Antimicrobial activity of isolated compounds and semisynthetic derivatives from Miconia ferruginata
Abstract
This study evaluated the antimicrobial activity of isolated compounds and semisynthetic derivatives from Miconia ferruginata (Melastomataceae) against five microorganisms: Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), Bacillus subtilis (ATCC 6623), Pseudomonas aeruginosa (ATCC 15442), and Candida albicans (ATCC 10231). The isomeric mixture of ursolic and oleanolic acids was active against S. aureus (MIC = 250 μg mL-1) and against E. coli, B. subtilis, and P. aeruginosa (MIC = 500 μg mL-1). The flavone 5,6,7-trihydroxy-4’-methoxyflavone and the methyl esters, semisynthetic derivatives of a mixture of ursolic and oleanolic acids, showed no activity against the tested microorganisms. These results suggest that the carboxyl group present in the triterpenes may contribute to antimicrobial activity.
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References
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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
Published
2020-01-20
How to Cite
CUNHA, Gracielle Oliveira Sabbag et al.
Antimicrobial activity of isolated compounds and semisynthetic derivatives from Miconia ferruginata.
Acta Brasiliensis, [S.l.], v. 4, n. 1, p. 49-52, jan. 2020.
ISSN 2526-4338.
Available at: <http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/249>. Date accessed: 26 apr. 2024.
doi: https://doi.org/10.22571/2526-4338249.
Section
Microbiology
