Isolation of a powerful antioxidant from Olea europaea fruit-mill waste: 3,4-Dihydroxyphenylglycol

Abstract

Nutritional and antioxidant properties of phenolic compounds are important in relation to human health and palatability of products. 3,4-Dihydroxyphenylglycol (DHPG) is a strong antioxidant found in small amounts in virgin olive oil and table olives, with an antioxidant activity even higher than that of the powerful hydroxytyrosol. The origin of this antioxidant is completely unclear since has never been reported as a free plant metabolite. In this respect possible precursors of DHPG have also been discussed in this study. The presence of soluble compounds that either contain DHPG in their molecular structure or act as substrates for its synthesis has been showed for the first time. The quantities of DHPG recovered in olive drupe tissue by thermal treatment exceed widely the values indicated in the literature, showing the release or formation of additional DHPG from precursors after heating. In addition, DHPG obtained under certain extraction conditions from fresh solid waste of two-phase olive oil extraction systems (alperujo) is its most important phenolic compound. Therefore, the solid olive waste is a good source of this simple monomer phenol. The chemical structure, purity and racemic nature of isolated DHPG were also analysed for the first time by NMR experiments.