Protocyanin
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 had been 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.
- 1 2 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.
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| 3-hydroxyanthocyanidins | |
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| 3-deoxyanthocyanidins | |
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| O-methylated anthocyanidins | |
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Anthocyanins
(anthocyaninidin glycosides) | Glucosides:
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)
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| Acylated 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
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| Coumaroylated anthocyanins
(cis- and trans-) | |
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| Caffeoylated anthocyanins |
- Malvidin-3-O-(6-p-caffeoyl)glucoside
- Peonidin-3-O-(6-p-caffeoyl)glucoside
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| Malonylated anthocyanins |
- Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
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| 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)
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| 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
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| Misc. | |
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