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IUBMB Comments Involved with EC 2.1.1.76 quercetin 3-O -methyltransferase and EC 2.1.1.83 3,7-dimethylquercetin 4′-O -methyltransferase in the methylation of quercetin to 3,7,4′-trimethylquercetin in Chrysosplenium americanum . Does not act on flavones, dihydroflavonols, or their glucosides.
Synonyms
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7-O-methyltransferase
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flavone 7-O-methyltransferase
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flavonoid O-methyltransferase
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flavonol 7-O-methyltransferase
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methyltransferase, flavonol 7-
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7-OMT
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S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxy-3-methoxyflavone = S-adenosyl-L-homocysteine + 5,3',4'-trihydroxy-3,7-dimethoxyflavone
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxy-3-methoxyflavone = S-adenosyl-L-homocysteine + 5,3',4'-trihydroxy-3,7-dimethoxyflavone
ordered bi bi mechanism, S-adenosyl-L-methionine binds first, S-adenosyl-L-homocysteine is the last product released
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S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxy-3-methoxyflavone = S-adenosyl-L-homocysteine + 5,3',4'-trihydroxy-3,7-dimethoxyflavone
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methyl group transfer
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MetaCyc
polymethylated quercetin biosynthesis, polymethylated quercetin glucoside biosynthesis I - quercetin series (Chrysosplenium)
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S-adenosyl-L-methionine:5,7,3',4'-tetrahydroxy-3-methoxyflavone 7-O-methyltransferase
Involved with EC 2.1.1.76 quercetin 3-O-methyltransferase and EC 2.1.1.83 3,7-dimethylquercetin 4'-O-methyltransferase in the methylation of quercetin to 3,7,4'-trimethylquercetin in Chrysosplenium americanum. Does not act on flavones, dihydroflavonols, or their glucosides.
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2 S-adenosyl-L-methionine + eriodictyol
2 S-adenosyl-L-homocysteine + 3',7-di-O-methyleriodictyol
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Substrates: -
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2 S-adenosyl-L-methionine + luteolin
2 S-adenosyl-L-homocysteine + velutin
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Substrates: -
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2 S-adenosyl-L-methionine + quercetin
2 S-adenosyl-L-homocysteine + rhamnazin
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Substrates: -
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2 S-adenosyl-L-methionine + taxifolin
2 S-adenosyl-L-homocysteine + 3',7-di-O-methyltaxifolin
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Substrates: -
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S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxy-3-methoxyflavone
S-adenosyl-L-homocysteine + 3',4',5-trihydroxy-3,7-dimethoxyflavone
S-adenosyl-L-methionine + kaempferol
7-O-methylkaempferol
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Substrates: -
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S-adenosyl-L-methionine + quercetin
7-O-methylquercetin
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Substrates: -
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S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxy-3-methoxyflavone
S-adenosyl-L-homocysteine + 3',4',5-trihydroxy-3,7-dimethoxyflavone
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Substrates: trivial name 3-methylquercetin, specific for 3-methylquercetin
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S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxy-3-methoxyflavone
S-adenosyl-L-homocysteine + 3',4',5-trihydroxy-3,7-dimethoxyflavone
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Substrates: trivial name 3-methylquercetin, specific for 3-methylquercetin
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S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxy-3-methoxyflavone
S-adenosyl-L-homocysteine + 3',4',5-trihydroxy-3,7-dimethoxyflavone
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Substrates: involved with EC 2.1.1.76 and 2.1.1.83 in the methylation of quercetin
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S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxy-3-methoxyflavone
S-adenosyl-L-homocysteine + 3',4',5-trihydroxy-3,7-dimethoxyflavone
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Substrates: involved with EC 2.1.1.76 and 2.1.1.83 in the methylation of quercetin
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S-adenosyl-L-methionine
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Ca2+
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1 mM, 20-50% inhibition
Co2+
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1 mM, 20-50% inhibition
Cu2+
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1 mM, 20-50% inhibition
p-chloromercuribenzoate
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Zn2+
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1 mM, 20-50% inhibition
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0.007
3',4',5,7-tetrahydroxy-3-methoxyflavone
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0.0324 - 0.0378
kaempferol
0.0298 - 0.0324
quercetin
0.065
S-adenosyl-L-methionine
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0.0324
kaempferol
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wild type enzyme, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
0.0378
kaempferol
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mutant enzyme D257G, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
