Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments

J Agric Food Chem. 2000 May;48(5):1623-9. doi: 10.1021/jf991178b.


Technomimetic NMR experiments were performed in accordance with the lye treatment adopted during table olive industrial procedures for the debittering process causing oleuropein degradation. The site selective hydrolysis of the two ester groups, characterizing the biophenolic secoiridoid molecule, was shown to be dependent on the different reactivities of these functionalities. The process is controlled by the experimental conditions exerted on the olive pulp and determined by the buffering capacity of the olive mesocarp and by the epicarp molecular components influencing the reactant penetration into the fruit pulp. The overall hydrolytic process of oleuropein, the bitter principle of olives, using the technomimetic experimental mode, gave rise to its catabolic derivatives, hydroxytyrosol, 11-methyloleoside, and the monoterpene glucoside, technomimetically produced, isolated, and structurally characterized by (1)H, (13)C, and COSY spectroscopy as the oleoside.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrolysis
  • Iridoid Glucosides
  • Iridoids
  • Magnetic Resonance Spectroscopy / methods*
  • Pyrans / chemistry*


  • Iridoid Glucosides
  • Iridoids
  • Pyrans
  • oleuropein