Chemical composition and seasonal variation of the volatile oils from Siparuna guianensis Aubl. leaves collected from Monte do Carmo, Tocantins
DOI:
https://doi.org/10.33448/rsd-v11i1.24908Keywords:
Siparunaceae; Essential oils; Insecticide; Negramin.Abstract
Siparuna guianensis Aubl., known as “negramina”, “capitu”, is a small tree used for headaches, colds, fevers, as a healing agent, insect, and tick repellents. This study aimed to evaluate the chemical composition and seasonal variability of essential oils from the leaves of S. guianensis. Botanical material was collected in Monte do Carmo, Tocantins, Brazil. The powder from the leaves was submitted to hydrodistillation in a Clevenger apparatus, and the identification of the compounds was performed by GC-MS. In volatile oils, 21.32% to 55.44% of sesquiterpenes, 19.95 to 49.73% of oxygenated sesquiterpenes, 0.48 to 1.55% of oxygenated monoterpenes, 0 to 5.67% of monoterpene hydrocarbons were identified, 0 to 48.2% of other compounds. The major compounds were γ-muurolene (13.99 to 35.97%), Curzerene (7.22-19.15%), Curzerenone (7.3-18.13%), 2-undecanone (3.99- 10.63%). The presence of two clusters was verified: cluster I, discriminated by the compounds Curzerenone, β-selinene, δ-elemene, corresponding to the months with the lowest index, and cluster II, discriminated by the β-burbonene, corresponding to the months with the highest index rainfall index. Comparing the present study with data from the literature, it is concluded that S. guianensis presents great chemical variability, which can be explained by genetic factors, seasonality, light, temperature, which can alter the production of metabolites. As S. guianensis has broad therapeutic potential as an antimicrobial and promising larvicidal activity, there is a need for agronomic studies to obtain specimens that require more interesting chemical components for the pharmaceutical industry. This study is the first carried out with oils from leaves collected in Monte do Carmo, Tocantins, Brazil.
References
Adams, R. P. (2007). Identification of essential oil components by Gas Chromatography/Mass Spectroscopy. (4th ed.) Carol Stream, IL: Allured Publ. Corp.
Aguiar, R. W. S., Santos, S. F. S., Morgado, F. S., Ascencio, S. D., Lopes, M. M., Viana, K. F., Didonet, J. & Ribeiro, B. M. (2015). Insecticidal and repellent activity of Siparuna guianensis Aubl. (Negramina) against Aedes aegypti and Culex quinquefasciatus, PLOS ONE 3, 1-14.
Andrade, M. A., Cardoso, M. G., Gomes, M. S., Azeredo, C. M. O., Batista, L. R., Soares, M. J. S., Rodrigues, L. M. A. & Figueiredo, A. C. S. (2015). Biological activity of the essential oils from Cinnamodendron dinisii and Siparuna guianensis. Brazilian Journal of Microbiology, 46(1), 189-194.
Bieras, A. C. & Sajo, M. G. (2009). Leaf structure of the cerrado (Brazilian savanna) woody plants. Trees, 23, 451–471.
Carvalho, M. G. T. & Vilarinho, C. S. P. S. (2017). Plantas medicinais: o ouro do nosso Cerrado. Goiânia: Kelps. 222p.
Carvalho, V. F., Ramos, L. A., Silva, C. A, Nebo, L., Moraes D., Silva, F. F. A., Costa, N. C. A., Rodrigues Junior, R. O. Souza, L. F. & Rodrigues, R. M. (2019). In vitro anthelmintic activity of Siparuna guianensis extract and essential oil against Strongyloides venezuelensis. Journal of Helminthology, 94, e50, 1–5. https://doi.org/10.1017/S0022149X19000282
Conegundes, J. L. M., Silva, J. M., Mendes, R. F., Fernandes, M. F., Pinto, N. C. C., Almeida, M. A., Dib, P. R. B., Andrade, R. O., Rodrigues, M. N., Castãnon, M. C. M. N., Macedo, G. C. & Scio, E. (2021). Anti-inflammatory and antinociceptive activity of Siparuna guianensis Aublet, an Amazonian plant traditionally used by indigenous communities. Journal of Ethnopharmacology 265 (113344), 1-12.
De La Cruz, M. G. (2008). Plantas Medicinais de Mato Grosso: A farmacopeia popular dos raizeiros. Carlini & Caniato. 224p.
Dias, D. A., Urban, S. & Roessner, U. (2012). A historical overview of natural products in drug discovery. Metabolites, 2 (2), 303-336.
Ferreira, T. P., Haddi, K., Corrêa, R. F. T., Zapata, V. L. B., Piau, T. B., Souza, L. F. N., Santos, S. G., Oliveira, E. E., Jumbo, L. O. V., Ribeiro, B. M., Grisolia, C. K., Fidelis, R. R., Maia, A. M. S., Raimundo W. S. & Aguiar, R. W. S. (2019). Prolonged mosquitocidal activity of Siparuna guianensis essential oil encapsulated in chitosan nanoparticles. PLoS Neglected Tropical Diseases, 13(8), 1-23. https://doi.org/10.1371/journal.pntd.0007624
Facundo, V. A., Azevedo, M. S., Rodrigues, R. V., Nascimento, L. F., Militão, J. S. L. T., Silva, G. V. J. & Braz-Filho, R. (2012). Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana. Brazilian Journal of Pharmacognosy, 22(5), 1134-1139. 2012
INMET (2021). Instituto Nacional de Meteorologia. Ministério da agricultura, pecuária e abastecimento. http://www.inmet.gov.br/portal/ (acessado em setembro de 2021).
