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EC Tree
IUBMB Comments Isolated from Malus X domestica (apple). Phlorizin inhibits sodium-linked glucose transporters. It gives the characteristic flavour of apples and cider.
The expected taxonomic range for this enzyme is: Malus domestica
Synonyms
ugt88f1, ugt88f8, mdpgt1, p2'gt, udp-glucose:phloretin 2'-o-glycosyltransferase, phloretin-specific glycosyltransferase, phloretin-2'-o-glycosyltransferase,
more
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phloretin-2'-O-glycosyltransferase
-
phloretin-specific glycosyltransferase
-
UDP-glucose:phloretin 2'-O-glycosyltransferase
-
-
UDP-glucose:phloretin 4'-O-glycosyltransferase
-
-
P2'GT
-
-
-
-
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UDP-alpha-D-glucose + phloretin = UDP + phlorizin
-
-
-
-
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UDP-alpha-D-glucose:phloretin 2'-O-D-glucosyltransferase
Isolated from Malus X domestica (apple). Phlorizin inhibits sodium-linked glucose transporters. It gives the characteristic flavour of apples and cider.
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ADP-alpha-D-glucose + phloretin
ADP + phlorizin
-
-
-
?
ADP-alpha-D-glucose + quercetin
ADP + isoquercitrin
-
-
-
?
UDP-alpha-D-galactose + phloretin
?
-
-
-
-
?
UDP-alpha-D-galactose + quercetin
UDP + hyperoside
-
-
-
?
UDP-alpha-D-glucose + butein
UDP + butein-4'-O-glucoside
-
23% activity compared to phloretin
-
-
r
UDP-alpha-D-glucose + isoliquiritigenin
UDP + isoliquiritin
-
-
-
?
UDP-alpha-D-glucose + kaempferol
UDP + astragalin
-
-
-
?
UDP-alpha-D-glucose + luteolin
UDP + cynaroside
-
-
-
?
UDP-alpha-D-glucose + naringenin
UDP + naringenin-7-O-glucoside
-
22% activity compared to phloretin
-
-
r
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
UDP-alpha-D-glucose + phloretin
UDP + trilobatin
-
100% activity
-
-
r
UDP-alpha-D-glucose + phlorizin
UDP + ?
-
13% activity compared to phloretin
-
-
r
UDP-alpha-D-glucose + quercetin
UDP + quercetin-3-O-glucoside
-
-
-
?
UDP-alpha-D-glucose + quercetin
UDP + quercetin-7-O-glucoside
-
20% activity compared to phloretin
-
-
r
UDP-alpha-D-glucose + trilobatin
UDP + ?
-
12% activity compared to phloretin
-
-
r
UDP-alpha-D-xylose + phloretin
?
-
-
-
-
?
additional information
?
-
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
specific substrate
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
UGT88F8 shows strict specificity of UGT88F8 for phloretin
-
-
?
additional information
?
-
-
no activity with caffeic acid, catechin, chlorogenic acid, 2-coumaric acid, 3-coumaric acid, 4-coumaric acid, cyanidin, 3-3,4 dihydroxyphenyl propionic acid, epicatechin, 3-hydroxybenzoic acid, naringenin, protocatechuic acid, quercetin and rutin
-
-
?
additional information
?
-
-
no activity with UDP-galactose, epicatechin, cyaniding, 4-coumaric acid, and caffeic acid
-
-
?
additional information
?
-
no activity with several flavonoid classes including chalcones which are structurally related to dihydrochalcones, i.e. eriodictyol chalcone, naringenin, eriodictyol, apigenin, luteolin, kaempferol, quercetin, myricetin, catechin, epicatechin, and cyanidin
-
-
-
additional information
?
-
no activity with several flavonoid classes including chalcones which are structurally related to dihydrochalcones, i.e. eriodictyol chalcone, naringenin, eriodictyol, apigenin, luteolin, kaempferol, quercetin, myricetin, catechin, epicatechin, and cyanidin
-
-
-
additional information
?
