Methyl Salicylate Glycosides in Some Italian Varietal Wines
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Materials
3.2. Solid Phase Extraction (ENV+) Procedure
3.3. GC–MS Analysis of Free Methyl Salicylate
3.4. UPLC-Q-TOF-HDMS for the Identification of Glycosides
3.5. UHPLC-MS/MS Ion Trap for the Quantification of Glycosides
3.6. Isolation of Glycosides from Gaultheria Procumbens L. Dry Leaves
3.7. Flash Chromatography with Isolute ENV+ and Preparative HPLC for the Isolation of the Single Glycosides
3.8. NMR Analysis
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Chemical name | Common Name | Wine | Gaultheria procumbens | Viola sp. | Passiflora edulis | Gaultheria yunnanensis |
---|---|---|---|---|---|---|
methyl salicylate 2-O-β-d-glucoside | MeSAG | |||||
methyl salicylate 2-O-β-d-xylopyranosyl (1-6) β-d-glucopyranoside | MeSA-primeveroside or gaultherin | |||||
methyl salicylate 2-O-α-l-arabinopyranosyl (1-6)-β-d-glucopyranoside | MeSA-vicianoside or violutoside | |||||
methyl salicylate 2-O-β-d-apiofuranosyl (1-6)-β-d-glucopyranoside | MeSA-canthoside A | |||||
methyl salicylate 2-O-β-d-galactopyranosyl (1-4)-β-d-glucopyranoside | MeSA-lactoside | |||||
methyl salicylate 2-O-β-d-glucopyranosyl (1-6)-O-β-d-glucopyranoside | MeSA-gentiobioside | |||||
methyl salicylate 2-O-α-l-rhamnopyranosyl (1-6)-β-d-glucopyranoside | MeSA-rutinoside | |||||
methyl salicylate 2-O-β-d-xylopyranosyl (1→2)-β-d-glucopyranoside | MeSA-sambubioside | |||||
methyl salicylate 2-O-β-d-glucopyranosyl (1→2)β-d-glucopyranoside | MeSA-sophoroside | |||||
methyl salicylate 2-O-β-d-xylopyranosyl (1-2)[O-β-d-xylopyranosyl(1-6)]-O-β-d-glucopyranoside | MSTG-A | |||||
methyl salicylate 2-O-β-d-glucopyranosyl (1-2)[O-β-d-xylopyranosyl(1-6)]-O-β-d-glucopyranoside | MSTG-B |
Variety | Vintage | Code | Glycosides | Free | ||||||
---|---|---|---|---|---|---|---|---|---|---|
Monoglycosides | Diglycosides | Sum of All | ||||||||
MeSAG | MeSA-Primeveroside | MeSA-Canthoside A a | MeSA-Violutoside a | MeSA-Gentiobioside a | MeSA-Rutinoside a | MeSA | ||||
Verdicchio | 2008 | Verd/Treb. S.L. | 2455 ± 369 | 57.1 ± 2.1 | <0.1 | 275 ± 6.3 | 476 ± 36.0 | 39.4 ± 0.9 | 3303 ± 389 | 83.1 ± 5.1 |
