Arctigenin

(−)-Arctigenin
Names
IUPAC name
(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH arctigenin
PubChem CID
UNII
InChI
  • InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 checkY
    Key: NQWVSMVXKMHKTF-JKSUJKDBSA-N checkY
  • InChI=1/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
    Key: NQWVSMVXKMHKTF-JKSUJKDBBB
SMILES
  • COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC
  • O=C2OC[C@H](Cc1cc(OC)c(OC)cc1)[C@H]2Cc3ccc(O)c(OC)c3
Properties
Chemical formula
 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).
☒N verify (what is checkY☒N ?)
Infobox references

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.; Zhang, Y. (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. ↑ Swarup V, Ghosh J, Mishra MK, Basu A (March 2008). "Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan". J. Antimicrob. Chemother. 61 (3): 679–88. doi:10.1093/jac/dkm503. PMID 18230688.
  4. ↑ Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE. 8 (5): e63354. Bibcode:2013PLoSO...863354S. doi:10.1371/journal.pone.0063354. PMC 3653934. PMID 23691032.
  • Arctigenin entry in the public domain NCI Dictionary of Cancer Terms

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


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