Information on EC 1.3.1.45 - 2'-hydroxyisoflavone reductase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY
1.3.1.45
-
RECOMMENDED NAME
GeneOntology No.
2'-hydroxyisoflavone reductase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
vestitone + NADP+ = 2'-hydroxyformononetin + NADPH + H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
redox reaction
-, Q8VYH7
-
reduction
-
-
-
-
reduction
C7BFZ4
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
Isoflavonoid biosynthesis
-
maackiain biosynthesis
-
medicarpin biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
vestitone:NADP+ oxidoreductase
In the reverse reaction, a 2'-hydroxyisoflavone is reduced to an isoflavanone; 2'-hydroxypseudobaptigenin also acts. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
CaIRL
C7BFZ4
gene name
GbIRL1
M1T9X3
-
IFR
C7BFZ4
-
IFR
Q8VYH7
-
IRL
A7Y232
-
isoflavone reductase
-
-
-
-
isoflavone reductase
C7BFZ4
-
isoflavone reductase
A7Y232
-
isoflavone reductase
-
-
isoflavone reductase
Q8VYH7
-
NADPH:2'-hydroxyisoflavone oxidoreductase
-
-
-
-
OsIRL
-
-
OsIRL
Q8VYH7
gene
reductase, 2',7-dihydroxy-4',5'-methylenedioxyisoflavone
-
-
-
-
reductase, 2'-hydroxyisoflavone
-
-
-
-
isoflavone reductase-like protein
C7BFZ4
-
additional information
A7Y232
FcIRL belongs to the class of pinoresinol-lariciresinol reductase, PRL, functioning in the biosynthesis of 8,8'-linked lignans
CAS REGISTRY NUMBER
COMMENTARY
128449-69-4
-
132264-36-9
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
variant Mundo Novo (IAC 388-17-1)
UniProt
Manually annotated by BRENDA team
alfalfa
-
-
Manually annotated by BRENDA team
cv. Apollo
-
-
Manually annotated by BRENDA team
L. cv. Jinheung
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
-, Q8VYH7
transgenic rice lines overexpressing the OsIRL gene under an abscisic acid inducible promoter are tolerant against methyl viologen (MV) and glucose/glucose oxidase-induced stress in rice leave and suspension-cultured cells
metabolism
A7Y232
FcIRL belongs to the class of pinoresinol-lariciresinol reductase, PRL, functioning in the biosynthesis of 8,8'-linked lignans, with function in catalyzing reduction of pinoresinol and lariciresinol into secoisolariciresinol, and medicinal secondary metabolism and resistance in Fagopyrum cymosum
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
show the reaction diagram
-
-
-
?
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
show the reaction diagram
-
trivial name 2'-hydroxypseudobaptigenin, incorporation of pro-R hydrogen from NADPH, i.e. A-specific
-
?
2',7-dihydroxy-4',5'-methylenedioxyisoflavone + NADPH
(3R)2',7-dihydroxy-dihydro-4',5'-methylenedioxyisoflavone + NADP+
show the reaction diagram
-
-
only the 3R-isomer is produced
?
2',7-dihydroxy-4',5'-methylenedioxyisoflavone + NADPH
(3R)2',7-dihydroxy-dihydro-4',5'-methylenedioxyisoflavone + NADP+
show the reaction diagram
-
-
trivial name (-)sophorol
?
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
show the reaction diagram
-
-
only the 3R-isomer is produced
?
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
show the reaction diagram
-
enzyme catalyzes the transfer of H from NADPH to the pro-S position at C-2, yielding 3R-vestitone
only the 3R-isomer is produced
-
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
show the reaction diagram
-
no reaction with isoflavones lacking 2'-hydroxy-group
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
-
-
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
involved in medicarpin and maackiain biosynthesis
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
enzyme is involved in the biosynthesis of the phytoalexin medicarpin, constitutively in roots and nodules and inducible in leaves, overview
-
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
key enzyme in the inducible pterocarpan specific biosynthesis of fungitoxic phytoalexins, e.g. medicarpin, sativan and coumestrol
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
show the reaction diagram
C7BFZ4
CaIRL protein is a new member of the PIP family of NADPH-dependent reductases, enzymes are involved in the biosynthesis of plant defense metabolites such as lignans and isoflavonoids
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
show the reaction diagram
-, Q8VYH7
key enzyme in isoflavonoid phytoalexin biosynthesis
-
-
?
dehydrodiconiferyl alcohol + NADPH
isodihydrodehydrodiconiferyl alcohol NADP+
show the reaction diagram
-, M1T9X3
-
-
-
?
isodihydrodehydrodiconiferyl alcohol + NADPH
tetrahydrodehydrodiconiferyl alcohol + NADP+
show the reaction diagram
-, M1T9X3
-
-
-
-
additional information
?
