1 s2.0 S0021967320302569 Main

Journal of Chromatography A 1621 (2020) 461044
Contents lists available at ScienceDirect
Journal of Chromatography A
journal homepage: www.elsevier.com/locate/chroma
Short communication
Thin-layer chromatography with eutectic mobile phases—preliminary

results
Danuta Raj
Department of Pharmacognosy and Herbal Medicines, Wroclaw Medical University, Borowska 211a, 50-556, Wrocław, Poland
a r t i c l e i n f o a b s t r a c t
Article history: The presented paper is the first to show thin layer chromatography (TLC) analysis based on eutectic mo-
Received 10 October 2019 bile phases (Deep Eutectic Solvents – DES). During the experiment 25 eutectic mixtures were investigated
Revised 10 March 2020
for their chromatographic properties. Most of them belong to the natural deep eutectic solvents (NADES)
Accepted 11 March 2020
group. Also, new eutectic liquids based on phenolics and terpenes, not previously employed in analyt-
Available online 14 March 2020
ical practice, were tested. The eutectic liquids were investigated as pure or diluted with solvents used
Keywords: in chromatographic routine: methanol, water, acetone, chloroform or diethyl ether. The analyses were
Chelidonium carried out using classic and high performance silica gel plates. The working solution was a mixture of
Chromatography five alkaloids found in genus Chelidonium, namely sanguinarine, coptisine, chelerythrine, chelidonine, and
Eutectic solvents berberine, with UV light detection of 366 nm. This report proves that eutectic TLC is possible and that the
Isoquinoline alkaloids eutectic interactions play a crucial role in the separation process. In most of the tested modifications at
NADES
least partial separation was achieved. The most successful mobile phase, which enabled separation of all
TLC
the tested alkaloids, was the equimolar mixture of menthol and phenol with a 35% addition of methanol.
The system was also effective in separating alkaloids in the real Chelidonium maius extract sample.
© 2020 The Author(s). Published by Elsevier B.V.
This is an open access article under the CC BY-NC-ND license.
(http://creativecommons.org/licenses/by-nc-nd/4.0/)
1. Introduction ruption of intramolecular bondings which create an eutectic matrix

[6]. To the Author’s best knowledge, at this time there is no report
From the physicochemical point of view DES is a class of liq- about the chromatographic system involving stationary phase and
uids composed of hydrogen bonds donors and acceptors, which pure eutectic solvents.
after mixing show strong melting point depression compared to In this work, I present the results of a preliminary investigation
the pure components. The mixture is characterized by minor va- of DES being employed as mobile phases in thin layer chromatog-
por pressure, overall high solvation capacity and – in many cases raphy (TLC). The work intends to present that eutectic liquids al-
– low toxicity and eco-friendliness [3]. In particular, the solubi- low chromatographic separation of mixtures of natural compounds,
lization properties exhibited by DES drew the attention of phyto- with particular regard to alkaloids. For this purpose several eutec-
chemists, as these solvents are able to efficiently extract a wide tic solvents have been selected, which are recognized as eutectic
range of compounds, including alkaloids, ginkgolides, ginsenosides, mixtures and classified as NADES. They were employed to sepa-
flavonoids, xanthones, catechins and essential oils [4–6]. This led rate a mixture of selected natural compounds, either as pure or
to the question of the possibility of employing eutectic solvents after dilution with methanol, water, acetone, chloroform or diethyl
in chromatographic techniques. Successful assays were performed ether.
in countercurrent separation [7,8]. One publication indicates that
NADES do not disrupt LC systems [9], however it does not consider
2. Materials and methods
the attempt of eutectic separation. Several reports can be found re-
garding a DES used as a mobile phase modifier in HPLC analyses
2.1. Preparation of mobile phases
[10–13]. In these cases eutectic mixtures were added to a mobile
phase in a maximum 4% concentration, far below the 50% concen-
The eutectic mobile phases were prepared according to one of
tration limit pointed to in the literature data as the moment of dis-
three procedures [2,6] (Table 1). Procedure 1 (P1) consisted of sim-
ply mixing the components with subsequent spontaneous lique-
E-mail address: danuta.raj@umed.wroc.pl fying, resulting in a homogenous and stable liquid. Procedure 2
https://doi.org/10.1016/j.chroma.2020.461044
0021-9673/© 2020 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY-NC-ND license.
(http://creativecommons.org/licenses/by-nc-nd/4.0/)
2 D. Raj / Journal of Chromatography A 1621 (2020) 461044
Table 1
The list of pure DES prepared within the experiment.
Components Molar ratio No Obtaining procedure
Camphor + phenyl salicylate 1:1 D1 P1

