Antibacterial and antifungal activities of natural deep eutectic solvents.

The increasing antibiotic resistance towards a panel of microorganisms is one of the public health concerns. For this reason, the search for alternatives to the widely used antibiotic has been undertaken. In the era of sustainable chemistry, deep eutectic solvents (DESs) have emerged as promising antimicrobial agents. These solvents possess several advantages such as low volatility, low flammability, ease of preparation, and typically low cost of production. These properties make DES suitable for various applications, including extraction of biomolecules and preparation of cosmetics. Natural DESs (NADESs) are special category of DESs prepared from natural sources, which matched the recent trends of leaning back to nature, and decreasing dependence on synthetic precursors. NADES can be prepared by heating and stirring, freeze-drying, evaporation, grinding, and ultrasound-assisted and microwave-assisted synthesis. Utilizing NADESs as an alternative to traditional antibiotics, which become ineffective over time due to bacterial resistance, holds great promise for these reasons. This review aims to discuss the antimicrobial properties of multiple NADESs, including antibacterial and antifungal activities. To the best of our knowledge, this review is the first literature survey of the antimicrobial activities of NADESs. KEY POINTS: • Natural deep eutectic solvents are promising antimicrobial alternative to antibiotics • NADES holds high potential for their activity against bacterial resistance • NADES have also substantial antifungal activities.

New Green Biorefinery Strategies to Valorize Bioactive Fractions from Palmaria palmata.

A biorefinery process was developed to isolate phycobiliproteins, sulfated polysaccharides, and phenolic compounds from Palmaria palmata. The extraction process was carried out in three stages using ultrasound-assisted extraction (UAE) and pressurized liquid extraction (PLE) integrated with different natural deep eutectic solvents (NaDESs). In general, PLE provided higher phycobiliprotein contents than UAE in the first step of the process. In fact, the hydrolysis product of the PLE-NaDES extracts achieved a higher antioxidant capacity than that of the UAE-NaDES extracts. Particularly, glycerol:glucose (2:1) with 50% water in combination with PLE was the most suitable NaDES to recover the highest phycobiliprotein, protein, and sulfated polysaccharide contents from Palmaria palmata in the first and second steps of the biorefinery process. Finally, a PLE-NaDES using choline chloride:glycerol (1:2) with 60% water as the NaDES was employed for the recovery of antioxidant and neuroprotective phenolic compounds from the residue of the second step, obtaining a higher total phenolic content than employing PLE with ethanol/water (70:30, v/v) as the extraction solvent. Moreover, a forced stability study revealed that the NaDESs provided a protective effect compared to the water extracts against the degradation of phycobiliproteins, preserving their color over time. This study contributes to the recovery of high-value components from an undervalued biomarine source through a sustainable biorefinery process.

Chemical profiling of botanical extracts obtained in NADES systems using centrifugal partition chromatography combined with 13 C NMR dereplication-Hypericum perforatum as a case study.

INTRODUCTION: Natural deep eutectic solvents (NADES) have emerged as interesting extractants to develop botanical ingredients. They are nontoxic and biodegradable, nonflammable, easy to prepare, and able to solubilize a wide range of molecules. However, NADES extracts remain difficult to analyze because the metabolites of interest stay highly diluted in the nonvolatile viscous NADES matrix. OBJECTIVE: This study presents a robust analytical workflow for the chemical profiling of NADES extracts. It is applied to Hypericum perforatum aerial parts extracted with the neutral mixture fructose/glycerol/water (3/1/1, w/w/w), and compared to the chemical profiling of a classical dry methanol extract. METHODS: Exploiting polarity differences between metabolites, the H. perforatum NADES extract was partitioned in a liquid-liquid solvent system to trap the hydrophilic NADES constituents in the lower phase. The upper phase, containing a diversity of secondary metabolites from H. perforatum, was fractionated by centrifugal partition chromatography. All fractions were chemically investigated using a 13 C NMR dereplication method which involves hierarchical clustering analysis of the whole NMR dataset, a natural metabolite database for metabolite identification, and 2D NMR analyses for validation. Liquid chromatography-mass spectrometry (LC-MS) analyses were also performed to complete the identification process. RESULTS: A range of 21 metabolites were unambiguously identified, including glycosylated flavonols, lactones, catechins, phenolic acids, lipids, and simple sugars, and 15 additional minor extract constituents were annotated by LC-MS based on exact mass measurements. CONCLUSION: The proposed identification process is rapid and nondestructive and provides good prospects to deeply characterize botanical extracts obtained in nonvolatile and viscous NADES systems.

