Delphinidin and cyanidin exhibit antiproliferative and apoptotic effects ...
Delphinidin
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
2-(3,4,5-Trihydroxyphenyl)chromenylium-3,5,7-triol
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.671 |
| E number | E163b (colours) |
PubChem CID
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| Properties | |
| C15H11O7+ | |
| Molar mass | 303.24 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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 verify (what is   ?) | |
| Infobox references | |
Delphinidin (also delphinidine[1][2]) is an anthocyanidin, a primary plant pigment, and also an antioxidant.[3] Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape that produces Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates,[4] and bilberries.[5]
Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, i.e. a natural pH indicator, and changes from red in acidic solution to blue in basic solution.
Glycosides[edit]
Several glycosides derived from delphinidin are known.
Myrtillin (delphinidin-3-O-glucoside) and tulipanin (delphinidin-3-O-rutinoside) can be found in blackcurrant pomace.
Violdelphin (delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside) is responsible for purplish blue flower color of Aconitum chinense.[6]
Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit purple skin.[7]
Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit purple skin.[7]
See also[edit]
- Prodelphinidin, a type of condensed tannins
Cyanidin
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol
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| Other names
Cyanidine
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| Identifiers | |
| |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| E number | E163a (colours) |
| KEGG | |
PubChem CID
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| 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).
| |
| verify (what is ?) | |
| 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.[citation needed]
List of cyanidin derivatives[edit]
- Antirrhinin (cyanidin-3-rutinoside or 3-C-R), found in black raspberry[2]
- Cyanidin-3-xylosylrutinoside, found in black raspberry[2]
- 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[3]
Biosynthesis[edit]
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.
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).
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[4](figure 2).
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[5](figure 3).
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