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]

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References

  1. 1 2 3 4 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
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