Chrysin 7-Glucuronide

Chrysin 7-glucuronide is a flavonoid glucuronide that has been found in S. baicalensis and has diverse biological activities and is an active metabolite of chrysin (Item No. 17402).^1,2,3,4 It is formed from chrysin by various UDP-glucuronosyltransferase (UGT) isoforms, including UGT1A3, UGT1A6, and UGT1A9.⁴ Chrysin 7-glucuronide inhibits α-glucosidase, α-amylase, and neuraminidase (IC₅₀s = 612, 980, and 428 µg/ml, respectively).^1,2 It also inhibits organic anion transporting polypeptide (OATP) isoforms OATP1A2, OATP1B1, OATP1B3, and OATP2B1 (IC₅₀s = 24.1, 4.4, 14.3, and 0.3 µM, respectively), as well as breast cancer resistance protein (BCRP) and multidrug resistance-associated protein 2 (MRP2; IC₅₀s = 19.8 and 11.2 µM, respectively).³

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1. Li, K., Yao, F., Xue, Q., et al. Inhibitory effects against α-glucosidase and α-amylase of the flavonoids-rich extract from Scutellaria baicalensis shoots and interpretation of structure-activity relationship of its eight flavonoids by a refined assign-score method. Chem. Cent. J. 12(1), 82 (2018).

2. Liu, W., Wang, H., Zhu, B., et al. An activity-integrated strategy of the identification, screening and determination of potential neuraminidase inhibitors from Radix Scutellariae. PLoS One 12(5), e0175751 (2017).

3. Mohos, V., Fliszár-Nyúl, E., Ungvári, O., et al. Effects of chrysin and its major conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide on cytochrome P450 enzymes and on OATP, P-gp, BCRP, and MRP2 Transporters. Drug Metab. Dispos. 48(10), 1064-1073 (2020).

4. Robotham, S.A., and Brodbelt, J.S. Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: Regioselectivity of uridine 5'-diphosphate-glucuronosyltransferase isozymes in the biotransformation of flavones. J. Agric. Food Chem. 61(7), 1457-1463 (2013).