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Beverages 2017, 3(4), 55; doi:10.3390/beverages3040055

Review
Phenolic Composition and Related Properties of Aged Wine Spirits: Influence of Barrel Characteristics. A Review
1,2
1
National Institute for Agrarian and Veterinary Research, INIAV-Dois Portos, Quinta da Almoínha, 2565-191 Dois Portos, Portugal
2
ICAAM—Institute of Mediterranean Agricultural and Environmental Sciences, University of Évora, Pólo da Mitra, Ap. 94, 7002-554 Évora, Portugal
Received: 20 September 2017 / Accepted: 10 November 2017 / Published: 14 November 2017

Abstract

:
The freshly distilled wine spirit has a high concentration of ethanol and many volatile compounds, but is devoid of phenolic compounds other than volatile phenols. Therefore, an ageing period in the wooden barrel is required to attain sensory fullness and high quality. During this process, several phenomena take place, namely the release of low molecular weight phenolic compounds and tannins from the wood into the wine spirit. Research conducted over the last decades shows that they play a decisive role on the physicochemical characteristics and relevant sensory properties of the beverage. Their contribution to the antioxidant activity has also been emphasized. Besides, some studies show the modulating effect of the ageing technology, involving different factors such as the barrel features (including the wood botanical species, those imparted by the cooperage technology, and the barrel size), the cellar conditions, and the operations performed, on the phenolic composition and related properties of the aged wine spirit. This review aims to summarize the main findings on this topic, taking into account two featured barrel characteristics—the botanical species of the wood and the toasting level.
Keywords:
wine spirit; ageing; wooden barrels; oak wood; chestnut wood; toasting level; phenolic composition; chromatic characteristics; sensory properties; antioxidant activity

1. Introduction

The aged wine spirit is one of the most representative alcoholic beverages, taking into account production, trade [1], and consumption [2] worldwide. Its manufacture has a long history and a relevant socioeconomic role in the traditional wine countries, mainly in Europe. Among them, it is worth mentioning France and its regions of Armagnac and Cognac that date back to the 15th and 16th centuries, respectively [3,4,5], producing the most prestigious and top-selling aged wine spirits. In this scenario, Portugal and its Lourinhã region should also be highlighted, whose historical references on wine spirit production date back to the early 20th century; it was delimited in 1992 as an exclusive denomination for aged wine spirits, like the above-mentioned French regions [6].
According to the European legislation [7], the wine spirit can be aged for at least one year in wood containers or for at least six months in wood containers with a capacity of less than 1000 L. For wine spirits with geographical denomination, the ageing period is at least one year for Armagnac [8], and two years for Cognac [9] and Lourinhã [10].
Actually, the freshly distilled wine spirit is characterised by a high concentration of ethanol and richness of volatile compounds, but is devoid of phenolic compounds other than volatile phenols [11]. Ageing in a wooden barrel (of oak, chestnut, …) is traditionally included in wine spirit production technology, being recognized as a crucial step for adding value to the product. During this process, the beverage undergoes important modifications and becomes a complex mixture of hundreds of compounds in an ethanol-water matrix [12], leading to sensory fullness and improvement of its quality. There is much to know about the chemistry underpinning the ageing of wine spirits, but the scientific community unquestionably accepts that those physicochemical and sensory changes result from several phenomena [13,14,15,16,17,18,19,20,21] such as:
  • Direct extraction of wood constituents;
  • Decomposition of wood biopolymers (lignin, hemicelluloses and cellulose) followed by the release of derived compounds into the distillate;
  • Chemical reactions involving only the wood extractable compounds;
  • Chemical reactions involving only the distillate compounds;
  • Chemical reactions between the wood extractable compounds and the distillate compounds;
  • Evaporation of volatile compounds and concentration of volatile and non-volatile compounds;
  • Formation of a hydrogen-bonded network between ethanol and water.
Among these phenomena, the release of wood extractable compounds into the wine spirit, namely low molecular weight phenolic compounds and tannins, plays a decisive role in its chemical composition, sensory properties [22,23,24] and overall quality. In addition, oxidation reactions involving these compounds and those of the distillate are of paramount importance [25,26,27,28,29]. They are triggered by the slow and continuous diffusion of oxygen through the space between staves and through the wood [30,31,32].
The research carried out over the last decades has shown that the aforementioned changes are closely related to the action of factors ruling the ageing process, namely:
(i)
The wooden barrel characteristics—the wood botanical species used, and the characteristics imparted by the cooperage technology (especially the seasoning/maturation of the wood and the heat treatment of the barrel), and the barrel size [33];
(ii)
The cellar conditions—temperature, relative humidity and air circulation [18,34,35];
(iii)
The technological operations performed during the ageing period, such as the refilling with the same wine distillate to offset the loss by evaporation [18,20,36], the addition of water to decrease the alcoholic strength [37], and stirring to homogenize the wine spirit and to enhance the extraction of wood compounds [38].
Concerning the resulting sensory properties, positive correlations between the phenolic composition and the color were established [23,39,40], which are in accordance with the findings in studies on Porto wine [41] and wine [42,43,44,45,46]. Notwithstanding the intricate effect of compounds on aroma and flavour owing to the complexity of their interactions and the multiple sensations involved [47,48], some features have been often related to the phenolic composition of the aged wine spirit and of other aged beverages. There is evidence on the relationship between: the vanilla aroma and vanillin concentration [24,49,50]; the bitterness and phenolic acids, their ethyl esters, and (+)-lyoniresinol concentrations [48,51,52,53,54]. Among these properties, the vanilla aroma should be highlighted due to its outstanding importance for aged wine spirit quality [55,56,57]. The relationship between astringency and ellagitannin and gallotannin concentrations is still unclear for thesekind of beverages [48,51,52,53,54,58,59].
In addition, the phenolic compounds (in this case almost exclusively extracted from the wood) exhibit a wide range of biological effects, many of which have been ascribed to their antioxidant activity. Several studies mention the antioxidant activity of some phenolic acids [60,61,62,63,64,65,66,67,68,69], phenolic aldehydes [70,71], coumarins [72], tannins [65,67,73,74,75], lignans [76], and of some volatile phenols [77]. This topic is of great relevance in a spirit drink, since the harmful effect of high alcoholic strength on consumer’s health can be offset by the intake of such bioactive compounds [74,78,79,80,81,82,83,84]. Such benefits are expected in beverages that have undergone ageing in wood, especially wine spirits and whisky, but not in the traditional gins and vodkas [78].
Despite the knowledge acquired through different studies on the phenolic composition and related properties of the aged wine spirit modulated by the ageing technology, so far there have been no published articles systematizing it. This review assembles the main findings on the topic, taking into account two featured barrel characteristics—the wood botanical species and the toasting level.

2. Phenolic Compounds Found in Aged Wine Spirits

Several low molecular weight phenolics (Table 1) have been identified and quantified in aged wine spirits using high performance liquid chromatography (HPLC) or capillary electrophoresis (EC). All of them are non-flavonoid compounds; therefore, the phenolic composition of the aged wine spirit differs from that of wine and wine aged in wood, in which flavonoid and non-flavonoid compounds coexist [85,86].
Regardless the ageing conditions and the analytical methodologies employed, the results presented in Table 1 show that phenolic acids are the most abundant phenolic compounds in wine spirits, accounting for ca. 70% of low molecular weight phenolic compounds, followed by phenolic aldehydes (ca. 15%), lignans (ca. 12%), phenyl ketones (ca. 3%) and coumarins (0.1%) (Figure 1).
These acids, aldehydes and coumarins already exist in oak and chestnut heartwoods in the free form or linked to parietal constituents [108]. Nevertheless, their contents change considerably through the thermal degradation of the wood lignin [109,110,111,112,113] together with the increase of wood permeability [114,115] during the heat treatment of the barrel. Hence, higher amounts can be released into the wine spirit over the ageing process. Besides, lignin’s hydrolysis occurring during ageing may also contribute to the enrichment in some phenolic aldehydes and phenolic acids [14,29,116].
Gallic acid and ellagic acid are the most representative phenolic acids, followed by syringic, vanillic, and ferulic acids. Protocatechuic acid and coumaric acid seem to be less important since they have not always been detected in the aged wine spirit.
The syringyl-type aldehydes (sinapaldehyde and syringaldehyde) are more plentiful than the guaiacyl-type aldehydes (vanillin and coniferaldehyde), probably due to the higher thermal stability of the former and their consequently greater accumulation in the toasted wood [117,118].
Among coumarins, the literature indicates scopoletin as more abundant than umbelliferone [38,93,102].
Concerning the lignans, few works report the presence of lyoniresinol in aged wine spirits. Despite the non-negligible amounts found, more advanced analytical conditions required for the separation and quantification of its two enantiomers [53,107,119] may justify their non-detection by HPLC under common chromatographic conditions. One of the enantiomers, (+)-lyoniresinol, was also quantified in oak wood [53,92,107], in which it remains stable under toasting until 200 °C [107,117].
As far as we know, acetovanillone was only quantified in small amounts in one study [106] and was also detected in toasted wood [14,120], being mainly formed by the thermal degradation of lignin [14,121].
In addition to the low molecular weight phenolic compounds, five hydrolysable tannins were identified and quantified in aged wine spirits by liquid chromatography coupled to mass spectrometry (LC-MS) and HPLC, respectively [122] (Table 2).
The four monomeric ellagitannins and the monomeric gallotannin are derived from the wood (oak or chestnut), in which they are present in higher amounts, together with four dimeric ellagitannins (roburins A, B, C and D) [67,123,124,125,126], and with other dimeric and trimeric gallotannins [127,128]. Therefore, their low content or absence in the aged wine spirits may result from the thermal degradation during the heat treatment of the wood [117,126,129,130,131]. Moreover, low extraction [132], as well as oxidation and hydrolysis of ellagitannins, may occur during ageing [99,101].
Among the identified ellagitannins, castalagin and vescalagin are the most representative ones, followed by xylose and lyxose derivatives (roburin E and grandinin, respectively), as in the wood. Taking into account the total average content of soluble ellagitannins in Cognacs (4–840 mg/L; [15,101]) and in Armagnacs (155–702 mg/L; [22]), the quantified ellagitannins (Table 2) only represent ca. 3%, 0.03%, 0.03% and 0.03%, respectively; that is, other unidentified ellagitannins are likely to be extracted from the wood into the wine spirit and to have a greater contribution to the total amount. Actually, so far, few soluble tannins have been found in the aged wine spirit, contrasting with the increasing number of tannins and derived compounds detected in the aged wine [43,133].
Data from Table 1 and Table 2 clearly illustrate the huge variability of the phenolic compounds concentrations in aged wine spirits. Indeed, it encompasses the effect of the analytical methodology used, but especially the impact of the barrel characteristics. Details on the last aspect and its repercussion on the chromatic characteristics, color, other related sensory properties, and antioxidant activity of the aged wine spirit are presented in the following sections.

3. Influence of the Wood Botanical Species

The wood most commonly used for the ageing of wine spirits is from the oak species Quercus robur L., principally from the French region of Limousin [37,134]. However, other wood botanical species have been increasingly studied to evaluate their potential for the cooperage, focusing their chemical composition: Quercus sessiliflora Salisb., particularly from the French region of Allier, and Quercus alba L., mainly from North America [67,108,135,136]; Quercus pyrenaica Willd., grown in Mediterranean countries [67,108,124,126,137]. Chestnut wood (Castanea sativa Mill.) has also been exploited for this purpose, and is of particular significance in the countries bordering the Mediterranean Sea due to historical, economical, and social aspects of its cultivation [138]. Its suitability for the cooperage aiming the ageing of wine spirit has also been investigated [6,102,108,120,139,140].

