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Choline-based deep eutectic solvents for green extraction of oil from sour cherry seeds

  • Belinda Amiti ORCID logo EMAIL logo , Kiril Lisichkov ORCID logo , Katerina Atkovska ORCID logo , Ahmed Jashari ORCID logo , Zehra Hajrulai Musliu ORCID logo , Hamdije Memedi and Arianit A. Reka ORCID logo EMAIL logo
Published/Copyright: November 26, 2025
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Open Chemistry
From the journal Open Chemistry Volume 23 Issue 1

Abstract

In last years, a plethora of extraction techniques has emerged as environmentally friendly alternatives to conventional extraction procedures. In this particular field, a novel class of solvents known as deep eutectic solvents (DES) has arisen as a new and very promising tool. For the extraction of oil from sour cherry seed, six types of these solvents were synthesized, with choline chloride as the hydrogen bond acceptor in combination with different hydrogen bond donors (alcohols, organic acids, glucose and urea). The experimental results proved that the use of ChCl:EG = 1:2 as co-solvent with n-hexane assisted by ultrasound under optimum conditions produced the highest yield of 16.15 % compared to pure n-hexane, which produced only 13.86 %. The fatty acid composition analysis revealed that linoleic acid (49.23–49.91 %) was the major fatty acid found in the oil, followed by oleic acid (40.73–41.04 %), palmitic (5.74–5.87 %) and stearic (2.02–2.13 %). The presented work emphasizes the role of green solvents in developing eco-efficient processes for oil extraction.

Keywords: oil extraction; sour cherry seed; n-hexane; ultrasonic; deep eutectic solvent

1 Introduction

Natural ingredients, chemical compounds or substances produced by living organisms in nature, often exhibit pharmacological or biological activity. These ingredients are widely used in the production of medicinal products, as well as in the design and discovery of new drugs [1]. They are also commonly used in cosmetics, the food industry, and other commercial applications [2]. Natural sources for obtaining such products include plants, marine organisms, microorganisms (especially products of fermentation), animal organisms, and natural poisons or toxins. These compounds form a large and diverse group, with varying chemical structures influenced by both biological (organisms) and geographical (origin) factors. Notably, many bioactive compounds have been discovered in plant materials, such as flowers, fruits, vegetables and nuts. Recent studies have also highlighted the value of plant waste such as seeds, peels, stems, leaves, and bark as valuable sources of bioactive compounds with diverse applications [3], [4], [5], [6], [7], [8], [9]. Several research groups [10], [11], [12], [13] have shown that plant seeds contain high levels of beneficial fatty acids, particularly oleic, linoleic, and linolenic acids, which contribute to improved memory, exhibit antioxidant properties, and significantly reduce blood cholesterol levels, thereby lowering the risk of coronary disease and other chronic diseases [14].

As such, oil extraction technology plays a crucial role in obtaining oils for their numerous health benefits. Several methods have been reported including cold press, maceration, Soxhlet, enzymatic, supercritical fluid extraction (SFE), microwave assisted extraction (MAE), ultrasound assisted extraction (UAE) or a combination of multiple techniques [15]. Conventional solvent extraction methods rely on hazardous petrochemical-derived volatile organic compounds (VOCs) including n-hexane, methanol, chloroform, petroleum ether, tetrahydrofuran [16].

The use of green solvents presents a promising solution to the limitations of conventional organic solvents. Deep eutectic solvents (DESs), first introduced by Abbot et al. [17], have rapidly emerged as a new class of sustainable and environmentally friendly solvents. These solvents are prepared by simply mixing two or more naturally occurring, inexpensive, and biodegradable components to form a eutectic mixture. The availability, low cost, biodegradability and environmental benefits of these components make DESs versatile alternatives to traditional organic solvents [18], [19], [20], [21]. Although deep eutectic solvents (DESs) have been successfully employed for the extraction of essential oils from various plant materials such as cinnamon [22], Angelica sinensis radix [23], roots of Nardostachys jatamansi [24], leaves of Perillae folium [25] and petals of Rosa damascena [26], there are limited reports on their application for oil extraction from plant seeds; flaxseed [27] and rubber seed [28].

