Eco-friendly bioherbicides are urgently needed for managing the problematic weed . A mass spectrometry- and bioassay-guided screening approach was employed to identify phytotoxic secondary metabolites from fungi for the development of such bioherbicides. This effort led to the discovery of six phytotoxic 16-residue peptaibols, including five new compounds (-) and a known congener (), from sp. XJ1056. Their planar structures were elucidated through the analysis of tandem mass and NMR spectroscopic data. The absolute configurations of the chiral amino acids were determined by advanced Marfey's method and chiral-phase liquid chromatography-mass spectrometry (LC-MS) analysis. Bioinformatic analysis and targeted gene disruption identified the biosynthetic gene cluster for these peptaibols. Compounds and significantly inhibited the radicle growth of seedlings, and demonstrated potent postemergence herbicidal activity against while exhibiting minimal toxicity to . Structure-activity relationship analysis underscored the importance of -4-hydroxy-l-prolines at both the 10th and 13th positions for the herbicidal activities of these peptaibols.
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