Total synthesis and the biological activities of (+/-)-norannuradhapurine

Molecules. 2008 Dec 29;14(1):89-101. doi: 10.3390/molecules14010089.

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

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology*
  • Aporphines / chemical synthesis*
  • Aporphines / pharmacology*
  • Candida albicans / drug effects
  • Cell Line
  • Cyclization
  • Cyclooxygenase 2 / drug effects
  • Dinoprostone / antagonists & inhibitors
  • Escherichia coli / drug effects
  • Interleukin-1beta / antagonists & inhibitors
  • Interleukin-6 / antagonists & inhibitors
  • Lipopolysaccharides / immunology
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / immunology
  • Magnoliopsida / chemistry
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Staphylococcus aureus / drug effects
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors

Substances

  • Anti-Inflammatory Agents
  • Aporphines
  • Interleukin-1beta
  • Interleukin-6
  • Lipopolysaccharides
  • Tumor Necrosis Factor-alpha
  • norannuradhapurine
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Ptgs2 protein, mouse
  • Cyclooxygenase 2
  • Dinoprostone