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Color is one of the most distinctive qualities of red wine. Despite new knowledge in the field of pigment identification, copigmentation, and oxidation being forthcoming, there is still a large gap between the fundamental research and practical winemaking outcomes. A state-of-art review from these two aspects is, therefore, necessary. This review first introduces updated knowledge about the primary pigments in wine, with emphasis on their physicochemical properties. Then, the mechanisms of copigmentation and oxidation are elucidated in detail, along with their relative contributions to wine color. Finally, the practical effects of copigmentation and micro-oxygenation (MOX) in winemaking are summarized and discussed. In general, wine coloration is ultimately determined by the anthocyanin flavylium cation, which is greatly influenced by wine pH. In young red wine, grape-derived anthocyanins and nonanthocyanin polyphenols (as copigments) are the foundation for wine coloration. During aging and storage, anthocyanin derivatives are formed via various chemical reactions, where moderate oxidation plays a vital role, whereas copigmentation constantly decreases. The essence of wine color evolution relates to the changes of physicochemical properties of primary pigments in wine, where the hydration equilibrium gradually diminishes. In practice, the effects of copigment addition and MOX during real vinification can be viewed as somewhat controversial, considering that many studies showed different effects on wine color and pigment concentration. Universal features can be summarized but some phenomena still remain unclear and deserve further exploration.

Berries of six Vitis davidii Foex (spine grape) cultivars (‘Baiputao’, ‘Gaoshan 1’, ‘Gaoshan 2’, ‘Seputao’, ‘Miputao’, and ‘Tianputao’) were harvested from a commercial vineyard in Hunan Province in China. Free and bound volatile compounds and fatty acids were analyzed by GC–MS, and amino acids were analyzed by HPLC. ‘Tianputao’ and ‘Miputao’ were characterized by relatively higher concentrations of aromatic amino acids and lower concentrations of branched-chain amino acids. The major free volatile compounds of spine grapes were hexanal, (E)-2-hexenal, 1-hexanol, (E)-2-hexenol, (E)-β-damascenone, and benzeneacetaldehyde. The major glycosidically bound volatile compounds identified were 1-hexanol, menthol, nerol, 1-butanol, 3-methyl-3-butenol, benzenemethanol, β-phenylethanol, eugenol, and guaiacol. (E)-β-damascenone, benzeneacetaldehyde, guaiacol, and eugenol had odor activity values (OAVs) > 1 in all cultivar grapes. Partial least squares discriminant analysis (PLS-DA) revealed ‘Tianputao’ to be distinct from the other cultivars due to its relatively higher concentrations of major terpenoids, norisoprenoids, higher alcohols, and aromatic amino acids.

Wine quality is closely related to various compounds including polysaccharides, a class of crucial macromolecules that affect its chemical and physical properties by influencing the colloidal state or interacting with other compounds via non-covalent bonds. Herein, the composition and structural characteristics of the major polysaccharides identified in wine and the factors influencing their contents are briefly described. An improved understanding of the molecular mechanisms of wine polysaccharides and their practical applications on wine stability and organoleptic qualities is thoroughly discussed. The effects of polysaccharides on wine quality are significantly correlated with their structure and composition as well as wine matrix composition. Thus, to better understand the chemical complexity of polysaccharides, relevant analytical methods are systematically summarized and highlighted, which may ultimately lead to the development of novel winery guidelines.

Freezing-thawing events contribute to the unique aroma profile of icewines. Differences in key odor-active volatile compounds between ‘Beibinghong’ (Vitis amurensis × V. vinifera) icewines and dry wines were investigated by gas chromatography-olfactometry and gas chromatography-mass spectrometry. Acceptable agreement between the olfactometric and quantitative results was obtained. ‘Beibinghong’ icewine was characterized by high concentrations of volatile phenols, lactones, (E)-β-damascenone, and phenylacetaldehyde, which were associated with on-vine freezing-thawing events in grape. Low concentrations of higher alcohol acetates and ethyl esters of fatty acids were attributed to hyperosmotic stress during fermentation. The overall aroma of icewine could be mimicked by reconstitution containing 44 identified volatiles. Partial least squares regression analysis demonstrated that the concentrations of these volatile compounds determined the distinct sensory profiles of icewines, which have higher intensities of honey/sweet, smoky, caramel, dried fruit, apricot/peach, and floral aromas, and lower intensities of fresh fruity and herbaceous notes in comparison with dry wines.