Kuhlmann, M. (2012). Frutos e sementes do Cerrado atrativos para fauna: guia de campo. Ed. Rede de Sementes do Cerrado. 360p.
Leitão, G. G., El-Adji, S. S., Melo, W. A. L. & Brown, S. G. L. L. (2005). Separation of free and glycosylated flavonoids from Siparuna guianensis by gradient and isocratic CCC. Journal of Liquid Chromatography & Related Technologiesw, 28, 2041–2051.
Lourenço, A. M., Haddi, K., Ribeiro, B. M., Corrêia, R. F. T., Tomé, H. V. V., Santos-Amaya, O., Pereira, E. J. G., Guedes, R. N. C., Santos, G. R., Oliveira, E. E. & Aguiar. R. W. S. (2018). Essential oil of Siparuna guianensis as an alternative tool for improved lepidopteran control and resistance management practices. Scientific Reports, 8(7215), 1-13. https://doi.org/10.1038/s41598-018-25721-0.
Marti, G., Eparvier, V., Morleo, B., Le Ven, J., Apel, C., Bodo, B., Amand, S., Dumontet, V., Lozach, O., Meijer, L., Françoise Guéritte, F. & Marc Litaudon, M. (2013). Natural aristolactams and aporphine alkaloids as inhibitors of CDK1/Cyclin B and DYRK1A. Molecules, 18, 3018-3027. https://doi:10.3390/molecules18033018.
Melo, D. C., Miranda, M. L. D., Ferreira, W. G., Andrade, P. (2017). Anticariogenic and antimycobacterial activities of the essential oil of Siparuna guianensis Aublet (Siparunaceae). Orbital: The Electronic Journal of Chemistry, 1-7.
Moura, W. S., Oliveira, E. E., Haddi, K., Corrêa, R. F. T., Piau, T. B., Moura, D. S., Santos, S. F., Grisolia, C. K., Ribeiro, B. M., Aguiar, R. W. S. (2021). Cassava starch-based essential oil microparticles preparations: Functionalities in mosquito control and selectivity against non-target organisms. Industrial Crops & Products, 162 (2021) 113289, 1-10.
NIST (1998). National Institute of Standards and Technology, PC version of the NIST/ EPA/NIH Mass Spectral Database. U.S. Gaithersburg: Department of Commerce.
Oliveira, M. S., Cruz, J. N., Costa, W. A., Silva, S. G., Brito, M. P., Menezes, S. A. F., Chaves Neto, A. M. J., Andrade, E. H. A. & Carvalho Junior, R. N. (2020). Chemical composition, antimicrobial properties of Siparuna guianensis essential oil and a molecular docking and dynamics molecular study of its major chemical constituent. Molecules, 25(3852), 1-15. https://doi:10.3390/molecules25173852.
Portella, A. C. F., Munaro, M., Ascêncio, S. D., Siqueira, C. A., Ferreira, T. P. S., Aguiar, R. W. S. (2014). Caracterização físico-química do óleo essencial da Siparuna guianensis Aublet. Química Nova, 37, (5), 844-849.
Simas, N. K., Ferrari, S. F., Pereira, S. N. & Leitão, G. G. (2001). Chemical ecological characteristics of herbivory of Siparuna guianensis seeds by buffy-headed marmosets (Callithrix flaviceps) in the atlantic forest of southeastern Brazil. Journal of Chemical Ecology, 27 (1), 93-107.
Taylor, P. G., Cesari, I. M., Arsenak, M., Ballen, D., Abad, M. J., Fernandez, A., Milano, B., Ruiz, M., Williams, B. & Michelangeli, F. (2006). Evaluation of Venezuelan medicinal plant extracts for antitumor and antiprotease activities. Pharmaceutical Biology, 44(5), 349–362.
Toledo, P. F. S., Ferreira, T. P., Bastos, I. M. A. S., Rezende, S. M., Jumbo, L. O. V., Julcemar Didonet, J., Bruno S. Andrade, B. S., Tarcisio S. Melo, T. S., Smagghe, G., Oliveira, E. E. & Aguiar R.W.S. (2019). Essential oil from negramina (Siparuna guianensis) plants controls aphids without impairing survival and predatory abilities of nontarget ladybeetles. Environmental Pollution, 255 (113153), 1-12.
Valentini, C. M. A., Silva, L. E., Maciel, E. N., Franceschini, E., Sousa Jr., P. T., Dall´Oglio, E. L. & Coelho, M. F. B. (2010). Variação anual do rendimento e composição química dos componentes voláteis da Siparuna guianensis Aublet. Química Nova, 33 (7), 1506-1509.
Van Den Dool, H. & Kratz, P. D. (1963). A generalization of the Retention Index system including linear temperature programmed gas – liquid partition chromatography. Journal of Chromatography, 11, 463–471. https://doi.org/10.1016/S0021-9673(01)80947-X
Ward, J. H. (1963). Hierarchical grouping to optimize an objective function. Journal of the American Statistical Association, 58, 236-244. https://doi.org/10.1080/01621459.1963.10500845
Zoghbi, M. G. B., Andrade, E. H. A., Santon, A. S., Silva, M. H. L. & Maia, J. B. S. (1998). Essential oils of Siparuna guianensis Aubl. Journal of Essential Oil Research, 10, 543-546.
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Copyright (c) 2022 Joaquim Aurélio Tomaz de Souza; Liliane de Sousa Silva; Camila Aline Romano; Luiz Carlos da Cunha; Jerônimo Raimundo Oliveira Neto ; Leonardo Luiz Borges; Tatiana de Sousa Fiuza; José Realino de Paula
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