A study of the precursors of the natural antioxidant phenol 3,4-dihydroxyphenylglycol in olive oil waste

3,4-Dihydroxyphenylglycol (DHPG) is a potent antioxidant recently found in the free form in olive oil and table olives. DHPG can be recovered from olive oil solid waste by a hydrothermal treatment. It was observed that an increase in the concentration of DHPG occurred when alperujo aqueous extracts were subjected to mild thermal conditions (post-treatment). This fact indicates that certain solubilized compounds or precursors containing DHPG which is released with the post-treatment. In the present study, the precursors of DHPG were identified and characterized after extraction from alperujo using thermal treatment and purification by fractionation on Amberlite® XAD16 polyamide and semi-preparative reverse-phase HPLC columns. Their structures were elucidated using HPLC coupled to diode array detector (DAD) and electrospray ionization mass spectrometry (ESI-MS). The results identified three compounds as precursors, and their structures can be attributed to the diastereoisomeric forms of the two β-hydroxy derivatives of verbascoside and isoverbascoside (β-hydroxyacteoside and β-hydroxyisoacteoside), and 2″-hydroxyoleuropein, all of which contain a DHPG moiety, potentially explaining the increases in the concentration of this phenolic compound in olive oil waste.

► We confirm the identity of precursors of 3,4-dihydroxyphenylglycol, a potent antioxidant found in olive oil.
► A thermal treatment of alperujo solubilizes compounds that contain a DHPG moiety.
► Two phenylpropanoidic compounds and one derivative of oleuropein have been identified.
► The hydrolysis of the precursors explains the increases in the concentration of DHPG.