Bioactive clerodane diterpenes of giant goldenrod (Solidago gigantea Ait.) root extract

J Chromatogr A. 2021 Jan 4:1635:461727. doi: 10.1016/j.chroma.2020.461727. Epub 2020 Nov 19.

Abstract

Giant goldenrod (Solidago gigantea Ait.) root extract was screened for bioactive compounds by high-performance thin-layer chromatography (HPTLC), coupled with effect-directed analysis including antibacterial (Bacillus subtilis F1276, B. subtilis subsp. spizizenii, Aliivibrio fischeri and Xanthomonas euvesicatoria), antifungal (Fusarium avenaceum) and enzyme inhibition (acetyl- and butyrylcholinesterases, α- and β-glucosidases and α-amylase) assays. Compounds of six multipotent zones (Sg1-Sg6) were characterized by HPTLC-heated electrospray ionization-high-resolution mass spectrometry (HRMS) and HPTLC-Direct Analysis in Real Time-HRMS. Apart from zone Sg3, containing three compounds, a single characteristic compound was detectable in each bioactive zone. The bioassay-guided isolation using preparative-scale flash chromatography and high-performance liquid chromatography provided eight compounds that were identified by NMR spectroscopy as clerodane diterpenes. All isolates possessed inhibiting activity against at least one of the tested microorganisms.

Keywords: Antibacterials and antifungals; Clerodane diterpenes; Fusarium avenaceum; Giant goldenrod (Solidago gigantea Ait.); High-performance thin-layer chromatography – effect directed analysis; High-performance thin-layer chromatography – high-resolution mass spectrometry.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / pharmacology*
  • Bacillus subtilis / drug effects
  • Bacteria / drug effects*
  • Cholinesterases / metabolism
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology*
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Fusarium / drug effects*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Solidago / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Xanthomonas / drug effects

Substances

  • Anti-Infective Agents
  • Diterpenes, Clerodane
  • Enzyme Inhibitors
  • Plant Extracts
  • Cholinesterases

Supplementary concepts

  • Fusarium avenaceum
  • Xanthomonas euvesicatoria