Abstract
[structure: see text] A novel Lycopodium alkaloid with an unprecedented fused-tetracyclic ring system consisting of an aza-cyclononane ring having a N-hydroxy group, a cyclohexanone, a cyclopentanone, and a tetrahydrofuran ring, sieboldine A (1), was isolated from the club moss Lycopodium sieboldii. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and X-ray analysis. Sieboldine A (1) exhibited a potent inhibitory activity against acetylcholinesterase and modest cytotoxicity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylcholinesterase / metabolism*
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Animals
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Cell Line, Tumor
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Cholinesterase Inhibitors / chemistry
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Cholinesterase Inhibitors / isolation & purification*
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Cholinesterase Inhibitors / pharmacology
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Crystallography, X-Ray
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / isolation & purification*
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Heterocyclic Compounds, 4 or More Rings / pharmacology
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Lycopodium / chemistry*
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Magnetic Resonance Spectroscopy
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Molecular Structure
Substances
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Cholinesterase Inhibitors
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Heterocyclic Compounds, 4 or More Rings
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sieboldine A
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Acetylcholinesterase