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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+
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
2'-hydroxyformononetin + NADPH
vestitone + NADP+
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
dehydrodiconiferyl alcohol + NADPH
isodihydrodehydrodiconiferyl alcohol + NADP+
-
-
-
?
isodihydrodehydrodiconiferyl alcohol + NADPH
tetrahydrodehydrodiconiferyl alcohol + NADP+
-
-
-
?
additional information
?
-
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+
-
-
only the 3R-isomer is produced
?
2',7-dihydroxy-4',5'-methylenedioxyisoflavone + NADPH
(3R)2',7-dihydroxy-dihydro-4',5'-methylenedioxyisoflavone + NADP+
-
-
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
?
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
-
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+
-
-
-
-
?
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+
-
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
GmIFR is an isoflavone reductase
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
key enzyme in isoflavonoid phytoalexin biosynthesis
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
-
-
-
-
?
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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2'-hydroxyformononetin + NADPH
vestitone + NADP+
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
additional information
?
-
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
-
-
?
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
-
-
-
-
?
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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Anaphylaxis
Cross-reactivity of IgE antibodies to allergens.
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.
Hypersensitivity
Pollensomes as Natural Vehicles for Pollen Allergens.
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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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
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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
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enzyme gene expression is associated with wheat yield performance under heat stress at anthesis
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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)
DNA and amino acid sequence dteremination and analysis, sequence comparisons and phylogenetic analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) by dialysis, nickel affinity chromatography, and proteolytic digestion of fusion protein with Factor Xa protease
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expression in Escherichia coli
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expression in Nicotiana tabacum
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expression in transgenic Nicotiana tabacum plants under control of the CaMV35S promotor
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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
into Escherichia coli expression vector pET28a
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isoflavone reductase-like gene gene by reverse transcription, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, recombinant expression in Escherichia coli strain BL21
recombinantly expressed in Escherichia coli
sequence comparisons and phylogenetic tree, quantitative real-time PCR enzyme expression analysis
-
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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.
enzyme expression and transcript levels of PvIFR1, detected preferentially in the susceptible zone of roots, are augmented upon nitrogen starvation and in response to Rhizobium etli inoculation at very early stages of the interaction
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higher enzyme expression in the leaf is recorded under the combined effect of heat stress (40/22 C day/night temperature for 4 days) and elevated CO2 (800 ppm)
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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 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
OsIRL transcript level in rice suspension-cultured cells is found to be by hydrogen peroxide, ferric chloride, methyl viologen and glucose/glucose oxidase
the enzyme expression is significantly induced by infection with Phytophthora sojae, as well as by treatment with ethephon, abscisic acid, and salicylic acid
the enzyme expression is upregulated in the common bacterial blight-resistant recombinant inbred line following Xanthomonas axonopodis treatment
-
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 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 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 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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Tiemann, K.; Hinderer, W.; Barz, W.
Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of pterocarpan phtoalexin biosynthesi in cell suspension cultures of Cicer arietinum
FEBS Lett.
213
324-328
1987
Cicer arietinum
-
brenda
Schlieper, D.; Tiemann, K.; Barz, W.
Stereospecificity of hydrogen transfer by fungal and plant NADPH:isoflavone oxidoreductases
Phytochemistry
29
1519-1524
1990
Cicer arietinum
-
brenda
Preisig, C.L.; Bell, J.N.; Sun, Y.; Hrazdina, G.; Matthews, D.E.; VanEtten, H.D.
Biosynthesis of the phytoalexin pisatin. Isoflavone reduction and further metabolism of the product sophorol by extracts of Pisum sativum
Plant Physiol.
94
1444-1448
1990
Pisum sativum
brenda
Paiva, N.L.; Sun, Y.; Dixon, R.A.; VanEtten, H.D.; Hrazdina, G.
Molecular cloning of isoflavone reductase from pea (Pisum sativum L.): evidence for a 3R-isoflavanone intermediate in (+)-pisatin biosynthesis
Arch. Biochem. Biophys.
312
501-510
1994
Pisum sativum
brenda
Cooper, J.D.; Qiu, F.; Paiva, N.L.
Biotransformation of an exogenously supplied isoflavonoid by transgenic tobacco cells expressing alfalfa isoflavone reductase
Plant Cell Rep.
20
876-884
2002
Medicago sativa
-
brenda
Saunders, J.; O'Neill, N.