NADES extraction, UHPLC-ELSD-based quantification, and network pharmacology-guided target identification of fourteen specialised metabolites from Trillium govanianum Wall. ex D.Don.

INTRODUCTION: Trillium govanianum Wall. ex D.Don is a folk medicinal herb rich in structurally diverse steroidal saponins. The annual demand for this herb in India is about 200-500 metric tons, highlighting the need for a thorough quality assessment. OBJECTIVE: The objective of this study is to develop an easy and reliable ultrahigh-performance liquid chromatography-evaporative light scattering detector (UHPLC-ELSD)-based quality assessment method with 14 specialised metabolites of T. govanianum and identify the potential targets of this herb using network pharmacology. MATERIAL AND METHODS: A UHPLC-ELSD method was developed and validated with 14 markers of T. govanianum. The developed method and natural deep eutectic solvent (NADES)-assisted extraction were utilised for the recovery enhancement study of targeted specialised metabolites from rhizome samples (collected from five geographically distinct areas). In addition, the network pharmacology approach was performed for these 14 markers to predict the plausible biological targets of T. govanianum. RESULT: The developed method showed good linearity (r2: 0.940-0.998), limit of detection (LOD) (2.4-9.0 µg), limit of quantification (LOQ) (7.92-29.7 µg), precision (intra-day relative standard deviations [RSDs] 0.77%-1.96% and inter-day RSDs 2.19-4.97%), and accuracy (83.24%-118.90%). NADES sample TG-1* showed the highest recovery (yield: 167.66 ± 4.39 mg/g of dry weight) of total saponin content (TSC) as compared to its hydroethanolic extract (yield: 103.95 ± 5.36 mg/g of dry weight). Sample TG-1* was the most favourable (yield: 167.66 ± 4.39 mg/g) in terms of TSC as compared to other analysed samples (32.68 ± 1.04-88.22 ± 6.79 mg/g). Govanoside D (yield: 3.43-28.06 mg/g), 22ß-hydroxyprotodioscin (yield: 3.22-114.79 mg/g), and dioscin (yield: 1.07-20.82 mg/g) were quantified as the major metabolites. Furthermore, network pharmacology analysis of targeted 14 markers indicated that these molecules could be possible therapeutic agents for managing neuralgia, diabetes mellitus, and hyperalgesia. CONCLUSION: The current study represents the first report for the simultaneous quantification and a network pharmacology-based analysis of 14 chemical marker compounds isolated from T. govanianum.

Advanced Extraction Techniques Combined with Natural Deep Eutectic Solvents for Extracting Phenolic Compounds from Pomegranate (Punica granatum L.) Peels.

Pomegranate (Punica granatum L.) peel is a potential source of bioactive phenolic compounds such as ellagic acid and α- and ß-punicalagin. This work explores the efficiency of natural deep eutectic solvents combined with ultrasound-assisted extraction (UAE) and pressurized liquid extraction (PLE) for their extraction. Five NaDESs were evaluated by employing UAE (25 °C, for 50 min) to determine their total phenolic content (Folin-Ciocalteu assay) and ellagic acid and α- and ß-punicalagin contents (high-performance liquid chromatography (HPLC-DAD)). The NaDES composed of choline chloride (ChCl) and glycerol (Gly) (1:2, molar ratio) was the most efficient in the UAE when compared with the rest of the NaDESs and water extracts. Therefore, ChCl:Gly was further evaluated using PLE at different temperatures (40, 80, 120 and 160 °C). The PLE-NaDES extract obtained at 80 °C for 20 min at 1500 psi exhibited the highest contents of ellagic acid and α- and ß-punicalagin compared to the rest of the temperatures and PLE-water extracts obtained under the same extraction conditions. Combining UAE or PLE with a NaDES emerges as a sustainable alternative for extracting ellagic acid and α- and ß-punicalagin from pomegranate peel.