Therefore, our research focused on optimizing the use of deep eutectic solvents (DESs) as co-solvent for the efficient extraction of oils from sour cherry seeds. A series of DESs was synthesized using choline chloride as the hydrogen bond acceptor (HBA), combined with a variety of hydrogen bond donors (HBDs), including urea, ethylene glycol, glycerol, glucose, lactic acid, and acetic acid. These HBDs were selected to represent different functional groups – amides, polyols, sugars, and carboxylic acids – with the aim of investigating how their structural characteristics and physical properties influence extraction performance. By evaluating these DESs under ultrasound-assisted extraction conditions, the process was optimized to improve both oil yield and quality. The findings highlight the potential of DESs as sustainable and selective co-solvents, offering an environmentally friendly alternative to conventional extraction methods.

2 Materials and methods

2.1 Chemicals and materials

Sour cherry fruit was obtained from a local fruit processing industry in North Macedonia. The seed were dried in oven (Electrothermal, Germany) at 60 °C for 24 h, grinded and sieved (Controls, Germany) in sizes 4 mm, 2 mm, 1 mm, 0.5 mm. Seeds with particle size of 0.5 mm were stored at −20 °C until oil extraction. n-hexane, choline chloride, urea, glucose, ethylene glycol, acetic acid, glycerol and lactic acid were purchased from Sigma Aldrich (Sweden) and used without further purification.

2.2 Conventional methods

Soxhlet extraction was conducted with n-hexane at a seed: solvent ratio of 1:30 (w/v) for 3 h using a heating mantle (Electrothermal, Germany) set at 70 °C. Maceration was carried out using n-hexane at a seed: solvent ratio of 1:10 (w/v), at 60 °C for 1 h. The resulting extract was cooled to room temperature and then filtered. The oil was recovered by evaporating the organic solvent with a rotary vacuum evaporator (IKA, Germany) at 50 °C. The extractions were performed in triplicate for reproducibility of results. The extracted oil was subjected to a nitrogen gas flush. Complete solvent removal was confirmed by the weight constancy method, whereby the sample was weighed before and after the nitrogen flushing and drying was considered complete once successive weights differed by less than 0.001 g.

2.3 Synthesis of DESs

In this study, choline chloride (ChCl) was selected as hydrogen bond acceptor (HBA). Ethylene glycol (EG), glycerol (GLY), lactic acid (LA), acetic acid (AA), urea (U) and glucose (GLU), were selected as hydrogen bond donors (HBDs). The DESs were synthesized by mixing HBA and HBD components at specific molar ratios, heated at 50 °C, stirring at a rate of 500 rpm for 30 min until viscous liquid was formed. The obtained solvents were stored in airtight glass bottles until further use.

2.4 Physical properties of DESs

The pH values of the synthesized DESs were measured using a calibrated digital pH meter (Mettler Toledo, Switzerland). The density of DESs were determined using glass pycnometer (25 mL), following a standard gravimetric method. The density of DESs was calculated using the following equation:

δ = m 1 − m 0 V

m1-mass of the pycnometer with solvent [g]

m0-mass of the empty pycnometer [g]

V-volume of the pycnometer [cm3]

The electrical conductivity of the solvents was determined by using a digital conductivity meter (Thermo Fisher Scientific, USA). The dynamic viscosity of the samples were measured using a rotational viscosimeter (Brookfield, USA). The measurements were performed at room temperature under constant stirring. ChCl:EG, ChCl:U and ChCl:GLU were previously heated in a water bath at 50 °C.

2.5 FTIR spectra of DESs

Shimadzu (Japan) instrument was used to perform FTIR analyses on the synthesized DESs. The spectrophotometer was equipped with ATR (attenuated total reflectance module), in the spectral range of 4,000–500 cm−1.

2.6 Extraction of oil by DESs as co-solvent

The eutectic solvent ChCl:EG = 1:2 was tested as co-solvent for oil extraction under varying conditions, with and without ultrasound (50 kHz) assistance. The experiments were conducted at different temperatures (40 °C, 50 °C, 60 °C) and durations (15, 30, 60 min) using a seed: n-hexane: DES ratio of 1:10:1 (w/v/w).