-
-, Q8VYH7
involvement of OsIRL in homeostasis of reactive oxygen species, products of OsIRL are positive regulators to suppress cell death under oxidative stress
-
-
-
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
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
involved in medicarpin and maackiain biosynthesis
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
enzyme is involved in the biosynthesis of the phytoalexin medicarpin, constitutively in roots and nodules and inducible in leaves, overview
-
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
-
key enzyme in the inducible pterocarpan specific biosynthesis of fungitoxic phytoalexins, e.g. medicarpin, sativan and coumestrol
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
show the reaction diagram
C7BFZ4
CaIRL protein is a new member of the PIP family of NADPH-dependent reductases, enzymes are involved in the biosynthesis of plant defense metabolites such as lignans and isoflavonoids
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
show the reaction diagram
-, Q8VYH7
key enzyme in isoflavonoid phytoalexin biosynthesis
-
-
?
additional information
?
-
-, Q8VYH7
involvement of OsIRL in homeostasis of reactive oxygen species, products of OsIRL are positive regulators to suppress cell death under oxidative stress
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NADH
-
25-40% of activity with NADPH
NADH
-, M1T9X3
-
NADPH
-, Q8VYH7
-
NADPH
C7BFZ4
-
NADPH
A7Y232
the enzyme sequence contains a NADPH-binding motif, G10GTG13YIG16, in the N-terminal region
NADPH
-, M1T9X3
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
A7Y232
the enzyme sequence contains a conserved NmrA, nitrogen metabolite repression regulator, domain, V6-N244
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
-
enzyme expression is induced in seedlings infected with the fungus Colletrichum trifolii, plant protection mechanism and phytoalexin synthesis in vivo, overview
-
additional information
-
enzyme expression is induced upon fungal infection in leaves and elicitation in cell culture
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.013
-
2'-Hydroxyformononetin
-
-
0.0142
-
2'-Hydroxyformononetin
-
wild-type
0.0157
-
2'-Hydroxyformononetin
-
mutant Y272A
0.0158
-
2'-Hydroxyformononetin
-
mutant R97G
0.0162
-
2'-Hydroxyformononetin
-
mutant DELTA39-47 IFR
0.0166
-
2'-Hydroxyformononetin
-
mutant Y169A
0.018
-
2'-Hydroxyformononetin
-
mutant D285G
0.0182
-
2'-Hydroxyformononetin
-
mutant H164A
0.035
-
NADPH
-
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.00383
-
2'-Hydroxyformononetin
-
mutant Y272A
0.004167
-
2'-Hydroxyformononetin
-
mutant D285G
0.0067
-
2'-Hydroxyformononetin
-
mutant Y169A
0.0097
-
2'-Hydroxyformononetin
-
mutant R97G
0.00983
-
2'-Hydroxyformononetin
-
mutant H164A
0.063
-
2'-Hydroxyformononetin
-
mutant DELTA39-47 IFR
0.215
-
2'-Hydroxyformononetin
-
wild-type
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.012
-
-
-
additional information
-
C7BFZ4
a 5'-deletion to -404 completely abolishes promoter activation by abiotic stimulus in transgenic plants
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.5
-
-, M1T9X3
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-, M1T9X3
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
constitutive expression
Manually annotated by BRENDA team
-
enzyme expression is induced upon fungal infection
Manually annotated by BRENDA team
-
constitutive expression
Manually annotated by BRENDA team
-, Q8VYH7
;
Manually annotated by BRENDA team
-
constitutive expression
Manually annotated by BRENDA team
C7BFZ4
specific
Manually annotated by BRENDA team
additional information
-
tissue and subcellular distribution in wild-type alfalfa plants and transgenic tobacco plants, overview
Manually annotated by BRENDA team
additional information
C7BFZ4
no expression in root, stem and flower
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-, M1T9X3
predicted from amino acid sequence
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
33280
-
-, M1T9X3
calculated from cDNA
34000
-
C7BFZ4
predicted from nucleotide sequence encoding 314 amino acids
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
monomer
-
gel filtration
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
phosphoprotein
A7Y232
the enzyme sequence contains multi-phosphorylation sites
glycoprotein
A7Y232
the enzyme sequence contains one conserved glycosylation site at N214
additional information
A7Y232
the enzyme sequence contains an N-terminal acetylation site M1-K5
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
at 1.6 A resolution by hanging-drop vapor-diffusion method
-
OXIDATION STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
complete inactivation without dithioerythritol in 6 h at 4C
-
390812
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, 20 mM potassium phosphate buffer, pH 7.5, 1 mM dithioerythritol, 5% glycerol
