Effect of Solvent Composition and Auxiliary Treatments on the Extraction of Dracocephalum kotschyi Boiss Extract Using Deep Eutectic Solvents

Articles in Press

Document Type : Research Article

Authors

• Sahar Kiani
• Hajar Abbasi

Department of Food Science and Technology, College of Agriculture, Isfahan (Khorasgan) Branch, Islamic Azad University, Isfahan, Iran

10.22067/ifstrj.2025.91737.1403

Abstract

Introduction
Recovery of active ingredients from plants is generally carried out using solid-liquid extraction. Selecting an appropriate solvent is one of the parameters that strongly affects the extraction performance and the type of extracted compounds. So far, various solvents have been used to extract these compounds. In addition to the need for large amounts of solvent, the high consumption of organic solvents causes problems such as environmental pollution and possible destruction of active compounds. Green solvents have been considered for the extraction process to reduce the consumption of non-toxic solvents and protect the environment. Natural deep eutectic solvents (NADES) are a new class of solvents used in extraction that consist of a mixture of two or more biodegradable natural compounds with low or no toxicity. The important features of these solvents are their low toxicity, biocompatibility, simple preparation, and low cost. Given the significant advantages of these solvents, in recent years, the use of NADES in the extraction of phenolic and antioxidant compounds has been considered. Applying appropriate auxiliary treatments to the sample or the sample-solvent combination during the extraction process can improve the performance of the extraction process. The use of ultrasonic waves allows for better extraction by creating shear force, disrupting the integrity of the cell wall, and better penetration of the solvent into the tissue. Pulsed electric waves also create pores in the cell membrane without causing minimal damage to the other parts, while maintaining consistency and structure, accelerating the permeability and transport of water and dissolved substances from the cell membrane, and allowing the extraction of active substances under better conditions.
Materials and Methods
This study was conducted in 3 phases to extract the compounds of the golden plant using natural deep eutectic solvents. In the first phase, effect of the type of solvent used including carboxylic acids (citric acid and malic acid), sugars (glucose and fructose), and sugar alcohols (ethylene glycol and glycerol) on the quality of the extracted material was evaluated. In the second phase, to improve the possibility of extracting the active ingredient of this plant, the sample was treated with pulsed electric waves, and in the third phase, the extraction of phenolic compounds from the sample was carried out with the solvent type selected from the first phase under the conditions of applying and non applying ultrasonic waves. Identification of the compounds present in the extract was carried out on the selected samples using HPLC. Finally, the ability to recover the extracted compounds was carried out from the best sample. Statistical analysis of the results was carried out using a completely randomized design - factorial test with SAS VERSION 9 software.
Results and Discussion
The extract from the eutectic solvent containing ethylene glycol due to its high antioxidant activity and the extract from the eutectic solvent containing maleic acid due to its high phenolic compounds were selected as the best solvents for making the Dracocephalum kotschyi extract. Considering the total number of identified compounds, the content of identified compounds in the extract with a eutectic solvent containing ethylene glycol was 17000.05 μg/g, and in the extract with a eutectic solvent containing maleic acid was 10029.1 μg/g. Therefore, the content of active compounds of an extract with a eutectic solvent containing ethylene glycol was about 70% higher than the content of active compounds of an extract with a eutectic solvent containing maleic acid, and this solvent was selected for further studies. The study of the effect of applying electric pulses and ultrasonic waves on the extraction process shows that by increasing the intensity of the electric pulse and the duration of using ultrasonic waves, the content of phenolic compounds and antioxidant properties of the extract increased. Electric pulses accelerate the permeability and transport of water and dissolved substances by creating pores in the cell membrane. The change in the properties of the cell wall membrane in such a way that the substances inside the cell can be quickly and easily removed from the cell, causes the extraction to be carried out in the minimum time and energy required. The total weight of phenolic compounds identified in the extract with a eutectic solvent containing ethylene glycol with the application of auxiliary was 25275.41 μg/g, without the application of auxiliary treatments was 17000.05 μg/g, and in the sample extracted with ethanol was 21652.89 μg/g. Therefore, the application of auxiliary treatments was effective and superior to the ethanol solvent in increasing the extraction of compounds from the plant. The polyphenol content extracted with ethylene glycol-choline chloride with and without auxiliary treatments was determined as 53 and 45 percent, respectively.
Conclusion
The solvent containing choline chloride-ethylene glycol had the best conditions for extracting the active compounds of Dracocephalum kotschyi. Applying a 5000 W electric pulse pretreatment and using ultrasonic waves for 30 minutes in the extraction stage had a significant effect in increasing the extractability of the active compounds. Using the anti-solvent (water) precipitation method, 53% of the phenolic compounds were recovered and the eutectic solvent was returned to the system.

