Thermal degradation kinetics of isoflavone aglycones from soy and red clover

Driven by their beneficial effects on human metabolism, isoflavonoids have gained considerable importance reflected by an increased number of isoflavone-rich foods, food supplements and pharmaceutical products on the market, mainly derived from soy and red clover. While it is well known that the genuine isoflavone pattern will be altered during processing, data on aglycone stability are rare. Therefore, a thorough study into the thermal sensitivities of biochanin A, daidzein, formononetin, flavone, genistein, glycitein and isoflavone was performed. Samples were heated at 150 degrees C over a period of 7 h at three different pH values, and degradation of the aglycones was monitored by HPLC-DAD analyses. Therefrom, structure-related stability characteristics could be established. While virtually no decay was observed at pH 7.0 and 5.6, degradation was most prominent at pH 3. 1. Individual aglycone retention was further dependent on heating time with daidzein being the most labile compound after any time interval. Curve fitting of the data revealed first-order degradation kinetics for flavone and glycitein, while the remaining aglycones exhibited a sigmoidal degradation pattern.