3.1. Phenolic Composition

Considerable attention has been devoted by several research teams to the chemical composition of wood used in oenology. However, only a limited number of studies about its impact on the chemical composition of the aged wine spirit have been published. Moreover, their experimental designs are not always fully described, hindering the comparison of results obtained in different approaches. To the best of our knowledge, the exception lies in four older works that examined the effect of one kind of wood. Baldwin et al. [13] found low levels of vanillin (ranging from 0.6 to 1.5 mg/L), syringaldehyde (varying from 1.2 to 7.6 mg/L), coniferaldehyde (ranging from 0.3 to 1.8 mg/L), and sinapaldehyde (ranging from 0.2 to 3.4 mg/L) in American wine spirits aged in new barrels of American oak. Similarly, Nabeta et al. [92] reported low average contents of vanillin (0.6 mg/L), syringaldehyde (0.35 mg/L), coniferaldehyde (1.4 mg/L), and sinapaldehyde (0.8 mg/L) in Japanese wine spirits aged over a six-year period in new barrels of French oak wood. Tricard et al. [94] also observed low amounts of vanillin (2.28 mg/L) and syringaldehyde (6.60 mg/L), but a considerable amount of scopoletin (109 mg/L), in Cognacs aged over a seven-year period in new barrels of French oak. In contrast, Puech and Moutounet [99] found higher contents of vanillin (8.2 mg/L), syringaldehyde (19.4 mg/L), coniferaldehyde (17.8 mg/L), and sinapaldehyde (19.8 mg/L) in wine brandies aged over a seven-year period in new barrels of Limousin oak. They also found high contents of ellagic acid (62.9 mg/L), gallic acid (31.0 mg/L), vanillic acid (7.9 mg/L), and syringic acid (8.2 mg/L).
The most recent works [6,56,105] were based on a factorial design using the same wine distillate from the Lourinhã region (produced by Adega Cooperativa da Lourinhã) aged over a four-year period in barrels made from the following kinds of wood: Limousin oak (Q. robur L.) and Allier oak (Q. sessiliflora Salisb.) from French forests; American oak (mixture of Q. alba L./Q. Stellata Wangenh. and Q. lyrata Walt./Q. bicolor Willd.) from Pennsylvania/USA; Portuguese oak (Q.pyrenaica Willd.) and chestnut (C. sativa Mill.) from the North of Portugal. The 250 L barrels were supplied by J. M. Gonçalves cooperage (Palaçoulo, Portugal) and were placed in the cellar of Adega Cooperativa da Lourinhã in similar environmental conditions.
Significant differences in the contents of the majority of low molecular weight phenolic compounds of the aged wine spirit according to the wood used were observed (Table 3). Chestnut wood induced the highest content of phenolic acids in the wine spirit, especially of gallic acid and ellagic acid, as noticed for the ageing of red wine [141,142]. The highest levels of vanillin and syringaldehyde were also found in the wine spirit aged in chestnut barrels. Portuguese oak wood promoted intermediate enrichment, with the highest level of sinapaldehyde, while the other kinds of oak had a weaker performance. However, the richness of coumarins associated with the American oak should be stressed, because these compounds can act as chemical markers of this kind of wood [56,95].
Comparing the results of the oldest and most recent works, important differences in the concentrations of phenolic aldehydes, phenolic acids and scopoletin in wine brandies aged in French oak wood and American oak wood are observed. They may express the effect of the geographical origin of the wood, as well as the interaction between the kind of wine distillate and the wood, in the extraction kinetics of such compounds. Despite the observed variability, the American oak wood had a lesser contribution to the phenolic composition of the aged wine spirit. Taking into account the results of Puech and Moutounet [99], the performance of Limousin oak wood resembled that of Portuguese oak wood.
The phenolic differentiation of wine spirits was ascribed to the pool of phenolic compounds in the different kinds of wood under study [108,126,140,143] and to lignin hydrolysis during ageing [14,29,102,116,144]. Furthermore, gallic acid and ellagic acid can be directly extracted from the wood, or derived from the hydrolysis of gallotannins [112] and ellagitannins [101], respectively, especially in the first years of ageing [22,101].
Comparing the hydrolysable tannins of the wine spirit aged in Limousin oak wood and in chestnut wood, Canas et al. [122] did not observe significant differences in their contents (Table 4). Monogalloyl-glucose was only present in the wine spirit aged in chestnut barrels, as in the corresponding wood [123], although detection of this monomeric gallotannin in Quercus robur wood already made by other authors [127]. The robustness of the methods used in the isolation and quantification of the tannin fraction pointed to the conclusion that the above-mentioned effect could be caused by the wood intraspecific variability [145].

3.2. Chromatic Characteristics and Sensory Properties

The color is a core element in the perception of wine spirit quality, as for other beverages [146]. It determines the first impression and rules the consumer’s choice [147]. Among the few authors who studied it in aged wine spirits [39,40,148], Canas et al. [23] remarked that the chromatic characteristics (CIELab parameters) are closely related to the kind of wood used (Figure 2). In this investigation [23], the wine spirit aged in chestnut wood stood out by its more evolved color than the wine spirits aged in oak wood. It displayed higher color intensity (lower L*), higher red (a*) and yellow (b*) hues, and higher saturation (C*) that made it look older than the latter. Indeed, there is scientific evidence about the color evolution of wine spirits over the ageing time, which is marked by a decreasing of lightness and an increasing of saturation, red hue and yellow hue [148]. Among the wine spirits aged in oak wood, the one aged in Portuguese oak exhibited greater evolution of the chromatic characteristics than those aged in Limousin oak, American oak and Allier oak. Once the wine distillate itself is colorless due to the absence of phenolic compounds other than volatile phenols [11], the observed changes are assigned to the wood stage. Recently, Rodríguez-Solana et al. [149] reported concordant results for a grape marc spirit aged in Q. robur, Q. alba and Q. petraea wooden barrels.
The different pool of phenolic compounds and extraction kinetics (Table 3), the oxidative phenomena occurring during ageing [26,27,101], and the condensation reactions between phenolic compounds promoted by each kind of wood possibly accounted for the differences in the chromatic characteristics. Condensation reactions between tannins mediated by acetaldehyde (resulting from ethanol oxidation and which may represent more than 90% of the aldehydes’ content of the aged wine spirit [14,16]), by phenolic aldehydes and furanic derivatives, such as furfural and 5-hydroxymethylfurfural, are likely to happen, as in wine during ageing [146,150,151,152].
Interestingly, as described in the same work [23], the color perceived by the tasters (Figure 3) was consistent with the chromatic characteristics of the aged wine spirits (Figure 2).
The wine spirits aged in chestnut barrels were characterized by a more evolved color owing to the highest intensities of topaz (orange, amber color), greenish color, and the lowest intensities of golden and yellow straw (Figure 3). The wine spirit aged in Portuguese oak wood had high intensity of topaz and golden while those aged in the other kinds of oak wood showed higher intensities of golden, yellow straw and yellow green. Topaz is the main color of older wine spirits, resulting from the combination of higher positive values of chromaticity coordinates a* (red hue) and b* (yellow hue), whereas the golden prevails in wine spirits with less ageing time. Therefore, as for the analytical color, the sensory color of the wine spirits expressed the differences in their phenolic composition.
Examining other sensory properties of the wine spirits, Caldeira et al. [153] found significantly higher intensities of vanilla and astringency underlying the cluster formed by the wine spirits aged in Portuguese oak and chestnut. For these attributes, the wine spirits aged in Allier oak and American oak presented the opposite features, while those aged in Limousin oak showed an intermediate profile. Similar results were obtained for grape marc spirits aged in Q. robur, Q. alba and Q. petraea barrels [149]. The observed behavior for the vanilla aroma is ascribed to the vanillin content (Table 2), while the astringency seems not be related to the content of hydrolysable tannins (Table 3).

3.3. Antioxidant Activity

The antioxidant activity of some spirit drinks, namely the aged wine spirit, has aroused the interest of the researchers. Indeed, the “French Paradox” showed that for apparently the same level of risk factors, cardiovascular mortality rate is lower in France than in the European Northern countries [154]. Moreover, among the French regions, this phenomenon was particularly evident in the southwest France, a region where people do not drink more wine than elsewhere, but often drink Armagnac [155]. Therefore, some research was conducted to evaluate the antioxidant activity of Armagnacs and Cognacs [74,78,80] as well as of Spanish brandies [82,156], revealing its positive correlation with the ageing time. Later on, the influence of the wood botanical species used was examined [122]. Similar studies were also done with brandies [84,157] but the corresponding experimental designs raise many doubts, and do not allow comparison of outcomes with those obtained for the aged wine spirits.
Studying the in vitro antioxidant activity of the same wine spirit aged in chestnut barrels and in Limousin oak barrels, Canas et al. [122] concluded that the wood botanical species induced significantly different antioxidant activity (measured by 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity—DPPH) regardless the toasting level. The antioxidant activity promoted by the chestnut wood (DPPH inhibition = 93.5%) was two-fold higher than that promoted by Limousin oak wood (DPPH inhibition = 45.7%)—Figure 4.
This effect is explained by the highest phenolic content of the wine spirit aged in chestnut barrels; synergistic phenomena [81,158] and antagonistic phenomena [159] between individual phenols are also likely to occur. The antioxidant activity was mainly correlated with gallic acid (r = 0.9555) and ellagic acid (r = 0.6138), whose contents were significantly higher in the wine spirit aged in chestnut wood (Table 3). Actually, these phenolic acids are well-known bioactive compounds [61,62,66,69,160]. Syringaldehyde may also have contributed to this feature [70,71], especially in the wine spirit aged in chestnut barrels. It is interesting to note that a similar relationship of the antioxidant capacity was reported by Rodríguez Madrera et al. [143] for C. sativa and Q. robur wood extracts based on the levels of phenolic acids and phenolic aldehydes. Regarding the role of hydrolysable tannins in the observed behavior, no significant correlations were pointed out by Canas et al. [122] for individual compounds and for the total content. However, strong correlations between the antioxidant capacity and monomeric ellagitannins (castalagin, vescalagin, roburin E and grandinin), and dimeric ellagitannins (roburins A–D) were emphasized for wood extracts including C. sativa and Q. robur [67]. On the other hand, Da Porto et al. [74] stated that ellagitannins are the major contributors to the overall antioxidant activity of Cognac. So, this kind of discrepancy could be justified by the variability of wood composition [145] plus the variability induced by the wood heat treatment together with differential extraction from the wood and reactions involving ellagitannins during ageing, as aforementioned.

4. Influence of the Heat Treatment of the Barrel

Research on oak wood and chestnut wood have shown that the heat treatment of the barrel is of remarkable importance to the pool of extractable compounds that can be released into the beverage when it contacts the wood [102,109,110,111,112,113,117,118].
The heat treatment is part of the barrel making process, being performed by the French technique using fire, or by the American technique using heated steam for bending the staves followed by fire [161]. In European cooperage, the barrel is heated over a fire of wood shavings with various techniques of spraying or swabbing with water to enable the bending of the staves to the concave shape of a barrel without breaking—the bending phase [110,161]. Then, the barrel is placed again over the fire to heat the inner surface and to cause significant toasting in order to modify the structure [114], the physical properties [115], and the chemical composition of the wood [109,110,121], which confer a distinct character to the wine or distillate aged in it—the toasting phase. Despite the diversity of toasting protocols, the toasting level is usually classified as light, medium or heavy. In practice, the result mostly depends on the binomial temperature/time applied to each wood botanical species [109,110,143,162,163].

