Nobiletin

Nobiletin

Names
IUPAC name 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
Other names Hexamethoxyflavone
Identifiers
CAS Number	478-01-3
ChEBI	CHEBI:7602
ChemSpider	65283
Jmol interactive 3D	Image
KEGG	C10112
PubChem	72344
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 COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
Properties
Chemical formula	C21H22O8
Molar mass	402.40 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 have anti-inflammatory and anti-tumor invasion, proliferation, and metastasis in vitro and in animal studies. Nobiletin was also found to potentially inhibit cartilage degradation.^[2]

Nobiletin was shown to augment AMPA receptor activity and long-term potentiation in cell culture.^[3]

References

1. Nagase, Hiroyuki; Tohru Yamakuni, Kentaro Matsuzaki, Yuji Maruyama, Jiro Kasahara, Yoshimi Hinohara, Shunzo Kondo, Yoshihiro Mimaki, Yutaka Sashida, A. William Tank, Kohji Fukunaga, Yasushi Ohizumi (2005). "Mechanism of Neurotrophic Action of Nobiletin in PC12D Cells". Biochemistry (American Chemical Society) 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 Cite uses deprecated parameter |coauthors= (help)
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.

External links

• Nobiletin, phytochemicals.info