Purification of Curcuminoids from Natural Deep Eutectic Solvents (NADES) Matrices Using Chromatography-Based Separation Methods


Orchidea Rachmaniah(1*), Muhammad Rifqy Muhsin(2), Angga Widya Putra(3), Muhammad Rachimoellah(4)

(1) Department of Chemical Engineering, Faculty of Industrial Technology and System Engineering, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, Indonesia
(2) Department of Chemical Engineering, Faculty of Industrial Technology and System Engineering, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, Indonesia
(3) Department of Chemical Engineering, Faculty of Industrial Technology and System Engineering, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, Indonesia
(4) Department of Chemical Engineering, Faculty of Industrial Technology and System Engineering, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, Indonesia
(*) Corresponding Author


Curcuminoids can be successfully extracted from Curcuma zedoaria using natural deep eutectic solvents (NADES) as extraction solvents. However, a mixture of extracted curcuminoids, NADES, and impurities from C. zedoaria was obtained as a slurry at the end of the extraction process. Therefore, further separation and purification were required to obtain the extracted compound in high purity. Herein, two purification methods based on classical column chromatography (CCC) and solid-phase extraction (SPE), were evaluated for the purification of curcuminoids from NADES matrices after extraction. Choline chloride–malic acid–water (CCMA–H2O) and choline chloride–citric acid–water (CCCA–H2O) in the molar ratio of 1:1:18 were selected as NADES matrices due to their high solubility and stabilization capability for curcuminoids. Ethanol-conditioned silica gel (60–200 µm) was applied as the bed resin for CCC, and a C18 cartridge was used for SPE. Acetonitrile/0.1% acetic acid, water/0.1% acetic acid, and iso-propanol/0.1% acetic acid were used as mobile phases for CCC. For SPE, methanol/0.05% acetic acid and water/0.05% acetic acid were applied in the conditioning step, water/0.05% acetic acid in the washing step, and methanol/acetonitrile (1:1) in the eluting step. The SPE method produced higher recovery of curcuminoids from the CCCA–H2O and CCMA–H2O matrices (75.27% and 73.40%, respectively) compared to CCC (51.9% and 61.0%, respectively). After removing the NADES constituents from the crude extract of curcuminoids, recrystallization was attempted.


curcumin; chromatography; recrystallization; separation; solid phase extraction

Full Text:

Full Text PDF


[1] Choi, Y.H., van Spronsen, J., Dai, Y., Verberne, M., Hollmann, F., Arends, I.W.C.E., Witkamp, G.J., and Verpoorte, R., 2011, Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology?, Plant Physiol., 156 (4), 1701–1705.

[2] Paiva, A., Craveiro, R., Aroso, I., Martins, M., Reis, R.L., and Duarte, A.R.C., 2014, Natural deep eutectic solvents – Solvents for the 21st century, ACS Sustainable Chem. Eng., 2 (5), 1063–1071.

[3] Gorke, J.T., Srienc, F., and Kazlauskas, R.J., 2008, Hydrolase-catalyzed biotransformations in deep eutectic solvents, Chem. Commun., 10, 1235–1237.

[4] Dai, Y., van Spronsen, J., Witkamp, G.J., Verpoorte, R., and Choi, Y.H., 2013, Natural deep eutectic solvents as new potential media for green technology, Anal. Chim. Acta, 766, 61–68.

[5] Dai, Y., Witkamp, G.J., Verpoorte, R., and Choi, Y.H., 2013, Natural deep eutectic solvents as new potential media for phenolic metabolites in Carthamus tinctorius L., Anal. Chem., 85 (13), 6272–6278.

[6] Liu, Y., Li, J., Fu, R., Zhang, L., Wang, D., and Wang, S., 2019, Enhanced extraction of natural pigments from Curcuma longa L. using natural deep eutectic solvents, Ind. Crops Prod., 140, 111620.

[7] Zullaikah, S., Rachmaniah, O., Utomo A.T., Niawati, H., and Ju, Y.H., 2018, “Green Separation of Bioactive Natural Products using Liquefied Mixture of Solidsin Green Chemistry, Eds. Saleh, H.E.D.M. and Koller, M., InTechOpen, London, UK.

[8] Rachmaniah, O., Fazriyah, L.J., Seftiyani, N.H., and Rachimoellah, M., 2018, Tailoring properties of acidic types of Natural Deep Eutectics Solvents (NADES): Enhanced solubility of curcuminoids from Curcuma zedoaria, MATEC Web Conf., 156, 01011.

[9] Chanioti, S., and Tzia, C., 2018, Extraction of phenolic compounds from olive pomace by using natural deep eutectic solvents and innovative extraction techniques, Innovative Food Sci. Emerging Technol., 48, 228–239.

[10] Panić, M., Radić Stojković, M., Kraljić, K., Škevin, D., Radojčić Redovniković, I., Gaurina Srček, V., and Radošević, K., 2019, Ready-to-use green polyphenolic extracts from food by-products, Food Chem., 283, 628–636.

[11] Hamany, D.C.Y., Piater, L.A., Steenkamp, P.A., Madala, N.E., and Dubery, I.A., 2018, Differential extraction of phytochemicals from the multipurpose tree, Moringa oleifera, using green extraction solvents, S. Afr. J. Bot., 115, 81–89.

[12] Ivanović, M., Alañón, M.E., Arráez-Román, D., and 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.

