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Information on EC 2.4.1.360 - 2-hydroxyflavanone C-glucosyltransferase and Organism(s) Fagopyrum esculentum and UniProt Accession A0A0A1HA03

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EC Tree
     2 Transferases
         2.4 Glycosyltransferases
             2.4.1 Hexosyltransferases
                2.4.1.360 2-hydroxyflavanone C-glucosyltransferase
IUBMB Comments
The enzyme has been characterized in Oryza sativa (rice), various Citrus spp., Glycine max (soybean), and Fagopyrum esculentum (buckwheat). Flavanone substrates require a 2-hydroxy group. The meta-stable flavanone substrates such as 2-hydroxynaringenin exist in an equilibrium with open forms such as 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione, which are the actual substrates for the glucosyl-transfer reaction (see EC 1.14.14.162, flavanone 2-hydroxylase). The enzyme can also act on dihydrochalcones. The enzymes from citrus plants can catalyse a second C-glycosylation reaction at position 5.
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This record set is specific for:
Fagopyrum esculentum
UNIPROT: A0A0A1HA03
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Word Map
The taxonomic range for the selected organisms is: Fagopyrum esculentum
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
oscgt, fccgt, ugt708c1, cucgt, 2-hydroxyflavanone c-glucosyltransferase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
UDP-glucose:2-hydroxyflavanone-6(or8)-C-glucosyltransferase
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -
SYSTEMATIC NAME
IUBMB Comments
UDP-alpha-D-glucose:2'-hydroxy-beta-oxodihydrochalcone C6/8-beta-D-glucosyltransferase
The enzyme has been characterized in Oryza sativa (rice), various Citrus spp., Glycine max (soybean), and Fagopyrum esculentum (buckwheat). Flavanone substrates require a 2-hydroxy group. The meta-stable flavanone substrates such as 2-hydroxynaringenin exist in an equilibrium with open forms such as 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione, which are the actual substrates for the glucosyl-transfer reaction (see EC 1.14.14.162, flavanone 2-hydroxylase). The enzyme can also act on dihydrochalcones. The enzymes from citrus plants can catalyse a second C-glycosylation reaction at position 5.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 UDP-alpha-D-glucose + 2-hydroxynaringenin
2 UDP + 6,8-di-(beta-D-glucopyranosyl)-2-hydroxynaringenin
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + ?
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone
UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
show the reaction diagram
-
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxyeriodictyol
2 UDP + ?
show the reaction diagram
-
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxynaringenin
2 UDP + 6,8-di-(beta-D-glucopyranosyl)-2-hydroxynaringenin
show the reaction diagram
-
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxypinocembrin
2 UDP + ?
show the reaction diagram
-
-
-
?
2 UDP-alpha-D-glucose + 2-phenyl-2',4',6'-trihydroxyacetophenone
2 UDP + ?
show the reaction diagram
-
-
-
?
2 UDP-alpha-D-glucose + phloretin
2 UDP + ?
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
show the reaction diagram
-
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + ?
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + isovitexin + H2O
show the reaction diagram
-
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + vitexin + H2O
show the reaction diagram
-
-
-
-
?
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone
UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
show the reaction diagram
-
-
-
?
UDP-D-galactose + 2-hydroxynaringenin
UDP + isovitexin
show the reaction diagram
-
-
-
-
?
UDP-D-galactose + 2-hydroxynaringenin
UDP + vitexin
show the reaction diagram
-
-
-
-
?
UDP-xylose + 2-hydroxynaringenin
UDP + isovitexin
show the reaction diagram
-
-
-
-
?
UDP-xylose + 2-hydroxynaringenin
UDP + vitexin
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL 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 + 2-hydroxynaringenin
UDP + ?
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone
UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + ?
show the reaction diagram
-
-
-
?