Verdicchio | 2010 | Verd/Treb. S.L. | 2427 ± 467 | 78.1 ± 3.8 | 38.2 ± 3.3 | 253 ± 15.9 | 323 ± 36.1 | 272 ± 10.4 | 3391 ± 487 | 63.5 ± 2.9 |
Verdicchio | 2013 | Verd/Treb. S.L. | 187 ± 29.7 | 22.8 ± 2.5 | 5.5 ± 0.3 | 113 ± 2.8 | 187 ± 8.2 | <0.1 | 515 ± 33.3 | 21.3 ± 1.9 |
Verdicchio | 2014 | Verd/Treb. S.L. | 244 ± 28.1 | 21.8 ± 1.1 | 18.4 ± 0.7 | 98.6 ± 2.3 | 82.6 ± 4.9 | 14.1 ± 0.3 | 479 ± 20.3 | 5.5 ± 0.3 |
Verdicchio | 2015 | Verd/Treb. S.L. | 520 ± 57.7 | 23.1 ± 1.2 | 8.8 ± 0.2 | 92.9 ± 1.2 | 48.3 ± 1.8 | 75.4 ± 2.6 | 769 ± 56.9 | 24 ± 0.2 |
Verdicchio | 2016 | Verd/Treb. S.L. | 1141 ± 145 | 38.7 ± 2.1 | 21.8 ± 2.2 | 148 ± 7 | 87 ± 1.8 | 98.3 ± 4.1 | 1535 ± 157 | 49.2 ± 0.7 |
Verdicchio | 2016 | Verd/Treb. S.L. | 785 ± 125 | 26.7 ± 2.1 | 10.6 ± 0.2 | 137 ± 4.4 | 42.9 ± 1.9 | 44.1 ± 2.0 | 1046 ± 135 | 48.5 ± 0.9 |
Verdicchio | 2016 | Verd/Treb. S.L. | 531 ± 74.8 | 32.9 ± 1.3 | 38.3 ± 0.3 | 172 ± 9.3 | 36.8 ± 1.5 | 11.6 ± 0.6 | 823 ± 83.5 | 25.4 ± 2.1 |
Verdicchio | 2016 | Verd/Treb. S.L. | 2243 ± 213 | 75.7 ± 2.5 | 112 ± 1.3 | 403 ± 54.8 | 155 ± 5.6 | 41.4 ± 1.6 | 3030 ± 267 | 44.3 ± 1.8 |
Verdicchio | 2016 | Verd/Treb. S.L. | 749 ± 103 | 18.9 ± 0.8 | 16.7 ± 1.3 | 99.7 ± 3.7 | 36.3 ± 1.9 | 27.9 ± 6.3 | 949 ± 109 | 30.3 ± 0.9 |
Verdicchio | 2016 | Verd/Treb. S.L. | 872 ± 67 | 23.9 ± 1.0 | 24.4 ± 0.8 | 110 ± 3.9 | 37.3 ± 1.2 | 57.5 ± 2.0 | 1125 ± 67.4 | 26.2 ± 0.2 |
Verdicchio | 2016 | Verd/Treb. S.L. | 955 ± 124 | 37.9 ± 0.8 | 14.3 ± 1.4 | 137.3 ± 5.4 | 128 ± 5.5 | 62.1 ± 0.6 | 1335 ± 111 | 21.6 ± 2.4 |
Verdicchio | 2017 | Verd/Treb. S.L. | 1120 ± 99 | 9.9 ± 0.6 | <0.1 | 157 ± 5.6 | 0.8 ± 0.1 | 67.8 ± 1.8 | 1356 ± 94 | 122 ± 9.1 |
Verdicchio | 2017 | Verd/Treb. S.L. | 990 ± 123 | 40.2 ± 1.6 | 22.9 ± 0.5 | 147 ± 5.4 | 86.8 ± 2.6 | 98.7 ± 2.7 | 1386 ± 128 | 57.5 ± 0.8 |
Verdicchio | 2017 | Verd/Treb. S.L. | 1033 ± 108 | 43.3 ± 0.1 | 23.6 ± 0.4 | 152 ± 8.3 | 83.4 ± 8.0 | 101 ± 2.8 | 1436 ± 95 | 57.1 ± 1.7 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1178 ± 217 | 33.8 ± 1.6 | 63.2 ± 3.7 | 128 ± 4.8 | 36.5 ± 1.2 | 82.6 ± 3.0 | 1522 ± 229 | 65.3 ± 2.1 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1151.5 ± 97 | 42.7 ± 2.9 | 78.4 ± 9.5 | 161 ± 11.1 | 40.7 ± 1.9 | 106 ± 9.5 | 1580 ± 102 | 35.2 ± 3.2 |
