Environmentally-Friendly Extraction of Flavonoids from Cyclocarya paliurus (Batal.) Iljinskaja Leaves with Deep Eutectic Solvents and Evaluation of Their Antioxidant Activities

Deep eutectic solvents (DESs) are commonly employed as environmentally-friendly solvents in numerous chemical applications owing to their unique physicochemical properties. In this study, a novel and environmentally-friendly extraction method based on ultrasound assisted-deep eutectic solvent extraction (UAE-DES) was investigated for the extraction of flavonoids from Cyclocarya paliurus (Batal.) Iljinskaja (C. paliurus) leaves, and the antioxidant activities of these flavonoids were evaluated. Nine different DES systems based on either two or three components were tested, and the choline chloride/1,4–butanediol system (1:5 molar ratio) was selected as the optimal system for maximizing the flavonoid extraction yields. Other extraction conditions required to achieve the maximum flavonoid extraction yields from the leaves of C. paliurus were as follows: DES water content (v/v), 30%; extraction time, 30 min; temperature, 60 °C; and solid-liquid ratio, 20 mg/mL. Liquid chromatography-mass spectrometry allowed the detection of five flavonoids in the extract, namely kaempferol-7-O-α-l-rhamnoside, kaempferol, quercetin, quercetin-3-O-β-d-glucuronide, and kaempferol-3-O-β-d-glucuronide. In vitro antioxidant tests revealed that the flavonoid-containing extract exhibited strong DPPH and ABTS radical-scavenging abilities. Results indicate that UAE-DES is a suitable approach for the selective extraction of flavonoids from C. paliurus leaves, and DESs can be employed as sustainable extraction media for other bioactive compounds.

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Toxico-metabolomics study of a deep eutectic solvent comprising choline chloride and urea suggests in vivo toxicity involving oxidative stress and ammonia stress

Green Chemistry ◽

10.1039/d0gc03927f ◽

2021 ◽

Vol 23 (3) ◽

pp. 1300-1311 ◽

Cited By ~ 1

Author(s):

Dasom Jung ◽

Jae Back Jung ◽

Seulgi Kang ◽

Ke Li ◽

Inseon Hwang ◽

...

Keyword(s):

Oxidative Stress ◽

Choline Chloride ◽

Deep Eutectic Solvent ◽

Deep Eutectic Solvents ◽

In Vivo Toxicity ◽

Metabolomics Study ◽

Ammonia Stress

The in vitro and in vivo studies suggest that choline chloride-based deep eutectic solvents may not be considered as pure, safe mixtures even if they consist of safe compounds.

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Deep Eutectic Solvents Based Ultrasonic Extraction of Polysaccharides from Edible Brown Seaweed Sargassum horneri

Journal of Marine Science and Engineering ◽

10.3390/jmse8060440 ◽

2020 ◽

Vol 8 (6) ◽

pp. 440

Author(s):

Jinggui Nie ◽

Danting Chen ◽

Yanbin Lu

Keyword(s):

Choline Chloride ◽

Brown Seaweed ◽

Deep Eutectic Solvents ◽

Significant Inhibition ◽

Hot Water ◽

Ultrasonic Extraction ◽

Sargassum Horneri ◽

Molar Ratio ◽

Extraction Temperature

In this work, a method for ultrasonic extraction of polysaccharides from Sargassum horneri using deep eutectic solvents was proposed. The studied deep eutectic solvents were composed of choline chloride, 1,2-propanediol and water. Based on the single-factor experiment results, four experimental factors were systematically evaluated, giving the optimal extraction conditions as follows: molar ratio of choline chloride to 1,2-propanediol of 1:2, water content of 30% (v/v), solid-liquid ratio of 1:30 (g/mL), and the extraction temperature of 70 °C. Fourier transform infrared spectroscopy and X-ray diffraction were utilized to investigate changes in the chemical characteristic of extracted polysaccharides. The results indicated that deep eutectic solvents had stronger protein and calcium carbonate removal ability than that of a conventional hot water extraction method. Moreover, in vitro antioxidant activity tests exhibited that the obtained polysaccharides had significant inhibition effects on DPPH and ABTS radicals. The proposed deep eutectic solvents assisted ultrasonic extraction protocol was considered to be a green, fast and effective protocol for extracting polysaccharides from Sargassum horneri.

