NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?

Detalhes bibliográficos
Autor(a) principal: Figueiredo, Paulo
Data de Publicação: 1996
Outros Autores: Elhabiri, Mourad, Toki, Kenjiro, Saito, Norio, 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/10884/504
Resumo: 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.
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spelling NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?AnthocyaninsIntramolecular copigmentationDissacharide Hydrophilic effectTwo 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.2012-03-06T16:12:54Z1996-01-01T00:00:00Z1996info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10884/504engFigueiredo, PauloElhabiri, MouradToki, KenjiroSaito, NorioDangles, OlivierBrouillard, Raymondinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-01-04T11:07:11Zoai:repositorio-cientifico.uatlantica.pt:10884/504Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:29:31.727829Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
title NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
spellingShingle NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
Figueiredo, Paulo
Anthocyanins
Intramolecular copigmentation
Dissacharide Hydrophilic effect
title_short NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
title_full NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
title_fullStr NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
title_full_unstemmed NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
title_sort NEW ASPECTS OF ANTHOCYANIN COMPLEXATION. INTRAMOLECULAR COPIGMENTATION AS A MEANS FOR COLOUR LOSS?
author Figueiredo, Paulo
author_facet Figueiredo, Paulo
Elhabiri, Mourad
Toki, Kenjiro
Saito, Norio
Dangles, Olivier
Brouillard, Raymond
author_role author
author2 Elhabiri, Mourad
Toki, Kenjiro
Saito, Norio
Dangles, Olivier
Brouillard, Raymond
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Figueiredo, Paulo
Elhabiri, Mourad
Toki, Kenjiro
Saito, Norio
Dangles, Olivier
Brouillard, Raymond
dc.subject.por.fl_str_mv Anthocyanins
Intramolecular copigmentation
Dissacharide Hydrophilic effect
topic Anthocyanins
Intramolecular copigmentation
Dissacharide Hydrophilic effect
description 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.
publishDate 1996
dc.date.none.fl_str_mv 1996-01-01T00:00:00Z
1996
2012-03-06T16:12:54Z
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