Ionic liquid-assisted micellar extraction for the quantitative determination of sesquiterpenic acids in Valeriana officinalis L. (Caprifoliaceae)

References

• Patočka, J.; Jakl, J. (2010) Biomedically relevant chemical constituents of Valeriana officinalis. Journal of Applied Biomedicine, 8: 11–18.
   Web of Science ®Google Scholar
• Hadley, S.; Petry, J.J. (2003) Valerian. American Family Physician, 67: 1755–1758.
   PubMed Web of Science ®Google Scholar
• Murti, K.; Kaushik, M.; Sangwan, Y.; Kaushik, A. (2011) Pharmacological properties of Valeriana officinalis: A review. Pharmacologyonline, 3: 641–646.
   Google Scholar
• Nurzyńska-Wierdak, R. (2014) Biological active compounds from roots of Valeriana officinalis L. cultivated in south-eastern region of Poland. Farmacia, 62: 683–692.
   Web of Science ®Google Scholar
• Damnjanović, I.; Kitić, D.; Zlatković-Guberinić, S.; Milosavljević, J.; Conić, I. (2010) Contemporary aspects of using Valerianae officinalis. Acta Medica Medianae, 49: 16–21
   Google Scholar
• Fugh-Berman, A.; Cott, J.M. (1999) Dietary supplements and natural products as psychotherapeutic agents. Psychosomatic Medicine, 61: 712–728.
   PubMed Web of Science ®Google Scholar
• Nam, S.M.; Choi, J.H.; Yoo, D.Y.; Kim, W.; Jung, H.Y.; Kim, J.W.; Kang, S.; Park, J.; Kim, D.; Kim, W.J.; Yoon, Y.S.; Hwang, I.K. (2013) Valeriana officinalis extract and its main component, valerenic acid, ameliorate D-galactose-induced reductions in memory, cell proliferation, and neuroblast differentiation by reducing corticosterone levels and lipid peroxidation. Experimental Gerontology, 48: 1369–1377.
   PubMed Web of Science ®Google Scholar
• Penzkofer, M.; Ziegler, E.; Heuberger, H. (2014) Contents of essential oil, valerenic acids and extractives indifferent parts of the rootstock of medicinal valerian (Valeriana officinalis L. s.l.), Journal of Applied Research on Medicinal and Aromatic Plants, 1: 98–106.
   Google Scholar
• Kelber, O.; Wegener, T.; Steinhoff, B.; Staiger, C.; Wiesner, J.; Knöss, W.; Kraft, K. (2014) Assessment of genotoxicity of herbal medicinal products: Application of the “bracketing and matrixing” concept using the example of Valerianae radix (valerian root). Phytomedicine, 21: 1124–1129.
   PubMed Web of Science ®Google Scholar
• American Herbal Pharmacopoeia^TM, Valerian Root, April 1999
   Google Scholar
• European Pharmacopoeia 8.0, 0453 (07/2010) and 2526 ( 07/2010)
   Google Scholar
• Becker, H.; Schrall, R. (1980) Valepotriates in tissue cultures of nine different Valerianaceae species in comparison to literature data of the intact plants. Journal of Natural Products, 43: 721–723.
   PubMed Web of Science ®Google Scholar
• Anastas, P.T.; Kirchhoff, M.M. (2002) Origins, current status, and future challenges of green chemistry. Accounts of Chemical Research, 35: 686–694.
   PubMed Web of Science ®Google Scholar
• Anastas, P.T.; Warner, J.C. (1998) Green Chemistry: Theory and Practice; Oxford University Press: New York.
   Google Scholar
• Bogdanov, M.G.; Kantlehner, W. (2009) Simple prediction of some physical properties of ionic liquids: The residual volume approach. Zeitschrift für Naturforschung, 64b: 215–222.
   Google Scholar
• Bogdanov, M.G.; Iliev, B.; Kantlehner, W. (2009) The residual volume approach II: Simple prediction of ionic conductivity of ionic liquids. Zeitschrift für Naturforschung, 64b: 756–764.
   Google Scholar
• Bogdanov, M.G.; Petkova, D.; Hristeva, S.; Svinyarov, I.; Kantlehner, W. (2010) New guanidinium-based room-temperature ionic liquids. Substituent and anion effect on density and solubility in water. Zeitschrift für Naturforschung, 65b: 37–48.
