title: Schistosomicidal Activity of Alkyl-phenols from the Cashew Anacardium occidentale against Schistosoma mansoni Adult Worms.
abstract: Bioassay-guided study of the ethanol extract from the cashew Anacardium occidentale furnished cardol triene (1), cardol diene (2), anacardic acid triene (3), cardol monoene (4), anacardic acid diene (5), 2-methylcardol triene (6), and 2-methylcardol diene (7). 1D- and 2D-NMR experiments and HRMS analysis confirmed the structures of compounds 1-7. Compounds 2 and 7 were active against Schistosoma mansoni adult worms in vitro, with LC50values of 32.2 and 14.5 μM and selectivity indices of 6.1 and 21.2, respectively. Scanning electron microscopy of the tegument of male worms in the presence of compound 7 at 25 μM after 24 h of incubation showed severe damage as well as peeling and reduction in the number of spine tubercles. Transmission electron microscopy analyses revealed swollen mitochondrial membrane, vacuoles, and altered tegument in worms incubated with compound 2 (25 μM after 24 h). Worms incubated with compound 7 (25 μM after 24 h) had lysed interstitial tissue, degenerated mitochondria, and drastically altered tegument. Together, the results indicated that compound 7 presents promising in vitro schistosomicidal activity.
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Tavane A
authors.initials: TA
authors.lastname: Alvarenga
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Pollyanna F
authors.initials: PF
authors.lastname: de Oliveira
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Julia M
authors.initials: JM
authors.lastname: de Souza
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Denise C
authors.initials: DC
authors.lastname: Tavares
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Márcio L
authors.initials: ML
authors.lastname: Andrade E Silva
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Wilson R
authors.initials: WR
authors.lastname: Cunha
authors.affiliation: Department of Biology, Faculdade de Filosofia, Ciências e Letras, Ribeirão Preto, University of São Paulo , Avenida Bandeirantes 3900, Ribeirão Preto, São Paulo 14040-901, Brazil.
authors.forename: Milton
authors.initials: M
authors.lastname: Groppo
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Ana H
authors.initials: AH
authors.lastname: Januário
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Lizandra G
authors.initials: LG
authors.lastname: Magalhães
authors.affiliation: Center for Research in Exact and Technological Sciences, University of Franca , Avenida Doutor Armando Salles Oliveira 201, Franca, São Paulo 14404-600, Brazil.
authors.forename: Patrícia M
authors.initials: PM
authors.lastname: Pauletti
mesh_terms: D031021:Anacardium / Q000737:chemistry*; D000818:Animals; D005260:Female; D008297:Male; D009754:Nuts / Q000737:chemistry; D010636:Phenols / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D012550:Schistosoma mansoni / Q000187:drug effects* / Q000254:growth & development; D012556:Schistosomicides / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D010636:Phenols; D010936:Plant Extracts; D012556:Schistosomicides
keywords: alkyl-phenols; cashew Anacardium occidentale; schistosomicidal activity