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 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL388452 Y

ChemSpider |

* 90827 Y

KEGG |

* C16915 Y

MeSH | arctigenin

PubChem CID

* 100528

UNII |

* TM5RQ949K7 Y

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

Tracking categories (test):

* SizeSet

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

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.
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.
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.

## 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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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

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