4.1. Phenolic Composition

Scientific data about the influence of the wood toasting level on the phenolic composition and related properties of the aged wine spirit are rather scarce. Notwithstanding, older works made on Spanish brandies by Artajona et al. [96], on Cognacs by Cantagrel et al. [164] and Viriot et al. [101], and on French wine spirits by Rabier and Moutounet [97] and Puech et al. [165] are noteworthy. Artajona et al. [96] found increasing contents of phenolic aldehydes in brandies with an increasing of barrel toasting intensity: ca 18 mg/L, 30 mg/L, and 58 mg/L under the influence of light, medium and heavy toasting, respectively. Rabier and Moutounet [97] observed increasing contents of ellagic acid (ca 15 mg/L and 60 mg/L), gallic acid (ca 4 mg/L and 9 mg/L), and vanillin (ca 0.5 mg/L and 1 mg/L) in a wine spirit aged over a two-year period in new oak barrels with light and heavy toasting levels. Puech et al. [165] also studied the influence of the toasting level (light, medium and heavy) in a wine spirit aged over a two-year period in new barrels of Limousin oak. They found an increasing content of vanillin with the rise of toasting intensity, which remained below 5 mg/L; a similar behavior was observed for syringaldehyde with ca.1 mg/L, 7 mg/L and 11 mg/L under the effect of light, medium and heavy toasting, respectively; for coniferaldehyde and sinapaldehyde, a sharp increase between light and medium toasting (from ca 3 to ca 13 mg/L, and from ca 2 to ca 22 mg/L, respectively) and a slight decrease under heavy toasting (ca 11 mg/L and 21 mg/L, respectively) were described.
In recent years, a comprehensive investigation was performed [6,56,120]. In that study, the same wine distillate from Lourinhã region (produced by Adega Cooperativa da Lourinhã) was aged over a four-year period in 250 L barrels. The barrels were made by J. M. Gonçalves cooperage (Palaçoulo, Portugal) using the following kinds of wood: Limousin oak (Q. robur L.) and Allier oak (Q. sessiliflora Salisb.) from French forests; American oak (mixture of Q. alba L./Q. Stellata Wangenh. and Q. lyrata Walt./Q. bicolor Willd.) from Pennsylvania/USA; Portuguese oak (Q. pyrenaica Willd.) and chestnut (C. sativa Mill.) from the North of Portugal. These barrels were divided into three groups. Then, each group were submitted to one of the three levels of toasting—light (LT), medium (MT) and heavy (HT)—according to the cooperage protocol: 10 min for light toasting, 20 min for medium toasting and 25 min for heavy toasting [120]. They were filled with the same wine distillate and kept in the cellar of Adega Cooperativa da Lourinhã in similar environmental conditions.
Analysing the low molecular weight phenolic compounds of the wine spirits aged in them, Canas [56] showed that the toasting level had a significant effect on the concentration of all phenolic compounds, except for scopoletin (Table 5), confirming the results of previous studies [96,97,164,165].
Furthermore, Viriot et al. [101] and Canas [56] emphasized a positive relationship between ellagic acid concentration in the wine spirits and the toasting intensity of the barrel. A different pattern is identified for gallic acid; its concentration in the aged wine spirits increases under the influence of medium toasting and slightly decreases under heavy toasting. Recent results obtained for grape marc spirit corroborate it [149]. This pattern expresses the behavior of gallic acid in the toasted wood, in which it undergoes degradation from the medium toasting as a consequence of higher thermal sensitivity [97,166]. In contrast, higher level of ellagic acid is ascribed to its high fusion point and greater accumulation in the toasted wood, as observed by Rabier and Moutounet [97]. As in the untoasted wood [108] and toasted wood [109,137], ellagic acid and gallic acid still remain the major phenolic acids of the aged wine spirits, being mainly derived from the wood ellagitannins and gallotannins [118,129,130,167].
It was also demonstrated that the rise of toasting level of the barrel promoted an increase of vanillic acid, syringic acid, ferulic acid and phenolic aldehydes contents in the aged wine spirits, as in the aforementioned studies, except for coniferaldehyde and sinapaldehyde [165]. It is well-known these compounds resulted from the wood lignin’s decomposition [117] (Figure 5). Under mild temperatures, decarboxylation and cleavage of the aryl-alkyl ether bonds of the terminal units of this biopolymer take place, originating the cinnamic aldehydes (coniferaldehyde and sinapaldehyde). At higher temperatures, an oxidative cleavage of double C-C bond of the aliphatic chain of these aldehydes may occur, yielding the corresponding benzoic aldehydes (vanillin and syringaldehyde). The resulting concentrations express the balance between synthesis and degradation reactions. Therefore, the slight decrease of coniferaldehyde and sinapaldehyde contents reported by Puech et al. [165] for heavy toasting should have resulted from specificity of the toasting protocol, which induced higher degradation of these aldehydes.As the temperature rises, the phenolic aldehydes thus formed give rise, by decarboxylation, to the corresponding phenolic acids. Hence, they accumulate in the toasted wood [109,130,137,163].
Furthermore, higher permeability of the wood and better access of the wine spirit to wood extraction sites caused by fragmentation of cell structures and reorganization of lignocellulose network [114,115] may also facilitate their release into the wine spirit. Likewise, lignin’shydrolysis during the ageing period may contribute to their increase in the beverage [14,29,102,116,144]. The presence of oxygen and the mild acidity of the medium, mainly modulated by the increase of acetic acid content over time, favor this pathway [37].
Regardless the toasting level of the barrel and the ageing time, it has been found [29,56,102] that syringyl-type aldehydes (sinapaldehyde and syringaldehyde) prevailed over those of guaiacyl-type (vanillin and coniferaldehyde) in the aged wine spirits. On the other hand, an increase in the syringyl/guaiacyl ratio with the toasting intensity has been referred [14,56,97]. In the above-mentioned work [56], mean values of 1.34, 1.82 and 2.41 were obtained for the same wine spirit aged during four years in barrels with light, medium and heavy toasting levels, respectively. This suggests that higher thermal stability of the syringyl compounds and subsequent higher availability in the toasted wood [117,118] was the causal effect.
There is also evidence of the increase of umbelliferone content in the wine spirit with the toasting level of the barrel [56], but the chemical mechanisms underpinning its formation/degradation during the heat treatment of the wood are still unknown.
Concerning the hydrolysable tannins, no significant differences in wine spirits aged in barrels with different toasting level were reported [122].

4.2. Chromatic Characteristics and Sensory Properties

As for the wood botanical species, data from the literature [23] show the modulating effect exerted by the toasting level of the barrel on the chromatic characteristics of this beverage (Figure 6). The higher the toasting level of the barrel the more the evolution of the aged wine spirit color (higher intensity, saturation and red and yellow hues) with significant increments between levels. Acquisition of these chromatic characteristics makes the wine spirit aged in heavy toasting barrels look older than those aged in medium and light toasting barrels (as noticed for the wine spirit aged in chestnut wood when compared with those aged in different kinds of oak wood). These outcomes are correlated with the phenolic compounds extracted from the wood (Table 5) and are in agreement with those obtained for wine aged in barrels with different toasting levels [167]. In addition, the oxidative phenomena underlying the ageing process may also be responsible for the color acquired by the aged wine spirit; the higher the toasting level the higher the wood permeability to oxygen [114,115], and therefore greater extension of oxidation reactions are expected.
From the sensory point of view, Canas et al. [23] indicated the predominance of yellow straw and yellow green in the wine spirits aged in light toasting barrels, and the prevalence of golden and topaz in those aged in medium and heavy toasting barrels, respectively (Figure 7). These results are consistent with those obtained by the CIELab method (Figure 6), showing a faster ageing of the wine spirit associated with the heavy and medium toasting levels.
Other sensory properties related to the phenolic composition, such as the vanilla aroma and astringency, had higher intensities associated with the heavy toasting barrels [153]. The wine spirits aged in light toasting barrels and medium toasting barrels revealed opposite and intermediate intensities of these attributes, respectively. Increasing concentrations of vanillin with the toasting intensity (Table 5) should explain the effect on the vanilla aroma. Regarding astringency, the existing information does not allow the establishment of a reliable relationship with the phenolic composition.

4.3. Antioxidant Activity

Only one approach [122] is found for the influence of the toasting level on the antioxidant activity of the aged wine spirit. Surprisingly, in this work, it was observed that a non-significant variation of the DPPH inhibition with the toasting intensity existed (60.6%, LT; 69.6%, MT; 63.5%, ST) (Figure 8). Such an effect was assigned to the high variability associated with the toasting operation [102,164], despite the significant influence found for the majority of low molecular weight phenolic compounds (Table 5). Nevertheless, Híc et al. [168] noticed a similar behavior for the oak wood antioxidant activity under the toasting effect.

5. Concluding Remarks

The reviewed literature demonstrates that the phenolic composition and some related properties of the aged wine spirit are effectively modulated by the kind of wood and the toasting level of the barrel. It is worth mentioning the highest enrichment of the wine spirit in low molecular weight phenolic compounds through the contact with chestnut wood (Castanea sativa). As a consequence, greater evolution of the chromatic characteristics and sensory color, as well as higher intensities of vanilla aroma, and higher antioxidant activity are achieved. Q. pyrenaica and Quercus robur exerts a similar influence. It means that these botanical species contribute to accelerate the ageing process and to give singular physicochemical characteristics and sensory profile to the aged wine spirit. The other kinds of oak (Q. petraea and Q. alba) show a weak performance, providing lower contents of phenolic compounds and promoting less intense related properties.
Regarding the toasting levels commonly used, higher concentrations of low molecular weight phenolic compounds, more evolved chromatic characteristics, sensory color, and other related sensory attributes are induced by the heavy toasting, followed by the medium toasting.
Thus, the wood botanical species together with the toasting level of the barrel are important resources for the industry for more sustainable management of the ageing process, to differentiate and to improve the quality of aged spirits. In addition, knowledge on the antioxidant activity of this beverage resulting from different ageing conditions may support a proper management of the ageing technology in order to add value to the final product. To be successful, the chemistry underlying the ageing process must be better understood. For this purpose, further research, supported by more advanced analytical methodologies, is needed on for key aspects such as: (1) identification and quantification of other phenolic compounds, coumarins and tannins of the aged wine spirit; (2) chemical reactions in which they are involved, and the relationship with chromatic characteristics and sensory properties of the aged wine spirit; (3) bioactive properties of the aged wine spirit modulated by thebarrel characteristics and other ageing factors. More studies about the heat treatment effect on the wood constituents and derived phenolic compounds, namely the coumarins, will also be of great relevance for a comprehensive insight into the ageing process.

Acknowledgments

The author thanks Professor Raúl Bruno de Sousa for his meaningful comments on this manuscript.

Conflicts of Interest

The author declares no conflicts of interest.

