<p><i>Sarcomphalus joazeiro</i> (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-<i>O</i>-[α-<span>l</span>-arabinofuranosyl-(1 → 2)-{β-<span>d</span>-glucopyranosyl-(1 → 3)-}-α-<span>l</span>-arabinopyranosyl] jujubogenin (bacopaside X) from the <i>S. joazeiro</i> 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:<i>n</i>-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 <sup>1</sup>H and <sup>13</sup>C-NMR. Bacopaside X exhibited potent antifungal activity against <i>Candida</i> spp., with MICs between 156 and 625&#xa0;µg/ml, up to 20-fold more active than the crude extract or <i>n</i>-butanolic fraction. This is the first report of targeted HSCCC isolation of bacopaside X from <i>S. joazeiro</i>, highlighting HSCCC’s value in isolating and purifying compounds from complex mixtures.</p> Graphical Abstract <p></p>

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Targeted Isolation of Bacopaside X by High-Speed Countercurrent Chromatography: A Chemotaxonomic Marker of Sarcomphalus joazeiro

  • Manoel André de Souza Neto,
  • Renato Dantas-Medeiros,
  • Emanuella de Aragão Tavares,
  • Edilane Rodrigues Dantas de Araújo,
  • Jovelina Samara Ferreira Alves,
  • Walicyranison Plinio da Silva-Rocha,
  • Guilherme Maranhão Chaves,
  • Freddy A. Ramos,
  • Silvana Maria Zucolotto

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