Extractions with the other DESs (Figure 1) were performed with ultrasound (50 kHz) at 60 °C for 60 min, maintaining the same seed: n-hexane: DES ratio of 1:10:1 (w/v/w). After extraction, the mixtures were cooled to room temperature and filtered. The filtrates were concentrated using a rotary vacuum evaporator (IKA, Germany) at 50 °C. The extracted oil was subjected to a nitrogen gas flush. Complete solvent removal was confirmed by the weight constancy method, whereby the sample was weighed before and after the nitrogen flushing and drying was considered complete once successive weights differed by less than 0.001 g. The presence of residual DES in the extracted oil was evaluated by performing a qualitative test for chloride ions using aqueous silver nitrate (0.1 M). The absence of a white silver chloride (AgCl) precipitate was taken as evidence that chloride-based DES components were not present in the final extract.

Figure 1: Ultrasound assisted extraction by DES.
Figure 1:

Ultrasound assisted extraction by DES.

2.7 GC-FID determination of fatty acids profile

The profile of fatty acids was determined by gas chromatograph (Agilent, GC 7890BA, USA) with flame ionization detector (GC-FID) and a capillary column (HP88-60 m × 250 mm x 0.2 mm). The samples were methylated to fatty acid methyl esters (FAMEs) using BF3 in methanol. Methyl esters were quantitatively measured using undecanoic acid (C11:0) as internal standard. 1 μL volume of each sample was analyzed in triplicate. Injection and detector temperatures were set at 250 °C and 300 °C, respectively. Helium was used as a carrier gas with a flow of 0.8 mL/min.

3 Results

3.1 Conventional methods

Soxhlet extraction and maceration as conventional methods, both employed n-hexane as solvent for oil extraction. The oil yields obtained from Soxhlet extraction and maceration were 15.65 ± 0.0017 % and 13.86 ± 0.0022 % (mean ± SD, n = 3), respectively. Statistical comparison using a two-sample t-test indicated that the 1.79 % difference between SE and MAC was statistically significant (p < 0.05), confirming that SE yielded more oil than MAC under the conditions tested (Figure 2).

Figure 2: Yield of extracted oil by conventional methods.
Figure 2:

Yield of extracted oil by conventional methods.

3.2 Physical properties of DESs

The physical properties of the newly synthesized deep eutectic solvents composed of choline chloride and various hydrogen bond donors (HBDs) vary significantly depending on the type of the HBD component (Table 1). pH values range from strongly acidc (1.69 for ChCl:AA) to nearly neutral (6.80 for ChCl:GLU), reflecting the acidic or basic characteristics of the individual components.

Table 1:

Physical properties of prepared DESs.

Deep eutectic solvent pH δ (g/cm3) μ (mPa·s) σ (mS)
Choline chloride: ethylene glycol = 1:2 5.31 1.17 45 7.78
Choline chloride: glycerol = 1:2 5.30 1.22 370 3.41
Choline chloride: lactic acid = 1:2 2.08 1.22 500 1.96
Choline chloride: acetic acid = 1:2 1.69 1.16 55 4.70
Choline chloride: urea = 1:2 6.30 1.25 750 0.47
Choline chloride: glucose = 2:1 6.80 1.30 8,000 0.003

The densities are relatively similar among DESs, ranging from 1.16 to 1.30 g/cm3 with the DES containing glucose exhibiting the highest density. Viscosity has greater variations, which ranges from only 45 mPa s in the solvent containg ethylene glycol to as high as 8,000 mPa s in the glucose system, which indicates that the molecular size of HBD component significantly influences viscosity. Electrical conductivity shows ana inverse correlation with viscosity; ChCl:EG exhibits high conductivity (7.78 mS), while ChCl:GLU has very low ionic mobility (0.003 mS).

3.3 FTIR spectra of the synthesized DESs

The successful synthesis of DESs based on choline chloride and various HBDs was confirmed using FTIR spectroscopy (supplementary material).

The FTIR spectrum of ChCl:EG (Figure 3) exhibited an intense absorption band at 3,250 cm−1, attributed to the stretching vibrations of the O–H group, characteristic of hydroxyl functionalities. The shift to a lower wavenumber compared to pure ethylene glycol [29] indicates the formation of a stable hydrogen bonding network between the components, confirming interactions leading to the formation of the eutectic mixture.