References

  1. IBIS World Industry Report 2010. Global Spirits Manufacturing: C1122-GL. Available online: https://www.just-drinks.com/store/samples/2010_ibisworld (accessed on 27 August 2017).
  2. Grigg, D. Wine, Spirits and Beer: World Patterns of Consumption. Geography 2004, 89, 99–110. [Google Scholar]
  3. Léauté, R. Distillation in alambic. Am. J. Enol. Vitic. 1990, 41, 90–103. [Google Scholar]
  4. Cantagrel, R. La qualité et le renom du Cognac dans le monde, sa place dans l’histoire. In Les Eaux-De-Vie Traditionnelles D’origine Viticole; Bertrand, A., Ed.; Lavoisier—Tec & Doc: Paris, France, 2008; pp. 15–38. ISBN 978-2-7430-1040-9. [Google Scholar]
  5. Garreau, C. L’Armagnac. In Les Eaux-De-Vie Traditionnelles D’origine Viticole; Bertrand, A., Ed.; Lavoisier—Tec & Doc: Paris, France, 2008; pp. 39–62. ISBN 978-2-7430-1040-9. [Google Scholar]
  6. Belchior, A.P.; Caldeira, I.; Costa, S.; Tralhão, G.; Ferrão, A.; Mateus, A.M.; Carvalho, E. Evolução das características fisico-químicas e organolépticas de aguardentes Lourinhã ao longo de cinco anos de envelhecimento em madeiras de carvalho e de castanheiro. Ciência e Técnica Vitivinícola 2001, 16, 81–94. [Google Scholar]
  7. Regulation (EC) No. 110/2008. Definition, description, presentation, labelling and protection of geographical indications of spirit drinks. Off. J. Eur. Union 2008, L39, 16–54.
  8. Décret No. 2009-1285. Appellations d’origine contrôlée “Armagnac”, “Blanche Armagnac”, “Bas Armagnac”, “Haut Armagnac” et “Armagnac-Ténarèze”. Journal Officiel de la République Française 2009, 247, 17916–17927.
  9. Décret No. 2009-1146. Appellation d’origine contrôlée “Cognac” ou “Eau-de-vie de Cognac” ou “Eau-de-vie des Charentes”. Journal Officiel de la République Française 2009, 221, 15619–15628.
  10. Decreto-Lei No. 323/94. Estatuto da Região Demarcada das Aguardentes Vínicas da Lourinhã. Diário da República I Série A 1994, 29, 7486–7489.
  11. Caldeira, I.; Santos, R.; Ricardo-da-Silva, J.; Anjos, O.; Belchior, A.P.; Canas, S. Kinetics of odorant compounds in wine brandies aged in different systems. Food Chem. 2016, 211, 937–946. [Google Scholar] [CrossRef] [PubMed]
  12. Canas, S. Aguardentes vínicas envelhecidas. In Química Enológica—Métodos Analíticos. Avanços Recentes No Controlo da Qualidade de Vinhos e de Outros Produtos Vitivinícolas; Curvelo-Garcia, A.S., Barros, P., Eds.; Publindústria, Edições Técnicas: Porto, Portugal, 2015; Capítulo 18.2; pp. 741–771. ISBN 978-989-723-118-6. [Google Scholar]
  13. Baldwin, S.; Black, R.A.; Andreasen, A.A.; Adams, S.L. Aromatic congener formation in maturation of alcoholic distillates. J. Agric. Food Chem. 1967, 15, 381–385. [Google Scholar] [CrossRef]
  14. Nishimura, K.; Ohnishi, M.; Masahiro, M.; Kunimasa, K.; Ryuichi, M. Reactions of wood components during maturation. In Flavour of Distilled Beverages: Origin and Development; Piggott, J.R., Ed.; Ellis Horwood Limited: Chichester, UK, 1983; pp. 241–255. ISBN 0-85312-546-5. [Google Scholar]
  15. Puech, J.-L.; Leauté, R.; Clot, G.; Momdedeu, L.; Mondies, H. Évolution de divers constituants volatils et phénoliques des eaux-de-vie de Cognac au cours de leur vieillissement. Sci. Aliments 1984, 4, 65–80. [Google Scholar]
  16. Nykanen, L. Formation and occurence of flavor compounds in wine and distilled alcoholic beverages. Am. J. Enol. Vitic. 1986, 37, 84–96. [Google Scholar]
  17. Piggott, J.R.; Conner, J.M.; Clayne, J.; Peterson, A. The influence of non-volatile constituents on the extraction of ethyl esters from brandies. J. Sci. Food Agric. 1992, 59, 477–482. [Google Scholar] [CrossRef]
  18. Singleton, V.L. Maturation of wines and spirits: Comparisons, facts and hypotheses. Am. J. Enol. Vitic. 1995, 46, 98–115. [Google Scholar]
  19. Parke, S.A.; Birch, G.G. Solution properties of ethanol in water. Food Chem. 1999, 67, 241–246. [Google Scholar] [CrossRef]
  20. Canas, S.; Belchior, A.P.; Mateus, A.M.; Spranger, M.I.; Bruno de Sousa, R. Kinetics of impregnation/evaporation and release of phenolic compounds from wood to brandy in experimental model. Ciência e Técnica Vitivinícola 2002, 17, 1–14. [Google Scholar]
  21. Aronson, J.; Ebeler, S.E. Effect of polyphenol compounds on the headspace volatility of flavours. Am. J. Enol. Vitic. 2004, 55, 13–21. [Google Scholar]
  22. Puech, J.-L.; Jouret, C.; Goffinet, B. Évolution des composés phénoliques du bois de chêne au cours du vieillissement de l’Armagnac. Sci. Aliments 1985, 5, 379–392. [Google Scholar]
  23. Canas, S.; Belchior, A.P.; Caldeira, I.; Spranger, M.I.; Bruno de Sousa, R. La couleur et son évolution dans les eaux-de-vie Lourinhã pendant les trois premières années du vieillissement. Ciência e Técnica Vitivinícola 2000, 15, 1–14. [Google Scholar]
  24. Caldeira, I.; Bruno de Sousa, R.; Belchior, A.P.; Clímaco, M.C. A sensory and chemical approach to the aroma of wooden aged Lourinhã wine brandy. Ciência e Técnica Vitivinícola 2008, 23, 97–110. [Google Scholar]
  25. Belchior, A.P.; San-Romão, V. Influence de l’oxygène et de la lumière sur l’évolution de la composition phénolique des eaux-de-vie vieillis en bois de chêne. Bull. Liaison Groupe Polyphenols 1982, 11, 598–604. [Google Scholar]
  26. Avakiants, S. Régulation des processus de vieillissement des eaux-de-vie. In Élaboration et Connaissance des Spiritueux; Cantagrel, R., Ed.; Lavoisier—Tec & Doc: Paris, France, 1992; pp. 595–600. ISBN 2-87777-3574. [Google Scholar]
  27. Mosedale, J.R.; Puech, J.-L. Wood maturation of distilled beverages. Trends Food Sci. Technol. 1998, 9, 95–101. [Google Scholar] [CrossRef]
  28. Canas, S.; Caldeira, I.; Belchior, A.P. Comparison of alternative systems for the ageing of wine brandy. Oxygenation and wood shape effect. Ciência e Técnica Vitivinícola 2009, 24, 33–40. [Google Scholar]
  29. Cernîsev, S. Analysis of lignin-derived phenolic compounds and their transformations in aged wine distillates. Food Control 2017, 73, 281–290. [Google Scholar] [CrossRef]
  30. Moutounet, M.; Mazauric, J.P.; Saint-Pierre, B.; Hanocq, J.F. Gaseous exchange in wines stored in barrels. J. Sci. Tech. Tonnellerie 1998, 4, 115–129. [Google Scholar]
  31. Del Álamo-Sanza, M.; Nevares, I. Recent advances in the evaluation of the oxygen transfer rate in oak barrels. J. Agric. Food Chem. 2014, 62, 8892–8899. [Google Scholar] [CrossRef] [PubMed]
  32. Del Álamo-Sanza, M.; Nevares, I.; Mayr, T.; Baro, J.A.; Martínez-Martínez, V.; Ehgartner, J. Analysis of the role of wood anatomy on oxygen diffusivity in barrel staves using luminescent imaging. Sens. Actuators B Chem. 2016, 237, 1035–1043. [Google Scholar] [CrossRef]
  33. Canas, S.; Vaz, M.; Belchior, A.P. Influence de la dimension du fût dans les cinétiques d’extraction/oxydation des composés phénoliques du bois pour les eaux-de-vie Lourinhã. In Les Eaux-de-vie Traditionnelles D’origine Viticole; Bertrand, A., Ed.; Lavoisier—Tec & Doc: Paris, France, 2008; pp. 143–146. ISBN 978-2-7430-1040-9. [Google Scholar]
  34. Philp, J.M. Cask quality and warehouse conditions. In The Science and Technology of Whiskies; Piggott, J.R., Sharp, R., Duncan, R.E.B., Eds.; Longman Scientific & Technical: Essex, UK, 1989; pp. 264–294. ISBN 978-0582044289. [Google Scholar]
  35. Cantagrel, R.; Mazerolles, G.; Vidal, J.P.; Galy, B.; Boulesteix, J.M.; Lablanquie, O.; Gaschet, J. Evolution analytique et organoleptique des eaux-de-vie de Cognac au cours du vieillissement. 2a partie: Incidence de la température et de l’hygrométrie des lieux de stockage. In Élaboration et Connaissance des Spiritueux; Cantagrel, R., Ed.; Lavoisier—Tec & Doc: Paris, France, 1992; pp. 573–576. ISBN 2-87777-3574. [Google Scholar]
  36. Feuillat, F.; Perrin, J.R.; Keller, R. Simulation expérimentale del’interface tonneau. mesure des cinétiques d’imprégnation du liquide dans le bois et d’évaporation de surface. OENO One 1994, 28, 227–245. [Google Scholar] [CrossRef]
  37. Puech, J.-L.; Léauté, R.; Mosedale, J.R.; Mourgues, J. Barrique et vieillissement des eaux-de-vie. In Enologie Fondements Scientifiques et Technologiques; Flanzy, C., Ed.; Lavoisier Tec & Doc: Paris, France, 1998; pp. 1110–1142. ISBN 978-2743002435. [Google Scholar]
  38. Patrício, I.; Canas, S.; Belchior, A.P. Effect of brandies’ agitation on the kinetics of extraction/oxidation and diffusion of wood extractable compounds in experimental model. Ciência e Técnica Vitivinícola 2005, 20, 1–15. [Google Scholar]
  39. Belchior, A.P.; Carvalho, E. A cor em aguardentes vínicas envelhecidas: Método espectrofotométrico de determinação e relação com os teores em fenólicas totais. Ciência e Técnica Vitivinícola 1983, 2, 29–37. [Google Scholar]
  40. Escolar, D.; Haro, M.; Saucedo, A.; Gòmes, J.; Alvàrez, J.A. Evolution de quelques paramètres physico-chimiques des brandies pendant leur vieillissement. Doc. Blanc OIV 1993, 2023, 1–9. [Google Scholar]
  41. Bakker, J.; Bridle, P.; Timberlake, C.F. Tristimulus measurements (CIELab 76) of port wine colour. Vitis 1993, 25, 67–78. [Google Scholar]
  42. Negueruela, A.I.; Echávarri, J.F.; Pérez, M.M. A study of correlation between enological colorimetric indexes and CIE colorimetric parameters in red wines. Am. J. Enol. Vitic. 1995, 46, 353–356. [Google Scholar]
  43. Chassaing, S.; Lefeuvre, D.; Jacquet, R.; Jourdes, M.; Ducasse, L.; Galland, S.; Grelard, A.; Saucier, C.; Teissedre, P.-L.; Dangles, O.; et al. Physicochemical studies of new anthocyan-ellagitannin hybrid pigments: About the origin of the influence of oak C-glycosidic ellagitannins on wine color. Eur. J. Org. Chem. 2015, 1, 55–63. [Google Scholar]
  44. Gambuti, A.; Capuano, R.; Lisanti, M.T.; Strollo, D.; Mioi, L. Effect of aging in new oak, one-year-used oak, chestnut barrels and bottle on color, phenolics and gustative profile of three monovarietal red wines. Eur. Food Res. Technol. 2010, 231, 455–465. [Google Scholar] [CrossRef]
