Information on EC 2.4.1.237 - flavonol 7-O-beta-glucosyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.237
-
RECOMMENDED NAME
GeneOntology No.
flavonol 7-O-beta-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + a flavonol = UDP + a flavonol 7-O-beta-D-glucoside
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
transfer of glycosyl group
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
eupatolitin 3-O-glucoside biosynthesis
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gossypetin metabolism
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kaempferol glycoside biosynthesis (Arabidopsis)
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quercetin glucoside biosynthesis (Allium)
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quercetin glycoside biosynthesis (Arabidopsis)
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:flavonol 7-O-beta-D-glucosyltransferase
Acts on the flavonols gossypetin (8-hydroxyquercetin) and to a lesser extent on quercetin, kaempferol and myricetin.
CAS REGISTRY NUMBER
COMMENTARY hide
83682-90-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
f. Ciliato-dentatus
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Manually annotated by BRENDA team
cv. Prado and Stern des Orients
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
var. Mairei
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Manually annotated by BRENDA team
line A 681-230
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-alpha-D-glucose + kaempferol
UDP + kaempferol 3-O-beta-D-glucoside
show the reaction diagram
-
17% of the activity with quercetin, UGT71F1
-
-
?
UDP-alpha-D-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
UDP-alpha-D-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-alpha-D-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside + quercetin 3-O-beta-D-glucoside
show the reaction diagram
-
UGT71F1
-
-
?
UDP-alpha-D-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside + quercetin 4'-O-beta-D-glucoside
show the reaction diagram
-
4'-OH glycosylation is preferred over 7-OH glycosylation, UGT73A4
-
-
?
UDP-glucose + 1-naphthol
UDP + naphthol 1-O-beta-D-glucoside
show the reaction diagram
-
44% of the activity with kaempferol
-
-
?
UDP-glucose + 2-coumaric acid
UDP + ?
show the reaction diagram
-
41% of the activity with kaempferol
-
-
?
UDP-glucose + 2-naphthol
UDP + naphthol 2-O-beta-D-glucoside
show the reaction diagram
-
14% of the activity with kaempferol
-
-
?
UDP-glucose + 3,5,7-trihydroxyflavanone
UDP + 3,5,7-trihydroxyflavanone 7-O-beta-D-glucoside
show the reaction diagram
-
pinobanksin, 55% of the activity with kaempferol as substrate
-
-
?
UDP-glucose + 3-hydroxycoumarin
UDP + coumarin 3-O-beta-D-glucoside
show the reaction diagram
-
310% of the activity with kaempferol
-
-
?
UDP-glucose + 3-hydroxyflavone
UDP + 3-hydroxyflavone 7-O-beta-D-glucoside
show the reaction diagram
-
12% of the activity with kaempferol
-
-
?
UDP-glucose + 4-coumaric acid
UDP + ?
show the reaction diagram
-
43% of the activity with kaempferol
-
-
?
UDP-glucose + 6-hydroxyflavone
UDP + 6-hydroxyflavone 7-O-beta-D-glucoside
show the reaction diagram
-
24% of the activity with kaempferol
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-
?
UDP-glucose + 7,4'-dihydroxyflavonol
UDP + 7,4'-dihydroxyflavonol 7-O-beta-D-glucoside
show the reaction diagram
-
53% of the activity with kaempferol as substrate
-
-
?
UDP-glucose + 7-hydroxyflavone
UDP + 7-hydroxyflavone 7-O-beta-D-glucoside
show the reaction diagram
-
53% of the activity with kaempferol
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-
?
UDP-glucose + a flavonol
UDP + a flavonol 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + apigenin
UDP + apigenin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + betanidin
UDP + betanidin 5-O-beta-D-glucoside + betanidin 6-O-beta-D-glucoside
show the reaction diagram
-
28% of the activity with quercetin, UGT71F1
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-
?
UDP-glucose + caffeic acid
UDP + caffeic acid 4-O-beta-D-glucoside
show the reaction diagram
-
14% of the activity with kaempferol as substrate
-
-
?
UDP-glucose + caffeic acid
UDP + caffeoyl 3-O-beta-D-glucoside
show the reaction diagram
-
90% of the activity with quercetin, UGT73A4
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-
?
UDP-glucose + chrysin
UDP + chrysin 7-O-beta-D-glucoside
show the reaction diagram
-
70% of the activity with quercetinUGT73A4
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-
?
UDP-glucose + eriodictyol
UDP + eriodictyol 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + esculetin
UDP + esculetin 6-O-beta-D-glucoside
show the reaction diagram
-
77% of the activity with quercetin, UGT73A4
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-
?
