Isomer composition of aroma compounds as a promising approach for wine characterization and differentiation: A review

References

• Agüero, C. B., J. G. Rodríguez, L. E. Martínez, G. S. Dangl, and C. P. Meredith. 2003. Identity and parentage of Torrontés cultivars in Argentina. American Journal of Enology and Viticulture 54:318–21.
   Web of Science ®Google Scholar
• Antalick, G., S. Tempère, K. Šuklje, J. W. Blackman, A. Deloire, G. de Revel, and L. M. Schmidtke. 2015. Investigation and sensory characterization of 1,4-cineole: a potential aromatic marker of Australian Cabernet Sauvignon wine. Journal of Agricultural and Food Chemistry 63 (41):9103–11. doi: 10.1021/acs.jafc.5b03847.
   PubMed Web of Science ®Google Scholar
• Black, C. A., M. Parker, T. E. Siebert, D. L. Capone, and I. L. Francis. 2015. Terpenoids and their role in wine flavour: recent advances. Australian Journal of Grape and Wine Research 21:582–600. doi: 10.1111/ajgw.12186.
   Web of Science ®Google Scholar
• Boido, E., A. Lloret, K. Medina, L. Fariña, F. Carrau, G. Versini, and E. Dellacassa. 2003. Aroma composition of Vitis vinifera Cv. Tannat: the typical red wine from Uruguay. Journal of Agricultural and Food Chemistry 51 (18):5408–13. doi: 10.1021/jf030087i.
   PubMed Web of Science ®Google Scholar
• Bosso, A., M. Petrozziello, D. Santini, S. Motta, M. Guaita, and C. Marulli. 2008. Effect of grain type and toasting conditions of barrels on the concentration of the volatile substances released by the wood and on the sensory characteristics of Montepulciano d’Abruzzo. Journal of Food Science 73 (7):S373–S82. doi:10.1111/j.1750-3841.2008.00891.x.
   PubMed Web of Science ®Google Scholar
• Bouchilloux, P., P. Darriet, D. Dubourdieu, R. Henry, S. Reichert, and A. Mosandl. 2000. Stereodifferentiation of 3-mercapto-2-methylpropanol in wine. European Food Research and Technology 210 (5):349–52. doi: 10.1007/s002170050562.
   Web of Science ®Google Scholar
• Bowers, J. E, and C. P. Meredith. 1996. Genetic similarities among wine grape cultivars revealed by restriction fragment–length polymorphism (RFLP) analysis. Journal of the American Society for Horticultural Science 121 (4):620–4. doi: 10.21273/JASHS.121.4.620.
   Web of Science ®Google Scholar
• Brenna, E., C. Fuganti, and S. Serra. 2003. Enantioselective perception of chiral odorants. Tetrahedron: Asymmetry 14 (1):1–42. doi: 10.1016/S0957-4166(02)00713-9.
   Google Scholar
• Caliari, V., C. Pretto Panceri, J. P. Rosier, and M. T. Bordignon-Luiz. 2015. Effect of the traditional, Charmat and Asti method production on the volatile composition of Moscato Giallo sparkling wines. LWT - Food Science and Technology 61 (2):393–400. doi: 10.1016/j.lwt.2014.11.039.
   Web of Science ®Google Scholar
• Capone, D. L, and D. W. Jeffery. 2011. Effects of transporting and processing Sauvignon blanc grapes on 3-mercaptohexan-1-ol precursor concentrations. Journal of Agricultural and Food Chemistry 59 (9):4659–67. doi:10.1021/jf200119z.
   PubMed Web of Science ®Google Scholar
• Capone, D. L., K. Van Leeuwen, D. K. Taylor, D. W. Jeffery, K. H. Pardon, G. M. Elsey, and M. A. Sefton. 2011. Evolution and occurrence of 1,8-cineole (eucalyptol) in Australian wine. Journal of Agricultural and Food Chemistry 59 (3):953–9. doi: 10.1021/jf1038212.
   PubMed Web of Science ®Google Scholar
• Carrau, F. M., K. Medina, E. Boido, L. Farina, C. Gaggero, E. Dellacassa, G. Versini, and P. A. Henschke. 2005. De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts. FEMS Microbiology Letters 243 (1):107–15. doi:10.1016/j.femsle.2004.11.050.
