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J. Agric. Sci. Technol. (2007) Vol. 9: 35-42
35
Total Phenolic Contents and Antioxidant Activity of
Pomegranate (Punica granatum L.) Peel Extracts
P. Yasoubi1, M. Barzegar1*, M. A. Sahari1 and M. H. Azizi2
ABSTRACT
The phenolic compounds of pomegranate (Punica granatum L.) peel extracted by two
methods (solvent and ultrasound-assisted) with five solvents (acetone, methanol, ethanol,
water and ethyl acetate) were compared with supercritical fluid extraction (SFE). The
total phenolic compounds were determined according to the Folin-Ciocalteu reagent using
tannic acid as standard. The overall results showed that acetone with sonication produced
the maximum amount of phenolic compounds from pomegranate peel extracts (PPE).
Furthermore, the effect of the acetone extract of pomegranate peel (0.010-0.050 %) on the
stability of soybean oil during heating at 60oC (oven test method) was determined by
measuring peroxide and thiobarbitoric acid values. At a 0.050 % level of pomegranate
peel extract, its antioxidant activity was greater than 0.02 % of the two synthetic
antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). The
pomegranate peel extract possessed a relatively high antioxidant activity and might be
considered as a rich source of natural antioxidant.
Keywords: Phenolic compounds, Pomegranate peel, SFE, Solvent extraction, Sonication.
_____________________________________________________________________________
1. Department of Food Technology, Tarbiat Modares University, P. O. Box: 14115-336, Tehran, Islamic Republic of
Iran.
2. National Nutrition and Food Technology Research Institiute, P. O. Box: 19395-4741, Tehran, Islamic Republic of
Iran.
* Corresponding author, e-mail: mbb@modares.ac.ir
INTRODUCTION
The search for cheap and abundant sources
of natural antioxidants is attracting
worldwide interest. Much research is needed
in order to select raw materials; those of
residual origin are especially promising due
to their lower costs.
The pomegranate (Punica granatum L.) is
one of the oldest edible fruits and is widely
grown in many tropical and subtropical
countries [1]. It is an important commercial
fruit in Iran with a total production of
665,000 tons in 2003 [2]. Pomegranate juice
and peel contain substantial amounts of
polyphenols such as ellagic tannins, ellagic
acid and gallic acid [3]. It has been used in
the preparation of tinctures, cosmetic,
therapeutic formula and food recipes [4] and
in this regard pomegranate peel is a good
source of antioxidants [5].
Antioxidants are the compounds that, when
added to food products, especially lipids and
lipid-containing systems, can increase the
shelf life of the product by retarding the
process of lipid peroxidation. Lipid
peroxidation in fats and fatty foods not only
brings about chemical spoilage in foods but
also produces free radicals such as peroxyl
and hydroxyl radicals, which are purportedly
associated with carcinogenesis, mutagenesis,
and aging [6, 7]. On the other hand, the most
widely used synthetic antioxidants, butylated
hydroxyanisole and butylated hydroxytol-
uene, which have been used as antioxidants
since the beginning of this century, and have
been restricted recently, mainly because of
their possible carcinogenicity [8] causing
liver swelling and changing liver enzyme
______________________________________________________________________Barzegar et al.
36
activities [9]. However, in recent years,
many attemps have been made to study
natural antioxidants, particularly those of
plant origin [10].
Great interest has recently been focused on
the addition of polyphenols to foods and
biological systems, due to their well-known
abilities to scavenge free radicals, i. e.
antioxidant power. The generation of free
radicals plays an important role in the
progression of numerous pathological
disturbances, such as atherosclerosis [11],
brain disfunction [12] and cancer [13].
Extraction is a key step for obtaining
antioxidants with an acceptable yield.
Solvent extraction is more frequently used
for the isolation of antioxidants and the
extraction yield and economic viability is
dependent on the type of solvent and method
of extraction, mostly due to the differing
polarity of these compounds. Several
extraction techniques have been reported for
the extraction of phenolic compounds from
different matrices using solvents with
different polarities, such as methanol, water,
ethyl acetate and petroleum ether [14, 15].
