Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships

Molecules

Thiago R. Morais¹  Thais A. da Costa-Silva⁴  Andre G. Tempone⁴  Samanta Etel T. Borborema⁴  Marcus T. Scotti²  Raquel Maria F. de Sousa³  Ana Carolina C. Araujo³  Alberto de Oliveira³  Sérgio Antônio L. de Morais³  Patricia Sartorelli¹ 

[1] Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema, SP 09972270, Brazil;Centro de Ciências Aplicadas e Educação, Universidade Federal da Paraíba, Rio Tinto, PB 58297000, Brazil;Instituto de Química, Universidade Federal de Uberlândia, Uberlândia, MG 38400902, Brazil;Centro de Parasitologia, Instituto Adolfo Lutz, São Paulo, SP 01246902, Brazil

关键词: Schinus terebinthifolius;    leaves;    tirucallane triterpenoids;    Leishmania (L.) infantum;    Trypanosoma cruzi;    structure-activity;   

DOI  :  10.3390/molecules19055761

来源: mdpi

【 摘 要 】

Leishmaniasis and Chagas are diseases caused by parasitic protozoans that affect the poorest population in the World, causing a high mortality and morbidity. As a result of highly toxic and long-term treatments, the discovery of novel, safe and more efficacious drugs is essential. In this work, the in vitro antiparasitic activity and mammalian cytotoxicity of three natural tirucallane triterpenoids, isolated from leaves of Schinus terebinthifolius (Anacardiaceae), and nine semi-synthetic derivatives were investigated against Leishmania (L.) infantum and Trypanosoma cruzi. Trypomastigotes of T. cruzi were the most susceptible parasites and seven compounds demonstrated a trypanocidal activity with IC₅₀ values in the range between 15 and 58 µg/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC₅₀ values in the range between 28 and 97 µg/mL. The complete characterization of triterpenoids was afforded after thorough analysis of nuclear magnetic resonance (NMR) data as well as electrospray ionization mass spectrometry (ESI-MS). Additionally, structure-activity relationships were performed using Decision Trees.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.