   Google Scholar
• Bogdanov, M.G.; Svinyarov, I.; Kunkel, H.; Steinle, C.; Arkhipova, M.; Kantlehner, W.; Maas, G. (2010) Empirical polarity parameters for hexaalkylguanidinium-based room-temperature ionic liquids. Zeitschrift für Naturforschung, 65b: 791–797.
   Google Scholar
• Plechkova, N.V.; Seddon, K.R. (2008) Applications of ionic liquids in the chemical industry. Chemical Society Reviews, 37: 123–150
   PubMed Web of Science ®Google Scholar
• Han, D.; Row, K.H. (2010) Recent applications of ionic liquids in separation technology. Molecules, 15: 2405–2426.
   PubMed Web of Science ®Google Scholar
• Hallett, J.P.; Welton, T. (2011) Room-temperature ionic liquids: Solvents for synthesis and catalysis. 2. Chemical Reviews, 111: 3508–3576.
   PubMed Web of Science ®Google Scholar
• Tan, Z.; Wang, C.; Yang, Z.; Yi, Y.; Wang, H.; Zhou, W.; Li, F. (2015) Ionic liquid-based ultrasonic-assisted extraction of secoisolariciresinol diglucoside from Flaxseed (Linum usitatissimum L.) with further purification by an aqueous two-phase system. Molecules, 20: 17929–17943.
   PubMed Web of Science ®Google Scholar
• Toledo Hijo, A.A.C.; Maximo, G.J.; Costa, M.C.; Batista, E.A.C.; Meirelles, A.J.A. (2016) Application of ionic liquids in the food and bioproducts industries. ACS Sustainable Chemistry & Engineering, 4: 5347–5369.
   Web of Science ®Google Scholar
• Dimitrijević, A.; Zec, N.; Zdolšek, N.; Dožić, S.; Tot, A.; Gadžurić, S.; Vraneš, M.; Trtić-Petrović, T. (2016) Aqueous biphasic system formation using 1-alkyl-3-ethylimidazolium bromide ionic liquids as new extractants. Journal of Industrial and Engineering Chemistry, 40: 152–160.
   Web of Science ®Google Scholar
• Nowicki, J.; Muszyński, M.; Mikkola, J.-P. (2016) Ionic liquids derived from organosuperbases: en route to superionic liquids. RSC Advances, 6: 9194–9208.
   Web of Science ®Google Scholar
• Bogdanov, M.G. (2014) Ionic liquids as alternative solvents for extraction of natural products. In Alternative Solvents for Natural Products Extraction, Green Chemistry and Sustainable Technology; Chemat, F.; Vian Abert, M.; Eds.; Springer-Verlag: Berlin, Germany; Heidelberg, Germany, pp.127–166.
   Google Scholar
• Bogdanov, M.G.; Svinyarov, I.; Keremedchieva, R.; Sidjimov A. (2012) Ionic liquid-supported solid-liquid extraction of bioactive alkaloids. I. New HPLC method for quantitative determination of glaucine in Glaucium flavum Cr. (Papaveraceae). Separation and Purification Technology, 97: 221–227.
   Web of Science ®Google Scholar
• Svinyarov, I.; Keremedchieva, R.; Bogdanov, M.G. (2016) Ionic liquid-supported solid-liquid extraction of bioactive alkaloids. IV. New HPLC method for quantitative determination of galantamine in Leucojum aestivum L. (Amaryllidaceae). Separation Science and Technology, 51: 2691–2699.
   Web of Science ®Google Scholar
• Wei, Z.; Zu, Y.; Fu, Y.; Wang, W.; Luo, M.; Zhao, C.; Pan, Y. (2013) Ionic liquids-based microwave-assisted extraction of active components from pigeon pea leaves for quantitative analysis. Separation and Purification Technology, 102: 75–81.
   Web of Science ®Google Scholar
• Chen, F.; Zhang, Q.; Gu, H.; Yang, L. (2016) An approach for extraction of kernel oil from Pinus pumila using homogenate-circulating ultrasound in combination with an aqueous enzymatic process and evaluation of its antioxidant activity, Journal of Chromatography A, 1471: 68–79.
   PubMed Web of Science ®Google Scholar
• Asensio-Ramos, M.; Ravelo-Pérez, L.M.; González-Curbelo, M.Á.; Hernández-Borges, J. (2011) Liquid phase microextraction applications in food analysis. Journal of Chromatography A, 1218: 7415–7437.