-
-
no activity with several flavonoid classes including chalcones which are structurally related to dihydrochalcones, i.e. eriodictyol chalcone, naringenin, eriodictyol, apigenin, luteolin, kaempferol, quercetin, myricetin, catechin, epicatechin, and cyanidin
-
-
-
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UDP-alpha-D-glucose + phloretin
UDP + phlorizin
UDP-alpha-D-glucose + phloretin
UDP + trilobatin
-
100% activity
-
-
r
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
-
-
?
UDP-alpha-D-glucose + phloretin
UDP + phlorizin
-
specific substrate
-
-
?
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Fe2+
119.43% activity at 5 mM
Mg2+
130.35% activity at 2 mM
additional information
-
Mg2+, Mn2+, Ca+ and K+ do not affect enzyme activity
additional information
-
the enzyme activity is not affected by the addition of divalent cations (Mg2+ or Mn2+, 0-25 mM) or monovalent cations (Na+, 0-100 mM or K+, 0-10 mM)
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Al3+
67.81% residual activity at 5 mM
Ca2+
54.21% residual activity at 5 mM
Co2+
complete inhibition at 5 mM
Cu2+
complete inhibition at 5 mM
Fe3+
60.78% residual activity at 5 mM
Mn2+
47.41% residual activity at 5 mM
N-ethylmaleimide
20.53% residual activity at 1 mM
p-hydroxymercuribenzoate
18.45% residual activity at 1 mM
UDP
complete inhibition at 5 mM
additional information
negligible inhibition by uridine, K+, Ni2+, and Ba2+
-
additional information
-
negligible inhibition by uridine, K+, Ni2+, and Ba2+
-
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additional information
not influenced by 20% (v/v) methanol, 20% (v/v) dimethyl sulfoxide, 5% (v/v) glycerol, 0.5 mM 4-(2-aminoethyl) benzenesulfonyl fluoride, 5 mM beta-mercaptoethanol, 5 mM dithiohtreitol, 0.5 mM NaCl, and 5 mM EDTA
-
additional information
-
not influenced by 20% (v/v) methanol, 20% (v/v) dimethyl sulfoxide, 5% (v/v) glycerol, 0.5 mM 4-(2-aminoethyl) benzenesulfonyl fluoride, 5 mM beta-mercaptoethanol, 5 mM dithiohtreitol, 0.5 mM NaCl, and 5 mM EDTA
-
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0.01457 - 0.05867
ADP-alpha-D-glucose
0.0024
isoliquiritigenin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.00209
kaempferol
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.00289
luteolin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.00106 - 0.00181
quercetin
0.02619
UDP-alpha-D-galactose
with quercetin as cosubstrate, at pH 7.5 and 30°C
0.00753 - 1.19203
UDP-alpha-D-glucose
0.01457
ADP-alpha-D-glucose
with quercetin as cosubstrate, at pH 7.5 and 30°C
0.05867
ADP-alpha-D-glucose
with phloretin as cosubstrate, at pH 7.5 and 30°C
0.0005
phloretin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.00409
phloretin
with ADP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.00772
phloretin
pH 7.5, 30°C, recombinant enzyme
0.02611
phloretin
-
at pH 7.5 and 30°C
0.62
phloretin
-
at pH 7.5 and 30°C
0.00106
quercetin
with ADP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.00181
quercetin
with UDP-alpha-D-galactose as cosubstrate, at pH 7.5 and 30°C
0.00753
UDP-alpha-D-glucose
with phloretin as cosubstrate, at pH 7.5 and 30°C
0.01084
UDP-alpha-D-glucose
pH 7.5, 30°C, recombinant enzyme
0.013
UDP-alpha-D-glucose
-
at pH 7.5 and 30°C
0.03043
UDP-alpha-D-glucose
with kaempferol as cosubstrate, at pH 7.5 and 30°C
0.03619
UDP-alpha-D-glucose
with isoliquiritigenin as cosubstrate, at pH 7.5 and 30°C
0.04259
UDP-alpha-D-glucose
with luteolin as cosubstrate, at pH 7.5 and 30°C
1.19203
UDP-alpha-D-glucose
-
at pH 7.5 and 30°C