Advances in Extracting Bioactive Compounds from Food and Agricultural Waste and By-Products Using Natural Deep Eutectic Solvents: A Circular Economy Perspective.

Due to the urgent need for a transition to sustainable, zero-waste green technology, the extraction of bioactives from food and agricultural by-products and waste has garnered increasing interest. Traditional extraction techniques often involve using organic solvents, which are associated with environmental and health risks. Natural deep eutectic solvents (NADESs) have emerged as a promising green alternative, offering advantages such as low toxicity, biodegradability, and the ability to dissolve a wide range of biomolecules. This review provides a comprehensive overview of recent trends in the application of NADESs for extracting bioactive compounds from sustainable sources. The review explains the composition and principles of preparation and highlights various applications of NADESs in extracting different classes of bioactive compounds, emphasizing their potential to revolutionize extraction processes. By summarizing the latest advancements and trends, this review aims to support research and industrial applications of NADESs, promoting more sustainable and efficient extraction methods in the food and agricultural sectors.

Ligand-Independent Activation of Aryl Hydrocarbon Receptor and Attenuation of Glutamine Levels by Natural Deep Eutectic Solvent.

Natural deep eutectic solvents (NADESs) are emerging sustainable alternatives to conventional organic solvents. Beyond their role as laboratory solvents, NADESs are increasingly explored in drug delivery and as therapeutics. Their increasing applications notwithstanding, our understanding of how they interact with biomolecules at multiple levels - metabolome, proteome, and transcriptome - within human cell remain poor. Here, we deploy integrated metabolomics, proteomics, and transcriptomics to probe how NADESs perturb the molecular landscape of human cells. In a human cell line model, we found that an archetypal NADES derived from choline and geranic acid (CAGE) significantly altered the metabolome, proteome, and transcriptome. CAGE upregulated indole-3-lactic acid and 4-hydroxyphenyllactic acid levels, resulting in ligand-independent activation of aryl hydrocarbon receptor to signal the transcription of genes with implications for inflammation, immunomodulation, cell development, and chemical detoxification. Further, treating the cell line with CAGE downregulated glutamine biosynthesis, a nutrient rapidly proliferating cancer cells require. CAGE's ability to attenuate glutamine levels is potentially relevant for cancer treatment. These findings suggest that NADESs, even when derived from natural components like choline, can indirectly modulate cell biology at multiple levels, expanding their applications beyond chemistry to biomedicine and biotechnology.

Effects of cryopreservation in the presence of Natural Deep Eutectic Solvents (NADESs) on sperm parameters.

Natural Deep Eutectic Solvents (NADESs) are being considered as a potential alternative to traditional cryoprotective agents (CPAs) in sperm freezing. The study aimed to assess the effects of NADESs as a CPA on human sperm parameters. A total of 32 normozoospermic semen samples were collected from the Alzahra infertility treatment center (Iran) between July 2021 and September 2022. The samples were categorized into eight different groups: 1) a control (nonfrozen), and groups frozen with 2) SpermFreeze Solution, 3) ChX (Choline chloride and Xylitol), 4) ChS (Choline chloride and D-sorbitol), 5) ChG (Choline chloride and Glucose), 6) ChU (Choline chloride and Urea), 7) EtP (Ethylene glycol and l-proline), and 8) GlyP (Glycerol and l-proline). The study also analyzed the quality of sperm parameters, such as chromatin condensation and integrity, acrosome integrity, and survival, along with the expression of some genes that affect sperm fertility (TRPV1, TRPV4, SPACA3, and OGG1). The study found there were notable variations in sperm parameters (such as viability, chromatin condensation and integrity, and acrosome integrity) among frozen groups with some NADESs compared to the SpermFreeze Solution and control groups (P < 0.05). Analysis of gene expression demonstrated that the levels of TRPV1, TRPV4, SPACA3, and OGG1 genes were superior in the GlyP group compared to the other groups (P < 0.05). Additionally, the ChS and ChU groups exhibited preserved expression of these genes compared with the SpermFreeze Solution group. The use of NADESs led to the discovery of a more appropriate CPA that has low toxicity and is highly effective in maintaining the fertility potential of sperm.

