IMIDAZOLIUM-BASED IONIC LIQUIDS FOR THE SELECTIVE SEPARATION OF TOCOTRIENOL HOMOLOGUES FROM PALM FATTY ACID DISTILLATE VIA LIQUID-LIQUID EXTRACTION

Authors

  • DIAN MARIA ULFA Faculty of Pharmacy, Universitas Indonesia, Cluster of Health Sciences Building, Depok-16424, West Java, Indonesia. National Metabolomics Collaborative Research Center, Faculty of Pharmacy, Universitas Indonesia, Kampus UI, Depok, West Java-16424, Indonesia. Health Polytechnic Jakarta II, Jalan raya Ragunan No. 29 C Jatipadang Pasar Minggu, South Jakarta-12540 Indonesia
  • ABDUL MUNIM Faculty of Pharmacy, Universitas Indonesia, Cluster of Health Sciences Building, Depok-16424, West Java, Indonesia
  • SITI IRMA RAHMAWATI National Metabolomics Collaborative Research Center, Faculty of Pharmacy, Universitas Indonesia, Kampus UI, Depok, West Java-16424, Indonesia. Research Center for Vaccine and Drugs, National Research and Innovation Agency (BRIN), Jalan raya Jakarta-Bogor KM 46, Cibinong, Bogor, West Java-16911, Indonesia
  • MASTERIA YUNOVILSA PUTRA National Metabolomics Collaborative Research Center, Faculty of Pharmacy, Universitas Indonesia, Kampus UI, Depok, West Java-16424, Indonesia. Research Center for Vaccine and Drugs, National Research and Innovation Agency (BRIN), Jalan raya Jakarta-Bogor KM 46, Cibinong, Bogor, West Java-16911, Indonesia
  • ASEP BAYU National Metabolomics Collaborative Research Center, Faculty of Pharmacy, Universitas Indonesia, Kampus UI, Depok, West Java-16424, Indonesia. Research Center for Vaccine and Drugs, National Research and Innovation Agency (BRIN), Jalan raya Jakarta-Bogor KM 46, Cibinong, Bogor, West Java-16911, Indonesia

DOI:

https://doi.org/10.22159/ijap.2024.v16s3.13

Keywords:

Ionic liquids, Green solvent extraction, Palm fatty acid distillate, Tocotrienols

Abstract

Objective: Tocotrienols have now stepped into the limelight of vitamin E research and have proven to have some exceptional benefits that are not shared by their “older” tocopherol siblings. Unlike tocopherols, tocotrienols are able to inhibit cholesterol biosynthesis, have specific neuroprotective activities stronger antioxidant effects, antihypertensive and anti-cancer. The purpose of this study was to carry out selective separation of tocotrienols homologues from Palm Fatty Acid Distillate (PFAD) by liquid-liquid extraction, using Ionic liquids (ILs) as extractants in the presence of diluent.

Methods: Four kinds of imidazolium-based ILs that used are 1-butyl-3-methylimidazolium chloride ([Bmim]Cl), 1-Butyl-3-methylimidazolium acetate ([Bmim]Ac), 1-Hexyl-3-methylimidazolium chloride ([Hmim]Cl) and 1-Ethyl-3-methylimidazolium chloride ([Emim]C]). The extraction is carried out by creating a two-phase system between ILs and PFAD in n-hexane. Quantification of extracted tocotrienols was performed using High-Performance liquid Chromatography (HPLC) with a C18 column, mobile phase methanol: water (97.5:2.5), flow rate 1 ml/min and Ultraviolet (UV) detector at 295 nm.

Results: The results showed that the concentration (extraction efficiency) of tocotrienols extracted using ILs in order were [Bmim] Ac 1611.09 mg/Kg (75.41%) and [Hmim][Cl] 1603.39 mg/Kg (75.05%), [Bmim]Cl 1523.60 mg/Kg (71.32%) and [Emim]Cl 1174.24 mg/Kg (54.96%).

Conclusion: [Bmim]Ac yielded the highest tocotrienols concentration and extraction efficiency.

Downloads

Download data is not yet available.

References

Niki E, Chapter AK. Vitamin E: structure, properties and functions. Food Chem Funct Anal. 2019;1(11):1-11.

Atkinson J, Marquardt D, DiPasquale M, Harroun T. From fat to bilayers: understanding where and how vitamin E works. Free Radical Biol Med. 2021;176:73-9. doi: 10.1016/j.freeradbiomed.2021.09.015, PMID 34555454.

