Two New Isomeric Andrographolides with Anti-Inflammatory and Cytotoxic Activity

Chem Biodivers. 2020 Nov;17(11):e1900494. doi: 10.1002/cbdv.201900494. Epub 2020 Oct 6.

Abstract

Two novel epimerized andrographolides, 8,17-dihydro-7,8-dehydroandrographolide and 10β-8,17-dihydro-7,8-dehydroandrographolide, were isolated from andrographolide sulfonates. Their structures were elucidated by detailed NMR analysis, single-crystal X-ray diffraction and quantum chemical ECD calculations. In addition, these compounds exhibited suppression of NO production in LPS-stimulated RAW264.7 cells over the range of 1.564 to 25.000 μg/mL.

Keywords: NO; derivatives; inflammation; isomeric andrographolide.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Cell Survival / drug effects
  • Circular Dichroism
  • Crystallography, X-Ray
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology
  • Isomerism
  • Lipopolysaccharides / pharmacology
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Nitric Oxide / metabolism
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents
  • Diterpenes
  • Lipopolysaccharides
  • Nitric Oxide
  • dehydroandrographolide