Abstract
Focused on our interest to develop novel antiparasistic agents, the present study was aimed to evaluate the biological activity of an extract of Laurencia johnstonii collected in Baja California Sur, Mexico, against an Acantamoeba castellanii Neff strain. Bioassay-guided fractionation allowed us to identify the amoebicidal diastereoisomers α-bromocuparane (4) and α-isobromocuparane (5). Furthermore, bromination of the inactive laurinterol (1) and isolaurinterol (2) yielded four halogenated derivatives, (6)–(9), which improved the activity of the natural sesquiterpenes. Among them, the most active compound was 3α-bromojohnstane (7), a sesquiterpene derivative which possesses a novel carbon skeleton johnstane.
Highlights
Free-living amoeba (FLA) are widely distributed protozoa in the environment [1,2,3]
We report the isolation of the known brominated johnstonii, both with a chamigrene carbon skeleton
To the best of our knowledge, red algae have never been evaluated as a potential source of amoebicidal agents
Summary
Free-living amoeba (FLA) are widely distributed protozoa in the environment [1,2,3] These parasites present a life cycle with two different stages: the trophozoite and the resistant phase, the cyst. Among FLA, Acanthamoeba genus [4] has been isolated from air, soil, water, contact lenses, air conditioning units, clinical samples, among others [5]. These parasites are able to cause pathologies in humans such as Granulomatous Amoebic Encephalitis (GAE) and Amoebic Keratitis (AK) [1,2,3,5]. The existing therapies are not fully effective against these organisms mainly due to the existence of the cyst phase, and due to the presence of strains that are resistant to the currently used anti-amoebic drugs [2,3,8]
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