Abstract
In the present investigation, the optimization of a pressurized solid–liquid extraction of polyphenols from Pinus pinaster Aiton needles and bark residues has been carried out using new deep eutectic solvent systems (DES). A Box–Behnken design with response surface methodology was implemented, with six variables, including solid:liquid ratio, water content, temperature, extraction time, reactor closure state, and catalyst concentration. The DES consisting of levulinic acid: formic acid exhibited the highest content, and the optimal conditions were determined to be 0.10 g of residue in 10 mL of solvent (without water) and without catalyst, at 60 °C for 5 min. The method demonstrated excellent repeatability and intermediate precision, with a coefficient of variation of less than 5%. In addition, the antimicrobial and antioxidant activities of the polyphenol-enriched extracts were evaluated, obtaining a total reduction in S. aureus cell growth and remarkable antioxidant levels of 144.72 ± 4.24 and 161.01 ± 4.70 mg Trolox equivalents/gram for needle and bark residues, respectively. Under the optimized conditions, the new DES are remarkably superior to conventional solvents and can be recycled and reused, demonstrating that these systems have a promising environmental profile, making them valuable alternatives for biomass fractionation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abdallah MM, Cardeira M, Matias AA et al (2022) Lactic acid-based natural deep eutectic solvents to extract bioactives from marine by-products. Molecules 27:4356. https://doi.org/10.3390/molecules27144356
Access2Markets (2023) Clasificar madera | Access2Markets. https://trade.ec.europa.eu/access-to-markets/es/content/clasificar-madera. Accessed 20 Mar 2023
Alam MdA, Muhammad G, Khan MN et al (2021) Choline chloride-based deep eutectic solvents as green extractants for the isolation of phenolic compounds from biomass. J Clean Prod 309:127445. https://doi.org/10.1016/j.jclepro.2021.127445
Alam T, Jilani G, Chaudhry AN et al (2022) Terpenes and phenolics in alcoholic extracts of pine needles exhibit biocontrol of weeds (Melilotus albus and Asphodelus tenuifolius) and insect-pest (Plutella xylostella). J King Saud Univ Sci 34:101913. https://doi.org/10.1016/j.jksus.2022.101913
Alegria C, Roque N, Albuquerque T et al (2021) Modelling maritime pine (Pinus pinaster Aiton) spatial distribution and productivity in Portugal: tools for forest management. Forests 12:368. https://doi.org/10.3390/f12030368
Aliaño-González MJ, Espada-Bellido E, Ferreiro-González M et al (2020) Extraction of anthocyanins and total phenolic compounds from Açai (Euterpe oleracea Mart.) using an experimental design methodology. Part 2: Ultrasound-assisted extraction. Agronomy 10:326. https://doi.org/10.3390/agronomy10030326
Alves TFP, Teixeira N, Vieira J et al (2022) Sustainable chitosan packaging films: Green tea polyphenolic extraction strategies using deep eutectic solvents. J Clean Prod 372:133589. https://doi.org/10.1016/j.jclepro.2022.133589
Ayyubi SN, Purbasari A, Kusmiyati (2022) The effect of composition on mechanical properties of biodegradable plastic based on chitosan/cassava starch/PVA/crude glycerol: optimization of the composition using Box Behnken Design. Mater Today 63:S78–S83. https://doi.org/10.1016/j.matpr.2022.01.294
Bacelo H, Vieira BRC, Santos SCR et al (2018) Recovery and valorization of tannins from a forest waste as an adsorbent for antimony uptake. J Clean Prod 198:1324–1335. https://doi.org/10.1016/j.jclepro.2018.07.086
Chen Z-L, Wang C, Ma H et al (2021) Physicochemical and functional characteristics of polysaccharides from okra extracted by using ultrasound at different frequencies. Food Chem 361:130138. https://doi.org/10.1016/j.foodchem.2021.130138
