Abstract
Three new triterpenoid alkaloids, (+)-N-benzoylbuxahyrcanine [(20S)-3beta-benzoylamino-20-dimethylaminobux-9(11)-ene-10alpha-ol] (1), (+)-N-tigloylbuxahyrcanine [(20S)-20-(dimethylamino)-3beta-(2'-methyl-2'-butenoylamino)bux-9(11)-en-10alpha-ol] (2), and (+)-N-isobutyroylbuxahyrcanine [(20S)-20-(dimethylamino)-3beta-(2'-methylpropanoyl)bux-9(11)-en-10alpha-ol] (3), have been isolated from the leaf extracts of Buxus hyrcana collected in Iran. Their structures were determined using spectroscopic methods. The structures of compounds 1 and 2 were unambiguously confirmed by single-crystal X-ray diffraction techniques. Compounds 1-3 were evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activities, and compound 2 was found to be active against both enzymes.
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 / isolation & purification*
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Alkaloids / pharmacology
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Butyrylcholinesterase
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Buxus / chemistry*
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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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Inhibitory Concentration 50
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Iran
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plants, Medicinal / chemistry*
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Stereoisomerism
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Triterpenes / chemistry
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Triterpenes / isolation & purification*
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Triterpenes / pharmacology
Substances
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(+)-N-benzoylbuxahyrcanine ((20S)-3beta-benzoylamino-20-dimethylaminobux-9(11)-ene-10alpha-ol)
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(+)-N-isobutyroylbuxahyrcanine ((20S)-20-(dimethylamino)-3beta-(2'-methylpropanoyl)bux-9(11)-en-10alpha-ol)
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(+)-N-tigloylbuxahyrcanine ((20S)-20-(dimethylamino)-3beta-(2'-methyl-2'-butenoylamino)bux-9(11)-en-10alpha-ol)
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Alkaloids
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Cholinesterase Inhibitors
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Triterpenes
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Butyrylcholinesterase