Journal of the Iranian Chemical Society

https://doi.org/10.1007/s13738-019-01622-5

ORIGINAL PAPER

Magnetic solid-phase extraction of quercetin on magnetic-activated

carbon cloth (MACC)
Muhammad Balal Arain1,2,3 · Erkan Yilmaz4,5 · Numan Hoda6 · Tasneem Gul Kazi7 · Mustafa Soylak1

Received: 29 October 2018 / Accepted: 23 January 2019

© Iranian Chemical Society 2019

Abstract
Magnetic-activated carbon cloth (MACC) was synthesized, characterized, and used as magnetic adsorbent in magnetic
solid-phase extraction of quercetin prior to UV–visible spectrophotometric determination. Different parameters such as pH,
amount of MACC, effect of volume, and elution time were optimized for the determination of quercetin using UV–visible
spectrophotometer at 370 nm. In this procedure, quercetin molecules in aqueous sample phase were adsorbed on the 10 mg
of the adsorbent at pH 4.0 and desorbed with acidic methanol solution by using vortex mixer. Limit of detection (LOD),
limit of quantification (LOQ), and relative standard deviation were found as 1.4 ng mL−1, 4.8 ng mL−1 and lower than 10%,
respectively. The applicability of the developed magnetic solid-phase extraction method was proved on onion samples.

Keywords  Quercetin · Magnetic solid-phase extraction · Activated carbon cloth · Spectrophotometry

Introduction studied in onions and apples. Green tea and red wine are also
rich source of quercetin. Amount of quercetin in onions is
Quercetin is known, as plant pigment flavonoid is variable of bulb color and type, mostly concentrated in the
widely distributed in nature with chemical composition outer skins and rings [2]. The estimated average daily con-
3,3′,4′,5,7-penta-hydroxy-flavone, having a catechol func- sumption of quercetin is 25–50 mg [3]. Clinical researches
tional unit on the B-ring structure. Quercetin has proven to tend to show that quercetin is responsible for the variety
be one of the most prominent bioflavonoids, mainly occurs of pharmacological activities due to the promising anti-
in leaves and other parts of the plants as a glycones and gly- oxidant and anti-inflammatory functions and the ability to
cosides. Almost 180 different glycosides of quercetin have sequester-free radicals [4]. Literature survey has explained
described in nature [1]. The highest level of quercetin is that during metabolism process quercetin plays a vital role
and suppresses oxidative stress, by controlling physiologi-
* Mustafa Soylak cal mechanisms to slow down free-radical formation [5].
soylak@erciyes.edu.tr Similarly, plants have also developed methods of stopping
free-radical damage. Polyphenol structure of quercetin
1
Department of Chemistry, Faculty of Sciences, Erciyes which contains double bonds and hydroxyl groups that can
University, 38039 Kayseri, Turkey
donate electrons through resonance to stabilize the free radi-
2
Department of Chemistry, University of Karachi, Karachi, cals [5]. Chronic administration of quercetin is marked to
Sindh 75270, Pakistan
improve dyslipidemia, hypertension, and hyper-insulinemia
3
Department of Chemistry, Abdul Wali Khan University, and also reduces plasma cholesterol, hepatic lipids, and body
Mardan, KPK 23200, Pakistan
weight gain, studied on both in animal and human models
4
Department of Analytical Chemistry, Faculty of Pharmacy, [6, 7]. The bioactivity of quercetin has been taken growing
Erciyes University, 38039 Kayseri, Turkey
attention in scientific research during the recent years and
5
Nanotechnology Research Center (ERNAM), Erciyes numerous works have been published on pharmacological
University, 38039 Kayseri, Turkey
interests of quercetin.
6
Engineering Faculty, Akdeniz University, 07058 Antalya, Several methodologies have been applied for the extrac-
Turkey
tion of quercetin from plants, foods, and beverages, such as
7
National Center of Excellence in Analytical Chemistry, solid0phase extraction (SPE), coprecipitation, cloud point
University of Sindh, Jamshoro 76080, Pakistan

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 Journal of the Iranian Chemical Society

extraction (CPE), and liquid–liquid extraction (LLE) [8–12]. Reagents and solutions

