-
ns
Xu
Chinnces
Received in revised form 9 September 2014Accepted 19 September
2014Available online 28 September 2014
Keywords:Bottle stoppers
ing 18-month aging in bottle. The wines were sealed with six
types of bottle stoppers. The results showed
determines red hues in wine (Revilla, GarcA-Beneytez, &
Cabello,2009). Typically, the reactions between anthocyanins and
otherphenolic compounds in wine change its purple tints toward
rubyred (Boulton, 2001; Fulcrand, Duenas, Salas, & Cheynier,
2006).These reactions also promote the stability of wine colour
andreduce the astringency of wine (Boulton, 2001). Meanwhile,
the
outhfeel mainlybottle s
ati, 2000;conrme
wine maturation in bottle was affected by the sealing sysbottle
stoppers (Godden et al., 2001), and oxygen transf(ORT) signicantly
determined the development of wine(Godden et al., 2001;
Skouroumounis et al., 2005). The increaseof ORT can markedly
enhance the degradation speed of anthocy-anins and monomer
avan-3-ols, accelerate the sulphite con-sumption, and increase the
chromaticity (related to the decreaseof sulphite content) (Wirth et
al., 2010). A continuous micro-aer-obic condition with appropriate
OTR in bottled wine can also helpto increase the accumulation of
pyranoanthocyanins and remove
Corresponding author. Tel.: +86 10 62736191; fax: +86 10
62738658.E-mail address: [email protected] (Q.-H. Pan).
1 Both of authors equally contributed to this work.
Food Chemistry 172 (2015) 565574
Contents lists availab
Food Che
lsenamic acids, avan-3-ols, avonols and stilbenes). Besides,
poly-meric phenolics can be formed through condensation
reactionsbetween avan-3-ols and anthocyanins during aging
period.Amongst these compounds, anthocyanins are the main factor
that
pounds on development of wine colour and mdepends on
transferring oxygen through the(Castellari, Matricardi, Arfelli,
Galassi, & AmJulien, Jourdes, & Teissedre, 2011). It has
beenhttp://dx.doi.org/10.1016/j.foodchem.2014.09.1150308-8146/ 2014
Elsevier Ltd. All rights reserved.topperSilva,
d thattem ofer ratequality1. Introduction
Phenolic compounds are responsible for sensory characteristicsin
wine, such as colour, mouthfeel, and avour, and they undergomany
compositional and content changes in the process of wineaging (Li
et al., 2009). Generally, wine phenolic compounds arecomposed of
two main groups, anthocyanins and non-anthocyaninphenolic compounds
(namely, hydroxybenzoic acids, hydroxycin-
unstable anthocyanins from grape skins are converted into
stableoligomeric and polymeric pigments via the combination with
vinylphenol and/or pyruvic acid during wine fermentation and
agingprocesses (Fulcrand, Benabdeljalil, Rigaud, Cheynier,
&Moutounet, 1998). Flavan-3-ols and hydroxycinnamic acids
areinvolved in redox reactions, causing browning reactions and
hazeformation (Cheynier & Ricardo-da-Silva, 1991).
During bottle aging, the effect of evolution of phenolic
com-Bottle agingPhenolic compoundsSensory qualitythat phenolic
compounds presented four evolution patterns along with wine aging
in bottle, mainlydepending on their chemical nature. Most of the
anthocyanins had signicant differences in concentra-tion amongst
the wines sealed with the six bottle stoppers at the 18-month
point. Analysis of partial leastsquares (PLS) revealed that wine
appearance quality was positively correlated with the levels of
malvi-din-3-O-(6-O-acetyl)-glucoside-4-vinylguaiacol, gallocatechin
and dihydrokaempferol-3-O-rhamnos,while the development of
mouthfeel properties was positively associated with the evolutions
ofmalvidin-3-O-glucoside-ethyl-(epi)catechin,
peonidin-3-O-(6-O-acetyl)-glucoside,
malvidin-3-O-(6-O-coumaryl)-glucoside-pyruvic acid and
peonidin-3-O-glucoside-4-vinylphenol. No obvious associationwas
observed between the development of wine sensory characteristics
and the evolution of dissolvedoxygen in wine.
2014 Elsevier Ltd. All rights reserved.Article history:Received
6 June 2014
This study aimed to assess the correspondence between the
evolution of phenolic compounds and thedevelopment of appearance
and mouthfeel in Cabernet Sauvignon (Vitis vinifera L. cv.) dry red
wines dur-Evolution of phenolic compounds and seand their
co-development
Yuan Gao a,1, Yuan Tian a,1, Di Liu a, Zheng Li b, Xiao-Jun Wang
a, Qiu-Hong Pan a,aCenter for Viticulture & Enology, College of
Food Science and Nutritional Engineering,b Food Science and Human
Nutrition Department, Institute of Food and Agricultural Scie
a r t i c l e i n f o a b s t r a c t
journal homepage: www.eory in bottled red wines
Zhang a, Jing-Ming Li a, Jing-Han Huang a,
a Agricultural University, Beijing 100083, China, University of
Florida, Gainesville, FL 32611, USA
le at ScienceDirect
mistry
vier .com/locate / foodchem
-
animal odors (Wirth et al., 2012). However, some different
opin-ions suggested that OTR only affected visual and olfactory
percep-tions of wine, but had little impact on in mouth
attributes(Caill et al., 2010).
