Estudo Químico de Hippeastrum puniceum (Lam.) Kuntze: uma espécie da família Amaryllidaceae

Abstract

The Amaryllidaceae family is known primarily for producing biologically active alkaloids, isoquinolines, which exhibit an extensive variety of biological activity as antitumor, antifungal, antiviral, antiparasitic, antimalarial and, no less importantly, the inhibitory activity of the enzyme acetylcholinesterase (AChE). In this work, the chemical study of the species Hippeastrum puniceum (Lam.) Kuntze collected in the Espírito Santo mountain region is reported. In this sense, solvent extraction and partitioning of methanolic extract of the H. puniceum plant material was performed, followed by chromatographic separation techniques in order to isolate alkaloids from this species. This work proposes a new alkaloid in H. puniceum species, narciclasine-4-O-β-D-xylopyranoside, isolated from the ethyl acetate fraction, originated from the extraction of the bulbs, leaves and roots of the species. Structural elucidation of the compound was performed through analysis of data obtained in one-dimensional (1H and 13C) nuclear magnetic resonance (NMR) spectra, and two-dimensional: 1H1H correlation spectroscopy (COSY), heteronuclear single-quantum corherence (HSQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY). The confirmation of stereochemistry was performed by crystallographic analysis. After comparison and review of literature, it was possible to verify that this is a new glycoside in the species. The substance was tested on colon (HCT 116) and breast (MCF-7) tumor cells, which showed no expressive activity.