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S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 7,2'-dihydroxy-4'-methoxyisoflavone
S-adenosyl-L-homocysteine + 2-hydroxy-7,4'-dimethoxyisoflavone
-
i.e. 2'-hydroxyformononetin. 55% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
additional information
?
-
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein, about 7% of the activity with 6,7,4'-trihydroxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein. 12.9% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
-
i.e. genistein. 50% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein. 49% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein. 61% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
(i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
136% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
-
i.e. glycitein. 178% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
preferred substrate
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
35% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
44% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
41% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
43% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
i.e. glycitein, 39% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
i.e. glycitein, 52% the activity with 6,7,4'-trihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
i.e. glycitein, preferred substrate
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
i.e. dihydrodaidzein. 15.6% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
i.e. dihydrodaidzein. 70% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein
i.e. isoformononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein
i.e. isoformononetin
-
?
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
-
?
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
-
?
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)
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The activity of alfalfa IOMT as an elicitor-inducible, operationally soluble enzyme with 7-position specificity for daidzein in vitro
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein
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
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The activity of alfalfa IOMT as an elicitor-inducible, operationally soluble enzyme with 7-position specificity for daidzein in vitro
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. 21% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. Preferred substrate
-
-
?
additional information
?
-
-
IOMT II does not catalyse the methylation of apigenin, kaempferol, flavonoids mono-hydroxylated in the 2,3,4,5, or 7 positions, flavanones such as naringenin or coumestans such as coumestrol
-
-
?
additional information
?
-
no activity with apigenin (a flavone), naringenine (a falvanone)
-
-
?
additional information
?
-
-
no activity with apigenin (a flavone), naringenine (a falvanone)
-
-
?
additional information
?
-
-
no activity with 6,7-dihydroxy-4'-methoxyisoflavone
-
-
?
additional information
?
-
no activity with 6,7-dihydroxy-4'-methoxyisoflavone
-
-
?
additional information
?
-
no activity with 6,7-dihydroxy-4'-methoxyisoflavone
-
-
?
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S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein
i.e. isoformononetin
-
?
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
-
?
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
-
?
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
-
?
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Dalkin, K.; Edwards, R.; Edington, B.; Dixon, R.A.
Stress responses in alfalfa (Medicago sativa L.). I. Induction of phenylpropanoid biosynthesis and hydrolytic enzymes in elicitor-treated cell suspension cultures
Plant Physiol.
92
440-446
1990
Medicago sativa
brenda
He, X.Z.; Dixon, R.A.
Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4'-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa
Plant Cell
12
1689-1702
2000
Medicago sativa, Medicago sativa cv Regen SY
brenda
He, X.Z.; Dixon, R.A.
Affinity chromatography, substrate/product specificity, and amino acid sequence analysis of an isoflavone O-methyltransferase from alfalfa (Medicago sativa L.)
Arch. Biochem. Biophys.
336
121-129
1996
Medicago sativa (O24529), Medicago sativa
brenda
He, X.Z.; Reddy, J.T.; Dixon, R.A.
Stress responses in alfalfa (Medicago sativa L). XXII. cDNA cloning and characterization of an elicitor-inducible isoflavone 7-O-methyltransferase
Plant Mol. Biol.
36
43-54
1998
Medicago sativa (O24529), Medicago sativa
brenda
Liu, C.J.; Dixon, R.A.
Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis
Plant Cell
13
2643-2658
2001
Medicago sativa (O24529), Medicago sativa, Medicago sativa cv Regen SY (O24529)
brenda
Zubieta, C.; He, X.Z.; Dixon, R.A.; Noel, J.P.
Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases
Nat. Struct. Biol.
8
271-279
2001
Medicago sativa (O24529), Medicago sativa
brenda
Deavours, B.E.; Liu, C.J.; Naoumkina, M.A.; Tang, Y.; Farag, M.A.; Sumner, L.W.; Noel, J.P.; Dixon, R.A.
Functional analysis of members of the isoflavone and isoflavanone O-methyltransferase enzyme families from the model legume Medicago truncatula
Plant Mol. Biol.
62
715-733
2006
Medicago truncatula, Medicago truncatula (Q06YR3), Medicago truncatula (Q06YR4)
brenda