Abstract
This was the first study to use local Southern Thai ingredients, namely, nipa palm syrup (NS) and nipa palm vinegar (NV), in the formulation of natural deep eutectic solvent (NADES) for the recovery of bioactive curcumin from turmeric. Five NADES formulations (A to E) were obtained by varying concentration of liquid media (NS, NV, and water) and characterized using FTIR. When compared to other formulations and 80% methanol, the NADES D with a NS to NV to water ratio of 1:5:5 (w/w/w) recovered the most curcumin content (p < 0.05). The extraction conditions of microwave-assisted extraction (MAE) with selected NADES were optimized using response surface methodology (RSM) to maximize curcumin recovery. NADES D achieved the highest curcumin content (43.04 mg/g) from turmeric at a solvent ratio of 1:10, microwave power of 1000 W, and extraction time of 51 s. The NADES D-based curcumin extract outperformed all antioxidant activities (DPPH∙ scavenging activity and FRAP). The NADES D–based extract is non-toxic to RAW264.7 cells at up to 62.50 µg/mL. As a result, NADES-based NS and NV are a viable green solvent for obtaining bioactive compounds, particularly curcumin from turmeric.
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References
Airouyuwa, J. O., Mostafa, H., Riaz, A., & Maqsood, S. (2022). Utilization of natural deep eutectic solvents and ultrasound-assisted extraction as green extraction technique for the recovery of bioactive compounds from date palm (Phoenix dactylifera L.) seeds: An investigation into optimization of process parameters. Ultrasonics Sonochemistry, 91, 106233.
Airouyuwa, J. O., Mostafa, H., Riaz, A., Stathopoulos, C., & Maqsood, S. (2023). Natural deep eutectic solvents and microwave-assisted green extraction for efficient recovery of bioactive compounds from by-products of date fruit (Phoenix dactylifera L.) processing: Modeling, optimization, and phenolic characterization. Food and Bioprocess Technology, 16(4), 824–843.
AOAC. (2000). Official methods of analysis. Association of Official Analytical Chemists.
Ashrafizadeh, M., Rafiei, H., Mohammadinejad, R., Afshar, E. G., Farkhondeh, T., & Samarghandian, S. (2020). Potential therapeutic effects of curcumin mediated by JAK/STAT signaling pathway: A review. Phytotherapy Research, 34(8), 1745–1760.
Bakirtzi, C., Triantafyllidou, K., & Makris, D. P. (2016). Novel lactic acid-based natural deep eutectic solvents: Efficiency in the ultrasound-assisted extraction of antioxidant polyphenols from common native Greek medicinal plants. Journal of Applied Research on Medicinal and Aromatic Plants, 3(3), 120–127.
Barbieri, J. B., Goltz, C., Cavalheiro, F. B., Toci, A. T., Igarashi-Mafra, L., & Mafra, M. R. (2020). Deep eutectic solvents applied in the extraction and stabilization of rosemary (Rosmarinus officinalis L.) phenolic compounds. Industrial Crops and Products 144, 112049.
Bellary, A. N., & Rastogi, N. K. (2014). Effect of selected pretreatments on impregnation of curcuminoids and their influence on physico-chemical properties of raw banana slices. Food and Bioprocess Technology, 7, 2803–2812.
Bener, M., Şen, F. B., Önem, A. N., Bekdeşer, B., Çelik, S. E., Lalikoglu, M., & Apak, R. (2022). Microwave-assisted extraction of antioxidant compounds from by-products of Turkish hazelnut (Corylus avellana L.) using natural deep eutectic solvents: Modeling, optimization and phenolic characterization. Food Chemistry, 385, 132633.
Choudhary, P., Guleria, S., Sharma, N., Salaria, K. H., Chalotra, R., Ali, V., & Vyas, D. (2021). Comparative phenolic content and antioxidant activity of some medicinal plant extracts prepared by choline chloride based green solvents and methanol. Current Research in Green and Sustainable Chemistry, 4, 100224.
