Disease relevance of Liquiritigenin

• Previously, we showed that liquiritigenin (LQ), an aglycone of liquiritin in G. radix, exerts cytoprotective effects against heavy metal-induced toxicity in vitro [1].
• Prenylation enhances cytotoxicity of apigenin and liquiritigenin in rat H4IIE hepatoma and C6 glioma cells [2].

High impact information on Liquiritigenin

• Comparisons of the 2.1-2.3 A resolution crystal structures of CHI complexed with the products 7,4'-dihydroxyflavanone, 7-hydroxyflavanone, and 4'-hydroxyflavanone show that the 7-hydroxyflavanones all share a common binding mode, whereas 4'-hydroxyflavanone binds in an altered orientation at the active site [3].
• When the flavanones liquiritigenin and naringenin were incubated with the recombinant yeast microsome expressing CYP93C2, major products emerged and were readily converted to the isoflavones daidzein and genistein by acid treatment [4].
• The chemical structures of the products from liquiritigenin (2-hydroxyisoflavanone and isoflavone) were confirmed by mass spectrometry [4].
• This inhibition of enzyme activity was found to be dose dependent, with an IC50 value of approximately 49.3 microM for liquiritigenin and 55.8 microM for isoliquiritigenin [5].
• In this study, we report the development of a liquid chromatography tandem mass spectrometry (LC-MS/MS)-based method capable of simultaneously quantifying multiple active licorice flavonoids (including liquiritin apioside, liquiritin, liquiritigenin, isoliquiritin apioside, isoliquiritin, and isoliquiritigenin) in plasma [6].

Chemical compound and disease context of Liquiritigenin

• Cytoprotective effects of Glycyrrhizae radix extract and its active component liquiritigenin against cadmium-induced toxicity (effects on bad translocation and cytochrome c-mediated PARP cleavage) [7].

Biological context of Liquiritigenin

• The kinetics of the isomerisation of isoliquiritigenin to liquiritigenin have been examined and show that at pH 7.6 the reaction is reversible with an equilibrium constant of 37 in favour of flavanone [8].
• The present investigation focused on the transepithelial flux of liquiritigenin (LG), davidigenin (DG), liquiritin (LQ), and liquiritin apioside (LA) using the human colonic cell line Caco-2 as a model of human intestinal absorption [9].

Anatomical context of Liquiritigenin

• Permeability of the flavonoids liquiritigenin and its glycosides in licorice roots and davidigenin, a hydrogenated metabolite of liquiritigenin, using human intestinal cell line Caco-2 [9].
• CONCLUSION: Liquiritigenin and isoliquiritigen inhibited the activity of MAO A and B in rat brain mitochondria, and the latter was more active than the former [10].

Associations of Liquiritigenin with other chemical compounds

• 2, 7, 4'-Trihydroxyisoflavonone was formed as a major product when liquiritigenin was incubated with carefully washed microsomes in the presence of NADPH [11].
• High-speed counter-current chromatography (HSCCC) technique in semi-preparative scale has been successfully applied to the separation of bioactive flavonoid compounds, liquiritigenin and isoliquiritigenin in one step from the crude extract of Glycyrrhiza uralensis Risch [12].
• The isolated flavonoids were identified as liquiritin, licuraside, isoliquiritin, liquiritigenin (from Glycyrrhiza uralensis Fisch.), and licochalcone A (from Glycyrrhiza inflate Bat.) by UV, MS, (1)H NMR, and (13)C NMR analyses [13].

Gene context of Liquiritigenin

• IC50 (95% of confidence limits) of liquiritigenin and isoliquiritigenin were 32 (26-36) and 13.9 (12.8-15.6) mumol/L for the inhibition of MAO A, and 104.6 (89.0-118.9) and 47.2 (39.5-54.5) mumol/L for that of MAO B, respectively [10].
• Liquiritigenin, which was previously reported to enhance IL-6 production in anti-CD3 monoclonal antibody-stimulated lung mononuclear cells of BALB, showed no effect on that of B6 [14].

Analytical, diagnostic and therapeutic context of Liquiritigenin

• The production of liquiritigenin in pl-chr overexpressed transgenic tobacco lines was confirmed by HPLC and MS analysis [15].
• Determination of liquiritigenin and isoliquiritigenin in Glycyrrhiza uralensis and its medicinal preparations by capillary electrophoresis with electrochemical detection [16].

References