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14.57 - 58.67
ADP-alpha-D-glucose
4.35
isoliquiritigenin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
5.65
kaempferol
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
3.24
luteolin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
26.19
UDP-alpha-D-galactose
with quercetin as cosubstrate, at pH 7.5 and 30°C
0.0943 - 42.59
UDP-alpha-D-glucose
14.57
ADP-alpha-D-glucose
with quercetin as cosubstrate, at pH 7.5 and 30°C
58.67
ADP-alpha-D-glucose
with phloretin as cosubstrate, at pH 7.5 and 30°C
0.0972
phloretin
-
at pH 7.5 and 30°C
0.0994
phloretin
-
at pH 7.5 and 30°C
2.95
phloretin
with ADP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
9.87
phloretin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
41.83
phloretin
pH 7.5, 30°C, recombinant enzyme
6.18
quercetin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
7.41
quercetin
with ADP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.0943
UDP-alpha-D-glucose
-
at pH 7.5 and 30°C
8.28
UDP-alpha-D-glucose
pH 7.5, 30°C, recombinant enzyme
21.33
UDP-alpha-D-glucose
with phloretin as cosubstrate, at pH 7.5 and 30°C
30.43
UDP-alpha-D-glucose
with kaempferol as cosubstrate, at pH 7.5 and 30°C
36.19
UDP-alpha-D-glucose
with isoliquiritigenin as cosubstrate, at pH 7.5 and 30°C
42.59
UDP-alpha-D-glucose
with luteolin as cosubstrate, at pH 7.5 and 30°C
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80 - 1040
ADP-alpha-D-glucose
1810
isoliquiritigenin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
2700
kaempferol
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
1120
luteolin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
500
UDP-alpha-D-galactose
with quercetin as cosubstrate, at pH 7.5 and 30°C
0.079 - 2830
UDP-alpha-D-glucose
80
ADP-alpha-D-glucose
with phloretin as cosubstrate, at pH 7.5 and 30°C
1040
ADP-alpha-D-glucose
with quercetin as cosubstrate, at pH 7.5 and 30°C
0.381
phloretin
-
at pH 7.5 and 30°C
720
phloretin
with ADP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
5418.4
phloretin
pH 7.5, 30°C, recombinant enzyme
19730
phloretin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
5240
quercetin
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
6990
quercetin
with ADP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.079
UDP-alpha-D-glucose
-
at pH 7.5 and 30°C
140
UDP-alpha-D-glucose
with luteolin as cosubstrate, at pH 7.5 and 30°C
240
UDP-alpha-D-glucose
with isoliquiritigenin as cosubstrate, at pH 7.5 and 30°C
360
UDP-alpha-D-glucose
with kaempferol as cosubstrate, at pH 7.5 and 30°C
763.8
UDP-alpha-D-glucose
pH 7.5, 30°C, recombinant enzyme
2830
UDP-alpha-D-glucose
with phloretin as cosubstrate, at pH 7.5 and 30°C
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2.5
3-hydroxyphloridzin
Malus domestica
at pH 7.5 and 30°C
8
Al3+
Malus domestica
at pH 7.5 and 30°C
5.5
Ca2+
Malus domestica
at pH 7.5 and 30°C
0.05
Co2+
Malus domestica
at pH 7.5 and 30°C
0.01
Cu2+
Malus domestica
at pH 7.5 and 30°C
6.5
Fe3+
Malus domestica
at pH 7.5 and 30°C
4.5
Mn2+
Malus domestica
at pH 7.5 and 30°C
0.28
N-ethylmaleimide
Malus domestica
at pH 7.5 and 30°C
0.24
p-hydroxymercuribenzoate
Malus domestica
at pH 7.5 and 30°C
3
trilobatin
Malus domestica
at pH 7.5 and 30°C
0.1
UDP
Malus domestica
at pH 7.5 and 30°C
4
UMP
Malus domestica
at pH 7.5 and 30°C
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7 - 8
-
the enzyme shows significant activity from pH 7.0-8.0. Activity decreases to 20% at pH 6.0 and 9.0 and less than 5% at pH 5.0 and 10.0, respectively
7 - 9
-