Anthocyanin derivatives and chromatic characteristics of 234 different-vintage red wine were investigated based on a targeted HPLC-MS/MS and CIELAB approach. The K-means cluster analysis showed that the evolution pattern varies amongst anthocyanin derivative classes. Their stabilities are: pinotins > flavanyl-pyranoanthocyanins, vitisin A > monomeric anthocyanin, direct anthocyanin-flavan-3-ols condensation products > vitisin B, anthocyanin ethyl-linked flavan-3-ols products. The proportion of most pyranoanthocyanins becomes more significant among all detected anthocyanin derivatives during wine aging, whereas flavanols-related anthocyanin derivatives (except for flavanyl-pyranoanthocyanins) decreased drastically. PLSR showed that aging tawny characteristics is related to pyranoanthocyanins except for vitisin B, especially pinotins, whereas monomeric anthocyanins and flavanol-related derivates (except for flavanyl-pyranoanthocyanins) contribute to red violet color. But aging color density is more associated with the content of vitisin A and flavanyl-pyranoanthocyanins. Two predictive models based on random forest and support vector machine modeling showed good performance in predicting the extent of wine aging.

The Xinjiang region is a major grape- and wine-production area in China, but the region’s notably high temperatures in the summer and year-round intense sun exposure play negative roles in the aroma, complexity, and elegance of Cabernet Sauvignon wine. In this study, Cabernet Sauvignon grapes harvested in this region were fermented on an industrial scale using four commercial yeast strains (L2323, D254, RVA, and CECA) and spontaneous yeast (NF). The results showed that a total of 123 volatile compounds were detected and 15 volatile compounds significantly contributed their flavor notes to the wine’s overall aroma. The use of RVA and CECA strains resulted in wine with higher concentrations of higher alcohols, terpenes and norisoprenoids. However, the D254-fermented wine showed high level of esters and carbonyl compounds. Wine fermented with the L2323 and D254 strain possessed a stronger fruity aroma, whereas the RVA strain enhanced the herbaceous, chemical, and fatty aromas in wine. Principal component analysis revealed that a significant aromatic feature difference was observed in these wines after alcoholic and malolactic fermentation. The use of different commercial yeast strains altered the aromatic profile of Cabernet Sauvignon wine.

Background: Monosaccharides, organic acids and amino acids are the important flavour-related components in wines. The aim of this article is to develop and validate a method that could simultaneously analyse these compounds in wine based on silylation derivatisation and gas chromatography-mass spectrometry (GC-MS), and apply this method to the investigation of the changes of these compounds and speculate upon their related influences on Cabernet Sauvignon wine flavour during wine ageing. This work presented a new approach for wine analysis and provided more information concerning red wine ageing.; Results: This method could simultaneously quantitatively analyse 2 monosaccharides, 8 organic acids and 13 amino acids in wine. A validation experiment showed good linearity, sensitivity, reproducibility and recovery. Multiple derivatives of five amino acids have been found but their effects on quantitative analysis were negligible, except for methionine. The evolution pattern of each category was different, and we speculated that the corresponding mechanisms involving microorganism activities, physical interactions and chemical reactions had a great correlation with red wine flavours during ageing.; Conclusion: Simultaneously quantitative analysis of monosaccharides, organic acids and amino acids in wine was feasible and reliable and this method has extensive application prospects. © 2017 Society of Chemical Industry.; © 2017 Society of Chemical Industry.

