Uquiche 2019
Uquiche 2019
Uquiche 2019
G R A P H I C A L A B S T R A C T
A R T I C LE I N FO A B S T R A C T
Keywords: Supercritical extraction from L. rivularis stalks using ethanol-modified supercritical CO2 was studied. The effects
Supercritical extraction of ethanol concentration (0.5―1.5 wt.%) and pressure (20―40 MPa) on the total extract yield (Y1, g/kg d.s.),
Leptocarpha rivularis phenolics extraction yield (Y2, mg GAE/kg d.s.), antioxidant (Y3, mmol TE/kg d.s.) and anti-inflammatory ac-
Bioactive properties tivities (Y4=IC50, mg/mL) were studied. The greatest total extract yield, phenolics extraction yield and anti-
Modifier ethanol
oxidant activity were reached at 1 wt.% and 40 MPa. Anti-inflammatory activity improved with the addition of
ethanol, being higher at 1.5 wt.%. The following results were obtained at the selected condition (1 wt.%,
40 MPa): Y1 = 34.15 g/kg d.s, Y2 = 658.44 mg GAE/kg d.s., Y3 = 0.103 mmol TE/kg d.s. and Y4 = 3.38 mg/mL.
Important bioactive compounds like caryophyllene oxide, quercetin, kaempferol and resveratrol were quantified
in the selected extract. The extract showed inhibitory capacity against α-amylase and α-glucosidase, demon-
strating important bioactive properties.
1. Introduction make infusions. Bioactive compounds present in the plant have shown
an inhibitory and cytotoxic effect on cancer cells [2]. Supercritical fluid
Leptocarpha rivularis is a medicinal plant endemic to southern Chile extraction is a technology for extraction of high quality natural com-
belonging to the Asteraceae family. L. rivularis is a Chilean medicinal pounds, and provides a more selective and efficient extraction by
plant and its application forms part of the ancestral medicine of the controlling temperature and pressure, which determine its solvent
Mapuche people (pre-Hispanic inhabitants of Chile) [1]. Nowadays it is power by regulating the density of the supercritical fluid. Carbon di-
marketed in pharmacies and alternative medicine shops as a product to oxide (CO₂) is the solvent most commonly used for supercritical
⁎
Corresponding author.
E-mail address: edgar.uquiche@ufrontera.cl (E. Uquiche).
https://doi.org/10.1016/j.supflu.2019.02.005
Received 24 November 2018; Received in revised form 6 February 2019; Accepted 7 February 2019
Available online 11 February 2019
0896-8446/ © 2019 Elsevier B.V. All rights reserved.
E. Uquiche, et al. The Journal of Supercritical Fluids 147 (2019) 1–8
extraction applications in the food industry. CO₂ is a solvent suitable for tetrahydrate, sodium hydroxide, lipoxygenase from Glycine max, α-
extraction of nonpolar organic compounds. Solubility of polar organic amylase from Bacillus licheniformis, α-glucosidase from Saccharomyces
compounds in supercritical CO₂ is low, however could improve by in- cerevisiae, TROLOX (6-hydroxy-2,5,7,8-tetramethylchromane-2-car-
creasing pressure or adding a polar modifier, such as ethanol, methanol boxylic acid), DNSA (3,5-Dinitrosalicylic acid), pNPG (p-Nitrophenyl β-
or water at a low concentration. Modifiers also can improve extraction D-glucopyranoside), p-Nitrophenol, 1,2,4,5-tetramethylbenzene, car-
yield by reducing solute/solid matrix interactions, facilitating the re- yophyllene oxide, gallic acid, catechin, naringenin, quercetin, resvera-
moval of solutes [3]. trol, maltose monohydrate from potato were procured from Sigma-
Studies on supercritical extraction using L. rivularis leaves were Aldrich (St. Louis, MO, USA). Starch soluble for analysis (potato starch,
carried out by Uquiche and Martínez [4] and Uquiche and Garcés [5]. solubility in water at 90 °C: 50 g/L) was acquired from Scharlau Chemie
Nowadays, the preparation of infusions of the plant is done with the S.A. (Barcelona, Spain). Phosphate buffer pH 7 was obtained from
mixture of stalks and leaves (90:10). There are no previous studies on Winkler Ltda. (Santiago, Chile).
supercritical extraction using stalks. A review on supercritical extrac- The L. rivularis stalks used as substrate were provided by Los Esteros
tion of polyphenols from plant substrates indicates a range of pressures Company (La Union, Chile) (39°52′S, 73°14′W). The material was dried
used between 10―50 MPa, and temperature range between 318―348 K in an oven (Memmert UF110, Schwabach, Germany) at 50 °C for 10 h.
