Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes

Wang, Tianze; Zhen, Dawei; Tan, Jia Heng; Xie, Jianchun; Cheng, Jie; Zhao, Jian

doi:10.1016/j.foodchem.2019.125482

Cited by 28 publications

(31 citation statements)

References 30 publications

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“… 23,24 It was reported that first reduction of hexanal and pentanal to hexanol and pentanol and then reacting with H 2 S could form 1‐pentanethiol and 1‐hexanethiol, respectively 24 . Moreover, the reaction of ( E,E )‐2,4‐nonadienal and ( E,E )‐2,4‐decadienal with H 2 S could lead to the generation of 2‐pentylthiophene and 2‐hexylthiophene, respectively, 24,25 while that of ( E,E )‐2,4‐nonadienal with NH 3 could form 2‐pentylpyridine 2 …”

Section: Resultsmentioning

confidence: 99%

“…In particular, they could be due to the instability of the lipid degradation aldehydes to form these lipid‐Maillard compounds during heating. It is known that these aldehydes could be oxidized and aldol/retro‐aldol reacted in the presence of an amino compound such as amino acids during heating 24,25,28 . For example, pentanal could be oxidized into pentanoic acid and ( E,E )‐2,4‐nonadienal could be retro‐aldol reacted into pentanal and 2‐butanenal.…”

Section: Resultsmentioning

confidence: 99%

“… a The retention indices (RIs) before “/” were determined in the experiments while after “/” were all copied from the published data in the Nist 11 database, except that with * from the Reference [10] and with ** from the reference [25]; “‐”, no data found. …”

Section: Methodsmentioning

confidence: 99%

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Effect of lipid on formation of Maillard and lipid‐Maillard meaty flavour compounds in heated cysteine‐xylose‐methyl linoleate system

Wang

Xie

Zhang

et al. 2022

Flavour & Fragrance J

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The effect of lipid level and reaction temperature and time on the heated cysteinexylose reaction to form meaty flavours was investigated. The presence of 1% or 2% methyl linoleate inhibited the formation of volatile sulfur-containing compounds and heterocyclic compounds via the Maillard reaction, that is Maillard compounds. However, the former was better because of the moderate inhibition and more compounds generated from the lipid-Maillard interaction, that is lipid-Maillard compounds. Partial least squares-discriminant analysis suggested the lipid-Maillard compounds were the main markers during varying dosage of methyl linoleate, reaction temperature (100-140°C) and reaction time (30-180 min). Lower temperatures increased formation of the Maillard compounds (eg, 2-furfurylthiol) or lipid-Maillard compounds (eg, 2-pentylpyridine) with reaction time. However, high temperatures caused their amounts changed in a curve or irregularly due to the complications from the Maillard and lipid oxidization reactions. By comparing time-courses of the levels of cysteine and Cys-Amadori compounds, and 294 and 420 nm UV absorbance values in the reaction systems under 120°C with or without 2% methyl linoleate, it was revealed that the underlying lipid effect mechanism was to initially inhibit and later attend the Maillard reaction, leading to less formation of the Maillard compounds and generation of the lipid-Maillard compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Effect of lipid on formation of Maillard and lipid‐Maillard meaty flavour compounds in heated cysteine‐xylose‐methyl linoleate system

Wang

Xie

Zhang

et al. 2022

Flavour & Fragrance J

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“…These suggested that brushing of suet not only elevated lipid degradation reaction but also the Maillard reaction in generation of volatile flavours as a result of its facilitation in heat transfer. Alternatively, interactions between the Maillard reaction and lipid degradation, 23 and some secondary reactions such as condensation between aliphatic aldehydes or between aliphatic aldehydes and amino compounds might occur 24 . Consequently, generation of certain lipid degradation‐related flavour could not be correlated well with a specific fatty acid.…”

Section: Resultsmentioning

confidence: 99%

Characterization of the key odorants in grilled mutton shashlik with or without suet brushing during grilling

