Abstract
The plant Zanthoxylum zanthoxyloides (Lam.) Zepern. & Timler is one of the most important medicinal species of the genus Zanthoxylum on the African continent. It is used in the treatment and management of parasitic diseases in sub-Saharan Africa. These properties have inspired scientists to investigate species within the genus for bioactive compounds. However, a study, which details a spectroscopic, spectrometric and bioactivity guided extraction and isolation of antiparasitic compounds from the genus Zanthoxylum is currently non-existent. Tortozanthoxylamide (1), which is a derivative of the known compound armatamide was isolated from Z. zanthoxyloides and the full structure determined using UV, IR, 1D/2D-NMR and high-resolution liquid chromatography tandem mass spectrometry (HRESI-LC-MS) data. When tested against Trypanosoma brucei subsp. brucei, the parasite responsible for animal African trypanosomiasis in sub-Saharan Africa, 1 (IC50 7.78 µM) was just four times less active than the commercially available drug diminazene aceturate (IC50 1.88 µM). Diminazene aceturate is a potent drug for the treatment of animal African trypanosomiasis. Tortozanthoxylamide (1) exhibits a significant antitrypanosomal activity through remarkable alteration of the cell cycle in T. brucei subsp. brucei, but it is selectively non-toxic to mouse macrophages RAW 264.7 cell lines. This suggests that 1 may be considered as a scaffold for the further development of natural antitrypanosomal compounds.
Highlights
African trypanosomiasis (AT) is a tsetse-transmitted disease of humans and other animals caused by the parasitic protozoan that belongs to the Trypanosoma genus
Tortozanthoxylamide (1) loses this fragment in its mass fragmentation pathway and since it is coming from the same genus, we proposed that it is similar in structure to lanyuamide I–III
The genus Zanthoxylum is a copious producer of many structurally intriguing and biologically active compounds [24]. This explains why several species belonging to the genus are found in many remedies used in the treatment and management of several diseases in sub-Saharan Africa and the rest of the world
Summary
African trypanosomiasis (AT) is a tsetse-transmitted disease of humans and other animals caused by the parasitic protozoan that belongs to the Trypanosoma genus. The overall aim is to fully characterize the active principles behind the efficacy of these remedies One of these plants belongs to the genus Zanthoxylum and is widely distributed in most temperate and subtropical zones of Africa, Asia, North America, South America and Australia [10]. A bioactivity, spectroscopy and spectrometry guided isolation process involving the use of thin layer and Sephadex LH20 chromatography followed by HPLC led to the discovery of a new derivative of armatamide [19] The structure of this new compound was determined using a combination of IR, UV, 1D and 2D-NMR spectroscopy and high-resolution liquid chromatography tandem mass spectrometry (HRESI-LC-MS) techniques as. This new compound was found to exhibit selectively significant antitrypanosomal activity against Trypanosoma brucei subsp. brucei through a marked inhibition of the cell cycle phases of the parasite
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