Phytochemical study and bioactivity of Eleutherine bulbosa (MILLER) Urb

Authors

DOI:

https://doi.org/10.33448/rsd-v11i14.36460

Keywords:

Quinones; Eleutherine; Antimicrobial; Antitumor; Amazon.

Abstract

The species Eleutherine bulbosa Miller (Urb.) has a vast wealth of isolated substances, however, there are few studies of individuals from the Amazon biome, which may present new substances or differentiated biological potentials. Therefore, the aim of the present study was to carry out a phytochemical analysis of E. bulbosa collected in the region of Altamira-PA, in the Amazon biome, and evaluate the biological potential of its extracts. The leaves, flowers and bulbs were dried and then ground. The plant material was then subjected to extraction with organic solvents, and its extracts analyzed by TLC. Through NMR analysis, it was possible to characterize 5 substances: eleutherin (1), eleutherinol-8-O-β-glycoside (2), eleutherol (3), isoeleutherin (4) and eleutherinol (5). The extracts and substances were submitted to antitumor test, however, only the samples that presented sufficient mass for testing were submitted. The hexane extract of the bulb proved to be significant in the antitumor test, causing 50-60% cell death against the tumor strains tested. In the antimicrobial assay, eleuterol and isoeleuterine showed inhibitory action against Staphylococcus aureus and Pseudomonas fluorescens. Eleutherin, eleutherinol and isoeleutherin proved to be important chemical markers of this species, due to their predominance in the plant. Through the results, it is concluded that the plant in question has antimicrobial and antitumor action, however, deeper studies with the isolated substances and extracts are necessary. Still, the results obtained can be used in future comparative studies of the species and genera of the tribe, combined with morphological and phylogeny data, to solve taxonomic problems.

Author Biographies

Maria Teresa Fachin Espinar, Instituto Nacional de Pesquisas da Amazônia

Laboratory of Bioprospecting and Biotechnology

Marne Carvalho de Vasconcellos, Universidade Federal do Amazonas

Professora Titular (Faculdade de Ciências Farmacêuticas) - UFAM

Cecilia Veronica Nunez, Instituto Nacional de Pesquisas da Amazônia

Pesquisadora (​ Laboratório de Bioprospecção e Biotecnologia - LABB, ​​​ Coordenação de Tecnologia e Inovação - COTEI) - Bolsista de produtividade em pesquisa do CNPq - nível 2 

References

Ahmed, S. a, Gogal, R. M., & Walsh, J. E. (1994). A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: an alternative to [3H] thymidine incorporation assay. Journal of Immunological Methods, 170(703), 211–224. https://doi.org/10.1016/0022-1759(94)90396-4.

Araújo, E. L., Alencar, J. R. B., & Rolim Neto, P. J. (2002). Lapachol: segurança e eficácia na terapêutica. Revista Brasileira de Farmacognosia, 12, 57–59. https://doi.org/10.1590/S0102-695X2002000300028.

Borges, E. S., Galucio, N. C. da R., Veiga, A. S. S., Busman, D. V., Lins, A. L. F. de A., Bahia, M. de O., Rissino, J. D., Correa, R. M. dos S., Burbano, R. M. R., Marinho, A. M. R., Casique, J. V., Percário, S., & Dolabela, M. F. (2020). Botanical studies, antimicrobial activity and cytotoxity of Eleutherine bulbosa (Mill.) Urb. Research, Society and Development, 9(11), e3369119992. https://doi.org/10.33448/rsd-v9i11.9992.

Brand, D. J., & Fisher, J. F. (1990). Reductive transformations of 10-deoxydaunomycinone. The Journal of Organic Chemistry, 55(2), 2518–2530. https://doi.org/10.1021/jo00295a052.

Cardoso, D., Särkinen, T., Alexander, S., Amorim, A. M., Bittrich, V., Celis, M., ... & Forzza, R. C. (2017). Amazon plant diversity revealed by a taxonomically verified species list. Proceedings of the National Academy of Sciences, 114(40), 10695-10700. https://doi.org/10.1073/pnas.1706756114.

