Skip to main content

Advertisement

SpringerLink
Log in

Physicochemical and Anti-bacterial Properties of Novel Osthole-Menthol Eutectic System

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Deep eutectic solvents (DES), as a new type of green solvent, show great advantages of easy preparation and no need of purification after synthesis and great potential applications in various fields. Osthole has shown wide variety of pharmacological functions like antimicrobial, anti-inflammatory, antioxidant, or anti-cancerous. To explore the efficient delivery of osthole, we have designed a new DES based on osthole and DL-menthol with molar ratio of 1:15. The interaction between osthole and DL-menthol was checked and verified by 1HNMR and FT-IR spectra. The physicochemical properties and anti-bacterial activity of the DES were investigated. Low viscosity and higher anti-bacterial activity against S. aureus make the DES suitable for the dermal or transdermal delivery of osthole. Therefore, the results presented herein indicated that DES may serve as a new strategy for the application of active pharmaceutical ingredients.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. You, L., Feng, S., An, T., Wang, X.: Osthole: a promising lead compound for drug discovery from a traditional Chinese medicine (TCM). Nat. Prod. Commum. 4, 297–302 (2009)

    CAS  Google Scholar 

  2. Wei, M., Mo, S.L., Nabar, N.R., Chen, Y., Zhang, J.J., He, Q.L., Zou, X.N., Liu, X.G., Sun, L.B., Zhou, S.F.: Modification of rat model of sciatica induced by lumber disc herniation and the anti-inflammatory effect of osthole given by epidural catheterization. Pharmacol. 90, 251–263 (2012)

    Article  CAS  Google Scholar 

  3. Wang, Y.J., Zhang, G.W., Pan, J.H., Gong, D.M.: Novel insights into the inhibitory mechanism of kaempferol on xanthine oxidase. J. Agric. Food Chem. 63, 526–534 (2015)

    Article  CAS  PubMed  Google Scholar 

  4. Renuka, N., Kumar, K.J.: Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents. Bioorg. Med. Chem. Lett. 23, 6406–6409 (2013)

    Article  CAS  Google Scholar 

  5. Sun, C.J., Gui, Y., Hu, R.F., Chen, J.Y., Wang, B., Guo, Y.X., Lu, W.J., Nie, X.J., Shen, Q., Gao, S., Fang, W.Y.: Preparation and pharmacokinetics evaluation of solid self-microemulsifying drug delivery system (S-SMEDDS) of osthole. AAPS PharmSciTech. 19, 2301–2310 (2018)

    Article  CAS  PubMed  Google Scholar 

  6. Meng, S., Zhang, C., Shi, W., Zhang, X.W., Liu, D.H., Wang, P., Jin, Y.: Preparation of osthole-loaded nano-vesicles for skin delivery: characterization, in vitro skin permeation and preliminary in vivo pharmacokinetic studies. Eur. J. Pharm. Sci. 92, 49–54 (2016)

    Article  CAS  PubMed  Google Scholar 

  7. Yun, F., Kang, A., Shan, J., Zhao, X., Bi, X., Li, J., Di, L.: Preparation of osthole-polymer solid dispersions by hot-melt extrusion for dissolution and bioavailability enhancement. Int. J. Pharm. 465, 436–443 (2014)

    Article  CAS  PubMed  Google Scholar 

  8. Wang, L.N., Zheng, S.Y., Huang, G.C., Sun, J., Pan, Y.L., Si, Y.H., Tu, P.C., Xu, G.H., Ma, Y., Guo, Y.: Osthole-loaded N-octyl-O-sulfonyl chitosan micelles (NSC-OST) inhibits RANKL-induced osteoclastogenesis and prevents ovariectomy-induced bone loss in rats. J. Cell. Mol. Med. 24, 4105–4117 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Guy, R.H.: Current status and future prospects of transdermal drug delivery. Pharm. Res. 13, 1765–1769 (1996)

