Glycosides are ubiquitous plant secondary metabolites consisting of a non-sugar component called an aglycone, attached to one or more sugars. One of the most interesting aglycones in grapes and wine is methyl salicylate (MeSA), an organic ester naturally produced by many plants, particularly wintergreens. To date, nine different MeSA glycosides from plants have been reported, mainly spread over the genera Gaultheria, Camellia, Polygala, Filipendula, and Passiflora. From a sensorial point of view, MeSA has a balsamic-sweet odor, known as Wintergreen. MeSA was found in Vitisriparia grapes, in Vitisvinifera sp. and in the Frontenac interspecific hybrid. We found that the MeSA glycosides content in Verdicchio wines and in some genetically related varieties (Trebbiano di Soave and Trebbiano di Lugana) was very high. In order to understand which glycosides were present in wine, the methanolic extract of Verdicchio wine was injected into a UPLC-Q-TOF-HDMS and compared to the extracts of different plants rich in such glycosides. Using pure standards, we confirmed the existence of two glycosides in wine: MeSA 2-O-beta-D-glucoside and MeSA 2-O-beta-D-xylopyranosyl (1-6) beta-D-glucopyranoside (gaultherin). For the first time, we also tentatively identified other diglycosides in wine: MeSA 2-O-alpha-L-arabinopyranosyl (1-6)-beta-D-glucopyranoside (violutoside) and MeSA 2-O-beta-D-apiofuranosyl (1-6)-beta-D-glucopyranoside (canthoside A), MeSA 2-O-beta-D-glucopyranosyl (1-6)-O-beta-D-glucopyranoside (gentiobioside) and MeSA 2-O-alpha-L-rhamnopyranosyl (1-6)-beta-D-glucopyranoside (rutinoside). Some of these glycosides have been isolated from Gaultheria procumbens leaves by preparative liquid chromatography and structurally annotated by 1H- and 13C-NMR analysis. Two of the peaks isolated from Gaultheria procumbens leaves, namely MeSA sambubioside and MeSA sophoroside, were herein observed for the first time. Six MeSA glycosides were quantified in 64 Italian white wines, highlighting the peculiar content and pattern in Verdicchio wines and related cultivars. The total concentration in bound and free MeSA in Verdicchio wines varied in the range of 456-9796 microg/L and 5.5-143 microg/L, respectively, while in the other wines the bound and free MeSA was below 363 microg/L and 12 microg/L, respectively. As this compound's olfactory threshold is between 50 and 100 microg/L, our data support the hypothesis that methyl salicylate can contribute to the balsamic scent, especially in old Verdicchio wines.

Methyl Salicylate Glycosides in Some Italian Varietal Wines / Carlin, Silvia; Masuero, Domenico; Guella, Graziano; Vrhovsek, Urska; Mattivi, Fulvio. - In: MOLECULES. - ISSN 1420-3049. - 24:18(2019), p. 3260. [10.3390/molecules24183260]

Methyl Salicylate Glycosides in Some Italian Varietal Wines

Masuero, Domenico;Guella, Graziano;Vrhovsek, Urska;Mattivi, Fulvio
2019

Abstract

Glycosides are ubiquitous plant secondary metabolites consisting of a non-sugar component called an aglycone, attached to one or more sugars. One of the most interesting aglycones in grapes and wine is methyl salicylate (MeSA), an organic ester naturally produced by many plants, particularly wintergreens. To date, nine different MeSA glycosides from plants have been reported, mainly spread over the genera Gaultheria, Camellia, Polygala, Filipendula, and Passiflora. From a sensorial point of view, MeSA has a balsamic-sweet odor, known as Wintergreen. MeSA was found in Vitisriparia grapes, in Vitisvinifera sp. and in the Frontenac interspecific hybrid. We found that the MeSA glycosides content in Verdicchio wines and in some genetically related varieties (Trebbiano di Soave and Trebbiano di Lugana) was very high. In order to understand which glycosides were present in wine, the methanolic extract of Verdicchio wine was injected into a UPLC-Q-TOF-HDMS and compared to the extracts of different plants rich in such glycosides. Using pure standards, we confirmed the existence of two glycosides in wine: MeSA 2-O-beta-D-glucoside and MeSA 2-O-beta-D-xylopyranosyl (1-6) beta-D-glucopyranoside (gaultherin). For the first time, we also tentatively identified other diglycosides in wine: MeSA 2-O-alpha-L-arabinopyranosyl (1-6)-beta-D-glucopyranoside (violutoside) and MeSA 2-O-beta-D-apiofuranosyl (1-6)-beta-D-glucopyranoside (canthoside A), MeSA 2-O-beta-D-glucopyranosyl (1-6)-O-beta-D-glucopyranoside (gentiobioside) and MeSA 2-O-alpha-L-rhamnopyranosyl (1-6)-beta-D-glucopyranoside (rutinoside). Some of these glycosides have been isolated from Gaultheria procumbens leaves by preparative liquid chromatography and structurally annotated by 1H- and 13C-NMR analysis. Two of the peaks isolated from Gaultheria procumbens leaves, namely MeSA sambubioside and MeSA sophoroside, were herein observed for the first time. Six MeSA glycosides were quantified in 64 Italian white wines, highlighting the peculiar content and pattern in Verdicchio wines and related cultivars. The total concentration in bound and free MeSA in Verdicchio wines varied in the range of 456-9796 microg/L and 5.5-143 microg/L, respectively, while in the other wines the bound and free MeSA was below 363 microg/L and 12 microg/L, respectively. As this compound's olfactory threshold is between 50 and 100 microg/L, our data support the hypothesis that methyl salicylate can contribute to the balsamic scent, especially in old Verdicchio wines.
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Carlin, Silvia; Masuero, Domenico; Guella, Graziano; Vrhovsek, Urska; Mattivi, Fulvio
Methyl Salicylate Glycosides in Some Italian Varietal Wines / Carlin, Silvia; Masuero, Domenico; Guella, Graziano; Vrhovsek, Urska; Mattivi, Fulvio. - In: MOLECULES. - ISSN 1420-3049. - 24:18(2019), p. 3260. [10.3390/molecules24183260]
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