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Molecules
2014 May 05;195:5761-76. doi: 10.3390/molecules19055761.
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Antiparasitic activity of natural and semi-synthetic tirucallane triterpenoids from Schinus terebinthifolius (Anacardiaceae): structure/activity relationships.
Morais TR
,
da Costa-Silva TA
,
Tempone AG
,
Borborema SE
,
Scotti MT
,
de Sousa RM
,
Araujo AC
,
de Oliveira A
,
de Morais SA
,
Sartorelli P
,
Lago JH
.
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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.
Figure 1. Structures of natural compounds 1–3 and semi-synthetic 1a–c, 2a–d, 3a, and 3b tirucallane triterpenoids.
Figure 2. Decision Trees (DT) generated for the set of triterpenoids with antiparasitic activity. (A) The compounds with higher values of DD5 (differences of the hydrophobic volumes at energy level of −1.0 kcal/mol) than 0.125 were active against T. cruzi trypomastigotes. (B) Compounds with higher values of DD8 (differences of the hydrophobic volumes at energy level of −1.6 kcal/mol) than 0.125 were active against L. infantum amastigotes. (C) Triterpenoids with DD4 (differences of the hydrophobic volumes at energy level of −0.8 kcal/mol) values higher than 0.8125 or DD5 values lower or equal to 0.25 were not cytotoxic against NCTC. The numbers in brackets show the number of compounds correctly classified/incorrectly as active (A) or inactive (I).
Abdel-Sattar,
In vitro activities of plant extracts from Saudi Arabia against malaria, leishmaniasis, sleeping sickness and Chagas disease.
2010, Pubmed
Abdel-Sattar,
In vitro activities of plant extracts from Saudi Arabia against malaria, leishmaniasis, sleeping sickness and Chagas disease.
2010,
Pubmed
Barrett,
Management of trypanosomiasis and leishmaniasis.
2012,
Pubmed
Bendaoud,
Chemical composition and anticancer and antioxidant activities of Schinus molle L. and Schinus terebinthifolius Raddi berries essential oils.
2010,
Pubmed
Bou,
Chemical composition and cytotoxicity evaluation of essential oil from leaves of Casearia sylvestris, its main compound α-zingiberene and derivatives.
2013,
Pubmed
,
Echinobase
Corrêa,
Anti-leishmanial and anti-trypanosomal potential of polygodial isolated from stem barks of Drimys brasiliensis Miers (Winteraceae).
2011,
Pubmed
Jain,
Specific competitive inhibitor of secreted phospholipase A2 from berries of Schinus terebinthifolius.
1995,
Pubmed
Johann,
Antifungal activity of schinol and a new biphenyl compound isolated from Schinus terebinthifolius against the pathogenic fungus Paracoccidioides brasiliensis.
2010,
Pubmed
Lane,
In vitro trypanocidal activity of tetraethylthiuram disulfide and sodium diethylamine-N-carbodithioate on Trypanosoma cruzi.
1996,
Pubmed
Mesquita,
Activity of imidazole compounds on Leishmania (L.) infantum chagasi: reactive oxygen species induced by econazole.
2014,
Pubmed
Moura-Costa,
Antimicrobial activity of plants used as medicinals on an indigenous reserve in Rio das Cobras, Paraná, Brazil.
2012,
Pubmed
Murray,
Roles of endogenous gamma interferon and macrophage microbicidal mechanisms in host response to chemotherapy in experimental visceral leishmaniasis.
2000,
Pubmed
Rea,
Soulamarin isolated from Calophyllum brasiliense (Clusiaceae) induces plasma membrane permeabilization of Trypanosoma cruzi and mytochondrial dysfunction.
2013,
Pubmed
,
Echinobase
Reimão,
Anti-leishmanial and anti-trypanosomal activities of 1,4-dihydropyridines: In vitro evaluation and structure-activity relationship study.
2010,
Pubmed
Santana,
Essential oils from Schinus terebinthifolius leaves - chemical composition and in vitro cytotoxicity evaluation.
2012,
Pubmed
,
Echinobase
Schmourlo,
Screening of antifungal agents using ethanol precipitation and bioautography of medicinal and food plants.
2005,
Pubmed
Tada,
An improved colorimetric assay for interleukin 2.
1986,
Pubmed
Tempone,
Current approaches to discover marine antileishmanial natural products.
2011,
Pubmed
Tempone,
Antileishmanial and antitrypanosomal activity of bufadienolides isolated from the toad Rhinella jimi parotoid macrogland secretion.
2008,
Pubmed
Yamamoto,
Treatment with triterpenic fraction purified from Baccharis uncinella leaves inhibits Leishmania (Leishmania) amazonensis spreading and improves Th1 immune response in infected mice.
2014,
Pubmed
da Silva,
The seasonal variation of the chemical composition of essential oils from Porcelia macrocarpa R.E. Fries (Annonaceae) and their antimicrobial activity.
2013,
Pubmed
,
Echinobase
de Lima,
Anti-bacterial activity of some Brazilian medicinal plants.
2006,
Pubmed
de Oliveira,
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption.
2012,
Pubmed
