Efficient and selective extraction of sinomenine by deep eutectic solvents

doi:10.1016/j.cjche.2022.09.016

Abstract

Abstract: Sinomenine is the main bio-active ingredient of Sinomenii Caulis and usually produced by solvent-extraction techniques. However, the extraction of sinomenine suffers from the lack of highly efficient and environmentally-benign solvents. In this work, deep eutectic solvents (DESs) based on fragrances were synthesized, hydrogen-bond donors (HBDs) and hydrogen-bond acceptors (HBAs) components of DESs were identified and their extraction ability for sinomenine was evaluated and the extraction conditions were optimized by single-factor and orthogonal design experiments. It was found that the hydrogen-bonding interaction between sinomenine and DESs was the main extraction driving force and there was no explicit relationship between the extraction ability and the hydrophobicity of the DESs. The DESs could be recycled and sinomenine could be recovered quantitatively via back-extraction. High-purity sinomenine ((95.0 ±2.3)%) could be produced. These findings suggest that DESs are highly-effective solvents for the isolation of sinomenine and exhibit great potential for the extraction of other bio-active compounds.

Key words: Sinomenine, Solvent extraction, Deep eutectic solvent (DES), Hydrogen-bonding interaction, Regeneration, Purification

摘要： Sinomenine is the main bio-active ingredient of Sinomenii Caulis and usually produced by solvent-extraction techniques. However, the extraction of sinomenine suffers from the lack of highly efficient and environmentally-benign solvents. In this work, deep eutectic solvents (DESs) based on fragrances were synthesized, hydrogen-bond donors (HBDs) and hydrogen-bond acceptors (HBAs) components of DESs were identified and their extraction ability for sinomenine was evaluated and the extraction conditions were optimized by single-factor and orthogonal design experiments. It was found that the hydrogen-bonding interaction between sinomenine and DESs was the main extraction driving force and there was no explicit relationship between the extraction ability and the hydrophobicity of the DESs. The DESs could be recycled and sinomenine could be recovered quantitatively via back-extraction. High-purity sinomenine ((95.0 ±2.3)%) could be produced. These findings suggest that DESs are highly-effective solvents for the isolation of sinomenine and exhibit great potential for the extraction of other bio-active compounds.

关键词: Sinomenine, Solvent extraction, Deep eutectic solvent (DES), Hydrogen-bonding interaction, Regeneration, Purification

Yunchang Fan, Chunyan Zhu, Sheli Zhang, Lei Zhang, Qiang Wang, Feng Wang. Efficient and selective extraction of sinomenine by deep eutectic solvents[J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 109-117.

Yunchang Fan, Chunyan Zhu, Sheli Zhang, Lei Zhang, Qiang Wang, Feng Wang. Efficient and selective extraction of sinomenine by deep eutectic solvents[J]. 中国化学工程学报, 2023, 57(5): 109-117.

