Maillard Degradation Pathways of Vitamin C

Smuda, Mareen; Glomb, Marcus A.

doi:10.1002/ange.201300399

Cited by 24 publications

(53 citation statements)

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“…As expected, acetic acid and the counterpart erythronic acid were detected. More recently, we performed a mechanistic in-depth investigation of the degradation pathways of ascorbic acid [70]. Based on the incorporation of activated molecular oxygen generated by e.g.…”

Section: Isomerizationmentioning

confidence: 99%

“…Investigations on the mechanistic reaction pathways in vivo often raise the question, if the observed AGEs stem mainly from glucose degradation or if ascorbic acid has to be considered as the dominant precursor. The discovery of ascorbic acid specific amide-AGEs N 6 -threonyl lysine and N 6 -xylonyl/lyxonyl lysine in in vitro studies [70] and their quantitation in human lens [77] were a first attempt to clarify this issue. Their low abundance raises questions about the role of ascorbic acid as the predominant precursor of AGEs in lens proteins.…”

Section: Relevance In Vivomentioning

confidence: 99%

“…The C5-enediol intermediate can dehydrate to form xylosone or isomerize to yield xylonic acid and lyxonic acid, respectively (Fig. 9)[70].…”

mentioning

confidence: 99%

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Pathways of the Maillard reaction under physiological conditions

2016

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Initially investigated as a color formation process in thermally treated foods, nowadays, the relevance of the Maillard reaction in vivo is generally accepted. Many chronic and age-related diseases such as diabetes, uremia, atherosclerosis, cataractogenesis and Alzheimer's disease are associated with Maillard derived advanced glycation endproducts (AGEs) and α-dicarbonyl compounds as their most important precursors in terms of reactivity and abundance. However, the situation in vivo is very challenging, because Maillard chemistry is paralleled by enzymatic reactions which can lead to both, increases and decreases in certain AGEs. In addition, mechanistic findings established under the harsh conditions of food processing might not be valid under physiological conditions. The present review critically discusses the relevant α-dicarbonyl compounds as central intermediates of AGE formation in vivo with a special focus on fragmentation pathways leading to formation of amide-AGEs.

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Section: Isomerizationmentioning

confidence: 99%

Section: Relevance In Vivomentioning

confidence: 99%

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Pathways of the Maillard reaction under physiological conditions

2016

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“…We found that the formation of N 6 -xylonyl/lyxonyl lysine and N 6 -threonyl lysine (C5 and C4 lysine amide-AGEs) is specific for the Maillard reaction of ascorbic acid degradation products. 10 …”

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confidence: 99%

Comprehensive Analysis of Maillard Protein Modifications in Human Lenses: Effect of Age and Cataract

et al. 2015

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In human lens proteins, advanced glycation endproducts (AGEs) originate from the reaction of glycating agents, e.g., vitamin C and glucose. AGEs have been considered to play a significant role in lens aging and cataract formation. Although several AGEs have been detected in the human lens, the contribution of individual glycating agents to their formation remains unclear. A highly sensitive liquid chromatography–tandem mass spectrometry multimethod was developed that allowed us to quantitate 21 protein modifications in normal and cataractous lenses, respectively. N6-Carboxymethyl lysine, N6-carboxyethyl lysine, N7-carboxyethyl arginine, methylglyoxal hydroimidazolone 1, and N6-lactoyl lysine were found to be the major Maillard protein modifications among these AGEs. The novel vitamin C specific amide AGEs, N6-xylonyl and N6-lyxonyl lysine, but also AGEs from glyoxal were detected, albeit in minor quantities. Among the 21 modifications, AGEs from the Amadori product (derived from the reaction of glucose and lysine) and methylglyoxal were dominant.

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“…The development of such mixing elements is mainly based on experience so far. Simulations have been used only in few cases, and most of them neglected the non-Newtonian flow behavior or dissipation effects [2,3,4,5,6]. Especially when processing shear-sensitive materials, only distributive mixing elements can be used to avoid excessive dissipative heating of the polymer melt.…”

Section: Introductionmentioning

confidence: 99%