Antioxidant Properties of Heterocyclic Intermediates of the Maillard Reaction and Structurally Related Compounds

Abstract

It is well established that a wide range of reductones is formed in the course of the Maillard reaction and that these substances contribute to the oxidative stability of food. The aim of this study was to analyze twelve important heterocyclic intermediates with and without reductone structure as well as structural related substances under equal conditions to compare their antioxidant properties in detail. For this purpose, five methods were selected including photometrical methods like the trolox equivalent antioxidant capacity assay and an electron paramagnetic resonance spectroscopic method. Reductones with furan-3-one structure and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one were reducing in all assays while isomaltol and maltol did not react in assays based on the reduction of metal ions because of their complexing abilities. The introduction of protecting groups to the free hydroxyl functions of selected reductones could nearly eliminate their reducing abilities. In addition, the oxidation products of the different reductive heterocycles were compared after treatment with iodine. Mainly short-chained organic acids like lactic, glycolic and glyceric acid are formed as result of the degradation which indicate 1,3-dicarbonyl cleavage reactions of corresponding tricarbonyl compounds as intermediates of the oxidation.

Inhalation of odors containing DMHF generated by the Maillard reaction affects physiological parameters in rats

“…Thus, changes in autonomic nerve activities indirectly affect hydroperoxide levels, suggesting that the inhalation of DMHF decreased hydroperoxide levels through the suppression of sympathetic nerve activity. On the other hand, DMHF exhibited antioxidative activity following its oral administration to mice 50,51 . Usually, such effect increases with the amount of ingestion.…”

Poster „Aktuelle Themen aus Wissenschaft, Wirtschaft, Recht und Überwachung”

“…Bei der Aufreinigung von MOSH und MOAH mittels planarer Festphasenextraktion ( pSPE ) [7] stören Terpene und Terpenoide aus Ölen ebenfalls, sie migrieren in die Zielzone der MOAH-Fraktion. Durch Imprägnierung der Startzone mit Silbernitrat wurde eine deutliche Reduktion von Squalen und β-Carotin erreicht, die als Beispielsubstanzen untersucht wurden.…”

“…Andererseits führt eine thermische Behandlung von kohlenhydratreichen Lebensmittel, etwa Backen oder Frittieren, zur Karamellsierung und / oder zur Maillardreaktion. Einige dieser Produkte zeigen ebenfalls eine antioxidative Aktivität [6,7].…”

Antioxidant capacity of Maillard reaction products’ fractions with different molecular weight distribution from chicken bone hydrolysate – galactose system

“…Most of brown polymers are high‐molecular‐weight (MW) compounds, while some reaction mixtures and conditions produced low‐MW coloured ones (Bekedam et al ., ; Wang et al ., ). Antioxidant capacity of MRP is also related to some low‐MW intermediates such as aldehyde, reductones and heterocyclic derivatives (Eichner, ; Kanzler et al ., ). Reductones are commonly considered as an effective antioxidant due to their reducing activity and metal chelating ability (Eichner, ), while heterocyclic derivatives substituted with some function groups can act as electron donors to scavenge free radicals (Yanagimote et al ., ; Kanzler et al ., ).…”

“…Antioxidant capacity of MRP is also related to some low‐MW intermediates such as aldehyde, reductones and heterocyclic derivatives (Eichner, ; Kanzler et al ., ). Reductones are commonly considered as an effective antioxidant due to their reducing activity and metal chelating ability (Eichner, ), while heterocyclic derivatives substituted with some function groups can act as electron donors to scavenge free radicals (Yanagimote et al ., ; Kanzler et al ., ). In the recent years, some research has been focused on the antioxidant function of different‐MW MRP fractions.…”