arctigenin

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 457138871

| Name = (−)-Arctigenin

| ImageFile = (−)-Arctigenin.svg

| ImageSize = 250

| IUPACName = (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 7770-78-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U76MR9VS6M

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10545

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 435734

| PubChem = 64981

| SMILES = COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 58506

| SMILES2 = O=C2OC[C@H](Cc1cc(OC)c(OC)cc1)[C@H]2Cc3ccc(O)c(OC)c3

| 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

| InChIKey = NQWVSMVXKMHKTF-JKSUJKDBBB

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NQWVSMVXKMHKTF-JKSUJKDBSA-N

| MeSHName = arctigenin

}}

|Section2={{Chembox Properties

| Formula = C₂₁H₂₄O₆

| MolarMass = 372.41166

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral{{Cite journal

| doi = 10.1248/bpb.33.1199

| last1 = Hayashi | first1 = K.

| last2 = Narutaki | first2 = K.

| last3 = Nagaoka | first3 = Y.

| last4 = Hayashi | first4 = T.

| last5 = Uesato | first5 = S.

| title = Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza a virus

| journal = Biological & Pharmaceutical Bulletin

| volume = 33

| issue = 7

| pages = 1199–1205

| year = 2010

| pmid = 20606313

| doi-access = free

}} and anticancer{{Cite journal

| last1 = Yang | first1 = S.

| last2 = Ma | first2 = J.

| last3 = Xiao | first3 = J.

| last4 = Lv | first4 = X.

| last5 = Li | first5 = X.

| last6 = Yang | first6 = H.

| last7 = Liu | first7 = Y.

| last8 = Feng | first8 = S.

| last9 = Zhang | first9 = Y.

| doi = 10.1002/ar.22497

| title = Arctigenin Anti-Tumor Activity in Bladder Cancer T24 Cell Line Through Induction of Cell-Cycle Arrest and Apoptosis

| journal = The Anatomical Record

| volume = 295

| issue = 8

| pages = 1260–1266

| year = 2012

| pmid = 22619087

| doi-access = free

}} effects in vitro. It is the aglycone of arctiin.

The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis.{{cite journal |vauthors=Swarup V, Ghosh J, Mishra MK, Basu A |title=Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan |journal=J. Antimicrob. Chemother. |volume=61 |issue=3 |pages=679–88 |date=March 2008 |pmid=18230688 |doi=10.1093/jac/dkm503 |doi-access=free }}

It has been found to act as an agonist of adiponectin receptor 1 (AdipoR1).{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354 | bibcode = 2013PLoSO...863354S | doi-access = free }}