Analytical Letters

ISSN: 0003-2719 (Print) 1532-236X (Online) Journal homepage: https://www.tandfonline.com/loi/lanl20

Application of a Novel Ionic Liquid as an

Alternative Green Solvent for the Extraction of
Curcumin from Turmeric with Response Surface
Methodology: Determination and Optimization
Study

Büşra Gökdemir, Nilay Baylan & Süheyla Çehreli

To cite this article: Büşra Gökdemir, Nilay Baylan & Süheyla Çehreli (2020): Application of a Novel
Ionic Liquid as an Alternative Green Solvent for the Extraction of Curcumin from Turmeric with
Response Surface Methodology: Determination and Optimization Study, Analytical Letters, DOI:
10.1080/00032719.2020.1730394

To link to this article: https://doi.org/10.1080/00032719.2020.1730394

Published online: 20 Feb 2020.

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ANALYTICAL LETTERS
https://doi.org/10.1080/00032719.2020.1730394

PRECONCENTRATION TECHNIQUES

Application of a Novel Ionic Liquid as an Alternative Green

Solvent for the Extraction of Curcumin from Turmeric with
Response Surface Methodology: Determination and
Optimization Study
Bu €kdemira, Nilay Baylanb, and Su
€şra Go €heyla Çehrelib
a
Chemistry Analysis Lab, Saniter Food-Environmental Science and Engineering Company, Ataşehir,
_Istanbul; bDepartment of Chemical Engineering, _Istanbul University-Cerrahpaşa, _Istanbul, Turkey

ABSTRACT ARTICLE HISTORY

Curcumin, a bio-active phytochemical, is a major component of tur- Received 9 January 2020
meric. It is also a significant food flavoring and potential therapeutic Accepted 12 February 2020
agent for diverse diseases. The traditional organic solvents are not
KEYWORDS
environmentally friendly because of their features including toxicity,
Curcumin; extraction; green
volatility and flammability. For this reason, in this study, the ionic solvent; high-performance
liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide liquid chromatography
([BMIM][Tf2N]), as an alternative green solvent, was investigated for (HPLC); response surface
the extraction of curcumin from turmeric. The curcumin in the tur- methodology; turmeric
meric samples under various extraction conditions was determined
by the use of high performance liquid chromatography (HPLC).
Response surface methodology (RSM) was utilized to investigate the
influence of extraction parameters including the time from 10 to
60 min, temperature from 25 to 55
C, and solvent volume from 10
to 30 mL. The experimentally determined curcumin yield ranged
between 0.76% and 2.94%. The optimal extraction conditions were
obtained employing an extraction time interval equal to 60 min,
temperature of 55
C and solvent volume of 30 mL. The maximum
curcumin yield extracted from turmeric was 2.94% using the optimal
conditions.

Introduction
In recent years, “green solvents” have been preferred instead of the conventional sol-
vents in order to prevent environmental pollution. For this purpose, “ionic liquids” are
considered to be alternatives to conventional extraction solvents. In this context, the use
of an imidazolium-based ionic liquid as an alternative green solvent for the extraction
of curcumin from turmeric was investigated. The curcumin in the turmeric samples was
determined by the use of high performance liquid chromatography for the different
extraction conditions. This study also aims to present novel measurements for the
extraction of curcumin from turmeric.
Curcumin, commonly known as a hydrophobic polyphenolic compound and a bio-
active phytochemical, is a major valuable ingredient of turmeric (Curcuma longa L.). It

CONTACT Nilay Baylan nilay.baylan@istanbul.edu.tr Department of Chemical Engineering, _Istanbul University-

Cerrahpaşa, Avcılar 34320, _Istanbul, Turkey.
ß 2020 Taylor & Francis Group, LLC
2 B. GÖKDEMIR ET AL.