Cho KJ, Yun CH, Yoon DY et al (2000) Effect of bioflavonoids extracted from the bark of Pinus maritima on proinflammatory cytokine interleukin-1 production in lipopolysaccharide-stimulated RAW 264.7. Toxicol Appl Pharmacol 168:64–71. https://doi.org/10.1006/taap.2000.9001
Chupin L, Maunu SL, Reynaud S et al (2015) Microwave assisted extraction of maritime pine (Pinus pinaster) bark: Impact of particle size and characterization. Ind Crop Prod 65:142–149. https://doi.org/10.1016/j.indcrop.2014.11.052
Chupin L, Motillon C, Charrier-El Bouhtoury F et al (2013) Characterisation of maritime pine (Pinus pinaster) bark tannins extracted under different conditions by spectroscopic methods, FTIR and HPLC. Ind Crop Prod 49:897–903. https://doi.org/10.1016/j.indcrop.2013.06.045
de Hoyos-Martínez PL, Merle J, Labidi J, Charrier – El Bouhtoury F, (2019) Tannins extraction: a key point for their valorization and cleaner production. J Clean Prod 206:1138–1155. https://doi.org/10.1016/j.jclepro.2018.09.243
Debnath B, Haldar D, Purkait MK (2021) A critical review on the techniques used for the synthesis and applications of crystalline cellulose derived from agricultural wastes and forest residues. Carbohydr Polym 273:118537. https://doi.org/10.1016/j.carbpol.2021.118537
Domínguez-Rodríguez G, Marina ML, Plaza M (2022) In vitro assessment of the bioavailability of bioactive non-extractable polyphenols obtained by pressurized liquid extraction combined with enzymatic-assisted extraction from sweet cherry (Prunus avium L.) pomace. Food Chem 385:132688. https://doi.org/10.1016/j.foodchem.2022.132688
Duarte H, Gomes V, Aliaño-González MJ et al (2022) Ultrasound-assisted extraction of polyphenols from maritime pine residues with deep eutectic solvents. Foods 11:3754. https://doi.org/10.3390/foods11233754
Fernandes C, Melro E, Magalhães S et al (2021) New deep eutectic solvent assisted extraction of highly pure lignin from maritime pine sawdust (Pinus pinaster Ait.). Int J Biol Macromol 177:294–305. https://doi.org/10.1016/j.ijbiomac.2021.02.088
Ferreira SLC, Bruns RE, Ferreira HS et al (2007) Box–Behnken design: an alternative for the optimization of analytical methods. Anal Chim Acta 597:179–186. https://doi.org/10.1016/j.aca.2007.07.011
Ferreira-Santos P, Ibarz R, Fernandes J-M et al (2021) Encapsulated pine bark polyphenolic extract during gastrointestinal digestion: bioaccessibility. Bioact Oxidat Stress Prevent Foods 10:328. https://doi.org/10.3390/foods10020328
Guerrero RF, Aliaño-González MJ, Puertas B et al (2020) Comparative analysis of stilbene concentration in grapevine shoots of thirteen Vitis during a three-year study. Ind Crop Prod 156:112852. https://doi.org/10.1016/j.indcrop.2020.112852
ICNF (2013) FN6-Áreas dos Usos do Solo e das Espécies Florestais de Portugal Continental. Resultados Preliminares. Instituto da Conservação da Natureza e das Florestas, Lisboa
Inkrod C, Raita M, Champreda V, Laosiripojana N (2018) Characteristics of lignin extracted from different lignocellulosic materials via organosolv fractionation. Bioenerg Res 11:277–290. https://doi.org/10.1007/s12155-018-9895-2
Jerez M, Pinelo M, Sineiro J, Núñez MJ (2006) Influence of extraction conditions on phenolic yields from pine bark: assessment of procyanidins polymerization degree by thiolysis. Food Chem 94:406–414. https://doi.org/10.1016/j.foodchem.2004.11.036
Khatib I, Chow MYT, Ruan J et al (2021) Modeling of a spray drying method to produce ciprofloxacin nanocrystals inside the liposomes utilizing a response surface methodology: Box–Behnken experimental design. Int J Pharm 597:120277. https://doi.org/10.1016/j.ijpharm.2021.120277
