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Glycyrrhizic acid

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Glycyrrhizic acid inhibits monoamine oxidase (MAO) with the IC50 value of 0.16 μM [1]. With midazolam as the probe substrate, GA greatly decreased CYP3A4 activity with IC50 values of 8.195 µM in HLMs and 7.498 µM in the recombinant cDNA-expressed CYP3A4 enzyme system, respectively. GA could also inhibit the activity of CYP3A4 competitively, with a Ki value of 1.57 µM in HLMs. CYP2C9 and CYP2C19 could also be inhibited strongly by GA with IC50 of 42.89 and 40.26 µM in HLMs, respectively [2].

Glycyrrhizic acid is a triterpenoid saponinl which acts as a direct HMGB1 (high mobility group box 1) antagonist that inhibits HMGB1-dependent inflammatory molecule expression and oxidative stress. It can also inhibit 11 beta-hydroxysteroid dehydrogenase and monoamine oxidase (MAO).

The inhibitory of glycyrrhizic acid to monoamine oxidase (MAO) was relatively not strong, yet it cannot be ignored because of its abundant presence in most species of licorice [1]. Glycyrrhizic acid also promotes GLP-1 secretion with a marked elevation of calcium levels in intestinal NCI-H716 cells that secrete GLP-1. Glycyrrhizic acid can enhance GLP-1 secretion through TGR5 activation [3].

Glycyrrhizic acid competitively inhibits 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 2 (11-HSD2) enzymatic activity. 11-HSD2 protein and mRNA levels were decreased in rats given 120 mg/kg of glycyrrhizic acid twice a day for 2 weeks [4]. Plasma HMGB1 level was significantly decreased compared with that observed in the NS group when rats were pre-treated with 4mg/kg glycyrrhizic acid [5].

[1]. Hatano T, et al. Phenolic constituents of licorice. III. Structures of glicoricone and licofuranone, and inhibitory effects of licorice constituents on monoamine oxidase. Chem Pharm Bull (Tokyo). 1991 May;39(5):1238-43.
[2]. Qiao-Li Lv, et al. In Vitro and in Vivo Inhibitory Effects of Glycyrrhetinic Acid in Mice and Human Cytochrome P450 3A4. Int J Environ Res Public Health. 2015 Dec 25;13(1):84.
[3]. Wang LY, et al. Glycyrrhizic acid increases glucagon like peptide-1 secretion via TGR5 activation in type 1-like diabetic rats. Biomed Pharmacother. 2017 Sep 4;95:599-604.
[4]. Tanahashi T, et al. Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo. J Steroid Biochem Mol Biol. 2002 Apr;80(4-5):441-7.
[5]. Gu Gong, et al. Protective Effect of Glycyrrhizin, a Direct HMGB1 Inhibitor, on Focal Cerebral Ischemia/Reperfusion-Induced Inflammation, Oxidative Stress, and Apoptosis in Rats. PLoS One. 2014; 9(3): e89450.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
Cas No.1405-86-3
SynonymsGlycyron; Glycyrrhetinic acid glycoside; Glycyrrhizin
Solubility≥36.55 mg/mL in DMSO; insoluble in H2O; ≥82.4 mg/mL in EtOH with gentle warming
Chemical NameGlycyron; Glycyrrhetinic acid glycoside; Glycyrrhizin
SDFDownload SDF
Canonical SMILESCC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C
Shipping ConditionEvaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

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