The downstream flux of carotenoid metabolism in grape berries includes the biosynthesis of norisoprenoids, a group of important aroma compounds, and the production of ABA, a well-known plant hormone. This study focused on the transcriptional profiling comparison of genes participating in the biosynthesis of carotenoids, norisoprenoids, and ABA in Vitis vinifera 'Cabernet Sauvignon' grapes at pea size, veraison, and ripening stages. The grapes were obtained from Changli (CL, eastern China) and Gaotai (GT, western China) regions and analyzed using RNA-sequencing technology. The transcripts required for the carotenoid biosynthesis pathway showed a coordinated expression pattern, mainly expressing at green stage for CL and at veraison for GT, respectively. However, the carotenoid content evolution was not coincident with the timing and pattern of related gene expressions, since more carotenoids were accumulated at veraison in CL relative to two weeks before veraison in GT. Interestingly, norisoprenoid content was higher in GT than in CL, particularly at veraison and ripening, while the key gene encoding carotenoid cleavage dioxygenases, VvCCD1, showed an inverse relationship within the two regions. Higher flux was expected through the carotenoid pathway into ABA production in GT, based on the higher expression level of 9-cis-epoxycarotenoid dioxygenase and drought growing conditions. Most components involved in ABA and ethylene signaling showed distinct expression profiles in the two regions. These results revealed that downstream flux of carotenoid metabolism in grape berries showed regional differences. This study lays a foundation for future research to explore the molecular basis of climatic influences on carotenoid, norisoprenoid, and ABA biosynthesis.

A number of lactones and furanones associated with pleasant odorants play a vital role in grape and wine aroma profiles. However, they are usually present at trace levels and are particularly challenging to measure. In this work, an optimized method based on solid-phase extraction (SPE) coupled with gas chromatography-triple quadrupole mass spectrometry (GC-QqQ-MS/MS) was developed for simultaneous determination of 14 lactones and 3 furanones. The validation was carried out using different types of wine as matrices, and satisfactory linearity, sensitivity, trueness and precision were confirmed. Furaneol and sotolon showed significantly lower limits of detection (LODs) in three real wines compared to model wine due to the matrix effect. Furthermore, the method was successfully applied to investigate the concentration range of lactones and furanones in several icewines, dry red and white wines. Icewines contained higher concentrations of most lactones and furanones compared with dry red and white wines. Partial least squares-discriminate analysis (PLS-DA) also indicated that γ-hexa-, γ-octa-, γ-nona-, γ-deca-, δ-hexa-, and δ-decalactone, as well as 5,6-dihydro-6-pentyl-2H-pyran-2-one (C10 massoia lactone), sotolon and homofuraneol contributed greatly to the discrimination between icewines and dry wines. Moreover, the calculation of odor activity value (OAV) suggested that γ-octa-, γ-nona-, and γ-decalactone, as well as furaneol and homofuraneol contributed greatest to the aroma of icewines.

Berries of six Vitis davidii Foex (spine grape) cultivars (‘Baiputao’, ‘Gaoshan 1’, ‘Gaoshan 2’, ‘Seputao’, ‘Miputao’, and ‘Tianputao’) were harvested from a commercial vineyard in Hunan Province in China. Free and bound volatile compounds and fatty acids were analyzed by GC–MS, and amino acids were analyzed by HPLC. ‘Tianputao’ and ‘Miputao’ were characterized by relatively higher concentrations of aromatic amino acids and lower concentrations of branched-chain amino acids. The major free volatile compounds of spine grapes were hexanal, (E)-2-hexenal, 1-hexanol, (E)-2-hexenol, (E)-β-damascenone, and benzeneacetaldehyde. The major glycosidically bound volatile compounds identified were 1-hexanol, menthol, nerol, 1-butanol, 3-methyl-3-butenol, benzenemethanol, β-phenylethanol, eugenol, and guaiacol. (E)-β-damascenone, benzeneacetaldehyde, guaiacol, and eugenol had odor activity values (OAVs) > 1 in all cultivar grapes. Partial least squares discriminant analysis (PLS-DA) revealed ‘Tianputao’ to be distinct from the other cultivars due to its relatively higher concentrations of major terpenoids, norisoprenoids, higher alcohols, and aromatic amino acids. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s10068-020-00823-6) contains supplementary material, which is available to authorized users.

