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The Chemical Reaction of Glutathione and trans-2-Hexenal in Grape Juice Media To Form Wine Aroma Precursors: The Impact of pH, Temperature, and Sulfur Dioxide
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-01-23 00:00:00 , DOI: 10.1021/acs.jafc.7b04991 Andrew C. Clark 1, 2 , Rebecca C. Deed 3
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-01-23 00:00:00 , DOI: 10.1021/acs.jafc.7b04991 Andrew C. Clark 1, 2 , Rebecca C. Deed 3
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The aldehyde 3-S-glutathionylhexanal is an intermediate which is produced during the formation of the wine aroma precursor 3-S-glutathionylhexanol, after the reaction of glutathione with trans-2-hexenal. This study was conducted to assess whether the chemical, as opposed to the enzymatic, production of 3-S-glutathionylhexanal could occur at a significant rate in grape juice. LC–MS/MS was used in low- and high-resolution modes, in combination with functional group derivatization, to identify and quantitate products. In comparison to cysteine, glutathione was found to induce less cyclized products on reaction with trans-2-alkanals and the glutathione-derived products were more reactive to hydrogen sulfite. The zero-order rates for 3-S-glutathionylhexanal formation in model grape juice were 1.08 ± 0.08 and 0.45 ± 0.05 mg/(L·day) glutathione equivalents at 25 and 13 °C, respectively, and the reaction rate increased 3-fold by increasing the pH from 3.2 to 3.8. 3-S-Glutathionylhexanal was detected in all five white grape juices examined. The concentration of the aldehyde could be increased by up to 10-fold after being released from hydrogen sulfite, demonstrating a potentially novel source for the production of varietal thiol aroma compounds in wine.
中文翻译：
葡萄汁中谷胱甘肽与反式-2-己烯醛的化学反应形成葡萄酒香气前体：pH，温度和二氧化硫的影响
醛3- S-谷胱甘肽己醛是谷胱甘肽与反式-2-己烯醛反应后在酒香气前体3- S-谷胱甘肽己醇形成过程中产生的中间体。进行这项研究的目的是评估在葡萄汁中是否能以显着的速率产生3- S-谷胱甘肽己醛的化学产物，而不是酶促产物。LC-MS / MS用于低分辨率和高分辨率模式，并与官能团衍生化结合使用，以鉴定和定量产品。与半胱氨酸相比，发现谷胱甘肽在与反式反应时诱导环化产物较少-2-烷基和谷胱甘肽衍生的产物对亚硫酸氢根更具反应性。模型葡萄汁中3- S-谷胱甘肽己醛形成的零级速率分别在25和13°C时分别为1.08±0.08和0.45±0.05 mg /（L·天）谷胱甘肽当量，反应速率提高了3倍通过将pH从3.2增加到3.8。在所检查的所有五种白葡萄汁中均检测到3- S-谷胱甘肽己醛。从亚硫酸氢盐释放后，醛的浓度最多可增加10倍，这证明了在葡萄酒中生产各种硫醇香气化合物的潜在新来源。
更新日期：2018-01-23
中文翻译：
葡萄汁中谷胱甘肽与反式-2-己烯醛的化学反应形成葡萄酒香气前体：pH，温度和二氧化硫的影响
醛3- S-谷胱甘肽己醛是谷胱甘肽与反式-2-己烯醛反应后在酒香气前体3- S-谷胱甘肽己醇形成过程中产生的中间体。进行这项研究的目的是评估在葡萄汁中是否能以显着的速率产生3- S-谷胱甘肽己醛的化学产物，而不是酶促产物。LC-MS / MS用于低分辨率和高分辨率模式，并与官能团衍生化结合使用，以鉴定和定量产品。与半胱氨酸相比，发现谷胱甘肽在与反式反应时诱导环化产物较少-2-烷基和谷胱甘肽衍生的产物对亚硫酸氢根更具反应性。模型葡萄汁中3- S-谷胱甘肽己醛形成的零级速率分别在25和13°C时分别为1.08±0.08和0.45±0.05 mg /（L·天）谷胱甘肽当量，反应速率提高了3倍通过将pH从3.2增加到3.8。在所检查的所有五种白葡萄汁中均检测到3- S-谷胱甘肽己醛。从亚硫酸氢盐释放后，醛的浓度最多可增加10倍，这证明了在葡萄酒中生产各种硫醇香气化合物的潜在新来源。
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