Skip to main content
Log in

Choline chloride–based deep eutectic solvents (Ch-DESs) as promising green solvents for phenolic compounds extraction from bioresources: state-of-the-art, prospects, and challenges

  • Review Article
  • Published:
Biomass Conversion and Biorefinery Aims and scope Submit manuscript

Abstract

As the demand for phenolic compounds in pharmaceutical, food, nutraceutical, and cosmetic production is escalating, recovery of phenolic compounds from bioresources has been receiving great concerns from the scientific community. Renewable, environmentally benign, and biocompatible choline chloride–based deep eutectic solvents (Ch-DESs) are considered potential alternatives to conventional solvents in phenolic compound extraction. In the past 2 years, numerous innovative studies centered on phenolic compound extraction using Ch-DESs and process variable optimization have been explored. Thus, this review aims to summarize the updated state-of-the-art effort dedicated to phenolic compounds extraction from various bioresources using Ch-DESs. Furthermore, impact factors, kinetic modeling, and chemical mechanisms of the process are thoroughly analyzed and discussed. Finally, prospects and challenges in commercialization of phenolic compound extraction from bioresources using Ch-DESs are indicated and extensively discussed.

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

  1. Ignat I, Volf I, Popa VI (2011) A critical review of methods for characterisation of polyphenolic compounds in fruits and vegetables. Food Chem 126(4):1821–1835. https://doi.org/10.1016/j.foodchem.2010.12.026

    Article  Google Scholar 

  2. Morowvat MH, Ghasemi Y (2016) Evaluation of antioxidant properties of some naturally isolated microalgae: Identification and characterization of the most efficient strain. Biocatal Agric Biotechnol 8:263–269. https://doi.org/10.1016/j.bcab.2016.09.010

    Article  Google Scholar 

  3. Jablonsky M, Skulcova A, Malvis A, Sima J (2018) Extraction of value-added components from food industry based and agro-forest biowastes by deep eutectic solvents. J Biotechnol 282:46–66. https://doi.org/10.1016/j.jbiotec.2018.06.349

    Article  Google Scholar 

  4. Makris DP (2018) Green extraction processes for the efficient recovery of bioactive polyphenols from wine industry solid wastes - Recent progress. Curr Opin Green Sustain Chem 13:50–55. https://doi.org/10.1016/j.cogsc.2018.03.013

    Article  Google Scholar 

  5. Sharma K, Mahato N, Lee YR (2019) Extraction, characterization and biological activity of citrus flavonoids. Rev Chem Eng 35(2):265–284. https://doi.org/10.1515/revce-2017-0027

    Article  Google Scholar 

  6. Routray W, Orsat V (2012) Microwave-assisted extraction of flavonoids: A review. Food Bioprocess Tech 5(2):409–424. https://doi.org/10.1007/s11947-011-0573-z

    Article  Google Scholar 

  7. Heleno SA, Martins A, Queiroz MJ, Ferreira IC (2015) Bioactivity of phenolic acids: metabolites versus parent compounds: a review. Food Chem 173:501–513. https://doi.org/10.1016/j.foodchem.2014.10.057

    Article  Google Scholar 

  8. da Costa AM, Lopes MB, Falé P, Roseiro LB, Bogel-Łukasik R (2016) Extraction and purification of phenolic compounds from lignocellulosic biomass assisted by ionic liquid, polymeric resins and supercritical CO2. ACS Sustainable Chem Eng 4(6):3357–3367. https://doi.org/10.1021/acssuschemeng.6b00429

    Article  Google Scholar 

  9. Fabrowska J, Ibanez E, Leska B, Herrero M (2016) Supercritical fluid extraction as a tool to valorize underexploited freshwater green algae. Algal Res 19:237–245. https://doi.org/10.1016/j.algal.2016.09.008

    Article  Google Scholar 

  10. Parniakov O, Apicella E, Koubaa M, Barba FJ, Grimi N, Lebovka N, Pataro G, Ferrari G, Vorobiev E (2015) Ultrasound-assisted green solvent extraction of high-added value compounds from microalgae Nannochloropsis spp. Bioresour Technol 198:262–267. https://doi.org/10.1016/j.biortech.2015.09.020

    Article  Google Scholar 

  11. Onofrejova L, Vasickova J, Klejdus B, Stratil P, Misurcova L, Kracmar S, Kopecky J, Vacek J (2010) Bioactive phenols in algae: The application of pressurized-liquid and solid-phase extraction techniques. J Pharmaceut Biomed 51(2):464–470. https://doi.org/10.1016/j.jpba.2009.03.027

