Bioactive cinchona alkaloids from Remijia peruviana.
Three known Cinchona alkaloids of the quinine type, quinine (1), cupreine (2), cinchonine (3), and the possible artifact cinchonine-HCl (3-HCl), along with two new ones, acetylcupreine (4) and N-ethylquinine (5), have been isolated from the bark of Remijia peruviana (Rubiaceae). Their stereochemical structures were established by high resolution NMR spectroscopy. Alkaloids 2-4 had antifeedant effects on Leptinotarsa decemlineata with varying potencies. Compound 4 was cytotoxic to both insect Sf9 and mammalian CHO cells after 48 h of incubation, while 3-HCl had stronger and selective cytotoxicity to Sf9. Quinine 1 had a moderate to low effect on Trypanosoma cruzi. Tumoral cells were also affected by these alkaloids, with 4 and 3-HCl being the most cytotoxic to all the cell lines tested. Overall, the 8R, 9S configurations, as in 3 and 3-HCl, as well as the C-6'acetylated alkaloid 4, with an 8S, 9R configuration, showed stronger biological effects.
Ruiz-Mesia
Lastenia
L
Laboratorio de Productos Naturales, Facultad de Ingeniería Química, Universidad Nacional de la Amazonía Peruana, Iquitos, Peru.
Ruiz-Mesía
Wilfredo
W
Reina
Matías
M
Martínez-Diaz
Rafael
R
de Inés
Concepción
C
Guadaño
Ana
A
González-Coloma
Azucena
A
D000818:Animals; D000970:Antineoplastic Agents; D016466:CHO Cells; D016923:Cell Death / Q000187:drug effects; D002930:Cinchona Alkaloids / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology; D006224:Cricetinae; D006801:Humans; D007306:Insecticides; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D019666:Rubiaceae / Q000737:chemistry*; D018411:Spodoptera; D014349:Trypanosoma cruzi / Q000187:drug effects; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D002930:Cinchona Alkaloids; D007306:Insecticides