   PubMed Web of Science ®Google Scholar
• Chira, K, and P. L. Teissedre. 2013. Relation between volatile composition, ellagitannin content and sensory perception of oak wood chips representing different toasting processes. European Food Research and Technology 236 (4):735–46. doi: 10.1007/s00217-013-1930-0.
   Web of Science ®Google Scholar
• Deloire, A., E. Vaudour, V. Carey, V. Bonnardot, and C. Van Leeuwen. 2005. Grapevine responses to terroir, a global approach. OENO One 39 (4):149–62. doi: 10.20870/oeno-one.2005.39.4.888.
   Google Scholar
• Dumitriu, G.-D., C. Teodosiu, I. Gabur, V. V. Cotea, R. A. Peinado, and N. López de Lerma. 2019. Evaluation of aroma compounds in the process of wine ageing with oak chips. Foods 8 (12):662. doi: 10.3390/foods8120662.
   PubMed Web of Science ®Google Scholar
• Dunkel, A., M. Steinhaus, M. Kotthoff, B. Nowak, D. Krautwurst, P. Schieberle, and T. Hofmann. 2014. Nature’s chemical signatures in human olfaction: a foodborne perspective for future biotechnology. Angewandte Chemie (International ed. in English) 53 (28):7124–43. doi:10.1002/anie.201309508.
   PubMed Web of Science ®Google Scholar
• Dziadas, M, and H. H. Jeleń. 2010. Analysis of terpenes in white wines using SPE-SPME-GC/MS approach. Analytica Chimica Acta 677 (1):43–9. doi: 10.1016/j.aca.2010.06.035.
   PubMed Web of Science ®Google Scholar
• Emanuelli, F., S. Lorenzi, L. Grzeskowiak, V. Catalano, M. Stefanini, M. Troggio, S. Myles, J. M. Martinez-Zapater, E. Zyprian, F. M. Moreira, et al. 2013. Genetic diversity and population structure assessed by SSR and SNP markers in a large germplasm collection of grape. BMC Plant Biology 13:39. doi:10.1186/1471-2229-13-39.
   PubMed Web of Science ®Google Scholar
• Farina, L., E. Boido, F. Carrau, G. Versini, and E. Dellacassa. 2005. Terpene compounds as possible precursors of 1,8-cineole in red grapes and wines. Journal of Agricultural and Food Chemistry 53 (5):1633–6. doi:10.1021/jf040332d.
   PubMed Web of Science ®Google Scholar
• Fernández de Simón, B., E. Esteruelas, A. M. Muñoz, E. Cadahía, and M. Sanz. 2009. Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage. Journal of Agricultural and Food Chemistry 57 (8):3217–27. doi: 10.1021/jf803463h.
   PubMed Web of Science ®Google Scholar
• Ferreira, V, and R. Lopez. 2019. The actual and potential aroma of winemaking grapes. Biomolecules 9 (12):818. doi: 10.3390/biom9120818.
   PubMed Web of Science ®Google Scholar
• Furdíková, K., L. Khvalbota, A. Machyňáková, and I. Špánik. 2021. Volatile composition and enantioselective analysis of chiral terpenoids in Tokaj varietal wines. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 1167:122565. doi:10.1016/j.jchromb.2021.122565.
   PubMed Web of Science ®Google Scholar
• Guth, H. 1997. Identification of character impact odorants of different white wine varieties. Journal of Agricultural and Food Chemistry 45 (8):3022–6. doi: 10.1021/jf9608433.
   Web of Science ®Google Scholar
• Holmberg, L. 2010. Wine fraud. International Journal of Wine Research 2:105–13. doi: 10.2147/IJWR.S14102.
   Google Scholar
• Jelén, H, and A. Gracka. 2017. Characterization of aroma compounds: structure, physico-chemical and sensory properties. In Flavour: From food to perception, ed. Guichard, E., Salles, C., Morzel, M., and Le Bon, A.-M., 126–53. Chichester, United Kingdom: John Wiley and Sons.
   Google Scholar
• Joubert, C., P. R. Young, H. A. Eyéghé-Bickong, and M. A. Vivier. 2016. Field-grown grapevine berries use carotenoids and the associated xanthophyll cycles to acclimate to UV exposure differentially in high and low light (shade) conditions. Frontiers in Plant Science 7:786. doi:10.3389/fpls.2016.00786.
   PubMed Web of Science ®Google Scholar
• Kalua, C. M, and P. K. Boss. 2010. Comparison of major volatile compounds from Riesling and Cabernet Sauvignon grapes (Vitis vinifera L.) from fruitset to harvest. Australian Journal of Grape and Wine Research 16 (2):337–48. doi: 10.1111/j.1755-0238.2010.00096.x.
   Web of Science ®Google Scholar
• Khvalbota, L., A. Machyňáková, J. Čuchorová, K. Furdíková, and I. Špánik. 2021. Enantiomer composition of chiral compounds present in traditional Slovak Tokaj wines. Journal of Food Composition and Analysis 96:103719. doi: 10.1016/j.jfca.2020.103719.
   Web of Science ®Google Scholar
• King, A, and J. R. Dickinson. 2000. Biotransformation of monoterpene alcohols by Saccharomyces cerevisiae, Torulaspora delbrueckii and Kluyveromyces lactis. Yeast 16 (6):499–506. doi: 10.1002/(SICI)1097-0061(200004)16:6≤499::AID-YEA548≥3.0.CO;2-E.
   PubMed Web of Science ®Google Scholar
• Koslitz, S., L. Renaud, M. Kohler, and M. Wüst. 2008. Stereoselective formation of the varietal aroma compound rose oxide during alcoholic fermentation. Journal of Agricultural and Food Chemistry 56 (4):1371–5. doi:10.1021/jf072518t.
   PubMed Web of Science ®Google Scholar
• Loreto, F, and J. P. Schnitzler. 2010. Abiotic stresses and induced BVOCs. Trends in Plant Science 15 (3):154–66. doi:10.1016/j.tplants.2009.12.006.
   PubMed Web of Science ®Google Scholar
• Luan, F., A. Mosandl, M. Gubesch, and M. Wüst. 2006. Enantioselective analysis of monoterpenes in different grape varieties during berry ripening using stir bar sorptive extraction- and solid phase extraction-enantioselective-multidimensional gas chromatography-mass spectrometry. Journal of Chromatography. A 1112 (1-2):369–74. doi:10.1016/j.chroma.2005.12.056.
   PubMed Web of Science ®Google Scholar
• Luan, F., A. Mosandl, A. Münch, and M. Wüst. 2005. Metabolism of geraniol in grape berry mesocarp of Vitis vinifera L. cv. Scheurebe: demonstration of stereoselective reduction, E/Z-isomerization, oxidation and glycosylation. Phytochemistry 66 (3):295–303. doi: 10.1016/j.phytochem.2004.12.017.
   PubMed Web of Science ®Google Scholar
• Luo, J., J. Brotchie, M. Pang, P. J. Marriott, K. Howell, and P. Zhang. 2019. Free terpene evolution during the berry maturation of five Vitis vinifera L. cultivars. Food Chemistry 299:125101. doi: 10.1016/j.foodchem.2019.125101.
   PubMed Web of Science ®Google Scholar
• Lytra, G., S. Tempere, G. de Revel, and J.-C. Barbe. 2012. Distribution and organoleptic impact of ethyl 2-hydroxy-4-methylpentanoate enantiomers in wine. Journal of Agricultural and Food Chemistry 60 (6):1503–9. doi: 10.1021/jf204378u.
   PubMed Web of Science ®Google Scholar
• Machyňáková, A., L. Khvalbota, and I. Špánik. 2021. Enantiomer distribution of major chiral volatile organic compounds in botrytized grapes and wines. European Food Research and Technology 247 (9):2321–31. doi: 10.1007/s00217-021-03792-0.
   Web of Science ®Google Scholar
• Marsol-Vall, A., B. Sgorbini, C. Cagliero, C. Bicchi, J. Eras, and M. Balcells. 2017. Volatile composition and enantioselective analysis of chiral terpenoids of nine fruit and vegetable fibres resulting from juice industry by-products. Journal of Chemistry 2017:1–11. doi: 10.1155/2017/8675014.
