Abstract
Mbandakamines A (1) and B (2), isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species, are the first dimeric naphthylisoquinoline alkaloids with an unsymmetrically coupled central biaryl axis. Their novel 6',1″-coupling type implies a hitherto unprecedented peri-peri coupling in one of the naphthalene parts, leading to the as yet highest steric hindrance at the central axis and a total of seven elements of chirality. Mbandakamine A exhibits good antimalarial activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemistry*
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Alkaloids / pharmacology
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Antimalarials / chemistry*
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Antimalarials / pharmacology
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Dimerization
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Isoquinolines / chemistry*
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Isoquinolines / isolation & purification
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Isoquinolines / pharmacology
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Naphthalenes / chemistry*
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Naphthalenes / isolation & purification
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Naphthalenes / pharmacology
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Plant Extracts / chemistry*
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Plant Extracts / isolation & purification
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Plant Leaves / chemistry*
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Plasmodium falciparum / chemistry*
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Plasmodium falciparum / drug effects*
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Stereoisomerism
Substances
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Alkaloids
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Antimalarials
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Isoquinolines
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Mbandakamine A
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Mbandakamine B
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Naphthalenes
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Plant Extracts