Targeted Isolation of Bacopaside X by High-Speed Countercurrent Chromatography: A Chemotaxonomic Marker of Sarcomphalus joazeiro
摘要
Sarcomphalus joazeiro (Mart.) Hauenschild, Rhamnaceae, a native Brazilian plant, has traditional use against fungal infections. In this study, we report a rapid and selective isolation of 3-O-[α-l-arabinofuranosyl-(1 → 2)-{β-d-glucopyranosyl-(1 → 3)-}-α-l-arabinopyranosyl] jujubogenin (bacopaside X) from the S. joazeiro hydroethanolic leaf extract using high-speed countercurrent chromatography (HSCCC) and reversed-phase liquid chromatography (RP-LC). After screening 11 biphasic solvent systems, the ethyl acetate:n-butanol:water system (1:0.4:1, v/v/v), operated under pH-zone refining conditions in reversed-phase mode, provided optimal stationary phase retention (81%) and allowed the isolation of bacopaside X. The structure was confirmed by 1H and 13C-NMR. Bacopaside X exhibited potent antifungal activity against Candida spp., with MICs between 156 and 625 µg/ml, up to 20-fold more active than the crude extract or n-butanolic fraction. This is the first report of targeted HSCCC isolation of bacopaside X from S. joazeiro, highlighting HSCCC’s value in isolating and purifying compounds from complex mixtures.
Graphical Abstract