Identification and characterization of reaction products of 5‐hydroxytryptamine with methylglyoxal and glyoxal by liquid chromatography/tandem mass spectrometry

Sachin, L. Sai; Chary, R. Nagarjuna; Pavankumar, P.; Prabhakar, S.

doi:10.1002/rcm.8195

Cited by 3 publications

(6 citation statements)

References 56 publications

(86 reference statements)

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“…The molecular formula of compound 3 was calculated as C 13 H 14 N 2 O 2 based on its positive HRESIMS at m / z 231.11227 (calculated, 231.11280), which is 42.010 26 mass units higher than that of compound 2 , suggesting that compound 3 is a typical β-carboline product produced through the Pictet–Spengler condensation reaction between serotonin and MGO. Therefore, the structure of compound 3 was deduced as shown in Figure , which is consistent with the literature …”

Section: Resultssupporting

confidence: 85%

“…MGO is approixmately 10 000–50 000-fold more reactive than glucose and is considered as the most potent glycating agent. , Plasma MGO levels in type 1 and 2 diabetes mellitus groups were around 2 times higher than those in non-diabetic groups. , In addition, many food products and beverages, such as cookies, breads, honeys, coffee, wine, and carbonated soft drinks, represent exogenous sources of MGO. − As the reactive dicarbonyl metabolite, MGO can react with not only amino acids in protein but also biogenic amines, such as serotonin. A recent in vitro study reported that MGO could react with serotonin in phosphate-buffered saline (PBS) through the Pictet–Spengler condensation pathway . Three reaction products were tentatively identified through liquid chromatography–tandem mass spectrometry (LC–MS/MS) analysis.…”

Section: Introductionmentioning

confidence: 99%

“…However, none of these reaction products were further purified through column chromatograph nor were their structures confirmed by one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) analyses. In addition, the authors did not show the chemical profile of all of the reaction products between serotonin and MGO and did not monitor the changes of these products during the reaction . Therefore, it is unknown whether these compounds are the major stable final products or just the intermediate products between serotonin and MGO.…”

Section: Introductionmentioning

confidence: 99%

“…A recent in vitro study reported that MGO could react with serotonin in phosphate-buffered saline (PBS) through the Pictet−Spengler condensation pathway. 17 Three reaction products were tentatively identified through liquid chromatography−tandem mass spectrometry (LC−MS/ MS) analysis. However, none of these reaction products were further purified through column chromatograph nor were their structures confirmed by one-dimensional (1D) and twodimensional (2D) nuclear magnetic resonance (NMR) analyses.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In addition, the authors did not show the chemical profile of all of the reaction products between serotonin and MGO and did not monitor the changes of these products during the reaction. 17 Therefore, it is unknown whether these compounds are the major stable final products or just the intermediate products between serotonin and MGO. Phenolic compounds have been reported to act as the nucleophiles to react with MGO through the benzene ring.…”

Section: ■ Introductionmentioning

confidence: 99%

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Characterization of Reaction Products and Mechanisms between Serotonin and Methylglyoxal in Model Reactions and Mice

Tang

Sang

2020

J. Agric. Food Chem.

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Serotonin is an important endogenous regulatory neurotransmitter and has also been found in fruits, vegetables, and nuts. Methylglyoxal (MGO) is a reactive dicarbonyl metabolite and also a food toxin that modifies protein and DNA to cause the development of many chronic diseases. The objective of this study is to understand the reaction mechanisms between serotonin and MGO and determine whether serotonin could trap MGO in vivo. Five products were detected in phosphate buffer (pH 7.4) at 37 °C. Four products (compounds 2 and 4–6) were purified from the reaction mixture, and their structures were characterized by the analysis of their high-resolution mass and one- and two-dimensional nuclear magnetic resonance spectra. One product (compound 3), as a result of its instability, could not be properly purified and was tentatively characterized on the basis of its high-resolution mass spectrum and corresponding mass fragments. On the basis of the structures of these five products, two reaction pathways were proposed. Compounds 2, 3, 5, and 6 were produced through the Pictet–Spengler condensation pathway between the primary amine of serotonin and the ketone of MGO, and compound 3 was identified as the intermediate product to form products 2, 5, and 6, whereas compound 4 was formed through nucleophilic substitution by the benzene ring of serotonin, which is a new reaction pathway between biogenic amines and reactive carbonyl species. More importantly, the detection of adducts 2 and 4–6 in mice supports our hypothesis that the reaction between serotonin and MGO also happens in vivo through the same pathways as those in model reactions, suggesting that dietary or endogenous serotonin has the capacity to trap MGO in vivo.

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Section: Resultssupporting

confidence: 85%