is widely used in foods for as a flavoring and coloring agent. It has significant properties
such as anti-inflammatory, antioxidant, anticancer, antibacterial, antifungal, antiallergic
and antiaging properties. It is also a potential therapeutic agent for diverse diseases
including allergies, diabetes, arthritis, Alzheimer’s disease, psoriasis and human
immunodeficiency virus (HIV). (Wakte et al. 2011; Zhan et al. 2011; Li, Ngadi, and Ma
2014; Kiamahalleh et al. 2016; Shirsath et al. 2017).
Chromatographic techniques are considered to be very suitable tools, particularly for
the separation and analysis of organic compounds. However, actual sample matrices are
complex. Hence, for appropriate detection and acceptable analysis, the material fre-
quently requires an initial step, such as pre-concentration or extraction (Dil, Ghaedi,
and Asfaram 2019).
The traditional organic solvents such as ethanol, methanol, acetone, ethyl acetate,
hexane, isopropanol are commonly used in the extraction of curcumin (Jayaprakasha,
Jagan Mohan Rao, and Sakariah 2002; Li, Ngadi, and Ma 2014; Shirsath et al. 2017).
These organic solvents are not environmentally friendly because of their toxic, flam-
mable and volatile properties (Li, Ngadi, and Ma 2014). Hence, the use of organic sol-
vents may cause undesirable impacts toward the environment and food components
(Kiamahalleh et al. 2016).
Nowadays, ionic liquids as green solvents are preferred instead of traditional organic sol-
vents. Ionic liquids are known to be green solvents because of their important environmen-
tal features. Ionic liquids are molten salts formed with matching of anions and cations and
they usually occur in the liquid phase around room temperature. Ionic liquids have negli-
gible volatility, very high thermal stability and tunable viscosity. However, ionic liquids are
very good solvents that can dissolve various compounds (Mikami 2008).
Based on these remarkable features, ionic liquids have been used in various applications
such as synthesis (Wasserscheid and Welton 2008), catalysis (Dupont, de Souza, and
Suarez 2002), bioelectrochemical systems (Ko ok et al. 2017; 2019) and separation processes
(Arce et al. 2007; Cserjesi, Nemest othy, and Belafi-Bak o 2010). It is noted that there are
limited number of studies related to using ionic liquids as the extraction solvents for the
determination of curcumin in turmeric. Several studies on the utilization of ionic liquids as
extraction solvents have been reported for the isolation of curcumin from turmeric.
A carbamate ionic liquid was examined for the extraction of curcumin from turmeric
by Sahne et al. (Sahne et al. 2017). Xu et al. (Xu et al. 2015) also investigated
[BMIM]Br (1-butyl-3-methylimidazolium bromide), [HMIM]Br (1-hexyl-3-methylimida-
zolium bromide), [OMIM]Br (1-octyl-3-methylimidazolium bromide), and
[OMIM][BF4] (1-octyl-3-methylimidazolium tetrafluoroborate) as solvents in ultrasonic
assisted extraction for curcuminoids from turmeric.
The aim of this work is to investigate the use of imidazolium-based ionic liquid as alter-
native green solvents for the isolation of curcumin from turmeric and determine the effect-
ive extraction parameters. As an alternative green solvent, the ionic liquid [BMIM][Tf2N]
(1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide) was used. In order to
determine the effect of various parameters on curcumin extraction, face-centered central
composite design (FCCCD) based on response surface methodology (RSM) was applied.
Also, the optimal extraction conditions were determined to obtain the highest curcu-
min yield.
 ANALYTICAL LETTERS 3

Materials and methods

Materials
Turmeric powder (Curcuma longa L.) was purchased from a local market in Turkey.
The ionic liquid [BMIM][Tf2N] (Iolitec, >99%) was used as extractive green solvent.
The curcumin standard (98%) was acquired from Sigma-Aldrich.
As HPLC-grade solvents, methanol (Merck), acetonitrile (Merck) and acetic acid
(Merck) were used.

