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7/26/2019 Analiza Compusilor Sulfurici Volatili Din Cabernet Sauvignon
1/11
Evolutions of volatile sulfur compounds of Cabernet Sauvignon wines
during aging in different oak barrels
Dong-Qing Ye a,b, Xiao-Tian Zheng b, Xiao-Qing Xu b, Yun-He Wang b, Chang-Qing Duan b, Yan-Lin Liu a,
a College of Enology, Northwest A&F University, Yangling, Shaanxi 712100, Chinab Centre for Viticulture and Enology, College of Food Science and Nutritional Engineering, China Agricultural University, Beijing 100083, China
a r t i c l e i n f o
Article history:
Received 29 October 2015
Received in revised form 28 January 2016
Accepted 29 January 2016
Available online 4 February 2016
Keywords:
Volatile sulfur compounds
Oak barrel aging
Wine
HS-SPME/GC-FPD
a b s t r a c t
The evolution of volatile sulfur compounds (VSCs) in Cabernet Sauvignon wines from seven regions of
China during maturation in oak barrels was investigated. The barrels were made of different wood grains
(fine and medium) and toasting levels (light and medium). Twelve VSCs were quantified by GC/FPD, with
dimethyl sulfide (DMS) and methionol exceeding their sensory thresholds. Most VSCs tended to decline
during the aging, while DMS was found to increase. After one year aging, the levels of DMS, 2-
methyltetrahy-drothiophen-3-one and sulfur-containing esters were lower in the wines aged in oak bar-
rels than in stainless steel tanks. The wood grain and toasting level of oak barrels significantly influenced
the concentration of S-methyl thioacetate and 2-methyltetrahy-drothiophen-3-one. This study reported
the evolutionof VSCs in wines duringoak barrel aging for the first time andevaluated the influence of bar-
rel types, which would provide wine-makers with references in making proposals about wine aging.
2016 Elsevier Ltd. All rights reserved.
1. Introduction
Volatile sulfur compounds (VSCs) have a strong impact on wine
aroma and mostly responsible for possible reduced flavor resem-
bling rotten eggs, cooked cabbage, onion, garlic and rubber
(Moreno-Arribas, Polo, & Polo, 2009, Chap. 8). It is usually caused
by the presence of excessive concentrations of short-chain thiols,
sulfides, disulfide, thioesters and heterocyclic compound
(Mestres, Busto, & Guasch, 2000). However, it may have possible
positive contributions to wine quality when some VSCs presented
at relatively low concentrations. For example,Segurel, Razungles,
Riou, Salles, and Baumes (2004) reported that dimethyl sulfide
(DMS) levels near 100 lg/L enhanced the fruity notes of Grenache
Noir and Syrah wines. There is an ongoing endeavor to establish
the relationship between the chemistry and sensory contributions
of VSCs to wine aroma. The relationship was report to be
influenced by the complex interactions between various wine con-
stituents (McGorrin, 2011). Recently,Coetzee et al. (2015)demon-
strated that methional can suppress pleasant aroma attributes
linked to volatile thiols, while contributing negative attributes
especially in the presence of 3-isobutyl-2-methoxypyrazine in
Sauvignon Blanc wine. Lytra, Tempere, Marchand, de Revel, and
Barbe (2015) used dynamic analytical and sensory methods to
reveal the variations of wines fruit notes contributed by DMS
and esters during wine tasting and highlighted significant differ-
ences for red-berry and fresh fruit after 5 min, black berry and
jammy fruit after 15 min.
Sulfur compounds can be generated through the biological or
chemical processes, that is, the enzymatic pathway in microorgan-
isms metabolism during wine fermentation involves sulfates, sul-
fites and sulfur containing amino acids (Landaud, Helinck, &
Bonnarme, 2008), or non-enzymatic mechanisms as photochemi-
cal and thermal reaction occurring in winemaking and storage
(Robinson et al., 2013). Therefore it is not surprising that VSCs
are found at various stages of wine production and storage
(Fedrizzi, Magno, Finato, & Versini, 2010; Kinzurik, Herbst-
Johnstone, Gardner, & Fedrizzi, 2015; Landaud et al., 2008;
Moreira et al., 2002; Robinson et al., 2013). However, apart from
the production of H2S in yeast, few of the chemical and/or meta-
bolic pathways for the formation of other VSCs have been reported
or verified during winemaking (Moreno-Arribas et al., 2009).
The effects of wine aging conditions on the evolution of VSCs
have previously been investigated. McCord (2003) demonstrated
that Cabernet Sauvignon wines aged in the stainless steel tanks
with micro-oxygenation had a significantly lower level of free mer-
captans. Meanwhile there was no increase of DMS concentration
with the addition of oxygen and significant decrease in all treat-
ments with adding toasted oak products. Nguyen, Nicolau, Dykes,
http://dx.doi.org/10.1016/j.foodchem.2016.01.139
0308-8146/ 2016 Elsevier Ltd. All rights reserved.
Corresponding author at: College of Enology, Northwest A&F University, No. 22
Xinong Road, Yangling, Shaanxi 712100, China.
E-mail address: [email protected](Y.-L. Liu).
