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IUBMB Comments This plant enzyme participates in the biosynthesis of the pterocarpan phytoalexins medicarpin, maackiain, and several forms of glyceollin. The enzyme has a strict stereo specificity for the 3R -isoflavanones.
Synonyms
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(3R,4R)-4'-methoxyisoflavan-2',4,7-triol:NADP+ 4-oxidoreductase
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EC 1.1.1.246
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formerly, part transferred
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pterocarpan synthase
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incorrect
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pterocarpin synthase
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incorrect
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vestitone reductase
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a (4R)-4,2'-dihydroxyisoflavan + NADP+ = a (3R)-2'-hydroxyisoflavanone + NADPH + H+
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MetaCyc
(-)-glycinol biosynthesis, (-)-maackiain biosynthesis, (-)-medicarpin biosynthesis
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(3R)-2'-hydroxyisoflavanone:NADP+ 4-oxidoreductase
This plant enzyme participates in the biosynthesis of the pterocarpan phytoalexins medicarpin, maackiain, and several forms of glyceollin. The enzyme has a strict stereo specificity for the 3R-isoflavanones.
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
vestitone + NADP+
7,2'-dihydroxy-4'-methoxyisoflavanol + NADPH + H+
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Substrates: -
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: -
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: vestitone reductase can only use (3R)-vestitone as substrate
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: vestitone reductase has strict substrate stereospecificity for (3R)-vestitone
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: -
ir
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
vestitone + NADP+
7,2'-dihydroxy-4'-methoxyisoflavanol + NADPH + H+
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Substrates: -
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: -
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: vestitone reductase can only use (3R)-vestitone as substrate
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: vestitone reductase has strict substrate stereospecificity for (3R)-vestitone
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(3R)-vestitone + NADPH + H+
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol + NADP+
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Substrates: -
ir
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vestitone
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vestitone reductase is noticeably inhibited by vestitone concentrations in excess of 0.05 mM, the activity being inhibited over 40% at 0.25 mM vestitone
additional information
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not inhibited by (3S)-vestitone
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additional information
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NADPH has no inhibitory effect even at a concentration of 2.5 mM
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0.045
(3R)-vestitone
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in 0.2 M sodium phosphate buffer, pH 6.0, at 30°C
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0.25
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crude extract, in 0.2 M sodium phosphate buffer, pH 6.0, at 30°C
461.1
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after 1844fold purification, in 0.2 M sodium phosphate buffer, pH 6.0, at 30°C
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brenda
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brenda
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brenda
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the highest levels of transcript is in the root
brenda
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relatively high transcript levels are found in the nodule samples
brenda
additional information
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not detected in stem, petiole and leaf
brenda
Highest Expressing Human Cell Lines
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Cell Line Links
Gene Links
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metabolism
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vestitone reductase is the penultimate enzyme in medicarpin biosynthesis
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VESTR_MEDSA
326
0
35918
Swiss-Prot
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35918
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x * 35918, calculated from amino acid sequence
34000
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gel filtration
34000
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1 * 34000, SDS-PAGE
38000
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x * 38000, SDS-PAGE
38000
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1 * 38000, SDS-PAGE
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?
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x * 35918, calculated from amino acid sequence
monomer
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1 * 34000, SDS-PAGE
monomer
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1 * 38000, SDS-PAGE
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hanging drop vapor diffusion method, using 0.1 M Tris-HCl (pH 8.0), 20% (w/v) polyethylene glycol 6000, 0.1 M MgCl2, at 4°C
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Y164A
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the mutation abolishes enzymatic activity
Y164G
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the mutation abolishes enzymatic activity
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Ni2+-NTA agarose column chromatography, Resource Q column chromatography, and Superdex 200 gel filtration
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PEG fractionation, Red-agarose column chromatography, MonoQ column chromatography, and DEAE-Sephacel gel filtration
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli DH5alpha cells
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the activity of vestitone reductase increases approximately 3fold 6 h after treatment with an elicitor preparation derived from yeast in alfalfa suspension cell culture. The activity remains at maximal level for 40 h
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the enzyme expression is upregulated in the common bacterial blight-resistant recombinant inbred line following Xanthomonas axonopodis treatment
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the levels of vestitone reductase transcript greatly increase within 2 h of elicitor addition to alfalfa cell suspension cultures
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Guo, L.; Paiva, N.L.
Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis
Arch. Biochem. Biophys.
320
353-360
1995
Medicago sativa
brenda
Guo, L.; Dixon, R.A.; Paiva, N.L.
The pterocarpan synthase of alfalfa: association and co-induction of vestitone reductase and 7,2-dihydroxy-4-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis
FEBS Lett.
356
221-225
1994
Medicago sativa
brenda
Guo, L.; Dixon, R.A.; Paiva, N.L.
Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2-dihydroxy-4-methoxyisoflavanol dehydratase
J. Biol. Chem.
269
22372-22378
1994
Medicago sativa
brenda
Shao, H.; Dixon, R.A.; Wang, X.
Crystal structure of vestitone reductase from alfalfa (Medicago sativa L.)
J. Mol. Biol.
369
265-276
2007
Medicago sativa
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
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