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 8 R, 9 S configurations, as in 3 and 3 −HCl, as well as the C-6‘ acetylated alkaloid 4, with an 8 S, 9 R configuration, showed stronger biological effects.
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Mesía et al. (2005) studied this question.
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