Enantioselective Complexation of Xylopinine: A Cyclodextrin-Assisted CE and NMR Study.

ABSTRACT: Tetrahydroprotoberberine alkaloids (THPBs) are bioactive natural products bearing stereogenic centers that frequently exhibit enantiomer-specific pharmacological effects. Xylopinine (XPN), a representative THPB, shows cytotoxic, antimicrobial, and antimalarial activity in vitro, and displays pronounced stereoselectivity in vivo, with the naturally occurring (S)-enantiomer emphasizing the need for reliable enantioselective analysis. In this study, we present the synthesis of racemic XPN from norlaudanosine, and its first comprehensive cyclodextrin-assisted capillary electrophoresis screening dedicated to the enantioseparation of XPN. Sulfated- and sulfobutyl-ether-β-cyclodextrin (S-β-CyD, SBE-β-CyD) provided efficient resolution (R_s > 3), while heptakis-(6-deoxy-6-(

SUBMITTER: Varnagy E 

PROVIDER: S-EPMC12524373 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature