The growing interest of the food, pharmaceutical and cosmetics industries in naturally occurring bioactive compounds or secondary plant metabolites also leads to a growing demand for the development of new and more effective analysis and isolation techniques. The extraction of bioactive compounds from plant material has always been a challenge, accompanied by increasingly strict control requirements for the final products and a growing interest in environmental protection. However, great efforts have been made in this direction and today a considerable number of innovative extraction techniques have been developed using green, environmentally friendly solvents. These solvents include the deep eutectic solvents (DES) and their natural equivalents, the natural deep eutectic solvents (NADES). Due to their adjustable physical-chemical properties and their green character, it is expected that DES/NADES could be the most widely used solvents in the future, not only in extraction processes but also in other research areas such as catalysis, electrochemistry or organic synthesis. Consequently, this review provided an up-to-date systematic overview of the use of DES/NADES in combination with innovative extraction techniques for the isolation of bioactive compounds from various plant materials. The topicality of the field was confirmed by a detailed search on the platform WoS (Web of Science), which resulted in more than 100 original research papers on DES/NADES for bioactive compounds in the last three years. Besides the isolation of bioactive compounds from plants, different analytical methods are presented and discussed.
The ginger family (Zingiberaceae) includes plants that are known worldwide to have a distinctive smell and taste, which are often used as spices in the kitchen, but also in various industries (pharmaceutical, medical, and cosmetic) due to their proven biological activity. The aim of this study was to investigate and compare the chemical composition and antioxidant activity (AA) of essential oils (EOs) of four characteristic ginger species: Elettaria cardamomum L. Maton (cardamom), Curcuma Longa L. (turmeric), Zingiber Officinale Roscoe (ginger), and Alpinia Officinarum Hance (galangal). Furthermore, the total phenolic content (TPC) and AA of crude extracts obtained after using ultrasound-assisted extraction (UAE) and different extraction solvents (80% ethanol, 80% methanol and water) were evaluated. A total of 87 different chemical components were determined by GC-MS/MS in the EOs obtained after hydrodistillation, 14 of which were identified in varying amounts in all EOs. The major compounds found in cardamom, turmeric, ginger, and galangal were α-terpinyl acetate (40.70%), β-turmerone (25.77%), α-zingiberene (22.69%) and 1,8-cineol (42.71%), respectively. In general, 80% ethanol was found to be the most effective extracting solvent for the bioactivities of the investigated species from the Zingiberaceae family. Among the crude extracts, ethanolic extract of galangal showed the highest TPC value (63.01 ± 1.06 mg GA g−1 DW), while the lowest TPC content was found in cardamom water extract (1.04 ± 0.29 mg GA g−1 DW). The AA evaluated by two different assays (ferric-reducing antioxidant power-FRAP and the scavenging activity of the cationic ABTS radical) proved that galangal rhizome is the plant with the highest antioxidant potential. In addition, no statistical difference was found between the AA of turmeric and ginger extracts, while cardamom rhizome was again inferior. In contrast to the crude extracts, the EOs resulted in significantly lower ABTS and FRAP values, with turmeric EO showing the highest AA.
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%.
In this study, the extraction efficiency of natural deep eutectic solvents (NADES) based on choline chloride as a hydrogen bond acceptor (HBA) and five different hydrogen bond donors (HBD; lactic acid, 1,4-butanediol, 1,2-propanediol, fructose and urea) was evaluated for the first time for the isolation of valuable bioactive compounds from Achillea millefolium L. The phytochemical profiles of NADES extracts obtained after ultrasound-assisted extraction were evaluated both spectrophotometrically (total phenolic content (TPC) and antioxidant assays) and chromatographically (UHPLC-MS and HPLC-UV). The results were compared with those obtained with 80% ethanol, 80% methanol, and water. The highest TPC value was found in the lactic acid-based NADES (ChCl-LA), which correlated with the highest antioxidant activity determined by the FRAP analysis. On the other hand, the highest antiradical potential against ABTS+• was determined for urea-based NADES. Phenolic acids (chlorogenic acid and dicaffeoylquinic acid isomers), flavones (luteolin and apigenin), and their corresponding glucosides were determined as the dominant individual phenolic compounds in all extracts. The antibacterial and antifungal properties of the extracts obtained against four bacterial cultures and two yeasts were evaluated using two methods: the agar dilution method to obtain the minimum inhibitory concentration (MIC) and the minimum bactericidal or fungicidal concentration (MBC or MFC), and the disc diffusion method. ChCl-LA had the lowest MIC and MBC/MFC with respect to all microorganisms, with an MIC ranging from 0.05 mg mL−1 to 0.8 mg mL−1, while the water extract had the weakest inhibitory activity with MIC and MBC/MFC higher than 3.2 mg mL−1.
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