Essential Oils From Neotropical Myrtaceae: Chemical Diversity And Biological Properties

Myrtaceae family (121 genera, 3800-5800 spp.) is one of the most important families in tropical forests. They are aromatic trees or shrubs, which frequently produce edible fruits. In the neotropics, ca. 1000 species were found. Several members of this family are used in folk medicine, mainly as an antidiarrheal, antimicrobial, antioxidant, cleanser, antirheumatic, and anti-inflammatory agent and to decrease the blood cholesterol. In addition, some fruits are eaten fresh or used to make juices, liqueurs, and sweets very much appreciated by people. The flavor composition of some fruits belonging to the Myrtaceae family has been extensively studied due to their pleasant and intense aromas. Most of the essential oils of neotropical Myrtaceae analyzed so far are characterized by predominance of sesquiterpenes, some with important biological properties. In the present work, chemical and pharmacological studies carried out on neotropical Myrtaceae species are reviewed, based on original articles published since 1980. The uses in folk medicine and chemotaxonomic importance of secondary metabolites are also briefly discussed. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.817394Wilson, P.G., O'Brien, M.M., Gadek, P.A., Quinn, C.J., (2001) Am. J. Bot., 88, p. 2013Conti, E., Litt, A., Wilson, P.G., Graham, S.A., Briggs, B.G., Johnson, L.A.S., Sytsma, K.J., (1997) Syst. Bot., 22, p. 629Wilson, P.G., O'Brien, M.M., Heslewood, M.M., Quinn, C.J., (2005) Plant Syst. Evol., 251, p. 3Lucas, E.J., Belsham, S.R., Lughadha, E.M.N., Orlovich, D.A., Sakuragui, C.M., Chase, M.W., Wilson, P.G., (2005) Plant Syst. Evol., 251, p. 35Barroso, G.M., Perón, V., Myrtaceae (1994) Reserva Ecológica de Macaé de Cima, Nova Friburgo, RJ. Aspectos Florísticos das Espécies Vasculares, 1, pp. 261-302. , Eds. M. P. M. Lima, R. R. Guedes-Bruni, Jardim Botânico do Rio de Janeiro, Rio de JaneiroFilho, H.F.L., (1993) Ecologia da Mata Atlântica em Cubatão, p. 184. , Editora da UNESP e Editora da Universidade de Campinas, CampinasMori, S.A., Boom, B.M., De Carvalino, A.M., Dos Santos, T.S., (1983) Biotropica, 15, p. 68Peixoto, A.L., Gentry, A., (1990) Rev. Bras. Bot., 13, p. 19Reitz, R., Klein, R.M., Reis, A., (1978) Projeto Madeiras de Santa Catarina, p. 320. , Itajaí, Herbário Barbosa RodriguesLandrum, L.R., Kawasaki, M.L., (1997) Brittonia, 49, p. 508Kahkonen, M.P., Hopia, A.I., Heinonen, M., (2001) J. Agric. Food Chem., 49, p. 4076Adams, R.P., (2007) Identification of Essential Oil Components by Gas Chromatography/mass Spectrometry, , 4th edn., Allured Publishing, Carol StreamApel, M.A., Sobral, M., Schapoval, E.E.S., Henriques, A.T., Menut, C., Bessiere, J.-M., (2004) J. Essent. Oil Res., 16, p. 321Setzer, W.N., Schmidt, J.M., Noletto, J.A., Vogler, B., (2006) Pharmacologyonline, 3, p. 794Maia, J.G.S., Zoghbi, M.G.B., Luz, A.I.R., (1997) J. Essent. Oil Res., 9, p. 337Ogunwande, I.A., Olawore, N.O., Ekundayo, O., Walker, T.M., Schmidt, J.M., Setzer, W.N., (2005) L. Int. J. Aromather., 15, p. 147Figueiredo, A.C., Barroso, J.G., Pedro, L.G., Scheffer, J.J.C., (2008) Flavour Fragrance J., 23, p. 213Vila, R., Iglesias, J., Cañigueral, S., Santana, A.I., Nolís, P.N., Gupta, M.P., (2004) J. Essent. Oil Res., 16, p. 384Apel, M.A., Sobral, M., Schapoval, E.E.S., Henriques, A.T., Menut, C., Bessière, J.-M., (2004) J. Essent. Oil Res., 16, p. 135Cole, R.A., Haber, W.A., Setzer, W.N., (2007) Biochem. Syst. Ecol., 35, p. 877Pino, J.A., Bello, A., Urquiola, A., Agüero, J., (2003) J. Essent. Oil Res., 15, p. 15Apel, M.A., Limberger, R.P., Sobral, M., Ntalani, H., Verin, P., Menut, C., Bessiere, J.-M., Henriques, A.T., (2002) J. Essent. Oil Res., 14, p. 163Bello, A., Rodrigues, M.L., Castineiras, N., Urquiola, A., Rosado, A., Pino, J.A., (1995) J. Essent. Oil Res., 7, p. 697Apel, M.A., Sobral, M., Schapoval, E.E.S., Henriques, A.T., Menut, C., Bessière, J.-M., (2004) J. Essent. Oil Res., 16, p. 191Magina, M.D.A., Dalmarco, E.M., Wisniewski Jr., A., Simionatto, E.L., Dalmarco, J.B., Pizzolatti, M.G., Brighente, I.M.C., (2009) J. Nat. Med., 63, p. 345Vera, R.R., Laurent, S.J., Fraisse, D.J., (1994) J. Essent. Oil Res., 6, p. 155Fischer, D.C.H., Limberger, R.P., Henriques, A.T., Moreno, P.R.H., (2005) J. Essent. Oil Res., 17, p. 499Lima, N.P., Cerqueira, S.H.F., Fávero, O.A., Romoff, P., Lago, J.H.G., (2008) J. Essent. Oil Res., 20, p. 223Ramos, M.F.S., Siani, A.C., Rosas, E.C., Henriques, M.G.M.O., (2006) Rev. Fitos., 2, p. 58Moreno, P.R.H., Lima, M.E.L., Sobral, M., Young, M.C.M., Cordeiro, I., Apel, M.A., Limberger, R.P., Henriques, A.T., (2007) Lam. Sci. Agric., 64, p. 428Stefanello, M.E.A., Cervi, A.C., Ito, I.Y., Salvador, M.J., Wisniewski Jr., A., Simionatto, E.L., (2008) J. Essent. Oil Res., 20, p. 75Setzer, W.N., Noletto, J.A., Vicent, M.A., (2006) Nat. Prod. Commun., 1, p. 43Pino, J., Bello, A., Urquiola, A., Garcia, S.A., (2001) J. Essent. Oil Res., 13, p. 407Costa, T.R., Fernandes, O.F.L., Santos, S.C., Oliveira, C.M.A., Lião, L.M., Ferri, P.H., Paula, J.R., Silva, M.R.R., (2000) J. Ethnopharmacol., 72, p. 111Duarte, A.R., Costa, A.R.T., Santos, S.C., Ferri, P.H., Paula, J.R., Naves, R.V., (2008) J. Essent. Oil Res., 20, p. 30Duarte, A.R., Naves, R.R., Santos, S.C., Seraphin, J.C., Ferri, P.H., (2009) J. Braz. Chem. Soc., 20, p. 967Pino, J.A., Marbot, R., Payo, A., Chao, D., Herrera, P., (2006) J. Essent. Oil Res., 18, p. 266Apel, M.A., Sobral, M., Schapoval, E.S., Henriques, A.T., Menut, C., Bessière, J.-M., (2004) J. Essent. Oil Res., 16, p. 437Henriques, A.T., Sobral, M., Cauduro, A.D., Schapoval, E.E.S., Bassani, V.L., Lamaty, G., Menut, C., Bessiere, J.-M., (1993) J. Essent. Oil Res., 5, p. 501Marin, R., Apel, M.A., Limberger, R.P., Raseira, M.C.B., Pereira, J.F.M., Zuanazzi, J.A.S., Henriques, A.T., (2008) Lat. Am. J. Pharm., 27, p. 172Apel, M.A., Sobral, M., Henriques, A.T., Menut, C., Bessière, J.-M., (2002) J. Essent. Oil Res., 14, p. 290Apel, M.A., Sobral, M., Schapoval, E.E.S., Henriques, A.T., Menut, C., Bessière, J.-M., (2005) J. Essent. Oil Res., 17, p. 284Pino, J.A., Marbot, R., Bello, A., Urquiola, A., (2003) J. Essent. Oil Res., 15, p. 256Martins, R.C.C., Alegrio, L.V., Castro, R.N., Godoy, R.L.O., (1999) J. Essent. Oil Res., 11, p. 724Godoy, R.L.O., Alegrio, L.V., Duarte, A.A.C., (1999) J. Essent. Oil Res., 11, p. 570Apel, M.A., Limberger, R.P., Sobral, M., Henriques, A.T., Ntalani, H., Verin, P., Menut, C., Bessière, J.-M., (2002) J. Essent. Oil Res., 14, p. 259Oliveira, R.N., Dias, I.J.M., Câmara, C.A.G., (2005) Braz. J. Pharmacogn., 15, p. 39Stefanello, M.E.A., Wisniewski Jr., A., Simionatto, E.L., Cervi, A.C., (2009) Lat. Am. J. Pharm., 28, p. 449Pino, J.A., Marbot, R., Payo, A., Chao, D., Herrera, P., Marti, M.P., (2005) J. Essent. Oil Res., 17, p. 278Pino, A.J., Bello, A., Urquiola, A., Aguero, J., (2002) J. Essent. Oil Res., 14, p. 412Stokes, S.L., Cole, R.A., Rangelova, M.P., Haber, W.A., Setzer, W., (2007) Nat. Prod. Commun., 2, p. 1211Alves, L.V., Alegrio, L.V., Castro, R.N., Godoy, R.L.O., (2000) J. Essent. Oil Res., 12, p. 693Limberger, R.P., Simões-Pires, C.A., Sobral, M., Menut, C., Bessière, J.