| 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
PubMed
Patents
Sample Use Guides
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
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.
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
