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Information on EC 1.14.14.83 - geraniol 8-hydroxylase
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1.14.14.83 geraniol 8-hydroxylaseIUBMB Comments
A cytochrome P-450 (heme thiolate) protein found in plants. Also hydroxylates nerol and citronellol, cf. EC 1.14.14.84, linalool 8-monooxygenase. The recommended numbering of geraniol gives 8-hydroxygeraniol as the product rather than 10-hydroxygeraniol as used by references 1-3. See prenol nomenclature {iupac/misc/prenol#p1::Pr-1}. The cloned enzyme also catalysed, but less efficiently, the 3'-hydroxylation of naringenin (cf. EC 1.14.14.82, flavonoid 3'-monooxygenase) .
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Word Map
- 1.14.14.83
- roseus
-
catharanthus
- indole
-
monoterpenoids
-
iridoids
- strictosidine
- ajmalicine
-
nadph-cytochrome
- vinblastine
-
terpenoid
-
co-overexpression
- periwinkle
- vincristine
-
croton
- acuminata
- synthesis
-
methyljasmonate
- vinca
-
camptotheca
- drug development
- pharmacology
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
geraniol 10-hydroxylase, geraniol-10-hydroxylase, cyp76f45, cr10hgo, monoterpene hydroxylase, cyp76b6, 10-hydroxygeraniol oxidoreductase, cyp76b10, geraniol 8-hydroxylase, cyp76b6 protein, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP76B10
CYP76B6
CYP76F45
EC 1.14.13.152
-
-
formerly
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G10H
geraniol 10-hydroxylase
geraniol-10-hydroxylase
monoterpene hydroxylase
G10H
-
-
G10H
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geraniol + [reduced NADPH-hemoprotein reductase] + O2 = (6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
geraniol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
A cytochrome P-450 (heme thiolate) protein found in plants. Also hydroxylates nerol and citronellol, cf. EC 1.14.14.84, linalool 8-monooxygenase. The recommended numbering of geraniol gives 8-hydroxygeraniol as the product rather than 10-hydroxygeraniol as used by references 1-3. See prenol nomenclature {iupac/misc/prenol#p1::Pr-1}. The cloned enzyme also catalysed, but less efficiently, the 3'-hydroxylation of naringenin (cf. EC 1.14.14.82, flavonoid 3'-monooxygenase) [3].
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CAS REGISTRY NUMBER
COMMENTARY
112198-82-0
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R,S)-citronellol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxycitronellol + [oxidized NADPH-hemoprotein reductase] + H2O
cis-nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
farnesol + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxyfarnesol + [oxidized NADPH-hemoprotein reductase] + H2O
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
16-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
nerol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
(R,S)-citronellol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxycitronellol + [oxidized NADPH-hemoprotein reductase] + H2O
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GC-MS product analysis
-
?
(R,S)-citronellol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxycitronellol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
GC-MS product analysis
-
?
cis-nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
GC-MS product analysis
-
?
cis-nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
GC-MS product analysis
-
?
farnesol + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxyfarnesol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
farnesol + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxyfarnesol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
GC-MS product analysis
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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GC-MS product analysis
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?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
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?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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development and validation of an HPLC detection method for quantification of geraniol and 10-hydroxygeraniol, with separation of geraniol and nerol, overview
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?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
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?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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mass spectrometrical product analysis
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?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
16-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
16-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
nerol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
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cis-isomer of geraniol
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-
?
nerol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
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cis-isomer of geraniol
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-
?
additional information
?
-
CrG10H also catalyzed 3'-hydroxylation of the flavanone naringenin to form eriodictyol, a reaction of the flavonoid 3'-hydroxylase. Analysis of the enzyme reactions of the recombinant enzyme with naringenin, apigenin, kaempferol, pcoumaric acid, and ferulic acid, mass spectrometric product analysis, overview
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?
additional information
?
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CrG10H also catalyzed 3'-hydroxylation of the flavanone naringenin to form eriodictyol, a reaction of the flavonoid 3'-hydroxylase. Analysis of the enzyme reactions of the recombinant enzyme with naringenin, apigenin, kaempferol, pcoumaric acid, and ferulic acid, mass spectrometric product analysis, overview
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?
additional information
?
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enzyme is a specialized multifunctional enzyme catalyzing two sequential oxidation steps leading to the formation of 8-oxogeraniol from geraniol. The first step, geraniol hydroxylation, is very efficient and fast enough to outcompete geraniol conjugation in plant tissues
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?
additional information
?
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enzyme is a specialized multifunctional enzyme catalyzing two sequential oxidation steps leading to the formation of 8-oxogeraniol from geraniol. The first step, geraniol hydroxylation, is very efficient and fast enough to outcompete geraniol conjugation in plant tissues
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?
additional information
?
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CYP76B10 is involved in production of swertiamarin
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?
additional information
?
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CYP76B10 is involved in production of swertiamarin
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R,S)-citronellol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxycitronellol + [oxidized NADPH-hemoprotein reductase] + H2O
cis-nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
nerol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
(R,S)-citronellol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxycitronellol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(R,S)-citronellol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxycitronellol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
cis-nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
cis-nerol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
(6E)-8-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
geranylgeraniol + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxygeranylgeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
nerol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
-
cis-isomer of geraniol
-
-
?
nerol + [reduced NADPH-hemoprotein reductase] + O2
10-hydroxynerol + [oxidized NADPH-hemoprotein reductase] + H2O
-
cis-isomer of geraniol
-
-
?
additional information
?
-
CYP76B10 is involved in production of swertiamarin
-
-
?
additional information
?
-
-
CYP76B10 is involved in production of swertiamarin
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
a cytochrome P450 monooxygenase
-
cytochrome P450
an NADPH-cytochrome P450 reductase
-
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
CO
-
inhibition increases with increasing CO concentrations and is almost completely reversed with the aid of a light spurce between 420 and 450 nm
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
dithiothreitol
-
3fold increase in activity in presence of dithiothreitol
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.66
-
purified enzyme, pH 7.6, temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.6
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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expression of G10H is almost undetectable in fruits from May to July, it increases more than 500 times in August and then decreases rapidly in September
brenda
additional information
-
G10H activity is correlated to the ability of the cells to accumulate terpenoid indole alkaloids. Alkaloid induction medium induces the enzyme, overview
brenda
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during the first week of growth, no activity in the stationary growth phase
brenda
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expression analysis of G10H and other enzyme of the monoterpene indole alkaloid biosynthesis pathway, overview
brenda
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expression of G10H in leaves maintains a low level during each growing stage
brenda
additional information
the enzyme is expressed in almost all tissues, except for flower and fruit, in situ RNA tissue hybridization, overview. Tissue localization of the enzyme and related primary metabolic pathways, overview
brenda
additional information
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the enzyme is expressed in almost all tissues, except for flower and fruit, in situ RNA tissue hybridization, overview. Tissue localization of the enzyme and related primary metabolic pathways, overview
brenda
additional information
no expression in hypocotyls, root cap and older developing areas of the root
brenda
additional information
-
no expression in hypocotyls, root cap and older developing areas of the root
brenda
additional information
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tissue-specific expression pattern and expression of PgG10H in response to various biotic and abiotic stresses
brenda
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