3-Hydroxy-3-(2-oxopropyl)indolin-2-one, a product of a human-derived Enterocloster strain, is an inhibitor of nitric oxide production

Biosci Biotechnol Biochem. 2024 Feb 21;88(3):316-321. doi: 10.1093/bbb/zbad172.

Abstract

When cultured anaerobically, Enterocloster sp. RD014215 was found to produce 1. Using nuclear magnetic resonance and mass spectroscopy, the planar structure of 1 was determined to be 3-hydroxy-3-(2-oxopropyl)indolin-2-one. The chirality of 1 was implied as S by comparing the optical rotation value of 1 with literature reports of the synthesized compounds. To our knowledge, this work represents the first discovery of the metabolite produced by Enterocloster strain. 1 exhibited inhibition of nitric oxide (NO) production, demonstrating a 50% inhibitory activity (IC50) of 34 µm for NO production by murine macrophage cells subjected to lipopolysaccharide stimulation.

Keywords: enterocloster; gut microbiome; immunity; metabolite; nitric oxide (NO).

MeSH terms

  • Animals
  • Humans
  • Indoles / metabolism
  • Indoles / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages* / metabolism
  • Mice
  • Nitric Oxide Synthase Type II
  • Nitric Oxide* / metabolism

Substances

  • Nitric Oxide
  • indolin-2-one
  • Nitric Oxide Synthase Type II
  • Indoles
  • Lipopolysaccharides