Green and efficient extraction of different types of bioactive alkaloids using deep eutectic solvents

Jiang, Zheng‐Meng; Wang, Lan-Jin; Zhao, Guang‐Chao; Zhuang, Bo; Yin, Qiang; Liu, E‐Hu

doi:10.1016/j.microc.2018.10.057

Cited by 95 publications

(53 citation statements)

References 30 publications

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“…To obtain better separation between the peak of rutaecarpine and other peaks, the chromatographic conditions were optimized. Different types of columns [ZORBAX Eclipse XDB-C18, ZORBAX Extent-C18, ZORBAX SB-C18 (250 mm × 4.6 mm, 5 µm, Agilent technologies, Santa Clara, CA, USA), and Generall-M C18 (250 mm × 4.6 mm, 5 µm, Guangzhou Yanchuang Biotechnologies, Guangzhou, China)], column temperatures (25,30,35, and 40 • C), flow rates (0.8. 1.0, and 1.2 mL/min), mobile phases (methanol-water and acetonitrile-water), types of acid (formic acid, acetic acid, and phosphoric acid), and concentrations of additive (0.05%, 0.1%, and 0.2%) were optimized.…”

Section: Evaluation Of Analytical Methodsmentioning

confidence: 99%

“…After initial screening of extraction solvents, La-Buta DES was chosen to optimize the extraction conditions. The conditions included each extraction temperature (25,35,45,55, and 65 • C), extraction time (10,20,30,40,50, and 60 min), and solid-liquid ratio (1:10, 1:20, 1:30, 1:40 and 1:50). The effect of ultrasonic power was not investigated, and 500 W, 20 kHz was directly adopted.…”

Section: Opimization Of Extraction Conditionsmentioning

confidence: 99%

“…Jiang et al studied the extraction of rutaecarpine from the unripe fruits of T. ruticarpum using DESs consisted of choline chloride (ChCl) and hydrogen bond donors (HBDs), such as organic acids (lactic acid (Laa) and levulinic acid (La)), amides (acetamide (Ace) and urea (Ur)), sugar alcohols (ethylene glycol (Eg) and glycerol (Gly)), and sugars (D-glucose (Glu) and maltose (Mal)). Unfortunately, the results showed that only ChCl-La DES produced similar extraction efficiency for rutaecarpine with methanol [25]. More research is required to make tailor-made DESs as green solvents to extract rutaecarpine from the unripe fruits of T. ruticarpum.…”

Section: Introductionmentioning

confidence: 97%

See 2 more Smart Citations

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Sun

Liu

et al. 2019

Processes

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Deep eutectic solvents (DESs) are increasingly receiving interest as a new type of green and sustainable alternative to hazardous organic solvents. In this work, a novel DES based on levulinic acid (La) and 1,4-butanediol (Buta) as an extraction media was developed for extracting the bioactive alkaloid rutaecarpine from the unripe fruits of Tetradium ruticarpum. 24 different DESs consisting of choline chloride, betaine, sugar alcohols, organic acids, amides, and sugars were prepared and tailored to test their extraction efficiency. After initial screening, a hydrophilic DES composed of La and Buta with 1:0.5 molar ratio containing 25% water was tailored for the highest extraction efficiency, followed by the optimizations of molar ratio and water content. The interaction between the molecules of La-Buta DES was investigated by nuclear magnetic resonance spectroscopy in order to confirm its deep eutectic supermolecular structure feature. The extraction conditions were optimized by single-factor experiments, including extraction temperature, extraction time, and solid-liquid ratio. The developed La-Buta DES extraction procedure was successfully applied for the analysis of rutaecarpine in Chinese patent medicines containing the unripe fruits of T. ruticarpum. The excellent property of La-Buta DES indicated its potential as a promising green solvent instead of conventional organic solvent for the extraction of rutaecarpine from the unripe fruits of T. ruticarpum, and that it can used as a sustainable and safe extraction media for other applications.

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Section: Evaluation Of Analytical Methodsmentioning

confidence: 99%

Section: Opimization Of Extraction Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

See 1 more Smart Citation

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Sun

Liu

et al. 2019

Processes

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“…The use of NADES in the extraction of alkaloids is still very limited and there are only a few reports of its use published in the last two years. One of the most recent works deals with the extraction of alkaloids derived from morphinane, protoberberine, bisbenzylisoquinoline, indole and quinolizidine alkaloids using 75 different DES [26]. Authors found that DES based on Choline-lactic acid were superior for the extraction of alkaloids derived from morphinane, protoberberine, indole, and quinolizidine alkaloids.…”

Section: Introductionmentioning

confidence: 99%

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

Torres-Vega

Gómez‐Alonso

Pérez‐Navarro

et al. 2020

Plants

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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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“…At present, NADESs are widely used in science for extraction of the following types of BASs: flavonoids [19,20], alkaloids [21], anthocyanins [22], flavors [23], saponins [24], etc. [25].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2020

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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 R2e = 0.993 for glycyram and R2e = 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.

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Green and efficient extraction of different types of bioactive alkaloids using deep eutectic solvents

Cited by 95 publications

References 30 publications

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

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

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

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