Isoliquiritin

The root of Glycyrrhiza uralensis Fisch.

Antifungal Activity of Isoliquiritin and Its Inhibitory Effect against Peronophythora litchi Chen through a Membrane Damage Mechanism.[Pubmed:26907232]

Molecules. 2016 Feb 19;21(2):237.

This study investigated the antifungal activity and potential antifungal mechanism(s) of Isoliquiritin against P. litchi Chen, one of the main litchi pathogens. The antifungal activity of Isoliquiritin against P. litchi Chen had been proven in a dose-dependent manner through in vitro (mycelial growth and sporangia germination) and in vivo (detached leaf) tests. Results revealed that Isoliquiritin exhibited significant antifungal activity against the tested pathogens, especially, P. litchi Chen, with a minimum inhibitory concentration of 27.33 mg/L. The morphology of P. litchi Chen was apparently changed by Isoliquiritin through cytoplasm leakage and distortion of mycelia. The cell membrane permeability of the P. litchi Chen increased with the increasing concentration of Isoliquiritin, as evidenced by a rise in relative electric conductivity and a decrease in reducing sugar contents. These results indicated that the antifungal effects of Isoliquiritin could be explained by a membrane lesion mechanism causing damage to the cell membrane integrity leading to the death of mycelial cells. Taken together, Isoliquiritin may be used as a natural alternative to commercial fungicides or a lead compound to develop new fungicides for the control of litchi downy blight.

The effect of ethanol extract of Glycyrrhiza uralensis on the voltage-gated sodium channel subtype 1.4.[Pubmed:29433959]

J Pharmacol Sci. 2018 Feb;136(2):57-65.

To investigate the inhibitory effect of Glycyrrhiza uralensis (G. uralensis) and its monomeric compounds on Nav1.4 voltage-gated sodium channels (VGSCs) and analyze the relationship between the content of its marker compounds and the inhibitory rate. Based on this study, we found that 4 mg/ml ethanol extract of G. uralensis at 30%, 50%, 70% and 90% (v/v) exhibited 77.00 +/- 0.03%, 34.75 +/- 0.09%, 100.00 +/- 0.01% and 2.00 +/- 0.01% inhibitory rates on INav1.4 respectively, and 8 mg/ml ethanol extract of G. uralensis at 30%, 50%, 70% and 90% (v/v) exhibited 99.00 +/- 0.01%, 97.10 +/- 0.02%, 100.00 +/- 0.01% and 17.00 +/- 0.04% inhibitory rates on INav1.4 respectively. Isoliquiritigenin, echinatin, liquiritin and glycyrrhizic acid exhibited higher inhibitory rates of 39.98 +/- 4.55%, 33.20 +/- 1.61%, 22.62 +/- 0.30% and 20.54 +/- 4.82% respectively. However, liquiritigenin, formononetin, neoIsoliquiritin and glycyrrhetinic acid exhibited lower inhibitory rates of less than 20%. Further, liquiritin apioside, Isoliquiritin and neoliquiritin exhibited almost no effect on INav1.4. These findings showed that glycyrrhizic acid reached a maximum concentration of 49.15 mug/ml, while echinatin had the lowest concentration. The ethanol extract of G. uralensis has significant inhibitory effects on Nav1.4 VGSCs. This may be an important mechanism in the treatment of gastrocnemius spasm and could guide further research regarding material basis and mechanism of the treatment of gastrocnemius spasm with peony and licorice decoction.

The application of HPLC-MS/MS to studies of pharmacokinetics and interconversion of isoliquiritigenin and neoisoliquiritigenin in rats.[Pubmed:26577957]

Biomed Chromatogr. 2016 Jul;30(7):1155-1161.

