Abstract
Campomanesia adamantium (Cambess.) O. Berg., Myrtaceae, is a plant popularly used for its antiinflammatory, anti-diarrhoeal and urinary antiseptic activities. The aims of this study were to obtain the crude ethanolic extract and the hexane, dichloromethane, ethyl acetate, aqueous and concentrated aqueous tannin fractions from C. adamantium leaves, perform biomonitored fractionation to isolate and identify chemical compounds, study the chemical composition of the volatile oils of the leaves and flowers and test the antimicrobial activity of the ethanolic extract, fractions, isolated substances and volatile oils. Phytochemical screening and chromatographic and spectrometric techniques were used. Volatile oils were isolated by hydrodistillation in a Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. The antimicrobial activity was tested by a broth microdilution test. The component stictane-3,22-diol was isolated and identified from the hexane fraction, while valoneic and gallic acid were isolated and identified from the concentrated aqueous tannin fraction. The major constituents of the volatile oils of the leaves were verbenene (13.91%), β-funebrene (12.05%) and limonene (10.32%), while those of the volatile oils of the flowers were sabinene (20.45%), limonene (19.33%), α-thujene (8.86%) and methyl salicylate (8.66%). Antibacterial activity was verified for the hexane fraction, while antifungal activity was observed for the aqueous fraction and concentrated aqueous tannin fraction and for vanoleic acid. These results may justify the popular use of C. adamantium.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Adams, R.P., 2007. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed. Allured Publishing Corporation, Illinois.
Adati, R.T., Dissertação (Mestradoem Farmaco e Medicamentos) 2001. Estudo biofarmacognóstico de Campomanesia phaea (O. Berg) Landrum, Myrtaceae. Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, 125 pp.
Adati, R.T., Ferro, V.O., 2006. Volatile oil constituents of Campomanesia phaea (O Berg) Landrum (Myrtaceae). J. Essent. Oil Res. 18, 691–692.
Alves, A.M., Alves, M.S.O., Fernandes, T.O., Naves, R.V., Naves, M.M.V., 2013. Caracterização física e química, fenólicos totais e atividade antioxidante da polpa e resíduo de gabiroba. Rev. Bras. Frutic. 35, 837–844.
Azevedo, P.R., Silva, L.C.N., Gomes-Silva, A., Macedo, A.J., Araújo, J.M., Silva, M.V., 2012. Antimicrobial activity and phytochemical screening of branches, fruits and leaves of Eugenia brejoensis. Sci. Plena 26, 76–80.
Barros, F.M.C., Zambarda, E.O., Heinzmann, B.M., Carlos, A., Mallmann, C.A., 2009. Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N E. Brown (Verbenaceae). Quim. Nova 32, 861–867.
Borges, L.L., Alves, S.F., Sampaio, B.L., Conceição, E.C., Bara, M.T.F., Paula, J.R., 2013. Environmental factors affecting the concentration of phenolic compounds in Myrcia tomentosa leaves. Rev. Bras. Farmacog. 23, 230–238.
2010. Farmacopeia Brasileira, 5th ed. Agência Nacional de Vigilância Sanitária, Ministério da Saúde, Brasília, DF.
Canton, M., Onofre, S.B., 2010. Interferência de extratos da Baccharis dracunculifolia DC, Asteraceae, sobre a atividade de antibióticos usados na clínica. Rev. Bras. Farmacog. 20, 348–354.
Cardoso, C.A.L., Silva, J.R.M., Kataoka, V.M.F., Brum, C.S., Poppi, N.R., 2008. Avaliação da atividade antioxidante, toxicidade e composição química por CG-EM do extrato hexânico das folhas de Campomanesia pubescens. Rev. Cien. Farm. Bas. Aplic. 29, 297–301.
Cardoso, C., Kataoka, V.M.F., Ré-Poppi, N., 2010a. Leaf oil of Campomanesia sessiliflora O. Berg. J. Essent. Oil 135, 303–304.
Cardoso, C., Salmazzo, G., Honda, N.K., Prates, C.B., Vieira, M., Coelho, C.R.G., 2010b. Antimicrobial activity of the extracts and fractions of hexanic fruits of Campomanesia species (Myrtaceae). J. Med. Food. 13, 1273–1276.
Carvalho Junior, A.R., Gomes, G.A., Ferreira, R.O., Carvalho, M.G., 2014. Chemical constituents and antioxidant activity of leaves and branches of Eugenia copaca-banensis Kiaersk (Myrtaceae). Quim. Nova 37, 477–482.
