Artículos de revistas
Asymmetric Total Synthesis And Antiproliferative Activity Of Goniothalamin Oxide Isomers
Registro en:
Bioorganic Chemistry. , v. 37, n. 2, p. 52 - 56, 2009.
452068
10.1016/j.bioorg.2008.12.001
2-s2.0-62749179591
Autor
Marquissolo C.
Fatima A.d.
Kohn L.K.
Ruiz A.L.T.G.
Carvalho J.E.d.
Pilli R.A.
Institución
Resumen
Goniothalamin oxide (1) is a styryl lactone which was isolated from bark and leaves of several Goniothalamus species. This natural product has some interesting biological properties such as larvicidal and tripanocidal activities. However, no studies on the antiproliferative profile of goniothalamin oxide (1) and its stereoisomers have been reported yet. Here, goniothalamin epoxide (1), isogoniothalamin epoxide (2) and their enantiomers were prepared via epoxidation of (R)-and (S)-goniothalamin (4). A 3:2 molar ratio in favor of goniothalamin oxide (1) and ent-1 was observed from (R)- and (S)-4, respectively, when 3-chloroperbenzoic acid (mCPBA) was employed while an increase to 6:1 molar ratio was achieved with (S,S)-Jacobsen's catalyst. Antiproliferative activity of these epoxides revealed that ent-isogoniothalamin oxide (ent-2) was the most active against the eight cancer cell lines studied. These results indicate that 6S, 7R and 8R absolute configurations are beneficial for the activity of these epoxides. © 2009. 37 2 52 56 Blázquez, M.A., Bermejo, A., Zafra-Polo, M.C., Cortes, D., (1999) Phytochem. Anal., 10, pp. 161-170 de Fátima, A., Modolo, L.V., Conegero, L.S., Pilli, R.A., Ferreira, C.V., Kohn, L.K., de Carvalho, J.E., (2006) Curr. Med. Chem., 13, pp. 3371-3384 de Fátima, A., Zambuzzi, W.F., Modolo, L.V., Tarsitano, C.A.B., Gadelha, F.R., Hyslop, S., de Carvalho, J.E., Pilli, R.A., (2008) Chem. Biol. Int., 176, pp. 143-150 Martins, C.V.B., de Resende, M.A., Magalhães, T.F.F., Lima, B.H.S., Watanabe, G.A., Ruiz, A.L.T.G., de Carvalho, J.E., de Fátima, A., (2008) Lett. Drug. Des. Discov., 5, pp. 74-78 Sam, T.W., Sew-Yeu, C., Matsjeh, S., Gan, E.K., Razak, D., Mohamed, A.L., (1987) Tetrahedron Lett., 28, pp. 2541-2544 Lan, Y.H., Chang, F.R., Yu, J.H., Yang, Y.L., Chang, Y.L., Lee, S.J., Wu, Y.C., (2003) J. Nat. Prod., 66, pp. 487-490 Goh, S.H., Ee, G.C.L., Chuah, C.H., Wei, C., (1995) Aust. J. Chem., 48, pp. 199-205 de Fátima, A., Marquissolo, C., de Albuquerque, S., Carraro-Abrahão, A.A., Pilli, R.A., (2006) Eur. J. Med. Chem., 41, pp. 1210-1213 Blagosklonny, M.V., (2005) Cell Cycle, 4, pp. 1518-1521 Weisz, B., Meirow, D., Schiff, E., Lishner, M., (2004) Expert Rev. Anticancer Ther., 4, pp. 889-902 Fuganti, C., Pedrocchi-Fantoni, G., Sarra, S., Servi, S., (1994) Tetrahedron: Asymmetry, 5, pp. 1135-1138 Surivet, J.-P., Vatèle, J.-M., (1999) Tetrahedron, 55, pp. 13011-13028 Peng, X., Li, A., Shen, H., Wu, T., Pan, X., (2002) J. Chem. Res.(S), pp. 330-332 Pospíšil, J., Markó, I.E., (2006) Tetrahedron Lett., 47, pp. 5933-5937 Bose, D.S., Reddy, A.V.N., Srikanth, B., (2008) Synthesis, pp. 2323-2326 Monks, A., Scudeiro, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Boyd, M., (1991) J. Nat. Can. Inst., 83, pp. 757-766 de Fátima, A., Pilli, R.A., (2003) Tetrahedron Lett., 44, pp. 8721-8724 de Fátima, A., Pilli, R.A., (2003) Arkivoc, 10, pp. 118-126 de Fátima, A., Kohn, L.K., Antônio, M.A., de Carvalho, J.E., Pilli, R.A., (2004) Bioorg. Med. Chem., 12, pp. 5437-5442 de Fátima, A., Kohn, L.K., de Carvalho, J.E., Pilli, R.A., (2006) Bioorg. Med. Chem., 14, pp. 622-631 Jacobsen, E.N., Zhang, W., Muci, A.R., Ecker, J.R., Deng, L., (1991) J. Am. Chem. Soc., 113, pp. 7063-7064 Hosoya, N., Irie, R., Katsuki, T., (1993) Synlett, pp. 261-263