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
using Ni-NTA agarose affinity chromatography
-, M1T9X3
Ni2+-NTA affinity chromatography and gel filtration
-
partially, subcellular fractions of cultured cells
-
as six-His tagged OsIRL protein, the generated recombinant OsIRL protein is used for antibody preparation
-, Q8VYH7
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
gene constructs lacking the promoter of CaIRL are introduced into Agrobacterium tumefaciens strain LBA4404 and used to transform tobacco leaf discs
C7BFZ4
cloning of full-length FcIRL, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, overview
A7Y232
recombinantly expressed in Escherichia coli
-, M1T9X3
expression in Nicotiana tabacum
-
expression in transgenic Nicotiana tabacum plants under control of the CaMV35S promotor
-
into Escherichia coli expression vector pET28a
-
generating of transgenic rice lines overexpressing the OsIRL gene under an abscisic acid inducible promoter, the OsIRL transgenic rice line activated by abscisic acid treatment is tolerant against methyl viologen and glucose/glucose oxidase-induced stress in rice leaves and suspension-cultured cells, cloning of recombinant enzyme as six-His tagged OsIRL protein for antibody production
-, Q8VYH7
expression in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
the full-length version of the CaIRL promoter directs a reporter gene expression that is stimulated by mechanical injury as the expression from the native CaIRL gene; the promoter of a gene encoding an isoflavone reductase-like protein in coffee drives a stress-responsive expression in leaves; transcript level is markedly increased in response to fungal infection and mechanical injury, a rapid and marked increase in CaIRL expression is also observed following mechanical injury of the leaves (75fold after 4 h treatment), this induction is followed by a progressive decrease in transcript accumulation at 8 and 12 h post injury, the activation of CaIRL expression by mechanical injury is faster than that observed in response to fungal inoculation
C7BFZ4
increased expression of GbIRL1 is detected when the seedlings are treated with ultraviolet-B, 5-aminolevulinic acid, wounding and ethephon, abscisic acid, salicylic acid
-, M1T9X3
After embedding of seeds in agar containing 2',7',-dichlorofluorescin, the H2O2 is highly stimulated in the elongation region compared with the root apex. The OsIRL mRNA expression level in 3-day-old roots is weakly expressed in the apex region, it shows an increment accompanying the increase in H2O2 concentration, results indicate that the expression level and localization of OsIRL is associated with H2O2 accumulation.; OsIRL gene and protein are downregulated in young seedling roots treated with diphenyleneiodonium, known quencher of reactive oxygen species, but to a lesser extent when compared with glutathione treatment in roots; OsIRL gene and protein are downregulated in young seedling roots treated with reduced glutathione, a known quencher of reactive oxygen species, in roots of 3 day-old young seedlings grown on glutathione, reactive oxygen species levels are significantly decreased by approximately 50% in the presence of 1 mM glutathione compared with untreated controls; OsIRL gene and protein are shown to be downregulated in young seedling roots treated with reduced glutathione and diphenyleneiodonium
-, Q8VYH7
OsIRL transcript level in rice suspension-cultured cells is found to be by hydrogen peroxide, ferric chloride, methyl viologen and glucose/glucose oxidase; the expression of OsIRL is slightly increased after treatment 0.02 mM abscisic acid in wild-type calli, suggesting a possible reason for glucose/glucose oxidase stress resistance; the OsIRL transcript level in rice suspension-cultured cells is induced by FeCl3 within 4 h after treatment, but down-regulated when co-treated with glutathione; the OsIRL transcript level in rice suspension-cultured cells is induced by glucose/glucose oxidase within 4 h after treatment, but down-regulated when co-treated with glutathione; the OsIRL transcript level in rice suspension-cultured cells is induced by methyl viologen within 4 h after treatment, but down-regulated when co-treated with glutathione; the OsIRL transcript level in rice suspension-cultured cells is induced by the oxidant H2O2, but down-regulated when co-treated with glutathione
-, Q8VYH7
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
D285G
-
decreased turnover rate
DELTA39-47
-
nine of the amino acid residues around position 40 deleted in the current construct D39-47 IFR to facilitate crystallization, affects enzyme activity only slightly
G14F
-
no detectable activity
H164A
-
decreased turnover rate
K144A
-
complete loss of enzyme activity
R97G
-
decreased turnover rate
Y169A
-
decreased turnover rate
Y272A
-
decreased turnover rate