Structural characterization of a A-type linked trimeric anthocyanin derived pigment occurring in a young Port wine.

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Abstract

A new trimeric flavylium derivative pigment was detected for the first time in a young Port wine and structurally characterised using both API-LC ESI MS/MS and NMR techniques. Its structure comprises a malvidin-3-glucoside molecule (terminal unit) linked to two units of flavans (extension units) involving two A-type linkages (C4→C8 and C7-O-C2 ether linkages). The energies of the minimized geometries for all four conformations of this compound were calculated and comparing the structures of all isomers, it was verified that the binding mode (α or β) between the first and second anthocyanin unit does not have a key role in the compound stability. However, for isomers 1 and 2 where the interaction between the second and third anthocyanin units occurs by a "β" mode in opposition to the "α" mode verified in isomers 3 and 4, revealed a higher stability. The presence of these compounds in red wines is thought to result from their extraction from grape skin during fermentation, as the presence of these trimeric pigments was detected in a grape skin extract by API-LC ESI MS/MS spectrometry.
Original languageUnknown
Pages (from-to)1987-1996
JournalFood Chemistry
Volume141
Issue number3
DOIs
Publication statusPublished - 1 Jan 2013

Keywords

    Cite this

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    title = "Structural characterization of a A-type linked trimeric anthocyanin derived pigment occurring in a young Port wine.",
    abstract = "A new trimeric flavylium derivative pigment was detected for the first time in a young Port wine and structurally characterised using both API-LC ESI MS/MS and NMR techniques. Its structure comprises a malvidin-3-glucoside molecule (terminal unit) linked to two units of flavans (extension units) involving two A-type linkages (C4→C8 and C7-O-C2 ether linkages). The energies of the minimized geometries for all four conformations of this compound were calculated and comparing the structures of all isomers, it was verified that the binding mode (α or β) between the first and second anthocyanin unit does not have a key role in the compound stability. However, for isomers 1 and 2 where the interaction between the second and third anthocyanin units occurs by a {"}β{"} mode in opposition to the {"}α{"} mode verified in isomers 3 and 4, revealed a higher stability. The presence of these compounds in red wines is thought to result from their extraction from grape skin during fermentation, as the presence of these trimeric pigments was detected in a grape skin extract by API-LC ESI MS/MS spectrometry.",
    keywords = "Quantum Mechanics, Flavan, Flavylium cation, Anthocyanins, A-type linkage, Grape skin, Malvidin-3-glucoside, Young Port wine",
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    Structural characterization of a A-type linked trimeric anthocyanin derived pigment occurring in a young Port wine. / Parola, António Jorge Dias.

    In: Food Chemistry, Vol. 141, No. 3, 01.01.2013, p. 1987-1996.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Structural characterization of a A-type linked trimeric anthocyanin derived pigment occurring in a young Port wine.

    AU - Parola, António Jorge Dias

    N1 - Sem PDF

    PY - 2013/1/1

    Y1 - 2013/1/1

    N2 - A new trimeric flavylium derivative pigment was detected for the first time in a young Port wine and structurally characterised using both API-LC ESI MS/MS and NMR techniques. Its structure comprises a malvidin-3-glucoside molecule (terminal unit) linked to two units of flavans (extension units) involving two A-type linkages (C4→C8 and C7-O-C2 ether linkages). The energies of the minimized geometries for all four conformations of this compound were calculated and comparing the structures of all isomers, it was verified that the binding mode (α or β) between the first and second anthocyanin unit does not have a key role in the compound stability. However, for isomers 1 and 2 where the interaction between the second and third anthocyanin units occurs by a "β" mode in opposition to the "α" mode verified in isomers 3 and 4, revealed a higher stability. The presence of these compounds in red wines is thought to result from their extraction from grape skin during fermentation, as the presence of these trimeric pigments was detected in a grape skin extract by API-LC ESI MS/MS spectrometry.

    AB - A new trimeric flavylium derivative pigment was detected for the first time in a young Port wine and structurally characterised using both API-LC ESI MS/MS and NMR techniques. Its structure comprises a malvidin-3-glucoside molecule (terminal unit) linked to two units of flavans (extension units) involving two A-type linkages (C4→C8 and C7-O-C2 ether linkages). The energies of the minimized geometries for all four conformations of this compound were calculated and comparing the structures of all isomers, it was verified that the binding mode (α or β) between the first and second anthocyanin unit does not have a key role in the compound stability. However, for isomers 1 and 2 where the interaction between the second and third anthocyanin units occurs by a "β" mode in opposition to the "α" mode verified in isomers 3 and 4, revealed a higher stability. The presence of these compounds in red wines is thought to result from their extraction from grape skin during fermentation, as the presence of these trimeric pigments was detected in a grape skin extract by API-LC ESI MS/MS spectrometry.

    KW - Quantum Mechanics

    KW - Flavan

    KW - Flavylium cation

    KW - Anthocyanins

    KW - A-type linkage

    KW - Grape skin

    KW - Malvidin-3-glucoside

    KW - Young Port wine

    U2 - 10.1016/j.foodchem.2013.04.091

    DO - 10.1016/j.foodchem.2013.04.091

    M3 - Article

    VL - 141

    SP - 1987

    EP - 1996

    JO - Food Chemistry

    JF - Food Chemistry

    SN - 0308-8146

    IS - 3

    ER -