Currently, magnetic solid-phase extraction (MSPE) has been
received prominent devotion for the trace-level analysis, Activated carbon cloth was produced, characterized, and
due to the high enrichment factor and maximum recover- obtained at the laboratories of Akdeniz University-Turkey
ies. MSPE technique describes the extraction of different [18, 19]. Quercetin was purchased from Sigma-Aldrich.
compounds from the sample using solids with magnetic ­FeSO4⋅7H2O and ­FeCl3⋅6H2O salts were purchased from
properties. It is based on the use of magnetic adsorbent and Sigma-Aldrich. Ultrapure water further purified through
the used adsorbents can be reproduced by the adsorption of reverse osmosis (0.055 µS cm−1, Millipore) was used as the
ionic surfactants on the surface of magnetite. The primary working medium. Methanol, ethanol and acetone, sodium
advantage of MSPE is that it eliminated problem related to acetate, sodium dihydrogen phosphate, disodium hydro-
column packing with the easy and rapid phase separation of gen phosphate dibasic, and acetic acid were obtained from
the sorbent which is achieved directly -using magnets and Sigma-Aldrich, St. Louis, MA, USA.
avoids the need for filtration and/or centrifugation steps.
Activated carbon cloths (ACC) behave as a dynamic and
Preparation of magnetic‑activated carbon cloth
versatile adsorbent and used for extraction due to their excel-
lent physical and chemical properties [11–13]. Activated
The fabrics of activated carbon cloth (ACC) were cut into
carbon cloth (ACC) is a highly microporous carbon material
small pieces and transferred into 500 mL of two-necked syn-
having larger pore volume and more uniform micropore size
thesis unit. Co-precipitation method was used for modifica-
distribution than granular activated carbon [14–17]. Acti-
tion of the ACC with F­ e3O4 nanoparticles. For this purpose,
vated carbon cloth immobilized magnetic nanoparticles in
2.2 g of ­FeSO4⋅7H2O and 3.3 g of ­FeCl3⋅6H2O salts were
solid-phase extraction for the separation and preconcentra-
solved in 100 mL of distilled water and the obtained solution
tion of quercetin can be a possible absorbent and has not
was added on the ACC in the two-necked synthesis unit. The
been explored according to the literature survey.
obtained mixture was stirred on the magnetic stirrer for 3 h
The present study is intended to establish a novel MSPE
between at 60 °C and concentrated ­NH3 was added drop-
technique based on ACC immobilized with magnetic
wise in the mixture. At this stage, black F
­ e3O4 nanoparticles
nanoparticles, for the separation and preconcentration of
were formed on the fabrics of the ACC. This experiment was
quercetin prior to UV–Vis spectrophotometric determina-
carried out under argon atmosphere to avoid oxidation of
tion. Different parameters such as pH, amount of adsorbent,
­Fe3O4–Fe2O3 and to obtained uniform particle size of ­Fe3O4,
extraction time, type of eluent, and sample volume have
respectively. Magnetic ACC particles were collected using a
been optimized. The developed extraction method was suc-
neodymium magnet, washed three times with distilled water
cessfully applied for the determination of quercetin in onion
and two times with methanol, to remove any impurities.
samples.

Preparation of onion samples

Experimental
The onion samples were obtained from local markets of
Apparatus Kayseri province in Turkey. One gram of onion sample were
taken, dried an oven at 70 °C, and homogenized using an
pH adjustments of sample solutions were carried out by a agate mortar. The homogenized sample was taken into a
Sartorius PT-10 model pH meter with glass electrode (Sar- centrifuge tube and 10 mL ethanol (99.8%, Sigma-Aldrich)
torius Co., Goettingen, Germany). An ultrasonic water bath was added. Quercetin was extracted into ethanol phase by
(Norwalk, CT, USA) was used to produce nanosized and/ shaking for 3 h at room temperature. Solid portions of the
or microsized emulsion in water phase. The centrifugation samples were removed by centrifugation and known vol-
for phase separation was achieved using an ALC PK 120 ume of supernatant solution was taken and completed to the
model centrifuge (Buckinghamshire, England). The quanti- 10 mL with water and then subjected to developed micro-
tative analyses were carried with the help UV–visible spec- extraction procedure.
trophotometer (UH5300 Hitachi Japan). FT-IR spectra of the
adsorbent were carried using Perkin-Elmer 400 FT-IR spec- Magnetic solid‑phase extraction procedure
trometer (Waltham, MA, USA). For surface morphology of
the adsorbent the SEM images were obtained using 440 LEO 10 mg of MACC in graduated was added to 15 mL test tube.
SEM (Leo Electron microscopy, Cambridge, UK). X-ray dif- Two mL of pH 4.0 buffer solution and 0.2 mL of 1 × 10−4 M
fraction (XRD) spectrum measurements for adsorbent was quercetin was added to the tube. It was completed to 10 mL
performed using a Bruker AXS D8 advanced diffractometer.

