Incubation of
Aminobacter aminovorans,
Paenibacillus polymyxa, and
Arthrobacter MPI764 with the microbial 2-benzoxazolinone (BOA)-degradation-product
2-acetamido-phenol, produced from 2-aminophenol, led to the recently identified
N-(2-hydroxy-5-nitrophenyl) acetamide, to the hitherto unknown
N-(2-hydroxy-5-nitrosophenyl)acetamide, and to
N-(2-hydroxy-3-nitrophenyl)acetamide. As an alternative to
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Incubation of
Aminobacter aminovorans,
Paenibacillus polymyxa, and
Arthrobacter MPI764 with the microbial 2-benzoxazolinone (BOA)-degradation-product
2-acetamido-phenol, produced from 2-aminophenol, led to the recently identified
N-(2-hydroxy-5-nitrophenyl) acetamide, to the hitherto unknown
N-(2-hydroxy-5-nitrosophenyl)acetamide, and to
N-(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
N-(2-hydroxy-5-nitrosophenyl)acetamide, additionally by 1D- and 2D-NMR. Incubation of microorganisms, such as the soil bacteria
Pseudomonas laurentiana,
Arthrobacter MPI763, the yeast
Papiliotrema baii and
Pantoea ananatis, and the plants
Brassica oleracea var.
gongylodes L. (kohlrabi) and
Arabidopsis thaliana Col-0, with
N-(2-hydroxy-5-nitrophenyl) acetamide, led to its glucoside derivative as a prominent detoxification product; in the case of
Pantoea ananatis, this was together with the corresponding glucoside succinic acid ester. In contrast,
Actinomucor elegans consortium synthesized 2-acetamido-4-nitrophenyl sulfate. 1 mM bioactive
N-(2-hydroxy-5-nitrophenyl) acetamide elicits alterations in the
Arabidopsis thaliana expression profile of several genes. The most responsive upregulated gene was pathogen-inducible terpene synthase
TPS04. The bioactivity of the compound is rapidly annihilated by glucosylation.
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