Metalloanthocyanin

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 forming 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. PMC 3720548. 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

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)