Characterization of fumonisin B(1)-glucose reaction kinetics and products

J Agric Food Chem. 2002 Jul 31;50(16):4726-33. doi: 10.1021/jf020134r.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Carboxylic Acids / chemistry*
  • Carboxylic Acids / isolation & purification
  • Carcinogens, Environmental / chemistry*
  • Carcinogens, Environmental / isolation & purification
  • Chromatography, High Pressure Liquid
  • Fumonisins*
  • Glucose / chemistry*
  • Hot Temperature
  • Kinetics
  • Maillard Reaction
  • Mass Spectrometry
  • Mycotoxins / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Thermodynamics
  • Zea mays / chemistry*

Substances

  • Carboxylic Acids
  • Carcinogens, Environmental
  • Fumonisins
  • Mycotoxins
  • fumonisin B1
  • Glucose