-M., Henriques, A.T., (2003) Flavour Fragrance J., 18, p. 144Mahmoud, I.I., Moharram, F.A., El-Gindi, M.R., Marzouk, M.S.A., Nolte, J., Hassam, A.M.K., (2002) Bull. Fac. Pharm., 40, p. 123Urbiego, G., Taher, H.A., Talenti, E.C., (1987) An. Asoc. Quim. Argentina, 75, p. 377Weyerstahl, P., Marschall-Weyerstahl, H., Christiansen, C., Oguntimein, B.O., Adeoye, A.O., (1988) Planta Med., 54, p. 546El-Shabrawy, A.O., (1995) Bull. Fac. Pharm., 33, p. 17Morais, S.M., Craveiro, A.A., MacHado, M.I.L., Alencar, J.W., Matos, F.J.A., (1996) J. Essent. Oil Res., 8, p. 449Maia, J.G.S., Andrade, E.H.A., Silva, M.H.L., Zoghbi, M.G.B., (1999) J. Essent. Oil Res., 11, p. 727El Alfy, T.S., Ibrahim, T.A., Sleem, A.A., (2003) Bull. Fac. Pharm., 41, p. 83Mello, R.M., Corrêa, V.F.S., Amorim, A.C.L., Miranda, A.L.P., Rezende, C.M., (2007) J. Braz. Chem. Soc., 18, p. 179Costa, D.P., Santos, S.C., Seraphin, J.C., Ferri, P.H., (2009) J. Braz. Chem. Soc., 20, p. 1287Pino, J.A., Bello, A., Urquiola, A., Aguero, J., Marbot, R., (2003) J. Essent. Oil Res., 15, p. 70Dellacassa, E., Lorenzo, D., Mondello, L., Cotroneo, A., (1997) J. Essent. Oil Res., 9, p. 295Cole, R.A., Bansal, A., Moriarity, D.M., Haber, W.A., Setzer, W.N., (2007) J. Nat. Med., 61, p. 414Gressler, E., Pizo, M.A., Morellato, L.P.C., (2006) Rev. Bras. Bot., 29, p. 509Malagón, O., Vila, R., Iglesias, J., Zarazoga, T., Cañigueral, S., (2003) Flavour Fragrance J., 18, p. 527Henriques, A.T., Sobral, M., Bridi, R., Vérin, P., Menut, C., Lamaty, G., Bessière, J.-M., (1997) J. Essent. Oil Res., 9, p. 13Limberger, R.P., Sobral, M., Henriques, A.T., Menut, C., Bessière, J.-M., (2004) Quim. Nova, 27, p. 916Zoghbi, M.G.B., Andrade, E.H.A., Da Silva, M.H.L., Carreira, L.M.M., Maia, J.G.S., (2003) Flavour Fragrance J., 18, p. 421Alarcón, L.D., Peña, A.E., Gonzales, N., Quintero, A., Meza, M., Usubillaga, A., Velasco, J., (2009) Rev. Soc. Quim. Perú, 75, p. 221Stefanello, M.E.A., Cervi, A.C., Wisniewski Jr., A., Simionatto, E.L., (2007) J. Essent. Oil Res., 19, p. 466Cerqueira, M.D.D., Souza-Neta, L.C., Passos, M.G.V.M., Lima, E.O., Roque, N.F., Martins, D., Guedes, M.L.S., Cruz, F.G., (2007) J. Braz. Chem. Soc., 18, p. 998Stefanello, M.E.A., Cervi, A.C., Wisniewski Jr., A., Simionatto, E.L., (2010) Braz. J. Pharmacogn., 20, p. 82Cerqueira, M.D., Marques, E.J., Martins, D., Roque, N.F., Cruz, F.G., Guedes, M.L.S., (2009) Quim. Nova, 32, p. 1544Moriarity, D.M., Bansal, A., Cole, R.A., Takaku, S., Haber, W.A., Setzer, W.N., (2007) Nat. Prod. Commun., 2, p. 1263Cole, R.A., Haber, W.A., Setzer, W.N., (2008) J. Essent. Oil-Bearing Plants, 11, p. 41Rotman, A., Ahumada, O., Faillaci, S.M., Zugadlo, J.A., (2001) J. Essent. Oil-Bearing Plants, 4, p. 37Tucker, A.O., MacIarello, M.J., Landrum, L.R., (1993) J. Essent. Oil Res., 5, p. 333Furlan, R., Zachino, S., Gattuso, M., Bradessi, P., Roser, J.C., (2002) J. Essent. Oil Res., 14, p. 175Limberger, R.P., Sobral, M.E.G., Zuanazzi, J.A.S., Moreno, P.R.H., Schapoval, E.E.S., Henriques, A.T., (2001) Pharm. Biol., 39, p. 308Dellacassa, E., Lorenzo, D., Mondello, L., Dugo, P., (1997) J. Essent. Oil Res., 9, p. 673Tucker, A.O., MacIarello, M.J., Landrum, L.R., Kawasaki, M.L., (2000) J. Essent. Oil Res., 12, p. 149Tucker, A.O., MacIarello, M.J., Landrum, L.R., (1993) J. Essent. Oil Res., 5, p. 561Apel, M.A., Sobral, M., Zuanazzi, J.A.S., Henriques, A.T., (2006) Flavour Fragrance J., 21, p. 656Menut, C., Verin, P., Bessière, J.M., Lamay, G., Henriques, A.T., Poser, G.L.V., Toffoli, M.E., Sobral, M.E., Chemical exploration of Brazilian aromatic species belonging to the Myrtaceae family (1997) Proceedings of 27th International Symposium on Essential Oils, pp. 171-183. , Eds. C. Franz, A. Mathé, G. Buchbauer, 1996, Vienna, Allured Publishing, Carol StreamLimberger, R.P., Simões-Pires, C.A., Sobral, M., Menut, C., Bessière, J.-M., Henriques, A.T., (2002) Braz. J. Pharm. Sci., 38, p. 355Bansal, A., Boehme, A.K., Eiter, L.C., Schmidt, J.M., Setzer, W.N., Vicent, M.A., (2006) Nat. Prod. Commun., 1, p. 303Cole, R.A., Haber, W.A., Setzer, W.N., (2007) J. Essent. Oil-Bearing Plants, 10, p. 273Tucker, A.O., MacIarello, M.J., Michael, J., Salywon, A.M., Landrum, L.R., (2001) J. Essent. Oil Res., 13, p. 427Stefanello, M.E.A., Cervi, A.C., Wisniewski Jr., A., Simionatto, E.L., (2008) J. Essent. Oil Res., 20, p. 424Coutinho, I.D., Poppi, N.R., Cardoso, C.L., (2008) J. Essent. Oil Res., 20, p. 405Vallilo, M.I., Lamardo, L.C.A., Gaberlotti, M.L., Oliveira, E., Moreno, P.R.H., (2006) Cienc. Tecnol. Aliment. Campinas, 26, p. 805Limberger, R.P., Apel, M.A., Sobral, M., Moreno, P.R.H., Henriques, A.T., Menut, C., (2001) J. Essent. Oil Res., 13, p. 113Adati, R.T., Ferro, V.O., (2006) J. Essent. Oil Res., 18, p. 691Silva, J.R.M., Cardoso, C.A.L., Re-Poppi, N., (2009) Chem. Nat. Comp., 45, p. 565Apel, M.A., Sobral, M., Menut, C., Bessière, J.-M., Zuanazzi, J.A., Schapoval, E.E.S., Henriques, A.T., (2005) Flavour Fragrance J., 20, p. 176Limberger, R.P., Sobral, M., Henriques, A.T., (2005) Biochem. Syst. Ecol., 33, p. 287Gonçalves, M.J., Cavaleiro, C., Cunha, A.P., Salgueiro, L.R., (2006) J. Essent. Oil Res., 18, p. 108Vallverdú, C., Vila, R., Tomi, F., Carhuapoma, M., Casanova, J., Cañigueral, S., (2006) Flavour Fragrance J., 21, p. 241Limberger, R.P., Simões-Pires, C.A., Sobral, M., Henriques, A.T.J., (2004) Essent. Oil Res., 16, p. 479Souza, A., Silva, M.C., Cardoso-Lopes, E.M., Cordeiro, I., Sobral, M.E., Young, M.C., Moreno, P.R., (2009) Nat. Prod. Commun., 4, p. 1143Limberger, R.P., Sobral, M., Henriques, A.T., Menut, C., Bessière, J.-M., (2002) J. Essent. Oil Res., 14, p. 302Limberger, R.P., Simões-Pires, C.A., Sobral, M., Menut, C., Bessière, J.-M., Henriques, A.T., (2002) Flavour Fragrance J., 17, p. 341Cole, R.A., Haber, W.A., Lawton, R.O., Setzer, W.N., (2008) Chem. Biodiversity, 5, p. 1327Zygadlo, J.A., Rotman, A.D., Alonso, M.J.P., Negucruela, A.V., (1997) J. Essent. Oil Res., 9, p. 237Lorenzo, D., Dellacassa, E., Bonaccorsi, I., Mondello, L., (2001) Flavour Fragrance J., 16, p. 97Apel, R.M., Sobral, M., Henriques, A.T., (2006) Braz. J. Pharmacogn., 16, p. 402Tucker, A.O., MacIarello, M.J., Michael, J., Landrum, L.R., (2002) J. Essent. Oil Res., 14, p. 40Tucker, A.O., MacIarello, M.J., Landrum, L.R., (1992) J. Essent. Oil Res., 4, p. 313Pino, J.A., Rosado, A., Bello, A., Urquiola, G., Garcia, G., (2000) J. Essent. Oil Res., 12, p. 225Arze, J.B.L., Jean, F.I., Gagnon, H., Collin, G., Garneau, F.X., Pichette, A., (2005) J. Essent. Oil Res., 17, p. 64Pino, J.A., Quijano, C.E., (2008) J. Essent. Oil Res., 20, p. 205Andrade, E.H.A., Zoghbi, M.G.B., Silva, A.C.M., (2006) J. Essent. Oil Res., 18, p. 93Schneider, N.F.Z., Moura, N.F., Colpo, T., Marins, K., Marangoni, C., Flach, A., (2008) Rev. Bras. Farm., 89, p. 131Limberger, R.P., Moreno, P.R.H., Farias, F.M., Sobral, M., Henriques, A.T., (2001) J. Essent. Oil Res., 13, p. 47Rotman, A., Ahumada, O., Demo, M.S., Oliva, M.M., Turina, A.V., López, M.L., Zyadlo, J.A., (2003) Flavour Fragrance J., 18, p. 211Limberger, R.M.P., Sobral, M., Menut, C., Henriques, A.T., (2001) J. Essent. Oil Res., 13, p. 250Pino, J., Rosado, A., Gonzalez, A., (1989) Nahrung, 33, p. 717Tucker, A.O., MacIarello, M.J., Michael, J., Landrum, L.R., (1992) J. Essent. Oil Res., 4, p. 195Lima, M.E.L., Cordeiro, I., Young, M.C.M., Sobra, M.E.G., Moreno, P.R.H., (2006) Pharmacologyonline, 3, p. 589Belo, A., Urquiola, A., Garcia, J.J., Rosado, A., Pino, J.A., (1998) Ingenr. Ciencia Quim., 18, p. 21Garcia, D., Alvarez, A., Tornos, P., Fernandez, A., Saenz, T., (2002) Z. Naturforsch. C, 57, p. 449Apel, M.A., Sobral, M., Zuanazzi, J.A., Henriques, A.T., (2006) Flavour Fragrance J., 21, p. 565Vila, R., Santana, A.I., Pérez-Rosés, R., Valderrama, A., Castelli, M.V., Mendonça, S., Zacchino, S., Cãnigueral, S., (2010) Bioresour. Technol., 101, p. 2510Pino, J.A., Bello, A., Urquiola, A., Aguero, J., (2003) J. Essent. Oil Res., 15, p. 23Pino, J.A., Bello, A., Urquiola, A., Correa, T., Rosado, A., (2002) J. Essent. Oil Res., 14, p. 372Silva, J.D., Luz, A.I.R., Silva, M.H.L.D., Andrade, E.H.A., Zoghbi, M.G.B., Maia, J.G.S., (2003) Flavour Fragrance J., 18, p. 240Santos, F.A., Cunha, G.M.A., Viana, G.S.B., Rao, V.S.N., Manoel, A.N., Silveira, E.R., (1997) Phytother. Res., 11, p. 67Tucker, A.O., MacIarello, M.J., Landrum, L.R., (1995) J. Essent. Oil Res., 7, p. 187Limberger, R.P., Faria, F.M., Sobral, M., Zuanazzi, J.A., Henriques, A.T., (2001) Rev. Bras. Farm., 82, p. 53Chen, J., Lichwa, J., Ray, C., (2007) J. Essent. Oil