Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum

Abstract

The chemical investigation of the crude extract of an ascidian of the genus Didemnum led 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 Didemnum sp. led to the isolation of N-acetyl-rodriguesine A (3) and N-acetyl-rodriguesine B (4). The absolute configuration of compounds 1 and 2 could 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 1 and 2 displayed moderate antibiotic activity against a clinical isolate of Streptococcus mutans and against S. mutans UA159 and Staphylococcus aureus ATCC6538. ©2009 Sociedade Brasileira de Química.