Verdicchio | 2018 | Verd/Treb. S.L. | 3700 ± 309 | 181 ± 15.3 | 348 ± 5.6 | 545 ± 11.4 | 87.1 ± 6.3 | 438 ± 34.0 | 5299 ± 333 | 117 ± 9.6 |
Verdicchio | 2018 | Verd/Treb. S.L. | 2183 ± 228 | 83.3 ± 25.4 | 95.3 ± 36.5 | 273 ± 13.0 | 60.1 ± 16.1 | 149 ± 16.5 | 2844 ± 312 | 77.5 ± 0.5 |
Verdicchio | 2018 | Verd/Treb. S.L. | 2456 ± 224 | 66.9 ± 16.6 | 102 ± 42.1 | 363 ± 39.6 | 57.1 ± 9.4 | 133 ± 26.8 | 3178 ± 349 | 75.5 ± 2.6 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1267 ± 95.8 | 43.6 ± 9.3 | 94.4 ± 18.2 | 152 ± 15.9 | 54.7 ± 10.9 | 101 ± 23.2 | 1713 ± 170 | 36.5 ± 0.4 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1485 ± 44.8 | 55.2 ± 4.8 | 89.3 ± 11.5 | 166 ± 7.4 | 104 ± 11.2 | 122 ± 12.1 | 2022 ± 83.2 | 60.5 ± 3.2 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1058 ± 84.8 | 26.1 ± 13.6 | 48.4 ± 17.4 | 107 ± 31.1 | 32.8 ± 9.8 | 65.2 ± 19.9 | 1338 ± 170 | 62.8 ± 6.2 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1151 ± 97 | 42.7 ± 2.9 | 78.4 ± 9.5 | 161 ± 11.1 | 40.7 ± 1.9 | 106 ± 9.5 | 1580 ± 102 | 35.1 ± 1.2 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1518 ± 120 | 27.4 ± 5.7 | 48.7 ± 7.8 | 276 ± 24.3 | 60.2 ± 3.1 | 89.7 ± 2.7 | 2020 ± 130 | 31.5 ± 2.1 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1451 ± 84.8 | 46.8 ± 1.3 | 82.5 ± 5.8 | 187 ± 12.9 | 47.3 ± 4.1 | 98.6 ± 3.9 | 1913 ± 86.5 | 106 ± 12.1 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1694 ± 110 | 49.8 ± 1.9 | 71.1 ± 5.8 | 185 ± 16.2 | 47.7 ± 3.4 | 148.7 ± 8.1 | 2196 ± 106 | 79.7 ± 5.8 |
Verdicchio | 2018 | Verd/Treb. S.L. | 6150 ± 330 | 443 ± 46.0 | 729 ± 32.6 | 1548 ± 16.6 | 423 ± 9.6 | 503 ± 27.5 | 9796 ± 398 | 143 ± 11.2 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1021 ± 89.2 | 37.1 ± 1.5 | 61.8 ± 9.5 | 142 ± 11.8 | 44.2 ± 7.2 | 98.2 ± 2.7 | 1404 ± 89.7 | 49.2 ± 6.3 |
Verdicchio | 2018 | Verd/Treb. S.L. | 1058 ± 120 | 26.1 ± 13.6 | 48.4 ± 7.8 | 107 ± 31.1 | 32.8 ± 9.8 | 65.2 ± 19.9 | 1338 ± 86.8 | 62.8 ± 6.9 |
Verdicchio | 2018 | Verd/Treb. S.L. | 375 ± 48.7 | 23.3 ± 0.9 | 10.3 ± 0.9 | 109 ± 6.5 | 38.3 ± 1.5 | 40.8 ± 0.7 | 597 ± 55.0 | 20.6 ± 0.3 |
Verdicchio | 2018 | Verd/Treb. S.L. | 667 ± 58.6 | 21.3 ± 1.1 | 18.3 ± 0.9 | 98.6 ± 1.3 | 28.9 ± 1.1 | 53.6 ± 3.6 | 888 ± 64.2 | 30.3 ± 1.2 |
