Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla.
The bark of Clathrotropis glaucophylla (Fabaceae) is used as admixture of curare arrow poison by the Yanomami; Amerindians in Venezuela. A new quinolizidine alkaloid (QA), (-)-13alpha-hydroxy-15alpha-(1-hydroxyethyl)-anagyrine [(-)-clathrotropine], was isolated from the alkaloid extract of C. glaucophylla bark, together with eleven known QAs: (-)-anagyrine, (-)-thermopsine, (-)-baptifoline, (-)-epibaptifoline, (-)-rhombifoline, (-)-tinctorine, (-)-cytisine, (-)-N-methylcytisine, (-)-lupanine, (-)-6alpha-hydroxylupanine and (+)-5,6-dehydrolupanine. The isolation and structure elucidation were performed with the aid of chromatographic (TLC, HPLC and CC) and spectroscopic (UV and 1D/2D NMR) methods, and mass spectrometry. To our knowledge, this is the first time quinolizidine alkaloids have been isolated from an arrow poison ingredient. It is also the first report on Clathrotropis species being used for preparation of arrow poison.
Sagen
Anne Lise
AL
Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zurich, Winterthurerstr 190, CH-8057, Zurich, Switzerland.
Gertsch
Jürg
J
Becker
Rita
R
Heilmann
Jörg
J
Sticher
Otto
O
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification*; D007887:Fabaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011042:Poisons / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry* / Q000302:isolation & purification*; D013056:Spectrophotometry, Ultraviolet
D000470:Alkaloids; D011042:Poisons; D011807:Quinolizines