Kotani A, Watanabe R, Hayashi Y, Hakamata H (2022) Chemometric evaluations of repeatability and detection limit in high-performance liquid chromatography with electrochemical detection. J Chromatogr A 1673:463075. https://doi.org/10.1016/j.chroma.2022.463075
Koutsoukos S, Tsiaka T, Tzani A et al (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
Li J, Chen W, Niu D et al (2022) Efficient and green strategy based on pulsed electric field coupled with deep eutectic solvents for recovering flavonoids and preparing flavonoid aglycones from noni-processing wastes. J Clean Prod 368:133019. https://doi.org/10.1016/j.jclepro.2022.133019
Lopez-Romero JC, González-Ríos H, Borges A, Simões M (2015) Antibacterial effects and mode of action of selected essential oils components against Escherichia coli and Staphylococcus aureus. Evid-Based Complement Altern Med 2015:795435. https://doi.org/10.1155/2015/795435
Magalhães S, Filipe A, Melro E et al (2021) Lignin extraction from waste pine sawdust using a biomass derived binary solvent system. Polymers 13:1090. https://doi.org/10.3390/polym13071090
Magalhães S, Moreira A, Almeida R et al (2022) Acacia wood fractionation using deep eutectic solvents: extraction, recovery, and characterization of the different fractions. ACS Omega 7:26005–26014. https://doi.org/10.1021/acsomega.1c07380
Meullemiestre A, Petitcolas E, Maache-Rezzoug Z et al (2016) Impact of ultrasound on solid–liquid extraction of phenolic compounds from maritime pine sawdust waste. Kinetics, optimization and large scale experiments. Ultrason Sonochem 28:230–239. https://doi.org/10.1016/j.ultsonch.2015.07.022
Naeem I, Maimoona A, Naeem I et al (2011) Analysis of total flavonoids and phenolics in different fractions of bark and needle extracts of Pinus roxburghii and Pinus wallichiana. J Med Plants Res 5:5216–5220
Pandey D, Daverey A, Dutta K et al (2022) Valorization of waste pine needle biomass into biosorbents for the removal of methylene blue dye from water: kinetics, equilibrium and thermodynamics study. Environ Technol Innov 25:102200. https://doi.org/10.1016/j.eti.2021.102200
Ramos PAB, Pereira C, Gomes AP et al (2022) Chemical characterisation, antioxidant and antibacterial activities of Pinus pinaster Ait. and Pinus pinea L. Bark polar extracts: prospecting forestry by-products as renewable sources of bioactive compounds. Appl Sci 12:784. https://doi.org/10.3390/app12020784
Rivera-Tovar PR, Torres MD, Camilo C et al (2021) Multi-response optimal hot pressurized liquid recovery of extractable polyphenols from leaves of maqui (Aristotelia chilensis [Mol.] Stuntz). Food Chem 357:129729. https://doi.org/10.1016/j.foodchem.2021.129729
Santos J, Pereira J, Ferreira N et al (2021) Valorisation of non-timber by-products from maritime pine (Pinus pinaster, Ait) for particleboard production. Ind Crop Prod 168:113581. https://doi.org/10.1016/j.indcrop.2021.113581
Singh SK, Dhepe PL (2016) Isolation of lignin by organosolv process from different varieties of rice husk: understanding their physical and chemical properties. Bioresour Technol 221:310–317. https://doi.org/10.1016/j.biortech.2016.09.042
Suresh PS, Singh PP, Sharma M, Sharma U (2023) Multicomponent natural deep eutectic solvents: Super solvents for the efficient extraction of steviol glycosides (rebaudioside A) from Stevia rebaudiana. J Clean Prod 385:135639. https://doi.org/10.1016/j.jclepro.2022.135639
Verbeyst L, Oey I, Van der Plancken I et al (2010) Kinetic study on the thermal and pressure degradation of anthocyanins in strawberries. Food Chem 123:269–274. https://doi.org/10.1016/j.foodchem.2010.04.027
