Neurite outgrowth-promoting active constituents of the Japanese cypress (Chamaecyparis obtusa)

Chem Pharm Bull (Tokyo). 2008 Jan;56(1):60-3. doi: 10.1248/cpb.56.60.

Abstract

In the screening of biologically active constituents from woody plants, the methanol extract of leaves of Chamaecyparis obtusa showed potent neurite outgrowth-promoting activity in neuronal PC12 cells. The ethyl acetate-soluble fraction of the methanol extract showed potent activity and was separated by means of various chromatographic methods to give the two new compounds 1 and 2, as well as 11 known lignan and sesquiterpene derivatives. The structures of the new compounds were determined to be 9-O-acetyldihydrosesamin (1) and 9-O-(11-hydroxyeudesman-4-yl)dihydrosesamin (2), respectively, in NMR studies including 2D-NMR experiments. Of the 13 compounds, the known compound hinokinin (5) and the new compound 2 showed potent neurite outgrowth-promoting activity in PC 12 cells.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Animals
  • Benzodioxoles
  • Chamaecyparis / chemistry*
  • Dioxoles / chemistry
  • Dioxoles / isolation & purification*
  • Dioxoles / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology*
  • Molecular Structure
  • Nerve Growth Factor / chemistry
  • Nerve Growth Factor / isolation & purification*
  • Nerve Growth Factor / pharmacology*
  • Neurites / drug effects*
  • PC12 Cells
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Rats

Substances

  • 9-O-(11-hydroxyeudesman-4-yl)dihydrosesamin
  • 9-O-acetyldihydrosesamin
  • Benzodioxoles
  • Dioxoles
  • Lignans
  • hinokinin
  • Nerve Growth Factor
  • 4-Butyrolactone