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Enzyme Nomenclature
Information on EC 2.4.1.81 - flavone 7-O-beta-glucosyltransferase
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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EC NUMBER 
COMMENTARY 
2.4.1.81
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RECOMMENDED NAME
GeneOntology No.
flavone 7-O-beta-glucosyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + 5,7,3',4'-tetrahydroxyflavone = UDP + 7-O-beta-D-glucosyl-5,7,3',4'-tetrahydroxyflavone
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:5,7,3',4'-tetrahydroxyflavone 7-O-beta-D-glucosyltransferase
A number of flavones, flavanones and flavonols can function as acceptors. Different from EC 2.4.1.91 (flavonol 3-O-glucosyltransferase).
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CAS REGISTRY NUMBER
COMMENTARY
37332-50-6
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
UDP-alpha-D-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
78.9% of the activity with eriodictyol
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-
?
UDP-alpha-D-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
64.1% of the activity with eriodictyol
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-
?
UDP-glucose + 3',4',5,7-tetrahydroxyflavone
UDP + 7-O-beta-D-glucosyl-3',4',5,7-tetrahydroxyflavone
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involved in biosynthesis of flavone glucosides
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-
?
UDP-glucose + eriodictyol
UDP + 7-O-beta-D-glucosyl-eriodictyol
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-
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?
UDP-glucose + luteolin
UDP + 7-O-beta-D-glucosyl-luteolin
92.1% of the activity with eriodictyol
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-
?
UDP-glucose + naringenin
UDP + 7-O-beta-D-glucosyl-naringenin
71.6% of the activity with eriodictyol
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-
?
UDPglucose + 3,7,4'-trihydroxyflavone
UDP + 7-O-beta-D-glucosyl-3,7,4'trihydroxyflavone
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9% of the activity with apigenin
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?
UDPglucose + 5,7-dihydroxyflavanone
UDP + 7-O-beta-D-glucosyl-5,7-dihydroxyflavanone
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15% of the activity with apigenin
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?
UDPglucose + 7,4'-dihydroxyflavone
UDP + 7-O-beta-D-glucosyl-7,4'-dihydroxyflavone
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20% of the activity with apigenin
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?
UDPglucose + acacetin
UDP + 7-O-beta-D-glucosylacacetin
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24% of the activity with apigenin
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?
UDPglucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
29.6% of the activity with eriodictyol
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-
?
UDPglucose + chrysoeriol
UDP + 7-O-beta-D-glucosylchrysoeriol
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63% of the activity with apigenin
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?
UDPglucose + datiscetin
UDP + 7-O-beta-D-glucosyldatiscetin
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9% of the activity with apigenin
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?
UDPglucose + fisetin
UDP + 7-O-beta-D-glucosylfisetin
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14% of the activity with apigenin
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?
UDPglucose + galangin
UDP + 7-O-beta-D-glucosylgalangin
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9% of the activity with apigenin
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?
UDPglucose + kaempferid
UDP + 7-O-beta-D-glucosylkaempferid
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16% of the activity with apigenin
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?
UDPglucose + kaempferol
UDP + 7-O-beta-D-glucosylkaempferol
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11% of the activity with apigenin
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?
UDPglucose + luteolin
UDP + 7-O-beta-D-glucosylluteolin
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210% of the activity with apigenin
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?
UDPglucose + naringenin
UDP + 7-O-beta-D-glucosylnaringenin
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45% of the activity with apigenin
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?
UDPglucose + quercetin
UDP + 7-O-beta-D-glucosylquercetin
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16% of the activity with apigenin
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?
UDP-glucose + apigenin
UDP + 4',7-O-beta-D-diglucosyl-apigenin
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-
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?
UDP-glucose + apigenin
UDP + 4',7-O-beta-D-diglucosyl-apigenin
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-
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?
UDP-glucose + apigenin
UDP + 4'-O-beta-D-glucosyl-apigenin
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?
