Navegando por Palavras-chave "tirucallane triterpenoids"

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    Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships
    (Mdpi Ag, 2014-05-01) Morais, Thiago R. [UNIFESP]; Costa-Silva, Thais A. da; Tempone, Andre G.; Borborema, Samanta Etel T.; Scotti, Marcus T.; Sousa, Raquel Maria F. de; Araujo, Ana Carolina C.; Oliveira, Alberto de; Morais, Sergio Antonio L. de; Sartorelli, Patricia [UNIFESP]; Lago, Joao Henrique G. [UNIFESP]; Universidade Federal de São Paulo (UNIFESP); Adolfo Lutz Inst; Univ Fed Paraiba; Universidade Federal de Uberlândia (UFU)
    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.
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    Application of an Ionic Liquid in the Microwave Assisted Extraction of Cytotoxic Metabolites from Fruits of Schinus terebinthifolius Raddi (Anacardiaceae)
    (Soc Brasileira Quimica, 2017) Morais, Thiago R. [UNIFESP]; Coutinho, Ana Paula R. [UNIFESP]; Camilo, Fernanda F. [UNIFESP]; Martins, Tereza S. [UNIFESP]; Sartorelli, Patricia [UNIFESP]; Massaoka, Mariana H. [UNIFESP]; Figueiredo, Carlos R. [UNIFESP]; Lago, Joao Henrique G. [UNIFESP]
    This work reports the application of an ionic liquid (1-butyl-3-methylimidazolium bromide, BMImBr) in the microwave assisted extraction (MAE) of metabolites from fruits of Schinus terebinthifolius. Dried fruits were individually extracted using BMImBr: H2O 1: 1, v/v (experiment 1) and pure H2O (experiment 2) by MAE (10 min at 60 degrees C). After partition using EtOAc, the yield to experiment 1 was about 23% while to experiment 2 was 0.1%. The EtOAc fraction obtained from experiment 1 was purified by chromatographic methods to afford 3-oxotirucalla-7,24Z-dien27- oic acid, 3a-hydroxytirucalla-7,24Z-dien-27-oic acid, 3 alpha-acetoxytirucalla-7,24Z-dien-27-oic acid, gallic acid, and ethyl gallate, being the first occurrence of the third compound as natural product. Cytotoxic activity was evaluated in vitro against cancer cell lines (A2058, HeLa, SiHa, HCT, SKBR-3, U87, and B16F2Nex2), being 3 alpha-acetoxytirucalla-7,24Z-dien-27-oic acid the more active metabolite with IC50 ranging from 10.9 +/- 1.3 to 17.3 +/- 1.4 mu g mL(-1), lower than that determined to positive control cisplatin.