The level of dissolved oxygen in bottled wine mainly dependsupon
oxygen concentration in the headspace at bottling and theingress
rate of oxygen into the bottle through stoppers (Goddenet al.,
2001). Therefore, bottle stoppers determine the dissolvedoxygen
concentration in wine to a large extent. Generally, syn-thetic
plugs lead to higher oxygen transmittance, whereas thelower oxygen
concentration is observed in screw-cap bottled
2. Materials and methods
2.1. Wine samples
The wine samples used for this trial were produced in
BeijingDragon Seal Winery Company during a 2009 vintage from
Caber-net Sauvignon (Vitis vinifera L. cv.) grapes grown in Huailai
County,Hebei Province, China. These wines had been aged in French
oakbarrels (Shenyang Fresh Wood Industry Co., Ltd. China) for12
months prior to being bottled. Bottling was performed in mid
Four bottles (considered four biological replicates) were used
for
plugs is smaller than that of the other three corks. The
synthetic
etic
522 284 288 256
566 Y. Gao et al. / Food Chemistry 172 (2015) 565574wines,
compared to other types of stoppers, such as technicalcorks and
natural corks (Lopes, Saucier, Teissedre, & Glories,2006,
2007). Polymer synthetic plugs have a good sealing capacitydue to
good performance on pullout force and resilience, whichleads wines
to a good quality at least within 24 months after bot-tle aging
(Silva, Lambri, & Faveri, 2003). Synthetic plugs tend toretain
more volatile acid and free and total SO2 in wine after8 months of
bottling. Beyond these, some studies suggested thatwines sealed
with synthetic plugs lacked fruity aroma and exhib-ited weak
anti-oxidative activity (Godden et al., 2001;Kwiatkowski,
Skouroumounis, Lattey, & Waters, 2007; Marin,Jorgensen,
Kennedy, & Ferrier, 2007; Silva et al., 2003). However,it also
has been reported that synthetic plugs effectively pre-vented the
generation of corked taste and provided white winewith fruity
aromas (Francis, 2003). Besides bottle stoppers, stor-age
temperature also can cause some differences in aroma,mouthfeel, and
colour of bottled wines (Hopfer, Buffon, Ebeler,& Heymann,
2013).
Bottle-aging is a necessary stage in the production process
ofwines because it helps to modify various organoleptic
propertiesfor good wine quality. The amount of oxygen ingress
related to bot-tle stopper types plays an important role in
development of wineorganoleptic properties. However, most of the
studies so far havebeen undertaken to study the impact of stopper
types on the chem-ical composition, colour, and avour of the
bottled wines. The lit-erature is scarce on the establishment of
the association betweenthe variation of phenolic compounds and the
development of winecolour and mouthfeel properties in bottled
wines. In the presentstudy we used the wine aged in advance in oak
barrels for12 months, and sealed the wine with six types of bottle
stoppersto provide different oxygen environments for post-bottling
matu-ration. Phenolic compounds were qualitatively and
quantitativelyexamined using high performance liquid
chromatography-massspectrometry (HPLCMS). Sensory evaluation was
carried out bya trained panel (20 tasters). The co-development
between phenoliccompounds and the properties of colour and
mouthfeel wasassessed by means of statistical tools. The results
screened outsome phenolic compounds that played a critical role in
the evolve-ment of colour and mouthfeel in wine during
bottle-aging, andthus provided important references for improvement
of Chinesewine quality.
Table 1Physical index of various bottle closures used in this
study (n = 10).
Physical index Closure types
Synthetic plug-1
Synth2
Diameter (mm) 21.74 21.58Length (mm) 44.72 36.41Ovality (mm)
0.18 0.2Moisture content (%) 1 0.9Density (kg/m3) 514 501
Percentage of compression to the original diameter (%) 72
72Rebound rate (%) 98 99plugs showed much lower moisture content
and much higher den-sity compared with the other three corks,
indicating that the poly-mer synthetic plugs possess poor
elasticity.
2.3. Chemicals and standards
Ethyl acetate (analytical grade) was purchased from
BeijingChemical Reagent Company (Beijing, China). Acetonitrile,
metha-nol, formic acid, and acetic acid (HPLC grade) were obtained
fromFisher Scientic Co. (Fairlawn, NJ, USA). Deionised water (
-
2.4.1. Anthocyanins
2000, Shanghai Yarong Biochemistry Factory, Shanghai, China)
at
Wine colour was evaluated using CIELab space, and CIELab
istrvalues were determined according to a published method
(Ayala,Echavarri, & Negueruela, 1997). The wine sample was
lteredthrough a 0.45 lm lter (cellulose acetate and
nitrocellulose,CAN) prior to analysis. Absorbance at 440 nm, 530
nm, and600 nm were measured through a 0.2 cm light path length on
aT6 Spectrophotometer (Shanghai, China). Distiled water was used30
C and re-dissolved in 5 mL methanol. The resultant methanolsolution
was ltered through 0.22 lm nylon membrane ltersprior to HPLCMS
analysis. A Zorbax SB-C18 column (3 50 mm,1.8 lm) was used for the
separation of non-anthocyanin phenoliccomponents. The mobile phase
consisted of (A) aqueous 1% aceticacid and (B) acetonitrile
containing 1% acetic acid. The gradientelution was performed at the
ow rate of 1 mL/min as follows:05% B for 5 min, 58% B for 5 min,
812% B for 5 min, 1218% Bfor 5 min,1822% B for 2 min, 2235% B for 2
min, and 35100%B for 4 min. Injection volume was 20 lL and the
detection wave-length on DAD was 280 nm. Mass spectrometry (MS)
conditionswere set as follows: negative electro-spray ionisation
(ESI) inter-face mode, 30 psi nebuliser pressure, 10 mL/min dry gas
ow rate,325 C dry gas temperature, andm/z 1001500 all mass scan
mode.External standard catechin, quercetin, gallic acid, caffeic
acid, andtrans-resveratrol were used for quantication of avan3-ols,
avo-nols, hydroxybenzoic acids, hydroxycinnamic acids and
stilbenes,respectively.
2.5. Characterisation of colour fractionAnthocyanins were
examined according to our previously pub-lished method (Han et al.,
2008). The wine samples were lteredthrough 0.22-lm lters (cellulose
acetate and nitrocellulose,CAN) and the resulting ltrates were
directly injected into an Agi-lent 1200 LC-UV-MS equipped with a
reversed-phase column [Kro-masil C18; 250 lm (length) 4.65 lm
(diameter)]. A gradientconsisting of solvent A
[water:formic:acetonitrile, 92:2:6 (v/v)]and solvent B
[water:formic:acetonitrile, 44:2:54 (v/v)] wasapplied at a ow rate
of 1 mL/min as follows: 010% B for 1 min,1025% B for 19 min, 2540%
B for10 min, 4070% B for 5 min,70100% B for 5 min. Injection volume
was 30 lL and the detectionwavelength on a diode array detector
(DAD) was 525 nm. Massspectrometry (MS) conditions were set as
follows: positive elec-tro-spray ionisation (ESI) interface mode,
30 psi nebulizer pressure,12 mL/min dry gas ow rate, 300 C dry gas
temperature, and m/z1001500 all mass scan mode. Anthocyanins were
quantied usingmalvidin-3-O-glucoside as an external standard, and
expressed asmilligram per litre on the basis of
malvidin-3-O-glucoside.