Differences in key odor-active volatile compounds among the head, heart, and tail fractions of freshly distilled spirits from Spine grape (Vitis davidii Foex) wine were identified for the first time by gas chromatography–olfactometry and gas chromatography-mass spectrometry. Results from aroma extract dilution analysis (AEDA) showed that there were 34, 45, and 37 odor-active compounds in the head, heart and tail fractions, respectively. Besides, 20, 22, and 17 quantified compounds, respectively, showed odor activity values (OAVs) > 1. The head fraction was characterized by fruity, fusel/solvent notes owing to higher concentrations of higher alcohols and esters, while the tail fraction had more intense smoky/animal, sweaty/fatty attributes due to higher concentrations of volatile phenols and fatty acids. Finally, the heart fraction was characterized by ethyl octanoate, ethyl hexanoate, ethyl 3-phenylpropanoate, ethyl cinnamate, isoamyl alcohol, guaiacol, 4-ethylguaiacol, 4-vinylguaiacol, 2,3-butanedione, and (E)-β-damascenone. Furthermore, observation of the distillation progress indicated that different volatiles with various boiling points and solubilities followed diverse distillation patterns: concentrations of most esters, higher alcohols, terpenes and C13-norisoprenoids decreased, while concentrations of volatile phenols, fatty acids and some aromatic compounds increased during distillation. As a result, their final concentrations in the three distillate fractions varied significantly.

Primary and secondary metabolism in grape berries is under the control of complex interactions among environmental conditions, genotypes, and management practices. To obtain an interpretation from the view of transcriptome on distinct metabolite accumulation between ecologically different regions in China, next-generation sequencing technology was performed on E-L 31, 35, and 38 stages of Cabernet Sauvignon grape berries from Changli (CL, eastern) and Gaotai (GT, western). The transcript abundance of epoxycarotenoid dioxygenase and xanthoxin dehydrogenase required for ABA biosynthesis was significantly higher in the GT berries at E-L 35 and 38 stages compared with the CL berries, which may explain the relatively short maturation period of berries in the western region. Some genes required for carbohydrate metabolism, such as hexose transporter, L-idonate dehydrogenase, and phosphoenolpyruvate carboxylase, were significantly up-regulated in the CL berries in relation to the GT berries, which positively correlated with the sugar and organic acid accumulations. Pathway enrichment analysis of differentially expressed genes revealed that the CL berries had higher levels of phenylpropanoid biosynthesis at E-L 38 stage than the GT berries, which may relate to the quick fading of the GT wines because of weak co-pigmentation. This observation lays a foundation for further study concerning the molecular basis for environmental effects on berry quality formation.

Vitis amurensis var. Zuoshanyi is a native red variety grown in Northeast China with excellent cold hardness for genetic breeding and winemaking potential, but the volatiles profile, especially key compounds related to aroma character, was not fully revealed. In this work, Zuoshanyi grapes were collected across two harvests (2010 and 2011) in Shangzhuang area in Beijing, China. Free and glycosidase enzymatic hydrolysis volatiles were analyzed using SPME coupled with gas chromatography and mass spectrometry. A total of 135 volatile compounds were identified and quantified. Among the 13 categories of constituents, C6 compounds were the most abundant, followed by alcohols and ketones, and esters were the least abundant in two vintages. C6/C9 compounds, MPs (3-isobutyl-2-methoxypyrazine and 3-isopropyl-2-methoxypyrazine) and (E)-β-damascenone were the major compounds of Zuoshanyi grapes, which contributed “grass, green, fruit, etc.,” aroma as characterization of this distinctive cultivar. Results from hierarchical clustering and heatmap visualization revealed the accumulation patterns of volatile compounds during berry development. Principal component analysis showed clear separation of free and enzyme-released components in two vintages. Rainfall was the major different climate factor in log phase and before veraison of Zuoshanyi grapes in two vintages, and this difference may potentially influence the volatile variances of Zuoshanyi grapes.

