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Effects of extraction methods on the phenolic compounds contents and

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Article  in  Food science and biotechnology · August 2015

DOI: 10.1007/s10068-015-0154-4

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Food Sci. Biotechnol. 24(4): 1201-1207 (2015)
DOI 10.1007/s10068-015-0154-4
RESEARCH ARTICLE
Effects of Extraction Methods on the Phenolic Compounds Contents
and Antioxidant Capacities of Cinnamon Extracts
Eva Dvorackova, Marie Snoblova, Lucie Chromcova, and Petr Hrdlicka
Received June 24, 2014; revised February 3, 2014; accepted February 10, 2014; published online August 31, 2015
© KoSFoST and Springer 2015
Abstract Extraction of the phenolic compounds, cinnamic
and benzoic acid derivates, from Cinnamonum cassia (Nees
& T.Nees) J.Presl was carried out. Classical solvent extraction,
ultrasonication, maceration, and shaking methods were
compared. Phenolic compounds were identified based on
ultrahigh-performance liquid chromatography with photodiode
array detector. The optimum solvent percentage was 60%
(v/v) ethanol (EtOH) in a ratio of 1:20 with the cinnamon
sample weight. The optimum extraction time was 90 min,
and the optimum extraction temperature was 50oC. Under
optimized conditions, the highest phenolic contents were
2.263±0.089 mg/g of free acids for sinapic acid, and the
contents of cinnamic acid were 0.103±0.031 mg/g of free
acids. The antioxidant capacity of the extract produced
using the best extraction conditions was 14.337±4.662
mmol/g and the total phenolic content was 1.918±0.528
mmol/g.
Keywords: phenolic compound, cinnamon, extraction,
ultrahigh-performance liquid chromatography, antioxidant
capacity
Introduction
An inappropriate diet that includes high levels of fats and/
or refined sugars leading to a high frequency of nutritional
imbalances is the major cause of obesity, metabolic syndrome,
and/or diabetes. Under such pathological conditions,
production of free radicals generated continuously via
normal physiological processes increases, along with other
Eva Dvorackova (
), Marie Snoblova, Lucie Chromcova, Petr Hrdlicka
Department of Chemistry and Biochemistry, Mendel University in Brno,
Zemedelska 1, CZ-61300 Brno, Czech Republic
Tel: +420 545 133 276; Fax: +420 545 212 044
E-mail: eva.dvorackova@mendelu.cz
reactive oxygen species (ROS). Damage from ROS has
been linked to some neurodegenerative diseases (1) and
cancers (2), and, due to oxidation of low-density lipoprotein,
plays a key role in promotion of cardiovascular diseases
and atherosclerosis (3-6). Therefore, foods or phytochemicals
with potent antioxidant and anti-inflammatory activities are
considered important resources. Spices have abundant
antioxidant capacities (AC) and excellent anti-inflammatory
activities (7-10) and should be an important resource when
developing dietary adjuvants for neurodegenerative diseases
(11).
Cinnamon is a common and well known spice obtained
from the inner bark of several trees of the genus Cinnamomum.
Cinnamon belongs to the Lauraceae family and is used as
a food and food flavoring material. The cinnamon used in
traditional Asian medicines is mainly Chinese cinnamon
[Cinnamonum cassia (Nees & T.Nees) J.Presl]. The
pharmacological properties of cinnamon, including stimulation
of digestive action, stimulation of hypolipidemic effects,
and antioxidant, anti-inflammatory, antifungal, antimutagenic,
and anticarcinogenic activities, have been documented
(12,13). Among sources of polyphenols, cinnamon may be
of special interest since cinnamon and aqueous cinnamon
extracts have been reported to be insulin sensitizers in vitro
and in vivo (14). In general, cinnamon contains high levels
of phenolic substances, including phenolic acids, coumarins,
and proanthocyanidins (15). Several studies have suggested
that cinnamon consumption has beneficial effects on
human health, including antidiabetic effects, a hypoglycemic
activity, and pancreas-protective effects (16), prevention of
urinary tract infections (17), and neuroprotection, reduction
of cardiovascular disease risk, and cancer prevention
(13,18,19).
