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Information on EC 2.4.1.170 - isoflavone 7-O-glucosyltransferase
for references in articles please use BRENDA:EC2.4.1.170
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EC Tree 2 Transferases
2.4 Glycosyltransferases
2.4.1 Hexosyltransferases
2.4.1.170 isoflavone 7-O-glucosyltransferase
IUBMB Comments
The 4′-methoxy isoflavones biochanin A and formononetin and, more slowly, the 4′-hydroxyisoflavones genistein and daidzein, can act as acceptors. The enzyme does not act on isoflavanones, flavones, flavanones, flavanols or coumarins.
The enzyme appears in viruses and cellular organisms
- 2.4.1.170
- soybean
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isoflavonoids
- cotyledon
- daidzin
- kaempferol
- genistin
- 2-hydroxyisoflavanone
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aglycones
- echinata
-
glycyrrhiza
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ammonia-lyase
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phytoalexins
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long-distance
- luteolin
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flooding
-
bradyrhizobium
- sojae
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pueraria
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cell-suspension
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phytophthora
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plant-microbe
- lobata
-
enrei
- naringenin
- glycitin
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cicer
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glucosyltransferases
- arietinum
- drug development
showSynonyms
gmif7gt, plugt1, isoflavone 7-o-glucosyltransferase, ugt73f1, atgt-2, if7gt, gmugt4, isoflavone-specific 7-o-glucosyltransferase, ugt709a4, gmugt1, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
glucosyltransferase, uridine diphosphoglucose-isoflavone 7-O-
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IF7GT
UDP-glucose-flavonoid 7-O-glucosyltransferase
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UDP-glucose:isoflavone 7-O-glucosyltransferase
UDPglucose-flavonoid 7-O-glucosyltransferase
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UDPglucose:isoflavone 7-O-glucosyltransferase
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uridine diphosphoglucose-isoflavone 7-O-glucosyltransferase
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additional information
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the enzyme belongs to the family of UDP-glycosyltransferases
UDP-glucose:isoflavone 7-O-glucosyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + an isoflavone = UDP + an isoflavone 7-O-beta-D-glucoside
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
biochanin A conjugates interconversion, daidzein conjugates interconversion, formononetin conjugates interconversion, genistein conjugates interconversion, maackiain conjugates interconversion, medicarpin conjugates interconversion
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
The 4'-methoxy isoflavones biochanin A and formononetin and, more slowly, the 4'-hydroxyisoflavones genistein and daidzein, can act as acceptors. The enzyme does not act on isoflavanones, flavones, flavanones, flavanols or coumarins.
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CAS REGISTRY NUMBER
COMMENTARY
97089-62-8
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-alpha-D-glucose + isoliquiritigenin
UDP + isoliquiritigenin 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + 4,2',4',6'-tetrahydroxychalcone
UDP + ?
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + an isoflavone
UDP + an isoflavone 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + apigenin
UDP + apigenin 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + aureusidin
UDP + aureusidin 6-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + baicalein
UDP + baicalein 7-O-beta-D-glucoside
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Substrates: very low activity
Products: -
Products: -
?
UDP-glucose + calycosin
UDP + calycosin 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + eriodictyol
UDP + eriodictyol 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + esculetin
UDP + esculetin 7-O-beta-D-glucoside
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Substrates: -
Products: -
Products: -
?
UDP-glucose + ferulic acid
UDP + 1-O-feruloyl-beta-D-glucose
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Substrates: low activity
Products: -
Products: -
?
UDP-glucose + isovitexin
UDP + isovitexin 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + liquiritigenin
UDP + liquiritigenin 7-O-beta-D-glucoside
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Substrates: very low activity
Products: -
Products: -
?
UDP-glucose + luteolin
UDP + luteolin 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + phloretin
UDP + phloretin glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + salicylic acid
UDP + salicylic acid 7-O-beta-D-glucoside
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Substrates: very low activity
Products: -
Products: -
?
UDP-glucose + scopoletin
UDP + scopoletin 7-O-beta-D-glucoside
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Substrates: low activity
Products: -
Products: -
?
