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Information on EC 1.14.14.89 - 4'-methoxyisoflavone 2'-hydroxylase
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EC Tree
1.14.14.89 4'-methoxyisoflavone 2'-hydroxylaseIUBMB Comments
A cytochrome P-450 (heme-thiolate) protein. Acts on isoflavones with a 4'-methoxy group, such as formononetin and biochanin A. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. EC 1.14.14.90, isoflavone 2'-hydroxylase, is less specific and acts on other isoflavones as well as 4'-methoxyisoflavones.
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
daidzein and genistein reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EC 1.14.13.53
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-
formerly
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isoflavone 2'-hydroxylase
isoflavone 2'-monooxygenase
isoflavone 2'-hydroxylase
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-
-
-
isoflavone 2'-monooxygenase
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-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
formononetin + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydroxylation
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-
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oxidation
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redox reaction
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-
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reduction
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-
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SYSTEMATIC NAME
IUBMB Comments
formononetin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein. Acts on isoflavones with a 4'-methoxy group, such as formononetin and biochanin A. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. EC 1.14.14.90, isoflavone 2'-hydroxylase, is less specific and acts on other isoflavones as well as 4'-methoxyisoflavones.
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CAS REGISTRY NUMBER
COMMENTARY
110183-49-8
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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
biochanin A + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
biochanin A + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
biochanin A + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O
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-
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ir
biochanin A + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O
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-
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ir
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
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2.0% of the activity with biochanin A
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-
?
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
ir
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
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ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
-
-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
-
-
ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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cytochrome P450-dependent monooxygenase
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-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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cytochrome P450-dependent monooxygenase
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-
ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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78.1% of the activity with biochanin A
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-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
cytochrome P450-dependent monooxygenase
-
-
ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
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ir
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
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2.2% of the activity with biochanin A
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-
?
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
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-
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ir
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
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?
additional information
?
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monohydroxylation of 4'-methoxyisoflavones, no substrates are genistein and daidzein
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?
additional information
?
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monohydroxylation of 4'-methoxyisoflavones, no substrates are genistein and daidzein
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?
additional information
?
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no substrates are 5,7,4'-trihydroxyflavone, 7,4'-dihydroxyflavone, trans-cinnamic acid and 4-coumaric acid
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?
additional information
?
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reduction of soy isoflavones daidzein and genistein under aerobic conditions by use of the recombinant Escherichia coli whole-cell expressing isoflavone reductase
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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
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
-
-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
-
-
ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
cytochrome P450-dependent monooxygenase
-
-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
cytochrome P450-dependent monooxygenase
-
-
ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
cytochrome P450-dependent monooxygenase
-
-
ir
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome c
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0.01 mM cytochrome c reduces activity to 14%, 0.1 mM cytochrome c reduces activity to 4%
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain ILC3279 resistant to Ascochyta rabiei and strain ILC susceptible to Ascochyta rabiei, elicitor-induced
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-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). C81E7_MEDTR
498
1
57641
Swiss-Prot
Secretory Pathway (Reliability: 2)
A0A072V6A2_MEDTR
500
1
58055
TrEMBL
Secretory Pathway (Reliability: 4)
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
reduction of soy isoflavones by use of Escherichia coli whole-cell biocatalyst expressing isoflavone reductase under aerobic conditions, optimization of the aerobic bioconversion conditions, overview. Addition of chloramphenicol significantly increases the bioconversion capacity of the recombinant Escherichia coli whole-cell, but addition of chloramphenicol does not increase the expression of S-DGR irrespective of whether the concentration of chloramphenicol is high. The maximal concentration of daidzein that the recombinant Escherichia coli whole-cell is able to convert efficiently is 0.8 mmol/l. The average bioconversion rate for daidzein is 85.0% and the yield of 2'-hydroxydaidzein is 0.545 mmol/l
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 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
LITERATURE
gene dgr, recombinant enzyme expression in Escherichia coli strain BL21(DE3), aerobic bioconversion capacity of the recombinant Escherichia coli whole-cell under the optimized conditions, method evaluation and optimization, overview
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hinderer, W.; Flentje, U.; Barz, W.
Microsomal isoflavone 2'- and 3'-hydroxylases from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formation
FEBS Lett.
214
101-106
1987
Cicer arietinum
-
brenda
Daniel, S.; Tiemann, K.; Wittkampf, U.; Bless, W.; Hinderer, W.; Barz, W.
Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabiei
Planta
182
270-278
1990
Cicer arietinum
brenda
Clemens, S.; Hinderer, W; Wittkampf, U; Barz, W.
Characterization of cytochrome P450-dependent isoflavone hydroxylases from chickpea
Phytochemistry
32
653-657
1993
Cicer arietinum
-
brenda
Akashi, T.; Aoki, T.; Ayabe, S.I.
CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2'-hydroxylase
Biochem. Biophys. Res. Commun.
251
67-70
1998
Glycyrrhiza echinata
brenda
Shimada, N.; Akashi, T.; Aoki, T.; Ayabe, S.i.
Induction of isoflavonoid pathway in the model legume Lotus japonicus: molecular characterization of enzymes involved in phytoalexin biosynthesis
Plant Sci.
160
37-47
2000
Lotus japonicus
brenda
Kochs, G.; Grisebach, H.
Enzymic synthesis of isoflavones
Eur. J. Biochem.
155
311-318
1986
Glycine max
brenda
Gao, Y.N.; Hao, Q.H.; Zhang, H.L.; Zhou, B.; Yu, X.M.; Wang, X.L.
Reduction of soy isoflavones by use of Escherichia coli whole-cell biocatalyst expressing isoflavone reductase under aerobic conditions
Lett. Appl. Microbiol.
63
111-116
2016
Slackia sp. AUH-JLC159 (A0A0U1WKA6)
brenda
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