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4 S-adenosyl-L-methionine + quercetin
4 S-adenosyl-L-homocysteine + 3,3',5,7-tetra-O-methyl-quercetin
-
-
-
?
luteolin + S-adenosyl-L-methionine
3'-O-methyl luteolin + S-adenosyl-L-homocysteine
-
high 3'-O-methyltransferase activity
i.e. chrysoeriol
-
?
luteolin + S-adenosyl-L-methionine
3'-O-methylluteolin + S-adenosyl-L-homocysteine
-
OMT-15 shows 92% activity and OMT-17 shows 84% activity compared to myricetin
-
-
?
quercetin + S-adenosyl-L-methionine
3'-O-methylquercetin + S-adenosyl-L-homocysteine
S-adenosyl-L-homocysteine + 6,7-dihydroxy-3'-methoxyisoflavone
?
-
-
-
-
?
S-adenosyl-L-methionine + (-)-epicatechin
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + (2S)-naringenin
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
?
-
-
-
-
?
S-adenosyl-L-methionine + 3,3',4',5,5',7-hexahydroxyflavone
S-adenosyl-L-homocysteine + 3,4',5,5',7-pentahydroxy-3'-methoxyflavone
i.e. mycricetin. 70% of the activity with quercetin
-
-
?
S-adenosyl-L-methionine + 3,3',4',5,7-pentahydroxy flavone
S-adenosyl-L-homocysteine + isorhamnetin
S-adenosyl-L-methionine + 3,3',4',5,7-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3,4',5,7-tetrahydroxy-3'-methoxyflavone
i.e. quercetin. Preferred substrate
i.e. isorhamnetin
-
?
S-adenosyl-L-methionine + 4,5-dihydroxy-3-methoxycinnamate
S-adenosyl-L-homocysteine + 4-hydroxy-3,5-dimethoxycinnamate
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavanone
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 3'-O-methylluteolin
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
S-adenosyl-L-methionine + 5,7,3'-trihydroxyflavone
?
-
-
-
-
?
S-adenosyl-L-methionine + 5,7,3'-trihydroxyflavone 7-O-glucoside
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone 7-O-glucoside
S-adenosyl-L-methionine + 5-hydroxyferulic acid
?
-
OMT-15 shows 25% activity and OMT-17 shows 18% activity compared to myricetin
-
-
?
S-adenosyl-L-methionine + 7,8-dihydroxyflavone
?
-
OMT-15 shows 102% activity and OMT-17 shows 143% activity compared to myricetin
-
-
?
S-adenosyl-L-methionine + dihydro-3,3',4',5,7-pentahydroxy flavone
S-adenosyl-L-homocysteine + dihydroisorhamnetin
S-adenosyl-L-methionine + equol
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3'-O-methylquercetin
-
-
-
-
?
S-adenosyl-L-methionine + quercetin 3-O-glucoside
S-adenosyl-L-homocysteine + ?
-
poor substrate
-
-
?
S-adenosyl-L-methionine + rutin
S-adenosyl-L-homocysteine + ?
-
poor substrate
-
-
?
taxifolin + S-adenosyl-L-methionine
3'-O-methyl taxifolin + S-adenosyl-L-homocysteine
-
3'-O-methyltransferase activity
-
-
?
additional information
?
-
quercetin + S-adenosyl-L-methionine
3'-O-methylquercetin + S-adenosyl-L-homocysteine
-
SOMT-9 is involved in the biosynthesis of isorhamnetin
-
-
?
quercetin + S-adenosyl-L-methionine
3'-O-methylquercetin + S-adenosyl-L-homocysteine
-
a flavone, 3'-O-methyltransferase activity, best substrate
i.e. isorhamnetin
-
?
S-adenosyl-L-methionine + 3,3',4',5,7-pentahydroxy flavone
S-adenosyl-L-homocysteine + isorhamnetin
-
quercetin
-
-
?
S-adenosyl-L-methionine + 3,3',4',5,7-pentahydroxy flavone
S-adenosyl-L-homocysteine + isorhamnetin
-
quercetin
-
-
?