2.4.2. Non-anthocyanin phenolic compoundsThe wine sample (100
mL), diluted with an equal volume of
distiled water, was extracted three times with ethyl acetate in
suc-cession and then separated by a separating funnel. The ethyl
ace-tate phase was evaporated to dryness in a rotary evaporator
(SY-Malvidin-3-O-glucoside was purchased from Extra synthese
SA(Genay, France), whereas gallic acid, catechin, caffeic acid,
querce-tin, and trans-resveratrol were received from Sigma Chemical
Co.(St. Louis, MI, USA). All the standards used for identication
andquantication in this study were of HPLC quality.
2.4. Determination of phenolic compounds
Y. Gao et al. / Food Chemas the blank. The colour parameters
that dene the CIELab spaceare lightness (L), redness/green
component (a), yellowness/bluecomponent (b), and hue angle
(Hab).
2.6. Determination of dissolved oxygen in wine
The dissolved oxygen was immediately measured at the open-ing
the bottle through an inoLabOxi730 dissolved oxygen instru-ment
equipped with an automatic mixing electrode (WTW,Germany). The
scale of sensor measurement ranges from 0 to50 mg/L. The
electro-chemical equipment was calibrated beforeevery measurement.
Measures were obtained from the mean valueof three readings after
it was stabilised on a certain value.
2.7. Sensory evaluation
Sensory evaluation of the wines was carried out using 100
posi-tive points provided by International Organisation of Vine
andWine (OIV) (NN106/04, 2004). The attributes were composed
ofappearance (20 score points), fragrance (30 points), mouthfeel(40
points), and overall impressions (10 points) of wines. In
thepresent study, the values of appearance and mouthfeel were
espe-cially taken into account to explore correlation between
theseattributes and phenolic compounds. Twenty panelists (ten
malesand ten females) participated in the sensory sessions every
timeand they were students with ages between 21 and 24, majoringin
Viticulture and Enology of our college. The participants
hadacquired the knowledge of wine tasting and completed a
40-htraining course of wine sensory evaluation. In each session the
par-ticipants were seated in separated booths and the wines,
sealedunder six different types of the stoppers, were presented in
a ran-dom order. The appearance characteristics (clarity, chroma
andhue) and mouthfeel characteristics (purity, intensity,
structure,harmony and aftertaste) were documented and scored. A 10
minbreak was taken between samples. To minimise the systemic
var-iance caused by tasters and to make data more objectively
reectthe difference amongst the wine samples, we performed the
stan-dardisation of the raw data according to condence intervals.
For awine sample sealed under the same type of stoppers (named
aswine-j), the average (named asMj) of the sensory evaluation
scoresfrom all the tasters was calculated and their standard
derivation(rj) was attained as well. The condence interval of
sensory eval-uation for this wine-j sample was in the range of Mj
rj. When asensory evaluation score of the wine-j sample that an
individualtaster gave was within this range of the condence
interval, theraw score was considered to be valid and did not need
to performstandardisation conversion. But when the score was
outside thisrange, the standardisation conversion was applied via
the rawscore plus or minus the rj value. As a result, a new set of
datawas generated for the sensory evaluation of the wine-j
sample,and these data were used for subsequent statistical
analysis.
2.8. Statistical analysis
In this study, quantitative analysis of phenolic compounds
andCIELab values was performed in four experimental sample
repli-cates for each stopper type. Cluster analysis was used to
highlightthe similarities and differences in the wines sealed under
differentstoppers using phenolic compounds as variables. Based on
the sen-sory description and principal component analysis (PCA) of
thewine samples with different stoppers and different bottle
agingperiods, a loading Biplot was provided to visualise the
positioningof sensory quality of various wine samples. Partial
least squares(PLS) regression was applied to establish the
correspondence
y 172 (2015) 565574 567between sensory characteristics and
phenolic components. Full
-
cross-validation was used to validate the PLS model. From
vari-ables importance plot (VIP) value, regression coefcients and
load-ing weights, we can determine that effects of phenolic
compoundson the development of sensory quality in bottle-aged wines
sealedwith different stoppers. All statistical analyses were
performed bySPSS 14.0 software (Chicago, IL, USA).
3. Results and discussion
3.1. Evolutions of dissolved oxygen and phenolic compounds in
winesduring aging in bottle
The dissolved oxygen concentration in the wine rapidlydropped
within the rst three months of the post-bottling, andsubsequently
remained at a low level (Fig. 1). The initial dissolvedoxygen
amount was obtained from the wines that were bottledand held
upright for 12 h. It was observed that the technical cork
568 Y. Gao et al. / Food Chemistrand natural cork allowed more
oxygen to stay inside the bottlecompared to the other stoppers just
after the bottling point. Fromthe 12th month of post-bottling, the
dissolved oxygen content inthe wines using the synthetic plug-3
exhibited an obviousincrease. At 18 months, the wines using the
synthetic plug-1, syn-thetic plug-3, and natural cork contained
higher levels of the dis-solved oxygen compared with the wines
sealed with the otherthree types of stoppers (Fig. 1). This
indicated that both of thesynthetic plugs provided a poor sealing
environment and allowedoxygen to enter the bottles after a year of
bottle storage, which isin agreement with a previous report (Mas,
Puig, Lladoa, & Zamora,2002).
