Bioactive Cinchona alkaloids from Remijia peruviana

Lastenia Ruiz-Mesia, Wilfredo Ruiz-Mesía, Matías Reina, Rafael Martínez-Diaz, Concepción De Inés, Ana Guadaño, Azucena González-Coloma

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

28 Citas (Scopus)

Resumen

Three known Cinchona alkaloids of the quinine type, quinine (1), cupreine (2), cinchonine (3), and the possible artifact cinchonine-HCI (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.

Idioma originalInglés
Páginas (desde-hasta)1921-1926
Número de páginas6
PublicaciónJournal of Agricultural and Food Chemistry
Volumen53
N.º6
DOI
EstadoPublicada - 23 mar. 2005

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