Natural deep eutectic solvents from choline chloride and betaine – Physicochemical properties

Oil palm (Elaeis guineensis Jacq.) leaf (OPL) is abundantly generated from oil palm plantations as biomass that is rich in bioactive metabolites, primarily flavonoids. Six natural deep eutectic solvents (NaDES) were synthesized using a direct heating technique from different combinations of choline chloride with 1,2-propanediol (PD), 1,4-butanediol (BD), glycerol (GLY), glucose (GLU), maltose (MAL) and lactic acid (LA). The synthesized NaDES were subjected to physicochemical and biological evaluations comprising physical appearance, density, water activity, viscosity, polarity, thermal behaviors, spectroscopic analysis, cytotoxicity, radical scavenging activities and solubility tests. Compared to aqueous methanol, the synthesized NaDES, which appeared as a slightly to moderately viscous transparent liquid, showed favorable physicochemical properties as extraction solvents with a low cytotoxicity profile on cultured fibroblast cells. Further, the NaDES obtained from the choline chloride:lactic acid (LA) combination showed high free radical scavenging characteristics. Hydrogen bonding interactions were shown to play a significant role in the formation of the NaDES. Further, ultra-high-performance liquid chromatography ultraviolet/photodiode array (UHPLC-UV/PDA) analysis revealed that the NaDES from the choline chloride:glycerol (GLY) combination had comparable efficiencies with aqueous methanol regarding extracting flavonoids (luteolin and apigenin derivatives) from OPLs. The results of the present study suggested that the tailor-made NaDES were not only easy-to-use, stable and safe solvents but also suitable for extracting bioactive phytochemical compounds. The study highlighted their potential as an alternative green technology for applications in oil palm biomass utilization programs.

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Effect of water on amine-based deep eutectic solvents (choline chloride + monoethanolamine): Structure and physicochemical properties

Journal of Environmental Chemical Engineering ◽

10.1016/j.jece.2021.106952 ◽

2022 ◽

Vol 10 (1) ◽

pp. 106952

Author(s):

Mingcheng Li ◽

Chunying Zhu ◽

Taotao Fu ◽

Xiqun Gao ◽

Youguang Ma

Keyword(s):

Physicochemical Properties ◽

Choline Chloride ◽

Deep Eutectic Solvents ◽

Effect Of Water

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Green Extraction of Alkaloids and Polyphenols from Peumus boldus Leaves with Natural Deep Eutectic Solvents and Profiling by HPLC-PDA-IT-MS/MS and HPLC-QTOF-MS/MS

Plants ◽

10.3390/plants9020242 ◽

2020 ◽

Vol 9 (2) ◽

pp. 242 ◽

Cited By ~ 4

Author(s):

Jeniffer Torres-Vega ◽

Sergio Gómez-Alonso ◽

José Pérez-Navarro ◽

Edgar Pastene-Navarrete

Keyword(s):

Mass Spectrometry ◽

Phenolic Compounds ◽

High Resolution Mass Spectrometry ◽

Choline Chloride ◽

Deep Eutectic Solvents ◽

Total Phenolic ◽

Array Detector ◽

Green Extraction ◽

Medicinal Tree ◽

Natural Deep Eutectic Solvents

Peumus boldus Mol., is a Chilean medicinal tree used for gastrointestinal and liver diseases. Such medicinal properties are associated with the presence of bioactive flavonoids and aporphine alkaloids. In this study, a new green and efficient extraction method used seven natural deep eutectic solvents (NADES) as extraction media. The extraction efficiency of these NADES was assessed, determining the contents of boldine and total phenolic compounds (TPC). Chemical profiling of P. boldus was done by high-performance liquid chromatography coupled to photo diode array detector and electrospray ion-trap mass spectrometry (HPLC-PDA-ESI-IT/MS) and electrospray ionization quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF-MS). Among the NADES tested, NADES4 (choline chloride-lactic acid) and NADES6 (proline-oxalic acid) enable better extraction of boldine with 0.427 ± 0.018 and 2.362 ± 0.055 mg of boldine g−1 of plant, respectively. Extraction of boldine with NADES4 and NADES6 was more efficient than extractions performed with methanol and water. On the other hand, the highest TPC were obtained using NADES6, 179.442 ± 3.79 mg of gallic acid equivalents (GAE g−1). Moreover, TPC in extracts obtained with methanol does not show significant differences with NADES6. The HPLC-PAD-MS/MS analysis enable the tentative identification of 9 alkaloids and 22 phenolic compounds. The results of this study demonstrate that NADES are a promising green extraction media to extract P. boldus bioactive compounds and could be a valuable alternative to classic organic solvents.

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Understanding the peculiar effect of water on the physicochemical properties of choline chloride based deep eutectic solvents theoretically and experimentally

Journal of Molecular Liquids ◽

10.1016/j.molliq.2019.01.053 ◽

2019 ◽

Vol 278 ◽

pp. 607-615 ◽

Cited By ~ 25

Author(s):

Muzammil Kuddushi ◽

Gurpreet Singh Nangala ◽

Sargam Rajput ◽

Sushma P. Ijardar ◽

Naved I. Malek

Keyword(s):

Physicochemical Properties ◽

Choline Chloride ◽

Deep Eutectic Solvents ◽

Effect Of Water

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Natural Deep Eutectic Solvents for Simultaneous Extraction of Multi-Bioactive Components from Jinqi Jiangtang Preparations

Pharmaceutics ◽

10.3390/pharmaceutics11010018 ◽

2019 ◽

Vol 11 (1) ◽

pp. 18 ◽

Cited By ~ 2

Author(s):

