Stereoselective separation of spiroindoline phytoalexins on R-naphthylethyl cyclofructan 6-based chiral stationary phase

In this study, the recently developed type of chiral stationary phase, R-naphthylethyl-derivatized cyclofructan 6 (RN-CF6) was used for direct enantioseparation of novel chiral analogs of spiroindoline phytoalexins with potential anticancer and antimicrobial activity using HPLC. The experiments were performed under normal phase elution. Effects of polar modifier, the structure of the analytes and temperature on the separation were investigated. The thermodynamic parameters were evaluated from van’t Hoff plots. Cyclofructan-based chiral stationary phase, RN-CF6, was able to separate all eighteen racemic mixtures of studied phytoalexins including cis- and trans-diastereoisomers.

► Cyclofructan-based RN-CF6 allowed enantioseparation of novel indole phytoalexins. ► The best results were achieved under normal phase elution. ► Effects of polar modifier and column temperature on the separation were investigated. ► Simultaneous separation of both cis- and trans-diastereoisomers was achieved.