Acetylenic fatty acids from Porcelia macrocarpa (Annonaceae) against trypomastigotes of Trypanosoma cruzi: Effect of octadec-9-ynoic acid in plasma membrane electric potential |
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| Affiliation: | 1. Institute of Environmental, Chemical and Pharmaceutical Sciences, Federal University of São Paulo, São Paulo 09972-270, Brazil;2. Center of Natural and Human Sciences, Federal University of ABC, Santo André 09210-580, Brazil;3. Center for Parasitology and Mycology, Adolfo Lutz Institute, São Paulo 01246-000, Brazil;4. Nucleus of Research in Physiology and Biochemistry, Institute of Botany of São Paulo, São Paulo 04301-902, Brazil;5. Institute of Food Chemistry, Technische Universität Braunschweig, Braunschweig 38106, Germany;1. Department of Chemistry, Sergipe Federal University, Campus Professor Alberto Carvalho, Itabaiana, SE, 49500-000, Brazil;2. Department of Chemistry, Sergipe Federal University, Jardim Rosa Elze, São Cristóvão, SE, 49100-000, Brazil;3. ‘NMR Center’, Paraná Federal University, Centro Politécnico, Jardim das Américas, PO Box 19081, Curitiba, PR 81531-990, Brazil;4. Department of Chemistry, Amazonas Federal University, Manaus, AM, 69077-000, Brazil;1. Univ Bourgogne Franche-Comté, Team ‘Biochemistry of the Peroxisome, Inflammation and Lipid Metabolism’ EA 7270/INSERM, Dijon, France;2. Univ. Tunis El Manar—Pasteur Institut, Lab. ‘Venoms & Therapeutic Biomolecules’, Tunis, Tunisia;3. Univ Monastir, LR12ES05, Lab-NAFS ‘Nutrition—Functional Food & Vascular Health’, Monastir, Tunisia;4. Univ Lorraine, LCPMC-A2, ICPM, Dept of Chemistry, Metz, France;5. Dept Neurology, Hôpital de Hautepierre, Strasbourg, France;6. Dept Neurology, Univ. Hospital of Dijon, Univ. Bourgogne Franche-Comté/EA7270, Dijon, France;1. Institute of Chemistry, Federal University of Mato Grosso do Sul, Av. Filinto Müller 1555, 79074-460, Campo Grande, MS, Brazil;2. Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508-000, São Paulo, SP, Brazil;3. Departamento de Estudos Básicos e Instrumentais, Universidade Estadual do Sudoeste da Bahia, BR 415, Km 03, 45700-000, Itapetinga, Bahia, Brazil;4. Departamento de Química, Universidade Federal Rural de Pernambuco, Rua Dom Manoel de Medeiros, 52171-030, Recife, PE, Brazil;5. Department of Organic Chemistry, Institute of Chemistry, Federal University of Bahia, Rua Barão de Jeremoabo 147, 40170-115 Salvador, BA, Brazil;1. Department of Entomology and Nematology, and UC Davis Comprehensive Cancer Center, University of California, Davis, CA, 95616, USA;2. Department of Chemistry, Technology and Equipment of Chemical Industry, Volzhsky Polytechnic Institute (branch) Volgograd State Technical University, Volzhsky, Russia |
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| Abstract: | 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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| Keywords: | Annonaceae Acetylenic fatty acids Plasma membrane disturbance |
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