Costa, F. S., Moreira, L. S., Silva, A. M., Silva, R. J., dos Santos, M. P., da Silva, E. G. P., & Amaral, C. D. (2022). Natural deep eutectic solvent-based microwave-assisted extraction in the medicinal herb sample preparation and elemental determination by ICP OES. Journal of Food Composition and Analysis, 109, 104510.
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. Journal of Cleaner Production, 184, 826–835.
da Silva, D. T., Pauletto, R., da Silva Cavalheiro, S., Bochi, V. C., Rodrigues, E., Weber, J., & Emanuelli, T. (2020). Natural deep eutectic solvents as a biocompatible tool for the extraction of blueberry anthocyanins. Journal of Food Composition and Analysis, 89, 103470.
Dai, Y., Rozema, E., Verpoorte, R., & Choi, Y. H. (2016). Application of natural deep eutectic solvents to the extraction of anthocyanins from Catharanthus roseus with high extractability and stability replacing conventional organic solvents. Journal of Chromatography A, 1434, 50–56.
Dai, Y., van Spronsen, J., Witkamp, G. J., Verpoorte, R., & Choi, Y. H. (2013). Natural deep eutectic solvents as new potential media for green technology. Analytica Chimica Acta, 766, 61–68.
Dai, Y., Verpoorte, R., & Choi, Y. H. (2014). Natural deep eutectic solvents providing enhanced stability of natural colorants from safflower (Carthamus tinctorius). Food Chemistry, 159, 116–121.
de los Ángeles Fernández, M., Boiteux, J., Espino, M., Gomez, F. J., & Silva, M. F. (2018). Natural deep eutectic solvents-mediated extractions: The way forward for sustainable analytical developments. Analytica Chimica Acta, 1038, 1–10.
Dhar, R., Kimseng, R., Chokchaisiri, R., Hiransai, P., Utaipan, T., Suksamrarn, A., & Chunglok, W. (2018). 2′, 4-Dihydroxy-3′, 4′, 6′-trimethoxychalcone from Chromolaena odorata possesses anti-inflammatory effects via inhibition of NF-κB and p38 MAPK in lipopolysaccharide-activated RAW 264.7 macrophages. Immunopharmacology and Immunotoxicology, 40(1), 43–51.
Díaz-Álvarez, M., & Martín-Esteban, A. (2022). Preparation and further evaluation of l-menthol-based natural deep eutectic solvents as supported liquid membrane for the hollow fiber liquid-phase microextraction of sulfonamides from environmental waters. Advances in Sample Preparation, 4, 100047.
Doldolova, K., Bener, M., Lalikoğlu, M., Aşçı, Y. S., Arat, R., & Apak, R. (2021). Optimization and modeling of microwave-assisted extraction of curcumin and antioxidant compounds from turmeric by using natural deep eutectic solvents. Food Chemistry, 353, 129337.
Fan, C., Sebbah, T., Liu, Y., & Cao, X. (2021). Terpenoid-capric acid based natural deep eutectic solvent: Insight into the nature of low viscosity. Cleaner Engineering and Technology, 3, 100116.
Hasanzadeh, S., Read, M. I., Bland, A. R., Majeed, M., Jamialahmadi, T., & Sahebkar, A. (2020). Curcumin: An inflammasome silencer. Pharmacological Research, 159, 104921.
Huber, V., Muller, L., Degot, P., Touraud, D., & Kunz, W. (2021). NADES-based surfactant-free microemulsions for solubilization and extraction of curcumin from Curcuma longa. Food Chemistry, 355, 129624.
Jansakun, C., Chulrik, W., Chaichompoo, W., Yotmanee, P., Lehboon, K., Chunglok, W., Sattayakhom, A., Hiransai, P., Kamdee, K., Utaipan, T., Suksamrarn, A., & Chunglok, W. (2021). 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one alleviates lipopolysaccharide-induced inflammation by targeting NF-κB translocation in murine macrophages and it interacts with MD2 in silico. Molecular Medicine Reports, 23(3), 209.