Extraction of curcumin
0.05 g turmeric powder was extracted with ionic liquid [BMIMTf2N] of different vol-
umes (10, 20 or 30 mL). The extraction experiments were carried out at different tem-
peratures (25, 40 or 55
C) and different extraction times (10, 35 or 60 min). The
extraction sample was passed through a 0.45 mm membrane filter and was analyzed by
HPLC (Agilent 1100).
The yield of curcumin yield (%) was determined by (Paulucci et al. 2013):


Curcumin extracted ðgÞ
Curcumin yield ð%Þ ¼ 100 (1)
Tumeric used ðgÞ

Determination of curcumin
An Agilent 1100 HPLC system with an ultraviolet detector and C18 column
(150x4.6 mm, 5 mm) was utilized for the determination of curcumin. The mobile phase
was 75:25 (v:v) acetonitrile:5% aqueous acetic acid. The rate of column flow was
1.0 mL/min. The chromatographic separation was carried out at 25
C.
The detection was performed at 425 nm. The injection volume was 20 lL. All of the
samples were passed through 0.45 mm membrane filters before being introduction into
the HPLC system. An HPLC chromatogram for the determination of curcumin is pre-
sented in Figure 1.
Curcumin standard solutions with six concentrations (0.2, 0.5, 1.0, 5.0, 10 and 50 mg/
L) were prepared by dissolution of standard curcumin in HPLC grade methanol. The
peak areas, as the average of three measurements of curcumin standard solutions plot-
ted versus concentration and the standard calibration curve, are shown in Figure 2. The
calibration curve showed good linearity between concentration and obtained peak area
with an R2 value equal to 0.9998.
The concentration of curcumin in the turmeric samples was determined by the use of
the calibration curve. The calibration range was selected to reflect the concentration of cur-
cumin in the samples. The limit of quantification (LOQ) was determined to be 0.2 mg/L.

Design of experiments and statistical analysis

Face-centered central composite design (FCCCD) based on response surface methodology
(RSM) was used to design the experiments and specify the relationship between the
4 B. GÖKDEMIR ET AL.

Figure 1. HPLC chromatogram of curcumin.

independent variables (factors) and the dependent variable (response). In this regard, the
software Design-Expert 11.0 Trial Version, (Stat-Ease, Minneapolis, USA) was used.
According to the literature, many factors may affect the curcumin yield, such as the
extraction time, extraction temperature, solvent volume, solvent type, and extraction
method (Mandal et al. 2009; Shirsath et al. 2017). In this work, three factors (extraction
time, extraction temperature, and solvent volume) were investigated. Their levels were
extraction time (X1; 10, 35 and 60 min), extraction temperature (X2; 25, 40 and 55
C)
and solvent volume (X3; 10, 20 and 30 mL). The factors and their levels in the coded
and actual values are shown in Table 1.
Thus, the FCCCD matrix employed 33 and the developed experimental plan is shown
in Table 2. The response was the curcumin yield (Y; %). The values of response were
calculated from the experimental measurements by the use of Equation 1 and are sum-
marized in Table 2.
ANOVA was utilized for the statistical analysis of experimental results. The mathem-
atical model for the response were created using a multiple regression method. The
second-order model equation proposed for the response was described by the following
relationship (Asghar et al. 2014):
X
3 X
3 X
2 X
3
Y ¼ b0 þ bi xi þ bii xi2 þ bij xi xj þ e (2)
i¼1 i¼1 i¼1 j¼2

where Y is the response; Xi, Xj are the coded factors; b0 are the constant coefficient; bi,
bii and bij are the coefficients of linear, quadratic and interaction parameters, respect-
ively; and e is the error.
 ANALYTICAL LETTERS 5

Figure 2. Linear relationship between peak area and curcumin concentration.

