Screening, Optimization, and Bioavailability Research of Natural Deep Eutectic Solvent Extracts from Radix Pueraria

Natural deep eutectic solvent (NaDES) is generally considered as a greener alternative to fossil solvent, with great potential in various areas. In the present work, 25 different NaDESs were screened for the extraction of puerarin (PUE) and its two natural derivatives from Radix Pueraria (RP). As the main isoflavone in RP, PUE has a wide range of biological activities. However, its application is restricted due to its poor solubility in water and low oral bioavailability. In this study, the extraction of PUE with NaDESs showed significant advantages compared with traditional solvents. While using L-Pro-Maa (L-proline-malic acid) under optimal conditions, the optimized yields of PUE, 3-MPR and PRX were 98.7 mg/g, 16.3 mg/g and 9.9 mg/g, respectively, which were 2.2-, 2.9- and 3.4-fold higher than that of water. Furthermore, the oral bioavailability of PUE in NaDES extracts was comparatively investigated in rats with HPLC-MS technique. Pharmacokinetic analysis revealed that the relative bioavailability of PUE in L-Pro-Maa extract is 323%. The result indicated that NaDES is not only a sustainable ionic liquid with higher extraction efficiency, but also an enhancer of oral bioavailability of specific natural products.

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Saffron Processing Wastes as a Bioresource of High-Value Added Compounds: Development of a Green Extraction Process for Polyphenol Recovery Using a Natural Deep Eutectic Solvent

Antioxidants ◽

10.3390/antiox8120586 ◽

2019 ◽

Vol 8 (12) ◽

pp. 586 ◽

Cited By ~ 15

Author(s):

Achillia Lakka ◽

Spyros Grigorakis ◽

Ioanna Karageorgou ◽

Georgia Batra ◽

Olga Kaltsa ◽

...

Keyword(s):

Hydrogen Bond ◽

Maximum Yield ◽

Deep Eutectic Solvent ◽

Value Added ◽

Extraction Process ◽

Mass Spectrometry Analysis ◽

Molar Ratio ◽

Optimal Conditions ◽

Hydrogen Bond Acceptor ◽

Natural Deep Eutectic Solvent

The current investigation was undertaken to examine saffron processing waste (SPW) as a bioresource, which could be valorized to produce extracts rich in antioxidant polyphenols, using a green, natural deep eutectic solvent (DES). Initially, there was an appraisal of the molar ratio of hydrogen bond donor/hydrogen bond acceptor in order to come up with the most efficient DES composed of L-lactic acid/glycine (5:1). The following step was the optimization of the extraction process using response surface methodology. The optimal conditions thus determined were a DES concentration of 55% (w/v), a liquid-to-solid ratio of 60 mL g−1, and a stirring speed of 800 rounds per minute. Under these conditions, the extraction yield in total polyphenols achieved was 132.43 ± 10.63 mg gallic acid equivalents per g of dry mass. The temperature assay performed within a range of 23 to 80 °C, suggested that extracts displayed maximum yield and antioxidant activity at 50–60 °C. Liquid chromatography-mass spectrometry analysis of the SPW extract obtained under optimal conditions showed that the predominant flavonol was kaempferol 3-O-sophoroside and the major anthocyanin delphinidin 3,5-di-O-glucoside. The results indicated that SPW extraction with the DES used is a green and efficient methodology and may afford extracts rich flavonols and anthocyanins, which are considered to be powerful antioxidants.

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Chemical basis underline the bioactivity fortification of licorice by honey-frying due to the natural deep eutectic solvent characteristics of honey

10.21203/rs.3.rs-915907/v1 ◽

2021 ◽

Author(s):

Shasha Kong ◽

Pengyue Li ◽

Robert Verpoorte ◽

Jia Wang ◽

Chao Zhu ◽

...

Keyword(s):

Medicinal Plants ◽

Biological Activities ◽

Deep Eutectic Solvent ◽

Chemical Mechanism ◽

Immunomodulatory Activity ◽

Chemical Basis ◽

Synergistic Mechanism ◽

Pharmacologically Active ◽

Natural Deep Eutectic Solvent ◽

Novel Applications

Abstract Background Honey has been widely used in medicine plants processing since ancient times. Honey-frying of herbal medicine is a well-known treatment in Chinese medicine. It has been reported that honey-frying can improve the immunomodulatory efficacy of licorice. However, it is still unknown why honey-frying improves the immunomodulatory activity of licorice. And our previous research demonstrated that honey has natural deep eutectic solvent (NADES) characteristics. NADES is a kind of solvent with broad polarity range and has attracted extensive attention of scholars in different fields. In the present study, we investigated chemical basis underline the possible potentiation of honey-frying on licorice to elucidate its chemical mechanism. Methods Firstly, immunological experiments were conducted to investigate whether the honey-processing could enhance the immunomodulatory efficacy of licorice. Then, the synergistic mechanism of honey-processed licorice was explored based on cell biological activity test, chemical composition test, bioavailability test, and Fourier transform-infrared (FT-IR) spectra. Results Pharmacological experiment verified that honey-processing enhanced the immunomodulatory efficacy of licorice. Moreover, honey increased the total flavonoid and polysaccharide contents in licorice decoction, improved the thermal stability and oral bioavailability of certain pharmacologically active constituents, and augmented their overall immunostimulatory functions. Similar effects of honey were also observed with NADES. The above effects are due to multiple molecular interactions between active compounds and sugar molecules of NADES. Conclusion These findings indicate that the biological activities of medicinal plants might be fortified by NADES/honey in the processing of the plant material. At the meantime, these findings provide theoretical and empirical basis for potential novel applications of honey or other NADESs at augmenting the health-promoting effects of medicinal plants.

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Sesquiterpene Lactones fromArtemisiaGenus: Biological Activities and Methods of Analysis

Journal of Analytical Methods in Chemistry ◽

10.1155/2015/247685 ◽

2015 ◽

Vol 2015 ◽

pp. 1-21 ◽

Cited By ~ 43

Author(s):

Bianca Ivanescu ◽

Anca Miron ◽

Andreia Corciova

Keyword(s):

Michael Addition ◽

Biological Activities ◽

Sesquiterpene Lactones ◽

Optimal Conditions ◽

Amino Groups ◽

Extraction And Separation ◽

Wide Range ◽

Lactone Group ◽

Problematic Aspect ◽

Identification And Quantification

Sesquiterpene lactones are a large group of natural compounds, found primarily in plants ofAsteraceaefamily, with over 5000 structures reported to date. Within this family, genusArtemisiais very well represented, having approximately 500 species characterized by the presence of eudesmanolides and guaianolides, especially highly oxygenated ones, and rarely of germacranolides. Sesquiterpene lactones exhibit a wide range of biological activities, such as antitumor, anti-inflammatory, analgesic, antiulcer, antibacterial, antifungal, antiviral, antiparasitic, and insect deterrent. Many of the biological activities are attributed to theα-methylene-γ-lactone group in their molecule which reacts through a Michael-addition with free sulfhydryl or amino groups in proteins and alkylates them. Due to the fact that most sesquiterpene lactones are thermolabile, less volatile compounds, they present no specific chromophores in the molecule and are sensitive to acidic and basic mediums, and their identification and quantification represent a difficult task for the analyst. Another problematic aspect is represented by the complexity of vegetal samples, which may contain compounds that can interfere with the analysis. Therefore, this paper proposes an overview of the methods used for the identification and quantification of sesquiterpene lactones found inArtemisiagenus, as well as the optimal conditions for their extraction and separation.

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Comparative Pharmacokinetic Profiles of Puerarin in Rat Plasma by UHPLC-MS/MS after Oral Administration of Pueraria lobata Extract and Pure Puerarin

Journal of Analytical Methods in Chemistry ◽

10.1155/2020/4258156 ◽

2020 ◽

Vol 2020 ◽

pp. 1-8

Author(s):

Guozhe Zhang ◽

Jianwei Ji ◽

Mingzhong Sun ◽

Yuqiao Ji ◽

Hongjian Ji

Keyword(s):

Oral Bioavailability ◽

Water Solubility ◽

Biological Activities ◽

Rat Plasma ◽

Biologically Active ◽

Maximum Plasma ◽

Pueraria Lobata ◽

Time Curve ◽

Elimination Half ◽

Wide Range

Puerarin is the main biologically active isoflavone in Pueraria lobata and has a wide range of biological activities. However, due to its poor water solubility and low oral bioavailability, its clinical applications are restricted. Compared with puerarin, the Pueraria lobata extract (PLE) has better water solubility, lower toxicity, and less side effects. In this study, the pharmacokinetics of orally administered puerarin (100 mg/kg) and PLE (763 mg/kg, equivalent to 100.0 mg/kg of puerarin) to rats was investigated by the UHPLC-MS/MS method. Results showed that when the rats were administered PLE, the area under the concentration-time curve from zero to infinity (AUC0-inf) dramatically increased from 219.83 ± 64.37 μg h/L to 462.62 ± 51.74 μg h/L (p<0.01). The elimination half-time (t1/2) also increased from 1.60 ± 0.38 h to 12.04 ± 5.10 h (p<0.01). The maximum concentration (Cmax) of puerarin decreased from 101.64 ± 41.82 ng/mL to 48.64 ± 21.47 ng/mL (p<0.01), and time to reach the maximum plasma concentration (Tmax) of puerarin decreased from 1.46 ± 1.08 h to 0.54 ± 0.30 h (p<0.01). Results indicated that the pharmacokinetics of puerarin in Pueraria lobata may be dramatically different from pure puerarin in the plasma of rat, and oral bioavailability of puerarin may be increased when PLE was administrated to rats.

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Biocompatible natural deep eutectic solvent-based extraction and cellulolytic enzyme-mediated transformation of Pueraria mirifica isoflavones: a sustainable approach for increasing health-bioactive constituents

Bioresources and Bioprocessing ◽

10.1186/s40643-021-00428-9 ◽

2021 ◽

Vol 8 (1) ◽

Author(s):

Fonthip Makkliang ◽

Boondaree Siriwarin ◽

Gorawit Yusakul ◽

Suppalak Phaisan ◽

Attapon Sakdamas ◽

...

Keyword(s):

Deep Eutectic Solvent ◽

Deep Eutectic Solvents ◽

Cellulolytic Enzymes ◽

Cellulolytic Enzyme ◽

Optimal Conditions ◽

Bioactive Constituents ◽

Pueraria Mirifica ◽

Assisted Extraction ◽

Natural Deep Eutectic Solvents ◽

Natural Deep Eutectic Solvent

AbstractThe presence of specific gut microflora limits the biotransformation of Pueraria mirifica isoflavone (PMI) glycosides into absorbable aglycones, thus limiting their health benefits. Cellulolytic enzyme-assisted extraction (CAE) potentially solves this issue; however, solvent extraction requires recovery of the hydrophobic products. Here, we established the simultaneous transformation and extraction of PMIs using cellulolytic enzymes and natural deep eutectic solvents (NADESs). The NADES compositions were optimized to allow the use of NADESs as CAE media, and the extraction parameters were optimized using response surface methodology (RSM). The optimal conditions were 14.7% (v/v) choline chloride:propylene glycol (1:2 mol ratio, ChCl:PG) at 56.1 °C for the cellulolytic enzyme (262 mU/mL) reaction in which daidzin and genistin were extracted and wholly transformed to their aglycones daidzein and genistein. The extraction of PMIs using ChCl:PG is more efficient than that using conventional solvents; additionally, biocompatible ChCl:PG enhances cellulolytic enzyme activity, catalyzing the transformation of PMIs into compounds with higher estrogenicity and absorbability.

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Recovery of metabolites from natural deep eutectic solvent matrices by countercurrent separation

Planta Medica ◽

10.1055/s-0035-1556494 ◽

2015 ◽

Vol 81 (11) ◽

Author(s):

Y Liu ◽

J Garzon ◽

JB Friesen ◽

DC Lankin ◽

JB McAlpine ◽

...

Keyword(s):

Deep Eutectic Solvent ◽

Natural Deep Eutectic Solvent

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Pharmacologically potentials of different substituted coumarin derivatives

10.31221/osf.io/w6hdg ◽

2019 ◽

Cited By ~ 1

Author(s):

Chem Int

Keyword(s):

Benzene Ring ◽

Bioactive Compounds ◽

Biological Activities ◽

Pharmacological Properties ◽

Coumarin Derivatives ◽

Wide Range ◽

Anti Oxidant ◽

Anti Inflammatory ◽

Coumarin Compounds

Coumarin and its derivatives are widely spread in nature. Coumarin goes to agroup as benzopyrones, which consists of a benzene ring connected to a pyronemoiety. Coumarins displayed a broad range of pharmacologically useful profile.Coumarins are considered as a promising group of bioactive compounds thatexhibited a wide range of biological activities like anti-microbial, anti-viral,antiparasitic, anti-helmintic, analgesic, anti-inflammatory, anti-diabetic, anticancer,anti-oxidant, anti-proliferative, anti-convulsant, and antihypertensiveactivities etc. The coumarin compounds have immense interest due to theirdiverse pharmacological properties. In particular, these biological activities makecoumarin compounds more attractive and testing as novel therapeuticcompounds.

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Synthesis, Characterization and Antiproliferative Activity Assessment of a Novel 1H-5-mercapto-1,2,4 Triazole Derivative

Revista de Chimie ◽

10.37358/rc.17.4.5544 ◽

2017 ◽

Vol 68 (4) ◽

pp. 745-747 ◽

Cited By ~ 1

Author(s):

Marius Mioc ◽

Sorin Avram ◽

Vasile Bercean ◽

Mihaela Balan Porcarasu ◽

Codruta Soica ◽

...

Keyword(s):

Antiproliferative Activity ◽

Biological Activities ◽

Cancer Cell Line ◽

Vascular Endothelial ◽

Triazole Derivative ◽

Activity Assessment ◽

Wide Range ◽

Specific Receptors ◽

Endothelial Growth Factor ◽

Selection Of

Angiogenesis plays an important function in tumor proliferation, one of the main angiogenic promoters being the vascular endothelial growth factor (VEGF) which activates specific receptors, particularly VEGFR-2. Thus, VEGFR-2 has become an essential therapeutic target in the development of new antitumor drugs. 1,2,4-triazoles show a wide range of biological activities, including antitumor effect, which was documented by numerous reports. In the current study the selection of 5-mercapto-1,2,4-triazole structure (1H-3-styryl-5-benzylidenehydrazino-carbonyl-methylsulfanil-1,2,4-triazole, Tz3a.7) was conducted based on molecular docking that emphasized it as suitable ligand for VEGFR-2 and EGFR1 receptors. Compound Tz3a.7 was synthesized and physicochemically and biologically evaluated thus revealing a moderate antiproliferative activity against breast cancer cell line MDA-MB-231.

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Potential Triazole-based Molecules for the Treatment of Neglected Diseases

Current Medicinal Chemistry ◽

10.2174/0929867324666170727103901 ◽

2019 ◽

Vol 26 (23) ◽

pp. 4403-4434 ◽

Cited By ~ 5

Author(s):

Susimaire Pedersoli Mantoani ◽

Peterson de Andrade ◽

Talita Perez Cantuaria Chierrito ◽

Andreza Silva Figueredo ◽

Ivone Carvalho

Keyword(s):

Effective Treatment ◽

Chagas Disease ◽

Medicinal Chemistry ◽

Biological Activities ◽

Neglected Diseases ◽

Triazole Derivatives ◽

Wide Range ◽

The World ◽

Great Relevance ◽

The Moment

Neglected Diseases (NDs) affect million of people, especially the poorest population around the world. Several efforts to an effective treatment have proved insufficient at the moment. In this context, triazole derivatives have shown great relevance in medicinal chemistry due to a wide range of biological activities. This review aims to describe some of the most relevant and recent research focused on 1,2,3- and 1,2,4-triazolebased molecules targeting four expressive NDs: Chagas disease, Malaria, Tuberculosis and Leishmaniasis.

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Heterocycle Compounds with Antimicrobial Activity

Current Pharmaceutical Design ◽

10.2174/1381612826666200206093815 ◽

2020 ◽

Vol 26 (8) ◽

pp. 867-904 ◽

Cited By ~ 2

Author(s):

Maria Fesatidou ◽

Anthi Petrou ◽

Geronikaki Athina

Keyword(s):

Heterocyclic Compounds ◽

Bacterial Infections ◽

Scientific Community ◽

Antimicrobial Agents ◽

Fungal Infections ◽

Biological Activities ◽

Literature Survey ◽

New Findings ◽

Wide Range ◽

Number Of Microorganisms

Background: Bacterial infections are a growing problem worldwide causing morbidity and mortality mainly in developing countries. Moreover, the increased number of microorganisms, developing multiple resistances to known drugs, due to abuse of antibiotics, is another serious problem. This problem becomes more serious for immunocompromised patients and those who are often disposed to opportunistic fungal infections. Objective: The objective of this manuscript is to give an overview of new findings in the field of antimicrobial agents among five-membered heterocyclic compounds. These heterocyclic compounds especially five-membered attracted the interest of the scientific community not only for their occurrence in nature but also due to their wide range of biological activities. Method: To reach our goal, a literature survey that covers the last decade was performed. Results: As a result, recent data on the biological activity of thiazole, thiazolidinone, benzothiazole and thiadiazole derivatives are mentioned. Conclusion: It should be mentioned that despite the progress in the development of new antimicrobial agents, there is still room for new findings. Thus, research still continues.

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