Shedding Light on the Black Boxes of the Proanthocyanidin Pathway with Grapevine

Huang, Yung‐Fen; Cheynier, Véronique; Terrier, Nancy

doi:10.1002/9781118299753.ch7

Cited by 6 publications

(8 citation statements)

References 156 publications

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“…The A-ring of flavan-3-ols is generally hydroxylated in C5 and C7 and the B-ring in C4. Diversity arises from the substitution pattern of the B-ring and can be increased by galloylation and glucosylation of the 3-hydroxyl group [76]. The presence of two asymmetric carbons (in C2 and C3) opens the possibility for different stereoisomers, that is, 2R,3S (2,3-trans), 2R,3R (2,3-cis), 2S,3R (2,3-trans), and 2S,3S (2,3-cis) configurations.…”

Section: Flavan-3-ols or Flavanolsmentioning

confidence: 99%

“…Substitution in the 4-position gives rise to another asymmetric center on extension and upper units, but the usual configuration is 3,4-trans (i.e., 3S,4S or 3R,4S). The chain length of one polymer is described by the degree of polymerization (DP), and the mean degree of polymerization (mDP) of a heterogeneous population of polymers [76]. The following nine proanthocyanidins are reported in grapevine leaves, stems, and canes: procyanidin A1, procyanidin B1, procyanidin B2, procyanidin B3, procyanidin B4, procyanidin C1, procyanidin T2, prodelphinidin A-type (reported as epigallocatechin-epicatechin dimer by some authors), and a procyanidin dimer gallate (Table 1) [33,50,53,69,76,77].…”

Section: Proanthocyanidinsmentioning

confidence: 99%

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A Reference List of Phenolic Compounds (Including Stilbenes) in Grapevine (Vitis vinifera L.) Roots, Woods, Canes, Stems, and Leaves

2020

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Due to their biological activities, both in plants and in humans, there is a great interest in finding natural sources of phenolic compounds or ways to artificially manipulate their levels. During the last decade, a significant amount of these compounds has been reported in the vegetative organs of the vine plant. In the roots, woods, canes, stems, and leaves, at least 183 phenolic compounds have been identified, including 78 stilbenes (23 monomers, 30 dimers, 8 trimers, 16 tetramers, and 1 hexamer), 15 hydroxycinnamic acids, 9 hydroxybenzoic acids, 17 flavan-3-ols (of which 9 are proanthocyanidins), 14 anthocyanins, 8 flavanones, 35 flavonols, 2 flavones, and 5 coumarins. There is great variability in the distribution of these chemicals along the vine plant, with leaves and stems/canes having flavonols (83.43% of total phenolic levels) and flavan-3-ols (61.63%) as their main compounds, respectively. In light of the pattern described from the same organs, quercetin-3-O-glucuronide, quercetin-3-O-galactoside, quercetin-3-O-glucoside, and caftaric acid are the main flavonols and hydroxycinnamic acids in the leaves; the most commonly represented flavan-3-ols and flavonols in the stems and canes are catechin, epicatechin, procyanidin B1, and quercetin-3-O-galactoside. The main stilbenes (trans-ε-viniferin, trans-resveratrol, isohopeaphenol/hopeaphenol, vitisin B, and ampelopsins) accumulate primarily in the woods, followed by the roots, the canes, and the stems, whereas the leaves, which are more exposed to environmental stresses, have a low concentration of these compounds. Data provided in this review could be used as (i) a metabolomic tool for screening in targeted and untargeted analyses and (ii) a reference list in studies aimed at finding ways to induce naturally occurring polyphenols on an industrial scale for pant and human disease control.

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Section: Flavan-3-ols or Flavanolsmentioning

confidence: 99%

Section: Proanthocyanidinsmentioning

confidence: 99%

A Reference List of Phenolic Compounds (Including Stilbenes) in Grapevine (Vitis vinifera L.) Roots, Woods, Canes, Stems, and Leaves

2020

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“…PA polymers are longer in skins than in seeds. Their average degree of polymerization (DP) ranges from three to 16 in seeds [ 6 ], whereas it varies from 10 to 40 in skins [ 7 , 8 ], though even higher values were measured (up to 100) [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…The roles of glycosylated flavanols in plant metabolism are not yet fully understood; it has been suggested that they could be involved in PA biosynthesis [ 17 ]. In fact, the polymerization mechanism of flavanol constitutes the black box of the PA pathway, and consequently is an important topic in current Enology research [ 10 ]. Dixon and collaborators -demonstrated that the over-expression of a glucosyltransferase, UGT72L1, in the seed coat of Medicago truncatula induced increased accumulation of PA-like compounds, and at the same time, catalyzed the formation of epicatechin 3′- O -glucoside [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Identification and Quantification of Flavanol Glycosides in Vitis vinifera Grape Seeds and Skins during Ripening

