Chemical investigation, antifungal activity and anatomical aspects of Protium puncticulatum J.F Macbr. and Protium tenuifolium (Engl.) Engl

Protium puncticulatum and Protium tenuifolium: Chemical and biological aspects

Authors

  • Henrique Cativo dos Santos Instituto Nacional de Pesquisas da Amazônia
  • Samirimi Januario Silva Instituto Nacional de Pesquisas da Amazônia
  • Claudete Catanhede do Nascimento Instituto Nacional de Pesquisas da Amazônia
  • Jorge Alves de Freitas Instituto Nacional de Pesquisas da Amazônia
  • João Vicente Braga de Souza Instituto Nacional de Pesquisas da Amazônia
  • Ana Claúdia Alves Cortez Instituto Nacional de Pesquisas da Amazônia
  • Antonio Gilberto Ferreira Federal University of São Carlos image/svg+xml
  • Sérgio Scherrer Thomasi Federal University of São Carlos image/svg+xml
  • Marcia Ortiz Mayo Marques Federal University of São Carlos image/svg+xml
  • Roselaine Facanali Instituto Agronômico
  • Maria da Paz Lima National Institute of Amazonian Research image/svg+xml

DOI:

https://doi.org/10.31686/ijier.vol9.iss5.3098

Keywords:

triterpenes, lignans, alkylresorcinols derivatives, essential oil, monoterpenes

Abstract

Protium Burm. f. (Burseraceae) is well known in the Brazilian Amazon for its diversity of species, though some of them are difficult to identify based on only morphological characteristics. We investigated the species Protium puncticulatum J.F. Macbr. and Protium tenuifolium (Engl.) Engl. in relation to their chemical constituents and some biological aspects. The phytochemical study of the hexane extract from the trunk of P. puncticulatum led to the identification of a mixture of triterpenes: α, β-amyrin (1 and 2), and lupeol (3); the methanolic extract gave the lignans 7-oxo-parabenzolactone (4) and 7’-hydroxy-9α-methylcubebin (5); this last lignan showed a MIC of 320 μg/mL for Candida albicans and 160 μg/mL for Cryptococcus neoformans and C. gattii. The hexane extract from the branches of P. tenuifolium also provided a mixture of α and β-amyrin (1, 2); the methanolic extract gave dimeric alkylresorcinols named integracin B (6) and integracin A (7). Analyses of anatomical characteristics confirmed the identity of the species Protium tenuifolium (Engl.) Engl. Essential oils obtained via hydrodistillation from the fresh bark of the trunk of P. tenuifolium showed a predominance of the monoterpenes limonene (56.17%), α-phellandrene (16.22%) and ρ-cymene (10.52%). This study is important since it increases knowledge on the volatile and non-volatile chemical constituents of the woody parts of two species of Protium from the Amazon.

Downloads

Download data is not yet available.

Author Biographies

Henrique Cativo dos Santos, Instituto Nacional de Pesquisas da Amazônia

Laboratório de Química de Produtos Naturais

Samirimi Januario Silva, Instituto Nacional de Pesquisas da Amazônia

Laboratório de Química de Produtos Naturais

Claudete Catanhede do Nascimento, Instituto Nacional de Pesquisas da Amazônia

Laboratório de Tecnologia da Madeira

Jorge Alves de Freitas , Instituto Nacional de Pesquisas da Amazônia

Laboratório de Tecnologia da Madeira

João Vicente Braga de Souza, Instituto Nacional de Pesquisas da Amazônia

Laboratório de Micologia Médica

Ana Claúdia Alves Cortez, Instituto Nacional de Pesquisas da Amazônia

Laboratório de Micologia Médica

Antonio Gilberto Ferreira, Federal University of São Carlos

Laboratório de Ressonância Magnética Nuclear

Sérgio Scherrer Thomasi, Federal University of São Carlos

Laboratório de Ressonância Magnética Nuclear

Marcia Ortiz Mayo Marques, Federal University of São Carlos

Laboratório de Ressonância Magnética Nuclear

Roselaine Facanali , Instituto Agronômico

Centro de Pesquisa de Recursos Genéticos Vegetais

Maria da Paz Lima, National Institute of Amazonian Research

Laboratório de Química de Produtos Naturais

References

Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry; Allured Publishing Corporation: Carol Stream, IL, USA, 2007.