Szymanska R, Nowicka B, Kruk J. Vitamin E-occurrence, biosynthesis by plants and functions in Human nutrition. Mini Rev Med Chem. 2017;17(12):1039-52. doi: 10.2174/1389557516666160725094819, PMID 27457214.

Suzuki YJ, Tsuchiya M, Wassall SR, Choo YM, Govil G, Kagan VE. Structural and dynamic membrane properties of α-tocopherol and α-tocotrienol: implication to the molecular mechanism of their antioxidant potency. Biochemistry. 1993;32(40):10692-9. doi: 10.1021/bi00091a020, PMID 8399214.

Khanna S, Parinandi NL, Kotha SR, Roy S, Rink C, Bibus D. Nanomolar vitamin E α-tocotrienol inhibits glutamate-induced activation of phospholipase A2 and causes neuroprotection. J Neurochem. 2010;112(5):1249-60. doi: 10.1111/j.1471-4159.2009.06550.x, PMID 20028458.

Serbinova EA, Packer L. Antioxidant properties of α-tocopherol and α-tocotrienol. Methods Enzymol. 1994;234(C):354-66. doi: 10.1016/0076-6879(94)34105-2, PMID 7808307.

Busing A, Ternes W. Separation of α-tocotrienol oxidation products and eight tocochromanols by HPLC with DAD and fluorescence detection and identification of unknown peaks by DAD, PBI-EIMS, FTIR, and NMR. Anal Bioanal Chem. 2011;401(9):2843-54. doi: 10.1007/s00216-011-5352-1, PMID 21901461.

Thiele JJ, Hsieh SN, Ekanayake Mudiyanselage S. Vitamin E: critical review of its current use in cosmetic and clinical dermatology. Dermatol Surg. 2005;31(7 Pt 2):805-13; discussion 813. doi: 10.1111/j.1524-4725.2005.31724, PMID 16029671.

Colombo ML. An update on vitamin E, tocopherol and tocotrienol-perspectives. Molecules. 2010;15(4):2103-13. doi: 10.3390/molecules15042103, PMID 20428030.

Shahidi F, Pinaffi Langley AC, Fuentes J, Speisky H, De Camargo AC. Vitamin E as an essential micronutrient for human health: common, novel, and unexplored dietary sources. Free Radic Biol Med. 2021;176:312-21. doi: 10.1016/j.freeradbiomed.2021.09.025, PMID 34610363.

Goh SH, Choo YM, Ong SH. Minor constituents of palm oil. J Am Oil Chem Soc. 1985;62(2):237-40. doi: 10.1007/BF02541384.

Ahsan H, Ahad A, Siddiqui WA. A review of characterization of tocotrienols from plant oils and foods. J Chem Biol. 2015;8(2):45-59. doi: 10.1007/s12154-014-0127-8, PMID 25870713.

Top AG, Leong LW, Ong AS, Kawada T, Watanabe H, Tsuchiya N. Production of high concentration tocopherols and tocotrienols from palm-oil by-products; 1993. p. US5190618A.

Batistella CB, Moraes EB, Maciel Filho RM, Maciel MR. Molecular distillation: rigorous modeling and simulation for recovering vitamin E from vegetal oils. Appl Biochem Biotechnol. 2002;98-100:1187-206. doi: 10.1385/abab:98-100:1-9:1187, PMID 12018240.

Chu BS, Baharin BS, Che Man YB, Quek SY. Separation of vitamin E from palm fatty acid distillate using silica: II. J Food Eng. 2004;62(1):105-11. doi: 10.1016/S0260-8774(03)00197-3.

Yort L, Singanusong R, Yuenyong J, Sookwong P, Jiamyangyuen S. Optimization of vitamin E extraction from rice bran oil deodorizer distillate using response surface methodology. Curr Res Nutr Food Sci. 2022;10(3):1150-60. doi: 10.12944/CRNFSJ.10.3.28.

Byrne FP, Jin S, Paggiola G, Petchey TH, Clark JH, Farmer TJ. Tools and techniques for solvent selection: green solvent selection guides. Sustain Chem Process. 2016;4(1):1-24.

Lin SW, Yoo CK. Short-path distillation of palm olein and characterization of products. Euro J Lipid Sci & Tech. 2009;111(2):142-7. doi: 10.1002/ejlt.200800092.

Othman N, Manan ZA, Wan Alwi SR, Sarmidi MR. A review of extraction technology for carotenoids and vitamin E recovery from palm oil. J Appl Sci. 2010;10(12):1187-91. doi: 10.3923/jas.2010.1187.1191.