(45―75 °C) [6]. In current work were selected pressures between 20 Substrate was placed in a freezer (–60 °C) for 2 days and stalks were
and 40 MPa because this range covers a large part of the pressure ground in a Moulinex chopper (model AD5661AR, Moulinex, Ecully,
conditions used in different studies. Likewise 60 °C was chosen as an France). Substrate was screened through a series of sieves using a Ro-
intermediate value in the temperature range reported in studies in the Tap testing sieve shaker (model RX-29-10, W.S. Tyler, Mentor, OH,
review. In the case of the modifier, to obtain a balanced three-level USA). Average particle diameter (dp) was calculated using standard
design, was used 0.5–1.0 - 1.5% by weight. method S319.3 [10].
Studies have been reported on the use of ethanol as a modifier in
supercritical CO2 extraction from medicinal plants. Daukšas et al. [7] 2.2. Supercritical extraction
informed that extract recovery increased with 1 wt.% of ethanol,
compared to extraction without modifier. However, extract recovery Supercritical extraction was carried out in a Spe-ed SFE unit
decreased when ethanol was increased to 2 wt.%. Michielin et al. [3] (Applied Separations, Allentown, PA) loading 12 g of substrate (feed) in
observed a decrease in extraction yield when an excess of ethanol as a 50 cm3 extraction vessel (14 mm inner diameter). The substrate had a
modifier was used in supercritical CO2 extraction from Cordia verbe- moisture content of 7.53 ± 0.55 g/100 g dry substrate, determined
nacea. They pointed out that the decrease in extraction yield was be- gravimetrically by drying in an air-convection oven (Memmert model
cause the addition of ethanol in 8 wt.% decreased the interactions be- UM-400, WTB Binder, Tuttlingen, Germany) set at 102 °C to a constant
tween solute and CO2. Thus, increase of modifier concentration does final weight (10 h) [11]. Dry substrate (d.s.) is the substrate loaded into
not necessarily mean a more efficient extract recovery. the extractor vessel discounting its moisture. Depending on the ex-
Lipoxygenase is an enzyme involved in the regulation of in- traction conditions (20―40 MPa, at 60 °C), between 3.7 and 4.6 L NPT
flammatory responses by biosynthesis of leukotrienes and lipoxins, per min of CO2 (Linde Chile S.A.) was used as solvent (superficial ve-
important mediators in inflammation. Leukotrienes have been related locity, 1 mm/s). The static 15-min extraction period was followed by a
to inflammatory diseases including cancer [8]. Phenolic compounds dynamic extraction period, which varied between 44 and 54 min in
exert an anti-inflammatory effect by lipoxygenase inhibition, through order to obtain a total solvent consumption of 30 kg CO2/kg d.s. In
their actions at the enzyme active site, and by chelating iron or redu- supercritical extractions involving the use of modifier, ethanol was
cing it to its ferrous form [9]. Phenolic compounds are known for their pumped into the CO2 feed line at a flow rate between 0.04 and 0.11 mL/
antioxidant properties. Free radicals can cause damage to molecules min so as to achieve three levels of modifier concentration (0.5, 1.0 and
such as DNA and proteins, resulting in pathologies associated with in- 1.5 wt.%) by using an HPLC pump (Knauer, model K-501, Berlin, Ger-
flammatory disorders, causing cancer, diabetes and cardiovascular many) (flow accuracy < 1%, at 1 mL/min, 12 MPa). The extracts were
diseases. Thus, between the production of free radicals and inflamma- collected during extraction in pre-weighed glass vials (60 cm3 capa-
tion exist a close relationship. Diabetes mellitus type 2 is a disease city). The extracts were subjected to a gentle stream of nitrogen (Linde
caused by deficiency in the action and/or secretion of insulin, causing Chile S.A.) to evaporate the ethanol. Extraction yield (Y1) was ex-
the accumulation of glucose in the blood (hyperglycaemia). α-amylase pressed as grams of extract per kilogram of dry substrate (g/kg d.s.).
