Chemistry:Arctigenin

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(−)-Arctigenin
(−)-Arctigenin.svg
Names
IUPAC name
(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
MeSH arctigenin
UNII
Properties
C21H24O6
Molar mass 372.41166
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
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Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral[1] and anticancer[2] effects in vitro. It is the aglycone of arctiin.

The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis.[3]

It has been found to act as an agonist of adiponectin receptor 1 (AdipoR1).[4]

References

  1. Hayashi, K.; Narutaki, K.; Nagaoka, Y.; Hayashi, T.; Uesato, S. (2010). "Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza a virus". Biological & Pharmaceutical Bulletin 33 (7): 1199–1205. doi:10.1248/bpb.33.1199. PMID 20606313. 
  2. Yang, S.; Ma, J.; Xiao, J.; Lv, X.; Li, X.; Yang, H.; Liu, Y.; Feng, S. et al. (2012). "Arctigenin Anti-Tumor Activity in Bladder Cancer T24 Cell Line Through Induction of Cell-Cycle Arrest and Apoptosis". The Anatomical Record 295 (8): 1260–1266. doi:10.1002/ar.22497. PMID 22619087. 
  3. "Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan". J. Antimicrob. Chemother. 61 (3): 679–88. March 2008. doi:10.1093/jac/dkm503. PMID 18230688. 
  4. "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE 8 (5): e63354. 2013. doi:10.1371/journal.pone.0063354. PMID 23691032. Bibcode2013PLoSO...863354S. 

External links

  • Arctigenin entry in the public domain NCI Dictionary of Cancer Terms

 This article incorporates public domain material from the U.S. National Cancer Institute document "Dictionary of Cancer Terms".