Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNIFESP |
Texto Completo: | http://repositorio.unifesp.br/handle/11600/35418 http://dx.doi.org/10.1016/j.exppara.2012.08.019 |
Resumo: | Leishmaniasis and Chagas disease are parasitic protozoan infections that affect the poorest population in the world, causing high mortality and morbidity. As a result of highly toxic and long-duration treatments, novel, safe and more efficacious drugs are essential. in this work, the methanol (MeOH) extract from the leaves of Piper malacophyllum (Piperaceae) was fractioned to afford one alkenylphenol, which was characterized as 4-[(3'E)-decenyl]phenol (gibbilimbol B) by spectroscopic methods. Anti-protozoan in vitro assays demonstrated for the first time that Leishmania (L.) infantum chagasi was susceptible to gibbilimbol B. with an in vitro EC50 of 23 mu g/mL against axenic promastigotes and an EC50 of 22 mu g/mL against intracellular amastigotes. Gibbilimbol B was also tested for anti-trypanosomal activity (Trypanosoma cruzi) and showed an EC50 value of 17 mu g/mL against trypomastigotes. To evaluate the cytotoxic parameters, this alkenylphenol was tested in vitro against NCTC cells, showing a CC50 of 59 mu g/mL and absent hemolytic activity at the highest concentration of 75 mu g/mL. Using the fluorescent probe SYTOX Green suggested that the alkenylphenol disrupted the Leishmania plasma membrane upon initial incubation. Further drug design studies aiming at derivatives could be a promising tool for the development of new therapeutic agents for leishmaniasis and Chagas disease. (C) 2012 Elsevier Inc. All rights reserved. |
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Oliveira, Alberto deMesquita, Juliana T.Tempone, Andre G.Lago, Joao Henrique Ghilardi [UNIFESP]Guimaraes, Elsie F.Kato, Massuo J.Universidade Federal de Uberlândia (UFU)Adolfo Lutz InstUniversidade Federal de São Paulo (UNIFESP)Inst Pesquisas Jardim Bot Rio de JaneiroUniversidade de São Paulo (USP)2016-01-24T14:27:54Z2016-01-24T14:27:54Z2012-11-01Experimental Parasitology. San Diego: Academic Press Inc Elsevier Science, v. 132, n. 3, p. 383-387, 2012.0014-4894http://repositorio.unifesp.br/handle/11600/35418http://dx.doi.org/10.1016/j.exppara.2012.08.019WOS000310497000012.pdf10.1016/j.exppara.2012.08.019WOS:000310497000012Leishmaniasis and Chagas disease are parasitic protozoan infections that affect the poorest population in the world, causing high mortality and morbidity. As a result of highly toxic and long-duration treatments, novel, safe and more efficacious drugs are essential. in this work, the methanol (MeOH) extract from the leaves of Piper malacophyllum (Piperaceae) was fractioned to afford one alkenylphenol, which was characterized as 4-[(3'E)-decenyl]phenol (gibbilimbol B) by spectroscopic methods. Anti-protozoan in vitro assays demonstrated for the first time that Leishmania (L.) infantum chagasi was susceptible to gibbilimbol B. with an in vitro EC50 of 23 mu g/mL against axenic promastigotes and an EC50 of 22 mu g/mL against intracellular amastigotes. Gibbilimbol B was also tested for anti-trypanosomal activity (Trypanosoma cruzi) and showed an EC50 value of 17 mu g/mL against trypomastigotes. To evaluate the cytotoxic parameters, this alkenylphenol was tested in vitro against NCTC cells, showing a CC50 of 59 mu g/mL and absent hemolytic activity at the highest concentration of 75 mu g/mL. Using the fluorescent probe SYTOX Green suggested that the alkenylphenol disrupted the Leishmania plasma membrane upon initial incubation. Further drug design studies aiming at derivatives could be a promising tool for the development of new therapeutic agents for leishmaniasis and Chagas disease. (C) 2012 Elsevier Inc. All rights reserved.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Univ Fed Uberlandia, Inst Quim, BR-38400 Uberlandia, MG, BrazilAdolfo Lutz Inst, Dept Parasitol, São Paulo, BrazilUniversidade Federal de São Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Diadema, SP, BrazilInst Pesquisas Jardim Bot Rio de Janeiro, Rio de Janeiro, RJ, BrazilUniv São Paulo, Inst Quim, São Paulo, BrazilUniversidade Federal de São Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Diadema, SP, BrazilWeb of Science383-387engElsevier B.V.Experimental Parasitologyhttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policyinfo:eu-repo/semantics/openAccessPiper malacophyllumPiperaceaeLeishmania (L.) infantum chagasiTrypanosoma cruziGibbilimbol BLeishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruptioninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlereponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESPORIGINALWOS000310497000012.pdfapplication/pdf274360${dspace.ui.url}/bitstream/11600/35418/1/WOS000310497000012.pdf1d36763de3efac0a6231dbe9bf22b4b5MD51open accessTEXTWOS000310497000012.pdf.txtWOS000310497000012.pdf.txtExtracted texttext/plain31119${dspace.ui.url}/bitstream/11600/35418/9/WOS000310497000012.pdf.txt702ac3dc7efad62d97ed5b125677d8a6MD59open accessTHUMBNAILWOS000310497000012.pdf.jpgWOS000310497000012.pdf.jpgIM Thumbnailimage/jpeg6949${dspace.ui.url}/bitstream/11600/35418/11/WOS000310497000012.pdf.jpgde3987fdf52d074d5c679a803626163dMD511open access11600/354182023-06-05 19:23:04.031open accessoai:repositorio.unifesp.br:11600/35418Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestopendoar:34652023-06-05T22:23:04Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false |