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone
UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Al3+
-
increases the enzyme activity at pH 8
Fe3+
-
stimulates activity
additional information
-
Mg2+, Ca2+, Co2+ and Cu2+ have no significant effect in activity
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4-dihydroxydibenzoylmethane
2-hydroxynaringenin
-
aglycon concentrations higher than 0.05 mM inhibit the reaction
additional information
-
concentrations of the glucosyldonor up to 0.5 mM increase the rate of product formation. EDTA has no significant effect in activity
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in the proposed biosynthetic pathway of C-glucosylflavones in buckwheat, overview. It starts with the hydroxylation of the 2-position of flavanone, which is the intermedixadate product of flavonol biosynthesis. The produced 2-hydroxyflavanone is in equilibrium with one of its open-circular forms (2',4',6'-trihydroxyacetophenone-like structure, dibenzoylxadmethane form), which is C-glucosylated by CGT. The formed C-glucoside is also in equilibrium with its two closed-circular forms, that is, 2-hydroxyflavanone 6-C-glucoside and 8-C-glucoside, because the sugar moiety of the open-circular form of C-glucoside can be rotated. They are then enzymatically dehydrated to produce two C-glucosylflavones
physiological function
FeCGT enxadzymes (UGT708C1 and UGT708C2) show C-glucosylation activity toward 2-hydroxyflavanones and related compounds having a 2',4',6'-trihydroxyacetophenone-like structure but not toward flavones or flavonols, indicating that the open-circular form of 2-hydroxyflavanones is their substrate
metabolism
the enzyme is involved in the proposed biosynthetic pathway of C-glucosylflavones in buckwheat, overview. It starts with the hydroxylation of the 2-position of flavanone, which is the intermedixadate product of flavonol biosynthesis. The produced 2-hydroxyflavanone is in equilibrium with one of its open-circular forms (2',4',6'-trihydroxyacetophenone-like structure, dibenzoylxadmethane form), which is C-glucosylated by CGT. The formed C-glucoside is also in equilibrium with its two closed-circular forms, that is, 2-hydroxyflavanone 6-C-glucoside and 8-C-glucoside, because the sugar moiety of the open-circular form of C-glucoside can be rotated. They are then enzymatically dehydrated to produce two C-glucosylflavones
physiological function
FeCGT enxadzymes (UGT708C1 and UGT708C2) show C-glucosylation activity toward 2-hydroxyflavanones and related compounds having a 2',4',6'-trihydroxyacetophenone-like structure but not toward flavones or flavonols, indicating that the open-circular form of 2-hydroxyflavanones is their substrate
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
708C1_FAGES
457
0
50375
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50380
calculated from amino acid sequence
41000
-
gel filtration
50430
calculated from amino acid sequence
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purification via a nickel-affinity column, concentration using Amicon-Ultra-15 Ultracel-10k
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli Rosetta 2(DE3)
expression in Escherichia coli
expressed in Escherichia coli Rosetta 2(DE3)
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
production of C-glucosides of flavonoids and related compounds (i.e., 2-hydroxyflavanone, dihydrochalcone, and trihydroxyacetophenone) by Escherichia coli expressing C-glucosyltransferase from Fagopyrum esculentum. The substrates in their respective cultures were taken up by the cells and C-glucosylated, and the products were released into the culture media. The bioconversion process was completed in 1-2 h, but products were already observed immediately after addition of the substrates (0.2 mM). The conversion rates of these substrates reaches 80-95%
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nagatomo, Y.; Usui, S.; Ito, T.; Kato, A.; Shimosaka, M.; Taguchi, G.
Purification, molecular cloning and functional characterization of flavonoid C-glucosyltransferases from Fagopyrum esculentum M. (buckwheat) cotyledon
Plant J.
80.
437-448
2014
Fagopyrum esculentum (A0A0A1H7N4), Fagopyrum esculentum (A0A0A1HA03)
Manually annotated by BRENDA team
Kerscher, F.; Franz, G.
Isolation and Some Properties of an UDP-glucose 2-hydroxyflavanone-6(or 8)-C-glucosyltransferase from Fagopyrum esculentum M. cotyledons
J. Plant Physiol.
132
110-115
1988
Fagopyrum esculentum
-
Manually annotated by BRENDA team
Ito, T.; Fujimoto, S.; Shimosaka, M.; Taguchi, G.
Production of C-glucosides of flavonoids and related compounds by Escherichia coli expressing buckwheat C-glucosyltransferase
Plant Biotechnol.
31
519-524
2014
Fagopyrum esculentum (A0A0A1HA03)
Manually annotated by BRENDA team
Taguchi, G.
Flavonoid biosynthesis in buckwheat
Molecular Breeding and Nutritional Aspects of Buckwheat (ed. Zhou M. and Kreft I. and Woo S.H.)
2016
377-386
2016
Fagopyrum esculentum (A0A0A1H7N4), Fagopyrum esculentum (A0A0A1HA03)
-
Manually annotated by BRENDA team