   Web of Science ®Google Scholar
• Mele, M. A., H. M. Kang, Y. T. Lee, and M. Zahirul Islam. 2021. Grape terpenoids: flavor importance, genetic regulation, and future potential. Critical Reviews in Food Science and Nutrition 61 (9):1429–47. doi: 10.1080/10408398.2020.1760203.
   PubMed Web of Science ®Google Scholar
• Oliveira, J. M., I. M. Araújo, Ó. M. Pereira, J. S. Maia, A. J. Amaral, and M. O. Maia. 2004. Characterization and differentiation of five “Vinhos Verdes” grape varieties on the basis of monoterpenic compounds. Analytica Chimica Acta 513 (1):269–75. doi: 10.1016/j.aca.2003.10.020.
   Web of Science ®Google Scholar
• Oliveira, J. M., M. Faria, F. Sá, F. Barros, and I. M. Araújo. 2006. C6-alcohols as varietal markers for assessment of wine origin. Analytica Chimica Acta 563 (1-2):300–9. doi: 10.1016/j.aca.2005.12.029.
   Web of Science ®Google Scholar
• Pérez-Prieto, L. J., J. M. López-Roca, A. Martínez-Cutillas, F. Pardo Mínguez, and E. Gómez-Plaza. 2002. Maturing wines in oak barrels. Effects of origin, volume, and age of the barrel on the wine volatile composition. Journal of Agricultural and Food Chemistry 50 (11):3272–6. doi: 10.1021/jf011505r.
   PubMed Web of Science ®Google Scholar
• Picard, M., G. De Revel, and S. Marchand. 2017. First identification of three p-menthane lactones and their potential precursor, menthofuran, in red wines. Food Chemistry 217:294–302. doi: 10.1016/j.foodchem.2016.08.070.
   PubMed Web of Science ®Google Scholar
• Picard, M., G. Lytra, S. Tempère, J. C. Barbe, G. de Revel, and S. Marchand. 2016b. Identification of piperitone as an aroma compound contributing to the positive mint nuances perceived in aged red Bordeaux wines. Journal of Agricultural and Food Chemistry 64 (2):451–60. doi: 10.1021/acs.jafc.5b04869.
   PubMed Web of Science ®Google Scholar
• Picard, M., S. Tempère, G. de Revel, and S. Marchand. 2016a. Piperitone profiling in fine red Bordeaux wines: geographical influences in the Bordeaux region and enantiomeric distribution. Journal of Agricultural and Food Chemistry 64 (40):7576–84. doi: 10.1021/acs.jafc.6b02835.
   PubMed Web of Science ®Google Scholar
• Pollon, M., F. Torchio, S. Giacosa, S. R. Segade, and L. Rolle. 2019. Use of density sorting for the selection of aromatic grape berries with different volatile profile. Food Chemistry 276:562–71. doi: 10.1016/j.foodchem.2018.10.040.
   PubMed Web of Science ®Google Scholar
• Pons, A., V. Lavigne, P. Darriet, and D. Dubourdieu. 2016. Identification and analysis of piperitone in red wines. Food Chemistry 206:191–6. doi: 10.1016/j.foodchem.2016.03.064.
   PubMed Web of Science ®Google Scholar
• Prida, A., A. Ducousso, R. J. Petit, G. Nepveu, and J.-L. Puech. 2007. Variation in wood volatile compounds in a mixed oak stand: strong species and spatial differentiation in whisky-lactone content. Annals of Forest Science 64 (3):313–20. doi: 10.1051/forest:2007008.
   Web of Science ®Google Scholar
• Rapp, A. 1995. Possibilities of characterizing wine varieties by means of volatile flavor compounds. Developments in Food Science 37:1703–22. doi: 10.1016/S0167-4501(06)80259-1.
   Google Scholar
• Robinson, A. L., P. K. Boss, P. S. Solomon, R. D. Trengove, H. Heymann, and S. E. Ebeler. 2014. Origins of grape and wine aroma. Part 1. Chemical components and viticultural impacts. American Journal of Enology and Viticulture 65 (1):1–24. doi: 10.5344/ajev.2013.12070.