   PubMed Web of Science ®Google Scholar
• Stanisz, E.; Werner, J.; Zgoła-Greśkowiak, A. (2014) Liquid-phase microextraction techniques based on ionic liquids for preconcentration and determination of metals. Trends in Analytical Chemistry, 61: 54–66.
   Web of Science ®Google Scholar
• Pratiwi, A.I.; Yokouchi, T; Matsumoto, M.; Kondo, K. (2015) Extraction of succinic acid by aqueous two-phase system using alcohols/salts and ionic liquids/salts. Separation and Purification Technology, 155: 127–132.
   Web of Science ®Google Scholar
• Ho, T.D.; Canestraro, A.J.; Anderson, J.L. (2011) Ionic liquids in solid-phase microextraction: a review. Analytica Chimica Acta, 695: 18–43.
   PubMed Web of Science ®Google Scholar
• Bogdanov, M.G.; Svinyarov I. (2013) Ionic liquid-supported solid-liquid extraction of bioactive alkaloids. II. Kinetics, modeling and mechanism of glaucine extraction from Glaucium flavum Cr. (Papaveraceae). Separation and Purification Technology, 103: 279–288.
   Web of Science ®Google Scholar
• Tonova, K.; Svinyarov, I.; Bogdanov, M.G. (2014) Hydrophobic 3-alkyl-1-methylimidazolium saccharinates as extractants for L-lactic acid recovery. Separation and Purification Technology, 125: 239–246.
   Web of Science ®Google Scholar
• Bogdanov, M.G.; Keremedchieva, R.; Svinyarov, I. (2015) Ionic liquid-supported solid-liquid extraction of bioactive alkaloids. III. Ionic liquid regeneration and glaucine recovery from ionic liquid-aqueous crude extract of Glaucium flavum Cr. (Papaveraceae). Separation and Purification Technology, 155: 13–19.
   Web of Science ®Google Scholar
• Keremedchieva, R.; Svinyarov, I.; Bogdanov, M.G. (2015) Ionic liquid-based aqueous biphasic systems: A facile approach for ionic liquid regeneration from crude plant extracts. Processes, 3: 769–778.
   Web of Science ®Google Scholar
• Reichardt, Ch. (2005) Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N-phenolate betaine dyes. Green Chemistry, 7: 339–351.
   Web of Science ®Google Scholar
• Jessop, P.G.; Jessop, D.A.; Fu, D.; Phan, L. (2012) Solvatochromic parameters for solvents of interest in green chemistry. Green Chemistry, 14: 1245–1259.
   Web of Science ®Google Scholar
• Machnová, K.; Jacquemin, J.; Wagner, Z.; Bendová, M. (2012) Mutual solubilities of ammonium-based ionic liquids with water and with water/methanol mixture. Procedia Engineering, 42: 1229–1241.
   Google Scholar
• Claudio, A.F.M; Swift, L.; Hallet, J.P; Welton, T.; Coutinho, J.A.P.; Freire, M.G. (2014) Extended scale for the hydrogen-bond basicity of ionic liquids. Physical Chemistry Chemical Physics, 16: 6593–6601.
   PubMed Web of Science ®Google Scholar
• Zhang, S.; Wang, J.; Lu, X.; Zhou Q. (2014) Structures and Interactions of Ionic Liquids; Springer: Berlin, Heidelberg.
   Google Scholar
• Gaillon, L.; Sirieix-Plénet, J.; Letellier, P. (2004) Volumetric study of binary solvent mixtures constituted by amphiphilic ionic liquids at room temperature (1-alkyl-3-methylimidazolium bromide) and water. Journal of Solution Chemistry, 33: 1333–1347.
   Web of Science ®Google Scholar
• Sirieix-Plénet, J.; Gaillon, L.; Letellier, P. (2004) Behaviour of a binary solvent mixture constituted by an amphiphilic ionic liquid, 1-decyl-3-methylimidazolium bromide and water: Potentiometric and conductometric studies. Talanta, 63: 979–986.
   PubMed Web of Science ®Google Scholar
• Inoue, T.; Dong, B.; Zheng, L.-Q. (2007) Phase behavior of binary mixture of 1-dodecyl-3-methylimidazolium bromide and water revealed by differential scanning calorimetry and polarized optical microscopy. Journal of Colloid and Interface Science, 307: 578–581.
