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

Molecular Formula	C21H22O4
Molecular Weight	338.397
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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
Anti-human immunodeficiency virus phenolics from licorice.	1988 Jun	3240462
Phenolic constituents of licorice. II. Structures of licopyranocoumarin, licoarylcoumarin and glisoflavone, and inhibitory effects of licorice phenolics on xanthine oxidase.	1989 Nov	2632045
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
Transcriptional suppression of the HIV promoter by natural compounds.	2003 Mar	12719011
Natural antimycobacterial metabolites: current status.	2004 Apr	15110681
Inhibition by licochalcone A, a novel flavonoid isolated from liquorice root, of IL-1beta-induced PGE2 production in human skin fibroblasts.	2005 Dec	16354411
Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans.	2011 Nov	21615543
Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species.	2014 Mar	24397541
Differential Effects of Glycyrrhiza Species on Genotoxic Estrogen Metabolism: Licochalcone A Downregulates P450 1B1, whereas Isoliquiritigenin Stimulates It.	2015 Aug 17	26134484
Induction of NAD(P)H:Quinone Oxidoreductase 1 (NQO1) by Glycyrrhiza Species Used for Women's Health: Differential Effects of the Michael Acceptors Isoliquiritigenin and Licochalcone A.	2015 Nov 16	26473469
Inhibition of human cytochrome P450 enzymes by licochalcone A, a naturally occurring constituent of licorice.	2015 Oct	26100226

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:19:05 GMT 2023` Edited by `admin` on `Sat Dec 16 04:19:05 GMT 2023`
Record UNII	JTV5467968
Record Status	`Validated (UNII)`
Record Version

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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