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Article Dans Une Revue Journal of Natural Products Année : 2016

Taste-guided isolation of bitter lignans from Quercus petraea and their identification in wine

Résumé

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.
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Dates et versions

hal-01601644 , version 1 (02-10-2017)

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Lauriane Sindt, Marine Gammacurta, Pierre Waffo-Teguo, Denis Dubourdieu, Axel Marchal. Taste-guided isolation of bitter lignans from Quercus petraea and their identification in wine. Journal of Natural Products, 2016, 79 (10), pp.2432-2438. ⟨10.1021/acs.jnatprod.6b00142⟩. ⟨hal-01601644⟩

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