Food Chemistry 202 (2016) 236246
Contents lists available at ScienceDirect
Food Chemistry
j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / f o o d c h e m
http://dx.doi.org/10.1016/j.foodchem.2016.01.139mailto:[email protected]://dx.doi.org/10.1016/j.foodchem.2016.01.139http://www.sciencedirect.com/science/journal/03088146http://www.elsevier.com/locate/foodchemhttp://www.elsevier.com/locate/foodchemhttp://www.sciencedirect.com/science/journal/03088146http://dx.doi.org/10.1016/j.foodchem.2016.01.139mailto:[email protected]://dx.doi.org/10.1016/j.foodchem.2016.01.139http://crossmark.crossref.org/dialog/?doi=10.1016/j.foodchem.2016.01.139&domain=pdf7/26/2019 Analiza Compusilor Sulfurici Volatili Din Cabernet Sauvignon
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and Kilmartin (2010)reported similar results that DMS and thioe-
sters were not affected by oxygen when wines were aged in poly-
ethylene tanks with micro-oxygenation while other compounds
were changed. The work of Ferreira, Rodrigues, Hogg, and De
Pinho (2003)also found that old port wine (barrel aged) contained
fewer VSCs than young port wines due to the decrease of thioalco-
hols during the aging. Although those studies had discussed the
various factors to the respective aging, oxygen in particular, whichgreatly influence the profile of VSCs during aging. However it is still
not well documented that the VSCs variation in such a complex
wine matrix. Nevertheless, the information is practically signifi-
cant to understand the contribution of VSCs on wine quality during
different vinification processes.
Maturation of the wine in oak barrel is commonly in the red
wine making and a complex process accompanied by the develop-
ment of color, aroma and flavor (Moreno-Arribas et al., 2009;
Ribreau-Gayon, Glories, Maujean, & Dubourdieu, 2006). In the
aspect of volatile composition, the wines aged in oak barrel can
acquire a complex aroma by extracting some substances such as
oak lactone and phenolic aldehydes from oak wood. Meanwhile
the oxygen permeation of natural barrel can modify the intrinsic
wine volatile compounds and those extracted from wood (Garde-
Cerdan & Ancin-Azpilicueta, 2006; Jackson, 2008; Ortega-Heras,
Gonzalez-Sanjose, & Gonzalez-Huerta, 2007). Although the low
oxidation conditions of oak barrel was reported to accelerate the
wine oxidation and eliminate VSCs (Jackson, 2008, Chap. 6 and
8), there are few quantitative studies regarding the evolution of
VSCs in wines during oak barrel aging.
Its well known that wine is a complex mixture of several hun-
dred compounds present at different concentrations (Jackson,
2008). The wine-production regions in China are scattered and
have different ecological conditions to enable the winemakers to
produce various types of wines with different styles and flavors.
In this study, the wine samples from seven regions of China in
two consecutive years maturated in four types of oak barrels was
investigated to evaluate a wide range of VSCs in those wines. It is
the first time to provide the information of their profiles affectedby the oak barrel aging.
2. Materials and methods
2.1. Wine samples and aging conditions
The Cabernet Sauvignon base wines were produced at an indus-
trial scale by four wine regions of China: Manasi County, Xinjiang
(44180 N, 86240 E); Hexi Corridor, Gansu (36040 N, 103470 E);
Shacheng County, Hebei (40250 N, 115310 E); Changli County,
Hebei (39440 N, 119110 E) in 2010 and five wine regions Manasi
County, Xinjiang; Hexi Corridor, Gansu; Helanshan, Ningxia
(38340
N, 106020
E); Yanqing County, Beijing (40270
N,115590 E); Deqin County; Yunnan (28290 N, 98550 E) in 2011
(Fig. 4B). The nine wines were abbreviated as 10MNS, 10HXC,
10SC, 10CL, 11MNS, 11HXC, 11HLS, 11YQ and 11DQ. After alcoholic
and malolactic fermentation, those wines were placed in stainless
steel tanks until they were transported to Beijing. The physico-
chemical parameters of those wines were shown inTable S1 (Sup-
plementary Table). The contents of reducing sugar were below
4.0 g/L and the alcoholic degrees were between 13% and 14% (v/
v) for all wines. Other physicochemical parameters of those wines
met the Standards of Wine Product in China (GB/15037-2006).
The wines were aged in four types of oak barrels which were
two wood grains (fine: 13 mm or medium: 35 mm) with two
toasting levels (light: toasting at 150 C for 15 min or medium:
toasting at 175 C for 15 min). These four oak barrels were (1) finewood grains and light toasting (FG_LT); (2) fine wood grains and
medium toasting (FG_MT); (3) medium wood grains and light
toasting (MG_LT); (4) medium wood grains and medium toasting
(MG_MT). The new 225 L barrels were made of 160-years old Quer-
cus petrea obtained from the same forest located in the center
region of France by Yantai Demptos Co., LTD (Yantai, China). The
wines aged in stainless steel tanks (100 L) were used as control
(abbreviated as SST).
The base wines were put into the barrels or stainless steel tanksin June 2011 and 2012 and kept for 12 months in a wine cellar
where relative humidity and temperature conditions were con-
trolled at 7080% and 1416 C, respectively. The barrels and tanks
were refilled every two months to compensate the losses of evap-
oration of water and ethanol. No racking was performed during
aging. The corrections of SO2 were done when the free SO2 levels
were below 30 mg/L.
