title: Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners.
abstract: Volatile and non-volatile molecules are directly responsible for the thrill and excitement provided by wine-tasting. Their elucidation requires powerful analytical techniques and innovative methodologies. In a recent work, two novel sweet compounds called quercotriterpenosides (QTT) were identified in oak wood used for wine-ageing. The aim of the present study is to discover structural analogs of such natural sweeteners in oak wood. For this purpose, an analytical approach was developed as an alternative to chemical synthesis. Orbitrap mass spectrometry proved to be a crucial technique both to demonstrate the presence of QTT analogs in oak wood by targeted screening and to guide the purification pathway of these molecules using complementary chromatographic tools. Four compounds were isolated and identified for the first time: two isomers, one glucosyl derivative and one galloyl derivative of QTT. Their tasting showed that only the two new isomers were sweet, thus demonstrating both the pertinence of the strategy and the influence of functional groups on gustatory properties. Finally, this paper presents some developments involving multistage Fourier transform mass spectrometry (FTMS) to provide solid structural information on these functional groups prior to any purification of compounds. Such analytical developments could be particularly useful for research on taste-active or bio-active products.
authors.affiliation: Univ. de Bordeaux, ISVV, EA 4577, Unité de recherche OENOLOGIE, F-33882 Villenave d'Ornon, France; INRA, ISVV, USC 1366 OENOLOGIE, 33882 Villenave d'Ornon, France. Electronic address: axel.marchal@u-bordeaux.fr.
authors.forename: Axel
authors.initials: A
authors.lastname: Marchal
authors.affiliation: Thermo Fisher Scientific, LC/MS Laboratory, 16 avenue du Québec, F-91140 Villebon sur Yvette, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Génin
authors.affiliation: Univ. de Bordeaux, ISVV, GESVAB, EA 3675, F-33882 Villenave d'Ornon, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Waffo-Téguo
authors.affiliation: Univ. de Bordeaux, ISVV, EA 4577, Unité de recherche OENOLOGIE, F-33882 Villenave d'Ornon, France; INRA, ISVV, USC 1366 OENOLOGIE, 33882 Villenave d'Ornon, France.
authors.forename: Alice
authors.initials: A
authors.lastname: Bibès
authors.affiliation: Univ. de Bordeaux, ISVV, GESVAB, EA 3675, F-33882 Villenave d'Ornon, France.
authors.forename: Grégory
authors.initials: G
authors.lastname: Da Costa
authors.affiliation: Univ. de Bordeaux, ISVV, GESVAB, EA 3675, F-33882 Villenave d'Ornon, France.
authors.forename: Jean-Michel
authors.initials: JM
authors.lastname: Mérillon
authors.affiliation: Univ. de Bordeaux, ISVV, EA 4577, Unité de recherche OENOLOGIE, F-33882 Villenave d'Ornon, France; INRA, ISVV, USC 1366 OENOLOGIE, 33882 Villenave d'Ornon, France.
authors.forename: Denis
authors.initials: D
authors.lastname: Dubourdieu
mesh_terms: D001688:Biological Products / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D055808:Drug Discovery; D005583:Fourier Analysis; D007536:Isomerism; D013058:Mass Spectrometry / Q000379:methods*; D029963:Quercus / Q000737:chemistry*; D013549:Sweetening Agents / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D014920:Wine; D014934:Wood / Q000737:chemistry*
chemical_list: D001688:Biological Products; D013549:Sweetening Agents
keywords: High resolution mass spectrometry; Liquid chromatography; Oak wood; Sweetness; Triterpenes