Food Chemistry 135 (2012) 1863–1867

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Food Chemistry
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Short communication

HPLC–PDA–MS fingerprinting to assess the authenticity of pomegranate beverages

Gina Borges, Alan Crozier ⇑
Plant Products and Human Nutrition Group, Joseph Black Building, School of Medicine, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow G12
8QQ, United Kingdom

a r t i c l e i n f o a b s t r a c t

Article history: HPLC with fluorescence, PDA and mass spectrometric detection were used to analyse the (poly)phenol
Received 16 November 2011 content of a Bordeaux red wine, POM Wonderful pomegranate juice and three other beverages advertised
Received in revised form 27 February 2012 as being made from 100% pomegranate juice. The red wine and POM Wonderful juice contained charac-
Accepted 25 May 2012
teristic anthocyanin profiles with the latter also being characterised by the presence of ellagitannins and
Available online 7 June 2012
the former by flavan-3-ols monomers and procyanidin dimers and trimers. The three other pomegranate
products all contained the expected ellagitannins but their anthocyanin profiles were a mixture of red
Keywords:
wine and pomegranate anthocyanins. They also contained flavan-3-ol monomers and procyanidin dimers
Pomegranate products
Authenticity
and trimers, components not usually detected in 100% pomegranate beverages. The HPLC-based proce-
HPLC profiling dures, therefore, provide a straight-forward means of accessing the authenticity of pomegranate-based
Anthocyanins products with the ready detection of constituents derived from red grapes.
Ellagitannins Ó 2012 Elsevier Ltd. All rights reserved.
Flavan-3-ols

1. Introduction
Pomegranate (Punica granatum L.) is a fruit that has generated
great interest in recent years as consumption has been related to
the decrease in the risk of certain diseases including atherosclero-
sis and prostate cancer (Faria & Calhau, 2011; Koyama et al., 2010;
Sezer, Akcay, Ianbey, Yildirim, & Sözmen, 2007; Viuda-Martos,
Fernández-López, & Pérez-Álvarez, 2010). The antioxidant capacity
of commercial pomegranate juices, some of which are higher than
that of several other (poly)phenolic-rich beverages, such as tea and
red wines, has been attributed to the presence of hydrolysable tan-
nins including gallotannins, and the ellagitannins, punicalagin and
punicalin (Seeram et al., 2008; Martin, Krueger, Rodriquez, Dreher
& Reed, 2008; Borges, Mullen & Crozier, 2010; Viuda-Martos &
Fernández-López, 2010; Faria, 2011). Pomegranates also contain
anthocyanins with the principal components being 3-O-glucosides
and 3,5-O-diglucosides of cyanidin and delphinidin (Gil, Tomás-
Barberán, Hess-Pierce, Holcroft, & Kader, 2000; Zhang et al.,
2009). The polyphenol composition of pomegranate is both com-
plex and unique and as such can be used as a fingerprint by the
food industry for quality control purposes.
Red wines phenolics play an important role in the health ben-
efits of moderate wine consumption (Crozier, Borges, & Ryan,
2010; Perez et al., 2002; Renaud & de Lorgeril, 1992) and they
are also responsible for colour, flavour, astringency, bitterness
and their levels, in general, are related to wine quality. Red wines,
⇑ Corresponding author.
E-mail address: alan.crozier@glasgow.ac.uk (A. Crozier).
depending upon the variety of Vitis vinifera grape from which they
are produced, contain their own characteristic array of anthocya-
nins with malvidin-3-O-glucoside being the main component in
Cabernet Sauvignon wines (Burns et al., 2002). Red wines do not
contain hydrolysable tannins, but seed-derived oligomeric and
polymeric procyanidins, referred to collectively as condensed tan-
nins, do occur and in some wines in considerable amounts. The
consumption of procyanidin-rich red wines produced from Tannat
grapes has been linked with enhanced male longevity in the
départmente of Gers in the Midi-Pyrenees region of south west
France (Corder et al., 2006). Red wines also contain in somewhat
lower concentrations benzoic acids, flavonols, stilbenes, flavan-3-
ol monomers and hydroxycinnamate tartrate esters (Burns et al.,
2000; Crozier, Borges & Ryan, 2010; Waterhouse, 2002).
With growing interest in the nutritional properties of polyphen-
olics, an increasing number of products derived from red wine and
pomegranates are now being marketed commercially. Numerous
pomegranate juices are now available for consumers although they
do contain greatly varying amounts of pomegranate (Borges, Mul-
len & Crozier, 2010). The extreme example was detected in a 2007
survey of the polyphenol content of fruit juices, where the sole
pomegranate juice to be analysed contained no detectable ellagit-
annins and an anthocyanin profile characteristic of red grapes
rather than pomegranate (Mullen, Marks, & Crozier, 2007). It was
against this background that the current study set out to use HPLC
methodology to evaluate the authenticity of pomegranate bever-
ages by analysing POM Wonderful pomegranate juice and three
additional 100% pomegranate beverages along with a Bordeaux
Cabernet Sauvignon red wine.