Wine samples were collected after 0 (before putting in contain-
ers), 4, 8 and 12 months aging in each container. There were 144
samples corresponding to the nine wines in the five aging types
to be used for following analysis. All samples were stored at
20 C before analysis. Each analysis for every sample was carried
out in triplicate. None of the samples presented reduced off-flavors
in the sensory evaluation carried out by the experienced enologist
of Centre for Viticulture and Enology during the aging period.
2.2. Chemicals
The sulfur compounds including (abbreviation and CAS number
in brackets): dimethyl sulfide [DMS, 75-18-3], S-methyl thioac-
etate [MTA, 1534-08-3], S-ethyl thioacetate [ETA, 625-60-5], 2,5-
dimethylthiophene [DMTh, 638-02-8], diethyl disulfide [DEDS,
110-81-6], 2-methyltetrahy-drothiophen-3-one [2MTHF, 13679-
85-1], 3-(methylthio)propionaldehyde (methional) [MTPA, 3268-
49-3], 2-mercaptoethanol [ME, 60-24-2], 2-(methylthio)ethanol
[MTE, 5271-38-5], methyl-3-methylthio propionate [MMTP,
13532-18-8], 3-(methylthio)propyl acetate [PMTE, 16630-55-0],
3-(methylthio)-1-propanol (methionol) [MTP, 505-10-2], 3-
(ethylthio)-1-propanol [ETP, 18721-61-4], 4-(methylthio)-1-butanol [MTB, 20582-85-8], benzothiazole [BT, 95-16-9], and
ethyl-3-methylthio propionate [EMTP, 13327-56-5] were pur-
chased with a purity above 98% from SigmaAldrich (St. Louis,
USA), Fluka (Buchs, Switzerland) and J&K Scientific Ltd. (Beijing,
China).
Individual standard solution for each sulfur compound was pre-
pared with HPLC grade ethanol obtained from Honeywell (New Jer-
sey, USA). Charcoal and inorganic reagents were supplied by
Beijing Chemical Works (Beijing, China). Purified water was gener-
ated using a Milli-Q purification system (Millipore, USA).
2.3. Volatiles extraction by HS-SPME method
The HS-SPME method for volatiles analysis was in accordancewith the study of Fedrizzi, Magno, Moser, Nicolini, and Versini
(2007). Since the mass spectrometer was used as detector in the
exemplary method, the factors (fibre, time of equilibrium and
adsorption, temperature of the sample, ionic strength) were stud-
ied to get the maximum signal for each compound on the FPD
detector. The optimal operating conditions were summarized as
follows. The SPME fibre was CAR/PDMS/DVB (50/30 lm 2 cm)
(Supelco, Bellefonte, PA, USA). For each analysis, 5.0 mL of the sam-
ple was placed in a 15 mL brown vial which contained 1.0 M
MgSO47H2O and a magnetic stirrer and was capped with a
PTFEsilicon septum. Then the sample vial was agitated at
500 rpm and incubated at 40 C for 10 min. Afterwards, the SPME
fibre was inserted through the vial septum and exposed to the
headspace over the liquid sample for 50 min. Then, the fibre wasimmediately desorbed in the GC injection for 8 min.
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2.4. Analysis of volatile sulfur compounds by GC/FPD
The analyses were performed on an Agilent 7890 gas chro-
matography equipped with a H9261 flame photometric detection
system (Varian, Walnut Creek, CA, USA) operating in the sulfur
mode. The gas chromatography conditions were based on the
study ofMestres, Marti, Busto, and Guasch (2000). The separation
was performed by a HP-INNOWAX capillary column
(60 m 0.25 mm I.D., 0.25 lm film thickness, J&W Scientific,
USA). The GC injection was in the splitless mode at temperature
250 C. The oven temperature was programmed as follows: 40 C
(initial hold for 5 min), ramp at 8 C/min to 150 C, and next ramp
at 2 C/min to 180 C, and then ramp at 15 C/min to 220 C
(final hold for 5 min). The carrier gas was pure nitrogen with a con-
stant flow rate at 60 mL/min. The FPD detector was set up at tem-
perature 250 C and supplied with 50 mL/min of hydrogen and
60 mL/min of air. All sulfur compounds were identified by compar-
ing their retention times with the pure standards. A typical chro-
matogram was displayed inFig. S1 (Supplementary Figure).
2.5. Quantification of the sulfur compounds
The standard solutions for the quantification were prepared fol-
lowing published method (Fedrizzi et al., 2007). A white wine
(alcohol strength: 12.0% v/v.; sugar content: 2.30 g/L) was treated
twice with charcoal (3.0 g/L) to remove any sulfur compounds
Fig. 1. Evolution of DMS during maturation of wines aged in five different containers. Within a column of the grid, different letters denote statistically significant differences
(p< 0.05) at each time point.
238 D.-Q. Ye et al./ Food Chemistry 202 (2016) 236246
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and used as a solution media. Because FPD response is a power
function, the calibration curve was constructed by plotting
the log [S-compound] peak area ratios against the log [S-
compound] concentration ratios to obtain the VSCs linear calibra-
tion graphs.