Sample preparation has become a key procedure in
chemical analysis. Classical solvent extraction, along with
modifications, is one of the simplest yet most effective and
1202
versatile methods of sample preparation. Numerous studies
of the contents of antioxidant compounds in cinnamon
have been performed using different isolation methods
(6,13,20). The form in which cinnamon is administered
may be important since extracts and powders of pulverized
bark material contain different phytochemical compositions
with different levels of bioavailability. Thus, the wide variety
of available extraction methods makes direct comparison
of results from different studies problematic (21).
Intensive studies of the bioactive components of cinnamon
and total contents have been carried out; however, phenolic
identification data are insufficient and incomplete. Structure-
activity relationships between obtained extracts of cinnamon
have not been thoroughly discussed or revealed. Phenolic
compounds in cinnamon have been reported to be responsible
for antioxidant activities, but established correlative
relationships are few and convincing statistical data revealing
relationships between antioxidant activities and phenolic
contents are rare (10).
There are almost no studies available discussing problems
arising from solvent extraction. Therefore, the aims of this
work were to (1) optimize and compare extraction techniques;
(2) separate phenolic acids into free and bound forms and
identify liberated phenolic acids; (3) identify and quantify
the main phenolic compounds present using ultrahigh-
performance liquid chromatography with photodiode array
detector (UHPLC-PDA); (4) investigate cinnamon for
scavenging activities against ABTS•+ radicals and for total
phenolic contents (TPC); and (5) consider the effects of
physico-chemical parameters on the antioxidant activities
of extracts.
Materials and Methods
Chemicals and reagents Acetonitrile (ACN) was obtained
from Biosolve BV (Valkenswaard, Netherlands). Methanol
(MeOH), ethanol, ethyl acetate (EtOAc), potassium persulfate,
phosphate buffer (sodium monohydrogen phosphate, sodium
dihydrogen phosphate, sodium chloride), hydrochloric
acid, and acetic acid were obtained from Penta (Praha,
Czech Republic). Gallic acid, benzoic acid, salicylic acid,
and caffeic acid were purchased from Dr. Ehrenstorfer
GmbH (Augsburg, Germany). Protocatechuic acid was
purchased from Chromadex (Irvine, CA, USA). Trolox (6-
hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid),
sodium carbonate, Folin-Ciocalteu reagent, trans-cinnamic
acid, 3,4-dihydroxybenzaldehyde, and vanillic acid were
purchased from Sigma-Aldrich (St. Louis, MO, USA).
ABTS•+, syringic acid, p-coumaric acid, vanillin, 4-
hydroxybenoic acid, 4-hydroxybenzaldehyde, ferulic acid,
and sinapic acid were also purchased from Sigma-Aldrich.
Dvorackova et al.
Plant materials Milled and dried cinnamon bark
[Cinnamonum cassia (Nees & T.Nees) J.Presl] was
purchased from Mikado (Lidl, Czech Republic).
Phenolic compound extraction from cinnamon Extraction
of phenolic compounds from cinnamon was conducted
using different extraction methods. These methods were
chosen from literature (9,20,21) and adjusted for our lab
equipment. Sonication, the classical solvent extraction
method, maceration, and shaking were tested, each using 5
solvents, including ethanol, methanol, ethyl acetate,
acetone followed by ethanol, and water.
First, 2 g of dried cinnamon bark with 20 mL of pure
organic solvent (or distilled water) was subjected to
extraction using sonication in a Bandelin Sonorex ultrasonic
cleaning instrument (Bandelin Electronic GmbH, Berlin,
Germany) for 15 min at ambient temperature. Randall
extraction (Behr Labor Technik, Düsseldorf, Germany)
was performed at 80oC for 30 min. Shaking for 1 h at
ambient temperature (laboratory shaker HS 260; IKA
Werke GmbH, Staufen, Germany) was also performed, as
was maceration for 24 h at 8oC (standing in Erlenmeyer
flasks in refrigerator). Aqueous solvent solutions of 0, 20,
40, 60, 80, and 96% (v/v) were used for determination of
the most efficient method of organic solvent extraction.
Extraction ratios of 1:10, 1:20, and 1:40, extraction
temperatures of 50, 80, and 110oC, and extraction times of
30, 60, and 90 min were also investigated.
