Molecules 2014, 19(5), 5761-5776; doi:10.3390/molecules19055761
Article

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

1, 2, 2, 2, 3, 4, 4, 4, 4, 1 and 1,* email
Received: 12 March 2014; in revised form: 26 April 2014 / Accepted: 28 April 2014 / Published: 5 May 2014
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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 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.
Keywords: Schinus terebinthifolius; leaves; tirucallane triterpenoids; Leishmania (L.) infantum; Trypanosoma cruzi; structure-activity
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MDPI and ACS Style

Morais, T.R.; da Costa-Silva, T.A.; Tempone, A.G.; Borborema, S.E.T.; Scotti, M.T.; de Sousa, R.M.F.; Araujo, A.C.C.; de Oliveira, A.; de Morais, S.A.L.; Sartorelli, P.; Lago, J.H.G. Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships. Molecules 2014, 19, 5761-5776.

AMA Style

Morais TR, da Costa-Silva TA, Tempone AG, Borborema SET, Scotti MT, de Sousa RMF, Araujo ACC, de Oliveira A, de Morais SAL, Sartorelli P, Lago JHG. Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships. Molecules. 2014; 19(5):5761-5776.

Chicago/Turabian Style

Morais, Thiago R.; da Costa-Silva, Thais A.; Tempone, Andre G.; Borborema, Samanta E.T.; Scotti, Marcus T.; de Sousa, Raquel M.F.; Araujo, Ana C.C.; de Oliveira, Alberto; de Morais, Sérgio A.L.; Sartorelli, Patricia; Lago, João H.G. 2014. "Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships." Molecules 19, no. 5: 5761-5776.

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