    Article  Google Scholar 

  12. Kudlak B, Owczarek K, Namiesnik J (2015) Selected issues related to the toxicity of ionic liquids and deep eutectic solvents-a review. Environ Sci Pollut R 22(16):11975–11992. https://doi.org/10.1007/s11356-015-4794-y

    Article  Google Scholar 

  13. Brglez Mojzer E, Knez Hrncic M, Skerget M, Knez Z, Bren U (2016) Polyphenols: Extraction methods, antioxidative action, bioavailability and anticarcinogenic effects. Molecules 21(7). https://doi.org/10.3390/molecules21070901

  14. Irakli M, Chatzopoulou P, Ekateriniadou L (2018) Optimization of ultrasound-assisted extraction of phenolic compounds: oleuropein, phenolic acids, phenolic alcohols and flavonoids from olive leaves and evaluation of its antioxidant activities. Ind Crop Prod 124:382–388. https://doi.org/10.1016/j.indcrop.2018.07.070

    Article  Google Scholar 

  15. Roohinejad S, Koubaa M, Barba FJ, Greiner R, Orlien V, Lebovka NI (2016) Negative pressure cavitation extraction: a novel method for extraction of food bioactive compounds from plant materials. Trends in Food Science & Technology 52:98–108. https://doi.org/10.1016/j.tifs.2016.04.005

    Article  Google Scholar 

  16. van Osch DJGP, Kollau LJBM, van den Bruinhorst A, Asikainen S, Rocha MAA, Kroon MC (2017) Ionic liquids and deep eutectic solvents for lignocellulosic biomass fractionation. Phys Chem Chem Phys 19(4):2636–2665. https://doi.org/10.1039/c6cp07499e

    Article  Google Scholar 

  17. Tang X, Zuo M, Li Z, Liu H, Xiong CX, Zeng XH, Sun Y, Hu L, Liu SJ, Lei TZ, Lin L (2017) Green processing of lignocellulosic biomass and its derivatives in deep eutectic solvents. Chemsuschem 10(13):2696–2706. https://doi.org/10.1002/cssc.201700457

    Article  Google Scholar 

  18. Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114(21):11060–11082. https://doi.org/10.1021/cr300162p

    Article  Google Scholar 

  19. Francisco M, van den Bruinhorst A, Kroon MC (2012) New natural and renewable low transition temperature mixtures (LTTMs): Screening as solvents for lignocellulosic biomass processing. Green Chem 14(8):2153. https://doi.org/10.1039/c2gc35660k

    Article  Google Scholar 

  20. Radosevic K, Bubalo MC, Srcek VG, Grgas D, Dragicevic TL, Redovnikovic IR (2015) Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol Environ Saf 112:46–53. https://doi.org/10.1016/j.ecoenv.2014.09.034

    Article  Google Scholar 

  21. Dai YT, Witkamp GJ, Verpoorte R, Choi YH (2015) Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem 187:14–19. https://doi.org/10.1016/j.foodchem.2015.03.123

    Article  Google Scholar 

  22. Murador DC, Mesquita LMD, Vannuchi N, Braga ARC, de Rosso VV (2019) Bioavailability and biological effects of bioactive compounds extracted with natural deep eutectic solvents and ionic liquids: advantages over conventional organic solvents. Curr Opin Food Sci 26:25–34. https://doi.org/10.1016/j.cofs.2019.03.002

    Article  Google Scholar 

  23. Espino M, Fernandez MD, Gomez FJV, Silva MF (2016) Natural designer solvents for greening analytical chemistry. Trac-Trend Anal Chem 76:126–136. https://doi.org/10.1016/j.trac.2015.11.006

    Article  Google Scholar 

  24. Zainal-Abidin MH, Hayyan M, Hayyan A, Jayakumar NS (2017) New horizons in the extraction of bioactive compounds using deep eutectic solvents: a review. Anal Chim Acta 979:1–23. https://doi.org/10.1016/j.aca.2017.05.012

    Article  Google Scholar 

  25. Ruesgas-Ramon M, Figueroa-Espinoza MC, Durand E (2017) Application of deep eutectic solvents (DES) for phenolic compounds extraction: overview, challenges, and opportunities. J Agr Food Chem 65(18):3591–3601. https://doi.org/10.1021/acs.jafc.7b01054

