Synthesis and Antioxidant Activity of Some Dibenzylidene-Cyclohexanones
Keywords:
Antioxidant, DPPH, FRAP, synthesis
Abstract
Dibenzylidene-cyclohexanone is a curcumin analog. Analog of curcumins showed activity as antioxidant. This research is aimed to synthesize and study the antioxidant activity of dibenzylidene-cyclohexanone compounds. The synthesis was carried out according to carbonyl condensation reaction and its antioxidant activity was tested by using DPPH radical scavenging activity and FRAP assay. Compound entry 1 (2,6-bis-(3’-Bromo-4’-methoxybenzylidene)-cyclohexanone) and entry 3 (2,6-bis-(2’-chloro-6’-fluorobenzylidene)- cyclohexanone) were obtained in 70 % yield. Compound entries 1 and 2 gave the same antioxidant activities according to the DPPH method and this result was not good enough compared to vitamin E. Compound entry 1 showed the best antioxidant activity among the series and also had a better antioxidant activity compared to vitamin E. From these results, it can be said that compound entry 1 was the best antioxidant agent in the series.
References
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Yuwono, T., & Oetari, R. A. (2004). The stability of PGV-0 (Pentagamavunon-0) as an Antiinflammatory drug in liquid dosage forms. Indonesian Journal of Pharmacy, 15(Vol 15 No 1, 2004), 20–25. http://indonesianjpharm.farmasi.ugm.ac.id/index.php/3/article/view/550
Ak, T., & Gülçin, I. (2008). Antioxidant and radical scavenging properties of curcumin. Chemico-Biological Interactions, 174(1), 27–37. https://doi.org/10.1016/j.cbi.2008.05.003
Allegra, A., Innao, V., Russo, S., Gerace, D., Alonci, A., & Musolino, C. (2016). Anticancer Activity of Curcumin and Its Analogues: Preclinical and Clinical Studies. Http://Dx.Doi.Org/10.1080/07357907.2016.1247166, 35(1), 1–22. https://doi.org/10.1080/07357907.2016.1247166
Anas Tomeh, M., Hadianamrei, R., & Zhao, X. (2019). Molecular Sciences A Review of Curcumin and Its Derivatives as Anticancer Agents. https://doi.org/10.3390/ijms20051033
Arsani, N. K. (2019). Sintesis dan Uji Aktivitas Antioksidan Senyawa 2,6-Bis-(2’,4’-Ddiklorobenziliden)-Ssikloheksanon Dengan Metode Penangkapan Radikal Bbebas DPPH dan Reduksi Ion Ferri. Gadjah Mada University.
Biswas, S. K. (2016). Does the Interdependence between Oxidative Stress and Inflammation Explain the Antioxidant Paradox? Oxidative Medicine and Cellular Longevity, 2016, 17–19. https://doi.org/10.1155/2016/5698931
De, A., Beligala, D. H., Birkholz, T. M., & Geusz, M. E. (2019). Anticancer Properties of Curcumin and Interactions With the Circadian Timing System. In Integrative Cancer Therapies (Vol. 18). https://doi.org/10.1177/1534735419889154
Ekananda, S. D. (2019). Sintesis dan Uji Aktivitas Antioksidan Senyawa 2,6-Bis-(2’-KLORO-6’-Fluorobenziliden)-Sikloheksanon. Gadjah Mada University.
Eryanti, Y., Nurulita, Y., Hendra, R., Syahri, J., & Zamri, A. (2011). Synthesizing Derivatives from Cyclopentanone Analogue Curcumin and Their Toxic, Antioxidant and Anti-Inflammatory Activities. 15(2), 117–123.
Fatmayanti, B. R. (2019). Sintesis dan Uji Aktivitas Antioksidan Senyawa Analaog Kurkumin 2,6-Bis-(3’-Bromo-4’-Metoksibenziliden)- Sikloheksanon Dengan Metode Penangkapan Radikal Bebas DPPH dan Reduksi Ion Ferri. Universitas Gadjah Mada.