   Web of Science ®Google Scholar
• Ruiz del Castillo, M. L., M. M. Caja, and M. Herraiz. 2003. Use of the enantiomeric composition for the assessment of the authenticity of fruit beverages. Journal of Agricultural and Food Chemistry 51 (5):1284–8. doi: 10.1021/jf025711q.
   PubMed Web of Science ®Google Scholar
• Ruiz, J., F. Kiene, I. Belda, D. Fracassetti, D. Marquina, E. Navascués, F. Calderón, A. Benito, D. Rauhut, A. Santos, et al. 2019. Effects on varietal aromas during wine making: a review of the impact of varietal aromas on the flavor of wine. Applied Microbiology and Biotechnology 103 (18):7425–50. doi: 10.1007/s00253-019-10008-9.
   PubMed Web of Science ®Google Scholar
• Schwab, W, and M. Wüst. 2015. Understanding the constitutive and induced biosynthesis of mono- and sesquiterpenes in grapes (Vitis vinifera): a key to unlocking the biochemical secrets of unique grape aroma profiles. Journal of Agricultural and Food Chemistry 63 (49):10591–603. doi: 10.1021/acs.jafc.5b04398.
   PubMed Web of Science ®Google Scholar
• Skinkis, P. A., B. P. Bordelon, and K. V. Wood. 2008. Comparison of monoterpene constituents in Traminette, Gewürztraminer, and Riesling winegrapes. American Journal of Enology and Viticulture 59:440–5.
   Web of Science ®Google Scholar
• Slaghenaufi, D., G. Luzzini, J. Samaniego Solis, F. Forte, and M. Ugliano. 2021b. Two sides to one story—Aroma chemical and sensory signature of Lugana and Verdicchio wines. Molecules 26 (8):2127. doi: 10.3390/molecules26082127.
   PubMed Web of Science ®Google Scholar
• Slaghenaufi, D., M. C. Perello, S. Marchand-Marion, S. Tempere, and G. De Revel. 2014. Quantitative solid phase microextraction – Gas chromatography mass spectrometry analysis of five megastigmatrienone isomers in aged wine. Analytica Chimica Acta 813:63–9. doi: 10.1016/j.aca.2014.01.019.
   PubMed Web of Science ®Google Scholar
• Slaghenaufi, D., E. Peruch, M. De Cosmi, L. Nouvelet, and M. Ugliano. 2021a. Volatile and phenolic composition of monovarietal red wines of Valpolicella appellations. OENO One 55 (1):279–94. doi: 10.20870/oeno-one.2021.55.1.3865.
   Web of Science ®Google Scholar
• Slaghenaufi, D, and M. Ugliano. 2018. Norisoprenoids, sesquiterpenes and terpenoids content of Valpolicella wines during aging: investigating aroma potential in relationship to evolution of tobacco and balsamic aroma in aged wine. Frontiers in Chemistry 6:66. doi: 10.3389/fchem.2018.00066.
   PubMed Web of Science ®Google Scholar
• Song, M., C. Fuentes, A. Loos, and E. Tomasino. 2018. Free monoterpene isomer profiles of Vitis vinifera L. cv. white wines. Foods 7 (2):27. doi: 10.3390/foods7020027.
   PubMed Web of Science ®Google Scholar
• Souza Gonzaga, L., D. L. Capone, S. E. P. Bastian, and D. W. Jeffery. 2021. Defining wine typicity: sensory characterisation and consumer perspectives. Australian Journal of Grape and Wine Research 27 (2):246–56. doi: 10.1111/ajgw.12474.
   Web of Science ®Google Scholar
• Stamatopoulos, P., E. Brohan, C. Prevost, T. E. Siebert, M. Herderich, and P. Darriet. 2016. Influence of chirality of lactones on the perception of some typical fruity notes through perceptual interaction phenomena in Bordeaux dessert wines. Journal of Agricultural and Food Chemistry 64 (43):8160–7. doi: 10.1021/acs.jafc.6b03117.
   PubMed Web of Science ®Google Scholar
• Tomasino, E., M. Song, and C. Fuentes. 2020. Odor perception interactions between free monoterpene isomers and wine composition of Pinot gris wines. Journal of Agricultural and Food Chemistry 68 (10):3220–7. doi: https://dx.doi.org/10.1021/acs.jafc.9b07505.
