New Thymoquinol Glycosides and Neuroprotective Dibenzocyclooctane Lignans from the Rattan Stems of Schisandra chinensis

Chem Biodivers. 2016 Sep;13(9):1118-1125. doi: 10.1002/cbdv.201500311. Epub 2016 Sep 10.

Abstract

Three new lignans (1 - 3), together with four new thymoquinol glycosides (4 - 7), were isolated from 70%-EtOH extract of the rattan stems of Schisandra chinensis. The structures of 1 - 7 were elucidated by detailed spectroscopic analyses, and these new compounds were identified as pinobatol-9-O-β-d-glucopyranoside (1), 1,2,13,14-tetramethoxydibenzocyclooctadiene 3,12-O-β-d-diglucopyranoside (2), 3,7-dihydroxy-1,2,13,14-tetramethoxydibenzocyclooctadiene 12-O-β-d-glucopyranoside (3), thymoquinol 2-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (4), thymoquinol 2-O-α-d-arabinofuranosyl-(1→6)-β-d-glucopyranoside (5), thymoquinol 5-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (6), and thymoquinol 5-O-α-d-arabinofuranosyl-(1→6)-β-d-glucopyranoside (7). The neuroprotective activity of 1 - 7 was evaluated on PC12 cells with neurotoxicity induced by amyloid-beta 1 - 42 (Aβ1 - 42 ). Compounds 2 and 3 showed protecting activity against Aβ-induced toxicity in PC12 cells.

Keywords: Schisandra chinensis; Lignans; Magnoliaceae; Neuroprotective activities; PC12 cell; Rattan stems; Thymoquinol glycosides.

MeSH terms

  • Amyloid beta-Peptides / antagonists & inhibitors
  • Amyloid beta-Peptides / toxicity
  • Animals
  • Benzoquinones / chemistry
  • Benzoquinones / isolation & purification
  • Benzoquinones / pharmacology*
  • Cell Survival / drug effects
  • Cyclooctanes / chemistry
  • Cyclooctanes / isolation & purification
  • Cyclooctanes / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification
  • Neuroprotective Agents / pharmacology*
  • PC12 Cells
  • Peptide Fragments / antagonists & inhibitors
  • Peptide Fragments / toxicity
  • Plant Stems / chemistry*
  • Rats
  • Schisandra / chemistry*

Substances

  • Amyloid beta-Peptides
  • Benzoquinones
  • Cyclooctanes
  • Glycosides
  • Lignans
  • Neuroprotective Agents
  • Peptide Fragments
  • amyloid beta-protein (1-42)
  • thymoquinone