Colour and antioxidant properties of malvidin-3-glucoside and Vitisin A

Tománková, Eva; Balík, Josef; Soural, Ivo; Bednář, Petr; Papoušková, Barbora

doi:10.1556/066.2016.45.1.11

Cited by 15 publications

(11 citation statements)

References 21 publications

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“…Due to the presence of the pyranoanthocyanins, the color of mature wines is much more pH-stable (Souza et al 2014 and much less susceptible to bleaching by additives such as sulfite than that of young wines (Marquez et al 2013, Tománková et al 2016. Pyranoanthocyanins make an important contribution to the antioxidant radical scavenging capacity of aged wine (Azevedo et al 2014) and current research is focusing on their contributions to the organoleptic properties of red wines in addition to color (Quaglieri et al 2016, Garcia-Estevez et al 2017.…”

Section: Pyranoanthocyanin Pigments Formed In Vitro From the Anthocyamentioning

confidence: 99%

Chemistry Inspired by the Colors of Fruits, Flowers and Wine

Quina

Bastos

2018

An. Acad. Bras. Ciênc.

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An overview is provided of the status of research at the frontiers of investigation of the chemistry and photochemistry of two classes of natural plant pigments, the anthocyanins and the betalains, as well as of the pyranoanthocyanin pigments formed from anthocyanins during the maturation of red wine. Together, anthocyanins and betalains are responsible for almost all of the red, purple and blue colors of fruits and flowers and anthocyanins and pyranoanthocyanins are major contributors to the color of red wines. All three types of pigments are cationic below about pH 3, highly colored, non-toxic, reasonably soluble in water or alcohol and fairly stable to light. They exhibit good antioxidant or antiradical activity and, as part of our diet, confer a number of important health benefits. Systematic studies of model compounds containing the basic chromophoric groups of these three types of pigments are providing a deeper understanding of the often complex chemistry and photochemistry of these pigments and their relationship to the roles in vivo of these pigments in plants. These natural pigments are currently being exploited as starting materials for the preparation of novel semi-synthetic dyes, pigments and fluorescence probes.

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Section: Pyranoanthocyanin Pigments Formed In Vitro From the Anthocyamentioning

confidence: 99%

Chemistry Inspired by the Colors of Fruits, Flowers and Wine

Quina

Bastos

2018

An. Acad. Bras. Ciênc.

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“…The pyranoanthocyanin chromophore is largely responsible for the color of aged red wines and presumably contributes to the taste (e.g. astringency) , antioxidant capacity and health benefits of moderate consumption of red wines.…”

Section: Introductionmentioning

confidence: 99%

Triplet Excited States and Singlet Oxygen Production by Analogs of Red Wine Pyranoanthocyanins

Silva

Thomas

Silva

et al. 2018

Photochem & Photobiology

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During the maturation of red wines, the anthocyanins of grapes are transformed into pyranoanthocyanins, which possess a pyranoflavylium cation as their basic chromophore. Photophysical properties of the singlet and triplet excited states of a series of synthetic pyranoflavylium cations were determined at room temperature in acetonitrile solution acidified with 0.10 mol dm trifluoroacetic acid (TFA, to inhibit competitive excited state proton transfer) and at 77 K in a rigid TFA-acidified isopropanol glass. In solution, the triplet states of these pyranoflavylium cations are efficiently quenched by molecular oxygen, resulting in sensitized formation of singlet oxygen, as confirmed by direct detection of the triplet-state decay by laser flash photolysis and of singlet oxygen monomol emission in the near infrared. The strong visible light absorption, the relatively small singlet-triplet energy differences, the excited state redox potentials and the reasonably long lifetimes of pyranoflavylium triplet states in the absence of molecular oxygen suggest that they might be useful as triplet sensitizers and/or as cationic redox initiators in polar aprotic solvents like acetonitrile.

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“…Among the products formed, those containing the pyranoanthocyanin chromophore (Scheme 1) are particularly important for imparting the color to aged red wines . In addition to a color that is more pH stable than that of anthocyanins , the pyranoanthocyanins have been implicated in contributing to the taste (e.g., astringency) , antioxidant capacity , and health benefits of moderate consumption of red wines.…”

Section: Introductionmentioning

confidence: 99%

Ground‐ and Excited‐State Acidity of Analogs of Red Wine Pyranoanthocyanins,

Freitas

Silva

et al. 2018

Photochem & Photobiology

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Pyranoflavylium cations are synthetic analogs containing the same basic chromophore as the pyranoanthocyanins that form in red wine during maturation and are responsible for its final color. Determination of the ground- and excited-state acidities for a series of eight substituted hydroxy pyranoflavylium cations shows that they are weak acids in the ground state (pK ranging from 3.4 to 4.4 in aqueous buffer solution), but substantially more acidic in the first excited singlet state (pK * ranging from ca. 0.2 to 0.7 in 30% methanol-water). Unlike the ground-state acidities, which show no obvious trend with electronic effects of the substituents, the excited-state pK * values correlate well with Hammett sigma parameters for the substituents on the pyranoflavylium chromophore. This difference in the transmission of electronic effects between ground and excited state is reflected in the localization of the HOMO of the cation and conjugate base in distinct regions of the chromophore as compared to delocalization of the LUMO over the entire molecule. The current results provide further support for the conclusion that excited-state proton transfer is the dominant deactivation pathway for the pyranoflavylium cation excited singlet state in aqueous or aqueous-organic media and presumably for pyranoanthocyanins as well.

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Colour and antioxidant properties of malvidin-3-glucoside and Vitisin A

Cited by 15 publications

References 21 publications

Chemistry Inspired by the Colors of Fruits, Flowers and Wine

Chemistry Inspired by the Colors of Fruits, Flowers and Wine

Triplet Excited States and Singlet Oxygen Production by Analogs of Red Wine Pyranoanthocyanins

Ground‐ and Excited‐State Acidity of Analogs of Red Wine Pyranoanthocyanins,

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