Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions

Biotechnol Lett. 2012 Jul;34(7):1351-6. doi: 10.1007/s10529-012-0909-4. Epub 2012 Mar 29.

Abstract

Nicotiana tabacum cell suspensions, 2 g wet wt/ml, rapidly took up 1 mM isonitrosoacetophenone (INAP), a plant-derived stress metabolite with anti-oxidative and anti-fungal properties, producing 4'-hexopyranosyloxy-3'-methoxyisonitrosoacetophenone in 54 % yield over 18 h. Unconverted INAP was at 33 μM. UPLC-MS/MS analyses with MassFragment software were used for metabolite identification. INAP had been hydroxylated at its meta- and para-positions as well as undergoing subsequent methoxylation and glycosylation. INAP is thus recognized by the enzymatic machinery of the phenylpropanoid pathway and is converted to a molecule with a substitution pattern similar to ferulic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Cells, Cultured
  • Chromatography, Liquid
  • Nicotiana / metabolism*
  • Phenylglyoxal / analogs & derivatives*
  • Phenylglyoxal / metabolism
  • Tandem Mass Spectrometry

Substances

  • isonitrosoacetophenone
  • Phenylglyoxal