The evolution of phenolic compounds during the wine bottle-aging
was assessed and heatmap cluster analysis was performedusing
package R based on 34 anthocyanins and 33 non-anthocyaninphenolic
compounds detected in this study (Appendix Figs. 16).Although
therewere certain differences in composition and concen-tration of
phenolic compounds amongst thewines using these typesof stoppers,
similar variation patterns were observed over the agingperiod. They
could be grouped into four changing trends. Firstly,phenolic
compounds only appeared at high levels during 9ththrough 12th month
of post-bottling, but stayed at a low level inthe other periods,
suggesting that no gradual evolvement occurred.These compounds
mainly included dephinidin-3-O-glucoside-4-vinylcatechol,
(epi)gallocatechin-(epi)catechin, gallocatechin, epi-catechin,
quercetin, isorhamnetin, and dihydrokaempferol-3-O-rhamnos. The
second trend showedagradual increase in the concen-Fig. 1. Changes
in dissoluble oxygen of Cabernet Sauvignon dry red wines with
thesix types of stoppers during bottle aging (mg/L).tration in 12
or 15-month of the post-bottling and then a decrease.These
compounds following such a trend included cyanidin-3-O-glucoside,
procyanidin B3 (P3),
dihydroquercetin-3-O-rhamnoside,malvidin-3-O-glucoside-(epi)
catechin, myricetin, cis-resveratrol,syringetin-3-O-glucoside, and
ethyl caffeate. The third trend wascharacterised by high
concentration at the early period of the winebottle-aging, followed
by a continuous decrease with the aging per-iod. Many anthocyanin
compounds followed this trend, such aspeonidin-3-O-glucoside,
malvidin-3-O-glucoside, dephinidin-3-O-(6-O-acetyl)-glucoside,
petunidin-3-O-(6-O-acetyl)-glucoside,
mal-vidin-3-O-(6-O-acetyl)-glucoside,
peonidin3-O-(cis-6-O-couma-ryl)-glucoside, and
malvidin-3-O-(cis-6-O-coumaryl)-glucoside.Similarly, procyanidin B2
(P2), ethylgallate and ethyl p-coumaratealso exhibited such a
variation trend. Fourthly, other phenolic com-pounds, such as
malvidin-3-O-(6-O-coumaryl)-glucoside-pyruvicacid, syringic acid,
kaempferol-3-O-glucoside, and glucose ester oftrans-p-coumaric
acid, showed the relatively high levels in the rst6 months of
bottle aging, and then dramatically dropped to a lowlevel. It can
be concluded from the above results that most of avo-nols and
avan-3-ols contributed to the rst and second variationtrends,
whereas some anthocyanins, benzoic acids, and cinnamicacids
affected the third and fourth trends during the wine bottle-aging.
In a word, most of the phenolic compounds had a low levelat the
later periodof aging inbottle (1518 months), except for
somepolymeric pigments such as
peonidin-3-O-(6-O-acetyl)-glucoside,peonidin-3-O-glucoside-4-vinylphenol,
malvidin-3-O-glucoside-ethyl-(epi) catechin, gallic acid,
andmalvidin-3-O-(6-O-acetyl)-glu-coside-4-vinylguaiacol.
Phenolic composition differences amongst the wines using
thedifferent types of stoppers were observed in these four
variationtrends. Compared to the agglomerated cork, the other types
ofstoppers caused more phenolic compounds to follow the secondand
third trends during the bottle-aging. For example,
malvidin-3-O-glucoside-pyruvic acid,
cyanidin-3-O-(6-O-acetyl)-glucoside,malvidin-3-O-(6-O-acetyl)-glucoside-pyruvic
acid, malvidin-3-O-glucoside-4-vinylguaiacol,
malvidin-3-O-(6-O-coumaryl)-gluco-side-4-vinylphenol,
trans-resveratrol, and caftaric acid ester com-plied with the
fourth variation trend in the wines using theagglomerated cork.
However, these phenolic compounds followedthe third trend in the
wines sealed with the other bottle stoppers.
It has been demonstrated that some phenolic compoundsdiminished
irreversibly or were converted into bigger pigmentmolecules along
with wine aging. Generally, phenolic compoundswith low molecular
weight showed a signicant reduction in theconcentration, such as
(+)-catechin, ()-epicatechin, trans-resvera-trol and anthocyanins,
whereas polymeric pigments started to beaccumulated in aged wines
(Castellari et al., 2000). Our resultswere in accordance with these
reports. The changes of phenoliccompounds resulted from various
chemical reactions, some ofwhich were associated with the presence
of oxygen dissolved inwine (Escribano-Bailn, lvarez-Garca,
Rivas-Gonzalo, Heredia, &Santos-Buelga, 2001). Oxygen has been
considered to be capableof causing the oxidation of ethanol to
acetaldehyde (Wildenradt& Singleton, 1974), resulting in the
formation of ethyl-linkedanthocyanins-avanols in wine, such as
methylmethineanthocya-nincatechin polymers and
pyranoanthocyanincatechin polymers(Escribano-Bailn et al., 2001;
Mateus et al., 2003). The polymeri-sation reactions of tannins and
anthocyanins mainly occur in theperiod of aging in barrel or
bottle, which leads wines to a more sta-ble colour and a better
mouthfeel and sensory quality (Mateuset al., 2003). Polymerisation
reactions can cause a rapid declineof free anthocyanins in wine.
Since polymerisation reactions arerelated to the dissolved oxygen
in wine, the evolution of phenolic
y 172 (2015) 565574compounds in wines using different types of
stoppers can be differ-ent during bottle-aging period due to the
different oxygen transferrate through different stoppers.
-
interpretation of the interaction amongst sensory
characteristics
value. Six of seven indices, apart from the value of L, were
all
istr3.2. Main difference of phenolic compounds amongst different
stoppersealed wines
To understand which component in various aging periods
hasstatistically signicant difference (p 6 0.05 or p 6 0.01) in the
con-centration amongst the wines sealed with these six stoppers,
one-way analysis of variance (ANOVA) was conducted based on
theconcentrations of individual phenolic compounds. As shown
inTable 2, most of the anthocyanins had statistically signicant
dif-ference amongst the wines using these stoppers at six
samplingpoints. In particular, ve basic anthocyanins and seven of
ten acyl-ated anthocyanins were obviously differentiated at
18-month ofthe post-bottling. This result indicated that the wine
colouringcomponents were easily affected by the stopper types,
whichwas consistent with the previous reports (Gambuti,
Rinaldi,Ugliano, & Moio, 2013; Godden et al., 2001; Mas et al.,
2002;Skouroumounis et al., 2005). Only a few avan-3-ols, avonolsand
phenolic acids exhibited statistically signicant differenceamongst
these six stopper-sealed wines. Apart from catechin,
ethylp-coumarate and p-coumaric acid, the other avan-3-ols and
phe-nolic acids as well as all avonols did not have signicant
differ-ence amongst the wine samples at 18-month of the
post-bottling(Table 2).
