Nobiletin: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
			\| Watchedfields = changed
	\| verifiedrevid = 449569282		\| verifiedrevid = 449569282
	\| Name = Nobiletin		\| Name = Nobiletin
	\| ImageFile = Nobiletin.svg		\| ImageFile = Nobiletin.svg
	\| ImageSize = ~~250px~~		\| ImageSize = 240
			\| ImageAlt = Skeletal formula of nobiletin
	\| ImageName = Nobiletin structure
			\| ImageFile1 = Nobiletin molecule ball.png
	\| IUPACName = 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
			\| ImageSize1 = 240
⚫	\| OtherNames = Hexamethoxyflavone
			\| ImageAlt1 = Ball-and-stick model of nobiletin
⚫	\| Section1 = {{Chembox Identifiers
			\| IUPACName = 3′,4′,5,6,7,8-Hexamethoxyflavone
⚫	\| CASNo_Ref = {{cascite\|correct\|??}}
			\| SystematicName = 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4''H''-1-benzopyran-4-one
		⚫	\| OtherNames = Hexamethoxyflavone
		⚫	\|Section1={{Chembox Identifiers
		⚫	\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 478-01-3		\| CASNo = 478-01-3
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| SMILES = ~~COC1=C~~(~~C=C~~(~~C=C1~~)C2=CC(=O)~~C3=C~~(O2)C(~~=C(C(=C3OC)~~OC)OC)OC)OC
	\| ~~InChI =~~		\| UNII = D65ILJ7WLY
		⚫	\| SMILES = c1c(OC)c(OC)ccc1C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2
⚫	\| PubChem = 72344
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 65283
			\| 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
			\| InChIKey = MRIAQLRQZPPODS-UHFFFAOYAI
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 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
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = MRIAQLRQZPPODS-UHFFFAOYSA-N
			\| RTECS =
			\| MeSHName =
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 7602
			\| KEGG_Ref = {{keggcite\|changed\|kegg}}
			\| KEGG = C10112
		⚫	\| PubChem = 72344
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=21 \| H=22 \| O=8
	\| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>8</sub>
			\| Density =
	\| MolarMass = 402.39 g/mol
		⚫	\| MeltingPt =
	\| ExactMass = 402.131468 u
	\| ~~Density~~ =		\| BoilingPt =
⚫	\| MeltingPt =
	\| BoilingPt =
	}}		}}
	}}		}}

			'''Nobiletin''' is a ] isolated from ]s. It is an ] that has the activity to rescue ]-induced memory impairment.<ref name="Nagase2005">{{cite journal\|vauthors = Nagase H, Yamakuni T, Matsuzaki K, Maruyama Y, Kasahara J, Hinohara Y, Kondo S, Mimaki Y, Sashida Y, Tank AW, Fukunaga K, Ohizumi Y \|year=2005 \|title=Mechanism of Neurotrophic Action of Nobiletin in PC12D Cells \|journal=Biochemistry \|volume=44 \|issue=42 \|pages=13683–13691 \|issn=0006-2960 \|doi=10.1021/bi050643x \|pmid=16229458 \|quote=Nobiletin is a nonpeptide compound with a low molecular weight from a citrus fruit and has the activity to rescue bulbectomy-induced memory impairment }}</ref>
	'''Nobiletin''' is a chemical compound. It is an ], a flavonoid isolated from citrus peels like in ].

			==Potential pharmacology==
	==Medical effects==
	Nobiletin was ~~found to have anti-inflammatory and anti-tumor invasion, proliferation, and metastasis in vitro and in vivo. Nobiletin was also~~ found to potentially inhibit cartilage degradation.<ref>{{cite journal\|first=Y.\|last=Henrotin\|~~coauthors~~=C. Lambert, D. Couchourel, C. Ripoll, E. Chiotelli \|~~year=2011\|month~~=January\|title=Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products\|journal=Osteoarthritis and Cartilage\|volume=19\|issue=1\|~~page~~=1–21\|doi=10.1016/j.joca.2010.10.017\|url=http://www.oarsijournal.com/article/S1063-4584%2810%2900358-4/fulltext#sec3.8\|accessdate=2011-12-27}}</ref>		Nobiletin was found to potentially inhibit cartilage degradation.<ref>{{cite journal\|first=Y.\|last=Henrotin\|author2=C. Lambert \|author3=D. Couchourel \|author4=C. Ripoll \|author5=E. Chiotelli \|date=January 2011\|title=Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products\|journal=Osteoarthritis and Cartilage\|volume=19\|issue=1\|pages=1–21\|doi=10.1016/j.joca.2010.10.017\|pmid=21035558\|url=http://www.oarsijournal.com/article/S1063-4584%2810%2900358-4/fulltext#sec3.8\|accessdate=2011-12-27\|doi-access=free}}</ref>

			Nobiletin was shown to augment ] activity and long-term potentiation in cell culture.<ref>{{cite journal \| journal = Eur J Pharmacol \| date = 2008 \| volume = 578 \| issue = 2–3 \| pages = 194–200 \| title = 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 \|vauthors=Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y \| pmid = 17976577 \| doi=10.1016/j.ejphar.2007.09.028}}</ref> Synergistic chemopreventive effects of nobiletin and ] on ] have been described.<ref>{{cite journal\|last1=Wu\|first1=Xian\|last2=Song\|first2=Mingyue\|last3=Qiu\|first3=Peiju\|last4=Rakariyatham\|first4=Kanyasiri\|last5=Li\|first5=Fang\|last6=Gao\|first6=Zili\|last7=Cai\|first7=Xiaokun\|last8=Wang\|first8=Minqi\|last9=Xu\|first9=Fei\|last10=Zheng\|first10=Jinkai\|last11=Xiao\|first11=Hang\|title=Synergistic chemopreventive effects of nobiletin and atorvastatin on colon carcinogenesis\|journal=Carcinogenesis\|date=1 April 2017\|volume=38\|issue=4\|pages=455–464\|doi=10.1093/carcin/bgx018\|pmid=28207072\|pmc=6248647\|url=\|language=en\|issn=0143-3334}}</ref>
⚫	==References==
			Nobiletin enhances antitumor efficacy via suppression of IκB/NF-κB signaling in triple-negative breast cancer.

		⚫	== References ==
	{{Reflist}}		{{Reflist}}
			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==		== External links ==
	* , phytochemicals.info		* {{usurped\|1=}}, phytochemicals.info

	{{flavone}}		{{flavone}}

	]		]
	]		]


	{{Natural-phenol-stub}}

			{{Aromatic-stub}}
	]
	]
	]

Latest revision as of 18:37, 22 September 2024

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,1-6H3Key: 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,1-6H3Key: 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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

Potential pharmacology

Nobiletin was found to potentially inhibit cartilage degradation.

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

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.

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

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide

Acetylated

Artocarpetin A

Artoindonesianin P

Sulfated glycosides

Theograndin I and II

Polymers

Drugs

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