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Research Articles

Ability of Exogenous or Wort Endogenous Enzymes to Release Free Thiols from Hop Cysteinylated and Glutathionylated S-Conjugates

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Pages 33-44 | Received 30 Sep 2021, Accepted 20 Dec 2021, Published online: 26 Jan 2022

Literature cited

  • Lermusieau, G.; Bulens, M.; Collin, S. Use of GC-Olfactometry to Identify the Hop Aromatic Compounds in Beer. J. Agric. Food Chem. 2001, 49, 3867–3874. DOI: 10.1021/jf0101509.
  • Gros, J.; Nizet, S.; Collin, S. Occurrence of Odorant Polyfunctional Thiols in the Super Alpha Tomahawk Hop Cultivar. Comparison with the Thiol-Rich Nelson Sauvin Bitter Variety. J. Agric. Food Chem. 2011, 59, 8853–8865. DOI: 10.1021/jf201294e.
  • Vermeulen, C.; Gijs, L.; Collin, S. Sensorial Contribution and Formation Pathways of Thiols in Foods: A Review. Food Rev. Int. 2005, 21, 69–137. DOI: 10.1081/FRI-200040601.
  • Vermeulen, C.; Lejeune, I.; Tran, T. T. H.; Collin, S. Occurrence of Polyfunctional Thiols in Fresh Lager Beers. J. Agric. Food Chem. 2006, 54, 5061–5068. DOI: 10.1021/jf060669a.
  • Gros, J.; Peeters, F.; Collin, S. Occurrence of Odorant Polyfunctional Thiols in Beers Hopped with Different Cultivars. First Evidence of an S-Cysteine Conjugate in Hop (Humulus lupulus L.). J. Agric. Food Chem. 2012, 60, 7805–7816. DOI: 10.1021/jf301478m.
  • Tominaga, T.; Peyrot Des Gachons, C.; Dubourdieu, D. A New Type of Flavor Precursors in Vitis vinifera L. Cv. Sauvignon Blanc: S-Cysteine Conjugates. J. Agric. Food Chem. 1998, 46, 5215–5219. DOI: 10.1021/jf980481u.
  • Roland, A.; Delpech, S.; Dagan, L. How to Monitor Positive Aromatic Thiols during Winemaking and Brewing. In Hop Flavor and Aroma: Proceedings of the 2nd International Brewers Symposium; Scientific Societies: St. Paul, MN, Chapter 4, 2020, pp 49–70.
  • Chenot, C.; Robiette, R.; Collin, S. First Evidence of the Cysteine and Glutathione Conjugates of 3-Sulfanylpentan-1-ol in Hop (Humulus lupulus L.). J. Agric. Food Chem. 2019, 67, 4002–4010. DOI: 10.1021/acs.jafc.9b00225.
  • Roland, A.; Viel, C.; Reillon, F.; Delpech, S.; Boivin, P.; Schneider, R.; Dagan, L. First Identification and Quantification of Glutathionylated and Cysteinylated Precursors of 3-Mercaptohexan-1-ol and 4-Methyl-4-Mercaptopentan-2-One in Hops (Humulus lupulus): Thiol Aroma Potential in Hops. Flavour Fragr. J. 2016, 31, 455–463. DOI: 10.1002/ffj.3337.
  • Chenot, C.; Collin, S. First Evidence of the Glutathione S-Conjugate of 3-Sulfanylheptanol in Green Malt. J. Inst. Brew. (in press).
  • Foyer, C. H.; Halliwell, B. The Presence of Glutathione and Glutathione Reductase in Chloroplasts: A Proposed Role in Ascorbic Acid Metabolism. Planta. 1976, 133, 21–25. DOI: 10.1007/BF00386001.
  • Gill, S. S.; Anjum, N. A.; Hasanuzzaman, M.; Gill, R.; Trivedi, D. K.; Ahmad, I.; Pereira, E.; Tuteja, N. Glutathione and Glutathione Reductase: A Boon in Disguise for Plant Abiotic Stress Defense Operations. Plant Physiol. Biochem. 2013, 70, 204–212. DOI: 10.1016/j.plaphy.2013.05.032.
