Arctigenin

(−)-Arctigenin
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
  • 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
  • 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
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).
X markN verify (what is checkYX markN ?)

Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral and anticancer 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.

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

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.

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