3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation
Autor(a) principal: | |
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Data de Publicação: | 1997 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10884/1341 |
Resumo: | This work describes a straightforward synthesis of two 3′‐(β‐D‐glycopyranosyloxy)flavylium ions thought to be good models of natural anthocyanins (pigments). For both pigments and for the non‐glycosylated flavylium ion taken as a reference, H2O addition and proton‐transfer reactions as well as formation of molecular complexes with chlorogenic acid and caffeine (copigmentation) are quantitatively investigated in mildly acidic aqueous solution. A remarkable affinity of caffeine for the trans‐chalcone form of the pigments is demonstrated. Moreover, the differences in the flavylium pKa values are interpreted in terms of possible intramolecular H‐bonding between the glycosyl residue and the chromophore. The discussion is then extended to a series of malonylated anthocyanins recently reported for their unusual pigmentation properties. A possible role for the malonyl group (frequently encountered in the structure of naturally occurring anthocyanins) in plant colour expression is outlined for the first time. |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
spelling |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variationThis work describes a straightforward synthesis of two 3′‐(β‐D‐glycopyranosyloxy)flavylium ions thought to be good models of natural anthocyanins (pigments). For both pigments and for the non‐glycosylated flavylium ion taken as a reference, H2O addition and proton‐transfer reactions as well as formation of molecular complexes with chlorogenic acid and caffeine (copigmentation) are quantitatively investigated in mildly acidic aqueous solution. A remarkable affinity of caffeine for the trans‐chalcone form of the pigments is demonstrated. Moreover, the differences in the flavylium pKa values are interpreted in terms of possible intramolecular H‐bonding between the glycosyl residue and the chromophore. The discussion is then extended to a series of malonylated anthocyanins recently reported for their unusual pigmentation properties. A possible role for the malonyl group (frequently encountered in the structure of naturally occurring anthocyanins) in plant colour expression is outlined for the first time.2018-09-04T10:19:28Z1997-03-01T00:00:00Z1997-03info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleimage/pnghttp://hdl.handle.net/10884/1341engEl Hajji, HakimaDangles, OlivierFigueiredo, PauloBrouillard, 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:RCAAP2024-01-04T11:08:04Zoai:repositorio-cientifico.uatlantica.pt:10884/1341Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:29:54.609026Repositório 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 |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
title |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
spellingShingle |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation El Hajji, Hakima |
title_short |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
title_full |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
title_fullStr |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
title_full_unstemmed |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
title_sort |
3′‐(β‐D‐Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation |
author |
El Hajji, Hakima |
author_facet |
El Hajji, Hakima Dangles, Olivier Figueiredo, Paulo Brouillard, Raymond |
author_role |
author |
author2 |
Dangles, Olivier Figueiredo, Paulo Brouillard, Raymond |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
El Hajji, Hakima Dangles, Olivier Figueiredo, Paulo Brouillard, Raymond |
description |
This work describes a straightforward synthesis of two 3′‐(β‐D‐glycopyranosyloxy)flavylium ions thought to be good models of natural anthocyanins (pigments). For both pigments and for the non‐glycosylated flavylium ion taken as a reference, H2O addition and proton‐transfer reactions as well as formation of molecular complexes with chlorogenic acid and caffeine (copigmentation) are quantitatively investigated in mildly acidic aqueous solution. A remarkable affinity of caffeine for the trans‐chalcone form of the pigments is demonstrated. Moreover, the differences in the flavylium pKa values are interpreted in terms of possible intramolecular H‐bonding between the glycosyl residue and the chromophore. The discussion is then extended to a series of malonylated anthocyanins recently reported for their unusual pigmentation properties. A possible role for the malonyl group (frequently encountered in the structure of naturally occurring anthocyanins) in plant colour expression is outlined for the first time. |
publishDate |
1997 |
dc.date.none.fl_str_mv |
1997-03-01T00:00:00Z 1997-03 2018-09-04T10:19:28Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10884/1341 |
url |
http://hdl.handle.net/10884/1341 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
image/png |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799136781060276224 |