In vitro antileishmanial activity of Anacardium othonianum and isolated compounds against Leishmania amazonensis
Abstract
This study analyzes the antileishmanial activity of the crude ethanol extract, fractions, and isolated compounds of A. othonianum nuts. Antileishmanial activity was evaluated against Leishmania amazonensis promastigotes in vitro. The phytochemical study was performed by high-performance liquid chromatography-high-resolution mass spectrometry-diode array detector (HPLC-HRMS-DAD) and by preparative HPLC. HPLC-HRMS-DAD analysis of the bioactive extract confirmed the presence of ten alkyl phenol derivatives that had previously been isolated from A. occidentale. Bioassay-guided isolation afforded cardanol triene, cardanol diene, cardanol monoene, cardol triene, anacardic acid triene, anacardic acid diene, and anacardic acid monoene. Cardol triene gave an IC50 of 80.66 µM. The obtained data suggest that the evaluated extract, fractions, and cardol triene had moderate activity against L. amazonensis promastigotes. This is the first description of alkyl phenols in A. othonianum.
Downloads
Download data is not yet available.
References
Alvarenga, T. A. (2020). Estudo fitoquímico e avaliação da atividade leishmanicida de Anacardium othonianum Riss. (Tese de doutorado). Universidade de Franca, Franca, São Paulo.
Alvarenga, T. A., de Oliveira, P. F., de Souza, J. M., Tavares, D. C., Andrade E Silva, M. L., Cunha, W. R., Groppo, M., Januário, A. H., Magalhães, L. G. & Pauletti, P. M. (2016). Schistosomicidal activity of alkyl-phenols from the cashew Anacardium occidentale against Schistosoma mansoni adult worms. Journal of Agricultural and Food Chemitry, 64(46), 8821-8827. doi: 10.1021/acs.jafc.6b04200
Andrade, P. M., Melo, D. C., Alcoba, A. E. T., Ferreira Júnior, W. G., Pagotti, M. C., Magalhães, L. G., Santos, T. C. L. D., Crotti, A. E. M., Alves, C. C. F. & Miranda, M. L. D. (2018). Chemical composition and evaluation of antileishmanial and cytotoxic activities of the essential oil from leaves of Cryptocarya aschersoniana Mez. (Lauraceae Juss.). Anais da Academia Brasileira de Ciências, 90(3), 2671-2678. doi: 10.1590/0001-3765201820170332
Bertanha, C. S., Gimenez, V. M. M., Furtado, R. A., Tavares, D. C., Cunha, W. R., Silva, M. L. A., Januário, A. H., Borges, A., Kawano, D. F., Parreira, R. L. T. & Pauletti, P. M. (2020). Isolation, in vitro and in silico evaluation of phenylethanoid glycoside from Arrabidaea brachypoda as lipoxygenase inhibitor. Journal of the Brazilian Chemical Society, 31(4), 849-855. doi: 10.21577/0103-5053.20190248
Bessa, N. G. F. de, Borges, J. C. M., Beserra, F. P, Carvalho, R. H. A., Pereira, M. A. B., Fagundes, R., Campos, S. L., Ribeiro, L. U, Quirino, M. S, Chagas Junior, A. F & Alves, A. (2013). Prospecção fitoquímica preliminar de plantas nativas do cerrado de uso popular medicinal pela comunidade rural do assentamento vale verde - Tocantins. Revista Brasileira de Plantas Medicinais, 15(4), 692-707. doi: 10.1590/S1516-05722013000500010
Charlton, R. L., Rossi-Bergmann, B., Denny, P. W. & Steel, P. G. (2018). Repurposing as a strategy for the discovery of new anti-leishmanials: the-state-of-the-art. Parasitology, 145(2), 219-236. doi: 10.1017/S0031182017000993
Correia, S. de J., David, J. P., David J. M. (2006). Metabólitos secundários de espécies de Anacardiaceae. Química Nova,29(6), 1287-1300. doi: 10.1590/S0100-40422006000600026
Curado, F. M. L. M. J., Gazolla, A. P., Pedroso, R. C. N., Pimenta, L. P., de Oliveira, P. F., Tavares, D. C., Silva, M. L. A., Cunha, W. R., Pietro, R. C. L. R., Januario, A. H., Pauletti, P. M., Sales, J. F. & Silva, F. G. (2016). Antifungal and cytotoxicity activities of Anacardium othonianum extract. Journal of Medicinal Plants Research, 10(29), 450-456. doi: 10.5897/JMPR2016.6115
Gazolla, A. P., Curado, F. M. L. M. J., Pedroso, R. C. N., Filho, L. C. K., Sales, J. F., Rosa, M., Costa, A. C., Pauletti, P. M., Januario, A. H. & Silva, F. G. (2017). The influence of light quality on phenolic acid and biflavonoid production in Anacardium othonianum Rizz. seedlings grown in vitro. Australian Journal of Crop Science, 11(5), 528-534. doi: 10.21475/ajcs.17.11.05.p314
Ghorbani, M. & Farhoudi, R. (2018). Leishmaniasis in humans: drug or vaccine therapy? Drug Design, Development and Therapy, 2018(12), 25-40. doi: 10.2147/DDDT.S146521
Gimenez, V. M. M., Alvarenga, T. A., Groppo, M., Silva, M. L. A., Cunha, W. R., Januario, A. H., Smilkstein, M. J., Riscoe, M. K. & Pauletti, P. M. (2019). Antiplasmodial evaluation of Anacardium occidentale and alkyl-phenols. Revista Brasileira de Farmacognosia, 29(1), 36-39. doi: 10.1016/j.bjp.2018.11.003
Hendrickx, S., Caljon, G. & Maes, L. (2019). Need for sustainable approaches in antileishmanial drug discovery. Parasitology Research, 118, 2743–2752. doi: 10.1007/s00436-019-06443-2.