Almeida, P. D., Boleti, A. P., Rüdiger, A. L., Lourenço, G. A., Veiga Junior, V. F. and Lima, E. S. (2015). Anti-inflammatory activity of triterpenes isolated from Protium paniculatum oil-resins. Complementary and Alternative Medicine 15, 1-10. https://doi.org/10.1155/2015/293768 DOI: https://doi.org/10.1155/2015/293768

Angiosperm Phylogeny Group (APG). Available at http://www.mobot.org. Accessed March, 2021.

Carvalho, L. E., Pinto, D. S., Magalhães, L. A. M., Lima, M. P., Marques, M. O. M. and Facanali, R. (2010). Chemical constituents of essential oil of Protium decandrum (Burseraceae) from Western Amazon. Journal of Essential Oil Bearing Plants 13, 181-184. https://doi.org/10.1080/0972060X.2010.10643809 DOI: https://doi.org/10.1080/0972060X.2010.10643809

CLSI (Clinical and Laboratory Standards Institute). Reference method for broth dilution antifungal susceptibility testing of yeast. Approved standard, M27-A3, 3rd ed. Wayne, PA, USA, 2008.

Coradin, V. T. R. and Muniz, G. I. B. Normas de procedimentos em estudos de anatomia da madeira - I. Angiospermae II. Gimnospermae. IBAMA: Brasilia, DF, 1991.

Costa, T. O. G., Almeida, R. A., Koolen, H. H. F., Silva, F. M. A. and Pinto, A. C. (2012). Constituintes químicos do caule de Protium hebetatum (Burseraceae). Acta Amazonica 42, 557-540. https://doi.org/ 10.1590/S0044-59672012000400014 DOI: https://doi.org/10.1590/S0044-59672012000400014

Daly, D. C. (1992). New taxa and combinations in Protium Burm. f. studies in neotropical Burseraceae VI. Brittonia 44, 280-299. ISSN: 0007-196X DOI: https://doi.org/10.2307/2806927

Daly, D.C. (1989). Studies in Neotropical Burseraceae II. Generic limits in Neotropical Protieae and Canarieae. Brittonia 41, 17-27. ISSN: 0007-196X DOI: https://doi.org/10.2307/2807583

Dang, P. H., Nguyen, L. T. T, Nguyen, H. T. T., Le, T. H., Do, T. N. V. and Nguyen, H. X. (2019). A new dimeric alkylresorcinol from the stem barks of Swintonia floribunda (Anacardiaceae). Natural Product Research 33, 2883-2889. https://doi.org/10.1080/14786419.2018.1509329 DOI: https://doi.org/10.1080/14786419.2018.1509329

Flora do Brasil. Available at http://servicos.jbrj.gov.br. Accessed March, 2021.

Guimarães, A. C. and Siani, A. C. (2007). Triterpenes from the leaves of Protium strumosum. Revista Fitos 3, 67-76. ISSN: 1808-9569

Lima, T. A. A. C., Rocha, K. R. A., Melo, M. F. F., Marques, M. O. M, Facanali, R. and Lima, M. P. (2014). Aspectos morfológicos e químicos de Protium spruceanum: uma contribuição ao conhecimento de espécies aromáticas do Bosque da Ciência do INPA. Scientia Amazonia 3, 6-10. ISSN 2238.1910

Lima, M. P., Lima, T. A. A. C., Ribeiro, J. E. L. S., Marques, M. O. M. and Facanali, R. (2016). Estimulo para produção de resina em Protium hebetatum Daly e avaliação dos constituintes químicos voláteis. Scientia Amazonia 5, 21-24. ISSN 2238.1910

Oliveira, L. M., Queiroz, D. P. K., Melo, L. E..S., Marques, M. O. M., Facanali, R. and Lima, M. P. (2018). Constituintes voláteis dos galhos de quatro espécies de Protium ocorrentes na flora da Reserva Ducke. Scientia Amazonia 7, 68-73. ISSN 2238.1910

Marco, J. A., Sanz-Cervera, J., Morante, M. D., Garcia-Lliso, V., Vallès-Xirau, J. and Jakupovic, J. (1996). Tricyclic sesquiterpenes from Artemisia chamaemelifolia. Phytochemistry 41, 837-844. https://doi.org/ 10.1016/0031-9422(95)00702-4 DOI: https://doi.org/10.1016/0031-9422(95)00702-4

McLafferty, F. W. and Stauffer, D.B. Wiley/NBS Registry of Mass Spectral Data. Wiley-Interscience: New York, USA, 1989.

