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Information on EC 2.1.1.232 - naringenin 7-O-methyltransferase
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EC Tree
2.1.1.232 naringenin 7-O-methyltransferaseIUBMB Comments
The enzyme is involved in the biosynthesis of the sakuranetin, an inducible defense mechanism of the plant Oryza sativa (Asian rice) against pathogen attack.
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Word Map
- 2.1.1.232
- sakuranetin
-
phytoalexins
-
jasmonic
- flavonoid
- oryzae
- sativa
-
momilactone
-
caffeic
-
3-o-methyltransferase
- nipponbare
- synthesis
-
biosynthesized
-
diterpenoid
-
phytopathogenic
-
uv-treated
-
purest
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
naringenin 7-o-methyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
7-O-methyltransferase
NOMT
SaOMT
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + (2S)-naringenin = S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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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.
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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
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
S-adenosyl-L-methionine + dihydrokaempferol
S-adenosyl-L-homocysteine + 7-O-methyl aromadendrin
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
i.e. (2S)-naringenin
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
mass spectrometric and chiral analysis of sakuranetin product
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
reaction of NOMT
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
-
i.e. luteolin, 148% of the activity with naringenin
-
-
?
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
-
i.e. luteolin, 767% of the activity with naringenin, crude enzyme preparation
-
-
?
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
-
i.e. luteolin, 767% of the activity with naringenin, crude enzyme preparation
-
-
?
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
-
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
-
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
-
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
-
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
-
i.e. apigenin, 81% of the activity with naringenin
i.e. genkwanin
-
?
S-adenosyl-L-methionine + dihydrokaempferol
S-adenosyl-L-homocysteine + 7-O-methyl aromadendrin
-
7-O-methyl aromadendrin is an aglycone moiety of one of the important flavonoid-glycosides found in several plants with various medicinal applications
-
?
S-adenosyl-L-methionine + dihydrokaempferol
S-adenosyl-L-homocysteine + 7-O-methyl aromadendrin
-
7-O-methyl aromadendrin is an aglycone moiety of one of the important flavonoid-glycosides found in several plants with various medicinal applications
-
?
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
?
-
the enzyme is also active on kaempferol, apigenin, luteolin, liquiritigenin, and quercetin
-
-
?
additional information
?
-
-
the enzyme is also active on kaempferol, apigenin, luteolin, liquiritigenin, and quercetin
-
-
?
additional information
?
-
-
no activity with 5,7,4'-trihydroxyisoflavone (genistein), 7,4'-dihydroxyisoflavone (daidzein) and 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin)
-
-
?
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)
-
-
?
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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
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
S-adenosyl-L-methionine + dihydrokaempferol
S-adenosyl-L-homocysteine + 7-O-methyl aromadendrin
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
-
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
-
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
-
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
-
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
-
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
-
i.e. (2S)-naringenin. Key enzyme of sakuranetin biosynthesis
i.e. (2S)-sakuranetin
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
reaction of NOMT
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + (2S)-sakuranetin
-
-
-
?
S-adenosyl-L-methionine + dihydrokaempferol
S-adenosyl-L-homocysteine + 7-O-methyl aromadendrin
-
7-O-methyl aromadendrin is an aglycone moiety of one of the important flavonoid-glycosides found in several plants with various medicinal applications
-
?
S-adenosyl-L-methionine + dihydrokaempferol
S-adenosyl-L-homocysteine + 7-O-methyl aromadendrin
-
7-O-methyl aromadendrin is an aglycone moiety of one of the important flavonoid-glycosides found in several plants with various medicinal applications
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
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
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0019
(2S)-naringenin
pH 8.5, 30°C, purified recombinant GST-tagged NOMT
additional information
additional information
kinetic analysis, overview
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
susceptible N and resistant IL7 rice cultivars, from Nipponbare, gene OsNOMT
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
irradiated with short wave UV light. NO activity in healthy rice leaves
brenda
-
application of methionine on wounded rice leaf stimulates naringenin 7-O-methyltransferase activity
brenda
-
irradiated with short wave UV light. NO activity in healthy rice leaves
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
additional information
metabolism
naringenin 7-O-methyltransferase is a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice
metabolism
the enzyme catalyzes the last step in sakuranetin biosynthesis, induced expression of a phytoalexin biosynthesis gene OsNOMT for naringenin 7-O-methyltransferase is found before accumulation of sakuranetin in both cultivars
metabolism
the enzyme catalyzes the last step in the biosynthesis of the bioactive flavonoid sakuranetin, biosynthetic pathway starting with glucose, overview
metabolism
the key enzyme produces the rice flavonoid phytoalexin sakuranetin, the enzyme catalyzes the last step in sakuranetin biosynthesis, rice phytoalxin and diterpenoid metabolism, overview
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
-
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
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
-
Sakuranetin is a the major flavonoid phytoalexin in rice, and is useful as plant antibiotic and pharmaceutical agent
physiological function
te enzyme is required for biosynthesis of sakuranetin, a phytoalexin in rice, enzyme upregulation might lead to increased plant pathogen resistance
physiological function