Kubo, I., Komatsu, S. & Ochi, M. (1986). Molluscicides from the cashew Anacardium occidentale and their large-scale isolation. Journal of Agricultural and Food Chemitry, 34(6), 970−973. doi: 10.1021/jf00072a010
Lomonaco, D., Francisco, D. L., Maia, F. J. N., Clemente, C. S., Mota, J. P. F., Costa Junior, J. E. & Mazzetto, S. E. (2012). Thermal studies of new biodiesel antioxidants synthesized from a natural occurring phenolic lipid. Fuel, 97, 552-559. doi: 10.1016/j.fuel.2012.01.059
Matutino Bastos, T., Mannochio Russo, H., Silvio Moretti, N., Schenkman, S., Marcourt, L., Gupta, M. P., Wolfender, J. L., Ferreira Queiroz, E. & Botelho Pereira Soares, M. (2019). Chemical Constituents of Anacardium occidentale as inhibitors of Trypanosoma cruzi Sirtuins. Molecules, 24(7), 1299. doi: 10.3390/molecules24071299.
Oliveira, M. S., Morais, S. M., Magalhães, D. V., Batista, W. P., Vieira, I. G., Craveiro, A. A., de Manezes, J. E., Carvalho, A. F. & de Lima, G. P. (2011). Antioxidant, larvicidal and antiacetylcholinesterase activities of cashew nut shell liquid constituents. Acta Tropica, 117(3), 165−170. doi: 10.1016/j.actatropica.2010.08.003
Souza, P. L. C. & Silva, M. R., 2015. Quality of granola prepared with dried caju-do-cerrado (Anacardium othonianum Rizz) and baru almonds (Dipteryx alata Vog). Journal of Food Science and Technology, 52, 1712-1717. doi: 10.1007/s13197-013-1134-4
Alvarenga, T. A., de Oliveira, P. F., de Souza, J. M., Tavares, D. C., Andrade E Silva, M. L., Cunha, W. R., Groppo, M., Januário, A. H., Magalhães, L. G. & Pauletti, P. M. (2016). Schistosomicidal activity of alkyl-phenols from the cashew Anacardium occidentale against Schistosoma mansoni adult worms. Journal of Agricultural and Food Chemitry, 64(46), 8821-8827. doi: 10.1021/acs.jafc.6b04200
Andrade, P. M., Melo, D. C., Alcoba, A. E. T., Ferreira Júnior, W. G., Pagotti, M. C., Magalhães, L. G., Santos, T. C. L. D., Crotti, A. E. M., Alves, C. C. F. & Miranda, M. L. D. (2018). Chemical composition and evaluation of antileishmanial and cytotoxic activities of the essential oil from leaves of Cryptocarya aschersoniana Mez. (Lauraceae Juss.). Anais da Academia Brasileira de Ciências, 90(3), 2671-2678. doi: 10.1590/0001-3765201820170332
Bertanha, C. S., Gimenez, V. M. M., Furtado, R. A., Tavares, D. C., Cunha, W. R., Silva, M. L. A., Januário, A. H., Borges, A., Kawano, D. F., Parreira, R. L. T. & Pauletti, P. M. (2020). Isolation, in vitro and in silico evaluation of phenylethanoid glycoside from Arrabidaea brachypoda as lipoxygenase inhibitor. Journal of the Brazilian Chemical Society, 31(4), 849-855. doi: 10.21577/0103-5053.20190248
Bessa, N. G. F. de, Borges, J. C. M., Beserra, F. P, Carvalho, R. H. A., Pereira, M. A. B., Fagundes, R., Campos, S. L., Ribeiro, L. U, Quirino, M. S, Chagas Junior, A. F & Alves, A. (2013). Prospecção fitoquímica preliminar de plantas nativas do cerrado de uso popular medicinal pela comunidade rural do assentamento vale verde - Tocantins. Revista Brasileira de Plantas Medicinais, 15(4), 692-707. doi: 10.1590/S1516-05722013000500010
Charlton, R. L., Rossi-Bergmann, B., Denny, P. W. & Steel, P. G. (2018). Repurposing as a strategy for the discovery of new anti-leishmanials: the-state-of-the-art. Parasitology, 145(2), 219-236. doi: 10.1017/S0031182017000993
