Artículos de revistas
Asymmetric Total Synthesis And Antiproliferative Activity Of Goniothalamin Oxide Isomers.
Registro en:
Bioorganic Chemistry. v. 37, n. 2, p. 52-6, 2009-Apr.
1090-2120
10.1016/j.bioorg.2008.12.001
19185327
Autor
Marquissolo, Cilene
de Fátima, Angelo
Kohn, Luciana K
Ruiz, Ana Lúcia T G
de Carvalho, João Ernesto
Pilli, Ronaldo 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. 37 52-6