et al. 2018

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Monomeric and dimeric flavanol glycosides were analyzed in Vitis vinifera grapes and seeds during ripening. An analytical method using ultra-high performance liquid chromatography coupled with a triple quadrupole mass spectrometry (UHPLC-ESI-QQQ-MS/MS) in multiple reaction monitoring (MRM) mode was employed. Three grape varieties (Merlot, Syrah and Tannat) were chosen and grape berries were sampled at different stages of development. Ten monoglycosylated and six diglycosylated flavanol monomers were detected. Twelve monoglycosylated and three diglycosylated flavanol dimers were also detected for all three grape varieties. All diglycosides were detected for the first time in Vitis vinifera grapes, though some of these compounds were only detected in skins or seeds. Furthermore, the evolution of all these compounds was studied, and a decrease in monomeric (epi) catechin monoglycosides was observed during ripening for Tannat, Merlot and Syrah grape skins. The dimers would appear to accumulate in skin tissues up to mid-summer (after veraison) and decrease when grape berries reached maturity.

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“…Strong correlations between terminal units and the corresponding monomers likely reflect the analytical method as monomers contribute to terminal units. Moreover, upper units, detected as the corresponding phloroglucinol adducts, were separated from terminal units, suggesting that both types of units have different precursors, as already suspected (Stafford et al, 1982 ; Huang et al, 2012a ). Acetylated anthocyanin derivatives were correlated, regardless of the anthocyanin B-ring substitution while glucosylated, coumaroylated, and caffeoylated anthocyanins derived from malvidin, petunidin, and delphinidin (trihydroxylated) and from other anthocyanidins formed distinct groups.…”

Section: Discussionmentioning

confidence: 53%

Cultivar Diversity of Grape Skin Polyphenol Composition and Changes in Response to Drought Investigated by LC-MS Based Metabolomics

et al. 2017

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Phenolic compounds represent a large family of plant secondary metabolites, essential for the quality of grape and wine and playing a major role in plant defense against biotic and abiotic stresses. Phenolic composition is genetically driven and greatly affected by environmental factors, including water stress. A major challenge for breeding of grapevine cultivars adapted to climate change and with high potential for wine-making is to dissect the complex plant metabolic response involved in adaptation mechanisms. A targeted metabolomics approach based on ultra high-performance liquid chromatography coupled to triple quadrupole mass spectrometry (UHPLC-QqQ-MS) analysis in the Multiple Reaction Monitoring (MRM) mode has been developed for high throughput profiling of the phenolic composition of grape skins. This method enables rapid, selective, and sensitive quantification of 96 phenolic compounds (anthocyanins, phenolic acids, stilbenoids, flavonols, dihydroflavonols, flavan-3-ol monomers, and oligomers…), and of the constitutive units of proanthocyanidins (i.e., condensed tannins), giving access to detailed polyphenol composition. It was applied on the skins of mature grape berries from a core-collection of 279 Vitis vinifera cultivars grown with or without watering to assess the genetic variation for polyphenol composition and its modulation by irrigation, in two successive vintages (2014)(2015). Distribution of berry weights and δ 13 C values showed that non irrigated vines were subjected to a marked water stress in 2014 and to a very limited one in 2015. Metabolomics analysis of the polyphenol composition and chemometrics analysis of this data demonstrated an influence of water stress on the biosynthesis of different polyphenol classes and cultivar differences in metabolic response to water deficit. Correlation networks gave insight on the relationships between Pinasseau et al.Grapevine Polyphenols Response to Drought the different polyphenol metabolites and related biosynthetic pathways. They also established patterns of polyphenol response to drought, with different molecular families affected either positively or negatively in the different cultivars, with potential impact on grape and wine quality.

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Shedding Light on the Black Boxes of the Proanthocyanidin Pathway with Grapevine

Cited by 6 publications

References 156 publications

A Reference List of Phenolic Compounds (Including Stilbenes) in Grapevine (Vitis vinifera L.) Roots, Woods, Canes, Stems, and Leaves

A Reference List of Phenolic Compounds (Including Stilbenes) in Grapevine (Vitis vinifera L.) Roots, Woods, Canes, Stems, and Leaves

Identification and Quantification of Flavanol Glycosides in Vitis vinifera Grape Seeds and Skins during Ripening

Cultivar Diversity of Grape Skin Polyphenol Composition and Changes in Response to Drought Investigated by LC-MS Based Metabolomics

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