Synthesis of the Proposed Structure of Damaurone D and Evaluation of Its Anti-inflammatory Activity.
Concise and efficient synthesis of the proposed structure of damaurone D is accomplished in five steps without protection-deprotection operations. The key feature of our synthesis includes a versatile aldol reaction of the benzofuranone, provided by selective α-halogenation and intramolecular O-alkylation. However, the H- and C-NMR spectral data of the synthesized damaurone D did not agree with previous reports. The structure of the synthesized damaurone D was confirmed using combined two dimensional (2D)-NMR analysis, including heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), and nuclear Overhauser effect spectroscopy (NOESY). The synthesized damaurone D was found to exhibit potent anti-inflammatory activity in murine macrophage RAW264.7 cells, which was demonstrated by the findings that damaurone D treatment in cells resulted in the inhibition of lipopolysaccharide (LPS)-stimulated inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression and nitrite production.
College of Pharmacy, Dankook University.
Young Taek
YT
Han
Zheng
Z
Wang
Eun Ju
EJ
Bae
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D051546:Cyclooxygenase 2 / Q000276:immunology; D054879:Halogenation; D008070:Lipopolysaccharides / Q000276:immunology; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D052247:Nitric Oxide Synthase Type II / Q000276:immunology
D000893:Anti-Inflammatory Agents; D001572:Benzofurans; D008070:Lipopolysaccharides; C486837:aurone; D052247:Nitric Oxide Synthase Type II; D051546:Cyclooxygenase 2