Cannabaceae

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[edit]

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[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. 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.

External links[edit]


One thought on “Cannabaceae

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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