UDP-glucose + esculetin
UDP + esculetin 7-O-beta-D-glucoside
show the reaction diagram
-
24% of the activity with kaempferol
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-
?
UDP-glucose + euonymin
UDP + euonymin 7-O-beta-D-glucoside
show the reaction diagram
-
16% of the activity with kaempferol as substrate
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-
?
UDP-glucose + gossypetin
UDP + gossypetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + hydroquinone
UDP + hydroquinone O-beta-D-glucoside
show the reaction diagram
-
10% of the activity with kaempferol as substrate
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?
UDP-glucose + isoquercitrin
UDP + isoquercitrin 7-O-beta-D-glucoside
show the reaction diagram
-
13% of the activity with kaempferol as substrate
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-
?
UDP-glucose + isorhamnetin
UDP + isorhamnetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + kaempferide
UDP + kaempferide 7-O-beta-D-glucoside
show the reaction diagram
-
104% of the activity with kaempferol as substrate
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-
?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + kaempferol 3,4'-di-O-glucoside
UDP + kaempferol 3,7,4'-tri-O-glucoside
show the reaction diagram
-
12% of the activity with kaempferol as substrate
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-
?
UDP-glucose + kaempferol 3,4'-dimethylether
UDP + kaempferol 3,4'-dimethylether 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + kaempferol 3-O-glucoside
UDP + kaempferol 3,7-O-beta-D-diglucoside
show the reaction diagram
-
astragalin, 17% of the activity with kaempferol as substrate
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-
?
UDP-glucose + kaempferol 3-O-glucoside
UDP + kaempferol 3,7-O-diglucoside
show the reaction diagram
-
astragalin, 20% of the activity with kaempferol as substrate
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?
UDP-glucose + kaempferol 3-O-glucoside
UDP + kaempferol 3,7beta-O-diglucoside
show the reaction diagram
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45% of the activity with kaempferol
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?
UDP-glucose + kaempferol 3-O-rhamnosylglucoside
UDP + kaempferol 3-O-rhamnosylglucoside 7-O-beta-D-glucoside
show the reaction diagram
-
11% of the activity with kaempferol as substrate
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?
UDP-glucose + kaempferol 5,7,4'-trimethylether
UDP + kaempferol 5,7,4'-trimethylether 3-O-beta-D-glucoside
show the reaction diagram
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9% of the activity with kaempferol as substrate
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?
UDP-glucose + kaempferol-4'-methylether
UDP + kaempferol-4'-methylether 7-O-beta-D-glucoside
show the reaction diagram
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42% of the activity with quercetin, UGT73A4
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?
UDP-glucose + luteolin
UDP + luteolin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + myricetin
UDP + myricetin 4'-O-beta-D-glucoside
show the reaction diagram
-
80% of the activity with quercetin, 4'-OH glycosylation is preferred over 7-OH glycosylation, UGT73A4
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-
?
UDP-glucose + myricetin
UDP + myricetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + naringenin
UDP + naringenin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + p-coumaric acid
UDP + (2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoic acid
show the reaction diagram
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9% of the activity with kaempferol as substrate
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?
UDP-glucose + pinocembrin
UDP + pinocembrin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + quercetagetin
UDP + quercetagetin 3-O-beta-D-glucoside + quercetagetin 7-O-beta-D-glucoside
show the reaction diagram
-
84% of the activity with quercetin, UGT71F1
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?
UDP-glucose + quercetagetin
UDP + quercetagetin 4'-O-beta-D-glucoside
show the reaction diagram
-
28% of the activity with quercetin, 4'-OH glycosylation is preferred over 7-OH glycosylation, UGT73A4
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-
?
UDP-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + quercetin 3-O-glucoside
UDP + quercetin 3,7-O-beta-D-diglucoside
show the reaction diagram
-
isoquercetin, 32% of the activity with kaempferol as substrate
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-
?
UDP-glucose + quercetin 5-methylether
UDP + quercetin 5-methylether 7-O-beta-D-glucoside
show the reaction diagram
-
13% of the activity with kaempferol as substrate
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-
?
UDP-glucose + rutin
UDP + rutin 7-O-beta-D-glucoside
show the reaction diagram
-
21% of the activity with kaempferol as substrate
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-
?
UDP-glucose + scopoletin
UDP + scopoletin 7-O-beta-D-glucoside
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
UDP-alpha-D-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
show the reaction diagram
-
gossypetin and quercetin are presumably the natural substrates
-
-
?