UDP-glucose + biochanin A
UDP + biochanin A 7-O-beta-D-glucoside
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Substrates: -
Products: -
Products: -
?
UDP-glucose + biochanin A
UDP + biochanin A 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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Substrates: poor substrate
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
Substrates: -
Products: i.e. daidzin
Products: i.e. daidzin
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
Substrates: 36% of the activity with genistein
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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Substrates: -
Products: i.e. daidzin
Products: i.e. daidzin
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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Substrates: high activity
Products: i.e. daidzin
Products: i.e. daidzin
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
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Substrates: -
Products: -
Products: -
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
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Substrates: best substrate
Products: -
Products: -
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
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Substrates: -
Products: i.e. ononin
Products: i.e. ononin
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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Substrates: poor substrate
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
Substrates: -
Products: i.e. genistin
Products: i.e. genistin
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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Substrates: -
Products: i.e. genistin
Products: i.e. genistin
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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Substrates: best substrate
Products: i.e. genistin
Products: i.e. genistin
?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + naringenin
UDP + naringenin 7-O-beta-D-glucoside
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Substrates: -
Products: -
Products: -
?
UDP-glucose + naringenin
UDP + naringenin 7-O-beta-D-glucoside
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Substrates: low activity
Products: -
Products: -
?
UDP-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
additional information
?
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Substrates: caffeic acid and esculetin do not react with the enzyme. AtGT-2 prefers flavonene to flavone or flavonol, both of which contain a double bond in the C ring. The relative conversion rate is 100% for eriodictyol, 71.6% for naringenin, 29.6% for apigenin, 92.1% for luteolin, 78.9% for kaempferol and 64.1% for quercetin.
Products: -
Products: -
?
additional information
?
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Substrates: caffeic acid and esculetin do not react with the enzyme. AtGT-2 prefers flavonene to flavone or flavonol, both of which contain a double bond in the C ring. The relative conversion rate is 100% for eriodictyol, 71.6% for naringenin, 29.6% for apigenin, 92.1% for luteolin, 78.9% for kaempferol and 64.1% for quercetin.
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme accepts isoflavones, flavones, flavanones, flavonols, dihydroflavonols, and dihydrochalcones as substrates and exclusively produces 7-O-glucosides
Products: -
Products: -
-
additional information
?
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Substrates: enzyme accepts isoflavones, flavones, flavanones, flavonols, dihydroflavonols, and dihydrochalcones as substrates and exclusively produces 7-O-glucosides
Products: -
Products: -
-
additional information
?
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Substrates: rates of conversion of flavonols are significantly higher than those of flavones
Products: -
Products: -
-
additional information
?
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Substrates: rates of conversion of flavonols are significantly higher than those of flavones
Products: -
Products: -
-
additional information
?
-
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Substrates: the relative activites for UDP-glucuronic acid and for UDP-galactose is 0% and for UDP-glucose 12%, all tested with genistein as glycosyl acceptor
Products: -
Products: -
?
additional information
?
-
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Substrates: none of the following phenolics serve as glucosyl acceptors: cyanidin, trans-p-coumaric acid, caffeic acid, benzoic acid, m- and p-hydroybenzoic acid, salicylic acid, salicyl alcohol and hydroquinone.
Products: -
Products: -
?
additional information
?
-
-
Substrates: in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT4, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
Products: -
Products: -
?
additional information
?
-
Substrates: in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT4, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
Products: -
Products: -
?
additional information
?
-
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Substrates: in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT3, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
Products: -
Products: -
?
additional information
?
-
Substrates: in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT3, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
Products: -
Products: -
?
additional information
?
-
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Substrates: GmUGT1 is active with UDP-galactose and UDP-glucuronic acid as substrates. It displays high specific activities toward isoflavones (genistein and daidzein) to produce their 7-O-beta-D-glucosides, it also shows considerable levels of activities toward other flavonoids such as kaempferol, quercetin, naringenin and apigenin. GmUGT1 is also capable of acting on the flavone luteolin, (S)-equol, a 4',7-isoflavandiol, and (R)-equol
Products: -
Products: -
?
additional information
?
