Formation of Sulfur-Containing Flavor Compounds from [<sup>13</sup>C]-Labeled Sugars, Cysteine, and Methionine

Tressl, Roland; Kersten, E.; Nittka, C.; Rewicki, Dieter

doi:10.1021/bk-1994-0564.ch018

Cited by 20 publications

(19 citation statements)

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“…Using 13 C-labeled pyruvic acid, Yaylayan and Wnorowski (2002) provided evidence for the formation of alanine and glycolaldehyde in pyruvic acid/ethanolamine model system. Tressl et al (1994) using labeled sugars confirmed the conversion of cystein into pyruvic acid through transamination reaction in a model glucose/ cysteine system. Similarly, Yaylayan et al (2000) confirmed the formation of alanine during thermal decomposition of L-serine, through transamination reaction between pyruvic acid and ethanolamine generated in situ, using 13 C-labeled L-serines.…”

Section: Formation Of Amadori Rearrangement Product Through Transaminmentioning

confidence: 70%

Recent Advances in the Chemistry of Strecker Degradation and Amadori Rearrangement: Implications to Aroma and Color Formation

Yaylayan

2003

FSTR

168

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The importance of Strecker degradation lies in its ability to produce Strecker aldehydes and 2-aminocarbonyl compounds, both are critical intermediates in the generation of aromas during Maillard reaction, however, they can also be formed independently of the pathways established for Strecker degradation. Strecker aldehyde can be formed directly either from free amino acids or from Amadori products. Several pathways have been proposed in the literature for the mechanism of this transformation. On the other hand, Amadori or Heyns rearrangements of ammonia with reducing sugars can also generate 2-aminocarbonyl compounds without the formation of Strecker aldehyde. In addition, isomerization of the imine bond of the Schiff base formed between a reducing sugar and an amino acid, can initiate a transamination reaction and convert the amino acid into the corresponding ␣-keto acid and the sugar into its ␣-amino alcohol derivative. The reverse of this reaction, has been documented to produce Amadori products. The ␣-keto acids can either decarboxylate to produce Strecker aldehydes or undergo Strecker degradation (as a ␣-dicarbonyl compound) with amino acids to also produce Strecker aldehydes. This review will examine the role of Strecker degradation and Amadori rearrangement, under the light of recent findings, in controlling the balance among four critically important key intermediates: ␣-dicarbonyl, ␣-hydroxycarbonyl, 2-amino carbonyls and 2-(amino acid)-carbonyl compounds, during the Maillard reaction and hence control relative importance of aromagenic versus chromogenic pathways.

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Section: Formation Of Amadori Rearrangement Product Through Transaminmentioning

confidence: 70%

Recent Advances in the Chemistry of Strecker Degradation and Amadori Rearrangement: Implications to Aroma and Color Formation

Yaylayan

2003

FSTR

168

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“…GSH could undergo self‐cyclization and cleavage reactions in Maillard reaction to form sulfur‐containing compounds. The content of sulfur‐containing compounds in heated ACX and ACG (3.31 and 18.14 ng/mL) were higher than in heated MGX (1.31 ng/mL), and a variety of complex thiazoles and thiophenes were produced, indicating that the free cysteine with higher reactivity was more likely to participate in flavor formation through Maillard reaction (Tressl, Kersten, Nittka, & Rewicki, ). However, the meat‐like aroma in ACX and ACG accompanied by a strong sulfur aroma, which may be result from the high content of thiazoles and thiophenes (Wang et al., ).…”

Section: Resultsmentioning

confidence: 99%

Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment

Sun

Cui

Zhan

et al. 2019

Journal of Food Science

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Maillard reaction intermediate (MGX) generated from glutathione and xylose in aqueous medium was prepared via the Maillard reaction performed under a two-stage temperature increase process. The purified MGX was identified by Fourier-transform infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance as N-(1-deoxyd-xylulos-1-yl)-glutathione (Amadori compound, C 15 H 25 O 10 N 3 S) with five main isomers. The method of Maillard reaction performed under a two-stage temperature increase process was further verified by high-performance liquid chromatography. The optimal reaction time and temperature for the preparation of MGX was determined as 60 min at 90°C. The yield of MGX was increased from 8.60% to 55.52% through thermal reaction coupled with vacuum dehydration. In addition, rapid and more Maillard-type volatile compounds were formed in MGX during thermal treatment than that in Maillard reaction products or glutathione-xylose mixture. Beside, MGX possessed more pleasing meat-like volatile profile compared with the Amadori compound of glutamic acid-xylose (AAX), cysteine-xylose (ACX), and glycinexylose (AGX). Therefore, it suggested that the MGX had the potential to achieve a better flavor formation during thermal treatment.Keywords: a 2-stage temperature increase process, Maillard reaction intermediate, Maillard-type volatile formation, N-(1-deoxy-d-xylulos-1-yl)-glutathione, thermal treatmentPractical Application: Maillard reaction intermediates, such as Amadori or Heyns rearrangement products (ARP or HRP), are important flavor precursors, which possess stable physicochemical properties, but tend to degrade into flavor compounds at high temperatures. Maillard reaction intermediate from glutathione and xylose acts as primary flavor enhancers to complete Maillard reaction to produce flavors in the subsequent thermal processing, which can significantly improve and stabilize the flavor quality of the meaty food, and deserves a very broad application prospects. The new developed method will be a significant theoretical basis on research preparation and properties of Maillard reaction intermediates in complex food systems.

