Identification of S-3-(hexanal)-glutathione and its bisulfite adduct in grape juice from Vitis vinifera L. cv. Sauvignon blanc as new potential precursors of 3SH

Food Chemistry
Cécile ThibonDenis Dubourdieu

Abstract

Two main precursors (S-3-(hexan-1-ol)-l-cysteine and S-3-(hexan-1-ol)-l-glutathione) of 3-sulfanylhexanol (3SH, formerly named 3-mercaptohexanol) have been identified so far in grape juice but a correlation between precursor concentrations in grape juices and 3SH concentrations in wines is not always observed. This suggests that there may be other compounds associated with the aromatic potential. In this work, S-3-(hexanal)-glutathione (Glut-3SH-Al) and its bisulfite (Glut-3SH-SO3) adduct were identified in Sauvignon blanc grape juice by liquid chromatography coupled to Fourier transform mass spectrometry experiments. A partial purification of the compounds was carried out by Medium Pressure Liquid Chromatography (MPLC) on the reverse phase using 5L of grape juice. The addition of synthetized Glut-3SH-Al and Glut-3SH-SO3 in the synthetic medium induced a significant release of 3SH after fermentation. Moreover, we demonstrate that Glut-3SH-Al and its bisulfite adduct are present in grape juice and could be considered as new direct 3SH precursors with molar conversion yields close to 0.4%.

References

Oct 20, 2005·Journal of Bioscience and Bioengineering·Marina BelyDenis Dubourdieu
Jan 5, 2006·Journal of Agricultural and Food Chemistry·Takatoshi Tominaga, Denis Dubourdieu
Mar 5, 2010·Journal of Agricultural and Food Chemistry·Aurélie RolandRémi Schneider
Sep 10, 2010·Journal of Agricultural and Food Chemistry·Aurélie RolandFlorine Cavelier
Jan 18, 2011·Journal of Agricultural and Food Chemistry·Cécile ThibonDenis Dubourdieu
Apr 1, 2011·Journal of Agricultural and Food Chemistry·Dimitra L Capone, David W Jeffery
Mar 28, 2013·Journal of Agricultural and Food Chemistry·Michael J HarschJean-Michel Salmon
Sep 5, 2013·Food Chemistry·Peggy RigouAlain Razungles
Jun 4, 2015·FEMS Yeast Research·Margarita Santiago, Richard C Gardner

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Citations

Aug 9, 2016·BMC Plant Biology·Pierre HelwiCornelis van Leeuwen
Feb 22, 2017·Journal of Agricultural and Food Chemistry·Mango ParkerMarkus J Herderich
Oct 25, 2017·Critical Reviews in Food Science and Nutrition·Julie DrappierLaurence Geny-Denis
Dec 11, 2019·Biomolecules·Vicente Ferreira, Ricardo Lopez
Feb 23, 2020·Journal of the Science of Food and Agriculture·Giorgio NicoliniRoberto Larcher
Oct 17, 2017·Scientific Reports·Andreja VanzoKlemen Lisjak
Sep 1, 2020·Food Chemistry·Hugo BonnaffouxFlorine Cavelier
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jennifer R MuhlRebecca C Deed

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