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Enzymatic Synthesis of a Novel Neuroprotective Hydroxytyrosyl Glycoside

AuthorsNieto-Domínguez, Manuel José ; de Eugenio, Laura I. ; Peñalver, Pablo ; Belmonte-Reche, Efres; Morales, Juan C.; Poveda, Ana; Jiménez-Barbero, Jesús ; Prieto, Alicia ; Plou Gasca, Francisco José ; Martínez, María Jesús
olive oil
plant phenols
Issue Date9-Nov-2017
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 65(48): 10526-10533 (2017)
AbstractThe eco-friendly synthesis of non-natural glycosides from different phenolic antioxidants was carried out using a fungal β-xylosidase to evaluate changes in their bioactivities. Xylosides from hydroquinone and catechol were successfully formed, although the best results were obtained for hydroxytyrosol, the main antioxidant from olive oil. The formation of the new products was followed by thin-layer chromatography, liquid chromatography, and mass spectrometry. The hydroxytyrosyl xyloside was analyzed in more detail, to maximize its production and evaluate the effect of glycosylation on some hydroxytyrosol properties. The synthesis was optimized up to the highest production reported for a hydroxytyrosyl glycoside. The structure of this compound was solved by two-dimensional nuclear magnetic resonance and identified as 3,4-dihydroxyphenyl-ethyl-O-β-d-xylopyranoside. Evaluation of its biological effect showed an enhancement of both its neuroprotective capacity and its ability to ameliorate intracellular levels of reactive oxygen species.
Publisher version (URL)http://doi.org/10.1021/acs.jafc.7b04176
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