Lele Yang ◽

Ling Li ◽

Hao Hu ◽

Jianbo Wan ◽

Peng Li

Keyword(s):

High Performance ◽

Choline Chloride ◽

Deep Eutectic Solvents ◽

Bioactive Components ◽

Operational Parameters ◽

Ultrasound Assisted Extraction ◽

Assisted Extraction ◽

Natural Deep Eutectic Solvents ◽

Quantification Analysis ◽

Chemical Profiles

Natural deep eutectic solvents (NADESs), composed of natural primary metabolites, are now widely used as green and sustainable extraction solvents of bioactive components. In the present study, various NADESs were prepared to extract multi-components from different preparations of an herbal formula (Chinese name: Jinqi Jiangtang, JQJT) using ultrasound-assisted extraction (UAE). Results showed that most prepared NADESs provided more effective extraction of phenolic acids and alkaloids from JQJT preparations than conventional solvents. Among the tested NADESs, the solvent formed by choline chloride and laevulinic acid was selected to optimize the operational parameters using response surface methodology. The optimized extraction method was successfully applied to extract six major components in four commercial JQJT products, and quantification analysis was performed by the validated high-performance liquid chromatography with ultraviolet detection (HPLC-UV) method. The quantitative results indicated that preparations from different manufacturers showed different chemical profiles. In conclusion, NADESs-based UAE shows considerable potential as an efficient and green method for extraction of multi-bioactive components from commercial herbal preparations.

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Extracts of medicinal plants with natural deep eutectic solvents: enhanced antimicrobial activity and low genotoxicity

BMC Chemistry ◽

10.1186/s13065-020-00726-x ◽

2020 ◽

Vol 14 (1) ◽

Author(s):

Tsvetinka Grozdanova ◽

Boryana Trusheva ◽

Kalina Alipieva ◽

Milena Popova ◽

Lyudmila Dimitrova ◽

...

Keyword(s):

Antimicrobial Activity ◽

Medicinal Plants ◽

Total Phenolics ◽

Choline Chloride ◽

Deep Eutectic Solvents ◽

Bioactive Constituents ◽

Primary Metabolites ◽

E Coli ◽

Natural Deep Eutectic Solvents ◽

Toxic Organic Solvents

AbstractNatural deep eutectic solvents (NADES) are a new alternative to toxic organic solvents. Their constituents are primary metabolites, non-toxic, biocompatible and sustainable. In this study four selected NADES were applied for the extraction of two medicinal plants: Sideritis scardica, and Plantago major as an alternative to water-alcohol mixtures, and the antimicrobial and genotoxic potential of the extracts were studied. The extraction efficiency was evaluated by measuring the extracted total phenolics, and total flavonoids. Best extraction results for total phenolics for the studied plants were obtained with choline chloride-glucose 5:2 plus 30% water; but surprisingly these extracts were inactive against all tested microorganisms. Extracts with citric acid-1,2-propanediol 1:4 and choline chloride-glycerol 1:2 showed good activity against S. pyogenes, E. coli, S. aureus, and C. albicans. Low genotoxicity and cytotoxicity were observed for all four NADES and the extracts with antimicrobial activity. Our results confirm the potential of NADESs for extraction of bioactive constituents of medicinal plants and further suggest that NADES can improve the effects of bioactive extracts. Further studies are needed to clarify the influence of the studied NADES on the bioactivity of dissolved substances, and the possibility to use such extracts in the pharmaceutical and food industry.

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Physicochemical Properties, Cytotoxicity, and Antioxidative Activity of Natural Deep Eutectic Solvents Containing Organic Acid

Chemical and Biochemical Engineering Quarterly ◽

10.15255/cabeq.2018.1454 ◽

2019 ◽

Vol 33 (1) ◽

pp. 1-18 ◽

Cited By ~ 14

Author(s):

Anamarija Mitar ◽

Manuela Panić ◽

Kristina Radošević ◽

Ivana Radojčić Redovniković ◽

Kristina Zagajski Kučan ◽

...

Keyword(s):

Physicochemical Properties ◽

Antioxidative Activity ◽

Deep Eutectic Solvents ◽

Oxygen Radical ◽

Structural Variations ◽

Natural Deep Eutectic Solvents ◽

Environmentally Safe ◽

Mcf 7

Natural deep eutectic solvents (NADES) may be considered ‘designer solvents’ due to their numerous structural variations and the possibility of tailoring their physicochemical properties. Prior to their industrial application, characterization of NADES is essential, including determination of their physicochemical properties, cytotoxicity, and antioxidative activity. The most important physicochemical properties of eight prepared NADES (choline chloride:malic acid, proline:malic acid, choline chloride:proline:malic acid, betaine:malic acid, malic acid:glucose, malic acid:glucose:glycerol, choline chloride:citric acid, and betaine:citric acid) were measured as functions of temperature and water content. In general, the structure of prepared NADES greatly influences their physical properties, which could be successfully modified and adjusted by addition of water. All tested NADES were absolutely benign and noncorrosive for investigated steel X6CrNiTi18-10. Furthermore, cytotoxicity of prepared solvents was assessed toward three human cell lines (HEK-293T, HeLa, and MCF-7 cells), and antioxidative activity was measured by the Oxygen Radical Absorbance Capacity (ORAC) method. With regard to cell viability, all tested NADES containing carboxylic acid could be classified as practically harmless and considered environmentally safe. The ORAC values indicated that the tested NADES displayed antioxidative activity.

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