Ribosides and Ribotide of a Fairy Chemical, Imidazole-4-carboxamide, as Its Metabolites in Rice

The metabolism of imidazole-4-carboxamide (ICA) in plants has been unknown. Two metabolites (1 and 2) were isolated from ICA-treated rice, and their structures were determined by spectroscopic analysis including the single-crystal X-ray diffraction technique and synthesis. The ribotide of ICA (3), whose existence was predicted, was also synthesized and detected from the treated rice by LC–MS/MS. These results indicated that rice might interconvert ICA, 1, and 3 to regulate the biological activity.