Figure 3: FTIR spectra of ChCl:EG = 1:2.
Figure 3:

FTIR spectra of ChCl:EG = 1:2.

Additionally, weak but well-defined absorption bands were observed in the region of 2,800–2,880 cm−1, corresponding to the symmetric and asymmetric stretching vibrations of methyl (–CH3) and methylene (–CH2) groups. An intense band around 1,450 cm−1 is likely due to the bending vibrations of –CH3 groups, further confirming the presence of the organic cation from choline chloride.

The band observed at 1,040 cm−1 is attributed to C–O stretching vibrations, characteristic of ethylene glycol, while a relatively strong band at 950 cm−1 likely originates from C–N bending vibrations characteristic of quaternary ammonium salts, specifically choline chloride.

3.4 Optimization of oil extraction using deep eutectic solvents

3.4.1 Effect of eutectic solvents on maceration

The use of deep eutectic solvent ChCl:EG = 1:2 significantly improved the oil extraction process. When applied in a maceration process at 60 °C for 60 min with a seed: n-hexane: DES = 1:10:1 (w/v/w), the yield of extracted oil reached 15.65 %. This represents a 1.8 % increase in yield compared to the same maceration process conducted without the DES (Figure 4).

Figure 4: Influence of DES on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 min extraction time and 60 °C extraction temperature.
Figure 4:

Influence of DES on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 min extraction time and 60 °C extraction temperature.

3.4.2 Influence of ultrasound-assisted extraction

Ultrasound-assisted extraction under the same conditions further increased the oil yield to 16.15 %, showcasing the synergistic effect of ultrasound and DES (Figure 5).

Figure 5: Influence of UAE on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 min extraction time and 60 °C extraction temperature.
Figure 5:

Influence of UAE on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 min extraction time and 60 °C extraction temperature.

3.4.3 Effect of DES concentration and viscosity

In a subsequent experiment, increasing the DES concentration to a seed: n-hexane: DES ratio of 1:10:2 (w/v/w) resulted in significantly lower yield of 5.80 %. This decrease is attributed to the increased viscosity of the medium, which hampers mass transfer during extraction (Figure 6).

Figure 6: Influence of viscosity of DES on oil yield, 60 min extraction time and 60 °C extraction temperature.
Figure 6:

Influence of viscosity of DES on oil yield, 60 min extraction time and 60 °C extraction temperature.

3.4.4 Optimization of temperature

Temperature optimization revealed that the highest yield (16.15 %) was achieved at 60 °C using ultrasound assisted extraction for 60 min with a seed: n-hexane: DES ratio of 1:10:1 (w/v/w). Lowering the temperature to 50 °C and 40 °C reduced the oil yield to 11.64 % and 10.26 %, respectively (Figure 7). At 60 °C n-hexane exists as a gas/liquid phase which reduces the viscosity and enables faster solvation of oil from the seeds.

Figure 7: Influence of extraction temperature on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 min extraction time and 60 °C extraction temperature.
Figure 7:

Influence of extraction temperature on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 min extraction time and 60 °C extraction temperature.

3.4.5 Optimization of extraction time

The duration extraction was also evaluated. At 60 °C, the yields for 15 and 30 min extraction time were 3.80 % and 10.70 %, respectively (Figure 8). Extending the extraction time to 60 min yielded the highest oil recovery.

Figure 8: Influence of extraction time on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 °C extraction temperature.
Figure 8:

Influence of extraction time on oil yield, at seed: solvent = 1:10 ratio (w/v), 60 °C extraction temperature.

3.4.6 Comparison of different eutectic solvents

Using ultrasound assisted extraction at 60 °C for 60 min with a seed: n-hexane: DES ratio 1:10:1 (w/v/w), various DES formulations were compared. The oil yields for DES composed of choline chloride with ethylene glycol, glucose, urea, glycerol, lactic acid and acetic acid were 16.15 %, 12.48 %, 11.72 %, 10.28 %, 10.17 % and 10.16 %, respectively (Figure 9). The results indicate that ethylene glycol is the most effective hydrogen bond donor, followed by glucose and urea, while lactic and acetic acid were the least effective.

