2.1.1.231: flavonoid 4'-O-methyltransferase
This is an abbreviated version!
For detailed information about flavonoid 4'-O-methyltransferase, go to the full flat file.
Word Map on EC 2.1.1.231
-
2.1.1.231
-
quercetin
-
4'-o-methylation
-
flavone
-
naringenin
-
luteolin
-
saccharopolyspora
-
4'-methylated
-
flavanones
-
acacetin
-
rebeccamycin
-
rhamnosyl
-
kaempferol
-
apigenin
-
spinosyn
-
indolocarbazole
-
synthesis
- 2.1.1.231
- quercetin
-
4'-o-methylation
- flavone
- naringenin
- luteolin
-
saccharopolyspora
-
4'-methylated
- flavanones
- acacetin
- rebeccamycin
-
rhamnosyl
- kaempferol
- apigenin
-
spinosyn
-
indolocarbazole
- synthesis
Reaction
Synonyms
4'-O-methyltransferase, 4'OMT, B-ring 4'OMT, F 4'-OMT, flavonoid 4'-O-methyltransferase, GerMIII, O-methyltransferase, OMT, regiospecific flavonoid 4'OMT, SOMT-2, SOMT2, soybean O-methyltransferase
ECTree
Advanced search results
Substrates Products
Substrates Products on EC 2.1.1.231 - flavonoid 4'-O-methyltransferase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
REACTION DIAGRAM
4'-hydroxyflavanone + S-adenosyl-L-methionine
4'-methoxyflavanone + S-adenosyl-L-homocysteine
-
-
-
-
?
apigenin + S-adenosyl-L-methionine
acacetin + S-adenosyl-L-homocysteine
-
-
-
-
?
genistein + S-adenosyl-L-methionine
biochanin A + S-adenosyl-L-homocysteine
-
-
-
-
?
kaempferol + S-adenosyl-L-methionine
kaempferide + S-adenosyl-L-homocysteine
-
-
-
-
?
S-adenosyl-L-methionine + 3'-O-methyleriodictyol
S-adenosyl-L-homocysteine + 3',4'-O-dimethyleriodictyol
-
product identification by mass spectrometry
-
?
S-adenosyl-L-methionine + alizarin
S-adenosyl-L-homocysteine + methylalizarin
-
-
-
?
S-adenosyl-L-methionine + apigenin
S-adenosyl-L-homocysteine + acacetin
-
36% of the activity relative to naringenin. Escherichia coli harboring SOMT-2 is grown with daidzein, geninstein, apigenin, naringenin, and quercetin, respectively, and reaction products were analyzed with thin layer chromatography and HPLC
-
-
?
S-adenosyl-L-methionine + chrysoeriol
S-adenosyl-L-homocysteine + 4'-O-methylchrysoeriol
-
-
-
?
S-adenosyl-L-methionine + daidzein
S-adenosyl-L-homocysteine + formononetin
-
90% of the activity relative to naringenin. Escherichia coli harboring SOMT-2 is grown with daidzein, geninstein, apigenin, naringenin, and quercetin, respectively, and reaction products were analyzed with thin layer chromatography and HPLC
-
-
?
S-adenosyl-L-methionine + eriodictyol
S-adenosyl-L-homocysteine + 4'-O-methyleriodictyol
-
-
-
?
S-adenosyl-L-methionine + fisetin
S-adenosyl-L-homocysteine + 4'-methoxyfisetin
8% activity with fisetin compared to quercetin
-
-
?
S-adenosyl-L-methionine + genistein
S-adenosyl-L-homocysteine + biochanin A
-
62% of the activity relative to naringenin. Escherichia coli harboring SOMT-2 is grown with daidzein, geninstein, apigenin, naringenin, and quercetin, respectively, and reaction products were analyzed with thin layer chromatography and HPLC
-
-
?
S-adenosyl-L-methionine + isorhamnetin
S-adenosyl-L-homocysteine + 4'-O-methylisorhamnetin
-
-
-
?
S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + 4'-O-methylkaempferol
-
-
-
?
S-adenosyl-L-methionine + luteolin
S-adenosyl-L-homocysteine + 4'-methoxyluteolin
67% activity with luteolin compared to quercetin
-
-
?
S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + 4'-methoxymyricetin
20% activity with luteolin compared to quercetin
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 4'-methoxyquercetin
best substrate, 85% conversion at 2 mM substrate
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 4'-methylquercetin
-
Escherichia coli harboring SOMT-2 is grown with daidzein, geninstein, apigenin, naringenin, and quercetin, respectively, and reaction products were analyzed with thin layer chromatography and HPLC
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 4'-O-methylquercetin
-
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + tamarixetin
-
-
-
?
