Alkaloid Constituents of the Amaryllidaceae Plant Amaryllis belladonna L.

Molecules. 2017 Aug 31;22(9). pii: E1437. doi: 10.3390/molecules22091437. Tallini LR1, Andrade JP2, Kaiser M3,4, Viladomat F5, Nair JJ6, Zuanazzi JAS7, Bastida J8. Author information 1 Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain. lucianatallini@gmail.com. 2 Departamento de Química Orgânica, Universidade Federal do Espírito Santo, Av. Fernando Ferrari 845, Victoria 29075-015, Brazil. deandradejp@gmail.com. 3 Medicinal Parasitology and Infection Biology, Swiss Tropical Institute, Socinstrasse 57, 4051 Basel, Switzerland. marcel.kaiser@unibas.ch. 4 University of Basel, Petersplatz 1, 4001 Basel, Switzerland. marcel.kaiser@unibas.ch. 5 Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain. fviladomat@ub.edu. 6 Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain. nairjj@gmail.com. 7 Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, Porto Alegre 90610-000, Brazil. zuanazzi@ufrgs.br. 8 Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain. jaumebastida@ub.edu. 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. KEYWORDS: Amaryllidaceae; Amaryllis belladonna; MS; NMR; alkaloids; biosynthetic pathways PMID: 28858260 DOI: 10.3390/molecules22091437 Free full text http://www.mdpi.com/1420-3049/22/9/1437