Figure 9: Yield of extracted oil by different DES as co-solvent, at seed: solvent = 1:10 (w/v), 60 min extraction time and 60 °C extraction temperature.
Figure 9:

Yield of extracted oil by different DES as co-solvent, at seed: solvent = 1:10 (w/v), 60 min extraction time and 60 °C extraction temperature.

3.5 Fatty acid analysis

The fatty acid profile of sour cherry seed oil obtained using different extraction techniques, including maceration, Soxhlet and DES as co-solvent revealed a composition dominated by unsaturated fatty acids (UFAs), accounting for over 91 % of total fatty acids (Table 2). Oleic acid was the most prevalent within the monounsaturated fatty acids, with contents ranging from 40.73 % to 41.04 % across all methods. As a representative of ω-9 family, oleic acid plays a crucial role in maintaining cardiovascular health, modulating inflammatory responses and improving insulin sensitivity. Its content in sour cherry seed oil is comparable to that of olive oil [30].

Table 2:

Fatty acid composition of extracted oil.

Fatty acid (%) MAC SE ChCl:EG ChCl:LA ChCl:GLU ChCl:U ChCl:GLY ChCl:AA
C18:1 40.91 41.04 40.83 40.73 40.90 40.79 40.76 41.03
C18:2 49.23 49.40 49.34 49.51 49.31 49.24 49.31 49.91
C18:3 0.40 0.41 0.41 0.42 0.39 0.41 0.40 /
C16:1 0.37 0.32 0.32 0.31 0.38 0.37 0.37 0.33
C16:0 5.77 5.84 5.74 5.87 5.75 5.77 5.80 5.82
C18:0 2.03 2.13 2.04 2.06 2.04 2.07 2.02 2.05
C10:0 0.05 0.05 / / / 0.06 0.05 0.12
C22:2 0.78 0.37 0.82 0.84 0.81 0.84 0.84 0.72
SFA 7.84 8.00 7.81 7.91 7.77 7.89 7.86 7.97
MUFA 41.29 41.37 41.15 41.05 41.27 41.17 41.13 41.36
PUFA 50.86 50.61 51.02 51.02 50.94 50.93 51.00 50.66

Among polyunsaturated fatty acids (PUFAs), linoleic acid (C18:2, n-6) an essential ω-6 fatty acid was found in very high concentration (49.23–49.91 %), with additional minor contributions from docosadienoic acid (C22:2, n-6), bringing the total ω-6 content to approximately 50–50.7 %. ω-6 fatty acids are necessary for cholesterol metabolism, skin health, immune response and growth [31]. In contrast, linolenic acid (C18:3, n-3), the only detected ω-3 fatty acid, was present at significantly lower levels (0.39–0.42 %) and was undetected in the oil extracted by DES co-solvent ChCl:AA. Palmitic (5.74–5.87 %) and stearic (2.02–2.13 %) were predominant among saturated fatty acids. Additional saturated fatty acid identified was capric acid (0.05–0.12 %).

4 Discussion

In our previous work [32], we have reviewed the available literature on oil extraction from sour cherry seeds. Different methods for extraction have been used starting from the conventional like cold press, Soxhlet extraction and innovative like superfluid extraction. Among these, Soxhlet extraction using nonpolar solvents like n-hexane and petroleum ether remains the most widely employed method. Reported oil yields from Soxhlet extractions range from 4 % to 36 %, while in this study we obtained 15.65 % oil yield.