camphor + chloral hydrate 1:1 D2 P1
phenol + chloral hydrate 1:1 D3 P1
phenol + menthol 1:1 D4 P1
phenol + thymol 1:1 D5 P1
choline chloride + lactic acid 1:1 D6 P1
choline chloride + malonic acid 1:1 D7 P1
choline chloride + raffinose 11:2 D8 P2
choline chloride + rhamnose 2:1 D9 P2
choline chloride + xylitol 5:2 D10 P3
choline chloride + malic acid + proline 1:1:1 D11 P3
citric acid + fructose 1:1 D12 P3
citric acid + xylitol 1:1 D13 P3
citric acid + raffinose 3:1 D14 P3
citric acid + L-α -alanine 1:1 D15 P3
citric acid + proline 1:1 D16 P3
citric acid + sorbitol 1:1 D17 P3
citric acid + glucose 1:1 D18 P3
malic acid + L-α -alanine 1:1 D19 P3
malic acid + xylitol 1:1 D20 P3
malic acid + sorbitol 1:1 D21 P3
malic acid + glucose 1:1 D22 P3
malic acid + fructose 1:1 D23 P3
malic acid + sucrose 1:1 D24 P3
proline + glucose 1:1 D25 P3
(P2) consisted of mixing the components and subsequent heating only recently separated on silica gel plates with a single mobile
to 50 °C until a homogenous and stable liquid was formed. Proce- phase [16].
dure 3 (P3) consisted of mixing the components with the addition The mobile phases tested within the experiment have low-
of water, using the smallest amount of water necessary for dis- volatility [6]. After development they did not evaporate from the
solution of the components, and subsequent evaporation of water chromatographic plates, and during the preliminary stage of exper-
using a rotary evaporator (R-210, Büchi, Germany) at 60 °C to the iment the resulting impregnation of silica gel with mobile phase,
stable mass. in many cases, blocked wetting it with spraying reagents. In some
The eutectic liquids were used as pure or diluted with the ad- cases, reactions between mobile phase components and a spray-
dition of 10, 20, 30 or 40% water, methanol, chloroform, diethyl ing reagent did not allow to form visualized bands (data not pre-
ether, or acetone (W, M, C, E or A, respectively), which was marked sented). Thus, UV 366 mn detection was applied.
in their names as a suffix containing an abbreviation of the solvent
and degree of dilution (e.g., D1 -W10 means that D1 DES contains 3.1. Preparation of mobile phases
10% water). The dilutions were made using wt/wt ratio (Table 2).
Additional information on the methodology for obtaining the In order to select DES for the purpose of the experiment, liter-
working solution, a real Chelidonium extract sample and chromato- ature data was reviewed for the information on eutectic mixtures
graphic parameters is included in Supplementary material. possible to be employed in the chromatographic process. During
the search the assumption was made that eutectic mixtures to be
3. Results and discussion included, must be liquid and stable in ambient temperature, should
contain nature-derived compounds or simple chemicals and shall
DES are characterized by a relatively high viscosity, which is be simple in preparation. Part of the examples of creating eutectic
probably the reason why researchers have not yet attempted sta- mixtures were defined as pharmaceutical incompatibilities (D1 –D5
tionary phase-based chromatographic separations using DES. How- [17]) and these were not previously employed in analytical prac-
