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Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 June 2021) | Viewed by 33154

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Special Issue Editors

Prof. Dr. Alexander Shikov

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Department of Pharmaceutical Formulations, Prof. Popov Street, 14a, 197376 Saint-Petersburg, Russia
Interests: natural products; medicinal plants; chemistry; pharmacology; pharmaceutical formulations with natural compounds
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Ivana Radojcic Redovnikovic

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Guest Editor

Department of Biochemical Engineering, Faculty of Food Technology and Biotechnology, Pierottijeva 6, 10 000 Zagreb, Croatia
Interests: green chemistry; green solvents; biologically active compounds; extraction; biocatalysis

Special Issue Information

Dear Colelagues,

The discovery of alternatives for toxic organic solvents used for the extraction of natural active compounds is a modern ecological trend in science. Recently, natural deep eutectic solvents (NADES) were proposed as the third solvent in living cells, which explains their high-solubilizing capacity for natural products. NADES have shown high-solubility for both water-soluble and non-water-soluble metabolites. This Special Issue encourages the publication of articles focused on the use of NADES for the extraction of biologically active compounds from natural sources.

Prof. Dr. Alexander Shikov
Prof. Dr. Ivana Radojcic Redovnikovic
Guest Editors

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Keywords

Natural deep eutectic solvents
Extraction
Active compounds
Medicinal plants

Published Papers (7 papers)

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Research

12 pages, 1120 KiB

Open AccessArticle

COSMOtherm as an Effective Tool for Selection of Deep Eutectic Solvents Based Ready-To-Use Extracts from Graševina Grape Pomace

by Manuela Panić, Veronika Gunjević, Kristina Radošević, Marina Cvjetko Bubalo, Karin Kovačević Ganić and Ivana Radojčić Redovniković

Molecules 2021, 26(16), 4722; https://doi.org/10.3390/molecules26164722 - 04 Aug 2021

Cited by 24 | Viewed by 3514

Abstract

The aim of this work is to develop an industrially suitable process for the sustainable waste disposal in wine production. The proposed process involves the development of an environmentally friendly method for the isolation of biologically active compounds from Graševina grape pomace according to the green extraction principles, in order to obtain a ready-to-use extract. In this process, deep eutectic solvents (DES) were used as extraction solvents. Aiming to save time in selecting the optimal DES that would provide the most efficient Graševina pomace polyphenols extraction, the user-friendly software COSMOtherm was used and 45 DES were screened. Moreover, the prepared extracts were chemically and biologically characterized to confirm their safety for human application. Computational and experimental results proved the applicability of COSMOtherm in the selection of the optimal DES for the environmentally friendly preparation of the ready-to-use extract from Graševina grape pomace with expected application in the cosmetic industry. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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14 pages, 1271 KiB

Open AccessArticle

Efficacy of Natural Deep Eutectic Solvents for Extraction of Hydrophilic and Lipophilic Compounds from Fucus vesiculosus

by Ekaterina D. Obluchinskaya, Olga N. Pozharitskaya, Lyubov V. Zakharova, Anna V. Daurtseva, Elena V. Flisyuk and Alexander N. Shikov

Molecules 2021, 26(14), 4198; https://doi.org/10.3390/molecules26144198 - 10 Jul 2021

Cited by 68 | Viewed by 3994

Abstract

The impact of the composition of natural deep eutectic solvents (NADES) and extraction conditions on the simultaneous extraction of hydrophilic ascorbic acid (AA), phlorotannins (TPhC), and lipophilic fucoxanthin (FX) from Fucus vesiculosus was investigated for the first time. In biological tests, the NADES extracts showed the promising ability to scavenge DPPH radicals. A positive correlation was observed between DPPH scavenging activity and AA, TPhC, and FX contents. We calculate the synergistic effect of antioxidants extracted by NADES from F. vesiculosus based on the mixture effect (ME). The addition of 30% water to the NADES and the prolongation of sonication time from 20 min up to 60 min were favorable for the ME. The ME for extracts with the NADES was increased by two folds (ME > 2). In contrast, conventional extraction by maceration with steering at 60 °C does not lead to the synergistic effect (ME = 1). It is notable that the NADES provides high stability and preserves the antioxidant activity of the extracts from F. vesiculosus during storage. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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14 pages, 3226 KiB

Open AccessArticle

Natural Deep Eutectic Solvents for the Extraction of Bioactive Steroidal Saponins from Dioscoreae Nipponicae Rhizoma

by Gui-Ya Yang, Jun-Na Song, Ya-Qing Chang, Lei Wang, Yu-Guang Zheng, Dan Zhang and Long Guo

Molecules 2021, 26(7), 2079; https://doi.org/10.3390/molecules26072079 - 05 Apr 2021

Cited by 35 | Viewed by 3501

Abstract

In the present study, a simple and environmentally friendly extraction method based on natural deep eutectic solvents (NADESs) was established to extract four bioactive steroidal saponins from Dioscoreae Nipponicae Rhizoma (DNR). A total of twenty-one types of choline chloride, betaine, and L-proline based NADESs were tailored, and the NADES composed of 1:1 molar ratio of choline chloride and malonic acid showed the best extraction efficiency for the four steroidal saponins compared with other NADESs. Then, the extraction parameters for extraction of steroidal saponins by selected tailor-made NADES were optimized using response surface methodology and the optimal extraction conditions are extraction time, 23.5 min; liquid–solid ratio, 57.5 mL/g; and water content, 54%. The microstructure of the DNR powder before and after ultrasonic extraction by conventional solvents (water and methanol) and the selected NADES were observed using field emission scanning electron microscope. In addition, the four steroidal saponins were recovered from NADESs by D101 macroporous resin with a satisfactory recovery yield between 67.27% and 79.90%. The present research demonstrates that NADESs are a suitable green media for the extraction of the bioactive steroidal saponins from DNR, and have a great potential as possible alternatives to organic solvents for efficiently extracting bioactive compounds from natural products. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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16 pages, 2119 KiB

Open AccessArticle

Ultrasound-Assisted Extraction of Anthocyanins Using Natural Deep Eutectic Solvents and Their Incorporation in Edible Films

by Patricia Velásquez, Daniela Bustos, Gloria Montenegro and Ady Giordano

Molecules 2021, 26(4), 984; https://doi.org/10.3390/molecules26040984 - 12 Feb 2021

Cited by 38 | Viewed by 4263

Abstract

Extracts rich in bioactive compounds added to edible films have allowed the development of active packaging that increases the shelf life of food. However, it is necessary to search for solvents that are nontoxic and not harmful to the environment, with natural deep eutectic solvents (NADES) being an attractive and easily synthesized alternative. This research aimed to design NADES by lyophilization to be used in the extraction of anthocyanins from the Chilean Luma chequen (Molina) A. Gray berry, and subsequently adding them to the matrix of edible ƙ-carrageenan films. For this purpose, ultrasound-assisted extraction (UAE) was used and the anthocyanin content was evaluated with the pH differential method. The antioxidant capacity of extracts was determined by DPPH assay and the antibacterial capacity by diffusion agar tests. The results obtained indicate that the designed NADES are efficient at extracting anthocyanins, reaching concentrations between 81.1 and 327.6 mg eq cyanidin 3-glucoside/100 g dw of L. chequen (Molina) A. Gray. The extracts reached inhibition diameters between 5 and 34 mm against Escherichia coli, Staphylococcus aureus, and Salmonella typhi strains. Once the extracts were incorporated into ƙ-carrageenan films, active edible films with antioxidant and antibacterial capacities were obtained. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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11 pages, 699 KiB

Open AccessArticle

Natural Deep Eutectic Solvents for the Extraction of Phenyletanes and Phenylpropanoids of Rhodiola rosea L.

by Alexander N. Shikov, Vera M. Kosman, Elena V. Flissyuk, Irina E. Smekhova, Abdelhameed Elameen and Olga N. Pozharitskaya

Molecules 2020, 25(8), 1826; https://doi.org/10.3390/molecules25081826 - 16 Apr 2020

Cited by 56 | Viewed by 4585

Abstract

The extraction of Rhodiola rosea rhizomes using natural deep eutectic solvent (NADES) consisting of lactic acid, glucose, fructose, and water was investigated. A two-level Plackett–Burman design with five variables, followed by the steepest ascent method, was undertaken to determine the optimal extraction conditions. Among the five parameters tested, particle size, extraction modulus, and water content were found to have the highest impact on the extrability of phenyletanes and phenylpropanoids. The concentration of active compounds was analyzed by HPLC. The predicted results showed that the extraction yield of the total phenyletanes and phenylpropanoids (25.62 mg/g) could be obtained under the following conditions: extraction time of 154 min, extraction temperature of 22 °C, extraction modulus of 40, molar water content of 5:1:11 (L-lactic acid:fructose:water, mol/mol), and a particle size of rhizomes of 0.5–1 mm. These predicted values were further verified by validation experiments in predicted conditions. The experimental yields of salidroside, tyrosol, rosavin, rosin, cinnamyl alcohol and total markers (sum of phenyletanes and phenylpropanoids in mg/g) were 11.90 ± 0.02, 0.36 ± 0.02, 12.23 ± 0.21, 1.41 ± 0.01, 0.20 ± 0.01, and 26.10 ± 0.27 mg/g, respectively, which corresponded well with the predicted values from the models. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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14 pages, 1565 KiB

