Abstract
The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (+/-)-norannuradhapurine inhibits the production of NO, PGE(2), TNF-alpha, IL-1beta and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro.
MeSH terms
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Animals
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Anti-Inflammatory Agents / chemical synthesis*
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Anti-Inflammatory Agents / pharmacology*
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Aporphines / chemical synthesis*
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Aporphines / pharmacology*
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Candida albicans / drug effects
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Cell Line
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Cyclization
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Cyclooxygenase 2 / drug effects
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Dinoprostone / antagonists & inhibitors
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Escherichia coli / drug effects
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Interleukin-1beta / antagonists & inhibitors
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Interleukin-6 / antagonists & inhibitors
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Lipopolysaccharides / immunology
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Lipopolysaccharides / pharmacology
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Macrophages / drug effects
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Macrophages / immunology
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Magnoliopsida / chemistry
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Mice
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Molecular Structure
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Nitric Oxide / antagonists & inhibitors
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Nitric Oxide Synthase Type II / antagonists & inhibitors
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Staphylococcus aureus / drug effects
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Tumor Necrosis Factor-alpha / antagonists & inhibitors
Substances
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Anti-Inflammatory Agents
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Aporphines
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Interleukin-1beta
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Interleukin-6
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Lipopolysaccharides
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Tumor Necrosis Factor-alpha
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norannuradhapurine
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Nitric Oxide
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Nitric Oxide Synthase Type II
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Ptgs2 protein, mouse
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Cyclooxygenase 2
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Dinoprostone