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Chiral Polyfunctional Thiols and Their Conjugated Precursors upon Winemaking with Five Vitis vinifera Sauvignon blanc Clones

  • Liang Chen
    Liang Chen
    Department of Wine and Food Science, The University of Adelaide (UA), PMB 1, Glen Osmond, South Australia 5064, Australia
    More by Liang Chen
  • Dimitra L. Capone
    Dimitra L. Capone
    The Australian Wine Research Institute (AWRI), PO Box 197, Glen Osmond, South Australia 5064, Australia
  • Federico A. Tondini
    Federico A. Tondini
    Department of Wine and Food Science, The University of Adelaide (UA), PMB 1, Glen Osmond, South Australia 5064, Australia
    The Australian Research Council Training Centre for Innovative Wine Production, The University of Adelaide, PMB 1, Glen Osmond, South Australia 5064, Australia
  • , and 
  • David W. Jeffery*
    David W. Jeffery
    Department of Wine and Food Science, The University of Adelaide (UA), PMB 1, Glen Osmond, South Australia 5064, Australia
    The Australian Research Council Training Centre for Innovative Wine Production, The University of Adelaide, PMB 1, Glen Osmond, South Australia 5064, Australia
    *E-mail: [email protected]; Telephone: +61 8 83136649.
Cite this: J. Agric. Food Chem. 2018, 66, 18, 4674–4682
Publication Date (Web):April 27, 2018
https://doi.org/10.1021/acs.jafc.8b01806
Copyright © 2018 American Chemical Society

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    Abstract

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    Five co-located clones of Sauvignon blanc grapes were fermented under controlled conditions at laboratory-scale to investigate the impact of yeast strain, commercial enzyme, or nutrient addition on the concentrations of enantiomers of 3-sulfanylhexan-1-ol (3-SH) and 3-sulfanylhexyl acetate (3-SHA) in resulting wines. The relationship of these enantiomers with the odorless 3-SH precursors present in diastereomeric forms in grape juice was also examined. Possible variations may have existed due to clone type, not only for the diastereomers of 3-SH precursors in juices but also for the enantiomers of 3-SH and 3-SHA in the resulting wines, although there was no obvious stereochemical relationship between precursors and free thiols. From a flavor enhancement perspective, the use of a commercial enzyme in the juice significantly enhanced 3-SH production for some clones. In contrast, less impact on the production of 3-SH and 3-SHA was seen as a result of yeast strain and nutrient regardless of clone type.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.8b01806.

    • Tables containing data for pH, TA, and concentrations of enantiomers of 3-SH and 3-SHA in wines from five clones of Sauvignon blanc, and a matrix of ANOVA multiple comparisons of chiral thiol data between clones; and a figure showing the fermentation profiles of juices from five clones of Sauvignon blanc (PDF)

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    Cited By

    This article is cited by 12 publications.

    1. Karl-Heinz Engel. Chirality: An Important Phenomenon Regarding Biosynthesis, Perception, and Authenticity of Flavor Compounds. Journal of Agricultural and Food Chemistry 2020, 68 (38) , 10265-10274. https://doi.org/10.1021/acs.jafc.0c01512
    2. Xingchen Wang, Liang Chen, Dimitra L. Capone, Aurélie Roland, David W. Jeffery. Evolution and Correlation of cis-2-Methyl-4-propyl-1,3-oxathiane, Varietal Thiols, and Acetaldehyde during Fermentation of Sauvignon blanc Juice. Journal of Agricultural and Food Chemistry 2020, 68 (32) , 8676-8687. https://doi.org/10.1021/acs.jafc.0c03183
    3. Liang Chen, Dimitra L. Capone, David W. Jeffery. Identification and Quantitative Analysis of 2-Methyl-4-propyl-1,3-oxathiane in Wine. Journal of Agricultural and Food Chemistry 2018, 66 (41) , 10808-10815. https://doi.org/10.1021/acs.jafc.8b04027
    4. Marina Tomašević, Katarina Lukić, Natka Ćurko, Ana-Marija Jagatić Korenika, Darko Preiner, Valentina Tuščić, Ana Jeromel, Karin Kovačević Ganić. The Influence of Grape Clone and Yeast Strain on Varietal Thiol Concentrations and Sensory Properties of Graševina Wines. Foods 2023, 12 (5) , 985. https://doi.org/10.3390/foods12050985
    5. Xingchen Wang, Dimitra L. Capone, Aurélie Roland, David W. Jeffery. Impact of accentuated cut edges, yeast strain, and malolactic fermentation on chemical and sensory profiles of Sauvignon blanc wine. Food Chemistry 2023, 400 , 134051. https://doi.org/10.1016/j.foodchem.2022.134051
    6. A. Tirelli, I. De Noni, M. Stuknyté, V. Pica, D. Fracassetti. Role of extraction procedures on the concentration of varietal thiol precursors in Grillo white grape must. Australian Journal of Grape and Wine Research 2022, 28 (1) , 61-69. https://doi.org/10.1111/ajgw.12514
    7. Xu Qian, Fangyuan Jia, Jian Cai, Ying Shi, Changqing Duan, Yibin Lan. Characterization and Evolution of Volatile Compounds of Cabernet Sauvignon Wines from Two Different Clones during Oak Barrel Aging. Foods 2022, 11 (1) , 74. https://doi.org/10.3390/foods11010074
    8. Xingchen Wang, Dimitra L. Capone, Aurélie Roland, David W. Jeffery. Chiral analysis of cis-2-methyl-4-propyl-1,3-oxathiane and identification of cis-2,4,4,6-tetramethyl-1,3-oxathiane in wine. Food Chemistry 2021, 357 , 129406. https://doi.org/10.1016/j.foodchem.2021.129406
    9. Jennifer R. Muhl, Lisa I. Pilkington, Rebecca C. Deed. First synthesis of 3-S-glutathionylhexanal-d and its bisulfite adduct. Tetrahedron Letters 2020, 61 (28) , 152100. https://doi.org/10.1016/j.tetlet.2020.152100
    10. Gerardo Alvarez-Rivera, Mónica Bueno, Diego Ballesteros-Vivas, Alejandro Cifuentes. Chiral analysis in food science. TrAC Trends in Analytical Chemistry 2020, 123 , 115761. https://doi.org/10.1016/j.trac.2019.115761
    11. Ronald S. Jackson. Postfermentation treatments and related topics. 2020, 573-723. https://doi.org/10.1016/B978-0-12-816118-0.00008-8
    12. Liang Chen, Dimitra L. Capone, Emily L. Nicholson, David W. Jeffery. Investigation of intraregional variation, grape amino acids, and pre-fermentation freezing on varietal thiols and their precursors for Vitis vinifera Sauvignon blanc. Food Chemistry 2019, 295 , 637-645. https://doi.org/10.1016/j.foodchem.2019.05.126

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