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.
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 |
|