Couto, C. L. L., Moraes, D. F. C., Cartágenes, M. do S. S., Amaral, F. M. M. do, & Guerra, R. N. (2016). Eleutherine bulbous (Mill.) Urb .: A review study. Journal of Medicinal Plants Research, 10(21), 286–297. https://doi.org/10.5897/JMPR2016.6106

Fitri, Y., & Rosidah, E. S. (2014). Effects of inhibition cell cycle and apoptosis of sabrang onion extract (Eleutherine bulbosa (Mill.) Urb.) on breast cancer cells. International Journal of PharmTech Research, 6(4), 1392-1396. https://doi.org/10.20902

Gallo, F. R., Palazzino, G., Federici, E., Iurilli, R., Galeffi, C., Chifundera, K., & Nicoletti, M. (2010). Polyketides from Eleutherine bulbosa. Natural Product Research, 24(16), 1578–1586. https://doi.org/10.1080/14786419.2010.500007

Galves, J., Oliveira, D. A., & Correia, K. B. (2021). Bioprospecção na Amazônia: um mapeamento sistemático dos recursos biológicos e genéticos. Em Sustentabilidade informacional em ecossistemas de conhecimentos. Manaus: EDUA. http://repositorioinstitucional.uea.edu.br/bitstream/riuea/3303/2/Sustentabilidade_informacional%20%282%29.pdf

Gaudiano, G., & Koch, T. H. (1991). Redox chemistry of anthracycline antitumor drugs and use of captodative radicals as tools for its elucidation and control. Chemical Research in Toxicology, 4(16), 2–16. https://doi.org/10.1021/tx00019a001

Hara, H., Maruyama, N., Yamashita, S., Hayashi, Y., Lee, K.-H., Bastow, K. F., Chairul, R. M., & Imakura, Y. (1997). Elecanacin, a novel new naphtoquinone from the bulb of Eleutherine americana. Chemical & Pharmaceutical Bulletin, 45(10), 1714–1716. https://doi.org/10.1248/cpb.45.1714

Ieyama, T., Gunawan-puteri, M. D. P. T., & Kawabata, J. (2011). a -Glucosidase inhibitors from the bulb of Eleutherine americana. Food Chemistry, 128(2), 308–311. https://doi.org/10.1016/j.foodchem.2011.03.021

Insanu, M., Kusmardiyani, S., & Hartati, R. (2014). Recent Studies on Phytochemicals and Pharmacological Effects of Eleutherine Americana Merr. Procedia Chemistry, 13, 221–228. https://doi.org/10.1016/j.proche.2014.12.032

Kamarudin, A.A.; Sayuti, N.H.; Saad, N.; Razak, N.A.A.; * Esa, N.M.(2021). Eleutherine bulbosa (Mill.) Urb. Bulb: Review of the Pharmacological Activities and Its Prospects for Application. Int. J. Mol. Sci. 2021, 22, 6747. https://doi.org/10.3390/ijms22136747.

Komura, H., Mizukawa, K., Minakata, H., Huang, H., Qin, G., & Xu, R. (1983). New Anthraquinones from Eleutherine americana. Chemical & Pharmaceutical Bulletin, 31(11), 4206–4208. https://doi.org/10.1248/cpb.31.4206

Krishnan, P., & Bastow, K. F. (2000). Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives-eleutherin, alpha lapachone, and beta lapachone. Biochemical Pharmacology, 60(00), 1367–1379. https://doi.org/10.1016/s0006-2952(00)00437-8

Kusuma, I. W., Arung, E. T., Rosamah, E., Purwatiningsih, S., Kuspradini, H., Syafrizal, Astuti, J., Kim, Y. U., & Shimizu, K. (2010). Antidermatophyte and antimelanogenesis compound from Eleutherine americana grown in Indonesia. Journal of Natural Medicines, 64(2), 223–226. https://doi.org/10.1007/s11418-010-0396-7

Lestari, D.; Kartika, R.; & Marliana, E. (2019) Antioxidant and anticancer activity of Eleutherine bulbosa (Mill.) Urb on leukemia cells L1210. Journal of Physics: Conference Series, The 2nd International Conference on Mathematics, Science and Computer Science, series 1277, Novotel Balikpapan Hotel, Balikpapan, Indonesia. https://doi.org/10.1088/1742-6596/1277/1/012022.