    Article  Google Scholar 

  26. Skarpalezos D, Detsi A (2019) Deep eutectic solvents as extraction media for valuable flavonoids from natural sources. Appl Sci-Basel 9(19):23. https://doi.org/10.3390/app9194169

    Article  Google Scholar 

  27. Dai Y, Witkamp GJ, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L. Anal Chem 85(13):6272–6278. https://doi.org/10.1021/ac400432p

    Article  Google Scholar 

  28. Dai Y, van Spronsen J, Witkamp GJ, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68. https://doi.org/10.1016/j.aca.2012.12.019

    Article  Google Scholar 

  29. Ozturk B, Parkinson C, Gonzalez-Miquel M (2018) Extraction of polyphenolic antioxidants from orange peel waste using deep eutectic solvents. Sep Purif Technol 206:1–13. https://doi.org/10.1016/j.seppur.2018.05.052

    Article  Google Scholar 

  30. Apostolakis A, Grigorakis S, Makris DP (2014) Optimisation and comparative kinetics study of polyphenol extraction from olive leaves (Olea europaea) using heated water/glycerol mixtures. Sep Purif Technol 128:89–95. https://doi.org/10.1016/j.seppur.2014.03.010

    Article  Google Scholar 

  31. Maugeri Z, Domínguez de María P (2012) Novel choline chloride based deep eutectic solvents with renewable hydrogen bond donors: levulinic acid and sugar-based polyols. RSC Adv 2(2):421–425. https://doi.org/10.1039/c1ra00630d

    Article  Google Scholar 

  32. Mahmood W, Lorwirachsutee A, Theodoropoulos C, Gonzalez-Miquel M (2019) Polyol-based deep eutectic solvents for extraction of natural polyphenolic antioxidants from Chlorella vulgaris. ACS Sustain Chem Eng 7(5):5018–5026. https://doi.org/10.1021/acssuschemeng.8b05642

    Article  Google Scholar 

  33. Mulia K, Fauzia F, Krisanti EA (2019) Polyalcohols as hydrogen-bonding donors in choline chloride-based deep eutectic solvents for extraction of xanthones from the pericarp of Garcinia mangostana L. Molecules 24(3):636. https://doi.org/10.3390/molecules24030636

    Article  Google Scholar 

  34. Bi W, Tian M, Row KH (2013) Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. J Chromatogr A 1285:22–30. https://doi.org/10.1016/j.chroma.2013.02.041

    Article  Google Scholar 

  35. Andrew P, Abbott DB, Capper G, Davies DL, Rasheed RK (2004) Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J Am Chem Soc 126:9142–9147

    Article  Google Scholar 

  36. Lu WD, Alam MA, Pan Y, Wu JC, Wang ZM, Yuan ZH (2016) A new approach of microalgal biomass pretreatment using deep eutectic solvents for enhanced lipid recovery for biodiesel production. Bioresource Technol 218:123–128. https://doi.org/10.1016/j.biortech.2016.05.120

    Article  Google Scholar 

  37. Vieira V, Prieto MA, Barros L, Coutinho JAP, Ferreira ICFR, Ferreira O (2018) Enhanced extraction of phenolic compounds using choline chloride based deep eutectic solvents from Juglans regia L. Ind Crop Prod 115:261–271. https://doi.org/10.1016/j.indcrop.2018.02.029

    Article  Google Scholar 

  38. Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Novel solvent properties of choline chloride/urea mixtures. Chem Commun (Camb) 1:70–71. https://doi.org/10.1039/b210714g

    Article  Google Scholar 

  39. Pal CBT, Jadeja GC (2019) Deep eutectic solvent-based extraction of polyphenolic antioxidants from onion (Allium cepa L.) peel. J Sci Food Agric 99(4):1969–1979. https://doi.org/10.1002/jsfa.9395

    Article  Google Scholar 

  40. Duan L, Zhang C, Zhang C, Xue Z, Zheng Y, Guo L (2019) Green extraction of phenolic acids from Artemisia argyi leaves by tailor-made ternary deep eutectic solvents. Molecules 24(15). https://doi.org/10.3390/molecules24152842

  41. 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 48:228–239. https://doi.org/10.1016/j.ifset.2018.07.001