Res., 19, p. 276Yáñez, X., Pinzón, M.L., Solano, F., Sánchez, L.R., (2002) Molecules, 7, p. 712Diaz, T., Mora, F.D., Velasco, J., Diaz, T., Rojas, L.B., Usubillaga, A., Juan, C.A., (2008) Nat. Prod. Commun., 3, p. 937Pino, J.A., Bello, A., Urquiola, A., Aguero, J., Marbot, R., (2003) J. Essent. Oil Res., 15, p. 187Ji, X., Pu, Q., Garrafo, H.M., Pannell, L.K., (1991) J. Essent. Oil Res., 3, p. 187Li, J., Chen, F., Luo, J., (1999) J. Chin. Med. Mat., 22, p. 78Pino, J.A., Aguero, J., Marbot, R., Fuentes, V., (2001) J. Essent. Oil Res., 13, p. 61Ogunwande, I.A., Olawore, N.O., Adeleke, K.A., Ekundayo, O., Koenig, W.A., (2003) Flavour Fragrance J., 18, p. 136Kumar, A., Tandon, S., Naqvi, A.A., Kahol, A.P., (2005) Indian Perfum., 49, p. 73Cole, R., Setzer, W.N., (2007) J. Essent. Oil-Bearing Plants, 10, p. 365Bhalke, R.D., Patel, S.J., Girme, A.S., Anarthe, S.J., (2008) Pharmacologyonline, 3, p. 187MacLeod, A.J., De Troconis, N.G., (1982) Phytochemistry, 21, p. 1339Ekundayo, O., Ajani, F., Seppännen-Laakso, T., Laakso, I., (1991) Flavour Fragrance J., 6, p. 233Paniandy, J.C., Chane-Ming, J., Pieribattesti, J.C., (2000) J. Essent. Oil Res., 12, p. 153Chen, H.-C., Sheu, M.-J., Lin, L.-Y., Wu, C.-M., (2008) Acta Hortic., 765, p. 273Rossini, C., Dellacassa, E., Moyna, P., (1994) J. Essent. Oil Res., 6, p. 513Setzer, W.N., Noletto, J.A., Vicent, M.A., (2007) J. Essent. Oil-Bearing Plants, 10, p. 486Pino, J.A., Rosado, A., Bello, A., Urquiola, A., Garcia, S., (1999) J. Essent. Oil Res., 11, p. 783Freitas, O.M., Morais, S.M., Silveira, E.R., (2002) J. Essent. Oil Res., 14, p. 364Aguilera, L., Navarro, A., Tacoronte, J.E., Leyva, M., Marquett, M.C., (2003) Rev. Cubana Med. Trop., 55, p. 100Pino, J.A., Bello, A., Urquiola, A., Aguero, J., (2003) J. Essent. Oil Res., 15, p. 19Apel, R.M., Limberger, P., Sobral, M., Menut, C., Henriques, A.T., (2001) J. Essent. Oil Res., 13, p. 429Kalemba, D., Kunicka, A., (2003) Curr. Med. Chem., 10, p. 813Adam, K., Sivropoulou, A., Kokkini, S., Lanaras, T., Arsenakis, M., (1998) J. Agric. Food Chem., 46, p. 1739Hulin, V., Mathot, A.G., Mafart, P., Dufossé, L., (1985) Sci. Aliment., 18, p. 563Galli, A., Franzetti, L., Briguglio, D., (1985) Ind. Aliment., 227, p. 463Issa, A.Y., Volate, S.R., Wargavich, M.J., (2006) J. Food Comp. Anal., 19, p. 405Lagouri, V., Blekas, G., Tsimidou, M., Kokkini, S., Boskou, D., (1993) Z. Lebensm.-Unters.-Forsch. A, 197, p. 20Lagouri, V., Boskou, D., Screening for antioxidant activity of essential oils obtained from spices (1995) Food Flavors: Generation, Analysis and Process Influence, pp. 868-879. , Ed. G. Charalambous, Elsevier, AmsterdamTsimidou, M., Boskou, D., Antioxidant activity of essential oils from plants of the Lamiaceae family (1994) Spices, Herbs and Edible Fungi, pp. 273-284. , Ed. G. Charalambous, Elsevier, Amsterdam, B.VSuhaj, M., Spice antioxidants isolation and their antiradical activity: A review (2006) J. Food Comp. Anal., 19, p. 531Young, I.S., Woodside, J.V., Antioxidants in health and disease (2001) J. Clin. Pathol., 54, p. 176Limberger, R.P., Apel, M.A., Sobral, M., Schapoval, E.E.S., Henriques, A.T., (1998) Rev. Bras. Farm., 79, p. 49Demo, M.S., Oliva, M.M., Zunino, M.P., Lopez, M.L., Zygadlo, J.A., (2002) Pharm. Biol., 40, p. 481Werka, J.S., Boehme, A.K., Setzer, W.N., (2007) Nat. Prod. Commun., 2, p. 1215Adebajo, A.C., Oloke, K.J., Aladesanmi, A.J., (1989) Fitoterapia, 60, p. 451Medeiros, J.R., Medeiros, N., Medeiros, H., Davin, L.B., Lewis, N.G., (2003) J. Essent. Oil Res., 15, p. 293Lima, E.O., Gompertz, O.F., Giesbrecht, A.M., Paulo, M.Q., (1993) Mycoses, 36, p. 333Adebayo, T.A., Gbolade, A.A., Olaifa, J.I., (1999) Nigerian J. Nat. Prod. Med., 3, p. 74Amorin, A.C.L., Lima, C.K.F., Hovell, A.M.C., Miranda, A.L.P., Rezende, C.M., (2009) Phytomedicine, 16, p. 923Apel, M.A., Lima, M.E.L., Souza, A., Cordeiro, I., Young, M.C.M., Sobral, M.E.G., Suffredini, I.B., Moreno, P.R.H., (2006) Pharmacologyonline, 3, p. 376Zabka, M., Pavela, R., Slezakova, L., (2009) Ind. Crops. Prod., 30, p. 250Aurore, G.S., Abaul, J., Bourgeois, P., Luc, J., (1998) J. Essent. Oil Res., 10, p. 161Santos, F.A., Rao, V.S.N., Silveira, E.R., (1998) Phytother. Res., 12, p. 24Santos, F.A., Rao, V.S.N., Silveira, E.R., (1997) Fitoterapia, 68, p. 65Santos, F.A., Rao, V.S.N., Silveira, E.R., (1996) Phytother. Res., 10, p. 655Santos, F.A., Rao, V.S.N., Silveira, E.R., (1996) Phytomedicine, 3, p. 197Barroso, G.M., (1991) Sistemática de Angiosperms Do Brasil, p. 114. , Universidade Federal de Viscosa, ViscosaCravo, A.B., (1994) Frutas e Ervas Que Curam: Panacéia Vegetal, p. 438. , Hemus, São PauloAlice, C.B., Siqueira, N.C.S., Mentz, L.A., Silva, G.A.A.B.E., José, K.F.D., (1995) Plantas Medicinais de Uso Popular, Atlas Farmacognóstico, pp. 59-61. , Ulbra, CanoasRahhal, M.M., (1997) Alexandria Sci. Exch., 18, p. 225Cruz, A.V.M., Kaplan, M.A.C., (2004) Floresta Ambiente, 11, p. 47Holetz, F.B., Pessini, G.L., Sanches, N.R., Cortez, D.A.G., Nakamura, C.V., Filho, B.P.D., (2002) Mem. Inst. Oswaldo Cruz, 97, p. 1027Agra, M.F., Silva, K.N., Basilio, I.J.L.D., Freitas, P.F., Barbosa-Filho, J.M., (2008) Braz. J. Pharmacogn., 18, p. 472Dickel, M.L., Rates, S.M.K., Ritter, M.R., (2007) J. Ethnopharmacol., 109, p. 60Yoshikawa, M., Shimada, H., Nishida, N., Li, Y., Toguchida, I., Yamahara, J., Matsuda, H., (1998) Chem. Pharm. Bull., 46, p. 113Markman, B.E.O., Bacchi, E.M., Kato, E.T.M., (2004) J. Ethnopharmacol., 94, p. 55Aguirre, M.C., Delporte, C., Backhouse, N., Erazo, S., Letelier, M.E., Cassels, B.K., Silva, X., Negrete, R., (2006) Med. Chem., 14, p. 5673Delporte, C., Backhouse, N., Inostroza, V., Aguirre, M.C., Peredo, N., Silva, X., Negrete, R., Miranda, H.F., (2007) J. Ethnopharmacol., 112, p. 16

Antioxidant Capacity And Phenolic Content Of Four Myrtaceae Plants Of The South Of Brazil

Antioxidant compounds can be useful to prevent several degenerative diseases or as preservative in food and toiletries. Species of the Myrtaceae family are able to accumulate phenolic substances and those are closely related to the antioxidant activity due to their capacity to scavenge free radicals, protect against lipid peroxidation and quench reactive oxygen species. These facts prompted us to investigate the antioxidant capacity of the ethanolic extracts of the leaves of four Myrtaceae plants collected of the south of Brazil: Eugenia chlorophylla O. Berg., Eugenia pyriformis Cambess, Myrcia laruotteana Cambess and Myrcia obtecta (Berg) Kiacrsk. The antioxidant potential was performed using the DPPH (a single electron transfer reaction based assay) and ORAC (Oxygen Radical Absorbance Capacity, a hydrogen atom transfer reaction based assay) assays. Moreover, the total soluble phenolic content was also measured using the Folin-Ciocalteu reagent. A preliminary evaluation of the ethanolic extracts of these Myrtaceae plants revealed high levels of phenolic compounds (343.7-429.3 mg GAE) as well as high antioxidant activity according to both methods (1338 a 3785 μmol of TE/g of extract in ORAC and SC 50 in the range of 1.70 and 33.7 μg/mL in the DPPH). The highest antioxidant activity obtained by DPPH assay was exhibited by ethanol extract of the leaves of E. pyriformis (1.70 μg/mL), followed by extracts of M. laruotteana (3.38 μg/mL) and M. obtecta (6.66 μg/mL). In comparison with controls, in the DPPH assay, the extract of E. pyriformis was more active than trolox (SC 50 = 2.55 μg/mL), while the extracts of M. laruotteana and M. obtecta were more actives than quercetin (SC 50 = 7.80 μg/mL). In the ORAC assay, all species also show good antioxidant capacity (> 1000 μmol of TE/g). Initial HPLC-UV/DAD and ESI-MS confirmed the presence of phenolic acids constituents in the ethanol extracts. The results indicate the presence of compounds possessing promising antioxidant/free-radical