Peres VF, Saffi J, Melecchi MI, Abad FC, Martinez MM, Oliveira EC. Optimization of pressurized liquid extraction of Piper gaudichaudianum kunth leaves. J Chromatogr A. 2006;1105(1-2):148-53. doi: 10.1016/j.chroma.2005.08.036, PMID 16439261.

Kraujalis P, Venskutonis PR. Supercritical carbon dioxide extraction of squalene and tocopherols from amaranth and assessment of extracts antioxidant activity. J Supercrit Fluids. 2013;80:78-85. doi: 10.1016/j.supflu.2013.04.005.

Chen B, Koo YM, MacFarlane DR. Introduction: Ionic liquids. Lei Z. Chem Rev. 2017;24;117(10):6633-5.

Favre Reguillon A, Wang XX, Fu X, Pellet Rostaing S, Toussaint G. Selective extraction of neutral nitrogen compounds found in diesel feed by 1-butyl-3-methyl-imidazolium chloride. Xie LL Green Chem. 2008;10(5):524.

Meindersma GW, de Haan AB. Conceptual process design for aromatic/aliphatic separation with ionic liquids. Chem Eng Res Des. 2008;86(7):745-52. doi: 10.1016/j.cherd.2008.02.016.

Ferreira AR, Freire MG, Ribeiro JC, Lopes FM, Crespo JG, Coutinho JA. Overview of the liquid-liquid equilibria of ternary systems composed of ionic liquid and aromatic and aliphatic hydrocarbons, and their modeling by COSMO-RS. Ind Eng Chem Res. 2012;51(8):3483-507. doi: 10.1021/ie2025322.

Mora Pale M, Meli L, Doherty TV, Linhardt RJ, Dordick JS. Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass. Biotechnol Bioeng. 2011;108(6):1229-45. doi: 10.1002/bit.23108, PMID 21337342.

Yang Q, Xing H, Cao Y, Su B, Yang Y, Ren Q. Selective separation of tocopherol homologues by liquid-liquid extraction using ionic liquids. Ind Eng Chem Res. 2009;48(13):6417-22. doi: 10.1021/ie801847e.

Ni X, Xing H, Yang Q, Wang J, Su B, Bao Z. Selective liquid-liquid extraction of natural phenolic compounds Using amino acid Ionic liquids: a case of α-tocopherol and methyl linoleate separation. Ind Eng Chem Res. 2012;51(18):6480-8. doi: 10.1021/ie201682h.

Qin L, Zhang J, Cheng H, Chen L, Qi Z, Yuan W. Selection of imidazolium-based Ionic liquids for vitamin E extraction from deodorizer distillate. ACS Sustainable Chem Eng. 2016;4(2):583-90. doi: 10.1021/acssuschemeng.5b01330.

Tian X, Zhang X, Wei L, Zeng S, Huang L, Zhang S. Multi-scale simulation of the 1,3-butadiene extraction separation process with an ionic liquid additive. Green Chem. 2010;12(7):1263-73. doi: 10.1039/b918924f.

Hunt PA. Why does a reduction in hydrogen bonding lead to an increase in viscosity for the 1-butyl-2,3-dimethyl-imidazolium-based ionic liquids? J Phys Chem B. 2007;111(18):4844-53. doi: 10.1021/jp067182p, PMID 17388550.

Zhou T, Chen L, Ye Y, Chen L, Qi Z, Freund H. An overview of mutual solubility of ionic liquids and water predicted by COSMO-RS. Ind Eng Chem Res. 2012;51(17):6256-64. doi: 10.1021/ie202719z.

Pandey A, Rai R, Pal M, Pandey S. How polar are choline chloride-based deep eutectic solvents? Phys Chem Chem Phys. 2014;16(4):1559-68. doi: 10.1039/c3cp53456a, PMID 24305780.

Spange S, Lungwitz R, Schade A. Correlation of molecular structure and polarity of ionic liquids. J Mol Liq. 2014;192:137-43. doi: 10.1016/j.molliq.2013.06.016.

Published

12-08-2024

How to Cite

ULFA, D. M., MUNIM, A., RAHMAWATI, S. I., PUTRA, M. Y., & BAYU, A. (2024). IMIDAZOLIUM-BASED IONIC LIQUIDS FOR THE SELECTIVE SEPARATION OF TOCOTRIENOL HOMOLOGUES FROM PALM FATTY ACID DISTILLATE VIA LIQUID-LIQUID EXTRACTION. International Journal of Applied Pharmaceutics, 16(3), 72–76. https://doi.org/10.22159/ijap.2024.v16s3.13

Issue

Section

Original Article(s)