Disease relevance of isoliquiritigenin

• Isoliquiritigenin prominently inhibited H(2)R selective agonist dimaprit-induced cAMP generation in MKN-45 gastric cancer cell [1].
• Molecular characterization and expression of alfalfa isoliquiritigenin 2'-O-methyltransferase, an enzyme specifically involved in the biosynthesis of an inducer of Rhizobium meliloti nodulation genes [2].
• In addition, isoliquiritigenin potently inhibited 7,12-dimethylbenz[alpha]anthracene (DMBA)-initiated and TPA-promoted skin papilloma formation [3].
• A topical application of a chalcone derivative, 4,2',4'-trihydroxychalcone (isoliquiritigenin) inhibited epidermal ornithine decarboxylase (ODC) induction and ear edema formation, i.e. inflammation, caused by a topical application of 12-O-tetradecanoylphorbol-13-acetate (TPA) in CD-1 mice [3].
• Isoliquiritigenin inhibits the growth of prostate cancer [4].

High impact information on isoliquiritigenin

• We have examined the spontaneous and CHI-catalyzed cyclization reactions of 4,2',4',6'-tetrahydroxychalcone, 4,2',4'-trihydroxychalcone, 2',4'-dihydroxychalcone, and 4,2'-dihydroxychalcone into the corresponding flavanones [5].
• Isoliquiritigenin, one of the major constituents of Glycyrrhiza uralensis (licorice), is a natural pigment with a simple chalcone structure 4,2',4'-trihydroxychalcone [1].
• Isoliquiritigenin also blocked the binding affinity of [(3)H]tiotidine to membrane receptors in HL-60 cells [1].
• Moreover, isoliquiritigenin reduced gastric acid secretion and protected gastric mucosal lesion formation in pylorus-ligated rat model [1].
• Inhibition of ODC induction by indomethacin was counteracted by a topical application of PGE2, while inhibition caused by isoliquiritigenin was not overcome by PGE2 [3].

Chemical compound and disease context of isoliquiritigenin

• S-Adenosyl-L-methionine (SAM): isoliquiritigenin (2',4,4'-trihydroxychalcone) 2'-O-methyltransferase (CHMT) of alfalfa (Medicago sativa) catalyses the formation of 4,4'-dihydroxy-2'-methoxychalcone, which is the most potent inducer of nodulation-genes of Rhizobium meliloti, the symbiont of alfalfa which forms nitrogen-fixing nodules [6].
• In addition, isoliquiritigenin prevented severe leukocytopenia caused by administration of 5-fluorouracil [7].
• Flowcytometric analysis showed that isoliquiritigenin and butein increased the proportion of hypodiploid cells in the population of B16 melanoma cells [8].

Biological context of isoliquiritigenin

• These results suggest that isoliquiritigenin induced apoptosis of MGC-803 cells through calcium- and Deltapsi(m)-dependent pathways, indicating that it is potentially useful as a natural anti-cancer agent [9].
• We examined the effects of isoliquiritigenin on cell proliferation, cell cycle regulation and cell cycle-regulating gene expression [4].
• Fluorescence-activated cell sorting (FACS) analysis indicated that isoliquiritigenin induced S and G2/M phase arrest [4].
• Isoliquiritigenin inhibits cell proliferation and induces apoptosis in human hepatoma cells [10].
• The inhibitory effect of isoliquiritigenin on platelet aggregation in vitro was comparable to that of aspirin [11].

Anatomical context of isoliquiritigenin

• Isoliquiritigenin inhibits neither 12-lipoxygenase nor cyclooxygenase in epidermal subcellular fractions [3].
• Isoliquiritigenin failed to inhibit phospholipase A2 activity of platelet sonicates, but inhibited platelet 12-lipoxygenase and 5-lipoxygenase in polymorphonuclear leukocytes [3].
• The highly efficient induction of nod genes and glyceollin resistance by isoliquiritigenin suggests the ecological significance of this compound, although it is not a major flavonoid constituent of the soybean root exudate in quantitative terms [12].
• In this study, we investigated the anti-tumor effect of isoliquiritigenin on prostate cancer in vitro.METHODS: DU145 and LNCaP prostate cancer cell lines were used as targets [4].
• Effect of isoliquiritigenin on viability and differentiated functions of human hepatocytes maintained on PEEK-WC-polyurethane membranes [13].

Associations of isoliquiritigenin with other chemical compounds

• The results suggest that a mechanism other than the inhibition of PGE2 production is involved in the anti-tumor-promoting action of isoliquiritigenin [3].
• 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 [14].
• Results indicated that glabrene and isoliquiritigenin, (2',4',4-three hydroxy chalcone) (ILC) in the licorice extract can bind to the human ER with higher affinity (IC50, 1 and 0.5 microM) than glabridin (IC50, 5 microM) [15].
• Identification, purification, and characterization of S-adenosyl-L-methionine: isoliquiritigenin 2'-O-methyltransferase from alfalfa (Medicago sativa L.) [16].
• The purified OMT had a pH optimum of 9.0, pI of 4.7, and was highly specific for the 2'-hydroxyl of 2',4,4'-trihydroxychalcone, with essentially no activity toward narigenin chalcone, caffeic acid, or daidzein [16].

Gene context of isoliquiritigenin

• The chalcone isoliquiritigenin (ISL) is a component of licorice extract exhibiting either antitumorigenic activity or estrogen receptor (ER) alpha-dependent growth promoting effects on breast cancer cells [17].
• Isoliquiritigenin induces apoptosis and cell cycle arrest through p53-dependent pathway in Hep G2 cells [18].
• Aim: To examine whether isoliquiritigenin (ISL) can attenuate myocardial ischemiareperfusion (MI/R) injury in rats by inducing metallothionein (MT) through activation of janus kinase 2 (JAK 2)/signal transducers and activators of transcription 3 (STAT 3) pathway [19].
• Isoliquiritigenin downregulated CAM proteins in TNF-alpha-activated HUVEC at the transcriptional levels by blocking degradation of IkappaBalpha and nuclear translocation of NF-kappaB [20].
• Extracellular glucose decreased the proportion of hypodiploid cells that appeared as a result of isoliquiritigenin treatment. p53 was not detected in cells treated with either of these chalcones, however, protein of the Bcl-2 family were detected [8].

Analytical, diagnostic and therapeutic context of isoliquiritigenin

• A simple, reliable, reproducible and sensitive method, based on capillary electrophoresis with electrochemical detection (ED), for the determination of liquiritigenin and isoliquiritigenin in Glycyrrhiza uralensis and its medicinal preparations was described [21].
• An O-methyltransferase (OMT) which methylates the 2'-hydroxyl of isoliquiritigenin (2',4,4'-trihydroxychalcone) was identified in alfalfa (Medicago sativa L.) seedlings and cell cultures [16].
• Selected compounds (3-5) were evaluated in a mouse mammary organ culture assay, with isoliquiritigenin (3) found to exhibit 76% inhibition at a dose of 10 microg/mL [22].
• Further examinations using cDNA arrays and real-time quantitative RT-PCR revealed that isoliquiritigenin enhanced the expression of p21(CIP1/WAF1), a universal inhibitor of cyclin-dependent kinases [23].
• The average number of tumors was 14.6+/-8.9 items in the control group and were 7.3+/-7.3, 3.9+/-5.6, 4.7+/-6.5 items in the 10, 100 and 250 ppm in the isoliquiritigenin treated groups, respectively [24].

References