Keywords

• Antioxidant activity
• Dracocephalum kotschyi
• Natural deep eutectic solvent
• Phenolic compounds
• Pulse electric field
• Ultrasonic waves

Main Subjects

• Food Technology

©2025 The author(s). This is an open access article distributed under Creative Commons Attribution 4.0 International License (CC BY 4.0)

References

1. Aghaei Shalmani, M., & Salehi, M.A. (2014). Effect of pulsed electric field extraction efficiency, University of Guilan, Faculty of Technology and Engineering, Department of Chemistry, 02_061. https://civilica.com/doc/343270.
2. Azmir, J., Zaidul, I.S.M., Rahman, M.M., Sharif, K.M., Mohamed, A., Sahena, F., Jahurul, M.H.A., Ghafoor, K., Norulaini, N.A.N., & Omar, A.K.M. (2013). Techniques for extraction of bioactive compounds from plant materials: a review. Journal of Food Engineering, 117, 426-436. https://doi.org/10.1016/j.jfoodeng. 2013.01.014
3. Aydin, F., Yilmaz, E., & Soylak, M. (2018). Vortex assisted deep eutectic solvent (DES) emulsification liquid microextraction of trace curcumin in food and herbal tea sample. Food Chemistry, 243, 442-447. https://doi.org/10.1016/j.foodchem.2017.09.154
4. Alanon, M.E., Ivanovi´c, M., Gomez-Caravaca, A.M., Arraez-Roman, D., & SeguraCarretero, A. (2020). Choline chloride derivative-based deep eutectic liquids as novel green alternative solvents for extraction of phenolic compounds from olive leaf. Arabian Journal of Chemistry, 13(1), 1685–1701. https://doi.org/10.1016/j.arabjc.2018.01.003
5. Bahadori, M.B., Zengin, G., Bahadori, Sh., Dinparast, L., & Movahhedin, N. (2018). Phenolic composition and functional properties of wild mint (Mentha longifolia calliantha (Stapf) Briq.). International Journal of Food Properties, 21, 183–193. https://doi.org/10.1080/10942912.2018.1440238
6. Doldolova, Kh., Bener, M., Lalikoglu ˘, M., Selim As¸çı, Y., Arat, R., & Apak, R. (2021). Optimization and modeling of microwave-assisted extraction of curcumin and antioxidant compounds from turmeric by using natural deep eutectic solvents. Food Chemistry, 353, 129337. https://doi.org/10.1016/j.foodchem.2021.129337
7. Dai, Y., Spronsenb, J., Witkampb, G., Verpoortea, R., & Hae Choi, Y. (2013). Natural deep eutectic solvents as new potential media for green technology. Analytica Chimica Acta, 766, 61-68. https://doi.org/10.1016/j.aca. 2012.12.019
8. Delos Angeles Fernandez, M., Espino, M., Gomez, F.J.V., & Silva, M.F. (2018). Novel approaches mediated by tailor-made green solvents for the extraction of phenolic compounds from agro-food industrial by-products. Food Chemistry, 239, 671–678. https://doi.org/10.1016/j.foodchem.2017.06.150
9. Foroozandeh, E., & Asadi-Gharneh, H. (2021). Dracocephalum kotschyi:An Iranian endemic medicinal plant; A review. Journal of Medicinal Herbs, 12, 9-17.
10. Florindo, C., Oliveira, F.S., Rebelo, L.P.N., Fernandes, A.M., & Marrucho, I.M. (2014). Insights into the synthesis and properties of deep eutectic solvents based on choline chloride and carboxylic acids. ACS Sustainable Chemistry & Engineering, 2(10), 2416−2425. https://doi.org/10.1021/sc500439w
11. García, A., Rodríguez-Juan, E., Rodríguez-Gutiérrez, G., Julian Rios, J., & Fernández-Bolaños, J. (2016). Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs). Food Chemistry, 197, 554-561. https://doi.org/10.1016/j.foodchem.2015.10.131
12. Huang, Y., Feng, F., Jiang, J., Qiao, Y., Wu, T., Voglmeir, J., & Chen, Z.G. (2017). Green and efficient extraction of rutin from tartary buckwheat hull by using natural deep eutectic solvents. Food Chemistry, 221, 1400–1405. https://doi.org/10.1016/j.foodchem. 2016.11.013
