2024-03-28T23:56:48Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1634092020-10-26T17:40:47Zcom_10261_86com_10261_1com_10261_64col_10261_339col_10261_317
00925njm 22002777a 4500
dc
Nieto-Domínguez, Manuel José
author
Eugenio, Laura I. de
author
Peñalver, Pablo
author
Belmonte-Reche, Efres
author
Morales, Juan C.
author
Poveda, Ana
author
Jiménez-Barbero, Jesús
author
Prieto, Alicia
author
Plou Gasca, Francisco José
author
Martínez, María Jesús
author
2017-11-09
The 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.
Journal of Agricultural and Food Chemistry 65(48): 10526-10533 (2017)
0021-8561
http://hdl.handle.net/10261/163409
10.1021/acs.jafc.7b04176
1520-5118
glycosylation
olive oil
plant phenols
regioselectivity
xyloside
Enzymatic Synthesis of a Novel Neuroprotective Hydroxytyrosyl Glycoside