Diterpenoids and Flavonoids from Andrographis paniculata

Chem Pharm Bull (Tokyo). 2020;68(1):96-99. doi: 10.1248/cpb.c19-00662.

Abstract

Chemical investigation of the aerial parts of Andrographis paniculata resulted in isolation of nine compounds, including a new ent-labdane diterpenoid, andrographic acid methyl ester (1), a new chalcone glucoside, pashanone glucoside (5), and seven known metabolites, andrograpanin (2), andrographolide (3), andropanolide (4), andrographidine A (6), andrographidine F (7), 6-epi-8-O-acetyl-harpagide (8), and curvifloruside F (9). Their chemical structures were elucidated based on comprehensive analyses of the spectroscopic data, including NMR and MS. Among the isolated compounds, andropanolide exerted cytotoxicity toward LNCaP, HepG2, KB, MCF7, and SK-Mel2 carcinoma cells, with IC50 values ranging from 31.8 to 45.9 µM. In addition, andropanolide significantly inhibited the overproduction of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with an IC50 value of 13.4 µM.

Keywords: Acanthaceae; Andrographis paniculata; cytotoxicity; diterpenoid; flavonoid; nitric oxide overproduction.

MeSH terms

  • Andrographis / chemistry*
  • Andrographis / metabolism
  • Animals
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Humans
  • Lipopolysaccharides / toxicity
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Nitric Oxide / metabolism
  • Plant Components, Aerial / chemistry
  • Plant Components, Aerial / metabolism
  • RAW 264.7 Cells

Substances

  • Diterpenes
  • Flavonoids
  • Lipopolysaccharides
  • Nitric Oxide