Results and discussion

Curcumin of extraction from turmeric
The experimental yield values for the extraction of curcumin from turmeric using
[BMIM][Tf2N] varied from 0.76 to 2.94% (Table 2). Curcumin is a valuable component
of turmeric, which makes up approximately 2 to 5% of the total sample content
(Kiamahalleh et al. 2016). Madhusankha et al. (Madhusankha et al. 2018) analyzed the
curcumin content of Sri Lankan and Indian turmeric using ethanol. The curcumin con-
tent was demonstrated to be in the range from 3.76 to 5.05%. The curcumin content
was reported to be between 2.08 and 4.73% by Shashidhar et al. (2018). Pawar et al.
(Pawar et al. 2014) extracted turmeric powder with ethanol and found the curcumin
content to be in the range from 2.85 to 4.85%.
A number of studies related to the utilization of organic solvents in curcumin extrac-
tion from turmeric have been published in the literature. Jayaprakasha et al.
(Jayaprakasha, Jagan Mohan Rao, and Sakariah 2002) reported the curcumin yield to be
in the range from 1.06 to 5.65% in various turmeric samples with using hexane as solv-
ent. Tayyem et al. (Tayyem et al. 2006) reported the curcumin content to be between
0.58 and 3.14% for different types of turmeric powder. Tayyem et al. reported that the
curcumin was separated and quantified by HPLC with the dissolution of the powders in
analytical grade methanol.
Wakte et al. (Wakte et al. 2011) reported that the curcumin yield was 2.1% in acetone
for Curcuma longa L. with conventional Soxhlet assisted extraction. Mandal et al.
(Mandal, Mohan, and Hemalatha 2007) evaluated the curcumin extraction by a micro-
wave assisted process and reported that the curcumin yields were in range from 2.83 to
3.28% in acetone. Sahne et al. (Sahne et al. 2017) used hydrophilic carbamate ionic
liquid for curcumin extraction from turmeric. The curcumin yield was determined to
be 3.58%.
Xu et al. (Xu et al. 2015) also examined hydrophilic ionic liquids [BMIM]Br,
[HMIM]Br, [OMIM]Br, and [OMIM][BF4] as the solvents for the ultrasonic assisted
extraction of curcuminoids from turmeric. They found the maximum total curcumi-
noids yield to be 6.18%. The extraction efficiencies of curcumin were determined to be
6 B. GÖKDEMIR ET AL.

Table 1. Factors studied and their levels in the coded and actual values.
Factor level
Factor Code 1 0 1
Extraction time (min) X1 10 35 60
Extraction temperature (
C) X2 25 40 55
Solvent volume (mL) X3 10 20 30

approximately 2.5% for [OMIM]Br and 0.75% for the [BMIM]Br, [HMIM]Br, and
[OMIM][BF4] ionic liquids.
In present study, the curcumin yield was obtained to be in the range from 0.76 to
2.94% with the use of various extraction parameters. The acquired maximum value of
curcumin yield (2.94%) was remarkable as compared to the previously reported studies.
These measurements show that [BMIM][Tf2N] is effective extraction solvent, and is a
suitable alternative green solvent for the isolation of curcumin from turmeric.

Response surface methodology

Table 3 shows the ANOVA results for the curcumin yield, Y, as the response. The sig-
nificance of the model for the response is analyzed by the F-value and p-value using
ANOVA (Chen et al. 2011). The results demonstrate that the response for the model is
substantial from the F-value (58.13) and p-value (<0.0001). However, the significance
of model terms is evaluated by the p-value.
The p-value less than 0.05 implies model terms are substantial and have a substantial
effect on the response (Asghar et al. 2014). According to the p-values in reported in
Table 3, all of the linear terms (X1, X2, X3), one interaction term (X1X3) and two quad-
ratic terms (X12, X32) were significant terms and had significant effects on the curcumin
yield. In other words, the model equation for curcumin yield was influenced by
these terms.
To develop the mathematical model equation, the coefficients of determination (R2)
of the candidate model equations (linear, quadratic, and cubic) were investigated and
the model that provided the highest values of R2 was determined. Consequently, the
second-order model equation regarding coded factors for curcumin yield (Y) was deter-
mined to be:
Y1 ¼ 1:48 þ 0:42 X1 þ 0:10 X2 þ 0:59 X3 þ 0:14 X1 X3 þ 0:17 X1 2 þ 0:15 X3 2 (3)
The model equation regarding coded factors is used to identify the relative effect of
factors by comparing the coefficient of factors. In this instance, solvent volume (X3) was
the most effective factor and temperature (X2) was the least influential factor on the
curcumin yield (Y). The predicted and experimental values for curcumin yield are plot-
ted in Figure 3. The experimental values were in good agreement with the predicted val-
ues as shown in Figure 3.
Table 4 summarizes the statistical parameters used to characterize the adequacy and
accuracy of model equation. The correlation coefficient, R2, is defined to be a measure
of the degree of compliance. As R2 approaches unity, the predicted model fits better
with the experimental measurements and the difference between the predicted and
experimental data is small (Chen et al. 2011).
 ANALYTICAL LETTERS 7

Table 2. Experimental plan and results.

