Abstract
Alstoscholarisine K, an indole alkaloid with eight chiral carbons and featuring a novel 6/5/6/6/6/6/6/5 octacyclic architecture, was found to be specific to the gall-infected leaves of Alstonia scholaris. Its structure was elucidated by spectroscopy, computational analysis, and single-crystal X-ray diffraction. The unusual highly fused cage-like pyrrolo[1,2-a]pyrimidine structure with an additional -C4N unit is possibly derived from a combination of monoterpenoid indole and polyamine pathways. The fascinating compound exhibited significant antibacterial bioactivities by targeting cell membranes.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alstonia / chemistry*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / pharmacology*
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Anti-Infective Agents / chemistry
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Anti-Infective Agents / isolation & purification
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Anti-Infective Agents / pharmacology*
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Crystallography, X-Ray
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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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Magnetic Resonance Spectroscopy
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Molecular Structure
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Monoterpenes / chemistry
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Monoterpenes / isolation & purification
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Monoterpenes / pharmacology*
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Plant Leaves / chemistry
Substances
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Anti-Bacterial Agents
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Anti-Infective Agents
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Indole Alkaloids
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Monoterpenes