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Journal of the Iranian Chemical Society

with milli-Q water. This solution was vortexed 5 min. All magnetic-ACC, a new intense peak is seen around 542 cm−1,
quercetin was adsorbed on MACC, separated this with a which is characteristic peak for Fe–O vibration and also this
magnet, and removed water phase. 5 mL methanol:acetic indicates that ­Fe3O4 is successfully formed within the struc-
acid (5%) solution was added to test tube that contain ture of the activated carbon cloth. Moreover, the important
adsorbed quercetin on MACC and placed into ultrasonic differences are seen between the FT-IR spectra of ACC and
bath for 10 min for desorption/elution. MACC was separated magnetic-ACC.
using neodymium magnet. Quercetin in the final solution
was determined with UV–visible spectrophotometer. In the Effect of solvent
presented solid-phase extraction procedure, methanol was
used as blank. For suitable solvent selection, we dissolved quercetin in
methanol, ethanol, and acetone. Maximum absorbance was
found with acetone at 300 nm. At the same time, second
Results and discussion peak obtained at 370 nm and with ethanol λmax at 375 nm.
With methanol, we found good absorbance at 370  nm.
Characterization of the magnetic‑activated carbon Therefore, methanol was selected for further study.
cloth
Effect of pH on preconcentration
The XRD spectrum of the magnetic-ACC is illustrated in
Fig. 1. The diffraction peaks at 2θ values 30.5, 35.0, 43.5, In the solid-phase extraction techniques, enrichment of
57.5, and 63.0 are characteristic for the crystalline reflection analyte is based on the interactions between analytes and
patterns (220), (311), (400), (511), and (440), respectively, sorbet, so that the pH of aqueous medium is considered as a
which can be readily indexed to from the JCPDS card no. dominating factor for quantitative recoveries of any chemi-
19–0629 for ­Fe3O4 nano-particles. The XRD results sug- cal constituent [20–24]. For this importance, the influence
gesting that the ­Fe3O4 nano-particles were well formed on of pH on the pretreatment of quercetin was examined in
the fabric of the ACC. the pH range of  2–10 (keeping the other factors constant).
SEM images of pristine activated carbon cloth fabrics The adjustment of the sample solution pH was carried out
and magnetic activated carbon cloth fabrics are illustrated using buffer solution. Deposition of analyte was cauterized
in Fig. 2a, b, respectively. The SEM image of MACC proved as pH of model solution, as shown in Fig. 4, presented the
that the uniform fabric structure of the ACC is deteriorated recovery % of analyte. It describes that the recoveries were
and magnetic F ­ e3O4 nano-particles are formed in different higher than 90% for all pH values and maximum recovery
regions of the fibers. was obtained at pH 4.0 (> 95%). The main interactions in
The FT-IR spectra of ACC and magnetic-ACC are illus- solid-phase extraction systems are Waals forces or dispersion
trated in Fig. 3. As it can be seen from FT-IR spectrum of forces, hydrogen bonding, and electrostatic interactions. The

Fig. 1  XRD spectrum of the

15
magnetic-ACC​
14
13
12
11
10
Lin (Counts)

9
8
7
6
5
4

3
2

1
0
10 20 30 40 50 60 70 80 90
2-Theta - Scale

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Fig. 2  SEM images of pristine-activated carbon cloth (a) and magnetic-activated carbon cloth (b)

63.5
62
60
58
56
54
52
50
48
%T 46 542.04
44
42
40
38
36
34
32
30.0
4000.0 3000 2000 1500 1000 450.0
cm-1

Fig. 3  FTIR spectrum of activated carbon cloth (red colour) and magnetic activated carbon cloth (blue colour)

100 results showed that adsorption of quercetin was not affected

by surface charge of magnetic-activated carbon cloth and
80
quercetin, which lead to electrostatic interactions. Hence, it
% Recovery

