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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH arctigenin
PubChem CID
UNII
InChI
  • 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 Y
    Key: XOJVHLIYNSOZOO-SWOBOCGESA-N Y
  • 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
SMILES
  • 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
Chemical formula
 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 YN ?)
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

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


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