Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments

Technomimetic NMR experiments were performed in accordance with the lye tre atment adopted during table olive industrial procedures for the debittering process causing oleuropein degradation. The site selective hydrolysis of t he two ester groups, characterizing the biophenolic secoiridoid molecule, w as shown to be dependent on the different reactivities of these functionali ties. The process is controlled by the experimental conditions exerted on t he olive pulp and determined by the buffering capacity of the olive mesocar p and by the epicarp molecular components influencing the reactant penetrat ion 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 struct urally characterized by H-1, C-13, and COSY spectroscopy as the oleoside.