Synthesis and structure-activity relationship of oleanolic mono- or di-glycosides against Magnaporthe oryzae

G. Huo, C. Liu, Y. Hui, X. Chen, D. Xiao
2016 Genetics and Molecular Research  
Saponins are naturally-occurring units with broad diversity and are usually recognized as phytoanticipins. In order to develop new saponin chemical entities with high activity against Magnaporthe oryzae, we selected oleanolic acid (OA), which has wide natural distribution and rich content in plants. We used the ability of OA to act as an aglycone for glycosylation to obtain information on the structure-activity relationship (SAR) for rational molecular pesticide design. Oleanolic mono-or
more » ... olic mono-or di-glycosides were synthesized at either the C 3 -hydroxy and/or C 28 -carboxyl position, using trichloroacetimidate or glycosyl bromide donors, respectively. Structures were confirmed by [ 1 H]-,[ 13 C]-NMR. Furthermore, the activity of the synthesized glycosides against M. oryzae was assessed in vitro, based on the mycelium growth rate. The twenty five oleanolic mono-or di-glycosides
doi:10.4238/gmr.15038998 pmid:27706788 fatcat:jwq7jrb3qvat7kfotid2gprs3y