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Information on EC 2.1.1.270 - (+)-6a-hydroxymaackiain 3-O-methyltransferase
for references in articles please use BRENDA:EC2.1.1.270
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EC Tree 2 Transferases
2.1 Transferring one-carbon groups
2.1.1 Methyltransferases
2.1.1.270 (+)-6a-hydroxymaackiain 3-O-methyltransferase
IUBMB Comments
The protein from the plant Pisum sativum (garden pea) methylates (+)-6a-hydroxymaackiain at the 3-position. It also methylates 2,7,4′-trihydroxyisoflavanone on the 4′-position (cf. EC 2.1.1.212, 2,7,4-trihydroxyisoflavanone 4-O-methyltransferase) with lower activity.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
showSynonyms
(+)-6a-hydroxymaackiain 3-o-methyltransferase, s-adenosyl-l-methionine 2-hydroxyisoflavanone 4'-o-methyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
6a-hydroxymaackiain methyltransferase
HMM1
hmm6
hydroxymaackiain methyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain = S-adenosyl-L-homocysteine + (+)-pisatin
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
MetaCyc
(+)-pisatin biosynthesis, superpathway of pterocarpan biosynthesis (via formononetin)
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:(+)-6a-hydroxymaackiain 3-O-methyltransferase
The protein from the plant Pisum sativum (garden pea) methylates (+)-6a-hydroxymaackiain at the 3-position. It also methylates 2,7,4'-trihydroxyisoflavanone on the 4'-position (cf. EC 2.1.1.212, 2,7,4-trihydroxyisoflavanone 4-O-methyltransferase) with lower activity.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + (+)-maackiain
S-adenosyl-L-homocysteine + ?
Substrates: at 1.7% of the activity with daidzein, the enzyme also catalyzes the reaction of EC 2.1.1.150
Products: -
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S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Substrates: at 49% of the activity with daidzein, the enzyme also catalyzes the reaction of EC 2.1.1.150
Products: -
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S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Substrates: the bifunctional enzyme also catalyzes the 4'-O-methylation of 2,7,4'-trihydroxyisoflavanonewith slightly higher catalytic efficiency
Products: -
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S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Substrates: -
Products: -
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?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
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Substrates: isoform HMM1 shows efficiencies for the methylation of 2,7,4'-trihydroxyisoflavanone 4times higher than for the methylation of (+)-6a-hydroxymaackiain, substrate of 6a-hydroxymaackiain-3-O-methyltransferase. Isoform HMM2 has a higher Vmax and lower Km on (+)-6a-hydroxymaackiain, and has a 67fold higher efficiency for the methylation of (+)-6a-hydroxymaackiain than that for 2,7,4'-trihydroxyisoflavanone
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S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
-
Substrates: isoform HMM2, 6a-hydroxymaackiain is the preferred substrate
Products: -
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?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
-
Substrates: HMM2 is involved primarily in the biosynthesis of (+)-pisatin
Products: -
Products: -
?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
-
Substrates: HMM2 shows efficiencies (relative Vmax/Km) for the 3-O-methylation of (+)-6a-hydroxymaackiain 67 times higher than for the 4'-O-methylation of 2,7,4'-trihydroxyisoflavanone
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S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Pisum sativum UWA H2012-81
Substrates: -
Products: -
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?
additional information
?
-
Substrates: in vivo reaction is 4'-O-methylation of isoflavones, in vitro reaction is 7-O-methylation
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additional information
?
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Substrates: in Pisum sativum, there are two highly similar hydroxymaackiain 3-O-methyltransferases HMM, with HMM1 prefering 2,7,4'-trihydroxyisoflavanone as a substrate and HMM2 being the specific O-methyltransferase that methylates (+)-6a-hydroxymaackiain
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
Substrates: in vivo reaction is 4'-O-methylation of isoflavones, in vitro reaction is 7-O-methylation
Products: -
Products: -
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S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
-
Substrates: HMM2 is involved primarily in the biosynthesis of (+)-pisatin
Products: -
Products: -
?
