seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

作者：Coy Barrera Carlos Andres; Coy Barrera Ericsson David; Granados Falla Diana Susana; Delgado Murcia Gabriela; Cuca Suarez Luis Enrique

来源：CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59(7): 855-859.

DOI：10.1248/cpb.59.855

• Rutaccae
• limonoid
• antileishmanial
• quinolone alkaloid
• Raputia heptaphylla

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 (OFT) 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 mu g/ml) and promastigotes (EC50: 14.3 mu g/ml), respectively.

• 出版日期2011-7