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Information on EC 2.4.1.170 - isoflavone 7-O-glucosyltransferase
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EC Tree
2.4.1.170 isoflavone 7-O-glucosyltransferaseIUBMB 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.
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Word Map
- 2.4.1.170
- soybean
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isoflavonoids
- cotyledon
- daidzin
- kaempferol
- genistin
- 2-hydroxyisoflavanone
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aglycones
- echinata
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glycyrrhiza
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ammonia-lyase
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phytoalexins
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long-distance
- luteolin
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flooding
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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
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enrei
- naringenin
- glycitin
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cicer
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glucosyltransferases
- arietinum
- drug development
The enzyme appears in viruses and cellular organisms
Synonyms
gmif7gt, plugt1, isoflavone 7-o-glucosyltransferase, ugt73f1, if7gt, gmugt4, atgt-2, ugt709a4, gmugt1, udp-glucose:isoflavone 7-o-glucosyltransferase, 
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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
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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
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 + isoliquiritigenin
UDP + isoliquiritigenin 7-O-beta-D-glucoside
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?
UDP-glucose + an isoflavone
UDP + an isoflavone 7-O-beta-D-glucoside
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?
UDP-glucose + baicalein
UDP + baicalein 7-O-beta-D-glucoside
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very low activity
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?
UDP-glucose + eriodictyol
UDP + eriodictyol 7-O-beta-D-glucoside
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?
UDP-glucose + ferulic acid
UDP + 1-O-feruloyl-beta-D-glucose
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low activity
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?
UDP-glucose + liquiritigenin
UDP + liquiritigenin 7-O-beta-D-glucoside
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very low activity
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?
UDP-glucose + salicylic acid
UDP + salicylic acid 7-O-beta-D-glucoside
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very low activity
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?
UDP-glucose + scopoletin
UDP + scopoletin 7-O-beta-D-glucoside
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low activity
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?
UDP-glucose + biochanin A
UDP + biochanin A 7-O-beta-D-glucoside
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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poor substrate
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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i.e. daidzin
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
36% of the activity with genistein
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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i.e. daidzin
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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high activity
i.e. daidzin
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?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
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best substrate
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?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
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i.e. ononin
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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poor substrate
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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i.e. genistin
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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i.e. genistin
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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best substrate
i.e. genistin
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?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
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?
UDP-glucose + naringenin
UDP + naringenin 7-O-beta-D-glucoside
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low activity
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?
UDP-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
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?
additional information
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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.
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additional information
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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.
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additional information
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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.
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additional information
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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
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additional information
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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
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additional information
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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
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additional information
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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
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additional information
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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
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additional information
?
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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
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additional information
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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
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additional information
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the enzyme might play a role in defense against external stresses such as UV radiation and pathogen attack
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additional information
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substrate specificity, the flavonoids kaempferol, apigenin, and quercetin are poor substrates
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additional information
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no activity with apigenin, kaempferol, luteolin, naringenin, and quercetin
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additional information
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no activity with apigenin, kaempferol, luteolin, naringenin, and quercetin
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additional information
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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
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NATURAL SUBSTRATE
NATURAL 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-glucose + an isoflavone
UDP + an isoflavone 7-O-beta-D-glucoside
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?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
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i.e. ononin
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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i.e. daidzin
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?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
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i.e. daidzin
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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i.e. genistin
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
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i.e. genistin
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?
additional information
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the enzyme might play a role in defense against external stresses such as UV radiation and pathogen attack
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?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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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
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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%).
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additional information
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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
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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
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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
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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
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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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