Acylated flavonol glycosides from the forage legume, Onobrychis viciifolia (sainfoin)

Nigel C. Veitch, Ionela Regos, Geoffrey C. Kite, Dieter Treutter

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Ten acylated flavonol glycosides were isolated from aqueous acetone extracts of the aerial parts of the forage legume, Onobrychis viciifolia, and their structures determined using spectroscopic methods. Among these were eight previously unreported examples which comprised either feruloylated or sinapoylated derivatives of 3-O-di- and 3-O-triglycosides of kaempferol (3,5,7,4′-tetrahydroxyflavone) or quercetin (3,5,7,3′,4′- pentahydroxyflavone). The diglycosides were acylated at the primary Glc residue of O-α-Rhap(1 → 6)-β-Glcp (rutinose), whereas the triglycosides were acylated at the terminal Rha residues of the branched trisaccharides, O-α-Rhap(1 → 2)[α-Rhap(1 → 6)]-β-Galp or O-α-Rhap(1 → 2)[α-Rhap(1 → 6)]-β-Glcp. Identification of the primary 3-O-linked hexose residues as either Gal or Glc was carried out by negative ion electrospray and serial MS, and cryoprobe NMR spectroscopy. Analysis of UV and MS spectra of the acylated flavonol glycosides provided additional diagnostic features relevant to direct characterisation of these compounds in hyphenated analyses. Quantitative analysis of the acylated flavonol glycosides present in different aerial parts of sainfoin revealed that the highest concentrations were in mature leaflets.

Original languageEnglish
Pages (from-to)423-429
Number of pages7
JournalPhytochemistry
Volume72
Issue number4-5
DOIs
StatePublished - Apr 2011

Keywords

  • Acylated flavonol glycosides
  • Cryoprobe NMR
  • Forage legume
  • Leguminosae
  • MS/MS
  • Onobrychis viciifolia
  • Sainfoin

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