Investigation into the formation of guaiacol conjugates in berries and leaves of grapevine Vitis vinifera L. Cv. cabernet sauvignon using stable isotope tracers combined with HPLC-MS and MS/MS analysis

J Agric Food Chem. 2010 Feb 24;58(4):2076-81. doi: 10.1021/jf903732p.


Fermentation of grapes that had been exposed to bushfire smoke can potentially yield unpalatable, smoke-affected wine. Guaiacol and its glucoconjugate were previously found in smoke-affected grapes at an elevated concentration. To find and identify further guaiacol conjugates in smoke-affected grapes, a stable isotope feeding experiment combined with extensive HPLC-MS and MS/MS investigations was carried out. Leaves and berries of a potted grapevine were placed in contact with an aqueous mixture of d(0)- and d(3)-guaiacol for 1-2 days and collected 5 weeks later. Screening for potential guaiacol conjugates in the leaves and berries was facilitated by monitoring the unique mass spectrometric signature of an isotopic doublet separated by 3 Da. Seven different conjugates were detected in leaves and berries and were tentatively identified as mono- and diglycosides of guaiacol. Quantitative analysis demonstrated that the guaiacol conjugates were translocated between leaves and berries to a very limited extent and were also present as low-level natural compounds of untreated leaves and berries. The same guaiacol conjugates were also found at a considerably elevated concentration in leaves and berries obtained from grapevines exposed to bushfire smoke.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Fruit / chemistry*
  • Glucosides / analysis
  • Glucosides / isolation & purification
  • Guaiacol / analysis*
  • Guaiacol / isolation & purification
  • Isotope Labeling
  • Mass Spectrometry / methods
  • Plant Leaves / chemistry*
  • Smoke
  • Spectrum Analysis / methods
  • Vitis / chemistry*
  • Wine / analysis*


  • Glucosides
  • Smoke
  • Guaiacol