Isoliquiritin

Catalog No. BCN5945
CAS RN 5041-81-6
Molecular Weight 418.39
Molecular Formula C21H22O9
Database [PubChem]:382161679
[ChEBI]:80839
[PCIDB]:7184

Definition

A monosaccharide derivative that is trans-chalcone substituted by hydroxy groups at positions 2' and 4' and a β-D-glucopyranosyloxy group at position 4 respectively.

Standard InChI

InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1

Biological Activity

Insampaedoksan is a traditional herbal medicine used for antipyretic and antiinflammatory diseases, isoliquiritigenin is the main compound of it , thus , isoliquiritigenin has bioactivity effects such as antioxidant, estrogenic and anticancer. [1]
Isoliquiritin, liquiritin,and isoliquirigenin are the active polyphenols present in Glycyrrhiza uralensis which has been used for the treatment of cancer and its complications, they induce apoptotic cell death through upregulating p53 and p21 in the A549 non-small cell lung cancer cells and inhibit the p53-dependent pathway and showed crosstalk between Akt activities,suggests they can be an alternative agent for the treatment of lung cancer.[2]
Isoliquiritin and liquiritin produce 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.[3]
Isoliquiritin has antifungal activity, and has inhibitory effect against peronophythora litchi chen through a membrane damage mechanism, it 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.[4]
Isoliquiritin has anti-tumor activity, can induce hepatoma cell apoptosis in H22-bearing mice by down-regulating the expression of Bcl-2 and up-regulating expression of Bax, Cyt-c and Caspase-3, it can also induce the apoptosis in MDA-MB-231 cells.[5]

Product information

English website: Isoliquiritin
Japanese website: Isoliquiritin
Chinese website: Isoliquiritin

References

[1] Lee K J, Jung P M, Roh J H, et al. Asian J Chem, 2014,26(8):24-5.
[2] Zhou Y, Ho W S. Oncol Rep, 2014, 31(1):298-304.
[3] Wang W, Hu X, Zhao Z, et al. Prog Neuro-psychoph, 2008, 32(5):1179-84.
[4] Luo J, Li Z, Wang J, et al. Molecules, 2016, 21(2):237.
[5] Luo J, Li Z, Wang J, et al. Central South Pharmacy,  2015(08):806-10.
[6] Liu Y, Yang J S. China Pharm (English), 2005, 14(4):227-30.