Furthermore, supercritical CO2 [16,17] and
solvent extraction along sonication have
been applied for this purpose [18].
The aim of this research was to compare
solvent extraction (acetone, methanol,
ethanol, water and ethyl acetate) with and
without Sonication and with the SFE
process. Furthermore, in this study, the
effect of concentrated pomegranate peel
extracts (PPEs) on the stability of soybean
oil during heating has been compared with
that of two synthetic antioxidants BHA and
BHT.
MATERIALS AND METHODS
Pomegranates (Poost Syah variety) were
obtained from the Agricultural Research
Centre of Yazd (Iran). The skins were
manually removed, sun-dried (ambient
temperature= 30 o
C and %RH= 32),
powdered in a grinder to reach 40-mesh and
then were packed and stored at -20 oC until
extraction. All chemicals were of analytical
grade and of the highest purity available
(>99.5 %) and obtained from Merck
(Darmstadt, Germany).
A Suprex MPS/225 system (Pittsburg,
USA) in the SFE mode was used for the
extraction of phenolic compounds. In this
study, extractions of 3.0 g of dried powder
from the peel were accomplished with a 10
mL volume extraction vessel. Nine
extractions were carried out at constant
static time of 20 minutes, temperatures of
35, 40 and 45 oC, pressures of 150, 250, and
350 bar, and dynamic times 10, 25 and 35
minutes. Two different concentrations of
methanol (10 and 15 %) were used, as a
modifier. The extracted phenolics were
collected in 5 mL methanol in 10 mL
volumetric flasks through a Duraflow
manual variable restrictor (Suprex, USA)
that avoided plugging and provided a
constant flow rate during the extraction
process. The compressed supercritical fluid
CO2 at a flow rate of approximately 0.35 ±
0.05 mL was passed through the variable
restrictor. During the dynamic time, the
volumetric flask was placed in an ice bath
for efficiency of collection. Methanol was
spiked directly into the extraction vessel
with a charged sample prior to extraction to
investigate the effect of the modifier. Table
1 shows the SFE experimental conditions for
phenolic extraction.
Dried powders of peels (2.5 g) were
extracted with 40 mL of each solvent at
room temperature for 6 hours. The extract
was filtered through Whatman No.42 filter
paper to remove fine particles. The residue
was re-extracted with the same solvent and
the extracts were added to each other [19].
After extraction, the solvent was evaporated
using a rotary evaporator (under vacuum and
at 30 oC) and the concentrated extracts were
stored in a freezer. The same procedure was
followed for other solvents and methods.
An Elma Transsonic model 690/H
ultrasonic bath (Germany) was used for
sonication and extraction of phenolic
compounds from mixture of solvents and
powdered peel. Forty mL of solvent was
Total Phenolic Contents and Antioxidant Activity of PPE___________________________
37
added to 2.5 g powdered peel; the mixture
was sonicated in this ultrasonic bath for 30
minutes. The extract was filtered through
Whatman No.42 filter paper.
The concentrations of phenolic compounds
in the extracts were determined according to
the Folin-Ciocalteu method [15], and the
results were expressed as tannic acid
equivalents per gram dry weight of sample
(TAE/gdw). The pomegranate peel extracts
were dissolved in a mixture of methanol and
water (2:1 V/V). Samples (0.2 mL) were
mixed with 1.0 mL of 10-fold-diluted Folin-
Ciocalteu reagent and 0.8 mL of 7.5%
sodium carbonate solution, after the mixture
had been allowed to stand for 30 minutes at
room temperature, the absorbance was
measured at 765 nm using Scinco 2120 UV-
Vis spectrophotometer (Seoul, South
Korea). The estimation of phenolic
compounds in the extracts was carried out in
triplicate. Antioxidant-free soybean oil was
obtained from Parsghoo Co. (Tehran, Iran).
