Arctiin

Arctiin

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^N
PubChem	100528
ChemSpider	90827^Y
MeSH	arctigenin
ChEMBL	CHEMBL388452^Y
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₂₇H₃₄O₁₁
Molar mass	534.55 g mol⁻¹
Melting point	110–112 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Arctiin is a lignan found in many plants of the Asteraceae family, 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.

References

^ Arvind Saklani; Manas Ranjan Sahoo, Prabhu Dutt Mishra, Ram Vishwakarma (2010). Indian Journal of Chemistry. 50B. India: NISCAIR-CSIR. pp. p. 624. ISSN 0975-0983. http://nopr.niscair.res.in/bitstream/123456789/11408/1/IJCB%2050B%284%29%20624-626.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. p. 172. ISBN 0-412-46630-9. http://books.google.com/books?id=DeX7jgInYFMC&pg=RA1-PA172&dq=arctiin&sig=ACfU3U1eUsRs0h6r9aei25x2WxRiRrqNIA#PRA1-PA172,M1. Retrieved on September 14, 2008 through Google Book Search.

Types of lignans

Lignans	Arctigenin \| Globoidnan A \| Macelignan \| Matairesinol \| Pinoresinol \| Podophyllotoxin \| Secoisolariciresinol \| Sesamin \| Steganacin

Lignan glycosides	Arctiin \| Secoisolariciresinol diglucoside

Mammalian lignans (enterolignans)	Enterodiol \| Enterolactone \| Lariciresinol \| Hydroxymatairesinol \| Syringaresinol

Neolignans	Eusiderin \| Megaphone \| Rhaphidecursinol A \| Rhaphidecursinol B

Flavonolignans	Silibinin