Information on EC 2.3.1.115 - isoflavone-7-O-beta-glucoside 6''-O-malonyltransferase

for references in articles please use BRENDA:EC2.3.1.115
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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
2.3.1.115
-
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RECOMMENDED NAME
GeneOntology No.
isoflavone-7-O-beta-glucoside 6''-O-malonyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
malonyl-CoA + biochanin A 7-O-beta-D-glucoside = CoA + biochanin A 7-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
apigenin glycosides biosynthesis
-
-
biochanin A conjugates interconversion
-
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daidzein conjugates interconversion
-
-
formononetin conjugates interconversion
-
-
genistein conjugates interconversion
-
-
maackiain conjugates interconversion
-
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medicarpin conjugates interconversion
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Isoflavonoid biosynthesis
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Flavone and flavonol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6''-O-malonyltransferase
The 6-position of the glucose residue of formononetin can also act as acceptor; some other 7-O-glucosides of isoflavones, flavones and flavonols can also act, but more slowly.
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CAS REGISTRY NUMBER
COMMENTARY hide
78413-09-9
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93585-97-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
chick pea
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-
Manually annotated by BRENDA team
parsley
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-
Manually annotated by BRENDA team
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
apigenin 7-O-apiosylglucoside + malonyl-CoA
apigenin 7-O-apiosylglucoside -6''-O-malonylester + CoA
show the reaction diagram
apigenin 7-O-glucoside + malonyl-CoA
CoA + apigenin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
apiin + malonyl-CoA
apigenin 7-O-apiosylglucoside -6''-O-malonylester + malonyl-CoA
show the reaction diagram
-
i.e. apigenin 7-O-apiosylglucoside, best substrate
-
-
?
diosmetin 7-O-glucoside + malonyl-CoA
CoA + diosmetin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
72% of the activity with apiin
-
-
?
isorhamnetin 3-O-glucoside + malonyl-CoA
CoA + isorhamnetin 3-O-glucoside 6''-O-malonylester
show the reaction diagram
-
11% of the activity with apiin
-
-
?
isorhamnetin 7-O-glucoside + malonyl-CoA
CoA + isorhamnetin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
12% of the activity with apiin
-
-
?
kaempferol 3-O-glucoside + malonyl-CoA
CoA + kaempferol 3-O-glucoside 6''-O-malonylester
show the reaction diagram
-
15% of the activity with apiin
-
-
?
luteolin 7-O-glucoside + malonyl-CoA
CoA + luteolin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
malonyl CoA + genistein 7-O-glucoside
CoA + genistein 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
malonyl-CoA + (-)-maackiain 3-O-beta-D-glucoside
CoA + (-)-maackiain 3-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
-
-
-
-
?
malonyl-CoA + 2',4,4'-trihydroxychalcone 4-O-glucoside
CoA + 2',4,4'-trihydroxychalcone 4-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
malonyl-CoA + 6,4'-dihydroxy-7-O-glucosyl isoflavone
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + biochanin A 7-O-glucoside
CoA + biochanin A 7-O-glucoside-6''-O-malonylester
show the reaction diagram
-
-
-
?
malonyl-CoA + cyanidin 3,5-O-di-beta-D-glucoside
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + daidzein 7-O-glucoside
CoA + daidzein 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
malonyl-CoA + daidzin
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + formononetin 7-O-glucoside
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + formononetin 7-O-glucoside
CoA + formononetin 7-O-glucoside-6''-O-malonylester
show the reaction diagram
-
-
-
?
malonyl-CoA + genistin
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + hyperoside
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + isoflavone
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + isoquercitrin
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + kaempferol 7-O-glucoside
CoA + kaempferol 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
malonyl-CoA + keracyanin
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + kuromanin
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + naringenin 7-O-glucoside
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + naringenin 7-O-neohesperidoside
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
malonyl-CoA + orobol 7-O-glucoside
CoA + orobol 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
malonyl-CoA + pratensein 7-O-glucoside
CoA + pratensein 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
malonyl-CoA + rutin
?
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
naringenin 7-O-glucoside + malonyl-CoA
CoA + naringenin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
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16% of the activity with apiin
-
-
?
quercetagetin 7-O-glucoside + malonyl-CoA
CoA + quercetagetin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
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-
-
-
?
quercetin 3-O-glucoside + malonyl-CoA
CoA + quercetin 3-O-glucoside 6''-O-malonylester
show the reaction diagram
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8% of the activity with apiin
-
-
?
quercetin 7-O-glucoside + malonyl-CoA
CoA + quercetin 7-O-glucoside 6''-O-malonylester
show the reaction diagram
-
-
-
-
?
additional information
?
-
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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
apigenin 7-O-apiosylglucoside + malonyl-CoA
apigenin 7-O-apiosylglucoside -6''-O-malonylester + CoA
show the reaction diagram
additional information
?
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-
last step in biosynthesis of flavonoid glycosides
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.054
(-)-maackiain 3-O-beta-D-glucoside
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-
0.11
2',4,4'-trihydroxychalcone 4'-O-glucoside
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0.014 - 0.16
Apigenin 7-O-glucoside
0.01
apiin
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-
0.036
Biochanin A
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-
0.065
daidzein 7-O-glucoside
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-
0.024
formononetin
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-
0.0512 - 0.736
formononetin 7-O-glucoside
0.088
genistein 7-O-glucoside
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-
0.114 - 0.3094
genistin
0.067
kaempferol 7-O-glucoside
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-
0.02 - 0.47
Luteolin 7-O-glucoside
0.006 - 0.5539
malonyl-CoA
0.028 - 0.1256
naringenin 7-O-glucoside
0.0063 - 0.0713
naringenin 7-O-neohesperidoside
0.46
orobol 7-O-glucoside
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-
0.098
pratensein 7-O-glucoside
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-
0.335
quercetagetin 7-O-glucoside
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0.381
quercetin 7-O-glucoside
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0.101
succinyl-CoA
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1152 - 1.52
formononetin 7-O-glucoside
0.08 - 6.57
genistin
0.2308 - 3.952
malonyl-CoA
0.6249 - 3.89
naringenin 7-O-glucoside
1.01 - 3.2
naringenin 7-O-neohesperidoside
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 9.5
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about 50% of activity maximum at pH 6.5 and 9.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
assay at; assay at; assay at
45 - 50
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
112000
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gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 50000, SDS-PAGE
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
acidic pH leads to rapid denaturation
486143
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
above 2 min, destroyed
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
most stable in Tris buffer at pH 8, unstable to repeated freezing and thawing, dithioerythritol stabilizes
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 10% glycerol, stable for 4 months
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-70°C, partially purified enzyme is stable for several months, extensively purified enzyme loses 50% of activity within 2-3 days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overexpression in Arabidopsis thaliana; overexpression in Arabidopsis thaliana; overexpression in Arabidopsis thaliana
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
decreased expression by copper treatment; decreased expression by drought stress; decreased expression by drought stress
high expression in root and leaf, induced expression by copper treatment, slightly induced expression after elicitation of a root cell suspension culture by yeast elicitor; high expression in root and leaf, induced expression by copper treatment, slightly induced expression after elicitation of a root cell suspension culture by yeast elicitor; induced expression by drought stress and fungal infection
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
health-promoting neutraceutical; health-promoting neutraceutical; health-promoting neutraceutical
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LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.115)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)