Isolation and characterisation of the monoterpenoid indole alkaloids of Aspidosperma pyrifolium
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Malaria is a major parasitic infection in many tropical and subtropical regions with the most severe forms of the disease being caused by Plasmodium falciparum. Dramatic increases in the resistance of this mosquito-transmitted parasite to classical treatments have been observed in recent years, and much research effort is now aimed at the discovery of novel natural products with antiplasmodial activities. On the basis of its use in popular medicine, Aspidosperma pyrifolium Mart. (Apocynaceae), a tree popularly known as “pereiro-do-sertão,” was selected for detailed study. A phytochemical investigation of the aqueous extract of its stem bark revealed the presence of two known monoterpenoid indole alkaloids, 15-demethoxypyrifoline and aspidofractinine, together with the novel compound N-formylaspidofractinine. The structures of these compounds were established from UV, IR, MS and NMR data, and their 1H- and 13C-NMR spectra have been unambiguously assigned for the first time.
KeywordsApocynaceae Aspidosperma pyrifolium Malaria Monoterpenoid indole alkaloids Plasmodium falciparum
The authors wish to thank Frederic Meistermann and Benoît Portron (Biotage, France) for their kind help during the Flash Chromatography experiment, Patrick Wehrung (LSMBO, Campus CNRS, Cronenbourg, France) for providing the MS analysis and Roland Graff (SCRMN, ULP, Strasbourg, France) for providing access to the 500 MHz NMR spectrometer. The authors are indebted to the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação de Amparo à Pesquisa do Estado de Alagoas (FAPEAL), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and Banco do Nordeste do Brasil (BNB) for financial support in Brazil. One of us (J.X.A-J) wishes to thank CAPES for sponsorship.
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