Advanced Extraction Techniques Combined with Natural Deep Eutectic Solvents for Extracting Phenolic Compounds from Pomegranate (Punica granatum L.) Peels
Abstract
:1. Introduction
2. Results
2.1. Physicochemical Characterization of NaDESs
2.2. NaDES Screening Applying UAE
2.3. Effect of PLE Temperature
2.4. Influence of the Advanced Extraction Technique Used on the Recovery of Target Compounds
3. Discussion
4. Materials and Methods
4.1. Chemical and Reagents
4.2. Sample
4.3. Synthesis of Natural Deep Eutectic Solvents (NaDESs)
4.4. NaDES Characterization
4.4.1. pH
4.4.2. Viscosity
4.4.3. Density
4.5. Ultrasound-Assisted Extraction (UAE) and Pressurized Liquid Extraction (PLE)
4.6. Total Phenolic Content (TPC)
4.7. High-Performance Liquid Chromatography (HPLC-DAD)
4.8. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Iriondo-DeHond, M.; Miguel, E.; Del Castillo, M.D. Food byproducts as sustainable ingredients for innovative and healthy dairy foods. Nutrients 2018, 10, 1358. [Google Scholar] [CrossRef] [PubMed]
- Bharat Helkar, P.; Sahoo, A. Review: Food industry by-products used as a functional food ingredients. Int. J. Waste Resour. 2016, 6, 1–6. [Google Scholar] [CrossRef]
- Maina, S.; Kachrimanidou, V.; Koutinas, A. A roadmap towards a circular and sustainable bioeconomy through waste valorization. Curr. Opin. Green Sustain. Chem. 2017, 8, 18–23. [Google Scholar] [CrossRef]
- Benetto, E.; Gericke, K.; Guiton, M. (Eds.) Designing Sustainable Technologies, Products and Policies: From Science to Innovation; Springer International Publishing: Cham, Switzerland, 2018. [Google Scholar] [CrossRef]
- Stratistics MRC. Market Resesarch Report. Pomegranate Market Forecasts to 2030-Global Analysis by Product (Pomegranate Powder, Pomegranate Concentrate and Pomegranate Juice), Category (Conventional and Organic), Application and by Geography. Global Market Research Company (Online Source). 2023. Available online: https://www.strategymrc.com/report/pomegranate-market (accessed on 15 August 2024).
- Harscoat-Schiavo, C.; Khoualdia, B.; Savoire, R.; Hobloss, S.; Buré, C.; Samia, B.A.; Subra-Paternault, P. Extraction of phenolics from pomegranate residues: Selectivity induced by the methods. J. Supercrit. Fluids 2021, 176, 105300. [Google Scholar] [CrossRef]
- Redha, A.A.A.; Hasan, A.M.; Mandeel, Q. Phytochemical determinations of pomegranate (Punica granatum) rind and aril extracts and their antioxidant, antidiabetic and antibacterial activity. Nat. Prod. Chem. Res. 2018, 6, 4. [Google Scholar] [CrossRef]
- Bertolo, M.R.V.; Martins, V.C.A.; Plepis, A.M.G.; Bogusz, S. Utilization of pomegranate peel waste: Natural deep eutectic solvents as a green strategy to recover valuable phenolic compounds. J. Clean. Prod. 2021, 327, 129471. [Google Scholar] [CrossRef]
- Salim, A.; Deiana, P.; Fancello, F.; Molinu, M.G.; Santona, M.; Zara, S. Antimicrobial and antibiofilm activities of pomegranate peel phenolic compounds: Varietal screening through a multivariate approach. J. Bioresour. Bioprod. 2023, 8, 146–161. [Google Scholar] [CrossRef]
- Selahvarzi, A.; Ramezan, Y.; Sanjabi, M.R.; Namdar, B.; Akbarmivehie, M.; Mirsaeedghazi, H.; Azarikia, F. Optimization of ultrasonic-assisted extraction of phenolic compounds from pomegranate and orange peels and their antioxidant activity in a functional drink. Food Biosci. 2022, 49, 101918. [Google Scholar] [CrossRef]
