Ancistroguineines A and B as well as ancistrotectorine-naphthylisoquinoline alkaloids from Ancistrocladus guineënsis

The isolation of three naphthylisoquinoline alkaloids from the leaves of Ancistrocladus guineënsis is described. Their complete structures were established by spectroscopic, chiroptical and degradative methods. Thus, two hitherto unknown 5,8′-coupled naphthylisoquinolines, named ancistroguineines A...

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Published in:Phytochemistry (Oxford) 1998, Vol.47 (1), p.37-43
Main Authors: Bringmann, Gerhard, Günther, Christian, Busemann, Stefan, Schäffer, Manuela, Olowokudejo, James D., Alo, Babajide I.
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Biological and medical sciences
Biotechnology
chemical constituents of plants
Chemical constitution
chemical structure
Circular Dichroism
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
isoquinoline alkaloids
Isoquinolines - chemistry
Isoquinolines - isolation & purification
leaves
Magnetic Resonance Spectroscopy
Magnoliopsida
Molecular Structure
Plant Leaves - chemistry
Plant physiology and development
spectral analysis
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Summary:The isolation of three naphthylisoquinoline alkaloids from the leaves of Ancistrocladus guineënsis is described. Their complete structures were established by spectroscopic, chiroptical and degradative methods. Thus, two hitherto unknown 5,8′-coupled naphthylisoquinolines, named ancistroguineines A and B, were isolated, constituting the first example of a pair of 3-epimeric naphthylisoquinoline alkaloids. Moreover, ancistrotectorine, a 7,3′-coupled alkaloid previously known only from the South-East Asian species Ancistrocladus tectorius, was isolated. Its absolute stereostructure was confirmed by oxidative degradation and by comparison of experimental and calculated CD spectra.
ISSN:0031-9422
1873-3700
DOI:10.1016/S0031-9422(97)00511-6