Cyanidin

Cyanidin
Names
IUPAC name
2-(3,4-Dihydroxyphenyl)chromenylium-3,5,7-triol
Other names
Cyanidine
3,3′,4′,5,7-Pentahydroxyflavylium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
E number E163a (colours)
KEGG
Properties
C15H11O6+
Molar mass 287.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin (glycoside version called anthocyanins). It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry.[1] It can also be found in other fruits such as apples and plums, 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. In a recent study, cyanidin was found to be a potent sirtuin 6 (SIRT6) activator.[2]

List of cyanidin derivatives

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-phenyl alanine, which is necessary in the production of cyanidin, is synthesized through the shikimate pathway.

Shikimate Pathway

In the synthesis of L-phenyl alanine, 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-phenyl alanine (figure 1).

Naringenin synthesis

L-phenyl alanine then undergoes an elimination of the primary amine with Phenylalanine ammonia-lyase (PAL) to form cinnamate. Through an oxidation with oxygen gas 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 ATP to attach CoA to the carboxyllic acid group. The compound reacts with naringenin-chalcone synthase and malonyl CoA to add three more keto groups to the benzene ring through PKS III. Aureusidin synthase catalyses the aromatization and cyclization of the newly added carbonyl groups and facilitates the release of CoA to reform the carboxyllic acid. The compound then spontaneously cyclizes to form naringenin[5](figure 2).

Cyanidin synthesis

Naringenin is then converted to cyanidin through several oxidizing and reducing steps. First naringenin is reacted with two equivalents of oxygen gas, alpha-Ketogluteratic acid, and flavanone 3-hydroxylase to form dihydrokaempferol. The compound is then treated with NADPH and dihydroflavinol 4-reductase to form leucopelargonidin, which is further oxidized with oxygen gas, alpha-Ketogluteratic acid, and anthocyanidin synthase. This compound is spontaneously dehydrated to form cyanidin[6] (figure 3).

References

  1. ↑ http://www.phytochemicals.info/phytochemicals/cyanidin.php%5Bself-published+source?%5D
  2. ↑ Rahnasto-Rilla,, M; Tyni, J; Huovinen, M; Jarho, E; Kulikowicz, T; Ravichandran, S; Bohr, V A; Ferrucci, L; Lahtela-Kakkonen, M; Moaddel, R (2018 Mar 7). "Natural polyphenols as sirtuin 6 modulators". Sci Rep. 7, 8 (1): 4163. doi:10.1038/s41598-018-22388-5. Check date values in: |date= (help)
  3. 1 2 Tulio AZ, Reese RN, Wyzgoski FJ, Rinaldi PL, Fu R, Scheerens JC, Miller AR (March 2008). "Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry". Journal of Agricultural and Food Chemistry. 56 (6): 1880–8. doi:10.1021/jf072313k. PMID 18290621. 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.
  4. ↑ He F, Liang NN, Mu L, Pan QH, Wang J, Reeves MJ, Duan CQ (February 2012). "Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression". Molecules. 17 (2): 1571–601. doi:10.3390/molecules17021571. PMID 22314380.
  5. ↑ http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/phenol/narin.html
  6. ↑ Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach, 3rd ed.; John Wiley and Sons, Ltd: United Kingdom 2009; pp 137-186
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