- Oudane, B.; Boudemagh, D.; Bounekhel, M.; Sobhi, W.; Vidal, M.; Broussy, S. Isolation, characterization, antioxidant activity, and protein-precipitating capacity of the hydrolyzable tannin punicalagin from pomegranate yellow peel (Punica granatum). J. Mol. Struct. 2018, 1156, 390–396. [Google Scholar] [CrossRef]
- Liu, Y.; Kong, K.W.; Wu, D.-T.; Liu, H.-Y.; Li, H.-B.; Zhang, J.-R.; Gan, R.-Y. Pomegranate peel-derived punicalagin: Ultrasonic-assisted extraction, purification, and its α-glucosidase inhibitory mechanism. Food Chem. 2022, 374, 131635. [Google Scholar] [CrossRef]
- Campos, L.; Seixas, L.; Henriques, M.H.F.; Peres, A.M.; Veloso, A.C.A. Pomegranate peels and seeds as a source of phenolic compounds: Effect of cultivar, by-product, and extraction solvent. Int. J. Food Sci. 2022, 2022, 1–11. [Google Scholar] [CrossRef]
- Ranjha, M.M.A.N.; Amjad, S.; Ashraf, S.; Khawar, L.; Safdar, M.N.; Jabbar, S.; Nadeem, M.; Mahmood, S.; Murtaza, M.A. Extraction of polyphenols from apple and pomegranate peels employing different extraction techniques for the development of functional date bars. Int. J. Fruit Sci. 2020, 20 (Suppl. S3), S1201–S1221. [Google Scholar] [CrossRef]
- Kennas, A.; Amellal-Chibane, H. Comparison of five solvents in the extraction of phenolic anti-oxidants from pomegranate (Punica granatum L.) peel. N. Afr. J. Food Nutr. Res. 2019, 3, 140–147. [Google Scholar] [CrossRef]
- Wang, Z. Extract of phenolics from pomegranate peels. Open Food Sci. J. 2011, 5, 17–25. [Google Scholar] [CrossRef]
- Wong-Paz, J.E.; Muñiz-Márquez, D.B.; Aguilar-Zárate, P.; Ascacio-Valdés, J.A.; Cruz, K.; Reyes-Luna, C.; Rodríguez, R.; Aguilar, C.N. Extraction of bioactive phenolic compounds by alternative technologies. In Ingredients Extraction by Physicochemical Methods in Food; Elsevier: Amsterdam, The Netherlands, 2017; pp. 229–252. [Google Scholar] [CrossRef]
- Plaza, M.; Domínguez-Rodríguez, G.; Sahelices, C.; Marina, M.L. A sustainable approach for extracting non-extractable phenolic compounds from mangosteen peel using ultrasound-assisted extraction and natural deep eutectic solvents. Appl. Sci. 2021, 11, 5625. [Google Scholar] [CrossRef]
- Cannavacciuolo, C.; Pagliari, S.; Frigerio, J.; Giustra, C.M.; Labra, M.; Campone, L. Natural deep eutectic solvents (NADESs) combined with sustainable extraction techniques: A review of the green chemistry approach in food analysis. Foods 2022, 12, 56. [Google Scholar] [CrossRef]
- Da Silva, D.T.; Smaniotto, F.A.; Costa, I.F.; Baranzelli, J.; Muller, A.; Somacal, S.; Monteiro, C.S.; Vizzotto, M.; Rodrigues, E.; Barcia, M.T.; et al. Natural deep eutectic solvent (NADES): A strategy to improve the bioavailability of blueberry phenolic compounds in a ready-to-use extract. Food Chem. 2021, 364, 130370. [Google Scholar] [CrossRef]
- Bragagnolo, F.S.; Socas-Rodríguez, B.; Mendiola, J.A.; Cifuentes, A.; Funari, C.S.; Ibáñez, E. Pressurized natural deep eutectic solvents: An alternative approach to agro-soy by-products. Front. Nutr. 2022, 9, 953169. [Google Scholar] [CrossRef]
- Benvenutti, L.; Zielinski, A.A.F.; Ferreira, S.R.S. Pressurized aqueous solutions of deep eutectic solvent (DES): A green emergent extraction of anthocyanins from a Brazilian berry processing by-product. Food Chem. X 2022, 13, 100236. [Google Scholar] [CrossRef]