Application of Natural Deep Eutectic Solvents for Extraction of Bioactive Components from Rhodiola rosea (L.).

Rhodiola rosea (L.) is a valuable source of nutrients. Nutrients have adaptogenic, immunostimulating, nootropic, anti-inflammatory and anti-cancer properties. Natural deep eutectic solvents (NADES) consisting of choline chloride and malonic, malic, tartaric or citric acids have been first used to extract biologically active substances from R. rosea. The total content of polyphenols has been determined by the Folin-Ciocalteu method for all extracts. Antioxidant activity has been determined by the phosphomolybdate method, and antiradical activity has been determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. Rosavin concentration has been determined by high-performance liquid chromatography (HPLC). Extraction kinetics has been evaluated regarding the effectiveness of NADES with each other and with reference solvents (water and 50% ethanol) has been made. Extraction conditions have been optimized according to the Box-Behnken design of the experiment. The optimal parameters of the extraction process have been established. The antibacterial activity of NADES-based extracts against bacterial cultures of Micrococcus luteus, Pseudomonas fluorescens, and Bacillus subtilis has been studied.

Mesoporous CuO Prepared in a Natural Deep Eutectic Solvent Medium for Effective Photodegradation of Rhodamine B.

Metal oxide nanoparticles (NPs) have been widely used as catalysts in the chemical industry, but their preparation is usually limited by strict conditions such as high temperature, elevated pressure, and the use of volatile and highly toxic organic solvents. To solve this problem, this work developed an environmentally benign method using green solvents, i.e., natural deep eutectic solvents (NADESs), as a reaction medium to prepare copper oxide (CuO) particles. The experimental results suggested that the synthesized CuO particles were sheet-like mesoporous NPs, and they exhibited excellent catalytic performance towards the photodegradation of rhodamine B (RhB) in the presence of potassium monopersulfate (PMS). The catalytic activity of the synthesized CuO NPs was better than that of the reported metal oxide-based catalysts. Reactive species such as photoexcited holes, superoxide radicals, and singlet oxygen were involved in the RhB degradation. These results indicated that NADESs are good media for the preparation of CuO NPs, and exhibit the potential for application to the preparation of other metal oxides.

From Nature to Innovation: The Uncharted Potential of Natural Deep Eutectic Solvents.

This review discusses the significance of natural deep eutectic solvents (NaDESs) as a promising green extraction technology. It employs the consolidated meta-analytic approach theory methodology, using the Web of Science and Scopus databases to analyze 2091 articles as the basis of the review. This review explores NaDESs by examining their properties, challenges, and limitations. It underscores the broad applications of NaDESs, some of which remain unexplored, with a focus on their roles as solvents and preservatives. NaDESs' connections with nanocarriers and their use in the food, cosmetics, and pharmaceutical sectors are highlighted. This article suggests that biomimicry could inspire researchers to develop technologies that are less harmful to the human body by emulating natural processes. This approach challenges the notion that green science is inferior. This review presents numerous successful studies and applications of NaDESs, concluding that they represent a viable and promising avenue for research in the field of green chemistry.

Natural Deep Eutectic Solvents for the Extraction of Triterpene Saponins from Aralia elata var. mandshurica (Rupr. & Maxim.) J. Wen.

