Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)

Phytochemistry. 2020 Feb:170:112189. doi: 10.1016/j.phytochem.2019.112189. Epub 2019 Nov 12.

Abstract

There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. lutea, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2'-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties - phenolic acid and phenylethanoid unit.

Keywords: Broomrape; HR-QTOF/MS; Iridoids; NMR; Orobanche; Phelipanche; Phenylethanoid glycosides.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / antagonists & inhibitors
  • Humans
  • Iridoid Glycosides / chemistry
  • Iridoid Glycosides / isolation & purification
  • Iridoid Glycosides / pharmacology*
  • Orobanchaceae / chemistry*
  • Orobanche / chemistry*
  • Phenylethyl Alcohol / chemistry
  • Phenylethyl Alcohol / isolation & purification
  • Phenylethyl Alcohol / pharmacology*
  • Phytochemicals / chemistry
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology*
  • Picrates / antagonists & inhibitors
  • Poland
  • Species Specificity

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Iridoid Glycosides
  • Phytochemicals
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl
  • Phenylethyl Alcohol