significant activity at pH 7.0-9.0. Activity decreases to 17% at pH 6.0 and less than 5% at pH 10.0
7 - 9
up to 80% of its maximal activity remains within the pH range of 7.0-9.0
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30
-
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25 - 45
-
significant activity between 25 and 45°C
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5.8
-
calculated from amino acid sequence
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-
-
-
brenda
-
UniProt
brenda
cultivar Golden Delicious
UniProt
brenda
cv. Golden Delicious
UniProt
brenda
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-
-
brenda
-
highest expression
brenda
-
-
brenda
-
-
brenda
-
-
brenda
-
-
brenda
-
-
brenda
-
-
brenda
-
brenda
-
-
brenda
-
brenda
-
brenda
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malfunction
enzyme-knockdown lines are severely dwarfed, with greatly reduced internode lengths, narrow lanceolate leaves, and changes in leaf and fruit cellular morphology
evolution
the enzyme belongs to the UDP-glycosyltransferase UGT88F subfamily, subfamily tree, genomic organization of the UGT88F members on chromosome 15 and 8, overview. UGT88F1 is located closer to UGT88F4 on chromosome 15 and both genes share the same orientation. On chromosome 8, UGT88F6, UGT88F7 and UGT88F8 form a physical cluster sharing the same orientation. The Km values of UGT88F8 are 0.0077 mM and 0.0108 mM for phloretin and UDP-glucose, respectively, and are in the same range as UGT88F1 catalytic parameters thus constituting two isoforms. Co-expression patterns of both UGT88F1 and UGT88F8 argue for a redundant function in phlorizin biosynthesis in planta
evolution
the enzyme belongs to the UDP-glycosyltransferase UGT88F subfamily, subfamily tree, genomic organization of the UGT88F members on chromosome 15 and 8, overview. UGT88F1 is located closer to UGT88F4 on chromosome 15 and both genes share the same orientation. On chromosome 8, UGT88F6, UGT88F7 and UGT88F8 form a physical cluster sharing the same orientation. The Km values of UGT88F8 are 7.72 microM and 10.84 microM for phloretin and UDP-glucose, respectively, and are in the same range as UGT88F1 catalytic parameters thus constituting two isoforms. Coexpression patterns of both UGT88F1 and UGT88F8 argue for a redundant function in phlorizin biosynthesis in planta
physiological function
involvement of the enzyme in phlorizin (i.e. phloridzin or phloretin 2'-O-glucoside) synthesis, the main apple tree dihydrochalcone
physiological function
involvement of the enzyme in phlorizin (i.e. phloridzin or phloretin 2'-O-glucoside) synthesis, the main apple tree dihydrochalcone. UGT88F1 is able to efficiently glycosylate dihydrochalcones
additional information
three-dimensional structure analysis, modeling, and structure-function relationship, overview
additional information
three-dimensional structure analysis, modeling, and structure-function relationship, overview
additional information
-
three-dimensional structure analysis, modeling, and structure-function relationship, overview
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88F1G_MALDO
483
0
53547
Swiss-Prot
other Location (Reliability: 2 )
88F1R_MALDO
483
0
53600
Swiss-Prot
other Location (Reliability: 2 )
S5VDV0_MALDO
480
0
53290
TrEMBL
-
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65300
deglycosylated protein, gel filtration
70700
native protein, gel filtration
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homodimer
1 * 35200 + 1 * 24900, deglycosylated protein, SDS-PAGE
?