Celli, G., Pereira-Netto, A., Beta, T., 2011. Comparative analysis of total phenolic content, antioxidant activity, and flavonoids profile of fruits from two varieties of Brazilian cherry (Eugenia uniflora L.) throughout the fruit developmental stages. Food Res. Int. 44, 2442–2451.
CLSI, 2005. M45-P: Methods for Antimicrobial Dilution and Disk Susceptibility Testing of Infrequently Isolated or Fastidious Bacteria. Approved Guideline, pp. 25, 27.
CLSI/NCCLS, 2008a. Método de referência para testes de diluição em caldo para determinação da sensibilidade de leveduras à terapia antifúngica: Documento M27-A3. Clinical and Laboratory Standards Institute, 22 (2).
CLSI/NCCLS, 2008b. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi: M38-A2. Clinical and Laboratory Standards Institute, 28 (2).
CLSI/NCCLS, 2009. Performance standards for antimicrobial susceptibility testing; 19th informational supplement. Document M100-S19. Clinical Laboratory Standards Institute, Wayne, PA, USA.
Coutinho, I.D., Coelho, R.G., Kataoka, V.M.F., Honda, N.K., Silva, J.R.M., Vilegas, W., Cardoso, C.A.L., 2008a. Determination of phenolic compounds and evaluation of antioxidant capacity of Campomanesia adamantium leaves. Eclet. Quim. 33, 53–60.
Coutinho, I.D., Poppi, N.R., Cardoso, C., 2008b. Identification of the volatile compounds of leaves and flowers in Guavira (Campomanesia adamantium O. Berg.). J. Essent. Oil. 20, 405–407.
Coutinho, I.D., Cardoso, C.A.L., Ré-Poppi, Melo, A.M., Vieira, M.C., Honda, N.K., Roberta Gomes Coelho, 2009. Gas chromatography-mass spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities of essential oil of Campomanesia adamantium (Cambess.) O. Berg (Guavira). Braz. J. Pharm. Sci. 45, 767–776.
Dambolena, J.S., Meriles, J.M., López, A.G., Gallucci, M.N., González, S.B., Guerra, P.E., Bruno, A., Zunino, M.P., 2011. Actividad antifúngica del aceite esencial de cinco especies de Juniperus de Argentina. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 10, 104–115.
Desoti, V.C., Maldaner, C.L., Carletto, M.S., Heinz, A.A., Coelho, M.S., Piati, D., Tiuman, T.S., 2011. Triagem fitoquímicae avaliação das atividades antimicrobiana e citotóxica de plantas medicinais nativas da região oeste do estado do Paraná. Arq. Cienc. Saude Unipar 15, 3–13.
Ferreira, L.C., Grabe-Guimarães, A., Michel, M.C., Guimarães, R.G., Rezende, S.A., 2013. Antiinflammatory and antinociceptive activities of Campomanesia adamantium. J. Ethnopharmacol. 145, 100–108.
Ferri, P.H., 1996. Química de produtos naturais: métodos gerais. Editora da Universidade Estadual Paulista, São Paulo.
Gobbo-Neto, L., Lopes, N.P., 2007. Plantas medicinais: fatores de influência no conteúdode metabólitos secundários. Quim. Nova 30, 374–381.
Govaerts, R., Sobral, M., Ashton, P.F., 2014. World Checklist of Myrtaceae. The Board of Trustees of the Royal Botanic Gardens, Kew. http://www.kew.org/wcsp (accessed 23.07.14).
Hatano, T., Yasuhara, T., Yoshihara, R., Agata, I., Noro, T., Okuda, T., 1990. Effects of interaction of tannins with co-existing substances VII. Inhibitory effects of tannins and related polyphenols on xanthine oxidase. Chem. Pharm. Bull. 38, 1224–1229.
Henriques, A.T., Simões-Pires, C.A., Apel, M.A., 2009. In: Yunes, F. (Ed.), Óleos essenciais: importânciae perspectivas terapêuticas. Editora Univali, Ijataí, pp. 221–250.
Hirano, Y., Kondo, R., Sakai, K., 2003. 5-alfa-Reductase inhibitory tannin-related compounds isolated from Shorea laeviforia. J. Wood Sci. 49, 339–343.
