Arctiin

Arctiin is a lignan found in many plants of the family Asteraceae, particularly the greater burdock (Arctium lappa) and Centaurea imperialis, and in Trachelospermum asiaticum, Saussurea heteromalla,[1] and Forsythia viridissima.[2] It is the glucoside of arctigenin.

Arctiin
Names
IUPAC name
(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl}oxolan-2-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
MeSH arctigenin
UNII
  • InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1 checkY
    Key: XOJVHLIYNSOZOO-SWOBOCGESA-N checkY
  • InChI=1/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1
    Key: XOJVHLIYNSOZOO-SWOBOCGEBY
  • O=C2OC[C@H](Cc1ccc(OC)c(OC)c1)[C@H]2Cc4ccc(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)c(OC)c4
Properties
C27H34O11
Molar mass 534.558 g·mol−1
Melting point 110 to 112 °C (230 to 234 °F; 383 to 385 K)
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

Arctiin and arctigenin have shown anticancer effects in animal research. They have been found to act as agonists of the adiponectin receptor 1.[3]

References
  1. Arvind Saklani; Manas Ranjan Sahoo; Prabhu Dutt Mishra; Ram Vishwakarma (2010). "Saussurea heteromalla (D. Don) Hand.-Mazz.: A new source of arctiin, arctigenin and chlorojanerin" (PDF). Indian Journal of Chemistry. India: NISCAIR-CSIR. 50B: 624. ISSN 0975-0983. Retrieved on April 25, 2011.
  2. David J. Triggle; C. R. Ganellin; F. MacDonald (1996). Dictionary of Pharmacological Agents. Vol. 1. Boca Raton: Chapman & Hall/CRC. p. 172. ISBN 0-412-46630-9. Retrieved on September 14, 2008 through Google Book Search.
  3. 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.
  • Arctiin entry in the public domain NCI Dictionary of Cancer Terms

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


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.