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Nobiletin

From Wikipedia, the free encyclopedia
Nobiletin
Skeletal formula of nobiletin
Ball-and-stick model of 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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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 ☒N
    Key: MRIAQLRQZPPODS-UHFFFAOYSA-N ☒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
  • c1c(OC)c(OC)ccc1C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2
Properties
C21H22O8
Molar mass402.399 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Nobiletin is aflavonoid isolated fromcitrus peels. It is anO-methylated flavone that has the activity to rescuebulbectomy-induced memory impairment.[1]

Potential pharmacology

[edit]

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

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

References

[edit]
  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. Retrieved2011-12-27.
  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.

[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

[edit]
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
Sulfated glycosides
Polymers
Drugs


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