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Deep eutectic solvents aqueous two-phase system based ultrasonically assisted extraction of ursolic acid (UA) from Cynomorium songaricum Rupr.

10.7287/peerj.preprints.3495 ◽

2017 ◽

Author(s):

Xifeng Zhang ◽

Ji Zhang

Keyword(s):

Ursolic Acid ◽

Choline Chloride ◽

Deep Eutectic Solvent ◽

Deep Eutectic Solvents ◽

Selective Extraction ◽

Phase System ◽

Green Solvents ◽

Active Components ◽

Two Phase ◽

Solid Ratio

Deep eutectic solvents (DESs) are new green solvents that have attracted the attention of the scientific community mainly due to their unique properties and special characteristics, which are different from those of traditional solvents.A method based on ultrasonically assisted deep eutectic solvent aqueous two-phase systems( UAE-DES-ATPS) was developed for extracting ursolic acid (UA) from Cynomorium songaricum Rupr. Four different types of choline chloride-based DESs were prepared.Choline chloride-glucose (ChCl-Glu) exhibited good selective extraction ability. An optimum DES-ATPS of 36% (w/w) ChCl-Glu and 25% (w/w) K2HPO4 was considered to be a satisfactory system for extracting UA. Response surface methodology (RSM) method was used to optimize the extraction of UA using UAE-DES-ATPS. The optimum ultrasound-assisted conditions were as follows: solvent to solid ratio of 15:1 (g/g), ultrasound power of 470 W, and extraction time of 54 min. Compared with the conventional UAE method, the yields were basically the same, but the presented method had higher purity. The structure of UA did not change between pure UA and UA in the upper phase by UV–vis and FT-IR. This approach using ChCl-based DES-ATPS as a novel extraction system and ultrasound as a source of energy provided better choice for the separation of active components from other natural products.

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Structural and Transport Properties of Binary Mixtures of Deep Eutectic Solvent (Ethaline) with Primary Alcohols: A Molecular Dynamics Study

10.26434/chemrxiv.14381996.v1 ◽

2021 ◽

Author(s):

kishant kumar ◽

Anand Bharti ◽

Aditya Sinha

Keyword(s):

Molecular Dynamics ◽

Transport Properties ◽

Binary Mixtures ◽

Choline Chloride ◽

Deep Eutectic Solvent ◽

Deep Eutectic Solvents ◽

Md Simulations ◽

Molar Ratio ◽

Green Solvents ◽

Primary Alcohols

<table><tr><td>Deep eutectic solvents (DESs) are classified as the green solvents which are considered as an alternative to volatile organic solvents. In this work, the thermophysical, structural and transport properties of binary mixtures of DES ethaline (choline chloride (ChCl) + ethylene glycol (etgly) at a molar ratio of 1:2) with primary alcohols (methanol/ethanol) are studied using molecular dynamics (MD) simulations</td></tr></table> <br>

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Deep eutectic solvents aqueous two-phase system based ultrasonically assisted extraction of ursolic acid (UA) from Cynomorium songaricum Rupr.

10.7287/peerj.preprints.3495v1 ◽

2017 ◽

Author(s):

Xifeng Zhang ◽

Ji Zhang

Keyword(s):

Ursolic Acid ◽

Choline Chloride ◽

Deep Eutectic Solvent ◽

Deep Eutectic Solvents ◽

Selective Extraction ◽

Phase System ◽

Green Solvents ◽

Active Components ◽

Two Phase ◽

Solid Ratio

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DES Based Efficient Extraction Method for Bioactive Coumarins from Angelica dahurica (Hoffm.) Benth. & Hook.f. ex Franch. & Sav.

