nobiletin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 449569282

| Name = Nobiletin

| ImageFile = Nobiletin.svg

| ImageSize = 240

| ImageAlt = Skeletal formula of nobiletin

| ImageFile1 = Nobiletin molecule ball.png

| ImageSize1 = 240

| ImageAlt1 = Ball-and-stick model of nobiletin

| IUPACName = 3′,4′,5,6,7,8-Hexamethoxyflavone

| SystematicName = 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one

| OtherNames = Hexamethoxyflavone

|Section1={{Chembox Identifiers

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

| CASNo = 478-01-3

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

| UNII = D65ILJ7WLY

| SMILES = c1c(OC)c(OC)ccc1C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 65283

| InChI = 1/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

| InChIKey = MRIAQLRQZPPODS-UHFFFAOYAI

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MRIAQLRQZPPODS-UHFFFAOYSA-N

| RTECS =

| MeSHName =

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 7602

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C10112

| PubChem = 72344

}}

|Section2={{Chembox Properties

| C=21 | H=22 | O=8

| Density =

| MeltingPt =

| BoilingPt =

}}

Nobiletin is a flavonoid isolated from citrus peels. It is an O-methylated flavone that has the activity to rescue bulbectomy-induced memory impairment.{{cite journal|vauthors = Nagase H, Yamakuni T, Matsuzaki K, Maruyama Y, Kasahara J, Hinohara Y, Kondo S, Mimaki Y, Sashida Y, Tank AW, Fukunaga K, Ohizumi Y |year=2005 |title=Mechanism of Neurotrophic Action of Nobiletin in PC12D Cells |journal=Biochemistry |volume=44 |issue=42 |pages=13683–13691 |issn=0006-2960 |doi=10.1021/bi050643x |pmid=16229458 |quote=Nobiletin is a nonpeptide compound with a low molecular weight from a citrus fruit and has the activity to rescue bulbectomy-induced memory impairment }}

Potential pharmacology

Nobiletin was found to potentially inhibit cartilage degradation.{{cite journal|first=Y.|last=Henrotin|author2=C. Lambert |author3=D. Couchourel |author4=C. Ripoll |author5=E. Chiotelli |date=January 2011|title=Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products|journal=Osteoarthritis and Cartilage|volume=19|issue=1|pages=1–21|doi=10.1016/j.joca.2010.10.017|pmid=21035558|url=http://www.oarsijournal.com/article/S1063-4584%2810%2900358-4/fulltext#sec3.8|accessdate=2011-12-27|doi-access=free}}

Nobiletin was shown to augment AMPA receptor activity and long-term potentiation in cell culture.{{cite journal | journal = Eur J Pharmacol | date = 2008 | volume = 578 | issue = 2–3 | pages = 194–200 | title = Nobiletin, a citrus flavonoid with neurotrophic action, augments protein kinase A-mediated phosphorylation of the AMPA receptor subunit, GluR1, and the postsynaptic receptor response to glutamate in murine hippocampus |vauthors=Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y | pmid = 17976577 | doi=10.1016/j.ejphar.2007.09.028}} Synergistic chemopreventive effects of nobiletin and atorvastatin on colon carcinogenesis have been described.{{cite journal|last1=Wu|first1=Xian|last2=Song|first2=Mingyue|last3=Qiu|first3=Peiju|last4=Rakariyatham|first4=Kanyasiri|last5=Li|first5=Fang|last6=Gao|first6=Zili|last7=Cai|first7=Xiaokun|last8=Wang|first8=Minqi|last9=Xu|first9=Fei|last10=Zheng|first10=Jinkai|last11=Xiao|first11=Hang|title=Synergistic chemopreventive effects of nobiletin and atorvastatin on colon carcinogenesis|journal=Carcinogenesis|date=1 April 2017|volume=38|issue=4|pages=455–464|doi=10.1093/carcin/bgx018|pmid=28207072|pmc=6248647|url=|language=en|issn=0143-3334}}

Nobiletin enhances antitumor efficacy via suppression of IκB/NF-κB signaling in triple-negative breast cancer[5].

References

[5] Kim E, Kim YJ, Ji Z, Kang JM, Wirianto M, Paudel KR, Smith JA, Ono K, Kim JA, Eckel-Mahan K, Zhou X. ROR activation by Nobiletin enhances antitumor efficacy via suppression of IκB/NF-κB signaling in triple-negative breast cancer. Cell death & disease. 2022 Apr 19;13(4):374.

External links

{{usurped|1=[https://web.archive.org/web/20080514040508/http://www.phytochemicals.info/phytochemicals/nobiletin.php Nobiletin]}}, phytochemicals.info

Category:O-methylated flavones

Category:Flavonoids found in Rutaceae