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EC Tree
IUBMB Comments The enzyme acts on the hydroxy group in the 4'-position of some flavones, flavanones and isoflavones. Kaempferol, apigenin and kaempferol triglucoside are substrates, as is genistein, which reacts more slowly. Compounds with an hydroxy group in the 3' and 4' positions, such as quercetin and eriodictyol, do not act as substrates. Similar to EC 2.1.1.75, apigenin 4'-O-methyltransferase and EC 2.1.1.83, 3,7-dimethylquercetin 4'-O-methyltransferase.
The enzyme appears in viruses and cellular organisms
Synonyms
cromt6, flavonoid methyltransferase,
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flavonoid methyltransferase
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flavonoid O-methyltransferase
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methyltransferase, flavonoid
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S-adenosyl-L-methionine:flavonoid 4-O-methyltransferase
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S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + kaempferide
S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + kaempferide
the enzyme acts on the hydroxy group in the 4'-position of some flavones, flavanones and isoflavones, kaempferol, apigenin and kaempferol triglucoside are substrates, as is genistein, which reacts more slowly, compounds with a hydroxy group in the 3' and 4' positions, such as quercetin and eriodictyol, do not act as substrates, similar to EC 2.1.1.75, apigenin 4'-O-methyltransferase and EC 2.1.1.83, 3,7-dimethylquercitin 4'-O-methyltransferase, ping-pong mechanism excluding the formation of a ternary complex
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S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + kaempferide
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transfer of methyl group
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S-adenosyl-L-methionine:kaempferol 4'-O-methyltransferase
The enzyme acts on the hydroxy group in the 4'-position of some flavones, flavanones and isoflavones. Kaempferol, apigenin and kaempferol triglucoside are substrates, as is genistein, which reacts more slowly. Compounds with an hydroxy group in the 3' and 4' positions, such as quercetin and eriodictyol, do not act as substrates. Similar to EC 2.1.1.75, apigenin 4'-O-methyltransferase and EC 2.1.1.83, 3,7-dimethylquercetin 4'-O-methyltransferase.
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S-adenosyl-L-methionine + 4'-hydroxyflavanone
S-adenosyl-L-homocysteine + 4'-methoxyflavanone
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S-adenosyl-L-methionine + a flavonoid
S-adenosyl-L-homocysteine + a 4'-methoxyflavonoid
S-adenosyl-L-methionine + apigenin
S-adenosyl-L-homocysteine + acacetin
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4-methoxyapigenin
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?
S-adenosyl-L-methionine + chrysoeriol
S-adenosyl-L-homocysteine + 4'-methoxychrysoeriol
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good substrate
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?
S-adenosyl-L-methionine + eriodictyol
S-adenosyl-L-homocysteine + 4'-methoxyeriodictyol
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lower activity than with homoeriodictyol, isorhamnetin or chrysoeriol
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?
S-adenosyl-L-methionine + genistein
S-adenosyl-L-homocysteine + biochanin A
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4-methoxygenistein
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?
S-adenosyl-L-methionine + homoeriodictyol
S-adenosyl-L-homocysteine + 4'-methoxyhomoeriodictyol
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best substrate
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?
S-adenosyl-L-methionine + isorhamnetin
S-adenosyl-L-homocysteine + 4'-methoxyisorhamnetin
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good substrate
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?