-
Substrates: GmUGT1 is active with UDP-galactose and UDP-glucuronic acid as substrates. It displays high specific activities toward isoflavones (genistein and daidzein) to produce their 7-O-beta-D-glucosides, it also shows considerable levels of activities toward other flavonoids such as kaempferol, quercetin, naringenin and apigenin. GmUGT1 is also capable of acting on the flavone luteolin, (S)-equol, a 4',7-isoflavandiol, and (R)-equol
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme might play a role in defense against external stresses such as UV radiation and pathogen attack
Products: -
Products: -
?
additional information
?
-
-
Substrates: substrate specificity, the flavonoids kaempferol, apigenin, and quercetin are poor substrates
Products: -
Products: -
?
additional information
?
-
Substrates: endogenous substrate not known
Products: -
Products: -
?
additional information
?
-
-
Substrates: endogenous substrate not known
Products: -
Products: -
?
additional information
?
-
Substrates: no activity with apigenin, kaempferol, luteolin, naringenin, and quercetin
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with apigenin, kaempferol, luteolin, naringenin, and quercetin
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is relatively specific for isoflavone aglycones, while flavonoid substrates are poorly accepted. No activity with cyanidin, luteolin, kaempferol, and quercetin, naringenin and apigenin are poor substrates, substrate specificity, overview
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-glucose + an isoflavone
UDP + an isoflavone 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
-
Substrates: -
Products: i.e. ononin
Products: i.e. ononin
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
Substrates: -
Products: i.e. daidzin
Products: i.e. daidzin
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
-
Substrates: -
Products: i.e. daidzin
Products: i.e. daidzin
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
Substrates: -
Products: i.e. genistin
Products: i.e. genistin
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
Substrates: -
Products: i.e. genistin
Products: i.e. genistin
?
additional information
?
-
-
Substrates: the enzyme might play a role in defense against external stresses such as UV radiation and pathogen attack
Products: -
Products: -
?
additional information
?
-
Substrates: endogenous substrate not known
Products: -
Products: -
?
additional information
?
-
-
Substrates: endogenous substrate not known
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
Ca2+, Cd2+, Co2+, Cu2+, Mg2+, Mn2+, Ni2+, Sn2+ or Zn2+ (all at 0.1 mM) have negligible effect on the catalytic activity.
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
1 mM EDTA, 1mM uridine, 1 mM UMP, 1 mM UDP, 1 mM UTP, 1 mM glucose, 1 mM diethylpyrocarbonatem or 1 mM phenylmethanesulfonyl fluoride have negligibel effect on the catalytic activity (residual activity, in excess of 64%).
-
additional information
-
the enzyme is stress-inducible, no inhibition by baicalein, kaempferol, naringenin, apigenin, quercetin, scopoletin, ferulic acid, and salicylic acid
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
the enzyme is stress-inducible, transient induction by cell suspension culture treatment with yeast extract
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infections
Transcription analyses of GmICHG, a gene coding for a ?-glucosidase that catalyzes the specific hydrolysis of isoflavone conjugates in Glycine max (L.) Merr
Infections
Transcription analyses of GmICHG, a gene coding for a ?-glucosidase that catalyzes the specific hydrolysis of isoflavone conjugates in Glycine max (L.) Merr.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
Kcat/Km for eriodictyol is 2.66 microM-1/mg-1, 1.32 microM-1/mg-1 for kaempferol and 250 microM-1/mg-1 for quercetin. Assay at pH 7.0 and 37°C
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additional information
additional information
-
Kcat/Km for eriodictyol is 2.66 microM-1/mg-1, 1.32 microM-1/mg-1 for kaempferol and 250 microM-1/mg-1 for quercetin. Assay at pH 7.0 and 37°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.253
additional information
additional information
Vmax for eriodictyol is 333.3 pkat/mg, 333.3 pkat/mg for kaempferol and 250 pkat/mg for quercetin. Assay at pH 7.0 and 37°C
additional information
-
Vmax for eriodictyol is 333.3 pkat/mg, 333.3 pkat/mg for kaempferol and 250 pkat/mg for quercetin. Assay at pH 7.0 and 37°C
additional information
-
as glucosyl acceptor genistein shows the highest activity (100%), daidzein has 73%, formononetin shows 67%, quercetin 32%, kaempferol 19%, 4,2',4',6'-tetrahydoxychalcone 15%, apigenin 14%, aureusidin 5%, esculetin 4% and naringenin shows 3% activity (all tested with UDP-glucose). Enzyme assay is run at pH 8.5 at 30°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
collected from Langxi County, Anhui Province, China, gene PlUGT1
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
during the riping process the enzyme shows two activity peaks: in green fruits and in full-ripe red fruits