As shown inTable S2 (Supplementary Table), the linearity and
precision were verified and could satisfactorily quantify the wine
samples. Also the recoveries were confirmed by spiking the red
wine with each analyte at three different levels (low, middle and
high concentration of the calibration graphs), and their ranges
were between 70% and 130% for all analytes, which were
satisfactory for analyzing those trace concentrations of sulfur com-
pounds (Mestres, Busto, & Guasch, 2002; Mestres, Marti, et al.,2000).
2.6. Statistical analysis
Linear regression analysis of all calibration standard curves was
carried out on Microsoft Excel 2010. The analysis of variance and
Duncans multiple range test were carried out via SPSS 20.0 Soft-
ware (SPSS Inc., Chicago, IL). The graphs were constructed using
Origin 8.5. Hierarchical clustering and heatmap visualization were
performed using pheatmap package in R (3.0.3) (Team, 2012).
3. Results and discussion
The volatile sulfur compounds were commonly presented in
wine, sixteen compounds presented inTable 1were the analytesof interest in the current study. The ranges of the concentrations
Fig. 2. Evolution of MTP during maturation of wines aged in five different containers. Within a column of the grid, different letters denote statistically significant differences
(p< 0.05) at each time point.
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together with their perception thresholds, odor descriptions and
typical concentration ranges of the nine types of wines were listed
inTable 1as well. DMTh, DEDS and ME were not detected in all
samples. MTB was detected in 11YQ, but two times lower than
its sensory threshold (28.44 lg/L). For ETA, PMTE, MTPA, ETP and
BT, they were quantified in just one or two wine types from
2011 during the aging and had the level below thresholds. These
results indicated that those compounds were not commonly in
Chinese wines, compared with some wines in other countries
(Belancic Majcenovic, Schneider, Lepoutre, Lempereur, & Baumes,
2002; Burin, Marchand, de Revel, & Bordignon-Luiz, 2013;
Fedrizzi, Magno, Badocco, Nicolini, & Versini, 2007; Ferreira et al.,
2003; Moreira et al., 2002).
On the other hand, the other seven compounds (DMS, MTA,
MMTP, MTE, 2MTHF, EMTP, MTP) were detected in almost all the
samples of this study. They were also present in different wines
from other countries, for example Merlot, Marzemino, Teroldego
and Chardonnay wines (Fedrizzi et al., 2007), dry red Botrytiswines
(Fedrizzi et al., 2011), port wines (Ferreira et al., 2003) and so on.
Among these compounds, MTP was the most prominent VSC in
all wine samples and reported as the most abundant VSC in wine
at up to mg/L levels (Landaud et al., 2008). DMS and MET were
the second most abundant VSCs in these wines. Its worth noting
that the DMS contents detected in the current study were remark-
ably higher than those reported in previous studies (Landaud et al.,
2008; Mestres, Busto, et al., 2000). Especially after the one year
Fig. 3. Evolution of MTA during maturation of wines aged in five different containers. Within a column of the grid, different letters denote statistically significant differences
(p< 0.05) at each time point. nq, not quantified.
240 D.-Q. Ye et al./ Food Chemistry 202 (2016) 236246
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aging, the concentration of DMS was over 100 lg/L in most wines.
As shown inTable 1, except for DMS and MTP, other compounds
presented below their perception thresholds. Nevertheless, theymay act synergistically to augment the detection of other
reduced-sulfur odorants (Coetzee et al., 2015; Jackson, 2008), so
we should closely pay attention to those compounds.
3.1. Increase of DMS during the aging
DMS, a light volatile sulfur compound, is found in a wide range
of beverages and foodstuffs and usually described as cabbage,
asparagus and corn (Moreno-Arribas et al., 2009). It has a percep-
tion threshold of 27 lg/L in red wine. Some researchers confirmed
that not only the DMS concentration but also the type of wine can
affect the wine aroma (De Mora, Knowles, Eschenbruch, & Torrey,
1987; Segurel et al., 2004). It could enhance the fruity notes of Gre-
nache Noir and Syrah wines at a level around 100 lg/L (Segurelet al., 2004), and contributed to additional truffle and quince notes
in Port wines (Ferreira et al., 2003). In the work ofSegurel et al.
(2004), it was never perceived as off-flavor even though the DMS
concentration reached 200 lg/L. In this study, the levels of DMS
ranged from 52.34 to 157.27 lg/L in all samples. However, none
of the wines had off-flavors. It indicates that the relatively high
DMS concentration in Cabernet Sauvignon wines might improve
the complexity of wine aroma rather than result in a negative note.
However, further research would be conduced to understand the
interaction of DMS with other compounds and their impact on
wine aroma.