Verdicchio | 2018 | Verd/Treb. S.L. | 423 ± 50.3 | 25.6 ± 0.7 | 12 ± 0.5 | 110 ± 3.5 | 39.5 ± 1.8 | 55.2 ± 2.3 | 665 ± 56.4 | 23 ± 0.5 |
Trebbiano di Soave | 2016 | Verd/Treb. S.L. | 3966 ± 742 | 140 ± 32.2 | 212 ± 48.3 | 882 ± 90.7 | 153 ± 4.1 | 41.9 ± 1.8 | 5395 ± 870 | 45.4 ± 2.5 |
Trebbiano di Soave | 2016 | Verd/Treb. S.L. | 369 ± 70.4 | 25.3 ± 0.6 | 17.4 ± 0.8 | 163 ± 3.6 | 39.1 ± 1.4 | 14.7 ± 0.6 | 629 ± 70.6 | 21 ± 1.2 |
Trebbiano di Soave | 2017 | Verd/Treb. S.L. | 262 ± 41.1 | 23.6 ± 1.1 | 16.3 ± 0.2 | 120 ± 2.8 | 46.5 ± 0.5 | 13.5 ± 0.1 | 482 ± 45.3 | 7.5 ± 0.5 |
Trebbiano di Soave | 2017 | Verd/Treb. S.L. | 319 ± 41.1 | 15.6 ± 0.5 | <0.1 | 87.5 ± 2.5 | 5.8 ± 0.3 | 28.2 ± 1.4 | 456 ± 42.5 | 68.6 ± 3.2 |
Trebbiano di Soave | 2017 | Verd/Treb. S.L. | 317 ± 25.4 | 14.6 ± 0.7 | <0.1 | 89.9 ± 4.1 | 5.7 ± 0.4 | 28.9 ± 1.4 | 456 ± 20.3 | 68.6 ± 3.1 |
Trebbiano di Lugana | 2016 | Verd/Treb. S.L. | 2960 ± 366 | 95.3 ± 2.5 | 158 ± 3.4 | 329 ± 28.7 | 194 ± 1.2 | 109 ± 3.4 | 3845 ± 361 | 110 ± 2.3 |
Trebbiano di Lugana | 2016 | Verd/Treb. S.L. | 1227 ± 126 | 50.5 ± 2.1 | 23.2 ± 0.9 | 234 ± 7.9 | 137 ± 4.3 | 28.3 ± 1.7 | 1700 ± 109 | 31.7 ± 1.8 |
Trebbiano di Lugana | 2016 | Verd/Treb. S.L. | 1244 ± 108 | 58.4 ± 1.4 | 23.8 ± 1.2 | 250 ± 10.8 | 159 ± 5.6 | 64.1 ± 1.8 | 1799 ± 93 | 35.6 ± 1.8 |
Trebbiano di Lugana | 2017 | Verd/Treb. S.L. | 1097 ± 105 | 37.5 ± 1.8 | 6.8 ± 0.9 | 97.9 ± 0.9 | 76.6 ± 5.0 | 54.1 ± 0.5 | 1370 ± 106 | 32 ± 0.9 |
Trebbiano di Lugana | 2017 | Verd/Treb. S.L. | 1028 ± 81.7 | 36.7 ± 1.3 | 6.3 ± 1.1 | 95.9 ± 5.4 | 77 ± 1.8 | 54.6 ± 0.4 | 1299 ± 72.5 | 34.0 ± 1.6 |
Bianca | 2016 | Others | 24.5 ± 9.9 | <0.1 | <0.1 | 20.3 ± 0.4 | 3.3 ± 0.2 | 5.8 ± 0.6 | 53.9 ± 9.7 | 12 ± 1.1 |
Trebbiano Abruzzo | 2014 | Others | 37.5 ± 0.9 | 4.5 ± 0.4 | <0.1 | 59.4 ± 1.1 | 5.3 ± 0.1 | 3.6 ± 0.9 | 110 ± 1.6 | 2.1 ± 0.01 |
Peverella | 2013 | Others | 8.8 ± 0.4 | 5.5 ± 0.2 | 4.7 ± 0.6 | 44.3 ± 2.1 | <0.1 | <0.1 | 63.3 ± 2.9 | 5.6 ± 0.8 |
Riesling Renano | 2016 | Others | 6.8 ± 0.2 | <0.1 | <0.1 | 12.5 ± 0.6 | 1.8 ± 0.3 | 5.8 ± 1.1 | 26.9 ± 1.0 | 3.1 ± 0.01 |
Helios | 2016 | Others | 10.7 ± 0.8 | <0.1 | 6.6 ± 1.0 | 53.8 ± 0.5 | 2.6 ± 0.4 | 5.6 ± 0.8 | 79.3 ± 2.4 | 2.1 ± 0.02 |
Moscato d’Asti | 2010 | Others | 7.3 ± 0.3 | <0.1 | <0.1 | 21.2 ± 2.2 | 3.0 ± 0.2 | 4.9 ± 0.5 | 36.4 ± 2.0 | 3.2 ± 0.01 |