Factor
HPLC results Response
Extraction Extraction Solvent Curcumin Curcumin
Run time X1 temperature X2 volume X3 Content (mg/g) yield (%) Y1
1 10 (1) 25 (1) 30 (þ1) 14.29 1.43
2 35 (0) 55 (þ1) 20 (0) 15.04 1.50
3 60 (þ1) 55 (þ1) 30 (þ1) 29.43 2.94
4 10 (1) 25 (1) 10 (1) 7.56 0.76
5 35 (0) 40 (0) 20 (0) 14.33 1.43
6 10 (1) 55 (þ1) 10 (1) 8.34 0.83
7 35 (0) 40 (0) 10 (1) 10.29 1.03
8 60 (þ1) 25 (1) 30 (þ1) 26.40 2.64
9 10 (1) 55 (þ1) 30 (þ1) 18.45 1.85
10 35 (0) 40 (0) 20 (0) 14.11 1.41
11 35 (0) 25 (1) 20 (0) 13.75 1.38
12 60 (þ1) 25 (1) 10 (1) 13.20 1.32
13 10 (1) 40 (0) 20 (0) 13.78 1.38
14 60 (þ1) 55 (þ1) 10 (1) 14.16 1.42
15 35 (0) 40 (0) 20 (0) 14.12 1.41
16 60 (þ1) 40 (0) 20 (0) 21.03 2.10
17 35 (0) 40 (0) 20 (0) 14.29 1.43
18 35 (0) 40 (0) 30 (þ1) 24.01 2.40
19 35 (0) 40 (0) 20 (0) 14.11 1.41
20 35 (0) 40 (0) 20 (0) 14.32 1.43

In this design work, the value of the R2 (0.98) shows that the experimental measure-
ments are in good agreement with the predicted values. The adjusted R2 is a measure of
the quantity of variation around the mean (Chen et al. 2011). The fact that the R2
(0.98) and adjusted R2 (0.96) values are close to each other signifies the model
adequately represented the experimental results.
The predicted R2 (0.89) is in acceptable agreement with the adjusted R2 as the differ-
ence is less than 0.2. The adequate precision (AP) is a measure of the proportion of the
signal to noise. AP values larger than 4 are desirable.
The coefficient of variation (CV), is a measure of the proportion of the standard
deviation to the average. A lower CV value is desirable (Baylan and Çehreli 2018). The
values of AP and CV were determined to be 29.84 and 6.67%, respectively. These results
showed that all of the parameters were in the acceptable range and express the suitabil-
ity of the model with the experimental measurements.
The response surface plots (Figure 4) are illustrated for two selected factors while
maintaining the zero coded level. The effects of extraction time, extraction temperature
and ionic liquid volume on curcumin yield are presented in Figure 4. As temperature
was increased (Figure 4a, b), the curcumin yield increased. This result is explained by
the enhanced solute solubility with increasing temperature. The extraction temperature
has been shown to influence the solute diffusivity and solubility (Shirsath et al. 2017).
As mentioned above, ionic liquids have very low vapor pressure. Hence, they do not
strongly interact with the atmosphere and are also stable at higher temperature. Hence,
solvent volatilization did not occur at higher temperature.
Sogi et al. (Sogi et al. 2010) showed that increases in temperature up to 60
C resulted
in an enhancement in the yield of curcumin. Shirsath et al. (Shirsath et al. 2017)
showed that the isolation of curcumin increased with temperature from 25 to 55
C. As
shown in Figure 4, the curcumin yield increased considerably with an enhancement in
the extraction time and solvent volume. Shirsath et al. (Shirsath et al. 2017) also
8 B. GÖKDEMIR ET AL.