Jurić, T., Mićić, N., Potkonjak, A., Milanov, D., Dodić, J., Trivunović, Z., & Popović, B. M. (2021). The evaluation of phenolic content, in vitro antioxidant and antibacterial activity of Mentha piperita extracts obtained by natural deep eutectic solvents. Food Chemistry, 362, 130226.
Khatun, M., Nur, M. A., Biswas, S., Khan, M., & Amin, M. Z. (2021). Assessment of the antioxidant, anti-inflammatory and anti-bacterial activities of different types of turmeric (Curcuma longa) powder in Bangladesh. Journal of Agriculture and Food Research, 6, 100201.
Kisanthia, R., Hunt, A. J., Sherwood, J., Somsakeesit, L. O., & Phaosiri, C. (2021). Impact of conventional and sustainable solvents on the yield, selectivity, and recovery of curcuminoids from turmeric. ACS Sustainable Chemistry & Engineering, 10(1), 104–114.
Lakka, A., Grigorakis, S., Karageorgou, I., Batra, G., Kaltsa, O., Bozinou, E., & Makris, D. P. (2019). Saffron processing wastes as a bioresource of high-value added compounds: Development of a green extraction process for polyphenol recovery using a natural deep eutectic solvent. Antioxidants, 8(12), 586.
Laklaeng, S. N., & Kwanhian, W. (2020). Immunomodulation effect of Nypa fruticans palm vinegar. Walailak Journal of Science and Technology, 17(11), 1200–1210.
Lanari, D., Zadra, C., Negro, F., Njem, R., & Marcotullio, M. C. (2022). Influence of choline chloride-based NADES on the composition of Myristica fragrans Houtt. essential oil. Heliyon, 8(5), e09531.
Laosam, P., Panpipat, W., Chaijan, M., Roytrakul, S., Charoenlappanit, S., Panya, A., Phonsatta, N., Cheong, L. Z., & Yusakul, G. (2022). Molecular structures and in vitro bioactivities of enzymatically produced porcine placenta peptides fractionated by ultrafiltration. Food and Bioprocess Technology, 15(3), 669–682.
Lateh, L., Yuenyongsawad, S., Chen, H., & Panichayupakaranant, P. (2019). A green method for preparation of curcuminoid-rich Curcuma longa extract and evaluation of its anticancer activity. Pharmacognosy Magazine, 15(65), 730.
Le-Tan, H., Fauster, T., Haas, K., & Jaeger, H. (2022). Aqueous extraction of curcuminoids from Curcuma longa: Effect of cell disintegration pre-treatment and extraction condition. Food and Bioprocess Technology, 15(6), 1359–1373.
Li, Q., Sun, J., Mohammadtursun, N., Wu, J., Dong, J., & Li, L. (2019). Curcumin inhibits cigarette smoke-induced inflammation via modulating the PPARγ-NF-κB signaling pathway. Food & Function, 10(12), 7983–7994.
Lim, J., Nguyen, T. T. H., Pal, K., Kang, C. G., Park, C., Kim, S. W., & Kim, D. (2022). Phytochemical properties and functional characteristics of wild turmeric (Curcuma aromatica) fermented with Rhizopus oligosporus. Food Chemistry: X, 13, 100198.
Lin, S., Meng, X., Tan, C., Tong, Y., Wan, M., Wang, M., & Ma, Y. (2022). Composition and antioxidant activity of anthocyanins from Aronia melanocarpa extracted using an ultrasonic-microwave-assisted natural deep eutectic solvent extraction method. Ultrasonics Sonochemistry, 89, 106102.
Liu, Y., Li, J., Fu, R., Zhang, L., Wang, D., & Wang, S. (2019). Enhanced extraction of natural pigments from Curcuma longa L. using natural deep eutectic solvents. Industrial Crops and Products, 140, 111620.
