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Enzyme Nomenclature
Information on EC 1.3.1.45 - 2'-hydroxyisoflavone reductase
Word Map on EC 1.3.1.45
- 1.3.1.45
-
phytoalexins
-
isoflavonoids
- medicarpin
- pisatin
-
phenylcoumaran
-
thaumatin-like
-
pinoresinol-lariciresinol
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.3.1.45
-
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RECOMMENDED NAME
GeneOntology No.
2'-hydroxyisoflavone reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
vestitone + NADP+ = 2'-hydroxyformononetin + NADPH + H+
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
reduction
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
128449-69-4
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132264-36-9
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
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
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
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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
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
2',7-dihydroxy-4',5'-methylenedioxyisoflavone + NADPH
(3R)2',7-dihydroxy-dihydro-4',5'-methylenedioxyisoflavone + NADP+
dehydrodiconiferyl alcohol + NADPH
isodihydrodehydrodiconiferyl alcohol + NADP+
-
-
-
?
isodihydrodehydrodiconiferyl alcohol + NADPH
tetrahydrodehydrodiconiferyl alcohol + NADP+
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-
-
-
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
-
-
-
?
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
-
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+
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-
only the 3R-isomer is produced
?
2',7-dihydroxy-4',5'-methylenedioxyisoflavone + NADPH
(3R)2',7-dihydroxy-dihydro-4',5'-methylenedioxyisoflavone + NADP+
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-
trivial name (-)sophorol
?
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
-
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
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2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
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no reaction with isoflavones lacking 2'-hydroxy-group
-
?
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
-
-
only the 3R-isomer is produced
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
-
involved in medicarpin and maackiain biosynthesis
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
-
enzyme is involved in the biosynthesis of the phytoalexin medicarpin, constitutively in roots and nodules and inducible in leaves, overview
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-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
-
key enzyme in the inducible pterocarpan specific biosynthesis of fungitoxic phytoalexins, e.g. medicarpin, sativan and coumestrol
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
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
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-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
key enzyme in isoflavonoid phytoalexin biosynthesis
-
-
?
additional information
?
-
-
involvement of OsIRL in homeostasis of reactive oxygen species, products of OsIRL are positive regulators to suppress cell death under oxidative stress
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-
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additional information
?
-
involvement of OsIRL in homeostasis of reactive oxygen species, products of OsIRL are positive regulators to suppress cell death under oxidative stress
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
2'-hydroxyformononetin + NADPH
vestitone + NADP+
-
involved in medicarpin and maackiain biosynthesis
-
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
-
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+
-
key enzyme in the inducible pterocarpan specific biosynthesis of fungitoxic phytoalexins, e.g. medicarpin, sativan and coumestrol
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
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+
Q8VYH7
key enzyme in isoflavonoid phytoalexin biosynthesis
-
-
?
additional information
?
-
-
involvement of OsIRL in homeostasis of reactive oxygen species, products of OsIRL are positive regulators to suppress cell death under oxidative stress
-
-
-
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
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
the enzyme sequence contains a NADPH-binding motif, G10GTG13YIG16, in the N-terminal region
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
the enzyme sequence contains a conserved NmrA, nitrogen metabolite repression regulator, domain, V6-N244
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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enzyme expression is induced in seedlings infected with the fungus Colletrichum trifolii, plant protection mechanism and phytoalexin synthesis in vivo, overview
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additional information
-
enzyme expression is induced upon fungal infection in leaves and elicitation in cell culture
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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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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
a 5'-deletion to -404 completely abolishes promoter activation by abiotic stimulus in transgenic plants
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
-
tissue and subcellular distribution in wild-type alfalfa plants and transgenic tobacco plants, overview
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
the enzyme sequence contains one conserved glycosylation site at N214
phosphoprotein
the enzyme sequence contains multi-phosphorylation sites
additional information
the enzyme sequence contains an N-terminal acetylation site M1-K5
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 20 mM potassium phosphate buffer, pH 7.5, 1 mM dithioerythritol, 5% glycerol
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
as six-His tagged OsIRL protein, the generated recombinant OsIRL protein is used for antibody preparation
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning of full-length FcIRL, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, overview
expression in transgenic Nicotiana tabacum plants under control of the CaMV35S promotor
-
gene constructs lacking the promoter of CaIRL are introduced into Agrobacterium tumefaciens strain LBA4404 and used to transform tobacco leaf discs
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
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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
increased expression of GbIRL1 is detected when the seedlings are treated with ultraviolet-B, 5-aminolevulinic acid, wounding and ethephon, abscisic acid, salicylic acid
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
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
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.45)
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