Analiza Compusilor Sulfurici Volatili Din Cabernet Sauvignon

7/26/2019 Analiza Compusilor Sulfurici Volatili Din Cabernet Sauvignon

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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

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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.

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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.



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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.

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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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Analiza Compusilor Sulfurici Volatili Din Cabernet Sauvignon

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