View source for Cyanidin

{{Short description|Anthocyanidin pigment in flowering plant petals and fruits}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443544194
| ImageFile = Cyanidin.svg
| ImageSize = 200px
| 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
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 114193
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C05905
| InChI = 1/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
| InChIKey = VEVZSMAEJFVWIL-IKLDFBCSAG
| SMILES1 = Oc1ccc(cc1O)c3[o+]c2cc(O)cc(O)c2cc3O
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 404515
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VEVZSMAEJFVWIL-UHFFFAOYSA-O
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=13306-05-3
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 528-58-5
| CASNo2_Comment = (chloride)
| UNII_Ref = {{fdacite|correct|FDA}}
| 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=[O+]2)O)O)O)O)O
  }}
|Section2= {{Chembox Properties
| Formula=C<sub>15</sub>H<sub>11</sub>O<sub>6</sub><sup>+</sup>
| MolarMass=287.24 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3= {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt=
  }}
}}
{{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 [[organic compound]].  It is a particular type of [[anthocyanidin]] ([[glycoside]] version called  [[anthocyanin#Structure|anthocyanin]]s).  It is a pigment found in many red berries including [[grapes]], [[bilberry]], [[blackberry]], [[blueberry]], [[cherry]], [[chokeberry]], [[cranberry]], [[elderberry]], [[Crataegus|hawthorn]], [[loganberry]], [[açai]] berry and [[raspberry]].<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 [[apple]]s and [[plum]]s, and in [[red cabbage]] and [[red onion]].  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.<ref>{{Cite journal |last=Veberic |first=Robert |last2=Slatnar |first2=Ana |last3=Bizjak |first3=Jan |last4=Stampar |first4=Franci |last5=Mikulic-Petkovsek |first5=Maja |date=2015-01-01 |title=Anthocyanin composition of different wild and cultivated berry species |url=https://www.sciencedirect.com/science/article/pii/S0023643814005416 |journal=LWT - Food Science and Technology |volume=60 |issue=1 |pages=509–517 |doi=10.1016/j.lwt.2014.08.033 |issn=0023-6438}}</ref> Cyanidin has been found to be a potent [[sirtuin 6]] (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 ==
* [[Antirrhinin]] (cyanidin-3-[[rutinoside]] or 3-C-R), found in [[black raspberry]]<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 [[black raspberry]]<ref name="pmid18290621"/>
* Cyanidin-3,4′-di-''O''-β-glucopyranoside, found in [[red onion]]
* Cyanidin-4′-''O''-β-glucoside, found in red onion
* [[Chrysanthemin]] (cyanidin-3-''O''-glucoside), found in [[blackcurrant]] pomace
* [[Ideain]] (cyanidin 3-O-galactoside), found in ''Vaccinium'' species
* Cyanin ([[cyanidin-3,5-O-diglucoside]]), found in [[red wine]]<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==

Cyanidin can be synthesized in berry plants through the [[shikimate pathway]] and [[polyketide synthase]] (PKS) III. The shikimate pathway is a biosynthetic pathways that uses the starting materials [[Phosphoenolpyruvic acid]] (PEP) and [[Erythrose 4-phosphate]] to form [[shikimic acid]], which then further reacts to form specific [[aromatic amino acids]]. L-[[phenylalanine]], which is necessary in the production of cyanidin, is synthesized through the shikimate pathway.

In the synthesis of L-phenylalanine, [[chorismate]] undergoes a [[Claisen rearrangement]] by a [[Chorismate mutase]] enzyme to form [[prephenate]]. Prephenate undergoes dehydration, decarboxylation, and transamination with [[Pyridoxal phosphate]] (PLP) and [[alpha-Ketoglutaric acid]] to form L-phenylalanine (figure 1).

[[File:Shikimate Pathway.png|600px|Shikimate Pathway]]

L-phenylalanine then undergoes an elimination of the primary amine with [[Phenylalanine ammonia-lyase]] (PAL) to form cinnamate. Through an oxidation with molecular oxygen and [[NADPH]], a hydroxyl group is added to the para position of the aromatic ring. The compound then reacts with [[Coenzyme A]] (CoA), CoA ligase, and [[Adenosine triphosphate|ATP]] to attach CoA to the carboxylic acid group. The compound reacts with [[naringenin]]-[[chalcone]] synthase and three malonyl CoA molecules to add six carbon atoms and three more keto groups ring through [[Type III polyketide synthase|PKS III]]. [[Aureusidin synthase]] catalyses the aromatization and cyclization of the newly added carbonyl groups and facilitates the release of CoA. The compound then spontaneously cyclizes to form [[naringenin]]<ref>{{cite web |title=Chalcone and Stilbene Biosynthesis |url=http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/phenol/chalcone.html |publisher=[[Queen Mary University of London]] |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).

[[File:Naringenin synthesis.png|600px|Naringenin synthesis]]

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 [[dihydrokaempferol]]. The compound then reacts with NADPH and dihydroflavonol 4-reductase to form [[leucopelargonidin]], 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).

[[File:Cyanidin synthesis.png|600px|Cyanidin synthesis]]

==Activation==
Among many [[anthocyanidin]]s studied, cyanidin most potently stimulated activity of the [[sirtuin 6]] 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=[[Journal of Biological Chemistry]] | 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 ==
{{Reflist}}

{{Anthocyanidins}}

[[Category:Anthocyanidins]]