ever, the literature data regarding DES point at two favorable tice, e.g. extraction. Other eutectic mixtures were found in the lit-
pieces of information: specific eutectic mixtures differ significantly erature describing NADES (D6 –D25 [2,6,9,15]). For the NADES-based
in viscosity, in a range of 20–10 0 0 times more than water [15] and eutectics, the main including criterion was relatively low viscosity
they can be diluted up to 50% without breaking the intramolecu- according to the data presented in the source papers. Furthermore,
lar interactions, which would allow further a further decrease in DES with water being the essential component (e.g., choline chlo-
viscosity and presumably could facilitate chromatography on a sta- ride:fructose:water 5:2:5; [9]) were excluded, as the initial water
tionary phase. Moreover, dilution with water was mentioned as a amount would interfere with the projected dilution steps. The clas-
way of fine-tuning the polarity of DES [6], which would ease the sic eutectic mixture containing choline chloride:urea 1:2 [18] was
optimization of a mobile phase’s elution strength. also excluded based on the preliminary experiments, as it proved
As the working solution, a mixture of alkaloids from genus Che- to solidify during the chromatographic process.
lidonium were selected (sanguinarine, coptisine, chelerythrine, che- DES used within the experiment were created using the molar
lidonine, berberine – Fig. S1), given that the plant alkaloids possess ratio suggested in the literature data. In the absence of such in-
numerous pharmacological effects, including spasmolytic, anti- formation a default ratio 1:1 was applied based on the available
inflammatory, antimicrobial, antiviral, cholagogue, and antiprolifer- information [1,6]. The preparation procedures for the specific eu-
ative, and it is widely used in traditional phytotherapy [14]. More- tectic liquids were taken from the literature data [2,6,17]. Where
over, the selected alkaloids are visible in 366 nm UV light [14], possible, spontaneous liquefaction was employed (P1) or liquefac-
which enables detection without derivatization. The working mix- tion supported by heating (P2). In the remaining cases water addi-
ture is also significantly complex, as the mentioned alkaloids were tion and subsequent evaporation was necessary (P3) [2,6].
Table 2
DESs dilutions and their chromatographic properties.
Modification
Methanol Water Acetone Chloroform Diethyl ether
D1 Pure D1 -M10 D1 -M20 D1 -M30 D1 -M40 D1 -W10 D1 -W20 D1 -W30 D1 -W40 D1 -A10 D1 -A20 D1 -A30 D1 -A40 D1 –C10 D1 –C20 D1 –C30 D1 –C40 D1 -E10 D1 -E20 D1 -E30 D1 -E40
2 – – – – – – – – 3 3 4 4 2 2 2 2 2 2 2 2
1 2 2 2 2 – – – – 1 1 1 1 1 1 1 1 1 1 1 1
1 2 2 2 3 – – – – 1 1 2 2 1 1 1 1 1 1 1 1
D4 Pure D4 -M10 D4 - M20 D4 -M30 D4 -M40 D4 -W10 D4 -W20 D4 -W30 D4 -W40 D4 -A10 D4 -A20 D4 -A30 D4 -A40 D4 –C10 D4 –C20 D4 –C30 D4 –C40 D4 -E10 D4 -E20 D4 -E30 D4 -E40
2 3 5 5 5 – – – – 3 3 4 5 2 2 2 2 2 2 2 2
2 2 3 4 5 – – – – 1 2 3 4 2 2 2 2 2 2 2 2
D6 Pure D6 -M10 D6 -M20 D6 -M30 D6 -M40 D6 -W10 D6 -W20 D6 -W30 D6 -W40
0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0
D. Raj / Journal of Chromatography A 1621 (2020) 461044

