Liquiritigenin

• CAT Number: R015796
• CAS Number: 578-86-9
• Molecular Formula: C15H12O4
• Molecular Weight: 256.25
• Purity: ≥95%
• Synonyms: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• InChI: InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
• InChIKey: FURUXTVZLHCCNA-AWEZNQCLSA-N
• SMILES: C1C(OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O

Liquiritigenin, a flavanone isolated from Glycyrrhiza uralensis, is a highly selective estrogen receptor β (ERβ) agonist with an EC50 of 36.5 nM for activation of the ERE tk-Luc.
Liquiritigenin produces a dose-response activation of ERE tk-Luc in the U2OS cells transfected with ERβ, but not ERα. Liquiritigenin produces a dose-dependent activation and a time-dependent increase of the CECR6, NKG2E and NKD with ERβ but not with ERα. The ERβ-selectivity of liquiritigenin is due to the selective recruitment of the coactivator steroid receptor coactivator-2 to target genes. Liquiritigenin exhibits similar binding affinities for ERα and ERβ, and causes the recruitment of SRC-2 to target genes selectively in ERβ cells[1]. Pretreatment of MC3T3-E1 cells with liquiritigenin prevents the MG-induced cell death and production of protein adduct, intracellular reactive oxygen species, mitochondrial superoxide, cardiolipin peroxidation, and TNF-α in osteoblastic MC3T3-E1 cells[2].
In a mouse xenograph model, liquiritigenin does not stimulate uterine size or tumorigenesis of MCF-7 breast cancer cells[1]. Treatment with liquiritigenin significantly reduces the concentrations of pro-inflammatory cytokines including interleukin (IL)-6, IL-1β and tumor necrosis factor (TNF)-α in serum and hippocampus[3].

Reference

[1]. Mersereau JE, et al. Liquiritigenin is a plant-derived highly selective estrogen receptor beta agonist. Mol Cell Endocrinol. 2008 Feb 13;283(1-2):49-57.
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[2]. Suh KS, et al. Protective effect of liquiritigenin against methylglyoxal cytotoxicity in osteoblastic MC3T3-E1 cells. Food Funct. 2014 Jul 25;5(7):1432-40.
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[3]. Tao W, et al. Liquiritigenin reverses depression-like behavior in unpredictable chronic mild stress-induced mice by regulating PI3K/Akt/mTOR mediated BDNF/TrkB pathway. Behav Brain Res. 2016 Jul 15;308:177-86.
 [Content Brief]