The characterization of defense responses to fungal infection in alfalfa
BioControl
49
715-728
2004
Medicago sativa
-
brenda
Lopez-Meyer, M.; Paiva, N.L.
Immunolocalization of vestitone reductase and isoflavone reductase, two enzymes involved in the biosynthesis of the phytoalexin medicarpin
Physiol. Mol. Plant Pathol.
61
15-30
2002
Medicago sativa
brenda
Wang, X.; He, X.; Lin, J.; Shao, H.; Chang, Z.; Dixon, R.A.
Crystal structure of isoflavone reductase from alfalfa (Medicago sativa L.)
J. Mol. Biol.
358
1341-1352
2006
Medicago sativa
brenda
Kim, S.G.; Kim, S.T.; Wang, Y.; Kim, S.K.; Lee, C.H.; Kim, K.K.; Kim, J.K.; Lee, S.Y.; Kang, K.Y.
Overexpression of rice isoflavone reductase-like gene (OsIRL) confers tolerance to reactive oxygen species
Physiol. Plant.
138
1-9
2009
Oryza sativa, Oryza sativa (Q8VYH7)
brenda
Brandalise, M.; Severino, F.E.; Maluf, M.P.; Maia, I.G.
The promoter of a gene encoding an isoflavone reductase-like protein in coffee (Coffea arabica) drives a stress-responsive expression in leaves
Plant Cell Rep.
28
1699-1708
2009
Coffea arabica (C7BFZ4)
brenda
Zhu, Q.L.; Guo, T.Y.; Sui, S.Z.; Liu, G.D.; Lei, X.H.; Luo, L.L.; Li, M.Y.
Molecular cloning and characterization of a novel isoflavone reductase-like gene (FcIRL) from high flavonoids-producing callus of Fagopyrum cymosum
Yao Xue Xue Bao
44
809-819
2009
Fagopyrum cymosum (A7Y232)
brenda
Hua, C.; Linling, L.; Feng, X.; Yan, W.; Honghui, Y.; Conghua, W.; Shaobing, W.; Zhiqin, L.; Juan, H.; Yuping, W.; Shuiyuan, C.; Fuliang, C.
Expression patterns of an isoflavone reductase-like gene and its possible roles in secondary metabolism in Ginkgo biloba
Plant Cell Rep.
32
637-650
2013
Ginkgo biloba (M1T9X3), Ginkgo biloba
brenda
Castro, L.; Crespo, J.F.; Rodriguez, J.; Rodriguez, R.; Villalba, M.
Immunoproteomic tools are used to identify masked allergens Ole e 12, an allergenic isoflavone reductase from olive (Olea europaea) pollen
Biochim. Biophys. Acta
1854
1871-1880
2015
Olea europaea
brenda
Cheng, Q.; Li, N.; Dong, L.; Zhang, D.; Fan, S.; Jiang, L.; Wang, X.; Xu, P.; Zhang, S.
Overexpression of soybean isoflavone reductase (GmIFR) enhances resistance to phytophthora sojae in soybean
Front. Plant Sci.
6
1024
2015
Glycine max (C6TER4), Glycine max
brenda
Qian, X.; Xu, S.; Zhao, C.; Meng, H.; Wen, G.
cDNA cloning and expression analyses of the isoflavone reductase-like gene of Dendrobium officinale
Pak. J. Bot.
47
1265-1270
2015
Dendrobium catenatum (A0A068ERY8)
-
brenda
Ripodas, C.; Via, V.D.; Aguilar, O.M.; Zanetti, M.E.; Blanco, F.A.
Knock-down of a member of the isoflavone reductase gene family impairs plant growth and nodulation in Phaseolus vulgaris
Plant Physiol. Biochem.
68
81-89
2013
Phaseolus vulgaris
brenda
Shokat, S.; Novak, O.; Siroka, J.; Singh, S.; Gill, K.S.; Roitsch, T.; Grosskinsky, D.K.; Liu, F.
Elevated CO2 modulates the effect of heat stress responses in Triticum aestivum by differential expression of isoflavone reductase-like (IRL) gene
J. Exp. Bot.
72
7594-7609
2021
Triticum aestivum
brenda
Cox, L.D.; Munholland, S.; Mats, L.; Zhu, H.; Crosby, W.L.; Lukens, L.; Pauls, K.P.; Bozzo, G.G.
The induction of the isoflavone biosynthesis pathway is associated with resistance to common bacterial blight in Phaseolus vulgaris L.
Metabolites
11
433
2021
Phaseolus vulgaris
brenda