Nobiletin

Nobiletin
Names
	IUPAC name 3′,4′,5,6,7,8-Hexamethoxyflavone
	Systematic IUPAC name 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
	Other names Hexamethoxyflavone
Identifiers
CAS Number	478-01-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7602 ;
ChemSpider	65283 ;
KEGG	C10112 ;
PubChem CID	72344;
UNII	D65ILJ7WLY ;
CompTox Dashboard (EPA)	DTXSID30197275 ;
	InChI InChI=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 Key: MRIAQLRQZPPODS-UHFFFAOYSA-N ; 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 Key: MRIAQLRQZPPODS-UHFFFAOYAI;
	SMILES c1c(OC)c(OC)ccc1C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2;
Properties
Chemical formula	C21H22O8
Molar mass	402.399 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Nobiletin is a flavonoid isolated from citrus peels. It is an O-methylated flavone that has the activity to rescue bulbectomy-induced memory impairment.^[1]

Potential pharmacology

Nobiletin was found to potentially inhibit cartilage degradation.^[2]

Nobiletin was shown to augment AMPA receptor activity and long-term potentiation in cell culture.^[3] Synergistic chemopreventive effects of nobiletin and atorvastatin on colon carcinogenesis have been described.^[4] Nobiletin enhances antitumor efficacy via suppression of IκB/NF-κB signaling in triple-negative breast cancer[5].

References

^ Nagase H, Yamakuni T, Matsuzaki K, Maruyama Y, Kasahara J, Hinohara Y, Kondo S, Mimaki Y, Sashida Y, Tank AW, Fukunaga K, Ohizumi Y (2005). "Mechanism of Neurotrophic Action of Nobiletin in PC12D Cells". Biochemistry. 44 (42): 13683–13691. doi:10.1021/bi050643x. ISSN 0006-2960. PMID 16229458. Nobiletin is a nonpeptide compound with a low molecular weight from a citrus fruit and has the activity to rescue bulbectomy-induced memory impairment
^ Henrotin, Y.; C. Lambert; D. Couchourel; C. Ripoll; E. Chiotelli (January 2011). "Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products". Osteoarthritis and Cartilage. 19 (1): 1–21. doi:10.1016/j.joca.2010.10.017. PMID 21035558. Retrieved 2011-12-27.
^ Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y (2008). "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". Eur J Pharmacol. 578 (2–3): 194–200. doi:10.1016/j.ejphar.2007.09.028. PMID 17976577.
^ Wu, Xian; Song, Mingyue; Qiu, Peiju; Rakariyatham, Kanyasiri; Li, Fang; Gao, Zili; Cai, Xiaokun; Wang, Minqi; Xu, Fei; Zheng, Jinkai; Xiao, Hang (1 April 2017). "Synergistic chemopreventive effects of nobiletin and atorvastatin on colon carcinogenesis". Carcinogenesis. 38 (4): 455–464. doi:10.1093/carcin/bgx018. ISSN 0143-3334. PMC 6248647. PMID 28207072.

[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

Nobiletin, phytochemicals.info

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[Nagase2005-1] Nagase H, Yamakuni T, Matsuzaki K, Maruyama Y, Kasahara J, Hinohara Y, Kondo S, Mimaki Y, Sashida Y, Tank AW, Fukunaga K, Ohizumi Y (2005). "Mechanism of Neurotrophic Action of Nobiletin in PC12D Cells". Biochemistry. 44 (42): 13683–13691. doi:10.1021/bi050643x. ISSN 0006-2960. PMID 16229458. Nobiletin is a nonpeptide compound with a low molecular weight from a citrus fruit and has the activity to rescue bulbectomy-induced memory impairment

[2] Henrotin, Y.; C. Lambert; D. Couchourel; C. Ripoll; E. Chiotelli (January 2011). "Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products". Osteoarthritis and Cartilage. 19 (1): 1–21. doi:10.1016/j.joca.2010.10.017. PMID 21035558. Retrieved 2011-12-27.

[3] Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y (2008). "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". Eur J Pharmacol. 578 (2–3): 194–200. doi:10.1016/j.ejphar.2007.09.028. PMID 17976577.

[4] Wu, Xian; Song, Mingyue; Qiu, Peiju; Rakariyatham, Kanyasiri; Li, Fang; Gao, Zili; Cai, Xiaokun; Wang, Minqi; Xu, Fei; Zheng, Jinkai; Xiao, Hang (1 April 2017). "Synergistic chemopreventive effects of nobiletin and atorvastatin on colon carcinogenesis". Carcinogenesis. 38 (4): 455–464. doi:10.1093/carcin/bgx018. ISSN 0143-3334. PMC 6248647. PMID 28207072.

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