Structural Diversification of Pyrazinone Metabolites via Spontaneous Oxa-Michael Addition in Staphylococcus xylosus

J Nat Prod. 2024 Jul 26;87(7):1881-1887. doi: 10.1021/acs.jnatprod.4c00252. Epub 2024 Jul 1.

Abstract

A family of pyrazinone metabolites (1-11) were characterized from Staphylococcus xylosus ATCC 29971. Six of them were hydroxylated or methoxylated, which were proposed to be produced by the rare noncatalytic oxa-Michael addition reaction with a water or methanol molecule. It was confirmed that isopropyl alcohol can also be the Michael donor of the reaction. 1-7 and the synthetic precursor 2a showed significant inhibition of breast cancer cell migration.

MeSH terms

  • Cell Movement / drug effects
  • Humans
  • Molecular Structure
  • Pyrazines* / chemistry
  • Pyrazines* / pharmacology
  • Staphylococcus* / drug effects

Substances

  • Pyrazines
  • N-(tert-butyl)hydroxylamine