    Article  CAS  PubMed  Google Scholar 

  10. Prausnitz, M.R., Mitragotri, S., Langer, R.: Current status and future potential of transdermal drug delivery. Nat. Rev. Drug Discov. 3, 115–124 (2004)

    Article  CAS  PubMed  Google Scholar 

  11. Abbott, A.P., Capper, G., Davies, D.L., Munro, H.L., Rasheed, R.K., Tambyrajah, V.: Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium slats with functional side chains. Chem. Commun. 19, 2010–2011 (2001)

    Article  Google Scholar 

  12. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., Tambyrajah, V.: Novel solvent properties of choline chloride/urea mixture. Chem. Commun. 2003, 70–71 (2003)

    Article  Google Scholar 

  13. Abbott, A.P., Boothby, D., Capper, G., Davies, D.L., Rasheed, R.K.: Deep Eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126, 9142–9147 (2004)

    Article  CAS  PubMed  Google Scholar 

  14. Vanda, H., Dai, Y., Wilson, E.G., Verpoorte, R., Choi, Y.H.: Green solvents from ionic liquids and deep eutectic solvents to natural deep eutectic solvents. C. R. Chimie. 21, 628–638 (2018)

    Article  CAS  Google Scholar 

  15. Pena-Pereira, F., Namiesnik, J.: Ionic liquids and deep eutectic mixtures: sustainable solvents for extraction processes. ChemSusChem. 7, 1784–1800 (2014)

    Article  CAS  PubMed  Google Scholar 

  16. Wagle, D.V., Zhao, H., Baker, G.A.: Deep eutectic solvents: sustainable media for nanoscale and functional materials. Acc. Chem. Res. 47, 2299–2308 (2014)

    Article  CAS  PubMed  Google Scholar 

  17. Alonso, D.A., Baeza, A., Chinchilla, R., Guillena, G., Pastor, I.M., Ramon, D.J.: Deep eutectic solvents: the organic reaction medium of the century. Eur. J. Org. Chem. 2016, 612–632 (2016)

    Article  CAS  Google Scholar 

  18. Sarmad, S., Mikkola, J.P., Ji, X.Y.: Carbon dioxide capture with ionic liquids and deep eutectic solvents: a new generation of sorbents. ChemSusChem. 10, 324–352 (2017)

    Article  CAS  PubMed  Google Scholar 

  19. Xu, P., Zheng, G.W., Zong, M.H., Li, N., Lou, W.Y.: Recent progress on deep eutectic solvents in biocatalysis. Bioresour. Bioprocess. 4, 34 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

  20. Stott, P.W., Williams, A.C., Barry, B.W.: Transdermal delivery from eutectic systems: enhanced permeation of a model drug, ibuprofen. J. Control Release 50, 297–308 (1998)

    Article  CAS  PubMed  Google Scholar 

  21. Al-Akayleh, F., Ali, H.H.M., Ghareeb, M.M., Al-Remawi, M.: Therapeutic deep eutectic system of capric acid and menthol: characterization and pharmaceutical application. J. Drug Del. Sci. Tech. 53, 101159 (2019)

    Article  CAS  Google Scholar 

  22. Aroso, I.M., Craveiro, R., Rocha, A., Dionisio, M., Barreiros, S., Reis, R.L., Duarte, A.R.C.: Design of controlled release systems for THEDES—Therapeutic deep eutectic solvents, using supercritical fluid technology. Int. J. Pharm. 492, 73–79 (2015)

    Article  CAS  PubMed  Google Scholar 

  23. Duarte, A.R.C., Ferreira, A.S.D., Barreiros, S., Cabrita, E., Reis, R.L., Paiva, A.: A comparison between pure active pharmaceutical ingredients and therapeutic deep eutectic solvents: solubility and permeability studies. Eur. J. Pharm. Biopharm. 114, 296–304 (2017)

    Article  CAS  PubMed  Google Scholar 

  24. Gutiérrez, A., Aparicio, S., Atilhan, M.: Design of arginine-based therapeutic deep eutectic solvents as drug solubilization vehicles for active pharmaceutical ingredients. Phys. Chem. Chem. Phys. 21, 10621–10634 (2019)

