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Enzyme Nomenclature
Information on EC 1.1.1.234 - flavanone 4-reductase
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1.1.1.234 flavanone 4-reductaseIUBMB Comments
Involved in the biosynthesis of 3-deoxyanthocyanidins from flavanones such as naringenin or eriodictyol.
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Word Map
- 1.1.1.234
- flavonoid
- sorghum
- bicolor
-
3-deoxyanthocyanidins
- dihydroflavonols
- moench
- flavone
- luteolinidin
-
purple
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
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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
-
(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
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PATHWAY SOURCE
PATHWAYS
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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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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
-
-
?
(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+
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
-
-
?
naringenin + NADPH + H+
apiforol + NADP+
recombinant Sb06g029550 protein
apiforol is converted to apigeninidin with Nar + protein + HCl treatment
-
?
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
-
-
?
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
enzyme FNR converts flavanones to flavan-4-ols
-
-
?
additional information
?
-
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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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
(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
-
-
?
(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+
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
?
-
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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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no cofactors are FAD, FMN or tetrahydropterin, with or without NADPH
-
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INHIBITOR
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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
purple Nakei-MS3B (PP) and tan Greenleaf (pp) cultivars
UniProt
brenda
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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
brenda
additional information
-
expression level of SmDFR is higher in flowers compared with both leaves and roots
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). DFRA_ANTMA
446
0
49633
Swiss-Prot
Chloroplast (Reliability: 4)
DFRA_ARATH
382
0
42775
Swiss-Prot
other Location (Reliability: 5)
DFRA_CALCH
364
0
40726
Swiss-Prot
other Location (Reliability: 3)
DFRA_DIACA
360
0
40430
Swiss-Prot
other Location (Reliability: 2)
DFRA_GERHY
366
1
41102
Swiss-Prot
other Location (Reliability: 3)
DFRA_HORVU
354
0
38435
Swiss-Prot
other Location (Reliability: 4)
DFRA_MAIZE
357
0
38856
Swiss-Prot
other Location (Reliability: 4)
DFRA_MALDO
348
0
39030
Swiss-Prot
other Location (Reliability: 3)
DFRA_MEDSA
217
0
24389
Swiss-Prot
other Location (Reliability: 4)
DFRA_PETHY
380
2
42435
Swiss-Prot
Chloroplast (Reliability: 5)
DFRA_PYRCO
347
0
38934
Swiss-Prot
other Location (Reliability: 3)
DFRA_SOLLC
379
0
42429
Swiss-Prot
other Location (Reliability: 2)
DFRA_VITVI
337
0
37757
Swiss-Prot
Chloroplast (Reliability: 5)
A0A087CHN5_9BIFI
360
0
38542
TrEMBL
-
A0A5B7AFJ3_DAVIN
342
1
38347
TrEMBL
other Location (Reliability: 5)
A0A2I0A6C5_9ASPA
325
0
36452
TrEMBL
Mitochondrion (Reliability: 4)
A0A2P6PYS2_ROSCH
349
0
38942
TrEMBL
other Location (Reliability: 3)
A0A5B7AFX8_DAVIN
342
1
38243
TrEMBL
other Location (Reliability: 3)
A0A5B7C2C6_DAVIN
155
0
17711
TrEMBL
other Location (Reliability: 2)
A0A6N9QMZ9_9LEPT
363
0
40355
TrEMBL
-
A0A2P6PQ57_ROSCH
403
0
43941
TrEMBL
other Location (Reliability: 3)
A0A5B7A981_DAVIN
196
0
21623
TrEMBL
other Location (Reliability: 2)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 40000, recombinant His-tagged enzyme, SDS-PAGE, x * 37800, about, sequence calculation
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C252Y
cultivar Greenleaf Sb06g029550 has a point mutation that causes the amino acid change
additional information
additional information
analysis of Sb06g029550 in four sorghum accessions with the tan phenotype, overview
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
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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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Stich, K.; Forkmann, G.
Biosynthesis of 3-deoxyanthocyanins with flower extracts from Sinningia cardinalis
Biochemistry
27
785-789
1988
Sinningia cardinalis
-
brenda
Stich, K.; Forkmann, G.
Studies on columnidin biosynthesis with flower extracts from Columnea hybrida
Z. Naturforsch. C
43
311-314
1988
Columnea hybrida, Columnea hybrida Heklua
-
brenda
Fischer, T.C.; Halbwirth, H.; Meisel, B.; Stich, K.; Forkmann, G.
Molecular cloning, substrate specificity of the functionally expressed dihydroflavonol 4-reductases from Malus domestica and Pyrus communis cultivars and the consequences for flavonoid metabolism
Arch. Biochem. Biophys.
412
223-230
2003
Pyrus communis, Malus domestica (Q9XES5), Malus domestica
brenda
Halbwirth, H.; Martnes, S.; Wienand, U.; Forkmann, G.; Stich, K.
Biochemical formation of anthocyanins in silk tissue of Zea mays
Plant Sci.
164
489-495
2003
Zea mays
-
brenda
Li, H.; Qiu, J.; Chen, F.; Lv, X.; Fu, C.; Zhao, D.; Hua, X.; Zhao, Q.
Molecular characterization and expression analysis of dihydroflavonol 4-reductase (DFR) gene in Saussurea medusa
Mol. Biol. Rep.
39
2991-2999
2012
Saussurea medusa (A5Z0G1), Saussurea medusa
brenda
Mizuno, H.; Yazawa, T.; Kasuga, S.; Sawada, Y.; Kanamori, H.; Ogo, Y.; Hirai, M.Y.; Matsumoto, T.; Kawahigashi, H.
Expression of flavone synthase II and flavonoid 3'-hydroxylase is associated with color variation in tan-colored injured leaves of Sorghum
Front. Plant Sci.
7
1718
2016
Sorghum bicolor (C5YGL7)
brenda
Kawahigashi, H.; Kasuga, S.; Sawada, Y.; Yonemaru, J.; Ando, T.; Kanamori, H.; Wu, J.; Mizuno, H.; Momma, M.; Fujimoto, Z.; Hirai, M.Y.; Matsumoto, T.
The sorghum gene for leaf color changes upon wounding (P) encodes a flavanone 4-reductase in the 3-deoxyanthocyanidin biosynthesis pathway
G3 (Bethesda)
6
1439-1447
2016
Sorghum bicolor (C5YGL7)
brenda
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