Evidence of Enzymatic and Chemical Interconversions of Barley Malt 3-Sulfanylhexanol Conjugates during Mashing

被引:4
作者
Chenot, Cecile [1 ]
Collin, Sonia [1 ]
Suc, Lucas [2 ]
Roland, Aurelie [2 ]
机构
[1] Catholic Univ Louvain, Unite Brasserie & Ind Alimentaires, Louvain Inst & Biomol Sci & Technol LIBST, Fac Bioingn, B-1348 Louvain La Neuve, Belgium
[2] Univ Montpellier, Inst Agro, SPO, INRAE, F-34060 Montpellier, France
关键词
polyfunctional thiols; glutathione; S-conjugates; barley malt; gamma GT; POLYFUNCTIONAL THIOLS; 1ST IDENTIFICATION; GLUTATHIONE; HOPS; CYSTEINE; 3-MERCAPTOHEXAN-1-OL; QUANTIFICATION; DEGRADATION; PRECURSORS; BEER;
D O I
10.1021/acs.jafc.3c03640
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Recent studies have highlighted in malt the occurrence of the glutathionylated precursor of 3-sulfanylhexanol (G-3SHol) at concentrations reaching hundreds of mu g/kg. Here, SIDA-LC-MS/MS was used to investigate the potential conversion of G-3SHol to its dipeptide and cysteinyl analogues during mashing. At 45 and 55 degrees C, malt gamma GT and carboxypeptidase activities quickly degrade G-3SHol (up to 90% loss), first to the cysteinylglycine conjugate and then to the cysteine conjugate (up to 205% increase). No gamma-glutamylcysteine S-conjugate formation is observed. At 80 degrees C, despite enzyme inactivation, the G-3SHol level decreases steadily because of suspected imine formation with wort aldehydes at pH 5.5. More surprisingly, CysGly-3SHol is still generated at 80 degrees C. This indicates the presence in the wort of as yet unidentified precursors.
引用
收藏
页码:13107 / 13113
页数:7
相关论文
共 38 条
[1]  
Balakrishna Sharath, 2014, [Frontiers in Biology, 生物学前沿], V9, P51
[2]   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 [J].
Bonnaffoux, Hugo ;
Roland, Aurelie ;
Remond, Emmanuelle ;
Delpech, Stephane ;
Schneider, Remi ;
Cavelier, Florine .
FOOD CHEMISTRY, 2017, 237 :877-886
[3]   Unusual Profile of Thiol Precursors in Special Malts: First Evidence of Chemical Glutathione-/γGluCys- and CysGly-/Cys- Conversions [J].
Chenot, Cecile ;
Collin, Sonia ;
Suc, Lucas ;
Roland, Aurelie .
JOURNAL OF THE AMERICAN SOCIETY OF BREWING CHEMISTS, 2024, 82 (01) :15-22
[4]   First evidence of the glutathione S-conjugate of 3-sulfanylheptanol in green malt: discrepancy with the ubiquitous 5-and 6-C analogues [J].
Chenot, Cecile ;
Robiette, Raphael ;
Collin, Sonia .
JOURNAL OF THE INSTITUTE OF BREWING, 2022, 128 (02) :43-51
[5]   Malt and Hop as Sources of Thiol S-Conjugates: Thiol-Releasing Property of Lager Yeast during Fermentation [J].
Chenot, Cecile ;
Donck, William ;
Janssens, Philippe ;
Collin, Sonia .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2022, 70 (10) :3272-3279
[6]   Ability of Exogenous or Wort Endogenous Enzymes to Release Free Thiols from Hop Cysteinylated and Glutathionylated S-Conjugates [J].
Chenot, Cecile ;
Willemart, Guillaume ;
Gros, Jacques ;
Collin, Sonia .
JOURNAL OF THE AMERICAN SOCIETY OF BREWING CHEMISTS, 2023, 81 (01) :33-44
[7]   Thiol S-Conjugate Profiles: A Comparative Investigation on Dual Hop and Grape Must with Focus on Sulfanylalkyl Aldehydes and Acetates Adducts [J].
Chenot, Cecile ;
Haest, Sebastien ;
Robiette, Raphael ;
Collin, Sonia .
JOURNAL OF THE AMERICAN SOCIETY OF BREWING CHEMISTS, 2023, 81 (01) :23-32
[8]   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].
Chenot, Cecile ;
de Chanvalon, Eloi Thibault ;
Janssens, Philippe ;
Collin, Sonia .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2021, 69 (21) :6005-6012
[9]   Ability of the Mandarina Bavaria hop variety to release free odorant polyfunctional thiols in late-hopped beers [J].
Chenot, Cecile ;
Collin, Sonia .
JOURNAL OF THE INSTITUTE OF BREWING, 2021, 127 (02) :140-148
[10]   First Evidence of the Cysteine and Glutathione Conjugates of 3-Sulfanylpentan-1-ol in Hop (Humulus lupulus L.) [J].
Chenot, Cecile ;
Robiette, Raphael ;
Collin, Sonia .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (14) :4002-4010