Abstract
Eight new pyrrolidinoindoline alkaloids (1-8) were isolated from the whole plant of Selaginella moellendorfii. Their structures were determined by mass spectrometry, 1D and 2D NMR spectroscopy, and chemical interconversions. These alkaloids have a 3-carboxybut-2-enyl group at C-3a and two methyl groups at N-8. The possible biogenetic route from selaginellic acid (1) to neoselaginellic acid (6) was postulated and chemically mimicked. Tautomerization between 6 and 6a was observed. Selected compounds were evaluated for antibacterial, cytotoxic, and acetylcholinesterase inhibitory activities.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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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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Drug Screening Assays, Antitumor
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Drugs, Chinese Herbal / chemistry
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Drugs, Chinese Herbal / isolation & purification*
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Drugs, Chinese Herbal / pharmacology
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Escherichia coli / drug effects
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Humans
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Indole Alkaloids / chemistry
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Indole Alkaloids / isolation & purification*
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Indole Alkaloids / pharmacology
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Microbial Sensitivity Tests
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Pyrrolidines / chemistry
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Pyrrolidines / isolation & purification*
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Pyrrolidines / pharmacology
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Selaginellaceae / chemistry*
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Staphylococcus aureus / drug effects
Substances
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Cholinesterase Inhibitors
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Drugs, Chinese Herbal
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Indole Alkaloids
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Pyrrolidines