Ikawati, M., Purwanto, H., Imaniyyati, N. N., Afifah, A., Sagiyo, M. L., Yohanes, J., Sismindari, & Ritmaleni. (2018). Cytotoxicity of Tetrahydropentagamavunon-0 (THPGV-0) and Tetrahydropentagamavunon-1 (THPGV-1) on several cancer cells lines. Indonesian Journal of Pharmacy, 29(4), 179–189. https://doi.org/10.14499/indonesianjpharm29iss4pp179
Marchiani, A., Rozzo, C., Fadda, A., Delogu, G., & Ruzza, P. (2013). Curcumin and Curcumin-like Molecules: From Spice to Drugs. Current Medicinal Chemistry, 21(2), 204–222. https://doi.org/10.2174/092986732102131206115810
Murwanti, R., Rahmadani, A., Ritmaleni, Hermawan, A., & Ari Sudarmanto, B. S. (2020). Curcumin analogs induce apoptosis and G2/M arrest in 4T1 murine triple-negative breast cancer cells. Indonesian Journal of Pharmacy, 31(1), 11–18. https://doi.org/10.14499/indonesianjpharm31iss1pp11
Nelson, K. M., Dahlin, J. L., Bisson, J., Graham, J., Pauli, G. F., & Walters, M. A. (2017). The Essential Medicinal Chemistry of Curcumin. Journal of Medicinal Chemistry, 60(5), 1620–1637. https://doi.org/10.1021/acs.jmedchem.6b00975
Panahi, Y., Hosseini, M. S., Khalili, N., Naimi, E., Simental-Mendía, L. E., Majeed, M., & Sahebkar, A. (2016). Effects of curcumin on serum cytokine concentrations in subjects with metabolic syndrome: A post-hoc analysis of a randomized controlled trial. Biomedicine and Pharmacotherapy, 82, 578–582. https://doi.org/10.1016/j.biopha.2016.05.037
Parihar, V. K., Dhawan, J., Kumar, S., Manjula, S. N., Subramanian, G., Unnikrishnan, M. K., & Rao, C. M. (2007). Free radical scavenging and radioprotective activity of dehydrozingerone against whole body gamma irradiation in Swiss albino mice. Chemico-Biological Interactions, 170(1), 49–58. https://doi.org/10.1016/j.cbi.2007.07.006
Reksohadiprodjo, M. S. ;, Timmerman, H. S., Margono, Supardjan Amir; Martono, S., & Hakim, Lukman; Hakim, Arief Rahman; Puspitasari, Ika; Nurrochmad, Arief ; Purwantiningsih; Oetari; Yuwono, T. (2004). Derivatives of Benzylidene Cyclohexanone, Benzylidene Cyclopentanone, and Benzylidene Acetone, and Theurapeutic Uses Thereof.
Ritmaleni. (2016). Synthesis of Curcumin Analogs. International Journal of Pharmaceutical Sciences Review and Research, 37(1), 236–241.
Ritmaleni, Hastutitama, A. N. A., Persitamaia, I., Restiwardani, T., Eksakta, A., Munandar, R. F., Abdullah, M. S., Purwanto, A. E., Astuti, P., & Sardjiman. (2021). Syntesis and antibacterial activity of dibenzylidene-cyclohexanone. Rasayan Journal of Chemistry, 14(3), 2090–2096. https://doi.org/10.31788/RJC.2021.1436240
Ritmaleni, & Simbara, A. (2010). Sintesis Tetrahidro Pentagamavunon-0. Majalah Farmasi Indonesia, 21(2), 100–105.
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
Simon, E., Aswini, P., Sameer Kumar, V. B., & Mankadath, G. (2018). Curcumin and its synthetic analogue dimethoxycurcumin differentially modulates antioxidant status of normal human peripheral blood mononuclear cells. Free Radical Research, 52(5), 583–591. https://doi.org/10.1080/10715762.2018.1455002
Tanvir, E. M., Sakib Hossen, M., Fuad Hossain, M., Afroz, R., Gan, S. H., Khalil, M. I., & Karim, N. (2017). Antioxidant Properties of Popular Turmeric (Curcuma longa) Varieties from Bangladesh. https://doi.org/10.1155/2017/8471785
Teixeira Lima, F., Seba, V., Silva, G., Silva Torrezan, G., Roberto Polaquini, C., Caressato Pinhanelli, V., Baek, S. J., Lúcia Fachin, A., Octavio Regasini, L., & Marins, M. (2018). The Curcumin Analog CH-5 Exerts Anticancer Effects in Human Osteosarcoma Cells via Modulation of Transcription Factors p53/Sp1. International Journal of Molecular Science, 19(1909). https://doi.org/10.3390/ijms19071909
Tranggono, B. N. (2019). Sintesis dan Uji Aktivitas Antioksidan Senyawa 2,6-Bis -(2’- Karboksibenziliden)Sikloheksanon Dengan Metode Penangkapan Radikal Bebas DPPH dan Reduksi Ion Ferri. Gadjah Mada University.
Wang, M., Jiang, S., Zhou, L., Yu, F., Ding, H., Li, P., Zhou, M., & Wang, K. (2019). Potential Mechanisms of Action of Curcumin for Cancer Prevention: Focus on Cellular Signaling Pathways and miRNAs. Int. J. Biol. Sci, 15(6), 1200–1214. https://doi.org/10.7150/ijbs.33710
Yuwono, T., & Oetari, R. A. (2004). The stability of PGV-0 (Pentagamavunon-0) as an Antiinflammatory drug in liquid dosage forms. Indonesian Journal of Pharmacy, 15(Vol 15 No 1, 2004), 20–25. http://indonesianjpharm.farmasi.ugm.ac.id/index.php/3/article/view/550
Published
2023-03-31
How to Cite
Ritmaleni, R., Fatmayanti, R. B., Ekananda, S. D., Tranggono, B. N., Arsani, N. K., & Rumiyati, R. (2023). Synthesis and Antioxidant Activity of Some Dibenzylidene-Cyclohexanones. Indonesian Journal of Pharmacy, 34(1), 93-102. https://doi.org/10.22146/ijp.4537
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Research Article
