3''-hydroxylase
-
 Lithospermum erythrorhizon

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.14.174 30
-
-
 Lithospermum erythrorhizon

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.14.174 7.4
-
 activity in K-phosphate buffer at pH 7.4 is only 40% of that observed in Tris-HCl buffer Lithospermum erythrorhizon

pH Range

EC Number pH Minimum pH Maximum Comment Organism
1.14.14.174 6.7 8.3 50% of maximal activiyt at pH 6.7 and pH 8.3. Tris-Cl buffer Lithospermum erythrorhizon

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.174 NADPH required, could not be replaced by NADH, FAD or FMN. The optimal concentration of NADPH for this reaction is between 1 and 5 mM Lithospermum erythrorhizon