A synthetic approach to the generation of quercetin sulfates and the detection of quercetin 3'-O-sulfate as a urinary metabolite in the rat.
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.
Jones
Donald J L
DJ
Cancer Biomarkers and Prevention Group, Departments of Biochemistry and Cancer Studies & Molecular Medicine, University of Leicester, Leicester LE1 7RH, UK. djlj1@le.ac.uk
Jukes-Jones
Rebekah
R
Verschoyle
Richard D
RD
Farmer
Peter B
PB
Gescher
Andreas
A
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011794:Quercetin / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology / Q000652:urine*; D051381:Rats; D011916:Rats, Inbred F344; D013431:Sulfates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
D013431:Sulfates; D011794:Quercetin