Yaoundamines A and B, new antimalarial naphthylisoquinoline alkaloids from Ancistrocladus korupensis

New monomeric naphthylisoquinoline alkaloids, yaoundamines A and B, were isolated from Ancistrocladus korupensis and their structures were determined by extensive chemical and spectroscopic analyses. The absolute configuration at C3 was established by chemical degradation, while the axial chirality...

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Bibliographic Details
Published in:Tetrahedron 1997-06, Vol.53 (24), p.8121-8128
Main Authors: Hallock, Yali F., Cardellina, John H., Schäffer, Manuela, Stahl, Martin, Bringmann, Gerhard, François, Guido, Boyd, Michael R.
Format: Article
Language:English
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Summary:New monomeric naphthylisoquinoline alkaloids, yaoundamines A and B, were isolated from Ancistrocladus korupensis and their structures were determined by extensive chemical and spectroscopic analyses. The absolute configuration at C3 was established by chemical degradation, while the axial chirality was deduced by comparison of experimental and calculated CD spectra. Yaoundamine B has an unprecedented glycosylated naphthylisoquinoline structure. Yaoundamines A and B are active in vitro against the malaria parasite Plasmodium falciparum. Yaoundamines A ( 1) and B ( 2) were isolated and identified from Ancistrocladus korupensis. The antimalarial yaoundamines have the very unusual 7/8′ axial linkage; yaoundamine B is the first glycosylated member of the naphthylisoquinoline family.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00502-4