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

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

Author Morais, Thiago R. Autor UNIFESP Google Scholar
Costa-Silva, Thais A. da Google Scholar
Tempone, Andre G. Google Scholar
Borborema, Samanta Etel T. Google Scholar
Scotti, Marcus T. Google Scholar
Sousa, Raquel Maria F. de Google Scholar
Araujo, Ana Carolina C. Google Scholar
Oliveira, Alberto de Google Scholar
Morais, Sergio Antonio L. de Google Scholar
Sartorelli, Patricia Autor UNIFESP Google Scholar
Lago, Joao Henrique G. Autor UNIFESP Google Scholar
Institution Universidade Federal de São Paulo (UNIFESP)
Adolfo Lutz Inst
Univ Fed Paraiba
Universidade Federal de Uberlândia (UFU)
Abstract 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 mu g/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC50 values in the range between 28 and 97 mu g/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.
Keywords Schinus terebinthifolius
leaves
tirucallane triterpenoids
Leishmania (L.) infantum
Trypanosoma cruzi
structure-activity
Language English
Sponsor Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG)
Grant number CNPq: 300546/2012-2
CNPq: 471458/2012-0
FAPESP: 2011/51739-0
FAPESP: 2012/18756-1
FAPESP: 2013/16320-4
Date 2014-05-01
Published in Molecules. Basel: Mdpi Ag, v. 19, n. 5, p. 5761-5776, 2014.
ISSN 1420-3049 (Sherpa/Romeo, impact factor)
Publisher Mdpi Ag
Extent 5761-5776
Origin http://dx.doi.org/10.3390/molecules19055761
Access rights Open access Open Access
Type Article
Web of Science ID WOS:000337113000020
URI http://repositorio.unifesp.br/handle/11600/37702

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