2.1.1.150: isoflavone 7-O-methyltransferase
This is an abbreviated version!
For detailed information about isoflavone 7-O-methyltransferase, go to the full flat file.
Word Map on EC 2.1.1.150
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2.1.1.150
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isoflavonoids
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alfalfa
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phytoalexins
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daidzein
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medicago
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sativa
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medicarpin
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formononetin
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pisum
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phenylpropanoid
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regiospecific
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leguminous
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chalcone
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4'-o-methylated
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b-rings
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7-hydroxyl
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caffeic
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4'-o-methyltransferase
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7-o-methylation
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cinnamic
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4\'-hydroxyl
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elicitor-induced
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chickpea
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pterocarpan
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elicitor-treated
- 2.1.1.150
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isoflavonoids
- alfalfa
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phytoalexins
- daidzein
-
medicago
- sativa
- medicarpin
- formononetin
-
pisum
-
phenylpropanoid
-
regiospecific
-
leguminous
- chalcone
-
4'-o-methylated
-
b-rings
-
7-hydroxyl
-
caffeic
-
4'-o-methyltransferase
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7-o-methylation
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cinnamic
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4\'-hydroxyl
-
elicitor-induced
- chickpea
-
pterocarpan
-
elicitor-treated
Reaction
Synonyms
7-IOMT, 8-IOMT, HI4'OMT, IOMT, IOMT II, IOMT8, isoflavone methyltransferase, isoflavone O-methyltransferase, methyltransferase, 4'-hydroxyisoflavone, MtIOMT1, MtIOMT2, MtIOMT3
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Natural Substrates Products
Natural Substrates Products on EC 2.1.1.150 - isoflavone 7-O-methyltransferase
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REACTION DIAGRAM
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein
i.e. isoformononetin
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?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein, about 20% of the activity with 6,7,4'-trihydroxyisoflavone (i.e. glycitein). Key enzyme in the biosynthesis of the phytoalexin medicarpin in Medicago sativa
i.e. formononetin
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?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
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i.e. daidzein. 4'-O-Methylation of an isoflavonoid intermediate is a key reaction in the biosynthesis of the phytoalexin medicarpin in legumes. However, isoflavone O-methyltransferase from alfalfa converts the isoflavone daidzein to 7-O-methyldaidzein (isoformononetin) in vitro as well as in vivo in unchallenged leaves of transgenic alfalfa ectopically expressing IOMT. In contrast, elicitation of IOMT-overexpressing plants with CuC2 or infecting these plants with Phoma medicaginis leads to greater accumulation of formononetin (4'-O-methyl daidzein) and medicarpin in the leaves than does elicitation or infection of control plants, and no isoformononetin is detected
i.e. formononetin
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?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The operationally soluble IOMT localizes to endomembranes after elicitation of the isoflavonoid pathway. IOMT colocalizes with the endoplasmic reticulumassociated isoflavone synthase cytochrome P450 to ensure rapid B-ring methylation of the unstable 2,7,4'-trihydroxyisoflavanone product of isoflavone synthase, thereby preventing its dehydration to daidzein and subsequent A-ring methylation by free IOMT. In this way, metabolic channeling at the entry point into isoflavonoid phytoalexin biosynthesis protects an unstable intermediate from an unproductive metabolic conversion
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein. 4'-O-Methylation of an isoflavonoid intermediate is a key reaction in the biosynthesis of the phytoalexin medicarpin in legumes. However, isoflavone O-methyltransferase from alfalfa converts the isoflavone daidzein to 7-O-methyldaidzein (isoformononetin) in vitro as well as in vivo in unchallenged leaves of transgenic alfalfa ectopically expressing IOMT. In contrast, elicitation of IOMT-overexpressing plants with CuC2 or infecting these plants with Phoma medicaginis leads to greater accumulation of formononetin (4'-O-methyl daidzein) and medicarpin in the leaves than does elicitation or infection of control plants, and no isoformononetin is detected
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The operationally soluble IOMT localizes to endomembranes after elicitation of the isoflavonoid pathway. IOMT colocalizes with the endoplasmic reticulumassociated isoflavone synthase cytochrome P450 to ensure rapid B-ring methylation of the unstable 2,7,4'-trihydroxyisoflavanone product of isoflavone synthase, thereby preventing its dehydration to daidzein and subsequent A-ring methylation by free IOMT. In this way, metabolic channeling at the entry point into isoflavonoid phytoalexin biosynthesis protects an unstable intermediate from an unproductive metabolic conversion
i.e. formononetin
-
?