  45. Chinnici, F.; Natali, N.; Sonni, F.; Bellachiona, A.; Riponi, C. Comparative changes in color features and pigment composition of red wines aged in oak and cherry wood casks. J. Agric. Food Chem. 2011, 59, 6575–6582. [Google Scholar] [CrossRef] [PubMed]
  46. Baiano, A.; De Gianni, A.; Mentana, A.; Quinto, M.; Centonze, D.; Del Nobile, M.A. Effects of the heat treatment with oak chips on color-related phenolics, volatile composition, and sensory profile of red wines: The case of Aglianico and Montepulciano. Eur. Food Res. Technol. 2016, 242, 745–767. [Google Scholar] [CrossRef]
  47. Louw, L.; Oelofse, S.; Naes, T.; Lambrechts, M.; van Rensburg, P.; Nieuwoudt, H. Optimisation of the partial napping approach for the sucessful capturing of mouthfeel differentiation between brandy products. Food Qual. Preference 2015, 41, 245–253. [Google Scholar] [CrossRef]
  48. Michel, J.; Albertin, W.; Jourdes, M.; Le Floch, A.; Giodanengo, T.; Mourey, N.; Teissedre, P.-L. Variations in oxygen and ellagitannins, and organoleptic properties of red wine aged in French oak barrels classified by a near infrared system. Food Chem. 2016, 204, 381–390. [Google Scholar] [CrossRef] [PubMed]
  49. Canas, S.; Leandro, M.C.; Spranger, M.I.; Belchior, A.P. Phenolic compounds in a Lourinhã brandy extracted from different woods. In Polyphenols Communications 98, Proceedings of the XIXth International Conference on Polyphenols, Lille, France, 1–4 September 1998; Charbonnier, F., Delacotte, J.-M., Rolando, C., Eds.; Groupe Polyphénols: Bordeaux, France, 1998; Volume 1, pp. 373–374. [Google Scholar]
  50. Lee, K.-Y.M.; Paterson, A.; Piggott, J.R.; Richardson, G.D. Origins of flavour in whiskies and revised flavour wheel: Review. J. Inst. Brew. 2001, 107, 287–313. [Google Scholar] [CrossRef]
  51. Herve du Penhoat, C.L.M.; Michon, V.M.F.; Peng, S.; Viriot, C.; Scalbert, A.; Gage, D. Structural elucidation of new dimeric ellagitannins from Quercus robur L. Roburins A-E. J. Chem. Soc. Perkin Trans. 1993, I, 1653–1660. [Google Scholar] [CrossRef]
  52. Edelmann, A.; Lendl, B. Toward the optical tongue: Flow-through sensing of tannin-protein interactions based on FTIR spectroscopy. J. Am. Chem. Soc. 2002, 124, 14741–14747. [Google Scholar] [CrossRef] [PubMed]
  53. Glabasnia, A.; Hofmann, T. Sensory-directed identification of taste-active ellagitannins in American (Quercus alba L.) and European oak wood (Quercus robur L.) and quantitative analysis in bourbon whiskey and oak-matured red wines. J. Agric. Food Chem. 2006, 54, 3380–3390. [Google Scholar] [CrossRef] [PubMed]
  54. Hufnagel, J.C.; Hofmann, T. Orosensory-directed identification of astringent mouthfeel and bitter-tasting compounds in red wine. J. Agric. Food Chem. 2008, 56, 1376–1386. [Google Scholar] [CrossRef] [PubMed]
  55. Marchal, A.; Cretin, B.N.; Sindt, L.; Waffo-Téguo, P.; Dubourdieu, D. Contribution of oak lignans to wine taste: Chemical identification, sensory characterization and quantification. Tetrahedron 2015, 71, 3148–3156. [Google Scholar] [CrossRef]
  56. Sindt, L.; Gammacurta, M.; Waffo-Teguo, P.; Dubourdieu, D.; Marchal, A. Taste-guided isolation of bitter lignans from Quercus petraea and their identification in wine. J. Nat. Prod. 2016, 79, 2432–2438. [Google Scholar] [CrossRef] [PubMed]
  57. Puech, J.-L. Vieillissement Des Eaux-de-vie en Futs de Chene. Extraction et Evolution de la Lignine et de ses Produits de Degradation. Ph.D. Thesis, Université Paul Sabatier de Toulouse, Toulouse, France, 1978. [Google Scholar]
  58. Canas, S. Study of the Extractable Compounds of Woods (Oak and Chestnut) and the Extraction Processes in the Enological Perspective. Ph.D.Thesis, Instituto Superior de Agronomia, Universidade Técnica de Lisboa, Lisbon, Portugal, 2003. [Google Scholar]
  59. Caldeira, I. The Aroma of Wine Brandies Aged in Wood. Cooperage Technology Relevance. Ph.D. Thesis, Instituto Superior de Agronomia, Universidade Técnica de Lisboa, Lisbon, Portugal, 2004. [Google Scholar]
  60. Chen, J.H.; Ho, C.-T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem. 1997, 45, 2374–2378. [Google Scholar] [CrossRef]
  61. Priyadarsini, K.I.; Khopde, S.M.; Kumar, S.S.; Mohan, H. Free radical studies of ellagic acid, a natural phenolic antioxidant. J. Agric. Food Chem. 2002, 50, 2200–2206. [Google Scholar] [CrossRef] [PubMed]
  62. Sroka, Z.; Cisowski, W. Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food Chem. Toxicol. 2003, 41, 753–758. [Google Scholar] [CrossRef]
  63. Ou, S.; Kwok, K.C. Ferulic acid: Pharmaceutical functions, preparation and applications in foods. J. Sci. Food Agric. 2004, 84, 1261–1269. [Google Scholar] [CrossRef]
  64. Soobrattee, M.A.; Neergheen, V.S.; Luximon-Ramma, A.; Arouma, O.I.; Bahorun, T. Phenolics as potential antioxidant therapeutic agents: Mechanisms and actions. Mutat. Res. 2005, 579, 200–213. [Google Scholar] [CrossRef] [PubMed]
  65. Bakkalbasi, E.; Mentes, O.; Artik, N. Food—Occurence, effects of processing and storage. Crit. Rev. Food Sci. Nutr. 2009, 49, 283–298. [Google Scholar] [CrossRef] [PubMed]
  66. Alañón, M.E.; Castro-Vázquez, L.C.; Diáz-Maroto, M.C.; Gordon, M.H.; Pérez-Coello, M.S. A study of the antioxidant capacity of oak wood used in wine ageing and the correlation with polyphenol composition. Food Chem. 2011, 128, 997–1002. [Google Scholar] [CrossRef]
  67. Alañón, M.E.; Castro-Vázquez, L.; Díaz-Maroto, M.C.; Hermosín-Gutiérrez, I.; Gordon, M.H. Antioxidant capacity and phenolic composition of different woods used in cooperage. Food Chem. 2011, 129, 1584–1590. [Google Scholar] [CrossRef]
  68. Kumar, K.N.; Raja, S.B.; Vidhya, N.; Devaraj, S.N. Ellagic acid modulates antioxidant status, ornithine decarboxylase expression, and aberrant crypt foci progression in 1,2-dimethylhydrazine-instigated colon preneoplastic lesions in rats. J. Agric. Food Chem. 2012, 60, 3665–3672. [Google Scholar] [CrossRef] [PubMed]
  69. Heleno, S.A.; Martins, A.; Queiroz, M.J.R.P.; Ferreira, I.C.F.R. Bioactivity of phenolic acids: Metabolites versus parent compounds: A review. Food Chem. 2015, 173, 501–513. [Google Scholar] [CrossRef] [PubMed]
  70. Bountagkidou, O.G.; Ordoudi, S.A.; Tsimidou, M.Z. Structure-antioxidant activity relationship of natural hydroxybenzaldehydes using in vitro assays. Food Res. Int. 2010, 43, 2014–2019. [Google Scholar] [CrossRef]
  71. Ibrahim, M.N.M.; Sriprasanthi, R.B.; Shamsudeen, S.; Adam, F.; Bhawani, S.A. A concise review of the natural existance, synthesis, properties, and applications of syringaldehyde. BioResources 2012, 7, 4377–4399. [Google Scholar]
  72. Skalicka-Wozniaka, K.; Erdogan Orhanb, I.A.; Cordellc, G.; Mohammad Nabavie, S.; Budzynska, B. Implication of coumarins towards central nervous system disorders. Pharmacol. Res. 2016, 103, 188–203. [Google Scholar] [CrossRef] [PubMed]
  73. Hagerman, A.E.; Riedl, K.M.; Jones, G.A.; Sovik, K.N.; Ritchard, N.T.; Hartzfeld, P.W.; Riechel, T.L. High molecular weight plant polyphenolics (tannins) as biological antioxidants. J. Agric. Food Chem. 1998, 46, 1887–1892. [Google Scholar] [CrossRef] [PubMed]
  74. Da Porto, C.; Calligaris, S.; Celotti, E.; Nicoli, M.C. Antiradical properties of commercial cognacs assessed by the DPPH test. J. Agric. Food Chem. 2000, 48, 4241–4245. [Google Scholar] [CrossRef] [PubMed]
  75. Jordão, A.M.; Correia, A.C.; DelCampo, R.; SanJosé, M.L.G. Antioxidant capacity, scavenger activity, and ellagitannins content from commercial oak pieces used in winemaking. Eur. Food Res. Technol. 2012, 235, 817–825. [Google Scholar] [CrossRef]
  76. Saleem, M.; Kim, J.H.; Alic, M.S.; Lee, Y.S. An update on bioactive plant lignans. Nat. Prod. Rep. 2005, 22, 696–716. [Google Scholar] [CrossRef] [PubMed]
  77. Marteau, C.; Nardello-Rajat, V.; Favier, V.; Aubry, J.-M. Dual role of phenols as fragances and antioxidants: Mechanism, kinetics and drastic solvent effect. Flavour Frag. J. 2013, 28, 30–38. [Google Scholar] [CrossRef]
  78. Goldberg, D.M.; Hoffman, B.; Yang, J.; Soleas, G.J. Phenolic constituents, furans, and total antioxidant status of distilled spirits. J. Agric. Food Chem. 1999, 47, 3978–3985. [Google Scholar] [CrossRef] [PubMed]
  79. Duriez, P.; Cren, C.; Luc, G.; Fruchart, J.C.; Rolando, C.; Teissier, E. Ingestion of cognac significantly increases plasma phenolic and ellagic acid concentrations and plasma antioxidant capacity in humans. In Proceedings of the 26th World Congress (81st Assembly of OIV)—Section Wine and Health, Adelaide, Australia, 11–17 October 2001; OIV: Adelaide, Australia, 2001; pp. 358–369. [Google Scholar]
  80. Umar, A.; Boisseau, M.; Segur, M.-C.; Begaud, B.; Moore, N. Effect of age of Armagnac extract and duration of treatment on antithrombotic effects in a rat thrombosis model. Thromb. Res. 2003, 111, 185–189. [Google Scholar] [CrossRef] [PubMed]
  81. Al Awwadi, N.A.; Borrot-Bouttefroy, A.; Umar, A.; Saucier, C.; Segur, M.-C.; Garreau, C.; Canal, M.; Glories, Y.; Moore, N. Effect of Armagnac fractions on human platelet aggregation in vitro and on rat arteriovenous shunt thrombosis in vivo probably not related only to polyphenols. Thromb. Res. 2007, 119, 407–412. [Google Scholar] [CrossRef] [PubMed]
  82. Schwarz, M.; Rodríguez, M.C.; Martínez, C.; Bosquet, V.; Guillén, D.; Barroso, C.G. Antioxidant activity of Brandy de Jerez and other distillates, and correlation with their polyphenolic content. Food Chem. 2009, 116, 29–33. [Google Scholar] [CrossRef]
  83. Ziyatdinova, G.; Salikhova, I.; Budnikov, H. Chronoamperometric estimation of cognac and brandy antioxidant capacity using MWNT modified glassy carbon electrode. Talanta 2014, 125, 378–384. [Google Scholar] [CrossRef] [PubMed]
  84. Muresan, B.; Cimpoiu, C.; Hosu, A.; Bischin, C.; Gal, E.; Damian, G.; Fischer-Fodor, E.; Silaghi-Dumitrescu, R. Antioxidant content in Romanian traditional distilled alcoholic beverages. Studia Ubb Chemia 2015, 60, 355–370. [Google Scholar]
  85. Garrido, J.; Borges, F. Wine and grape polyphenols—A chemical perspective. Food Res. Int. 2013, 54, 1844–1858. [Google Scholar] [CrossRef]
