title: Antitrypanosomal Acetylene Fatty Acid Derivatives from the Seeds of Porcelia macrocarpa (Annonaceae).
abstract: Chagas' disease is caused by a parasitic protozoan and affects the poorest population in the world, causing high mortality and morbidity. As a result of the toxicity and long duration of current treatments, the discovery of novel and more efficacious drugs is crucial. In this work, the hexane extract from seeds of Porcelia macrocarpa R.E. Fries (Annonaceae) displayed in vitro antitrypanosomal activity against trypomastigote forms of T. cruzi by the colorimetric MTT assay (IC50 of 65.44 μg/mL). Using chromatographic fractionation over SiO2, this extract afforded a fraction composed by one active compound (IC50 of 10.70 µg/mL), which was chemically characterized as 12,14-octadecadiynoic acid (macrocarpic acid). Additionally, two new inactive acetylene compounds (α,α'-dimacro-carpoyl-β-oleylglycerol and α-macrocarpoyl-α'-oleylglycerol) were also isolated from the hexane extract. The complete characterization of the isolated compounds was performed by analysis of NMR and MS data as well as preparation of derivatives.
authors.affiliation: Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais-NuBBE, Instituto de Química, Universidade Estadual Paulista, 14800-060 Araraquara, SP, Brazil. lsantos.avila@gmail.com.
authors.forename: Luciana
authors.initials: L
authors.lastname: de Á Santos
authors.affiliation: Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais-NuBBE, Instituto de Química, Universidade Estadual Paulista, 14800-060 Araraquara, SP, Brazil. lsantos.avila@gmail.com.
authors.forename: Alberto J
authors.initials: AJ
authors.lastname: Cavalheiro
authors.affiliation: Centro de Parasitologia e Micologia, Instituto Adolfo Lutz, 01246-902 São Paulo, SP, Brazil. atempone@usp.br.
authors.forename: Andre G
authors.initials: AG
authors.lastname: Tempone
authors.affiliation: Centro de Parasitologia e Micologia, Instituto Adolfo Lutz, 01246-902 São Paulo, SP, Brazil. nanisaraiva@yahoo.com.br.
authors.forename: Daniela S
authors.initials: DS
authors.lastname: Correa
authors.affiliation: Centro de Parasitologia e Micologia, Instituto Adolfo Lutz, 01246-902 São Paulo, SP, Brazil. tatilontani@hotmail.com.
authors.forename: Tatiana R
authors.initials: TR
authors.lastname: Alexandre
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema, SP, Brazil. nquintiliano@hotmail.com.
authors.forename: Natalia F
authors.initials: NF
authors.lastname: Quintiliano
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema, SP, Brazil. andre.filipe@unifesp.br.
authors.forename: André F
authors.initials: AF
authors.lastname: Rodrigues-Oliveira
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema, SP, Brazil. dosilva@unifesp.br.
authors.forename: Diogo
authors.initials: D
authors.lastname: Oliveira-Silva
authors.affiliation: Instituto de Pesquisa em Produtos Naturais, Universidade Federal do Rio de Janeiro, 21941-902 Rio de Janeiro, RJ, Brazil. roberto@correio.nppn.ufrj.br.
authors.forename: Roberto Carlos C
authors.initials: RC
authors.lastname: Martins
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema, SP, Brazil. joao.lago@unifesp.br.
authors.forename: João Henrique G
authors.initials: JH
authors.lastname: Lago
mesh_terms: D000114:Acetylene / Q000737:chemistry / Q000494:pharmacology*; D029061:Annonaceae / Q000737:chemistry*; D014355:Chagas Disease / Q000188:drug therapy; D005227:Fatty Acids / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D012639:Seeds / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D014349:Trypanosoma cruzi / Q000187:drug effects*
chemical_list: D005227:Fatty Acids; D010936:Plant Extracts; D012822:Silicon Dioxide; D000114:Acetylene