Iridoid glucosides and a C₁₃-norisoprenoid from Lamiophlomis rotata and their effects on NF-κB activation

Bioorg Med Chem Lett. 2012 Jul 1;22(13):4447-52. doi: 10.1016/j.bmcl.2012.04.087. Epub 2012 May 5.

Abstract

Four new iridoid glucosides, 7-dehydroxyzaluzioside (1), 6'-O-syringylphlorigidoside C (2), barlerin-6″-hydroxy-2″,6″-dimethylocta-2″,7″-dienate ester (3), 6β-n-butoxy-7,8-dehydropenstemonoside (4), and a new C(13)-norisoprenoid derivative, 5β,6α-dihydroxy-3β-(β-D-glucoyranosyloxy)-7-megastigmen-9-one (5), together with 16 known iridoid glucosides, were isolated from Lamiophlomis rotata. The structures of these new compounds were elucidated by HRMS, 1D and 2D NMR spectroscopy. A stable nuclear factor kappaB (NF-κB)-luciferase-expressing human embryonic kidney 293 cell line was used in the luciferase assay for monitoring the anti-inflammatory activity of the compounds. It was found that 6β-n-butoxy-7,8-dehydropenstemonoside (4) and two known compounds (8-epi-7-deoxyloganin and 7,8-dehydropenstemonoside) had a significant inhibitory effect on lipopolysaccharide-stimulated NF-κB activation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Genes, Regulator / drug effects
  • HEK293 Cells
  • Humans
  • Iridoid Glucosides / chemistry*
  • Iridoid Glucosides / isolation & purification
  • Iridoid Glucosides / pharmacology
  • Lamiaceae / chemistry*
  • Lipopolysaccharides / toxicity
  • Luciferases / genetics
  • Luciferases / metabolism
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • NF-kappa B / metabolism*
  • Norisoprenoids / chemistry*
  • Norisoprenoids / isolation & purification
  • Norisoprenoids / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Iridoid Glucosides
  • Lipopolysaccharides
  • NF-kappa B
  • Norisoprenoids
  • Luciferases