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Revision as of 09:51, 11 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit		Latest revision as of 09:39, 22 September 2024 edit undoCitation bot (talk | contribs)Bots5,439,567 edits Altered url. URLs might have been anonymized. | Use this bot. Report bugs. | Suggested by Abductive | Category:Misplaced Pages articles needing clarification from September 2024 | #UCB_Category 147/962
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	{{chembox		{{Chembox
			| Verifiedfields = changed
	| verifiedrevid = 411550215
			| Watchedfields = changed
	| ImageFile=Luteolin.svg
			| verifiedrevid = 413273231
	| ImageSize=250px
			| ImageFile = Luteolin.svg
	| ImageName=The chemical structure of luteolin
			| ImageSize = 220px
	| IUPACName=2-(3,4-Dihydroxyphenyl)- 5,7-dihydroxy-4-chromenone
			| ImageName = The chemical structure of luteolin
	| OtherNames=Luteolol<br>Digitoflavone<br>Flacitran<br>Luteoline
			| ImageFile1 = Luteolin molecule ball.png
	|Section1= {{Chembox Identifiers
			| ImageSize1 = 220
	| CASNo_Ref = {{cascite|correct|CAS}}
			| ImageAlt1 = Ball-and-stick model of Luteolin
	| CASNo = 491-70-3
			| IUPACName = 3′,4′,5,7-Tetrahydroxyflavone
	| PubChem = 5280445
			| SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4''H''-1-benzopyran-4-one
	| SMILES = C1=CC(=C(C=C1C2=CC (=O)C3=C(C=C(C=C3O2)O)O)O)O
			| OtherNames = Luteolol<br>Digitoflavone<br>Flacitran<br>Luteoline
	}}
	|Section2= {{Chembox Properties		|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 5215
	| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>6</sub>
			| CASNo_Ref = {{cascite|correct|CAS}}
	| MolarMass = 286.24 g/mol
			| CASNo = 491-70-3
	| ExactMass = 286.047738
			| PubChem = 5280445
	| Appearance=
			| ChEBI_Ref = {{ebicite|changed|EBI}}
	| Density=
			| ChEBI = 15864
	| MeltingPt=
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| BoilingPt=
			| ChEMBL = 151
	| Solubility=
			| UNII_Ref = {{fdacite|changed|FDA}}
	}}
			| UNII = KUX1ZNC9J2
	|Section3= {{Chembox Hazards
			| KEGG = C01514
	| MainHazards=
			| SMILES = C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
	| FlashPt=
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| Autoignition=
			| ChemSpiderID = 4444102
	}}
			| InChI = 1/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
			| InChIKey = IQPNAANSBPBGFQ-UHFFFAOYAY
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = IQPNAANSBPBGFQ-UHFFFAOYSA-N
			}}
			|Section2={{Chembox Properties
			| C=15 | H=10 | O=6
			| Appearance =
			| Density =
			| MeltingPt =
			| BoilingPt =
			| Solubility =
			}}
			|Section3={{Chembox Hazards
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
			}}
	}}		}}
	'''Luteolin''' is a ]; more specifically, it is one of the more common ].<ref name=MannSecondaryMetabolism>{{cite book		'''Luteolin''' is a ], a type of ], with a yellow crystalline appearance.<ref name=MannSecondaryMetabolism>{{cite book
	| last = Mann		| last = Mann
	| first = John		| first = John
	| title = Secondary Metabolism (2nd. ed.)		| title = Secondary Metabolism
	| publisher = ]		| edition = 2nd
			| publisher = ]
	| year = 1992		| year = 1992
	| location = Oxford, UK		| location = Oxford, UK
	| pages = 279–280		| pages =
			| isbn = 978-0-19-855529-2
	| isbn = 0-19-855529-6}}</ref> From preliminary research, it is thought to play a role in the human body possibly as an ], a ] scavenger, a promoter of ] metabolism, or an ] modulator. If applicable to the human condition, these characteristics may inhibit ] mechanisms. ] results indicate luteolin as an ] agent<ref name=Johnson2008>{{cite journal |doi=10.1073/pnas.0802865105 |url=http://www.pnas.org/cgi/content/abstract/105/21/7534?lookupType=volpage&vol=105&fp=7534&view=short |journal=Proceedings of the National Academy of Sciences of the United States of America |title=Luteolin reduces IL-6 production in microglia by inhibiting JNK phosphorylation and activation of AP-1 — PNAS |first3=RW |last3=Johnson |first2=KW |last2=Kelley |volume=105 |author=Johnson et al. |issue=21 |pages=7534–9 |date=May 2008 |pmid=18490655 |pmc=2396685 }}</ref> with other potential effects on ].{{Citation needed|date=January 2011}} It has been suggested for ] on the basis of in vitro work.<ref>{{cite journal |doi=10.1186/1742-2094-6-29 |title=Luteolin as a Therapeutic Option for Multiple Sclerosis |url=http://www.jneuroinflammation.com/content/6/1/29 |journal=Journal of Neuroinflammation |author=Theoharides |volume=6 |pages=29 |year=2009}}</ref>
