Characterisation of taxlllaids A-G; natural products from Xenorhabdus indica.
2014
Kronenwerth, Max | Bozhüyük, Kenan a J | Kahnt, Astrid S | Steinhilber, Dieter | Gaudriault, Sophie | Kaiser, Marcel | Bode, Helge B | Merck Stiftungsprofessur für Molekulare Biotechnologie ; Goethe University Frankfurt = Goethe-Universität Frankfurt am Main | Institut für pharmazeutische Chemie ; Goethe University Frankfurt = Goethe-Universität Frankfurt am Main | Goethe University Frankfurt = Goethe-Universität Frankfurt am Main | Diversité, Génomes & Interactions Microorganismes - Insectes [Montpellier] (DGIMI) ; Institut National de la Recherche Agronomique (INRA)-Université Montpellier 2 - Sciences et Techniques (UM2)-Université de Montpellier (UM) | Parasite Chemotherapy ; Swiss Tropical and Public Health Institute [Basel]
Six new lipodepsipeptides and an additional linear derivative named taxlllaids A-G (1-7) have been identified in the entomopathogenic bacterium Xenorhabdus indica. The structures of the main compounds have been solved by detailed NMR spectroscopic analysis and the structures of minor derivatives were elucidated by a combination of labelling experiments and detailed MS experiments. The absolute configuration of the taxlllaids was deduced by using the advanced Marfey method and analysis of the biosynthesis gene cluster showing the presence of epimerisation domains, which was subsequently proved to be correct by solid-phase peptide synthesis of all taxlllaids. The exchange of a single amino acid in the adenylation domain was shown to be responsible for substrate promiscuity of the third A domain, resulting in the incorporation of leucine, phenylalanine or tyrosine. Bioactivity testing revealed the taxlllaids to be weakly active against Plasmodium falciparum and against a number of eukaryotic cell lines.
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