S-adenosyl-L-methionine + quercetin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + 4'-methoxyquercetin 3-O-beta-D-glucoside
16% activity with quercetin glucoside compared to quercetin
-
-
?
S-adenosyl-L-homocysteine + ponciretin
-
i.e. 4',5,7-trihyroxyflavanone. Escherichia coli harboring SOMT-2 is grown with daidzein, geninstein, apigenin, naringenin, and quercetin, respectively, and reaction products were analyzed with thin layer chromatography and HPLC
i.e. 4'-methoxy-5,7-dihydroxyflavanone
-
?
S-adenosyl-L-methionine + naringenin
S-adenosyl-L-homocysteine + ponciretin
i.e. 4',5,7-trihyroxyflavanone, the enzyme transfers a methyl group to 4'-hydroxyl group of naringenin
i.e. 4'-methoxy-5,7-dihydroxyflavanone
-
?
S-adenosyl-L-methionine + naringenin
S-adenosyl-L-homocysteine + ponciretin
i.e. 4',5,7-trihyroxyflavanone, reaction of SOMT-2
i.e. 4'-methoxy-5,7-dihydroxyflavanone
-
?
?
-
the only substrates found for CrOMT6 are 3'-O-methyl-eriodictyol (homoeriodictyol) and the corresponding flavones and flavonols, substrate specificty, overview. No or poor activity with naringenin, pentahydroxyflavanone, hesperetin, myricetin, 7,3'-O-dimethylquercetin, 7-O-methylquercetin, syringetin, apigenin, luteolin, tricetin, velutin, dihydrokaempferol, dihydroquercetin, dihydromyricetin, and 3'-O-methyl-dihydroquercetin, and also no activity with ferulic acid, coniferyl alcohol, vanillic acid vanillin, eugenol, isoeugenol, and guaicol. Not only the B-ring configuration, but also the size and shape of the A-ring are critical parts of the substrate specificity
-
-
?
additional information
?
-
-
the only substrates found for CrOMT6 are 3'-O-methyl-eriodictyol (homoeriodictyol) and the corresponding flavones and flavonols, substrate specificty, overview. No or poor activity with naringenin, pentahydroxyflavanone, hesperetin, myricetin, 7,3'-O-dimethylquercetin, 7-O-methylquercetin, syringetin, apigenin, luteolin, tricetin, velutin, dihydrokaempferol, dihydroquercetin, dihydromyricetin, and 3'-O-methyl-dihydroquercetin, and also no activity with ferulic acid, coniferyl alcohol, vanillic acid vanillin, eugenol, isoeugenol, and guaicol. Not only the B-ring configuration, but also the size and shape of the A-ring are critical parts of the substrate specificity
-
-
?
additional information
?
-
-
enzyme specifically methylates the hydroxy substituent in 4'-position of the flavones, flavanones and isoflavones in the presence of S-adenosyl-L-methionine. No activity towards hydroxycinnamic acid derivatives
-
-
?
additional information
?
-
-
SOMT-2 has a regiospecific methylation activity, resulting in transforming 4'-hydroxyl group of flavonoids B-ring to 4'-methyl group. Caffeic acid, catechol, ferulic acid, and oricinol are biotransformed at less than 1%
-
-
?
additional information
?
-
among the flavonoids, quercetin is the most favorable substrate, followed by luteolin, myricetin, quercetin glucoside, and fisetin, while only a single product is formed in each case. Product identification by mass-spectrometry and NMR spectrometric analysis. Susbtrate specificity, overview. Mechanistic overview of the regiospecific modification, a double bond between the C2 and the C3 and a single-ring-appended conjugate-hydroxyl group are crucial for the favorable enzymatic conversions of the GerMIII catalysis, modeling and molecular docking. Of all of the anthraquinones that are tested, only alizarin is methylated by the GerMIII at a detectable amount, whereas the methylation of all of the other remaining compounds is not evident. The common feature among the GerMIII substrates is the existence of two neighboring hydroxyl groups in the presence of a double bond between the C2 and the C3, as found in the quercetin, luteolin, myricetin, fisetin, and quercetin glucoside. GerMIII does not methylate many substrates including the close flavonoid relative catechin, which lacks the double bond between the C2 and the C3
-
-
-