0308-8146/$ - see front matter Ó 2012 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.foodchem.2012.05.108
1864 G. Borges, A. Crozier / Food Chemistry 135 (2012) 1863–1867

Table 1
HPLC-MS2 based identifications of (poly)phenolic compounds in a red wine (RW), POM Wonderful pomegranate juice (PG1), and three other 100% pomegranate beverages
(PG2–PG4)a.

Rt (min) [MH] (m/z) MS2 (m/z) Compound Occurrence

RW PG1 PG2 PG3 PG4
6.7 169 125 Gallic acid
7.1 1101 781, 601, 301 Punicalagin-like
7.6 781 601, 301 Punicalin A
8.1 781 601, 301 Punicalin B
8.5 781 601, 301 Punicalin isomer
8.6 865 577, 289 Procyanidin trimer
10.5 577 451, 289, 425, 559, 407 Procyanidin dimer
11.1 627+ 465, 303 Delphinidin-3,5-O-diglucoside
11.5 933 781, 721, 601 2-O-Galloylpunicalin
12.8 1083 781, 601 Punicalagin A
13.8 1083 781, 601 Punicalagin B
14.5 175 157, 127, 115, 113, 85 Unknown
14.6 611+ 449, 287 Cyanidin-3,5-O-diglucoside
16.2 1083 781, 601 Punicalagin isomer
16.4 577 451, 289, 425, 559, 407 Procyanidin dimer B1
16.5 577 451, 289, 425, 559, 407 Procyanidin dimer
16.5 625 463, 301 Ellagic acid dihexoside
16.7 465+ 303 Delphinidin-3-O-glucoside
17.5 289 245, 205 Catechin
17.9 311 149, 179 Caftaric acid
17.9 1083 781, 601 Punicalagin isomer
19.3 449+ 287 Cyanidin-3-O-glucoside
20.5 865 577, 289 Procyanidin trimer
21.5 479 317 Petunidin-3-O-glucoside
21.6 577 451, 289, 425, 559, 407 Procyanidin dimer B2
21.8 433+ 271 Pelargonidin-3-O-glucoside
22.8 919 757, 595, 449, 287 Cyanidin-O-p-coumaroyl-triglucoside
23.3 289 245, 205 Epicatechin
23.5 295 163, 149 Coutaric acid
23.6 783 Pedunculagin isomer
23.9 463+ 301 Peonidin-3-O-glucoside
24.0 631 451, 301 Tergallagic acid-O-glucoside isomer
25.2 419+ 287 Cyanidin-O-pentoside
25.4 197 169, 125 Dimethyl-gallic acid
25.4 493+ 331 Malvidin-3-O-glucoside
25.9 631 451, 301 Tergallagic acid-O-glucoside isomer
26.9 865 577, 289 Procyanidin trimer
27.9 577 451, 289, 425, 559, 407 Procyanidin dimer
29.1 507 303 Delphinidin-3-O-(600 -O-acetyl)glucoside
32.7 425 (469) 301 Valoneic acid dilactone – CO2
32.7 463 301 Ellagic acid-hexoside
33.1 521+ 317 Petunidin-3-O-(600 -O-acetyl)glucoside
34.7 547+ 385, 301 Unidentified anthocyanin
34.8 479 317 Myricetin-3-O-glucoside
35.7 505+ 301 Peonidin-3-O-(600 -O-acetyl)glucoside
36.4 535+ 331 Malvidin-3-O-(600 -O-acetyl)glucoside
38.2 611+ 303 Delphinidin-3-O-(600 -O-p-coumaroyl)glucoside
39.3 561+ 399 Vitisin A
39.9 301 257, 229 Ellagic acid
41.7 477 301 Quercetin-3-O-glucuronide
42.7 317 271, 179, 151 Myricetin
43.0 625+ 463, 317 Petunidin-3-O-(600 -O-p-coumaroyl)glucoside
44.2 609+ 447, 301 Peonidin-3-O-(600 -O-p-coumaroyl)glucoside
44.7 639+ 331 Malvidin-3-O-(600 -O-p-coumaroyl)glucoside
45.6 507 345 Syringetin-O-hexoside
49.8 301 179, 151 Quercetin
a
Rt, retention time; [MH] , negatively charged molecular ion; +, positively charge molecular ion; MS2, daughter ions produced from fragmentation of the molecular ion.