hydrolyzes the α-1,4 glycosidic linkages of complex carbohydrates (e.g.
starch); while α-glucosidase catalyzes the final step of carbohydrate 2.3. Analysis of extracts
hydrolysis, releasing glucose. Thus inhibition of α-amylase and α-glu-
cosidase activity may potentially offer a means of regulating blood 2.3.1. Total phenolics extraction yield
glucose levels. The aim of our work was to evaluate the effect of Total phenolics content was determined according to Folin-
modifier (ethanol) concentration and extraction pressure on the total Ciocalteu’s method [12] with minor modifications as described pre-
extract yield, total phenolics extraction yield, antioxidant activity and viously [4]. Extract solution (5 mg/mL) was prepared by dissolving
anti-inflammatory activity of extract from L. rivularis stalks. 10 mg of extract in 2 mL of ethanol. Quantification was done using a
calibration curve constructed with gallic acid solution and expressed as
2. Materials and methods milligrams of gallic acid equivalents (GAE) per gram of extract (Cph, mg
GAE/g). Total phenolics extraction yield (Y2, mg GAE/kg d.s.) was
2.1. Materials calculated as Y1×Cph.
Ethanol and methanol both analytical grade were procured from 2.3.2. Antioxidant activity
J.T. Baker (Phillipsburg, NJ, USA). DPPH (2,2-diphenyl-1-picrylhy- Antioxidant activity was measured by DPPH radical scavenging
drazyl) was purchased from Calbiochem Co. (San Diego, CA, USA). assay based on the standard calibration curve, according to Brand-
Acetonitrile, methanol and water, all grade for chromatography Williams [13] with minor modifications [4]. Extract solution (10 mg/
(LiChrosolv Reag. Ph Eur) and DMSO (dimethyl sulfoxide) and formic mL) was prepared by dissolving 50 mg of extract in 5 mL of ethanol.
acid were obtained from Merck KGaA (Darmstadt, Germany). Iron (II) Antioxidant activity was expressed as mmol TROLOX equivalent (TE)
sulfate heptahydrate and iron (III) chloride anhydrous were purchased per kilogram of dried substrate (Y3, mmol TE/kg d.s.). Additionally,
from ACROS Organics (Morris, NJ, USA). Potassium sodium tartrate antioxidant activity was measured by Ferric-Reducing Antioxidant
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E. Uquiche, et al. The Journal of Supercritical Fluids 147 (2019) 1–8
Power (FRAP) assay according to Benzie and Strain [14]. Extract so- mg maltosesample ⎤
lution (10 mg/mL) was prepared by dissolving 50 mg of extract in 5 mL % Inhibition = ⎡1 − × 100
⎢ mg maltosecontrol ⎥ (1)
⎣ ⎦
of ethanol. A standard calibration curve was constructed using aqueous
solutions of FeSO4·7H2O at different concentrations. The FRAP value
was calculated and expressed as mmol Fe+2 equivalents per kilogram of 2.3.7. Inhibition of α-glucosidase
dried substrate (mmol Fe+2/kg d.s.) based on the standard calibration The inhibition of α-glucosidase was determined according to
curve. Muccilli et al. [19] with some modifications. Extract solutions in DMSO
at different concentrations were prepared (1.0―3 mg/mL). A 3 mM
2.3.3. Anti-inflammatory activity solution of pNPG was prepared as substrate. The enzyme solution was
Anti-inflammatory activity was measured by lipoxygenase inhibi- prepared at a concentration of 1 U/mL in phosphate buffer. For the
tion assay according to Ahmed et al. [15], with some modifications [4]. inhibition test 50 μL of extract solution was mixed in a test tube with
Anti-inflammatory activity (Y4) was expressed as IC50 value (mg/mL), 125 μL of pNPG and 1250 μL of phosphate buffer, and incubated for
which represents the extract concentration sufficient to obtain 50% 10 min at 37 °C. To start the reaction, 50 μL of the enzyme solution was
inhibition of maximum capacity for lipoxygenase activity. added and incubated for 20 min at 37 °C. Then the reaction was stopped
