Abstract
The plant family Amaryllidaceae is well-known for its unique alkaloid constituents, which exhibit a wide range of biological activities. Its representative, Amaryllis belladonna, has a geographical distribution covering mainly southern Africa, where it has significant usage in the traditional medicine of the native people. In this study, A. belladonna samples collected in Brazil were examined for alkaloid content. Alkaloid profiles of A. belladonna bulbs were generated by a combination of chromatographic, spectroscopic and spectrometric methods, including GC–MS and 2D NMR. In vitro screening against four different parasitic protozoa (Trypanosoma cruzi, T. brucei rhodesiense, Leishmania donovani and Plasmodium falciparum) was carried out using the A. belladonna crude methanol extract, as well as three of its alkaloid isolates. Twenty-six different Amaryllidaceae alkaloids were identified in the A. belladonna bulb samples, and three of them were isolated. Evidence for their respective biosynthetic pathways was afforded via their mass-spectral fragmentation data. Improved data for 1-O-acetylcaranine was provided by 2D NMR experiments, together with new 1H-NMR data for buphanamine. The crude extract and 3-O-acetylhamayne exhibited good antiprotozoal activity in vitro, although both with a high cytotoxic index.
Highlights
The plant family Amaryllidaceae has attracted considerable attention in view of the fascinating structural features and varied biological activities manifested by its alkaloid principles
Alkaloids Identified in A. belladonna by Gas chromatography-mass spectrometry (GC–mass spectrometry (MS))
The structural types of the alkaloids from A. belladonna were identified by comparing their GC–MS
Summary
The plant family Amaryllidaceae has attracted considerable attention in view of the fascinating structural features and varied biological activities manifested by its alkaloid principles. Anti-bacterial, anti-fungal and anti-neoplastic effects are associated with some of the alkaloids isolated from A. belladonna [2,20]. Protozoal diseases such as leishmaniasis, trypanosomiasis and malaria are still the most prevalent parasitic diseases worldwide, with a significant social and economic impact [22]. The aim of this work was to perform a detailed study of the alkaloid constituents of A. belladonna utilizing spectroscopic and chromatographic methods, including GC–MS and NMR. In this way, twenty-six alkaloids were identified and evidence presented for their respective biosynthetic pathways. Anti-parasitological activities of the crude extract and three isolated alkaloids from A. belladonna are reported for the first time
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