title: Thiophene derivatives with antileishmanial activity isolated from aerial parts of Porophyllum ruderale (Jacq.) Cass.
abstract: Porophyllum ruderale (Jacq.) Cass. is a plant native to Brazil and in the northwest region of the state of Paraná, Brazil, aerial parts of P. ruderale have been used popularly in the treatment of lesions caused by Leishmania sp.. In this study the antileishmanial and cytotoxic activities of the crude extract, fractions, and isolated compounds from aerial parts of P. ruderale was evaluated. The dichloromethane extract was submitted to chromatography to yield compounds active against Leishmania amazonensis. Their structures were established by comparison of their spectroscopic data with literature values. The activities of crude extract against promastigote and axenic amastigote forms of L. amazonensis (IC(50)) were 60.3 and 77.7 μg/mL, respectively. Its cytotoxic activity against macrophage cells (CC(50)) was 500 μg/mL. The thiophene derivatives isolated were: 5-methyl-2,2':5',2"-terthiophene (compound A) and 5'-methyl-[5-(4-acetoxy-1-butynyl)]-2,2'-bithiophene (compound B). The activity of compound A against promastigote and axenic amastigote forms were 7.7 and 19.0 μg/mL and of compound B were 21.3 and 28.7 μg/mL, respectively. The activity of the isolated compounds against promastigote and axenic amastigote forms was better than that of the crude extract and more selective against protozoa than for macrophage cells.
authors.affiliation: Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Estadual de Maringá, Av. Colombo, 5790, 87020-900, Maringá, PR, Brazil.
authors.forename: Helena Teru
authors.initials: HT
authors.lastname: Takahashi
authors.forename: Cláudio Roberto
authors.initials: CR
authors.lastname: Novello
authors.forename: Tânia
authors.initials: T
authors.lastname: Ueda-Nakamura
authors.forename: Benedito Prado Dias
authors.initials: BP
authors.lastname: Filho
authors.forename: João Carlos
authors.initials: JC
authors.lastname: Palazzo de Mello
authors.forename: Celso Vataru
authors.initials: CV
authors.lastname: Nakamura
mesh_terms: D019659:Asteraceae / Q000737:chemistry*; D007891:Leishmania / Q000187:drug effects*; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D035261:Plant Components, Aerial / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013876:Thiophenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D014344:Trypanocidal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D010936:Plant Extracts; D013876:Thiophenes; D014344:Trypanocidal Agents