Reaction of Folic Acid with Reducing Sugars and Sugar Degradation Products

Abstract

The reaction of folic acid with reducing sugars (nonenzymatic glycation) under conditions that can occur during food processing and preparation was studied by high-performance liquid chromatography with diode array detection. N-(p-Aminobenzoyl)-L-glutamic acid, a well-established oxidation product, was detected in the reaction mixtures. Furthermore, a new product was isolated and identified as N2-[1-(carboxyethyl)]folic acid (CEF). CEF was the main product that was formed by the nonenzymatic glycation of folic acid. For preparation, N2-[1-(carboxyethyl)]folic acid was obtained in high yields when folic acid and dihydroxyacetone (DHA), a sugar degradation product, were heated at 100 degrees C in phosphate buffer. Mixtures of folic acid and different sugars or DHA were heated under variation of reaction time and temperature, and CEF was quantified. Up to 50% of the vitamin was converted to CEF, with highest yields formed from maltose (49%) and lactose (43%).

Nonenzymatic glycation reaction of folate with reducing sugars: A case study on [6S]-5-methyltetrahydrofolate and fructose

“…Secondly fructose (1.5 M) influenced the estimated temperature dependence of the rate constants, showing a lower temperature dependence when fructose was added to the samples prior to the treatment. MS analysis of a heated (90°C, 120 min) [6S]-5-CH 3 PteH 4 Glu solution (0.4 µM) with fructose (1.5M) suggested that natural folates are probably subjected to a similar nonenzymatic glycation reaction with fructose, as has been reported for PteGlu (Schneider et al, 2002). Conclusion Addition of fructose to [6S]-5-CH 3 PteH 4 Glu solutions prior to thermal treatments, resulted in a higher folate instability, probably caused by a nonenzymatic glycation reaction.…”

Assessment of Feasibility of Maillard Reaction between Baclofen and Lactose by Liquid Chromatography and Tandem Mass Spectrometry, Application to Pre Formulation Studies

“…Maillard reaction has been extensively studied and reviewed, especially in the food-and nutrition-related literature and it is a well-documented process for the degradation of lactose during the heating of milk (3,(10)(11)(12)(13)(14). Nowadays, mass spectrometry (MS) has been adopted by many researchers attempting to reveal the details of Maillard chemistry (9,(15)(16)(17)(18).…”

Studies on New Folates in Fortified Foods and Assessment of Their Bioavailability and Bioactivity

“…[2] found a glycation product of FA, CEF, in models containing sugars and FA, CEF is a conceivable compound in fortifi ed foods that are similarly composed and undergo a similar treatment to that in the models used by Schneider et al . Possible examples are multivitamin juices containing carbohydrates that are pasteurized to make them shelf -stable.…”

“…The most successful way was that described by Schneider et al . [2] by reacting FA with dihydroxyacetone ( DHA ) and purifying CEF from unreacted FA by preparative HPLC [5] . NMR experiments revealed similar data to those reported by Schneider et al .…”

“…In this context, a nonenzymatic glycation involving carbohydrates and FA acting as an amino compound was reported in 2002 [2] . The product, N 2 -[1 -(1 -carboxy) ethyl]folic acid (CEF) was structurally characterized and its formation was followed in models involving different carbohydrates and their degradation products.…”