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Revision as of 18:24, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 10:13, 9 April 2024 edit undoPlantsurfer (talk | contribs)Extended confirmed users40,022 edits Reverted 1 edit by 114.108.236.200 (talk): No source given, not notableTags: Twinkle Undo
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			{{Short description|Anthocyanidin pigment in flowering plant petals and fruits}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 407652235
			| Watchedfields = changed
⚫	| ImageFile=Cyanidin.svg
		⚫	| verifiedrevid = 443544194
⚫	| ImageSize=200px
		⚫	| ImageFile = Cyanidin.svg
⚫	| IUPACName=2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol
		⚫	| ImageSize = 200px
	| OtherNames=Cyanidine
			| ImageFile1 = Cyanidin-cation-from-xtal-3D-bs-17.png
			| IUPACName = 3,3′,4′,5,7-Pentahydroxyflavylium
			| SystematicName = 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1λ<sup>4</sup>-benzopyran-1-ylium
		⚫	| OtherNames = Cyanidine <br /> 2-(3,4-Dihydroxyphenyl)chromenylium-3,5,7-triol
	|Section1= {{Chembox Identifiers		|Section1= {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 114193		| ChemSpiderID = 114193
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = VEVZSMAEJFVWIL-UHFFFAOYSA-O		| StdInChIKey = VEVZSMAEJFVWIL-UHFFFAOYSA-O
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo=13306-05-3		| CASNo=13306-05-3
			| CASNo2_Ref = {{cascite|correct|CAS}}
⚫	| CASOther = 528-58-5 (chloride)
			| CASNo2 = 528-58-5
⚫	| PubChem=128861
			| CASNo2_Comment = (chloride)
⚫	| ChEBI = 27843
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES=C1=CC(=C(C=C1C2= C(C=C3C(=CC(=CC3= 2)O)O)O)O)O
			| UNII = 7732ZHU564
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = 2G4283G96U
		⚫	| UNII2_Comment = (chloride)
		⚫	| PubChem=128861
			| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEBI = 27843
		⚫	| SMILES=C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=2)O)O)O)O)O
	}}		}}
	|Section2= {{Chembox Properties		|Section2= {{Chembox Properties
	| Formula=C<sub>15</sub>H<sub>11</sub>O<sub>6</sub><sup>+</sup>		| Formula=C<sub>15</sub>H<sub>11</sub>O<sub>6</sub><sup>+</sup>
	| MolarMass=287.24 g/mol		| MolarMass=287.24 g/mol
	| Appearance=		| Appearance=
	| Density=		| Density=
	| MeltingPt=		| MeltingPt=
	| BoilingPt=		| BoilingPt=
	| Solubility=		| Solubility=
	}}		}}
	|Section3= {{Chembox Hazards		|Section3= {{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt=
	| Autoignition=
	}}		}}
	}}		}}
			{{Ph indicator template|high_pH=11|high_pH_color=blue|indicator_name=Cyanidin|low_pH=3|low_pH_text=white|low_pH_color=red|high_pH_text=white}}
		⚫	'''Cyanidin''' is a natural ]. It is a particular type of ] (] version called ]s). It is a pigment found in many red berries including ], ], ], ], ], ], ], ], ], ], ] berry and ].<ref>{{cite web|url=https://healthknight.com/cyanidin-e163a-side-effects-benefits |title=Cyanidin (E163a) – Overview, Uses, Side Effects & More |date=27 April 2022 |publisher=HealthKnight |access-date=2022-04-30}}</ref> It can also be found in other fruits such as ]s and ]s, and in ] and ]. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin.{{citation needed|date=November 2011}} Cyanidin has been found to be a potent ] (SIRT6) activator.<ref>{{cite journal|last1=Rahnasto-Rilla|first1=M|last2=Tyni|first2=J|last3=Huovinen|first3=M|last4=Jarho|first4=E|last5=Kulikowicz|first5=T|last6=Ravichandran|first6=S|last7=Bohr|first7=V A|last8=Ferrucci|first8=L|last9=Lahtela-Kakkonen|first9=M|last10=Moaddel|first10=R|title=Natural polyphenols as sirtuin 6 modulators.|journal=Sci Rep|date=2018-03-07|volume=7;8|issue=1|page=4163|doi=10.1038/s41598-018-22388-5|pmid=29515203|pmc=5841289|bibcode=2018NatSR...8.4163R}}</ref><ref name="pmid32518153" />
		⚫	== List of cyanidin derivatives ==
⚫	'''Cyanidin''' is a natural ]. It is a particular type of ] (not to be confused with ]s which are ]s of anthocyanidins). It is a pigment found in many redberries including but not limited to ], ], ], ], ], ], ], ], ], ] berry and ].<ref>* at phytochemicals.info</ref> It can also be found in other fruits such as ]s and ]s. It is also found in ] and ]. It has a characteristic reddish-orange color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. The highest concentrations of cyanidin are found in the skin of the fruit.