The roots of the medicinal plant Aralia elata are rich in biologically active natural products, with triterpene saponins constituting one of their major groups. These metabolites can be efficiently extracted by methanol and ethanol. Due to their low toxicity, natural deep eutectic solvents (NADES) were recently proposed as promising alternative extractants for the isolation of natural products from medicinal plants. However, although NADES-based extraction protocols are becoming common in routine phytochemical work, their application in the isolation of triterpene saponins has not yet been addressed. Therefore, here, we address the potential of NADES in the extraction of triterpene saponins from the roots of A. elata. For this purpose, the previously reported recoveries of Araliacea triterpene saponins in extraction experiments with seven different acid-based NADES were addressed by a targeted LC-MS-based quantitative approach for, to the best of our knowledge, the first time. Thereby, 20 triterpene saponins were annotated by their exact mass and characteristic fragmentation patterns in the total root material, root bark and root core of A. elata by RP-UHPLC-ESI-QqTOF-MS, with 9 of them being identified in the roots of this plant for the first time. Triterpene saponins were successfully extracted from all tested NADES, with the highest efficiency (both in terms of the numbers and recoveries of individual analytes) achieved using a 1:1 mixture of choline chloride and malic acid, as well as a 1:3 mixture of choline chloride and lactic acid. Thereby, for 13 metabolites, NADES were more efficient extractants in comparison with water and ethanol. Our results indicate that new, efficient NADES-based extraction protocols, giving access to high recoveries of triterpene saponins, might be efficiently employed in laboratory practice. Thus, our data open the prospect of replacing alcohols with NADES in the extraction of A. elata roots.

Characteristics and antioxidant properties of Harpadon nehereus protein hydrolysate-xylose conjugates obtained from the Maillard reaction by ultrasound-assisted wet heating in a natural deep eutectic solvents system.

BACKGROUND: Harpadon nehereus is a high-protein marine fish. A valuable way to add value to H. nehereus is to convert it into protein hydrolysate. The Maillard reaction is an effective way to improve the functional properties of peptides and proteins, which are affected by many factors such as reactant concentration, water activity, pH, temperature, and heating time. However, the traditional Maillard reaction method is inefficient. The purpose of this study was therefore to explore the effect of the ultrasound-assisted wet heating method on the Maillard reaction of H. nehereus protein hydrolysate (HNPH) in a new-type green solvent - a natural hypereutectic solvent (NADES). RESULTS: Harpadon nehereus protein hydrolysate-xylose (Xy) conjugates were prepared via a Maillard reaction in a NADES system using an ultrasound-assisted wet heating method. The effects of different treatment conditions on the Maillard reaction were studied. The optimized glycation degree (DG) of HNPH-Xy conjugates was obtained with a water content of 10%, a reaction temperature of 80 °C, a reaction time of 35 min, and an ultrasonic power level of 300 W. Compared with HNPH, the structure of HNPH-Xy conjugates were significantly changed. Moreover, the functional properties and antioxidant activity of HNPH-Xy were all superior to the HNPH. CONCLUSIONS: An ultrasound-assisted wet-heating Maillard reaction between HNPH and Xy in the NADES system could be a promising way to improve the functional properties of HNPH. © 2023 Society of Chemical Industry.

Microwave-ultrasonic technique development coupled with natural deep eutectic solvents in anthocyanin extraction from perilla leaves (Perilla frutescens var. Acuta).

BACKGROUND: As potent antioxidants, anthocyanins can protect the body from free radicals. However, the traditional solvent extraction method has the disadvantages of requiring a high extraction temperature and long extraction time, so it is necessary to develop an efficient extraction method for anthocyanins. RESULTS: In this study, the technique of natural deep eutectic solvents (DESs) was applied to extract anthocyanins from purple perilla leaves with the aid of microwave-ultrasonic assisted extraction (MUAE). The response surface methodology (RSM), based on the Box-Behnken design (BBD), predicted the maximum extraction yield of anthocyanins to be 619.62 mg (100 g)-1 under the following conditions: x1 (ultrasonic extraction power) = 357.25 W, x2 (time) = 25.62 min, and x3 (temperature) = 57.80 °C. The biological activity of the extract obtained was evaluated by examining its radical-scavenging effect on 1,1-diphenyl-2-picrylhydrazyl, hydroxyl radical, and superoxide anion radicals. Its bacteriostatic impact was investigated on four typical bacteria: Shewanella putrefaciens (S. putrefaciens), Pseudomonas fluorescens (P. fluorescens), Escherichia coli (E. coli), and Staphylococcus aureus (S. aureus). CONCLUSION: The integrated extraction method of DESs with MUAE was efficient, energy-saving, green, and sustainable. © 2022 Society of Chemical Industry.

