Information on EC 2.1.1.232 - naringenin 7-O-methyltransferase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


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

EC NUMBER
COMMENTARY
2.1.1.232
-
RECOMMENDED NAME
GeneOntology No.
naringenin 7-O-methyltransferase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
S-adenosyl-L-methionine + (2S)-naringenin = S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
sakuranetin biosynthesis
-
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7-O-methyltransferase
Q79ZE8
-
NOMT
I2FFE9
-
NOMT
Oryza sativa L. Hitomebore
-
-
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
gene Os12g0240900
-
-
Manually annotated by BRENDA team
var. japonica and cv. Nipponbare, gene Os12g0240900
UniProt
Manually annotated by BRENDA team
Oryza sativa L. Hitomebore
-
-
-
Manually annotated by BRENDA team
Oryza sativa Nipponbare
-
-
-
Manually annotated by BRENDA team
7-O-methyltransferase; gene SaOMT or SAV_2382
Q79ZE8
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
-
the enzyme catalyzes the terminal step in the biosynthesis of the flavanone sakuranetin, the major phytoalexin produced by Oryza sativa that is involved in defense related response
physiological function
-
key enzyme of sakuranetin biosynthesis
physiological function
-
the enzyme is involved in the biosynthesis of the flavanone phytoalexin sakuranetin. Plants possess inducible defence mechanisms against pathogen attack that include the production of phytoalexins. The product of the reaction, sakuranetin is a major rice phytoalexin accumulating both in ultraviolet irradiated and blast infected as well as in copper chloride or jasmonic acid, treated rice leaves
physiological function
-
Sakuranetin is a the major flavonoid phytoalexin in rice, and is useful as plant antibiotic and pharmaceutical agent
physiological function
I2FFE9
naringenin 7-O-methyltransferase is a key enzyme in biosynthesis of major flavonoid phytoalexin sakuranetin in rice, sakuranetin is a useful compound as a plant antibiotic and a potential pharmaceutical agent
physiological function
Oryza sativa L. Hitomebore
-
the enzyme catalyzes the terminal step in the biosynthesis of the flavanone sakuranetin, the major phytoalexin produced by Oryza sativa that is involved in defense related response; the enzyme is involved in the biosynthesis of the flavanone phytoalexin sakuranetin. Plants possess inducible defence mechanisms against pathogen attack that include the production of phytoalexins. The product of the reaction, sakuranetin is a major rice phytoalexin accumulating both in ultraviolet irradiated and blast infected as well as in copper chloride or jasmonic acid, treated rice leaves
-
physiological function
Oryza sativa Nipponbare
-
key enzyme of sakuranetin biosynthesis
-
metabolism
I2FFE9
naringenin 7-O-methyltransferase is a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice
additional information
I2FFE9
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 ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
i.e. (2S)-naringenin. Key enzyme of sakuranetin biosynthesis
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
-
i.e. (2S)-naringenin. The enzyme catalyzes the terminal step in the biosynthesis of the flavanone sakuranetin, the major phytoalexin produced by Oryza sativa that is involved in defense related response
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
-
i.e. (2S)-naringenin. The enzyme is involved in the biosynthesis of the flavanone phytoalexin sakuranetin. Plants possess inducible defence mechanisms against pathogen attack that include the production of phytoalexins
i.e. (2S)-sakuranetin. The product of the reaction, sakuranetin is a major rice phytoalexin accumulating both in ultraviolet irradiated and blast infected as well as in copper chloride or jasmonic acid, treated rice leaves
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
-
i.e. (2S)-naringenin
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa Nipponbare
-
i.e. (2S)-naringenin. Key enzyme of sakuranetin biosynthesis, i.e. (2S)-naringenin
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. (2S)-naringenin. The enzyme catalyzes the terminal step in the biosynthesis of the flavanone sakuranetin, the major phytoalexin produced by Oryza sativa that is involved in defense related response, i.e. (2S)-naringenin
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. (2S)-naringenin. The enzyme is involved in the biosynthesis of the flavanone phytoalexin sakuranetin. Plants possess inducible defence mechanisms against pathogen attack that include the production of phytoalexins
i.e. (2S)-sakuranetin. The product of the reaction, sakuranetin is a major rice phytoalexin accumulating both in ultraviolet irradiated and blast infected as well as in copper chloride or jasmonic acid, treated rice leaves
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. (2S)-naringenin
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
I2FFE9
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
Q79ZE8, -
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
I2FFE9
-
mass spectrometric and chiral analysis of sakuranetin product
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 5,3',4'-trihydroxy-7-methoxyflavanone
show the reaction diagram
-
i.e. luteolin, 148% of the activity with naringenin
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 5,3',4'-trihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa, Oryza sativa L. Hitomebore
-
i.e. luteolin, 767% of the activity with naringenin, crude enzyme preparation
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 5,3',4'-trihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. luteolin, 148% of the activity with naringenin
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
-
i.e. apigenin, 81% of the activity with naringenin
i.e. genkwanin
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
Oryza sativa, Oryza sativa L. Hitomebore
-
i.e. apigenin, 98% of the activity with naringenin, crude enzyme preparation
i.e. genkwanin
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. apigenin, 81% of the activity with naringenin
i.e. genkwanin
-
?
additional information
?
-
-
no activity with 3,5,7,4'-tetrahydroxyflavanone (kaempferol), 5,7,4'-trihydroxyisoflavone (genistein), 7,4'-dihydroxyisoflavone (daidzein), 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin), or 3,4-dihydroxycinnamic acid (caffeic acid)
-
-
-
additional information
?
-
-
no activity with 5,7,4'-trihydroxyisoflavone (genistein), 7,4'-dihydroxyisoflavone (daidzein) and 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin)
-
-
-
additional information
?
