Interaction of Added <scp>l</scp>-Cysteine with 2-Threityl-thiazolidine-4-carboxylic Acid Derived from the Xylose–Cysteine System Affecting Its Maillard Browning

Zhai, Yun; Cui, Heping; Hayat, Khizar; Hussain, Shahzad; Tahir, Muhammad Usman; Yu, Jun; Jia, Chengsheng; Zhang, Xiaoming; Ho, Chi‐Tang

doi:10.1021/acs.jafc.9b04374

Cited by 28 publications

(42 citation statements)

References 38 publications

(75 reference statements)

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“…Synthesis and Purification Asp−Xyl-ARP. The aspartic acid− xylose ARP (Asp−Xyl-ARP) were prepared according to the method of Zhai et al 21 Xylose and aspartic acid were dissolved in 200 mL of deionized water (total concentration of 43 mg/mL) in a 2:1 M ratio. The conditions were scaled down based on industrial conditions, and ARP preparation would be scaled up proportionally for industrialization in the future.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Accelerated Dissipation of Free and Immobilized Water Facilitating the Intramolecular Dehydration of N-Xylosamine and Conversion Improvement of the Amadori Rearrangement Product of Aspartic Acid–Xylose Reaction

Zhang

Cui

Hayat

et al. 2021

J. Agric. Food Chem.

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Compared to the method of aqueous Maillard reaction at atmospheric pressure tandem vacuum concentration, a coupling dehydration method combining spray drying and vacuum drying was used to increase aspartic acid−xylose conversion to the Amadori rearrangement product (ARP). The water activity and moisture states were found as effective indicators to characterize the degree of dehydration of Maillard reaction intermediates and efficient formation of ARP. During the vacuum drying process, the water activity of the product powder decreased significantly. Because the formation of ARP was accompanied by intramolecular dehydration, combining spray drying and vacuum drying increased the proportion of bound water in the vacuum-dried product. Free water was easily dissipated via dehydration, which then converted the immobilized water continuously to free water, and the decreased immobilized water further converted the bound water to immobilized water. The reduction in bound water contributed to the intramolecular dehydration of N-substituted D-xylosamine, which would further be transformed to be the ARP through an intramolecular rearrangement. The yield of ARP was increased from 1.68 to 21.53% after spray drying. The ARP yield was substantially increased up to 77.9% by subsequent vacuum drying.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Accelerated Dissipation of Free and Immobilized Water Facilitating the Intramolecular Dehydration of N-Xylosamine and Conversion Improvement of the Amadori Rearrangement Product of Aspartic Acid–Xylose Reaction

Zhang

Cui

Hayat

et al. 2021

J. Agric. Food Chem.

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“…The solution was rapidly cooled in an ice bath for further purification. The purification procedure of TTCA was accomplished according to our previous study …”

Section: Methodsmentioning

confidence: 99%

“…The quantitative analysis of TTCA and ARP was performed by high-performance liquid chromatography–evaporative light scattering detection (HPLC-ELSD) using the purified compounds prepared in our laboratory as external standards, referring to our previous study . The analytical-grade Cys and Xyl were used as external standards for their quantitation.…”

Section: Methodsmentioning

confidence: 99%

“…Deng et al also confirmed that the addition of extra methionine to the thermal reaction system of methionine–glucose-derived ARP could contribute to the acceleration of browning formation, which was ascribed to the fact that the additional amino acid could promote the formation of some color precursors, including short-chained α-dicarbonyl compounds. According to the MR mechanism, the amino acids actively participate in a series of reactions with α-dicarbonyl compounds through the retro-aldolization and dehydration reactions. , However, existing studies revealed that additional Cys could inhibit the normal degradation pathways from TTCA to its downstream products and finally obtain a product with light color . Therefore, Cys addition is not suitable for the acceleration of TTCA degradation as well as the rapid generation of browning and flavor.…”

Section: Introductionmentioning

confidence: 99%

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Degradation of 2-Threityl-Thiazolidine-4-Carboxylic Acid and Corresponding Browning Accelerated by Trapping Reaction between Extra-Added Xylose and Released Cysteine during Maillard Reaction

Zhai

Cui

Zhang

et al. 2021

J. Agric. Food Chem.

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2-Threityl-thiazolidine-4-carboxylic acid (TTCA), a nonvolatile precursor of flavor and color, is considered to be more stable than its isomeric Amadori compound (ARP). The degradation behavior of TTCA favors higher temperatures and pH. In order to adjust and control the thermal degradation of TTCA to improve its food processing adaptability, a TTCA−Xyl thermal reaction model was constructed to explore the effect of extra-added Xyl on the thermal degradation behavior of TTCA. The results confirmed that the extra-added Xyl was involved in the degradation pathway of TTCA and accelerated its depletion, thus promoting the formation of characteristic downstream products of TTCA including some α-dicarbonyl compounds, and consequently accelerating the browning formation. The isotope-labeling technique was further applied to confirm that the added Xyl could trap the Cys released from the decomposition of ARP and formed additional TTCA, which could promote the movement of chemical equilibrium and gradually accelerate the degradation rate of TTCA as well as melanoidins formation. The higher pH value could even promote this phenomenon.

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“…Previous studies have reported that addition of cysteine to MR system can inhibit the brown color formation and lead to light‐colored Maillard flavor‐enhancing peptides (Eric et al., 2013). Another study revealed that these peptides are generated after the interaction of cysteine and amadori compound and inhibition of dicarbonyl compound (Zhai et al., 2019). A recent study reported the use of glucosamine, a highly reactive amino sugars for the generation of light‐colored Maillard flavor‐enhancing peptides (Fu et al., 2019).…”

Section: Biological Activity Of Mr Productsmentioning

confidence: 99%

Maillard conjugates and their potential in food and nutritional industries: A review

Liu

Xia

et al. 2020

Food Frontiers

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Maillard reaction (MR) is a cascade of complex interactions between reducing sugars and amine groups in food processing and storage. It produces a variety of volatile compound, nonenzymatic intermediates, and high molecular weight melanoidin contributing improved aroma, color, flavor, and antioxidant properties to the final food products. When uncontrolled, it can produce some harmful derivatives such as acrylamide, heterocyclic amine, advanced glycation end Products (AGEs), and other substances that can be detrimental to human health leading to cancer and chronic diseases. Herein, we reviewed the MR leading to different MRPs and factors affecting the MR and MRPs, their application in food model systems, their biological activities, and the formation mechanism and effective inhibition methods of common harmful MRPs. The updated overview can be useful to explore the rational use of MR, which can ameliorate its positive biological features with reduced adverse effects.

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Interaction of Added l-Cysteine with 2-Threityl-thiazolidine-4-carboxylic Acid Derived from the Xylose–Cysteine System Affecting Its Maillard Browning

Cited by 28 publications

References 38 publications

Accelerated Dissipation of Free and Immobilized Water Facilitating the Intramolecular Dehydration of N-Xylosamine and Conversion Improvement of the Amadori Rearrangement Product of Aspartic Acid–Xylose Reaction

Accelerated Dissipation of Free and Immobilized Water Facilitating the Intramolecular Dehydration of N-Xylosamine and Conversion Improvement of the Amadori Rearrangement Product of Aspartic Acid–Xylose Reaction

Degradation of 2-Threityl-Thiazolidine-4-Carboxylic Acid and Corresponding Browning Accelerated by Trapping Reaction between Extra-Added Xylose and Released Cysteine during Maillard Reaction

Maillard conjugates and their potential in food and nutritional industries: A review

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