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The pyrrolobenzodiazepine tilivalline ( 1 ) was originally identified in the human gut pathobiont  Klebsiella oxytoca , the causative agent of antibiotic-associated hemorrhagic colitis. Here we show the identification of tilivalline and analogs thereof in the entomopathogenic bacterium  Xenorhabdus eapokensis  as well as the identification of its biosynthesis gene cluster encoding a bimodular non-ribosomal peptide synthetase. Heterologous expression of both genes in  E .  coli  resulted in the production of  1  and from mutasynthesis and precursor directed biosynthesis 11 new tilivalline analogs were identified in  X .  eapokensis . These results allowed the prediction of the tilivalline biosynthesis being similar to that in  K .  oxytoca .

The benzodiazepine-like natural product tilivalline is produced by the entomopathogenic bacterium Xenorhabdus eapokensis