Holetz, F.B., Pessini, G.L., Sanches, N.R., Cortez, D.A.G., Nakamura, C.V., Dias Filho, B.P., 2002. Screening of some plants used in the Brazilian folk medicine for the treatment of infectious diseases. Mem. I. Oswaldo Cruz 97, 1027–1031.
Imatomi, M., Novaes, P., Gualtieri, S.C.J., 2013. Interspecific variation in the allelopathic potential of the family Myrtaceae. Acta Bot. Bras. 27, 54–61.
Lima, C.P., Queiroz, J.E., Santana, D.P., Ribeiro, E.L., Menezes, A.C.S., Naves, P.L.F., 2005. Atividade do ácido gálico sobre o crescimento e a formação de biofilme por Candida albicans. Rev. Biotecnol. Cienc. 2, 87.
Lima, D.F., Goldenberg, R., Sobral, M., 2011. O gênero Campomanesia (Myrtaceae) no estado do Paraná, Brasil. Rodriguésia 62, 683–693.
Lima, A.M.B., D’Avila, L.A., Siani, A.C., 2014. Comparison between methyl and trimethylsilyl ester derivatives in the separation and GC quantification of triterpene acids in Eugenia brasiliensis leaf extract. Chromatographia 77, 629–635.
Lima, C.A., Faleiro, F.G., Junqueira, N.T.V., Cohen, K.O., Guimarães, T.G., 2013. Características físico-químicas, polifenóis e flavonoides amarelos em frutos de espécies de pitaias comerciais e nativas do Cerrado. Rev. Bras. Frutic. 35, 565–570.
Limberger, R.P., Apel, M.A., Sobral, M., Menut, L.C., 2001. Chemical composition of essential oils from some Campomanesia species (Myrtaceae). J. Essent. Oil Res. 13, 113–115.
Liu, W.R., Qiao, W.L., Liu, Z.Z., Wang, X.H., Jiang, R., Li, S.Y., Ren-Bing Shi, R.B., She, G.M., 2013. Gaulteria: phytochemical and pharmacological characteristics. Molecules 18, 12071–12108.
Lorenzi, H., Lacerda, M., Bacheret, L., 2008. Frutas brasileiras e exóticas cultivadas. Instituto Plantarum, São Paulo.
Monteiro, J.M., Albuquerque, U.P., Araújo, E.L., Amorin, E.L.C., 2005. Taninos: uma abordagem da química à ecologia. Quim. Nova 28, 892–896.
Moura-Costa, G.F., Nocchi, S.R., Ceole, L.F., Mello, J.C.P., Nakamura, C.V., Dias Filho, B.P., Temponi, L.G., Ueda-Nakamura, T., 2012. Antimicrobial activity of plants used as medicinals on an indigenous reserve in Rio das Cobras Paraná, Brazil. J. Ethnopharmacol. 143, 631–638.
Mulyaningsih, S., Sporer, F., Reichling, J., Wink, M., 2011. Antibacterial activity of essential oils from Eucalyptus and of selected components against multidrug-resistant bacterial pathogens. Pharm. Biol. 49, 893–899.
Namkung, W., Thiagarajah, J.R., Phuan, P.W., Verkman, A.S., 2010. Inhibition of Ca2+ activated Cl− channels by gallotannins as a possible molecular basis for health benefits of red wine and green tea. FASEBJ. 24, 4178–4186.
NIST, 1998. National Institute of Standards and Technology. PC Version of the NIST/EPA/NIH Mass Spectral Database. U.S. Department of Commerce, Gaithersburg.
Okuda, T., Yoshida, T., Hatano, T., 1989. New methods of analyzing tannins. J. Nat. Prod. 52, 1–31.
Pai, S.R., Joshi, R.K., 2014. Distribution of betulinic acid in plant kingdom. Plant Sci. Today 1, 103–107.
Pascoal, A.C.R.F., Ehrenfried, C.A., Lopez, B.G.C., Araujo, T.M., Pascoal, V.D.B., Gilioli, R., Anhê, G.F., Ruiz, A.L.T.G., Carvalho, J.E., Stefanello, M.E.A., Salvador, M.J., 2014. Antiproliferative activity and induction of apoptosis in PC-3 cells by the chalcone cardamonin from Campomanesia adamantium (Myrtaceae) in a bioactivity-guided study. Molecules 19, 1843–1855.
Pavan, F.R., Leite, C.Q.F., Coelho, R.G., Coutinho, I.D., Honda, N.K., Cardoso, C.A.L., Vilegas, W., Leite, S.R.A., Sato, D.N., 2009. Evaluation of anti-Mycobacterium tuberculosis activity of Campomanesia adamantium (Myrtaceae). Quim. Nova 32, 1222–1226.
