Analysis of phenolic compounds in Extra Virgin Olive Oil by LC-NMR/MS. Differentiation and identification of diastereoisomeric molecules

“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”, by Míriam Pérez-Trujillo, Ana María Gómez-Caravaca, Antonio Segura-Carretero, Alberto Fernández-Gutiérrez, Teodor Parella; Journal of Agricultural and Food Chemistry 58, 9129-9136 (2010). DOI: 10.1021/jf101847e

The phenolic fraction of a monovarietal extra virgin olive oil (EVOO) from Olea europaea L. var. Cornezuelo 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.

Identification of a New Diastereoisomer of the Aldehydic Form of Oleuropein Aglycone in Olive Oil


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