Separations ◽

10.3390/separations9010005 ◽

2021 ◽

Vol 9 (1) ◽

pp. 5

Author(s):

Ting Wang ◽

Qian Li

Keyword(s):

Choline Chloride ◽

Radical Scavenging ◽

Deep Eutectic Solvents ◽

Extraction Yield ◽

Molar Ratio ◽

Angelica Dahurica ◽

Extraction Temperature ◽

Solid Ratio ◽

Before And After ◽

Ultrasonic Assisted

In this study, a simple and environmentally friendly method was developed for the extraction of seven active coumarins from Angelica dahurica (Hoffm.) Benth. & Hook.f. ex Franch. & Sav.(A. dahurica) based on deep eutectic solvents (DESs). Among the 16 kinds of DES based on choline chloride, the DES system with the molar ratio of choline chloride, citric acid, and water as 1:1:2 had the best extraction effect. Ultrasonic-assisted response surface methodology (RSM) was used to investigate the optimal extraction scheme. The results showed that the optimal extraction conditions were a liquid–solid ratio of 10:1 (mL/g), an extraction time of 50 min, an extraction temperature of 59.85 °C, and a moisture content of 49.28%. Under these conditions, the extraction yield reached 1.18%. In addition, scanning electron microscopy (SEM) was used to observe the degree of powder fragmentation before and after extraction with different solvents. The cells of A. dahurica medicinal materials obtained by DES ultrasonic-assisted treatment were the most seriously broken, indicating that DES had the highest efficiency in the treatment of A. dahurica. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) DPPH radical scavenging model was used to evaluate the biological activity of DES extract. The results showed that DES extract had better scavenging ability of DPPH free radical. Therefore, DES is a green solvent suitable for extracting coumarin compounds of A. dahurica, with great potential to replace organic solvents.

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Metal- and solvent-free preparation of benzo[4,5]imidazo[1,2-a]pyrimidine derivatives catalysed by deep eutectic solvents

Vietnam Journal of Science Technology and Engineering ◽

10.31276/vjste.63(3).15-17 ◽

2021 ◽

Vol 63 (3) ◽

pp. 15-17

Author(s):

Thuy-Duy Thi Nguyen ◽

◽

Anh Vy Truong ◽

Hoang Phuong Tran ◽

◽

...

Keyword(s):

Ethyl Acetoacetate ◽

Good Yield ◽

Choline Chloride ◽

Biginelli Reaction ◽

Deep Eutectic Solvent ◽

Environmentally Friendly ◽

Deep Eutectic Solvents ◽

Solvent Free ◽

Pyrimidine Derivatives ◽

Solvent Free Conditions

by an acidic deep eutectic solvent from choline chloride (ChCl) and phenol via the Biginelli reaction of 2-aminobenzimidazole, ethyl acetoacetate, and aldehydes has been developed under metal- and solvent-free conditions. The desired products were obtained in moderate to good yield (49-79%) and the DESs were known as an economical and environmentally friendly catalyst.

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Three-Phase Partitioning for the Extraction and Purification of Polysaccharides from the Immunomodulatory Medicinal Mushroom Inonotus obliquus

Molecules ◽

10.3390/molecules24030403 ◽

2019 ◽

Vol 24 (3) ◽

pp. 403 ◽

Cited By ~ 5

Author(s):

Zhendong Liu ◽

Dongsheng Yu ◽

Liang Li ◽

Xiaoxiao Liu ◽

Henan Zhang ◽

...

Keyword(s):

Antioxidant Activities ◽

Extraction Procedure ◽

Radical Scavenging ◽

Molar Ratio ◽

Medicinal Mushroom ◽

Inonotus Obliquus ◽

Phase Partitioning ◽

Reducing Ability ◽

Three Phase

Polysaccharides from the immunomodulatory medicinal mushroom Inonotus obliquus (IOPS) were extracted and purified using three-phase partitioning (TPP), which is an efficient, fast, safe, and green purification technique. An optimal extraction procedure that gave a good 2.2% isolated yield was identified, using the following protocol: a solid-liquid ratio of 1 g to 12 mL; mass fraction of (NH4)2SO4 20% (w/v); 11 mL t-butanol; pH 8.0; temperature 30 °C; and extraction time 30 min. The purified IOPS was shown to be a proteoglycan of 40 kDa molecular weight comprising of d-galactose, d-glucose, d-xylose, and d-mannose in a molar ratio of 2.0:3.5:1.0:1.5. The purified IOPS displayed strong free-radical scavenging abilities, antioxidant activities, and immunological activity in vitro. IOPS’ Trolox antioxidant equivalent capacity and ferric-reducing ability of plasma were 251.2 μmol Trolox/g sample and 1040.5 μmol Fe2+/g sample, respectively, with the activity of its immunomodulatory behavior shown to be gradient dependent.

