BioCyc:RXN-3481

Isoflavone O-methylation is a key reaction for the formation of pterocarpan phytoalexins such as medicarpin. Isoflavone specific O-methyltransferases have been purified expressing a high in vitro affinity for the methylation ofthe A-ring 7-hydroxyl group of daidzein.The resulting product, isoformononetin (7-O-methyldaidzein), is a rare naturally occurring compound which is unlikelyto be involved in the formation of medicarpin. No products of the 7-O-methylation of daidzein have been demonstratedto accumulate in elicited alfalfa cell cultures suggesting that this reaction may not occur in vivo.Recently, a daidzein-7-O-methyltransferase (D7OMT) has been purified from Glycyrrhiza echinata. |CITS: [12610212]|The distinct biochemistry of D7OMT and the distant phylogenetic relationship to another O-methyltransferase(2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase - HI4'OMT) acting specifically on 2,7,4'-trihydroxyisoflavanoneimplies a new scheme of formonetin biosynthesis which excludes the 4-O-methylation of daidzein.

S-ADENOSYLMETHIONINE + DAIDZEIN --> PROTON + CPD-3343 + ADENOSYL-HOMO-CYS

S-Adenosylmethionine[C15H23N6O5S] + Daidzein[C15H10O4] = H+[H] + Isoformononetin[C16H12O4] + S-Adenosyl-L-homocysteine[C14H20N6O5S]

DB Links

Alias

Metabolites

Substrates
metabolite compartment Structure
S-Adenosylmethionine

Formula: C15H23N6O5S
Cytoplasm
Daidzein

Formula: C15H10O4
Cytoplasm
Products
metabolite compartment Structure
H+

Formula: H
Cytoplasm
Isoformononetin

Formula: C16H12O4
Cytoplasm
S-Adenosyl-L-homocysteine

Formula: C14H20N6O5S
Cytoplasm