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{{Wikify|date=September 2011}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 434462859 |
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| Watchedfields = changed |
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| Name = Nobiletin |
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| verifiedrevid = 449569282 |
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| ImageFile = Nobiletin.svg |
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| Name = Nobiletin |
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| ImageSize = 250px |
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| ImageName = Nobiletin structure |
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| ImageFile = Nobiletin.svg |
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| ImageSize = 240 |
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| IUPACName = 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one |
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| ImageAlt = Skeletal formula of nobiletin |
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| OtherNames = Hexamethoxyflavone |
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| ImageFile1 = Nobiletin molecule ball.png |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 478-01-3 |
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| ImageSize1 = 240 |
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| ImageAlt1 = Ball-and-stick model of nobiletin |
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| SMILES = COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC |
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| IUPACName = 3′,4′,5,6,7,8-Hexamethoxyflavone |
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| InChI = |
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| SystematicName = 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4''H''-1-benzopyran-4-one |
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| PubChem = 72344 |
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| OtherNames = Hexamethoxyflavone |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 478-01-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = D65ILJ7WLY |
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| SMILES = c1c(OC)c(OC)ccc1C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 65283 |
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| 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 |
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| InChIKey = MRIAQLRQZPPODS-UHFFFAOYAI |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MRIAQLRQZPPODS-UHFFFAOYSA-N |
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| RTECS = |
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| MeSHName = |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 7602 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C10112 |
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| PubChem = 72344 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=21 | H=22 | O=8 |
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| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>8</sub> |
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| Density = |
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| MolarMass = 402.39 g/mol |
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| MeltingPt = |
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| ExactMass = 402.131468 u |
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| Density = |
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| BoilingPt = |
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| MeltingPt = |
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| BoilingPt = |
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'''Nobiletin''' is a ] isolated from ]s. It is an ] that has the activity to rescue ]-induced memory impairment.<ref name="Nagase2005">{{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 }}</ref> |
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'''Nobiletin''' is a chemical compound. It is an ], a flavonoid isolated from citrus peels like in ]. |
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==Potential pharmacology== |
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==References== |
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Nobiletin was found to potentially inhibit cartilage degradation.<ref>{{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}}</ref> |
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{{Unreferenced|date=June 2011}} |
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Nobiletin was shown to augment ] activity and long-term potentiation in cell culture.<ref>{{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}}</ref> Synergistic chemopreventive effects of nobiletin and ] on ] have been described.<ref>{{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}}</ref> |
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Nobiletin enhances antitumor efficacy via suppression of IκB/NF-κB signaling in triple-negative breast cancer. |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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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. |
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==External links== |
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== External links == |
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* , phytochemicals.info |
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* {{usurped|1=}}, phytochemicals.info |
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{{flavone}} |
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{{flavone}} |
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{{Natural-phenol-stub}} |
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{{Aromatic-stub}} |
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