Wang M, Morón-Ortiz Á, Zhou J et al (2023) Effects of pressurized liquid extraction with dimethyl sulfoxide on the recovery of carotenoids and other dietary valuable compounds from the microalgae Spirulina, Chlorella and Phaeodactylum tricornutum. Food Chem 405:134885. https://doi.org/10.1016/j.foodchem.2022.134885
Wood JE, Senthilmohan ST, Peskin AV (2002) Antioxidant activity of procyanidin-containing plant extracts at different pHs. Food Chem 77:155–161. https://doi.org/10.1016/S0308-8146(01)00329-6
Yu Q, Wang F, Baroutian S et al (2023) A deep eutectic solvent binary-phase system for alkaloid extraction from Chinese herb Evodia lepta residue and its mechanism. J Clean Prod 398:136645. https://doi.org/10.1016/j.jclepro.2023.136645
Zhang Y, Qiao Q, Abbas UL et al (2023) Lignin derived hydrophobic deep eutectic solvents as sustainable extractants. J Clean Prod 388:135808. https://doi.org/10.1016/j.jclepro.2022.135808
Zhao L, Li H, Wang K et al (2022) Effects of electrolysed water and levulinic acid combination on microbial safety and polysaccharide nanostructure of organic strawberry. Food Chem 394:133533. https://doi.org/10.1016/j.foodchem.2022.133533
Zhou M, Doyle MP, Chen D (2020) Combination of levulinic acid and sodium dodecyl sulfate on inactivation of foodborne microorganisms: a review. Crit Rev Food Sci Nutr 60:2526–2531. https://doi.org/10.1080/10408398.2019.1650249
Zhu H, Saddler J, Bi X (2022) An economic and environmental assessment of biofuel produced via microwave-assisted catalytic pyrolysis of forest residues. Energy Conv Manag 263:115723. https://doi.org/10.1016/j.enconman.2022.115723
Zwingelstein M, Draye M, Besombes J-L et al (2020) Viticultural wood waste as a source of polyphenols of interest: Opportunities and perspectives through conventional and emerging extraction methods. Waste Manage 102:782–794. https://doi.org/10.1016/j.wasman.2019.11.034
Acknowledgements
María José Aliaño-González would like to thank the University of Cádiz for the grant in the modality "Margarita Salas," of the call for the Recualification of the Spanish University System for 2021–2023 (Resolution of the Rector of the University of Cadiz UCA/R155REC/2021, of 2 July), and financed by the Ministry of Universities of the Government of Spain through the European Recovery Instrument "Next Generation EU," of the European Union (Order UNI/551/2021, of 26 May).
Funding
This research was funded by National Funds through FCT—Foundation for Science and Technology under the Project UIDB/05183/2020. This work was also supported by funding from the Portuguese Foundation for Science and Technology (FCT) through the projects PTDC/ASP-SIL/30619/2017, UIDB/05183/2020 and the researcher Grant CEECIND/01014/2018.
Author information
Authors and Affiliations
Contributions
Hugo Duarte: Formal analysis; investigation; writing—original draft; software. Valentim Soares Gomes: Formal analysis; investigation; writing—original draft; data curation. María José Aliaño–González: Conceptualization; methodology; writing—review & editing; supervision. Anabela Romano: Resources; visualization; project administration; funding acquisition; review & editing. Leonor Faleiro: methodology; resources; visualization; project administration. Bruno Medronho: Validation; resources; writing—review & editing; supervision.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare they do not have Conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
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.
About this article
Cite this article
Duarte, H., Gomes, V., Aliaño-González, M.J. et al. Optimization of the extraction of polyphenols from Pinus pinaster residues using deep eutectic solvents: a sustainable approach. Wood Sci Technol 57, 1175–1196 (2023). https://doi.org/10.1007/s00226-023-01493-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00226-023-01493-3