New nitrogen-containing metabolites from cultures of rice false smut pathogen Villosiclava virens

Nat Prod Res. 2021 Jan;35(2):272-281. doi: 10.1080/14786419.2019.1627354. Epub 2019 Jun 10.

Abstract

Two new nitrogen-containing metabolites methyl N-acetyl-O-(4-acetylphenyl)-L-homoserinate (1), dimethyl (1H-indole-3-carbonyl)-D-glutamate (2), and two new natural products, 1,2-O-isopropylidene-D-mannitol (3), N-acetyl-β-methyl-L-phenylalanine (4), along with five known compounds (5-9) were isolated from the rice false smut pathogen Villosiclava virens UV-8b cultured in the solid rice medium. The structures were elucidated by spectroscopic analysis and by comparison of their physical and spectroscopic data with the literature. These metabolites were evaluated for their antibacterial and phytotoxic activities. Compounds 5-7 showed weak inhibition against the tested bacteria, while compounds 4-6 and 9 displayed inhibitory activity against the radicle elongation of rice seeds.

Keywords: Rice false smut; Villosiclava virens; antibacterial activity; nitrogen-containing metabolites; phytotoxic activity.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Hypocreales / metabolism*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nitrogen / chemistry
  • Oryza / drug effects
  • Oryza / microbiology*
  • Plant Diseases / microbiology
  • Seeds / drug effects
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Nitrogen

Supplementary concepts

  • Ustilaginoidea virens