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Investigation of Total Phenolic Content and Antioxidant Activities of Spruce Bark Extracts Isolated by Deep Eutectic Solvents

Crystals ◽

10.3390/cryst10050402 ◽

2020 ◽

Vol 10 (5) ◽

pp. 402 ◽

Cited By ~ 2

Author(s):

Michal Jablonsky ◽

Veronika Majova ◽

Petra Strizincova ◽

Jozef Sima ◽

Jozef Jablonsky

Keyword(s):

Total Phenolic Content ◽

Phenolic Content ◽

Antioxidant Activities ◽

Radical Scavenging Activity ◽

Choline Chloride ◽

Radical Scavenging ◽

Deep Eutectic Solvents ◽

Total Phenolic ◽

Molar Ratios ◽

Spruce Bark

Extracts from spruce bark obtained using different deep eutectic solvents were screened for their total phenolic content (TPC) and antioxidant activities. Water containing choline chloride-based deep eutectic solvents (DESs) with lactic acid and 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and 1,5-pentanediol, with different molar ratios, were used as extractants. Basic characteristics of the DESs (density, viscosity, conductivity, and refractive index) were determined. All the DESs used behave as Newtonian liquids. The extractions were performed for 2 h at 60 °C under continuous stirring. TPC was determined spectrophotometrically, using the Folin-Ciocalteu reagent, and expressed as gallic acid equivalent (GAE). The antioxidant activity was determined spectrophotometrically by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. The TPC varied from 233.6 to 596.2 mg GAE/100 g dry bark; radical scavenging activity (RSA) ranged between 81.4% and 95%. This study demonstrated that deep eutectic solvents are suitable solvents for extracting phenolic compounds from spruce bark.

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Greener Is Better: First Approach for the Use of Natural Deep Eutectic Solvents (NADES) to Extract Antioxidants from the Medicinal Halophyte Polygonum maritimum L.

Molecules ◽

10.3390/molecules26206136 ◽

2021 ◽

Vol 26 (20) ◽

pp. 6136

Author(s):

Iva Rukavina ◽

Maria João Rodrigues ◽

Catarina G. Pereira ◽

Inês Mansinhos ◽

Anabela Romano ◽

...

Keyword(s):

Radical Scavenging Activity ◽

Choline Chloride ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Deep Eutectic Solvents ◽

Acetone Extract ◽

Dpph Radical ◽

Dpph Assay ◽

Natural Deep Eutectic Solvents

In this study, natural deep eutectic solvents (NADES) formed by choline chloride (ChCl), sucrose, fructose, glucose, and xylose, were used to extract antioxidants from the halophyte Polygonum maritimum L. (sea knotgrass) and compared with conventional solvents (ethanol and acetone). NADES and conventional extracts were made by an ultrasound-assisted procedure and evaluated for in vitro antioxidant properties by the radical scavenging activity (RSA) on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, oxygen radical absorbance capacity (ORAC), and copper chelating activity (CCA). Samples were profiled by liquid chromatography (LC)-electrospray ionization (ESI)-QTOF-MS analysis. ChCl:fructose was more efficient in the DPPH assay, than the acetone extract. ChCl:sucrose and ChCl:fructose extracts had the highest ORAC when compared with the acetone extract. NADES extracts had higher CCA, than the acetone extract. The phenolic composition of the NADES extracts was less complex than the conventional extracts, but the proportions of major antioxidants, such as flavonols and flavan-3-ols, were similar in all the solvents. Myricitrin was the major flavonoid in all of the samples, while gallic acid was the main phenolic acid in the conventional extracts and present in a greater amount in ChCl:fructose. Results suggest that NADES containing ChCl and sucrose/fructose can replace conventional solvents, especially acetone, in the extraction of antioxidants from sea knotgrass.

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