Development and Box-Behnken design optimization of a green extraction method natural deep eutectic solvent-based for phenolic compounds from barley malt rootlets.

In recent years, attention has been turned finding new sources of phenolic compounds, antioxidant molecules, main by-products from the agri-food chain like barley malt rootlets (BMRs). Traditionally, phenolic compounds are extracted from food matrices using different procedures, for example, solid-liquid, liquid-liquid, or solid-phase extraction techniques employing organic solvents. With the advent of green chemistry, attention has been paid to the search for green, nontoxic, inexpensive, and nonflammable solvents and the natural deep eutectic solvents (NADESs) respect these characteristics. The aim of this project was to develop and optimize an environmentally friendly, inexpensive, and rapid extraction method for phenolic compounds from BMRs using natural DESs as extractive solvents. Several natural DESs were tested as extractive solvents and, among them, the best results in terms of total phenolic content were obtained using a choline chloride-malic acid (1:2 molar ratio)-based mixture. Box-Behnken experimental design guaranteed the extraction of 9.51 ± 0.83 gallic acid equivalent/g of BMRs, under the following optimal extraction conditions: 1:21 solid-to-liquid ratio, 80°C as extraction temperature, 43 min as the time of extraction, and 29% as a percentage of added water in the NADESs. Phenolic acids and flavonoids were detected in the BMRs extract through HPLC-PDA/MS analysis.

Optimization of the extraction process of flavonoids from Trollius ledebouri with natural deep eutectic solvents.

In recent years, natural deep eutectic solvents have been favored greatly due to their environment friendly, mild biological toxicity and simple biodegradability. Natural deep eutectic solvents gradually applied for the extracting bioactive compounds from natural products efficiently. In this study, 20 natural deep eutectic solvents were prepared and their physical and chemical properties were tested. The ultrasonic-assisted extraction method was used to extract flavonoids from Trollius ledebouri and high-performance liquid chromatography-ultraviolet was applied to examine two main bioactive flavonoids (orientin and vitexin). Compared with traditional solvents (water and 60% ethanol solution), natural deep eutectic solvents composed of L(-)-proline and levulinic acid (molar ratio 1:2) show a super extraction efficiency. On this basis, the response surface method was used to optimize the extraction temperature, extraction time, water contents, and solid-liquid ratio. As a consequence, the extraction temperature 60℃, extraction time 18 min, water content 14% (v/v), and the solid-liquid ratio 48 mL·g-1 were chosen as the best extraction process. This study shows that natural deep eutectic solvents can effectively extract flavonoids from T. ledebouri, laying a foundation for the further application of natural deep eutectic solvents to extract bioactive compounds from natural products.

Antimicrobial potential of natural deep eutectic solvents.

Natural deep eutectic solvents (NADES) are a new class of green solvents, which can solubilize natural and synthetic chemicals of low water solubility. NADES are mixtures of two or three compounds of hydrogen bond acceptors and hydrogen bond donors. Many NADES' components are of natural origin and therefore, NADES are presumed to be nontoxic and often exhibit antimicrobial activity. This work aimed to investigate the potential antimicrobial effect of menthol, capric acid and Solutol™, and their associated eutectic system on two Gram-positive bacteria (Staphylococcus aureus ATCC 6538 and Bacillus subtilis ATCC 6633), two Gram-negative bacteria (Escherichia coli ATCC 8739 and Pseudomonas aeruginosa ATCC 9027) and one fungus (the yeast Candida albicans ATCC 10231). The results obtained showed a stronger antimicrobial effect for the NADES when compared to their individual components and that they exhibit a promising antimicrobial activity against S. aureus and C. albicans and good activity against P. aeruginosa. NADES exhibited no observable antimicrobial activity against spore-forming B. subtilis.