To understand overall similarities and differences in the
varia-tion of phenolic compounds during bottle storage amongst
thewines with six types of bottle stoppers, we performed
hierarchicalcluster analysis using these identied phenolic
compounds as vari-ables (Fig. 2). The wines with the same bottle
storage time wereclustered together within the shortest distance,
regardless of thebottle stopper types used, further demonstrating
that the winesunder different sealing systems possessed the similar
variationtrends of phenolic compounds. The wines aged in the bottle
for0, 3 and 6 months were closer at hierarchical distance and
thewines bottle-aged up to 15 and 18 months were also clustered ina
short distance. The wines bottle-aged for12 months were closeto the
wines aged in the bottle for 0, 3 and 6 months. The
farthesthierarchical distance was observed between the 9-month
bottle-aged wines and the other aging-period wines. This suggested
thatthe 9-month period might be a key turning point to the
variation ofphenolic compounds in the bottle-aged wines. The
results abovealso showed that most of the phenolic compounds in the
winesdecreased to a relatively low concentration after 9 or 12
monthsof the post-bottling. Combined with the varying trends of
dissolvedoxygen throughout the bottle storage, we speculated that
theimpact of bottle stopper types on wine phenolic compounds
beganto be highlighted after 9 months of the bottle aging.
3.3. Variation of colour characteristics in bottled wines
Wine colour characteristics were evaluated using the
CIELabmethod (Appendix Fig. 7). For the wines using different
bottle stop-pers, the value of L all increased within the rst
3-month aging,decreased in succession during the aging period of
615 months,and nally rose slightly during the following 3 months.
As similarto a previous report (Skouroumounis et al., 2005), the
wines usingthe agglomerated corks, technical corks, and natural
corks hadhigher L value than those sealed with the synthetic plugs.
Thewines with the synthetic plug-2 showed the most obvious
uctua-tion of L value over the bottle-aging period. This suggested
thatstopper types could affect the evolution of colour intensity
duringbottle aging, and synthetic plugs can be more suitable for
short-term bottling due to a fast oxidation process (Mas et al.,
2002).Stopper types appeared to affect the redness (a value) of the
bot-
Y. Gao et al. / Food Chemtle-aging wines as well. The wines with
the three synthetic plugshad higher a value than those with the
other three corks. The syn-thetic plugs enhanced the a value of the
wines within 3 months oflocated at the right side of the plot,
corresponding to the principalcomponent 1 (PC1) scores from 6.8 to
8.8. In particular, clarity, col-our depth, and hue were all
distributed in the fourth quadrant andrelatively close to each
other, suggesting that there was an interde-pendent relationship
amongst these three appearance attributes. L
value was in the left of the plot, opposite to the other index.
Thewines at 3-month aging had the highest brightness (L),
especiallythe wines sealed with the natural corks. Overall, the
wines sealedwith the different bottle stoppers gradually proceeded
towardthe six colour index along with the bottle aging process.
Fromthe positioning of these wine samples in the plot, it could be
con-sidered that the wines aged in bottle for 15 months, except
thewines with the synthetic plug-2 (B15), attained a relatively
goodappearance evaluation in terms of clarity, colour depth, and
colourhue. However, the 18-month bottle-aged wines showed a
slightdecrease in appearance quality. The wines using the
syntheticplug-2 for 9 months or longer (B9-B18) appeared at the rst
quad-rant near to a and b values in the plot, representing deeper
red-ness and yellowness. However, these wines were all given
poorappearance description. According to the distance between
thepoints representing the wine samples and wine appearance
attrib-uters, we observed that the wines with the technical cork
(D1218), agglomerated cork (E1218), and natural cork (F1218)and was
allowed to understand how these index affected overallsensory
quality of the wine samples analysed.
3.4.1.1. Positioning analysis of appearance characteristics.
Fig. 3Ashows a loading Biplot of three appearance attributes and
four col-our parameters. Appearance attributes include clarity,
colourdepth (saturation), and colour hue (shade or tint), whereas
fourcolour parameters consist of L value, a value, b value, and
Habthe post-bottling, whereas the opposite observations were found
inthe wines sealed by the other three types of corks. The value of
b
continually increased during the 18 months of bottle-aging, and
itsenhancement showed the largest in the wines using the
syntheticplug-2. Meanwhile, the wines with the synthetic plug-2 had
highervalue of Hab in comparison with the other wine samples. In
short,amongst six bottle stoppers used in this study, the short
syntheticplug-2 imparted the lowest lightness (L), strongest
redness (a),deepest yellowness (b), and highest hue (Hab) to the
wines at18 months (Appendix Fig. 7). Mas et al. reported that
syntheticplugs allowed oxygen to enter the bottles after a year of
bottle-aging (Mas et al., 2002). The effect of OTR on colour change
inred wine has been reported, and the wine aged with the
minimalheadspace presented the least redness and lightness
throughoutthe bottle-aging period of 24 months (Kwiatkowski et al.,
2007).These explained why the wine using the short synthetic plug
hadthe highest colour parameters after 18-month bottle aging in
thisstudy. However, there are also some different viewpoints.
Forexample, Hopfer et al. thought that the changes in yellownessand
hue value, expressed as b and h values, greatly differedamongst the
wines mainly owing to the difference in the bottle-aging
temperature rather than the sealing systems (Hopfer et
al.,2013).
3.4. Correlation between phenolic compounds and development
ofsensory characteristics
3.4.1. Positioning analysis of sensory characteristicsLoading
Biplot of PCA on sensory characteristics provided an
y 172 (2015) 565574 569showed better appearance quality in
comparison with the winesusing the polymeric synthetic plugs.
Combined with the variationof dissolved oxygen during this period
(Fig. 1), the development
-
Table 2One-Way ANOVA of various phenolic compounds amongst red
wines sealed with different stoppers.
Numbers Phenolic compounds Aging time (months)