    Article  Google Scholar 

  42. Prasad KN, Yang B, Shi J, Yu C, Zhao M, Xue S, Jiang Y (2010) Enhanced antioxidant and antityrosinase activities of longan fruit pericarp by ultra-high-pressure-assisted extraction. J Pharm Biomed Anal 51(2):471–477. https://doi.org/10.1016/j.jpba.2009.02.033

    Article  Google Scholar 

  43. Guo X, Zhao W, Liao X, Hu X, Wu J, Wang X (2017) Extraction of pectin from the peels of pomelo by high-speed shearing homogenization and its characteristics. LWT-Food Sci Technol 79:640–646. https://doi.org/10.1016/j.lwt.2016.12.001

    Article  Google Scholar 

  44. Briones-Labarca V, Plaza-Morales M, Giovagnoli-Vicuña C, Jamett F (2015) High hydrostatic pressure and ultrasound extractions of antioxidant compounds, sulforaphane and fatty acids from Chilean papaya (Vasconcellea pubescens) seeds: Effects of extraction conditions and methods. LWT-Food Sci Technol 60(1):525–534. https://doi.org/10.1016/j.lwt.2014.07.057

    Article  Google Scholar 

  45. Yang LL, Li L, Hu H, Wan JB, Li P (2019) Natural deep eutectic solvents for simultaneous extraction of multi-bioactive components from Jinqi Jiangtang preparations. Pharmaceutics 11(1):18. https://doi.org/10.3390/pharmaceutics11010018

    Article  Google Scholar 

  46. Panic M, Gunjevic V, Cravotto G, Redovnikovic IR (2019) Enabling technologies for the extraction of grape-pomace anthocyanins using natural deep eutectic solvents in up-to-half-litre batches extraction of grape-pomace anthocyanins using NADES. Food Chem 300:125185. https://doi.org/10.1016/j.foodchem.2019.125185

    Article  Google Scholar 

  47. Chanioti S, Tzia C (2017) Optimization of ultrasound-assisted extraction of oil from olive pomace using response surface technology: oil recovery, unsaponifiable matter, total phenol content and antioxidant activity. LWT - Food Sci Technol 79:178–189. https://doi.org/10.1016/j.lwt.2017.01.029

    Article  Google Scholar 

  48. Chemat F, Rombaut N, Sicaire AG, Meullemiestre A, Fabiano-Tixier AS, Abert-Vian M (2017) Ultrasound assisted extraction of food and natural products. Mechanisms, techniques, combinations, protocols and applications. A review. Ultrason Sonochem 34:540–560. https://doi.org/10.1016/j.ultsonch.2016.06.035

    Article  Google Scholar 

  49. Chen J, Liu MJ, Wang Q, Du HZ, Zhang LW (2016) Deep eutectic solvent-based microwave-assisted method for extraction of hydrophilic and hydrophobic components from Radix Salviae miltiorrhizae. Molecules 21(10):1383. https://doi.org/10.3390/molecules21101383

    Article  Google Scholar 

  50. Bagherian H, Zokaee Ashtiani F, Fouladitajar A, Mohtashamy M (2011) Comparisons between conventional, microwave- and ultrasound-assisted methods for extraction of pectin from grapefruit. Chem Eng Process 50(11-12):1237–1243. https://doi.org/10.1016/j.cep.2011.08.002

    Article  Google Scholar 

  51. Koutsoukos S, Tsiaka T, Tzani A, Zoumpoulakis P, Detsi A (2019) Choline chloride and tartaric acid, a natural deep eutectic solvent for the efficient extraction of phenolic and carotenoid compounds. J Clean Prod 241:118384. https://doi.org/10.1016/j.jclepro.2019.118384

    Article  Google Scholar 

  52. Wang XH, Wang JP (2019) Effective extraction with deep eutectic solvents and enrichment by macroporous adsorption resin of flavonoids from Carthamus tinctorius L. J Pharm Biomed Anal 176:112804. https://doi.org/10.1016/j.jpba.2019.112804

    Article  Google Scholar 

  53. Alañón ME, Ivanović M, Gómez-Caravaca AM, Arráez-Román D, Segura-Carretero A (2020) Choline chloride derivative-based deep eutectic liquids as novel green alternative solvents for extraction of phenolic compounds from olive leaf. Arab J Chem 13(1):1685–1701. https://doi.org/10.1016/j.arabjc.2018.01.003