DMS was found to increase during the one year aging ( Fig. 1),
except that the 10MNS wine aged in FG_LT oak barrel showed no
obvious change after aging for 12 months. The results were consis-tent with some previous findings (Fedrizzi et al., 2007; Ferreira
et al., 2003; Segurel, Razungles, Riou, Trigueiro, & Baumes, 2005;
Segurel et al., 2004). Although the DMS contents of most wines
fluctuated during the aging process, they significantly increasedby 9.42142.44% at the end of the trial period, compared with their
base wines (52.3491.19 lg/L). This result confirmed the findings
that DMS released from precursors presented in young wines dur-
ing the aging (Nguyen et al., 2010; Segurel et al., 2005; Ugliano
et al., 2012). DMS is usually generated by yeast from various sulfur
amino acids and derived compounds during alcoholic fermentation
(De Mora et al., 1987). Since DMS is quite volatile and could be
stripped off by CO2, its levels in young wines are usually low
(Moreno-Arribas et al., 2009). However, they can significantly
increase through chemical pathways during wine aging (Segurel
et al., 2005). Furthermore, Loscos et al. (2008) revealed that S-
methyl methionine (SMM) was the principal precursor of DMS in
grapes, accounting for more than 70% of the potential DMS (PDMS).
Segurel et al. (2005)demonstrated the chemical reactivity of SMMconverting into DMS during the model aging of wine. Recently, De
Royer Dupr, Schneider, Payan, Salanon, and Razungles (2014)
reported that vine water deficit could increase the accumulation
of PDMS in berries to result in a better preservation of PDMS dur-
ing winemaking. In this study, a large variation of DMS in different
wines might correlate to their individual matrices and the content
of SMM in individual base, although the reason resulting in is still
not understood. The clear correlations between DMS and SMM in
wine matrix have yet been fully elucidated.
During the aging process, the evolution pattern of DMS (Fig. 1)
in wines aged in stainless steel tanks was obviously different from
that in oak barrels, especially in the wines from 2011 vintage. For
the major wine types, the contents of DMS were significantly lower
in wines matured in oak barrels than in stainless steel tanks after
aging for 8 months. However, the DMS level in wines from
Fig. 4. Hierarchical clustering andheatmap visualization of volatile sulfur compoundsof Cabernet Sauvignon wines from seven regions of China during aging. Numbers 15
after the abbreviations of wine types stand for five aging containers (MG_LT, MG_MT, FG_MT, FG_LT, SST) during wines maturation, separately; numbers after the underline
represent aging time (months).
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Table 1Odor descriptors, thresholds and content ranges of volatile sulfur compounds in wines during aging.
No. Analytea Odor descriptorsb Thresholdb
(wine,lg/L)
Literature
valuesb (lg/L)
Contents in wines (lg/L)
10MNS 10HXC 10SC 10CL 11MNS 11HXC
1 DMS Cooked cabbage, canned
corn, asparagus
27 (red); 25
(white)
162 64.93
146.41
52.34
107.66
85.63
111.76
77.39
115.11
70.76
145.92
61.72
140.30
2 MTA Sulfurous, cheesy, egg 50 (beer) nd 115 3.767.78 nq 2.054.94 2.1416.04 3.2913.31 nq
3 ETA Sulfurous, garlic, onion 10 (beer) nd 180 nq nq nq nq nq nq
4 DMTh Green-like, nutty, sulfury nd 0.7 nd nd nd nd nd nd
5 DEDS Onion, burnt rubber 4.3 nd 85 nd nd nd nd nd nd
6 MTPA Onion, mashed potatoes 250 (beer) nd 57.5 nd nq nd nq nd nd
7 ME Poultry, farmyard, alliaceous 450600 nd 400 nd nd nd nd nd nd
8 MMTP Sulfurous nd 0.04 nd 1.592.69 4.015.91 0.811.31 nq 1.77 1.022.08
9 MTE French bean 250 5139 36.05
112.95
31.2597.32 21.5279.58 17.3769.36 nq 35.22
164.3
10 2MTHF Metallic, natural gas, butane-
like
250 (red); 150
(white)
3.3478 2.266.16 45.3367.56 16.3842.57 18.5128.15 1.8716.37 2.918.50
11 EMTP Sulfurous, metallic 3001000 nd 14.3 1.081.96 4.235.01 1.802.28 2.764.09 1.433.15 1.342.15
12 PMTE Mushroom, onion, garlic 115 (red); 100
(white)
nd 17 nq nq nq nq nq nq
13 MTP Cauliflower, cooked cabbage,
potato
1200 1405000 419.87
1177.12
1991.97
2880.75
1375.30
1761.28
3278.06
4917.15
617.62
1448.12
836.27
1633.47
14 ETP Rancid, sweaty 1188 nq nq nq nq nq 26.04
42.58
15 MTB Metallic-bitter,earthy,chive-
garlic
80 nd 181 nd nd nd nd nd nd
16 BT Smoky, flintstone 50 nd 6 nq nq nd nd 3.004.18 4.18.45
nd, not detected; nq, not quantified.a DMS, dimethyl sulfide; MTA, S-methyl thioacetate; ETA, S-ethyl thioacetate; DMTh, 2,5-dimethylthiophene; DEDS, diethyl disulfide; MTPA, 3-(methylthio)propionaldehyde; ME
propionate; MTE, 2-(methylthio)ethanol; 2MTHF, 2-methyltetrahy-drothiophen-3-one; EMTP, ethyl-3-methylthiopropionate; PMTE, 3-(methylthio)propyl acetate; MTP, 3-(methy
MTB, 4-(methylthio)-1-butanol; BT, benzothiazole.b Reported odor descriptor, threshold and values (Mestres, Busto, & Guasch, 2000; Landaud et al., 2008; Burin et al., 2013; Moreira et al., 2010 ).
