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N-(Isobutyl)-3,4-methylenedioxy Cinnamoyl Amide

1
West African Center for Cell Biology of Infectious Pathogens, University of Ghana, P.O. Box LG 54 Legon-Accra, Ghana
2
Department of Biochemistry, Cell and Molecular Biology, University of Ghana, P.O. Box LG 54 Legon-Accra, Ghana
3
Marine and Plant Research Laboratory of Ghana, Department of Chemistry, School of Physical and Mathematical Sciences, University of Ghana, P.O. Box LG 56 Legon-Accra, Ghana
4
Department of Parasitology, Noguchi Memorial Institute for Medical Research, University of Ghana, P.O. Box LG 581 Legon-Accra, Ghana
*
Authors to whom correspondence should be addressed.
Molbank 2019, 2019(3), M1070; https://doi.org/10.3390/M1070
Received: 19 June 2019 / Revised: 2 July 2019 / Accepted: 3 July 2019 / Published: 5 July 2019
(This article belongs to the Section Natural Products)
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PDF [1841 KB, uploaded 9 July 2019]
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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. View Full-Text
Keywords: trypanosomiasis; antitrypanosomals; cell cycle; cell viability; Zanthoxylum; Rutaceae; 1,3-benzodioxole; spectroscopy trypanosomiasis; antitrypanosomals; cell cycle; cell viability; Zanthoxylum; Rutaceae; 1,3-benzodioxole; spectroscopy
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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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Dofuor, A.K.; Kwain, S.; Osei, E.; Mawuli Tetevi, G.; Okine, L.K.; Ohashi, M.; Gwira, T.M.; Kyeremeh, K. N-(Isobutyl)-3,4-methylenedioxy Cinnamoyl Amide. Molbank 2019, 2019, M1070.

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