Metalloanthocyanin

Blue color inflorescences of Hydrangea macrophylla

A metalloanthocyanin is a chemical complex giving color to petals of certain plants.

These complexes are self-assembled, supramolecular metal complex pigment composed of stoichiometric amounts of anthocyanins, flavones, and metal ions. The various colors, such as red, mauve, purple, violet and blue, in Hydrangea macrophylla are developed from one simple anthocyanin, delphinidin 3-glucoside foming complexes with metal ions.^[1]

Examples

Commelinin, a blue pigment from the flowers of Commelina communis, is a complex of 4 Mg²⁺ ions chelating six anthocyanin molecules.^[2]

Cyanosalvianin, a blue pigment from the flowers of Salvia uliginosa, is a complex formed of six molecules of the anthocyanin type, six molecules of the flavone type and two magnesium ions.^[3]

References

↑ Yoshida K, Mori M, Kondo T (2009). "Blue flower color development by anthocyanins: from chemical structure to cell physiology". Nat. Prod. Rep. 26 (7): 884–915. doi:10.1039/b800165k. PMID 19554240.
↑ Shiono M, Matsugaki N, Takeda K (2008). "Structure of commelinin, a blue complex pigment from the blue flowers of Commelina communis". Proc. Jpn. Acad., Ser. B, Phys. Biol. Sci. 84 (10): 452–6. doi:10.2183/pjab.84.452. PMID 19075517.
↑ Mori M, Kondo T, Yoshida K (December 2008). "Cyanosalvianin, a supramolecular blue metalloanthocyanin, from petals of Salvia uliginosa". Phytochemistry 69 (18): 3151–8. doi:10.1016/j.phytochem.2008.03.015. PMID 18466933.

External links

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins

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)-beta-D-glucosyl)oxybenzoyl)-beta-D-glucoside)

Flavanol-anthocyanin adducts

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 (degradation product of oenin)
Malvone (oxidation product of malvin)

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