brenda
additional information
-
transient induction by cell suspension culture treatment with yeast extract
brenda
AtGT-2 is expressed in this tissue, higher in the flowers and leaves than in roots and stems
brenda
AtGT-2 is expressed in this tissue, higher in the flowers and leaves than in roots and stems
brenda
AtGT-2 is expressed in this tissue, higher in the flowers and leaves than in roots and stems
brenda
the expression of UGT4, an isoflavone-specific 7-O-glucosyltransferase (UGT4), is decreased during the reproductive stages. Expression of UGT4 is high in the vegetative stages, and decreased by over 90% during the reproductive stages
brenda
AtGT-2 is expressed in this tissue, higher in the flowers and leaves than in roots and stems
brenda
additional information
real-time RT-PCR tissue expression analysis of GmIF7GT gene homologues 1-6, overview. The transcript level of a less known gene homologue of isoflavone 7-O-glucosyltransferase GmIF7GT4 is significantly higher by about 11fold, in the roots than the gene homologue mIF7GT1 and the other homologues. Transcript levels of other homologues of GmIF7GT are much lower than the transcript levels of GmIF7GT1 or GmIF7GT4, overview
brenda
additional information
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real-time RT-PCR tissue expression analysis of GmIF7GT gene homologues 1-6, overview. The transcript level of a less known gene homologue of isoflavone 7-O-glucosyltransferase GmIF7GT4 is significantly higher by about 11fold, in the roots than the gene homologue mIF7GT1 and the other homologues. Transcript levels of other homologues of GmIF7GT are much lower than the transcript levels of GmIF7GT1 or GmIF7GT4, overview
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additional information
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gene GmUGT4 encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, followed by taproots, cotyledon, and hypocotyls
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additional information
gene GmUGT4 encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, followed by taproots, cotyledon, and hypocotyls
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additional information
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gene GmUGT3 encodes a UGT that is highly specific for isoflavones
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additional information
gene GmUGT3 encodes a UGT that is highly specific for isoflavones
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additional information
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gene GmUGT9 encodes a UGT that is highly specific for isoflavones, the levels of the GmUGT9 transcripts are highest in roots, followed by taproots, cotyledon, and hypocotyls
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additional information
gene GmUGT9 encodes a UGT that is highly specific for isoflavones, the levels of the GmUGT9 transcripts are highest in roots, followed by taproots, cotyledon, and hypocotyls
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additional information
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the levels of the most abundant GmUGT1 transcripts in cotyledons are much higher than those in lateral roots
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additional information
the levels of the most abundant GmUGT1 transcripts in cotyledons are much higher than those in lateral roots
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additional information
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the levels of the most abundant GmUGT7 transcripts in cotyledons are much higher than those in lateral roots
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additional information
the levels of the most abundant GmUGT7 transcripts in cotyledons are much higher than those in lateral roots
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additional information
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transcript abundance of gee PlUGT1 is correlated with the accumulation pattern of isoflavone glycosides such as daidzin in Pueraria lobata plants or in cell suspension culture
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Highest Expressing Human Cell Lines
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
additional information
evolution
nine different GmUGT cDNAs that are related to GmUGT1, UniProt ID A6BM07, are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview. The enzymes of subgroup A, GmUGT3, GmUGT4, and GmUGT9, all are highly specific for isoflavones. Gene GmUGT4, a representative of subgroup A, encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, while gene GmUGT1, a representative of subgroup B, encodes an enzyme displaying a broad glucosyl-acceptor specificity and is expressed in the aerial parts, i.e. cotyledons, hypocotyls and pods
evolution
nine different GmUGT cDNAs that are related to GmUGT1, UniProt ID A6BM07, are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview. The enzymes of subgroup A, GmUGT3, GmUGT4, and GmUGT9, all are highly specific for isoflavones
evolution
nine different GmUGT cDNAs that are related to GmUGT1 are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview. The enzymes of subgroup A, GmUGT3, GmUGT4, and GmUGT9, all are highly specific for isoflavones. Gene GmUGT4, a representative of subgroup A, encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, while gene GmUGT1, a representative of subgroup B, encodes an enzyme displaying a broad glucosyl-acceptor specificity and is expressed in the aerial parts, i.e. cotyledons, hypocotyls and pods
evolution
nine different GmUGT cDNAs that are related to GmUGT1, UniProt ID A6BM07, are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview
metabolism
the enzyme take part in the isoflavonoid pathway, in silico expression profiles of genes involved in the pathway, isoflavonoid pathway overview
metabolism
the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis
metabolism
the enzyme is involved in the isoflavone biosynthesis, pathway overview. The expressions of UGT4, an isoflavone-specific 7-O-glucosyltransferase, and of ICHG (isoflavone conjugates hydrolyzing beta-glucosidase) are decreased during the reproductive stages. Isoflavone contents are higher in rhizosphere soil than in bulk soil during both vegetative and reproductive stages, and are comparable in the rhizosphere soil between these two stages
metabolism
-
involved in isoflavonoid metabolism. Key enzyme in the synthesis of isoflavone conjugates in the downstream of flavonoid biosynthetic pathway, which could convert daidzein, genistein, and formononetin to daidzin, genistin, and ononin, respectively
physiological function
the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis. Isoflavone conjugates, 7-O-beta-D-glucosides and 7-O-(6''-malonyl-beta-D-glucosides) of daidzein and genistein, accumulate in soybean roots and serve as the stored precursors of isoflavones (aglycons), which play very important roles in the rhizobia-mediated nodulation of this plant. Isozyme GmUGT4, but not GmUGT1, plays an exclusive role in the conjugation of isoflavones in the lateral roots of the soybean plant
physiological function
the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis. Isoflavone conjugates, 7-O-beta-D-glucosides and 7-O-(6''-malonyl-beta-D-glucosides) of daidzein and genistein, accumulate in soybean roots and serve as the stored precursors of isoflavones (aglycons), which play very important roles in the rhizobia-mediated nodulation of this plant
physiological function
the enzyme is involved in the synthesis and secretion of isoflavones, e.g. daidzein and genistein, by field-grown soybean. Isoflavone glucosides are secreted into the apoplast. Isoflavones in the rhizosphere soil were shown to induce the expression of rhizobial Nod genes, which initiate the formation of the nodules that fix nitrogen. In addition, isoflavones act as antimicrobial phytoalexins and modulate rhizosphere microbial communities
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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). I7GT1_SOYBN
474
0
52036
Swiss-Prot
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D125A
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in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E376A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E392A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E392D
-
in the mutant the kcat is higher and the Km is lower than in wild type enzyme
E456A
-
in the mutant the kcat is lower and the Km is slightly lower than in wild type enzyme
H15A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
H359A
-
in the mutant the kcat is lower and the Km has the same level as in wild type enzyme
H368A
-
in the mutant the kcat is higher and the Km is higher than in wild type enzyme
additional information
additional information
cell engineering by GmIF7GT enzyme coexpression with acyl-CoA carboxylase alpha and beta subunits, biotin ligase, and acetyl-CoA synthetase from Nocardia farcinia for subsequent malonylization of the reaction product of GmIF7GT-encoded isoflavone 7-O-glucosyltransferase. The isoflavonoids are glycosylated at position 7 by 7-O-glycosyltranferase and are further malonylated at position 6' of glucose by malonyl-CoA:isoflavone 7-O-glucoside-6'-O-malonyltransferase both from Glycine max, Scale up for production using a fermentor
additional information
-
Saccharomyces cerevisiae cells expressing PlUGT1 are not able to glycosylate daidzin and puerarin
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
DEAE-Sepharose Fast Flow column, Q-Sepharose HP column, Phenyl-Sepharose HP column (pH 8.5), hydroxyapatite column, gel filtration (HiLoad 26/60 Superdex 200pg column), resource Q column and chromatofocusing on Mono P (Mono P column), all at 4°C. The activity in the crude extract is extremely unstable to oxidation and the addition of 2-mercaptoethanol is essential for its efficient purification. The addition of CHAPS to purification buffers is also essential for purification after step 6 (hydroxyapatite chromatography), otherwise the activity is irreversibly lost.