This paper reports the occurrence of both free and glycosidically bound aroma compounds in three sweet cherry cultivars (‘Hongdeng’, ‘Hongyan’ and ‘Rainier’), with 97 compounds being identified in the three cultivars. The major free volatile compounds found were hexanal, (E)-2-hexenal, (E)-2-hexen-1-ol, benzyl alcohol and benzaldehyde. The major bound volatile compounds found were benzyl alcohol, geraniol, 2-phenylethanol. Also 4-vinylphenol was found in cherry fruit for the first time, and has a relatively high concentration of the glycosidically-bound form in ‘Rainier’. Odour activity values (OAVs) were determined for both free and bound volatiles, with 18 compounds having an OAV above 1. The highest OAVs for three cultivars were (E)-β-ionone, hexanal, decanal and (E)-2-hexenal with the highest being over 800 for (E)-β-ionone in ‘Honyang’. From these results, it was concluded that the aroma compounds present were similar in all three cultivars, but there was significant variation found in their levels and hence contribution to the aroma of these cultivars.

Monosaccharides, organic acids and amino acids are the important flavour-related components in wines. The aim of this article is to develop and validate a method that could simultaneously analyse these compounds in wine based on silylation derivatisation and gas chromatography-mass spectrometry (GC-MS), and apply this method to the investigation of the changes of these compounds and speculate upon their related influences on Cabernet Sauvignon wine flavour during wine ageing. This work presented a new approach for wine analysis and provided more information concerning red wine ageing.This method could simultaneously quantitatively analyse 2 monosaccharides, 8 organic acids and 13 amino acids in wine. A validation experiment showed good linearity, sensitivity, reproducibility and recovery. Multiple derivatives of five amino acids have been found but their effects on quantitative analysis were negligible, except for methionine. The evolution pattern of each category was different, and we speculated that the corresponding mechanisms involving microorganism activities, physical interactions and chemical reactions had a great correlation with red wine flavours during ageing.Simultaneously quantitative analysis of monosaccharides, organic acids and amino acids in wine was feasible and reliable and this method has extensive application prospects. © 2017 Society of Chemical Industry.

The evolution of free and glycosidically bound volatile compounds in ‘Beibinghong’ (Vitis vinifera × Vitis amurensis) grape berries throughout on-vine over-ripening and freezing processes was studied in two vintages. The aroma profiles of ‘Beibinghong’ icewine berries were characterized by C6 compounds, higher alcohols and terpenoids in free fractions and carbonyl compounds, higher alcohols, C6 alcohols and terpenoids in bound fractions. With regard to free volatile compounds, there was a decrease in the concentration of C6 compounds, terpenols and norisoprenoids and an increase of terpene oxides during over-ripening process. A striking alteration of volatile profile occurred at sub-zero temperatures, particularly for the free fractions such as C6 alcohols, higher alcohols and oxidative terpene derivatives. These changes were attributed to a series of reactions (biotransformation, oxidation and anaerobic metabolism) induced by water loss and especially freeze-thaw cycles. PCA revealed temperature and rainfall affected the accumulation of volatile compounds during over-ripening processes.