   PubMed Web of Science ®Google Scholar
• Bhargava, B.L.; Klein, M.L. (2009) Formation of micelles in aqueous solutions of a room temperature ionic liquid: a study using coarse grained molecular dynamics. Molecular Physics, 107: 393–401.
   Web of Science ®Google Scholar
• Bhargava, B.L.; Yasaka, Y.; Klein, M.L. (2011) Computational studies of room temperature ionic liquid–water mixtures. Chemical Communications, 47: 6228–6241.
   PubMed Web of Science ®Google Scholar
• Li, X.; Kersten, S.R.A.; Schuur, B. (2017) Extraction of acetic acid, glycolaldehyde and acetol from aqueous solutions mimicking pyrolysis oil cuts using ionic liquids. Separation and Purification Technology, 175: 498–505.
   Web of Science ®Google Scholar
• Cognigni, A.; Gaertner, P.; Zirbs, R.; Peterlik, H.; Prochazka, K.; Schröder, C.; Bica, K. (2016) Surface-active ionic liquids in micellar catalysis: Impact of anion selection on reaction rates in nucleophilic substitutions. Physical Chemistry Chemical Physics, 18: 13375–13384.
   PubMed Web of Science ®Google Scholar
• Matrak, J.; Schlosser, S. (2016) New mechanism and model of butyric acid extraction by phosphonium ionic liquid. Journal of Chemical & Engineering Data, 61: 2979–2996.
   Web of Science ®Google Scholar
• Zhou, Y.; Wu, D.; Cai, P.; Cheng, G.; Huang, C.; Pan, Y. (2015) Special effect of ionic liquids on the extraction of flavonoid glycosides from Chrysanthemum morifolium ramat by microwave assistance. Molecules, 20: 7683–7699.
   PubMed Web of Science ®Google Scholar
• Ressman, A.K.; Zirbs, R.; Pressler, M.; Gaertner, P.; Bica, K. (2013) Surface active ionic liquids for micellar extraction of piprine from black paper. Zeitschrift für Naturforschung, 68b: 1129–1137.
   Google Scholar
• Sanan, R.; Kang, T.S.; Mahajan, R.K. (2014) Complexation, dimerisation and solubilisation of methylene blue in the presence of biamphiphilicionic liquids: A detailed spectroscopic and electrochemical study. Physical Chemistry Chemical Physics, 16:5667–5677.
   PubMed Web of Science ®Google Scholar
• Vashishat, R.; Sanan, R.; Mahajan, R.K. (2015) Bile salt-surface active ionic liquid mixtures; mixed micellization and solubilization of phenothiazine. RSC Advances, 5: 72132–72141.
   Web of Science ®Google Scholar
• Łuczak, J.; Jungnickel, C.; Markiewicz, M.; Hupka, J. (2013) Solubilization of benzene, toluene, and xylene (BTX) in aqueous micellar solutions of amphiphilic imidazolium ionic liquids. The Journal of Physical Chemistry B, 117: 5653–5658.
   PubMed Web of Science ®Google Scholar
• Jungnickel, C.; Łuczak, J.; Ranke, J.; Fernández, J.F.; Müller, A.; Thöming, J. (2008) Micelle formation of imidazolium ionic liquids in aqueous solution. Colloids and Surfaces A: Physicochem. Eng. Aspects, 316: 278–284.
   Web of Science ®Google Scholar
• Rather, M.A.; Rather, G.M.; Pandit, S.A.; Bhat, S.A.; Bhat, M.A. (2015) Determination of cmc of imidazolium based surface active ionic liquids through probe-less UV–vis spectrophotometry. Talanta, 131: 55–58.
   PubMed Web of Science ®Google Scholar
• Gao, X.Q.; Björk, L. (2000) Valerenic acid derivatives and valepotriates among individuals, varieties and species of Valeriana. Fitoterapia, 71: 19–24.
   PubMed Web of Science ®Google Scholar
• Mirzaei, M.; Dinpanah, H. (2011) Three phases hollow fiber LPME combined with HPLC-UV for extraction, preconcentration and determination of valerenic acid in Valeriana officinalis. Journal of Chromatography B, 879: 1870–1874.
   Google Scholar
• LoBrutto, R.; Patel, T. (2007) Method Validation. in: Kazakevich, Y.; LoBrutto R. (Eds.), John Wiley and Sons Inc., Hoboken, New Jersey, pp. 455–502.
   Google Scholar