Separation and identification of phenolic compounds of extra virgin Olive Oil from Olea Europaea L. by HPLC-DAD-SPE-NMR/MS. Identification of a new diastereoisomer of the aldehydic form of oleuropein aglycone

Míriam Pérez-Trujillo, Ana María Gómez-Caravaca, Antonio Segura-Carretero, Alberto Fernández-Gutiérrez, Teodor Parella

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45 Citations (Scopus)

Abstract

The phenolic fraction of a monovarietal extra virgin olive oil (EVOO) from Olea europaea L.var.Cornezu elo was studied by the hyphenated HPLC-DAD-SPE-NMR/MS techniques.This survey led to the identification of 25 main compounds. One was identified as a new diastereoisomer of the aldehydic form of oleuropein aglycone (AOA) and characterized by 1D and 2D NMR techniques. The relative configuration of this new AOA was determined as 5R*,8S*, 9S* on the basis of the results obtained from the combination of NOE experiments and Monte Carlo conformational search calculations. Assuming, as for the described diastereoisomers, that the new AOA comes from the natural oleuropein aglycone (OA), the absolute configuration was proposed as 5S,8R,9R. ©2010 American Chemical Society.
Original languageEnglish
Pages (from-to)9129-9136
JournalJournal of Agricultural and Food Chemistry
Volume58
Issue number16
DOIs
Publication statusPublished - 25 Aug 2010

Keywords

  • aldehydic form of oleuropein aglycone
  • HPLC-DAD-SPE-NMR/MS
  • Olea europaea L
  • olive oil
  • phenolic compounds

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