Erysiopeptides A−D, Lipopeptides from the Marine Bacterium Vibrio sp. AFB22-4MB1

Abstract

Four new lipopeptides, erysiopeptides A−D, were isolated from the marine bacterium Vibrio sp. AFB22-4MB1. Their planar structures were elucidated on the basis of comprehensive spectroscopic analyses. A candidate biosynthetic gene cluster (BGC) for their production, encoding a non-ribosomal peptide synthetase, was identified in the genome sequence, and a corresponding biosynthetic proposal was developed. The absolute configurations of the component amino acids were established by advanced Marfey’s analysis and corroborated by bioinformatic predictions from the BGC. The stereochemistry of the β-hydroxyl group in the fatty chain was determined by derivatization of the hydrogenated product. Erysiopeptides exhibited moderate iron chelating as well as antibacterial activity against the Gram-positive bacterium Bacillus subtilis.