After each procedure, extracts were evaporated to dryness
under a nitrogen flow and reconstituted using acidified
distilled water (hydrochloric acid; Penta) (pH of approximately
2). Extracts were put on 1 mL/30 mg solid-phase extraction
(SPE) cartridges (Strata-X; Phenomenex, Torrance, CA,
USA) using a modified procedure of Inbaraj et al. (22).
The SPE procedure was performed using (a) conditioning
with methanol and water, (b) sample loading, (c) sample
washing in 5% (v/v) methanol, and (d) elution using
methanol. SPE extracts were filtered through 45 µm nylon
filters and individual phenols were analyzed using UHPLC
(Knauer Platin Blue, Berlin, Germany) coupled with a
PDA detector. Final extracts were subjected to hydrolysis
(proper procedure is subscribed in results and discussion-
final approach and hydrolysis) to obtain information on
free, ester, and glycoside-bound forms of phenolic compounds
in cinnamon. Each extraction was carried out in triplicate.
Values were expressed as mg/g of dry weight (DW).
Determination of the free radical scavenging activity
using the stable ABTS radical cation The free radical-
scavenging activity was determined using the ABTS
radical cation decolorization assay described by Re et al.
(23). ABTS was dissolved in MilliQ water to a 7.50 µM
Effects of Extractions on Phenols from Cinnamon
concentration. The ABTS radical cation (ABTS•+) was
produced based on reaction of an ABTS stock solution
with 4.95 µM potassium persulfate and keeping the product
in the dark at room temperature for 12-16 h before use.
ABTS•+ was dissolved at a ratio of 1:18 in a phosphate
buffer prior to analysis. A calibration curve for Trolox was
prepared at a concentration range 0-50 µmol/L. Samples of
cinnamon were diluted if necessary. The absorbance of the
resulting blue color was measured at 734 nm using a
Genesys 100 UV-VIS (Thermo Fisher Scientific Inc.,
Waltham, MA, USA) spectrophotometer exactly 20 min
after initial mixing. Quantification was performed based on
the standard curve for Trolox. Results were expressed as
mmol of Trolox per 1 g of dry weight as Trolox equivalents
(TEAC). Values were expressed as a mean (n=3)±standard
deviation (SD).
Spectrophotometric determination of total polyphenols
Determination of the total polyphenol content (TPC) of
extracts was performed following the modified Folin-
Ciocalteu colorimetric method (24) calibrated against gallic
acid as a reference standard in a concentration range 0-100
µmol/L. Samples of cinnamon were diluted if necessary.
The absorbance of the resulting blue color was measured at
765 nm using a Genesys 100 UV-VIS spectrophotometer
(Thermo Fisher Scientific Inc.) exactly 40 min after initial
mixing. Results were corrected for dilution and expressed
in mmol of gallic acid per 1 g of dry weight as gallic acid
equivalents (GAE). Values were expressed as a mean
(n=3)±SD.
UHPLC-PDA instrumentation and conditions Separation
of cinnamon phenols was performed based on UHPLC
(Knauer Platin Blue) equipped with 2 pumps (Platin Blue
P-1 and Platin Blue P-2), a Platin Blue AS-1 autosampler,
a Platin Blue T-1 column thermostat, and a Platin Blue
PDA-1 photodiode array detector. Chromatographic separation
was performed on a Kinetex C18 column (I.D. 4.6 mm×
100 mm, 2.6 µm particle size; Phenomenex). Phenolic
compounds were analyzed using an acetonitrile-water
gradient with addition of 0.8 % formic acid following a
solvent program with A, acetic acid/B, acetonitrile of
0.0 min, 90%A/10%B; 1.0 min, 92%A/8%B; 1.1-4.0 min,
97%A/3%B; 5.0-8.9 min, 92%A/8%B; 9.0-13.0 min,
89%A/11%B; 13.6-15.5 min, 65%A/35%B; and 16.0-18.0
min, 90%A/10%B. The operating conditions were a column
temperature of 30oC, an injection volume of 5 µL, and
PDA detector wavelengths set to 270, 290, 310, and 324
nm. Before injection, extracts were filtered through a
0.45 µL nylon membrane filter Supelco (Sigma-Aldrich).