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recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) to near homogeneity by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning of gene homologues GmIF7GT1-GmIF7GT6, DNA and amino acid sequence determination, expression analysis
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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gene GmIF7GT, DNA and amino acid sequence determination and analysis, expression analysis
gene GmIF7GT, recombinant functional expression in Escherichia coli strain BL21(DE3), coexpression with acyl-CoA carboxylase alpha and beta subunits, biotin ligase, and acetyl-CoA synthetase from Nocardia farcinia for subsequent malonylization of the reaction product of GmIF7GT-encoded isoflavone 7-O-glucosyltransferase. The isoflavonoids are glycosylated at position 7 by 7-O-glycosyltranferase and are further malonylated at position 6' of glucose by malonyl-CoA:isoflavone 7-O-glucoside-6'-O-malonyltransferase both from Glycine max
gene GmIF7GT1, quantitative real-time reverse transcription-PCR enzyme expression analysis
gene GmUGT1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis
gene GmUGT3, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis
gene GmUGT4, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis
gene GmUGT7, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis
gene GmUGT9, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis
gene PlUGT1 or UGT88E12, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli and in Saccharomyces cerevisiae strain WAT11
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is strongly induced by methyl jasmonate signal in cell suspension culture
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug development
isoflavonoids and their glycosides may prove useful as anticancer drugs with added advantage of increased solubility, stability and bioavailability. Among the six compounds tested, genistein most effectively inhibits the growth of B16F10 and AGS cells, with IC50 values of 0.0077 mM and 0.0398 mM, respectively. Unlike derivatives of genistein (genistin and biochanin A), the glycosylated and methylated forms of daidzein (daidzin and formononetin) exhibit more effective growth inhibition than aglycon, daidzein
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Koester, J.; Barz, W.
UDP-glucose:isoflavone 7-O-glucosyltransferase from roots of chick pea (Cicer arietinum L.)
Arch. Biochem. Biophys.
212
98-104
1981
Cicer arietinum
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Vellekoop, P.; Lugones, L.; van Brederode, J.
Purification of an UDP-glucose:flavone, 7-O-glucosyltransferase, from Silene latifolia using a specific interaction between the enzyme and phenyl-Sepharose
FEBS Lett.
330
36-40
1993
Silene latifolia
brenda
Nagashima, S.; Inagaki, R.; Kubo, A.; Hirotani, M.; Yoshikawa, T.
cDNA cloning and expression of isoflavonoid-specific glucosyltransferase from Glycyrrhiza echinata cell-suspension cultures
Planta
218
456-459
2004
Glycyrrhiza echinata
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Kim, J.H.; Kim, B.G.; Park, Y.; Ko, J.H.; Lim, C.E.; Lim, J.; Lim, Y.; Ahn, J.
Characterization of flavonoid 7-O-glucosyltransferase from Arabidopsis thaliana
Biosci. Biotechnol. Biochem.
70
1471-1477
2006
Arabidopsis thaliana (Q8VZE9), Arabidopsis thaliana
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Halbwirth, H.; Puhl, I.; Haas, U.; Jezik, K.; Treutter, D.; Stich, K.
