Protocyanin

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Protocyanin is an anthocyanin pigment that is responsible for the red colouration of roses, but in cornflowers is blue. The pigment was first isolated in 1913 from the blue cornflower (Centaurea cyanus),^[1] and the identical pigment was isolated from a red rose in 1915.^[2] The difference in colour was previously explained as a difference in flower-petal pH,^[2] but the pigment in the blue cornflower has been shown to be a supermolecular pigment consisting of anthocyanin, flavone, one ferric ion, one magnesium and two calcium ions^[3] forming a copigmentation complex.

The molecular formula of protocyanin complex is of the type of C₃₆₆H₃₈₄O₂₂₈FeMg.

References

↑ Willstätter R & Everest RW (1913). "Untersuchungen über die Anthocyane. I. Über den Farbstoff der Kornblume". Justus Liebigs Ann. Chem. 401 (2): 189–232. doi:10.1002/jlac.19134010205.
↑ 2.0 2.1 Willstätter R & Mallison H (1915). "Untersuchungen über die Anthocyane. X. Über Variationen der Blütenfarben". Justus Liebigs Ann. Chem. 408: 147–162. doi:10.1002/jlac.19154080110.
↑ Shiono M, Matsugaki N, Takeda K (2005). "Structure of the blue cornflower pigment". Nature 436 (7052): 791. Bibcode:2005Natur.436..791S. doi:10.1038/436791a. PMID 16094358.

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 Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins	Antirrhinin (Cyanidin-3-O-rutinoside) Callistephin (Pelargonidin 3-O-glucoside) Chrysanthemin (Cyanidin-3-O-glucoside) Malvin (Malvidin 3,5-diglucoside) Myrtillin (Delphinidin-3-O-glucoside) Oenin (Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin 3,5-O-diglucoside Petunidin 3-O-arabinoside Petunidin 3-O-galactoside Petunidin-3-O-glucoside Petunidin 3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin 3-glucoside Pulchellidin 3-rhamnoside Tulipanin (Delphinidin 3-O-rutinoside)

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 Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) 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 Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Flavanol-anthocyanin adducts	Malvidin glucoside-ethyl-catechin

Misc.	Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation

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