13. Jeong, K.M., Jin, Y., Yoo, D.E., Han, S.Y., Kim, E.M., & Lee, J. (2018). One-step sample preparation for convenient examination of volatile monoterpenes and phenolic compounds in peppermint leaves using deep eutectic solvents. Food Chemistry, 251, 69–76. https://doi.org/10.1016/j.foodchem.2018.01.079
14. Juri´c, T., Mi´ci´c, N., Potkonjak, A., Milanov, D., Dodi´c, J., Trivunovi´c, Z., & Popovi´c, B. (2021). The evaluation of phenolic content, in vitro antioxidant and antibacterial activity of Mentha piperita extracts obtained by natural deep eutectic solvents. Food Chemistry, 362, 130226. https://doi.org/10.1016/j.foodchem.2021.130226
15. Li, B., Du, W., Jin, J., & Du, Q. (2012). Preservation of epigallocatechin-3-gallate antioxidant properties loaded in heat treated -lactoglobulin nanoparticles. Journal of Agricultural and Food Chemistry, 60, 3477–3484. https://doi.org/10.1021/jf300307t
16. Mozaffarian, V. (2008). A dictionary of Iranian plant names. Latin, English, Persian, FarhangMo'aser. 740.
17. Nam, M.W., Zhao, J., Lee, M.S., Jeong, J.H., & Lee, J. (2015). Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: Application to flavonoid extraction from Flos sophorae. Green Chemistry, 17(3), 1718–1727. https://doi.org/10.1039/c4gc01556h
18. Paiva, A., Craveiro, R., Aroso, I., Martins, M., Reis, R.L., & Duar, A.R.C. (2014). Natural deep eutectic solvents-solvents for the 21^st ACS Sustainable Chemistry & Engineering, 2(5), 1063-1071. https://doi.org/10.1021/sc500096j
19. Patil, S.S., Pathak, A., & Rathod, V.K. (2020). Optimization and kinetic study of ultrasound assisted deep eutectic solvent based extraction: A greener route for extraction of curcuminoids from Curcuma longa. Ultrasonics Sonochemistry, 70, 105267. https://doi.org/10.1016/j.ultsonch.2020.105267
20. Smith, E.L., Abbott, A.P., & Ryder, K.S. (2014). Deep eutectic solvents (DESs) and their applications. Chemistry, 114, 11060–11082. https://doi.org/10.1021/cr300162p
21. Santos, S., Pinto, P., Silvestre, A., & Pascoal Neto, C. (2010). Chemical composition and antioxidant activity of phenolic extracts of cork from Quercus suber Industrial Crops and Products, 31, 521-526. https://doi.org/10.1016/j.indcrop.2010.02.001
22. Vorobiev, E, & Lebovka, N. (2010). Enhanced extraction from solid foods and biosuspensions by pulsed electrical energy. Food Engineering, 2, 95–108. https://doi.org/10.1007/s12393-010-9021-5
23. Wu, L., Li, L., Chen, Sh., Wang, L., & Lin, X. (2020). Deep eutectic solvent-based ultrasonic-assisted extraction of phenolic compounds from Moringa oleifera leaves: Optimization, comparison and antioxidant activity. Separation and Purification Technology, 247, 117014. https://doi.org/10.1016/j.seppur.2020.117014
24. Wei, Z.F., Wang, X.Q., Peng, X., Wang, W., Zhao, C.J., Zu, Y.G., & Fu, Y.J. (2015). Fast and green extraction and separation of main bioactive flavonoids from Radix scutellariae. Industrial Crops and Products, 63, 175–181. https://doi.org/10.1016/j.indcrop.2014.10.013
25. Zhang, Q., De Oliveira-Vigier, K., Royer, S., & Jérôme, F. (2012). Deep eutectic solvents: Syntheses, properties and applications. Chemical Society Reviews, 41, 7108–7146. https://doi.org/10.1039/c2cs35178a
26. Zhou, P., Wanga, X., Liub, P., Huanga, J., Wanga, Ch., Pana, M., & Kuanga, Z. (2018). Enhanced phenolic compounds extraction from Morus alba leaves by deep eutectic solvents combined with ultrasonic-assisted extraction. Industrial Crops & Products, 120, 147-154. https://doi.org/10.1016/j.indcrop.2018.04.071