In Mexico, Pentalinon andrieuxii roots have been used traditionally for the treatment of leishmaniasis (a parasitic disease affecting 12 million people worldwide). Research aimed at the identification of the natural products responsible for this activity and ultimately the discovery of new leads for the treatment of leishmaniasis led to the isolation and structural elucidation of 20 compounds, of which 18 were known. Five sterols (e.g., pentalinonsterol) showed potent in vitro and in vivo leishmanicidal activity. The most potent compounds, however, were obtained in only very limited quantities. These sterols, therefore, were prepared on larger scale via semi-synthesis from readily available starting materials. The synthetic routes were then modified to enable the systematic modification of the sterol functionality for structure-activity relationship studies, evaluation of their pharmacological profiles, and elucidation of their mechanism of action. An overview of these efficient and cost-effective semisynthetic strategies will be presented.

Synthesis and modification of natural sterols possessing antileishmanial activity

243rd National Meeting (2012)

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