  86. Botelho, G.; Canas, S.; Lameiras, J. Development of phenolic compounds encapsulation techniques as a major challenge for food industry and for health and nutrition fields. In Nanotechnology in Agri-Food Industry; Grumezescu, A.M., Ed.; Elsevier: London, UK, 2017; Chapter 14; Volume 5, pp. 535–586. ISBN 978-0-12-804304-2. [Google Scholar]
  87. Deibner, L.; Jouret, C.; Puech, J.-L. Substances phénoliques des eaux-de-vie d’Armagnac. I. La lignin d’extraction et les produits de sa dégradation. Ind. Aliment. Agricoles 1976, 93, 401–414. [Google Scholar]
  88. Puech, J.-L.; Jouret, C.; Deibner, L.; Alibert, G. Substances phénoliques des eaux-de-vie d’Armagnac et de rhum. II. Produits de la degradation de la lignin: Les aldéhydes et les acides aromatiques. Ind. Aliment. Agricoles 1977, 94, 483–493. [Google Scholar]
  89. Puech, J.-L. Extraction and evolution of lignin products in Armagnac matured in oak. Am. J. Enol. Vitic. 1981, 32, 111–114. [Google Scholar]
  90. Puech, J.-L.; Jouret, C. Dosage des aldéhydes aromatiques des eaux-de-vie conservées en fûts de chêne: Détection d’adultération. Ann. Falsif. Exp. Chim. 1982, 805, 81–90. [Google Scholar]
  91. Belchior, A.P.; Puech, J.-L.; Carvalho, E.; Mondies, H. Caractéristiques de la composition phénolique du bois de chêne portugais et de quelques eaux-de-vie de vin. Ciência e Técnica Vitivinícola 1984, 2, 57–65. [Google Scholar]
  92. Nabeta, K.; Yonekubo, J.; Miyake, M. Phenolic compounds from the heartwood of European oak (Quercus robur L.) and brandy. Mokuzai Gakkaishi 1987, 33, 408–415. [Google Scholar]
  93. Salagoity-Auguste, M.H.; Tricard, C.; Sudraud, P. Dosage simultané des aldéhydes aromatiques et des coumarines par chromatographie liquide haute performance. J. Chromatogr. 1987, 392, 379–387. [Google Scholar] [CrossRef]
  94. Tricard, C.; Salagoity, M.H.; Sudraud, P. La scopolétine: Un marqueur de la conservation en fûts de chêne. OENO One 1987, 21, 33–41. [Google Scholar] [CrossRef]
  95. Puech, J.-L.; Moutounet, M. Liquid chromatographic determination of scopoletin in hydroalcoholic extract of oak wood and in matured distilled alcoholic beverages. J. Assoc. Off. Anal. Chem. 1988, 71, 512–514. [Google Scholar] [PubMed]
  96. Artajona, J.; Barbero, E.; Llobet, M.; Marco, J.; Parente, F. Influence du “bousinage” de la barrique sur les qualités organoleptiques des brandies vieillies en fûts de chêne. In Les Eaux-de-Vie Traditionnelles D’origine Viticole; Bertrand, A., Ed.; Lavoisier—Tec & Doc: Paris, France, 1991; pp. 197–205. ISBN 2-85206-765-X. [Google Scholar]
  97. Rabier, P.; Moutounet, M. Evolution d’extractibles de bois de chêne dans une eau-de-vie de vin. Incidence du thermotraitement des barriques. In Les Eaux-de-vie Traditionnelles D’origine Viticole; Bertrand, A., Ed.; Lavoisier—Tec & Doc: Paris, France, 1991; pp. 220–230. ISBN 2-85206-765-X. [Google Scholar]
  98. Calvo, A.; Caumeil, M.; Pineau, J. Extraction des polyphénols et des aldéhydes aromatiques pendant le vieillissement du cognac, en fonction du titre alcoolique et du degré d’épuisement des fûts. In Élaboration et Connaissance des Spiritueux; Cantagrel, R., Ed.; Lavoisier—Tec & Doc: Paris, France, 1992; pp. 562–566. ISBN 2-87777-3574. [Google Scholar]
  99. Puech, J.-L.; Moutounet, M. Phenolic compounds in an ethanol-water extract of oak wood and in brandy. Food Sci. Technol. 1992, 25, 350–352. [Google Scholar]
  100. Puech, J.-L.; Maga, J. Influence du brûlage du fût sur la composition des substances volatiles et non volatiles d’une eau-de-vie. Rev. Oenol. 1993, 70, 13–16. [Google Scholar]
  101. Viriot, C.; Scalbert, A.; Lapierre, C.; Moutounet, M. Ellagitannins and lignins in aging of spirits in oak barrels. J. Agric. Food Chem. 1993, 41, 1872–1879. [Google Scholar] [CrossRef]
  102. Canas, S.; Leandro, M.C.; Spranger, M.I.; Belchior, A.P. Low molecular weight organic compounds of chestnut wood (Castanea sativa L.) and corresponding aged brandies. J. Agric. Food Chem. 1999, 47, 5023–5030. [Google Scholar] [CrossRef] [PubMed]
  103. Panosyan, A.G.; Mamikonyan, G.V.; Torosyan, M.; Gabrielyan, E.S.; Mkhitaryan, S.A.; Tirakyan, M.R.; Ovanesyan, A. Determination of the composition of volatiles in Cognac (brandy) by headspace gas chromatography—Mass spectrometry. J. Anal. Chem. 2001, 56, 1078–1085. [Google Scholar] [CrossRef]
  104. Savchuk, S.A.; Vlasov, V.N.; Appolonova, S.S.; Arbuzov, V.N.; Vedenin, A.N.; Mezinov, A.B.; Grigor’yan, B.R. Application of chromatography and spectrometry to the authentication of alcoholic beverages. J. Anal. Chem. 2001, 56, 214–231. [Google Scholar] [CrossRef]
  105. Canas, S.; Belchior, A.P.; Spranger, M.I. Bruno de Sousa R.High-performance liquid chromatography method for analysis of phenolic acids, phenolic aldehydes and furanic derivatives in brandies. Development and validation. J. Sep. Sci. 2003, 26, 496–502. [Google Scholar] [CrossRef]
  106. Canas, S.; Silva, V.; Belchior, A.P. Wood related chemical markers of aged wine brandies. Ciência e Técnica Vitivinícola 2008, 23, 45–52. [Google Scholar]
  107. Cretin, B.N.; Dubourdieu, D.; Marchal, A. Development of a quantitation method to assay both lyoniresinol enatiomers in wines, spirits, and oak wood by liquid chromatography-high resolution mass spectrometry. Anal. Bioanal. Chem. 2016, 408, 3789–3799. [Google Scholar] [CrossRef] [PubMed]
  108. Canas, S.; Leandro, M.C.; Spranger, M.I.; Belchior, A.P. Influence of botanical species and geographical origin on the content of low molecular weight phenolic compounds of woods used in Portuguese cooperage. Holzforschung 2000, 54, 255–261. [Google Scholar] [CrossRef]
  109. Canas, S.; Grazina, N.; Spranger, M.I.; Belchior, A.P. Modelisation of heat treatment of Portuguese oak wood (Quercus pyrenaica Willd.). Analysis of the behaviour of low molecular weight phenolic compounds. Ciência e Técnica Vitivinícola 2000, 15, 75–94. [Google Scholar]
  110. Canas, S.; Belchior, A.P.; Falcão, A.; Gonçalves, J.A.; Spranger, M.I.; Bruno de Sousa, R. Effect of heat treatment on the thermal and chemical modifications of oak and chestnut wood used in brandy ageing. Ciência e Técnica Vitivinícola 2007, 22, 5–14. [Google Scholar]
  111. Alañón, M.E.; Rubio, H.; Díaz-Maroto, M.C.; Pérez-Coello, M.S. Monosaccharide anhydrides, new markers of toasted oak wood used for ageing wines and distillates. Food Chem. 2010, 119, 505–512. [Google Scholar] [CrossRef]
  112. Sanz, M.; Cadahía, E.; Esteruelas, E.; Muñoz, A.M.; Fernández de Simón, B.; Hernández, T.; Estrella, I. Phenolic compounds in chestnut (Castanea sativa Mill.) heartwood. Effect of toasting at cooperage. J. Agric. Food Chem. 2010, 58, 9631–9640. [Google Scholar] [CrossRef] [PubMed]
  113. Le Floch, A.; Jourdes, M.; Teissedre, P.-L. Polysaccharides and lignin from oak wood used in cooperage: Composition, interest, assays: A review. Carbohydr. Res. 2015, 417, 94–102. [Google Scholar] [CrossRef] [PubMed]
  114. Hale, M.D.; McCafferty, K.; Larmie, E.; Newton, J.; Swan, J.S. The influence of oak seasoning and toasting parameters on the composition and quality of wine. Am. J. Enol. Vitic. 1999, 50, 495–502. [Google Scholar]
  115. Acuña, L.; Gonzalez, D.; de la Fuente, J.; Moya, L. Influence of toasting treatment on permeability of six wood species for enological use. Holzforschung 2014, 68, 447–454. [Google Scholar] [CrossRef]
  116. Puech, J.-L. Characteristics of oak wood and biochemical aspects of Armagnac aging. Am. J. Enol. Vitic. 1984, 35, 77–81. [Google Scholar]
  117. Sarni, F.; Moutounet, M.; Puech, J.-L.; Rabier, P. Effect of heat treatment of oak wood extractable compounds. Holzforschung 1990, 44, 461–466. [Google Scholar] [CrossRef]
  118. Chatonnet, P. Influence des Procédés de Tonnellerie et des Conditions D’élevage sur la Composition et la Qualité des Vins Elevés en Fûts de Chêne. Ph.D. Thesis, Institut d’Oenologie, Université de Bordeaux II, Bordeaux, France, 1995. [Google Scholar]
  119. Cretin, B.N.; Sallembien, Q.; Sindt, L.; Daugey, N.; Buffeteau, T.; Waffo-Teguo, P.; Dubourdieu, D.; Marchal, A. How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers. Anal. Chim. Acta 2015, 888, 191–198. [Google Scholar] [CrossRef] [PubMed]
  120. Caldeira, I.; Clímaco, M.C.; Bruno de Sousa, R.; Belchior, A.P. Volatile composition of oak and chestnut woods used in brandy ageing: Modification induced by heat treatment. J. Food Eng. 2006, 76, 202–211. [Google Scholar] [CrossRef]
  121. Chatonnet, P.; Boidron, J.N.; Pons, M. Incidence du traitement thermique du bois de chêne sur sa composition chimique. 2e partie: Évolution de certains composés en fonction de l’intensité de brûlage. Définition des paramètres thermiques de la chauffe des fûts en tonnellerie. OENO One 1989, 4, 223–250. [Google Scholar] [CrossRef]
  122. Canas, S.; Casanova, V.; Belchior, A.P. Antioxidant activity and phenolic content of Portuguese wine aged brandies. J. Food Compos. Anal. 2008, 21, 626–633. [Google Scholar] [CrossRef]
  123. Canas, S.; Spranger, M.I.; Belchior, A.P.; Bruno-de-Sousa, R. Isolation and identification by LC-ESI-MS of hydrolyzable tannins from Quercus pyrenaica Willd and Castanea sativa Mill heartwoods. In Proceedings of the 228th ACS National Meeting, Abstracts of the 4th Tannin Conference, Philadelphia, PA, USA, 22–26 August 2004; Gatenholm, P., Ed.; American Chemical Society: Philadelphia, PA, USA, 2004. [Google Scholar]
  124. Fernández de Simón, B.F.; Sanz, M.; Cadahía, E.; Poveda, P.; Broto, M. Chemical characterization of oak heartwood from Spain forests of Quercus pyrenaica (Willd.) Ellagitannins, low molecular weight phenolic, and volatile compounds. J. Agric. Food Chem. 2006, 54, 8314–8321. [Google Scholar] [CrossRef] [PubMed]
  125. Prida, A.; Boulet, J.-C.; Ducousso, A.; Nepveu, G.; Puech, J.-L. Effect of species and ecological conditions on ellagitannins content in oak wood from na even-aged and mixed stand of Quercus robur L. and Quercus petraea Liebl. Ann. For. Sci. 2006, 63, 415–424. [Google Scholar] [CrossRef]