0.0298
quercetin
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wild type enzyme, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
0.0324
quercetin
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mutant enzyme D257G, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
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0.064
kaempferol
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wild type enzyme, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
0.07
kaempferol
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mutant enzyme D257G, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
0.064
quercetin
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mutant enzyme D257G, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
0.071
quercetin
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wild type enzyme, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
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17
kaempferol
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mutant enzyme D257G, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
19
kaempferol
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wild type enzyme, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
19
quercetin
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mutant enzyme D257G, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
24
quercetin
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wild type enzyme, in 10 mM Tris/HCl buffer (pH 7.5), at 37°C
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7.2 - 9.5
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approx. 50% of maximal activity at pH 7.2 and 9.5
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brenda
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brenda
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brenda
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brenda
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shoot tip
brenda
Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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60000
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x * 60000, SDS-PAGE
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D257G
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the mutant methylates the 3-hydroxyl group of flavonols in addition to the 7-hydrdoxyl group
L101M
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the mutant shows wild type reactivity with kaempferol and quercetin
additional information
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generation of a multifunctional FOMT fusing a 3'-OMT (SlOMT3, EC 2.1.1.267) and a 7-OMT (OsNOMT, EC 2.1.1.82). The SlOMT3/OsNOMT fusion enzyme possesses both 3'- and 7-OMT activities to diverse flavonoid substrates, which are comparable to those of individual SlOMT3 and OsNOMT. The SlOMT3/OsNOMT enzyme also shows 3'- and 7-OMT activity for 7- or 3'-O-methylflavonoids, respectively, suggesting that the fusion enzyme can sequentially methylate flavonoids into di-O-methylflavonoids. The biotransformation of the flavonoids quercetin, luteolin, eriodictyol, and taxifolin using SlOMT3/OsNOMT-transformed Escherichia coli generated corresponding di-O-methylflavonoids, rhamnazin, velutin, 3',7-di-O-methyleriodictyol, and 3',7-di-O-methyltaxifolin, respectively. These results indicate that dimethoxyflavonoids may be efficiently produced from non-methylated flavonoid precursors through a one-step biotransformation using the engineered Escherichia coli harboring the SlOMT3/OsNOMT fusion gene
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loss of activity during chromatofocusing
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-15°C, 200 mM potassium phosphate buffer, pH 8, 20% v/v glycerol, 5 mM dithiothreitol, several months, no loss of activity
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-20°C, 200 mM Tris-HCl, pH 8.0, 10 mM dithiothreitol, 2 months, no loss of activity
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4°C, 4-6 weeks, 80% loss of activity
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ammonium sulfate, gel filtration, chromatofocusing, ion exchange
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GST affinity column chromatography
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loss of activity during chromatofocusing possibly due to instability of the enzyme in the purified form or to the loss of some factors required for activity
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expressed as fusion protein with Solanum lycopersiucm 3'-O-methyltransferase OMT3 in Escherichia coli
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expressed in Escherichia coli BL21 cells
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recombinant expression of wild-type and chimeric mutant enzymes in Escherichia coli
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De Luca, V.; Ibrahim, R.K.
Enzymatic synthesis of polymethylated flavonols in Chrysosplenium americanum. I. Partial purification and some properties of S-adenosyl-L-methionine:flavonol 3-, 6-, 7-, and 4-O-methyltransferases
Arch. Biochem. Biophys.
238
596-605
1985
Chrysosplenium americanum
brenda
Khouri, H.E.; De Luca, V.; Ibrahim, R.K.
Enzymic synthesis of polymethylated flavonols in Chrysosplenium americanum. III. Purification and kinetic analysis of S-adenosyl-L-methionine:3-methylquercetin 7-O-methyltransferase
Arch. Biochem. Biophys.
265
1-7
1988
Chrysosplenium americanum
brenda
Joe, E.J.; Kim, B.G.; An, B.C.; Chong, Y.; Ahn, J.H.
Engineering of flavonoid O-methyltransferase for a novel regioselectivity
Mol. Cells
30
137-141
2010
Populus sp.
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
Oryza sativa
brenda
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