Chemistry:Delphinidin
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| IUPAC name
3,3′,4′,5,5′,7-Hexahydroxyflavylium
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| Systematic IUPAC name
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ4-1-benzopyran-1-ylium | |
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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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Tracking categories (test):
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 variety 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 blue in basic solution to red in acidic 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]
- Delphinidin ternatins including Clitoria ternatea ternatins
See also
- Prodelphinidin, a type of condensed tannins
References
- ↑ "Delphinidine". http://www.chemindustry.com/chemicals/0934666.html.
- ↑ "Delphinidine". http://en.chembase.cn/substance-136982.html.
- ↑ Afaq, F.; Syed, D. N.; Malik, A.; Hadi, N.; Sarfaraz, S.; Kweon, M.-H.; Khan, N.; Zaid, M. A. et al. (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.
- ↑ "Analysis of anthocyanin variation in wild populations of bilberry (Vaccinium myrtillus L.) in Finland". J Agric Food Chem 56 (1): 190–6. 2008. 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 (2–3): 119–23. doi:10.1016/s0300-483x(00)00202-x. PMID 10962130.
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