LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Licochalcone A

Systematic Name

Synonyms

LM ID

LMPK12120424

Formula

C₂₁H₂₂O₄

Exact Mass

Calculate m/z

338.15181

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Licochalcone A is a natural chalcone first identified in roots and rhizomes of licorice (Glycyrrhiza spp.). It has anti-inflammatory actions, supporting its use as a skin lightening agent, particularly for rosacea and atopic dermatitis.^1,2,3 Licochalcone A (10-50 µM) induces apoptosis and suppresses migration and invasion of cancer cells in vitro.^4,5 It also has antibacterial properties against spore-forming bacteria (MIC = 2-15 µg/ml) and anti-parasitic actions (IC50 = 2 µg/ml).^6,7

This information has been provided by Cayman Chemical

References

1. Smit, N., Vicanova, J., and Pavel, S. The hunt for natural skin whitening agents. Int. J. Mol. Sci. 10(12), 5326-5349 (2009).

2. Ziegler, H.L., Hansen, H.S., Staerk, D., et al. The antiparasitic compound licochalcone a is a potent echinocytogenic agent that modifies the erythrocyte membrane in the concentration range where antiplasmodial activity is observed. Antimicrob. Agents Chemother. 48(10), 4067-4071 (2004).

3. Yuan, X., Li, D., Zhao, H., et al. Licochalcone A-induced human bladder cancer T24 cells apoptosis triggered by mitochondria dysfunction and endoplasmic reticulum stress. Biomed Res. Int. 2013, 1-9 (2013).

4. Weber, T.M., Ceilley, R.I., Buerger, A., et al. Skin tolerance, efficacy, and quality of life of patients with red facial skin using a skin care regimen containing Licochalcone A. J. Cosmet. Dermatol. 5(3), 227-232 (2006).

5. Tsukiyama, R.I., Katsura, H., Tokuriki, N., et al. Antibacterial activity of licochalcone A against spore-forming bacteria. Antimicrob. Agents Chemother. 46(5), 1226-1230 (2002).

6. Tsai, J.P., Hsiao, P.C., Yang, S.F., et al. Licochalcone A suppresses migration and invasion of human hepatocellular carcinoma cells through downregulation of MKK4/JNK via NF-κB mediated urokinase plasminogen activator expression. PLoS One 9(1), 1-12 (2014).

7. Angelova-Fischer, I., Neufang, G., Jung, K., et al. A randomized, investigator-blinded efficacy assessment study of stand-alone emollient use in mild to moderately severe atopic dermatitis flares. J. Eur. Acad. Dermatol. Venereol. 28(Suppl 3), 9-15 (2014).