Trebbiano Abruzzo | 2012 | Others | 29 ± 9.6 | 2.6 ± 0.3 | <0.1 | 46.7 ± 1.4 | 2.6 ± 0.6 | 8.3 ± 0.1 | 89.2 ± 8.1 | 1.3 ± 0.05 |
Müller Thurgau | 2016 | Others | 7.5 ± 0.4 | <0.1 | <0.1 | 6.1 ± 0.8 | <0.1 | <0.1 | 13.6 ± 0.9 | 5.2 ± 0.3 |
Grüner Veltliner | 2009 | Others | 4.2 ± 0.2 | <0.1 | <0.1 | 8.1 ± 0.5 | <0.1 | <0.1 | 12.3 ± 0.7 | 2.1 ± 0.1 |
Sauvignon Blanc | 2011 | Others | 62.4 ± 11.8 | <0.1 | <0.1 | 52.6 ± 2.1 | 5.2 ± 0.6 | 2.3 ± 1.1 | 123 ± 14.7 | 3.2 ± 0.04 |
Pinot grigio | 2015 | Others | 8.2 ± 0.2 | <0.1 | <0.1 | 32.1 ± 1.7 | 1.2 ± 0.3 | 7.7 ± 0.3 | 49.2 ± 2.0 | 3.1 ± 0.05 |
Chardonnay | 2016 | Others | 4.9 ± 0.3 | <0.1 | 2.8 ± 0.02 | <0.1 | <0.1 | <0.1 | 7.7 ± 0.9 | 7.4 ± 1.0 |
Cataratto | 2016 | Others | 236 ± 11.7 | 15.5 ± 0.4 | 17.2 ± 0.9 | 52.5 ± 1.4 | 14 ± 0.3 | 28.2 ± 2.2 | 363 ± 10.3 | 7.7 ± 0.6 |
Friulano | 2012 | Others | 9.0 ± 0.6 | <0.1 | <0.1 | 5.4 ± 0.4 | <0.1 | 6.3 ± 0.4 | 20.7 ± 0.9 | 3.0 ± 0.05 |
Ribolla gialla | 2016 | Others | 1.5 ± 0.01 | <0.1 | 0.5 ± 0.02 | <0.1 | <0.1 | <0.1 | 2.0 ± 0.06 | 2.1 ± 0.06 |
Riesling renano | 2014 | Others | 2.6 ± 0.04 | 2.5 ± 0.04 | 1.4 ± 0.01 | <0.1 | <0.1 | <0.1 | 6.5 ± 1.6 | 12.0 ± 0.9 |
Pinot grigio | 2015 | Others | <0.05 | <0.1 | 0.2 ± 0.02 | <0.1 | <0.1 | <0.1 | 0.2 ± 0.02 | 2.9 ± 0.01 |
Psarades | 2016 | Others | 5.1 ± 0.06 | <0.1 | 2.5 ± 0.01 | <0.1 | <0.1 | <0.1 | 7.6 ± 0.5 | 7.7 ± 0.6 |
Baiano | 2017 | Others | 0.7 ± 0.01 | <0.1 | 8.9 ± 0.5 | <0.1 | <0.1 | <0.1 | 9.6 ± 0.4 | 2.1 ± 0.01 |
Muscaris | 2017 | Others | <0.05 | 2.5 ± 0.01 | 0.1 | <0.1 | <0.1 | <0.1 | 2.5 ± 0.3 | 5.2 ± 0.4 |
Gewürztraminer | 2009 | Others | <0.05 | <0.1 | <0.1 | <0.1 | <0.1 | <0.1 | <0.1 | 4.0 ± 0.3 |
Name | Common Name | Molecular Formula | Ionization Mode | Precursor Ion | Q1 Product Ion | DP | EP | CE | CXP | Q2 Product Ion | DP | EP | CE | CXP | tR | Q2/Q1 |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
methyl salicylate 2-O-β-d-glucoside | MeSAG | C14H18O8 | [M + Na]+ | 337.0 | 337.0 | 80 | 10 | 10 | 15 | 185.2 | 80 | 10 | 24 | 15 | 15.6 | 17 |
methyl salicylate 2-O-α-l-arabinopyranosyl(1→6)-β-d-glucopyranoside | MeSA-Violutoside/Vicianoside | C19H26O12 | [M + Na]+ | 469.1 | 469.1 | 80 | 10 | 10 | 15 | 337.2 | 80 | 10 | 38 | 15 | 15.2 | 108 |