    Article  PubMed  Google Scholar 

  25. Mano, F., Martins, M., Sa-Nogueira, I., Barreiros, S., Borges, J.P., Reis, R.L., Paiva, A.: Production of electrospun fast-dissolving drug delivery systems with therapeutic eutectic systems encapsulated in gelatin. AAPS Pharm. Sci. Tech. 18, 2579–2585 (2017)

    Article  CAS  Google Scholar 

  26. Mokhtarpour, M., Shekaari, H., Shayanfar, A.: Design and characterization of ascorbic acid based therapeutic deep eutectic solvent as a new ion-gel for delivery of sunitinib malate. J. Drug Del. Sci. Tech. 56, 101512 (2020)

    Article  CAS  Google Scholar 

  27. Silva, J.M., Pereira, C.V., Mano, F., Silva, E., Castro, V.I., Sá-Nogueira, I., Duarte, A.R.C.: Therapeutic role of deep eutectic solvents based on menthol and saturated fatty acids on wound healing. ACS Appl. Bio. Mater. 2, 4346–4355 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Rahman, M.S., Roy, R., Jadhav, B., Hossain, M.N., Halim, M.A., Raynie, D.E.: Formulation, structure, and applications of therapeutic and amino acid-based deep eutectic solvents: an overview. J. Mol. Liq 321, 114745 (2021)

    Article  CAS  Google Scholar 

  29. Yang, S.F., Wang, R., Wan, G., Wu, Z.M., Guo, S.J., Dai, X.X., Shi, X.Y., Qiao, Y.J.: A multiscale study on the penetration enhancement mechanism of menthol to osthole. J. Chem. Inf. Model. 56, 2234–2242 (2016)

    Article  CAS  PubMed  Google Scholar 

  30. Kamal, M.A.H.M., Iimura, N., Nabekura, T., Kitagawa, S.: Enhanced skin permeation of salicylate by ion-pair formation in non-aqueous vehicle and further enhancement by ethanol and l-menthol. Chem. Pharm. Bull. 54, 481–484 (2006)

    Article  CAS  Google Scholar 

  31. Patel, T., Ishiuji, Y., Yosipovitch, G.: Menthol: A refreshing look at this ancient compound. J. Am. Acad. Dermatol. 57, 873–878 (2007)

    Article  PubMed  Google Scholar 

  32. Wang, W., Cai, Y., Liu, Y., Zhao, Y., Feng, J., Liu, C.: Microemulsions based on paeonol:menthol eutectic mixture for enhanced transdermal delivery: formulation development and in vitro evaluation, Artif. Cells Nanomed. Biotechnol. 45, 1241–1246 (2017)

    CAS  Google Scholar 

  33. Syed, U.T., Leonardo, I.C., Mendoza, G., Gaspar, F.B., Gamez, E., Huertas, R.M., Crespo, M.T.B., Arruebo, M., Crespo, J.G., Sebastian, V., Brazinha, C.: On the role of components of therapeutic hydrophobic deep eutectic solvent-based nanoemulsions sustainably produced by membrane-assisted nanoemulsification for enhanced antimicrobial activity. Sep. Purif. Technol. 285, 120319 (2022)

    Article  CAS  Google Scholar 

  34. Zeng, C.X., Liu, Y.G., Ding, Z.M., Xia, H.P., Guo, S.Y.: Physicochemical properties and antibacterial activity of hydrophobic deep eutectic solvent-in-water nanoemulsion. J. Mol. Liq. 338, 116950 (2021)

    Article  CAS  Google Scholar 

  35. Fernandes, C.C., Haghbakhsh, R., Marques, R., Paiva, A., Carlyle, L., Duarte, A.R.C.: Evaluation of deep eutectic systems as an alternative to solvents in painting conservation. ACS Sustainable Chem. Eng. 9, 15451–15460 (2021)

