N-(Isobutyl)-3,4-methylenedioxy Cinnamoyl Amide
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Date
2019-07-03
Journal Title
Journal ISSN
Volume Title
Publisher
Molbank
Abstract
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 M) was
just four times less active than the commercially available drug diminazene aceturate (IC50 1.88 M).
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 sca old for the further development of
natural antitrypanosomal compounds.
Description
Research Article
Keywords
Trypanosomiasis, Antitrypanosomals, Cell cycle, Cell viability, Zanthoxylum, Rutaceae, 1,3-benzodioxole, Spectroscopy