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

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.