S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + kaempferide
S-adenosyl-L-methionine + kaempferol 3-O-beta-D-glucopyranosyl-1,4-O-alpha-L-rhamnopyranosyl-1,2-beta-D-glucopyranoside
S-adenosyl-L-homocysteine + 4'-O-methylkaempferol 3-O-beta-D-glucopyranosyl-1,4-O-alpha-L-rhamnopyranosyl-1,2-beta-D-glucopyranoside
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 4'-methoxyquercetin
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lower activity than with homoeriodictyol, isorhamnetin or chrysoeriol
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additional information
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S-adenosyl-L-methionine + a flavonoid
S-adenosyl-L-homocysteine + a 4'-methoxyflavonoid
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4-OMT methylates the position 4 in the B-ring of flavonoids, uses flavonoids methylated in the 3-position of the B-ring to synthesize a 3,4-methylated product, a methylated flavanone, homoeriodictyol, is the best substrate
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S-adenosyl-L-methionine + a flavonoid
S-adenosyl-L-homocysteine + a 4'-methoxyflavonoid
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F 4-OMT specifically methylates the hydroxy substituent in 4-position of the flavones, flavanones and isoflavones in the presence of S-adenosyl-L-methionine, enzyme affinity for the substrate and catalytic efficiency decreases in the following order: 4-hydroxyflavones, 4-hydroxyflavanones, 4-hydroxyisoflavones, ping-pong mechanism, which excludes the formation of a ternary complex
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S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + kaempferide
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lower activity than with homoeriodictyol, isorhamnetin or chrysoeriol
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S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + kaempferide
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additional information
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not: naringenin, pentahydroxyflavanone, hesperetin, myricetin, 7,3-O-dimethylquercetin, 7-O-methylquercetin, syringetin, apigenin, luteolin, tricetin, velutin, dihydrokaempferol, dihydroquercetin, dihydromyricetin, 3-O-methyl-dihydroquercetin
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additional information
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the role of F 4-OMT is mainly defensive against parasites, rather than structural
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additional information
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not: 4-hydroxybenzoic acid, gallic acid, p-coumaric acid, caffeic acid, caffeoyl-CoA, quercetin, rutin, luteolin, eriodictyol, 3,4,7-trihydroxyisoflavone, datiscetin
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additional information
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the role of F 4-OMT is mainly defensive against parasites, rather than structural
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additional information
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no divalent metal ion requirement
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Ca2+
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10 mM, 19% inhibition
iodoacetamide
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1 mM, 60% inhibition
Mg2+
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10 mM, 27% inhibition
Mn2+
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1 mM: 21% inhibition, 10 mM: 57% inhibition
Phenylmercuriacetate
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1 mM, 80% inhibition
S-adenosyl-L-homocysteine
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competitive, inhibition kinetics
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additional information
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activity is increased, in both in vitro and in vivo carnation tissues, by the inoculation with Fusarium oxysporum f. sp.dianthi
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0.011
4'-hydroxyflavanone
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pH 7, 25°C
0.0033
apigenin
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pH 7, 25°C
0.0735
genistein
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pH 7, 25°C
0.0017
kaempferol
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pH 7, 25°C
additional information
additional information
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kinetic mechanism
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0.012
S-adenosyl-L-homocysteine
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pH 7, 25°C
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5 - 8.5
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50% of maximum activity at pH 5.5 and 8.5, 4% of maximum activity at pH 5
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4.2
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isoelectric focusing, pH-gradient: 3-9
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line CP3a
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brenda
cv. Novada
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brenda
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brenda
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brenda
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brenda
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recombinant enzyme
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brenda
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43000 - 45000
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gel filtration, native PAGE
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5 - 8.5
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50% of maximum activity at pH 5.5 and 8.5, 4% of maximum activity at pH 5
655462
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-20°C, 2 weeks, 50% loss of activity
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CrOMT6 gene, expression in Escherichia coli, gene structure
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Curir, P.; Lanzotti, V.; Dolci, M.; Dolci, P.; Pasini, C.; Tollin, G.
Purification and properties of a new S-adenosyl-L-methionine:flavonoid 4'-O-methyltransferase from carnation (Dianthus caryophyllus L.)
Eur. J. Biochem.
270
3422-3431
2003
Dianthus caryophyllus
brenda
Schroeder, G.; Wehinger, E.; Lukacin, R.; Wellmann, F.; Seefelder, W.; Schwab, W.; Schroeder, J.
Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases
Phytochemistry
65
1085-1094
2004
Catharanthus roseus
brenda
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