Title of article :
Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers
Author/Authors :
Marquissolo، نويسنده , , Cilene and Fلtima، نويسنده , , آngelo de and Kohn، نويسنده , , Luciana K. and Ruiz، نويسنده , , Ana Lْcia T.G. and Carvalho، نويسنده , , Joمo Ernesto de and Pilli، نويسنده , , Ronaldo A.، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2009
Abstract :
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.
Keywords :
Enantiomers , Antiproliferative activity , epoxidation , Cancer cells , Goniothalamin oxides
Journal title :
Bioorganic Chemistry: an International Journal
Journal title :
Bioorganic Chemistry: an International Journal