Antioxidant Activity Assay
The pomegranate peel extracted by acetone
as solvent along with Sonication had the
highest phenolic content. Therefore, this
extract was added to soybean oil (refining
oil with approximately 40 ppm naturally-
occurring tocopherols, measured in the
quality control laboratory of Parsghoo Co.)
at levels of 0.010, 0.025, 0.035 and 0.050 %.
Synthetic antioxidants (BHA and BHT) at
0.010 and 0.020 % levels were added to
soybean oil for comparison, and the stability
of the oil at 60 oC was monitored, according
to the oven test method [20]. Oxidation was
periodically assessed by the measurement of
peroxide value (PV) [21], and thiobarbituric
acid (TBA) value [22]. A control sample
was prepared under the same conditions,
without adding any antioxidant. All the
experiments were carried out in triplicate.
Statistical Analysis
Experimental data was analysed using
analysis of variance (ANOVA) and signifi-
cant differences among means from a
triplicate analysis at (P<0.05) were determ-
ined by Duncan’s multiple range test
(DMRT) using the SPSS software.
RESULTS AND DISCUSSION
Optimization of SFE Variables
The first step in the SFE of phenolic
compounds is to optimize the operating
conditions (especially the pressure and the
percentage of the modifier) to obtain an
efficient extraction of phenolics. In fact, the
fluid pressure and temperature, the
percentage of modifier and the extraction
Table 1. Taguchi experimental design for extraction of phenolic compounds from pomegranate
peel using SFE.
Run No. P (bar) T (oC) t (min) Modifier (MeOH, %) Phenolic content (%)a
1 150 35 10 0 0.73
2 150 40 25 10 0.53
3 150 45 35 15 0.38
4 250 35 25 15 0.75
5 250 40 35 0 0.66
6 250 45 10 10 0.32
7 350 35 35 10 0.77
8 350 40 10 15 0.84
9 350 45 25 0 0.75
a Based on dry weight of extracted peel.
______________________________________________________________________Barzegar et al.
38
time are generally considered as the most
important factors. The optimization of the
method can be carried out step-by-step or by
using an experimental design. Table 1 shows
different conditions of experiments in the
extraction of phenolic compounds according
to the Taguchi experimental design [23]. All
the selected factors were examined using a
three-level orthogonal array design with a L9
(34) matrix.
Total Phenolic Content
The concentration of phenolics in the
extracts, expressed as tannic acid was
dependent on the polarity of solvent and
method used in the extraction as shown in
Figures 1A and 1B. The amount of phenolic
compounds in the acetone extracts (in either
solvent or ultrasound-assisted solvent
extraction methods) were the highest (40.0
and 35.0 % for sonication and solvent
extraction, respectively (P< 0.05)), followed
by methanol (34.5 and 31.0 %), ethanol
(25.3 and 23.0 %), and water (10.0 and 12.0
%), and ethyl acetate extracts (0.2 and 0.2
%). There was a significant difference (P<
0.05) in the extraction yields between the
extracts of the five solvents used (Figures
1A and 1B). Extraction in acetone by
sonication was found to be more efficient
than other solvents studied in extracting the
antioxidant present in the pomegranate peel.
These antioxidative activity results were
comparable to the values previously reported
by Negi, et al. [24]. Ethyl acetate extract and
extract of modified SF CO2 had similar (at
P< 0.05), but comparatively small extraction
yield (as shown in Figures 1A and 1B). As
shown in Table 1, in run No. 8 (T= 40 oC, P=
350 bar, dynamic time= 10 min and 15% of
modifier), the maximum extraction yield of
phenolic acids was obtained (0.84
g/100gdw) that in comparison with solvent
extraction, its yield is very low.
Effect of Addition of PPEs on the Stability
of Soybean Oil
As a general trend, antioxidant activity
increased with increasing extract
concentration, as indicated by lower PV and
TBA values in Figures 2 and 3, but the
concentration leading to maximum
antioxidant activity is closely dependent on
the extracts. Often, natural antioxidants
show antioxidant powers lower than those of
synthetic ones, but they are not law-limited
in quantity. Also, this observation is limited
to a certain level, which depends on both the
antioxidant and the test [25]. For most
natural antioxidant and tests, maximum
antioxidant activity was achieved using a
0.05 % concentration.