0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0
n.s. n.s. n.s. n.s. n.s. n.s. 3 3 3
DES
n.s. n.s. n.s. n.s. n.s. n.s. 2 2 2
n.s. n.s. n.s. n.s. n.s. n.s. 1 1 1
n.s. n.s. n.s. n.s. n.s. n.s. n.s 2 2
n.s. n.s. n.s. n.s. n.s. n.s. 0 0 0
n.s. n.s. n.s. n.s. n.s. n.s. n.s 3 3
n.s. n.s. n.s. n.s. n.s. n.s. n.s 4 4
n.s. n.s. n.s. n.s. n.s. n.s. n.s 2 2
n.s. n.s. n.s. n.s. n.s. n.s. n.s 2 2
n.s. n.s. n.s. n.s. n.s. n.s. 0 0 0
n.s. n.s. n.s. n.s. n.s. n.s. n.s 3 3
n.s. n.s. n.s. n.s. n.s. n.s. n.s 4 4
n.s. n.s. n.s. n.s. n.s. n.s. 3 3 3
n.s. n.s. n.s. n.s. n.s. n.s. 0 0 0
Numbers refer to the number of bands possible to distinguish in the chromatogram: 0 – no separation; 5 – all the compounds were detectable; n.s. – the mobile phase not suitable for chromatographic purposes (timeout); - –
the mobile phase components were not miscible. For the sake of readability of the Table, the non-miscible D6 –D25 dilutions with acetone, chloroform, and diethyl ether were excluded.
3
The experiments were projected to investigate the chromato- of the ring of the terpenoid compound (in menthol the ring is sat-
graphic properties of both pure DES and their dilutions. It was de- urated while in thymol it is aromatic), and the unsaturation is as-
cided that 10%, 20%, 30% and 40% diluting solvent would be added sociated with lower polarity. Moreover, the lowest polarity is noted
to the initial DES. The 50% dilution is indicated as a boundary for for D1 which contains phenyl salicylate that includes two aromatic
the eutectic properties [2,6], and thus it was excluded. Apart from rings. The observation is contrary to the standard eluotropic series,
water, which was the main dilution agent in the literature data where a saturated ring indicates a much lower elution strength
[6], methanol, chloroform, acetone and diethyl ether, the solvents than an aromatic one (e.g., cyclohexane vs. benzene). This is note-
widely used in TLC routine, were included. worthy, considering methanol dilutions, neither the pure DES nor
D1 –D5 did not mix with water in any proportion. Methanol was pure solvent were able to move efficiently the investigated com-
expected to be a proper solvent as the solubility of all the chemi- pounds (Fig. 1A, N). It was only the mixture of both that managed
cals included in D1 –D5 in the alcohol is at least good. Surprisingly, to move the alkaloids towards the solvent front (Fig. 1E). Thus, it
D1 did not mix with methanol up to a concentration of 60%, while may be concluded that the diluted DES was more polar than ei-
further addition of methanol allowed the components to dissolve. ther the pure eutectic or solvent individually. The nature of the
Apart from water (and regarding the case mentioned above) the phenomenon has yet to be investigated.
D1 –D5 were miscible with the tested solvents. In turn, the choline The D6 –D11 were diluted with water or methanol, which in ev-
chloride-based DES (D6 –D11 ) were fully miscible only with water ery case accelerated the chromatographic process. Regarding po-
and methanol and to some extent with acetone (from 10 to 20%, larity of the solvents, the standards could not be withdrawn from
depending on the particular DES). Since the acetone dilutions were the solvent front. For D12 –D24 water dilution decreased the devel-
not possible to obtain within the whole investigated range, they opment time in a concentration-dependent manner (Table 2) – 40%
were excluded from the experiment. The D12 –D25 were miscible dilutions were developed between 240 and 360 min. The same DES
only with water and methanol, in every investigated ratio. mixed with methanol, however, were much slower (800 min. and
more) and were disqualified as mobile phases. The degree of sep-
3.2. Chromatography with pure DES aration was differential. The best chromatographic properties, re-
garding both time and separation, were observed for D18 -W40 and
TLC analyses performed with pure eutectic solvents were able D23 -W40 modifications (Fig. 1K – L). Water had a negligible impact
to carry out the separation of the investigated mixture depending on resolution.
on the properties of the individual tested DES (Table 2). For the Given that D4 -M30 and D4 -M40 gave promising results, it was
pure DES the whole chromatographic process is relatively long and decided to lower the threshold of dilution, testing also D4 -M27.5,
