Skip to main content
Log in

Partitioning behavior of arbutin in aqueous biphasic systems with deep eutectic solvents and polypropylene glycol: experimental and thermodynamic study

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

This study explored using deep eutectic solvents (DESs) to separate arbutin, a natural hydroquinone variant used in food and pharmaceuticals. While DESs are commonly used for natural product extraction, their potential for arbutin separation has not been studied until now. To address this gap, the authors selected a qualified aqueous biphasic system (ABS) composed of polypropylene glycol and DESs made with choline chloride and various carboxylic acids (lactic, acetic, and citric acid). To assess the effectiveness of the system, the partition coefficient and recovery of arbutin were determined as quantitative measures. The effects of different variables affecting the arbutin partitioning such as weight percentages of DES and polypropylene glycol, types of DES, and temperatures on the partitioning of arbutin were also investigated. Furthermore, thermodynamic transfer properties such as molar Gibbs energy, molar enthalpy, and molar entropy were calculated to analyze the effect of temperature on arbutin partitioning. The results indicated that increasing the weight percentages of polypropylene glycol and DESs resulted in higher partition coefficients of arbutin. The highest values of arbutin recovery (≈99.14%) and partition coefficient (≈166.22) were obtained using an ABS containing polypropylene glycol and DES-Lactic acid, suggesting the potential of this system for the separation of arbutin.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  • Abolghasembeyk T, Shahriari S, Salehifar M (2017) Extraction of stevioside using aqueous two-phase systems formed by choline chloride and K3PO4. Food Bioprod Proc 102:107–115

    Article  CAS  Google Scholar 

  • Buarque FS, Gautério GV, Coelho MA, Lemes AC, Ribeiro BD (2023) Aqueous two-phase systems based on ionic liquids and deep eutectic solvents as a tool for the recovery of non-protein bioactive compounds—a review. Processes 11(1):31

    Article  CAS  Google Scholar 

  • Cai C, Wu S, Wang C, Yang Y, Sun D, Li F, Tan Z (2019) Deep eutectic solvents used as adjuvants for improving the salting-out extraction of ursolic acid from cynomorium songaricum Rupr. in aqueous two-phase system. Sep Purif Technol 209:112–118

    Article  CAS  Google Scholar 

  • Cao J, Chen L, Li M, Cao F, Zhao L, Su E (2018) Two-phase systems developed with hydrophilic and hydrophobic deep eutectic solvents for simultaneously extracting various bioactive compounds with different polarities. Green Chem 20:1879–1886

    Article  CAS  Google Scholar 

  • Chanioti S, Tzia C (2018) Extraction of phenolic compounds from olive pomace by using natural deep eutectic solvents and innovative extraction techniques. Innov Food Sci Emerg Technol 48:228–239

    Article  CAS  Google Scholar 

  • Cho JY, Park KY, Lee KH, Lee HJ, Lee SH, Cho JA, Kim WS, Shin SC, Park KH, Moon JH (2011) Recovery of arbutin in high purity from fruit peels of pear (Pyrus pyrifolia Nakai). Food Sci Biotechnol 20:801–807

    Article  CAS  Google Scholar 

  • Cvjetko Bubalo M, Ćurko N, Tomašević M, Kovačević Ganić K, Radojcic Redovnikovic I (2016) Green extraction of grape skin phenolics by using deep eutectic solvents. Food Chem 200:159–166

    Article  CAS  PubMed  Google Scholar 

  • de Sousa RD, dos Reis Coimbra JS, da Silva LH, da Silva MD, Rojas EE, Vicente AA (2009) Thermodynamic studies of partitioning behavior of lysozyme and conalbumin in aqueous two-phase systems. J Chromatogr B 877(24):2579–2584

    Article  Google Scholar 

  • Deshasteh N, Shahriari S, Mostaghim T (2023) Use of aqueous two-phase systems consisting of sugar alcohols and polymer as a new platform for arbutin separation. Chem Pap 77:1645–1654

    Article  CAS  Google Scholar 

  • Ghasemzadeh B, Shahriari S, Pazuki G (2019) Efficient separation of curcumin using tetra butyl phosphonium bromide / carbohydrates (sorbitol, fructose) aqueous two-phase system. Fluid Phase Equilib 498:51–58

    Article  CAS  Google Scholar 

  • Inoue Y, Hasegawa S, Yamada T, Date Y, Mizutani H, Nakata S, Matsunaga K, Akamatsu H (2013) Analysis of the effects of hydroquinone and arbutin on the differentiation of melanocytes. Biol Pharm Bull 36:1722–1730

    Article  CAS  PubMed  Google Scholar 

  • Juneidi I, Hayyan M, Hashim MA (2018) Intensification of biotransformations using deep eutectic solvents: overview and outlook. Process Biochem 66:33–60

    Article  CAS  Google Scholar 

  • Karimi S, Shekaari H (2022) Application of acidic deep eutectic solvents in green extraction of 5-hydroxymethylfurfural. Sci Rep 12:13113