  126. Jordão, A.M.; Ricardo da Silva, J.M.; Laureano, O. Ellagitannins from Portuguese oak wood (Quercus pyrenaica Willd.) used in cooperage: Influence of geographical origin, coarseness of the grain and toasting level. Holzforschung 2007, 61, 155–160. [Google Scholar] [CrossRef]
  127. Mammela, P.; Savolainen, H.; Lindroos, L.; Kangas, J.; Vartiainen, T. Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. J. Chromatogr. A 2001, 891, 75–83. [Google Scholar] [CrossRef]
  128. Garcia, R.; Soares, B.; Dias, C.B.; Freitas, A.M.C.; Cabrita, M.J. Phenolic and furanic compounds of Portuguese chestnut and French, American and Portuguese oak wood chips. Eur. Food Res. Technol. 2012, 235, 457–467. [Google Scholar] [CrossRef]
  129. Matricardi, L.; Waterhouse, A. Influence of toasting technique on color and ellagitannins of oak wood in barrel making. Am. J. Enol. Vitic. 1999, 50, 519–526. [Google Scholar]
  130. Doussot, F.; De Jeso, B.; Quideau, S.; Pardon, P. Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects. J. Agric. Food Chem. 2002, 50, 5955–5961. [Google Scholar] [CrossRef] [PubMed]
  131. Chira, K.; Teissedre, P.-L. Relation between volatile composition, ellagitannin content and sensory perception of oak wood chips representing different toasting processes. Eur. Food Res. Technol. 2013, 236, 735–746. [Google Scholar] [CrossRef]
  132. García-Estévez, I.; Alcalde-Eon, C.; Le Grottaglie, L.; Rivas-Gonzalo, J.C.; Escribano-Bailón, M.T. Understanding the ellagitannin extraction process from oak wood. Tetrahedron 2015, 71, 3089–3094. [Google Scholar] [CrossRef]
  133. Jourdes, M.; Michel, J.; Saucier, C.; Quideau, S.; Teissedre, P.-L. Identification, amounts, and kinetics of extraction of C-glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips. Anal. Bioanal. Chem. 2011, 401, 1531–1539. [Google Scholar] [CrossRef] [PubMed]
  134. Lurton, L.; Ferrari, G.; Snakkers, G. Cognac: Production and aromatic characteristics. In Alcoholic beverages. Sensory Evaluation and Consumer Research; Piggott, J., Ed.; Woodhead Publishing Limited: Cambridge, UK, 2012; pp. 242–266. ISBN 978-0-85709-051-5. [Google Scholar]
  135. Snakkers, G.; Nepveu, G.; Guilley, E.; Cantagrel, R. Variabilités géographique, sylvicole et individuelle de la teneur en extractibles de chênes sessiles français (Quercus petraea Liebl.): Polyphénols, octalactones et phénols volatils. Ann. For. Sci. 2000, 57, 251–260. [Google Scholar] [CrossRef]
  136. Marchal, A.; Prida, A.; Dubourdieu, D. New approach for differentiating sessile and pedunculate oak: Development of a LC-HRMS method to quantitate triterpenoids in wood. J. Agric. Food Chem. 2016, 64, 618–628. [Google Scholar] [CrossRef] [PubMed]
  137. Cadahía, E.; Munoz, L.; Simón, B.F.; Garcia-Vallejo, M.C. Changes in low molecular weight phenolic compounds in Spanish, French, and American oak woods during natural seasoning and toasting. J. Agric. Food Chem. 2001, 49, 1790–1798. [Google Scholar] [CrossRef] [PubMed]
  138. Canas, S.; Caldeira, I.; Belchior, A.P.; Spranger, M.I.; Clímaco, M.C.; Bruno de Sousa, R. Chestnut wood: A sustainable alternative for the aging of wine brandies. In Food Quality: Control, Analysis and Consumer Concerns; Medina, D.A., Laine, A.M., Eds.; Nova Science Publishers Inc.: New York, NY, USA, 2011; pp. 181–228. ISBN 978-1-61122-917-2. [Google Scholar]
  139. Canas, S.; Caldeira, I.; Mateus, A.M.; Belchior, A.P.; Clímaco, M.C.; Bruno de Sousa, R. Effect of natural seasoning on the chemical composition of chestnut wood used for barrel making. Ciência e Técnica Vitivinícola 2006, 21, 1–16. [Google Scholar]
  140. De Rosso, M.; Cancian, D.; Panighel, A.; Vedova, A.D.; Flamini, R. Chemical compounds release from five different woods used to make barrels for aging wines and spirits. Volatile compounds and polyphénols. Wood Sci. Technol. 2009, 43, 375–385. [Google Scholar] [CrossRef]
  141. Castellari, M.; Piermattei, B.; Arfelli, G.; Amati, A. Influence of aging conditions on the quality of red sangiovese wine. J. Agric. Food Chem. 2001, 49, 3672–3676. [Google Scholar] [CrossRef] [PubMed]
  142. Alañón, M.E.; Schumacher, R.; Castro-Vásquez, L.; Díaz-Maroto, M.C.; Hermosín-Gutiérrez, I.; Pérez-Coello, M.S. Enological potential of chestnut wood for aging Tempranillo wines. Part II: Phenolic compounds and chromatic characteristics. Food Res. Int. 2013, 51, 536–543. [Google Scholar] [CrossRef]
  143. Rodríguez Madrera, R.; Suárez Valles, B.; Diñeiro García, Y.; del Valle Arguelles, P.; Picinelli Lobo, A. Alternative woods for aging distillates—An insight into their phenolic profiles and antioxidant activities. Food Sci. Biotechnol. 2010, 19, 1129–1134. [Google Scholar] [CrossRef]
  144. Canas, S.; Quaresma, H.; Belchior, A.P.; Spranger, M.I.; Bruno de Sousa, R. Evaluation of wine brandies authenticity by the relationships between benzoic and cinnamic aldehydes and between furanic aldehydes. Ciência e Técnica Vitivinícola 2004, 19, 13–27. [Google Scholar]
  145. Doussot, F.; Pardon, P.; Dedier, J.; De Jeso, B. Individual, species and geographic origin influence on cooperage oak extractible content (Quercus robur L. and Quercus petraea Liebl.). Analusis 2000, 28, 960–965. [Google Scholar] [CrossRef]
  146. Quaglieri, C.; Jourdes, M.; Waffo-Teguo, P.; Teissedre, P.-L. Updated knowledge about pyranoanthocyanins: Impact of oxygen on their contents, and contribution in the winemaking process to overall wine color. Trends Food Sci. Technol. 2017, 67, 139–149. [Google Scholar] [CrossRef]
  147. Christensen, C.M. Effects of colour on aroma, flavour and texture judgements of foods. J. Food Sci. 1983, 48, 787–790. [Google Scholar] [CrossRef]
  148. Schwarz, M.; Rodríguez, M.C.; Guillén, D.A.; Barroso, C.G. Analytical charactisation of a Brandy de Jerez during its ageing. Eur. Food Res. Technol. 2011, 232, 813–819. [Google Scholar] [CrossRef]
  149. Rodríguez-Solana, R.; Salgado, J.M.; Domínguez, J.M.; Cortés-Diéguez, S. First approach to the analytical characterization of barrel-aged grape marc distillates using phenolic compounds and colour parameters. Food Technol. Biotechnol. 2014, 52, 391–402. [Google Scholar] [CrossRef] [PubMed]
  150. Es-Safi, N.; Cheynier, V.; Moutounet, M. Study of the reactions between (+)-catechin and furfural derivatives in the presence or absence of anthocyanins and their implication in food color change. J. Agric. Food Chem. 2002, 48, 5946–5954. [Google Scholar] [CrossRef]
  151. Es-Safi, N.; Cheynier, V.; Moutounet, M. Role of aldehydes in the condensation of phenolic compounds with emphasis on food organoleptic properties. J. Agric. Food Chem. 2002, 50, 5571–5585. [Google Scholar] [CrossRef] [PubMed]
  152. Sousa, C.; Mateus, N.; Perez-Alonso, J.; Santos-Buelga, C.; De Freitas, V. Preliminary study of oaklins, a new class of brick-red catechinpyrylium pigments resulting from the reaction between catechin and wood aldehydes. J. Agric. Food Chem. 2005, 53, 9249–9256. [Google Scholar] [CrossRef] [PubMed]
  153. Caldeira, I.; Mateus, A.M.; Belchior, A.P. Flavour and odour profile modifications during the first five years of Lourinhã brandy maturation on different wooden barrels. Anal. Chim. Acta 2006, 563, 264–273. [Google Scholar] [CrossRef]
  154. Renaud, S.; De Lorgeril, M. Wine, alcohol, platelets and The French Paradox for coronary heart disease. Lancet 1992, 339, 1523–1526. [Google Scholar] [CrossRef]
  155. Tunstall-Pedoe, H.; Kuulasmaa, K.; Mahonen, M.; Tolonen, H.; Ruokokoski, E.; Amouyed, P. Contribution of trends in survival and coronary-event rates to changes in coronary heart disease mortality: 10-year results from 37 WHO MONICA project populations. Monitoring trends and determinants in cardiovascular disease. Lancet 1999, 353, 1547–1557. [Google Scholar] [CrossRef]
  156. Alonso, A.M.; Castro, R.; Rodriguez, M.C.; Guillen, D.A.; Barroso, C.G. Study of the antioxidant power of brandies and vinegars derived from Sherry wines and correlation with their content in polyphenols. Food Res. Int. 2004, 37, 715–721. [Google Scholar] [CrossRef]
  157. Pecic, S.; Veljovic, M.; Despotovic, S.; Leskosek-Cukalovic, I.; Jadranin, M.; Tesevic, V.; Niksic, M.; Nikicevic, N. Effect of maturation conditions on sensory and antioxidant properties of old Serbian plum brandies. Eur. Food Res.Technol. 2012, 235, 479–487. [Google Scholar] [CrossRef]
  158. Psarra, E.; Makris, D.P.; Kallithraka, S.; Kefalas, P. Evaluation of the antiradical and reducing properties of selected Greek white wines: Correlation with polyphenolic composition. J. Sci. Food Agric. 2002, 82, 1014–1020. [Google Scholar] [CrossRef]
  159. Ávila-Reyes, J.; Almarz-Abarca, N.; Delgado-Alvarado, E.A.; González-Valdez, L.; Del Toro, G.V.; Páramo, E.D. Phenol profile and antioxidant capacity of mescal aged in oak wood barrels. Food Res. Int. 2010, 43, 296–300. [Google Scholar] [CrossRef]
  160. Yeh, C.-T.; Yen, G.-C. Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats. J. Nutr. Biochem. 2006, 17, 561–569. [Google Scholar] [CrossRef] [PubMed]
  161. Chatonnet, P.; Boindron, J.N. Incidence du traitement thermique du bois de chêne sur sa composition chimique. 1ere partie: Définition des paramètres thermiques de la chauffe des fûts en tonnellerie. OENO One 1989, 23, 77–87. [Google Scholar] [CrossRef]
  162. Sanz, M.; Fernández de Simón, B.; Cadahía, E.; Esteruelas, E.; Muñoz, A.M.; Hernández, M.T.; Estrella, I. Polyphenolic profile as a useful tool to identify the wood used in wine aging. Anal. Chim. Acta 2012, 732, 33–45. [Google Scholar] [CrossRef] [PubMed]
  163. Duval, C.J.; Sok, N.; Laroche, J.; Gourrat, K.; Prida, A.; Lequin, S.; Chassagne, D.; Gougeon, R.D. Dry vs soaked wood: Modulating the volatile extractible fraction of oak wood by heat treatments. Food Chem. 2013, 138, 270–277. [Google Scholar] [CrossRef] [PubMed]
