Characterization of Secondary Metabolites in Flowers of Sanguisorba officinalis L. by HPLC-DAD-MSn and GC/MS

Chem Biodivers. 2020 Apr;17(4):e1900724. doi: 10.1002/cbdv.201900724. Epub 2020 Mar 30.

Abstract

The investigations reported here focus on an in-depth characterization of the secondary metabolite profile of Sanguisorba officinalis flowers. For this purpose, fresh flowers were extracted with MeOH/H2 O and EtOH/H2 O and the resulting crude extracts fractionated using CH2 Cl2 , AcOEt, and BuOH. Individual compounds were characterized by high performance liquid chromatography and gas chromatography coupled with mass spectrometric detection (HPLC-DAD-MSn and GC/MS). MeOH/H2 O extraction and LC/MSn investigations revealed the occurrence of flavonoid glycosides (quercetin, kaempferol), ellagitannin glycosides and four anthocyanins. Among the latter, two components, i. e., cyanidin-malonyl-glucose and cyanidin-galloyl-hexose, have not been reported for S. officinalis so far. Furthermore, phenylethylamine was characterized for the first time in Sanguisorba by pH value dependent extraction with CH2 Cl2 . In addition, AcOEt and BuOH extracts were analyzed by GC/MS both prior to and after acid hydrolysis of secondary metabolites. For this purpose, the extracts were treated with 1 n HCl solution (105 °C, 1 h) and derivatized with BSTFA. Analyses revealed the occurrence of several classes of phenolic compounds, such as gallic acid, hydroxybenzoic acid, hydroxycinnamic acid and ellagic acid derivatives. Additionally, the most prominent ursane-type triterpenoid (ziyu-glycoside I) from Sanguisorba and its corresponding aglycone isomers were detected and assigned based on their characteristic fragmentation patterns.

Keywords: Sanguisorba officinalis; amines; anthocyanins; gas chromatography; phenolics.

MeSH terms

  • Amines / analysis
  • Amines / chemistry
  • Amines / metabolism
  • Anthocyanins / analysis
  • Anthocyanins / chemistry
  • Anthocyanins / metabolism
  • Chromatography, High Pressure Liquid
  • Flowers / chemistry
  • Flowers / metabolism
  • Gas Chromatography-Mass Spectrometry*
  • Glycosides / analysis
  • Glycosides / chemistry
  • Glycosides / metabolism
  • Isomerism
  • Phenols / analysis
  • Phenols / chemistry
  • Phenols / metabolism
  • Plant Extracts / chemistry
  • Sanguisorba / chemistry*
  • Sanguisorba / metabolism
  • Tandem Mass Spectrometry*

Substances

  • Amines
  • Anthocyanins
  • Glycosides
  • Phenols
  • Plant Extracts