References

[1] H. Zhou, Y.F. Wong, J. Wang, X. Cai, L. Liu, Sinomenine ameliorates arthritis via MMPs, TIMPs, and cytokines in rats, Biochem. Biophys. Res. Commun. 376 (2) (2008) 352–357.
[2] T. Sano, I. Matsumura, R. Nakamura, H. Yamaji, K. Hashimoto, O. Takeda, F. Kiuchi, T. Takeda, Genetic and chemical comparison of Boi (Sinomeni Caulis et Rhizoma) and Seifuto (Caulis Sinomenii), J Nat Med 64 (3) (2010) 257–265.
[3] L. Qian, Z.L. Xu, W. Zhang, B. Wilson, J.S. Hong, P.M. Flood, Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase, J. Neuroinflammation 4 (2007) 23.
[4] J. Qiu, M. Wang, J. Zhang, Q. Cai, D. Lu, Y. Li, Y. Dong, T. Zhao, H. Chen, The neuroprotection of Sinomenine against ischemic stroke in mice by suppressing NLRP3 inflammasome via AMPK signaling, Int. Immunopharmacol. 40 (2016) 492–500.
[5] B. Liu, H.L. Jiang, B. Shen, Y.L. Chang, Supercritical fluid extraction of sinomenine from Sinomenium acutum (Thumb) Rehd et Wils, J. Chromatogr. A 1075 (1–2) (2005) 213–215.
[6] L.Q. Lin, J. Zhang, Q. Fu, L.C. He, Y.C. Li, Concentration and extraction of sinomenine from herb and plasma using a molecularly imprinted polymer as the stationary phase, Anal. Chimica Acta 561 (1–2) (2006) 178–182.
[7] J.H. Cheong, C.Y. Kim, J. Kim, Preparative isolation and purification of sinomenine from Sinomenium acutum by centrifugal partition chromatography, J. Sep. Sci. 30 (13) (2007) 2105–2108.
[8] Q. Li, S. Wu, C. Wang, Y. Yi, W. Zhou, H. Wang, F. Li, Z. Tan, Ultrasonic-assisted extraction of sinomenine from Sinomenium acutum using magnetic ionic liquids coupled with further purification by reversed micellar extraction, Process Biochem. 58 (2017) 282–288.
[9] F.F. Li, Q. Li, S.G. Wu, D.Y. Sun, Z.J. Tan, Salting-out extraction of sinomenine from Sinomenium acutum by an alcohol/salt aqueous two-phase system using ionic liquids as additives, J. Chem. Technol. Biotechnol. 93 (7) (2018) 1925–1930.
[10] Z. Peng, W. Wang, X. Long, P. Qiu, Q. Liu, Y. Yang, X. Yang, M. Wang, S. Yin, X. Gong, Sinomenine purification by continuous liquid-liquid extraction process with centrifugal extractors, Adv. Chem. Eng. Sci. 10 (3) (2020) 171–180.
[11] X. Gao, S. Zhu, W. Zhang, D. Li, W. Dai, S. He, Analysis of crude oils using gas purge microsyringe extraction coupled to comprehensive two dimensional gas chromatography-time-of-flight mass spectrometry, Fuel 182 (2016) 788–797.
[12] W.E. Luttrell, Toxic tips: Chloroform, Chem. Health Saf. 12 (3) (2005) 36–37.
[13] A.R. Dahl, The fate of inhaled octane and the nephrotoxicant, isooctane, in rats, Toxicol Appl Pharmacol 100 (2) (1989) 334–341.
[14] M.J.L. Costa, M.T. Cunha, J.M.S. Cabral, M.R. Aires-Barros, Scale-up of recombinant cutinase recovery by whole broth extraction with PEG-phosphate aqueous two-phase, Biosep. 9 (4) (2000) 231–238.
[15] J. Cao, L. Chen, M. Li, F. Cao, L. Zhao, E. Su, Two-phase systems developed with hydrophilic and hydrophobic deep eutectic solvents for simultaneously extracting various bioactive compounds with different polarities, Green Chem. 20 (8) (2018) 1879–1886.
[16] A. Söldner, J. Zach, B. König, Deep eutectic solvents as extraction media for metal salts and oxides exemplarily shown for phosphates from incinerated sewage sludge ash, Green Chem. 21 (2) (2019) 321–328.
[17] Y.H. Liu, J. Li, R.X. Fu, L.L. Zhang, D.Z. Wang, S. Wang, Enhanced extraction of natural pigments from Curcuma longa L. using natural deep eutectic solvents, Ind. Crops Prod. 140 (2019) 111620.
[18] K.M. Lee, C.D. Han, Effect of hydrogen bonding on the rheology of polycarbonate/organoclay nanocomposites, Polymer 44 (16) (2003) 4573–4588.
[19] I. Erel, H. Schlaad, A.L. Demirel, Effect of structural isomerism and polymer end group on the pH-stability of hydrogen-bonded multilayers, J. Colloid Interface Sci. 361 (2) (2011) 477–482.
[20] T.B. Adams, M.M. McGowen, M.C. Williams, S.M. Cohen, V.J. Feron, J.I. Goodman, L.J. Marnett, I.C. Munro, P.S. Portoghese, R.L. Smith, W.J. Waddell, The FEMA GRAS assessment of aromatic substituted secondary alcohols, ketones, and related esters used as flavor ingredients, Food Chem. Toxicol. 45 (2) (2007) 171–201.
[21] J. Scognamiglio, L. Jones, C.S. Letizia, A.M. Api, Fragrance material review on α-methylbenzyl alcohol, Food Chem. Toxicol. 50 (Suppl 2) (2012) S124–S129.
[22] J. Scognamiglio, L. Jones, C.S. Letizia, A.M. Api, Fragrance material review on 2-methyl-4-phenyl-2-butanol, Food Chem. Toxicol. 50 (Suppl 2) (2012) S184–S188.
[23] S.P. Bhatia, G.A. Wellington, J. Cocchiara, J. Lalko, C.S. Letizia, A.M. Api, Fragrance material review on methyl cinnamate, Food Chem. Toxicol. 45 (Suppl 1) (2007) S113–S119.
