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Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships
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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271887/ https://www.ncbi.nlm.nih.gov/pubmed/24802987 http://dx.doi.org/10.3390/molecules19055761 |
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author | Morais, Thiago R. da Costa-Silva, Thais A. Tempone, Andre G. Borborema, Samanta Etel T. Scotti, Marcus T. de Sousa, Raquel Maria F. Araujo, Ana Carolina C. de Oliveira, Alberto de Morais, Sérgio Antônio L. Sartorelli, Patricia Lago, João Henrique G. |
author_facet | Morais, Thiago R. da Costa-Silva, Thais A. Tempone, Andre G. Borborema, Samanta Etel T. Scotti, Marcus T. de Sousa, Raquel Maria F. Araujo, Ana Carolina C. de Oliveira, Alberto de Morais, Sérgio Antônio L. Sartorelli, Patricia Lago, João Henrique G. |
author_sort | Morais, Thiago R. |
collection | PubMed |
description | 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 IC(50) values in the range between 15 and 58 µg/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC(50) 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. |
format | Online Article Text |
id | pubmed-6271887 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62718872018-12-21 Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships Morais, Thiago R. da Costa-Silva, Thais A. Tempone, Andre G. Borborema, Samanta Etel T. Scotti, Marcus T. de Sousa, Raquel Maria F. Araujo, Ana Carolina C. de Oliveira, Alberto de Morais, Sérgio Antônio L. Sartorelli, Patricia Lago, João Henrique G. Molecules Article 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 IC(50) values in the range between 15 and 58 µg/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC(50) 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. MDPI 2014-05-05 /pmc/articles/PMC6271887/ /pubmed/24802987 http://dx.doi.org/10.3390/molecules19055761 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Morais, Thiago R. da Costa-Silva, Thais A. Tempone, Andre G. Borborema, Samanta Etel T. Scotti, Marcus T. de Sousa, Raquel Maria F. Araujo, Ana Carolina C. de Oliveira, Alberto de Morais, Sérgio Antônio L. Sartorelli, Patricia Lago, João Henrique G. Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships |
title | Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships |
title_full | Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships |
title_fullStr | Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships |
title_full_unstemmed | Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships |
title_short | Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae): Structure/Activity Relationships |
title_sort | antiparasitic activity of natural and semi-synthetic tirucallane triterpenoids from schinus terebinthifolius (anacardiaceae): structure/activity relationships |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271887/ https://www.ncbi.nlm.nih.gov/pubmed/24802987 http://dx.doi.org/10.3390/molecules19055761 |
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