2. Materials and Methods pelargonidin-3-O-glucoside were supplied by Extrasynthese (Gen-

2.1. Chemicals
Gallic acid, ellagic acid, quercetin, quercetin-3-rutinoside,
myricetin, (+)-catechin, ()-epicatechin and procyanidins B1 and
B2 were purchased from Sigma–Aldrich (Poole, UK). Punicalagin
was purchased from LGC Standards (Teddington, Middlesex, UK).
Caftaric acid, cyanidin-3-O-glucoside, malvidin-3-O-glucoside and
ay, France). Methanol was obtained from Rathburn Chemicals
(Walkerburn, Scotland). Formic acid and acetic acid were supplied
by Fisher Scientific (Loughborough, UK).
2.2. Beverages
Red wine (RW), a 2005 Amarande, oak-aged Bordeaux made
from Cabernet Sauvignon grape was purchased from Oddbins,
 G. Borges, A. Crozier / Food Chemistry 135 (2012) 1863–1867 1865

Fig. 1. HPLC-520 nm profiles of anthocyanins in a red wine (RW), POM Wonderful pomegranate juice (PG1) and three other pomegranate beverages (PG2–PG4). For peak
numbers and quantifications, see Table 2. Yellow peaks are pomegranate anthocyanins, red peaks are red wine anthocyanins, while the grey peak 7, a cyanidin-O-(p-
coumaroyl)triglucoside was detected in PG2–PG4 but not PG1. (For interpretation of the references to colour in this figure legend, the reader is referred to the web version of
this article.)

Table 2
Quantification of anthocyanins in a red wine (RW), POM Wonderful pomegranate juice (PG1), and three other 100% pomegranate beverages (PG2–PG4)a.

Peak # Anthocyanin RW PGJ PG2 PG3 PG4

1 Delphinidin-3,5-O-diglucoside n.d. 15.8 ± 0.6 2.2 ± 0.0 2.8 ± 0.0 1.6 ± 0.0
2 Cyanidin-3,5-O-diglucoside n.d. 32.2 ± 0.5 3.5 ± 0.0 5.8 ± 0.0 2.5 ± 0.0
3 Delphinidin-3-O-glucoside 4.2 ± 0.0 17.7 ± 0.5 4.1 ± 0.1 1.2 ± 0.0 0.5 ± 0.0
4 Cyanidin-3-O-glucoside 1.0 ± 0.0 53.0 ± 1.1 1.0 ± 0.0 0.6 ± 0.0 0.5 ± 0.0
5 Petunidin-3-O-glucoside 3.5 ± 0.0 n.d. 3.7 ± 0.0 1.2 ± 0.0 0.8 ± 0.0
6 Pelargonidin-3-O-glucoside n.d. 3.4 ± 0.1 n.d. n.d. n.d.
7 Cyanidin-O-(p-coumaroyl)triglucoside n.d. n.d. 4.0 ± 0.0 3.4 ± 0.0 3.3 ± 0.1
8 Peonidin-3-O-glucoside 2.3 ± 0.0 n.d. 1.8 ± 0.0 1.0 ± 0.0 0.8 ± 0.0
9 Malvidin-3-O-glucoside 13.6 ± 0.2 n.d. 7.2 ± 0.1 1.8 ± 0.0 0.7 ± 0.0
10 Delphinidin-3-O-(600 -O-acetyl)glucoside 1.3 ± 0.0 n.d. 0.4 ± 0.0 0.2 ± 0.0 0.2 ± 0.0
11 Petunidin-3-O-(600 -O-acetyl)glucoside 0.8 ± 0.0 n.d. 0.4 ± 0.0 n.d. n.d.
12 Unknown anthocyanin 0.7 ± 0.0 n.d. 0.1 ± 0.0 0.1 ± 0.0 0.1 ± 0.0
13 Peonidin-3-O-(600 -O-acetyl)glucoside 0.4 ± 0.0 n.d. n.d. n.d. n.d.
14 Malvidin-3-O-(600 -O-acetyl)glucoside 3.3 ± 0.1 n.d. 0.7 ± 0.0 0.2 ± 0.0 n.d.
15 Delphinidin-3-O-(600 -O-p-coumaroyl)glucoside 0.6 ± 0.0 n.d. n.d. n.d. n.d
16 Vitisin A 3.6 ± 0.0 n.d. 1.0 ± 0.0 0.8 ± 0.0 0.5 ± 0.0
17 Petunidin-3-O-(600 -O-p-coumaroyl)glucoside 0.4 ± 0.0 n.d. n.d. n.d. n.d.
18 Peonidin-3-O-(600 -O-p-coumaroyl)glucoside 0.5 ± 0.0 n.d. 0.2 ± 0.0 0.2 ± 0.0 n.d.
19 Malvidin-3-O-(600 -O-p-coumaroyl)glucoside 1.3 ± 0.1 n.d. 0.8 ± 0.0 0.2 ± 0.0 n.d.
a
Data expressed in lg/mL ± standard error. n.d. – not detected. For peak numbers see HPLC-520 nm traces illustrated in Fig. 1.