    Article  Google Scholar 

  54. Cao Q, Li JH, Xia Y, Li W, Luo S, Ma CH, Liu SX (2019) Green extraction of six phenolic compounds from rattan (Calamoideae faberii) with deep eutectic solvent by homogenate-assisted vacuum-cavitation method. Molecules 24:113–127. https://doi.org/10.3390/molecules24010113

    Article  Google Scholar 

  55. Asyraf WM, Wan Mahmood AL, Theodoropoulos C, Gonzalez-Miquel M (2019) Polyol-based deep eutectic solvents for extraction of natural polyphenolic antioxidants from Chlorella vulgaris. ACS Sustainable Chem Eng 7(5):5018–5026. https://doi.org/10.1021/acssuschemeng.8b05642

    Article  Google Scholar 

  56. Peng F, Xu P, Zhao BY, Zong MH, Lou WY (2018) The application of deep eutectic solvent on the extraction and in vitro antioxidant activity of rutin from Sophora japonica bud. J Food Sci Technol 55(6):2326–2333. https://doi.org/10.1007/s13197-018-3151-9

    Article  Google Scholar 

  57. Shang X, Dou Y, Zhang Y, Tan J-N, Liu X, Zhang Z (2019) Tailor-made natural deep eutectic solvents for green extraction of isoflavones from chickpea (Cicer arietinum L.) sprouts. Ind Crop Prod 140:111724. https://doi.org/10.1016/j.indcrop.2019.111724

    Article  Google Scholar 

  58. Fraige K, Arrua RD, Sutton AT, Funari CS, Cavalheiro AJ, Hilder EF, Bolzani VDS (2019) Using natural deep eutectic solvents for the extraction of metabolites in Byrsonima intermedia leaves. J Sep Sci 42(2):591–597. https://doi.org/10.1002/jssc.201800905

    Article  Google Scholar 

  59. Xie YL, Liu HR, Lin L, Zhao MJ, Zhang L, Zhang YS, Wu YC (2019) Application of natural deep eutectic solvents to extract ferulic acid from Ligusticum chuanxiong Hort with microwave assistance. RSC Adv 9(39):22677–22684. https://doi.org/10.1039/c9ra02665g

    Article  Google Scholar 

  60. Meng Z, Zhao J, Duan H, Guan Y, Zhao L (2018) Green and efficient extraction of four bioactive flavonoids from Pollen Typhae by ultrasound-assisted deep eutectic solvents extraction. J Pharm Biomed Anal 161:246–253. https://doi.org/10.1016/j.jpba.2018.08.048

    Article  Google Scholar 

  61. Huang Y, Feng F, Jiang J, Qiao Y, Wu T, Voglmeir J, Che ZG (2017) Green and efficient extraction of rutin from tartary buckwheat hull by using natural deep eutectic solvents. Food Chem 221:1400–1405. https://doi.org/10.1016/j.foodchem.2016.11.013

    Article  Google Scholar 

  62. Wang G, Cui Q, Yin LJ, Zheng X, Gao MZ, Meng Y, Wang W (2019) Efficient extraction of flavonoids from Flos Sophorae Immaturus by tailored and sustainable deep eutectic solvent as green extraction media. J Pharm Biomed Anal 170:285–294. https://doi.org/10.1016/j.jpba.2018.12.032

    Article  Google Scholar 

  63. Cui Q, Liu J-Z, Wang L-T, Kang Y-F, Meng Y, Jiao J, Fu Y-J (2018) Sustainable deep eutectic solvents preparation and their efficiency in extraction and enrichment of main bioactive flavonoids from sea buckthorn leaves. J Clean Prod 184:826–835. https://doi.org/10.1016/j.jclepro.2018.02.295

    Article  Google Scholar 

  64. Zeng J, Dou Y, Yan N, Li N, Zhang H, Tan JN (2019) Optimizing ultrasound-assisted deep eutectic solvent extraction of bioactive compounds from Chinese wild rice. Molecules 24(15):2718. https://doi.org/10.3390/molecules24152718

    Article  Google Scholar 

  65. Mansur AR, Song NE, Jang HW, Lim TG, Yoo M, Nam TG (2019) Optimizing the ultrasound-assisted deep eutectic solvent extraction of flavonoids in common buckwheat sprouts. Food Chem 293:438–445. https://doi.org/10.1016/j.foodchem.2019.05.003

    Article  Google Scholar 

  66. Ali MC, Chen J, Zhang H, Li Z, Zhao L, Qiu H (2019) Effective extraction of flavonoids from Lycium barbarum L. fruits by deep eutectic solvents-based ultrasound-assisted extraction. Talanta 203:16–22. https://doi.org/10.1016/j.talanta.2019.05.012