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10HXC was not significantly different between these two kinds of
containers during the first 8 months, but it reduced in the one in
stainless steel tank at 12th month, whereas it kept rising in oak
barrel. These results suggested that the 8-month period might be
a key turning point to the variation of DMS between the two kinds
of aging wines. Although the evolution of DMS was not affected by
oxygen exposure during microoxygenated tank (McCord, 2003;
Nguyen et al., 2010) and bottle maturation (Ugliano et al., 2012),wines aged in oak barrels are not only exposed to small amounts
of air that penetrates the wood pores but also in contact with
oak staves. In such a natural micro-oxygenation, some substances
formed by certain physical and chemical processes (Ortega-Heras
et al., 2007) which possibly inhibited the formation of DMS from
its precursors already presented in the wine, or catalyzed the
degradation of DMS. McCord (2003) reported the similar results
that lower concentration of DMS was observed in all treatments
with added toasted oak products in the aging of Cabernet Sauvi-
gnon wine.
3.2. Decrease of thioalcohols during the aging
MTP as an amino acid-related thioalcohol, is considered the
most important heavy volatile sulfur compound in wine, which
can confer odors of cauliflower and cooked cabbage at a concentra-
tion above its perception threshold (1200 lg/L) (Mestres, Busto,
et al., 2000). The contents of MTP in those base wines from differ-
ent regions of China all reached its threshold, which indicated that
it would contribute to aroma defects in wines if no effective control
has been practiced during the following process.
The formation of MTP is clearly related to the catabolism of
methionine via the Ehrlich pathway during alcohol fermentation
(Landaud et al., 2008). As shown inFig. 2, a great variety of MTP
concentration was found in different base wines, this suggested
the difference of methionine metabolism routes in wines from var-
ious regions. However, there was uninvolved biochemical process
in the current study, so as expected, in most wines there was a
propensity of decreasing of MTP during aging, although the trendswere wine-dependent. In addition, this trend was much stronger in
the cases of 11MNS and 11YQ, which showed a noticeable drop
above 30 percent for the five aging containers at the end of the
experiment period. Previous studies reported that MTP decreased
with the presence of oxygen (Ferreira et al., 2003; Nguyen et al.,
2010), likely due to the direct oxidation of MTP to form methional.
Escudero, Hernandez-Orte, Cacho, and Ferreira (2000) found a
decline of methionol along with the formation of methional in a
white wine. However, a study did not find that methional was pre-
sent in a Port wine treated with oxygen (Ferreira et al., 2003). Fur-
thermore, the Strecker mechanism was considered to be the main
pathway for the formation of methional (Silva Ferreira, Guedes de
Pinho, Rodrigues, & Hogg, 2002). For all the samples monitored in
this study, methional was only found in 11HLS wines at a ratherlow level (approximately 20 lg/L) with less change during aging.
Its acetate ester (PMTE) was only detected in the samples from
11YQ in low contents (below 2 lg/L), which were not enough to
offset the decline of MTP. These results indicated that the decrease
of MTP would lead to the formation of other unidentified com-
pounds, such as methionol-S-oxide tentatively identified in a dry
Botrytized red wine (Fedrizzi et al., 2011).
2MTHF as a food flavor constituent is observed in such food-
stuffs as coffee, roasting peanuts and whisky and has a metallic
or natural gas odor when its concentration occurred at a level
above the threshold in wine (250lg/L) (Moreira, de Pinho,
Santos, & Vasconcelos, 2010). It was proposed to be synthesized
from methionine in yeast, but details of this process remained
unclear.Nawrath, Gerth, Muller, and Schulz (2010) have provedthat homocysteine and pyruvate are the precursors of 2MTHF in
the bacteriumChitinophagaFx7914. The contents of 2MTHF in dif-
ferent base wines varied significantly (data was available in Sup-
plementary Fig. S2). Its level in base wine from 11YQ (82.62 lg/
L) was up to 17 times more than that from 11HXC (4.86 lg/L). It
indicated the importance of fermentation control for the formation
of 2MTHF during winemaking. The wines aged in oak barrels all
showed a tendency to deplete 2MTHF during the aging, whereas
some wines aged in stainless steel tank had a propensity to accu-mulate 2MTHF in the early stages of the aging, such as wines from
11HXC and 11YQ, which showed a net increase in 2MTHF across
the whole period studied. At the end of 12 months, it was signifi-
cant lower in wines aged in oak barrels than in stainless steel tank.
This marked decrease observed in barrel-aged wines suggested
that the rate of formation of 2MTHF was slower or the ability of
the wine consumed this compound was more strong.
MTE, another thioether alcohol, has a perception threshold of
250lg/L in hydroalcoholic solution and was described as French
bean-like odor (Mestres, Busto, et al., 2000). Karagiannis and
Lanaridis (1999) considered that it is synthesized via a different
biochemical path than that of methionol, after investigating the
effect of some vinification parameters on it. However, its formation
mechanism during winemaking is not well documented. Nguyen
et al. (2010) reported that the concentration of MTE decreased dur-
ing wine aging in stainless steel tanks, and higher oxygen dosage
(20 mg/L/month) resulted in a greater drop. In the current study,
except for 11MNS, other wines contained abundant contents of
MTE, and the highest level was detected in the base wine from
11HXC (data was available in Supplementary Fig. S3). Besides
slight accumulations of MTE were observed in 10MNS, MTE in
other wines showed a downward trend during the whole aging
period, even if the differences among containers were generally
restricted by wine types. And interestingly, medium grain with
light toasting barrels resulted in a general increase of MTE concen-
trations after 12 months aging, compared with fine grain with the
same level of toasting.