dc.title.en.fl_str_mv |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
title |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
spellingShingle |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption Oliveira, Alberto de Piper malacophyllum Piperaceae Leishmania (L.) infantum chagasi Trypanosoma cruzi Gibbilimbol B |
title_short |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
title_full |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
title_fullStr |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
title_full_unstemmed |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
title_sort |
Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption |
author |
Oliveira, Alberto de |
author_facet |
Oliveira, Alberto de Mesquita, Juliana T. Tempone, Andre G. Lago, Joao Henrique Ghilardi [UNIFESP] Guimaraes, Elsie F. Kato, Massuo J. |
author_role |
author |
author2 |
Mesquita, Juliana T. Tempone, Andre G. Lago, Joao Henrique Ghilardi [UNIFESP] Guimaraes, Elsie F. Kato, Massuo J. |
author2_role |
author author author author author |
dc.contributor.institution.none.fl_str_mv |
Universidade Federal de Uberlândia (UFU) Adolfo Lutz Inst Universidade Federal de São Paulo (UNIFESP) Inst Pesquisas Jardim Bot Rio de Janeiro Universidade de São Paulo (USP) |
dc.contributor.author.fl_str_mv |
Oliveira, Alberto de Mesquita, Juliana T. Tempone, Andre G. Lago, Joao Henrique Ghilardi [UNIFESP] Guimaraes, Elsie F. Kato, Massuo J. |
dc.subject.eng.fl_str_mv |
Piper malacophyllum Piperaceae Leishmania (L.) infantum chagasi Trypanosoma cruzi Gibbilimbol B |
topic |
Piper malacophyllum Piperaceae Leishmania (L.) infantum chagasi Trypanosoma cruzi Gibbilimbol B |
description |
Leishmaniasis and Chagas disease are parasitic protozoan infections that affect the poorest population in the world, causing high mortality and morbidity. As a result of highly toxic and long-duration treatments, novel, safe and more efficacious drugs are essential. in this work, the methanol (MeOH) extract from the leaves of Piper malacophyllum (Piperaceae) was fractioned to afford one alkenylphenol, which was characterized as 4-[(3'E)-decenyl]phenol (gibbilimbol B) by spectroscopic methods. Anti-protozoan in vitro assays demonstrated for the first time that Leishmania (L.) infantum chagasi was susceptible to gibbilimbol B. with an in vitro EC50 of 23 mu g/mL against axenic promastigotes and an EC50 of 22 mu g/mL against intracellular amastigotes. Gibbilimbol B was also tested for anti-trypanosomal activity (Trypanosoma cruzi) and showed an EC50 value of 17 mu g/mL against trypomastigotes. To evaluate the cytotoxic parameters, this alkenylphenol was tested in vitro against NCTC cells, showing a CC50 of 59 mu g/mL and absent hemolytic activity at the highest concentration of 75 mu g/mL. Using the fluorescent probe SYTOX Green suggested that the alkenylphenol disrupted the Leishmania plasma membrane upon initial incubation. Further drug design studies aiming at derivatives could be a promising tool for the development of new therapeutic agents for leishmaniasis and Chagas disease. (C) 2012 Elsevier Inc. All rights reserved. |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-11-01 |
dc.date.accessioned.fl_str_mv |
2016-01-24T14:27:54Z |
dc.date.available.fl_str_mv |
2016-01-24T14:27:54Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
Experimental Parasitology. San Diego: Academic Press Inc Elsevier Science, v. 132, n. 3, p. 383-387, 2012. |
dc.identifier.uri.fl_str_mv |
http://repositorio.unifesp.br/handle/11600/35418 http://dx.doi.org/10.1016/j.exppara.2012.08.019 |
dc.identifier.issn.none.fl_str_mv |
0014-4894 |
dc.identifier.file.none.fl_str_mv |
WOS000310497000012.pdf |
dc.identifier.doi.none.fl_str_mv |
10.1016/j.exppara.2012.08.019 |
dc.identifier.wos.none.fl_str_mv |
WOS:000310497000012 |
identifier_str_mv |
Experimental Parasitology. San Diego: Academic Press Inc Elsevier Science, v. 132, n. 3, p. 383-387, 2012. 0014-4894 WOS000310497000012.pdf 10.1016/j.exppara.2012.08.019 WOS:000310497000012 |
url |
http://repositorio.unifesp.br/handle/11600/35418 http://dx.doi.org/10.1016/j.exppara.2012.08.019 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartof.none.fl_str_mv |
Experimental Parasitology |
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http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy |
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openAccess |
dc.format.none.fl_str_mv |
383-387 |
dc.publisher.none.fl_str_mv |
Elsevier B.V. |
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Elsevier B.V. |
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