Hyndland Road, Glasgow. POM Wonderful pomegranate juice 2.3. HPLC–PDA–MS2 analysis
(PG1) was obtained from Waitrose, Byers Road, Glasgow. The other
100% pomegranate beverages (PG2–PG4) were supplied by the Analysis was carried out on a Surveyor HPLC system comprising
manufacturer. of an autosampler with sampler cooler maintained at 4 °C, a
1866 G. Borges, A. Crozier / Food Chemistry 135 (2012) 1863–1867

Table 3
Quantification of flavan-3-ols in a red wine (RW), POM Wonderful pomegranate juice (PG1), and three other 100% pomegranate beverages (PG2–PG4)a.

Peak # Flavan-3-ol RW PG1 PG2 PG3 PG4

1 Unknown n.q. n.d. n.q. n.q. n.q.
2 Procyanidin dimer B1 15.6 ± 0.3 n.d. 9.9 ± 0.3 10.1 ± 0.2 11.1 ± 0.5
3 Procyanidin dimer 35.1 ± 0.5 n.d. 7.3 ± 0.1 2.7 ± 0.0 1.6 ± 0.1
4 Catechin 20.2 ± 0.1 n.d. 5.5 ± 0.1 3.2 ± 0.0 3.1 ± 0.4
5 Procyanidin trimer 9.8 ± 0.1 n.d. n.d. n.d. n.d.
6 Procyanidin dimer B2 27.2 ± 0.5 n.d. 6.8 ± 0.1 2.5 ± 0.1 2.2 ± 0.1
7 Epicatechin 12.9 ± 0.1 n.d. 4.7 ± 0.0 2.4 ± 0.2 1.7 ± 0.1
a
Data expressed in lg/mL ± standard error. n.d. – not detected; n.q. – not quantified. For peak numbers see HPLC-fluorescence traces illustrated in Fig. 1.

photodiode array detector (PDA), (Thermo Fisher Scientific, San

Jose, CA, USA) scanning from 200 to 600 nm and a fluorimetric
detector system as employed in a previous study (Borges, Mullen
& Crozier, 2010). Samples were analysed on a 250  4.6 mm Gem-
ini C6 phenyl column (Phenomenex, Macclesfield, UK), maintained
at 40 °C, eluted at a flow rate of 1 ml/min with a 60 min gradient of
5–60% methanol in 1% aqueous formic acid. After passing through
the flow cells of the PDA and a fluorimetric detector (excitation
280 nm and emission 310 nm) the eluate was split and 200 lL di-
rected to a LCQ Advantage ion trap mass spectrometer fitted with
an electrospray interface (Thermo Fisher Scientific). Capillary tem-
perature was 300 °C, sheath gas and auxiliary gas were 60 and
20 units, respectively, the source voltage was 4 kV. Samples were
analysed using full scan in both positive and negative ionisation
modes, the scan range was from 150 to 2000 m/z for negative ion
and 190 to 1000 m/z for positive ion. Identifications were based
on a combination of co-chromatography with authentic standards,
absorbance spectra and mass spectrometric fragmentation pat-
terns which, when references compounds were not available, were
matched with published data (Borges, Mullen & Crozier, 2010; Gil
et al., 2000; Martin, Krueger, Rodriquez, Dreher, & Reed, 2009; Ta-
naka, Nonaka, & Nishioka, 1986). Anthocyanins were quantified at
520 nm in cyanidin-3-O-glucoside equivalents and flavan-3-ols
and procyanidins were quantified on the basis of fluorescence
detection in ()-epicatechin equivalents.

