Natural Deep Eutectic Solvents Combined with Supercritical Carbon Dioxide for the Extraction of Curcuminoids from Turmeric

Overview

Journal Pharmaceuticals (Basel)

Publisher MDPI

Specialty Chemistry

Date 2025 Jan 8

PMID 39770438

Authors

Anna Stasilowicz-Krzemien

Julia Wojcik

Anna Gosciniak

Marcin Szymanski

Piotr Szulc

Krzysztof Gorecki

Judyta Cielecka-Piontek

Affiliations

Soon will be listed here.

Abstract

Background: Curcuminoids, the bioactive compounds found in turmeric, exhibit potent antioxidant, anti-inflammatory, and neuroprotective properties. This study aims to enhance the extraction of curcuminoids from turmeric using environmentally friendly solvents supercritical CO (scCO) combined with natural deep eutectic solvents (NADESs) in one process, and to evaluate the resulting biological activity.

Methods: A Box-Behnken statistical design was applied to optimize scCO extraction conditions-pressure, CO volume, and temperature-to maximize curcuminoid yield. Next, the menthol and lactic acid NADESs were selected, and these two solvents were combined into a single turmeric extraction process. The biological activity of the resulting extract was evaluated using antioxidant assays (ferric reducing antioxidant power and 2,2-diphenyl-1-picrylhydrazyl) and enzyme inhibition assays (acetylcholinesterase, butyrylcholinesterase, and tyrosinase). Toxicity assessments were conducted on the aquatic invertebrates , sp., and .

Results: The most effective extraction was achieved using a menthol-lactic acid NADES as a cosolvent, integrated at a 1:20 ratio of plant material to NADESs while in combination with scCO. The optimized scCO-NADES extraction resulted in a high curcuminoid yield (33.35 mg/g), outperforming scCO extraction (234.3 μg/g), NADESs ultrasound-assisted extraction (30.50 mg/g), and alcohol-based solvents (22.95-26.42 mg/g). In biological assays, the extract demonstrated significant antioxidant activity and effective inhibition of enzymes (acetylcholinesterase, butyrylcholinesterase, and tyrosinase). Toxicity studies showed a concentration-dependent response, with EC for at the level of 0.098 μL/mL and exhibiting high sensitivity to the extract.

Conclusions: This study highlights the potential of combining NADESs and scCO extraction in one process, demonstrating the effectiveness of scCO-NADES extraction in maximizing curcuminoid yield and enhancing bioactivity.

References

Vladic J, Kovacevic S, Aladic K, Jokic S, Radman S, Podunavac-Kuzmanovic S . Innovative Strategy for Aroma Stabilization Using Green Solvents: Supercritical CO Extracts of Dispersed in Deep Eutectic Solvents. Biomolecules. 2023; 13(7). PMC: 10377330. DOI: 10.3390/biom13071126. View

Hansen B, Spittle S, Chen B, Poe D, Zhang Y, Klein J . Deep Eutectic Solvents: A Review of Fundamentals and Applications. Chem Rev. 2020; 121(3):1232-1285. DOI: 10.1021/acs.chemrev.0c00385. View

Usmani Z, Sharma M, Tripathi M, Lukk T, Karpichev Y, Gathergood N . Biobased natural deep eutectic system as versatile solvents: Structure, interaction and advanced applications. Sci Total Environ. 2023; 881:163002. DOI: 10.1016/j.scitotenv.2023.163002. View

Jelinski T, Przybylek M, Cysewski P . Natural Deep Eutectic Solvents as Agents for Improving Solubility, Stability and Delivery of Curcumin. Pharm Res. 2019; 36(8):116. PMC: 6546644. DOI: 10.1007/s11095-019-2643-2. View

Puzeryte V, Martusevice P, Sousa S, Balciunaitiene A, Viskelis J, Gomes A . Optimization of Enzyme-Assisted Extraction of Bioactive Compounds from Sea Buckthorn ( L.) Leaves: Evaluation of Mixed-Culture Fermentation. Microorganisms. 2023; 11(9). PMC: 10536544. DOI: 10.3390/microorganisms11092180. View

Ciuca M, Racovita R . Curcumin: Overview of Extraction Methods, Health Benefits, and Encapsulation and Delivery Using Microemulsions and Nanoemulsions. Int J Mol Sci. 2023; 24(10). PMC: 10219365. DOI: 10.3390/ijms24108874. View

