Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid

Jasmonic acid (JA) is a plant hormone involved in the defense response against insects and fungi. JA is synthesized from alpha-linolenic acid (LA) by the octadecanoid pathway in plants. 12-oxo-Phytodienoic acid (OPDA) is one of the biosynthetic intermediates in this pathway. The reported stereo selective total synthesis of cis-(+)-OPDA is not very efficient due to the many steps involved in the reaction as well as the use of water sensitive reactions. Therefore, we developed an enzymatic method for the synthesis of OPDA using acetone powder of flax seed and allene oxide cyclase (PpAOC2) from Physcomitrella patens. From this method, natural cis-(+)-OPDA can be synthesized in the high yield of approximately 40%. In this study, we investigated the substrate specificity of the enzymatic synthesis of other OPDA analogs with successions to afford OPDA amino acid conjugates, dinor-OPDA (dn-OPDA), and OPDA monoglyceride, and it was suggested that the biosynthetic pathway of arabidopsides could occur via MGDG.

Automated summary

In this study, an enzymatic method using flax seed acetone powder and allene oxide cyclase from Physcomitrella patens was developed for the synthesis of OPDA. Various OPDA analogs were successfully synthesized through this method, shedding light on the biosynthetic pathway of arabidopsides. The enzymatic synthesis of OPDA is significant for the efficient and convenient access to these compounds.