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

Author(s):Show less -

Morais, Thiago R. ^[1] ; da Costa-Silva, Thais A. ^[2] ; Tempone, Andre G. ^[2] ; Borborema, Samanta Etel T. ^[2] ; Scotti, Marcus T. ^[3] ; de Sousa, Raquel Maria F. ^[4] ; Araujo, Ana Carolina C. ^[4] ; de Oliveira, Alberto ^[4] ; de Morais, Sergio Antonio L. ^[4] ; Sartorelli, Patricia ^[1] ; Lago, Joao Henrique G. ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP - Brazil

^[2] Adolfo Lutz Inst, Ctr Parasitol, BR-01246902 Sao Paulo - Brazil

^[3] Univ Fed Paraiba, Ctr Ciencias Aplicadas & Educ, BR-58297000 Rio Tinto - Brazil

^[4] Univ Fed Uberlandia, Inst Quim, BR-38400902 Uberlandia, MG - Brazil

• Document type: Journal article
• Source: Molecules; v. 19, n. 5, p. 5761-5776, MAY 2014.
• Web of Science Citations: 8

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. (AU)

• FAPESP's process: 11/51739-0 - Sustainable use of biodiversity in Atlantic Forest remnants in São Paulo: evaluation, isolation and molecular characterization of bioactive secondary metabolites in plant species
• Grantee: João Henrique Ghilardi Lago
• Support type: BIOTA-FAPESP Program - Regular Research Grants
• FAPESP's process: 12/18756-1 - Evaluation of novel alternative therapies with synthetic drugs using in vitro and experimental models of Leishmania (L.) infantum chagasi
• Grantee: André Gustavo Tempone Cardoso
• Support type: Regular Research Grants
• FAPESP's process: 13/16320-4 - Prospection of anti-parasitic and anti-tumor metabolites from plant species of the Atlantic Forest
• Grantee: Patricia Sartorelli
• Support type: Regular Research Grants