Abstract
The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (+/-)-laurelliptinhexadecan-1-one (1a) and (+/-)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.
MeSH terms
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Anti-Infective Agents / chemical synthesis*
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Anti-Infective Agents / chemistry
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Anti-Infective Agents / pharmacology*
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Candida albicans / drug effects
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Cell Line, Tumor
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Cocculus / chemistry
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Escherichia coli / drug effects
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / pharmacology*
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Humans
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Magnetic Resonance Spectroscopy
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Microbial Sensitivity Tests
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Molecular Structure
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Spectrophotometry, Ultraviolet
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Staphylococcus aureus / drug effects
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Stereoisomerism
Substances
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Anti-Infective Agents
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Heterocyclic Compounds, 4 or More Rings
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laurelliptinhexadecan-1-one
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laurelliptinoctadecan-1-one