A synthetic approach to the generation of quercetin sulfates and the detection of quercetin 3′- O-sulfate as a urinary metabolite in the rat

• Published in: Bioorganic & medicinal chemistry 2005-12, Vol.13 (24), p.6727-6731
• Main Authors: Jones, Donald J.L., Jukes-Jones, Rebekah, Verschoyle, Richard D., Farmer, Peter B., Gescher, Andreas
• Format: Article
• Language: English
• Subjects: Animals; Biological and medical sciences; Chromatography, High Pressure Liquid; Feeding. Feeding behavior; Fundamental and applied biological sciences. Psychology; Magnetic Resonance Spectroscopy; Mass spectrometry; Medical sciences; Miscellaneous; Molecular Structure; NMR; Pharmacology. Drug treatments; Quercetin; Quercetin - chemistry; Quercetin - metabolism; Quercetin - pharmacology; Quercetin - urine; Rats; Rats, Inbred F344; Sulfate synthesis; Sulfates - chemical synthesis; Sulfates - chemistry; Sulfates - metabolism; Vertebrates: anatomy and physiology, studies on body, several organs or systems
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2005.07.021

The synthesis and characterization of quercetin sulfate isomers, which are putative metabolites of quercetin, are described herein. To study the biological effects of quercetin, authentic products of quercetin metabolism are required as standards. The synthesis of quercetin sulfate standards is thus described. Quercetin was reacted with a 10-fold molar excess of sulfur trioxide- N-triethylamine, and the products were analyzed by HPLC and mass spectrometry. Four monosulfates and three disulfates were identified, and structural inferences were drawn by 1H NMR spectrometry of HPLC peak isolates. Analysis of the urine of rats that had received quercetin (1.9 g/kg po) yielded a single peak, which by comparison with the products of the reaction between quercetin and sulfur trioxide- N-triethylamine was identified as quercetin 3′- O-sulfate.