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EC Tree
IUBMB 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.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
daidzein and genistein reductase,
more
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daidzein and genistein reductase
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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'-hydroxylase
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ambiguous
isoflavone 2'-monooxygenase
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isoflavone 2'-monooxygenase
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ambiguous
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formononetin + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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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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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
additional information
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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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ir
biochanin A + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxybiochanin A + [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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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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ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
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formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
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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
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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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ir
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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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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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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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
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [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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involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
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?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
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involved in the biosynthesis of the pterocarpin phytoalexin medicarpin
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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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cytochrome P450-dependent monooxygenase
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ir
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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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additional information
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no cofactors are FAD and FMN
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Mn2+
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cells treated with MnCl2 exhibit 5fold activity after 12 hours
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CO
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ratio CO:O2 of 9:1 leads to 88-96% inhibition
cytochrome c
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0.01 mM cytochrome c reduces activity to 14%, 0.1 mM cytochrome c reduces activity to 4%
juglone
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0.001 mM juglone reduces activity to 50%
additional information
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no inhibition by 5 mM KCN and 1 mM EDTA
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additional information
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cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity
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NADH
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synergistic effect with NADPH
NADH
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135% of NADPH activity
NADH
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synergistic effect with NADPH
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7.5
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assay conditions
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30
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Mervill cv. Harosoy 63, elicitor-induced
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elicitor-induced
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UniProt
brenda
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strain ILC3279 resistant to Ascochyta rabiei and strain ILC susceptible to Ascochyta rabiei, elicitor-induced
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brenda
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suspension
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brenda
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brenda
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brenda
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C81E7_MEDTR
498
1
57641
Swiss-Prot
Secretory Pathway (Reliability: 2 )
A0A072V6A2_MEDTR
500
1
58055
TrEMBL
Secretory Pathway (Reliability: 4 )
A0A0U1WKA6_9ACTN
644
0
68911
TrEMBL
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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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-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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expressed in Saccharomyces cerevisae
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expressed in Saccharomyces cerevisae overexpressing CYP81E1
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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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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
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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
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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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