Bioactive Nitrosylated and Nitrated -(2-hydroxyphenyl)acetamides and Derived Oligomers: An Alternative Pathway to 2-Amidophenol-Derived Phytotoxic Metabolites.

Incubation of , , and MPI764 with the microbial 2-benzoxazolinone (BOA)-degradation-product -acetamido-phenol, produced from 2-aminophenol, led to the recently identified -(2-hydroxy-5-nitrophenyl) acetamide, to the hitherto unknown (2-hydroxy-5-nitrosophenyl)acetamide, and to (2-hydroxy-3-nitrophenyl)acetamide. As an alternative to the formation of phenoxazinone derived from aminophenol, dimers- and trimers-transformation products have been found. Identification of the compounds was carried out by LC/HRMS and MS/MS and, for the new structure (2-hydroxy-5-nitrosophenyl)acetamide, additionally by 1D- and 2D-NMR. Incubation of microorganisms, such as the soil bacteria , MPI763, the yeast and and the plants var. L. (kohlrabi) and Col-0, with -(2-hydroxy-5-nitrophenyl) acetamide, led to its glucoside derivative as a prominent detoxification product; in the case of , this was together with the corresponding glucoside succinic acid ester. In contrast, consortium synthesized 2-acetamido-4-nitrophenyl sulfate. 1 mM bioactive -(2-hydroxy-5-nitrophenyl) acetamide elicits alterations in the expression profile of several genes. The most responsive upregulated gene was pathogen-inducible terpene synthase The bioactivity of the compound is rapidly annihilated by glucosylation.