Acylated anthocyanin pigments in Vitis vinifera grapes: Identification of malvidin-3-(6-p-coumaroyl) glucoside

Gueffroy, Donald E.; Kepner, Richard E.; Webb, A. Dinsmoor

doi:10.1016/s0031-9422(00)97151-6

Cited by 28 publications

(7 citation statements)

References 10 publications

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“…40 , 41 However, phenolic acids, such as p -coumaric acid, are derived from the esterification of glucose in position 6 in Vitis vinifera L. grapes. 30 , 42 Phenolic acids, such as hydroxycinnamic and p -coumaric acids, are commonly part of the esterification of the polysaccharides in the cell walls. 43 With regard to the precedence of ellagic acid, this compound is a hydrolyzed product of the tannins, consisting of a carbohydrate core attached to ellagic acid that may either come from wooden barrels or from the addition of enological tannins.…”

Section: Resultsmentioning

confidence: 99%

Fractionation of Nanoparticle Matter in Red Wines Using Asymmetrical Flow Field-Flow Fractionation

Osorio-Macías

Song

Thuvander

et al. 2020

J. Agric. Food Chem.

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The particle matter of wine is mainly composed of wine colloids and macromolecules. The present work develops a methodology using asymmetrical flow field-flow fractionation coupled with multi-angle light scattering, differential refractive index detector, and ultraviolet detector (AsFlFFF–MALS–dRI–UV) for the fractionation and determination of the molar mass, the hydrodynamic radius, and the apparent densities of the aggregates and macromolecules present in wine samples. The results from a set of six Argentinian high-altitude wines showed two main populations: the first population composed of wine colloids with higher UV-specific absorptivity and the second population composed of polysaccharides, such as arabinogalactans. The conformation results showed that population 1 consists of small and dense particles, while population 2 showed high molar masses and lower densities. The results demonstrated the use of AsFlFFF as a new, effective method for the fractionation and characterization of wine colloids and wine macromolecules in red wines with further potential applications.

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Section: Resultsmentioning

confidence: 99%

Fractionation of Nanoparticle Matter in Red Wines Using Asymmetrical Flow Field-Flow Fractionation

Osorio-Macías

Song

Thuvander

et al. 2020

J. Agric. Food Chem.

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“…In addition, many anthocyanins have sugar residues which are acylated with aromatic (such as p -coumaric acid, caffeic acid, ferulic and sinapic acid) or aliphatic acids (such as acetic, malic, malonic, oxalic and succinic acid) at the C 6″ position at the glucose moiety. The acylation of the sugar in the anthocyanins can also promote their chemical stability [ 62 , 63 , 64 ]. Interestingly, with p -coumaric acid, two stereoisomers of anthocyanidin-3- O - p -coumarylglucosides can be detected in grapes, which have the opposite directions of the p -coumaric acid moieties ( cis or trans forms) [ 61 ].…”

Section: Structural Diversity Of Anthocyanins In Red Grapesmentioning

confidence: 99%

Biosynthesis of Anthocyanins and Their Regulation in Colored Grapes

et al. 2010

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Anthocyanins, synthesized via the flavonoid pathway, are a class of crucial phenolic compounds which are fundamentally responsible for the red color of grapes and wines. As the most important natural colorants in grapes and their products, anthocyanins are also widely studied for their numerous beneficial effects on human health. In recent years, the biosynthetic pathway of anthocyanins in grapes has been thoroughly investigated. Their intracellular transportation and accumulation have also been further clarified. Additionally, the genetic mechanism regulating their biosynthesis and the phytohormone influences on them are better understood. Furthermore, due to their importance in the quality of wine grapes, the effects of the environmental factors and viticulture practices on anthocyanin accumulation are being investigated increasingly. The present paper summarizes both the basic information and the most recent advances in the study of the anthocyanin biosynthesis in red grapes, emphasizing their gene structure, the transcriptional factors and the diverse exterior regulation factors.

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“…Besides, there is also a series of acylated anthocyanins in red grapes, including the aliphatic acetyl and the aromatic p -coumaroyl, caffeoyl that occur at the C6″ position of the glucose moiety [ 57 , 58 , 59 ]. Interestingly, even the 3- O -(6- p -coumaroyl)-glucosides of the same anthocyanidin can have two different stereoisomerism structures, the cis- and trans- isomers [ 60 ].…”

Section: Free Anthocyanins In Winesmentioning

confidence: 99%

“…However, not all the V. vinifera red varieties, such as ‘Pinot noir’ and red-colored mutants of the white grape varieties, contain acylated anthocyanins [ 61 , 62 ]. Moreover, the amount of acylated anthocyanins is highly variable according to the grape variety [ 57 , 58 , 59 , 60 , 61 , 62 ]. Some other grape species, such as muscadine grapes ( V. rotunidfolia ) also do not accumulate acylated anthocyanins [ 63 ].…”

Section: Free Anthocyanins In Winesmentioning

confidence: 99%

Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression

et al. 2012

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Originating in the grapes, monomeric anthocyanins in young red wines contribute the majority of color and the supposed beneficial health effects related to their consumption, and as such they are recognized as one of the most important groups of phenolic metabolites in red wines. In recent years, our increasing knowledge of the chemical complexity of the monomeric anthocyanins, their stability, together with the phenomena such as self-association and copigmentation that can stabilize and enhance their color has helped to explain their color representation in red wine making and aging. A series of new enological practices were developed to improve the anthocyanin extraction, as well as their color expression and maintenance. This paper summarizes the most recent advances in the studies of the monomeric anthocyanins in red wines, emphasizing their origin, occurrence, color enhancing effects, their degradation and the effect of various enological practices on them.

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Acylated anthocyanin pigments in Vitis vinifera grapes: Identification of malvidin-3-(6-p-coumaroyl) glucoside

Cited by 28 publications

References 10 publications

Fractionation of Nanoparticle Matter in Red Wines Using Asymmetrical Flow Field-Flow Fractionation

Fractionation of Nanoparticle Matter in Red Wines Using Asymmetrical Flow Field-Flow Fractionation

Biosynthesis of Anthocyanins and Their Regulation in Colored Grapes

Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression

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