3 6 9 12 15 18
1 Dephinidin-3-O-glucoside 1.329 35.586 1.581 2.872 57.773
6.873
2 Cyanidin-3-O-glucoside 7.952** 0.810 1.130 0.745 n.s.
3358.897
3 Petunidin-3-O-glucoside 17.715 26.736 0.543 1.202 202.259
17.512
4 Malvidin-3-O-(6-O-caffeoyl)-glucoside 35.360 7.945** n.s. n.s.
n.s. n.s.5 Peonidin-3-O-glucoside 2.082 3.448* 0.820 1.038 3.818*
23.898
6 Malvidin-3-O-glucoside 3.401* 69.962 14.198 5.219** 20.944
20.936
7 Dephinidin-3-O-(6-O-acetyl)-glucoside 3.934* 1.979 1.105 0.833
7.983** 20.277
8 Peonidin-3-O-glu-pyruvic acid 6.112** 46.072 8.235** 46.696
n.s. n.s.9 Malvidin-3-O-glu-pyruvic acid 2.600 81.967 1.309 0.506
0.130 0.927
10 Malvidin-3-O-glu-acetaldehyde 3.166* 6.510** 9.969** 20.086
n.s. 1871.357
11 Cyanidin-3-O-(6-O-acetyl)-glucoside 9.164** 5.062* 3.939*
3.678* 2180.576 0.08512 Malvidin-3-O-(6-O-acetyl)-glu-pyruvic acid
5.035* 2.389 1.454 0.801 58.921** 77.680
13 Petunidin-3-O-(6-O-acetyl)-glucoside 4.032* 2.025 1.345 1.951
n.s. 62.484
14 Malvidin-3-O-(6-O-acetyl)-glu-acetaldehyde n.s. 17.005 41.852
58.278 467.753 4.000*
15 Malvidin-3-O-glu-ethyl-(epi)catechin 28.052 12.756 87.849
n.s. 85.008 171.002
16 Peonidin-3-O-(6-O-acetyl)-glu-pyruvic acid 50.318 n.s.
243.992 57.384 n.s. n.s.17 Dephinidin-3-O-glu-4-vinylphenol 4.146*
1.756 n.s. n.s. 75.358 853.884
18 Peonidin-3-O-(6-O-acetyl)-glucoside 17.912 1.363 1.403 1.388
24.304 62.067
19 Malvidin-3-O-(6-O-acetyl)-glucoside 0.867 9.324** 1.100
9.610** n.s. 92.382
20 Cyanidin-3-O-(6-O-coumaryl)-glucoside n.s. n.s. n.s. n.s.
n.s. 103.458
21 Malvidin-3-O-(6-O-coumaryl)-glu-pyruvic acid 12.094 5.976**
n.s. n.s. n.s. 151.857
22 Dephinidin-3-O-glu-4-vinylcatechol 2.353 n.s. 15.644 3.198*
n.s. n.s.23 Malvidin-3-O-(trans-6-O-coumaryl)-glucoside 58.450
4.365* n.s. n.s. 2.319 16.668
24 Peonidin-3-O-glu-4-vinylcatechol 36.021 141.544 4.440*
7.711** 11.472 465.777
25 Peonidin-3-O-(cis-6-O-coumaryl)-glucoside 2.443 1.908 4.090*
7.452** 730.251 3.01726 Malvidin-3-O-(cis-6-O-coumaryl)-glucoside
19.100 4.747* 0.316 9.199** n.s. 451.876
27 Peonidin-3-O-glu-4-vinylphenol 1.039 511.079 4764.110 614.620
4.376* n.s.28 Malvidin-3-O-glu-4-vinylphenol 1.541 1.826 0.825
15.010 n.s. 3.00829 Malvidin-3-O-glu-4-vinylguaiacol 10.491 200.526
829.226 402.542 3.424* n.s.30
Malvidin-3-O-(6-O-acetyl)-glu-4-vinylphenol 1.839 94.123 1.379
11.137 490.006 1.77931
Malvidin-3-O-(6-O-caffeoyl)-glu-4-vinylphenol 23.030 293.783 n.s.
n.s. n.s. n.s.32 Malvidin-3-O-(6-O-acetyl)-glu-4- vinylguaiacol
n.s. n.s. n.s. 4.638* n.s. 1.11233
Malvidin-3-O-(6-O-coumaryl)-glu-4-vinylphenol 1.097 6.776** 2.542
5.806** n.s. n.s.34 Cinnamic acid 9.819** 3.501* 1.061 0.792 2.601
n.s.35 Gallic acid 4.924* 0.213 0.674 0.558 3.908* 2.40736
Dimer(epi)gallocatechin-(epi)catechin 6.175** 61.307 10.190** 0.601
1.389 n.s.37 Gallocatechin n.s. n.s. n.s. 0.875 0.924 n.s.38
Procyanidin B2 (P2) 0.725 1.191 2.162 1.607 2.923 n.s.39 Catechin
2.705 0.425 n.s. 0.720 4.956* 109.755
40 Caffeic acid 2.644 0.327 0.741 1.230 0.807 2.58041
Procyanidin B3 (P3) n.s. 1.501 15.936 1.698 n.s. n.s.42 Syringic
acid 4.666* 0.693 n.s. n.s. n.s. n.s.43 Enthylgallate 1.317 0.130
0.436 1.668 0.982 n.s.44 Epicatechin 2.019 n.s. 0.189 n.s. n.s.
n.s.45 p-Coumaric acid 5.468** 0.413 n.s. 0.316 1.861 4.547*
46 Dihydroquercetin-3-O-hexoside n.s. n.s. 5.749** n.s. n.s.
n.s.47 Dihydroquercetin 2.218 0.270 6.418** 0.359 0.508 n.s.48
Myricetin-3-O-glucoside n.s. 668.961 n.s. n.s. 1.347 n.s.49 Ethyl
protocatechuate 1.002 0.417 0.960 0.292 1.265 n.s.50
Dihydroquercetin-3-O-rhamnoside 2.092 0.027 1.692 1.179 n.s. n.s.51
Quercetin-3-O-glucuronide 2.654 0.110 1.641 0.051 n.s. n.s.52
Malvidin-3-glucoside-(epi)catechin 9.238** 10.933 5.169** 0.736
n.s. n.s.53 Laricitrin-3-O-glucoside 309.525 63.657 0.807 1.117
n.s. n.s.54 Dihydrokaempferol-3-O-rhamnos n.s. n.s. n.s. 0.610
1.402 n.s.55 Myricetin 8.907** 2.865 1.173 1.353 2.983 n.s.56
Cis-resveratrol 2.942 0.273 2.992 n.s. 1.786 n.s.57
Syringetin-3-O-glucoside 13.881 3.862* 69.260 0.424 2.759 n.s.58
Kaempferol-3-O-glucoside 2.937 6.462** n.s. n.s. n.s. n.s.59
Isorhamnetin-3-O-glucoside n.s. n.s. n.s. n.s. n.s. n.s.60 Ethyl
caffeate 3.081 0.747 2.226 0.378 1.160 2.12961 Trans-resveratrol
0.218 0.142 1.431 0.364 1.011 n.s.62 Quercetin n.s. n.s. 1.583 n.s.
n.s. n.s.63 Iaricitrin 4.839* 0.106 1.225 0.180 n.s. n.s.64 Ethyl
p-coumarate 1.490 0.089 2.346 0.805 0.964 10.914
65 Isorhamnetin n.s. n.s. 1.513 n.s. n.s. n.s.66 Caftaric acid
ester n.s. 9.756** 302.282 2.576 4.635* n.s.67 Glucose ester of
trans-p-coumaric acid 27.149 26.323 347.375 n.s. n.s. n.s.
n.s. No signicant differerce there. The data in bold are
highlighted due to very high F-value.** A signicance level of p
< 0.01.* A signicance level of p < 0.05.