Identification of phenolic compounds was carried out
based on comparison of retention times and spectral data
with authentic standards. Quantitative determinations were
1203
performed using standard calibration curves prepared
based on dilution of stock standards in 80% methanol.
Values were expressed as a mean (n=3)±SD and expressed
as mg of phenolic compounds/g of dry cinnamon.
For the majority of phenolic compounds, limits of
detection (calculated by software) ranged from 0.116 µg/
mL to 0.953 µg/mL, except for ferulic acid (1.470 µg/mL),
sinapic acid (3.115 µg/mL), and cinnamic acid (0.065 µg/
mL).
Statistics and interpretation of results Values were
expressed as a mean (n=3)±SD and expressed as mg of
phenolic compounds/g of dry cinnamon. Statistical evaluation
was performed using Statistica software version 12
(StatSoft Inc., Tulsa, OK, USA).
Results and Discussion
The most influential experimental variables for extraction
of phenolic compounds from the bark of dry cinnamon
were the extraction method (sonication, classical solvent
extraction, maceration, and shaking), the type of solvent
(ethanol, methanol, ethyl acetate, water, acetone, followed
by ethanol), the solvent concentration (0, 20, 40, 60, 80,
and 96% aqueous solutions), the solvent/sample weight
ratio (1:10, 1:20, 1:30), the extraction time (30, 60, and 90
min), and the extraction temperature (50, 80, and 110oC).
These variables were evaluated for optimization of the
extraction efficiency (Fig. 1) and were the key factors in the
extraction processes as they affected both the kinetics of
phenolic release from the solid matrix and the AC of
extracts. Analyses were performed in several steps. First,
the optimal extraction method and optimal extraction
solvent were determined on the basis of amounts of
phenolics in cinnamon extracts. In subsequent steps,
remaining variables relating to the most suitable extraction
method and solvent were optimized.
Influence of the extraction method and solvent Cinnamon
contains large amounts of fiber and carbohydrates that can
cause problems during sample extraction. Sonication, shaking,
and maceration produced large amounts of slime and,
therefore, were considered inappropriate methods. Extracts
produced using sonication, maceration, and shaking were
analyzed despite a high density. However, analysis was
possible after many hours of filtration and passing through
SPE columns, after which some extracts caused blockage
of the UHPLC column. The best option was, therefore,
Randall extraction with modification. Instead of using a
standard extraction thimble, an infusion sock was used,
which greatly increased the availability of the solvent to
cinnamon sample particles. The sock also eliminated
1204
Fig. 1. Optimization of extraction steps.
Fig. 2. Comparison of extraction techniques using different
solvents. Value=mean (n=3 for each solvent), box=standard error,
clamps=confidence interval (α=0.05, thus p=0.95). Within
treatments, different small letters indicate significant differences
(α=0.05, thus p=0.95) between solvents. Between treatments,
different uppercase letters indicate significant differences for
solvent (only MeOH as other solvents showed no differences).
formation of slime in the solvent.
The solvents methanol, ethanol, acetone, and ethyl acetate
at different concentrations in water have commonly been
applied for extraction of phenols from plants (20).
Methanol, ethanol, acetone, ethyl acetate, and distilled
water were used in this study for extraction of cinnamon
phenols during optimization of extraction, and different
polyphenol yields were obtained (Fig. 2). Recovery of
phenolic compounds was dependent on the solvent used
and the solvent polarity. Highest yields were obtained
using ethanol, which is a commonly used solvent (25).
Other solvents produced much lower extraction yields and,
for an acetone/ethanol mixture, it was not possible to
analyze produced extracts because of a high density.
Solvent composition The influence of the ethanol content
Dvorackova et al.
Fig. 3. Varying proportions of ethanol.
in the extraction solvent was investigated based on varying
the ethanol proportion in the range 0-96% (v/v) using
Randall extraction. An adequate balance between solvent
polarity and phenolic compound extraction yield was
important. The percentage concentration of the solvent is
critical with respect to extraction of components, and 60%
(v/v) ethanol was the most efficient solvent concentration
for extraction of phenolic compounds from cinnamon (Fig.