    Article  Google Scholar 

  67. Mamilla JLK, Novak U, Grilc M, Likozar B (2019) Natural deep eutectic solvents (DES) for fractionation of waste lignocellulosic biomass and its cascade conversion to value-added bio-based chemicals. Biomass Bioenergy 120:417–425. https://doi.org/10.1016/j.biombioe.2018.12.002

    Article  Google Scholar 

  68. Obluchinskaya ED, Daurtseva AV, Pozharitskaya ON, Flisyuk EV, Shikov AN (2019) Natural deep eutectic solvents as alternatives for extracting phlorotannins from brown algae. Pharm Chem J 53(3):243–247. https://doi.org/10.1007/s11094-019-01987-0

    Article  Google Scholar 

  69. Ivanovic M, Alanon ME, Arraez-Roman D, Segura-Carretero A (2018) Enhanced and green extraction of bioactive compounds from Lippia citriodora by tailor-made natural deep eutectic solvents. Food Res Int 111:67–76. https://doi.org/10.1016/j.foodres.2018.05.014

    Article  Google Scholar 

  70. Maja Molnar MJ, Jokic S (2018) Optimization of the process conditions for the extraction of rutin from Ruta graveolens L. by choline chloride based deep eutectic solvents. Solvent Extr Res Dev 25(2):109–116. https://doi.org/10.15261/serdj.25.109

    Article  Google Scholar 

  71. Pavic V, Flacer D, Jakovljevic M, Molnar M, Jokic S (2019) Assessment of total phenolic content, in vitro antioxidant and antibacterial activity of Ruta graveolens L. Extracts obtained by choline chloride based natural deep eutectic solvents. Plants-Basel 8(3). https://doi.org/10.3390/plants8030069

  72. Zhou PF, Wang XP, Liu PZ, Huang J, Wang C, Pan MS, Kuang ZS (2018) Enhanced phenolic compounds extraction from Morus alba L. leaves by deep eutectic solvents combined with ultrasonic-assisted extraction. Ind Crop Prod 120:147–154. https://doi.org/10.1016/j.indcrop.2018.04.071

    Article  Google Scholar 

  73. Xu M, Ran L, Chen N, Fan X, Ren D, Yi L (2019) Polarity-dependent extraction of flavonoids from citrus peel waste using a tailor-made deep eutectic solvent. Food Chem 297:124970. https://doi.org/10.1016/j.foodchem.2019.124970

    Article  Google Scholar 

  74. Duan L, Zhang WH, Zhang ZH, Liu EH, Guo L (2019) Evaluation of natural deep eutectic solvents for the extraction of bioactive flavone C-glycosides from Flos Trollii. Microchem J 145:180–186. https://doi.org/10.1016/j.microc.2018.10.031

    Article  Google Scholar 

  75. Guo N, Ping K, Jiang YW, Wang LT, Niu LJ, Liu ZM, Fu YJ (2019) Natural deep eutectic solvents couple with integrative extraction technique as an effective approach for mulberry anthocyanin extraction. Food Chem 296:78–85. https://doi.org/10.1016/j.foodchem.2019.05.196

    Article  Google Scholar 

  76. Liu YJ, Zhang H, Yu HM, Guo SH, Chen DW (2019) Deep eutectic solvent as a green solvent for enhanced extraction of narirutin, naringin, hesperidin and neohesperidin from Aurantii Fructus. Phytochem Analysis 30(2):156–163. https://doi.org/10.1002/pca.2801

    Article  Google Scholar 

  77. Saha SK, Dey S, Chakraborty R (2019) Effect of choline chloride-oxalic acid based deep eutectic solvent on the ultrasonic assisted extraction of polyphenols from Aegle marmelos. J Mol Liq 287:110956. https://doi.org/10.1016/j.molliq.2019.110956

    Article  Google Scholar 

  78. Liu X, Fu NJ, Zhang QG, Cai SF, Wang Q, Han DD, Tang BK (2019) Green tailoring with water of choline chloride deep eutectic solvents for the extraction of polyphenols from palm samples. J Chromatogr Sci 57(3):272–278. https://doi.org/10.1093/chromsci/bmy099