[13] Miličević, N., Panić, M., Valinger, D., Cvjetko Bubalo, M., Benković, M., Jurina, T., Gajdoš Kljusurić, J., Radojčić Redovniković, I., and Jurinjak Tušek, A., 2020, Development of continuously operated aqueous two-phase microextraction process using natural deep eutectic solvents, Sep. Purif. Technol., 244, 116746.

[14] Kocaadam, B., and Şanlier, N., 2017, Curcumin, an active component of turmeric (Curcuma longa), and its effects on health, Crit. Rev. Food Sci. Nutr., 57 (13), 2889–2895.

[15] Patra, D., and Sleem, F., 2013, A new method for pH triggered curcumin release by applying poly(L-lysine) mediated nanoparticle-congregation, Anal. Chim. Acta, 795, 60–68.

[16] Tønnesen, H.H., and Karlsen, J., 1985, Studies on curcumin and curcuminoids, Z. Lebensm. Unters. Forsch., 180 (5), 402–404.

[17] Patil, S.S., Bhasarkar, S., and Rathod, V.K., 2019, Extraction of curcuminoids from Curcuma longa: Comparative study between batch extraction and novel three phase partitioning, Prep. Biochem. Biotechnol., 49 (4), 407–418.

[18] Patil, S.S., Pathak, A., and Rathod, V.K., 2021, Optimization and kinetic study of ultrasound assisted deep eutectic solvent based extraction: A greener route for extraction of curcuminoids from Curcuma longa, Ultrason. Sonochem., 70, 105267.

[19] Neves, M.I.L., Strieder, M.M., Vardanega, R., Silva, E.K., and Meireles, M.A.A., 2020, Biorefinery of turmeric (Curcuma longa L.) using non-thermal and clean emerging technologies: An update on the curcumin recovery step, RSC Adv., 10 (1), 112–121.

[20] Kiamahalleh, M.V., Najafpour-Darzi, G., Rahimnejad, M., Moghadamnia, A.A., and Kiamahalleh, M.V., 2016, High performance curcumin subcritical water extraction from turmeric (Curcuma longa L.), J. Chromatogr. B, 1022, 191–198.

[21] Osorio-Tobón, J.F., Carvalho, P.I.N., Rostagno, M.A., and Meireles, M.A.A., 2016, Process integration for turmeric products extraction using supercritical fluids and pressurized liquids: Economic evaluation, Food Bioprod. Process., 98, 227–235.

[22] Yuwono, M., and Indrayanto, G., 2005, Validation of chromatographic methods of analysis. In profiles of drug substances, Profiles Drug Subst., Excipients, Relat. Method., 32, 243–259.

[23] Fagundes, T.S.F., Dutra, K.D.B., Ribeiro, C.M.R., Epifanio, R.A., and Valverde, A.L., 2015, Using a Sequence of experiments with turmeric pigments from food to teach extraction, distillation, and thin layer chromatography to introductory organic chemistry students, J. Chem. Educ., 93 (2), 326–329.

[24] Nugroho, A.E., Yuniarti, N., Istyastono, E.P., Supardjan, S., and Hakim, L., 2006, Determination of antioxidant activity of dehydro-zingerone through hydroxyl radical scavengers using deoxyribose method, Indones. J. Pharm., 17 (3), 116–122.

[25] Istyastono, E.P., Martono, S., Pranowo, H.D., and Tahir, I., 2003, Quantitative structure activity relationship analysis of curcumin and its derivate as GST inhibitors bases on computational chemistry calculation, Indones. J. Chem., 3 (3), 179–186.

[26] Rachmaniah, O., Muhsin, M.R., Widya, A.P., and Rachimoellah, M., 2020, Process development for the enrichment of curcuminoids in the extract of ionic type of NADES, IOP Conf. Ser.: Mater. Sci. Eng., 732, 012005.

[27] Yadav, D., and Kumar, N., 2014, Nanonization of curcumin by antisolvent precipitation: Process development, characterization, freeze drying and stability performance, Int. J. Pharm., 477 (1-2), 564–577.

[28] Kulkarni, S.J., Maske, K.N., Budre, M.P., and Mahajan, R.P., 2017, Extraction and purification of curcuminoids from turmeric (Curcuma longa L.), Int. J. Pharmacol. Pharm. Technol., 1 (2), 81–84.

[29] Revathy, S., Elumalai, S., Benny, M., and Antony, B., 2011, Isolation, purification and identification of curcuminoids from turmeric (Curcuma longa L.) by column chromatography, J. Exp. Sci., 2 (7), 21–25.

[30] Heffernan, C., Ukrainczyk, M., Gamidi, R.K., Hodnett, B.K., and Rasmuson, Å.C., 2017, Extraction and purification of curcuminoids from crude curcumin by a combination of crystallization and chromatography, Org. Process Res. Dev., 21 (6), 821–826.

[31] Pushpakumari, K.N., Varghese, N., and Kottol, K., 2014, Purification and separation of individual curcuminoids from spent turmeric oleoresin, a by-product from curcumin production industry, Int. J. Pharm. Sci. Res., 5 (8), 3246–3254.

DOI: https://doi.org/10.22146/ijc.58935

Article Metrics

Abstract views : 4098 | views : 3213

Copyright (c) 2021 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Analytics View The Statistics of Indones. J. Chem.