- De Almeida Pontes, P.V.; Ayumi Shiwaku, I.; Maximo, G.J.; Caldas Batista, E.A. Choline chloride-based deep eutectic solvents as potential solvent for extraction of phenolic compounds from olive leaves: Extraction optimization and solvent characterization. Food Chem. 2021, 352, 129346. [Google Scholar] [CrossRef]
- Vo, T.P.; Pham, T.V.; Weina, K.; Tran, T.N.H.; Vo, L.T.V.; Nguyen, P.T.; Bui, T.L.H.; Phan, T.H.; Nguyen, D.Q. Green extraction of phenolics and flavonoids from black mulberry fruit using natural deep eutectic solvents: Optimization and surface morphology. BMC Chem. 2023, 17, 119. [Google Scholar] [CrossRef]
- Cvjetko Bubalo, M.; Ćurko, N.; Tomašević, M.; Kovačević Ganić, K.; Radojčić Redovniković, I. Green extraction of grape skin phenolics by using deep eutectic solvents. Food Chem. 2016, 200, 159–166. [Google Scholar] [CrossRef] [PubMed]
- Jamshaid, S.; Ahmed, D. Optimization of ultrasound-assisted extraction of valuable compounds from fruit of Melia azedarach with glycerol-choline chloride deep eutectic solvent. Sustain. Chem. Pharm. 2022, 29, 100827. [Google Scholar] [CrossRef]
- Rodriguez, N.R.; Ferre Guell, J.; Kroon, M.C. Glycerol-based deep eutectic solvents as extractants for the separation of MEK and ethanol via liquid–liquid extraction. J. Chem. Eng. Data 2016, 61, 865–872. [Google Scholar] [CrossRef]
- Zannou, O.; Pashazadeh, H.; Ghellam, M.; Ibrahim, S.A.; Koca, I. Extraction of anthocyanins from borage (Echium amoenum) flowers using choline chloride and a glycerol-based, deep eutectic solvent: Optimization, antioxidant activity, and in vitro bioavailability. Molecules 2021, 27, 134. [Google Scholar] [CrossRef] [PubMed]
- Sánchez-Martínez, J.D.; Valdés, A.; Gallego, R.; Suárez-Montenegro, Z.J.; Alarcón, M.; Ibáñez, E.; Álvarez-Rivera, G.; Cifuentes, A. Blood–brain barrier permeability study of potential neuroprotective compounds recovered from plants and agri-food by-products. Front. Nutr. 2022, 9, 924596. [Google Scholar] [CrossRef]
- Lapeña, D.; Lomba, L.; Artal, M.; Lafuente, C.; Giner, B. The NADES glyceline as a potential green solvent: A comprehensive study of its thermophysical properties and effect of water inclusion. J. Chem. Thermodyn. 2019, 128, 164–172. [Google Scholar] [CrossRef]
- Tan, Y.T.; Ngoh, G.C.; Chua, A.S.M. Effect of functional groups in acid constituent of deep eutectic solvent for extraction of reactive lignin. Bioresour. Technol. 2019, 281, 359–366. [Google Scholar] [CrossRef]
- Rente, D.; Paiva, A.; Duarte, A.R. The role of hydrogen bond donor on the extraction of phenolic compounds from natural matrices using deep eutectic systems. Molecules 2021, 26, 2336. [Google Scholar] [CrossRef]
- Palos-Hernández, A.; Gutiérrez Fernández, M.Y.; Escuadra Burrieza, J.; Pérez-Iglesias, J.L.; González-Paramás, A.M. Obtaining green extracts rich in phenolic compounds from underexploited food by-products using natural deep eutectic solvents. Opportunities and challenges. Sustain. Chem. Pharm. 2022, 29, 100773. [Google Scholar] [CrossRef]
- Radošević, K.; Cvjetko Bubalo, M.; Gaurina Srček, V.; Grgas, D.; Landeka Dragičević, T.; Radojčić Redovniković, I. Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol. Environ. Saf. 2015, 112, 46–53. [Google Scholar] [CrossRef] [PubMed]
- Castro, V.I.B.; Mano, F.; Reis, R.L.; Paiva, A.; Duarte, A.R.C. Synthesis and physical and thermodynamic properties of lactic acid and malic acid-based natural deep eutectic solvents. J. Chem. Eng. Data 2018, 63, 2548–2556. [Google Scholar] [CrossRef]
