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Information on EC 1.3.1.45 - 2'-hydroxyisoflavone reductase
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1.3.1.45 2'-hydroxyisoflavone reductaseIUBMB Comments
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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Word Map
- 1.3.1.45
-
isoflavonoids
-
phytoalexins
- medicarpin
-
phenylcoumaran
- pisatin
-
pinoresinol-lariciresinol
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pterocarpans
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thaumatin-like
- pollinosis
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
isoflavone reductase, osirl, isoflavone reductase-like protein, gbirl1, ole e 12, cairl, gmifr, pvifr1, 2'-hydroxyisoflavone reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IFR
IRL
isoflavone reductase
isoflavone reductase-like protein
NADPH:2'-hydroxyisoflavone oxidoreductase
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reductase, 2',7-dihydroxy-4',5'-methylenedioxyisoflavone
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reductase, 2'-hydroxyisoflavone
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additional information
FcIRL belongs to the class of pinoresinol-lariciresinol reductase, PRL, functioning in the biosynthesis of 8,8'-linked lignans
isoflavone reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
vestitone + NADP+ = 2'-hydroxyformononetin + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
reduction
redox reaction
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reduction
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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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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+
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-
-
?
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+
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-
-
?
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
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trivial name 2'-hydroxypseudobaptigenin, incorporation of pro-R hydrogen from NADPH, i.e. A-specific
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?
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+
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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+
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no reaction with isoflavones lacking 2'-hydroxy-group
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?
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
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only the 3R-isomer is produced
?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
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involved in medicarpin and maackiain biosynthesis
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?
2'-hydroxyformononetin + NADPH
vestitone + NADP+
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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+
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key enzyme in the inducible pterocarpan specific biosynthesis of fungitoxic phytoalexins, e.g. medicarpin, sativan and coumestrol
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-
?
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+
GmIFR is an isoflavone reductase
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-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
key enzyme in isoflavonoid phytoalexin biosynthesis
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-
?
additional information
?
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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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?
additional information
?
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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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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
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+
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+
GmIFR is an isoflavone reductase
-
-
?
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
-
-
?
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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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
the enzyme sequence contains a NADPH-binding motif, G10GTG13YIG16, in the N-terminal region
NADPH
the enzyme contains a NAD(P)H-binding motif (GGTGYIG) in the N-terminal region
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INHIBITOR
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
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enzyme expression is induced upon fungal infection in leaves and elicitation in cell culture
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Dehydration
Gene expression analysis in Eucalyptus globulus exposed to drought stress in a controlled and a field environment indicates different strategies for short- and longer-term acclimation.
Dehydration
Proteomic analyses unraveling water stress response in two Eucalyptus species originating from contrasting environments for aridity.
Food Hypersensitivity
Structural functionality, catalytic mechanism modeling and molecular allergenicity of phenylcoumaran benzylic ether reductase, an olive pollen (Ole e 12) allergen.
Infections
Suppression of an Isoflavonoid Phytoalexin Defense Response in Mycorrhizal Alfalfa Roots.
Mycoses
Expression patterns of an isoflavone reductase-like gene and its possible roles in secondary metabolism in Ginkgo biloba.
Mycoses
The promoter of a gene encoding an isoflavone reductase-like protein in coffee (Coffea arabica) drives a stress-responsive expression in leaves.
Rhinitis, Allergic, Seasonal
Immunoproteomic tools are used to identify masked allergens: Ole e 12, an allergenic isoflavone reductase from olive (Olea europaea) pollen.
Starvation
Knock-down of a member of the isoflavone reductase gene family impairs plant growth and nodulation in Phaseolus vulgaris.