Open AccessArticle

Choline Chloride Based Natural Deep Eutectic Solvents as Extraction Media for Extracting Phenolic Compounds from Chokeberry (Aronia melanocarpa)

by Maša Islamčević Razboršek, Milena Ivanović, Peter Krajnc and Mitja Kolar

Molecules 2020, 25(7), 1619; https://doi.org/10.3390/molecules25071619 - 01 Apr 2020

Cited by 48 | Viewed by 5621

Abstract

For the isolation of selected phenolic compounds from dried chokeberries, natural deep eutectic solvents (NADESs) were investigated as a green alternative to conventionally used extraction solvents. Four types of NADESs were synthesised, with choline chloride as the hydrogen bond acceptor in combination with different hydrogen bond donors (sugars, organic acid and urea). Ultrasound-assisted extraction was used to improve the extractability of the phenolic compounds and the results were compared to those obtained with 80% methanol as the extraction media. The highest values of total phenols and total flavonoids were found in the extract obtained with choline chloride–fructose NADES (36.15 ± 3.39 mg gallic acid g⁻¹ dry weight (DW) and 4.71 ± 0.33 mg rutin g⁻¹ DW, respectively). The extraction recoveries for the individual phenolic compounds depended strongly on the phenolic compound’s structure, with relative mean values between 70% and 97%. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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10 pages, 566 KiB

Open AccessArticle

Studying and Modeling of the Extraction Properties of the Natural Deep Eutectic Solvent and Sorbitol-Based Solvents in Regard to Biologically Active Substances from Glycyrrhizae Roots

by Nikolay Boyko, Elena Zhilyakova, Anastasiya Malyutina, Oleg Novikov, Dmitriy Pisarev, Rimma Abramovich, Olga Potanina, Simon Lazar, Praskovia Mizina and Rita Sahaidak-Nikitiuk

Molecules 2020, 25(7), 1482; https://doi.org/10.3390/molecules25071482 - 25 Mar 2020

Cited by 12 | Viewed by 3062

Abstract

The purpose of this work was the studying and modeling of the extraction properties of the sorbitol-based natural deep eutectic solvent (NADES) and sorbitol-based solvents in regard to biologically-active substances (BASs) from Glycyrrhizae roots using theoretical fundamentals based on the laws of statistical physics, thermodynamics, and physical chemistry previously developed by us. In our studies, we used Glycyrrhizae roots, simple maceration, plant raw material:solvent ratio 1:10 w/v, temperature 25 °C, extraction time 24 h; standards of licuroside and glycyram; RP HPLC, differential scanning calorimetry, integral dielectric, impedance and conductivity spectroscopy method of analysis; the following solvents: sorbitol-based NADES sorbitol:malic acid:water (1:1:3 in molar ratio), a modified solvent based on NADES sorbitol:malic acid:water:glycerin (1:1:1:1 in molar ratio) and sorbitol-based solvents sorbitol:ethanol:water at different ratios. It has been found that regression equations for sorbitol-based solvents in coordinates predicted by the theory have a high value of determination coefficient that equals to R²_e = 0.993 for glycyram and R²_e = 0.976 for licuroside. It has been found that the extraction properties of sorbitol-based NADES with a dielectric constant (ε) equal to 33 ± 2 units are equivalent to those of the sorbitol:ethanol:water solvent with ε = 34 units, and the extraction properties of modified solvent based on NADES with ε = 41 ± 2 units are inferior to those of the sorbitol-ethanol-water solvents with maximum value of BASs yield with the dielectric constant range 40 ÷ 50 units. The theoretical fundamentals suggested provide a possibility for an explanation of the mechanism, quantitative description of the extraction properties of the solvent, and target search of the optimal solvent by its dielectric constant. Full article

(This article belongs to the Special Issue Natural Deep Eutectic Solvents (NADES) for Isolation of Biological Active Compounds)

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