NoteA concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol
Graphical abstract
A simple and direct strategy to chemically synthesize O-β-d-glucuronides of biologically relevant dietary bioactive phenolics: urolithin-B, resveratrol, and hydroxytyrosol is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of different reaction parameters.
Section snippets
General methods
All chemicals were obtained from chemical suppliers and used without further purification, unless otherwise noted. All reactions were monitored by TLC on precoated Silica-Gel 60 plates F254, and detected by heating with Mostain (500 mL of 10% H2SO4, 25 g of (NH4)6Mo7O24·4H2O, 1 g Ce(SO4)2·4H2O). Products were purified by flash chromatography with Silica Gel 60 (200–400 mesh). NMR spectra were recorded on 300, 400 or 500 MHz NMR equipment, at room temperature for solutions in CDCl3, D2O or CD3OD.
Acknowledgments
We would like to thank JAE-Doc program (R.L.) and Intramural Frontier Projects (200680F0132) from CSIC for financial support.
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