Information on EC 1.3.1.77 - anthocyanidin reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.1.77
-
RECOMMENDED NAME
GeneOntology No.
anthocyanidin reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a (2R,3R)-flavan-3-ol + 2 NAD(P)+ = an anthocyanidin with a 3-hydroxy group + 2 NAD(P)H + H+
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,3-cis-flavanols biosynthesis
-
-
Biosynthesis of secondary metabolites
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Flavonoid biosynthesis
-
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proanthocyanidins biosynthesis from flavanols
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-
SYSTEMATIC NAME
IUBMB Comments
flavan-3-ol:NAD(P)+ oxidoreductase
The enzyme participates in the flavonoid biosynthesis pathway found in plants. It catalyses the double reduction of anthocyanidins, producing (2R,3R)-flavan-3-ol monomers required for the formation of proanthocyanidins. While the enzyme from the legume Medicago truncatula (MtANR) can use both NADPH and NADH as reductant, that from the crucifer Arabidopsis thaliana (AtANR) uses only NADPH. Also, while the substrate preference of MtANR is cyanidin>pelargonidin>delphinidin, the reverse preference is found with AtANR. cf. EC 1.3.1.112, anthocyanidin reductase [(2S)-flavan-3-ol-forming].
CAS REGISTRY NUMBER
COMMENTARY hide
93389-48-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene BANYULS orthologue, BAN
UniProt
Manually annotated by BRENDA team
gene BANYULS orthologue, four copies of BAN, two originating from each diploid progenitor
UniProt
Manually annotated by BRENDA team
gene BANYULS orthologue, four copies of BAN, two originating from each diploid progenitor
UniProt
Manually annotated by BRENDA team
gene BANYULS orthologue, BAN
D0QXJ3, D0QXJ3 and D0QXJ4
UniProt
Manually annotated by BRENDA team
gene BANYULS orthologue, BAN
UniProt
Manually annotated by BRENDA team
gene BANYULS orthologue, BAN
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
cultivar Hiratanenashi
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
brown-fiber cotton line T586
UniProt
Manually annotated by BRENDA team
cultivar Golden Delicious, Niedzwetz-kyana, Weirouge, Klarapfel, Red Delicious, Elstar, Holsteiner Cox, Pinova and Pilot; cv Golden Delicious
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-epicatechin + 2 NADP+
cyanidin + 2 NADPH + 2 H+
show the reaction diagram
-
-
-
-
?
2,3-cis-flavan-3-ol + NAD(P)+
anthocyanidin + NAD(P)H + H+
show the reaction diagram
the enzyme is involved in formation of condensed tannins. The enzyme competes with anthocyanidin synthase, for the pool of flavan-3,4-diol
-
-
?
anthocyanidin + NAD(P)H
2,3-cis-flavan-3-ol + NAD(P)+
show the reaction diagram
anthocyanidin + NAD(P)H + H+
2,3-cis-flavan-3-ol + NAD(P)+
show the reaction diagram
cyanidin + 2 NADPH + 2 H+
(-)-catechin + (-)-epicatechin + 2 NADP+
show the reaction diagram
-
-
-
?
cyanidin + 2 NADPH + 2 H+
epicatechin + 2 NADP+
show the reaction diagram
-
-
-
-
?
cyanidin + NAD(P)H + H+
(-)-epicatechin + NAD(P)+
show the reaction diagram
cyanidin + NADPH
(-)-epicatechin + NAD(P)+
show the reaction diagram
cyanidin + NADPH
epicatechin + NADP+
show the reaction diagram
-
-
-
-
?
cyanidin + NADPH + H+
(-)-epicatechin + NADP+
show the reaction diagram
cyanidin + NADPH + H+
epicatechin + NADP+
show the reaction diagram
-
-
-
?
delphinidin + 2 NADH + 2 H+
(-)-epigallocatechin + (-)-gallocactechin + 2 NAD+
show the reaction diagram
-
-
-
?
delphinidin + 2 NADPH + 2 H+
epigallocatechin + 2 NADP+
show the reaction diagram
-
-
-
-
?
delphinidin + 2 NADPH + H+
(-)-epigallocatechin + 2 NADP+
show the reaction diagram
delphinidin + NADPH
(-)-epigallocatechin + NAD(P)+
show the reaction diagram
-
changes in the concentration of products and coenzyme in the ANR assay are determined by thin layer chromatography (TLC), HPLC, mass spectrometry (MS) and UV spectrophotometry
-
-
?
delphinidin + NADPH
(-)-epigallocatechin + NADP+
show the reaction diagram
-
-
-
-
?
NADPH + H+ + cyanidin
NADP+ + (-)-epicatechin
show the reaction diagram
-
-
-
-
?
NADPH + H+ + delphinidin
NADP+ + (-)-epigallocatechin
show the reaction diagram
NADPH + H+ + pelargonidin
NADP+ + (-)-epiafzelechin
show the reaction diagram
-
-
-
-
?
