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Copigmentation

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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.

Examples

Flowers

An example is the bluish purple flowers of the Japanese garden iris (Iris ensata). 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.

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. 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.

See also

References

  1. 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
  2. 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
  3. 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
  4. 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
  5. 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

Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins
3-Deoxyanthocyanidins
O-Methylated anthocyanidins
Anthocyanins
(anthocyaninidin glycosides)
Glucosides:

Diglucosides:

Others glycosides:

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-)
    Caffeoylated anthocyanins
    Malonylated anthocyanins
    Acylated anthocyanin diglycosides
    Flavanol-anthocyanin adducts
    Miscellaneous
    Categories: