Neolignans from the fruits of Magnolia obovata and their inhibition effect on NO production in LPS-induced RAW 264.7 cells

Planta Med. 2013 Sep;79(14):1335-40. doi: 10.1055/s-0033-1350673. Epub 2013 Aug 22.

Abstract

Three new neolignans, named 9-methoxyobovatol (6), magnobovatol (7), and 2-hydroxyobovaaldehyde (9), along with six known ones, magnolol (1), honokiol (2), isomagnolol (3), obovatol (4), obovatal (5), and obovaaldehyde (8), were isolated from the fruits of Magnolia obovata using silica gel and ODS column chromatography. From the results of spectroscopic data including EIMS, IR, 1H- and 13C-NMR, DEPT, and 2D-NMR (gCOSY, gHSQC, gHMBC), the chemical structures were determined. All isolated compounds were evaluated for inhibition activity on nitric oxide production in LPS-induced RAW 264.7 cells, and compounds 1-4, 6, 7, and 9 showed significant activity with IC50 values of 15.8 ± 0.3, 3.3 ± 1.2, 14.1 ± 0.9, 6.2 ± 1.2, 14.8 ± 2.3, 14.2 ± 1.2, and 14.8 ± 3.2 µM, respectively, without any visible toxic effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Line
  • Fruit / chemistry
  • Inflammation / chemically induced
  • Inflammation / metabolism
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Lipopolysaccharides
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnolia / chemistry*
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*

Substances

  • 2-hydroxyobovaaldehyde
  • 9-methoxyobovatol
  • Anti-Inflammatory Agents
  • Lignans
  • Lipopolysaccharides
  • Plant Extracts
  • magnobovatol
  • Nitric Oxide