the key enzyme produces the rice flavonoid phytoalexin sakuranetin for resistance against blast fungus infection. The concentration of sakuranetin accumulated in infected regions in the resistant rice line is effective enough to restrict the fungus, while that in susceptible rice is too low for it. Blast fungus converts sakuranetin to less toxic compounds
physiological function
-
leaves of rice cultivar Nipponbare predominantly accumulate the phytoalexin sakuranetin after jasmonic acid induction. The Kasalath cultivar accumulates only low amounts of sakuranetin. Both NOMT expression and NOMT enzymatic activity are lower in Kasalath than in Nipponbare. A proline to threonine substitution in Kasalath relative to Nipponbare NOMT is the main cause of the lower enzymatic activity. The relative amounts of naringenin and sakuranetin may provide protection against specific pathogen profiles in different rice-growing environments. Naringenin is more effective against bacterial pathogens and sakuranetin is more effective against fungal pathogens
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
-
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
-
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
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
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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). NOMT_ORYSJ
375
0
39702
Swiss-Prot
other Location (Reliability: 1)
Q79ZE8_STRAW
Streptomyces avermitilis (strain ATCC 31267 / DSM 46492 / JCM 5070 / NBRC 14893 / NCIMB 12804 / NRRL 8165 / MA-4680)
359
0
37545
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
T130P
-
mutation in cultivar Kassalth gene to match the corresonding residue in cultivar Nipponbare. Mutant shows activity comparable to Nipponbare NOMT
additional information
additional information
-
domain swapping experiments between Nipponbare and Kasalath NOMT genes. The replacement of the Kasalath O-methyltransferase domain with the Nipponbare domain increases the enzyme activity to the level of the Nipponbare enzyme
additional information
-
construction of a multifunctional flavonoid O-methyltransferase fusing tomato 3'-O-methyltransferase OMT3 and Oryza sativa naringenin 7-O-methyltransferase NOMT. The OMT3/NOMT fusion enzyme possesses both 3'- and 7-OMT activities to diverse flavonoid substrates, which are comparable to those of individual OMT3 and NOMT. The OMT3/OsNOMT enzyme also shows 3'- and 7-OMT activity for 7- or 3'-O-methylflavonoids, respectively. The biotransformation of the flavonoids quercetin, luteolin, eriodictyol, and taxifolin using OMT3/NOMT-transformed Escherichia coli generates corresponding di-O-methylflavonoids, rhamnazin, velutin, 3',7-di-O-methyleriodictyol, and 3',7-di-Omethyltaxifolin, respectively
additional information
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
additional information
production of 7-O-methyl aromadendrin in Escherichia coli strain BL21(DE3) recombinantly expressing the genes of several origins encoding enzymes 4-coumaratecoenzyme A ligase from Petroselinum crispum, chalcone synthase from Petunia hybrida, and chalcone flavanone isomerase from Medicago sativa to produce (2S)-naringenin, and further genes encoding flavanone-3-hydroxylase from Arabidopsis thaliana and the 7-O-methyltransferase from Streptomyces avermitilis to transform (2S)-naringenin into 7-O-methyl aromadendrin via dihydrokaempferol and (2S)-sakuranetin, method and pathway, overview
additional information
-
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
-
additional information
-
production of 7-O-methyl aromadendrin in Escherichia coli strain BL21(DE3) recombinantly expressing the genes of several origins encoding enzymes 4-coumaratecoenzyme A ligase from Petroselinum crispum, chalcone synthase from Petunia hybrida, and chalcone flavanone isomerase from Medicago sativa to produce (2S)-naringenin, and further genes encoding flavanone-3-hydroxylase from Arabidopsis thaliana and the 7-O-methyltransferase from Streptomyces avermitilis to transform (2S)-naringenin into 7-O-methyl aromadendrin via dihydrokaempferol and (2S)-sakuranetin, method and pathway, overview
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
after affinity chromatography, the enzyme becomes labile, losing almost all activity after 24 h storage at 4°C or at -20°C
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enzyme preparation after gel filtration retains more than 50% of its activity after 2 weeks at -20°C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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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
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene Os12g0240900, DNA and amino acid sequence determination and analysis, expression of GST-tagged NOMT in Escherichia coli strain Rosetta II (DE3)
gene Os12g0240900, DNA and amino acid sequence determination and analysis, recombinant expression in Escherichia coli, functional coexpression of plant enzymes, e.g. 4-coumaroyl-CoA ligase and chalcone synthase, of different origins catalyzing steps in flavonoid biosynthesis pathways for production of naringenin from p-coumaric acid and synthesis of ponciretin and sakuranetin from naringenin in engineered and transformed Escherichia coli strain BL21(DE3)
subcloning in Escherichia coli strain DH5alpha, recombinant expression in Arabidopsis thaliana
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
blast fungus infection induces the enzyme and phytoalexin sakuranetin production in rice, overview
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
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)
the transcription of gene Os12g0240900 and enzyme expression is induced by jasmonic acid in rice leaves
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
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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
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the enzyme is induced by UV irradiation, jasmonic acid and CuCl2 (weak)
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
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
synthesis
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production of sakuranetin (7-O-methylnaringenin) and ponciretin (4-O-methylnaringenin) in Escherichia coli by reconstruction of the naringenin biosynthesis pathway. Engineering the shikimic acid pathway, and overexpression of several genes for the biosynthesis of ponciretin and sakuranetin such as tyrosine ammonia lyase, 4-coumaroyl CoA ligase, chalcone synthase, and O-methyltransferase and deletion of isocitrate dehydrogenase finally gives ponciretin and sakuranetin from glucose in Escherichia coli at the concentration of 42.5 mg/l and 40.1 mg/l, respectively
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
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Rakwal, R.; Hasegawa, M.; Kodama, O.
