Isoflavones occur primarily as glycosides (namely, malonyl-, acetyl-, and non-conjugated beta-glycosides) and a small percentage as the bioactive aglycon. The different chemical structures of isoflavones can dictate their stability during processing. Therefore, our objective was to determine the effects of pH and thermal treatments on conjugated isoflavones with regard to interconversions and loss. Conjugated daidzin and genistin were heated at 25, 80, and 100 degrees C under neutral, acidic, and basic conditions. Changes in isoflavone derivatives were monitored using high-performance liquid chromatography. Along with interconversions, considerable loss in total known isoflavone derivatives was noted for each isoflavone, especially under elevated pH and temperature. The malonylglycosides showed more stability than acetylglycosides, especially under acidic conditions. Overall, loss in isoflavone derivatives was significantly higher for daidzin than for genistin glycoside forms. Our results highlighted the significance of chemical structure with regard to stability, which is a key factor in determining soy processing conditions.

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The conversion and degradation of malonylglucosides were kinetically characterized under elevated pH/heat conditions. Malonylgenistin and malonyldaidzin were heated at 60, 80, and 100 degrees C and pH values of 8.5, 9, and 9.5. A simple kinetic model was developed, which adequately predicted the conversion and degradation reactions. The conversion and degradation rates increased as temperature and pH increased. The rates of conversion of both malonylglucosides into their respective beta-glucosides were comparable under all pH/heat treatments. However, at 100 degrees C, the rates of degradation of malonyldaidzin were approximately double those of malonylgenistin, under all pH treatments. When malonlydaidzin was heated at 100 degrees C and pH 9.5, degradation of the produced daidzin occurred. Therefore, an alternative kinetic model was developed to better predict the conversion and degradation of malonyldaidzin occurring at 100 degrees C and pH 9.5. The models developed provide soy food manufacturers with guidelines for better control of the profile and level of isoflavones..

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