- García-Roldán, A.; Piriou, L.; Jauregi, P. Natural deep eutectic solvents as a green extraction of polyphenols from spent coffee ground with enhanced bioactivities. Front. Plant Sci. 2023, 13, 1072592. [Google Scholar] [CrossRef]
- Koh, Q.Q.; Kua, Y.L.; Gan, S.; Tan, K.W.; Lee, T.Z.E.; Cheng, W.K.; Lau, H.L.N. Sugar-based natural deep eutectic solvent (NADES): Physicochemical properties, antimicrobial activity, toxicity, biodegradability and potential use as green extraction media for phytonutrients. Sustain. Chem. Pharm. 2023, 35, 101218. [Google Scholar] [CrossRef]
- Sumere, B.R.; De Souza, M.C.; Dos Santos, M.P.; Bezerra, R.M.N.; Da Cunha, D.T.; Martinez, J.; Rostagno, M.A. Combining pressurized liquids with ultrasound to improve the extraction of phenolic compounds from pomegranate peel (Punica granatum L.). Ultrason. Sonochem. 2018, 48, 151–162. [Google Scholar] [CrossRef]
- Skulcova, A.; Russ, A.; Jablonsky, M.; Sima, J. The pH behavior of seventeen deep eutectic solvents. BioResources 2018, 13, 5042–5051. [Google Scholar] [CrossRef]
- Kim, H.J.; Yoon, K.Y. Optimization of ultrasound-assisted deep eutectic solvent extraction of bioactive compounds from pomegranate peel using response surface methodology. Food Sci. Biotechnol. 2023, 32, 1851–1860. [Google Scholar] [CrossRef]
- Mansinhos, I.; Gonçalves, S.; Rodríguez-Solana, R.; Ordóñez-Díaz, J.L.; Moreno-Rojas, J.M.; Romano, A. Ultrasonic-assisted extraction and natural deep eutectic solvents combination: A green strategy to improve the recovery of phenolic compounds from Lavandula pedunculata subsp. lusitanica (Chaytor) Franco. Antioxidants 2021, 10, 582. [Google Scholar] [CrossRef]
- García, A.; Rodríguez-Juan, E.; Rodríguez-Gutiérrez, G.; Rios, J.J.; Fernández-Bolaños, J. Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs). Food Chem. 2016, 197, 554–561. [Google Scholar] [CrossRef]
- Chaves, J.O.; Sanches, V.L.; Viganó, J.; De Souza Mesquita, L.M.; De Souza, M.C.; Da Silva, L.C.; Acunha, T.; Faccioli, L.H.; Rostagno, M.A. Integration of pressurized liquid extraction and in-line solid-phase extraction to simultaneously extract and concentrate phenolic compounds from lemon peel (Citrus limon L.). Food Res. Int. 2022, 157, 111252. [Google Scholar] [CrossRef]
- Višnjevec, A.M.; Barp, L.; Lucci, P.; Moret, S. Pressurized liquid extraction for the determination of bioactive compounds in plants with emphasis on phenolics. TrAC Trends Anal. Chem. 2024, 173, 117620. [Google Scholar] [CrossRef]
- Talekar, S.; Patti, A.F.; Vijayraghavan, R.; Arora, A. Recyclable enzymatic recovery of pectin and punicalagin rich phenolics from waste pomegranate peels using magnetic nanobiocatalyst. Food Hydrocoll. 2019, 89, 468–480. [Google Scholar] [CrossRef]
- Hernández-Corroto, E.; Plaza, M.; Marina, M.L.; García, M.C. Sustainable extraction of proteins and bioactive substances from pomegranate peel (Punica granatum L.) using pressurized liquids and deep eutectic solvents. Innov. Food Sci. Emerg. Technol. 2020, 60, 102314. [Google Scholar] [CrossRef]
- Singleton, V.L.; Orthofer, R.; Lamuela-Raventós, R.M. [14] Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent. In Methods in Enzymology; Elsevier: Amsterdam, The Netherlands, 1999; Volume 299, pp. 152–178. [Google Scholar] [CrossRef]