Table 3. ANOVA results for the curcumin yield (Y).

Source Sum of squares df Mean Square F-value p-value Prob > F
Model 5.77 9 0.6413 58.13 <0.0001
X1 1.74 1 1.74 157.63 <0.0001
X2 0.1020 1 0.1020 9.25 0.0124
X3 3.48 1 3.48 315.55 <0.0001
X1X2 0.0010 1 0.0010 0.0918 0.7681
X1X3 0.1653 1 0.1653 14.99 0.0031
X2X3 0.0378 1 0.0378 3.43 0.0938
X12 0.0816 1 0.0816 7.40 0.0216
X22 0.0449 1 0.0449 4.07 0.0714
X32 0.0596 1 0.0596 5.41 0.0424
Residual 0.1103 10 0.0110
Lack of Fit 0.1097 5 0.0219 182.86 <0.0001
Pure Error 0.0006 5 0.0001
Cor. Total 5.88 19

Figure 3. Predicted and experimental curcumin yield values for the FCCCD experimental runs.

Table 4. Statistical parameters for the curcumin yield (Y).

Determination coefficient (R2) 0.9812 Standard deviation 0.1050
Adjusted R2 0.9644 Adequate precision (AP) 29.8376
Predicted R2 0.8915 Coefficient of variation (CV) % 6.67

explained that the extent of curcumin extraction increased with an enhanced solvent
ratio. As the volume of solvent used for a constant quantity of solid was increased, the
concentration gradient between the solid interior and the external solvent is greater,
resulting in faster mass transfer and a higher extraction rate.
Compared with extraction time, the solvent volume had a larger impact on the curcu-
min yield (Figure 4b). The increase in the curcumin yield with temperature was less
compared to the enhancement in extraction time and solvent volume. The ANOVA
results showed that X1 (extraction time) and X3 (solvent volume) had lower p-values
(< 0.0001) than X3 (extraction temperature, p-value ¼ 0.0124). Hence, the extraction
time and solvent volume had higher impacts upon the curcumin yield.
 ANALYTICAL LETTERS 9

Figure 4. Characterization of the influence of (a) a solvent volume of 20 mL, (b) extraction tempera-
ture of 40
C, and (c) extraction time of 35 minutes upon the curcumin yield.

Lastly, an optimization study for the response was exerted by the use of the Design-
Expert software. All of the independent variables were kept within in range while the
dependent variable was maximized. The optimal extraction conditions with higher desir-
ability (1.00) were obtained using an extraction time of 60 min, extraction temperature
of 55
C and solvent volume of 30 mL. Under these optimal conditions, the values of
predicted and experimental curcumin yield were 2.98% and 2.94%, respectively. These
results indicate that the model provided good agreement with the experimentally deter-
mined values of the curcumin yield.

Conclusion
In this work, a novel [BMIM][Tf2N] ionic liquid as green alternative to classical organic
solvents was investigated for the extraction of curcumin from turmeric. This ionic liquid
was shown to provide remarkable performance for the extraction and determination of
curcumin in turmeric. The obtained remarkable curcumin yield indicated that
[BMIM][Tf2N] may be used as an alternative green solvent for the isolation of curcu-
min from turmeric.
10 B. GÖKDEMIR ET AL.

The optimal extraction conditions were also determined for the extraction of curcu-
min from turmeric by a face-centered central composite design protocol based on
response surface methodology. The results demonstrated that the extraction time, tem-
perature and solvent volume affected the curcumin yield. Among the investigated
parameters, the solvent volume was shown to be the most influential factor upon the
curcumin yield. The yield of curcumin from the turmeric samples were between 0.76%
and 2.94%.
The obtained model equation for the yield of curcumin was adequate and good
accuracy considering the explained ANOVA results. The optimal conditions were deter-
mined to be an extraction time of 60 min, extraction temperature of 55
C and solvent
volume of 30 mL. Using the optimum extraction conditions, the yield of curcumin was
determined as 2.94%.

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