Abstract
A new lycosinine derivative, 9-O-demethyllycosinine B, was isolated from the native Brazilian Hippeastrum breviflorum Herb., Amaryllidaceae, along with the well-known alkaloids lycosinine B and lycorine. The structure of the new compound was established by physical and spectroscopic methods. 9-Odemethyllycosinine B is the third lycosinine variant identified in the Amaryllidaceae family.
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Bastida, J., Lavilla, R., Viladomat, F., 2006. Chemical and biological aspects of Narcissus alkaloids. In: Cordell, G.A. (Ed.), The Alkaloids, vol. 63. Elsevier Inc., Amsterdam, pp. 87–179.
Berkov, S., Codina, C., Viladomat, F., Bastida, J., 2008. N-alkylated galathamine derivatives: potent acetylcholinesterase inhibitors from Leucojum aestivum. Bioorg. Med. Chem. Lett. 18. 2263–2266.
Cordell, G.A., 2001. The potential of alkaloids in drug discovery. Phytother. Res. 15. 183–205.
da Silva, A.F.S., (Ph.D. thesis) 2005. Estudo Químico e Biológico de Hippeastrum vittatum (L Hér.) Herberte Hippeastrum striatum (Lam.) Moore (Amaryllidaceae). Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, pp. 119.
da Silva, A.F.S., Andrade, J.P., Bevilaqua, L.R.M., De Souza, M.M., Izquierdo, I., Henriques, A.T., Zuanazzi, J., 2006. Anxiolitic-, antidepressant- and anticonvulsant- like effects of the alkaloid montanine isolated from Hippeastrum vittatum. Pharmacol. Biochem. Behav. 85. 148–154.
da Silva, A.F.S., Andrade, J.P., Machado, K.R.B., Rocha, A.B., Apel, M.A., Sobral, M., Henriques, A.T., Zuanazzi, J.A.S., 2008. Screening for cytotoxic activity of extracts and isolated alkaloids from bulbs of Hippeastrum vittatum. Phytomedicine 15. 882–885.
de Andrade, J.P., Berkov, S., Viladomat, F., Codina, C., Zuanazzi, J.A.S., Bastida, J., 2011. Alkaloids from Hippeastrum papilio. Molecules 16. 7097–7104.
de Andrade, J.P., Guo, Y., Font-Bardia, M., Calvet, T., Dutilh, J., Viladomat, F., Codina, C., Nair, J.J., Zuanazzi, J.A.S., Bastida, J., 2014. Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum. Phytochemistry 103. 188–195.
de Andrade, J.P., Giordani, R.B., Torras-Claveria, L., Pigni, N.B., Berkov, S., Font-Bardia, M., Calvet, T., Konrath, E., Bueno, K., Sachett, L.G., Dutilh, J.H., Borges, W.S., Viladomat, F., Henriques, A.T., Nair, J.J., Zuanazzi, J.A.S., Bastida, J., 2015. The Brazilian Amaryllidaceae as a source of acetylcholinesterase inhibitory alkaloids. Phytochem. Rev., https://doi.org/10.1007/s11101-015-9411-7.
Dutilh, J.H., Fernandez, E.P., Penedo, T.S.A., de Moraes, M.M.V., Messina, T., 2013. Amaryllidaceae. In: Martinelli, G., Moraes, M.A. (Eds.), Livro Vermelho da Flora do Brasil. CNCFLORA, Rio de Janeiro, pp. 126–139.
Ghosal, S., Saini, K.S., Razdan, S., 1985. Crinum alkaloids: their chemistry and biology. Phytochemistry 24. 2141–2156.
Giordani, R.B., Vieira, P.B., Weizenmann, M., Rosember, D.B., Souza, A.P., Bonorino, C., de Carli, G.A., Bogo, M.R., Zuanazzi, J.A.S., Tasca, T., 2011a. Lycorine induces cell death in the amitochondriate parasite, Trichomonas vaginalis, via an alternative non-apoptotic death pathway. Phytochemistry 72. 645–650.
Giordani, R.B., de Andrade, J.P., Verli, H., Dutilh, J.H., Henriques, A.T., Berkov, S., Bastida, J., Zuanazzi, J.A.S., 2011b. Alkaloids from Hippeastrum morelianum Lem. (Amaryllidaceae). Magn. Reson. Chem. 49. 668–672.
Giordani, R.B., Rezende Junior, C.O., Andrade, J.P., Bastida, J., Zuanazzi, J.A.S., Tasca, T., De Almeida, M.V., 2012. Lycorine derivatives against Trichomonas vaginalis. Chem. Biol. Drug Des. 80. 129–133.
Hofmann Jr., A.E., Sebben, C., Sobral, M., Dutilh, J., Henriques, A.T., Zuanazzi, J.A.S., 2003. Alkaloids of Hippeatrum glaucescens. Biochem. Syst. Ecol. 31. 1455–1456.
McNulty, J., Nair, J.J., Codina, C., Bastida, J., Pandey, S., Gerasimoff, J., Griffin, C., 2007. Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids. Phytochemistry 68. 1068–1074.
Pagliosa, L.B., Monteiro, S., Andrade, J.P., Dutilh, J., Bastida, J., Cammarota, M., Zuanazzi, J.A.S., 2010. Effect of isoquinoline alkaloids from two Hippeastrum species on in vitro acetylcholinesterase activity. Phytomedicine 17. 698–701.
Ünver, N., 2007. New skeletons and new concepts in Amaryllidaceae alkaloids. Phytochem. Rev. 6. 125–135.
Yang, Y., Huang, S., Zhao, Y., Sun, H., 2005. Alkaloids from the bulbs of Lycoris aurea. Helv. Chim. Acta 88. 2550–2553.
Acknowledgments
This investigation was supported by grants of CAPES, FAPERGS CNPq (Brazil). JPA the Agencia Española de Cooperación Internacional para el Desarollo (BECASMAEC-AECID) for a doctoral fellowship. JASZ and ATH are grateful to CNPq for researcher fellowships.
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CS carried out the phytochemical process for isolation and wrote the manuscript. RBG and JPA also contributed in writing the manuscript. SB and EJO performed NMR analysis and MS helped in the collection and identification of the plant material. MVA and ATH contributed to the critical reading the manuscript. CS, RBG, JPA, SB, JASZ and JB were responsible for the spectral analysis and critical reading of the text. All authors have approved the final version for publishing.
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Sebben, C., Giordani, R.B., de Andrade, J.P. et al. New lycosinine derivative from Hippeastrum breviflorum. Rev. Bras. Farmacogn. 25, 353–355 (2015). https://doi.org/10.1016/j.bjp.2015.06.005
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DOI: https://doi.org/10.1016/j.bjp.2015.06.005