3). Cinnamon phenolic contents differed considerably as a
function of solvent composition, in agreement with previous
studies that showed that the nature of the solvent exerts a
great influence on phenolic extraction capacities with regard
to many species, and in agreement with previous reports
suggesting that a binary solvent system is more efficient
than a mono-solvent system (water or pure ethanol) for
extraction of phenolic compounds regarding relative polarity
(26). Wang et al. (27) investigated the influence of solvents
on the amount of extracted phenolic compounds and
concluded that the optimal extraction capacity was achieved
with a 30-60% (v/v) aqueous solution of ethanol. Compared
with other solvents, such as 30% (v/v) methanol, acetone,
and acetonitrile, the difference in the yield of polyphenol
compounds was not substantial. The amount of water in
the aqueous solution was more important for polyphenol
extraction than the solvent used.
After extraction and reconstitution, pure ethanol and
80% (v/v) ethanol were difficult to work with on SPE
cartridges because of the extract density in agreement with
other reports dealing with determination of natural phenols
in other sample types (25).
Solvent volume, extraction time, and temperature
optimization Optimum ratios of sample weight to
solvent volume for extraction of phenolic compounds from
cinnamon of 1:10, 1:20, and 1:30 were compared. Optimum
extraction of phenolic compounds was achieved using a
ratio of 1:20 with 60% (v/v) ethanol (Fig. 4A). Extraction
was performed under optimal conditions for different
durations (Fig. 4B) to investigate the effect of time on
extraction of phenolic compounds. The phenolic compound
Effects of Extractions on Phenols from Cinnamon
Fig. 4. Optimization steps for solvent volume, time, and temperature.
content in extracts obtained using a 60% (v/v) aqueous
ethanol solution increased with longer extraction times, in
agreement with Dent et al. (26) who showed an increasing
phenolic content with time obtained during extraction
using a 70% (v/v) aqueous solution of ethanol, acetone,
and distilled water with the highest values observed at 90
min.
Temperatures of 50, 80, and 110oC (Fig. 4C) were
applied to determine the optimum phenolic contents. Cinnamon
extracts obtained at an extraction temperature of 50oC
contained the highest content of phenolic compounds due
to increased solubility and relevant diffusion coefficients.
Higher temperatures probably produced a decrease in the
extraction yield due to degradation of phenolic compounds
caused by hydrolysis, internal redox reactions, and
polymerization (25,28). Increased solvent losses at high
temperatures were also reported.
Final approach and hydrolysis Different extraction
variables had substantial effects on extraction of phenolic
compounds. Randall extraction yielded the best extraction
potential using 60% (v/v) ethanol as the solvent at an
extraction time of 90 min, an extraction temperature of
50oC, and an extraction ratio of 1:20.
Phenolic compounds usually occur in conjugated forms
and many phenolic compounds occur as glycosides or
esters. Thus, sample preparation included alkaline and acid
hydrolysis to free bound phenolic compounds. Hydrolysis
of phenolic glycosides to corresponding aglycones offers a
practical method for quantification of phenolic compounds
in natural matrices (29,30). In the extraction optimization
procedure, the hydrolysis step was omitted because phenolic
compounds were analyzed as derivatives. Only in the final
1205
approach was hydrolysis performed using addition of 2 M
natrium hydroxide and/or 2 M hydrochloric acid at a ratio
1:1. For a complete hydrolysis reaction, cinnamon samples
were left to stand in darkness for 15 min. The hydrolysis
procedure was modified from the procedure of Mattila and
Kumpulainen (31). Temperatures (ambient temperature of
80 and 100oC in a water bath) and times (4, 1 h, 30,
15 min) of both hydrolysis steps were determined based on
a series of experiments. After alkaline hydrolysis, cinnamon
samples were adjusted by adding 6 M hydrochloric acid to
approximately pH 2 (checked by pH meter EL20; Mettler-
Toledo Inc., Columbus, OH, USA).
