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Enzyme Nomenclature
Information on EC 1.1.1.234 - flavanone 4-reductase
for references in articles please use BRENDA:EC1.1.1.234
Word Map on EC 1.1.1.234
- 1.1.1.234
- flavonoid
- bicolor
- dihydroflavonols
-
3-deoxyanthocyanidins
- sorghum
-
purple
- flavone
-
cultivars
- luteolinidin
- moench
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.1.1.234
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RECOMMENDED NAME
GeneOntology No.
flavanone 4-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
-
-
-
-
(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
enzyme acts as flavone 4-reductase as well as dihydroflavonol 4-reductase
(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
enzyme acts as flavone 4-reductase as well as dihydroflavonol 4-reductase
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
-
-
redox reaction
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-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(2S)-flavan-4-ol:NADP+ 4-oxidoreductase
Involved in the biosynthesis of 3-deoxyanthocyanidins from flavanones such as naringenin or eriodictyol.
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CAS REGISTRY NUMBER
COMMENTARY
115232-53-6
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
the enzyme belongs to the plant DFR superfamily, phylogenetic analysis
malfunction
Sorghums with a tan injury response have non-functional FNR alleles (p). The FNR gene of cultivar M36001 has an insertion in the coding region. Sorghums with a tan injury response have lower levels of flavan-4-ols (precursors of apigeninidin and luteolinidin-apiforol and luteoforol, respectively) than do sorghums with a purple or red injury response and are unable to synthesize 3-deoxyanthocyanidins
metabolism
physiological function
additional information
homology modeling on the basis of the crystal structure of grape dihydroflavonol 4-reductase, PDB ID 3C1T
metabolism
the DFR gene is a key gene late in the flavonoid biosynthesis pathway, overview. The enzyme posesses flavanone 4-reductase activity and also is a key enzyme in the biosynthesis of anthocyanidins, proanthocyanidins, and other flavonoids
metabolism
the enzyme, encoded by gene Sb06g029550, is involved in the 3-deoxyanthocyanidin synthesis pathway
physiological function
the enzyme is of importance in plant development
physiological function
the enzyme is responsible for the synthesis of 3-deoxyanthocyanidins. The variation of purple-red-orange is explained by the balance of two 3-deoxyanthocyanidins, uteolinidin and apigeninidin. The balance is controlled by the expression level of flavonoid 3'-hydroxylase (F3'H), which encodes a protein that hydroxylates the 3' position of the B-ring of naringenin to produce a precursor of luteolinidin
physiological function
upon wounding or pathogen invasion, leaves of Sorghum bicolor plants with the P gene turn purple, whereas leaves with the recessive allele turn brown or tan. This purple phenotype is determined by the production of two 3-deoxyanthocyanidins, apigeninidin and luteolinidin, which are not produced by the tan-phenotype plants
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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
5,7,3',4',5'-pentahydroxyflavanone + NADPH
5,7,3',4',5'-pentahydroxyflavan-4-ol + NADP+
-
-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida
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involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida Heklua
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involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
eriodictyol + NADP+
luteoforol + NADPH + H+
recombinant Sb06g029550 protein
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-
?
naringenin + NADPH + H+
apiforol + NADP+
recombinant Sb06g029550 protein
apiforol is converted to apigeninidin with Nar + protein + HCl treatment
-
?
additional information
?
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the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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-
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additional information
?
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-
the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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additional information
?
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as dihydroxyflavonols, such as dihydrokaempferol, dihydroquercetin and dihydromyricetin are substrates for the Sinningia enzyme preparation, too, the enzyme might be identical with dihydroflavonol-4-reductase
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additional information
?
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enzyme FNR converts flavanones to flavan-4-ols
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additional information
?
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the reaction mixtures are acid-treated to convert the direct reaction products, flavan-3,4-diol, and flavan-4-ol, to their respective anthocyanidin or 3-deoxyanthocyanidins, and analyzed by LC-MS/MS
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-
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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
(2S)-eriodictyol + NADPH
luteoforol + NADP+
Q9XES5
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida Heklua
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Q9XES5
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
additional information
?
-
A5Z0G1
the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
-
-
-
additional information
?
-
-
the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no cofactors are FAD, FMN or tetrahydropterin, with or without NADPH
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no inhibition by KCN, EDTA, diethyl dithiocarbamate, phenanthroline or N-ethylmaleimide, 2 mM each
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
40
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
expression level of SmDFR is higher in flowers compared with both leaves and roots
additional information
-
expression level of SmDFR is higher in flowers compared with both leaves and roots
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 40000, recombinant His-tagged enzyme, SDS-PAGE, x * 37800, about, sequence calculation
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
freezing fresh flowers in liquid nitrogen and storing them at -80°C enhances extractable activity compared to fresh flowers
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21 Star(DE3)pLysS by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene P or Sb06g029550, genetic structure, quantitative RT-PCR enzyme expression analysis
gene P or Sb06g029550, quantitative RT-PCR enzyme expression analysis, genetic mapping, phylogenetic analysis and tree, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21 Star(DE3)pLysS
gene SmDFR, DNA and amino acid sequence determination and analysis, phylogenetic analysis, quantitative real-time PCR expression analysis, functional expression in Saccharomyces cerevisiae strain INV Sc1
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is highly induced by wounding and pathogen invasion, analysis of 3-deoxyanthocyanidin accumulation
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C252Y
cultivar Greenleaf Sb06g029550 has a point mutation that causes the amino acid change
additional information
additional information
expression of both flavone synthase II (FNSII) and flavonoid 3'-hydroxylase (F3'H) leads to the synthesis of apigenin and luteolin in cultivar #7, and expression of both flavanone 4-reductase and F3'H leads to the synthesis of 3-deoxyanthocyanidins in cultivar Nakei-MS3B
additional information
analysis of Sb06g029550 in four sorghum accessions with the tan phenotype, overview
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.234)
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