Abbreviation | Component 1 (HBA) | Component 2 (HBD) | Molar Ratio | Reference |
---|---|---|---|---|
ChCl:AA | Choline chloride | Acetic acid | 1:1 | [23] |
ChCl:LA | Choline chloride | Lactic acid | 1:1 | [8] |
ChCl:LA | Choline chloride | Lactic acid | 1:2 | [8] |
ChCl:Gly | Choline chloride | Glycerol | 1:2 | [8] |
ChCl:Glu | Choline chloride | Glucose | 1:2 | [8] |
NaDES | Molar Ratio | pH | Density (g/mL) | Viscosity (mPas·s) | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|
25 °C | 160 °C | 25 °C | 40 °C | 80 °C | 100 °C | 25 °C | 40 °C | 80 °C | 100 °C | ||
ChCl:AA | 1:1 | 1.40 ± 0.06 c | 1.61 ± 0.07 b | 1.10 ± 0.03 b | 0.99 ± 0.03 b | 0.99 ± 0.02 a,b | 1.07 ± 0.04 b,c | 6.6 ± 0.2 e | 5.6 ± 0.2 e | 3.7 ± 0.1 d | 3.1 ± 0.2 d |
ChCl:LA | 1:1 | 0.80 ± 0.01 d | 0.82 ± 0.01 c | 1.09 ± 0.02 b | 1.027 ± 0.008 b | 1.1 ± 0.1 a | 1.11 ± 0.02 b | 52.6 ± 0.2 a | 20.7 ± 0.8 a | 15.5 ± 0.7 a | 8.7 ± 0.3 a |
ChCl:LA | 1:2 | 0.70 ± 0.09 d | 0.9 ± 0.1 c | 1.11 ± 0.03 b | 1.06 ± 0.02 b | 1.08 ± 0.03 a,b | 1.098 ± 0.008 b,c | 8.0 ± 0.3 d | 6.7 ± 0.2 d | 5.1 ± 0.2 c | 3.7 ± 0.1 c |
ChCl:Gly | 1:2 | 1.60 ± 0.02 b | 1.70 ± 0.04 b | 0.984 ± 0.006 b | 1.04 ± 0.02 b | 1.053 ± 0.007 a,b | 1.07 ± 0.02 b,c | 10.1 ± 0.3 c | 10.5 ± 0.4 c | 5.7 ± 0.2 c | 3.8 ± 0.1 c |
ChCl:Glu | 1:2 | 3.70 ± 0.02 a | 3.09 ± 0.02 a | 1.20 ± 0.04 a | 1.128 ± 0.005 a | 1.16 ± 0.02 a | 1.23 ± 0.1 a | 23.1 ± 0.8 b | 15.7 ± 0.6 b | 6.7 ± 0.2 b | 5.7 ± 0.2 b |
Compound | Water | ChCl:AA (1:1) | ChCl:LA (1:1) | ChCl:LA (1:2) | ChCl:Gly (1:2) | ChCl:Glu (1:2) |
---|---|---|---|---|---|---|
Ellagic acid | 98 ± 2 b | 78 ± 5 c | 97 ± 3 b | 79 ± 1 c | 111.0 ± 0.9 a | 62.3 ± 0.9 d |
α-punicalagin | 76 ± 6 a | 53 ± 10 c | 68 ± 4 b | 54 ± 5 c | 82.4 ± 0.5 a | 36 ± 0.2 d |
β-punicalagin | 55 ± 5 e | 96 ± 3 c | 111 ± 1 a | 89 ± 2 d | 105.9 ± 0.7 b | 57 ± 2 e |
PLE-NaDES with ChCl:Gly (1:2) | PLE-Water | ||||
---|---|---|---|---|---|
Extraction temperature | 40 °C | 80 °C | 120 °C | 160 °C | 80 °C |
Ellagic acid (µg/g sample) | 125 ± 2 c | 191 ± 36 b | 216 ± 3 b | 408 ± 7 a | 117 ± 6 c |
α-punicalagin (µg/g sample) | 79 ± 1 b | 93 ± 1 a | 82 ± 15 a,b | 63 ± 7 c | 94 ± 8 a |
β-punicalagin (µg/g sample) | 106 ± 1 a,b | 114 ± 1 a | 92 ± 7 b | 97.6 ± 0.4 b | 84 ± 5 c |
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Oliveira, I.L.d.; Domínguez-Rodríguez, G.; Montero, L.; Viganó, J.; Cifuentes, A.; Rostagno, M.A.; Ibáñez, E. Advanced Extraction Techniques Combined with Natural Deep Eutectic Solvents for Extracting Phenolic Compounds from Pomegranate (Punica granatum L.) Peels. Int. J. Mol. Sci. 2024, 25, 9992. https://doi.org/10.3390/ijms25189992
Oliveira ILd, Domínguez-Rodríguez G, Montero L, Viganó J, Cifuentes A, Rostagno MA, Ibáñez E. Advanced Extraction Techniques Combined with Natural Deep Eutectic Solvents for Extracting Phenolic Compounds from Pomegranate (Punica granatum L.) Peels. International Journal of Molecular Sciences. 2024; 25(18):9992. https://doi.org/10.3390/ijms25189992
Chicago/Turabian StyleOliveira, Isadora Lopes de, Gloria Domínguez-Rodríguez, Lidia Montero, Juliane Viganó, Alejandro Cifuentes, Mauricio Arial Rostagno, and Elena Ibáñez. 2024. "Advanced Extraction Techniques Combined with Natural Deep Eutectic Solvents for Extracting Phenolic Compounds from Pomegranate (Punica granatum L.) Peels" International Journal of Molecular Sciences 25, no. 18: 9992. https://doi.org/10.3390/ijms25189992