Bioactive cinchona alkaloids from Remijia peruviana.

نویسندگان

  • Lastenia Ruiz-Mesia
  • Wilfredo Ruiz-Mesía
  • Matías Reina
  • Rafael Martínez-Diaz
  • Concepción de Inés
  • Ana Guadaño
  • Azucena González-Coloma
چکیده

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.

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عنوان ژورنال:
  • Journal of agricultural and food chemistry

دوره 53 6  شماره 

صفحات  -

تاریخ انتشار 2005