Antiophidic Solanidane Steroidal Alkaloids From Solanum Campaniforme

Three new solanidane alkaloids bearing a 22,23-epoxy ring (1-3) and four known compounds were isolated from leaves of Solanum campaniforme. The structures were determined using spectroscopic techniques, including 1Dand 2D NMR, and HRESIMS experiments. The antiophidic activity of the alkaloids was tested against Bothrops pauloensis venom. Compounds 1-3 completely inhibited myotoxicity without inhibiting phospholipase A 2 activity of the venom, while hemorrhage and skin necrosis were significantly reduced in the presence of alkaloids 1 and 2. © 2011 The American Chemical Society and American Society of Pharmacognosy.741021682173Wink, M., (2003) Phytochemistry, 64, pp. 3-19Nino, J., Correa, Y.M., Mosquera, O.M., (2009) Pharm. Biol., 47, pp. 255-259Ikeda, T., Tsumagari, H., Honbu, T., Nohara, T., (2003) Biol. Pharm. Bull., 26, pp. 1198-1201Kodoru, S., Grierson, D.S., Van De Venter, M., Afolayan, A.J., (2007) Pharm. Biol., 45, pp. 613-618Sun, L., Zhao, Y., Li, X., Yuan, H., Cheng, A., Lou, H., (2010) Toxicol. in Vitro, 24, pp. 1504-151Emmanuel, S., Ignacimuthu, S., Perumalsamy, R., Amalraj, T., (2006) Fitoterapia, 77, pp. 611-612Pandurangan, A., Khosa, R.L., Hemalatha, S., (2010) J. Asian Nat. Prod. Res., 12, pp. 691-695Fenner, R., Betti, A.H., Mentz, L.A., Rates, S.M.K., (2006) Rev. Bras. Cienc. Farm., 42, pp. 369-394Harrison, R.A., Hargreaves, A., Wagstaff, S.C., Faragher, B., Lalloo, D.G., (2009) PLoS Negl. Trop. Dis., 3, p. 569Mors, W.B., Nascimento, M.C., Pereira, B.M.R., Pereira, N.A., (2000) Phytochemistry, 55, pp. 627-642Correa-Netto, C., Teixeira-Araujo, R., Aguiar, A.S., Melgarejo, A.R., De-Simone, S.G., Soares, M.R., Foguel, D., Zingali, R.B., (2010) Toxicon, 55, pp. 1222-1235Gutiérrez, J.M., Rucavado, A., Chaves, F., Díaz, C., Escalante, T., (2009) Toxicon, 54, pp. 958-975Caron, E.J., Manock, S.R., Maudlin, J., Koleski, J., Theakston, R.D., Warrell, D.A., Smalligan, R.D., (2009) Toxicon, 54, pp. 779-83Cotrim, C.A., De Oliveira, S.C., Diz Filho, E.B., Fonseca, F.V., Baldissera, Jr.L., Antunes, E., Ximenes, R.M., Toyama, M.H., (2011) Chem. Biol. Interact., 15, pp. 9-16Lomonte, B., León, G., Angulo, Y., Rucavado, A., Núñez, V., (2009) Toxicon, 54, pp. 1012-1028Coelho, R.M., Souza, M.C., Giotto, M.H.S., (1998) Phytochemistry, 49, pp. 893-897Lawson, D.R., Green, T.P., Haynes, L.W., Miller, A.R., (1997) J. Agric. Food Chem., 45, pp. 4122-4126Chiesa, F.A.F., Moyna, P., Alcaloides Esteroidales (2004) Farmacognosia: Da Planta Ao Medicamento, pp. 869-883. , In, 5 th ed. Simões, C. M. O. Schenkel, E. P. Gosmann, G. Mello, J. C. P. Mentz, L. A. Petrovick, P. R. Ed.a da UFRGS: Porto AlegreDraper, R.W., Puar, M.S., Vater, E.J., McPhail, A.T., (1998) Steroids, 63, pp. 135-140Jiang, Z.H., Wang, J.R., Li, M., Liu, Z.Q., Chau, K.Y., Zhao, C., Liu, L., (2005) J. Nat. Prod., 68, pp. 397-399Daneluttea, A.P., Costantina, M.B., Delgadob, G.E., Braz-Filho, R., Kato, M.J., (2005) J. Braz. Chem. Soc., 16, pp. 1425-1430Slimestad, R., Fossen, T., Verheul, M.J., (2008) J. Agric. Food Chem., 56, pp. 2436-2441Friedman, M., Lee, K.-R., Kim, H.-J., Lee, I.-S., Kozukue, N., (2005) J. Agric. Food Chem., 53, pp. 6162-6169Milner, S.E., Brunton, N.P., Jones, P.W., Brien, N.M.O., Collins, S.G., Maguire, A.R., (2011) J. Agric. Food Chem., 59, pp. 3454-3484Corrêa, L.C., Marchi-Salvador, D.P., Cintra, A.C.O., Sampaio, S.V., Soares, A.M., Fontes, M.R.M., (2008) Biochim. Biophys. Acta, 1784, pp. 591-599Cintra-Francischinelli, M., Pizzo, P., Angulo, Y., Gutiérrez, J.M., Montecucco, C., Lomonte, B., (2010) Toxicon, 55, pp. 590-596Montecucco, C., Ornella, R., Caccin, P., Rigoni, M., Carli, L., Morbiato, L., Muraro, L., Paoli, M., (2009) Toxicon, 54, pp. 561-564Fernandes, C.A., Marchi-Salvador, D.P., Salvador, G.M., Silva, M.C., Costa, T.R., Soares, A.M., Fontes, M.R., (2010) J. Struct. Biol., 171, pp. 31-43Silva, J.O., Fernandes, R.S., Ticli, F.K., Oliveira, C.Z., Mazzi, M.V., Franco, J.J., Giuliatti, S., Sampaio, S.V., (2007) Toxicon, 50, pp. 283-291Esmeraldino, L.E., Souza, A.M., Sampaio, S.V., (2005) Phytomedicine, 12, pp. 570-57