			| url-access = registration
			| url = https://archive.org/details/secondarymetabol00mann/page/279
			}}</ref>
			Luteolin is the main yellow dye from the '']'' plant, used for dyeing since at least the first millennium B.C. Luteolin was first isolated in pure form, and named, in 1829 by the French chemist ].<ref>{{cite book |last1=Chevreul |first1=M.E. |title=Leçons de Chimie Appliquée à la Teinture |trans-title=Lessons on Chemistry Applied to Dyeing |date=1829 |publisher=Pichon et Didier |location=Paris, France |pages=143–148 |url=https://books.google.com/books?id=-McPAAAAQAAJ&pg=PA143 |language=French |chapter=30<sup>e</sup> Leçon, Chapitre XI. De la Gaude. }} Chevreul named luteolin on p. 144: ''"J'ai fait des recherches sur la composition de la gaude, j'ai obtenu le principe colorant critalisé par sublimation; je l'ai nommé ''lutéolin''."'' (I have done some research on the composition of weld; I obtained the principal colorant crystallized via sublimation; I have called it "luteolin".)</ref><ref>{{cite book |last1=Thomson |first1=Thomas |title=Chemistry of Organic Bodies. Vegetables |date=1838 |publisher=J.B. Baillière |location=London, England |pages=415–416 |url=https://books.google.com/books?id=Wq45AAAAcAAJ&pg=PA415}}</ref><ref>However, Perkin claimed (without citing a source) that Chevreul had isolated luteolin as early as 1814–1815. See: {{cite book |last1=Perkin |first1=Arthur George |last2=Everest |first2=Arthur Ernest |title=The Natural Organic Colouring Matters |date=1918 |publisher=Longmans, Green and Co. |location=London, England |page= |url=https://archive.org/details/naturalorganicc00evergoog}}</ref> The luteolin ] was determined by the Austrian chemists ] and ] in 1864.<ref>{{cite journal |last1=Hlasiwetz |first1=H. |last2=Pfaundler |first2=L. |title=Über das Morin, Maclurin und Quercitrin |journal=Sitzungsberichte der Kaiserlichen Akademie der Wissenschaften. Mathematisch-Naturwissenschaftliche Classe. (Part 2) |date=1864 |volume=50 |pages=6–59 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015073681051&view=1up&seq=18 |language=German}} ; see pp. 44–45.</ref><ref>{{cite journal |last1=Hlasiwetz |first1=H. |last2=Pfaundler |first2=L. |title=Ueber das Morin, Maclurin und Quercitrin |journal=Journal für praktische Chemie |year=1865 |volume=94 |pages=65–106 |doi=10.1002/prac.18650940112 |url=https://zenodo.org/record/2030398 |language=German}} Hlasiwetz and Pfaundler melted ] with potassium carbonate. Among the reaction's products, they found paradatiscetin, whose empirical formula they determined to be C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> (p. 94). They concluded that although luteolin and paradatiscetin were isomeric (i.e., had the same empirical formula), they were distinct compounds. From p. 94: ''"Das Luteolin scheint demnach wohl als isomer oder metamer mit unserer Substanz betrachtet werden zu können. Eine Identität beider liegt jedoch nicht vor, denn an einer Probe Luteolin fanden wir die charakteristischen Farben-reactionen nicht, welche das Paradatiscetin kaum verwechseln lassen."'' (Luteolin thus seems to be able to be regarded perhaps as an isomer or metamer of our substance . However, the two are evidently not identical, for upon a test of luteolin, we did not find the characteristic color reactions, which hardly allows paradatiscetin to be confused .)</ref> In 1896, the English chemist ] proposed the correct structure for luteolin.<ref>{{cite journal |last1=Perkin |first1=A. G. |title=Luteolin. Part II. |journal=Journal of the Chemical Society |date=1896 |volume=69 |pages=799–803 |doi=10.1039/CT8966900799 |url=https://zenodo.org/records/2057511/files/article.pdf}} See p. 803.</ref> Perkin's proposed structure for luteolin was confirmed in 1900 when the Polish-Swiss chemist ] (1860–1910) and his students A. Różycki and J. Tambor synthesized luteolin.<ref>{{cite journal |last1=Kostanecki |first1=St. v. |last2=Róžycki |first2=A. |last3=Tambor |first3=J. |title=Synthese des Luteolins |journal=Berichte der Deutschen Chemischen Gesellschaft |date=1900 |volume=33 |issue=3 |pages=3410–3417 |doi=10.1002/cber.190003303121 |url=https://zenodo.org/records/2400108/files/article.pdf |language=German}}</ref><ref>{{cite book |editor1-last=Thorpe |editor1-first=Edward |title=A Dictionary of Applied Chemistry |date=1913 |publisher=Longmans, Green, and Co. |location=London, England |volume=5 |pages=747–748 |url=https://books.google.com/books?id=YWxbAAAAcAAJ&pg=PA747}}</ref>
