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Physicochemical Properties and Isoflavone Content Of PHYSICOCHEMICAL PROPERTIES AND ISOFLAVONE CONTENT OF BREAD MADE WITH SOY Dissertation Presented in Partial Fulfillment of the Requirements for The Degree Doctor of Philosophy in the Graduate School of The Ohio State University By YU CHU ZHANG, M.S. * * * * The Ohio State University 2004 Dissertation Committee: Dr. Yael Vodovotz, Advisor Approved by Dr. Steven J. Schwartz Dr. Joshua Bomser Dr. Joseph Sachleben Advisor Dr. Mark L. Failla Department of Food Science and Technology Copyright by Yu Chu Zhang 2004 ABSTRACT Epidemiological and experimental evidence suggests that consumption of soybean products may significantly impact upon health. Bread made partially with soy represents a traditional alternative for increased soy consumption, and, if successfully formulated and well accepted, may offer an attractive delivery system for isoflavones and soy proteins. The overall objective of this research was to assess the impact of soy addition on physico-chemical properties in fresh and stored soy bread. Addition of large amounts of soy (60%) significantly increases the bread density due to lack of gluten network formation and smaller air cell structure in soy bread. Total moisture content in soy bread (44.7%) was higher than in wheat bread (39.9%) and the distribution of water was found to be affected by soy addition. Upon storage, soy bread firmed at a lower rate (1.6 times) than wheat bread (6.7 times), which may be attributed to various factors: 1). Water distribution in the soy bread that favored easily removed bulk water pool that can act as a plasticizer throughout storage and maintain heterogeneity of the product, 2). A lack of recrystallized amylopectin, and 3). No change in mobility of liquid-like protons and a decrease in mobility of solid-like protons. ii Total isoflavones were found to be stable during bread making, although their profile was largely altered. The proofing stage in bread preparation was key in the production of isoflavone aglycones in bread dough through β-glucosidase activity with 48 °C for two hours being optimal for aglycone production. Five percent almond addition was found to be an effective and economic level to enhance isoflavone aglycones in the soy bread formula. No significant changes were found between the isoflavone content and composition in fresh soy bread and soy bread stored for 14 days, showing good stability of isoflavones in soy bread under room temperature. Therefore changes in the water distribution and starch and protein mobility during storage did not affect the amount or profile of isoflavones indicating that bread eaten even a week or two after storage will deliver the same enhanced nutrition. iii Dedicated to my loving family iv ACKNOWLEDGMENTS I wish to thank my advisor, Dr. Yael Vodovotz, for her support, encouragement, and patience that made this dissertation possible. I am grateful to Dr. Steven J. Schwartz, who provided me with intellectual guidance for my study on isoflavones. I would like to thank all of my colleagues for their help and understanding. I would especially like to thank Stefano Tiziani for his help with NMR experiments, Elizebath A. Clubbs for her help with thermal analysis, Dr. Torsten Bohn for the stimulating discussion on isoflavones and statistical analysis, and Dr. Jae Hwan Lee for his help with isoflavone analysis. I also wish to thank my dear friends at OSU during my study, especially Dr. Josephine Kuo, Dr. Nuray Unlu, and Elizebath A. Clubbs, for their loving care and support. v VITA July 29, 1972 ……….... Born - Shanghai, People’s Republic of China 1990-1996 ………......... Department of Chemistry East China Normal University, People’s Republic of China July 1996 …………….. B.S. Chemistry 1998-1999..…………….Department of Food Science Nottingham University, United Kingdom July 1999 ………………M.Sc. Food Production Management 2001-present……………Graduate Research and Teaching Associate, Department of Food Science and Technology, The Ohio State University, United States PUBLICATIONS 1. Walsh, K.R., Zhang, Y.C., Vodovotz, Y., Schwartz, S.J., and Failla, M. 2003. Stability and bioaccessibility of isoflavones from soy bread during in vitro digestion. Journal of Agricultural and Food Chemistry. 51(16): 4603-4609. 2. Zhang, Y.C., Albrecht, D., Bomser, J., Schwartz, S.J., and Vodovotz, Y. 2003. Isoflavone profile and biological activity of soy bread. Journal of Agricultural and Food Chemistry. 51(26):7611-7616. 3. Zhang, Y.C. and Schwartz, S.J. 2003. Analysis of isoflavones in soy foods. In: Current protocol in food analytical chemistry. John Wiley & Son. New York. FIELDS AND STUDY Major Field: Food Science and Nutrition vi TABLE OF CONTENTS Page Abstract…………………………………………………………………………… ii Dedication………………………………………………………………………… iv Acknowledgment…………………………………………………………………. v Vita………………………………………………………………………………... vi List of Tables……………………………………………………………………... vii List of Figures…………………………………………………………………….. xiv List of Equations………………………………………………………………….. xvii Chapters: 1. Introduction…………………………………………………………………… 1 2. Statement of Problem…………………………………………………………. 