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…

DNA and type of grain: which factor does better explain sensory differences of sessile and pedunculate oaks?

Sessile oak and pedunculate oak have shown several differences of interest for enological purposes. Tannic and aromatic composition among sessile oak or pedonculate oak has been well studied. Sessile oak is generally more aromatic than pedunculated, while the later is more tannic. This scientific point of view is rarely applied to classify oak in cooperages. Most coopers use the type of grain to distinguish wide and thin grain.

The effect of cropload on the volatile aroma characteristics of ‘Beihong’ and ‘Beimei’ red wine

Beihong and Beimei were bred as winemaking cultivars released by Institute of Botany, the Chinese Academy of Sciences in 2008. The cultivars are selected from the population of ‘Muscat Hamburg’ (Vitis vinifera) ×V. amurensis. They are extended to most provinces in North of China because they have strong resistance to cold and disease and need not be buried in soil in winter. To better understand the effect of cropload on volatile compounds during wine-making, we surveyed volatiles composition and content of different cropload level in 3-years-old ‘Beihong’ and ‘Beimei’ vines which planted in east foot of Helan mountain of Ningxia (EHN).

Analysis of off flavours in grapes infected with the fungal bunch rot pathogens, Aspergillus, Botrytis and Pencillium

Fungal bunch rots of grapes cause major losses to grape yield worldwide, yet the impact these moulds have on grape and wine quality is not well characterised. We sought to investigate the formation of unwanted volatile compounds of fungal origin in both synthetic grape juice culture media and in inoculated grape berries. Botrytis cinerea, Aspergillus niger, Aspergillus carbonarius, or Pencillium expansum were grown in synthetic grape juice medium and the culture homogenates analysed 4 and 7 days post inoculation. HS-SPME-GC-MS analysis of the culture homogenates 4 days post inoculation demonstrated that each of the fungi examined produced varying quantities of the mushroom or fungus-like aroma compounds, 1-Octen-3-ol, 1-Octen-3-one and 3-Octanone with A. carbonarius producing up to ten times the amounts of all three metabolites per mg of dry mycelium.

Ageing of Sauvignon Blanc white wines with Specific Inactivated Dry Yeasts: Effect on physical and chemical characteristics

Del Barrio-Galán, R.a, b, Gómez-Parrini, A.a, Peña-Neira, A.b a Lallemand Inc. Chile y Compañía Limitada, Rosario Norte 407, piso 6, Las condes, Santiago, Chile b Department of Agro-Industry and Enology, Faculty of Agronomical Sciences, University of Chile, Post Office Box 1004, Santa Rosa 11315, La Pintana, Santiago, Chile It is well known that polysaccharides, mainly mannoproteins, play an important role on physical, chemical and sensory quality of wines. The ageing of white wines on lees is used in order to release higher amounts of polysaccharides by the autolytic processes in order to obtain higher-quality wines. However, this technique is too slow, because the temperature and pH conditions are not the most suitable for this process. In addition, it can also involve certain disadvantages such as a greater demand on winery resources, a longer period of wine storage, the appearance of reduction notes and some microbiological alterations.

Development and validation of a standardized oxidation assay for the accurate measurement of the ability of different wines to form “de novo” oxidation-related aldehydes

From the standpoint of wine aroma oxidation there are two effects observed: aroma degradation of oxygen sensitive compounds (polyfunctional mercaptans) and the appearance of new substances with high aromatic power (acetaldehyde, methional, phenylacetaldehyde, sotolon, alkenals, isobutanal and 2, 3-metylbutanals) (1-5). According to our experience, Strecker aldehydes are compounds with highest sensory relevance in the oxidative degradation of many wines (5-7).