UV-guided isolation of enantiomeric polyacetylenes from Bupleurum scorzonerifolium Willd. with inhibitory effects against LPS-induced NO release in BV-2 microglial cells

Bioorg Chem. 2022 Feb:119:105521. doi: 10.1016/j.bioorg.2021.105521. Epub 2021 Nov 29.

Abstract

UV-guided fractionation led to the isolation of thirteen new polyacetylenes (1-13) from the roots of Bupleurum scorzonerifolium Willd. All polyacetylenes were analyzed as racemates since the lack of optical activity and Cotton effects in the ECD spectra. The sequent chiral-phase HPLC resolution successfully gave twelve pairs of enantiomers 1a/1b and 3a/3b-13a/13b. Their structures were elucidated based on the HRESIMS and NMR data analyses. The absolute configurations were determined by the combination of Snatzke's method, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Using Griess methods and MTT assays, polyacetylenes 1a, 3a, 4a/4b-12a/12b, and 13a displayed inhibitory activities against LPS-induced NO release in BV-2 microglial cells.

Keywords: Antineuroinflammatory; Bupleurum scorzonerifolium; Chiral-phase resolution; Polyacetylenes; Snatzke’s method; UV-guided isolation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bupleurum / chemistry*
  • Cells, Cultured
  • Dose-Response Relationship, Drug
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Plant Roots / chemistry
  • Polyacetylene Polymer / chemistry
  • Polyacetylene Polymer / isolation & purification
  • Polyacetylene Polymer / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Ultraviolet Rays

Substances

  • Lipopolysaccharides
  • Plant Extracts
  • Polyacetylene Polymer
  • Nitric Oxide