Characterization of fumonisin B(1)-glucose reaction kinetics and products.
The reaction of fumonisin B(1) with the reducing sugar D-glucose can block the primary amine group of fumonisin B(1) and may detoxify this mycotoxin. A method to separate hundred milligram quantities of fumonisin B(1)-glucose reaction products from the excess D-glucose with a reversed-phase C(18) cartridge was developed. Mass spectrometry revealed that there were four primary products in this chain reaction when fumonisin B(1) was heated with D-glucose at 65 degrees C for 48 h: N-methyl-fumonisin B(1), N-carboxymethyl-fumonisin B(1), N-(3-hydroxyacetonyl)-fumonisin B(1), and N-(2-hydroxy, 2-carboxyethyl)-fumonisin B(1). The N-(1-deoxy-D-fructos-1-yl) fumonisin B(1) (fumonisin B(1)-glucose Schiff's base) was detected by mass spectrometry when fumonisin B(1) was heated with D-glucose at 60 degrees C. The nonenzymatic browning reaction of fumonisin B(1) with excess D-glucose followed apparent first-order kinetics. The activation energy, E(a), was 105.7 kJ/mol. Fumonisin B(1) in contaminated corn could precipitate the nonenzymatic browning reaction with 0.1 M D-glucose at 60 and 80 degrees C.
Department of Food Science and Human Nutrition, Iowa State University, Ames, Iowa 50011, USA.
Yun
Y
Lu
Laura
L
Clifford
Catherine C
CC
Hauck
Suzanne
S
Hendrich
Gary
G
Osweiler
Patricia A
PA
Murphy
D002264:Carboxylic Acids / Q000737:chemistry* / Q000302:isolation & purification; D002274:Carcinogens, Environmental / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D037341:Fumonisins; D005947:Glucose / Q000737:chemistry*; D006358:Hot Temperature; D007700:Kinetics; D015416:Maillard Reaction; D013058:Mass Spectrometry; D009183:Mycotoxins / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013816:Thermodynamics; D003313:Zea mays / Q000737:chemistry*
D002264:Carboxylic Acids; D002274:Carcinogens, Environmental; D037341:Fumonisins; D009183:Mycotoxins; C056933:fumonisin B1; D005947:Glucose