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Molecules 2017, 22(9), 1437; doi:10.3390/molecules22091437

Alkaloid Constituents of the Amaryllidaceae Plant Amaryllis belladonna L

1
Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII 27–31, 08028 Barcelona, Spain
2
Departamento de Química Orgânica, Universidade Federal do Espírito Santo, Av. Fernando Ferrari 845, Victoria 29075-015, Brazil
3
Medicinal Parasitology and Infection Biology, Swiss Tropical Institute, Socinstrasse 57, 4051 Basel, Switzerland
4
University of Basel, Petersplatz 1, 4001 Basel, Switzerland
5
Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, Porto Alegre 90610-000, Brazil
*
Author to whom correspondence should be addressed.
Received: 19 July 2017 / Accepted: 26 August 2017 / Published: 31 August 2017
(This article belongs to the Collection Herbal Medicine Research)
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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. View Full-Text
Keywords: Amaryllis belladonna; Amaryllidaceae; alkaloids; biosynthetic pathways; NMR; MS Amaryllis belladonna; Amaryllidaceae; alkaloids; biosynthetic pathways; NMR; MS
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tallini, L.R.; Andrade, J.P.; Kaiser, M.; Viladomat, F.; Nair, J.J.; Zuanazzi, J.A.S.; Bastida, J. Alkaloid Constituents of the Amaryllidaceae Plant Amaryllis belladonna L. Molecules 2017, 22, 1437.

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