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Título

Enzymatic Synthesis of a Novel Neuroprotective Hydroxytyrosyl Glycoside

AutorNieto-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
Palabras claveglycosylation
olive oil
plant phenols
regioselectivity
xyloside
Fecha de publicación9-nov-2017
EditorAmerican Chemical Society
CitaciónJournal of Agricultural and Food Chemistry 65(48): 10526-10533 (2017)
ResumenThe 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.
Versión del editorhttp://doi.org/10.1021/acs.jafc.7b04176
URIhttp://hdl.handle.net/10261/163409
DOI10.1021/acs.jafc.7b04176
ISSN0021-8561
E-ISSN1520-5118
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