3.3. Lower content of esters in wines aged in oak barrel than instainless steel tank
MTA and ETA were found and monitored during the aging of the
nine types of wine. ETA was only quantified in 11HLS and 11YQ
wines. MTA was detected in all samples, but its level didnt reached
the limit of quantification (2.61 lg/L) in wines from Hexi Corridor
in two vintages (Fig. 3). In wines with off-flavor, their concentra-
tions can reach to 85 and 180 ppb, respectively (Mestres, Busto,
et al., 2000). These compounds not only produce sulfurous or veg-
etable smells for wine, but also can be hydrolyzed to give free thi-
ols at wine pH, which confer a poultry-like or rotten egg off-odors
to wine (Landaud et al., 2008). The formation of these esters is
attributed to the enzymatic esterification of methyl mercaptan
via acetyl coenzyme A (acetyl-CoA) (Landaud et al., 2008). In thecase of MTA, a decline was observed for all cases across the whole
period studied, especially for 10CL and 11MNS, which showed
much greater decreases. After aging for 12 months, there was no
significant effect of aging containers on MTA contents of 10CL,
11MNS and 11DQ, but in the case of 10MNS, 10SC, 11HLS and
11YQ, its content was significantly lower in wines aged in oak bar-
rels than in stainless steel tanks. It seems that MTA was harder to
be kept in wines aged in oak barrels. Though recent studies have
shown that oxygen did not influence this hydrolysis during the
aging (Nguyen et al., 2010; Ugliano et al., 2012), oak wood may
have ability to sorb MTA like other esters (Garde-Cerdan &
Ancin-Azpilicueta, 2006). As displayed in Fig. 3, the effects of types
of oak barrel were significant only at some point of wine matura-
tion, also there were inconsistencies among different wines. Forexample, after 4 months aging, the MTA contents of 10MNS wines
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aged in oak barrels with medium grain were significantly higher
than that with fine grain, whereas 11MNS wines showed opposite
results. Furthermore, this difference didnt remain later.
As other esters quantified in this study, MMTP and EMTP are
considered to have a sulfurous or metallic odor and methionine
may act as their precursors (Mestres, Busto, et al., 2000; Moreira
et al., 2002). AlthoughKaragiannis and Lanaridis (1999)reportedthat concentration of EMTP could be raised by increasing bisulfite,
fermentation temperature and time of wine contacted with yeast
deposit during winemaking, much less information is available
on the evolution of those compounds during wine aging. In the cur-
rent study, their contents were in accordance with the previous
reports (Karagiannis & Lanaridis, 1999; Mestres, Busto, et al.,
2000; Moreira et al., 2002), and the highest content of MMTP
was found in wines from 10SC, while the most abundant EMTP
appeared in wines from 11HLS (data was available in Supplemen-
tary Figs. S4 and S5). During the aging process, their evolution pat-
terns were more restricted by wine types, compared with other
sulfur compounds abovementioned. Moreover the differences of
various aging treatments were generally smaller and not signifi-
cant in all cases at any given time. But interestingly, similar tothe result of MTA, in most cases the highest concentrations of
MMTP and EMTP were observed in wines aged in stainless steel
tanks at the end of aging, it seemed that these esters were also
more difficult to be kept in oak barrel.
3.4. Factors influencing VSCs during the aging
Formation of VSCs during aging can be a challenge for wine-
makers to deal with. To date, however, little research has focused
on the evolution of sulfur compound during aging in oak barrels,
with the exception of some polyfunctional thiols (Blanchard,
Tominaga, & Dubourdieu, 2001; Piano et al., 2014) which are not
considered here.
Table 2showed the results of the multiway ANOVA carried outon the seven VSCs data to evaluate the effect of individual vari-
ables, as well as of interactions among variables. Among the four
variables, wine type and aging time showed the strongest signifi-
cance on all compounds analyzed. This observation supported
the researchers view that wines differ in their patterns of VSCs
evolution (Fedrizzi et al., 2010; Ugliano et al., 2012) and reflected
the fact that the concentration of VSCs changes during aging. The
influences of wood grain and toasting level were significant only
for MTA and 2MTHF. Interactions were in most cases significant
except for MMTP, 2MTHF and MTP in a certain combination. In
general, wood grain is related to the diffusion of oxygen through
the oak barrel (Jackson, 2008), and toasting level is considered to
have the most important influence on the chemical composition
of oak wood (Garde-Cerdan & Ancin-Azpilicueta, 2006). Althoughtheir influences on some volatile compounds such as oak lactones,
volatile phenols and furanic compounds have been reported fre-
quently (Garde-Cerdan & Ancin-Azpilicueta, 2006; Jackson, 2008;
Ortega-Heras et al., 2007; Ribreau-Gayon et al., 2006), there is
very limited data on VSCs. Due to the different changes of oxygen
permeability with time between these two kinds of grain (Del
Alamo-Sanza & Nevares, 2014), and the discrepant reactivities of
wood with the surrounding environment in different wine matri-ces, its easy to understand that the effects of those factors on each
compound of different wine types were not consistent at different
timing. And it also partly reflected the importance of the compat-
ibility of wine and oak barrel. Regardless, we could attain the intu-
itionistic results affected by those combinations in each wine
through the present work.
