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

Autor(es):Mostrar menos -

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: Molecules; v. 19, n. 5, p. 5761-5776, MAY 2014.
• Citações Web of Science: 8

Resumo

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)

• Processo FAPESP: 11/51739-0 - Uso sustentável da biodiversidade de áreas remanescentes da Mata Atlântica do Estado de São Paulo: avaliação, isolamento e caracterização molecular de metabólitos secundários bioativos em espécies vegetais
• Beneficiário: João Henrique Ghilardi Lago
• Modalidade de apoio: Auxílio à Pesquisa - Programa BIOTA - Regular
• Processo FAPESP: 13/16320-4 - Prospecção de metabólitos anti-parasitários e anti-tumorais de espécies vegetais da Mata Atlântica
• Beneficiário: Patricia Sartorelli
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 12/18756-1 - Avaliação de novas alternativas terapêuticas com fármacos sintéticos em modelos in vitro e experimentais de Leishmania (L.) infantum chagasi
• Beneficiário: André Gustavo Tempone Cardoso
• Modalidade de apoio: Auxílio à Pesquisa - Regular