Arctiin

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	20362-31-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL388452 ;
ChemSpider	90827 ;
KEGG	C16915 ;
MeSH	arctigenin
PubChem CID	100528;
UNII	TM5RQ949K7 ;
	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 Key: XOJVHLIYNSOZOO-SWOBOCGESA-N ; 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).
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	Infobox references

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

References

↑ 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". Indian Journal of Chemistry (India: NISCAIR-CSIR) 50B: 624. ISSN 0975-0983. http://nopr.niscair.res.in/bitstream/123456789/11408/1/IJCB 50B(4) 624-626.pdf. Retrieved on April 25, 2011.
↑ David J. Triggle; C. R. Ganellin; F. MacDonald (1996). Dictionary of Pharmacological Agents. 1. Boca Raton: Chapman & Hall/CRC. pp. 172. ISBN 0-412-46630-9. https://books.google.com/books?id=DeX7jgInYFMC&q=arctiin&pg=RA1-PA172. Retrieved on September 14, 2008 through Google Book Search.
↑ "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. Bibcode: 2013PLoSO...863354S.

External links

Arctiin 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".

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Original source: https://en.wikipedia.org/wiki/Arctiin. Read more

[IJCB-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". Indian Journal of Chemistry (India: NISCAIR-CSIR) 50B: 624. ISSN 0975-0983. http://nopr.niscair.res.in/bitstream/123456789/11408/1/IJCB 50B(4) 624-626.pdf. Retrieved on April 25, 2011.

[DPA-2] David J. Triggle; C. R. Ganellin; F. MacDonald (1996). Dictionary of Pharmacological Agents. 1. Boca Raton: Chapman & Hall/CRC. pp. 172. ISBN 0-412-46630-9. https://books.google.com/books?id=DeX7jgInYFMC&q=arctiin&pg=RA1-PA172. Retrieved on September 14, 2008 through Google Book Search.

[pmid23691032-3] "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. Bibcode: 2013PLoSO...863354S.

v t e Types of lignans
Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin
Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B
Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether