Licochalcone A

Last updated
Licochalcone A
Licochalcone A2DCSD.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 635-678-2
PubChem CID
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+ X mark.svgN
    Key: KAZSKMJFUPEHHW-DHZHZOJOSA-N X mark.svgN
  • 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
Safety data sheet
GHS pictograms GHS-pictogram-exclam.svg [1]
GHS Signal word Warning
H302, H312, H332 [1]
P261, P264, P280 [1]
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

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]

Related Research Articles

Liquorice Root of Glycyrrhiza glabra from which a somewhat sweet flavour can be extracted

Liquorice or licorice is the common name of Glycyrrhiza glabra, a flowering plant of the bean family Fabaceae, from the root of which a sweet, aromatic flavouring can be extracted.

Glycyrrhizin Main sweet-tasting constituent of liquorice

Glycyrrhizin is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally, it is a saponin used as an emulsifier and gel-forming agent in foodstuffs and cosmetics. Its aglycone is enoxolone.

<i>Orthomyxoviridae</i> Family of RNA viruses including the influenza viruses

Orthomyxoviridae is a family of negative-sense RNA viruses. It includes seven genera: Alphainfluenzavirus, Betainfluenzavirus, Deltainfluenzavirus, Gammainfluenzavirus, Isavirus, Thogotovirus, and Quaranjavirus. The first four genera contain viruses that cause influenza in birds and mammals, including humans. Isaviruses infect salmon; the thogotoviruses are arboviruses, infecting vertebrates and invertebrates. The Quaranjaviruses are also arboviruses, infecting vertebrates (birds) and invertebrates (arthropods).

Zanamivir

Zanamivir is a medication used to treat and prevent influenza caused by influenza A and B viruses. It is a neuraminidase inhibitor and was developed by the Australian biotech firm Biota Holdings. It was licensed to Glaxo in 1990 and approved in the US in 1999, only for use as a treatment for influenza. In 2006, it was approved for prevention of influenza A and B. Zanamivir was the first neuraminidase inhibitor commercially developed. It is currently marketed by GlaxoSmithKline under the trade name Relenza as a powder for oral inhalation.

<i>Glycyrrhiza lepidota</i> Species of legume

Glycyrrhiza lepidota is a species of Glycyrrhiza native to most of North America, from central Canada south through the United States to California, Texas and Virginia, but absent from the southeastern states. It is also sometimes known in the United States as "wild licorice", to distinguish it from the related European licorice which is occasionally cultivated.

Neuraminidase Glycoside hydrolase enzymes that cleave the glycosidic linkages of neuraminic acids

Neuraminidase (Sialidase) enzymes are glycoside hydrolase enzymes that cleave (cut) the glycosidic linkages of neuraminic acids. Neuraminidase enzymes are a large family, found in a range of organisms. The best-known neuraminidase is the viral neuraminidase, a drug target for the prevention of the spread of influenza infection. The viral neuraminidases are frequently used as antigenic determinants found on the surface of the influenza virus. Some variants of the influenza neuraminidase confer more virulence to the virus than others. Other homologues are found in mammalian cells, which have a range of functions. At least four mammalian sialidase homologues have been described in the human genome . Sialidases may act as pathogenic factors in microbial infections.

Neuraminidase inhibitors (NAIs) are a class of drugs which block the neuraminidase enzyme. They are commonly used as antiviral drugs because they block the function of viral neuraminidases of the influenza virus, by preventing its reproduction by budding from the host cell. Oseltamivir (Tamiflu), zanamivir (Relenza), laninamivir (Inavir), and peramivir belong to this class. Unlike the M2 inhibitors, which work only against the influenza A virus, neuraminidase inhibitors act against both influenza A and influenza B.

Glycyrrhizol Chemical compound

Glycyrrhizol A is a prenylated pterocarpan and an isoflavonoid derivative. It is a compound isolated from the root of the Chinese licorice plant.

Influenza treatment

Treatments for influenza include a range of medications and therapies that are used in response to disease influenza. Treatments may either directly target the influenza virus itself; or instead they may just offer relief to symptoms of the disease, while the body's own immune system works to recover from infection.

<i>Dichroa febrifuga</i> Species of plant

Dichroa febrifuga is a flowering plant in the family Hydrangeaceae. In the Indonesian language it is called gigil, alternatively tataruman in Sundanese, ramram in Papua, Hom dong (ฮอมดง) in Thai, but Yai khlang yai (ยายคลังใหญ่) in Nakhon Sri Thammarat, Yai Krang (ยายกรัง) in the South, and Hom Kham (ฮอมคำ) in Lanna.

Baicalein Chemical compound

Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also reported in Oroxylum indicum and Thyme. It is the aglycone of baicalin. Baicalein is one of the active ingredients of Sho-Saiko-To, which is a Chinese classic herbal formula, and listed in Japan as Kampo medicine. As a Chinese herbal supplement, it is believed to enhance liver health.

Viral neuraminidase

Viral neuraminidase is a type of neuraminidase found on the surface of influenza viruses that enables the virus to be released from the host cell. Neuraminidases are enzymes that cleave sialic acid groups from glycoproteins. Neuraminidase inhibitors are antiviral agents that inhibit influenza viral neuraminidase activity and are of major importance in the control of influenza.

Hemagglutinin-neuraminidase

Hemagglutinin-neuraminidase refers to a single viral protein that has both hemagglutinin and (endo) neuraminidase EC 3.2.1.18 activity. This is in contrast to the proteins found in influenza, where both functions exist but in two separate proteins. Its neuraminidase domain has the CAZy designation glycoside hydrolase family 83 (GH83).

Dihydrofolate reductase inhibitor

A dihydrofolate reductase inhibitor is a molecule that inhibits the function of dihydrofolate reductase, and is a type of antifolate.

Laninamivir

Laninamivir (CS-8958) is a neuraminidase inhibitor that is a drug used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B. It is currently in Phase III clinical trials. It is a long-acting neuraminidase inhibitor administered by nasal inhalation.

Taxifolin Chemical compound

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

Glycyrrhiza inflata is a plant species in the genus Glycyrrhiza from China, with common name Chinese licorice. A related species, G. uralensis, however, is more likely the licorice species one finds in traditional Chinese medicine.

Liquiritigenin Chemical compound

Liquiritigenin is a flavanone that was isolated from Glycyrrhiza uralensis, and is found in a variety of plants, including Glycyrrhiza glabra (licorice). It is an estrogenic compound which acts as a selective agonist of the ERβ subtype of the estrogen receptor (ER), though it is also reported to act as an ERα partial agonist at sufficient concentrations. It also has a choleretic effect.

Neuraminidase inhibitors inhibit enzymatic activity of the enzyme neuraminidase (sialidase). These type of inhibitors have been introduced as anti-influenza drugs as they prevent the virus from exiting infected cells and thus stop further spreading of the virus. Neuraminidase inhibitors for human neuraminidase (hNEU) have the potential to be useful drugs as the enzyme plays a role in several signaling pathways in cells and is implicated in diseases such as diabetes and cancer.

Glabrene Chemical compound

Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra (licorice). It has estrogenic activity, showing estrogenic effects on breast, vascular, and bone tissue, and hence is a phytoestrogen (IC50 for estrogen receptor binding = 1 μM). It has also been found to act as a tyrosinase inhibitor (IC50 = 3.5 μM) and to inhibit the formation of melanin in melanocytes, and for these reasons, has been suggested as a potential skin-lightening agent.

References

  1. 1 2 3 "Licochalcone A Safety Data Sheet" (PDF). Cayman Chemicals.
  2. 1 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. 1 2 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.