The applied hydrolysis procedure increased the extraction
efficiency with respect to phenolic compounds by more
than 2×. UHPLC analytical results for hydrolyzed extracts
of cinnamon are shown in Fig. 5. Phenolic compounds
obtained as hydrolysates were substantially more abundant
than free derivates. Rommel and Wrolstad (32,33) used
alkaline hydrolysis (2 M NaOH) to study hydroxycinnamic
and hydroxybenzoic acids in red raspberry juices and
reported that the rate of acid/base hydrolysis of glycosides
depended on the acid/base strength, the nature of the sugar
moiety, and the position of the moiety in the phenolic
nucleus. Glucuronides resist acid hydrolysis better than
glucosides, which are rapidly cleaved (29,30).
The phenolic compounds, sinapic acid, cinnamic acid, p-
coumaric acid, protocatechuic acid, caffeic acid, 3,4-
dihydroxybenzaldehyde, and vanillin were identified (Fig.
5) in cinnamon based on retention times and spectral peak
characteristics against standards using UHPLC coupled
with a PDA detector. Randall extraction with 60% (v/v)
ethanol at a ratio of 1:20 for 90 min at 50oC yielded the
highest content of sinapic acid. The mass fraction of most
1206 Dvorackova et al.

Fig. 5. HPLC analysis of phenolic compounds in cinnamon before and after hydrolysis.

Table 1. AC and TPC in optimization steps with relative method and in the solvent-type optimization procedure,
standard deviations (RSD) and results were in agreement with the phenolic compound
AC TCP AC TCP contents determined based on UHPLC-PDA. Due to
[mmol/g] [mmol/g] % RSD % RSD difficulties caused by creation of slime using methanol,
Water 0.268 0.167 0.151 0.097 ethanol was used in combination with Randall extraction as
20% EtOH 8.175 1.049 0.853 0.371 the second most appropriate extraction system yielding the
40% EtOH 14.634 1.506 5.298 0.092 second highest AC value of 2.109±0.458 mmol/g of DW.
60% EtOH 17.139 1.259 8.890 0.182 In the optimization step, the AC and the TPC were
20 mL 17.139 1.259 8.890 0.182 measured. Results were in agreement with the TPC (Table
40 mL 11.675 1.415 8.264 0.301 1). The AC increased proportionally with the TPC, indicating
60 mL 1.121 1.233 0.672 0.074 that polyphenols were responsible for the AC of cinnamon.
30 min 11.675 1.415 8.264 0.301 However, such a correlation was not confirmed with
60 min 2.720 1.051 3.012 0.064 phenolic contents determined using UHPLC, probably
90 min 10.531 1.556 3.557 0.250 because of an absence of the whole phenolic spectrum
50oC 14.337 1.918 4.662 0.528 measured chromatographically. Thus, compounds affecting
80oC 10.531 1.556 3.557 0.250
AC and TPC were missing.
110oC 46.448 3.482 16.245 0.020
The main phenolic compounds in cinnamon [Cinnamonum
cassia (Nees & T.Nees) J.Presl] extracts were sinapic and
represented phenolic compounds varied from 0.303 mg/g cinnamic acids. Caffeic, vanillic acid, and 3,4-dihydroxy-
of DW for cinnamic acid to 5.796 mg/g of DW for sinapic benzaldehyde were also identified. The contents of total
acid. and individual phenols depended on the extraction method,
the type of extraction solvent, the solvent composition, and the
TPC and AC The chemical complexity of extracts, often extraction temperature. Binary solvent systems are more
mixtures of dozens of compounds with differences in efficient than mono-solvent systems for extraction of
functional groups, polarity, and chemical behavior, can phenolic compounds with regard to relative polarity. An
lead to complex results, depending on the assay method aqueous solution of 60% (v/v) ethanol, an extraction
used for analysis. In order to test the radical scavenging temperature of 50oC, an extraction ratio of 1:20, and an
activities of medicinal plant extracts, reaction of the stable extraction time of 90 min were the optimum conditions for
ABTS radical with extracts was performed. The extent of extraction of phenolic compounds from dry cinnamon
decolorization of the evaluated radical was proportional to bark. The applied extraction methods provided advantages
the concentration of antioxidant present in the reaction in extraction efficiency.
mixture.
The AC was measured in the first step of the extraction Disclosure The authors declare no conflict of interest.
 Effects of Extractions on Phenols from Cinnamon
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