    Article  Google Scholar 

  79. Kuddushi M, Nangala GS, Rajput S, Ijardar SP, Malek NI (2019) Understanding the peculiar effect of water on the physicochemical properties of choline chloride based deep eutectic solvents theoretically and experimentally. J Mol Liq 278:607–615. https://doi.org/10.1016/j.molliq.2019.01.053

    Article  Google Scholar 

  80. Bosiljkov T, Dujmić F, Cvjetko Bubalo M, Hribar J, Vidrih R, Brnčić M, Zlatic E, Radojčić Redovniković I, Jokić S (2017) Natural deep eutectic solvents and ultrasound-assisted extraction: Green approaches for extraction of wine lees anthocyanins. Food Bioprod Process 102:195–203. https://doi.org/10.1016/j.fbp.2016.12.005

    Article  Google Scholar 

  81. Wang T, Jiao J, Gai QY, Wang P, Guo N, Niu LL, Fu YJ (2017) Enhanced and green extraction polyphenols and furanocoumarins from Fig (Ficus carica L.) leaves using deep eutectic solvents. J Pharm Biomed Anal 145:339–345. https://doi.org/10.1016/j.jpba.2017.07.002

    Article  Google Scholar 

  82. Gabriele F, Chiarini M, Germani R, Tiecco M, Spreti N (2019) Effect of water addition on choline chloride/glycol deep eutectic solvents: characterization of their structural and physicochemical properties. J Mol Liq 291:111301. https://doi.org/10.1016/j.molliq.2019.111301

    Article  Google Scholar 

  83. Yadav A, Pandey S (2014) Densities and viscosities of (choline chloride+urea) deep eutectic solvent and its aqueous mixtures in the temperature range 293.15 K to 363.15 K. Journal of Chemical & Engineering Data 59(7):2221–2229. https://doi.org/10.1021/je5001796

    Article  Google Scholar 

  84. Zhao B-Y, Xu P, Yang F-X, Wu H, Zong M-H, Lou W-Y (2015) Biocompatible deep eutectic solvents based on choline chloride: Characterization and application to the extraction of rutin from Sophora japonica. ACS Sustain Chem Eng 3(11):2746–2755. https://doi.org/10.1021/acssuschemeng.5b00619

    Article  Google Scholar 

  85. Ghaedi H, Ayoub M, Sufian S, Shariff AM, Lal B (2017) The study on temperature dependence of viscosity and surface tension of several Phosphonium-based deep eutectic solvents. J Mol Liq 241:500–510. https://doi.org/10.1016/j.molliq.2017.06.024

    Article  Google Scholar 

  86. Chilev C, Koleva V, Simeonov E (2014) A new empirical model for calculation the effective diffusion coefficient for solid-liquid extraction from plants. Ind Eng Chem Res 53(15):6288–6296. https://doi.org/10.1021/ie402473r

    Article  Google Scholar 

  87. Athanasiadis V, Grigorakis S, Lalas S, Makris DP (2017) Highly efficient extraction of antioxidant polyphenols from Olea europaea leaves using an eco-friendly glycerol/glycine deep eutectic solvent. Waste Biomass Valori 9(11):1985–1992. https://doi.org/10.1007/s12649-017-9997-7

    Article  Google Scholar 

  88. Chew KK, Khoo MZ, Ng SY, Thoo YY, Wan Mustapha WA, Ho CW (2011) Effect of ethanol concentration, extraction time and extraction temperature on the recovery of phenolic compounds and antioxidant capacity of Orthosiphon stamineus extracts. Int Food Res J 18(4):1427–1435. https://doi.org/10.1111/jfpp.13417

    Article  Google Scholar 

  89. Gąsecka M, Siwulski M, Magdziak Z, Budzyńska S, Stuper-Szablewska K, Niedzielski P, Mleczek M (2020) The effect of drying temperature on bioactive compounds and antioxidant activity of Leccinum scabrum (Bull.) Gray and Hericium erinaceus (Bull.) Pers. J Food Sci Technol 57:513–525. https://doi.org/10.1007/s13197-019-04081-1

    Article  Google Scholar 

  90. Park HE, Tang B, Row KH (2014) Application of deep eutectic solvents as additives in ultrasonic extraction of two phenolic acids from Herba Artemisiae Scopariae. Anal Lett 47(9):1476–1484. https://doi.org/10.1080/00032719.2013.874016