Background Terpenes are of great interest to winemakers because of their extremely low perception thresholds and pleasant floral odors. Even for the same variety, terpene profile can be substantially different for grapevine growing environments. Recently a series of genes required for terpene biosynthesis were biochemically characterized in grape berries. However, the genes that dominate the differential terpene accumulation of grape berries between regions have yet to be identified. Methods Free and glycosidically-bound terpenes were identified and quantified using gas chromatography-mass spectrometry (GC-MS) technique. The transcription expression profiling of the genes was obtained by RNA sequencing and part of the results were verified by quantitative real time PCR (QPCR). The gene co-expression networks were constructed with the Cytoscape software v 2.8.2 (www.cytoscape.org). Results ‘Muscat Blanc a Petits Grains’ berries were collected from two wine-producing regions with strikingly different climates, Gaotai (GT) in Gansu Province and Changli (CL) in Hebei Province in China, at four developmental stages for two consecutive years. GC-MS analysis demonstrated that both free and glycosidically bound terpenes accumulated primarily after veraison and that mature grape berries from CL contained significantly higher concentrations of free and glycosidically bound terpenes than berries from GT. Transcriptome analysis revealed that some key genes involved in terpene biosynthesis were markedly up-regulated in the CL region. Particularly in the MEP pathway, the expression of VviHDR (1-hydroxy-2-methyl-2-butenyl 4-diphosphate reductase) paralleled with the accumulation of terpenes, which can promote the flow of isopentenyl diphosphate (IPP) into the terpene synthetic pathway. The glycosidically bound monoterpenes accumulated differentially along with maturation in both regions, which is synchronous with the expression of a monoterpene glucosyltransferase gene (VviUGT85A2L4 (VviGT14)). Other genes were also found to be related to the differential accumulation of terpenes and monoterpene glycosides in the grapes between regions. Transcription factors that could regulate terpene synthesis were predicted through gene co-expression network analysis. Additionally, the genes involved in abscisic acid (ABA) and ethylene signal responses were expressed at high levels earlier in GT grapes than in CL grapes. Conclusions Differential production of free and glycosidically-bound terpenes in grape berries across GT and CL regions should be related at least to the expression of both VviHDR and VviUGT85A2L4 (VviGT14). Considering the expression patterns of both transcription factors and mature-related genes, we infer that less rainfall and stronger sunshine in the GT region could initiate the earlier expression of ripening-related genes and accelerate the berry maturation, eventually limiting the production of terpene volatiles. Electronic supplementary material The online version of this article (doi:10.1186/s12870-015-0631-1) contains supplementary material, which is available to authorized users.

Volatile compounds are considered important for plants to communicate with each other and interact with their environments. Most wine-producing regions in China feature a continental monsoon climate with hot-wet summers and dry-cold winters, giving grapes markedly different growing environments compared to the Mediterranean or oceanic climates described in previous reports. This study focused on comparing the volatile profiles of Vitis vinifera L. cv. Cabernet Sauvignon berries from two regions with distinct climate characteristics: Changli has a warm and semi-humid summer, and Gaotai has a cool-arid summer and a cold winter. The relationship between meteorological metrics and the concentrations of grape volatiles were also examined. In harvested grapes, benzyl alcohol, phenylethyl alcohol, 1-hexanol and 1-octen-3-ol were more abundant in the Changli berries, while hexanal, heptanal, 2-methoxy-3-isobutylpyrazine, and (E)-β-damascenone presented higher levels in the Gaotai berries. The fluctuation in the accumulation of volatile compounds observed during berry development was closely correlated with variations in short-term weather (weather in a week), especially rainfall. The concentration of some volatiles, notably aliphatic aldehydes, was significantly related to diurnal temperature differences. The variability during berry development of concentrations for compounds such as C6 volatile compounds, 2-methoxy-3-isobutylpyrazine and (E)-β-damascenone strongly depended upon weather conditions. This work expands our knowledge about the influence of continental monsoon climates on volatile compounds in developing grape berries. It will also improve the comprehension of the plant response to their surrounding environments through the accumulation of volatiles. The results will help growers to alter viticultural practices according to local conditions to improve the aromatic quality of grapes.

The influence of pre-fermentation cold maceration (CM) on Cabernet Sauvignon wines fermented in two different industrial-scale fermenters was studied. CM treatment had different effects on wine aroma depending on the types of fermenter, being more effective for automatic pumping-over tank (PO-tank) than automatic punching-down tank (PD-tank). When PO-tank was used, CM-treated wine showed a decrease in some fusel alcohols (isobutanol and isopentanol) and an increase in some esters (especially acetate esters). However, no significant changes were detected in these compounds when PD-tank was used. Ethyl 2-hexenoate and diethyl succinate were decreased, while geranylacetone was increased by the CM treatment in both fermenters. β-Damascenone was increased by the CM treatment in PO-tank fermented wines but decreased in PD-tank fermented wines. The fruity, caramel and floral aroma series were enhanced while chemical series were decreased by the CM treatment in PO-tank fermented wines. The content of (Z)-6-nonen-1-ol in the final wines was positively correlated to CM treatment.