methyl salicylate 2-O-β-d-xylopyranosyl (1→6)-β-d-glucopyranoside | MeSA-Primeveroside/Gaultherin | C19H26O12 | [M + Na]+ | 469.1 | 469.1 | 80 | 10 | 10 | 15 | 337.2 | 80 | 10 | 38 | 15 | 15.7 | 108 |
methyl salicylate 2-O-β-d-apiofuranosyl(1→6)-β-d-glucopyranoside | MeSA-Canthoside A | C19H26O12 | [M + Na]+ | 469.1 | 469.1 | 80 | 10 | 10 | 15 | 337.2 | 80 | 10 | 38 | 15 | 14.9 | 108 |
methyl salicylate 2-O-α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside | MeSA-rutinoside | C20H28O12 | [M + Na]+ | 483.1 | 483.1 | 80 | 10 | 10 | 15 | 337.1 | 80 | 10 | 35 | 15 | 16.8 | 60 |
methyl salicylate 2-O-β-d-glucopyranosyl(1→6)-O-β-d-glucopyranoside | MeSA-gentiobioside | C20H28O13 | [M + Na]+ | 499.1 | 499.1 | 80 | 10 | 10 | 15 | 347.2 | 80 | 10 | 31 | 15 | 13.6 | 20 |
methyl salicylate 2-O-β-d-xylopyranosyl (1→2)[O-β-d-xylopyranosyl(1→6)]-O-β-d-glucopyranoside | MSTG-A | C24H34O16 | [M + Na]+ | 601.1 | 601.1 | 80 | 10 | 10 | 15 | 449.2 | 80 | 10 | 38 | 15 | 14.5 | 14 |
Name | Common Name | Linearity Range (µg/L) | Solvent Calibration Curves Equation | R2 | LOQ (µg/L) |
---|---|---|---|---|---|
methyl salicylate 2-O-β-d-glucoside | MeSAG | 0.05–200 | Y = 1377830x + 268124 | 0.99 | 0.05 |
methyl salicylate 2-O-β-d-xylopyranosyl (1→6)-β-d-glucopyranoside | MeSA-primeveroside/gaultherin | 0.1–200 | Y = 1671150x + 2311990 | 0.98 | 0.1 |
methyl salicylate 2-O-β-d-xylopyranosyl (1→2)[O-β-d-xylopyranosyl(1→6)]-O-β-d-glucopyranoside | MSTG-A | 0.1–200 | Y = 603915x + 269546 | 0.99 | 0.1 |
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Carlin, S.; Masuero, D.; Guella, G.; Vrhovsek, U.; Mattivi, F. Methyl Salicylate Glycosides in Some Italian Varietal Wines. Molecules 2019, 24, 3260. https://doi.org/10.3390/molecules24183260
Carlin S, Masuero D, Guella G, Vrhovsek U, Mattivi F. Methyl Salicylate Glycosides in Some Italian Varietal Wines. Molecules. 2019; 24(18):3260. https://doi.org/10.3390/molecules24183260
Chicago/Turabian StyleCarlin, Silvia, Domenico Masuero, Graziano Guella, Urska Vrhovsek, and Fulvio Mattivi. 2019. "Methyl Salicylate Glycosides in Some Italian Varietal Wines" Molecules 24, no. 18: 3260. https://doi.org/10.3390/molecules24183260