UDP-glucose + a flavonol
UDP + a flavonol 7-O-beta-D-glucoside
show the reaction diagram
-
plays a role in the glycosylation steps of flavonols
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-
?
UDP-glucose + gossypetin
UDP + gossypetin 7-O-beta-D-glucoside
show the reaction diagram
-
gossypetin and quercetin are presumably the natural substrates
gossypetin 7-O-glucoside is particularly responsible for the yellow coloration of the petals
-
?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
slight stimulation
KCN
-
slight stimulation
Mg2+
-
slight stimulation
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid
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0.01 mM, UGT71F1; 0.01 mM, UGT73A4
diethyldicarbonate
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5 mM, 98% inhibition with quercetin or gossypetin as substrate
dithioerythritol
Fe2+
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1 mM, 98% inhibition with quercetin as substrate
Hg2+
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1 mM, 99% inhibition with quercetin as substrate
iodoacetamide
iodoacetate
N-ethylmaleimide
p-chloromercuribenzene sulfonic acid
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UGT71F1, 0.01mM, 22% inhibition; UGT73A4 activity is completely inhibited at 0.01mM
p-chloromercuribenzoate
p-hydroxymercuribenzoate
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strong, 0.1 mM, 99.3% inhibition with quercetin as substrate, 14 mM 2-mercaptoethanol protects and addition after 15 min also reduces the inhibitory effect
Phenylmercuriacetate
additional information
-
not inhibited by EDTA
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
bovine serum albumin
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addition to the assay system causes 2.5fold higher reaction rate
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EDTA
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1 mM: slight activation, 10 mM: 36% inhibition
additional information
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enzyme expression is inducible by plant hormones, such as salicylic acid, auxin, 2,4-dichorophenoxyacetic acid, and jasmonate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0236
3-hydroxycoumarin
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pH 8.0, 30°C, recombinant enzyme
0.0192 - 0.078
apigenin
0.029
betanidin
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UGT71F1
0.071
eriodictyol
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pH 7.5, 25°C
0.032
gossypetin
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pH 6.9, 25°C
0.0065 - 0.029
kaempferol
0.084
luteolin
-
pH 8.1, 25°C
0.067
myricetin
-
pH 8.1, 25°C
0.073
naringenin
-
pH 6.9, 25°C
0.0024 - 0.049
quercetin
0.002 - 0.0432
UDP-glucose
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00015
-
in vivo, pH and temperature not specified in the publication
1.63
-
pH 7.5
1.76
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pH 7.5, 30°C, kaempferol as substrate
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
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UGT73A4
6.9
-
gossypetin or naringenin as substrate
7 - 9
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UGT71F1
7.7
-
apigenin as substrate
7.8
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kaempferol as substrate
8.1
-
myricetin or luteolin as substrate
8.3
-
quercetin as substrate
additional information
-
the pH-optimum is highly dependent on the substrate used
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
UGT71F1
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0
-
7-O-glucosylation also proceeds at low temperatures, e.g. 0°C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.6
-
calculated from sequence, MALDI-TOF-MS analysis with molecular masses of tags subtracted, UGT71F1
5.8
-
calculated from sequence, MALDI-TOF-MS analysis with molecular masses of tags subtracted, UGT73A4
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
43000
-
gel filtration
48000
-
gel filtration
54070
-
calculated from sequence, UGT73A4
54390
-
calculated from sequence, UGT71F1
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
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10 min, no influence on the reaction up to 40°C, higher temperatures lead to loss of activity
60
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10 min, incubation without UDP-glucose, complete loss of activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, partially purified enzyme, 20 mM Tris-HCl, pH 7.5, 14 mM 2-mercaptoethanol, 10% glycerol, 2 days: 15% loss of activity, 8 days: 60% loss of activity
-
-20°C, partially purified enzyme, 20 mM Tris-HCl, pH 7.5, 14 mM 2-mercaptoethanol, 10% glycerol, 2 days: 18% loss of activity, 8 days: 64% loss of activity
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UGT71F1 can not be frozen nor stored at 4°C as 50% activity is lost within 24 h
-
UGT73A4 can be stored at 4°C or frozen at -20°C or -80°C for several months without requiring addition of stabilizing agents such as bovine serum albumin or glycerol
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
135.5fold, partial
-
139.9fold, partial
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recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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recombinant UGT71F1; recombinant UGT73A4
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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expression of iozymes as GST-tagged proteins
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functionally expressed in Escherichia coli as His- and GST-tagged protein, UGT71F1; functionally expressed in Escherichia coli as His- and GST-tagged protein, UGT73A4
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