Liu, Y., Chen, W., Xia, Q., Guo, B., Wang, Q., Liu, S., & Yu, H. (2017). Efficient cleavage of lignin–carbohydrate complexes and ultrafast extraction of lignin oligomers from wood biomass by microwave-assisted treatment with deep eutectic solvent. Chemsuschem, 10(8), 1692–1700.
Liu, Y., Friesen, J. B., McAlpine, J. B., Lankin, D. C., Chen, S. N., & Pauli, G. F. (2018). Natural deep eutectic solvents: Properties, applications, and perspectives. Journal of Natural Products, 81(3), 679–690.
López-Cruz, R., Sandoval-Contreras, T., & Iñiguez-Moreno, M. (2023). Plant pigments: classification, extraction, and challenge of their application in the food industry. Food and Bioprocess Technology, 1–17.
Martinović, M., Krgović, N., Nešić, I., Žugić, A., & Tadić, V. M. (2022). Conventional vs. green extraction using natural deep eutectic solvents—Differences in the composition of soluble unbound phenolic compounds and antioxidant activity. Antioxidants, 11(11), 2295.
Nam, N. N., Do, H. D. K., Trinh, K. T. L., & Lee, N. Y. (2023). Design strategy and application of deep eutectic solvents for green synthesis of nanomaterials. Nanomaterials, 13(7), 1164.
Obluchinskaya, E. D., Pozharitskaya, O. N., Zakharova, L. V., Daurtseva, A. V., Flisyuk, E. V., & Shikov, A. N. (2021). Efficacy of natural deep eutectic solvents for extraction of hydrophilic and lipophilic compounds from Fucus vesiculosus. Molecules, 26(14), 4198.
Ozturk, B., Esteban, J., & Gonzalez-Miquel, M. (2018). Deterpenation of citrus essential oils using glycerol-based deep eutectic solvents. Journal of Chemical & Engineering Data, 63(7), 2384–2393.
Pavić, V., Flačer, D., Jakovljević, M., Molnar, M., & Jokić, 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, 8(3), 69.
Peng, Y., Ao, M., Dong, B., Jiang, Y., Yu, L., Chen, Z., & Xu, R. (2021). Anti-inflammatory effects of curcumin in the inflammatory diseases: Status, limitations and countermeasures. Drug Design, Development and Therapy, 15, 4503–4525.
Phetrit, R., Chaijan, M., Sorapukdee, S., & Panpipat, W. (2020). Characterization of nipa palm’s (Nypa fruticans Wurmb.) sap and syrup as functional food Ingredients. Sugar Tech, 22(1), 191–201.
Saengkrajang, W., Chaijan, M., & Panpipat, W. (2021). Physicochemical properties and nutritional compositions of nipa palm (Nypa fruticans Wurmb) syrup. NFS Journal, 23, 58–65.
Stupar, A., Šeregelj, V., Ribeiro, B. D., Pezo, L., Cvetanović, A., Mišan, A., & Marrucho, I. (2021). Recovery of β-carotene from pumpkin using switchable natural deep eutectic solvents. Ultrasonics Sonochemistry, 76, 105638.
Tamprasit, P., Panpipat, W., & Chaijan, M. (2020). Improved radical scavenging activity and stabilised colour of nipa palm syrup after ultrasound-assisted glycation with glycine. International Journal of Food Science & Technology, 55(11), 3424–3431.
Wang, J., Jing, W., Tian, H., Liu, M., Yan, H., Bi, W., & Chen, D. D. Y. (2020a). Investigation of deep eutectic solvent-based microwave-assisted extraction and efficient recovery of natural products. ACS Sustainable Chemistry & Engineering, 8(32), 12080–12088.
Wang, S., Cao, M., Xu, S., Shi, J., Mao, X., Yao, X., & Liu, C. (2020b). Luteolin alters macrophage polarization to inhibit inflammation. Inflammation, 43, 95–108.
Wils, L., Leman-Loubière, C., Bellin, N., Clément-Larosière, B., Pinault, M., Chevalier, S., & Boudesocque-Delaye, L. (2021). Natural deep eutectic solvent formulations for spirulina: Preparation, intensification, and skin impact. Algal Research, 56, 102317.
