Abstract
Herein, new function-oriented deep eutectic solvents (DESs) with on l-proline or betaine and DL-lactic acid were designed extraction of polyphenol compounds from grape pomace. The formations of new hydrogen between the two components of DESs were evidenced by FTIR and 1H NMR spectra. Physicochemical characteristics of deep eutectic solvents under the effect of water on density, viscosity, electrical resistance have been revealed. The betaine-based DES could changes the electrical resistance depending on the concentration of water. The feasibility of using ultrasound-assisted extraction of phytochemicals combined with betaine-based and proline-based DES as a green chemistry technique to improve extraction of green (polyphenols) compounds from grape pomace was evaluated. Grape pomace extracts were analyzed by LC-DAD-MS to identify extracted compounds and analyze the impact of type DES on compound chemical profile. LC results indicated that ultrasound-assisted extraction of phytochemicals using betaine-based and proline-based deep eutectic solvent application allowed enhanced hydroxycinnamic acids extraction, while the use of proline-based DES resulted in a more diverse compound profile. The highest recovery efficiencies were recorded with DESs giving the highest total phenolic content (80–92 mg EGE//g d.w), total flavonoid content (47–51 QUE/g d.w), antiradical activity (80% at 100 mg/ml) and reducing power (310–468 mg ASE/g extract). Scanning electron microscope (SEM) results further verified DESs intensified the destruction of cell wall structure, and thereby allowed greater release of polyphenolic from grape pomace.
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References
Aazza S (2021) Application of multivariate optimization for phenolic compounds and antioxidants extraction from moroccan cannabis sativa waste. J Chem 2021:1–11. https://doi.org/10.1155/2021/9738656
Alibade A, Lakka A, Bozinou E, Lalas SI, Chatzilazarou A, Makris DP (2021) Development of a green methodology for simultaneous extraction of polyphenols and pigments from red winemaking solid wastes (pomace) using a novel glycerol-sodium benzoate deep eutectic solvent and ultrasonication pretreatment. Environments 8(9):90. https://doi.org/10.3390/environments8090090
Athanasiadis V, Palaiogiannis D, Poulianiti K, Bozinou E, Lalas SI, Makris DP (2022) Extraction of polyphenolic antioxidants from red grape pomace and olive leaves: process optimization using a tailor-made tertiary deep eutectic solvent. Sustainability 14(11):6864. https://doi.org/10.3390/su14116864
Castro Vânia IB, Reis MF, Rui L, Alexandre P, Duarte Ana Rita C (2018) Synthesis and physical and thermodynamic properties of lactic acid and malic acid-based natural deep eutectic solvents. Chem Eng Data 63(7):2548–2556. https://doi.org/10.1021/acs.jced.7b01037
Cheng C-G, Jin W-Y, Wu L-J (2005) Study on microwave-assisted extraction of baicalin from scutellariabaicalensis. Chem Indus for Prod 25:81–83
Chyhyrynets OE, Vorob’Iova VI (2013) Anticorrosion properties of the extract of rapeseed oil cake as a volatile inhibitor of the atmospheric corrosion of steel. Mater Sci 49(3):318–325
Cvjetko Bubalo M, Ćurko N, Tomašević M, Kovačević Ganić K, Radojčić RI (2016) Green extraction of grape skin phenolics by using deep eutectic solvents. Food Chem 1(200):159–166. https://doi.org/10.1016/j.foodchem.2016.01.040
Dai Y, Van Spronsen J, Witkamp G-J, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68
Georgantzi C, Antonia-Eleni L, Dimitris PN, Makris P (2017) Combination of lactic acid-based deep eutectic solvents (DES) with β-Cyclodextrin: performance screening using ultrasound-assisted extraction of polyphenols from selected native greek medicinal plants. Agronomy 7:54. https://doi.org/10.3390/agronomy7030054
Gustinelli G, Eliasson L, Svelander C, Andlid T, Lundin L, Ahrné L, Alminger M (2018) Supercritical fluid extraction of berry seeds: chemical composition and antioxidant activity. J Food Qual 2018:1–10. https://doi.org/10.1155/2018/6046074
Jeong KM, Lee MS, Nam MW et al (2015) Tailoring and recycling of deep eutectic solvents as sustainable and efficient extraction media. J Chromatogr A 1424:10–17. https://doi.org/10.1016/j.chroma.2015.10.083
Kovač MJ, StelaJokić IJ, Molnar M (2022) Optimization of deep eutectic solvent extraction of phenolic acids and tannins from alchemilla Vulgaris L. Plants 11(4):474. https://doi.org/10.3390/plants11040474
Mustafa Bener, FurkanBurakŞen, Ayşe NurÖnem, BurcuBekdeşer, SalihaEsinÇelik, Melisa Lalikoglu, YavuzSelimAşçı, EsraCapanoglu, ReşatApak,"Microwave-assisted extraction of antioxidant compounds from by-products of Turkish hazelnut (Corylusavellana L.) using natural deep eutectic solvents: modeling, optimization and phenolic characterization" Food Chem., 385 (2022).