S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain
S-adenosyl-L-homocysteine + (+)-pisatin
Pisum sativum UWA H2012-81
Substrates: -
Products: -
Products: -
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
metabolism
the differential expression of 13 defence-related genes during Phoma koolunga infection of stems and leaves of susceptible versus resistant field pea (Pisum sativum) determined by quantitative RT-PCR shows that expression, in terms of relative mRNA level ratios, of genes encoding ferredoxin NADP oxidoreductase, 6a-hydroxymaackiain methyltransferase (hmm6), chalcone synthase (PSCHS3) and ascorbate peroxidase in leaves and stems vary during 6-72 hours post-inoculation (hpi) and reflecting host resistance levels in leaves versus stems. In comparison to the susceptible genotype, at 24, 48 and 72 hpi, two genes, hmm6 (122, 207 and 32fold, respectively) and PSCHS3 are strongly upregulated in leaves of the resistant genotype, highlighting that resistance against Phoma koolunga in field pea is governed by the early synthesis of pisatin, overview
metabolism
Pisum sativum UWA H2012-81
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the differential expression of 13 defence-related genes during Phoma koolunga infection of stems and leaves of susceptible versus resistant field pea (Pisum sativum) determined by quantitative RT-PCR shows that expression, in terms of relative mRNA level ratios, of genes encoding ferredoxin NADP oxidoreductase, 6a-hydroxymaackiain methyltransferase (hmm6), chalcone synthase (PSCHS3) and ascorbate peroxidase in leaves and stems vary during 6-72 hours post-inoculation (hpi) and reflecting host resistance levels in leaves versus stems. In comparison to the susceptible genotype, at 24, 48 and 72 hpi, two genes, hmm6 (122, 207 and 32fold, respectively) and PSCHS3 are strongly upregulated in leaves of the resistant genotype, highlighting that resistance against Phoma koolunga in field pea is governed by the early synthesis of pisatin, overview
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physiological function
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hairy roots containing RNAi constructs of HMM are deficient in (+)-pisatin biosynthesis, and accumulate 2,7,4'-trihydroxyisoflavanone, daidzein, isoformononetin, and liquiritigenin. Accumulation of compounds is consistent with the blockage of the synthesis of (+)-pisatin at the HI4'OMT catalyzed step resulting in the accumulation of liquiritigenin and 2,7,4'-trihydroxyisoflavanone and the diversion of the pathway to produce daidzein and isoformononetin
physiological function
resistance against Phoma koolunga in field pea is governed by the early synthesis of pisatin involving the enzyme hydroxymaackiain methyltransferase
physiological function
Pisum sativum UWA H2012-81
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resistance against Phoma koolunga in field pea is governed by the early synthesis of pisatin involving the enzyme hydroxymaackiain methyltransferase
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). M3OM1_PEA
360
0
40351
Swiss-Prot
other Location (Reliability: 2)
M3OM2_PEA
360
0
40380
Swiss-Prot
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystallized from a polyethylene glycol precipitant containing 2.5 mM of the reaction product S-adenosyl-L-homocysteine, 2.5 A resolution
homology modeling of the active sites of both HMM1 and HMM2 with substrate (+)-6a-hydroxymaackiain
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
gene hmm6, genotyping, gene expression analysis by quantitative real-time RT-PCR
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
Pisum sativum ssp. syriacum P665 shows constitutively an increased expression of the defense related genes as 6a-hydroxymaackiain methyltransferase. the hmm6 gene, encoding a 6a-hydroxymaackiain methyltransferase, is constitutively around 2 times more expressed in P665 than in Messire. After inoculation with Mycosphaerella pinodes this gene is overexpressed in both genotypes but more strongly in Messire. As a result this gene shows a similar level of expression in both genotypes after inoculation
Pisum sativum ssp. syriacum P665 shows constitutively an increased expression of the defense related genes as 6a-hydroxymaackiain methyltransferase. the hmm6 gene, encoding a 6a-hydroxymaackiain methyltransferase, is constitutively around 2 times more expressed in P665 than in Messire. After inoculation with Mycosphaerella pinodes this gene is overexpressed in both genotypes but more strongly in Messire. As a result this gene shows a similar level of expression in both genotypes after inoculation
Pisum sativum ssp. syriacum P665 shows constitutively an increased expression of the defense related genes as 6a-hydroxymaackiain methyltransferase. the hmm6 gene, encoding a 6a-hydroxymaackiain methyltransferase, is constitutively around 2 times more expressed in P665 than in Messire. After inoculation with Mycosphaerella pinodes this gene is overexpressed in both genotypes but more strongly in Messire. As a result this gene shows a similar level of expression in both genotypes after inoculation
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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)
brenda
Akashi, T.; VanEtten, H.D.; Sawada, Y.; Wasmann, C.C.; Uchiyama, H.; Ayabe, S.
Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis
Phytochemistry
67
2525-2530
2006
Pisum sativum
brenda
Kaimoyo, E.; VanEtten, H.
Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin
Phytochemistry
69
76-87
2008
Pisum sativum
brenda
Fondevilla, S.; Kster, H.; Krajinski, F.; Cubero, J.I.; Rubiales, D.
Identification of genes differentially expressed in a resistant reaction to Mycosphaerella pinodes in pea using microarray technology
BMC Genomics
12
28
2011
Pisum sativum (O24305), Pisum sativum P665 (O24305)
brenda
Liu, C.J.; Deavours, B.E.; Richard, S.B.; Ferrer, J.L.
Blount, J.W.; Huhman, D.; Dixon, R.A.; Noel, J.P.: Structural basis for dual functionality of isoflavonoid O-methyltransferases in the evolution of plant defense responses
Plant Cell
18
3656-3669
2006
Medicago truncatula (Q29U70)
brenda
Tran, H.; You, M.; Barbetti, M.
Expression of defence-related genes in stems and leaves of resistant and susceptible field pea (Pisum sativum) during infection by Phoma koolunga
Plant Pathol.
67
156-166
2018
Pisum sativum (O24305), Pisum sativum UWA H2012-81 (O24305)
-
brenda
EXTERNAL LINKS (specific for EC-Number 2.1.1.270)
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