Figure 1. Total phenolic contents of
pomegranate peels extracted by (A) sonication
and (B) solvent extraction methods.
Total Phenolic Contents and Antioxidant Activity of PPE___________________________
39
The PPEs at 0.010, 0.025, 0.035 and 0.050
% levels and synthetic antioxidants (BHA
and BHT) were added at 0.010 and 0.020 %,
because the latter were pure compounds
whereas the former were complex mixtures,
with active components being present at
lower levels.
The addition of natural and synthetic
antioxidants to soybean oil affected, to
differing degrees, the peroxide and TBA
values during accelerated oxidation at 60 oC
for 12 and 13 days, respectively. The
peroxide value (PV) measures primary
products of lipid oxidation and the TBA
value measures the formation of secondary
oxidation products, mainly malonaldehyde,
which may contribute to an off-flavour in
oxidized oil [26]. All those samples with an
added PPEs level at 0.010-0.050 % were
more stable on heating at 60 oC than the
control, when assessed by the change in
peroxide (Figure 2) and TBA (Figure 3)
values. The antioxidant effect of PPE
increased with concentration and, at a
concentration of 0.050 %, its antioxidant
activity was higher and significantly
different (P<0.05) from that of the synthetic
antioxidant (BHA and BHT) at the 0.010
and 0.020 % levels.
CONCLUSION
These results suggest that the PPE may be
used as a natural antioxidant to improve the
quality, stability and safety of foods such as
edible oils. Phenolic compounds are widely
distributed in nature and, according to the
findings of this study, pomegranate peel is a
natural source of phenolic compounds.
Acetone extracts were found to contain high
phenolic contents (35.0-40.0 %), so it is
suggested that the best method for extraction
of antioxidant-containing phenolic compo-
unds is by sonication with acetone or
methanol. These results suggest that the PPE
possesses antioxidant properties and, after
purification, could be used as an alternative
natural antioxidant. However, extensive
research is required on potential sources,