    Article  Google Scholar 

  91. Vu HT, Scarlett CJ, Vuong QV (2019) Maximising recovery of phenolic compounds and antioxidant properties from banana peel using microwave assisted extraction and water. J Food Sci Technol 56(3):1360–1370. https://doi.org/10.1007/s13197-019-03610-2

    Article  Google Scholar 

  92. Athanasiadis V, Grigorakis S, Lalas S, Makris DP (2018) Methyl β-cyclodextrin as a booster for the extraction for Olea europaea leaf polyphenols with a bio-based deep eutectic solvent. Biomass Convers Bior 8(2):345–355. https://doi.org/10.1007/s13399-017-0283-5

    Article  Google Scholar 

  93. Cui Q, Peng X, Yao XH, Wei ZF, Luo M, Wang W, Zhao CJ, Fu YJ, Zu YG (2015) Deep eutectic solvent-based microwave-assisted extraction of genistin, genistein and apigenin from pigeon pea roots. Sep Purif Technol 150:63–72. https://doi.org/10.1016/j.seppur.2015.06.026

    Article  Google Scholar 

  94. Nam MW, Zhao J, Lee MS, Jeong JH, Lee J (2015) Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: application to flavonoid extraction from Flos sophorae. Green Chem 17(3):1718–1727. https://doi.org/10.1039/c4gc01556h

    Article  Google Scholar 

  95. Yoo DE, Jeong KM, Han SY, Kim EM, Jin Y, Lee J (2018) Deep eutectic solvent-based valorization of spent coffee grounds. Food Chem 255:357–364. https://doi.org/10.1016/j.foodchem.2018.02.096

    Article  Google Scholar 

  96. Carmela Conidi AC, Caiazzo F, Drioli E (2017) Separation and purification of phenolic compounds from pomegranate juice by ultrafiltration and nanofiltration membranes. J Food Eng 195:1–13. https://doi.org/10.1016/j.jfoodeng

    Article  Google Scholar 

  97. Crespo JG, Brazinha C (2010) Membrane processing: Natural antioxidants from winemaking by-products. Filtr Separat 47(2):32–35. https://doi.org/10.1016/S0015-1882(10)70079-3

    Article  Google Scholar 

  98. Sami Yammine SB, Manteau S, Turk M, Ghidossi R, Vorobiev E, Mietton-Peuchot M (2018) Extraction and purification of high added value compounds from by-products of the winemaking chain using alternative/nonconventional processes/technologies. Crit Rev Food Sci Nutr 58(8):1375–1390. https://doi.org/10.1080/10408398.2016.1259982

    Article  Google Scholar 

  99. Zainal-Abidin MH, Hayyan M, Ngoh GC, Wong WF, Looi CY (2019) Emerging frontiers of deep eutectic solvents in drug discovery and drug delivery systems. J Controlled Release 316:168–195. https://doi.org/10.1016/j.jconrel.2019.09.019

    Article  Google Scholar 

  100. Jeong KM, Ko J, Zhao J, Jin Y, Yoo DE, Han SY, Lee J (2017) Multi-functioning deep eutectic solvents as extraction and storage media for bioactive natural products that are readily applicable to cosmetic products. J Clean Prod 151:87–95. https://doi.org/10.1016/j.jclepro.2017.03.038

    Article  Google Scholar 

  101. Durand E, Lecomte J, Upasani R, Chabi B, Bayrasy C, Barea B, Jublanc E, Clarke MJ, Moore DJ, Crowther J, Wrutniak-Cabello C, Villeneuve P (2017) Evaluation of the ROS inhibiting activity and mitochondrial targeting of phenolic compounds in fibroblast cells model system and enhancement of efficiency by natural deep eutectic solvent (NADES) formulation. Pharm Res 34(5):1134–1146. https://doi.org/10.1007/s11095-017-2124-4

    Article  Google Scholar 

Download references

Acknowledgments

The authors are thankful for the valuable comments by anonymous reviewers, which help greatly improve the manuscript.

Funding

The study was financially supported by the Shaoguan University key research project (grant no. SZ2016KJ02) and the China Scholarship Council (grant no. 201708440546).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Weidong Lu.

Additional information

Publisher’s note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lu, W., Liu, S. Choline chloride–based deep eutectic solvents (Ch-DESs) as promising green solvents for phenolic compounds extraction from bioresources: state-of-the-art, prospects, and challenges. Biomass Conv. Bioref. 12, 2949–2962 (2022). https://doi.org/10.1007/s13399-020-00753-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13399-020-00753-7

Keywords

Navigation