	Luteolin is most often found in leaves, but it is also seen in celery, thyme, dandelion, rinds, ]s, ] blossom and ] pollen.<ref name="MannSecondaryMetabolism"/> It has also been isolated from ''] tomentosa''.<ref>{{cite journal
	| author = A. Ulubelen, M. Miski, P. Neuman, and T. J. Mabry
			== Natural occurrences ==
	| title = Flavonoids of Salvia tomentosa (Labiatae)
			Luteolin is most often found in leaves, but it is also present in rinds, ]s, ] blossoms, and ] pollen.<ref name="MannSecondaryMetabolism"/> It has also been isolated from the aromatic flowering plant, ''Salvia tomentosa'' in the mint family, '']''.<ref>{{cite journal
	| journal = ]
			|author1=A. Ulubelen |authorlink1=Ayhan Ulubelen |author2=M. Miski |author3=P. Neuman |author4=T. J. Mabry | title = Flavonoids of Salvia tomentosa (Labiatae)
	| volume = 42
			| journal = ]
	| year = 1979
	| issue = 4		| volume = 42
	| pages = 261–263		| year = 1979
			| issue = 4
			| pages = 261–63
	| doi = 10.1021/np50003a002		| doi = 10.1021/np50003a002
	}}		}}
	</ref>		</ref>
	Dietary sources include celery, green pepper, thyme, ], ] tea, carrots, olive oil, peppermint, rosemary and oregano.<ref>{{cite journal | author = Kayoko Shimoi, Hisae Okada, Michiyo Furugori, Toshinao Goda, Sachiko Takase, Masayuki Suzuki, Yukihiko Hara, Hiroyo Yamamoto, Naohide Kinae | title = Intestinal absorption of luteolin and luteolin 7-O--glucoside in rats and humans | journal = FEBS Letters | volume = 438 | year = 1998 | pages = 220–224 | doi = 10.1016/S0014-5793(98)01304-0 | issue = 3 | pmid = 9827549
	}}
	</ref><ref>{{cite journal|author= López-Lázaro M.|title= |journal= Mini Rev Med Chem. |volume=9|issue=1|pages=31–59|year=2009|pmid=19149659|doi= 10.2174/138955709787001712}}</ref>
			Dietary sources include ], ], ], ], ], ], dandelion, ], ] tea, carrots, olive oil, peppermint, ], navel oranges, and ].<ref>{{cite journal|display-authors=3 |author1=Kayoko Shimoi |author2=Hisae Okada |author3=Michiyo Furugori |author4=Toshinao Goda |author5=Sachiko Takase |author6=Masayuki Suzuki |author7=Yukihiko Hara |author8=Hiroyo Yamamoto |author9=Naohide Kinae | title = Intestinal absorption of luteolin and luteolin 7-O--glucoside in rats and humans | journal = FEBS Letters | volume = 438 | year = 1998 | pages = 220–24 | doi = 10.1016/S0014-5793(98)01304-0 | issue = 3 | pmid = 9827549
	==Metabolism==
			|s2cid=10640654 |doi-access= }}</ref><ref name="lopez">{{cite journal|author= López-Lázaro M.|title=Distribution and biological activities of the flavonoid luteolin |journal= Mini Rev Med Chem|volume=9|issue=1|pages=31–59|year=2009|pmid=19149659|doi= 10.2174/138955709787001712}}</ref> It can also be found in the seeds of the palm '']''.<ref>{{Cite journal|pmid=11440571|year=2001|last1=Lee|first1=D|last2=Cuendet|first2=M|last3=Vigo|first3=JS|last4=Graham|first4=JG|last5=Cabieses|first5=F|last6=Fong|first6=HH|last7=Pezzuto|first7=JM|last8=Kinghorn|first8=AD|display-authors=3|title=A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata|volume=3|issue=14|pages=2169–71|journal=Organic Letters|doi=10.1021/ol015985j}}</ref>
	* ]
	* ]
	==Glycosides==		==References==
			{{Reflist}}
	* ], the 8-C glucoside of luteolin
	* ], the 6-C glucoside
	* Luteolin-7-glucoside (]) and ] found in ]
	* Luteolin-7-] (])
	==Mechanism of action==		==External links==
			*{{Commons category-inline}}
	Luteolin is a ] and a general ]<ref>Eur J Pharmacol. 2009 Oct 22.
	Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1-5, displaced -rolipram from high-affinity rolipram binding sites and reversed xylazine/ketamine-induced anesthesia.
	Yu MC, Chen JH, Lai CY, Han CY, Ko WC. PMID: 19853596</ref>, and an ] inhibitor.<ref name=Johnson2008/>
			{{Flavones}}
	It significantly reversed the ]/]-induced anesthesia in mice.<ref name=pmid19853596>{{pmid|19853596}}</ref>
			{{Dopaminergics}}
			{{GABAAR PAMs}}
	==Side effects==
	Gastrointestinal adverse effects, such as nausea, vomiting and gastric hypersecretion, may occur.{{Citation needed|date=January 2011}}
	==References==
	{{reflist}}
	{{Flavone}}
	]		]
			]
			]
			]
			]
	]		]
	]		]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]