Delphinidin
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]
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| Names | |
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| IUPAC name
2-(3,4,5-Trihydroxyphenyl)chromenylium-3,5,7-triol | |
| Other names
3,3′,4′,5,5′,7-Hexahydroxyflavylium | |
| Identifiers | |
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3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.671 |
| E number | E163b (colours) |
PubChem CID |
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| UNII | |
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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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| Infobox references | |
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
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 the purplish-blue flower color of Aconitum chinense.[6]
- Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit's purple skin.[7]
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See also
- Prodelphinidin, a type of condensed tannins
References
- "Delphinidine".
- "Delphinidine".
- Afaq, F.; Syed, D. N.; Malik, A.; Hadi, N.; Sarfaraz, S.; Kweon, M.-H.; Khan, N.; Zaid, M. A.; Mukhtar, H. (2007). "Delphinidin, an Anthocyanidin in Pigmented Fruits and Vegetables, Protects Human HaCaT Keratinocytes and Mouse Skin Against UVB-Mediated Oxidative Stress and Apoptosis". Journal of Investigative Dermatology. 127 (1): 222–232. doi:10.1038/sj.jid.5700510. PMID 16902416.
- Ribéreau-Gayon, J.; Ribéreau-Gayon, P. (1958). "The Anthocyans and Leucoanthocyans of Grapes and Wines". American Journal of Enology and Viticulture. 9: 1–9.
- Lätti AK, Riihinen KR, Kainulainen PS (2008). "Analysis of anthocyanin variation in wild populations of bilberry (Vaccinium myrtillus L.) in Finland". J Agric Food Chem. 56 (1): 190–6. doi:10.1021/jf072857m. PMID 18072741.
- CID 3083066 from PubChem
- Noda Y, Kneyuki T, Igarashi K, Mori A, Packer L (2000). "Antioxidant activity of nasunin, an anthocyanin in eggplant peels". Toxicology. 148: 119–23. doi:10.1016/s0300-483x(00)00202-x. PMID 10962130.CS1 maint: multiple names: authors list (link)
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