570 Y. Gao et al. / Food Chemistry 172 (2015) 565574
-
istrY. Gao et al. / Food Chemof the wine appearance quality did
not seem to have the directassociation with dissolved oxygen
content.
3.4.1.2. Positioning analysis of mouthfeel features. In this
study themouthfeel terms included genuineness, positive intensity,
struc-ture, harmony, and aftertaste. These mouthfeel features were
allpositioned at the right side of the plot, scoring from 0.75 to
0.95of PC1 (Fig. 3B). There was a synergistic effect as to
structure andharmony of wine, the two being close to each other in
the plot.Overall, most of the wines bottle-aged for 36 months had a
rela-tively good genuineness and aftertaste, especially for the
winesusing the technical corks (E6), natural corks (F6), and
syntheticplug-3 (C6). The 15-month bottle-aged wines with the
syntheticplug-1(A15), synthetic plug-3 (C15), agglomerated cork
(D15),and technical cork (E15) were the nearest to the points
represent-ing wine structure and harmony. Relative to the 12-month
wines,the 15-month wines with the short synthetic plug-2 (B15) and
nat-ural cork (F15) also had a good mouthfeel description. In
contrast,most of 9- and 18-month wines were separated from the
pointsrepresenting six mouthfeel features, implying that these
wineshad a poor mouthfeel performance at the two aging periods.
Com-bined with the result of PCA, we speculated that the poor
overallmouthfeel description of the 9-month wines might be related
toa dramatic alteration of phenolic compounds (Lorrain et al.,2013;
Marquez, Serratosa, & Merida, 2014). The point representing
Fig. 2. Cluster analysis based on phenolic compounds in
bottle-aged dry red winessealed with different bottle stoppers.
Letters represent six bottle stoppers: syntheticplug-1 (A),
synthetic plug-2 (B), synthetic plug-3 (C), aglomerated cork (D), 1
+ 1technical cork (E) and natural cork (F), respectively. Numbers
after the letterrepresent aging time (months).the 18-month
bottle-aged wines with the synthetic plug-2 (B18)was at the far
left, which indicated that the mouthfeel quality ofthe wines
declined signicantly.
3.4.2. Correlation between variation of phenolic compounds
anddevelopment of sensory attributes3.4.2.1. Correlation between
phenolic compounds and appearancecharacteristics. Partial least
squares (PLS) regression analysis wasused to establish the
association between the variation of com-pounds and the development
of sensory properties during the wineaging in bottle. The
correlation between matrix X (phenolic com-pounds) and matrix Y
(sensory properties) was reected by a load-ing plot (Fig. 4). A
series of numbers (167) in this plotcorresponded to these phenolic
compounds in Table 2. The rsttwo principal components (PCs)
accounted for about 62% of thetotal variables. As shown in the
loading plot (Fig. 4A) and variablesimportance plot (VIP) value of
the rst two PCs (Appendix Table 1),the points representing these
appearance characteristics, exceptfor L value, were all positioned
at the right side of the loading plot,and they had a closely
positive correlation with
malvidin-3-O-(6-O-acetyl)-glucoside-4-vinylguaiacol (No. 32),
gallocatechin (No.37), and dihydrokaempferol-3-O-rhamnos (No. 54).
These sug-gested that the increase in the concentration of these
three com-pounds might improve the appearance characteristics of
thewine, but could cause the reduction of the wine lightness.
Previousreports provided some explanations regarding the promotion
ofthe phenolic compounds on wine appearance quality. For
example,pyranoanthocyanins, like
malvidin-3-O-(6-O-acetyl)-glucoside-4-vinylguaiacol (No. 32), have
been conrmed to have the visiblemaximum absorbance at a higher
wavelength than their corre-sponding anthocyanins (e.g.
malvidin-3-O-(6-O-acetyl)-glucoside),which imparted a reddish
tonality to red wine. Moreover, thesevinyl pyranoanthocyanins were
relatively more stable and stayedlonger in aged red wines (de
Freitas & Mateus, 2011; Mateuset al., 2003). In the present
study, the above three phenolic com-pounds all followed the rst
varying trend along with the processof the bottle-aging for all the
wines, that is, high levels appeared at12 months of the
post-bottling and stayed at a low level in theother periods. It can
be concluded that the attenuation of wineappearance quality in the
late period of bottle-aging might berelated to the decline of these
three compounds.
Except for these three components, other phenolic compoundswere
distributed at the left side of the plot and they were nega-tively
correlated with ve appearance indicators, especially
peoni-din-3-O-glucoside (No. 5), malvidin-3-O-glucoside (No.
6),dephinidin-3-O-(6-O-acetyl)-glucoside (No. 7),
petunidin-3-O-(6-O-acetyl)-glucoside (No. 13),
malvidin-3-O-(6-O-acetyl)-glucoside(No. 19), gallic acid (No. 35),
caffeic acid (No. 40), and ethyl p-coumarate (No. 64). This
suggests that wines develop toward agood appearance evaluation
accompanying the reduction in theconcentrations of these compounds
during bottle-aging. Thisobservation can be explained by the
previous reports. For example,it has been observed that the content
of the free or monomericanthocyanins gradually decrease or even
disappeared with aging(Eiro & Heinonen, 2002; Gutirrez,
Lorenzo, & Espinosa, 2005).Instead, the stable pigments, such
as pyranoanthocyanins andpolymeric pigments, as red wine aged, were
formed through chem-ical modications of anthocyanin molecules, or
condensation reac-tions between avan-3-ols and anthocyanidins
(Carvalho, Oliveira,De Freitas, Mateus, & Melo, 2010). On the
other hand, these mono-meric anthocyanins could be oxidised and
degraded. These reac-tions produced brick redness in red wine with
a long time aging(Rentzsch, Schwarz, & Winterhalter, 2007).
