Cyclic, Hydrophobic Hexapeptide Fusahexin Is the Product of a Nonribosomal Peptide Synthetase in Fusarium graminearum

J Nat Prod. 2021 Aug 27;84(8):2070-2080. doi: 10.1021/acs.jnatprod.0c00947. Epub 2021 Jul 22.

Abstract

The plant pathogenic fungus Fusarium graminearum is known to produce a wide array of secondary metabolites during plant infection. This includes several nonribosomal peptides. Recently, the fusaoctaxin (NRPS5/9) and gramilin (NRPS8) gene clusters were shown to be induced by host interactions. To widen our understanding of this important pathogen, we investigated the involvement of the NRPS4 gene cluster during infection and oxidative and osmotic stress. Overexpression of NRPS4 led to the discovery of a new cyclic hexapeptide, fusahexin (1), with the amino acid sequence cyclo-(d-Ala-l-Leu-d-allo-Thr-l-Pro-d-Leu-l-Leu). The structural analyses revealed an unusual ether bond between a proline Cδ to Cβ of the preceding threonine resulting in an oxazine ring system. The comparative genomic analyses showed that the small gene cluster only encodes an ABC transporter in addition to the five-module nonribosomal peptide synthetase (NRPS). Based on the structure of fusahexin and the domain architecture of NRPS4, we propose a biosynthetic model in which the terminal module is used to incorporate two leucine units. So far, iterative use of NRPS modules has primarily been described for siderophore synthetases, which makes NRPS4 a rare example of a fungal nonsiderophore NRPS with distinct iterative module usage.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Cluster Analysis
  • Computational Biology
  • Fungal Proteins / genetics
  • Fungal Proteins / metabolism*
  • Fusarium / enzymology*
  • Fusarium / genetics
  • Molecular Structure
  • Multigene Family
  • Peptide Synthases / genetics
  • Peptide Synthases / metabolism*
  • Peptides / metabolism*
  • Triticum / microbiology

Substances

  • Fungal Proteins
  • Peptides
  • Peptide Synthases
  • non-ribosomal peptide synthase

Supplementary concepts

  • Fusarium graminearum