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Cyclodextrin polymers in combination with water and deep eutectic solvent for the retention of Eucalyptus citriodora essential oil

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Abstract

Eucalyptus citriodora is one of the most widely used essential oils (EOs) because of its various antimicrobial, antioxidant and anti-inflammatory activities. However, its limited aqueous solubility restricts its use. The aim of this study was to develop supramolecular formulations able to retain E. citriodora EO in solution. For this purpose, new cyclodextrin (CD) polymers were synthesized and characterized using gel permeation chromatography, FTIR and NMR spectroscopies. Their retention ability toward E. citriodora in non-conventional green media (deep eutectic solvent (DES):water mixture), more precisely choline chloride:urea DES:water (70:30 wt%), was evaluated and compared to the corresponding native CD [β-cyclodextrin (β-CD)] or CD derivatives [hydroxypropylated-β-cyclodextrin (HP-β-CD) and low methylated-β-cyclodextrin (CRYSMEB)] using static headspace-gas chromatography (SH-GC). All the studied formulations showed a great capacity to retain and reduce the volatility of E. citriodora. The various polymers showed divergent retention efficiencies.

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References

  1. Sebaaly, C., Jraij, A., Fessi, H., Charcosset, C., Greige-Gerges, H.: Preparation and characterization of clove essential oil-loaded liposomes. Food Chem. 178, 52–62 (2015). https://doi.org/10.1016/j.foodchem.2015.01.067

    Article  PubMed  CAS  Google Scholar 

  2. Kfoury, M., Hădărugă, N.G., Hădărugă, D.I., Fourmentin, S.: Cyclodextrins as encapsulation material for flavors and aroma. In: Encapsulations, pp. 127–192. Elsevier, Amsterdam (2016)

    Chapter  Google Scholar 

  3. Nakhle, L., Kfoury, M., Greige-Gerges, H., Fourmentin, S.: Effect of dimethylsulfoxide, ethanol, α- and β-cyclodextrins and their association on the solubility of natural bioactive compounds. J. Mol. Liq. 310, 113156 (2020). https://doi.org/10.1016/j.molliq.2020.113156

    Article  CAS  Google Scholar 

  4. Kfoury, M., Geagea, C., Ruellan, S., Greige-Gerges, H., Fourmentin, S.: Effect of cyclodextrin and cosolvent on the solubility and antioxidant activity of caffeic acid. Food Chem. 278, 163–169 (2019). https://doi.org/10.1016/j.foodchem.2018.11.055

    Article  PubMed  CAS  Google Scholar 

  5. Crini, G.: Review: a history of cyclodextrins. Chem. Rev. 114, 10940–10975 (2014). https://doi.org/10.1021/cr500081p

    Article  PubMed  CAS  Google Scholar 

  6. Kfoury, M., Auezova, L., Greige-Gerges, H., Fourmentin, S.: Promising applications of cyclodextrins in food: improvement of essential oils retention, controlled release and antiradical activity. Carbohydr. Polym. 131, 264–272 (2015). https://doi.org/10.1016/j.carbpol.2015.06.014

    Article  PubMed  CAS  Google Scholar 

  7. Kfoury, M., Landy, D., Fourmentin, S.: Characterization of cyclodextrin/volatile inclusion complexes: a review. Molecules 23, 1204 (2018). https://doi.org/10.3390/molecules23051204

    Article  PubMed Central  CAS  Google Scholar 

  8. Kfoury, M., Auezova, L., Fourmentin, S., Greige-Gerges, H.: Investigation of monoterpenes complexation with hydroxypropyl-β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 80, 51–60 (2014). https://doi.org/10.1007/s10847-014-0385-7

    Article  CAS  Google Scholar 

  9. Kfoury, M., Auezova, L., Ruellan, S., Greige-Gerges, H., Fourmentin, S.: Complexation of estragole as pure compound and as main component of basil and tarragon essential oils with cyclodextrins. Carbohydr. Polym. 118, 156–164 (2015). https://doi.org/10.1016/j.carbpol.2014.10.073

    Article  PubMed  CAS  Google Scholar 

  10. Crini, G., Fourmentin, S., Fenyvesi, É., Torri, G., Fourmentin, M., Morin-Crini, N.: Cyclodextrins, from molecules to applications. Environ. Chem. Lett. 16, 1361–1375 (2018). https://doi.org/10.1007/s10311-018-0763-2

    Article  CAS  Google Scholar 

  11. McCune, J.A., Kunz, S., Olesińska, M., Scherman, O.A.: DESolution of CD and CB macrocycles. Chem. Eur. J. 23, 8601–8604 (2017). https://doi.org/10.1002/chem.201701275

    Article  PubMed  CAS  Google Scholar 

  12. Rubin Pedrazzo, A., Trotta, F., Hoti, G., Cesano, F., Zanetti, M.: Sustainable mechanochemical synthesis of β-cyclodextrin polymers by twin screw extrusion. Environ. Sci. Pollut. Res. 29, 251–263 (2022). https://doi.org/10.1007/s11356-021-15187-5