60 can be explained nonpolar–nonpolar attractive forces called

van der Waals forces, or dispersion forces between mag-
40
netic activated carbon cloth and quercetin. For maximum
20 efficiency and good selectivity, pH 4.0 was selected for fur-
ther subsequent experiment.
0
2 3 4 5 6 7 8 9 10
pH
Amount of MACC​
Fig. 4  Relations between pH and recovery values of querce-
tin (amount of sorbent 10  mg, vortex time 5  min, eluent 5  mL For the quantitative recoveries of analytes on the solid-phase
methanol:acetic acid (5%) solution, N = 3) extraction studies, the amount of the adsorbent is one of

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Journal of the Iranian Chemical Society

100
Effect of the sample volume

80 Optimization of the highest possible volume to which the

proposed solid-phase extraction method is successfully
% Recovery

60 applied is of immense importance, because the efficiency of

the adsorbent can be determined by calculating the highest
40
preconcentration factor of the developed method [30–38].
20
For this purpose, the developed solid-phase extraction was
carried out at different sample volumes ranging from 10 to
0 60 mL and the results are given in Fig. 6. The quantita-
0 10 20 30 40 50
MACC (mg)
tive recoveries were obtained in the sample volume range
of 10–45 mL. The preconcentration factor was calculated
Fig. 5  Influences of the amount of MACC on the recovery values of
as 9 when the final eluent volume was 5 mL.
quercetin [pH of aqueous sample solution 4.0, vortex time 5 min, elu-
ent 5 mL methanol:acetic acid (5%) solution, N = 3] Effect of diverse ions

The influences of matrix components of environmental

the critical analytical parameter [25–29]. The effects of the samples are one of the main problems in the determination
amounts of MACC were investigated in the optimal condi- of the organic, inorganic, and bio-active-based analytes at
tion in the range of 2.5–50 mg of MACC. The results are trace levels. Separation processes have been used to solve
shown in Fig. 5. The quantitative recoveries for quercetin these effects by the analytical chemists [39–50]. Most of the
were obtained in the range of 2.5–30 mg range. For further potential ions, such as alkali and alkaline earth elements,
works, 10 mg of MACC was selected as optimal amount of usually present in the real sample. Therefore, it is necessary
MACC. to check effect of these diversifying ions in the sample to
get optimum condition. Hence, the effect of these ions was
examined and results are shown in Table 1. The developed
Elution solid-phase extraction method has strong selectivity and the
common ions have no interference effect on the determina-
Elution of the adsorbed species on the adsorbent signifi- tion of quercetin.
cantly effect on the preconcentration procedure has been
used for the removal of analyte ions from the sorbent. To Analytical performance
get maximum recoveries within the minimal concentra-
tion and volume, optimization of the elution condition was The absorption spectra of quercetin after magnetic solid-
performed. For the selection of suitable eluent solvent, two phase extraction procedure on MACC are given in Fig. 7.
different types of eluent solvent, 5% and 10% acetic acid The limit of detection (LOD) and the limit of quantification
solution in methanol, were studied. Quantitative results (LOQ) for the developed analytical method were calculated
were obtained using 5% of acetic acid/methanol solution. from the equation 3s/m and 10s/m, respectively, where s
Based on the experiment results, we selected 5% of acetic
acid/methanol solution as eluent. Literature survey supports
selection of acidic methanol for elution [25]. To find opti- 100
mum eluent volume, the effect of the elution solvent volume
was studied in the range of 1.0–5.0 mL. Clearly, with the 80

increase of the elution volume, the recoveries of analytes

% Recovery

60
were increased sharply. When the volume was reached to
5.0 mL, quantitative results were obtained. Hence, the elut- 40

ing solvent volume was chosen as 5.0 mL.

20
Ultrasonication time is considered as one of the important
factor in the solid-phase extraction studies for the quantita- 0
0 10 20 30 40 50 60
tive recoveries. The effect of the elution time of the under-
Sample Volume (mL)
study sample solution over the recoveries of analyte on
MACC was investigated. Time studied from 1 to 55 min at
Fig. 6  Effect of sample volume on the recoveries of quercetin [pH of
different temperatures. At 60 °C, 5 min was received quan- aqueous sample solution 4.0, amount of sorbent 10  mg, vortex time
titative results. 5 min, eluent 5 mL methanol:acetic acid (5%) solution, N = 3]

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 Journal of the Iranian Chemical Society

Table 1  Effect of diverse ions (N = 3) several earlier studies carried out on quercetin showed that
Ion Added as Concentration Recovery (%) our method provides better or comparable limit of detection
(mg L−1) and relative standard deviation than these methods (Table 2).

