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Acetylenic fatty acids from Porcelia macrocarpa (Annonaceae) against trypomastigotes of Trypanosoma cruzi: Effect of octadec-9-ynoic acid in plasma membrane electric potential.
Londero, Vinicius S; da Costa-Silva, Thais A; Gomes, Kaio S; Ferreira, Daiane D; Mesquita, Juliana T; Tempone, Andre G; Young, Maria Claudia M; Jerz, Gerold; Lago, João Henrique G.
Afiliação
  • Londero VS; Institute of Environmental, Chemical and Pharmaceutical Sciences, Federal University of São Paulo, São Paulo 09972-270, Brazil.
  • da Costa-Silva TA; Center of Natural and Human Sciences, Federal University of ABC, Santo André 09210-580, Brazil.
  • Gomes KS; Center of Natural and Human Sciences, Federal University of ABC, Santo André 09210-580, Brazil.
  • Ferreira DD; Center for Parasitology and Mycology, Adolfo Lutz Institute, São Paulo 01246-000, Brazil.
  • Mesquita JT; Center for Parasitology and Mycology, Adolfo Lutz Institute, São Paulo 01246-000, Brazil.
  • Tempone AG; Center for Parasitology and Mycology, Adolfo Lutz Institute, São Paulo 01246-000, Brazil.
  • Young MCM; Nucleus of Research in Physiology and Biochemistry, Institute of Botany of São Paulo, São Paulo 04301-902, Brazil.
  • Jerz G; Institute of Food Chemistry, Technische Universität Braunschweig, Braunschweig 38106, Germany.
  • Lago JHG; Center of Natural and Human Sciences, Federal University of ABC, Santo André 09210-580, Brazil. Electronic address: joao.lago@ufabc.edu.br.
Bioorg Chem ; 78: 307-311, 2018 08.
Article em En | MEDLINE | ID: mdl-29625270
Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae) is an endemic plant in Brazil where its tasty pulp has been eaten fresh. The hexane extract from its flowers was subjected to chromatographic procedures to afford four acetylene derivatives identified as octadec-9-ynoic (stearolic acid - 1), (11E)-octadec-11-en-9-ynoic (santalbic acid - 2), 8-hydroxyoctadec-9,11-diynoic (3) and 8-hydroxyoctadec-17-en-9,11-diynoic (isanolic acid - 4) acids by NMR and HRESIMS. Among tested compounds against trypomastigote forms of T. cruzi, octadec-9-ynoic acid (1) displayed higher potential with IC50 = 27.6 µM and a selectivity index (SI) higher than 7. Compounds 2 and 3 showed IC50 of approximately 60 µM while compound 4 was inactive. The lethal action of the compound 1 was investigated using spectrofluorometric techniques to detect ROS content, plasma membrane permeability and plasma membrane potential by flow cytometry. Compound 1 showed no alteration in the production of ROS of treated trypomastigotes and no alteration of the plasma membrane permeability was observed as detected by the fluorescent probe SYTOX-green after 120 min of incubation. However, by using the potential-sensitive fluorescent probe DiSBAC2(3), compound 1 caused depolarization of the plasma membrane potential when compared to untreated parasites. Our results demonstrated the anti-T. cruzi effects of compounds 1-3 isolated from flowers of P. macrocarpa and indicated that the lethal effect of compound 1 in T. cruzi could be associated to the plasma membrane disturbance of the parasite.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Tripanossomicidas / Trypanosoma cruzi / Membrana Celular / Annonaceae / Alcinos / Ácidos Graxos Limite: Animals Idioma: En Revista: Bioorg Chem Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos
Texto completo
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XML
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Tripanossomicidas / Trypanosoma cruzi / Membrana Celular / Annonaceae / Alcinos / Ácidos Graxos Limite: Animals Idioma: En Revista: Bioorg Chem Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos