Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/198663
Type: Artigo de periódico
Title: Asymmetric Total Synthesis And Antiproliferative Activity Of Goniothalamin Oxide Isomers.
Author: Marquissolo, Cilene
de Fátima, Angelo
Kohn, Luciana K
Ruiz, Ana Lúcia T G
de Carvalho, João Ernesto
Pilli, Ronaldo A
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.
Subject: Antineoplastic Agents
Catalysis
Cell Line, Tumor
Chlorobenzoates
Drug Screening Assays, Antitumor
Epoxy Compounds
Humans
Pyrones
Stereoisomerism
Rights: fechado
Identifier DOI: 10.1016/j.bioorg.2008.12.001
Address: http://www.ncbi.nlm.nih.gov/pubmed/19185327
Date Issue: 2009
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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