3-Deoxyanthocyanidin

Anthocyanins chemical structure, carbon 3 is represented as the R3 group

Luteolinidin chemical structure

The 3-Deoxyanthocyanidins and their glycosides (3-deoxyanthocyanins or 3-DA) are molecules with an anthocyanidins backbone lacking an hydroxyl group on carbon 3.

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

References

1. ^ ^{a b c d} Effect of substitution on the stability of 3-deoxyanthocyanidins in aqueous solutions, James G. Sweeny, Guillermo A. Iacobucci, 1983
2. ^ Inclusions of flavonoid 3-deoxyanthocyanidins in Sorghum bicolor self-organize into spherical structures, NIELSEN Kirsten A.; GOTFREDSEN Charlotte H.; BUCH-PEDERSEN Morten J.; AMMITZBØLL Henriette; MATTSSON Ole; DUUS Jens Ø.; NICHOLSON Ralph L, 1986
3. ^ Behavior of 3-deoxyanthocyanidins in the presence of phenolic copigments, Joseph M. Awika, 2008
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 and Clive Lo, 2006
5. ^ Biosynthesis and regulation of 3-deoxyanthocyanidin phytoalexins induced during Sorghum-Colletotrichum interaction: Heterologous expression in maize. Chopra, Surinder Gaffoor, Iffa Ibraheem, Farag