5-Hydroxy-2-methyl-4-(alkylamino)-2H-pyran-3(6H)-one: A New Sugar-Derived Aminoreductone

Knerr, Thomas; Pischetsrieder, Monika; Severin, Theodor

doi:10.1021/jf00044a014

Cited by 9 publications

(5 citation statements)

References 13 publications

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“…Scorbamic acid, which has the same substitution pattern (amino group at C-2, hydroxyl group at C-3), displays a similar UV maximum at 246.5 nm (H 2 O) (Kurata et al, 1973). The 13 C NMR and UV spectral data are in accordance with literature values of betaines (Knerr et al, 1994). This leads to the conclusion that the previously unknown Maillard reaction product of DHA is 1.…”

Section: Resultssupporting

confidence: 85%

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine

Larisch

Pischetsrieder

Severin

1996

J. Agric. Food Chem.

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The reaction of l-dehydroascorbic acid (DHA) with primary aliphatic amines including N α-acetyllysine was examined by HPLC. A new aminoreductone, 2-deoxy-2-(propylamino)ascorbic acid (1) was isolated and the structure elucidated by spectroscopic data. Furthermore oxalic acid mono- (2) and diamides (3) were identified as important degradation products of DHA under Maillard conditions. 3-Deoxy-3-(alkylamino)ascorbic acids (4), typical condensation products of l-ascorbic acid and amines, were also detected in the reaction mixtures of DHA. All products are formed under oxidative and nonoxidative conditions from DHA. Keywords: Maillard reaction; l-dehydroascorbic acid; l-ascorbic acid; oxalic acid amides; aminoreductones; protein glycation; protein cross link

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Section: Resultssupporting

confidence: 85%

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine

Larisch

Pischetsrieder

Severin

1996

J. Agric. Food Chem.

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“…In 1912, Louis Camille Maillard, for the first time, discovered chemical changes during food processing, describing the reaction between amino acids and sugars at elevated temperatures, typical for food processing conditions [ 3 ]. Since then, only a few defined reaction products of food processing have been isolated and structurally characterized [ 4 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

An Investigation of the Complexity of Maillard Reaction Product Profiles from the Thermal Reaction of Amino Acids with Sucrose Using High Resolution Mass Spectrometry

Golon

Kropf

Vockenroth

et al. 2014

Foods

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Thermal treatment of food changes its chemical composition drastically with the formation of “so-called” Maillard reaction products, being responsible for the sensory properties of food, along with detrimental and beneficial health effects. In this contribution, we will describe the reactivity of several amino acids, including arginine, lysine, aspartic acid, tyrosine, serine and cysteine, with carbohydrates. The analytical strategy employed involves high and ultra-high resolution mass spectrometry followed by chemometric-type data analysis. The different reactivity of amino acids towards carbohydrates has been observed with cysteine and serine, resulting in complex MS spectra with thousands of detectable reaction products. Several compounds have been tentatively identified, including caramelization reaction products, adducts of amino acids with carbohydrates, their dehydration and hydration products, disproportionation products and aromatic compounds based on molecular formula considerations.

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“…The effect was not specific for C 4 -AR, but was evoked in a similar way by two other Maillard products with AR structure, C 6 -AR and AHR. The AR substructure is a group that is found in several Maillard products [48][49][50][51][52][53]. Therefore, it can be assumed that the activity of complex Maillard mixtures or processed foods, such as coffee, is not necessarily related to a defined AR, but to a group of reaction products with AR substructures.…”

Section: Discussionmentioning

confidence: 99%

Identification of aminoreductones as active components in Maillard reaction mixtures inducing nuclear NF-κB translocation in macrophages

Wühr

Deckert

Pischetsrieder

2010

Mol. Nutr. Food Res.

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Coffee, a highly processed food, and Maillard mixtures are able to activate nuclear factor kappaB translocation in macrophages via generation of hydrogen peroxide. In this study, a substructure library was prepared and used to identify Maillard products that are responsible for this effect. Three different Maillard reaction products with aminoreductone substructure (C(6)-aminoreductone, C(4)-aminoreductone, and aminohexose reductone) strongly induce nuclear factor kappaB translocation in macrophages. The effect was almost completely blocked by co-incubation with catalase, indicating that cellular activation was mediated by the ability of the test compounds to generate hydrogen peroxide. The cellular effect of a Maillard mixture, which was produced under conditions favoring aminoreductone formation, could be almost completely related to the presence of C(6)-aminoreductone.

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5-Hydroxy-2-methyl-4-(alkylamino)-2H-pyran-3(6H)-one: A New Sugar-Derived Aminoreductone

Cited by 9 publications

References 13 publications

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine

An Investigation of the Complexity of Maillard Reaction Product Profiles from the Thermal Reaction of Amino Acids with Sucrose Using High Resolution Mass Spectrometry

Identification of aminoreductones as active components in Maillard reaction mixtures inducing nuclear NF-κB translocation in macrophages

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5-Hydroxy-2-methyl-4-(alkylamino)-2H-pyran-3(6H)-one: A New Sugar-Derived Aminoreductone

Cited by 9 publications

References 13 publications

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including Nα-Acetyllysine

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including Nα-Acetyllysine

An Investigation of the Complexity of Maillard Reaction Product Profiles from the Thermal Reaction of Amino Acids with Sucrose Using High Resolution Mass Spectrometry

Identification of aminoreductones as active components in Maillard reaction mixtures inducing nuclear NF-κB translocation in macrophages

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Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine

Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine