Ionic Liquids as Efficient Extractants for Quercetin from Red Onion (Allium cepa L.)

Urszula Domanska; Anna Wisniewska; Zbigniew Dabrowski; Mikolaj Wieckowski

doi:10.6000/1929-5030.2018.07.04

Authors

Urszula Domanska Industrial Chemistry Research Institute, Rydygiera 8, 01-793 Warsaw, Poland; Thermodynamic Research Unit, School of Engineering, University of KwaZulu-Natal, Howard College Campus, King George V Avenue, Durban 4041
Anna Wisniewska Industrial Chemistry Research Institute, Rydygiera 8, 01-793 Warsaw
Zbigniew Dabrowski Industrial Chemistry Research Institute, Rydygiera 8, 01-793 Warsaw
Mikolaj Wieckowski Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw

DOI:

https://doi.org/10.6000/1929-5030.2018.07.04

Keywords:

Quercetin, Ionic liquids, Solubility, Extraction from red onion, Hydrogen bonding interaction.

Abstract

The solubility of Quercetin in alcohols, esters and in 1-ethyl-3-methylimidazolium trifluoroacetate, [EMIM][TFA] ionic liquid (IL) using the dynamic method was measured at constant pH in a range of temperature 233-373 K and compare to the literature data. The experimental solubility data have been correlated by means of commonly known G^Emodels,UNIQUAC and NRTL with the assumption that the systems studied here present simple eutectic behaviour. The basic thermal properties of Quercetin, i.e., fusion temperature and the enthalpy of fusion have been measured with differential scanning microcalorimetry technique (DSC).The application of alcohols, esters and ionic liquids (ILs) as alternatives to conventional organic solvents in the liquid-liquid extraction of Quercetin from different medicinal plants, flowers and frozen red onion (Allium cepa L.) was investigated. The parameters affecting the extraction yield using ILs such as chemical structures of the IL cation and anion, the phase volume ratio of extracting solvent, time of extraction and the Quercetin form of sample and concentration were evaluated. Specific Quercetin composition was performed through HPLC measurements. Using the most effective ILs in extraction, the 14.3±0.1g^.kg^-1and 5.9±0.1g^.kg^-1of Quercetin from frozen pure red onion was obtained with N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium tetrafluoroborate, [N_2,2,1,2OCH3][BF₄] and 1-ethyl-3-methylimidazolium trifluoroacetate, [EMIM][TFA], respectively.

References

[1] Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoids antioxidants: chemistry, metabolism and structure-activity relationships. J Nutritional Biochem 2002; 13: 572-584. https://doi.org/10.1016/S0955-2863(02)00208-5
[2] Wojdy?o A, Oszmia?ski J, Czemerys R. Antioxidant activity and phenolic compounds in 32 selected herbs. Food Chem 2007; 105: 940-949. https://doi.org/10.1016/j.foodchem.2007.04.038
[3] Ibibia E-KTh. A review on antimicrobial and other beneficial effects of flavonoids. Int J Pharm Sci Rev Res 2013; 21: 20- 33.
[4] Li Y, Yao J, Han Ch, Yang J, Tabassum Chaudhry M, Wang S, Liu H, Yin Y. Quercetin, inflammation and immunity. Nutrients 2016; 8: 167-169. https://doi.org/10.3390/nu8030167
[5] El-Abyad MS, Morsi NM, Zaki DA, Shaaban MT. Preliminary screening of some Egyptian weeds for antimicrobial activity. Microbios 1990; 62: 47-57.
[6] Askari G, Ghiasvand R, Feizi A, Ghanadian SM, Karimian J. The effect of quercetin supplementation on selected markers of inflammation and oxidative stress. J Res Med Sci 2012; 17: 637-641.
[7] Wo?nicka E, Ku?miar A, Nowak D, Nykiel E, Kopacz M, Gruszecka J, Golec K. Comparative study on the antibacterial activity of some flavonoids and their sulfonic derivatives. Acta Poloniae Pharmaceutica 2013; 70: 567-571.
[8] Olayerijua OS, Olaleye MT, Crown OO, Komolafe K, Boligon AA, Athayde ML, Akindahunsi AA. Ethylacetate extract of red onion (Allium cepa L.) tunic affects hemodynamic parameters in rats. Food Sci Human Wellness 2015; 4: 115-122. https://doi.org/10.1016/j.fshw.2015.07.002
[9] Jaiswal N, Kumar D, Rizvi SI. Red onion extract (Allium cepa L.) supplementation improves redox balance in oxidatively stressed rats. Food Sci Human Wellness 2013; 2: 99-104. https://doi.org/10.1016/j.fshw.2013.05.003
[10] Batubara I, Suparto IH, Wulandari NS. The best extraction technique for kaempferol and quercetin isolation from Guava Leaves (Psidiumguajava). IOP Conf. Series: Earth Env Sci 58: 012060.
[11] Adamczewski B, Lutomski J, Marciniak K, Schmidt K. Pat. 56118, Poland, P116 568, 22.09.1966
[12] Singh BN, Singh BR, Singh RL, Prakash D, Singh DP, Sarma BK, Upadhyay G. Polyphenolic from various extractants of red onion (Allium cepa) peel with potent antioxidant and antimutagenic activities. Food Chem Tox 2009; 47: 1161- 1167. https://doi.org/10.1016/j.fct.2009.02.004
[13] Du F-Y, Xiao X-H, Luo X-J, Li G-K. Application of ionic liquids in the microwave-assisted extraction of polyphenolic compounds from medicinal plants Talanta 2009; 78: 1177- 1184. https://doi.org/10.1016/j.talanta.2009.01.040
[14] Ma W, Ho Row K. Optimized extraction of bioactive compounds from HerbaArtemisiaeScopariae with ionic liquids and deep eutectic solvents. J Liq Chrom Related Techn 2017; 40: 459-466. https://doi.org/10.1080/10826076.2017.1322522
[15] Hallet JP, Welton T. Room-temperature ionic liquids: solvents for synthesis and catalysis. 2. Chem Rev 2011; 111: 3508- 3576. https://doi.org/10.1021/cr1003248
[16] Doma?ska U. Ionic Liquids in Chemical Analysis, Chapter 1, General Review of Ionic Liquids and Their Properties, CRC Pres, Taylor & Francis Group, Abingdon, UK, 2008.
[17] Plechkova NV, Seddon KS. Application of ionic liquids in chemical industry. Chem Soc Rev 2008; 37: 123-150. https://doi.org/10.1039/B006677J
[18] Bogel-?ukasik E, Santos S, Bogel-?ukasik R, Nunes da Ponte M. Selectivity enhancement in the catalytic heterogeneous hydrogenation of limonene in supercritical carbon dioxide by an ionic liquid. J Supercrit Fluids 2010; 54: 210-217. https://doi.org/10.1016/j.supflu.2010.04.011
[19] Pernak J, Syguda A, Janiszewska D, Materna K, Praczyk T. Ionic liquids with herbicidal anions. Tetrahedron 2011; 67: 4838-4844. https://doi.org/10.1016/j.tet.2011.05.016
[20] Egorova KS, Gordeev EG, Ananikov VP. Biological activity of ionic liquids and their application in pharmaceutical and medicine. Chem Rev 2017; 117: 7132-7145. https://doi.org/10.1021/acs.chemrev.6b00562
[21] Freire MG, Neves CMSS, Marrucho IM, Canongia-Lopes JN, Rebelo LPN, Coutinho JAP. High-performance extraction of alkaloids using aqueous two-phase systems with ionic liquids. Green Chem 2010; 12: 1715-1725. https://doi.org/10.1039/c0gc00179a
[22] Fan Y, Dong X, Li Y, Zhong Y, Miao J, Hua JS, Sun Y. Extraction of l-Tryptophan by hydroxyl-functionalized ionic liquids. Ind Eng Chem Res 2015; 54: 12966-12973. https://doi.org/10.1021/acs.iecr.5b03651
[23] Louros LSC, Cláudio AFM, Neves CMSS, Freire MG, Marrucho IM, Pauly J, Coutinho JAP. Extraction of biomolecules using phosphonium-based ionic liquids + K3PO4 aqueous biphasic systems. Int J Mol Sci 2010; 11: 1777-1791. https://doi.org/10.3390/ijms11041777
[24] Ventura SPM, E Silva FA, Quental MV, Mondal D, Freire MG, Coutinho JAP. Ionic-liquid-mediated extraction and separation processes for bioactive compounds: Past, present, and future trends. Chem Rev 2017; 117: 6984-7052. https://doi.org/10.1021/acs.chemrev.6b00550
[25] Bécard G, Douds DD, Pfeffer PE. Extensive in vitro hyphal growth of vesicular-arbuscularmycorrhizal fungi in the presence of CO2 and flavonols. Appl Environ Microbiol 1992; 58: 821-825.
[26] Martino KG, Guyer D. Supercritical fluid extraction of quercetin from onion skins. J Food Proc Eng 2004; 27: 17- 28. https://doi.org/10.1111/j.1745-4530.2004.tb00620.x
[27] Dimitrieska-Stojkovi? E, Zdravkovski Z. Supercritical fluid extraction of quercetin and rutin from Hypericiherba. J Liq Chrom Related Techn 2003; 26: 2517-2533. https://doi.org/10.1081/JLC-120023798
[28] Ghoreishi SM. Ali H, Mousavi SO. Quercetin extraction from Rosa damascena Mill via supercritical CO2: Neural network and adaptive neuro fuzzy interface system modeling and response surface optimization. J Superc Fluids 2016; 112: 57-66. https://doi.org/10.1016/j.supflu.2016.02.006
[29] Ruan X, Yan LY, Li XX, Liu B, Zhang H, Wang Q. Optimization of process parameters of extraction of amentoflavone, quercetin and ginkgetin from Taxuschinensis using supercritical CO2 plus co-solvent. Molec 2014; 19: 17682-17696. https://doi.org/10.3390/molecules191117682
[30] Razmara RS, Daneshfar A, Sahraei R. Solubility of quercetin in water + methanol and water + ethanol from (292.8 to 333.8) K. J Chem Eng Data 2010; 55: 3934-3936. https://doi.org/10.1021/je9010757
[31] Abraham MH, Acree WE Jr. On the solubility of quercetin. J Mol Liq 2014; 197: 157-159. https://doi.org/10.1016/j.molliq.2014.05.006
[32] Patidar P, Pillai SA, Bahadur P, Bahadur A. Tuning the selfassembly of EO-PO block copolymers and quercetin solubilization in the presence of some common pharmaceutical excipients: A comparative study on a linear triblock and a starblock copolymer. J Mol Liq 2017; 241: 511- 519. https://doi.org/10.1016/j.molliq.2017.06.035
[33] Bogel-?ukasik R, Gon?alves LMN, Bogel-?ukasik E. Phase equilibrium phenomena in solution involving tannins, flavonoids and ionic liquids. Green Chem 2010; 12: 1947- 1953. https://doi.org/10.1039/c0gc00308e
[34] Pernak J, ?miglak M, Griffin ST, Hough WL, Wilson TB, Pernak A, Zabielska-Matejuk J, Fojutowski A, Kita K, Rogers RD. Long alkyl chain quaternary ammonium-based ionic liquids and potential applications. Green Chem 2006; 8: 798- 806. https://doi.org/10.1039/b604353d
[35] Hough WL, Rogers RD. Ionic liquids then and now: From solvents to materials to active pharmaceutical ingredients. Bull Chem Soc Jpn 2007; 80: 2262-2269. https://doi.org/10.1246/bcsj.80.2262
[36] Hough WL, ?miglak M, Rodriguez H, Swatloski RP, Spear SK, Daly DT, Pernak J, Grisel JE, Carliss RD, Soutullo MD, Davis JH, Rogers RD. The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem 2007; 31: 1429-1436. https://doi.org/10.1039/b706677p
[37] Rogers RD, Seddon KR. Ionic liquids-solvents of the future? Science 2003; 302: 792-793. https://doi.org/10.1126/science.1090313
[38] Moriel P, García-Suárez EJ, Martínez M, García AB, MontesMorán MA, Calvino-Casilda V, Beñares MA. Synthesis, characterization, and catalytic activity of ionic liquids based on biosources. Tetrahedron Lett 2010; 51: 4877-4881. https://doi.org/10.1016/j.tetlet.2010.07.060
[39] Gorke J, Srienc F, Kazlauskas R. Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnol. Bioprocess Eng 2010; 15: 40-53. https://doi.org/10.1007/s12257-009-3079-z
[40] Pernak J, Feder-Kubis J. Synthesis and properties of chiral ammonium-based ionic liquids. Chem Eur J 2005; 11: 4441- 4449. https://doi.org/10.1002/chem.200500026
[41] Pernak J, Skrzypczak A, Lota G, Fr?ckowiak E. Synthesis and properties of trigeminal tricationic ionic liquids. Chem Eur J 2007; 13: 3106-3112. https://doi.org/10.1002/chem.200601243
[42] Lopes JM, Paninho AB, Môlho MF, Nunes AVM, Rocha A, Lourenço NMT, Najdanovic-Visak V. Biocompatible choline based ionic salts: Solubility in short-chain alcohols. J Chem Thermodyn 2013; 67: 99-105. https://doi.org/10.1016/j.jct.2013.07.025
[43] Costa AJL, Soromenho MRC, Shimizu K, Marucho IM, Esperança JMSS, Lopes JNC, Rebelo LPN. Liquid–liquid equilibrium of cholinium-derived bistriflimide ionic liquids with water and octanol. J Phys Chem B 2012; 116: 9186-9195. https://doi.org/10.1021/jp3053168
[44] Costa AJL, Soromenho MRC, Shimizu K, Esperança JMSS, Lopes JNC, Rebelo LPN. Unusual LCST-type behaviour found in binary mixtures of choline-based ionic liquids with ethers. RSC Adv 2013; 3: 10262-10271. https://doi.org/10.1039/c3ra40327k
[45] Nockemann P, Binnemans K, Thijs B, Parac-Vogt TN, Merz K, Mudring AV, et al. Temperature-driven mixing-demixing behavior of binary mixtures of the ionic liquid choline bis(trifluoromethylsulfonyl)imide and water. J Phys Chem B 2009; 113: 1429-1437. https://doi.org/10.1021/jp808993t
[46] Weaver KD, Kim HJ, Sun J, MacFarlane DR, Elliott GD. Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications. Green Chem 2010; 12: 507-513. https://doi.org/10.1039/b918726j
[47] Petkovic M, Ferguson JL, Gunaratne HQN, Ferreira R, Leit?o MC, Sedon KR, Rebelo LPN, Pereira CS. Novel biocompatible cholinium-based ionic liquids—toxicity and biodegradability. Green Chem 2010; 12: 643-649. https://doi.org/10.1039/b922247b
[48] Doma?ska U, Bogel-?ukasik R. Physicochemical properties and solubility of alkyl-(2-hydroxyethyl)-dimethylammonium bromide. J Phys Chem B 2005; 109: 12124-12132. https://doi.org/10.1021/jp058015c
[49] Karpi?ska M, Wlaz?o M, Zawadzki M, Doma?ska U. Separation of binary mixtures hexane/hexene, cyclohexane/cyclohexene and ethylbenzene/styrene based on limiting activity coefficients. J Chem Thermodyn 2017; 110: 227-236. https://doi.org/10.1016/j.jct.2017.03.004
[50] Doma?ska U, Wlaz?o M, Karpi?ska M, Zawadzki M. High selective water/butan-1-ol separation on investigation of limiting activity coefficients with
[P8,8,8,8]
[NTf2] ionic liquid. Fluid Phase Equilibria 2017; 449: 1-9. https://doi.org/10.1016/j.fluid.2017.06.001
[51] Doma?ska U, Marciniak A. Liquid phase behaviour of 1- hexyloxymethyl-3-methyl-imidazolium-based ionic liquids with hydrocarbons: The influence of anion. J Chem Thermodyn 2005; 37: 577-585. https://doi.org/10.1016/j.jct.2005.02.012
[52] Doma?ska U, Zawadzki M, Królikowski M, Tshibangu MM, Ramjugernath D, Letcher TM. Measurements of activity coefficients at infinite dilution of organic compounds and water in isoquinolinium-based ionic liquid
[C8iQuin]
[NTf2] using GLC. J Chem Thermodyn 2011; 43: 499-504. https://doi.org/10.1016/j.jct.2010.10.026
[53] Zalewska A, Dumi?ska J, Langwald N, Syzdek J, Zawadzki M. Preparation and performance of gel polymer electrolytes doped with ionic liquids and surface-modified inorganic fillers. Electrochemica Acta 2014; 121: 337-344. https://doi.org/10.1016/j.electacta.2013.12.135
[54] Doma?ska U. Vapour-liquid-solid equilibrium of eicosanoic acid in one- and two-component solvents. Fluid Phase Equilib 1986; 26: 201-220. https://doi.org/10.1016/0378-3812(86)90006-3
[55] Abrams DS, Prausnitz JM. Statistical thermodynamics of liquid mixtures: A new expression for the excess Gibbs energy of partly or completely miscible systems. AIChE J 1975; 21: 116-128. https://doi.org/10.1002/aic.690210115
[56] Renon H, Prausnitz JM. Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J 1968; 14: 135–144. https://doi.org/10.1002/aic.690140124
[57] Passos H, Trindade MP, Vaz TSM, da Costa LP, Freire MG, Coutinho JAP. The impact of self-aggregation on the extraction of biomolecules in ionic-liquid-based aqueous twophase systems. Sep Purif Technol 2013; 108: 174-180. https://doi.org/10.1016/j.seppur.2013.02.008
[58] Doma?ska U, Okuniewska P, Królikowski M. Separation of 2- phenylethanol (PEA) from water using ionic liquids. Fluid Phase Equilib 2016; 423: 109-119. https://doi.org/10.1016/j.fluid.2016.04.022