Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

• Friederike I. Nollmann,
• Andrea Dowling,
• Marcel Kaiser,
• Klaus Deckmann,
• Sabine Grösch,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

• -60590 Frankfurt a. M., Germany 10.3762/bjoc.8.60 Abstract The synthesis of the recently characterized depsipeptide szentiamide (1), which is produced by the entomopathogenic bacterium Xenorhabdus szentirmaii, is described. Whereas no biological activity was previously identified for 1, the material

• derived from the efficient synthesis enabled additional bioactivity tests leading to the identification of a notable activity against insect cells and Plasmodium falciparum, the causative agent of malaria. Keywords: cyclic depsipeptide; esterification; natural product; szentiamide; Xenorhabdus

• ], xenematide [8] and the GameXPeptides [9]. Analysis of the genome sequences of the fully sequenced members of Xenorhabdus and Photorhabdus [10][11] has revealed that several additional compounds and especially even much larger compounds await isolation and structure elucidation. Recently, szentiamide (1) has