scavenging activity in the analyzed extracts of Myrcia and Eugenia plants of the south of Brazil.67977982Abdel-Hammeed, S.S., Total phenolic contents and free radical scavenging activity of certain Egyptian Ficus species leaf samples (2009) Food Chemistry, 114, pp. 1271-1277Mosquera, O.M., Correa, Y.M., Buitrago, D.C., Nino, J., Antioxidant activity of twenty five plants from Colombian biodiversity (2007) Memorias do Instituto Oswaldo Cruz, 102 (5), pp. 631-634. , http://memorias.ioc.fiocruz.br/5817.pdfNabavi, S.M., Ebrahimzadeh, M.A., Nabavi, S.F., Jafari, M., Free radical savenging activity and antioxidant capacity of Eryngium caucasicum Trautv and Froripia subpinnata (2008) Pharmacologyonline, 3, pp. 19-25Muraina, I.A., Suleiman, M.M., Eloff, J.N., Can MTT be used to quantify the antioxidant activity of plant extracts? (2009) Phytomedicine, 16, pp. 665-668Landrum, L.R., Kawasaki, M.L., The genera of Myrtaceae in Brazil: An illustrated synoptic treatment and identification keys (1997) Brittonia, 49 (4), pp. 508-536Gressler, E., Pizo, M.A., Morellato, L.P.C., Pollination and seed dispersal of Brazilian Myrtaceae (2006) Revista Brasileira de Botanica, 29 (4), pp. 509-530. , http://www.scielo.br/pdf/rbb/v29n4/01.pdf, DOI 10.1590/S0100-84042006000400002Rufino, M.S.M., Fernandes, F.A.N., Alves, R.E., Brito, E.S., Free radical-scavenging behaviour of some North-east Brazilian fruits in a DPPH system (2009) Food Chemistry, 114, pp. 693-695Marin, R., Apel, M.A., Limberger, R.P., Raseira, M.C.B., Pereira, J.F.M., Zuanazzi, J.A.S., Henriques, A.T., Volatile components and antioxidant activity from some myrtaceous fruits cultivated in Southern Brazil (2008) Latin American Journal of Pharmacy, 27 (2), pp. 172-177Reynertson, K.A., Yang, H., Jiang, B., Basile, M.J., Kennely, E.J., Quantitative analysis of antiradical phenolic constituents from fourteen edible Myrtaceae fruits (2008) Food Chemistry, 109, pp. 883-890Coutinho, I.D., Coelho, R.G., Kataoka, V.M.F., Honda, N.K., Silva, J.R.M., Vilegas, W., Cardoso, C.A.L., Determination of phenolic compounds and evaluation of antioxidant capacity of Campomanesia adamantium leaves (2008) Ecletica Química, 33, pp. 53-60Legrand, C.D., Klein, R.M., (1969) Mirtáceas, , Reizi, R. Flora Ilustrada Catarinense", (R. Reitz, ed.) Herbário Barbosa Rodrigues, ItajaíStefanello, M.E.A., Cervi, A.C., Wisniewski Jr., A., Simionatto, E.L., Composition and seasonal variation of essential oils of Myrcia obtecta (O.Berg) Kiaersk. var. obtecta, Myrtaceae (2010) Brazilian Journal of Pharmacognosy, 20, pp. 82-86Stefanello, M.E.A., Wisniewski-Jr, A., Simionatto, E.L., Cervi, A.C., Chemical Composition and Seasonal variation of Essential Oils of Eugenia pyriformis (Myrtaceae) (2009) Latin American Journal of Pharmacy, 28, pp. 449-453Stefanello, M.E.A., Cervi, A.C., Ito, I.Y., Salvador, M.J., Wisniewski Jr., A., Simionatto, E.L., Chemical composition and antimicrobial activity of essential oils of Eugenia chlorophylla (Myrtaceae) (2008) Journal of Essential Oil Research, 20 (1), pp. 75-78Stefanello, M.E.A., Cervi, A.C., Wisniewski Jr., A., Simionatto, E.L., Essential oil composition of Myrcia laruotteana Camb (2007) Journal of Essential Oil Research, 19 (5), pp. 466-467Apel, Ma., Sobral, M., Schapoval, E.E.S., Rodrigues, A.T., Menut, C., Bessière, J., Chemical Composition of the essential oils of Eugenia beaurepaireana and E. pyriformis: Section Dichotomae (2004) Journal of Essential Oil Research, 16, pp. 191-192Limberger, R.P., Sobral, M., Henriques, A.T., Menut, C., Bessiere, J.-M., Essential oils from Myrcia species native to Rio Grande do Sul (2004) Quimica Nova, 27 (6), pp. 916-919. , http://www.scielo.br/pdf/qn/v27n6/22281.pdfSchmeda-Hirschmann, G., Flavonoids from Calycorectes, Campomanesia, Eugenia and Hexachlamys species (1995) Fitoterapia, 66, pp. 373-374Rufino, M.S.M., Alves, R.E., Brito, E.S., Pérez-Jiménez, J., Saura-Calixto, F., Mancini-Filho, J., Bioactive compounds and antioxidant capacities of 18 non-traditional tropical fruits from Brazil (2010) Food Chemistry, 121, pp. 996-1002Stieven, A.C., Moreira, J.J.S., Silva, C.F., Óleos essenciais de uvaia (Eugenia pyriformis Cambess): Avaliação das atividades microbiana e antioxidante (2009) Eclética Química, 34, pp. 7-13Gu, J.-Q., Park, E.J., Luyengi, L., Hawthorne, M.E., Mehta, R.G., Farnsworth, N.R., Pezzuto, J.M., Kinghorn, A.D., Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity (2001) Phytochemistry, 58 (1), pp. 121-127. , DOI 10.1016/S0031-9422(01)00180-7, PII S0031942201001807Mahmoud, I.I., Marzouk, M.S.A., Moharram, F.A., El-Gindi, M.R., Hassan, A.M.K., Acylated flavonol glycosides from Eugenia jambolana leaves (2001) Phytochemistry, 58 (8), pp. 1239-1244. , DOI 10.1016/S0031-9422(01)00365-X, PII S003194220100365XMatsuda, H., Morikawa, T., Yoshikawa, M., Antidiabetogenic constituents from several natural medicines (2002) Pure and Applied Chemistry, 74, pp. 1301-1308Hussein, S.A.M., Hashem, A.N.M., Seliemb, M.A., Lindequist, U., Nawwar, M.A.M., Polyoxygenated flavonoids from Eugenia edulis (2003) Phytochemistry, 64 (4), pp. 883-889. , DOI 10.1016/S0031-9422(03)00437-0Frighetto, N., Welendorf, R.M., Silva, A.M.P., Nakamura, M.J., Siani, A.C., Aplicação de cromatografia centrífuga de contra-corrente na purificação de ácido ursólico das folhas de Eugenia brasiliensis Lam (2005) Brazilian Journal of Pharmacognosy, 15, pp. 338-343Oliveira, A.M., Humberto, M.M.S., Silva, J.M., Rocha, R.F.A., Sant'Ana, A.E.G., Estudo fitoquímico e avaliação das atividades moluscicida e larvicida dos extratos da casca do caule e folha de Eugenia malaccensis (Myrtaceae) (2006) Brazilian Journal of Pharmacognosy, 16, pp. 618-624Pietta, P.G., Flavonoids as antioxidants (2000) Journal of Natural Products, 63, pp. 1035-1042Huang, D., Boxin, O.U., Prior, R.L., The chemistry behind antioxidant capacity assays (2005) Journal of Agricultural and Food Chemistry, 53 (6), pp. 1841-1856. , DOI 10.1021/jf030723cOu, B., Hampsch-Woodill, M., Prior, R.L., Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe (2001) Journal of Agricultural and Food Chemistry, 49 (10), pp. 4619-4626. , DOI 10.1021/jf010586oRice-Evans, C.A., Miller, N.J., Paganga, G., Structure-antioxidant activity relationships of flavonoids and phenolic acids (1996) Free Radical Biology and Medicine, 20 (7), pp. 933-956. , DOI 10.1016/0891-5849(95)02227-9Soares, S.E., Ácidos fenólicos como antioxidantes (2002) Revista de Nutrição, 15, pp. 71-81Theoduloz, C., Franco, L., Ferro, E., Hirschmann, G.S., Xanthine oxidase inhibitory activity of Paraguayan Myrtaceae (1988) Journal of Ethnopharmacology, 24 (2-3), pp. 179-183. , DOI 10.1016/0378-8741(88)90149-3Ye, M., Han, J., Chen, H., Zheng, J., Guo, D., Analysis of Phenolic Compounds in Rhubarbs Using Liquid Chromatography Coupled with Electrospray Ionization Mass Spectrometry (2007) Journal of the American Society for Mass Spectrometry, 18 (1), pp. 82-91. , DOI 10.1016/j.jasms.2006.08.009, PII S1044030506007811Moller, J.K.S., Catharino, R.R., Eberlin, M.N., Electrospray ionization mass spectrometry fingerprinting of essential oils: Spices from the Labiatae family (2007) Food Chemistry, 100 (3), pp. 1283-1288. , DOI 10.1016/j.foodchem.2005.10.013, PII S0308814605009118Roesler, R., Catharino, R.R., Malta, L.G., Eberlin, M.N., Pastore, G., Antioxidant activity of Annona crassiflora: Characterization of major components by electrospray ionization mass spectrometry (2007) Food Chemistry, 104 (3), pp. 1048-1054. , DOI 10.1016/j.foodchem.2007.01.017, PII S0308814607000702Clifford, M.N., Johnstton, K., Knight, S., Kuhnert, N., Hierarchical scheme for LC-MS n identification of chlorogenic acids (2003) Journal of Agricultural and Food Chemistry, 51, pp. 2900-2911Clifford, M.N., Knight, S., Kuhnert, N., Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS n (2005) Journal of Agricultural and Food Chemistry, 53 (10), pp. 3821-3832. , DOI 10.1021/jf050046hKim, H.J., Kim, E.J., Seo, S.H., Shin, C.