The Impact of Natural Deep Eutectic Solvents and Extraction Method on the Co-Extraction of Trace Metals from Fucus vesiculosus.

In recent years, natural deep eutectic solvents (NADES) have been widely investigated for the extraction of food and medicinal plants as well as seaweeds. However, the ability of NADES for trace elements co-extraction from natural sources is not well investigated. The aim of this study was to investigate the ability of common NADES for trace elements co-extraction from Fucus vesiculosus. All of the tested NADES did not recover As and Co (concentration

Simultaneous determination of seven anthraquinones in Cassiae semen by natural deep eutectic solvent extraction.

INTRODUCTION: Anthraquinones are considered to be an important class of bioactive substances in Cassiae semen, and the content of anthraquinones is an essential indicator of the quality of Cassiae semen raw herbal materials. OBJECTIVES: The present study aimed to propose a novel, efficient and effective ultra-high-performance liquid chromatography (UHPLC) method for the simultaneous determination of aurantio-obtusin, aloe-emodin, rhein, obtusin, emodin, chrysophanol and physcion, with the help of natural deep eutectic solvents (NADESs) as extraction solvents. METHODOLOGY: NADESs were introduced to the simultaneous extraction of anthraquinones from Cassiae semen samples. Several NADESs were designed by menthol, choline chloride, d-glucose as hydrogen bond acceptors, with nine different acids and appropriate water as hydrogen bond donors. The parameters affecting the extraction efficiency of seven anthraquinones were demonstrated in detail. RESULTS: Among the obtained NADESs, the highest extraction efficiency was demonstrated by a solution consisting of d-glucose, lactic acid and water with a molar ratio of 1:5:4. The seven anthraquinones were separated on an ACQUITY UPLC® BEH C18 column (2.1 mm × 100 mm, 1.8 µm) and detected within 12 min by a photodiode array (PDA) detector at 254 and 284 nm. The limits of detection and quantitation were from 1.00 to 7.26 µg/l and 3.29 to 24.22 µg/l, respectively. And Cassiae semen sample-based recoveries ranged from 81.13% to 113.78% with the relative standard deviation (RSD) (n = 6) of 1.4% to 10.1%. CONCLUSION: The developed method demonstrated that NADESs were applied successfully to analyse the anthraquinones in Cassiae semen samples collected from different regions in China.

Elaboration and Characterization of Natural Deep Eutectic Solvents (NADESs): Application in the Extraction of Phenolic Compounds from pitaya.

In this paper, natural deep eutectic solvents (NADESs) with lactic acid, glycine, ammonium acetate, sodium acetate, and choline chloride were prepared with and without the addition of water. NADES formation was evaluated using FTIR and Raman, where hydrogen bonds were identified between the hydroxyl group of lactic acid and the amino and carboxyl groups of glycine. Acetate and ammonium ions were also identified as forming bonds with lactic acid. The addition of water did not cause changes in the vibrational modes of the FTIR and Raman spectra but contributed to a reduction in NADES viscosity and density. Viscosity ranged from 0.335 to 0.017 Pa s-1, and density ranged from 1.159 to 0.785 g mL-1. The best results for the extraction of phenolic compounds from pitaya (dragon fruit) were achieved with an organic solvent (450. 41 mg 100 g-1 dry bases-db) in comparison to NADESs lactic acid:glycine (193.18 mg 100 g-1 db) and lactic acid:ammonium acetate (186.08 mg 100 g-1 db). The antioxidant activity of the extracts obtained with the NADESs was not statistically different from that of the extract obtained with organic solvents.