			* ] (cyanidin-3-] or 3-C-R), found in ]<ref name="pmid18290621">{{cite journal | vauthors = Tulio AZ, Reese RN, Wyzgoski FJ, Rinaldi PL, Fu R, Scheerens JC, Miller AR | title = Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry | journal = Journal of Agricultural and Food Chemistry | volume = 56 | issue = 6 | pages = 1880–8 | date = March 2008 | pmid = 18290621 | doi = 10.1021/jf072313k | quote = <small>Five anthocyanins were present in black raspberries: cyanidin 3-sambubioside, cyanidin 3-glucoside, cyanidin 3-xylosylrutinoside, cyanidin 3-rutinoside, and pelargonidin 3-rutinoside. Their identities and structures, with particular emphasis on cyanidin 3-xylosylrutinoside, were confirmed by NMR spectroscopy. Two of these anthocyanins, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside, predominated, comprising 24-40 and 49-58%, respectively, of the total anthocyanins in black raspberries. On the basis of both potency and concentration, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside were found to be the significant contributors to the antioxidant systems of black raspberries.</small> }}</ref>
			* Cyanidin-3-xylosylrutinoside, found in ]<ref name="pmid18290621"/>
		⚫	* Cyanidin-3,4′-di-''O''-β-glucopyranoside, found in ]
		⚫	* Cyanidin-4′-''O''-β-glucoside, found in red onion
		⚫	* ] (cyanidin-3-''O''-glucoside), found in ] pomace
			* ] (cyanidin 3-O-galactoside), found in ''Vaccinium'' species
			* Cyanin (]), found in ]<ref name="pmid22314380">{{cite journal | vauthors = He F, Liang NN, Mu L, Pan QH, Wang J, Reeves MJ, Duan CQ | title = Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression | journal = Molecules | volume = 17 | issue = 2 | pages = 1571–601 | date = February 2012 | pmid = 22314380 | pmc = 6268338 | doi = 10.3390/molecules17021571 | doi-access = free }}</ref>
			==Biosynthesis==
	== Effects on the human body ==
			Cyanidin can be synthesized in berry plants through the ] and ] (PKS) III. The shikimate pathway is a biosynthetic pathways that uses the starting materials ] (PEP) and ] to form ], which then further reacts to form specific ]. L-], which is necessary in the production of cyanidin, is synthesized through the shikimate pathway.
	Cyanidin, like other anthocyanidins, has putative ] and ]-scavenging effects which may protect cells from oxidative damage and reduce risk of ]s and ]. One theory is that dietary intake of cyanidins may inhibit development of ] and ] as well as contain inflammatory mechanisms.<ref>Sasaki R, Nishimura N, Hoshino H, Isa Y, Kadowaki M, Ichi T, Tanaka A, Nishiumi S, Fukuda I, Ashida H, Horio F, Tsuda T. Cyanidin 3-glucoside ameliorates hyperglycemia and insulin sensitivity due to downregulation of retinol binding protein 4 expression in diabetic mice. Biochem Pharmacol. 2007 Dec 3;74(11):1619-27.</ref>
			In the synthesis of L-phenylalanine, ] undergoes a ] by a ] enzyme to form ]. Prephenate undergoes dehydration, decarboxylation, and transamination with ] (PLP) and ] to form L-phenylalanine (figure 1).
