title: 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.
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%.
authors.affiliation: INRA, ISVV, USC 1366 Œnologie, FR-33140 Villenave d'Ornon, France; Univ. de Bordeaux, ISVV, EA4577 Œnologie, FR-33140 Villenave d'Ornon, France. Electronic address: cecile.thibon@u-bordeaux.fr.
authors.forename: Cécile
authors.initials: C
authors.lastname: Thibon
authors.affiliation: Univ. de Bordeaux, ISVV, EA4577 Œnologie, FR-33140 Villenave d'Ornon, France; Biolaffort, F33100 Bordeaux, France.
authors.forename: Caroline
authors.initials: C
authors.lastname: Böcker
authors.affiliation: Univ. de Bordeaux, Bordeaux Sciences Agro, CS 40201, Bordeaux FR-33000, France.
authors.forename: Svitlana
authors.initials: S
authors.lastname: Shinkaruk
authors.affiliation: Biolaffort, F33100 Bordeaux, France.
authors.forename: Virginie
authors.initials: V
authors.lastname: Moine
authors.affiliation: Univ. de Bordeaux, ISVV, EA4577 Œnologie, FR-33140 Villenave d'Ornon, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Darriet
authors.affiliation: Univ. de Bordeaux, ISVV, EA4577 Œnologie, FR-33140 Villenave d'Ornon, France.
authors.forename: Denis
authors.initials: D
authors.lastname: Dubourdieu
mesh_terms: D000447:Aldehydes / Q000032:analysis / Q000737:chemistry*; D001628:Beverages; D005285:Fermentation; D005978:Glutathione / Q000032:analysis / Q000737:chemistry*; D013447:Sulfites / Q000737:chemistry*; D027843:Vitis / Q000737:chemistry*; D014920:Wine / Q000032:analysis*
chemical_list: D000447:Aldehydes; D013447:Sulfites; C010463:n-hexanal; D005978:Glutathione; C042345:hydrogen sulfite
keywords: 3-Sulfanylhexan-1-ol (PubChem CID: 521348); 3-Sulfanylhexanol; Fractionation; Identification; LC–FTMS; Sauvignon blanc; Thiol precursor