lasts from 3 to more than 12 h. In the case of development lasting D4 -M32.5, D4 -M35 and D4 -M37.5. The best results were achieved
longer than 12 h, it was assumed that the specific mobile phase with D4 -M35, which interestingly had a different pattern of the
(either pure or diluted DES) is unsuitable for the TLC purposes. D1 standards compared to D4 -M30 and D4 -M40. Using the HPTLC
- D5 had a development time between 180 and 240 min. They en- plate for the selected mobile phase further improved the re-
abled forming bands, and the initial separation could be seen, with sults. D4 -M35 was subsequently tested with the real sample ob-
up to two recognizable bands (Table 2, Fig. 1A - B). D1 , D4 and D5 tained from the Chelidonium maius herb and proved to be efficient
as pure enabled low retention which indicates low polarity, while (Fig. 1T; Table S1-S2) and is considered to be applicable.
D2 and D3 DES were moving the investigated compounds close to The influence of methanol and diethyl ether on a development
the solvent front. D6 –D11 had development time of 120–210 min. time was ambiguous. In silica gel-based TLC, due to the low viscos-
They were characterized by too high polarity for the tested stan- ity, they generally enabled short-lasting analyzes. Thus, the men-
dards, which resulted in moving the investigated compounds to tioned solvents were supposed to decrease the development time.
the solvent front (Fig. 1I). The pure D12 –D25 were unsuitable for Actually, their effect was incongruous. Diethyl ether slowed down
chromatographic purposes due to excessive time of development. the process in every investigated case, but methanol either im-
proved (D2 –D11 ) or worsened (D12 –D25 ) the parameter. The ob-
3.3. Chromatography with diluted DES served phenomenon could be linked with the viscosity changes of
the mobile phase, but the parameter was not tested during the in-
The addition of diluting solvents to DES influenced to varying vestigation and the explanation needs additional experiments.
degrees the resolution and time of development. In order to ensure Water addition had little impact on the elution strength of the
comparability of the results, the chromatograms of the pure sol- tested DES. This is contrary to what was expected regarding the
vents were also presented (Fig. 1N-R). For the D1 –D5 dilutions had information presented in the literature data [6], where water was
an impact on the chromatogram development time, but interest- being used for modifications of DES polarity. The phenomenon may
ingly, not all the diluting solvents decreased it. The 40% methanol result from additional interactions between water and stationary
and acetone dilutions were the quickest, allowing 70–90 min de- phase’s functional groups that do not occur during extraction from
velopment, while the diethyl ether proportionally slowed it down, plant material.
reaching 410 min for the 40% dilution. The addition of polar com- It was a matter of interest whether other solvents apart from
pounds, like acetone or methanol, significantly improved the res- water would dilute DES without disrupting the eutectic matrix.
olution, whereas non-polar ones (chloroform, diethyl ether) did At the initial stage of the experiment, it was taken under con-
not. Nevertheless, chloroform managed to shorten the develop- sideration that after dilution the separation may depend only on
ment time, which may be an advantageous observation for future chromatographic properties of the solvents, leaving DES as an in-
eutectic-TLC use. For acetone and methanol, the ability to fine-tune ert part of the mobile phase. That would give the same separa-
the elution strength was proved and resulted in good resolution of tion pattern for all same-solvent dilutions (e.g., 40% acetone di-
the alkaloids. The most efficient were DES containing a terpenoid lutions would be similar regardless of DES used). However, chro-
and compound with phenolic ring (D1 , D4 , D5 ). The differences matograms obtained with different eutectics and the same solvent
could be better observed after dilution due to increased Rf in such were not alike but had similar features to the specific pure DES
cases. The most efficient were D1 -A40, D4 -M30, D4 -M40, D4 -A40, (Fig. 1E, G). This means that the eutectic matrix was preserved af-