    Article  CAS  PubMed  Google Scholar 

  36. van Osch, D.J.G.P., Dietz, C.H.J.T., van Spronsen, J., Kroon, M.C., Gallucci, F., Annaland, M., van Tuinier, S.: A search for natural hydrophobic deep eutectic solvents based on natural components. ACS Sustainable Chem. Eng. 7, 2933–2942 (2019)

    Article  Google Scholar 

  37. Nunes, R.J., Saramago, B., Marrucho, I.M.: Surface tension of DL-menthol:octanoic acid eutectic mixtures. J. Chem. Eng. Data 64, 4915–4923 (2019)

    Article  CAS  Google Scholar 

  38. Toprakçı, Ä., Pekel, A.G., Kurtulbaş, E., Şahin, S.: Special designed mentholbased deep eutectic liquid for the removal of herbicide 2,4dichlorophenoxyacetic acid through reactive liquid–liquid extraction. Chem. Pap. 74, 3995–4002 (2020)

    Article  Google Scholar 

  39. Lalikoglu, M.: Separation of butyric acid from aqueous media using menthol–based hydrophobic deep eutectic solvent and modeling by response surface methodology. Biomass Convers. Bior. (2021). https://doi.org/10.1007/s13399-021-01711-7

    Article  Google Scholar 

  40. Ma, C.Y., Laaksonen, A., Liu, C., Lu, X.H., Ji, X.Y.: The peculiar effect of water on ionic liquids and deep eutectic solvents. Chem. Soc. Rev. 47, 8685–8720 (2018)

    Article  CAS  PubMed  Google Scholar 

  41. Pandey, A., Pandey, S.: Solvatochromic Probe behavior within choline chloride-based deep eutectic solvents: effect of temperature and water. J. Phys. Chem. B. 118, 14652–14661 (2014)

    Article  CAS  PubMed  Google Scholar 

  42. Meng, X.Q., Ballerat-Busserolles, K., Husson, P., Andanson, J.M.: Impact of water on the melting temperature of urea + choline chloride deep eutectic solvent. New. J. Chem. 40, 4492–4499 (2016)

    Article  CAS  Google Scholar 

  43. Shah, D., Mjalli, F.S.: Effect of water on the thermo-physical properties of Reline: an experimental and molecular simulation based approach. Phys. Chem. Chem. Phys. 16, 23900–23907 (2014)

    Article  CAS  PubMed  Google Scholar 

  44. Ferreira, A.S.D., Craveiro, R., Duarte, A.R., Barreiros, S., Cabrita, E.J., Paiva, A.: Effect of water on the structure and dynamics of choline chloride/glycerol eutectic systems. J. Mol. Liq. 342, 117463 (2021)

    Article  CAS  Google Scholar 

  45. İşcan, G., Kirimer, N., Kürkcüoğlu, M., Başer, K.H.C., Demirci, F.: Antimicrobial screening of mentha piperita essential oils. J. Agric. Food Chem. 50, 3943–3946 (2002)

    Article  PubMed  Google Scholar 

  46. Silva, J.M., Pereira, C.V., Mano, F., Silva, E., Castro, V.I.B., Sa-Nogueira, I., Reis, R.L., Paiva, A., Matias, A.A., Duarte, A.R.: Therapeutic role of deeo eutectic solvents based on menthol and saturated fatty acids on wound healing. ACS Appl. Bio Mater. 2, 4346–4355 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Projects 21773063).

Author information

Authors and Affiliations

  1. School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China

    Jieyu Wu, Tianxiang Yin & Xiaoyong Wang

Authors
  1. Jieyu Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tianxiang Yin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiaoyong Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Tianxiang Yin or Xiaoyong Wang.

Ethics declarations

Conflict of interest

The authors declare no competing financial interest.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary Material 1

Rights and permissions

Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, J., Yin, T. & Wang, X. Physicochemical and Anti-bacterial Properties of Novel Osthole-Menthol Eutectic System. J Solution Chem 51, 1199–1208 (2022). https://doi.org/10.1007/s10953-022-01195-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-022-01195-7

Keywords

Search

Navigation