Pinto, D. S., Carvalho, L. E., Lima, M. P., Marques, M. O. M., FacanalI, R. and Ribeiro, J. E. L. S. (2013). Volatiles of foliar rachis, branches and resin elicited by insects from Protium hebetatum grows wild in Amazon. Journal Essential of the Oil Bearing Plants 13, 699-703. https://doi.org/10.1080/ 0972060X.2010.10643881 DOI: https://doi.org/10.1080/0972060X.2010.10643881

Siani, A. C., ZoghbI, M. G. B., Wolter, E. L. A. and Vencato, I. (1998). 5-Methoxyjusticidin A, a new arylnaphthalene lignan from Protium unifoliolatum. Journal of Natural Product 61, 796-797. https:// doi.org/10.1021/np9702291 DOI: https://doi.org/10.1021/np9702291

Singh, S.B., Zink, D. L., Bills, G. F., Pelaez, F., Teran, A., Collado, J., Silverman, K. C., Lingham, R. B., Felock, P. and Hazuda, D. J. (2002). Discovery, structure and HIV-1integrase inhibitory activities of integracins, novel dimeric alkyl aromatics from Cytonaema sp. Tetrahedron Letters 43, 1617-1620. https://doi.org/10.1016/S0040-4039(02)00083-7 DOI: https://doi.org/10.1016/S0040-4039(02)00083-7

Siqueira, J. B. G., Zoghbi, M. G. B., Cabral, J. A. and Wolter Filho, W. (1995). Lignans from Protium tenuifolium. Journal of Natural 58, 730-732. https://doi.org/10.1021/np50119a011 DOI: https://doi.org/10.1021/np50119a011

Susunaga, G. S., Siani, A. C., Pizzolatti, M. G., Yunes, R. A. and Monache, F. D. (2001). Triterpenes from the resin of Protium heptaphyllum. Fitoterapia 72, 709-711. https://doi.org/10.1016/S0367-326X(01) 00289-1 DOI: https://doi.org/10.1016/S0367-326X(01)00289-1

Zoghbi, M. G. B., Siqueira, J. B. G., Wolter, E. L. A. and Pereira Junior, O. L. (1993). Constituintes químicos de Protium paniculatum (Burseraceae). Acta Amazonica 23, 187-189. https://doi.org/ 10.1590/1809-43921993233189 DOI: https://doi.org/10.1590/1809-43921993233189

Zoghbi, M. G. B., Andrade, E. H. A., Lima, M. P., Silva, T. M. D. and Daly, D. C. (2005). The essential oils of five species of Protium growing in the north of Brazil. Journal of Essential Oil Bearing Plants 8, 312-317. https://doi.org/10.1080/0972060X.2005.10643458 DOI: https://doi.org/10.1080/0972060X.2005.10643458

Downloads

Published

01-05-2021

How to Cite

dos Santos, H. C. ., Silva, S. J. ., do Nascimento, C. C. ., de Freitas , J. A. ., de Souza, J. V. B. ., Cortez, A. C. A. ., Ferreira, A. G., Thomasi, S. S. ., Marques, M. O. M. ., Facanali , R., & Lima, M. da P. (2021). Chemical investigation, antifungal activity and anatomical aspects of Protium puncticulatum J.F Macbr. and Protium tenuifolium (Engl.) Engl: Protium puncticulatum and Protium tenuifolium: Chemical and biological aspects. International Journal for Innovation Education and Research, 9(5), 798–811. https://doi.org/10.31686/ijier.vol9.iss5.3098