Avaliação in vitro do potencial antioxidante de derivados de eugenol via ensaio de captura de radicais ABTS
Atividade antioxidante in vitro de derivados de eugenol
Resumo
O eugenol é um produto natural presente em diferentes espécies vegetais, com destaque, nos botões florais de Syzygiu Aromatum. Esse metabólito secundário exibe ação antioxidante, além de atuar como anti-inflamatório, antitumoral, antibacteriano, antifúngico, antipirético, anestésico e analgésico. Dado o potencial biológico do eugenol, foi avaliada a atividade antioxidante dos derivados do eugenol. Assim, o eugenol isolado dos botões florais de Syzygiu Aromatum foi submetido a diferentes tipos de reações, como a O-alquilação. Os derivados de eugenol foram caracterizados pelas técnicas de RMN de 1H e 13C. A avaliação da atividade antioxidante foi realizada utilizando o ensaio de captura de radicais ABTS. Seis derivados foram sintetizados com rendimentos variando de 75 a 92%, os quais exibiram baixo potencial antioxidante em comparação aos ensaios de captura de radicais, com valores de CE50 de 0,085 a 0,327 mg/mL. Estes resultados motivam novos estudos, uma vez que a busca por novos agentes antioxidantes é extremamente necessária em face as inúmeras patologias que estão associadas ao estresse oxidativo.
##plugins.generic.usageStats.downloads##
Não há dados estatísticos.
Referências
Adams, R.P. (2017). Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy, (4.1th ed. 809p) Allured Publishing Corporation: Carol Stream, Illinois.
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
Farias, M.D., Oliveira, P.S., Dutra, F.S.P., Fernandes, T.J., Pereira, C.M.P., Oliveira, S.Q., Stefanello, F.M., Lencina, C.L. & Barschaka, A.G. (2014). Eugenol derivatives as potential anti-oxidants: is phenolic hydroxyl necessary to obtain an effect?. Journal Pharmacy and Pharmacology, 66(5), 733-46. doi: 10.1111/jphp.12197
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.
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
Farias, M.D., Oliveira, P.S., Dutra, F.S.P., Fernandes, T.J., Pereira, C.M.P., Oliveira, S.Q., Stefanello, F.M., Lencina, C.L. & Barschaka, A.G. (2014). Eugenol derivatives as potential anti-oxidants: is phenolic hydroxyl necessary to obtain an effect?. Journal Pharmacy and Pharmacology, 66(5), 733-46. doi: 10.1111/jphp.12197
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.
Publicado
2023-12-30
Como Citar
CUNHA LIMA, Josefa Aqueline et al.
Avaliação in vitro do potencial antioxidante de derivados de eugenol via ensaio de captura de radicais ABTS.
Acta Brasiliensis, [S.l.], v. 7, n. 3, p. 80-84, dez. 2023.
ISSN 2526-4338.
Disponível em: <http://www.revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/666>. Acesso em: 19 maio 2024.
doi: https://doi.org/10.22571/2526-4338666.
Seção
Farmácia