7 3. Literature Review …………………………………………………………….. 10 The effect of soy on physico-chemical properties of fresh bread ………………………………………………………............... 10 Mechanism of breadmaking………………………………………. 10 Addition of soy to baked products………………………………... 13 The effect of soy on physico-chemical properties of bread upon 14 storage…………………………………………………………………….. Mechanism of bread staling………………………………………. 14 The impact of added soy on bread staling………………………… 18 Instrumental analysis for characterization of mechanical, physico- chemical, and molecular properties of bread……………………............... 19 Texture……………………………………………………………. 20 Physico-chemical properties……………………………………… 20 Differential scanning calorimetry (DSC)………………… 23 vii Dynamical mechanical analysis (DMA)……………….... 25 Thermogravimetric Analyzer (TGA)……………............. 29 Molecular properties…………………………………………….. 32 NMR methodology……………………………………… 33 Proton NMR ……………………………………………. 33 1. Relaxation times………………………............. 33 2. Cross-relaxation NMR………………………... 34 The effect of breadmaking and storage on isoflavones in soy containing bread…………………………………………………............................... 38 Isoflavone stability during bread making……………………….. 38 Enhancing bioavailability of isoflavones in soy bread……………………………………………………... 41 Stability of isoflavones during storage…………………... 43 Analysis of isoflavones in soy foods……………………………. 43 Spectra fine structure of soy isoflavones………………… 44 Solvent extraction of isoflavones from soy foods………. 49 Isoflavone anlaysis using High Pressure Liquid Chromatography (HPLC)……………………………….. 52 4. Materials and Methods………………………………………………............ 54 The effects of soy addition on the physicochemical properties of fresh and stored bread on a structural and molecular level……………………. 55 Bread preparation………………………………………………... 55 Bread storage…………………………………………………….. 55 Instrumental analysis……………………………………………. 59 Tests on physical properties of bread……………............ 59 Loaf volume……………………………………... 59 Bread firmness…………………………………… 59 Moisture content………………………………… 60 Thermal analysis………………………………………… 60 Dynamic mechanical analysis (DMA)…………... 60 Differential scanning calorimetry (DSC)……….. 61 Thermogravimetric analyzer…………………….. 65 Molecular properties using NMR……………………….. 66 Sample preparation………………………………. 66 viii Liquid state Proton (1H) NMR…………………... 66 Spin-lattice relaxation time (T1 ) measurement…………………………….. 66 Spin-spin relaxation time (T2) measurement…………………………….. 67 Data analysis…………………………….. 67 Solid state 1H Cross-Relaxation NMR………….. 68 Statistical analysis………………………………………. 69 Isoflavone content and composition in the soy bread and their stability through processing and storage………………………………………….. 69 Extraction of isoflavones………………………………………… 69 Sample preparation for extraction………………………. 69 Solvent extraction of isoflavones in their natural forms……………………………………………………... 69 Isoflavone analysis using HPLC-UV spectrophotometry……….. 70 Sample preparation…………………………………….... 70 Isoflavone quantification………………………………… 71 Stock standard solutions…………………............ 71 Working standard solutions……………………… 74 Absorbance measurement using a UV spectrophotometer……………………………….. 74 Calibration curve preparation using HPLC……… 74 Gradient separation and identification of isoflavones in sample……………………………..................................... 75 Mobile phase preparation………………………... 75 HPLC set-up……………………………………... 75 HPLC analysis…………………………………… 76 Statistical analysis……………………………………….. 76 The effect of the processing and almond addition on the isoflavone content and composition in the soy bread……………………………….. 79 Dough and bread preparation……………………………………. 80 Isoflavone analysis………………………………………............. 80 β-Glucosidase activity assay…………………………………….. 81 Statistical analysis……………………………………………….. 81 ix 5. Results and Discussion………………………………………………………. 83 The effect of soy on physico-chemical properties of fresh bread……….. 83 Bread Macroscopic properties…………………………………… 83 Loaf volume……………………………………………... 83 Bread firmness from Instron…………………………….. 83 Physico-chemical properties by thermal analysis……………….. 84 Moisture content and state of water (DSC and TGA)…… 84 Dynamic mechanical analyzer (DMA) results…………... 89 Molecular properties by NMR…………………………………... 94 Relaxation times of liquid proton……………………….. 94 1H cross relaxation………………………………………. 96 The effect of soy on physico-chemical properties of bread upon storage………………………………………………………............ 100 Bread macroscopic properties…………………………………….
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