Macrowine 2021
IVES 9 IVES Conference Series 9 Crown procyanidin: a new procyanidin sub-family with unusual cyclic skeleton in wine

Crown procyanidin: a new procyanidin sub-family with unusual cyclic skeleton in wine

Abstract

Condensed tannins (also called proanthocyanidins) are a widely distributed throughout in plants kingdom and are one of the most important classes of secondary metabolites, in addition, they are part of the human diet. In wine, they are extracted during the winemaking process from grape skins and seeds. These compounds play an important role in red wine organoleptic characteristics such as color, bitterness and astringency. Condensed tannins in red wine are oligomers and polymers of flavan-3-ols unit such as catechin, epicatechin, epigallocatechin and epicatechin-3-O-gallate. The monomeric units can be linked among them with direct interflavanoid linkage or mediated by aldehydes. During our investigation on red wine condensed tannins, three surprisingly polar tannins oligomers (one tetramer and two pentamers) were detected by HPLC-UV-MS (Tof) and their concentrations remained stable during wine aging. The objective of this study was (1) to develop a purification method for these three oligomers of condensed tannins observed in red wine, (2) to determine their structures by high resolution mass spectrometry, chemical depolymerization strategy, as well as NMR, (3) to quantify them in various red wine and to estimate their organoleptic properties. The new procyanidin tetramer and the two new procyanidin pentamers have been purified by a “three steps-two gels” strategy with the first step of C-18 Solid Phase Extraction, the second step of TSK-40S Gel Filtration Chromatography and the last step of C-18 HPLC semi-preparative. Their fragmentation pattern obtained by MS/MS analysis using a high resolution mass spectrometry revealed that these three compounds belong to the procyanidin family. Moreover the inter-flavanoid linkages, sub-units information as well as overall configuration of the tetramer were established by 1D and 2D NMR. The structure of the tetramer have been determined to be a symmetric procyanidin with four sub-units of (−)-epicatechin link together by B-type interflavanoid linkage in the following sequence of Unit 1-(4-8)-Unit 2-(4-6)-Unit 3-(4-8)-Unit 4 (4-6)-Unit 1 with the first unit linked with the last unit via the forth interflavanoid linkage C6-C4 to form the macrocyclic structure. Since such carbon skeleton has never been reported before for procyanidins in wine, neither in plants kingdom, we decide to name this new group of procyanidins “crown procyanidins”. This new procyanidin sub-family has been quantified in three different red wines (merlot, cabernet sauvignon and shiraz) with various vintages (from 1991 to 2011). The concentration of the crown procyanidin remains stable in wine during ageing and their concentration shows higher stability than linear B-type procyanidins which their content decrease during aging. Moreover, a strong correlation between these new procyanidin and the red wine astringency level has been observed.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Article

Authors

Michael Jourdes*, Liming Zeng, Pere Pons-Mercadé, Pierre-Louis Teissedre, Stéphanie Krisa, Tristan Richard

*UMR 1219 OEnologie

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Sensory definition of green aroma concept in red French wines. Evidence for the contribution of novel volatile markers

The aromatic complexity of a wine results from the perception of the association of volatile molecules and each aroma can be categorized into different families. The “green” aromas family in red wines has retained our attention by its close link with the fruity perception. In that study, the “green” olfactory concept of red wines was considered through a strategy combining both sensory analysis and hyphenated chromatographic techniques including HPLC and MDGC (Multidimensional Gas Chromatography). The aromatic space of this concept was specified by lexical generation through a free association task on 22 selected wines by a panel of wine experts. Then, 70 French red wines were scored on the basis of the intensity of their “green” and “fruity” attributes.

Impact of glutathione and elemental sulphur juice addition on the volatile thiol production in South African Sauvignon blanc wine

Three compounds, 3-mercaptohexanol (3MH), 3-mercaptohexyl-acetate (3MHA) and 4-mercapto-4-methylpentan-2-one (4MMP), also known as varietal thiols, have been identified to contribute positively to wine aroma and are responsible for the distinct gooseberry, grapefruit, guava and box tree character found in Sauvignon blanc wines. Certain volatile thiol compounds though, can cause off-aromas of onion, garlic, rubber and rotten egg, this group of molecules is known as reductive sulphur compounds (RSC). This study looks into how the addition of sulphur-compounds to Sauvignon blanc juice contributes to the varietal thiol (3MH and 3MHA) concentration and reductive sulphur compound concentration in South African Sauvignon blanc wine.

Novel contribution to the study of mouth-feel properties in wines

In general, there is a well-established lexicon related to wine aroma and taste properties; however mouth-feel-related vocabulary usually includes heterogeneous, multimodal and personalized terms. Gawel et al.
(2000) published a wheel related to mouthfeel properties of red wine. However, its use in scientific publications has been limited. The authors accepted that the approach had certain limitations as it included redundant and terms with hedonic tone and some others were absent. It is of high interest to generate a mouth-feel lexicon and finding the chemical compound or group of compounds responsible for such properties in red wine. In the present work a chemical fractionation method has been developed.

Anthropogenic factors in modulations of fungal populations from grapes to wines and their repercussions on wine characteristics

The effects of anthropogenic activities on vineyard (different plant protections) and in winery
(pressing/clarification step, addition of sulfur dioxide) on fungal populations from grape to wine were studied. The studied anthropogenic activities modify the fungal diversity. Thus, lower biodiversity of grapes from organic modality was measured for the three vintages considered compared to biodiversity from ecophyto modality and conventional modality. The pressing / clarification steps strongly modify fungal populations and the influence of the winery flora is highlighted.

Effect of non-Saccharomyces yeast and lactic acid bacteria on selected sensory attributes and polyphenols of Syrah wines

Consumers predominantly use visual, aromatic and texture cues as quality/preference indicators to describe olfactory sensations. In this study, the effect of micro-organism in wine production was investigated using analytical and sensory techniques to achieve relevant analytical characterisation. Selected anthocyanins, flavan-3-ols, flavonols and phenolic acids were quantified in Syrah wines using RP-HPLC-DAD. Standard oenological parameters were also measured. Syrah grape must was fermented with various combinations of Saccharomyces cerevisiae (S. cerevisiae) and non-Saccharomyces (Metschnikowia pulcherrima or Hanseniaspora uvarum) yeasts, which was followed by sequential inoculation of lactic acid bacteria (LAB) (Oenococcus oeni or Lactobacillus plantarum).