  164. Cantagrel, R.; Mazerolles, G.; Vidal, J.P.; Galy, B. Evolution analytique et organoleptique des eaux-de-vie de cognac au cours du vieillissement. 1ère partie: Incidence des techniques de tonnelleries. In Élaboration et Connaissance des Spiritueux; Cantagrel, R., Ed.; Lavoisier—Tec & Doc: Paris, France, 1992; pp. 567–572. ISBN 2-87777-3574. [Google Scholar]
  165. Puech, J.-L.; Lepoutre, J.-P.; Baumes, R.; Bayonove, C.; Moutounet, M. Influence du thermotraitement des barriques sur l’évolution de quelques composants issus du bois de chêne dans les eaux-de-vie. In Élaboration et Connaissance des Spiritueux; Cantagrel, R., Ed.; Lavoisier—Tec & Doc: Paris, France, 1992; pp. 583–594. ISBN 2-87777-3574. [Google Scholar]
  166. Sanz, M.; Cadahia, E.; Esteruelas, E.; Muñoz, A.M.; Fernández de Simon, B.; Hernández, T.; Estrella, I. Effect of toasting intensity at cooperage on phenolic compounds in acacia (Robinia pseudoacacia) heartwood. J. Agric. Food Chem. 2011, 59, 3135–3145. [Google Scholar] [CrossRef] [PubMed]
  167. Chira, K.; Teissedre, P.-L. Chemical and sensory evaluation of wine matured in oak barrel: Effect of oak species involved and toasting process. Eur. Food Res. Technol. 2015, 240, 533–547. [Google Scholar] [CrossRef]
  168. Híc, P.; Soural, I.; Balík, J.; kulichová, J.; Vrchotová, N.; Tríska, J. Antioxidant capacities of extracts in relation to toasting oak and acacia wood. J. Food Nutr. Res. 2017, 56, 129–137. [Google Scholar]
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Figure 1. Relative importance of some phenolic classes in the aged wine spirits.
Figure 1. Relative importance of some phenolic classes in the aged wine spirits.
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Figure 2. Mean values (n = 24) of chromatic characteristics of the wine brandies aged in different kinds of wood: (a) lightness (L*) and saturation (C*); (b) chromaticity coordinates (a*, b*); AmO—American oak; AO—Allier oak; LO—Limousin oak; PO—Portuguese oak; CT—Chestnut. For each chromatic characteristic, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
Figure 2. Mean values (n = 24) of chromatic characteristics of the wine brandies aged in different kinds of wood: (a) lightness (L*) and saturation (C*); (b) chromaticity coordinates (a*, b*); AmO—American oak; AO—Allier oak; LO—Limousin oak; PO—Portuguese oak; CT—Chestnut. For each chromatic characteristic, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
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Figure 3. Color profile based on the average panel score’s attributes of the wine spirits aged four years in different kinds of wood. For each color attribute, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
Figure 3. Color profile based on the average panel score’s attributes of the wine spirits aged four years in different kinds of wood. For each color attribute, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
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Figure 4. Mean values of antioxidant activity of the wine spirits aged in different kinds of wood (LO—Limousin oak; CT—chestnut). Adapted from [122].
Figure 4. Mean values of antioxidant activity of the wine spirits aged in different kinds of wood (LO—Limousin oak; CT—chestnut). Adapted from [122].
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Figure 5. Mechanism of lignin’s decomposition and formation of derived compounds; proposed by [117].
Figure 5. Mechanism of lignin’s decomposition and formation of derived compounds; proposed by [117].
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Figure 6. Mean values (n = 56) of chromatic characteristics of the wine spirits aged in barrels with different toasting levels: (a) lightness (L*) and saturation (C*); (b) chromaticity coordinates (a*, b*); LT—light toasting; MT—medium toasting; HT–heavy toasting. For each chromatic characteristic, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
Figure 6. Mean values (n = 56) of chromatic characteristics of the wine spirits aged in barrels with different toasting levels: (a) lightness (L*) and saturation (C*); (b) chromaticity coordinates (a*, b*); LT—light toasting; MT—medium toasting; HT–heavy toasting. For each chromatic characteristic, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
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Figure 7. Color profile based on the average panel score’s attributes of the wine spirits aged during four years in barrels with different toasting levels (LT—light toasting; MT—medium toasting; HT—heavy toasting). For each color attribute, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
Figure 7. Color profile based on the average panel score’s attributes of the wine spirits aged during four years in barrels with different toasting levels (LT—light toasting; MT—medium toasting; HT—heavy toasting). For each color attribute, the differences between the aged wine spirits are very significant (p < 0.01). Adapted from [23].
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Figure 8. Mean values of antioxidant activity of the wine spirits aged in barrels with different toasting levels (LT—light toasting; MT—medium toasting; HT—heavy toasting). Adapted from [122].
Figure 8. Mean values of antioxidant activity of the wine spirits aged in barrels with different toasting levels (LT—light toasting; MT—medium toasting; HT—heavy toasting). Adapted from [122].
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Table
Table 1. Low molecular weight phenolic compounds found in aged wine spirits.
Table 1. Low molecular weight phenolic compounds found in aged wine spirits.
ClassCompoundConcentration Range *ReferencesWine Spirits **
Phenolic aldehydesSinapaldehyde0.05–42.31[13,15,29,38,74,87,88,89,90,91,92,93,94,95,96,97,98,99,100,101,102,103,104,105]a,b,c,d,e,j,l
Syringaldehyde0.20–34.20[13,15,17,29,38,74,87,88,89,90,91,92,93,94,98,99,100,101,102,103,104,105]a,b,c,d,e,j,l
Vanillin0.10–18.40[13,15,17,29,38,87,88,89,90,91,92,93,94,97,98,99,100,101,102,103,104,105]a,b,c,d,e,j,k,l
Coniferaldehyde0.05–12.94[13,15,29,38,74,87,88,89,91,92,93,98,99,100,102,103,105]a,b,c,d,e,j,l
Phenolic acidsGallic acid1.00–168.67[15,17,38,74,96,97,99,101,102,105]a,c,f,k,l
Ellagic acid3.90–104.00[38,74,97,99,101,102,105]a,c,k,l
Syringic acid0.40–17.18[15,17,29,38,74,88,89,99,100,101,102,105]a,b,c,d,l
Vanillic acid0.20–10.95[15,17,29,38,74,88,89,99,100,101,102,105]a,b,c,d,l
Ferulic acid0.05–9.94[15,88,89,102,105]a,b,c
Protocatechuic acid0.12–2.27[15]a
Coumaric acid0.02–1.20[15,88]a,b
CoumarinsScopoletin6.00–301.10[38,74,93,94,95,99,102]a,b,c,e,f,g,h,i,l
Umbelliferone0.11–7.00[38,93,102]a,b,c
LignansLyoniresinol3.40–17.50[92,99,106]c,j,l
Phenyl ketonesAcetovanillone0.51–6.21[107]a
* Concentration in mg/L except for coumarins, which are in μg/L; the compounds are arranged in descending order of quantitative importance within each class; ** a—Cognac; b—Armagnac; c—Lourinhã; d—Moldovan; e—American; f—Spanish; g—Bulgarian; h—Canadian; i—Russian; j—Japanese; k—French; l—wine brandy.
Table
Table 2. Hydrolysable tannins found in aged wine spirits.
Table 2. Hydrolysable tannins found in aged wine spirits.
ClassCompoundConcentration Range
EllagitanninsCastalagin2.81–20.75
Vescalagin0.03–0.24
Roburin E0.08–0.19
Grandinin0.06–0.16
GallotanninsMonogalloyl-glucose0.47–5.95
Concentration in mg/L gallic acid. Adapted from [122].
Table
Table 3. Mean concentrations of low molecular weight compounds in wine spirits aged four years in different kinds of wood.
Table 3. Mean concentrations of low molecular weight compounds in wine spirits aged four years in different kinds of wood.
CompoundAmerican oakAllier OakLimousin OakPortuguese OakChestnut
Ellagic acid32.45 a37.19 a49.38 b81.16 c91.27 d
Gallic acid10.49 a13.46 a11.52 a37.80 b218.19 c
Vanillic acid2.97 b2.04 a2.62 a,b2.96 b6.15 c
Syringic acid3.56 a3.58 a,b4.09 a,b,c5.03 c19.77 d
Ferulic acid2.97 a2.85 a3.03 a6.06 b6.39 c
Vanillin6.21 a,b5.50 a6.33 b6.41 b8.28 c
Syringaldehyde15.06 b11.73 a15.02 b14.94 b15.89 b
Coniferaldehyde9.048.279.128.757.78
Sinapaldehyde16.71 b14.63 a,b16.76 b19.65 c11.94 a
Umbelliferone1.48 c0.78 a0.95 b0.98 b0.92 b
Scopoletin164.77 d19.74 b37.12 c10.33 a8.63 a
ΣLMW122.68 a127.68 a144.03 a224.0 b395.93 c
Concentration in mg/L absolute ethanol except for coumarins, which are in μg/L absolute ethanol; mean values (n = 24) followed by different letters (a, b, c, d) in a row are significantly different (p < 0.05); ΣLMW—Sum of low molecular weight phenolic compounds concentrations. Adapted from [56].
Table
Table 4. Mean concentrations of hydrolysable tannins in wine spirits aged four years in different kinds of wood.
Table 4. Mean concentrations of hydrolysable tannins in wine spirits aged four years in different kinds of wood.
CompoundLimousin OakChestnut
Castalagin12.076.33
Vescalagin0.110.17
Roburin E0.140.12
Grandinin0.120.14
Monogalloyl-glucosend5.16
Concentration in mg/L gallic acid; mean values (n = 9); nd—not detected. Adapted from [122].
Table
Table 5. Mean concentrations of low molecular weight compounds in wine spirits aged four years in barrels with different toasting levels.
Table 5. Mean concentrations of low molecular weight compounds in wine spirits aged four years in barrels with different toasting levels.
CompoundLight ToastingMedium ToastingHeavy Tosating
Ellagic acid38.85 a57.69 b87.36 c
Gallic acid42.27 a55.44 b54.22 b
Vanillic acid2.05 a3.20 b4.48 c
Syringic acid5.08 a6.00 b8.64 c
Ferulic acid4.30 a4.49 a5.00 b
Vanillin2.94 a6.43 b10.07 c
Syringaldehyde4.31 a13.00 b26.28 c
Coniferaldehyde3.25 a8.64 b13.55 c
Sinapaldehyde3.99 a14.49 b30.60 c
Umbelliferone0.47 a0.92 b1.64 c
Scopoletin37.3639.4236.58
ΣLMW117.82 a197.10 b295.08 c
Concentration in mg/L absolute ethanol except for coumarins, which are in μg/L absolute ethanol; mean values (n = 56) followed by different letters (a, b, c) in a row are significantly different (p < 0.05); ΣLMW—Sum of low molecular weight phenolic compounds concentrations. Adapted from [56].
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