Zhen

Wang

et al. 2020

Flavour & Fragrance J

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Grilled mutton shashlik is highly preferred by Chinese consumers. In this study, the key odorants in grilled mutton shashlik prepared in the traditional Chinese way under open carbon fire with or without suet (mutton fat) brushing during grilling were identified. Solvent‐assisted flavour evaporation (SAFE), combined with gas chromatography‐mass spectrometry (GC‐MS) and gas chromatography‐olfactometry (GC‐O), quantitation, recovery factor correction, and aroma recombination and omission were performed. In total, 57 odorants were identified, which predominantly included aliphatic aldehydes, sulphur‐containing compounds and pyrazines. In comparison, the suet‐brushed mutton shashlik had stronger fatty and sheep‐like odours due to higher levels of odorants generated via lipid degradation. However, the key odorants in both mutton shashlik with or without suet brushing during grilling were identified to be 3‐(methylthio)propanal, 2‐methyl‐3‐furanthiol, 2‐acetylthiazole, 2‐furfurylthiol, bis(2‐methyl‐3‐furyl)disulphide, 2‐acetylpyrazine, 2,5‐dimethylpyrazine, 2‐ethyl‐3,5‐dimethylpyrazine, 2,5‐dimethyl‐4‐hydroxy‐3(2H)furanone, 3‐hydroxy‐2‐butanone, 1‐octen‐3‐ol, (E)‐2‐octenal, (E,Z)‐2,6‐nonadienal, octanal, (E)‐2‐nonenal, nonanal, 4‐methyloctanoic acid and 4‐methylphenol. Notably, (E,E)‐2,4‐decadienal, which usually contributes significantly to cooked meat aroma, was excluded as a key odorant here. The results can help understand effect of fat on meat flavour and provide guidance for preparation of processed meat flavourings with the preferred flavour of grilled mutton shashlik.

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“…In our results, the relative expression level of this gene was increased in the group with high relative content of hexanal, suggesting a link among hexanal, DUSP1 and sugar metabolism. Lipid degradation is also accompanied by changes in glucose-glutathione intermediates [ 33 ], but there is no direct evidence for a role of this gene during changes in the relative hexanal content, and additional studies are needed.…”

Section: Discussionmentioning

confidence: 99%

The SLC27A1 Gene and Its Enriched PPAR Pathway Are Involved in the Regulation of Flavor Compound Hexanal Content in Chinese Native Chickens

Jin

Yuan

Zhao

et al. 2022

Genes

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The role of hexanal in flavor as an indicator of the degree of oxidation of meat products is undeniable. However, the genes and pathways of hexanal formation have not been characterized in detail. In this study, we performed differential gene expression analysis and weighted gene co-expression network analysis (WGCNA) on groups of Tiannong partridge chickens with different relative hexanal content in order to find the genes involved in the formation of hexanal and the specific pathways of hexanal formation. Then we confirmed the relationship of these candidate genes with hexanal using Jingxing Yellow chicken and Wenchang chicken. In this study, WGCNA revealed a module of co-expressed genes that were highly associated with the volatile organic compound hexanal. We also compared transcriptome gene expression data of samples from chicken groups with high and low relative contents of hexanal and identified a total of 651 differentially expressed genes (DEGs). Among them, 356 genes were up regulated, and 295 genes were downregulated. The different biological functions associated with the DEGs, hub genes and hexanal were identified by functional analysis using the Kyoto Encyclopedia of Genes and Genomes (KEGG) annotations. Among all the hub genes in the significant module identified by WGCNA, more were enriched in the PPAR signaling pathway, the proteasome pathway, etc. Additionally, we found that DEGs and hub genes, including SLC27A1, ACOX3, NR4A1, VEGFA, JUN, EGR1, CACNB1, GADD45A and DUSP1, were co-enriched in the peroxisome proliferator-activated receptor (PPAR) signaling pathway, p53 signaling pathway and mitogen-activated protein kinases (MAPK) signaling pathway, etc. Transcriptome results of the Jingxing Yellow chicken population showed that the SLC27A1 gene was significantly associated with hexanal and enriched in the PPAR pathway. Our study provides a comprehensive insight into the key genes related to hexanal content, and can be further explored by functional and molecular studies.

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Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes

Cited by 28 publications

References 30 publications

Effect of lipid on formation of Maillard and lipid‐Maillard meaty flavour compounds in heated cysteine‐xylose‐methyl linoleate system

Effect of lipid on formation of Maillard and lipid‐Maillard meaty flavour compounds in heated cysteine‐xylose‐methyl linoleate system

Characterization of the key odorants in grilled mutton shashlik with or without suet brushing during grilling

The SLC27A1 Gene and Its Enriched PPAR Pathway Are Involved in the Regulation of Flavor Compound Hexanal Content in Chinese Native Chickens

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