Nobiletin

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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 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).
☒N verify (what is checkY☒N ?)

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

  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.

[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.

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