UDP-glucose + apigenin
UDP + 4'-O-beta-D-glucosyl-apigenin
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?
UDP-glucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
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?
UDP-glucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
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?
additional information
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glucosylation at the phenolic groups of C-4' and C-7 positions ensuing apigenin 4'-O-glucoside, apigenin 7-O-glucoside and apigenin 4',7-O-diglucoside as the products leaving the C-5 position unglucosylated. Position of glucosylation and the chemical structures of glucosides are elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The UDP-glucose concentration and the pH value influence the synthesis of particular glucosides, i.e. the site of glucosylation. Formation of 7-O-beta-D-glucosyl-apigenin is higher in more alkaline conditions, whereas 4',7-O-beta-D-diglucosyl-apigenin prefers a pH range of pH 7.5-8.8. The formation of 4'-O-beta-D-glucosyl-apigenin is highest at a 3 mM concentration of UDP-glucose, while formation of 7-O-beta-D-glucosyl-apigenin is highest with a 6 mM concentration of UDP-glucose, but it decreases slightly at 9 mM concentration. Similarly, 4',7-O-beta-D-diglucosyl-apigenin formation is highest with 9 mM UDP-glucose and lowest with 3 mM UDP-glucose. Not much difference is observed in the amount of 4',7-O-beta-D-diglucosyl-apigenin between the two reactions with 6 mM and 9 mM UDP-glucose
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additional information
?
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glucosylation at the phenolic groups of C-4' and C-7 positions ensuing apigenin 4'-O-glucoside, apigenin 7-O-glucoside and apigenin 4',7-O-diglucoside as the products leaving the C-5 position unglucosylated. Position of glucosylation and the chemical structures of glucosides are elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The UDP-glucose concentration and the pH value influence the synthesis of particular glucosides, i.e. the site of glucosylation. Formation of 7-O-beta-D-glucosyl-apigenin is higher in more alkaline conditions, whereas 4',7-O-beta-D-diglucosyl-apigenin prefers a pH range of pH 7.5-8.8. The formation of 4'-O-beta-D-glucosyl-apigenin is highest at a 3 mM concentration of UDP-glucose, while formation of 7-O-beta-D-glucosyl-apigenin is highest with a 6 mM concentration of UDP-glucose, but it decreases slightly at 9 mM concentration. Similarly, 4',7-O-beta-D-diglucosyl-apigenin formation is highest with 9 mM UDP-glucose and lowest with 3 mM UDP-glucose. Not much difference is observed in the amount of 4',7-O-beta-D-diglucosyl-apigenin between the two reactions with 6 mM and 9 mM UDP-glucose
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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
UDP-glucose + 3',4',5,7-tetrahydroxyflavone
UDP + 7-O-beta-D-glucosyl-3',4',5,7-tetrahydroxyflavone
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involved in biosynthesis of flavone glucosides
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?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Tris-HCl
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in 1 M Tris-HCl buffer the reaction rate is 70% of that observed in 0.1 M buffer
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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
6 - 9
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pH 6.0: about 35% of maximal activity, pH 9.0: about 50% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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extractable activity is drastically increased by illuminating the cells with white light and the maximum activity is reached 24 h after the onset of illumination
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
3�C, t1/2: 1 month in 0.05 M Tris-HCl buffer, pH 7.5, 7 mM 2-mercaptoethanol
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and dialysis
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli as a glutathione S-transferase fusion protein
gene yjiC, cloned from genomic DNA, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
biotransformation of eriodictyol using Escherichi coli expressing AtGT-2
synthesis
the enzyme is used for the synthesis of apigenin glucosides, that have higher water solubility, increased chemical stability, and enhanced biological activities compared to the aglycon apigenin
synthesis
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the enzyme is used for the synthesis of apigenin glucosides, that have higher water solubility, increased chemical stability, and enhanced biological activities compared to the aglycon apigenin
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LINKS TO OTHER DATABASES (specific for EC-Number 2.4.1.81)
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