    Article  CAS  Google Scholar 

  13. Cecone, C., Hoti, G., Krabicová, I., Appleton, S.L., Caldera, F., Bracco, P., Zanetti, M., Trotta, F.: Sustainable synthesis of cyclodextrin-based polymers by exploiting natural deep eutectic solvents. Green Chem. 22, 5806–5814 (2020). https://doi.org/10.1039/D0GC02247K

    Article  CAS  Google Scholar 

  14. Ciobanu, A., Mallard, I., Landy, D., Brabie, G., Nistor, D., Fourmentin, S.: Inclusion interactions of cyclodextrins and crosslinked cyclodextrin polymers with linalool and camphor in Lavandula angustifolia essential oil. Carbohydr. Polym. 87, 1963–1970 (2012). https://doi.org/10.1016/j.carbpol.2011.10.005

    Article  CAS  Google Scholar 

  15. Ciobanu, A., Mallard, I., Landy, D., Brabie, G., Nistor, D., Fourmentin, S.: Retention of aroma compounds from Mentha piperita essential oil by cyclodextrins and crosslinked cyclodextrin polymers. Food Chem. 138, 291–297 (2013). https://doi.org/10.1016/j.foodchem.2012.10.106

    Article  PubMed  CAS  Google Scholar 

  16. Shishov, A., Bulatov, A., Locatelli, M., Carradori, S., Andruch, V.: Application of deep eutectic solvents in analytical chemistry. A review. Microchem. J. 135, 33–38 (2017). https://doi.org/10.1016/j.microc.2017.07.015

    Article  CAS  Google Scholar 

  17. El Achkar, T., Greige-Gerges, H., Fourmentin, S.: Basics and properties of deep eutectic solvents: a review. Environ. Chem. Lett. (2021). https://doi.org/10.1007/s10311-021-01225-8

    Article  Google Scholar 

  18. Martins, M.A.R., Pinho, S.P., Coutinho, J.A.P.: Insights into the nature of eutectic and deep eutectic mixtures. J. Solution Chem. 48, 962–982 (2019). https://doi.org/10.1007/s10953-018-0793-1

    Article  CAS  Google Scholar 

  19. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., Tambyrajah, V.: Novel solvent properties of choline chloride/urea mixturesElectronic supplementary information (ESI) available: spectroscopic data. See http://www.rsc.org/suppdata/cc/b2/b210714g/. Chemical Communications. 70–71 (2003). https://doi.org/10.1039/b210714g

  20. Smith, E.L., Abbott, A.P., Ryder, K.S.: Deep eutectic solvents (DESs) and their applications. Chem. Rev. 114, 11060–11082 (2014). https://doi.org/10.1021/cr300162p

    Article  PubMed  CAS  Google Scholar 

  21. El Achkar, T., Moura, L., Moufawad, T., Ruellan, S., Panda, S., Longuemart, S., Legrand, F.-X., Costa Gomes, M., Landy, D., Greige-Gerges, H., Fourmentin, S.: New generation of supramolecular mixtures: characterization and solubilization studies. Int. J. Pharm. (2020). https://doi.org/10.1016/j.ijpharm.2020.119443

    Article  PubMed  Google Scholar 

  22. Martel, B., Ruffin, D., Weltrowski, M., Lekchiri, Y., Morcellet, M.: Water-soluble polymers and gels from the polycondensation between cyclodextrins and poly(carboxylic acid)s: a study of the preparation parameters. J. Appl. Polym. Sci. 97, 433–442 (2005). https://doi.org/10.1002/app.21391

    Article  CAS  Google Scholar 

  23. Luppi, F., Cavaye, H., Dossi, E.: Nitrated cross-linked β-cyclodextrin binders exhibiting low glass transition temperatures. Propellants, Explos., Pyrotech. 43, 1023–1031 (2018). https://doi.org/10.1002/prep.201800137

    Article  CAS  Google Scholar 

  24. Wintgens, V., Dalmas, F., Sébille, B., Amiel, C.: Novel phosphorus-containing cyclodextrin polymers and their affinity for calcium cations and hydroxyapatite. Carbohydr. Polym. 98, 896–904 (2013). https://doi.org/10.1016/j.carbpol.2013.06.073

    Article  PubMed  CAS  Google Scholar 

  25. Ohno, K., Wong, B., Haddleton, D.M.: Synthesis of well-defined cyclodextrin-core star polymers. J. Polym. Sci. A Polym. Chem. 39, 2206–2214 (2001). https://doi.org/10.1002/pola.1197