NADPH + H+ + petunidin
NADP+ + ?
show the reaction diagram
-
-
-
-
?
pelargonidin + 2 NADPH + 2 H+
(-)-epiafzelechin + (-)-afzelechin + 2 NADP+
show the reaction diagram
-
-
-
?
pelargonidin + 2 NADPH + 2 H+
epiafzelechin + 2 NADP+
show the reaction diagram
-
-
-
-
?
pelargonidin + 2 NADPH + H+
(-)-epiafzelechin + 2 NADP+
show the reaction diagram
pelargonidin + NAD(P)H + H+
epiafzelechin + NAD(P)+
show the reaction diagram
-
-
-
-
?
pelargonidin + NADPH + H+
epiafzelechin + NADP+
show the reaction diagram
-
-
-
-
?
petunidin + 2 NADPH + 2 H+
? + 2 NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2,3-cis-flavan-3-ol + NAD(P)+
anthocyanidin + NAD(P)H + H+
show the reaction diagram
Q84XT1
the enzyme is involved in formation of condensed tannins. The enzyme competes with anthocyanidin synthase, for the pool of flavan-3,4-diol
-
-
?
anthocyanidin + NAD(P)H
2,3-cis-flavan-3-ol + NAD(P)+
show the reaction diagram
cyanidin + NADPH + H+
epicatechin + NADP+
show the reaction diagram
Q6DV46
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)H
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-catechin
-
0.5 mM, 50% inhibition
(+/-)-dihydroquercetin
-
0.025 mM
Na+
-
above 200 mM
quercetin
sodium chloride
500 mm, almost complete loss of activity
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0129 - 0.176
cyanidin
0.0142 - 0.131
delphinidin
0.817 - 0.94
NADH
0.097 - 0.45
NADPH
0.013 - 0.135
pelargonidin
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0012 - 1.66
cyanidin
0.0012 - 2.01
delphinidin
2
pelargonidin
Vitis bellula
H9TZS7
pH 4.0, 40°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9.48
cyanidin
Vitis bellula
H9TZS7
pH 4.0, 40°C
1072
16.4
delphinidin
Vitis bellula
H9TZS7
pH 4.0, 40°C
1824
14.9
pelargonidin
Vitis bellula
H9TZS7
pH 4.0, 40°C
2754
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
in 50 mM citrate/phosphate buffer
6
-
in 50 mM MES buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8.9
-
pH 7.0: about 40% of maximal activity, pH 8.9: about 90% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
preferrently expressed
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37000
-
calculated from cDNA
39000
-
SDS-PAGE, recombinant protein
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 56000, SDS-PAGE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
constitutive expression of the enzyme under control of the cauliflower mosaic virus 35S promoter in Nicotiana tabacum and Arabidopsis. Tobacco lines expressing the enzyme from Medicago trunculata lose the pink flower pigmentation characteristics of wild-type and empty vector control plants
expressed in Escherichia coli strain BL21
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expressed in Escherichia coli. To investigate the function of PtrANR1, the open reading frame in sense or antisense orientation is introduced into Populus tomentosa Carr. plants for ectopic expression under the control of the cauliflower mosaic virus 35S promoter, respectively
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expressed in Escherichia coli; expressed in Escherichia coli. Overexpressed in Nicotiana tabacum and Medicago truncatula for functional analysis
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expressed in Escherichia coli; expressed in Escherichia coli; expressed in Escherichia coli; expressed in Escherichia coli; expressed in Escherichia coli; expressed in Escherichia coli; expressed in Escherichia coli
expressed in Malus domestica via Agrobacterium tumefaciens-mediated transformation
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expression in Escherichia coli
expression in Escherichia coli as a fusion protein with maltose-binding protein
expression in Saccharomyces cerevisiae
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for expression in Escherichia coli cells
gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview
gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview; gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview
D0QXJ3 and D0QXJ4, D0QXJ3
gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview; gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview; gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview; gene BAN, DNA and amino acid sequence determination and analysis, sequence comparisons and genetic mapping, phylogenetic tree, overview
genetic transformation of Arabidopsis thaliana with the Arabidopsis TT2 MYB transcription factor results in ectopic expression of the BANYULS gene, encoding anthocyanidin reductase, AHA10 encoding a P-type proton-pump and TT12 encoding a transporter involved in proanthocyanidin biosynthesis. When coupled with constitutive expression of PAP1, a positive regulator of anthocyanin biosynthesis, TT2 expression in Arabidopsis leads to the accumulation of proanthocyanidins, but only in a subset of cells in which the BANYULS promoter is naturally expressed. Ectopic expression of the maize Lc MYC transcription factor weakly induces AHA10 but does not induce BANYULS, TT12 or accumulation of proanthocyanidins
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recombinantly expressed in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
abscisic acid decreases ANR activity and represses the expression a few days after application
-
expression of anthocyanidin reductase is down-regulated in response to drought, abscisic acid and gibberellic acid
expression of anthocyanidin reductase is up-regulated in response to wounding
gene expression and enzymatic activity are higher in the developping leaves than in the mature leaves and lower than in the tender bud and first leaves
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
N185I/G214A
-
mutant shows minor reductions in activity. Calculated Km and Vmax values are not given as the enzymes are intensely inhibited by cyanidin concentrations above 0.1 mM
V122A/G214A
-
mutant shows minor reductions in activity. Calculated Km and Vmax values are not given as the enzymes are intensely inhibited by cyanidin concentrations above 0.1 mM
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
molecular biology
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a method for the analysis of ANR activity using the detection of coenzyme is established