	Other studies have generally shown that the ] derivative of cyanidin may have a role in cancer therapy.<ref>{{cite journal |author=Fimognari C, Berti F, Nusse M, Cantelli Forti G, Hrelia P |title=In vitro antitumor activity of cyanidin-3-O-beta-glucopyranoside |journal=Chemotherapy |volume=51 |issue=6 |pages=332–5 |year=2005 |pmid=16224184 |doi=10.1159/000088956}}</ref><ref>{{cite journal |author=Chen PN, Chu SC, Chiou HL, Kuo WH, Chiang CL, Hsieh YS |title=Mulberry anthocyanins, cyanidin 3-rutinoside and cyanidin 3-glucoside, exhibited an inhibitory effect on the migration and invasion of a human lung cancer cell line |journal=Cancer Lett. |volume=235 |issue=2 |pages=248–59 |year=2006 |pmid=15975709 |doi=10.1016/j.canlet.2005.04.033}}</ref><ref>Tulio AZ Jr, Reese RN, Wyzgoski FJ, Rinaldi PL, Fu R, Scheerens JC, Miller AR. Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry. J Agric Food Chem. 2008 Mar 26;56(6):1880-8.</ref>
			]
⚫	== List of cyanidin derivates ==
	* ] (cyanidin-3-rutinoside or 3-C-R)
			L-phenylalanine then undergoes an elimination of the primary amine with ] (PAL) to form cinnamate. Through an oxidation with molecular oxygen and ], a hydroxyl group is added to the para position of the aromatic ring. The compound then reacts with ] (CoA), CoA ligase, and ] to attach CoA to the carboxylic acid group. The compound reacts with ]-] synthase and three malonyl CoA molecules to add six carbon atoms and three more keto groups ring through ]. ] catalyses the aromatization and cyclization of the newly added carbonyl groups and facilitates the release of CoA. The compound then spontaneously cyclizes to form ]<ref>{{cite web |title=Chalcone and Stilbene Biosynthesis |url=http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/phenol/chalcone.html |publisher=] |archive-url=https://web.archive.org/web/20151018000745/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/phenol/chalcone.html |archive-date=18 October 2015 |url-status=dead}}</ref> (figure 2).
	* cyanidin 3-O, found in ]
	* cyanidin 7-O, found in red onion
			]
⚫	* cyanidin 3,4′-di-O-β-glucopyranoside, found in red onion
⚫	* cyanidin 4′-O-β-glucoside, found in red onion
			Naringenin is then converted to cyanidin through several oxidizing and reducing steps. First naringenin is reacted with two equivalents of oxygen, ''alpha''-Ketogluteratic acid, and flavanone 3-hydroxylase to form ]. The compound then reacts with NADPH and dihydroflavonol 4-reductase to form ], which is further oxidized with oxygen, ''alpha''-Ketogluteratic acid, and anthocyanidin synthase. This compound spontaneously loses a water molecule and a hydroxide ion to form cyanidin<ref>Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach, 3rd ed.; John Wiley and Sons, Ltd: United Kingdom 2009; pp 137-186</ref> (figure 3).
⚫	* ] (cyanidin-3-O-glucoside) found in ] pomace
			]
			==Activation==
			Among many ]s studied, cyanidin most potently stimulated activity of the ] enzyme.<ref name="pmid32518153">{{cite journal | vauthors=Klein MA, Denu JM | title=Biological and catalytic functions of sirtuin 6 as targets for small-molecule modulators | journal=] | volume=295 | issue=32 | pages=11021–11041 | year=2020 | url=https://www.jbc.org/content/295/32/11021.long | doi = 10.1074/jbc.REV120.011438| pmc= 7415977 | pmid=32518153| doi-access=free }}</ref>
	== References ==		== References ==
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