-G., Jin, C., Lee, Y.S., Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus (2006) Journal of Natural Products, 69 (4), pp. 600-603. , DOI 10.1021/np050447rRoche, M., Dufour, C., Mora, N., Dangles, O., Antioxidant activity of olive phenols: Mechanistic investigation and characterization of oxidation products by mass spectrometry (2005) Organic and Biomolecular Chemistry, 3 (3), pp. 423-430. , DOI 10.1039/b416101gKweon, M.-H., Hwang, H.-J., Sung, H.-C., Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis) (2001) Journal of Agricultural and Food Chemistry, 49 (10), pp. 4646-4655. , DOI 10.1021/jf010514xHarbone, J.B., (1998) Phytochemical Methods. A Guide to Modern Techniques of Plant Analysis, , Chapman & Hall, LondonPiccinelli, A.L., De Simone, F., Passi, S., Rastrelli, L., Phenolic constituents and antioxidant activity of Wendita calysina leaves (burrito), a folk Paraguayan tea (2004) Journal of Agricultural and Food Chemistry, 52, pp. 5863-5868Aquino, S.D., Angioni, M., Schirru, S., Agabbio, M., Quality and physiological changes of film packaged 'Malvasio' mandarins during long term storage (2001) Lebensmittel-Wissenschaft Und-Technologie, 34, pp. 206-214Cuendet, M., Hostettman, K., Potterat, O., Dyatmko, W., Iridoid glucosides with free radical scavenging properties from Fagraea blumei (1997) Helvetica Chimica Acta, 80, pp. 1144-1152Salvador, M.J., Ferreira, E.O., Mertens-Talcott, S.U., Castro, W.V., Butterweck, V., Derendorf, H., Dias, D.A., Isolation and HPLC quantitative analysis of antioxidant flavonoids from Alternanthera tenella Colla (2006) Zeitschrift fuer Naturforschung, 100 (61), pp. 19-2

Bioactive Chemical Constituents And Biotechnological Production Of Secondary Metabolites In Amaranthaceae Plants, Gomphreneae Tribe

The Amaranthaceae family comprises of many species, which are used in nutrition and in traditional folk medicine for the treatment of several diseases such as infections, inflammation and fever. Gomphrena, Pfaffia and Alternanthera species are used in the extraction of natural pigments such as betaxanthin and betalains for application as food colorants and antioxidants. Pfaffia paniculata (Brazilian ginseng or Suma) has been indicated as a tonic, as well as having aphrodisiac, analgesic, and antidiabetic properties and may act against cancer. Gomphreneae is the major tribe of Amaranthaceae and previous chemical analyses have demonstrated the occurrence of anthraquinones, aurone, betacyanins, betaxanthins, betalains, chromoalkaloids, ecdysteroids, flavonoids, protoalkaloids, saponins, steroids and triterpenes. Biotechnological investigation with Amaranthaceae plants from the Gomphreneae tribe, demonstrated their potential for bioprospection of bioactive natural compounds such as flavonoids, steroids, terpenoides and saponins. Plant cell cultures, nowadays, are an important strategy for bioprospection of natural products. The in vitro large-scale production of bioactive compounds or extracts used as phytotherapics, pharmaceutical products, food additives and cosmetics should be encouraged because of their scientific, economical or ecological importance. Therefore, the present chapter reviews the literature data of the bioactive chemical constituents and biotechnological production of secondary metabolites in Amaranthaceae plants (Gomphreneae tribe), species that have many pharmacological properties and other applications. © 2012 Bentham Science Publishers. All rights reserved.124158Salvador, M.J., Pereira, P.S., Franca, S.C., Candido, R.C., Ito, I.Y., Dias, D.A., Bioactive chemical constituents and comparative antimicrobial activity of callus culture and adult plants extracts from Alternanthera tenella (2009) Z Naturforsch, 64, pp. 373-381Salvador, M.J., Ferreira, E.O., Pral, E.M.F., Bioactivity of crude extracts and some constituents of Blutaparon portulacoides (Amaranthaceae) (2002) Phytomedicine, 9Salvador, M.J., Zucchi, O.L.A.D., Candido, R.C., Ito, I.Y., Dias, D.A., In vitro antimicrobial activity of crude extracts and isolated constituents of Alternanthera maritima (Amaranthaceae) (2004) Pharm Biol, 42Cai, Y., Sun, M., Corke, H., Antioxidant activity of betalains from plants of Amaranthaceae (2003) J Agric Food Chem, 51Gorinstein, S., Nue, J.A., Arruda, P., Alcohol trace soluble and total proteins from Amaranth seeds and their comparison with other cereals (1991) J Agric Food Chem, 39Siqueira, J.C., Importância alimentícia e medicinal das Amaranthaceaes do Brasil (1987) Acta Biol Leopold, 9Siqueira, J.C., Phytogeography of Brasilian Amaranthaceae (1994) Pesquisa Botânica, 45, pp. 5-21Qureshi, R., Bhatti, G.H., Foklore uses of Amaranthaceae family from Nara desert, Pakistan (2009) Pak J Bot, pp. 1565-1572Ferreira, E.O., Salvador, M.J., Pral, E.M., Alfieri, S.C., Ito, I.Y., Dias, D.A., A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity (2004) Z Naturforsch, 59, pp. 499-505Salvador, M.J., Dias, D.A., Flavone C-glycosides from Alternanthera maritima (Mart.) St (2004) Hil. (Amaranthaceae). Biochem Syst Ecol, 32Brochado, C.D., De Almeida, A.P., Barreto, B.P., Costa, L.P., Ribeiro, L.S., Pereira, R.L.D., Koatz, V.L.G., Costa, S.S., Flavonol robinobiosides and rutinosides and their effects on lymphocyte proliferation in vitro (2003) J Braz Chem Soc, 14Zhou, B., Blaskò, G., Cordell, G.A., Alternanthin, a C-glycosylated flavonoid from Alternanthera philoxeroides (1988) Phytochemistry, 27Siqueira, J.C., A família Amaranthaceae nas restingas do Brasil (1987) Acta Biol Leopold, 9Siqueira, J.C., Guimarães, E.F., Amaranthaceae do Rio de Janeiro - gênero Alternanthera Forsskal (1984) Rodriguésia, 36Salvador, M.J., Ferreira, E.O., Mertens-talcott, S.U., Castro, W.V., Butterweck, V., Derendorf, H., Dias, D.A., Isolation and HPLC quantitative analysis of antioxidant flavonoids from Alternanthera tenella Colla (2006) Z Naturforsch, 61, pp. 19-25Souza, J.G., Tomei, R.R., Kanashiro, A., Kabeya, L.M., Azzolini, A.E.C.S., Dias, D.A., Salvador, M.J., Lucisano-valim, Y.M., Ethanolic crude extract and flavonoids isolated from Alternanthera maritima: neutrophil chemiluminescence inhibition and free radical scavenging activity (2007) Z Naturforsch, 62, pp. 339-347Patterson, G.W., Xu, S., Salt, T.A., Sterols of Caryophyllales with emphasis on Amaranthaceae (1991) Phytochemistry, 30Macedo, A.F., Barbosa, N.C., Esquibel, M.A., Souza, M.M., Cechinel, V., Pharmacological and phytochemical studies of callus culture extracts from Alternanthera brasiliana (1999) Pharmazie, 54Calderon, C.P., Asself, S.B.G., Fuentes, L.B., Evaluation of diuretic activity of Alteranthera pungens extract in rats (1997) Phytoth Res, 11Calderon, C.P., Asself, S.B.G., Fuentes, L.B., Ruiz, R.E.L., Ruiz, S.O., Constituents and purgative activity of fruits from Alternanthera pungens (1996) Acta Farm Bonaerense, 15Salt, T.A., Xu, S., Patterson, G.W., Adler, J.H., Diversity of sterol biosynthetic capacity in the Caryophyllidae (1991) Lipids, 26Lin, S.R., Chen, A.H., Constituents of Alternanthera sessilis (1975) T'ai-wan Yoo Hsueh Tsa Chih, 27, pp. 103-104. , abstract in: CA, v. 85, p. 189263g, 1976Dogra, J.V.V., Jha, O.P., Mishra, A., Chemotaxonomy of Amaranthaceae-study of triterpenes (1977) Plant Biochem J, 4Agrawal, Y.K., Jain, R.K., Chemical analysis of medicinal plant Alternanthera sessilis (1978) Pol J Chem, 52, p. 2495. , abstract in: CA, v. 91, p. 207493w, 1979Kapundu, M., Lami, N., Delaude, C., A saponin from Alternanthera sessilis (L.) R. Br (1986) Bull Soc R Sci Liege, 55, pp. 605-606. , abstract in: CA, v. 107, p. 4297c, 1987Penders, A., Kapundu, M., Delaude, C., Structure of principal saponin of Alternanthera sessilis (1992) Bull Soc Chem Belg, 101, pp. 227-232. , (abstract