First identification of 4-S-glutathionyl-4-methylpentan-2-one, a potential precursor of 4-mercapto-4-methylpentan-2-one, in Sauvignon Blanc juice

J Agric Food Chem. 2009 Feb 11;57(3):991-5. doi: 10.1021/jf802799w.

Abstract

The identification of 4-S-glutathionyl-4-methylpentan-2-one (glut-4-MMP) by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) experiments in a Sauvignon Blanc juice extract is described. Synthesis of an authentic reference compound enabled confirmation of the presence of glut-4-MMP in a Sauvignon Blanc juice for the first time. The juice extract was obtained by batch-wise percolation of 6 L of juice through a sintered glass funnel packed with C18 sorbent, followed by further purification using low-pressure chromatography on C18. Analysis of the juice extract revealed a chromatographic peak with the same retention time and mass spectrum as the synthetic reference compound, and spiking experiments verified the findings. The presence of glut-4-MMP in grape juice may be related to the biosynthesis of the relevant S-cysteinyl conjugate and, subsequently, to the formation of aroma-active 4-mercapto-4-methylpentan-2-one (4-MMP). This compound has a very low reported sensory threshold (3 ng/L) in wine and is partially responsible for the aromas that are important to the quality and style of some wine varieties.

MeSH terms

  • Beverages / analysis*
  • Chromatography, High Pressure Liquid
  • Fruit / chemistry*
  • Glutathione / analogs & derivatives*
  • Glutathione / analysis
  • Odorants / analysis
  • Pentanones / analysis*
  • Plant Extracts / chemistry
  • Sulfhydryl Compounds / analysis*
  • Tandem Mass Spectrometry
  • Vitis / chemistry*

Substances

  • 4-S-glutathionyl-4-methylpentan-2-one
  • 4-mercapto-4-methyl-pentan-2-one
  • Pentanones
  • Plant Extracts
  • Sulfhydryl Compounds
  • Glutathione