4-Hydroxychalcone

4'-hydroxy Chalcone is a chalcone metabolite with diverse biological activities. It is formed when chalcone is metabolized by the cytochrome (CYP) P450 isoform CYP1A1 or CYP2C6.¹ 4'-hydroxy Chalcone is estrogenic in MCF-7 cells and is cytotoxic at concentrations higher than 100 nM. It inhibits TNF-α-induced NF-κB signaling and the trypsin-, chymotrypsin-, and caspase-like proteolytic activities of the 26S proteasome in K562 cells in a dose-dependent manner.² 4'-hydroxy Chalcone reduces growth of K562, U937, and Jurkat cancer cell lines in a dose-dependent manner without effecting viability of peripheral blood mononuclear cells (PBMCs). It also inhibits glutathione reductase (GSH-RD; IC₅₀ = 47.3 μM) in vitro in a reversible and non-competitive manner.³

1.Kohno, Y., Kitamura, S., Sanoh, S., et al.Metabolism of the α,β-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolitesDrug Metab. Dispos.33(8)1115-1123(2005) 2.Orlikova, B., Tasdemir, D., Golais, F., et al.The aromatic ketone 4'-hydroxychalcone inhibits TNFα-induced NF-κB activation via proteasome inhibitionBiochem. Pharmacol.82(6)620-631(2011) 3.Zhang, K., Yang, E.-B., Tang, W.-Y., et al.Inhibition of glutathione reductase by plant polyphenols.Biochem. Pharmacol.54(9)1047-1053(1997)