in: CA, 23287xSanoko, R., Esperanza, G., Pizza, C., De Tommasi, N., Triterpene saponins from Alternanthera repens (1999) Phytochemistry, 51Sahu, B.R., Chakrabarty, A., A flavone glycoside, robinitin-7-O-β-D-glucopyranoside from Alternanthera sessilis (1993) Asian J Chem, 5, pp. 1148-1150. , abstract in : CA, 265763dPiattelli, M., Minale, L., Pigments of Centrospermae-II (Distribution of Betacyanins) (1964) Phytochemistry, 3Rutz, R.E.L.D., Fusco, M., Ruiz, S.O., Constituents of Alternanthera pungens (1993) Fitoterapia, 64Blunden, G., Yang, M., Janicsak, G., Mathe, I., Cabarot-cuervo, C., Betaine distribution in the Amaranthaceae (1999) Biochem Syst Ecol, 27Ferreira, E.O., Dias, D.A., Phytochemical investigation of Gomphrena claussenii Moq (2004) Biochem Syst Ecol, 32Lewis, W.H., Elvin-lewis, M.P.F., Medical Botany (1977) Plants Affecting Man's Health, , New York: John Wiley and SonsPomilio, A.B., Sola, G.A., Mayer, A.M., Rumi, L.S., Antitumor and cytotoxic screen of 5,6,7-trisubstituted flavones from Gomphrena martiana (1994) J Ethnopharmacol, 44Siqueira JC.Ogênero Gomphrena, L., (1984), VI, pp. 183-194. , (Amaranthaceae) nos cerrados do Brasil. Acta Biológica LeopoldensiaPomilio, A.B., Buschi, C.A., Tomes, C.N., Viale, A.A., Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana (1992) J Ethnopharmacol., 36Siqueira, J.C., (1989), Flora do Estado de Goiás. Goiânia: Centro Editorial e Gráfico da UFGOBuschi, C.A., Pomilio, A.B., Comparative studies on species (1983) Anal Asocc Quim Argentina, 71, pp. 319-325Savchenko, T., Whiting, P., Sarker, S.D., Dinan, L., Ecdysteroids from Gomphrena haageana (Amaranthaceae) (1998) Biochem Syst Ecol, 24, pp. 177-178Buschi, C.A., Pomilio, A.B., Isorhammetin 3-O-robinobioside from Gomphrena martiana (1982) J Nat Prod, 45Buschi, C.A., Pomilio, A.B., Terpenoids, flavonoids and protoalkaloids from Gomphrena boliviana (1982) Anal Asocc Quim Argentina, 70Buschi, C.A., Pomilio, A.B., Gros, E.G., 5,6,7- trisubstituted flavones from Gomphrena martiana (1981) Phytochemistry, 20Buschi, C.A., Pomilio, A.B., Gros, E.G., New methylated flavones from Gomphrena martiana (1980) Phytochemistry, 19Buschi, C.A., Pomilio, A.B., Gros, E.G., A new flavona from Gomphrena martiana (1979) Phytochemistry, 18Sarker, S.D., Girault, J.P., Lafont, R., Dian, L.N., Ecdysteroids from Gomphrena haageana (Amaranthaceae) (1996) Biochem Sys Ecol, 24Young, M.C.M., Vieira, C.C.J., Chu, E.P., Haraguchi, M., Figueiredo-ribeiro, R.C.I., Ecdysterone and saponins from tuberous roots of Gomphrena officinalis Mart (1992) (Amaranthaceae). Rev Latinoamer Quim, 23Barneji, A., Chintalwar, G.J., Joshi, N.K., Chadha, M.S., Isolation of ecdysterone from Indian plants (1971) Phytochemistry, 10, p. 2225Sant́Ana, B.M.S., De Siqueira, N.C.S., Brasil, E., Silva, G.A.A., phenolic and steroid compounds of Gomphrena holosericea (1977) Rev Cent Cienc Biomed Univ Fed St Maria, 5, p. 55André, A.C.G.M., Dias, D.A., Pereira, O.S., Abreu, L.C.P., França, S.C., Estudo comparativo da produção de metabólitos secundários em cultura de células e na planta in natura de Gomphrena globosa (Amaranthaceae) (2003) Rev Bras Farmacogn, 13André, A.C.G.M., Dias, D.A., Chemical study of Gomphrena globosa (2001) Eur J Pharm Sci, 13, pp. 13.8. , In: 3rd Congresso of Pharmaceutical Sciences, 2001, Águas de LindóiaBouillant, M.L., Redolfi, P., Cantisani, A., Chopin, J., Gomphrenol, a new methylenedioxyflavonol from the leaves of Gomphrena globosa (Amaranthaceae) (1978) Phytochemistry, 17Chong, L.H.K., Ching, T., Chu, I., Expectorant principle from Gomphrena globosa structural determination of a new flavone glycoside (1981) Yao Hsueh Tung Pao, 16, p. 55Young, M.C.M., Potomati, A., Chu, E.P., Haraguchi, M., Yamamoto, M., Kawano, T., 13C NMR analysis of monodesmosidic saponins from Gomphrena macrocephala (1997) Phytochemistry, 46Tsuji, T., Yada, Y., Yamaguchi, K., Yamazaki, K., Kasai, R., Otani, K., Anti-helicobactor pylori saponin from Gomphrena globosa (1998) Jpn Kobai Tokkyo Koho JP, 10, p. 488Cai, Y., Sun, M., Corke, H., Identification and distribution of simple and acylated betacyanins in the Amaranthaceae (2001) J Agric Food Chem, 49Minale, L., Piattelli, M., De Stefano, S., Pigments of Centrospermae-VII (1967) Betacianins from Gomphrena globosa L. Phytochemistry, 6Heuer, S., Wray, V., Metzger, J.W., Strack, D., Betacyanins from flowers of Gomphrena globosa (1992) Phytochemistry, 31Stutzer, O., Die Gattung Pffafia mit einem Anhang neurer Arten von Alternanthera (1935) Feddes Repertorium Specierum Novarum Regni Vegetabilis, 88Siqueira, J.C., Grandi, T.S.M., O genero Pfaffia Mart (1986) (Amaranthaceae) nos cerrados e campos rupestres de Minas Gerais. Acta Biologica Leopoldensia, 8Marchioretto, M.S., Miotto, S.T.S., Siqueira, J.C., Pfaffia cipoana e Pfaffia rupestris (Amaranthaceae), duas novas especies para o Brasil (2008) Rodiguesia, 59Oliveira, F., Pfaffia paniculata (Martius) Kuntze - O ginseng-brasileiro (1986) Rev Bras Farmacogn, 1Nakai, S., Pfaffosides and nortriterpenoid saponins from Pfaffia paniculata (1984) Phytochemistry, 23, pp. 1703-1705Nishimoto, N., Nakai, S., Takagi, N., Pfaffosides and nortriterpenoids saponins from Pfaffia paniculata (1984) Phytochemistry, 23Shiobara, Y., Inoue, S.S., Kato, K., A nortriterpenoid, triterpenoids and acdysteroidsbfrom Pfaffia glomerata (1993) Phytochemistry, 32Zimmer, A.R., Bruxel, F., Bassani, V.L., Gosmann, G., HPLC method for the determination of ecdysterone in extractive solution from Pfaffia glomerata (2006) J. Pharm Biom Analysis, 40Takemoto, T., Pafaffic acid, a novel nortriterpene from Pfaffia paniculata Kuntze (1983) Tetrahedron Lett, 24Nishimoto, N., Shobara, Y., Fujino, M., Ecdysteroids from Pfaffia iresinoides and reassignment of some 13-C NMR Chemical shifts (1987) Phytochemistry, 26Nishimoto, N., Shibara, Y., Inoue, S.S., Three ecdysteroid glycosides from Pfaffia iresinoides (1988) Phytochemistry, 27Ferreira, E.O., Dias, D.A., A methylenedioxyflavonol from aerial parts of Blutaparon portulacoides (2000) Phytochemistry, 53Li, J.X., Hareyama, T., Tezuka, Y., Zhang, Y., Miyahara, T., Kadota, S., Five new oleanolic acid glycosides from Achyranthes bidentata with inhibitory activity on osteoclast formation (2005) Planta Medica, 71Cai, Y.Z., Sun, M., Corke, H., Characterization and application of betalain pigments from plants of the Amaranthaceae (2005) Trends Food Sci Technol, 16Khandaker, L., Ali, M.B., Oba, S., Influence of cultivar and growth stage on pigments and processing factors on betacyanins in red amaranth (Amaranthus tricolor L.) (2009) Trends Food Sci Technol., 15Zhu, F., Cai, Y.Z., Corke, H., Evaluation of Asian salted noodles in the presence of Amaranthus betacyanin pigments (2010) Food Chem, 118Naqvi, S.M., Rizvi, S.A., Accumulation of chromium and copper in three different soils and bioaccumulation in an aquatic plant, Alternanthera philoxeroides (2000) Bull Environ Contam Toxicol, 65, pp. 55-61Zucchi, O.L.A.D., Dias, D.A., Nascimento Filho, V.F., Salvador, M.J., Characterization of two medicinal plants by X-ray spectrometry (2000) J Trace Microprobe Tech, 18Salvador, M.J., Dias, D.A., Nascimento Filho, V.F., Zucchi, O.L.A.D., Análise elementar de Alternanthera maritima e Blutaparon portulacoides (Gomphreneae, Amaranthaceae) por fluorescência de raios X (2002), In: "VI ENAN (National Meeting on Nuclear Applications) e INAC 2002 (International Nuclear Atlantic Conference)", Rio de Janeiro, RJ - Brasil, 11 a 16 de agosto de 2002, Proceedings, VI National Meeting on Nuclear Apllications, Cd RomSalvador, M.J., Moreira, S., Dias, D.A., Zucchi, O.L.A.D., Determination of trace elements in Alternanthera brasiliana and Pfaffia glabrata by SR-TXRF: application in environmental pollution control (2004) Instrum Sci Technol, 32Rai, V., Sinha, S., Tripathi, R.D., Waste-water treatability