title: Influence of Chirality of Lactones on the Perception of Some Typical Fruity Notes through Perceptual Interaction Phenomena in Bordeaux Dessert Wines.
abstract: Recent studies concerning the aroma of noble rot dessert wines revealed the importance of a well-known phenomenon in perfumery, the perceptual blending, to create the perception of "overripe orange" nuances. Thus, compounds associated with both oak wood aging (3-methyl-4-octanolide and eugenol) and Botrytis cinerea development under the form of noble rot (2-nonen-4-olide and γ-nonalactone) contribute to a specific aroma of great noble rot dessert wines through perceptual interaction phenomena. This synthetic perception phenomenon was established from reconstitution, addition, and omission sensory experiments, using wine extract fractions supplemented with the volatile compounds previously mentioned. To better understand the sensory impact of these compounds, the goal of this research was to study the contributions of enantiomeric forms of 2-nonen-4-olide and γ-nonalactone and the diastereoisomers of 3-methyl-4-octanolide. After multidimensional chiral chromatography analysis, the relative proportions of enantiomers or diastereomeric forms were first established and then sensory experiments were carried out using the reference compounds with isolated fractions from dessert wines. A dominance of the R form was established for 2-nonen-4-olide, which was correlated with wine aging, while the S form is more dominant in young dessert wines. Furthermore, the reconstitution experiments confirmed perceptual interaction phenomena and revealed the sensory contribution of (R)-2-nonen-4-olide and cis-3-methyl-4-octanolide concerning the "overripe orange" nuances, whereas no sensory impact for the γ-nonalactone isomers was observed.
authors.affiliation: Univ. de Bordeaux, ISVV , EA4577 Œnologie, F-33140 Villenave d'Ornon, France.|INRA, ISVV , USC 1366 Œnologie, F-33140 Villenave d'Ornon, France.
authors.forename: Panagiotis
authors.initials: P
authors.lastname: Stamatopoulos
authors.affiliation: Sanofi , 13 Quai Jules Guesde, 94400 Vitry, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Brohan
authors.affiliation: Sanofi , 13 Quai Jules Guesde, 94400 Vitry, France.
authors.forename: Celine
authors.initials: C
authors.lastname: Prevost
authors.affiliation: The Australian Wine Research Institute , Post Office Box 197, Glen Osmond, South Australia 5064, Australia.
authors.forename: Tracey E
authors.initials: TE
authors.lastname: Siebert
authors.affiliation: The Australian Wine Research Institute , Post Office Box 197, Glen Osmond, South Australia 5064, Australia.
authors.forename: Markus
authors.initials: M
authors.lastname: Herderich
authors.affiliation: Univ. de Bordeaux, ISVV , EA4577 Œnologie, F-33140 Villenave d'Ornon, France.|INRA, ISVV , USC 1366 Œnologie, F-33140 Villenave d'Ornon, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Darriet
mesh_terms: D000328:Adult; D005260:Female; D006801:Humans; D007783:Lactones / Q000032:analysis / Q000737:chemistry*; D008297:Male; D012684:Sensory Thresholds; D013237:Stereoisomerism; D055697:Taste Perception; D014920:Wine / Q000032:analysis
chemical_list: D007783:Lactones
keywords: chirality; dessert wine aroma; diastereoisomers; enantiomers; lactones; perceptual interactions