To date, DESs have not been reported for the extraction of oil from sour cherry seeds, despite a numerous studies as green alternatives to conventional methods. In this study, we synthesized a series of choline-based DESs using ethylene glycol, glycerol, urea, glucose, lactic and acetic acid as hydrogen bond donors (HDBs). The properties of the synthesized DES systems were found to significantly influence their capacity to extract oils from seeds, which predominantly consist of triglycerides with nonpolar or slightly polar characteristics. In this regard, systems with lower viscosity, such as ChCl:EG (45 mPa s), were shown to enable better penetration into the plant matrix and more efficient release of lipophilic components. Additionally, the moderate pH value (5.31) and relatively low density (1.17 g/cm3) facilitated phase separation following the extraction process. In contrast, DES systems with high viscosity, such as ChCl:GLY (370 mPa s), ChCl:LA (500 mPa s), and particularly ChCl:GLU (8,000 mPa s), were found to exhibit limitations in molecular mass transport, resulting in reduced extraction efficiency. The elevated viscosity was observed to hinder the diffusion of oils through the solvent, as well as their desorption from the surface of the cell walls. Furthermore, the low electrical conductivity recorded for ChCl:GLU (0.003 mS) indicated restricted ionic mobility and poor molecular dissociation, which may further diminish interactions with lipophilic components. Acidic DES formulations, such as ChCl:LA (pH 2.08) and ChCl:AA (pH 1.69), were found to be unsuitable for oil extraction. The low pH values may cause partial hydrolysis of sensitive lipid components or lead to emulsion formation, which hinders phase separation and complicates subsequent processing steps. The formation of DESs was confirmed by FTIR spectroscopy, where red shifts in characteristic bands indicated the establishment of hydrogen bonding between the hydrogen bond donor and acceptor, in accordance with already published spectra [33].

Ultrasound assisted extraction using DESs has been widely studied for recovery of bio compounds from plants and has proven effective in increasing yield while minimizing extraction time, temperature and energy consumption [34], [35], [36], [37], [38]. During our research, under optimized conditions assisted by ultrasound ChCl:EG = 1:2 exhibited higher oil recovery in contrast to conventional methods. This approach aligns with findings by Zare Nezhad et al. [39] who demonstrated the effectiveness of ChCl:EG = 1:2 as co-solvent in enhancing oil extraction yields, particularly in halophytic safflower and salicornia plants. When used as a co-solvent ChCl:EG = 1:2 with n-hexane for flaxseed oil extraction, slightly improved the oil yield compared to n-hexane and significantly lowered the optimum extraction temperature under optimized conditions [27]. Similarly, using ChCl:GLY = 1:2 as a co-solvent for rubber seed oil extraction increased the oil yield to 30.7 % compared to 27.0 % with pure diethyl ether [28].

The analysis of fatty acids revealed that the extraction technique did not contribute to considerable differences between fatty acids profiles of oil samples recovered by maceration, Soxhlet and by DES as co-solvent. However, subtle but notable differences in oil quality emerged depending on the extraction method. The extraction assisted by ChCl:GLU, exhibited slightly higher UFA content and lower SFA levels compared to conventional methods, suggesting an enhanced selectivity of this DES towards unsaturated fatty acids. Specifically, SFA was reduced by 0.07–0.23 % points relative to MAC and SE, while UFA increased by 0.06–0.23 % points. Compared to other DES, ChCl:GLU demonstrated SFA decreases of 0.04–0.20 % points and UFA increases between 0.04 and 0.19 % points. On the other hand, the use of ChCl:AA resulted in the lowest UFA recovery and absence of detectable linolenic acid, indicating lower extraction efficiency. The absence of linolenic acid (C18:3, n-3) in the oil extracted with ChCl:AA is attributed to the strongly acidic nature of the system (pH 1.69), under which polyunsaturated fatty acids may be degraded or isomerized. Due to its high degree of unsaturation, C18:3 is particularly susceptible to acid-catalyzed transformation, which has resulted in its absence. This finding highlights the risk of PUFA degradation when highly acidic DESs are applied for oil extraction.These observations highlight that the choice of DES composition influences oil quality, with ChCl:GLU standing out as the most effective system.

Gornaś et al. [40] reported that sour cherry seed extracts obtained with n-hexane were primarily composed of oleic (25.25–45.30 %) and linoleic acids (35.50–46.06 %), with lower levels of palmitic, α-eleostearic, stearic, and arachidic acids, while palmitoleic, α-linolenic, and gondoic acids were detected at <1.00 %. Similarly, Yilmaz and Gokmen [41] found oleic (46.30 %) and linoleic acid (41.50 %) to be the dominant fatty acids in oils extracted with n-hexane and supercritical CO2, accompanied by smaller proportions of palmitic (6.40 %), linolenic (4.60 %), and stearic acid (1.20 %). In contrast, Dimić et al. [42] identified linoleic acid (47.00 %) as the major component, followed by oleic acid (41.46 %), while palmitic (6.62 %), stearic (2.21 %), and arachidic acid (1.12 %) were present in lower concentrations.

