The first total synthesis of phytoglandins, prostaglandin-like natural products in plants
Ullrich Jahn’s research group from IOCB Prague has developed the first asymmetric total synthesis of phytoglandins (PhytoG), which are diastereomeric to the known phytoprostanes. The method is based on radical anion oxidative cyclization, copper(I)-mediated alkyl-alkyl coupling, and enantioselective reduction.
Thanks to the available PhytoG standards, the scientists were able to identify these compounds in aged vegetable oils using UHPLC-MS/MS, performed in collaboration with Josef Cvacka’s group. This is the first evidence of PhytoGs as natural products.
Since prostaglandins are mammalian and human local hormones, the plant PhytoGs might also be biologically active. Therefore, the scientist studied their interaction with prostaglandin F receptor but did not observe any activity.
The novel synthesis and the identification from natural sources have been recently published in Chemistry – A European Journal with Jakub Smrček as the first author.
Read the paper:
- Smrček, J., Hájek, M., Hodek, O., Čížek, K., Pohl, R., Jahn, E., Galano, J.-M., Oger, C., Durand, T., Cvačka, J. and Jahn, U. (2021), First Total Synthesis of Phytoprostanes with Prostaglandin-Like Configuration, Evidence for Their Formation in Edible Vegetable Oils and Orienting Study of Their Biological Activity. Chem. Eur. J. https://doi.org/10.1002/chem.202100872
