HOME
The Info List - 3-deoxyanthocyanidin


--- Advertisement ---



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

References[edit]

^ a b c d Sweeny, James G.; Iacobucci, Guillermo A. (May 1, 1983). "Effect of substitution on the stability of 3-deoxyanthocyanidins in aqueous solutions". Journal of Agricultural and Food Chemistry. 31 (3): 531–533. doi:10.1021/jf00117a017. Retrieved June 25, 2017 – via ACS Publications.  ^ "Inclusions of flavonoid 3-deoxyanthocyanidins in Sorghum bicolor self-organize into spherical structures". Physiological and molecular plant pathology. 65 (4). Archived from the original on March 3, 2016. Retrieved June 25, 2017.  ^ Awika, Joseph M. (January 1, 2008). "Behavior of 3-deoxyanthocyanidins in the presence of phenolic copigments". Food Research International. 41 (5): 532–538. doi:10.1016/j.foodres.2008.03.002. Retrieved June 25, 2017 – via ScienceDirect.  ^ Shih, Chun-Hat; Chu, Ivan K.; Yip, Wing Kin; Lo, Clive (October 1, 2006). "Differential Expression of Two Flavonoid 3′-Hydroxylase cDNAs Involved in Biosynthesis of Anthocyanin
Anthocyanin
Pigments and 3-Deoxyanthocyanidin
3-Deoxyanthocyanidin
Phytoalexins in Sorghum". Plant and Cell Physiology. 47 (10): 1412–1419. doi:10.1093/pcp/pcl003. Retrieved June 25, 2017 – via pcp.oxfordjournals.org.  ^ "Biosynthesis and regulation of 3-deoxyanthocyanidin phytoalexins induced during Sorghum- Colletotrichum
Colletotrichum
interaction: Heterologous expression in maize. Chopra, Surinder Gaffoor, Iffa Ibraheem, Farag". aspb.org. Archived from the original on July 25, 2011. Retrieved June 25, 2017. 

v t e

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins

5-Desoxy-peonidin Aurantinidin Cyanidin 6-Hydroxycyanidin Delphinidin Fisetinidin Guibourtinidin Pelargonidin Robinetinidin

3-deoxyanthocyanidins

Apigeninidin Columnidin Diosmetinidin Gesneridin Luteolinidin Tricetinidin

O-methylated anthocyanidins

5-Desoxy-malvidin Capensinidin Europinidin Hirsutidin Kaempferidinidin Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins (anthocyaninidin glycosides)

Glucosides:

Callistephin
Callistephin
( Pelargonidin
Pelargonidin
3-O-glucoside) Chrysanthemin
Chrysanthemin
(Cyanidin-3-O-glucoside) Myrtillin
Myrtillin
(Delphinidin-3-O-glucoside) Oenin
Oenin
(Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin-3-O-glucoside Pulchellidin
Pulchellidin
3-glucoside

Diglucosides:

Cyanin (Cyanidin-3,5-O-diglucoside) Delphin (Delphinidin-3,5-O-diglucoside) Malvin
Malvin
( Malvidin
Malvidin
3,5-diglucoside) Pelargonin
Pelargonin
(Pelargonidin-3,5-O-diglucoside) Peonin ( Peonidin
Peonidin
3,5-O-diglucoside) Petunin ( Petunidin
Petunidin
3,5-O-diglucoside)

Others glycosides:

Antirrhinin
Antirrhinin
(Cyanidin-3-O-rutinoside) Ideain
Ideain
( Cyanidin
Cyanidin
3-O-galactoside) Delphinidin
Delphinidin
3-O-rhamnoside Petunidin
Petunidin
3-O-arabinoside Petunidin
Petunidin
3-O-galactoside Petunidin
Petunidin
3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin
Pulchellidin
3-rhamnoside Tulipanin
Tulipanin
( Delphinidin
Delphinidin
3-O-rutinoside)

Acylated anthocyanins

Acetylated anthocyanins

Cyanidin-3-O-(6-acetyl)-glucoside Delphinidin-3-O-(6-acetyl)-glucoside Malvidin-3-O-(6-acetyl)-glucoside Petunidin-3-O-(6-acetyl)-galactoside Petunidin-3-O-(6-acetyl)-glucoside Peonidin-3-O-(6-acetyl)-glucoside

Coumaroylated anthocyanins (cis- and trans-)

Cyanidin-3-O-(6-p-coumaroyl)glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petunidin-3-O-(6-p-coumaroyl)glucoside Peonidin-3-O-(6-p-coumaroyl)glucoside

Caffeoylated anthocyanins

Malvidin-3-O-(6-p-caffeoyl)glucoside Peonidin-3-O-(6-p-caffeoyl)glucoside

Malonylated anthocyanins

Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)

Acylated anthocyanin diglycosides

Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside)) Nasunin (Delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) Violdelphin
Violdelphin
(Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-beta-D-glucosyl)oxybenzoyl)-beta-D-glucoside)

Flavanol-anthocyanin adducts

Malvidin
Malvidin
glucoside-ethyl-catechin Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside

Misc.

Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation Anthocyanone A
Anthocyanone A
(degradation product of oenin) Malvone (oxidation produc

.