by adding 4000 μL of 0.1 M solution of Na2CO3. A blank solution was
2.3.4. Individual quantification of flavonoids prepared by replacing 50 μL of the enzyme solution with 50 μL phos-
Quantification of catechin, quercetin and resveratrol was carried phate buffer. A control assay representing 100% of the enzymatic re-
out according to Kim [16], using a HPLC–DAD 1260 infinity system action was performed by replacing the 50 μL of the extract solution with
(Agilent Technologies, Santa Clara, CA, USA), equipped with a qua- 50 μL DMSO. The activity of α-glucosidase was determined by mea-
ternary pump. Stock solution of samples were prepared at the con- suring the p-nitrophenol released from the hydrolysis of pNPG at
centration of 10 mg/mL in methanol. Chromatographic separations 400 nm in the spectrophotometer. The inhibition (%) was calculated
were performed on an column Agilent Zorbax rapid resolution high- with the following Eq. (2):
definition (RRHD) SB-C18 (2.1 mm i.d. × 100 mm, 1.8 μm, catalog
number: 858758-902). The column temperature was 30 °C, the flow Asample − Ablank ⎞ ⎤
Inhibition (%) = ⎡1 − ⎛ ⎜ ⎟ × 100
rate was 0.3 mL/min and injection volume was 20 μL. Mobile phase A ⎢ ⎝ Acontrol ⎠⎥ (2)
⎣ ⎦
(water with 0.1% formic acid) and B (acetonitrile with 0.1% formic
acid) were used for gradient elution.
The gradient elution program was used as follows: 0% B (0 min), 5% 2.4. Experimental design
(0―3.5 min), 15% (3.5―7.1 min), 40% (7.1―25 min), 40%
(25―26 min), 100% (26―27 min), 100% (27―29 min), and 0% A two-level full factorial design [22] with four replicates in the
(29―35 min). central point was used to evaluate the effects of the independent vari-
Flavonoids were identified by comparing their retention times with ables coded modifier concentration (X1) and coded pressure (X2) on the
those of standards. Solution of standards were prepared at the con- total extract yield (Y1, g/kg d.s.), total phenolics extraction yield (Y2,
centration of 0.1 mg/mL in methanol. Quantification was carried out by mg GAE/kg d.s.), antioxidant (Y3, mmol TE/kg d.s.) and anti-in-
the internal standard method [17] using naringenin. The HPLC-DAD flammatory (Y4=IC50, mg/mL) activities. A second-order model (Eq.
was controlled using the Agilent ChemStation Software. (3)) was used to describe the response variable as a function of coded
modifier concentration (X1) and coded pressure (X2), where A0 is a
2.3.5. Individual quantification of terpenes constant; A1 and A2 are linear coefficients; A12 is a cross-product
coefficient; and A12 and A22 are quadratic coefficients. Coefficients of the
Quantification of caryophyllene oxide was carried out according to
second-order model were estimated using Design-Expert Software,
Uquiche and Martínez [4] using a GC-FID 6850 (Agilent Technologies,
version 6.0.1 (Stat-Ease, Inc., Minneapolis, MN, USA). Goodness of fit of
Santa Clara, CA, USA) with a flame ionization detector equipped with a
the second-order model was evaluated by analysis of variance. Statis-
HP-5 capillary column (0.25 mm i.d. × 30 m, 0.25 μm, catalog number:
tical significance was based on the total error criteria with a confidence
19091S-433). Internal standard method [17] was used for quantifica-
level of 95%.
tion with 1,2,4,5-tetramethylbenzene as the internal standard. The GC-
FID was controlled using the Agilent ChemStation Software. Y = A0 + A1 X1 + A2 X2 + A12 X1 X2 + A12 X12 + A22 X22 (3)
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E. Uquiche, et al. The Journal of Supercritical Fluids 147 (2019) 1–8
Table 1
Total extract yield (Y1, g/kg d.s.), total phenolics extraction yield (Y2, mg GAE/kg d.s.), antioxidant activity (Y3, mmol TE/kg d.s.), anti-inflammatory activity (Y4,
mg/mL) and extraction rate parameter (k1, min−1) as a function of modifier concentration (C, wt.%) and pressure conditions (P, MPa).