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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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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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transcripts of PvIFR1 are detected preferentially in the susceptible zone II of roots, quantitative expression anaysis, overview
brenda
additional information
tissue expression levels of the enzyme, overview
brenda
additional information
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tissue and subcellular distribution in wild-type alfalfa plants and transgenic tobacco plants, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
subcellular localization analysis in transgenic protoplasts
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
the enzyme contains a conserved nitrogen metabolite repression regulator (NmrA) domain and a phenylcoumaran benzylic ether reductase (PCBER) domain
evolution
isoflavone reductases (IFRs) are unique to the plant kingdom. The enzyme is a member of the soybean isoflavone reductase gene family GmIF
evolution
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the allergen, named Ole e 12, is a polymorphic isoflavone reductase-like protein of 308 amino acids showing 80% and 74% identity with birch and pear allergens, Bet v 6 and Pyr c 5, respectively. Analysis of the presence of Ole e 12 homologues in different pollens from other species, overview
evolution
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the enzyme is a member of the isoflavone reductase gene family
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
malfunction
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knockdown of PvIFR1 mediated by RNA interference (RNAi) in common bean composite plants results in a reduction of shoot and root length. Reduction of PvIFR1 mRNAs also affects growth of lateral roots after emergence, a stage in which auxins are required to establish a persistent meristem. Upon inoculation, the number of nodules formed by different strains of Rhizobium etli is significantly lower in IFR RNAi than in control roots. Transcript levels of two auxin-regulated genes are consistent with lower levels of auxin in PvIFR1 silenced roots. No differences in mRNA levels of PvIFR1 are observed between shoots of IFR and GUS RNAi composite plants, indicating that the shoot phenotype is not caused by systemic silencing of PvIFR1. Root phenotype, overview
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
metabolism
-
the enzyme participates in the last steps of the biosynthetic pathway of isoflavonoids
physiological function
isoflavonereductase (IFR)is an enzyme involved in the biosynthetic pathway of isoflavonoid phytoalexin in plants. The enzyme is considered to have a crucial role in plant response to various biotic and abiotic environmental stresses. Overexpression of soybean isoflavone reductase (GmIFR) enhances resistance to Phytophthora sojae in soybean. Enzyme GmIFR might play an important role as an antioxidant to reduce ROS in soybean
physiological function
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the 37-kDa enzyme protein seems to be associated to the IgE-binding profile of a group of patients suffering allergy to peach and olive pollen. The allergen, named Ole e 12, is a polymorphic isoflavone reductase-like protein of 308 amino acids showing 80% and 74% identity with birch and pear allergens, Bet v 6 and Pyr c 5, respectively. Ole e 12 is a minor olive pollen allergen, which gains relevance in patients allergic to peach with olive pollinosis
physiological function
-
enzyme gene expression is associated with wheat yield performance under heat stress at anthesis
Show AA Sequence and Transmembrane Helices (122 entries)
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Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
?
x * 34000, about, sequence calculation, x * 33000, recombinant enzyme, SDS-PAGE
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x * 34920, sequence calculation, x * 34000, recombinant enzyme, SDS-PAGE
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x * 37000, SDS-PAGE, x * 34285, recombinant His-tagged enzyme, mass spectrometry
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
phosphoprotein
the enzyme sequence contains multi-phosphorylation sites
additional information
the enzyme sequence contains an N-terminal acetylation site M1-K5
glycoprotein
the enzyme sequence contains two conserved N-glycosylation sites
glycoprotein
the enzyme sequence contains one conserved glycosylation site at N214
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
DELTA39-47
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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
additional information
additional information
enzyme overexpression in Glycine max transgenic plants results in highly reduced daidzein levels, while the relative content of glyceollins in transgenic plants is significantly higher than that of non-transgenic plants. The relative expression levels of reactive oxygen species (ROS) of transgenic soybean plants are significantly lower than those of non-transgenic plants after incubation with Phytophthora sojae. Overexpression of GmIFR in soybean seed affects isoflavone and glyceollins expression levels, as well as the transcriptional level of multiple genes involved in the phenylpropanal pathway
additional information
-
enzyme overexpression in Glycine max transgenic plants results in highly reduced daidzein levels, while the relative content of glyceollins in transgenic plants is significantly higher than that of non-transgenic plants. The relative expression levels of reactive oxygen species (ROS) of transgenic soybean plants are significantly lower than those of non-transgenic plants after incubation with Phytophthora sojae. Overexpression of GmIFR in soybean seed affects isoflavone and glyceollins expression levels, as well as the transcriptional level of multiple genes involved in the phenylpropanal pathway
additional information
-
knockdown of PvIFR1 mediated by RNA interference (RNAi) in common bean composite plants results in a reduction of shoot and root length. Reduction of PvIFR1 mRNAs also affects growth of lateral roots after emergence, a stage in which auxins are required to establish a persistent meristem. IFR RNAi affects the number of nodules
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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
recombinant His-tagged enzyme from cell free extract of Escherichia coli strain BL21(DE3)
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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
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, transient expression of GFP-tagged enzyme in Glycine max protoplasts' cytoplasm, recombinant overexpression of the enzyme under the control of a CaMV35S promoter via Agrobacterium tumefaciens strain LBA4404 and tri-parental mating in transgenic Glycine max plants, quantitative real-time PCR enzyme expression analysis, recombinant expression of Nterminally His6-tagged enzyme in Escherichia coli strain Transetta (DE3)