3-Deoxyanthocyanidin Explained

The 3-Deoxyanthocyanidins and their glycosides (3-deoxyanthocyanins or 3-DA) are molecules with an anthocyanidins backbone lacking an hydroxyl group at position 3 on the C-ring. This nomenclature is the inverse of that which is commonly used in flavonoids, where the hydroxy-group is assumed absent if it is not specified, e. g. flavan-3-ol, flavan-4-ol, flavan-3,4-ol and flavonol.

3-Deoxyanthocyanidins are yellow anthocyanidins that can be found primarily in ferns and mosses (Timberlake and Bridle, 1975, 1980),^[1] in Sorghum bicolor^{[1] [2]} and in purple corn (Nakatani et al., 1979)^[1] (maíz morado).

3-Deoxyanthocyanidins are reported to be stable to color loss due to change in pH.^[3] Synthetic 3-deoxyanthocyanidins with a carboxylate group at carbon 4 show unusually stable colorant properties at pH 7.^[1]

In Sorghum, the SbF3'H2 gene, encoding a flavonoid 3'-hydroxylase, seems to be expressed in pathogen-specific 3-deoxyanthocyanidin phytoalexins synthesis,^[4] for example in Sorghum-Colletotrichum interactions.^[5]

This category include:

• Apigeninidin
• Columnidin
• Diosmetinidin
• Luteolinidin
• Tricetinidin

Notes and References

1. Effect of substitution on the stability of 3-deoxyanthocyanidins in aqueous solutions. James G.. Sweeny. Guillermo A.. Iacobucci. May 1, 1983. Journal of Agricultural and Food Chemistry. 31. 3. 531–533. 10.1021/jf00117a017.
2. Inclusions of flavonoid 3-deoxyanthocyanidins in Sorghum bicolor self-organize into spherical structures . Physiological and Molecular Plant Pathology . 65 . 4 . June 25, 2017 . live . https://web.archive.org/web/20160303204401/http://cat.inist.fr/?aModele=afficheN&cpsidt=16787373 . March 3, 2016 .
3. Behavior of 3-deoxyanthocyanidins in the presence of phenolic copigments. Joseph M.. Awika. January 1, 2008. Food Research International. 41. 5. 532–538. 10.1016/j.foodres.2008.03.002.
4. Differential Expression of Two Flavonoid 3′-Hydroxylase cDNAs Involved in Biosynthesis of Anthocyanin Pigments and 3-Deoxyanthocyanidin Phytoalexins in Sorghum. Chun-Hat. Shih. Ivan K.. Chu. Wing Kin. Yip. Clive. Lo. October 1, 2006. Plant and Cell Physiology. 47. 10. 1412–1419. 10.1093/pcp/pcl003. 16943219. free.
5. Web site: Biosynthesis and regulation of 3-deoxyanthocyanidin phytoalexins induced during Sorghum-Colletotrichum interaction: Heterologous expression in maize. Chopra, Surinder Gaffoor, Iffa Ibraheem, Farag . aspb.org . June 25, 2017 . dead . https://web.archive.org/web/20110725021532/http://abstracts.aspb.org/pb2009/public/P48/P48067.html . July 25, 2011 . mdy-all .