Characterization of Fumonisin B1-GlucoseReaction Kinetics and Products
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Abstract
The reaction of fumonisin B1 with the reducing sugar D-glucose can block the primary amine group of fumonisin B1 and may detoxify this mycotoxin. A method to separate hundred milligram quantities of fumonisin B1-glucose reaction products from the excess D-glucose with a reversed-phase C18 cartridge was developed. Mass spectrometry revealed that there were four primary products in this chain reaction when fumonisin B1 was heated with D-glucose at 65 C for 48 h: N-methyl-fumonisin B1, N-carboxymethyl-fumonisin B1, N-(3-hydroxyacetonyl)-fumonisin B1, and N-(2-hydroxy, 2-car- boxyethyl)-fumonisin B1. The N-(1-deoxy-D-fructos-1-yl) fumonisin B1 (fumonisin B1-glucose Schiff’s base) was detected by mass spectrometry when fumonisin B1 was heated with D-glucose at 60 C. The nonenzymatic browning reaction of fumonisin B1 with excess D-glucose followed apparent first- order kinetics. The activation energy, Ea, was 105.7 kJ/mol. Fumonisin B1 in contaminated corn could precipitate the nonenzymatic browning reaction with 0.1 M D-glucose at 60 and 80
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Reprinted with permission from Journal of Agricultural and Food Chemistry. 50(16):4726-4733. doi: 10.1021/jf020134r. Copyright 2002 American Chemical Society.