A specific and sensitive HPLC-MS/MS method was developed and validated for the simultaneously quantification of isoliquiritigenin (ISL) and neoIsoliquiritin (NIS) in rat plasma by oral administration. Analytes were analyzed on an Agilent 6460 LC-MS/MS system (Agilent, USA) using an Agilent Zorbax SB-C18 column (4.6 x 150 mm, 5 mum). Gradient elution was applied for the analyte separation using a mobile phase composed of 0.1% formic acid aqueous solution and methanol at a flow rate of 1.0 mL/min with a total running time of 12 min. The calibration curves for ISL and NIS showed good linearity in the concentrations ranging from 0.001 to 4.000 mug/mL with correlation coefficients >0.998. The precision, accuracy, recovery and stability were deemed acceptable. The method was applied to the pharmacokinetics study of ISL and NIS in rats by single and combination administration. The result showed that Cmax and AUC0-->t of ISL were markedly increased from 0.53 to 1.20 mug/mL, and from 69.63 to 200.74 min mug/mL by combination administration. The mean t1/2 value was also prolonged from 64.55 to 203.74 min in the combination group. These results indicated that NIS may have been metabolized to ISL which increased the absorption and extended the elimination of ISL. However, little difference was found for NIS pharmacokinetics parameters between single NIS and the combination group, which suggested that there was no significant biotransformation of ISL to NIS. Copyright (c) 2015 John Wiley & Sons, Ltd.

Assessment of genetic fidelity and composition: Mixed elicitors enhance triterpenoid and flavonoid biosynthesis of Glycyrrhiza uralensis Fisch. tissue cultures.[Pubmed:26872048]

Biotechnol Appl Biochem. 2017 Mar;64(2):211-217.

Glycyrrhiza uralensis has acquired significant importance due to its medicinal properties and health function. In this study, the quality of G. uralensis adventitious roots was evaluated in terms of genetic stability, active compounds, and anti-inflammatory activity. Monomorphic banding pattern obtained from the mother plant and tissue cultures of G. uralensis with randomly amplified polymorphic DNA markers confirmed the genetic stability of adventitious roots. Neoliquiritin (neoIsoliquiritin), ononin, liquiritin, and glycyrrhizic acid were identified from G. uralensis adventitious roots on the basis of high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry analysis. This study also revealed that adventitious roots possessed a better anti-inflammatory effect than native roots. To increase the contents of G. uralensis active components, elicitors were used in the adventitious roots culture. The combination of methyl jasmonate and phenylalanine synergistically stimulated the accumulation of glycyrrhetinic acid (0.22 mg/g) and total flavonoid (5.43 mg/g) compared with single treatment. In conclusion, G. uralensis adventitious roots can be an exploitable system for the production of licorice.

Antidepressant-like effects of liquiritin and isoliquiritin from Glycyrrhiza uralensis in the forced swimming test and tail suspension test in mice.[Pubmed:18289754]

Prog Neuropsychopharmacol Biol Psychiatry. 2008 Jul 1;32(5):1179-84.

Two classic animal behavior despair tests--the Forced Swimming Test (FST) and the Tail Suspension Test (TST) were used to evaluate the antidepressant activity of liquiritin and Isoliquiritin from Glycyrrhiza uralensis in mice. It was observed that both liquiritin and Isoliquiritin at doses of 10, 20 and 40 mg/kg significantly reduced the immobility time in the FST and TST in mice 30 min after treatment. Measurement of locomotor activity indicated that liquiritin and Isoliquiritin had no central nervous system (CNS)-stimulating effects. The main monoamine neurotransmitters and their metabolites in mouse brain regions were also simultaneously determined by HPLC-ECD. It was found that these two compounds significantly increased the concentrations of the main neurotransmitters 5-HT and NE in the hippocampus, hypothalamus and cortex. Liquiritin and Isoliquiritin also significantly reduced the ratio of 5-HIAA/5-HT in the hippocampus, hypothalamus and cortex, slowing down 5-HT metabolism compared with mice treated with vehicle+stress. In conclusion, liquiritin and Isoliquiritin produced significant antidepressant-like effects, and their mechanism of action may be due to increased 5-HT and NE in the mouse hippocampus, hypothalamus and cortex.

Combination of the advantages of chromatographic methods based on active components for the quality evaluation of licorice.[Pubmed:26472171]

J Sep Sci. 2015 Dec;38(24):4180-6.

