title: seco-limonoids and quinoline alkaloids from Raputia heptaphylla and their antileishmanial activity.
abstract: A novel seco-limonoid, rel-(1S,5R,9S,7R,8S,9R,10S,11R,13S,14R,15R,17R)-11,19-dihydroxy-7-acetoxy-7-deoxoichangin (raputiolide) (1), and two novel quinolone alkaloids N-methyl-2-phenoxyquinolin-4(1H)-one (heptaphyllone A) (2) and 6-methylbenzofuro[2,3-b]quinolin-4(1H)-one (heptaphyllone B) (3), along with the known seco-limonoid ichangin (4), were isolated from Raputia heptaphylla PITTIER (Rutaceae) stem bark. Five known alkaloids, N-methyl-8-methoxyflindersine (5), skimmianine (6), kokusaginine (7), dictamnine (8) and flindersiamine (9), were also isolated from R. heptaphylla leaves. Their structures were established on the basis of full spectroscopic data interpretation supported by data from the pertinent literature. seco-Limonoid 1 configuration was determined by enhanced nuclear Overhauser effect spectroscopy (NOESY) experiments and density functional theory (DFT) molecular modeling. The antileishmanial effect of the isolated compounds was evaluated on Leishmania Viannia panamensis (promastigotes and amastigotes). Whereas alkaloids 2-3, 6-8 and limonoid 4 exhibited no significant parasitocide activity against internalized L. (V.) panamensis amastigotes, limonoid 1 and alkaloid 5 had leishmanicidal activity on intracellular amastigotes (EC₅₀: 8.7 µg/ml) and promastigotes (EC(50): 14.3 µg/ml), respectively.
authors: Universidad Nacional de Colombia, Facultad de Ciencias, Departamento de Química, Laboratorio de Investigación en Productos Naturales Vegetales, Ciudad Universitaria, Bogotá D.C., Colombia.
authors: Carlos Andres
authors: CA
authors: Coy Barrera
authors: Ericsson David
authors: ED
authors: Coy Barrera
authors: Diana Susana
authors: DS
authors: Granados Falla
authors: Gabriela
authors: G
authors: Delgado Murcia
authors: Luis Enrique
authors: LE
authors: Cuca Suarez
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007891:Leishmania / Q000187:drug effects*; D036701:Limonins / Q000737:chemistry*; D008968:Molecular Conformation; D024301:Plant Bark / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D027821:Rutaceae / Q000737:chemistry*; D014344:Trypanocidal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000470:Alkaloids; D036701:Limonins; D011804:Quinolines; D014344:Trypanocidal Agents; C037219:quinoline