To understand overall similarities and differences in the varia-
tion of VSCs during maturation among the wines with the five
types of aging containers, hierarchical cluster analysis was per-
formed by using these identified VSCs as variables (Fig. 4). Samples
from the same base wine were obviously clustered together within
a short distance, further demonstrating that the original wine
matrix does has the most significant influence on its profile of
VSCs. And in each wine type, samples with the same aging timegenerally showed the shortest distance, regardless of the aging
containers used. These observations were consistent with the
ANOVA results that wine type and aging time were the most
important factors influencing the evolution of VSCs. Observing
from the farthest hierarchical distance, nine types of wines could
be divided into two major clusters according to VSCs accumulation
pattern. Cluster 1 was composed mainly by 10HXC, 10CL, 11DQ,
11YQ and 11HLS, which presented the similar profiles with more
abundant such sulfur compounds. In this group, wines from
11YQ and 11HLS were closely clustered with richer contents of
most compounds. Wine types in cluster 2 were wines from 10SC,
11MNS, 11HXC and 10MNS, with relatively lower levels of VSCs,
in particular, the concentrations of MTP, EMTP and 2MTHF were
lowest. The formations of these three compounds were associatedwith the methionine metabolism of microorganism during wine-
making (Landaud et al., 2008; Lopez Del Castillo-Lozano, Delile,
Spinnler, Bonnarme, & Landaud, 2007). This suggested that the
methionine metabolism routes in wines from those regions were
not so active, especially in the wines from Manasi County, which
was consistent in two vintages. Its observed that the content of
MMTP in wines from 10SC was the highest among all wines, this
was why samples of 10SC showed more far distance compared
with other wines in this group.
4. Conclusion
This work provided detailed information on the volatile sulfur
compounds profiles of Cabernet Sauvignon wines produced fromseven distinctive wine regions in China during oak barrel matura-
Table 2
Fvalues and significancea of different variables for VSCs during wine aging.
DMS MTA MMTP MTE 2MTHF EMTP MTP
Grain 1.18 ns 7.67 0.05 ns 2.56 ns 22.93 0.03 ns 0.18 ns
Toasting 3.79 ns 4.37 1.47 ns 2.06 ns 6.56 0.95 ns 0.07 ns
Wine type 339.75 7677.83 8526.66 2208.43 10220.15 3416.10 3926.42
Aging time 2498.35 1461.40 100.05 1914.14 1033.80 148.67 526.51
Grain toasting 15.15 12.54 4.79 5.62 0.01 ns 7.08 6.73
Grain wine type 24.03
24.10
2.68
17.42
62.59
3.55
5.85
Grain aging time 7.09 18.94 12.44 64.34 22.38 12.42 6.46
Toasting wine type 9.80 27.00 1.72 ns 19.77 5.15 2.18 11.43
Toasting aging time 9.87 9.87 5.06 14.90 2.92 7.71 2.42 ns
Wine type aging time 71.54 598.57 98.14 276.63 102.98 74.22 46.93
DMS, dimethyl sulfide; MTA, S-methyl thioacetate; MMTP, methyl-3-methylthio propionate; MTE, 2-(methylthio)ethanol; 2MTHF, 2-methyltetrahy-drothiophen-3-one;
EMTP, ethyl-3-methylthiopropionate; MTP, 3-(methylthio)-1-propanol.a *p< 0.05; **p< 0.01, ***p< 0.001; ns, not significant.
244 D.-Q. Ye et al./ Food Chemistry 202 (2016) 236246
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tion and revealed the effect of different containers on the volatiles
evolution during one year aging. Seven compounds (DMS, MTA,
MMTP, MTE, 2MTHF, EMTP, MTP) were commonly found in Chi-
nese wines and discriminated the wines from different regions in
two vintages according to hierarchical cluster analysis. It indicated
that the wine matrix significantly affected the evolution of VSCs
during aging. During the aging process, DMS was found to increase,
in contrast with other sulfur volatiles. VSCs were greatly influ-enced by aging containers, and most compounds were harder to
be kept in oak barrel than in stainless steel tank during the one
year aging. The wood grain and toasting level of oak barrel signif-
icantly affected the concentration of MTA and 2MTHF. The results
of this work would improve the understanding of volatile sulfur
compounds of wines aged in oak barrels and provide winemakers
with references in making the proposals about oak barrel aging
of red wines as well.
Acknowledgments
This work was financially supported by the National Natural
Science Fund of China (Grant No. 31271917) and the China Agricul-
ture Research System (CARS-30-jg-03). The authors thank Dr. Zhi-min Xu of LouisianaState University for the English proofreading of
this manuscript.
Appendix A. Supplementary data
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.foodchem.2016.
01.139.
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