optimisation of the extraction process,
knowledge about the in vivo mechanisms
and assimilation. No single compound alone
can be considered responsible for this
stability.
0
10
20
30
40
50
60
02468101214
control
0.010% PPE
0.025% PPE
0.035% PPE
0.050% PPE
0.01% BHA
0.02% BHA
0.01% BHT
0.02% BHT
Day
Figure 2. Changes in the peroxide values (PVs) of soybean oil treated with different concentrations
of PPEs during storage at 60 oC.
PV (meq/kg oil)
______________________________________________________________________Barzegar et al.
40
ACKNOWLEDGMENT
We gratefully acknowledge the financial
support of the National Nutrition and Food
Technology Research Institiute and Tarbiat
Modares University Research Council.
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0.2
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0.050% PPE
0.01% BHA
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راﺪﻘﻣﻚﻴﻟﻮﻨﻓ ﻞﻛ رﺎﻧا ﺖﺳﻮﭘ ةرﺎﺼﻋ ﻲﻧاﺪﻴﺴﻛا ﻲﺘﻧآ ﺖﻴﻟﺎﻌﻓ و ﺎﻫ)Punica granatum L.(
پ .ﻲﺑﻮﺜﻌﻳ،م .ﺮﮔزﺮﺑ،م .ع .م و يﺮﺤﺳ .ح .يﺰﻳﺰﻋ
هﺪﻴﻜﭼ
رﺎﻧا ﺖﺳﻮﭘ ﻚﻴﻟﻮﻨﻓ تﺎﺒﻴﻛﺮﺗ) Punica granatum L.( زا هدﺎﻔﺘﺳا ﺎﺑ 5 لﻼﺣ )ﻦﺘﺳا،لﻮﻧﺎﺘﻣ ،
لﻮﻧﺎﺗا،تﺎﺘﺳا ﻞﻴﺗا و بآ ( هاﺮﻤﻫﻪﺑ نوﺪﺑ ﺎﻳ و ﺎﺑ ﺎﻬﻧآ ﺞﻳﺎﺘﻧ و ﺪﻧﺪﺷ جاﺮﺨﺘﺳا تﻮﺻ اﺮﻓ جاﻮﻣا يﺮﻴﮔرﺎﻛ
ﻲﻧاﺮﺤﺑ قﻮﻓ لﺎﻴﺳ ﺎﺑ جاﺮﺨﺘﺳا شور) Supercritical fluid extraction, SFE (ﺪﺷ ﻪﺴﻳﺎﻘﻣ . ﻞﻛ راﺪﻘﻣ
ﻚﻴﻟﻮﻨﻓ ﻦﻴﻟﻮﻓ شور ﻪﺑ ﺎﻫ-ﻪﺑ ﺪﻴﺳا ﻚﻴﻧﺎﺗ زا هدﺎﻔﺘﺳا ﺎﺑ و ﻮﻴﺘﻟﺎﻛﻮﻴﺳ هزاﺪﻧا دراﺪﻧﺎﺘﺳا ناﻮﻨﻋ ﺪﺷ يﺮﻴﮔ . ﺞﻳﺎﺘﻧ
ﺸﻧهرﺎﺼﻋ ﻪﻛ داد نﺎ هاﺮﻤﻫ ﻦﺘﺳا لﻼﺣ و ﺪﻨﺘﺴﻫ ﻚﻴﻟﻮﻨﻓ تﺎﺒﻴﻛﺮﺗ ﻲﻬﺟﻮﺗ ﻞﺑﺎﻗ راﺪﻘﻣ ياراد رﺎﻧا ﺖﺳﻮﭘ يﺎﻫ
______________________________________________________________________Barzegar et al.
42
تﻮﺻ اﺮﻓ جاﻮﻣا ﺎﺑ) Sonication (ﺖﺳا نﺎﻣﺪﻧار ﻦﻳﺮﺘﺸﻴﺑ ياراد .هوﻼﻌﺑ، رﺎﻧا ﺖﺳﻮﭘ ﻲﻨﺘﺳا ةرﺎﺼﻋ ﺮﻴﺛﺎﺗ
)05/0-01/0 (% يﺎﻣد رد ﺎﻳﻮﺳ ﻦﻏور يراﺪﻳﺎﭘ ﺮﺑ60ﺔﺟرد ﻲﺘﻧﺎﺳ داﺮﮔ)ﺟا نﻮﻣزآقﺎ ( ﺪﺷ ﻦﻴﻴﻌﺗ) ﺎﺑ
هزاﺪﻧا ﺪﻴﺳا ﻚﻳرﻮﺘﻴﺑرﺎﺑﻮﻴﺗ و ﺪﻴﺴﻛاﺮﭘ ﺮﻳدﺎﻘﻣ يﺮﻴﮔ .( رد05/0 % رﺎﻧا ﺖﺳﻮﭘ ةرﺎﺼﻋ زا، ﻲﺘﻧآ ﺖﻴﻟﺎﻌﻓ
زا ﺮﺘﺸﻴﺑ نآ ﻲﻧاﺪﻴﺴﻛا02/0 % يﺰﺘﻨﺳ ناﺪﻴﺴﻛا ﻲﺘﻧآ ودBHA) Butylated hydroxyanisole ( وBHT
)
Butylated hydroxyltoluene(دﻮﺑ .ﻮﭘ ةرﺎﺼﻋ ﻪﻛ ﺪﻧداد نﺎﺸﻧ ﺞﻳﺎﺘﻧرﺎﻧا ﺖﺳ) Pomegranate peel
extract, PPE (
ﺖﺳا ﻲﻌﻴﺒﻃ ناﺪﻴﺴﻛا ﻲﺘﻧآ زا ﻲﻨﻏ ﻊﺒﻨﻣ و دراد ﻲﻳﻻﺎﺑ ﻲﻧاﺪﻴﺴﻛا ﻲﺘﻧآ ﺖﻴﻟﺎﻌﻓ.