   PubMed Web of Science ®Google Scholar
• Tominaga, T., Y. Niclass, E. Frérot, and D. Dubourdieu. 2006. Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (var. Sauvignon blanc and Semillon). Journal of Agricultural and Food Chemistry 54 (19):7251–5. doi: 10.1021/jf061566v.
   PubMed Web of Science ®Google Scholar
• Torchio, F., S. Giacosa, M. Vilanova, S. Río Segade, V. Gerbi, M. Giordano, and L. Rolle. 2016. Use of response surface methodology for the assessment of changes in the volatile composition of Moscato Bianco (Vitis vinifera L.) grape berries during ripening. Food Chemistry 212:576–84. doi: 10.1016/j.foodchem.2016.05.191.
   PubMed Web of Science ®Google Scholar
• Torchio, F., S. Río Segade, V. Gerbi, E. Cagnasso, M. Giordano, S. Giacosa, and L. Rolle. 2012. Changes in varietal volatile composition during shelf-life of two types of aromatic red sweet Brachetto sparkling wines. Food Research International 48 (2):491–8. doi: 10.1016/j.foodres.2012.04.014.
   Web of Science ®Google Scholar
• Usseglio Tomasset, L. 1983. Influence de la témperature de conservation sur le caractéristiques physico-chimiques et organoleptiques des vins (vins aromatiques). Bulletin de l’O.I.V 56 (523):19–34.
   Google Scholar
• Versari, A., V. F. Laurie, A. Ricci, L. Laghi, and G. P. Parpinello. 2014. Progress in authentication, typification and traceability of grapes and wines by chemometric approaches. Food Research International 60:2–18. doi: 10.1016/j.foodres.2014.02.007.
   Web of Science ®Google Scholar
• Versini, G., I. Orriols, and A. D. Serra. 1994. Aroma components of Galician Albariño, Loureira and Godello wines. Vitis 33:165–70.
   Web of Science ®Google Scholar
• Vilanova, M., Z. Genisheva, M. Graña, and J. M. Oliveira. 2013. Determination of odorants in varietal wines from international grape cultivars (Vitis vinífera) grown in NW Spain. South African Journal of Enology and Viticulture 34 (2):212–22. doi: 10.21548/34-2-1097.
   Web of Science ®Google Scholar
• Villano, C., M. T. Lisanti, A. Gambuti, R. Vecchio, L. Moio, L. Frusciante, R. Aversano, and D. Carputo. 2017. Wine varietal authentication based on phenolics, volatiles and DNA markers: state of the art, perspectives and drawbacks. Food Control. 80:1–10. doi: 10.1016/j.foodcont.2017.04.020.
   Web of Science ®Google Scholar
• Waterhouse, A. L, and J. P. Towey. 1994. Oak lactone isomer ratio distinguishes between wines fermented in American and French oak barrels. Journal of Agricultural and Food Chemistry 42 (9):1971–4. doi: 10.1021/jf00045a026.
   Web of Science ®Google Scholar
• Williams, P. J., C. R. Strauss, and B. Wilson. 1980. Hydroxylated linalool derivatives as precursors of volatile monoterpenes of Muscat grapes. Journal of Agricultural and Food Chemistry 28 (4):766–71. doi: 10.1021/jf60230a037.
   Web of Science ®Google Scholar
• Young, P. R., H. A. Eyeghe-Bickong, K. du Plessis, E. Alexandersson, D. A. Jacobson, Z. Coetzee, A. Deloire, and M. A. Vivier. 2016. Grapevine plasticity in response to an altered microclimate: sauvignon blanc modulates specific metabolites in response to increased berry exposure. Plant Physiology 170 (3):1235–54. doi: 10.1104/pp.15.01775.
   PubMed Web of Science ®Google Scholar
• Zamuz, S, and M. Vilanova. 2006. Volatile composition of the Vitis vinifera Albariño musts according to geographic areas from Rías Baixas D.O. (Spain). Italian Journal of Food Science 18:323–8.
   Web of Science ®Google Scholar