S-adenosyl-L-methionine + 4,5-dihydroxy-3-methoxycinnamate
S-adenosyl-L-homocysteine + 4-hydroxy-3,5-dimethoxycinnamate
-
5-hydroxy ferulic acid
-
-
?
S-adenosyl-L-methionine + 4,5-dihydroxy-3-methoxycinnamate
S-adenosyl-L-homocysteine + 4-hydroxy-3,5-dimethoxycinnamate
-
5-hydroxy ferulic acid
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavanone
-
eriodictyol
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavanone
-
eriodictyol
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 3'-O-methylluteolin
-
i.e. luteolin, the enzyme also catalyzes the methylation of tricetin and the methylation of quercetin, prefers tricetin over luteolin
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 3'-O-methylluteolin
-
i.e. lutepolin, the enzyme also catalyzes the methylation of tricetin and the methylation of 5-hydroxyferulic acid and quercetin, prefers tricetin over luteolin
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
i.e. luteolin. 15% of the activity with quercetin
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
-
luteolin
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
-
luteolin
-
-
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
-
luteolin
chrysoeriol
?
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
-
luteolin, enzyme directly related to flavone glycoside biosynthesis, biosynthesis of 3'-methoxyflavonoids
chrysoeriol
?
S-adenosyl-L-methionine + 5,7,3'-trihydroxyflavone 7-O-glucoside
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone 7-O-glucoside
-
-
chrysoeriol-7-O-glucoside
?
S-adenosyl-L-methionine + 5,7,3'-trihydroxyflavone 7-O-glucoside
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone 7-O-glucoside
-
-
chrysoeriol-7-O-glucoside
?
S-adenosyl-L-methionine + 5,7,3'-trihydroxyflavone 7-O-glucoside
S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone 7-O-glucoside
-
luteolin 7-O-glucoside
chrysoeriol-7-O-glucoside
?
S-adenosyl-L-methionine + dihydro-3,3',4',5,7-pentahydroxy flavone
S-adenosyl-L-homocysteine + dihydroisorhamnetin
-
dihydroquercetin
-
-
?
S-adenosyl-L-methionine + dihydro-3,3',4',5,7-pentahydroxy flavone
S-adenosyl-L-homocysteine + dihydroisorhamnetin
-
dihydroquercetin
-
-
?
additional information
?
-
only flavonols with vicinal B-ring hydroxyl groups, such as quercetin and myricetin are good methyl acceptor
-
-
?
additional information
?
-
-
only flavonols with vicinal B-ring hydroxyl groups, such as quercetin and myricetin are good methyl acceptor
-
-
?
additional information
?
-
enzyme additionally shows N-acetylserotonin methyltransferase activity, reaction of EC 2.1.1.4, and caffeic acid methyltransferase activity, reaction of EC 2.1.1.68. The catalytic efficiency for N-acetylserotonin methyltransferase activity is 709fold lower than for caffeic acid methyltransferase. In vitro, N-acetylserotonin methyltransferase activity is dramatically decreased by the addition of caffeic acid in a dose-dependent manner, but the activity of caffeic acid methyltransferase is not altered by N-acetylserotonin
-
-
?
additional information
?
-
enzyme shows methylation activity for the 3-, 5-, 6-, and 7-hydroxyl groups of flavones. The highest activity is observed for 3-hydroxyflavone (flavonol), followed by 7-hydroxyflavone with a relative activity of 15.6% of that of 3-hydroxyflavone and 5-hydroxyflavone with that of 13.5%. Very weak activity is observed for 6-hydroxyflavone and no activity for 3'- or 4'-hydroxyflavone and 7-methoxy-8-hydroxyflavone. FOMT5 does not exhibit a sequential methylation order for 3-, 5-, and 7-hydroxyl groups of quercetin. No detection of polymethylated products from naringenin, (-)-epicatechin, and equol, and cyanidin is not a substrate
-
-
-
additional information
?
