Taste-Guided Isolation of Bitter Lignans from Quercus petraea and Their Identification in Wine.
Quercoresinosides A and B (1 and 2), two new lignans, were isolated from a toasted Quercus petraea heartwood extract along with a known compound, 3-methoxy-4-hydroxyphenol 1-O-β-d-(6'-O-galloyl)glucopyranoside (3). The purification protocol was based on a taste-guided approach that sought to reveal new bitter compounds released from oak wood into wines and spirits. HRMS and NMR data were used to establish that compounds 1 and 2 are lignan derivatives bearing a glucosyl unit and a galloyl unit at the same positions. Hydrolysis of these compounds showed that they could be distinguished by the absolute configuration of their respective lyoniresinol genin as determined by chiral LC-HRMS in comparison with (+)- and (-)-lyoniresinol standards. Sensory analyses were performed in a non-oaked wine on the pure compounds 1-3. The three molecules exhibited a bitter taste at 2 mg/L that was particularly intense for compounds 2 and 3. Finally, LC-HRMS demonstrated the occurrence of compounds 1-3 in oaked wine and brandy, which supports the hypothesis of their contributions to the increase in bitterness during oak aging.
Université de Bordeaux, ISVV , EA 4577, Unité de Recherche OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.|INRA, Institut des Sciences de la Vigne et du Vin , USC 1366 OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.
Lauriane
L
Sindt
Université de Bordeaux, ISVV , EA 4577, Unité de Recherche OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.|INRA, Institut des Sciences de la Vigne et du Vin , USC 1366 OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.
Marine
M
Gammacurta
Université de Bordeaux, ISVV , EA 4577, Unité de Recherche OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.|INRA, Institut des Sciences de la Vigne et du Vin , USC 1366 OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.
Pierre
P
Waffo-Teguo
Université de Bordeaux, ISVV , EA 4577, Unité de Recherche OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.|INRA, Institut des Sciences de la Vigne et du Vin , USC 1366 OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.
Denis
D
Dubourdieu
Université de Bordeaux, ISVV , EA 4577, Unité de Recherche OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.|INRA, Institut des Sciences de la Vigne et du Vin , USC 1366 OENOLOGIE, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon, France.
Axel
A
Marchal
D000840:Anisoles; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D006801:Humans; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D009281:Naphthalenes; D019906:Nuclear Magnetic Resonance, Biomolecular; D029963:Quercus / Q000737:chemistry*; D013649:Taste; D014920:Wine; D014934:Wood / Q000737:chemistry
D000840:Anisoles; D017705:Lignans; D009281:Naphthalenes; C502379:lyoniresinol; C000620401:quercoresinoside A; C000620402:quercoresinoside B