    Article  CAS  Google Scholar 

  26. Anand, R., Malanga, M., Manet, I., Manoli, F., Tuza, K., Aykaç, A., Ladavière, C., Fenyvesi, E., Vargas-Berenguel, A., Gref, R., Monti, S.: Citric acid–γ-cyclodextrin crosslinked oligomers as carriers for doxorubicin delivery. Photochem. Photobiol. Sci. 12, 1841 (2013). https://doi.org/10.1039/c3pp50169h

    Article  PubMed  CAS  Google Scholar 

  27. Wintgens, V., Lorthioir, C., Dubot, P., Sébille, B., Amiel, C.: Cyclodextrin/dextran based hydrogels prepared by cross-linking with sodium trimetaphosphate. Carbohydr. Polym. 132, 80–88 (2015). https://doi.org/10.1016/j.carbpol.2015.06.038

    Article  PubMed  CAS  Google Scholar 

  28. Li, Y.-F., Ha, Y.-M., Guo, Q., Li, Q.-P.: Synthesis of two β-cyclodextrin derivatives containing a vinyl group. Carbohydr. Res. 404, 55–62 (2015). https://doi.org/10.1016/j.carres.2014.11.012

    Article  PubMed  CAS  Google Scholar 

  29. Nakhle, L., Kfoury, M., Mallard, I., Greige-Gerges, H., Landy, D.: Solubilization of Eucalyptus citriodora essential oil and citronellal in deep eutectic solvents:water:cyclodextrins mixtures. J. Mol. Liq. 359, 119371 (2022). https://doi.org/10.1016/j.molliq.2022.119371

    Article  CAS  Google Scholar 

  30. Dugoni, G.C., Di Pietro, M.E., Ferro, M., Castiglione, F., Ruellan, S., Moufawad, T., Moura, L., Costa Gomes, M.F., Fourmentin, S., Mele, A.: Effect of water on deep eutectic solvent/β-cyclodextrin systems. ACS Sustain. Chem. Eng. 7, 7277–7285 (2019). https://doi.org/10.1021/acssuschemeng.9b00315

    Article  CAS  Google Scholar 

  31. Cao, J., Cao, J., Wang, H., Chen, L., Cao, F., Su, E.: Solubility improvement of phytochemicals using (natural) deep eutectic solvents and their bioactivity evaluation. J. Mol. Liq. 318, 113997 (2020). https://doi.org/10.1016/j.molliq.2020.113997

    Article  CAS  Google Scholar 

  32. Morin-Crini, N., Winterton, P., Fourmentin, S., Wilson, L.D., Fenyvesi, É., Crini, G.: Water-insoluble β-cyclodextrin–epichlorohydrin polymers for removal of pollutants from aqueous solutions by sorption processes using batch studies: a review of inclusion mechanisms. Prog. Polym. Sci. 78, 1–23 (2018). https://doi.org/10.1016/j.progpolymsci.2017.07.004

    Article  CAS  Google Scholar 

  33. Saokham, P., Muankaew, C., Jansook, P., Loftsson, T.: Solubility of cyclodextrins and drug/cyclodextrin complexes. Molecules 23, 1161 (2018). https://doi.org/10.3390/molecules23051161

    Article  PubMed Central  CAS  Google Scholar 

  34. Landy, D., Fourmentin, S., Salome, M., Surpateanu, G.: Analytical improvement in measuring formation constants of inclusion complexes between β-cyclodextrin and phenolic compounds. J. Incl. Phenom. Macrocycl. Chem. 38, 187–198 (2000). https://doi.org/10.1023/A:1008156110999

    Article  CAS  Google Scholar 

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Acknowledgements

The authors would like to acknowledge the National Council for Scientific Research of Lebanon (CNRS-L) and Université du Littoral Côte d'Opale (ULCO) for granting a doctoral fellowship to Lamia Nakhle. This work is a contribution to the CPER (Contrat de Plan Etat-Région) research project IRenE (Innovation et Recherche en Environnement) and is supported by the French Ministère de l’Enseignement Supérieur, the region Hauts-de-France and the European Regional Development Fund.

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Authors and Affiliations

  1. Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, UR 4492), SFR Condorcet FR CNRS 3417, Université du Littoral Côte d’Opale (ULCO), 145 Av. M. Schumann, 9140, Dunkirk, France

    Lamia Nakhle, Miriana Kfoury, Isabelle Mallard & David Landy

  2. Bioactive Molecules Research Laboratory, Faculty of Sciences, Lebanese University, Jdeidet el-Metn, 90656, Lebanon

    Lamia Nakhle & Hélène Greige-Gerges

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  1. Lamia Nakhle
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Correspondence to Miriana Kfoury.

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Nakhle, L., Kfoury, M., Mallard, I. et al. Cyclodextrin polymers in combination with water and deep eutectic solvent for the retention of Eucalyptus citriodora essential oil. J Incl Phenom Macrocycl Chem 102, 831–840 (2022). https://doi.org/10.1007/s10847-022-01161-2

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