5 Conclusions

In this study, an eco-friendly process for oil extraction from sour cherry seed is developed. The extraction process assisted by ultrasound, resulted in higher yield of extracted oil when choline chloride: ethylene glycol = 1:2 was employed as co-solvent in comparison to n-hexane. Also, the optimized process achieved in this study showed advantages in the extraction temperature (70 °C vs 60 °C), time (3 h vs 1 h), amount of solvent (150 mL vs 50 mL) and a higher yield of extracted oils compared to Soxhlet extraction. The presented approach can have wide application in extraction of oils by reducing energy consumption and environmental hazards associated with the use of conventional solvents, particularly n-hexane.

The profile of fatty acids revealed that sour cherry seed oil represents a valuable source of ω-6 and ω-9 fatty acids, with modest amount of ω-3. Its high degree of unsaturation and low SFA/UFA ration make it suitable for use in nutraceuticals and cosmetics.

Corresponding author: Belinda Amiti, Faculty of Technology and Metallurgy, University “Ss. Cyril and Methodius”, Skopje, North Macedonia; and Faculty of Natural Sciences and Mathematics, University of Tetovo, Tetovo, North Macedonia, E-mail: ; and Arianit A. Reka, Faculty of Natural Sciences and Mathematics, University of Tetovo, Tetovo, North Macedonia, E-mail:

Abbreviations

The following abbreviations are used in this manuscript:

ChCl:GLU

Choline chloride: glucose

ChCl:AA

Choline chloride: acetic acid

ChCl:EG

Choline chloride: ethylene glycol

ChCl:GLY

Choline chloride: glycerol

ChCl:LA

Choline chloride: lactic acid

ChCl:U

Choline chloride: urea

DES

Deep eutectic solvent

FAME

Fatty acid methyl esters

HBA

Hydrogen bond acceptor

HBD

Hydrogen bond donor

MAC

Maceration

MAE

Microwave assisted extraction

MUFA

Monounsaturated fatty acids

PUFA

Polyunsaturated fatty acids

SE

Soxhlet extraction

SFA

Saturated fatty acids

SFE

Superfluid extraction

UAE

Ultrasound assisted extraction

UFA

Unsaturated fatty acids

VOC

Volatile organic compounds

  1. Funding information: The authors received no funding for this research.

  2. Author contributions: Conceptualization: Belinda Amiti and Kiril Lisichkov; data curation and formal analysis: Belinda Amiti, Kiril Lisichkov, Katerina Atkovska, Ahmed Jashari, Zehra Hajrulai Musliu, Hamdije Memedi and Arianit A. Reka; investigation: Belinda Amiti and Kiril Lisichkov; methodology: Belinda Amiti and Kiril Lisichkov; project administration: Belinda Amiti and Kiril Lisichkov; resources: Kiril Lisichkov; supervision: Kiril Lisichkov and Arianit A. Reka; validation: Belinda Amiti and Kiril Lisichkov; visualization: Belinda Amiti; writing – original draft: Belinda Amiti and Kiril Lisichkov; writing – review and editing: Belinda Amiti, Kiril Lisichkov, Katerina Atkovska, Ahmed Jashari, Zehra Hajrulai Musliu, Hamdije Memedi and Arianit A. Reka.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: The datasets generated during and/or analysed during the current study are available from the corresponding author on reasonable request.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/chem-2025-0199).

Received: 2025-07-02
Accepted: 2025-09-11
Published Online: 2025-11-26

© 2025 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2025-0199
Keywords for this article
oil extraction; sour cherry seed; n-hexane; ultrasonic; deep eutectic solvent
Creative Commons
BY 4.0

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  79. Characterization of organic arsenic residues in livestock and poultry meat and offal and consumption risks
  80. Synthesis and characterization of zinc sulfide nanoparticles and their genotoxic and cytotoxic effects on acute myeloid leukemia cells
  81. Activity of Coriandrum sativum methanolic leaf extracts against Eimeria papillata: a combined in vitro and in silico approach
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