  • Hasanuzzaman, M.; Nahar, K.; Anee, T. I.; Fujita, M. Glutathione in Plants: Biosynthesis and Physiological Role in Environmental Stress Tolerance. Physiol. Mol. Biol. Plants. 2017, 23, 249–268. DOI: 10.1007/s12298-017-0422-2.
  • Edwards, R.; Dixon, D. P.; Walbot, V. Plant Glutathione S-Transferases: Enzymes with Multiple Functions in Sickness and in Health. Trends Plant Sci. 2000, 5, 193–198. DOI: 10.1016/S1360-1385(00)01601-0.
  • Foyer, C. H.; Theodoulou, F. L.; Delrot, S. The Functions of Inter- and Intracellular Glutathione Transport Systems in Plants. Trends Plant Sci. 2001, 6, 486–492. DOI: 10.1016/S1360-1385(01)02086-6.
  • Lappartient, A. G.; Touraine, B. Demand-Driven Control of Root ATP Sulfurylase Activity and SO42- Uptake in Intact Canola (the Role of Phloem-Translocated Glutathione). Plant Physiol. 1996, 111, 147–157. DOI: 10.1104/pp.111.1.147.
  • Herschbach, C.; Rennenberg, H. Influence of Glutathione (GSH) on Net Uptake of Sulphate and Sulphate Transport in Tobacco Plants. J. Exp. Bot. 1994, 45, 1069–1076. DOI: 10.1093/jxb/45.8.1069.
  • Lancaster, J. E.; Shaw, M. L. Characterization of Purified Gamma-Glutamyl Transpeptidase in Onions: Evidence for In Vivo Role as a Peptidase. Phytochem. 1994, 36, 1351–1358. DOI: 10.1016/S0031-9422(00)89723-X.
  • Storozhenko, S.; Belles-Boix, E.; Babiychuk, E.; Hérouart, D.; Davey, M. W.; Slooten, L.; Van Montagu, M.; Inzé, D.; Kushnir, S. Gamma-Glutamyl Transpeptidase in Transgenic Tobacco Plants. Cellular Localization, Processing, and Biochemical Properties. Plant Physiol. 2002, 128, 1109–1119. DOI: 10.1104/pp.010887.
  • Quiocho, F. A.; Lipscomb, W. N. Carboxypeptidase A: A Protein and an Enzyme. Adv. Protein Chem. 1971, 25, 1–78. DOI: 10.1016/s0065-3233(08)60278-8.
  • Steinkamp, R.; Rennenberg, H. Degradation of Glutathione in Plant Cells: Evidence against the Participation of a γ-Glutamyltranspeptidase. Z. Naturforsch. C. 1985, 40, 29–33. DOI: 10.1515/znc-1985-1-208.
  • Schneider, A.; Rennenberg, H. Degradation of Glutathione (GSH) in Heterotrophic Tobacco Cells. Phyton. 1993, 32, 113–117.
  • Bonnaffoux, H.; Roland, A.; Rémond, E.; Delpech, S.; Schneider, R.; Cavelier, F. First Identification and Quantification of S-3-(Hexan-1-ol)-γ-Glutamyl-Cysteine in Grape Must as a Potential Thiol Precursor, Using UPLC-MS/MS Analysis and Stable Isotope Dilution Assay. Food Chem. 2017, 237, 877–886. DOI: 10.1016/j.foodchem.2017.05.116.
  • Wolf, A. E.; Dietz, K. J.; Schröder, P. Degradation of Glutathione S-Conjugates by a Carboxypeptidase in the Plant Vacuole. FEBS Lett. 1996, 384, 31–34. DOI: 10.1016/0014-5793(96)00272-4.
  • Cooper, A. J. L. Mechanisms of Cysteine S-Conjugate β-Lyases. In Advances in Enzymology - and Related Areas of Molecular Biology; Purich, D. L., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2006; pp 199–238. DOI: 10.1002/9780470123188.ch6.
  • Starkenmann, C.; Troccaz, M.; Howell, K. The Role of Cysteine and Cysteine-S Conjugates as Odour Precursors in the Flavour and Fragrance Industry. Flavour Fragr. J. 2008, 23, 369–381. DOI: 10.1002/ffj.1907.