Lin, T.-S., Antonini, I., Cosby, L. A., & Sartorelli, A. C. (1984). 2,3-Dimethyl-1,4-naphthoquinone Derivatives as Bioreductive Alkylating Agents with Cross-Linking Potential. Journal of Medicinal Chemistry, 27(6), 813–815. https://doi.org/10.1017/CBO9781107415324.004

Malheiros, L. C. D. S. (2008). “Isoeleuterol e Isoeleuterina : Potenciais marcadores químicos da tintura de Eleutherine plicata Herb (Iridaceae) e atividades microbiológica e antioxidante .” Universidade Federal do Pará. http://repositorio.ufpa.br:8080/jspui/handle/2011/3030

Malheiros, L. C. da S., Mello, J. C. P. de, & Barbosa, W. L. R. (2015). Eleutherine plicata – Quinones and Antioxidant Activity. In A. V. Rao & L. G. Rao (Eds.), Phytochemicals - Isolation, Characterisation and Role in Human Health (pp. 323–338). InTech - Open science, open minds. https://doi.org/10.5772/59865

Martins, A. G., Rosário, D. L. do, Barros, M. N. de, & Jardim, M. A. G. (2005). Levantamento etnobotânico de plantas medicinais, alimentares e tóxicas da Ilha do Combu, Município de Belém, Estado do Pará, Brasil. Revista Brasileira de Farmácia, 86(1), 21–30. http://repositorio.museu-goeldi.br/handle/mgoeldi/184.

Nascimento, M. S., Vieira, J. M. S., Malheiros, L. C. S., Júnior, J. O. C. S., Rodrigues, L. C. S., & Barbosa, W. L. R. (2012). Characterisation of isoeleutherine in aqueous extract of Eleutherine plicata herb, Iridaceae, active against entamoeba hystolitica/ Entamoeba dispar in-vitro. International Journal of Pharmaceutical Sciences and Research, 3(4), 1096–1100. http://dx.doi.org/10.13040/IJPSR.0975-8232.3(4).1096-00

Oliveira Neto, A. R., Pinto, M. A., Silva, I. R., Moraes, S. C., & Gomes, M. L. (2007). O uso de Eleutherine plicata no tratamento de doenças gastrointestinais na amazônia paraense. In Anais do VIII Congresso de Ecologia do Brasil (pp. 1–2). Anais do VIII Congresso de Ecologia do Brasil. http://www.seb-ecologia.org.br/revistas/indexar/anais/viiiceb/pdf/633.pdf

Ottobelli, I., Facundo, V. A., Zuliani, J., Luz, C. C., Brasil, H. O. B., Militão, J. S. L. T., & Braz-Filho, R. (2011). Estudo químico de duas plantas medicinais da amazônia: Philodendron scabrum k. Krause (Araceae) e Vatairea guianensis aubl. (Fabaceae). Acta Amazonica, 41(3), 393–400. https://doi.org/10.1590/S0044-59672011000300009

Pereira, A. S., Shitsuka, D. M., Parreira, F., & Shitsuka, R. (2018). Metodologia da pesquisa científica. Santa Maria: UAB/NTE/UFSM. https://repositorio.ufsm.br/bitstream/handle/1/15824/Lic_Computacao_Metodologia-Pesquisa-Cientifica.pdf?sequence=1

Reeves, G., Chase, M. W., Goldblatt, P., Rudall, P., Fay, M. F., Cox, A. V., Lejeune, B., & Souza-chies, T. (2001). Molecular systematics of Iridaceae: evidence from four plastid dna regions. American Journal of Botany, 88(11), 2074–2087. https://doi.org/10.2307/3558433

Ribeiro, C., Souza, K., Ribeiro, T., Vieira, A., Mendonça, L., Barbosa, W., & Vieira, J. (2013). Avaliação da atividade antimicrobiana de plantas utilizadas na medicina popular da amazônia. Infarma - Ciências Farmacêuticas, 21(1/2), 45-49. Recuperado de http://revistas.cff.org.br/?journal=infarma&page=article&op=view&path%5B%5D=172&path%5B%5D=162

Salmon-Chemin, L., Buisine, E., Yardley, V., Kohler, S., Debreu, M. A., Landry, V., Sergheraert, C., Croft, S. L., Krauth-Siegel, R. L., & Davioud-Charvet, E. (2001). 2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: Synthesis and correlation between redox cycling activities and in vitro cytotoxicity. Journal of Medicinal Chemistry, 44(4), 548–565. https://doi.org/10.1021/jm001079l