Furthermore, the poly-
y 172 (2015) 565574 571merisation reaction of anthocyanins
protected from nucleophilicattack or oxidisation by other molecules
in aqueous solution, hencemaintaining the wine colour (Somers,
1971). The present study
-
istr572 Y. Gao et al. / Food Chemalso showed that gallic acid
presented a signicant decline alongwith aging time, which is
probably due to the esterication andacetylation as previously
reported (Bentez, Castro, & GarcaBarroso, 2003). Similarly,
caffeic acid and ethyl p-coumarate alsoexhibited a concentration
decline, which might result from theincorporation of
hydroxycinnamic acid into pyranoanthocyaninsand even
hydroxyphenylpyranoanthocyanins (Pinotin)(Rentzsch, Schwarz,
Winterhalter, & Hermosn-Gutirrez, 2007;Schwarz, Hofmann, &
Winterhalter, 2004). Considering the occur-rence of these reactions
during wine bottle-aging, it is easy tounderstand the negative
correlation between the reduction of themonomeric anthocyanin and
phenolic acid components, and thedevelopment of wine appearance
during wine bottling.
3.4.2.2. Correlation between phenolic compounds and
mouthfeelperceptions. Fig. 4B reects a weak correlation between
phenolic
Fig. 3. Loadings BiPlot of appearance characteristics (A) and
mouthfeel characteristics (bottle stoppers: synthetic plug-1 (A),
synthetic plug-2 (B), synthetic plug-3 (C), aglomerafter the letter
represent aging time (months).y 172 (2015) 565574compounds (matrix
X) and mouthfeel characteristics (matrix Y),because the rst two PCs
only explained 40.1% of the total vari-ables. It was still observed
that the mouthfeel indicators were con-centrated on the rst
quadrant of the diagram corresponding to thepositive scores in PC1
and PC2, and wine structure and harmonyinuenced each other.
Malvidin-3-O-glucoside-ethyl-(epi)catechin(No. 15),
peonidin-3-O-(6-O-acetyl)-glucoside (No. 18),
malvidin-3-O-(6-O-coumaryl)-glucoside-pyruvic acid (No. 21), and
peoni-din-3-O-glucoside-4-vinylphenol (No. 27) were located in the
mostright side, which indicated that these four compounds were
posi-tively related to the development of the mouthfeel,
particularlythe aftertaste and genuineness of the red wine.
Additionally, mal-vidin-3-O-(6-O-acetyl)-glucoside-4-vinylguaiacol
(No. 32) wasassociated with the wine intensity, whilst
gallocatechin (No. 37),dihydrokaempferol-3-O-rhamnos (No. 54), and
glucose ester oftrans-p-coumaric acid (No. 67) had a positive
correlation with
B) of bottle aged dry red wines sealed with different stoppers.
Letters represent sixated cork (D), 1 + 1 technical cork (E) and
natural cork (F), respectively. Numbers
-
istrY. Gao et al. / Food Chemthe wine structure and harmony.
Oppositely, cyanidin-3-O-(6-O-coumaryl)-glucoside (No. 20),
malvidin-3-O-(6-O-acetyl)-gluco-side-4-vinylphenol (No. 30),
malvidin-3-O-(6-O-coumaryl)-glucoside-4-vinylphenol (No. 33),
dimer(epi)gallocatechin-(epi)catechin (No. 36), procyanidin B3 (P3)
(No. 41), dihydroqu-ercetin-3-O-hexoside (No. 46),
malvidin-3-glucoside-(epi) catechin(No. 52), and
isorhamnetin-3-O-glucoside (No. 59) were positionedin the most left
side, far away from the points of the mouthfeelcharacteristics,
suggesting that wines developed toward goodmouthfeel as these
phenolic compounds decreased or were con-verted into the lager
molecules during bottle-aging.
4. Conclusions
In conclusion, four groups of phenolic compounds (phenolicacids,
avonols, avan-3-ols, and anthocyanins) and sensory char-acteristics
in the wines sealed with six types of stoppers wereassessed during
18-month of the bottle aging. Phenolic compounds
Fig. 4. Loading plot of partial least squares regression
analysis between phenolic compoaged dry red wines sealed with
different stoppers. Numbers represent the phenolic comy 172 (2015)
565574 573in the red wines followed four evolution patterns,
depending onthe group of these compounds. The ninth month of the
bottle agingwas a key turning point for the overall evolution of
phenolic com-pounds. Both the appearance and mouthfeel attributes
of the winesin bottle developed toward a good quality during the
15-monthperiod, regardless of the types of bottle stoppers used.
This sensorydevelopment appeared to have fair association with the
variationof dissolved oxygen in the aged wines. The phenolic
compoundspositively or negatively correlated with the development
of thewine appearance and mouthfeel characteristics were
bothscreened out through the analysis of Partial least square.
Furtherconcern would be focused on how these compounds affect
winesensory attributes.
Acknowledgement
This work was nancially supported by the project of
ChinaAgriculture Research System (CARS-30).
unds and appearance characteristics (A), and mouthfeel
characteristics (B) of bottlepounds listed in Appendix Table 1.
-
Appendix A. Supplementary data
Supplementary data associated with this article can be found,
inthe online version, at
http://dx.doi.org/10.1016/j.foodchem.2014.09.115.
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Evolution of phenolic compounds and sensory in bottled red wines
and their co-development1 Introduction2 Materials and methods2.1
Wine samples2.2 Stoppers2.3 Chemicals and standards2.4
Determination of phenolic compounds2.4.1 Anthocyanins2.4.2
Non-anthocyanin phenolic compounds
2.5 Characterisation of colour fraction2.6 Determination of
dissolved oxygen in wine2.7 Sensory evaluation2.8 Statistical
analysis
3 Results and discussion3.1 Evolutions of dissolved oxygen and
phenolic compounds in wines during aging in bottle3.2 Main
difference of phenolic compounds amongst different stopper sealed
wines3.3 Variation of colour characteristics in bottled wines3.4
Correlation between phenolic compounds and development of sensory
characteristics3.4.1 Positioning analysis of sensory
characteristics3.4.1.1 Positioning analysis of appearance
characteristics3.4.1.2 Positioning analysis of mouthfeel
features
3.4.2 Correlation between variation of phenolic compounds and
development of sensory attributes3.4.2.1 Correlation between
phenolic compounds and appearance characteristics3.4.2.2
Correlation between phenolic compounds and mouthfeel
perceptions
4 ConclusionsAcknowledgementAppendix A Supplementary
dataReferences