potential of some aquatic macrophytes-removal of heavy metals (1995) Ecol Eng, 5Naqvi, S.M., Howell, R.D., Sholas, M., Cadmium and lead residues in field-collected red swamp crayfish (procambarusclarkii) and uptake by aligator weed, Alternanthera philoxeroides (1993) J Environ Sci Health part B, 28Informacoes sobre a Agencia Nacional de Vigilancia Sanitaria (Anvisa) e medicamento generico http://www.anvisa.gov.br, ANVISA - Agencia Nacional de Vigilancia Sanitaria, Disponivel em, acesso em 20 de abril de 2010Zucchi, O.L.A.D., Moreira, S., De Jesus, E.F.O., Salvio Neto, H., Salvador, M.J., Characterization of hypoglycemiant plants by total reflection X-ray fluorescence spectrometry (2005) Biol Trace Element Res., 103Chausmer, A.B., Zinc, insulin and diabetes (1998) J Am Coll Nutr, 17, pp. 109-115Kruse-jarres, J.D., Rukgauer, R., Trace elements in diabetes mellitus (2000) Peculiarities and clinical validity of determinations in blood cells. J Trace Elements Med Biol, 14Morris, B.W., Macneil, S., Stanley, K., Gray, T.A., Fraser, R., The interrelationship between insulin and chromium in hiperinsulinemic euglycaemic clamps in healthy volunteers (1993) J Endocrinol, 139Anderson, R.A., Nutritional factorsninfluenting the glucose/insulin system: chromium (1997) J Am Coll Nutr, 16Anderson, R.A., Cheng, N., Bryden, N.A., Elevated intakes of supplemental chromium improve glucose and insulin variables in individual with type 2 diabetes (1997) Diabetes, 46, pp. 1786-1791Salvador, M.J., Dias, D.A., Moreira, S., Zucchi, O.L.A.D., Analysis of medicinal plants and crude extracts by synchrotron radiation total reflection X-ray fluorescence (2003) J Trace Microprobe Tech, 21Murungi, J.I., Robinson, J.W., Studies on the toxic effects of dissolved aluminum on plant growth alligator grass (Alternanthera philoxeroides): the modifying effects of pH, humic substances and small quantities of cations (calcium, magnesium, iron) (1992) J Environ Sci Health part A, 27Olivares, E., Pena, E., Bioconcentration of mineral elements in Amaranthus dubius (wild spinach, Imbuya) growing wild in crops from Miranda state, Venezuela, and used as food (2009) Interciencia., 34Moraes, V.L.G., Santos, L.F.M., Castro, S.B., Inhibition of lymphocyte activation by extracts and fractions of Kalanchoe, Alternanthera, Paullinia and Mikania species (1994) Phytomedicine, 1, pp. 199-204Gasparetto, A., Lapinski, T.F., Zamuner, S.R., Khouris, S., Alves, L.P., Munin, E., Salvador, M.J., Extracts from Alternanthera maritima as natural photosensitizers in photodynamic antimicrobial chemoterapy (PACT) (2010) J Photochem Photobiol B: Biology, 99Biella De, A., Salvador, M.J., Dias, D.A., Dias-baruffi, M., Crotti, L.S.P., Evaluation of immunomodulatory and antiinflammatory effects and phytochemical screening of Alternanthera tenella Colla (Amaranthaceae) aqueous extracts (2008) Memorias do Instituto Oswaldo Cruz, 103De Souza, M.M., Kern, P., Floriani, A.E.O., Cechinel, V., Analgesic properties of a hydroalcoholic extract obtained from Alternanthera brasiliana (1998) Phytother Res, 12Lagrota, M.H.C., Wigg, M.D., Santos, M.M.G., Miranda, M.M.F.S., Camara, F.P., Couceiro, J.N.S.S., Costa, S.S., Inhibitory activity of extracts of Alternanthera brasiliana (Amaranthaceae) against the Herpes simplex virus (1994) Phytother Res, 8Mesa, J., Blair, S., Saez, J., Correa, A., Carmona, J., In vitro antimalarial evaluation of extracts of the plants Alternanthera lanceolata and Pollalesta discolor (1998) An Quim, 94Dewanji, A., Matai, S., Nutritional evaluation of leaf protein extracted from three aquatic plants (1996) J Agr Food Chem, 44Basnet, P., Kadota, S., Pandey, R.R., Screening of traditional medicines for their hypoglycemic activity in streptozotocin (stz)-Induced diabetic rats and a detailed study on psidium guajava (1995) J Trad Med, 12Si-man, Z., Young-sheng, H., Tabbo, J.D., Smith, K.M., Inhibitor against three human immunodeficiency virus in aqueous extract of Alternanthera phyloxeroides (1988) Clin Med J, 101Gerald, B., Yang, M., Janicsak, G., Mathe, I., Carabot-cuervo, A., Betaine distribution in the Amaranthaceae Biochem Syst Ecol, 199 (27), pp. 87-92Battha, R., Paes, T.K., Chemical and amino acid composition of alligatorweed (Alternanthera philoxeroides) (1996) Indian Vet J, 73He, L., Meng, Z., Studies on chemical constituents of Alternanthera philoxeroides (Mart.) Griseb (1995) Zhongguo Yaoke Daxue Xuebao, 26Dogra, J.V.V., Ojbra, O.P., Saponin from Alternanthera philoxeroides (Mart.) Griseb (1978) Comp Physiol Ecol, 3Zielske, A.G., Simons, J.N., Silverst, R.M., Flavone feeding stimulant in alligatorweed (1972) Phytochemistry, 11Garcia, S.B., Calderon, C.P., Fuentes, L.B., Preliminary evaluation of the gastrointestinal activity of Alternanthera pungens (1995) Fitoterapia, 66Zavala, M.A., Perez, S., Perez, C., Vargas, R., Perez, R.M., Antidiarrhoeal activity of Waltheria americana, Commelina coelestis and Alternanthera repens (1998) J Ethnopharmacol, 61Ragasa, C.Y., Tremor, N., Rideout, J.A., Iodone derivatives from Alternanthera sessilis (2002) J Asian Nat Prod Res, 4Edwin, D., Geetha, V.R., Vishwanathan, H., Rani, M.V.U., Studies on the mutagenic effects of Centella asiatica, Alternanthera sessilis and Embrica officinalis in somatic cells of mice (2000) J Environ Biol, 21Kumar, S., Bacchi, C.D., Darokar, M.P., Antibacterial activity observed in the seeds of some coprophilous plants (1997) Int J Pharmacog, 35Ali, A.M., Mackeen, M.M., El-sharlawy, S.H., Antiviral and cytotoxic activities of some plants used in Malaysian indigenous medicine (1996) Pertanika J Trop Agr Sci, 19Gupta, R.K., Sascena, V.K., Volatile constituents from the flowers of Alternanthera pungens H. B. K (1987) Indian Perfum, 31, pp. 366-369Lin, S.C., Lin, Y.H., Shyuu, S.J., Lin, C.C., Hepatoprotective effects of Taiwan folk medicine Alternanthera sessilis on liver damage induceg by various hepatotoxins (1994) Phytother Res, 8Aruna, K., Sivaramakrisham, V.M., Anticarcinogenic effects of some indian plant products (1992) Food Chem Toxicol, 30Mokkhasmit, M., Ngarmwathana, W., Sawasdimongkol, K., Permphiphat, V., Pharmacological evaluation of medicinal plants (1971) J Med Ass Thailand, 54Bhaskarachary, K., Rao, D.S.S., Deosthale, Y.G., Reddy, V., Carotene content of some common and less familiar foods of plants origin (1995) Food Chem, 54Sahu, B.R., Chakrabarty, A., A flavone glycoside, robinitin-7-O-β-D-glucopyranoside from Alternanthera sessilis (1993) Asian J Chem, 5Sridhar, R., Lakshminarayana, G., Lipid classes, fatty-acids and tocopherols of leaves of 6 edible plant species (1993) J Agr Food Chem, 41Baruah, P., Sarma, G.C., Study of amino acid composition of certain pollen grains (1984) J Paly Nol, 20Sinha, P., Arora, V.K., Wahi, S.P., Chemical investigation on Alternanthera sessilis R (1984) B. Indian Drugs, 21Ahmed, E.M., Bashir, A.K., El Kheir, Y.M., Investigations of molluscicidal activity of certain sudanese plants used in folkmedicine (1984) Part IV. Planta Med, 50Guerra, R.N.M., Pereira, H.A.W., Silveira, L.M.S., Olea, R.S.G., Immunomodulatory properties of Alternanthera tenella Colla aqueous extracts in mice (2003) Braz J Med Biol Res, 36Pomilio, A.B., Buschi, C.A., Sola, G.A.R., Rumi, L.S., Antitumor screening of Gomphrena species (1991) Fitoterapia, 62de Moura, R.M., Pereira, P.S., Januário, A.H., França, S.C., Dias, D.A., Antimicrobial screening and quantitative determination of benzoic acid derivative of Gomphrena celosioides by TLC-densitometry (2004) Chem Pharm Bull, 52, pp. 1342-1344Dhawan, B.N., Patnaik, G.K., Rastogi, R.P., Singh, K.K., Tandon, J.S., Screening of Indian plants for biological activity (1977) Indian J Exp Biol, 15Gbeassor, M., Kossou, Y., Amegbo, K., De Souza, C., Koumaglo, K., Antimalarial effects of eight African medicinal plants (1989) J Ethnopharmacol, 25Gessler, M.C., Nkunyak, M.H.H., Mwasumbi, L.B., Heinrich, M., Tanner, M., Screening Tanzanian medicinal plants for antimalarial