Santos, D. L., Silva, G. de N. F. da, Moraes, J. S., Souza, K. O. da, Rodrigues, E. M. da S., Fecury, A. A., Dendasck, C. V., Dias, C. A. G. de M., Pinheiro, M. da C. N., Moreira, E. C. de M., Araújo, M. H. M. de, da Silva, I. R., & Oliveira, E. de. (2020). Traditional herbal medicine in a community in northeastern Pará: the use of Eleutherine plicata Herb. in the treatment of Amebiasis. Research, Society and Development, 9(7), e620974539. https://doi.org/10.33448/rsd-v9i7.4539

Shi, P, Du, W, Wang, Y, Teng, X, Chen, X, Ye, L. (2019). Total phenolic, flavonoid content, and antioxidant activity of bulbs, leaves, and flowers made from Eleutherine bulbosa (Mill.) Urb. Food Sci Nutr. 2019; 7: 148– 154. https://doi.org/10.1002/fsn3.834.

Shibuya, H., Fukushima, T., Ohashi, K., Nakamura, A., Riswan, S., & Kitagawa, I. (1997). Indonesian Medicinal Plants. XX. Chemical Structures of Eleuthosides A, B, and C, Three New Aromatic Glucosides from the Bulbs of Eleutherine palmifolia (Iridaceae). Chemical & Pharmaceutical Bulletin, 45(7), 1130–1134. https://doi.org/10.1248/cpb.45.1130

Silva, M. N. da, Ferreira, V. F., & Souza, M. C. B. V. de. (2003). Um panorama atual da química e da farmacologia de naftoquinonas, com ênfase na β-lapachona e derivados. Química Nova, 26(3), 407–416. https://doi.org/10.1590/S0100-40422003000300019

Vale, V.V.; Cruz, J.N.; Viana, G.M.; Póvoa, M.M.; Brasil, D.D.; Dolabela, M.F. (2020). Naphthoquinones isolated from Eleutherine plicata herb: In vitro antimalarial activity and molecular modeling to investigate their binding modes. Med. Chem. Res., 3, 487–494. https://doi.org/10.1007/s00044-019-02498-z.

Vásquez, S. P. F., Mendonça, M. S. De, & Noda, S. do N. (2014). Etnobotânica de plantas medicinais em comunidades ribeirinhas do Município de Manacapuru , Amazonas , Brasil. Acta Amazonica, 44(4), 457–472. https://doi.org/10.1590/1809-4392201400423

Wagner, H., Bladt, S., & Zgainski, E. M. (1984). Plant drug analysis. New York: Springer Verlag. https://link.springer.com/book/10.1007/978-3-662-02398-3

Waode, M.; Widanarni; Yuhana M.; Setiawati M.; Setiawati, M.; & Wahyudi, A. T. (2019) Phytochemical analysis and antibacterial activities of Eleutherine bulbosa (Mill.) Urb. extract against Vibrio parahaemolyticus. Asian Pacific Journal of Tropical Biomedicine, 9 (9), 397-404. https://doi.org/10.4103/2221-1691.267669

Waode, M.; Widanarni; Yuhana M.; Setiawati M.; Setiawati, M.; & Wahyudi, A. T. (2020). Effect in white shrimp Litopenaeus vannamei of Eleutherine bulbosa (Mill.) Urb. Powder on immune genes expression and resistance against Vibrio parahaemolyticus infection. Fish & Shellfish Immunology, 102, 218-227. https://doi.org/10.1016/j.fsi.2020.03.066.

Zhengxiong, C., Huizhu, H., Chengrui, W., Yuhui, L., Jianmi, D., Sankawa, U., Noguchi, H., & Iitaka, Y. (1986). Hongconin, a New Naphtalene Derivative from Hong-Cong, the Rhizome of Eleutherine americana Merr. et Heyne (Iridaceae). Chemical & Pharmaceutical Bulletin, 34(7), 2743–2746. https://doi.org/10.1248/cpb.34.2743

Published

30/10/2022

How to Cite

ALMEIDA, Y. de S. A. P.; ESPINAR, M. T. F. .; ARANHA, E. S. P. .; VASCONCELLOS, M. C. de; NUNEZ, C. V. Phytochemical study and bioactivity of Eleutherine bulbosa (MILLER) Urb. Research, Society and Development, [S. l.], v. 11, n. 14, p. e369111436460, 2022. DOI: 10.33448/rsd-v11i14.36460. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/36460. Acesso em: 22 nov. 2024.

Issue

Section

Agrarian and Biological Sciences