-
-
methylation proceedes only in the meta-position, enzyme is unable to catalyze the methylation of p-coumaric acid, m-coumaric acid, ferulic acid, isoferulic acid, sinapic acid, apigenin and naringenin
-
-
?
additional information
?
-
-
isoflavones biochanin A and daidzein do not serve as substrates
-
-
?
additional information
?
-
-
SOMT-9 transfers a methyl group to the 3'-OH group of substrates having ortho-hydroxyl groups and uses a flavonoids as a substrates, no activity with 3,3'-dihydroxyflavone, 5,3'-dihydroxyflavone, 6,3'-dihydroxyflavone, 3'-hydroxyflavone, and 3'-hydroxyflavanone
-
-
?
additional information
?
-
-
rutin is no substrate
-
-
?
additional information
?
-
-
OMT-15 and -17 cannot utilize naringenin, apigenin, or kaempferol as substrates, taxifolin and eriodictyol do not serve as methyl acceptors
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
isomeric substances isoferulic acid and diosmetin, chrysoeriol, apigenin p-cumaric acid and ferulic acid are not substrates
-
-
?
additional information
?
-
-
only ortho-dihydric phenols can function as substrates and only the meta-hydroxyl group is methylated, no reaction takes place if one of the two phenolic hydroxyls is methylated or if only one hydroxyl group is present
-
-
?
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Ebel, J.; Hahlbrock, K.; Grisebach, H.
Purification and properties of an o-dihydricphenol meta-O-methyltransferase from cell suspension cultures of parsley and its relation to flavonoid biosynthesis
Biochim. Biophys. Acta
269
313-326
1972
Petroselinum crispum
-
brenda
Ebel, J.; Hahlbrock, K.
Enzymes of flavone and flavonol-glycoside biosynthesis. Coordinated and selective induction in cell-suspension cultures of Petroselinum hortense
Eur. J. Biochem.
75
201-209
1977
Petroselinum crispum
brenda
Poulton, J.E.; Hahlbrock, K.; Grisebach, H.
O-Methylation of flavonoid substrates by a partially purified enzyme from soybean cell suspension cultures
Arch. Biochem. Biophys.
180
543-549
1977
Glycine max, Petroselinum crispum
brenda
Legrand, M.; Fritig, B.; Hirth, L.
O-Diphenol O-methyltransferases of healthy and tobacco-mosaic-virus-infected hypersensitive tobacco
Planta
144
101-108
1978
Nicotiana tabacum
brenda
Muzac, I.; Wang, J.; Anzellotti, D.; Zhang, H.; Ibrahim, R.K.
Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3'-O-methyltransferase and characterization of the gene product
Arch. Biochem. Biophys.
375
385-388
2000
Arabidopsis thaliana (Q9FK25), Arabidopsis thaliana
brenda
Kim, B.G.; Lee, H.J.; Park, Y.; Lim, Y.; Ahn, J.H.
Characterization of an O-methyltransferase from soybean
Plant Physiol. Biochem.
44
236-241
2006
Glycine max
brenda
Lee, Y.; Kim, B.; Chong, Y.; Lim, Y.; Ahn, J.
Cation dependent O-methyltransferases from rice
Planta
227
641-647
2008
Oryza sativa
brenda
Zhou, J.-M.; Fukushi, Y.; Wollenweber, E.; Ibrahim, R.K.
Characterization of two O-methyltransferase-like genes in barley and maize
Pharm. Biol.
46
26-34
2008
Hordeum vulgare, Zea mays
-
brenda
Byeon, Y.; Lee, H.Y.; Lee, K.; Back, K.
Caffeic acid O-methyltransferase is involved in the synthesis of melatonin by methylating N-acetylserotonin in Arabidopsis
J. Pineal Res.
57
219-227
2014
Arabidopsis thaliana (Q9FK25)
brenda
Itoh, N.; Iwata, C.; Toda, H.
Molecular cloning and characterization of a flavonoid-O-methyltransferase with broad substrate specificity and regioselectivity from Citrus depressa
BMC Plant Biol.
16
180
2016
Citrus depressa (A0A125T1T5)
brenda