Na+ NaCl 2000 86 ± 3a

K+ KCl 1000 102 ± 3 Applications
Ca2+ Ca(NO3)2⋅4H2O 500 105 ± 7
Fe3+ Fe(NO3)3⋅9H2O 10 91 ± 5 Method was used to extract quercetin from onion collected
Zn2+ Zn(NO3)2⋅6H2O 10 96 ± 6 from local market. It was found that the best solvent for the
SO42− Na2SO4 2000 84 ± 4 extraction of quercetin flavonoids was methanol (MeOH);
a
the efficiency of the extraction of flavonoids in other solvents
 Mean ± standard deviation
decreases in the order: MeOH > tetrahydrofuran > acetone
hexane, dichloromethane [46, 47]. Therefore, methanol
2.5
used for the quercetin extraction. Standard addition method
was used for determining the concentration of quercetin
2
in real samples and recoveries were found in the ranges
92.7–101.9%. Reaction was repeated three times and con-
1.5 centration calculations were based on average value querce-
Absorbance

tin concentration in onion samples was determined which

1 was 268 ± 1 mg L− 1. Results of this investigation are given
in Table 3.
0.5

0
300 350 400 450 500 Conclusions
Vawelength, nm

The present study demonstrates a new MACC SPME method

Fig. 7  Absorption spectra of quercetin after magnetic solid-phase
extraction procedure for the instantaneous separation and enrichment of quercetin,
combined with UV–visible spectrometry. MACC for SPME
is proven to be a useful tool for the extraction and pretreat-
represents standard deviation of the ten blank solutions and ment of most of quercetin in real objects and can be consid-
m is the slope of the calibration curve. The LOD and LOQ ered as complementary to commonly used methods. Never-
were found as 1.4 ng mL−1 and 4.8 ng mL−1, respectively. theless, SPME provides many advantages over conventional
The repeatability of the developed method, which given with sample preparation techniques. SPME with MACC as adsor-
relative standard deviation (RSD) were less than 10%. The bent which will broaden the scope of applications for SPME,
linear equation was Y = 0.0522x − 0.0051 with a correlation in selecting a method for sample preparation those can be
coefficient (R2) of 0.997. The linear range for the develop- taken first to provide the most complete extraction of target
ment method was 16.8–3358 ng mL− 1. The comparison of compounds from the analyzed samples, preferably, in their
the suggested magnetic solid-phase extraction method with native form. In the proposed application, an ultrasonic water

Table 2  Comparison of Procedure LOD (µg L−1) RSD (%) Sample matrix Refs.

analytical features of the
developed magnetic SPE–UV– SPE–HPLC 7–35 4–9.4 Biological samples [51]
Vis method with other literature
SPE–HPLC–UV 60 1.9–10.1 Honey [52]
reports for determination of
quercetin DLLME–HPLC 133 1.18–2.73 Wine [53]
IL–PLE–HPLC 3.8 < 5.7 Herbal medicine [54]
UA-D-µ-SPE–UV–Vis 4.35 < 6.0 Nasturtium officinale [55]
extract and fruit juice
UE–RP-HPLC 790–2900 1.55 Sea buckthorn [56]
LLE–GC–MS 610 0.61–1.41 Wine [57]
Magnetic SPE–UV–Vis 1.4 < 10 Onion This study

SPE solid-phase extraction, DLLME dispersive liquid–liquid microextraction, LLE Liquid–liquid extrac-
tion, IL-PLE ionic liquid-based pressurized liquid extraction, UA-D-µ-SPE ultrasound-assisted dispersive
micro-solid-phase extraction, GC–MS gas chromatography–mass spectroscopy

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Journal of the Iranian Chemical Society

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Added (mg/L) Measured (mg/L) Recovery (%) (2006)
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0 268 ± 1a – 21. M. Soylak, M. Khan, R. Alosmanov, J. Shah, M.R. Jan, J. Radio-
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