Systematic studies of sulfation and glucuronidation of 12 flavonoids in the mouse liver S9 fraction reveal both unique and shared positional preferences.

Journal of Agricultural and Food Chemistry
Lan TangZhong-Qiu Liu

Abstract

Sulfation and glucuronidation are the principal metabolic pathways of flavonoids, and extensive phase II metabolism is the main reason for their poor bioavailabilities. The purpose of this study was to compare the similarities and differences in the positional preference of glucuronidation versus sulfation in the mouse liver S9 fraction. The conjugating rates of seven monohydroxyflavones (HFs) (i.e., 2'-, 3'-, 4'-, 3-, 5-, 6-, and 7-HF), and five dihydroxyflavones (diHFs) (i.e., 6,7-, 4',7-, 3,7-, 5,7-, and 3,4'-diHF) were determined in three separate enzymatic reaction systems: (A) sulfation only, (B) glucuronidation only, or (C) simultaneous sulfation and glucuronidation (i.e., Sult-Ugt coreaction). In general, glucuronidation rates were much faster than sulfation rates. Among the HFs, 7-HF was the best substrate for both conjugation reactions, whereas 3-HF was rapidly glucuronidated but was not sulfated. As a result, the rank order of sulfation was very different from that of glucuronidation. Among the diHFs, regiospecific glucuronidation was limited to 7-OH and 3-OH positions, whereas regiospecific sulfation was limited to 7-OH and 4'-OH positions. Other positions (i.e., 6-OH and 5-OH) in diHFs were not conjugated. The posi...Continue Reading

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Citations

Oct 10, 2013·Journal of Agricultural and Food Chemistry·Jasmina Petreska Stanoeva, Marina Stefova
Sep 17, 2013·Molecular Nutrition & Food Research·Toshiyuki NakamuraJunji Terao
Mar 29, 2014·Molecular Nutrition & Food Research·Mohammed A IslamIvonne M C M Rietjens
Mar 31, 2015·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Yan XieGuang Ji
Nov 3, 2016·Expert Opinion on Drug Metabolism & Toxicology·Ding TangJuan Li
Feb 4, 2014·Environmental Science & Technology·Mohamed Abou-Elwafa AbdallahStuart Harrad
Nov 21, 2013·Electrophoresis·Maria Rotches-RibaltaCristina Andres-Lacueva
May 31, 2014·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Voon OngPhilippe Prokocimer
Apr 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Han XingYang Lu

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