Genistein 7-β-D-Glucuronide  (Synonyms: Genistein 7-O-glucuronide)

Genistein 7-β-D-Glucuronide (Genistein 7-O-glucuronide) is the primary phase II metabolite of Genistein (HY-14596) in human and rat hepatocytes. Genistein 7-β-D-Glucuronide undergoes distinct deconjugation in different functional assays. Genistein 7-β-D-Glucuronide is produced via hepatic microsomal glucuronidation and shows a mild age-related increase in intrinsic clearance in male F344 rats. Genistein 7-β-D-Glucuronide can be used for research on metabolism^[1][2][3].

Genistein 7-β-D-Glucuronide (10 μM) exerts no inhibitory effects on either tubulogenesis or migration in primary human aortic endothelial cells (HAECs)^[1].
Genistein 7-β-D-Glucuronide undergoes partial deconjugation to free Genistein in primary human aortic endothelial cells (HAECs), with significantly more deconjugation occurring in tubulogenesis assay conditions (~3.77 μM free genistein) than in migration assay conditions (~0.11 μM free genistein) after 24 hours of incubation^[1].
Genistein 7-β-D-Glucuronide (15 μM ¹⁴C-genistein; 2 h) is produced as the predominant metabolite by incubation of Genistein with cryopreserved human and rat hepatocytes, accounting for over 50% of the incubated dose in both species with no significant difference in production rates^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Genistein 7-β-D-Glucuronide (30-300 μM; 30 min) formation rates in individual hepatic microsomes from male F344 rats are 29% higher at 30 μM Genistein and 34% higher at 300 μM Genistein in 28-month-old rats compared to 4-month-old rats^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

446.36

C₂₁H₁₈O₁₁

38482-81-4

Solid

White to light yellow

O=C1C(C(OC=C1C(C=C2)=CC=C2O)=CC(O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]([C@H]3O)C(O)=O)=C4)=C4O

Room temperature in continental US; may vary elsewhere.

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

• [1]. Giménez-Bastida JA, et al. (R,S)-Equol 7-β-D-glucuronide, but not other circulating isoflavone metabolites, modulates migration and tubulogenesis in human aortic endothelial cells targeting the VEGF pathway. Food Funct. 2024;15(14):7387-7399. Published 2024 Jul 15.  [Content Brief]

  [2]. Bursztyka J, et al. Comparison of genistein metabolism in rats and humans using liver microsomes and hepatocytes. Food Chem Toxicol. 2008;46(3):939-948.

  [3]. Bolling BW, et al. The kinetic basis for age-associated changes in quercetin and genistein glucuronidation by rat liver microsomes. J Nutr Biochem. 2010;21(6):498-503.