In vitro evaluation of the antioxidant potential of derivatives eugenol via ABTS radical capture assay
In vitro antioxidant activity of eugenol derivatives
Abstract
Eugenol is a natural product present in different plant species, especially in the flower buds of Syzygiu Aromatum. This secondary metabolite exhibits antioxidant action, in addition to acting as an anti-inflammatory, antitumor, antibacterial, antifungal, antipyretic, anesthetic and analgesic agent. Given the biological potential of eugenol, the antioxidant activity of eugenol derivatives was evaluated. Thus, eugenol isolated from flower buds of Syzygiu aromaticum was subjected to different types of reactions such as O-alkylation. The eugenol derivatives were characterized by 1H and 13C NMR techniques. The evaluation of antioxidante activity was carried out using the ABTS radical capture assay. Six derivatives were synthesized with yields ranging from 75-92%, which exhibited low antioxidant potential compared to radical capture assays, with EC50 values from 0.085 to 0.327 mg/mL. These results motivate new studies, since the search for new antioxidant agents is extremely necessary in view of the numerous pathologies that are associated with oxidative stress.
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References
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Arfa, A.B., Combes, S., Preziosi-Belloy, L., Gontard, N. & Chalier, P. (2006). Antimicrobial activity of carvacrol related to its chemical structure. Letters in Applied Microbiology, 43(2), 149–154. doi: 10.1111/j.1472-765X.2006.01938.x
Ashok, D., Gundu, S., Amate, V.K. & Devulapally, M.G. (2018). Conventional and microwave- assisted synthesis of new indole-tethered benzimidazole-based 1,2,3-triazoles and evaluation of their antimycobacterial, antioxidant and antimicrobial activities. Molecular Diversity, 22(4):769-778. doi: 10.1007/s11030-018-9828-1
Barbosa, J.D., Silva, V.B., Alves, P.B., Gumina, G., Santos, R.L., Sousa, D.P. & Cavalcanti, S.C. (2012). Structure-activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae. Pest Management Science, 68(11), 1478-1483. doi: 10.1002/ps.3331
Batiha, G.E., Alkazmi, L.M., Wasef, L.G., Beshbishy, A.M., Nadwa, E.H. & Rashwan, E.K. (2020). Syzygium aromaticum L. (Myrtaceae): Traditional Uses, Bioactive Chemical Constituents, Pharmacological and Toxicological Activities. Biomolecules, 10(2), 202. doi: 10.3390/biom10020202
Chan, D.M., Monaco K.L., Wang, R. & Winters, M.P. (1998). New N- and O-Arylations with Phenylboronic Acids and Cupric Acetate. Tetrahedron Letters, 39(19), 2933-2936. doi: 10.1016/S0040-4039(98)00503-6
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Ferroni, C., Pepe, A., Kim, Y. S., Lee, S., Guerriri, A., Parenti, M. D. & Varchi, G. (2017). 1,4-Substituted Triazoles as Non-Steroidal Antiandrogens for Prostate Cancer Treatment. Journal of Medicinal Chemistry, 60(7), 3082-3093. doi: 10.1021/acs.jmedchem.7b00105
Gulçin, İ. (2011). Antioxidant Activity of Eugenol: A Structure–Activity Relationship Study. Journal of Medicinal Food, 14(9), 975–985. doi: 10.1089/jmf.2010.0197
Gupta, A., Kumar, R., Ganguly, R., Singh, A.K., Rana, H.K. & Pandey, A.K. (2020). Antioxidant, anti-inflammatory and hepatoprotective activities of Terminalia bellirica and its bioactive component ellagic acid against diclofenac induced oxidative stress and hepatotoxicity. Toxicology Reports, 24(8), 44-52. doi: 10.1016/j.toxrep.2020.12.010
Kumar, N.V., Kumar, S.C.S., Srinivas, P. & Bettadaiah, B.K. (2015). An Improved Route to the Preparation of 6-, 8-, 10-Gingerols. Organic Preparations and Procedures International, 47(6), 443-448. doi: 10.1080/00304948.2015.1088754
Kumar, N.V., Srinivas, P. & Bettadaiah, B.K. (2012). New scalable and eco-friendly synthesis of gingerols. Tetrahedron Letters, 53(24), 2993-2995. doi: 10.1016/j.tetlet.2012.03.092
Lalwani, K.G. & Sudalai, A. (2015). First Enantioselective Synthesis of Surinamensinol B and a Non-Natural Polysphorin Analogue by a Two-Stereocentered Hydrolytic Kinetic Resolution. European Journal Organic Chemistry, 2015(33), 7344–7351. https://doi.org/10.1002/ejoc.201501009
Rahim, N.H.C.A., Asari, A., Ismail, N. & Osman, H. (2016). Synthesis and Antibacterial Study of Eugenol Derivatives. Asian Journal of Chemistry, 29(1), 22-26. Doi: 10.14233/ajchem.2017.20100
Silva, F.F.M., Monte, F.J.Q., Lemos, T.L.G., Nascimento, P.G.G., Costa, A.K.M. & Paiva, L.M.M. (2018). Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities. Chemistry Central Journal, 12, 34. doi: 10.1186/s13065-018-0407-4
Spurg, A. & Waldvogel, S.R. (2008). High-Yielding Cleavage of (Aryloxy)acetates. Eur Journal of Organic Chemistry, 2, 337–342. https://doi.org/10.1002/ejoc.200700769
Tan, B.L., Norhaizan, M.E., Liew, W.P.P. & Rahman, H.S. (2018). Antioxidant and Oxidative Stress: A Mutual Interplay in Age-Related Diseases. Front Pharmacol, 9, 1162. doi: 10.3389/fphar.2018.01162.
Teixeira, R.R., Gazolla, P.A.R., Da Silva, A.M., Borsodi, M.P.G., Bergmann, B.R, Ferreira, R.S., Vaz, B.G., Vasconcelos, G.A. & Lima, W.P. (2018). Synthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities. European Journal Medicinal Chemistry, 146, 274-286. doi: 10.1016/j.ejmech.2018.01.046
Van, D.E.N., Dool, H. & Kratz, P.D. (1963). A Generalization of the Retention Index System Including Linear Temperature Programmed Gas-Liquid Partition Chromatography. Journal of Chromatography A, 11, 463-471. https://doi.org/10.1016/S0021-9673(01)80947-x.
Published
2023-12-30
How to Cite
CUNHA LIMA, Josefa Aqueline et al.
In vitro evaluation of the antioxidant potential of derivatives eugenol via ABTS radical capture assay.
Acta Brasiliensis, [S.l.], v. 7, n. 3, p. 80-84, dec. 2023.
ISSN 2526-4338.
Available at: <http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/666>. Date accessed: 03 july 2024.
doi: https://doi.org/10.22571/2526-4338666.
Section
Pharmacy
