Information on EC 2.1.1.232 - naringenin 7-O-methyltransferase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.1.1.232
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RECOMMENDED NAME
GeneOntology No.
naringenin 7-O-methyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + (2S)-naringenin = S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sakuranetin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:(2S)-5,7,4'-trihydroxyflavanone 7-O-methyltransferase
The enzyme is involved in the biosynthesis of the sakuranetin, an inducible defense mechanism of the plant Oryza sativa (Asian rice) against pathogen attack.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Oryza sativa L. Hitomebore
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Manually annotated by BRENDA team
Oryza sativa Nipponbare
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Manually annotated by BRENDA team
7-O-methyltransferase; gene SaOMT or SAV_2382
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
naringenin 7-O-methyltransferase is a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice
physiological function
additional information
sakuranetin has anti-inflammatory activity, anti-mutagenic activity, anti-pathogenic activities against Helicobacter pylori, Leishmania, and Trypanosoma and contributes to the maintenance of glucose homeostasis in animals
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
show the reaction diagram
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
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
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ba2+
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5 mM, 60% inhibition
Ca2+
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5 mM, 63% inhibition
Cd2+
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5 mM, complete inhibition
Co2+
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5 mM, 39% inhibition
Cu2+
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5 mM, complete inhibition
EDTA
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10 mM, 31% inhibition
Hg2+
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5 mM, complete inhibition
Mg2+
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5 mM, 40% inhibition
Mn2+
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5 mM, complete inhibition
Ni2+
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5 mM, complete inhibition
Zn2+
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5 mM, complete inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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application of methionine on wounded rice leaf stimulates naringenin 7-O-methyltransferase activity. The induction pathway is not regulated by ethylene or jasmonic acid
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0019
(2S)-naringenin
pH 8.5, 30C, purified recombinant GST-tagged NOMT
additional information
additional information
kinetic analysis, overview
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
25
(2S)-naringenin
Oryza sativa
I2FFE9
pH 8.5, 30C, purified recombinant GST-tagged NOMT
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0036
purified NOMT, pH 8.5, 28C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 9
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Tris-HCl buffer
8 - 10
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glycine-NaOH buffer
8.5
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28 - 30
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
38000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
after affinity chromatography, the enzyme becomes labile, losing almost all activity after 24 h storage at 4C or at -20C
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enzyme preparation after gel filtration retains more than 50% of its activity after 2 weeks at -20C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, enzyme in crude homogenates is stable for over 1 month
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purification of native enzyme 400fold from caffeic acid 3-O-methyltransferase-deficient mutant rice plant leaves
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purification of native enzyme 400fold from caffeic acid 3-O-methyltransferase-deficient oscomt1 mutant rice plant leaves induced with UV-light by ammonium sulfate fractionation and adenosine affinity chromatography, recombinant GST-tagged NOMT from Escherichia coli strain Rosetta II (DE3) by glutathione affinity chromatography and ultrafiltration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene Os12g0240900, DNA and amino acid sequence determination and analysis
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gene Os12g0240900, DNA and amino acid sequence determination and analysis, expression of GST-tagged NOMT in Escherichia coli strain Rosetta II (DE3)
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme expression is inducible by by ultraviolet irradiation, CuCl2 treatment, jasmonic acid treatment, and infection by phytopathogens, e.g. fungus Magnaporthe oryzae
gene Os12g0240900 expression is inducible by CuCl2, jasmonic acid, and phytopathogenic infection
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increases upon irradiation with UV light
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increases upon irradiation with UV light; the enzyme is induced by UV irradiation, jasmonic acid and CuCl2 (weak)
Oryza sativa L. Hitomebore
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induction of naringenin 7-O-methyltransferase by amino acid conjugates of jasmonic acid. The (-)-phenylalanine conjugate, one of the active compounds, is characterized by high activity for enzyme induction and low phytotoxicity against rice growth. Both (+)-enantiomers of the conjugates and free amino acids do not show any activity. The amino acid conjugate of jasmonic acid is speculated to be the later component in the signaling transduction chain in stressed rice plants
the enzyme is induced by UV irradiation, jasmonic acid and CuCl2 (weak)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
the recombinant SaOMT is used for 7-O-methylation of naringenin in recombinantly engineered production of 7-O-methyl aromadendrin, which is important in medicinal applications, via sakuranetin from 4-coumaric acid in Escherichia coli, overview