The impact of simulated digestion on the stability and bioaccessibility of isoflavonoids from soy bread was examined using simulated oral, gastric, and small intestinal digestion. The aqueous (bioaccessible) fraction was isolated from digesta by centrifugation, and samples were analyzed by high-performance liquid chromatography (HPLC). Isoflavonoids were stable during simulated digestion. Partitioning of aglycones, acetylgenistin, and malonylgenistin into the aqueous fraction was significantly (P < 0.01) affected by the concentration of bile present during small intestinal digestion. Omission of bile resulted in nondetectable genistein and <40% of total daidzein, glycitein, and acetylgenistin in the aqueous fraction of digesta. Partitioning of these compounds into the aqueous fraction was increased by physiological concentrations of bile extract. These results suggest that micellarization is required for optimal bioaccessibility of isoflavonoid aglycones. We propose that the bioavailability of isoflavones from foods containing fat and protein may exceed that of supplements due to enhanced bile secretion.

The present study examines the ability of isoflavone extracts from whole soy bread and two soy bread fractions, crumb and crust, to modulate the proliferation of human prostate cancer PC-3 cells. Total isoflavone content in the two fractions of soy bread were similar (3.17 micromol/g dry basis). However, their conjugate patterns were altered. Both fractions of soy bread contained a similar level of isoflavone aglycones ( approximately 24%). Low concentrations of soy bread extracts increased PC-3 cell proliferation as much as 47% compared to untreated control. This proliferative effect in cell growth was reduced at higher extract concentration. Soy bread crust extract (10 mg/mL) reduced PC-3 cell proliferation by 15% compared to untreated control. Interestingly, wheat bread extracts increased cell proliferation at all concentrations tested. Although extracts from both breads possessed biological activity, only soy bread crust extract reduced PC-3 cell proliferation. This observation may be related to the presence of soy in this bread.

Bread made partially with soy may represent a viable alternative for increasing soy consumption in populations consuming Western diets. The potential health‐promoting activity of soy isoflavones may depend on their abundance and chemical form. The objective of this study was to characterize the changes in isoflavone distribution and β‐glucosidase activity during the soy breadmaking process. Soy bread ingredients were combined and mixed to form a dough that was subsequently proofed at 48°C for 1–4 hr and baked at 165°C for 50 min to produce breads. The isoflavone composition and β‐glucosidase activity in bread ingredients, doughs, and breads were monitored. Soy ingredients and wheat flour (not bread yeast) were the major contributors of the β‐glucosidase activity in bread. No degradation of isoflavones was observed during breadmaking but the isoflavone distribution was largely altered. Proofing and baking have important but different roles in changing the isoflavone distribution. Proofing converted isoflavone β‐glucosides to aglycones by highly specific β‐glucosidase activity. Thermal treatment during baking significantly decreased the isoflavone malonylglucosides and increased isoflavone β‐glucosides. Enzyme activity during proofing and the balance between formation and deconjugation of isoflavones during baking determine the isoflavone content and composition in the final product.

Native beta-glucosidase activity in soy bread can convert isoflavone glucosides to aglycones during proofing, and this study determined the time-temperature dependence of this process. Samples were taken every hour for 4 h during proofing at 22, 32, and 48 degrees C to determine beta-glucosidase activity and isoflavone profiles of the dough. After 1-2 h, the beta-glucosidase activity increased 43-84% achieving a plateau value at 22 degrees C but declining when proofed beyond 2 h at 32 degrees C and 48 degrees C. Large increases in aglycones and corresponding decreases in the simple glucosides were observed during proofing. The level of malonyl-glucosides decreased 3-15%, and acetyl-glucosides were fairly constant. The two higher temperatures drove more rapid conversion: 70-73% of simple glucosides in 2-4 h. The extent of conversion in the early proofing periods corresponded to beta-glucosidase activity. The optimum time-temperature protocol was 2 h at 48 degrees C resulting in a rapid, high conversion.

Supplement 10 Current Protocols in Food Analytical Chemistry I1.6.2 Analysis of Isoflavones in Soy Foods I1.6.3 Bioactive Food Components I1.6.5 Bioactive Food Components I1.6.7 Bioactive Food Components I1.6.9 Bioactive Food Components Supplement 10 Current Protocols in Food Analytical Chemistry I1.6.10 Analysis of Isoflavones in Soy Foods Supplement 10 Current Protocols in Food Analytical Chemistry I1.6.14 Analysis of Isoflavones in Soy Foods Current Protocols in Food Analytical Chemistry Supplement 10 I1.6.15 Bioactive Food Components Key References Griffith and Collison, 2001. See above. A systematic investigation in extraction and analysis of isoflavones from soy-containing foods and nutritional supplements. Murphy et al., 2002. See above. A systematic review and comparison of different solvents and aqueous-to-solvent ratios for isoflavone extraction efficiency.