Copigmentation

Copigmentation is a phenomenon where pigmentation due to anthocyanidins is reinforced by the presence of other colorless flavonoids known as cofactors or “copigments”. This occurs by the formation of a non-covalently-linked complex.^[1]

Examples

Flowers

An example is the bluish purple flowers of the Japanese garden iris (Iris ensata).^[2] The characteristic floral jade coloration of Strongylodon macrobotrys has been shown to be an example of copigmentation, a result of the presence of malvin (the anthocyanin) and saponarin (a flavone glucoside) in the ratio 1:9.^[3]

Berries

It is a phenomenon observed in the berry color of the porcelain berry (Ampelopsis glandulosa).

Food

Part of the color of red wine can be due to the copigmentation phenomenon.^[4] Copigmentation is only important during the early stages of a wine's age. Anthocyanins begin to polymerize with other wine compounds, such as hydroxycinnamic acids, tannins, glyceraldehyde or proteins, to form more complex structures with covalent C–C bonds.^[5]

References

^ Stabilizing and Modulating Color by Copigmentation: Insights from Theory and Experiment. Trouillas P, Sancho-García JC, De Freitas V, Gierschner J, Otyepka M, Dangles O, Chem. Rev., 116(9), 4937–4982, 2016, doi:10.1021/acs.chemrev.5b00507
^ Anthocyanin-flavone copigmentation in bluish purple flowers of Japanese garden iris (Iris ensata Thunb.) T. Yabuya, M. Nakamura, T. Iwashina, M. Yamaguchi and T. Takehara, EUPHYTICA, Volume 98, Number 3, 163-167, doi:10.1023/A:1003152813333
^ Greenish blue flower colour of Strongylodon macrobotrys. Kosaku Takeda, Aki Fujii, Yohko Senda and Tsukasa Iwashina, Biochemical Systematics and Ecology, Volume 38, Issue 4, August 2010, Pages 630–633, doi:10.1016/j.bse.2010.07.014
^ The Copigmentation of Anthocyanins and Its Role in the Color of Red Wine: A Critical Review. Roger Boulton, Am. J. Enol. Vitic. 52:2 (2001) Archived 2013-11-09 at the Wayback Machine
^ Transformation of stacked π–π-stabilized malvidin-3-O-glucoside — Catechin complexes towards polymeric structures followed by anisotropy decay study. Sándor Kunsági-Máté, Bianca May, Christopher Tschiersch, Dirk Fetzer, Ibolya Horváth, László Kollár, Martin Pour Nikfardjam, Food Research International, Volume 44, Issue 1, January 2011, Pages 23–27, doi:10.1016/j.foodres.2010.11.033

External links

Copigmentation reactions and color stability of berry anthocyanins. Academic dissertation by Maarit Rein, Helsinki 2005

Anthocyanidins and their anthocyanin glucosides

3-Hydroxyanthocyanidins

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

3-Deoxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

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

Diglucosides:

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

Others glycosides:

Antirrhinin (Cyanidin 3-O-rutinoside)
Ideain (Cyanidin 3-O-galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin 3-O-rutinoside
Primulin (Malvidin 3-O-galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (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 (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)