title: How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers.
abstract: Wine expresses its beauty by sending a sensory message to the taster through molecules coming from grapes, yeast metabolism or oak wood. Among the compounds released during barrel aging, lyoniresinol has been recently reported as a relevant contributor to wine bitterness. As this lignan contains three stereogenic carbons, this work aimed at investigating the influence of stereochemistry on wine taste by combining analytical and sensorial techniques. First, an oak wood extract was screened by Liquid Chromatography-High Resolution Mass Spectrometry to target isomers separable in a symmetric environment and a diastereoisomer called epi-lyoniresinol was isolated for the first time. Then, an original racemic resolution based on natural xylose-derivatives was carried out to obtain lyoniresinol enantiomers. Chiroptical spectroscopic measurements associated with theoretical calculations allowed the unambiguous determination of their absolute configuration. The taste properties of all these stereoisomers revealed that only one lyoniresinol enantiomer is strongly bitter whereas the other one is tasteless and the diastereoisomer is slightly sweet. The presence of these three compounds was established in an oaked Bordeaux wine by chiral and non-chiral chromatography, suggesting the significant influence of stereochemistry on wine taste.
authors: Université 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: Blandine N
authors: BN
authors: Cretin
authors: Université 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: Quentin
authors: Q
authors: Sallembien
authors: Université 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: Lauriane
authors: L
authors: Sindt
authors: Université de Bordeaux, UMR 5255-CNRS, Institut des Sciences Moléculaires, 351 Cours de la Libération, F-33405 Talence, France.
authors: Nicolas
authors: N
authors: Daugey
authors: Université de Bordeaux, UMR 5255-CNRS, Institut des Sciences Moléculaires, 351 Cours de la Libération, F-33405 Talence, France.
authors: Thierry
authors: T
authors: Buffeteau
authors: Université de Bordeaux, ISVV, GESVAB, EA 3675, F-33882 Villenave d'Ornon, France.
authors: Pierre
authors: P
authors: Waffo-Teguo
authors: Université 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: Denis
authors: D
authors: Dubourdieu
authors: Université 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: Axel
authors: A
authors: Marchal
mesh_terms: D000840:Anisoles / Q000032:analysis* / Q000737:chemistry; D002853:Chromatography, Liquid; D003377:Countercurrent Distribution; D006801:Humans; D013058:Mass Spectrometry; D009281:Naphthalenes / Q000032:analysis* / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*; D029963:Quercus / Q000737:chemistry*; D013237:Stereoisomerism; D013649:Taste; D055697:Taste Perception; D014920:Wine / Q000032:analysis*; D014934:Wood / Q000737:chemistry*
chemical_list: D000840:Anisoles; D009281:Naphthalenes; D010936:Plant Extracts; C502379:lyoniresinol
keywords: Bitterness; Chiral Liquid Chromatography–High Resolution Mass Spectrometry; Counter Current Chromatography; Lignan; Oak wood; Vibrational circular dichroism