D5 -M40 and D5 -A40 (Fig. 1C–H). Comparison of 40% dilution with ter dilution with the tested solvents in the investigated range and
acetone of D1 , D4 and D5 indicates their rank according to polarity that the matrix had a substantial impact on the chromatographic
as follows: D1 < D5 < D4 . D4 and D5 differ only in the saturation process. Additional support for that conclusion is an observation
D. Raj / Journal of Chromatography A 1621 (2020) 461044 5
Fig. 1. Chromatograms obtained with the selected mobile phases, using TLC Si60 plates, unless otherwise noted. All the pictures were taken at 366 nm. Mobile phases,
left to right: A–D4 ; B–D5 ; C–D1 -A40; D–D4 -M30; E–D4 -M40; F–D4 -A40; G–D5 -M40; H–D5 -A40; I–D7 ; J–D7 -W40; K–D18 -W40; L–D23 -W40; M–D4 -M35 on HPTLC plate. The
working solution developed in pure solvents: N – methanol; O – water; P – acetone; Q – chloroform; R – diethyl ether; S – the working solution developed in D4 -M60; T
– Chelidonium maius root extract developed with D4 -M35 mobile phase on HPTLC plate. Alkaloids marked in the chromatograms: Be – berberine, Ce – chelerythrine, Ci –
chelidonine, Co – coptisine, Sa – sanguinarine.
made at the preliminary stage of the experiment: a chromatogram matographic mobile phases based on non-classical interactions to
made using 60% dilution (Fig. 1S) was significantly different from be widely employed.
the one obtained within the eutectic range while similar to the
pure methanol one (Fig. 1N). Author contribution
The issue observed during the experiment is problematic down-
regulation of specific DES elution strength. While DES polarity can I am the only Author of the manuscript, therefore I am re-
be easily up-regulated with the addition of polar solvents, the non- sponsible for the: Conceptualization, Methodology, Validation, In-
polar ones do not change the elution. Lowering DES content along vestigation, Resources, Writing - Original Draft, Writing - Review &
with replacing it with less polar compounds in case of eutectic Editing, Visualization, Supervision, Project administration
mobile phases is not effective. Thus, the solution to the presented
problem may be using different DES with lower polarity as a start- Declaration of Competing Interests
ing point.
None.
4. Conclusions
CRediT authorship contribution statement
Eutectic TLC is possible and can result in good separation, even
for the complicated matrices that proved to be problematic for a Danuta Raj: Conceptualization, Investigation, Methodology, Val-
classic TLC. It is most probable that, in a short time, new DES types idation, Visualization, Writing - original draft, Writing - review &
with low viscosity will emerge, allowing for a new class of chro- editing.
Acknowledgments [7] S. Roehrer, F. Bezold, E.M. García, M. Minceva, Deep eutectic solvents in coun-
tercurrent and centrifugal partition chromatography, J. Chromatogr. A. 1434
(2016) 102–110, doi:10.1016/j.chroma.2016.01.024.
I would like to thank Dr. Sylwia Zielińska for advising and sup- [8] F. Bezold, M. Minceva, A water-free solvent system containing an l-menthol-
plying with standards, and Natalia Maryniak for her technical sup- based deep eutectic solvent for centrifugal partition chromatography applica-
port. tions, J. Chromatogr. A. 1587 (2019) 166–171, doi:10.1016/j.chroma.2018.11.083.
[9] Y. Dai, E. Rozema, R. Verpoorte, Y.H. Choi, Application of natural deep eutectic
solvents to the extraction of anthocyanins from Catharanthus roseus with high
Supplementary materials extractability and stability replacing conventional organic solvents, J. Chro-
matogr. A. 1434 (2016) 50–56, doi:10.1016/j.chroma.2016.01.037.
[10] G. Li, T. Zhu, Y. Lei, Choline chloride-based deep eutectic solvents as additives
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Journal of Chromatography A 1621 (2020) 461044

Contents lists available at ScienceDirect

Thin-layer chromatography with eutectic mobile phases—preliminary

1. Introduction ruption of intramolecular bondings which create an eutectic matrix

Components Molar ratio No Obtaining procedure

Camphor + phenyl salicylate 1:1 D1 P1

Methanol Water Acetone Chloroform Diethyl ether

D. Raj / Journal of Chromatography A 1621 (2020) 461044

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