Wu, J., Sun, X., Guo, X., Ji, M., Wang, J., Cheng, C., Chen, Li., Wen, C., & Zhang, Q. (2018). Physicochemical, antioxidant, in vitro release, and heat sealing properties of fish gelatin films incorporated with β-cyclodextrin/curcumin complexes for apple juice preservation. Food and Bioprocess Technology, 11, 447–461.
Wu, Y. X., Jiang, F. J., Liu, G., Wang, Y. Y., Gao, Z. Q., Jin, S. H., & Pang, Q. F. (2021). Dehydrocostus lactone attenuates methicillin-resistant Staphylococcus aureus-induced inflammation and acute lung injury via modulating macrophage polarization. International Journal of Molecular Sciences, 22(18), 9754.
Yang, B., Liu, X., & Gao, Y. (2009). Extraction optimization of bioactive compounds (crocin, geniposide and total phenolic compounds) from Gardenia (Gardenia jasminoides Ellis) fruits with response surface methodology. Innovative Food Science & Emerging Technologies, 10(4), 610–615.
Yusoff, N. A., Yam, M. F., Beh, H. K., Razak, K. N. A., Widyawati, T., Mahmud, R., Ahmad, M., & Asmawi, M. Z. (2015). Antidiabetic and antioxidant activities of Nypa fruticans Wurmb. vinegar sample from Malaysia. Asian Pacific Journal of Tropical Medicine, 8(8), 595–605.
Zhang, Y., Bian, S., Hu, J., Liu, G., Peng, S., Chen, H., & Zhu, H. (2022). Natural deep eutectic solvent-based microwave-assisted extraction of total flavonoid compounds from spent sweet potato (Ipomoea batatas L.) leaves: Optimization and antioxidant and bacteriostatic activity. Molecules, 27(18), 5985.
Zhang, J., Zheng, Y., Luo, Y., Du, Y., Zhang, X., & Fu, J. (2019). Curcumin inhibits LPS-induced neuroinflammation by promoting microglial M2 polarization via TREM2/TLR4/NF-κB pathways in BV2 cells. Molecular Immunology, 116, 29–37.
Zhao, Y., Wang, P., Zheng, W., Yu, G., Li, Z., She, Y., & Lee, M. (2019). Three-stage microwave extraction of cumin (Cuminum cyminum L.) seed essential oil with natural deep eutectic solvents. Industrial Crops and Products, 140, 111660.
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This work was supported by the National Research Council of Thailand (NRCT) under the Royal Golden Jubilee PhD (RGJ) program, Thailand (Grant no. N41A640228).
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Tanatchapond Rodsamai: Conceptualization, Methodology, Investigation, Formal analysis, Data curation, Software, writing – original draft, Writing – review & editing. Manat Chaijan: Conceptualization, Methodology, Supervision, Writing – original draft, Writing – review & editing. Mudtorlep Nisoa: Methodology, Writing – review & editing. Natthawuddhi Donlao: Writing – review & editing. Saroat Rawdkuen: Writing – review & editing Warangkana Chunglok: Methodology, Writing – review & editing. Ling-Zhi Cheong: Writing – review & editing. Worawan Panpipat: Conceptualization, Methodology, Validation, Resources, Funding acquisition, Supervision, Project administration, Writing – original draft, Writing – review & editing. All authors reviewed the manuscript.
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Rodsamai, T., Chaijan, M., Nisoa, M. et al. Improved Curcumin Recovery and In Vitro Biological Activity of Turmeric Extracts Using Nipa Palm Syrup– and Nipa Palm Vinegar–Based Natural Deep Eutectic Solvent (NADES) Hybridized with Microwave-Assisted Extraction. Food Bioprocess Technol (2023). https://doi.org/10.1007/s11947-023-03253-4
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DOI: https://doi.org/10.1007/s11947-023-03253-4