Atividade antimicrobiana de compostos isolados e derivados semissintéticos de Miconia ferruginata
DOI:
https://doi.org/10.22571/2526-4338249Palavras-chave:
Melastomataceae, Ácido oleanólico, triterpenos, ácido ursólicoResumo
Este estudo descreve a avaliação da atividade antimicrobiana de compostos isolados e derivados semissintéticos de Miconia ferruginata (Melastomataceae) contra cinco microorganismos: Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), Bacillus subtilis (ATCC 6623), Pseudomonas aeruginosa (ATCC 15442) and Candida albicans (ATCC 10231). A mistura isomérica dos ácidos ursólico e oleanólico foi ativa contra S. aureus (CIM = 250 μg mL-1) e contra E. coli, B. subtilis e P. aeruginosa (CIM = 500 μg mL-1). A flavona 5,6,7-trihidroxi-4’-metóxiflavona e os ésteres metílicos, derivados semissintéticos da mistura dos ácidos ursólico e oleanólico, não apresentaram atividade contra os microrganismos testados. Estes resultados sugerem que o grupo carboxila presente nos triterpenos podem contribuir para a atividade antimicrobiana.
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Referências
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Lima, R.C.L., Kongstad, K.T., Kato, L., das Silva, M.J., Franzyk, H., & Staerk, D. (2018). High-Resolution PTP1B Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of PTP1B Inhibitors from Miconia albicans. Molecules, 23(7), 1755. doi:10.3390/molecules23071755
Liu J. (1995). Pharmacology of oleanolic acid and ursolic acid. Journal of Ethnopharmacology, 49(2), 57-68. doi:10.1016/0378-8741(95)90032-2
Liu, Y., Ding, S., Shenab, & J., Zhu, K. (2019). Nonribosomal antibacterial peptides that target multidrug-resistant bacteria. Natural Product Reports, 36(4), 573–592. doi:10.1039/c8np00031j
Peixoto, J.A., Andrade e Silva, M.L., Crotti, A.E.M., Veneziani, R.C.S., Gimenez, V.M.M., Januário, A.H., Groppo, M., Magalhães, L.G., dos Santos, F.F., Albuquerque, S., da Silva Filho, A.A., & Cunha, W.R. (2011). Antileishmanial activity of the hydroalcoholic extract of Miconia langsdorffii, isolated compounds, and semi-synthetic derivatives. Molecules, 16(2), 1825-1833. doi:10.3390/molecules16021825
Renner, S.S. (1993). Phylogeny and classification of the Melastomataceae and Memecylaceae. Nordic Journal of Botany, 13 (5), 519-540. doi:10.1111/j.1756-1051.1993.tb00096.x
Rodrigues, J., Rinaldo, D., da Silva, M.A., dos Santos, L.C., & Vilegas, W. (2011). Secondary Metabolites of Miconia rubiginosa. Journal of Medicinal Food, 14(7-8), 834-839. doi:10.1089/jmf.2010.0157
Savant, C., Venkatesh, Mannasaheb, B.A., & Joshi, H. (2014). Importance of antimicrobial agents from plants in present scenario: a review. International Journal of pharmacognosy, 1(8), 472-484. doi:10.13040/IJPSR.0975-8232.IJP.1(8).472-84
Vasconcelos, M.A.L, Royo, V.A., Ferreira, D.S., Crotti, A.E.M., Andrade e Silva, M.L., Carvalho, J.C., Bastos, J.K., & Cunha, W.R. (2006). In vivo analgesic and anti-inflammatory activities of ursolic acid and oleanoic acid from Miconia albicans (Melastomataceae). Zeitschrift für Naturforschung C, 61(7-8), 477-482. doi:10.1515/znc-2006-7-803
Viegas, F.P.D., Espuri, P.F., Oliver, J.C., Silva, N.C., Dias, A.L.T., Marques, M.J., & Soares, M.G. (2019). Leishmanicidal and antimicrobial activity of primin and primin-containing extracts from Miconia willdenowii. Fitoterapia, (138), 1-5. doi:10.1016/j.fitote.2019.104297
Wolska, K.I., Grudniak, A.M., Fiecek, B., Kraczkiewicz-Dowjat, A., & Kurek, A. (2010). Antibacterial activity of oleanolic and ursolic acids and their derivatives. Central European Journal of Biology, 5(5), 543-553. doi:10.2478/s11535-010-0045-x
Boscolo, O.H. & Valle, L.S. (2008). Plantas de uso medicinal em Quissamã, Rio de Janeiro, Brasil. Editora Iheringia: Série Botânica. 63(2), 263-277.
Clinical and Laboratory Standards Institute. (2003). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, Approved Standard – M7-A6, 6th ed., NCCLS/CLSI: Wayne, vol. 23.