-
I2FFE9
the enzyme is also active on kaempferol, apigenin, luteolin, liquiritigenin, and quercetin
-
-
-
additional information
?
-
Oryza sativa L. Hitomebore
-
no activity with 5,7,4'-trihydroxyisoflavone (genistein), 7,4'-dihydroxyisoflavone (daidzein) and 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin)
-
-
-
additional information
?
-
Oryza sativa L. Hitomebore
-
no activity with 3,5,7,4'-tetrahydroxyflavanone (kaempferol), 5,7,4'-trihydroxyisoflavone (genistein), 7,4'-dihydroxyisoflavone (daidzein), 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin), or 3,4-dihydroxycinnamic acid (caffeic acid)
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
i.e. (2S)-naringenin. Key enzyme of sakuranetin biosynthesis
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
-
i.e. (2S)-naringenin. The enzyme catalyzes the terminal step in the biosynthesis of the flavanone sakuranetin, the major phytoalexin produced by Oryza sativa that is involved in defense related response
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
-
i.e. (2S)-naringenin. The enzyme is involved in the biosynthesis of the flavanone phytoalexin sakuranetin. Plants possess inducible defence mechanisms against pathogen attack that include the production of phytoalexins
i.e. (2S)-sakuranetin. The product of the reaction, sakuranetin is a major rice phytoalexin accumulating both in ultraviolet irradiated and blast infected as well as in copper chloride or jasmonic acid, treated rice leaves
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa Nipponbare
-
i.e. (2S)-naringenin. Key enzyme of sakuranetin biosynthesis
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. (2S)-naringenin. The enzyme catalyzes the terminal step in the biosynthesis of the flavanone sakuranetin, the major phytoalexin produced by Oryza sativa that is involved in defense related response
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
Oryza sativa L. Hitomebore
-
i.e. (2S)-naringenin. The enzyme is involved in the biosynthesis of the flavanone phytoalexin sakuranetin. Plants possess inducible defence mechanisms against pathogen attack that include the production of phytoalexins
i.e. (2S)-sakuranetin. The product of the reaction, sakuranetin is a major rice phytoalexin accumulating both in ultraviolet irradiated and blast infected as well as in copper chloride or jasmonic acid, treated rice leaves
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
show the reaction diagram
I2FFE9
-
-
-
?
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
S-adenosyl-L-methionine
Q79ZE8, -
-
S-adenosyl-L-methionine
-
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Ba2+
-
5 mM, 60% inhibition
Ca2+
-
5 mM, 63% inhibition
Cd2+
-
5 mM, complete inhibition
Co2+
-
5 mM, 39% inhibition
Cu2+
-
5 mM, complete inhibition
EDTA
-
10 mM, 31% inhibition
Hg2+
-
5 mM, complete inhibition
Mg2+
-
5 mM, 40% inhibition
Mn2+
-
5 mM, complete inhibition
Ni2+
-
5 mM, complete inhibition
Zn2+
-
5 mM, complete inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
-
application of methionine on wounded rice leaf stimulates naringenin 7-O-methyltransferase activity. The induction pathway is not regulated by ethylene or jasmonic acid
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0019
-
(2S)-naringenin
I2FFE9
pH 8.5, 30C, purified recombinant GST-tagged NOMT
additional information
-
additional information
I2FFE9
kinetic analysis, overview
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
25
-
(2S)-naringenin
I2FFE9
pH 8.5, 30C, purified recombinant GST-tagged NOMT
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.0036
-
I2FFE9
purified NOMT, pH 8.5, 28C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.5
9
-
Tris-HCl buffer
8
10
-
glycine-NaOH buffer
8.5
-
I2FFE9
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
28
30
I2FFE9
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
irradiated with short wave UV light. NO activity in healthy rice leaves
Manually annotated by BRENDA team
-
UV-irradiated
Manually annotated by BRENDA team
-
application of methionine on wounded rice leaf stimulates naringenin 7-O-methyltransferase activity
Manually annotated by BRENDA team
Oryza sativa L. Hitomebore
-
irradiated with short wave UV light. NO activity in healthy rice leaves; UV-irradiated
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
38000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
monomer
-
1 * 41000, SDS-PAGE
monomer
Oryza sativa L. Hitomebore
-
1 * 41000, SDS-PAGE
-
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
after affinity chromatography, the enzyme becomes labile, losing almost all activity after 24 h storage at 4C or at -20C
-
enzyme preparation after gel filtration retains more than 50% of its activity after 2 weeks at -20C
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, enzyme in crude homogenates is stable for over 1 month
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
purification of native enzyme 400fold from caffeic acid 3-O-methyltransferase-deficient mutant rice plant leaves
-
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
I2FFE9
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
gene Os12g0240900, DNA and amino acid sequence determination and analysis
-
gene Os12g0240900, DNA and amino acid sequence determination and analysis, expression of GST-tagged NOMT in Escherichia coli strain Rosetta II (DE3)
I2FFE9
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
increases upon irradiation with UV light
-
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)
-
gene Os12g0240900 expression is inducible by CuCl2, jasmonic acid, and phytopathogenic infection
-
enzyme expression is inducible by by ultraviolet irradiation, CuCl2 treatment, jasmonic acid treatment, and infection by phytopathogens, e.g. fungus Magnaporthe oryzae
I2FFE9
increases upon irradiation with UV light; the enzyme is induced by UV irradiation, jasmonic acid and CuCl2 (weak)
Oryza sativa L. Hitomebore
-
-
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
Oryza sativa Nipponbare
-
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
Q79ZE8, -
the recombinant SaOMT is used for 7-O-methylation of naringenin in recombinantly engineered production of 7-O-methyl aromadendrin via sakuranetin from 4-coumaric acid in Escherichia coli, overview
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
synthesis
Q79ZE8, -
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