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“…Hexanal, heptanal, octanal, nonanal, and decanal result from the autoxidation of unsaturated fatty acids through the spontaneous decomposition of hydroperoxides promoted by heat (Grosch 1982). Volatile sulfur compounds are generated during thermal decomposition of sulfur containing amino acids of milk proteins, mainly β‐lactoglobulin (Parry 1974; de Koning and others 1990; Chan and Reineccius 1994; Tressl and others 1994; Zheng and Ho 1994). Methyl ketones are formed during heat treatment by β‐oxidation of saturated fatty acids followed by decarboxylation (Nawar 1996) or by decarboxylation of β‐keto acids naturally present in milk fat (Grosch 1982; Jensen and others 1995).…”

Section: Resultsmentioning

confidence: 99%

Kinetic Analysis of Volatile Formation in Milk Subjected to Pressure‐Assisted Thermal Treatments

Vázquez‐Landaverde¹,

Qian²,

Torres³

2007

Journal of Food Science

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Volatile formation in milk subjected to pressure-assisted thermal processing (PATP) was investigated from a reaction kinetic analysis point of view to illustrate the advantages of this technology. The concentration of 27 volatiles of different chemical class in milk subjected to pressure, temperature, and time treatments was fitted to zero-, 1st-, and 2nd-order chemical reaction models. Temperature and pressure effects on rate constants were analyzed to obtain activation energy (E(a)) and activation volume (deltaV*) values. Hexanal, heptanal, octanal, nonanal, and decanal followed 1st-order kinetics with rate constants characterized by E(a) values decreasing with pressure reflecting negative deltaV* values. Formation of 2-methylpropanal, 2,3-butanedione, and hydrogen sulfide followed zero-order kinetics with rate constants increasing with temperature but with unclear pressure effects. E(a) values for 2-methylpropanal and 2,3-butanedione increased with pressure, that is, deltaV* > 0, whereas values for hydrogen sulfide remained constant, that is, deltaV* = 0. The concentration of all other volatiles, including methanethiol, remained unchanged in pressure-treated samples, suggesting large negative deltaV* values. The concentration of methyl ketones, including 2-pentanone, 2-hexanone, 2-heptanone, 2-octanone, 2-nonanone, 2-decanone, and 2-undecanone, was independent of pressure and pressure-holding time. PATP promoted the formation of few compounds, had no effect on some, and inhibited the formation of volatiles reported to be factors of the consumer rejection of "cooked" milk flavor. The kinetic behavior observed suggested that new reaction formation mechanisms were not likely involved in volatile formation in PATP milk. The application of the Le Chatelier principle frequently used to explain the high quality of pressure-treated foods, often with no supporting experimental evidence, was not necessary.

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Formation of Sulfur-Containing Flavor Compounds from [¹³C]-Labeled Sugars, Cysteine, and Methionine

Cited by 20 publications

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Recent Advances in the Chemistry of Strecker Degradation and Amadori Rearrangement: Implications to Aroma and Color Formation

Recent Advances in the Chemistry of Strecker Degradation and Amadori Rearrangement: Implications to Aroma and Color Formation

Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment

Kinetic Analysis of Volatile Formation in Milk Subjected to Pressure‐Assisted Thermal Treatments

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Formation of Sulfur-Containing Flavor Compounds from [13C]-Labeled Sugars, Cysteine, and Methionine

Cited by 20 publications

References 0 publications

Recent Advances in the Chemistry of Strecker Degradation and Amadori Rearrangement: Implications to Aroma and Color Formation

Recent Advances in the Chemistry of Strecker Degradation and Amadori Rearrangement: Implications to Aroma and Color Formation

Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment

Kinetic Analysis of Volatile Formation in Milk Subjected to Pressure‐Assisted Thermal Treatments

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Formation of Sulfur-Containing Flavor Compounds from [¹³C]-Labeled Sugars, Cysteine, and Methionine