Neto RT, Santos SAO, Oliveira J, Silvestre AJD (2020) Tuning of proanthocyanidin extract’s composition through quaternary eutectic solvents extraction. Antioxidants 9(11):1124. https://doi.org/10.3390/antiox9111124
Pivovarov OA, Skiba MI, Makarova AK, Vorobyova VI, Pasenko OO (2017) Preparation of silver nanoparticles by contact nonequilibrium low-temperature plasma in the presence of sodium alginate. Voprosy Khimii i Khimicheskoi Tekhnologii 6:82–88
Sánchez PB, González B, Salgado J, Parajó JJ, Domínguez Á (2019) Physical properties of seven deep eutectic solvents based on l-proline or betaine. J Chem Thermodyn 131:517–523. https://doi.org/10.1016/j.jct.2018.12.017
Sánchez-Moreno C, Larrauri JA, Saura-Calixto F (1998) A procedure to measure the antiradical efficiency of polyphenols. J Sci Food Agric 76(2):270–276. https://doi.org/10.1002/(SICI)1097-0010(199802)76:2%3c270::AID-JSFA945%3e3.0.CO
Shuai Xu, Zhu Qi, Shaojie Xu, Yuan M, Lin X, Lin W, Qin Y, Li Y (2021) The phase behavior of n-ethylpyridinium tetrafluoroborate and sodium-based salts ATPS and its application in 2-chlorophenol extraction. Chin J Chem Eng 33:76–82. https://doi.org/10.1016/j.cjche.2020.07.024
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
Souza OA, Rinaldo D, Porto CM, Sambrano JR, Morgon NH, de Souza AR (2022) Computer simulation applied to structural analysis and experimental applications of natural deep eutectic solvents. Green chemistry and computational chemistry. Elsevier, pp 281–297. https://doi.org/10.1016/B978-0-12-819879-7.00043-X
Vasyliev G (2017) Polarization resistance measurement in tap water: the influence of rust electrochemical activity. J Mater Eng Perform 26(8):3939–3945
Vasyliev G, Vorobyova V, Zhuk T (2020) Raphanus sativus L. extract as a scale and corrosion inhibitor for mild steel in tap Water. J Chem 2020:1–9. https://doi.org/10.1155/2020/5089758
Vasyliev GS, Vorobyova VI, Linyucheva OV (2020) Evaluation of reducing ability and antioxidant activity of fruit pomace extracts by spectrophotometric and electrochemical methods. J Anal Methods Chem 2020:1–16. https://doi.org/10.1155/2020/8869436
Vasyliev G, Lyudmyla K, Hladun K (2022) Valorization of tomato pomace: extraction of value-added components by deep eutectic solvents and their application in the formulation of cosmetic emulsion. Biomass Conv Bioref 12:95–111. https://doi.org/10.1007/s13399-022-02337-z
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 Crops Prod 115:261–271. https://doi.org/10.1016/j.indcrop.2018.02.029
Vorobyova V, Chygyrynetś O, Skiba M, KurmakovaI BO (2017) Self-assembled monoterpenoid phenol as vapor phase atmospheric corrosion inhibitor of carbon steel. Int J Corros Scale Inhib 6(4):485–503
Wang H, Ma X, Cheng Q, Xi X, Zhang L (2018) Deep Eutectic Solvent-Based Microwave-Assisted Extraction of Baicalin from Scutellaria baicalensis Georgi. J Chem 2018:1–10. https://doi.org/10.1155/2018/9579872
Zheng B, Yuan Y, Xiang J, Jin W, Johnson JB, Li Z, Wang C, Luo D (2022) Green extraction of phenolic compounds from foxtail millet bran by ultrasonic-assisted deep eutectic solvent extraction: optimization, comparison and bioactivities. LWT 154:112740. https://doi.org/10.1016/j.lwt.2021.112740
Zhu S, Liu D, Zhu X, Along S, Zhang H (2017) Extraction of illegal dyes from red chili peppers with cholinium-based deep eutectic solvents. J Anal Methods Chem 2017:1–6. https://doi.org/10.1155/2017/2753752
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This work was supported by the Ministry of Education and Science of Ukraine [grant no. 2403, 2021].
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VV contributed to conceptualization, discussion, supervision, and coordination of the whole study, data analysis, main manuscript designing, editing, and finalization. GV contributed to preparation of NADESs, extraction, cyclic voltammetry analysis writing–review and editing draft. MS contributed to definition density. SF contributed to viscosity study. JZ contributed to definition 1H nuclear magnetic resonance. OG contributed to SEM analysis. OL contributed to formal analysis.
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Vorobyova, V., Vasyliev, G., Skiba, M. et al. Green extraction of phenolic compounds from grape pomace by deep eutectic solvent extraction: physicochemical properties, antioxidant capacity. Chem. Pap. 77, 2447–2458 (2023). https://doi.org/10.1007/s11696-022-02635-w
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DOI: https://doi.org/10.1007/s11696-022-02635-w