C P X1 X2 Y1 Y2 Y3 Y4 k1 RMSD
wt.% MPa (―) (―) g/kg d.s. mg GAE/kg d.s. mmol TE/kg d.s. mg/mL min−1
0.5 20 ―1 ―1 6.29 ± 1.33 72.89 ± 15.03 0.0224 ± 0.0034 2.50 ± 0.01 0.154 0.04969
1.5 20 1 ―1 5.69 ± 0.42 79.75 ± 5.68 0.0130 ± 0.0015 1.72 ± 0.16 0.150 0.02742
0.5 40 ―1 1 21.86 ± 1.80 202.77 ± 17.30 0.0576 ± 0.0001 3.90 ± 0.12 0.163 0.03866
1.5 40 1 1 19.11 ± 1.73 148.70 ± 13.78 0.0450 ± 0.0093 2.90 ± 0.11 0.199 0.03440
1.0 30 0 0 22.70 ± 0.95 352.68 ± 1.68 0.0474 ± 0.0017 3.17 ± 0.27 0.231 0.05439
1.0 30 0 0 24.46 ± 1.13 371.37 ± 1.36 0.0572 ± 0.0049 3.27 ± 0.08 0.216 0.10466
1.0 30 0 0 22.61 ± 1.04 346.54 ± 2.51 0.0536 ± 0.0005 2.87 ± 0.17 0.203 0.02681
1.0 30 0 0 22.35 ± 0.71 352.81 ± 2.07 0.0567 ± 0.0090 3.31 ± 0.04 0.220 0.04561
Table 2
Analysis of variance of regression coefficients and statistical appropriateness indicators of the second-order models selected.
Regression coefficients Y1 Y2 Y3 Y4
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E. Uquiche, et al. The Journal of Supercritical Fluids 147 (2019) 1–8
herbaceous matrices has been extensively reported. Fig. 1 shows non- parameter related to extraction rate at the very beginning of the process
linear effect (p = 0.0002) of modifier concentration on total extract (min−1); k2, the parameter related to maximum extraction yield
yield, regardless of pressure. At 40 MPa, Y1 increased when C increased (min−1); q, amount of extract (g/kg d.s.); q0, maximum amount ex-
from 0.5 to 1 wt.% (from 21.3 to 30.3 g/kg d.s.) and then it decreased tracted (g/kg d.s.); and t, time (min). Parameters k1 and k2 were ob-
until 19.7 g/kg d.s. when C changed to 1.5 wt.%. de Campos et al. [21] tained by adjusting experimental extraction data to the kinetic model
have pointed out that the increase in ethanol concentration can affect for each extraction condition. The difference between values observed
extraction yield by: (a) the saturation of CO2 with ethanol, which re- experimentally (Yexp) and values predicted by the kinetic model (Ypred)
sults in the formation of two phases, reducing the solvent capacity of were established by root mean square deviation (RMSD) (Eq. (9)).
the CO2-ethanol mixture; (b) the formation of hydrogen bonds between q k1 t
the hydrogen from one molecule with oxygen from another molecule =
q0 1 + k2 t (8)
(ethanol–ethanol hydrogen bonding). The formation of ethanol–ethanol
hydrogen bonding reduces the availability of ethanol to interact with n
∑i (Yexp − Ypred )2
solute molecules; and therefore less solute molecules are solubilized, RMSD =
thereby decreasing the extraction yield [21,22]. Addition of ethanol as n (9)
a modifier affects the temperature (Tc) and pressure (Pc) critical for Initial extraction rate parameter (k1) ranged between 0.150 and
CO2. Aidil et al. [23] reported the corresponding critical values for a 0.231 min−1 (Table 1). Value of k1 increased with pressure at a con-
concentration of 5 wt.% of ethanol in CO2 as Tc = 42.5 °C and stant temperature; and increased and decreased with the concentration
Pc = 7.32 MPa. In the current work, temperature was at 60 °C and of modifier, similar to behaviour of Y1. In fact, there was a positive
pressure over 20 MPa, so that our working conditions were in the su- correlation between Y1 and k1 (r = 0.804; p ≤ 0.05). This positive
percritical region for ethanol-modified CO2. Thus, the decrease in total correlation may be because the initial extraction rate depends on the
extract yield may be due to the prevalent formation of ethanol–ethanol solute solubility in supercritical CO2. This condition does not necessa-
hydrogen bonding. rily indicate that equilibrium was attained. Therefore, the differences
The increase and decrease of extraction yield with the modifier observed in the total extract yield are mainly explained by the effects of
addition in supercritical extraction from herbaceous matrices has been extraction conditions on the solvation power of CO2 and consequently
reported in the literature. Daukšas et al. [7] studied supercritical ex- on the initial extraction rate.
