Discovery of cycloneolignan enantiomers from Isatis indigotica Fortune with neuroprotective effects against MPP+-induced SH-SY5Y cell injury

Bioorg Chem. 2019 Jul:88:102926. doi: 10.1016/j.bioorg.2019.102926. Epub 2019 Apr 15.

Abstract

A pair of new cycloneolignan enantiomers (1a and 1b) were isolated from the leaves of Isatis indigotica Fortune. Their structures were elucidated by extensive spectroscopic data analysis, including 1D and 2D NMR, HRESIMS, MS/MS analysis, together with theoretical electronic circular dichroism (ECD) calculations. Compounds 1a and 1b were then evaluated for their neuroprotective effects against MPP+-induced SH-SY5Y cell injury. As a result, compounds 1a (77.64%) and 1b (78.62%) exhibited moderate neuroprotective activity at the concentration of 12.5 µM compared with that of MPP+ treated group (62.00% at 1 mM) by MTT assay. Furthermore, Annexin V-FITC/PI analysis showed that apoptosis ratios of 1a and 1b were reduced to 10.99% and 9.31%, respectively.

Keywords: Apoptosis; Cycloneolignan; Enantiomers; Isatis indigotica; Neuroprotective effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Methyl-4-phenylpyridinium / antagonists & inhibitors*
  • 1-Methyl-4-phenylpyridinium / pharmacology
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Humans
  • Isatis / chemistry*
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification
  • Neuroprotective Agents / pharmacology*
  • Plant Leaves / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Lignans
  • Neuroprotective Agents
  • 1-Methyl-4-phenylpyridinium