Correia, S. de J., David, J. P., David J. M. (2006). Metabólitos secundários de espécies de Anacardiaceae. Química Nova,29(6), 1287-1300. doi: 10.1590/S0100-40422006000600026
Curado, F. M. L. M. J., Gazolla, A. P., Pedroso, R. C. N., Pimenta, L. P., de Oliveira, P. F., Tavares, D. C., Silva, M. L. A., Cunha, W. R., Pietro, R. C. L. R., Januario, A. H., Pauletti, P. M., Sales, J. F. & Silva, F. G. (2016). Antifungal and cytotoxicity activities of Anacardium othonianum extract. Journal of Medicinal Plants Research, 10(29), 450-456. doi: 10.5897/JMPR2016.6115
Gazolla, A. P., Curado, F. M. L. M. J., Pedroso, R. C. N., Filho, L. C. K., Sales, J. F., Rosa, M., Costa, A. C., Pauletti, P. M., Januario, A. H. & Silva, F. G. (2017). The influence of light quality on phenolic acid and biflavonoid production in Anacardium othonianum Rizz. seedlings grown in vitro. Australian Journal of Crop Science, 11(5), 528-534. doi: 10.21475/ajcs.17.11.05.p314
Ghorbani, M. & Farhoudi, R. (2018). Leishmaniasis in humans: drug or vaccine therapy? Drug Design, Development and Therapy, 2018(12), 25-40. doi: 10.2147/DDDT.S146521
Gimenez, V. M. M., Alvarenga, T. A., Groppo, M., Silva, M. L. A., Cunha, W. R., Januario, A. H., Smilkstein, M. J., Riscoe, M. K. & Pauletti, P. M. (2019). Antiplasmodial evaluation of Anacardium occidentale and alkyl-phenols. Revista Brasileira de Farmacognosia, 29(1), 36-39. doi: 10.1016/j.bjp.2018.11.003
Hendrickx, S., Caljon, G. & Maes, L. (2019). Need for sustainable approaches in antileishmanial drug discovery. Parasitology Research, 118, 2743–2752. doi: 10.1007/s00436-019-06443-2.
Kubo, I., Komatsu, S. & Ochi, M. (1986). Molluscicides from the cashew Anacardium occidentale and their large-scale isolation. Journal of Agricultural and Food Chemitry, 34(6), 970−973. doi: 10.1021/jf00072a010
Lomonaco, D., Francisco, D. L., Maia, F. J. N., Clemente, C. S., Mota, J. P. F., Costa Junior, J. E. & Mazzetto, S. E. (2012). Thermal studies of new biodiesel antioxidants synthesized from a natural occurring phenolic lipid. Fuel, 97, 552-559. doi: 10.1016/j.fuel.2012.01.059
Matutino Bastos, T., Mannochio Russo, H., Silvio Moretti, N., Schenkman, S., Marcourt, L., Gupta, M. P., Wolfender, J. L., Ferreira Queiroz, E. & Botelho Pereira Soares, M. (2019). Chemical Constituents of Anacardium occidentale as inhibitors of Trypanosoma cruzi Sirtuins. Molecules, 24(7), 1299. doi: 10.3390/molecules24071299.
Oliveira, M. S., Morais, S. M., Magalhães, D. V., Batista, W. P., Vieira, I. G., Craveiro, A. A., de Manezes, J. E., Carvalho, A. F. & de Lima, G. P. (2011). Antioxidant, larvicidal and antiacetylcholinesterase activities of cashew nut shell liquid constituents. Acta Tropica, 117(3), 165−170. doi: 10.1016/j.actatropica.2010.08.003
Souza, P. L. C. & Silva, M. R., 2015. Quality of granola prepared with dried caju-do-cerrado (Anacardium othonianum Rizz) and baru almonds (Dipteryx alata Vog). Journal of Food Science and Technology, 52, 1712-1717. doi: 10.1007/s13197-013-1134-4
Published
2021-01-27
How to Cite
ALVARENGA, Tavane Aparecida et al.
In vitro antileishmanial activity of Anacardium othonianum and isolated compounds against Leishmania amazonensis.
Acta Brasiliensis, [S.l.], v. 5, n. 1, p. 44-47, jan. 2021.
ISSN 2526-4338.
Available at: <http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/429>. Date accessed: 24 apr. 2024.
doi: https://doi.org/10.22571/2526-4338429.
Section
Note
