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Bioactive cinchona alkaloids from Remijia peruviana

AuthorsRuiz-Mesía, Lastenia; Ruiz-Mesía, Wilfredo; Reina, Matías ; Martínez Díaz, Rafael; Inés, Concepción de; Guadaño, Ana; González-Coloma, Azucena
KeywordsRemijia peruviana (Rubiaceae)
Cinchona alkaloids
Structural elucidation
Antifeedant effects
Spodoptera littoralis
Leptinotarsa decemlineata
Cytotoxic activity
Issue Date23-Feb-2005
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 53(6): 1921-1926 (2005)
AbstractThree 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.
Description6 pages, 6 tables, 1 scheme.-- PMID: 15769114 [PubMed].-- Printed version published Mar 23, 2005.
Supporting information (2 pages) available at: http://pubs.acs.org/doi/suppl/10.1021/jf048880e
Publisher version (URL)http://dx.doi.org/10.1021/jf048880e
Appears in Collections:(ICA) Artículos
(IPNA) Artículos
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