A methyltransferase for synthesis of the flavanone phytoalexin sakuranetin in rice leaves
Biochem. Biophys. Res. Commun.
222
732-735
1996
Oryza sativa, Oryza sativa L. Hitomebore
brenda
Tamogami, S.; Rakwal, R.; Kodama, O.
Phytoalexin production by amino acid conjugates of jasmonic acid through induction of naringenin-7-O-methyltransferase, a key enzyme on phytoalexin biosynthesis in rice (Oryza sativa L.)
FEBS Lett.
401
239-242
1997
Oryza sativa, Oryza sativa Nipponbare
brenda
Rakwal R, Agrawal GK, Yonekura M, Kodama O.
Naringenin 7-O-methyltransferase involved in the biosynthesis of the flavanone phytoalexin sakuranetin from rice (Oryza sativa L.)
Plant Sci.
155
213-221
2000
Oryza sativa, Oryza sativa L. Hitomebore
brenda
Nakazato, Y.; Tamogami, S.; Kawai, H.; Hasegawa, M.; Kodama, O.
Methionine-induced phytoalexin production in rice leaves
Biosci. Biotechnol. Biochem.
64
577-583
2000
Oryza sativa
brenda
Malla, S.; Koffas, M.A.; Kazlauskas, R.J.; Kim, B.G.
Production of 7-O-methyl aromadendrin, a medicinally valuable flavonoid, in Escherichia coli
Appl. Environ. Microbiol.
78
684-694
2012
Streptomyces avermitilis (Q79ZE8), Streptomyces avermitilis MA-4680 (Q79ZE8)
brenda
Shimizu, T.; Lin, F.; Hasegawa, M.; Nojiri, H.; Yamane, H.; Okada, K.
The potential bioproduction of the pharmaceutical agent sakuranetin, a flavonoid phytoalexin in rice
Bioengineered
3
352-357
2012
Oryza sativa
brenda
Shimizu, T.; Lin, F.; Hasegawa, M.; Okada, K.; Nojiri, H.; Yamane, H.
Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice
J. Biol. Chem.
287
19315-19325
2012
Oryza sativa (I2FFE9), Oryza sativa
brenda
Kim, M.; Kim, B.; Ahn, J.
Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli
Appl. Microbiol. Biotechnol.
97
7195-7204
2013
Oryza sativa (Q0IP69)
brenda
Yamane, H.
Biosynthesis of phytoalexins and regulatory mechanisms of it in rice
Biosci. Biotechnol. Biochem.
77
1141-1148
2013
Oryza sativa (Q0IP69), Oryza sativa
brenda
Hasegawa, M.; Mitsuhara, I.; Seo, S.; Okada, K.; Yamane, H.; Iwai, T.; Ohashi, Y.
Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus
Molecules
19
11404-11418
2014
Oryza sativa (Q0IP69), Oryza sativa
brenda
Kim, B.
Biosynthesis of bioactive isokaemferide from naringenin in Escherichia coli
J. Appl. Biol. Chem.
62
1-6
2019
Oryza sativa
brenda
Lee, D.; Park, H.L.; Lee, S.W.; Bhoo, S.H.; Cho, M.H.
Biotechnological production of dimethoxyflavonoids using a fusion flavonoid O-methyltransferase possessing both 3- and 7-O-methyltransferase activities
J. Nat. Prod.
80
1467-1474
2017
Solanum lycopersicum
brenda
Murata, K.; Kitano, T.; Yoshimoto, R.; Takata, R.; Ube, N.; Ueno, K.; Ueno, M.; Yabuta, Y.; Teraishi, M.; Holland, C.; Jander, G.; Okumoto, Y.; Mori, N.; Ishihara, A.
Natural variation in the expression and catalytic act