Two-phase flavonoid formation in developing strawberry (Fragaria x ananassa) fruit
J. Agric. Food Chem.
54
1479-1485
2006
Fragaria x ananassa
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Noguchi, A.; Saito, A.; Homma, Y.; Nakao, M.; Sasaki, N.; Nishino, T.; Takahashi, S.; Nakayama, T.
A UDP-glucose:isoflavone 7-O-glucosyltransferase from the roots of soybean (Glycine max) seedlings: Purification, gene cloning, phylogenetics, and an implication for an alternative strategy of enzyme catalysis
J. Biol. Chem.
282
23581-23590
2007
Glycine max
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Ko, J.H.; Kim, B.G.; Kim, J.H.; Kim, H.; Lim, C.E.; Lim, J.; Lee, C.; Lim, Y.; Ahn, J.
Four glucosyltransferases from rice: cDNA cloning, expression, and characterization
J. Plant Physiol.
165
435-444
2008
Oryza sativa (Q7XHR3), Oryza sativa
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Suita, K.; Kiryu, T.; Sawada, M.; Mitsui, M.; Nakagawa, M.; Kanamaru, K.; Yamagata, H.
Cyclic GMP acts as a common regulator for the transcriptional activation of the flavonoid biosynthetic pathway in soybean
Planta
229
403-413
2009
Glycine max
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Livingstone, J.M.; Zolotarov, Y.; Stroemvik, M.V.
Transcripts of soybean isoflavone 7-O-glucosyltransferase and hydroxyisoflavanone dehydratase gene homologues are at least as abundant as transcripts of their well known counterparts
Plant Physiol. Biochem.
49
1071-1075
2011
Glycine max (A6BM07), Glycine max, Glycine max Williams 82 (A6BM07)
brenda
Livingstone, J.; Seguin, P.; Strmvik, M.
An in silico study of the genes for the isoflavonoid pathway enzymes in soybean reveals novel expressed homologues
Can. J. Plant Sci.
90
453-469
2010
Glycine max (A6BM07)
-
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Koirala, N.; Pandey, R.P.; Thang, D.V.; Jung, H.J.; Sohng, J.K.
Glycosylation and subsequent malonylation of isoflavonoids in E. coli: strain development, production and insights into future metabolic perspectives
J. Ind. Microbiol. Biotechnol.
41
1647-1658
2014
Glycine max (A6BM07)
brenda
Funaki, A.; Waki, T.; Noguchi, A.; Kawai, Y.; Yamashita, S.; Takahashi, S.; Nakayama, T.
Identification of a highly specific isoflavone 7-O-glucosyltransferase in the soybean (Glycine max (L.) Merr.)
Plant Cell Physiol.
56
1512-1520
2015
Glycine max, Glycine max (A6BM07)
brenda
Li, J.; Li, Z.; Li, C.; Gou, J.; Zhang, Y.
Molecular cloning and characterization of an isoflavone 7-O-glucosyltransferase from Pueraria lobata
Plant Cell Rep.
33
1173-1185
2014
Pueraria montana var. lobata
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Sugiyama, A.; Yamazaki, Y.; Hamamoto, S.; Takase, H.; Yazaki, K.
Synthesis and secretion of isoflavones by field-grown soybean
Plant Cell Physiol.
58
1594-1600
2017
Glycine max (A6BM07), Glycine max
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Huang, X.; Chu, G.; Wang, J.; Luo, H.; Yang, Z.; Sun, L.; Rong, W.; Wang, M.
Integrated metabolomic and transcriptomic analysis of specialized metabolites and isoflavonoid biosynthesis in Sophora alopecuroides L. under different degrees of drought stress
Ind. Crops Prod.
197
116595
2023
Sophora alopecuroides
-
brenda
Hao, Y.; Fu, J.; Zhang, J.; Du, N.; Ta, H.; Zhu, T.T.; Wang, H.; Lou, H.X.; Cheng, A.X.
Identification and functional characterization of UDP-glycosyltransferases involved in isoflavone biosynthesis in Astragalus membranaceus
J. Agric. Food Chem.
71
12775-12784
2023
Astragalus membranaceus (A0AA49KF26), Astragalus membranaceus (A0AA49KF33)
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