Information on EC 1.14.13.52 - isoflavone 3'-hydroxylase

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The expected taxonomic range for this enzyme is: Papilionoideae

EC NUMBER
COMMENTARY
1.14.13.52
-
RECOMMENDED NAME
GeneOntology No.
isoflavone 3'-hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
formononetin + NADPH + H+ + O2 = calycosin + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
hydroxylation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
Isoflavonoid biosynthesis
-
isoflavonoid biosynthesis II
-
maackiain biosynthesis
-
rot-2'-enonate biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
formononetin,NADPH:oxygen oxidoreductase (3'-hydroxylating)
A heme-thiolate protein (P-450). Also acts on biochanin A and other isoflavones with a 4'-methoxy group. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
isoflavone 3'-hydroxylase
Q2ENF7
-
isoflavone 3'-monooxygenase
-
-
-
-
MtCYP81E9
-
-
CAS REGISTRY NUMBER
COMMENTARY
110183-50-1
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
var. mongholicus
UniProt
Manually annotated by BRENDA team
strain ILC3279 resistant to Ascochyta rabiei and strain ILC susceptible to Ascochyta rabiei, elicitor-induced
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
-
calycosin-7-O-beta-D-glucoside pathway, calycosin and calycosin-7-O-beta-D-glucoside accumulate in whole plants, mainly leaves, in response to low temperature
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2'-hydroxyformononetin + NADPH + O2
2',3' dihydroxyformononetin + H2O
show the reaction diagram
-
39% of activity with biochanin A
-
-
?
biochanin A + NADPH + O2
pratensein + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
biochanin A + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-, Q2ENF7
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-, Q2ENF7
calycosin concentration in different tissues, biosynthetic pathway leading to calycosin-7-O-beta-D-glucoside, overview
-
-
?
formononetin + NADPH + O2
3'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
formononetin + NADPH + O2
3'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
-
involved in the biosynthesis of the pterocarpin phytoalexin maackiain, cytochrome P450-dependent monooxygenase
-
-
ir
formononetin + NADPH + O2
calycosin + NADP+ + H2O
show the reaction diagram
-
50% of activity with biochanin A
-
-
?
genistein + NADPH + O2
?
show the reaction diagram
-
19% of activity with biochanin A
-
-
?
additional information
?
-
-
no substrates are genistein and daidzein, monohydroxylation of 4'-methoxyisoflavones
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-, Q2ENF7
calycosin concentration in different tissues, biosynthetic pathway leading to calycosin-7-O-beta-D-glucoside, overview
-
-
?
formononetin + NADPH + O2
3'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
-
involved in the biosynthesis of the pterocarpin phytoalexin maackiain, cytochrome P450-dependent monooxygenase
-
-
ir
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NADH
-
8.5% of NADPH under same conditions
additional information
-
no cofactors are FAD and FMN
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
CO
-
ratio CO:O2 of 9:1 leads to 88-96% inhibition
cytochrome c
-
0.01 mM reduces activity to 4%, 0.1 mM reduces activity to 1%
juglone
-
0.001 mM juglone reduces activity to 50%
tetcyclasis
-
-
Triadimefone
-
-
ketoconazol
-
-
additional information
-
no inhibition by 5 mM KCN and 1 mM EDTA
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ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NADH
-
synergistic effect with NADPH, 150% of NADPH activity
additional information
-
cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.11
-
Biochanin A
-
pH 8.0, 2 mM NADPH
12.5
-
Biochanin A
-
-
0.05
-
formononetin
-
pH 8.0, 2 mM NADPH
11
-
formononetin
-
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.1
-
Biochanin A
-
pH 8.0, 2 mM NADPH
0.028
-
formononetin
-
pH 8.0, 2 mM NADPH
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
calycosin concentration in different tissues, overview
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.5
-
-
assay conditions
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
assay conditions
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
low mRNA levels
Manually annotated by BRENDA team
-
MRNA is found after arbuscular mycorrhizal colonization
Manually annotated by BRENDA team
additional information
-
calycosin concentration in different tissues, quantitative enzyme expression analysis, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, 100 mM potassium phosphate, pH 7.5 containing 400 mM sucrose and 3.5 mM 2-mercaptoethanol, 24 h
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Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
DNA and amino acid sequence determination and analysis, quantitative tissue-dependent expression analysis, overview
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PCR-amplification
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EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
gradual increase (1.8fold) of enzyme expression after low-temperature treatment (4 h 2C) of plants adapted to 16C, dramatic increase of expression in warm-treatment plants (16C to 25C or from 2C to 25C), maximum at h 4 during treatment, higher levels than at low-temperature induction, cold-induced mRNA accumulation is light dependent
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APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
medicine
-
Astragalus membranaceus var. mongholicus is a medicinal plant in traditional Chinese medicine, the enzyme products calycosin and calycosin-7-O-beta-D-glucoside are two major isoflavones related to the bioactivity of the herb