traction from sage (Salvia officinalis L.) with ethanol-modified CO2 at
100 °C and 35 MPa. Extraction yield increases with 1 wt.% of modifier; 3.4. Total phenolics extraction yield
but decreases with an increase to 2 wt.%. Biscaia and Ferreira [24] used
ethanol-modified CO2 (2―7 wt.%) to extract propolis at 40 °C and Fig. 3 shows an increase in total phenolics extraction yield with
15 MPa. Higher recovery of extract was achieved with 5 wt.% modifier. pressure increase (p = 0.0051), at every modifier concentration. To
Similar behavior was informed by Kamali et al. [25] in supercritical exemplify, Y2 increased from 88.12 to 187.54 mg GAE/kg d.s and from
extraction from Biebersteinia multifida DC using ethanol-modified CO2. 64.52 to 163.93 mg GAE/kg d.s through increase from 20 to 40 MPa, at
Therefore, an increase and subsequent decrease of total extract yield 0.5 and 1.5 wt.%, respectively. Fig. 3 shows significant quadratic effect
with an increase of modifier concentration, has been observed. (p < 0.0001) of modifier concentration on phenolic extraction yield
To illustrate the effect of modifier concentration and pressure on (Y2) regardless of pressure, increasing and decreasing with the increase
extraction kinetics, cumulative extraction curves were constructed at of modifier concentration. To exemplify, at 40 MPa, Y2 increased from
the extraction conditions studied (Fig. 2). The curves show the constant 187.54 to 405.56 mg GAE/kg d.s. by increase from 0.5 to 1 wt.% of
extraction rate (CER) period, where the extraction mechanism is con- modifier. Then it decreased until 163.93 mg GAE/kg d.s. when 1.5 wt.%
trolled by solubility and the diffusion-controlled rate (DCR) period, was used. As has been argued before, the decrease in the phenolic ex-
where the extraction mechanism is controlled by diffusion [20,26]. traction yield at 1.5% may be due to the prevalence of the ethanol-
Differences between extraction curves in the CER period were observed. ethanol interaction, reducing the availability of ethanol to interact with
Cumulative extraction curves were modeled using Peleg’s model (Eq. the solute molecules [21,22]. Machado et al. [28] studied conditions to
(8)) [27] and the following kinetic parameters were estimated: k1 is the extract phenolic compounds from propolis using supercritical CO2
modified with 1 and 2 wt.% of ethanol at 50 °C and 25 MPa. Addition of
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E. Uquiche, et al. The Journal of Supercritical Fluids 147 (2019) 1–8
Table 4
Percent inhibition of α-amylase and α-glucosidase at varying concentrations of extract obtained with ethanol-modified CO2 at 1 wt.% and 40 MPa (60 °C).
Enzyme α-amylase Enzyme α-glucosidase
0.1 24.6 ± 1.2 15.1 ± 1.1 0.1 38.4 ± 3.4 2.7 ± 0.1
0.5 28.6 ± 1.9 0.5 46.6 ± 1.4
2 32.5 ± 2.0 0.8 48.6 ± 2.6
6 34.4 ± 1.7 1.0 53.6 ± 0.3
10 43.9 ± 2.6 1.5 72.4 ± 0.3
14 48.8 ± 2.1 3.0 78.5 ± 1.2
20 56.8 ± 4.4
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pogon citratus (lemongrass) [18] and Ocimum basilicum (sweet basil)
3.7. Characteristics of the selected extract [47]. Thus sesquiterpenes may have antidiabetic properties.
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E. Uquiche, et al. The Journal of Supercritical Fluids 147 (2019) 1–8
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