Vieira C, Rebocho S, Craveiro R, Paiva A, Duarte A . Selective extraction and stabilization of bioactive compounds from rosemary leaves using a biphasic NADES. Front Chem. 2022; 10:954835. PMC: 9412766. DOI: 10.3389/fchem.2022.954835. View

Genchi G, Lauria G, Catalano A, Carocci A, Sinicropi M . Neuroprotective Effects of Curcumin in Neurodegenerative Diseases. Foods. 2024; 13(11). PMC: 11172163. DOI: 10.3390/foods13111774. View

Patil S, Pathak A, Rathod V . Optimization and kinetic study of ultrasound assisted deep eutectic solvent based extraction: A greener route for extraction of curcuminoids from Curcuma longa. Ultrason Sonochem. 2020; 70:105267. PMC: 7786552. DOI: 10.1016/j.ultsonch.2020.105267. View

10.

Oomen W, Begines P, Mustafa N, Wilson E, Verpoorte R, Choi Y . Natural Deep Eutectic Solvent Extraction of Flavonoids of as a Replacement for Conventional Organic Solvents. Molecules. 2020; 25(3). PMC: 7038101. DOI: 10.3390/molecules25030617. View

11.

Kaltsa O, Lakka A, Grigorakis S, Karageorgou I, Batra G, Bozinou E . A Green Extraction Process for Polyphenols from Elderberry () Flowers Using Deep Eutectic Solvent and Ultrasound-Assisted Pretreatment. Molecules. 2020; 25(4). PMC: 7070494. DOI: 10.3390/molecules25040921. View

12.

Vladic J, Kovac M, Pavic V, Jokic S, Simic S, Paiva A . Towards a Greener Approach for Biomass Valorization: Integration of Supercritical Fluid and Deep Eutectic Solvents. Antibiotics (Basel). 2023; 12(6). PMC: 10295627. DOI: 10.3390/antibiotics12061031. View

13.

Widmann A, Wahl M, Kammerer D, Daniels R . Supercritical Fluid Extraction with CO of L. in Comparison to Conventional Solvent Extraction. Pharmaceutics. 2022; 14(9). PMC: 9502963. DOI: 10.3390/pharmaceutics14091943. View

14.

Stasilowicz-Krzemien A, Rosiak N, Plazinska A, Plazinski W, Miklaszewski A, Tykarska E . Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid. Pharmaceutics. 2022; 14(10). PMC: 9611598. DOI: 10.3390/pharmaceutics14102098. View

15.

Cannavacciuolo C, Pagliari S, Frigerio J, Giustra C, Labra M, Campone L . Natural Deep Eutectic Solvents (NADESs) Combined with Sustainable Extraction Techniques: A Review of the Green Chemistry Approach in Food Analysis. Foods. 2023; 12(1). PMC: 9818194. DOI: 10.3390/foods12010056. View

16.

Ahmed T, Gilani A . Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease. Pharmacol Biochem Behav. 2008; 91(4):554-9. DOI: 10.1016/j.pbb.2008.09.010. View

17.

Shen L, Pang S, Zhong M, Sun Y, Qayum A, Liu Y . A comprehensive review of ultrasonic assisted extraction (UAE) for bioactive components: Principles, advantages, equipment, and combined technologies. Ultrason Sonochem. 2023; 101:106646. PMC: 10594638. DOI: 10.1016/j.ultsonch.2023.106646. View

18.

Vahidi S, Monhemi H, Hojjatipour M, Hojjatipour M, Eftekhari M, Vafaeei M . Supercritical CO/Deep Eutectic Solvent Biphasic System as a New Green and Sustainable Solvent System for Different Applications: Insights from Molecular Dynamics Simulations. J Phys Chem B. 2023; 127(37):8057-8065. DOI: 10.1021/acs.jpcb.3c04292. View

19.

Liu Y, Friesen J, McAlpine J, Lankin D, Chen S, Pauli G . Natural Deep Eutectic Solvents: Properties, Applications, and Perspectives. J Nat Prod. 2018; 81(3):679-690. PMC: 5913660. DOI: 10.1021/acs.jnatprod.7b00945. View

20.

Chatzimitakos T, Athanasiadis V, Kotsou K, Mantiniotou M, Kalompatsios D, Makrygiannis I . Optimization of Pressurized Liquid Extraction (PLE) Parameters for Extraction of Bioactive Compounds from Leaves and Bioactivity Assessment. Int J Mol Sci. 2024; 25(9). PMC: 11083225. DOI: 10.3390/ijms25094628. View