Jump to content

Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

Search

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

Contents

(Top) 1 References 2 External links

Arctigenin

●تۆرکجه ●Español ●فارسی ●Русский ●Српски / srpski ●Srpskohrvatski / српскохрватски ●Tiếng Việt Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version Appearance From Wikipedia, the free encyclopedia

(−)-Arctigenin
Names

IUPAC name (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone
Identifiers
CAS Number	7770-78-7^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL435734^Y
ChemSpider	58506^Y
KEGG	C10545^Y
MeSH	arctigenin
PubChem CID	64981
UNII	U76MR9VS6M^Y
CompTox Dashboard (EPA)	DTXSID60998919
InChI InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1^Y Key: NQWVSMVXKMHKTF-JKSUJKDBSA-N^Y InChI=1/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 Key: NQWVSMVXKMHKTF-JKSUJKDBBB
SMILES COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC O=C2OC[C@H](Cc1cc(OC)c(OC)cc1)[C@H]2Cc3ccc(O)c(OC)c3
Properties
Chemical formula	C₂₁H₂₄O₆
Molar mass	372.41166
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

Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral^[1] and anticancer^[2] effects in vitro. It is the aglyconeofarctiin.

The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis.^[3]

It has been found to act as an agonistofadiponectin receptor 1 (AdipoR1).^[4]

References[edit]

^ Hayashi, K.; Narutaki, K.; Nagaoka, Y.; Hayashi, T.; Uesato, S. (2010). "Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza a virus". Biological & Pharmaceutical Bulletin. 33 (7): 1199–1205. doi:10.1248/bpb.33.1199. PMID 20606313.

^ Yang, S.; Ma, J.; Xiao, J.; Lv, X.; Li, X.; Yang, H.; Liu, Y.; Feng, S.; Zhang, Y. (2012). "Arctigenin Anti-Tumor Activity in Bladder Cancer T24 Cell Line Through Induction of Cell-Cycle Arrest and Apoptosis". The Anatomical Record. 295 (8): 1260–1266. doi:10.1002/ar.22497. PMID 22619087.

^ Swarup V, Ghosh J, Mishra MK, Basu A (March 2008). "Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan". J. Antimicrob. Chemother. 61 (3): 679–88. doi:10.1093/jac/dkm503. PMID 18230688.

^ 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.

External links[edit]

Arctigenin 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.

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 Interiotherin 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

This article about a heterocyclic compound is a stub. You can help Wikipedia by expanding it.

t

e

This antineoplasticorimmunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

t

e

Retrieved from "https://en.wikipedia.org/w/index.php?title=Arctigenin&oldid=1130013386" Categories: ●Adiponectin receptor agonists ●Lignans ●O-methylated natural phenols ●Tetrahydrofurans ●Lactones ●Heterocyclic compound stubs ●Antineoplastic and immunomodulating drug stubs Hidden categories: ●Chemical articles with multiple compound IDs ●Multiple chemicals in an infobox that need indexing ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description matches Wikidata ●Wikipedia articles incorporating text from the National Cancer Institute Dictionary of Cancer Terms ●All stub articles ●This page was last edited on 28 December 2022, at 06:07 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view