Purification of Curcumin Derivate (1,5-bis(4’-hydroxy-3’-methoxyphenyl)-1,4-pentadien-3-on) Using Chromatotron

Sabtanti Harimurti(1*), Alfan Fadhilah(2), Hari Widada(3), Vella Lailli Damarwati(4)

(1) School of Pharmacy, Faculty of Medicine and Health Sciences, Universitas Muhammadiyah Yogyakarta, Indonesia, Jl. Brawijaya, Tamantirto, Kasihan, Bantul, Yogyakarta, 55183, Indonesia
(2) School of Pharmacy, Faculty of Medicine and Health Sciences, Universitas Muhammadiyah Yogyakarta, Indonesia, Jl. Brawijaya, Tamantirto, Kasihan, Bantul, Yogyakarta, 55183, Indonesia
(3) School of Pharmacy, Faculty of Medicine and Health Sciences, Universitas Muhammadiyah Yogyakarta, Indonesia, Jl. Brawijaya, Tamantirto, Kasihan, Bantul, Yogyakarta, 55183, Indonesia
(4) School of Pharmacy, Faculty of Medicine and Health Sciences, Universitas Muhammadiyah Yogyakarta, Indonesia, Jl. Brawijaya, Tamantirto, Kasihan, Bantul, Yogyakarta, 55183, Indonesia
(*) Corresponding Author

Abstract

Curcumin derivate with IUPAC name 1,5-bis(4’-hydroxy-3’-methoxyphenyl)-1,4-pentadien-3-on is also known as Gamavuton-0 (GVT-0) reported has an activity as anti-inflammation and anti-cancer. GVT-0 can be synthesized using vanillin and acetone as starting material by aldol condensation. Purification process of GVT-0 after synthesis usually was done using maceration. This method resulting un-pure GVT-0, therefore, another separation technique of Chromatotron was chosen. This research aims to investigate the effectiveness of Chromatotron towards the purity of GVT-0. The study was started by GVT-0 synthesis. The synthesis was using 4.4 mole of vanillin and 1 mole acetone as the raw material. Microwave irradiation was used as the energy source. Isolation of GVT-0 using hot water maceration. Further, the purification of GVT-0 was conducted using Chomatotron. First step of purification using Chomatotron was preparing best ratio between hexane and chloroform as solvent to remove vanillin. Further, the best combination of solvent was used to separate all the vanillin remaining in the bulk of GVT-0. Last step after all vanillin was removed, the GVT-0 remining in the silica was elucidated using chloroform. The purity was evaluated using Melting-point analysis and Thin Layer Chromatography (TLC) with four different mobile phases. Based on the data of melting point and TLC, a pure GVT-0 was obtained. The Chomatotron may be recommended for purification of GVT-0, however this method consumes a lot of organic solvent that may need to be improved in the future with more environmentally process

Keywords

Chromatotron; GVT-0; melting point; TLC

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References

Agrawal, V., & Desai, S., 2015. Centrifugally accelerated thin layer chromatography for isolation of marker compounds and bioactives. Journal of Pharmacognosy and Phytochemistry, 3(6), 145–149.

Atun, S., 2014. Metode Isolasi dan Identifikasi Struktural Senyawa Organik Bahan Alam. Borobudur, 8(2), 53–61. https://doi.org/10.33374/jurnalkonservasicagarbudaya.v8i2.132

Balasubramanyam, M., Koteswari, A. A., Kumar, R. S., Monickaraj, S. F., Maheswari, J. U., & Mohan, V., 2003. Curcumin-induced inhibition of cellular reactive oxygen species generation: Novel therapeutic implications. Journal of Biosciences 2003 28:6, 28(6), 715–721. https://doi.org/10.1007/BF02708432

Harimurti, S., Setyonugroho, W., & Pramono, A., 2019. Energy Savings on Curcumine Derivative Gamavuton-0 Synthesis Using Microwave Irradiation. International Journal of Applied Pharmaceutics, 11(3), 155–158. https://doi.org/10.22159/IJAP.2019V11I3.31979

Jandera, P., & Churáček, J., 1981. Advances in Chromatography (pp. 125–260). Boca Raton: CRC Press. https://doi.org/10.1201/9781003209690-5

Móricz, M., & Vovk, I., 2016. Centrifugal layer chromatography—Rotation planar chromatography in Forced-Flow Layer Chromatography (pp. 187–222). https://doi.org/10.1016/B978-0-12-420161-3.00003-4

Muti’ah, R., 2015. Evidence Based Kurkumin dari Tanaman Kunyit (Curcuma longa) sebagai Terapi Kanker pada Pengobatan Modern. Journal of Islamic Pharmacy, 1(1), 28–41. https://doi.org/10.18860/JIP.V1I1.4178

Raflizar, R. (Raflizar), & Nainggolan, O. (Olwin)., 2010. Faktor Determinan Tumor/kanker Kulit di Pulau Jawa (Analisis Data Riskesdas 2007). Buletin Penelitian Sistem Kesehatan, 13(4), 21319. https://doi.org/10.22435/BPSK.V13I4

Sabet, S., Rashidinejad, A., Melton, L. D., & McGillivray, D. J., 2021. Recent advances to improve curcumin oral bioavailability. Trends in Food Science & Technology, 110, 253–266. https://doi.org/10.1016/J.TIFS.2021.02.006

Safitri, C., Ritmaleni, R., Rintiswati, N., Sardjiman, S., & Kaneko, T., 2018. Antimycobacterial Activity of Benzylidene Acetone analogues of Curcumin Againts Resistant and Sensitive Mycobacterium tuberculosis. IOSR JDMS, 16(12), 21–26.

Sardjiman, S. S., Reksohadiprodjo, M. S., Hakim, L., Van Der Goot, H., & Timmerman, H., 1997. 1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship. European Journal of Medicinal Chemistry, 32(7–8), 625–630. https://doi.org/10.1016/S0223-5234(97)83288-6

Singh, N., Kumar, A., Gupta, V. K., & Sharma, B., 2018. Biochemical and Molecular Bases of Lead-Induced Toxicity in Mammalian Systems and Possible Mitigations. Chemical Research in Toxicology, 31(10), 1009–1021. https://doi.org/10.1021/acs.chemrestox.8b00193/

Siviero, A., Gallo, E., Maggini, V., Gori, L., Mugelli, A., Firenzuoli, F., & Vannacci, A., 2015. Curcumin, a golden spice with a low bioavailability. Journal of Herbal Medicine, 5(2), 57–70. https://doi.org/10.1016/j.hermed.2015.03.001

Tønnesen, H. H., 2002. Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Studies of curcumin and curcuminoids, XXVIII. Die Pharmazie, 57(12), 820–824. https://europepmc.org/article/med/12561244

Valko, M., Jomova, K., Rhodes, C. J., Kuča, K., & Musílek, K., 2015. Redox- and non-redox-metal-induced formation of free radicals and their role in human disease. Archives of Toxicology 2015 90:1, 90(1), 1–37. https://doi.org/10.1007/S00204-015-1579-5

Yalkowsky, S. H., & Alantary, D. 2018. Estimation of Melting Points of Organics. Journal of Pharmaceutical Sciences, 107(5), 1211–1227. https://doi.org/10.1016/j.xphs.2017.12.013

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