Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides

J Am Chem Soc. 2005 Mar 2;127(8):2414-6. doi: 10.1021/ja0452166.

Abstract

Many phytopathogenic bacteria display lipopolysaccharides (LPS) with the O-chain repeating unit [alpha-l-Rha-(1-->3)-alpha-l-Rha-(1-->3)-alpha-l-Rha-(1-->2)](n)(). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabidopsis / drug effects
  • Arabidopsis / genetics
  • Arabidopsis / immunology
  • Arabidopsis / microbiology
  • Arabidopsis Proteins / biosynthesis
  • Arabidopsis Proteins / genetics
  • Carbohydrate Sequence
  • Deoxy Sugars / chemistry
  • Deoxy Sugars / pharmacology
  • Gene Expression / drug effects
  • Mannans / chemistry
  • Mannans / pharmacology
  • Models, Molecular
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • O Antigens / chemistry*
  • O Antigens / pharmacology*
  • Plant Diseases / genetics
  • Plant Diseases / microbiology*
  • Pseudomonas syringae / immunology
  • Pseudomonas syringae / pathogenicity*
  • Structure-Activity Relationship

Substances

  • Arabidopsis Proteins
  • Deoxy Sugars
  • Mannans
  • O Antigens
  • rhamnan
  • PR-1 protein, Arabidopsis