Licochalcone A

Licochalcone A is a chalconoid, a type of natural phenol. It can be isolated from the root of Glycyrrhiza glabra[2] (liquorice) or Glycyrrhiza inflata.[3] It shows antimalarial, anticancer, antibacterial and antiviral (specifically against influenza neuraminidase) properties in vitro.[2][3][4][5]

Licochalcone A
Chemical structure of licochalcone A
Names
Preferred IUPAC name
(2E)-3-[4-Hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Other names
Licochalcone a
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.163.544
EC Number
  • 635-678-2
UNII
  • 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+ ☒N
    Key: KAZSKMJFUPEHHW-DHZHZOJOSA-N ☒N
  • InChI=1/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+
    Key: KAZSKMJFUPEHHW-DHZHZOJOBU
  • CC(C)(C=C)c1cc(c(cc1O)OC)/C=C/C(=O)c2ccc(cc2)O
Properties
C21H22O4
Molar mass 338.403 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark[1]
Warning
H302, H312, H332[1]
P261, P264, P280[1]
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. "Licochalcone A Safety Data Sheet" (PDF). Cayman Chemicals.
  2. Fu, Y.; Hsieh, T. C.; Guo, J.; Kunicki, J.; Lee, M. Y. W. T.; Darzynkiewicz, Z.; Wu, J. M. (2004). "Licochalcone-A, a novel flavonoid isolated from licorice root (Glycyrrhiza glabra), causes G2 and late-G1 arrests in androgen-independent PC-3 prostate cancer cells". Biochemical and Biophysical Research Communications. 322 (1): 263–270. doi:10.1016/j.bbrc.2004.07.094. PMID 15313200.
  3. Friis-Møller, A.; Chen, M.; Fuursted, K.; Christensen, S. R. B. G.; Kharazmi, A. (2002). "In Vitro Antimycobacterial and Antilegionella Activity of Licochalcone a from Chinese Licorice Roots". Planta Medica. 68 (5): 416–419. doi:10.1055/s-2002-32087. PMID 12058317.
  4. Chen, M.; Theander, T. G.; Christensen, S. B.; Hviid, L.; Zhai, L.; Kharazmi, A. (1994). "Licochalcone A, a new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. Yoelii infection". Antimicrobial Agents and Chemotherapy. 38 (7): 1470–1475. doi:10.1128/aac.38.7.1470. PMC 284578. PMID 7979274.
  5. Dao, TT; Nguyen, PH; Lee, HS; Kim, E; Park, J; Lim, SI; Oh, WK (January 2011). "Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata". Bioorganic & Medicinal Chemistry Letters. 21 (1): 294–8. doi:10.1016/j.bmcl.2010.11.016. PMID 21123068.


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