New aspects of anthocyanin complexation. Intramolecular copigmentation as a means for colour loss?

• Autor(a) principal: Figueiredo, Paulo
• Data de Publicação: 1996
• Outros Autores: Elhabiri, Mourad, Toki, Kenjiro, Saito, Nairo, Dangles, Olivier, Brouillard, Raymond
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10884/1337

Two series of structurally related anthocyanins, extracted from the blue flowers of Evolvulus pilosus cv. Blue Daze and from the blue-purple flowers of Eichhornia crassipes, exhibit remarkable colour stabilities in aqueous solution at mildly acidic pH values. All the pigments possess the same chromophore (delphinidin), but a different pattern of glycosylation and acylation. Moreover, one of the pigments has an apigenin 7-glucoside molecule (a flavone) attached to the glycosidic chain by two ester bonds with malonic acid, instead of an aromatic acid and is the only known anthocyanin with such a structure. All the molecules studied, except one which has only a 3-gentiobioside (a disaccharide) as substituent, denote an effect of reduction in the hydration constant when compared with the parent delphinidin 3-glucoside or 3,5-diglucoside molecules, which supports the existence of intramolecular hydrophobic interactions between the chromophoric skeleton and the acyl or flavonoid groups. The role played by the sugar units on the hydrophobicity/hydrophilicity of the pigments is also discussed.