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BIBTEX RIS

Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum

2009; Brazilian Chemical Society; Volume: 20; Issue: 4 Linguagem: Inglês

10.1590/s0103-50532009000400014

1678-4790

M. H. Kossuga, Simone Possedente de Lira, Shayna McHugh, Yohandra Reyes Torres, Bruna de Araújo Lima, Reginaldo Bruno Gonçalves, Katyuscya Veloso, Antônio G. Ferreira, Rosana Moreira da Rocha, Roberto G. S. Berlinck,

Synthesis and Catalytic Reactions

The chemical investigation of the crude extract of an ascidian of the genus Didemnumled to the isolation of the modified diketopiperazine rodriguesines A (1) and (2) as a mixture of homologues, which could be identified by analysis of spectroscopic data including MS/MS experiments. The investigation of a second Didemnumsp. led to the isolation of N-acetyl-rodriguesine A (3) and N-acetyl-rodriguesine B (4). The absolute configuration of compounds 1and 2could be established by hydrolysis and Marfey's analysis and comparison with literature data reported for compound 3, previously obtained as a synthetic product. The mixture of 1and 2displayed moderate antibiotic activity against a clinical isolate of Streptococcus mutansand against S. mutansUA159 and Staphylococcus aureusATCC6538.