Antiproliferative Activity And Induction Of Apoptosis In Pc-3 Cells By The Chalcone Cardamonin From Campomanesia Adamantium (myrtaceae) In A Bioactivity-guided Study

The Myrtaceae family is a common source of medicines used in the treatment of numerous diseases in South America. In Brazil, fruits of the Campomanesia species are widely used to make liqueurs, juices and sweets, whereas leaves are traditionally employedas a medicine for dysentery, stomach problems, diarrhea, cystitis and urethritis. Ethanol extracts of Campomanesia adamantium (Myrtaceae) leaves and fruits were evaluated against prostate cancer cells (PC-3). The compound (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3- phenylprop-2-en-1-one, cardamonin) was isolated from ethanol extracts of C. adamantium leaves in a bioactivity-guided study and quantified by UPLC-MS/MS. In vitro studies showed that the isolated chalcone cardamonin inhibited prostate cancer cell proliferation and decreased the expression of NFkB1. Moreover, analysis by flow cytometry showed that this compound induced DNA fragmentation, suggesting an effect on apoptosis induction in the PC-3 cell line. © 2014 by the authors; licensee MDPI, Basel, Switzerland.19218431855Brandão, H.N., David, J.P., Couto, R.D., Nascimento, J.A.P., David, J.M., Química e farmacologia de quimioterápicos antineoplásicos derivados de plantas (2010) Quim. Nova, 33, pp. 1359-1369Newman, D.J., Cragg, G.M., Snader, K.M., Natural products as sources of new drugs over the period 1981-2002 (2003) J. Nat. Prod., 66, pp. 1022-1037Newman, D.J., Cragg, G.M., Snader, K.M., Natural products as sources of new drugs over the 30 years from 1981 to 2010 (2012) J. Nat. Prod., 75, pp. 311-335Stefanello, M.E.A., Pascoal, A.C.R.F., Salvador, M.J., Essential oils from neo-tropical myrtaceae: Chemical diversity and biological properties (2011) Chem. Biodivers., 8, pp. 73-94Lorenzi, H., Árvores brasileiras: Manual de identificação e cultivo de plantas arböreas nativas do brasil, 1st ed (2002) Editora Plantarum: Nova Odessa, p. 352. , BrazilPavan, F.R., Leite, C.Q.F., Coelho, R.G., Coutinho, I.D., Honda, N.K., Cardoso, C.A.L., Vilegas, W., Sato, D.N., Evaluation of anti-mycobacterium tuberculosis activity of campomanesia adamantium (myrtaceae (2009) Quim. Nova, 32, pp. 1222-1226Coutinho, I.D., Coelho, R.G., Kataoka, V.M.F., Honda, N.K., Silva, J.R.M., Vilegas, W., Cardoso, C.A.L., Determination of phenolic compounds and evaluation of antioxidant capacity of campomanesia adamantium leaves (2008) Ecletíca Quím., 33, pp. 53-60Pascoal, A.C.R.F., Erenfried, C.A., Eberlin, M.N., Stefanello, M.E.A., Salvador, M.J., Free radical scavenging activity, determination of phenolic compounds and hplc-dad/esi-ms profile of campomanesia adamantium leaves (2011) Nat. Prod. Commun., (6), pp. 969-972Ferreira, L.C., Grabe-Guimarães, A., De Paula, C.A., Michel, M.C.P., Guimarães, R.G., Rezende, S.A., De Souza-Filho, J.D., Guimarães, D.A.S., Anti-inflammatory and antinociceptive activities of campomanesia adamantium (2013) J. Ethnopharmacol., 145, pp. 100-108Zi, X., Simoneau, A.R., Flavokawain, A., A novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice (2005) Cancer Res., 65, pp. 3479-3486Solomon, V.R., Lee, H., Anti-breast cancer activity of heteroaryl chalcone derivatives (2012) Biomed. Pharmacother., 66, pp. 213-220Itokawa, H., Morita, M., Mihashi, S., Phenolic compounds from the rhizomes of alpinia speciosa (1981) Phytochemistry, 20, pp. 2503-2506Kamal, A., Mallareddy, A., Suresh, P., Shaik, T.B., Lakshma-Nayak, V., Kishor, C., Shetti, R.V., Ramakrishna, S., Synthesis of chalcone-amidobenzothiazole conjugates as antimitotic and apoptotic inducing agents (2012) Bioorg. Med. Chem., 20, pp. 3480-3492Baldwin, A.S., Series introduction: The transcription factor of nfk-b and humam disease (2001) J. Clin. Invest., 107, pp. 3-6Karin, M., Cao, Y., Greten, F.R., Li, Z.W., Nfk-b in cancer: From innocent bystander to major culprit (2002) Nat. Rev. Cancer, 2, pp. 301-310Luo, J.L., Maeda, S., Hsu, L.C., Yagita, H., Karin, M., Inhibition of nfk-b in cancer cells converts inflammation-induced tumor growth mediated by tnfa to trail-mediated tumor regression (2004) Cancer Cell., 6, pp. 297-305Sladkova, L.V., Moskaleva, E.V., Posypanova, G.A., Apoptosis of cells of different lines and the characteristics of internucleosomal dna fragmentation in cells: Connection with the cell cycle (2000) Tsitologiia, 42, pp. 309-313Rahman, M.A., Chalcone: A valuable insight into the recent advances and potential pharmacological activities (2011) Chem. Sci. J., 29, pp. 1-16Syam, S., Abdelwahab, S.I., Al-Mamary, M.A., Mohan, S., Synthesis of chalcones with anticancer activities (2012) Molecules, 17, pp. 6179-6195Szliszka, E., Czuba, Z.P., Mazur, B., Paradysz, A., Krol, W., Chalcones and dihydrochalcones augment trail-mediated apoptosis in prostate cancer cells (2010) Molecules, 15, pp. 5336-5353Simirgiotis, M.J., Adachi, S., To, S., Yanga, H., Reynertson, K.A., Basile, M., Gil, J.R.R., Kennellya, E.J., Cytotoxic chalcones and antioxidants from the fruits of syzygium samarangense wax jambu (2008) Food Chem., 107, pp. 813-819Park, S., Gwak, J., Han, S.J., Oh, S., Cardamonin suppresses the proliferation of colon cancer cells by promoting β-catenin degradation (2013) Biolog. Pharm. Bull., 36, pp. 1040-1044Qin, Y., Sun, C.Y., Lu, F.R., Shu, X.R., Yang, D., Chen, L., She, X.M., Hu, Y., Cardamonin exerts potent activity against multiple myeloma through blockade of nf-κb pathway in vitro Leuk. Res., 2012 (36), pp. 514-520Teodori, E., Dei, S., Scapecchi, S., Gualtieri, F., The medicinal chemistry of multidrug resistence reversing drugs (mrd (2002) Farmaco, 57, pp. 385-414Baguley, B.C., Multiple drug resistence mechanisms in cancer (2010) Mol. Biotechnol., 46, pp. 308-316Kale, A., Gawande, S., Kotwal, S., Cancer phytotherapeutics: Role for flavonoids at the cellular level (2008) Phytother. Res., 22, pp. 567-577Skehan, P., Storeng, R., Scudiero, D., Monks, A., Mcmahon, J., Vistica, D., Warren, J.T., Boyd, M.R., New colorimetric cytotoxicity assay for anticancer-drug screening (1990) J. Nat. Cancer Instit., 82, pp. 1107-1118Shoemaker, R.H., The nci60 human tumour cell line anticancer drug screen (2006) Nat. Rev. Cancer, 6, pp. 813-823Nicoletti-Carvalho, J.E., Nogueira, T.C.A., Gorjão, R., Bromati, C.R., Yamanaka, T.S., Boschero, A.C., Velloso, L.A., Bordin, S., Upr-mediated trib3 expression correlates with reduced akt phosphorylation and inability of interleukin 6 to overcome palmitate-induced apoptosis in rinm5f cells (2010) J. Endocrinol., 206, pp. 183-19

Bioactivity And Chemical Composition Of The Essential Oil From The Leaves Of Guatteria Australis A.st.-hil

Essential oil from the leaves of Guatteria australis was obtained by hydrodistillation, analyzed by Gas Chromatography coupled to Mass Spectromery (GC–MS) and their antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant activities were also evaluated. Twenty-three compounds were identified among which germacrene B (50.66%), germacrene D (22.22%) and (E)-caryophyllene (8.99%) were the main compounds. The highest antiproliferative activity was observed against NCI-ADR/RES (TGI = 31.08 μg/ml) and HT-29 (TGI = 32.81 μg/ml) cell lines. It also showed good antileishmanial activity against Leishmania infantum (IC50 = 30.71 μg/ml). On the other hand, the oil exhibited a small effect against Staphylococcus aureus ATCC 6538, S. aureus ATCC 14458 and Escherichia coli ATCC 10799 (MIC = 250 μg/ml), as well as small antioxidant activity (457 μmol TE/g) assessed through ORACFL assay. These results represent the first report regarding chemical composition and bioactivity of G. australis essential oil