Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/55104
Type: Artigo de periódico
Title: Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers
Author: Marquissolo, C
de Fatima, A
Kohn, LK
Ruiz, ALTG
de Carvalho, JE
Pilli, RA
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 anti proliferative 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. Anti proliferative 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. (C) 2009 Published by Elsevier Inc.
Subject: Goniothalamin oxides
Enantiomers
Epoxidation
Antiproliferative activity
Cancer cells
Country: EUA
Editor: Academic Press Inc Elsevier Science
Rights: fechado
Identifier DOI: 10.1016/j.bioorg.2008.12.001
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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