Glycosylated narciclasine alkaloid in Hippeastrum puniceum (Lam.) Kuntze.

• Crude methanolic extract as starting material for Amaryllidaceae alkaloid isolation. • Unusual glycosylated alkaloid derivative isolated avoiding acid-base procedure. • Complete characterization by means of NMR spectroscopy and X-Ray crystallography. • The isolated alkaloid showed no significant cytotoxicity at tested concentrations. The present work focused on the chemical study of the main alkaloid component in Brazilian indigenous Amaryllidaceae species Hippeastrum puniceum (Lam.) Kuntze. The strategy applied was based on a distinct partitioning process and chromatographic-purification steps using the crude methanolic extract as the starting material. In this way, the glycosylated derivative narciclasine-4- O - β -D-xylopyranoside was isolated from the ethyl acetate fraction of H. puniceum. Structural elucidation of the compound was performed through NMR (Nuclear Magnetic Resonance) analysis including mono- and bi-dimensional experiments. The absolute configuration was determined herein for the first time by means of X-Ray Crystallography. The compound was also evaluated as cytotoxic agent against colon (HCT 116) and breast (MCF-7) tumor cells, showing no significant activity at the tested concentrations of 10 and 50 μM. [ABSTRACT FROM AUTHOR]