Thermal Degradation Products of Several Amadori Compounds

Shigematsu, Hitoshi; Shibata, Saizo; Kurata, Tadao; Kato, Hiromichi; Fujimaki, Masao

doi:10.1080/00021369.1977.10862868

Cited by 11 publications

(16 citation statements)

References 2 publications

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“…Similar to pyrraline and formyline, a low stability of rhamnolysine was expected; however, the apparent stability of the compound may result from degradation reactions of ARPs during roasting that may lead to formation of rhamnolysine. This has been described for other N -substituted methylpyrrolealdehydes . The lysine and arginine contents decrease in parallel to the appearance of glycated amino acids.…”

Section: Resultssupporting

confidence: 65%

“…The rhamnolysine precursor 3-deoxyrhamnosone was detectable only in one sample of Munich malt (0.1 μmol/kg dry mass); therefore, it was not further regarded. The fact that rhamnolysine can be quantitated in malt samples but not its precursor may substantiate the proposed formation of rhamnolysine from ARPs. , …”

Section: Resultsmentioning

confidence: 75%

“…This has been described for other N-substituted methylpyrrolealdehydes. 39 The lysine and arginine contents decrease in parallel to the appearance of glycated amino acids. The concentration of glycated amino acids also decreased during roasting, indicating that not only lysine and arginine are incorporated into melanoidins 40 but also the glycated amino acids.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The fact that rhamnolysine can be quantitated in malt samples but not its precursor may substantiate the proposed formation of rhamnolysine from ARPs. 18,39 The concentrations of (Z)-3,4-DGE were astonishingly high (5−382 μmol/kg or 0.7−55 mg/kg), and in many of the dark and all roasted malts, it exceeded the concentration of 3-DGal. This may be due to the fact that formation of 3-DGal from 3,4-DGE requires the addition of water, which becomes limited at the high processing temperatures applied during production of the respective malts.…”

Section: Determination Of 12-dicarbonyl Compounds and Other Carbohydr...mentioning

confidence: 99%

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Maillard Reaction Products in Different Types of Brewing Malt

Hellwig

Henle

2020

J. Agric. Food Chem.

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Individual Maillard reaction products (MRPs), namely, free and protein-bound glycated amino acids as well as dicarbonyl compounds, were quantitated in various types of brewing malt using chromatographic means. Among the protein-bound glycated amino acids, which were analyzed following enzymatic hydrolysis, N-ε-fructosyllysine was the dominating compound in light (EBC < 10) and dark (10 < EBC < 500) malts, accounting for up to 15.9% of lysine derivatization, followed by N-ε-maltulosyllysine (light malts, up to 4.9% lysine derivatization) or pyrraline (dark malts, up to 10.4% lysine derivatization). Roasting of malt led to the degradation of most of the protein-bound glycated amino acids. The same trends were visible for free glycated amino acids. A novel MRP-derived Strecker aldehyde, namely, 5-(2′-formyl-5′-hydroxymethylpyrrol-1′-yl)-pentanal (pyrralinal), was detected in dark malt. The most abundant 1,2-dicarbonyl compound in malt samples was 3-deoxyglucosone (up to 9 mmol/kg), followed by 3-deoxymaltosone (up to 2 mmol/kg). Only few MRPs such as 5-hydroxymethylfurfural, furfural, the dicarbonyl compounds glyoxal, methylglyoxal, and diacetyl as well as protein-bound rhamnolysine and MG-H1 correlated with the malt color. A comparison of MRPs present in malt with corresponding amounts in beer points to neoformation of MRPs such as MG-H1 and 3-deoxygalactosone during the brewing process.

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Section: Resultssupporting

confidence: 65%

Section: Resultsmentioning

confidence: 75%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Determination Of 12-dicarbonyl Compounds and Other Carbohydr...mentioning

confidence: 99%

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Maillard Reaction Products in Different Types of Brewing Malt

Hellwig

Henle

2020

J. Agric. Food Chem.

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“…Methional was generated from methionine through the Shigematsu reaction. 38,39 The concentrations of methional in hawthorn puree samples of Y1, Y2, and Y3 were, respectively, 0.893, 1.24, and 0.762 μg/kg (Table 2). From Table 2, methional might greatly contribute to the aroma of hawthorn puree with the great OAVs in samples.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Characterization of Odor-Active Volatiles in Hawthorn Puree Using Thermal Desorption System Coupled to Gas Chromatography–Mass Spectrometry–Olfactometry and GC-Flame Photometric Detector

Zhu

Xiao

2018

J. Agric. Food Chem.

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The volatile compounds in hawthorn puree obtained from three cultivars (Y1, Crataegus pinnatif ida Bunge cv. "Waibahong", Y2, Crataegus pinnatif ida Bunge cv. "Damianqiu", and Y3, Crataegus pinnatif ida Bunge cv. "Dajinxing") were analyzed by the thermal desorption system coupled to gas chromatography−mass spectrometry−olfactometry and GC-flame photometric detector. In the samples of Y1, Y2, and Y3, 40, 42, and 42 odor-active compounds were, respectively, identified by olfactometry. Methyl 2-methylbutanoate, methyl hexanoate, hexyl isobutanoate, methional, heptanal, and (Z)-3-hexenyl acetate contributed largely to the characteristic aroma of the three samples. Additionally, the odor activity value (OAV) was used to determine the main compounds and 3-mercaptohexyl acetate (OAV: 10−18), 3-mercapto-2-methylpentanal (OAV: 4−7), methyl 2-methylbutanoate (OAV: 9−21), methyl hexanoate (OAV: 8−16), and 2-pentyl acetate (OAV: 5−12) were considered as the important contributors to the aroma of hawthorn samples.

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