[24] T.A. Loomis, A.W. Hayes, Loomis’s Essentials of Toxicology, fourth ed., Academic Press, San Diego, CA, USA, 1996, pp. 208–245.
[25] D.J.G.P. van Osch, C.H.J.T. Dietz, J. van Spronsen, M.C. Kroon, F. Gallucci, M. van Sint Annaland, R. Tuinier, A search for natural hydrophobic deep eutectic solvents based on natural components, ACS Sustain. Chem. Eng. 7 (3) (2019) 2933–2942.
[26] M. Gilmore, É.N. McCourt, F. Connolly, P. Nockemann, M. Swadźba-Kwaśny, J.D. Holbrey, Hydrophobic deep eutectic solvents incorporating trioctylphosphine oxide: Advanced liquid extractants, ACS Sustain. Chem. Eng. 6 (12) (2018) 17323–17332.
[27] Q. Xia, Y. Liu, J. Meng, W. Cheng, W. Chen, S. Liu, Y. Liu, J. Li, H. Yu, Multiple hydrogen bond coordination in three-constituent deep eutectic solvents enhances lignin fractionation from biomass, Green Chem. 20 (12) (2018) 2711–2721.
[28] S.H. Lee, S.B. Lee, Octanol/water partition coefficients of ionic liquids, J. Chem. Technol. Biotechnol. 84 (2) (2009) 202–207.
[29] L. Ropel, L.S. Belvèze, S.N.V.K. Aki, M.A. Stadtherr, J.F. Brennecke, Octanol–water partition coefficients of imidazolium-based ionic liquids, Green Chem. 7 (2) (2005) 83–90.
[30] Y.Y. Ning, J. Tang, Y.W. Liu, J. Jing, Y.S. Sun, J.L. Zhang, Highly luminescent, biocompatible ytterbium(iii) complexes as near-infrared fluorophores for living cell imaging, Chem. Sci. 9 (15) (2018) 3742–3753.
[31] M. Silva, H. Stray, M. Ould Metidji, T. Bjørnstad, Variation of the partition coefficient of phase-partitioning compounds between hydrocarbon and aqueous phases: An experimental study, Fuel 300 (2021) 120915.
[32] J.C. Dearden, G.M. Bresnen, The measurement of partition coefficients, Quant. Struct. Activity Relatio. 7 (3) (1988) 133–144.
[33] J.J. Gu, Q. Xu, H.B. Zhou, W. Li, J.L. Zhang, Liquid-liquid mass transfer property of two inline high shear mixers, Chem. Eng. Process. Process. Intensif. 101 (2016) 16–24.
[34] B. Bernet, A. Vasella, 1H-NMR analysis of intra- and intermolecular H-bonds of alcohols in DMSO: Chemical shift of hydroxy groups and aspects of conformational analysis of selected monosaccharides, inositols, and ginkgolides, Helvetica Chimica Acta 83 (5) (2000) 995–1021.
[35] C.M. Gowda, F. Vasconcelos, E. Schwartz, E.R.H. van Eck, M. Marsman, J.J.L.M. Cornelissen, A.E. Rowan, G.A. de Wijs, A.P.M. Kentgens, Hydrogen bonding and chemical shift assignments in carbazole functionalized isocyanides from solid-state NMR and first-principles calculations, Phys. Chem. Chem. Phys. 13 (28) (2011) 13082–13095.
[36] S. Prause, S. Spange, Adsorption of polymers on inorganic solid acids investigated by means of coadsorbed solvatochromic probes, J. Phys. Chem. B 108 (18) (2004) 5734–5741.
[37] R. Lungwitz, V. Strehmel, S. Spange, The dipolarity/polarisability of 1-alkyl-3-methylimidazolium ionic liquids as function of anion structure and the alkyl chain length, New J. Chem. 34 (6) (2010) 1135–1140.
[38] Y.R. Lee, K.H. Row, Comparison of ionic liquids and deep eutectic solvents as additives for the ultrasonic extraction of astaxanthin from marine plants, J. Ind. Eng. Chem. 39 (2016) 87–92.
[39] B. Ozturk, C. Parkinson, M. Gonzalez-Miquel, Extraction of polyphenolic antioxidants from orange peel waste using deep eutectic solvents, Sep. Purif. Technol. 206 (2018) 1–13.
[40] X. Peng, M.H. Duan, X.H. Yao, Y.H. Zhang, C.J. Zhao, Y.G. Zu, Y.J. Fu, Green extraction of five target phenolic acids from Lonicerae japonicae Flos with deep eutectic solvent, Sep. Purif. Technol. 157 (2016) 249–257.
[41] L.L. Yang, L. Li, H. Hu, J.B. Wan, P. Li, Natural deep eutectic solvents for simultaneous extraction of multi-bioactive components from jinqi Jiangtang preparations, Pharmaceutics 11 (1) (2019) 18.
[42] J. Cao, M. Yang, F. Cao, J. Wang, E. Su, Well-designed hydrophobic deep eutectic solvents as green and efficient media for the extraction of artemisinin from Artemisia annua leaves, ACS Sustain. Chem. Eng. 5 (4) (2017) 3270–3278.
[43] W. Wang, B. Zheng, J. Wu, W. Lv, P. Lin, X. Gong, Determination of the dissociation constants of 16 active ingredients in medicinal herbs using a liquid–liquid equilibrium method, Separations 8 (4) (2021) 49.
[44] Y.C. Fan, X.J. Li, L.F. Song, J. Li, L. Zhang, Effective extraction of quinine and gramine from water by hydrophobic ionic liquids: The role of anion, Chem. Eng. Res. Des. 119 (2017) 58–65.
[45] Z.M. Jiang, L.J. Wang, H.Q. Pang, Y. Guo, P.T. Xiao, C. Chu, L. Guo, E.H. Liu, Rapid profiling of alkaloid analogues in Sinomenii Caulis by an integrated characterization strategy and quantitative analysis, J. Pharmaceut. Biomed. Anal. 174 (2019) 376–385.