C18‐COOH Silica: Preparation, Characterisation and Its Application in Purification of Quaternary Ammonium Alkaloids from <i>Coptis chinensis</i>

Abstract

INTRODUCTION: Traditional methods for isolating and purifying quaternary ammonium alkaloids from Coptis chinensis do not discriminate the target alkaloids from co-extractives. Mixed-mode analytical chromatography has the potential to improve the separation of analytes in more complex extracts and, when used in a solid-phase extraction mode, improve the purity of isolated compounds. OBJECTIVE: To examine the high-performance liquid chromatographic separation capabilities of a mixed-mode, silica-based adsorbent and its application to the purification of quaternary ammonium alkaloids from Coptis chinensis based on solid-phase extraction. METHODOLOGY: The C18-COOH silica was prepared via "thiol-ene" click chemistry. Its chromatographic performance was firstly investigated. It was employed as the solid-phase extraction sorbent to purify quaternary ammonium alkaloids. RESULTS: Hydrophobic, attractive/repulsive electrostatic and ion-exchange interactions were demonstrated to be the possible retention mechanisms of a C18-COOH silica stationary phase, which could separate analytes of various properties. In addition, to purify quaternary ammonium alkaloids from Coptis chinensis, the solid-phase extraction approach based on the C18-COOH silica provided a slightly higher purification efficiency (6.7%) than an alkaloid-salt precipitation protocol (5.3%). The method had satisfactory reproducibility, re-using the same solid-phase extraction column three times, with relative standard deviations ranging from 1.99% to 8.02% for the six target alkaloids. CONCLUSION: A multi-functionalised silica was synthesised via "click chemistry". As the high-performance liquid chromatographic stationary phase, the C18-COOH silica could be operated in trimodal reversed-phase/weak cation exchange/hydrophilic interaction mode. The C18-COOH silica also exhibited potential as solid-phase extraction sorbent in the purification of quaternary ammonium alkaloids from complex matrices. Copyright © 2017 John Wiley & Sons, Ltd.