Lignan derivatives from Selaginella tamariscina and their nitric oxide inhibitory effects in LPS-stimulated RAW 264.7 cells

Bioorg Med Chem Lett. 2017 Feb 1;27(3):524-529. doi: 10.1016/j.bmcl.2016.12.028. Epub 2016 Dec 9.

Abstract

The chemical characterization of Selaginella tamariscina leaves resulted in the isolation of five lignanoside derivatives (1-4 and 6) and one neolignan (5). These compounds include three new lignanosides, tamariscinosides D-F (1-3), and one liriodendrin (4) that were isolated for the first time from this plant, together with two known compounds, (2R,3S)-dihydro-2-(3,5-dimethoxy-4-hydroxyphenyl)-7-methoxy-5-acetyl-benzofuran (5) and moellenoside B (6). The chemical structures of these isolated compounds were determined using 1D and 2D NMR, MS, and CD spectroscopic data, and the results were compared to data previously reported in the literatures. These compounds were also evaluated in terms of their inhibition of NO production in lipopolysaccharide (LPS)-stimulated activity in the macrophage cell line RAW 264.7. Among them, compounds 1, 2, 5, and 6 exhibited a significant inhibition with IC50 values ranging from 32.3 to 55.8μM.

Keywords: F; Lignan; NO production inhibition; Selaginella tamariscina; Tamariscinosides D.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • RAW 264.7 Cells
  • Selaginellaceae / chemistry*
  • Structure-Activity Relationship

Substances

  • Lignans
  • Lipopolysaccharides
  • Nitric Oxide