Cunha, L.C.S., Silva, M.L.A., Furtado, N.A.J.C., Vinhólis, A.H.C., Martins, C.H.G., da Silva Filho, A.A., & Cunha, W.R. (2007). Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogens. Zeitschrift für Naturforschung C, 62(9-10), 668-672. doi:10.1515/znc-2007-9-1007
Cunha, G.O.S., Matos, A.P., Bernardo, A.R., Menezes, A.C.S., Burger, M.C.M., Vieira, P.C., Forim, M.R., Fernandes, J.B., & Silva, M.F.G.F. (2017). Constituintes químicos e atividade inseticida de Miconia ferruginata. Química Nova, (40), 1158-1163. doi:10.21577/0100-4042.20170126
Cunha, W.R., Crevelin, E.J., Arantes, G.M., Crotti, A.E.M., Andrade e Silva, M. L., Furtado, N.A.J.C., Albuquerque, S., & Ferreira, D.S. (2006). A study of the trypanocidal activity of triterpene acids isolated from Miconia species. Phytotherapy Research, 20(6), 474-478. doi:10.1002/ptr.1881
Cunha, W.R., Matos, G.X., Souza, M.G.M., Tozatti, M.G., Andrade e Silva, M.L., Martins, C.H.G., Silva, R., & Filho, A.A.S. (2010). Evaluation of the antibacterial activity of the methylene chloride extract of Miconia ligustroides, isolated triterpene acids, and ursolic acid derivatives. Pharmaceutical Biology, 48(2), 166-169. doi:10.3109/13880200903062648
Cunha, W.R., Silva, M.L.A., Santos, F.M., Montenegro, I.M., Oliveira, A.R.A., Tavares, H.R., Santos, H.S.L., & Bizário, J.C.S. (2008). In vitro Inhibition of tumor cell growth by Miconia fallax. Pharmaceutical Biology, 46(4), 292-294. doi:10.1080/13880200701741245
Goldenberg, R., Penneys, D.S., Almeda, F., Judd, W.S., & Michelangeli, F.A. (2008). Phylogeny of Miconia (Melastomataceae): patterns of stamen diversification in a megadiverse neotropical genus. International Journal of Plant Sciences, 169(7), 963-979. doi:10.1086/589697
Gontijo, D.C., Gontijo, P.C., Brandão, G.C., Diaz, M.A.N., Oliveira, A.B., Fietto, L.G., & Leite, J.P.V. (2019). Antioxidant study indicative of antibacterial and antimutagenic activities of an ellagitannin-rich aqueous extract from the leaves of Miconia latecrenata. Journal of Ethnopharmacology, (236), 114-123. doi:10.1016/j.jep.2019.03.007
Heinemann, J.A. (2001). Can smart bullets penetrate magic bullet-proof vest? Drug Discovery Today, 6(17), 875-878. doi:10.1016/S1359-6446(01)01857-8
Jesus, J.A., Lago, J.H.G., Laurenti, M.D., Yamamoto, E.S., & Passero, L.F.D. (2015). Antimicrobial activity of oleanolic and ursolic acids: An update. Evidence-Based Complementary and Alternative Medicine, (2015), 1-14. doi:10.1155/2015/620472
Leonard, J., Lygo, B., & Procter, G. (1995). Advanced Practical Organic Chemistry. 2a ed. Oxford: Chapman & Hall.
Lima, R.C.L., Kongstad, K.T., Kato, L., das Silva, M.J., Franzyk, H., & Staerk, D. (2018). High-Resolution PTP1B Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of PTP1B Inhibitors from Miconia albicans. Molecules, 23(7), 1755. doi:10.3390/molecules23071755
Liu J. (1995). Pharmacology of oleanolic acid and ursolic acid. Journal of Ethnopharmacology, 49(2), 57-68. doi:10.1016/0378-8741(95)90032-2
Liu, Y., Ding, S., Shenab, & J., Zhu, K. (2019). Nonribosomal antibacterial peptides that target multidrug-resistant bacteria. Natural Product Reports, 36(4), 573–592. doi:10.1039/c8np00031j
Peixoto, J.A., Andrade e Silva, M.L., Crotti, A.E.M., Veneziani, R.C.S., Gimenez, V.M.M., Januário, A.H., Groppo, M., Magalhães, L.G., dos Santos, F.F., Albuquerque, S., da Silva Filho, A.A., & Cunha, W.R. (2011). Antileishmanial activity of the hydroalcoholic extract of Miconia langsdorffii, isolated compounds, and semi-synthetic derivatives. Molecules, 16(2), 1825-1833. doi:10.3390/molecules16021825
Renner, S.S. (1993). Phylogeny and classification of the Melastomataceae and Memecylaceae. Nordic Journal of Botany, 13 (5), 519-540. doi:10.1111/j.1756-1051.1993.tb00096.x
Rodrigues, J., Rinaldo, D., da Silva, M.A., dos Santos, L.C., & Vilegas, W. (2011). Secondary Metabolites of Miconia rubiginosa. Journal of Medicinal Food, 14(7-8), 834-839. doi:10.1089/jmf.2010.0157
Savant, C., Venkatesh, Mannasaheb, B.A., & Joshi, H. (2014). Importance of antimicrobial agents from plants in present scenario: a review. International Journal of pharmacognosy, 1(8), 472-484. doi:10.13040/IJPSR.0975-8232.IJP.1(8).472-84
Vasconcelos, M.A.L, Royo, V.A., Ferreira, D.S., Crotti, A.E.M., Andrade e Silva, M.L., Carvalho, J.C., Bastos, J.K., & Cunha, W.R. (2006). In vivo analgesic and anti-inflammatory activities of ursolic acid and oleanoic acid from Miconia albicans (Melastomataceae). Zeitschrift für Naturforschung C, 61(7-8), 477-482. doi:10.1515/znc-2006-7-803
Viegas, F.P.D., Espuri, P.F., Oliver, J.C., Silva, N.C., Dias, A.L.T., Marques, M.J., & Soares, M.G. (2019). Leishmanicidal and antimicrobial activity of primin and primin-containing extracts from Miconia willdenowii. Fitoterapia, (138), 1-5. doi:10.1016/j.fitote.2019.104297
Wolska, K.I., Grudniak, A.M., Fiecek, B., Kraczkiewicz-Dowjat, A., & Kurek, A. (2010). Antibacterial activity of oleanolic and ursolic acids and their derivatives. Central European Journal of Biology, 5(5), 543-553. doi:10.2478/s11535-010-0045-x
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Publicado
2020-01-20
Edição
Seção
Microbiologia