3. Results and discussion

The composition of the five beverages was investigated further

using HPLC-fluorescence, PDA and MS2 detection. Table 1 provides
details of the 54 identified/tentatively identified compounds. As
previously reported (Borges, Mullen & Crozier, 2010) POM Won-
derful, a well established 100% pomegranate juice (PG1) contained
a number of ellagitannins principally in the form of punicalin and
punicalagin isomers along with ellagic acid and an ellagic acid
hexoside. The anthocyanins comprised a typical pomegranate pro-
file with the presence of the 3-O-glucosides and 3,5-O-diglucoside
of both cyanidin and delphinidin (Borges, Mullen & Crozier, 2010;
Gil et al., 2000) as well as pelargonidin-3-O-glucoside. The Caber-
net Sauvignon red wine contained a somewhat different spectrum
of (poly)phenolic compounds many of which were not present in
the pomegranate juice, namely catechin, epicatechin and several
procyanidin dimers and trimers and a diversity of anthocyanins
including malvidin-3-O-glucoside and 3-O-(600 -O-p-coumaroyl)glu-
cosides and 3-O-(600 -O-acetyl)glucosides of delphinidin, petunidin,
peonidin and malvidin (Table 1).
All three of the other pomegranate beverages contained a char-
acteristic array of punicalin and punicalagins isomers as well as
cyanidin- and delphinidin-3,5-O-diglucosides. Some other com-
pounds like pedunculagin, tergallagic acids and valoneic acid dilac-
tone, previously reported ellagic acid derivatives (Cantos et al.,
2003; Fisher, Carle, & Kammerer, 2011), were also detected. How-
Fig. 2. HPLC-fluorescence profiles monitoring flavan-3-ols in a red wine (RW), POM
Wonderful pomegranate juice (PG1) and three other pomegranate beverages (PG2–
PG4). For peak numbers and quantifications, see Table 3. (For interpretation of the
references to colour in this figure legend, the reader is referred to the web version of
this article.)
ever, it is evident from the data in Table 1 that the pomegranate
beverages, PG2–PG4, also contained flavan-3-ol monomers, dimers
and trimers and flavonol derivatives, as well as several anthocya-
nins, such malvidin-3-O-glucoside, malvidin-3-O-(600 -O-p-couma-
royl)glucosides and malvidin-3-O-(600 -O-acetyl)glucosides, that
are characteristic of red wines (Burns et al., 2002) and Cabernet
Sauvignon and Merlot grapes (Burns et al., 2001).
The presence of the red grape/wine anthocyanins in the pome-
granate PG2–PG4 beverages is clearly evident from the
HPLC-520 nm traces illustrated in Fig. 1 and the accompanying
quantitative data in Table 2. Likewise, the HPLC-fluorescence pro-
files in Fig. 2 and the data in Table 4, show that PG2–PG4 contained
flavan-3-ol monomers and dimer and trimer procyanidins, none of
which were present in the 100% POM Wonderful juice, but did oc-
cur in the red wine that was analysed.
 G. Borges, A. Crozier / Food Chemistry 135 (2012) 1863–1867 1867

Table 4 Cantos, E., Espín, J. C., López-Bote, C., de la Hoz, L., Ordóñez, A. J., & Tomás-Barberán,
Contribution of red wine/grape anthocyanins and flavan-3-ols to three pomegranate F. A. (2003). Phenolic compounds and fatty acids from acorns (Quercus spp.), the
beverages (PG2–PG4). main dietary constituent of free-ranged Iberian pigs. Journal of Agricultural and
Food Chemistry, 51(21), 6248–6255.
PG2 PG3 PG4 Corder, R., Mullen, W., Khan, Q. N., Marks, S. C., Wood, E. G., Carrier, M. J., et al.
(2006). Red wine procyanidins and vascular health. Nature, 444(7119), 566.
Total anthocyanins 30.4 lg/mL 19.5 lg/mL 11.5 lg/mL
Crozier, A., Borges, G., & Ryan, D. (2010). Red wine procyanidins and vascular health.
Red wine anthocyanins 20.3 lg/mL 8.7 lg/mL 6.4 lg/mL The Biochemist, 32(6), 4–9.
Red wine anthocyanins 67% 45% 56% Faria, A., & Calhau, C. (2011). The bioactivity of pomegranate: Impact on health and
as a% of total disease. Critical Reviews in Food Science and Nutrition, 51(7), 626–634.
Total flavan-3-ols 28.8 lg/mL 20.0 lg/mL 18.5 lg/mL Fisher, U., Carle, R., & Kammerer, D. (2011). Identification and quantification of
Flavan-3-ols as a% of 24% 17% 15% phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp,
amount in red wine aril and differentially produced juices by HPLC-DAD-ESI/MSn. Food Chemistry,
127(2), 807–821.
Gil, M. I., Tomás-Barberán, F. A., Hess-Pierce, B., Holcroft, D. M., & Kader, A. A. (2000).
Antioxidant activity of pomegranate juice and its relationship with phenolic
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4581–4589.
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Koyama, S., Cobb, J. L., Mehta, H. H., Seeram, N. P., Heber, D., Pantuck, A. J., et al.
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