Piva, M.G., 2002. O Caminho das plantas medicinais: estudo etnobotânico, vol. 1. Editora Mondrian, Rio de Janeiro.
Ramos, D.D., Cardoso, C.A.L., Yamamoto, N.T., 2008. Avaliação do potencial citotóxico e atividade antioxidante em Campomanesia adamantium (Cambess.) O. Berg (Myrtaceae). Rev. Bras. Biociênc. 5, 774–776.
Sameermahmood, Z., Raji, L., Saravanan, T., Vaidya, A., Mohan, V., Balasubramanyam, M., 2010. Gallic acid protects RINm5F beta-cells from glucolipotoxicity by its antiapoptotic and insulin-secretagogue actions. Phytother. Res. 24, 83–94.
Santos, A.C.A., Rossato, M., Serafini, L.A., Bueno, M., Liziane, B., Crippa, L.B., Sartori, V.C., Dellacassa, E., Moyna, P., 2010. Efeito fungicida dos óleos essenciais de Schinus molle L. e Schinus terebinthifolius Raddi Anacardiaceae, do Rio Grande do Sul. Rev. Bras. Farmacog. 20, 154–159.
Shao, M., Wang, Y., Huang, X.J., Fan, C.L., Zhang, Q.W., Zhang, X.Q., Ye, W.C., 2012. Four new triterpenoids from the leaves of Psidium guajava. J. Asian Nat. Prod. Res. 14, 348–354.
Shimizu, M.T., Bueno, L.J.F., Rodrigues, R.F.O., Sallowicz, F.A., Sawaya, A.C.H.F., Marques, M.O.M., 2006. Essential oil of Lithraea molleoides (Vell.): chemical composition and antimicrobial activity. Braz. J. Microbiol. 37, 556–560.
Sobral, M., et al., 2010. Myrtaceae. Lista de espécies da flora do Brasil. http://www.floradobrasil.jbrj.gov.br/ (accessed July 2018).
Stefanello, M.E.A., Cervi, A.C., Wisniewski Jr., A., Simionatto, E.L., 2008. Essential oil composition of Campomanesia adamantium (Camb) O. Berg. J. Essent. Oil Res. 20, 424–425.
Tahara, K., Hashida, K., Otsuka, Y., Ohara, S., Kojima, K., Shinohara, K., 2014. Identification of a hydrolyzable tannin, oenothein B, as an aluminum-detoxifying ligand in a highly aluminum-resistant tree, Eucalyptus camaldulensis. Plant Physiol. 164, 683–693.
Topcu, G., Yapar, G., Türkmen, Z., Gören, A.C., Öksüz, S., Schilling, J.K., Kingston, D.G.I., 2011. Ovarian antiproliferative activity directed isolation of triterpenoids from fruits of Eucalyptus camaldulensis Dehnh. Phytochem. Lett. 4, 421–425.
Unno, T., Sugimoto, A., Kakuda, T., 2004. Xanthine oxidase inhibitors from the leaves of Lagerstroemia speciosa (L.) Pers. J. Ethnopharmacol. 93, 391–395.
Vallilo, M.I., Lamardo, L.C.A., Gaberlotti, M.L., Oliveira, E., Moreno, P.R.H., 2006. Composição química dos frutos de Campomanesia adamantium. Cienc. Tecnol. Aliment. 26, 805–810.
Van Den Dool, H., Kratz, P.D., 1963. Generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. 11, 463–471.
Author information
Authors and Affiliations
Corresponding author
Additional information
Author contributions
SS contributed to the design and implementation of the experiment. LTC contributed to implementation of the experiment. VFA contributed to the design of the experiment. TSF contributed to a critical reading of the manuscript. LMFT contributed to a critical reading of the manuscript. BGV contributed to the mass spectrometric analysis. PHF contributed to the chromatographic analysis. LLB contributed to a critical reading of the manuscript. Professor JRP was responsible for overall planning and experimental design.
Rights and permissions
This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
About this article
Cite this article
Sá, S., Chaul, L.T., Alves, V.F. et al. Phytochemistry and antimicrobial activity of Campomanesia adamantium. Rev. Bras. Farmacogn. 28, 303–311 (2018). https://doi.org/10.1016/j.bjp.2018.02.008
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1016/j.bjp.2018.02.008