Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H12O4 |
Molecular Weight | 256.2534 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2)C=C1
InChI
InChIKey=DXDRHHKMWQZJHT-FPYGCLRLSA-N
InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
Trihydroxychalcone (Isoliquiritigenin, ISL) is a flavonoid found in licorice root and several other plants that displays antioxidant,anti-inflammatory,and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress. Trihydroxychalcone is a potent antimetastatic agent, which can markedly inhibit the metastatic and invasive capacity of prostate cancer cells. The inhibition of JNK/AP-1 signaling may be one of the mechanisms by which ISL inhibits cancer cell invasion and migration. Trihydroxychalcone has been shown to be a BACE1 inhibitor, which could ameliorate memory impairment in mice, and is expected to be potentially used as a lead compound for further anti-AD reagent development.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3544905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15664435 |
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Target ID: CHEMBL1900 |
320.0 nM [IC50] | ||
Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11501051 |
13.9 µM [IC50] | ||
Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11501051 |
47.2 µM [IC50] | ||
Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20412384 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Studies on cancer chemoprevention by traditional folk medicines XXV. Inhibitory effect of isoliquiritigenin on azoxymethane-induced murine colon aberrant crypt focus formation and carcinogenesis. | 2002 Feb |
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Isoliquiritigenin inhibits cell proliferation and induces apoptosis in human hepatoma cells. | 2005 Feb |
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Isoliquiritigen enhances the antitumour activity and decreases the genotoxic effect of cyclophosphamide. | 2013 Jul 24 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20412384
In APP-PS1 double transgenic mice model the treatment of 9 mg/kg/day of Trihydroxychalcone could obviously decrease Abeta production and Abeta plaque formation, while efficiently improve the memory impairment based on Morris water maze test.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18824345
DU145 cells were cultured in the presence of 0-20 umol/L Trihydroxychalcone with or without 10 ug/L epidermal growth factor (EGF). Trihydroxychalcone inhibited basal and EGF-induced cell migration, invasion and adhesion dose dependently. Trihydroxychalcone decreased EGF-induced secretion of urokinase-type plasminogen activator (uPA), matrix metalloproteinase (MMP)-9, tissue inhibitor of metalloproteinase-1 (TIMP-1), and vascular endothelial growth factor (VEGF), but increased TIMP-2 secretion in a concentration-dependent manner.
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13745-20-5
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ISOLIQUIRITIGENIN
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PRIMARY | A group of neolignan lipid esters and phenolic compounds isolated from the roots and stolons of liquorice (Glycyrrhiza glabra) were found to have chemopreventive properties. Of these compounds, hispaglabridin B isoliquiritigenin, and paratocarpin B were found to be the most potent anti-oxidant agents (Chin et al. 2007). | ||
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DB03285
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ISOLIQUIRITIGENIN
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ACTIVE MOIETY
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