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kim J, Kim JI, Lee CW (2016) Development and validation of a modified QuEChERS method coupled with LC-MS/MS to determine arbutin in pear peels. Food Sci Biotechnol 25:987–992

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Moradi M, Mohammadian M, Pazuki G, Shahriari S (2022) Partitioning of crocin in a novel aqueous two-phase system composed of a deep eutectic solvent and acetonitrile. J Chem Eng Data. https://doi.org/10.1021/acs.jced.2c00027

    Article  Google Scholar 

  • Parejo I, Viladomat F, Bastida J, Codina C (2001) A single extraction step in the quantitative analysis of arbutin in bearberry (Arctostaphylos uva-ursi) leaves by high-performance liquid chromatography. Phytochem Anal 12:336–339

    Article  CAS  PubMed  Google Scholar 

  • Passos H, Tavares DJP, Ferreira AM, Freire MG, Coutinho JAP (2016) Are aqueous biphasic systems composed of deep eutectic solvents ternary or quaternary systems? ACS Sustain Chem Eng 4:2881–2886

    Article  CAS  Google Scholar 

  • Pereira JF, Ventura SP, e Silva FA, Shahriari S, Freire MG, Coutinho JA (2013) Aqueous biphasic systems composed of ionic liquids and polymers: a platform for the purification of biomolecules. Sep Purif Technol 113:83–89

    Article  CAS  Google Scholar 

  • Pop C, Vlase L, Tamas M (2009) Natural resources containing arbutin. Determination of arbutin in the leaves of Bergenia crassifolia (L.) Fritsch. acclimated in Romania. Not Bot Horti Agrobot Cluj-Napoca 37:129–132

    CAS  Google Scholar 

  • Prabhune A, Dey R (2023) Green and sustainable solvents of the future: deep eutectic solvents. J Mol Liq 379:121676

    Article  CAS  Google Scholar 

  • Sasaki C, Ichitani M, Kunimoto KK, Asada C, Nakamura Y (2014) Extraction of arbutin and its comparative content in branches, leaves, stems and fruits of Japanese pear Pyrus pyrifolia cv. Kousui. Biosci Biotechnol Biochem 78(5):874–877

    Article  CAS  PubMed  Google Scholar 

  • Vorobiev E, Lebovka N (2011) Pulse electric field-assisted extraction. CRC Press, Taylor & Francis Group, Boca Raton, Florida, USA

    Book  Google Scholar 

  • Wu L, Li L, Chen S, Wang L, Lin X (2020) Deep eutectic solvent-based ultrasonic-assisted extraction of phenolic compounds from Moringa oleifera L. leaves: optimization, comparison and antioxidant activity. Sep Purif Technol 247:117014

    Article  CAS  Google Scholar 

  • Xu P, Wang Y, Chen J, Wei X, Xu W, Ni R, Meng J, Zhou Y (2018) A novel aqueous biphasic system formed by deep eutectic solvent and ionic liquid for DNA partitioning. Talanta 189:467–479

    Article  CAS  PubMed  Google Scholar 

  • Yang H, Chen L, Zhou C, Yu X, Yagoub AEGA, Ma H (2018) Improving the extraction of L-phenylalanine by the use of ionic liquids as adjuvants in aqueous biphasic systems. Food Chem 245:346–352

    Article  CAS  PubMed  Google Scholar 

  • Yazdabadi A, Shahriari S, Salehifar M (2019) Extraction of caffeine using aqueous two-phase systems containing ionic liquid and sorbitol. Fluid Phase Equilib 502:112287

    Article  CAS  Google Scholar 

  • Zhao RT, Pei D, Yu PL, Wei JT, Wang NL, Di DL, Liu YW (2020) Aqueous two-phase systems based on deep eutectic solvents and their application in green separation processes. J Sep Sci 43(1):348–359

    Article  CAS  PubMed  Google Scholar 

  • Zhou P, Wang X, Liu P, Huang J, Wang C, Pan M, Kuang Z (2018) Enhanced phenolic compounds extraction from Morus alba L. leaves by deep eutectic solvents combined with ultrasonic-assisted extraction. Ind Crops Prod 120:147–154

    Article  CAS  Google Scholar 

  • Zhou Y, Yang X, Bai L, Wu Z, Zhang J, Qin Z, Fan J (2022) Investigation on the phase behaviors of aqueous surfactant two-phase systems containing Alkyl polyglucosides (APG) and alkyl polyglucoside sulfosuccinate (APGSS). J Mol Liq 368:120630

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Shahla Shahriari.

Ethics declarations

Conflict of interest

The corresponding author states that there is no conflict of interest.

Additional information

Publisher's Note

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

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) 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

Feyzi, M., Shahriari, S. Partitioning behavior of arbutin in aqueous biphasic systems with deep eutectic solvents and polypropylene glycol: experimental and thermodynamic study. Chem. Pap. 78, 2955–2966 (2024). https://doi.org/10.1007/s11696-023-03284-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-023-03284-3

Keywords

Navigation