  • Tran, T. T. H.; Cibaka, M.-L. K.; Collin, S. Polyfunctional Thiols in Fresh and Aged Belgian Special Beers: Fate of Hop S-Cysteine Conjugates. J. Am. Soc. Brew. Chem. 2015, 73, 61–70. DOI: 10.1094/ASBCJ-2015-0130-01.
  • Nizet, S.; Gros, J.; Peeters, F.; Chaumont, S.; Robiette, R.; Collin, S. First Evidence of the Production of Odorant Polyfunctional Thiols by Bottle Refermentation. J. Am. Soc. Brew. Chem. 2013, 71, 15–22. DOI: 10.1094/ASBCJ-2013-0117-01.
  • Chenot, C.; Thibault de Chanvalon, E.; Janssens, P.; Collin, S. Modulation of the Sulfanylalkyl Acetate/Alcohol Ratio and Free Thiol Release from Cysteinylated and/or Glutathionylated Sulfanylalkyl Alcohols in Beer under Different Fermentation Conditions. J. Agric. Food Chem. 2021, 69, 6005–6012. DOI: 10.1021/acs.jafc.1c01610.
  • Gros, J.; Tran, T. T. H.; Collin, S. Enzymatic Release of Odourant Polyfunctional Thiols from Cysteine Conjugates in Hop: Enzymatic Release of Hop Thiols. J. Inst. Brew. 2013, 119, 221–227. DOI: 10.1002/jib.80.
  • Kankolongo Cibaka, M.-L.; Gros, J.; Nizet, S.; Collin, S. Quantitation of Selected Terpenoids and Mercaptans in the Dual-Purpose Hop Varieties Amarillo, Citra, Hallertau Blanc, Mosaic, and Sorachi Ace. J. Agric. Food Chem. 2015, 63, 3022–3030. DOI: 10.1021/jf5058556.
  • Ohkama-Ohtsu, N.; Fukuyama, K.; D. J. Chapter, O. 4 Roles of γ-Glutamyl Transpeptidase and γ-Glutamyl Cyclotransferase in Glutathione and Glutathione-Conjugate Metabolism in Plants. In Advances in Botanical Research; Elsevier: Cambrige, MA, 2009; Vol. 52, pp 87–113. DOI: 10.1016/S0065-2296(10)52004-4.
  • Kankolongo Cibaka, M.-L.; Decourrière, L.; Lorenzo-Alonso, C.-J.; Bodart, E.; Robiette, R.; Collin, S. 3-Sulfanyl-4-Methylpentan-1-ol in Dry-Hopped Beers: First Evidence of Glutathione S-Conjugates in Hop (Humulus lupulus L.). J. Agric. Food Chem. 2016, 64, 8572–8582. DOI: 10.1021/acs.jafc.6b03788.
  • Ferguson, L. R. Role of Plant Polyphenols in Genomic Stability. Mutat. Res. Mol. Mech. Mutagen. 2001, 475, 89–111. DOI: 10.1016/S0027-5107(01)00073-2.
  • Nikolantonaki, M.; Chichuc, I.; Teissedre, P.-L.; Darriet, P. Reactivity of Volatile Thiols with Polyphenols in a Wine-Model Medium: Impact of Oxygen, Iron, and Sulfur Dioxide. Anal. Chim. Acta. 2010, 660, 102–109. DOI: 10.1016/j.aca.2009.11.016.
  • Wang, X.; Chen, L.; Capone, D. L.; Roland, A.; Jeffery, D. W. Evolution and Correlation of Cis-2-Methyl-4-Propyl-1,3-Oxathiane, Varietal Thiols, and Acetaldehyde during Fermentation of Sauvignon Blanc Juice. J. Agric. Food Chem. 2020, 68, 8676–8687. DOI: 10.1021/acs.jafc.0c03183.
  • Chen, L.; Capone, D. L.; Nicholson, E. L.; Jeffery, D. W. Investigation of Intraregional Variation, Grape Amino Acids, and Pre-Fermentation Freezing on Varietal Thiols and Their Precursors for Vitis Vinifera Sauvignon Blanc. Food Chem. 2019, 295, 637–645. DOI: 10.1016/j.foodchem.2019.05.126.

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