A rapid, improved and comprehensive method including high-performance thin-layer chromatography, fingerprint technology and single standard to determine multiple components was developed and validated for the quality evaluation of licorice. In this study, a newly developed high-performance thin-layer chromatography method was first used for authentication of licorice, which achieved simultaneous identification of multiple bands including five bands for known bioactive components by comparing their retention factor values and colors with the standards. For fingerprint analysis, 8 of 16 common peaks were identified. Simultaneously, similarity analysis which showed very similar patterns and hierarchical clustering analysis were performed to discriminate and classify the 27 batches of samples. Additionally, the single standard to determine multiple components method was first successfully achieved to quantify the eight important active markers in licorice including liquiritin apioside, liquiritin, Isoliquiritin apioside, isoliquritin, neoIsoliquiritin, liquiritigenin, isoliquiritigenin and glycyrrhizic acid. The easily available glycyrrhizic acid was selected as the reference substance to calculate relative response factors. Compared with the normal external standard method, this alternative method can be used to determine the multiple indices effectively and accurately. The validation result showed that the developed method was specific, accurate, precise, robust and reliable for the overall quality assessment of licorice.

Combination of liquiritin, isoliquiritin and isoliquirigenin induce apoptotic cell death through upregulating p53 and p21 in the A549 non-small cell lung cancer cells.[Pubmed:24247527]

Oncol Rep. 2014 Jan;31(1):298-304.

Liquiritin, Isoliquiritin and isoliquirigenin are the active polyphenols present in Glycyrrhiza uralensis which has been used for the treatment of cancer and its complications. The present study was conducted to evaluate the cytotoxicity and antitumor activity of liquiritin, Isoliquiritin and isoliquirigenin on human non-small lung cancer cells including apoptosis-induction, inhibition of apoptotic pathways and to explore the underlying mechanism. Lactate dehydrogenase assays, FITC Annexin V staining assay were performed to evaluate cellular cytotoxicity and apoptosis activity. The results showed that pretreatment with these polyphenols induced apoptosis in A549 cells. Liquiritin, Isoliquiritin and isoliquirigenin significantly increased cytotoxicity of, and upregulated p53 and p21 and downregulated the apoptotic pathways. Furthermore, it inhibited cell cycle at the G2/M phase. Western blot analysis showed it significantly decreased the protein expression of PCNA, MDM2, p-GSK-3beta, p-Akt, p-c-Raf, p-PTEN, caspase-3, pro-caspase-8, pro-caspase-9 and PARP, Bcl-2 in a concentration-dependent manner while the protein expression of p53, p21 and Bax was increased. In addition, Akt pathway was downregulated. These findings suggest that liquiritin, Isoliquiritin and isoliquirigenin inhibited the p53-dependent pathway and showed crosstalk between Akt activities. These active polyphenols can be an alternative agent for the treatment of lung cancer.

Inhibitory effect of isoliquiritin, a compound in licorice root, on angiogenesis in vivo and tube formation in vitro.[Pubmed:8593441]

Biol Pharm Bull. 1995 Oct;18(10):1382-6.

A water extract of licorice root inhibits granuloma angiogenesis in adjuvant-induced chronic inflammation (Phytother. Res., 5, 195. 1991). The present study has investigated the effects of licorice-derived compounds on granuloma angiogenesis. Isoliquiritin (0.31-3.1 mg/kg), a licorice-derived flavonoid, inhibited the carmine content of granuloma tissue 50-fold greater than licorice extract. Glyeyrrhizin (20-80 mg/kg), a licorice-derived saponin, inhibited carmine content with a weak potency. The licorice extract (0.01-1 mg/ml) also inhibited tube formation from vascular endothelial cells in a concentration-dependent manner. From the chemical structure-activities of used licorice-derived flavonoids (0.1-100 microM), their potencies for anti-tube formation were in the order isoliquiritigenin > Isoliquiritin > liquiritigenin >> Isoliquiritin-apioside. Glycyrrhizin (0.1-100 microM) and glycyrrhetinic acid (0.1-10 microM) increased tube formation. A glycyrrhizin (82 micrograms/ml)-induced increase in tube formation was inhibited by Isoliquiritin. The combined effect of a mixture of 82 micrograms/ml glycyrrhizin and 4.2 micrograms/ml Isoliquiritin, a similar concentration ratio to their yield ratio in the licorice extract, corresponded to the effect of 100 micrograms/ml extract. In conclusion, the anti-angiogenic effect of licorice extract depended on the anti-tube formation effect of Isoliquiritin.

Isoliquiritin, isolated from Licorice Root, inhibits angiogenesis and tube formation. Isoliquiritin also exhibits antidepressant-like effects and antifungal activity.

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