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

Org Lett. 2019 Oct 4;21(19):7841-7845. doi: 10.1021/acs.orglett.9b02833. Epub 2019 Sep 13.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoimidazole Carboxamide / analogs & derivatives*
  • Aminoimidazole Carboxamide / chemistry
  • Aminoimidazole Carboxamide / metabolism
  • Models, Molecular
  • Molecular Structure
  • Oryza / chemistry*
  • Oryza / metabolism
  • Ribonucleosides / chemistry*
  • Ribonucleosides / metabolism
  • Ribonucleotides / chemistry*
  • Ribonucleotides / metabolism

Substances

  • Ribonucleosides
  • Ribonucleotides
  • imidazole-4-carboxamide
  • Aminoimidazole Carboxamide