LICOCHALCONE A

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22O4
Molecular Weight	338.397
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=C(C(O)=C1)C(C)(C)C=C

InChI

InChIKey=KAZSKMJFUPEHHW-DHZHZOJOSA-N

InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28957807 | https://www.ncbi.nlm.nih.gov/pubmed/28498645 | https://www.ncbi.nlm.nih.gov/pubmed/28756519

Licochalcone A (LicA) is a flavonoid isolated from the famous Chinese medicinal herb Glycyrrhiza uralensis Fisch and has a wide spectrum of pharmacological activities such as anti-oxidant, anti-bacterial, anti-viral, and anti-cancer. However, its pharmacological mechanism is not well defined. The anti-Inflammatory effects of LicA on IL-1β-Stimulated human osteoarthritis chondrocytes was reached by activating Nrf2 signaling pathway. LicA showed anti-proliferative and apoptotic effects in breast cancer cells through regulating Sp1 and apoptosis-related proteins in a dose- and a time-dependent manner. In addition, the chemotherapeutic potential of LicA for treatment of human cervical cancer was achieved by inhibition of PI3K/Akt/mTOR signaling.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nrf2 signaling pathway 1 Target ID: Nrf2 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28756519	Activator 1430
Transcription factor Sp1 1 Target ID: P08047 Gene ID: 6667.0 Gene Symbol: SP1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28498645	Inhibitor 8297
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26311737	Inhibitor 8297
mTOR signaling pathway 7 Target ID: map04150 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26311737	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28957807	Palliative	Basic research	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28937602	Palliative	Basic research	Unknown Approved Use Unknown
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28805696	Primary	Basic research	Unknown Approved Use Unknown
Lung infections 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12058317	Curative	Basic research	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28498645	Primary	Basic research	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26311737	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Phenolic constituents of licorice. II. Structures of licopyranocoumarin, licoarylcoumarin and glisoflavone, and inhibitory effects of licorice phenolics on xanthine oxidase.	1989 Nov	2632045
Transcriptional suppression of the HIV promoter by natural compounds.	2003 Mar	12719011
Inhibition by licochalcone A, a novel flavonoid isolated from liquorice root, of IL-1beta-induced PGE2 production in human skin fibroblasts.	2005 Dec	16354411

Patents

Sample Use Guides

In Vivo Use Guide

Nude mice inoculated with Human cervical cancer cell lines (SiHa) were fed with 0, 10, or 20 mg/kg Licochalcone A

Route of Administration: Oral

In Vitro Use Guide

It was investigated the anti-osteoarthritic effects of licochalcone A (Lico A) in rat chondrocytes. Polymerase chain reaction and Western blotting were performed to evaluate the expression of a disintegrin and metalloproteinase with thrombospondin motifs (ADAMTS)-5, ADAMTS-4, collagen II, matrix metalloproteinase (MMP)-13 and MMP-1 at both the gene and protein levels, respectively. In addition, the wnt/β-catenin and nuclear factor kappa B (NF-κB) signaling pathways were also analyzed by Western blotting. Lico A downregulated ADAMTS-5, ADAMTS-4,MMP-13 and MMP-1 expression, and diminished the IL-1β-induced inhibition of collagen II. In addition, the activation of β-catenin and phosphorylation of p65 and IKKα/β were suppressed by Lico A.

Name

Type

Language

LICOCHALCONE A

Common Name

English

2-PROPEN-1-ONE, 3-(5-(1,1-DIMETHYL-2-PROPENYL)-4-HYDROXY-2-METHOXYPHENYL)-1-(4-HYDROXYPHENYL)-, (E)-

Systematic Name

English

LICOCHALCONE A [MI]

Common Name

English

(2E)-3-(5-(1,1-DIMETHYL-2-PROPENYL)-4-HYDROXY-2-METHOXYPHENYL)-1-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE

Systematic Name

English

Licochalcone A [WHO-DD]

Common Name

English

2-PROPEN-1-ONE, 3-(5-(1,1-DIMETHYL-2-PROPENYL)-4-HYDROXY-2-METHOXYPHENYL)-1-(4-HYDROXYPHENYL)-, (2E)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2189