Synthesis and trypanocidal activity of ent-kaurane glycosides

Novel ent-kaurane glucosides were synthezised by a Koenigs–Knorr reaction between C17 and C19 alcohols derived from kaurenoic acid and 2,3,4,6-tetra-O-acetyl-glucopyranosyl bromide, followed by the hydrolysis of the acetates. Main products were assayed in vitro and in vivo against blood trypomastigote forms of Trypanosoma cruzi, the aetiological agent of Chagas’ disease (American trypanosomiasis). The results allowed to establish structure–activity relationships among these derivatives, as well as pointed out the C19-methylester-C17-O-glucoside as a potential trypanocidal agent, whose trypanocidal profile was shown to be comparable to those of gentian violet and benznidazole.

Starting from kaurenoic acid, novel ent-kaurane glycosides were synthesized and evaluated by in vitro and in vivo assays against Trypanosoma cruzi, the aetiological agent of Chagas’ disease.Figure optionsDownload as PowerPoint slide