Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

• Published in: Journal of natural products (Washington, D.C.) Vol. 54; no. 3; pp. 774 - 784
• Main Authors: McInerney, Bernie V, Gregson, Richard P, Lacey, Michael J, Akhurst, Raymond J, Lyons, Graham R, Rhodes, Stuart H, Smith, Donald R. J, Engelhardt, Lutz M, White, Allan H
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.05.1991
• Subjects: Anti-Bacterial Agents - isolation & purification; Enterobacteriaceae - isolation & purification; Fermentation; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Pyrrolidinones - isolation & purification; Pyrrolidinones - pharmacology
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np50075a005

Five related antibiotic compounds, named xenorhabdins, were isolated from cultures of Xenorhabdus spp., bacteria symbiotically associated with insect-pathogenic nematodes. Their chemical structures were elucidated by X-ray crystallography, nmr, and mass spectral analyses to be N-acyl derivatives of either 6-amino-4,5-dihydro-5-oxo-1,2-dithiolo [4,3-b] pyrrole (compounds 1-3) or 6-amino-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b] pyrrole (compounds 4 and 5). They are previously unreported members of the pyrrothine family of antibiotics. Antimicrobial and insectidical activities were found. These metabolites are specific to phase one Xenorhabdus.