-
x * 53500, calculated from amino acid sequence
?
-
x * 59000, His6-tagged enzyme, SDS-PAGE
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7 - 9
the enzyme remains stable in the pH range of 7.0-9.0 incubated at 30°C for 24 h
749324
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25 - 35
the enzyme remains stable at 25-35°C for 1 h, retains 75% and 45% of its activity after 1 h at 45°C and 55°C, respectively, and is inactivated after 1 h at 65°C
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purified enzyme exhibits higher activity and stability in Tris/HCl buffer than in potassium phosphate buffer at pH 7.0
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DEAE anion exchange chromatography, His-Trap affinity chromatography, and Superdex G75 gel filtration
His-Trap column chromatography and Superdex 200 gel filtration
-
recombinant C-terminally His-tagged isozyme UGT88F8 from Saccharomyces cerevisiae strain W303 by nickel affinity chromatography and ultrafiltration
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expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli BL21-Codon-Plus-RIL cells
-
expressed in Pichia pastoris strain GS115
gene UGTF1, located on chromosome 15, DNA and amino acid sequence determination and analysis, quantitative RT-PCR expression analysis
gene UGTF8, located on chromosome 8, DNA and amino acid sequence determination and analysis, quantitative RT-PCR expression analysis, recombinant expression of C-terminally His-tagged isozyme UGT88F8 in Saccharomyces cerevisiae strain W303
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Jugde, H.; Nguy, D.; Moller, I.; Cooney, J.M.; Atkinson, R.G.
Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple
FEBS J.
275
3804-3814
2008
Malus domestica
brenda
Gutmann, A.; Bungaruang, L.; Weber, H.; Leypold, M.; Breinbauer, R.; Nidetzky, B.
Towards the synthesis of glycosylated dihydrochalcone natural products using glycosyltransferase-catalysed cascade reactions
Green Chem.
16
4417-4425
2014
Malus domestica
-
brenda
Yahyaa, M.; Davidovich-Rikanati, R.; Eyal, Y.; Sheachter, A.; Marzouk, S.; Lewinsohn, E.; Ibdah, M.
Identification and characterization of UDP-glucose phloretin 4'-O-glycosyltransferase from Malus x domestica Borkh
Phytochemistry
130
47-55
2016
Malus domestica
brenda
Gosch, C.; Halbwirth, H.; Stich, K.
Phloridzin biosynthesis, distribution and physiological relevance in plants
Phytochemistry
71
838-843
2010
Malus domestica
brenda
Dare, A.; Yauk, Y.; Tomes, S.; McGhie, T.; Rebstock, R.; Cooney, J.; Atkinson, R.
Silencing a phloretin-specific glycosyltransferase perturbs both general phenylpropanoid biosynthesis and plant development
Plant J.
91
237-250
2017
Malus domestica (B3TKC8), Malus domestica
brenda
Zhang, T.; Liang, J.; Wang, P.; Xu, Y.; Wang, Y.; Wei, X.; Fan, M.
Purification and characterization of a novel phloretin-2'-O-glycosyltransferase favoring phloridzin biosynthesis
Sci. Rep.
6
35274
2016
Malus domestica (D3UAG5), Malus domestica
brenda
Elejalde-Palmett, C.; Billet, K.; Lanoue, A.; De Craene, J.O.; Glevarec, G.; Pichon, O.; Clastre, M.; Courdavault, V.; St-Pierre, B.; Giglioli-Guivarch, N.; Duge de Bernonville, T.; Besseau, S.
Genome-wide identification and biochemical characterization of the UGT88F subfamily in Malus x domestica Borkh
Phytochemistry
157
135-144
2019
Malus domestica (B3TKC8), Malus domestica (S5VDV0), Malus domestica
brenda
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