New tridecapeptides of the theonellapeptolide family from the Indonesian sponge Theonella swinhoei

• Annamaria Sinisi,
• Barbara Calcinai,
• Carlo Cerrano,
• Henny A. Dien,
• Angela Zampella,
• Claudio D’Amore,
• Barbara Renga,
• Stefano Fiorucci and
• Orazio Taglialatela-Scafati

Beilstein J. Org. Chem. 2013, 9, 1643–1651, doi:10.3762/bjoc.9.188

• hepatic carcinoma cell line. Keywords: antiproliferative activity; cyclic peptides; marine metabolites; theonellapeptolides; 2D NMR; Introduction Three decades of extensive chemical investigation [1] have clearly evidenced that marine sponges of the genus Theonella (Lithistida, Theonellidae) are

• theonellapeptolides (cyclic tridecapeptides including several N-methylated and D-amino acids) [17]. In the context of our long-standing interest for bioactive secondary metabolites from marine invertebrates, we have recently investigated a specimen of T. swinhoei collected off the coasts of Manado (North Sulawesi

• report the results of the chemical analysis of the polypeptide-containing fraction, which resulted in the isolation of two new theonellapeptolides, namely sulfinyltheonellapeptolide (2) and theonellapeptolide If (3) (Figure 2). We describe the structural elucidation of these new metabolites and the