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Isoflavone Levels and the Effect of Processing

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Isoflavone Levels and the Effect of Processing View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by ScholarBank@NUS ISOFLAVONE LEVELS AND THE EFFECT OF PROCESSING ON THE CONTENT OF ISOFLAVONES DURING THE PREPARATION OF SOYMILK AND TOFU MOLAMMA P PRABHAKARAN B.Sc (Tech), UDCT, Mumbai. A THESIS SUBMITTED FOR THE DEGREE OF DOCTOR OF PHILOSOPHY FOOD SCIENCE AND TECHNOLOGY PROGRAMME DEPARTMENT OF CHEMISTRY NATIONAL UNIVERSITY OF SINGAPORE 2005 ACKNOWLEDGMENTS I would like to take this opportunity to express my sincere gratitude to my supervisors, Dr. Conrad O Perera and Dr. Suresh Valiyaveettil for introducing me to the field of phytochemicals and for placing outstanding working facilities at my disposal. I am deeply grateful to them for their support, encouragement, patient guidance and suggestions in bringing this thesis to completion. I am also thankful to Dr. Philip J Barlow for his continuous support and advice during this research tenure. Thanks are also given to my colleagues in the Food Science & Technology programme, and especially to Dr. Lina Goh, Ms. Nang Sabei Myint and Ms. Mya Mya Khin, who have given me great help in my research work. I would like to thank Ms. Ravinder Kaur from Unicurd Food Company in helping to carry out different soy based preparations and for providing the samples. I appreciate the great help from Madam Lee Chooi Lan for her numerous acts of help in solving day to day laboratory problems. Special thanks also go to ADM Company, USA for providing me with a free gift of defatted soy flour during this research work. I am grateful to the National University of Singapore for providing me the research scholarship and funds to let me have this great opportunity to complete this research study. I am extremely grateful to my family members and especially to my husband, Mr. Biju Nair for his substantial support with endless love, advice and encouragement in my life. Last but not least, many thanks to all those who have contributed in one-way or another in making this thesis possible. i TABLE OF CONTENTS Acknowledgements i Table of Contents ii Summary viii List of Tables x List of Figures xii Abbreviations xiii List of Publications xiv PART I INTRODUCTION AND EXPERIMENTAL………………………………1 Chapter 1 Introduction and literature review………………………………………….…2 1.1 Soybean………………………………………………………………………………..2 1.1.1 Origin of soybeans…………………………………………………………..2 1.1.2 Agronomic characteristics.………………………………………………….2 1.1.3 Composition of soybean.…………………………………………………....3 1.2 Soy foods……………………………………………………………………………...4 1.2.1 Soymilk……………………..……………………………………………….4 1.2.1.1 Composition of soymilk…………………………………………..5 1.2.1.2 Status of soymilk in Asian countries……………………………...6 1.2.1.3 Soymilk preparation methods.…………………………………….7 1.2.1.4 Soy pulp or Okara – the byproduct during soymilk making……..12 1.2.2 Tofu………………………………………………………………………...13 1.2.2.1 Types of tofu……………………………………………………..14 ii 1.2.2.2 Tofu coagulants…………………………………………………..15 1.2.2.3 Tofu gelation mechanism………………………………………...16 1.2.2.4 Factors affecting the quality attributes of tofu……………….......16 1.2.2.5 Tofu wheys……………………………………………………….18 1.2.3 Other soy based products.………………………………………………….18 1.2.3.1 Soy supplements and health products.…………………………...18 1.2.3.2 Soy based infant formulas.…………………………………….…20 1.3 Isoflavones.…………………………………………………………………………..22 1.3.1 Isomers, structure and occurrences………………………………………...23 1.3.2 Soy and role of isoflavones in disease prevention…………………………25 1.3.2.1 Soy intake and heart disease……………………………………..26 1.3.2.2 Soy intake and menopause……………………………………….27 1.3.2.3 Soy intake and bone health……………………………………....28 1.3.2.4 Soy intake and breast health……………………………………..29 1.3.2.5 Major concerns about soy supplements and health products.……30 1.3.3 Isoflavones as phytoestrogens……………………………………………...31 1.3.4 Absorption and metabolism………………………………………………..32 1.3.5 Adverse effects of phytoestrogens…………………………………………34 1.4 Soy isoflavones – analysis and processing effects.…………………………….……35 1.4.1 Methods for extraction and analysis of soy isoflavones…………………...35 1.4.2 Concentration of isoflavones in soybeans and soy foods……...…………..37 1.4.3 Effects of processing on isoflavone levels……………................................39 1.4.4 Methods for reporting the concentration of isoflavones …………………..42 iii 1.5 Objectives of the study…………………………………………………………….…43 Chapter 2 Materials and methods………………………………………………………45 2.1 Materials..…………………………………………………………………………....45 2.1.1 Chemicals………………………………………………………..………....45 2.1.2 Food materials.……………………………………………………………..46 2.1.2.1 Commercially available brands of soymilk and tofu samples.…..46 2.1.2.2 Preparation of soymilk – traditional method.………..…………..46 2.1.2.3 Preparation of soymilk – UHT processing system.……………...47 2.1.2.4 Preparation of tofu……………………………………………….51 2.1.2.5 Soy supplements, health products and infant formulas………….52 2.2 Methodologies adopted.…………………………………………………………….54 2.2.1 Sampling procedure ……………………………………………………….54 2.2.1.1 Soybean seeds…………………………………………………....54 2.2.1.2 Sampling of soymilk, tofu, whey and related products………….54 2.2.1.3 Sampling of soy supplements, health products and infant formulas …………………………………………………..55 2.2.2 Moisture analysis…………………………………………………………..55 2.2.3 Protein assay ……………………………………………………………....56 2.2.3.1 Measurement of protein in soy based samples…………………..58 2.2.4 Yield of tofu………………………………………………………………..58 2.2.5 Texture measurement………………………………………………………59 2.2.5.1 Principle of texture measurement…………………………….….59 iv 2.2.5.2 Method used for texture analysis of tofu………………………...61 2.2.6 Color analysis………………………………………………………………61 2.2.6.1 Principle of color analysis……………………………………..…61 2.2.6.2 Color analysis of tofu ……………………………………………63 2.2.7 pH measurement.…………………………………………………………..63 2.2.8 Isoflavone analysis.………………………………………………………...64 2.2.8.1 Method adopted for extraction of isoflavones from soy samples..64 2.2.8.2 Optimization of gradient profile for HPLC analysis of isoflavones ……………………………………………………….….67 2.2.8.3 Calibration curve for isoflavone standards……………………....70 2.2.8.4 Isoflavone structure confirmation by LC-MS…………………....71 2.2.8.5 Procedure for calculation and expression of isoflavone amounts..71 2.2.9 Statistical analysis of data………………………………………………….74 PART II RESULTS AND DISCUSSIONS……..........................................................75 Chapter 3 Method application for the quantification of isoflavones in soy based foods...76 3.1 Application of method developed for isoflavone analysis…………………………...76 3.2 Results of LC-MS analysis of isoflavones…………………………………………...79 3.3 Quantification of isoflavones in soymilk…………………………………………….84 3.3.1 Isoflavone concentrations in soymilk samples from Singapore…………...84 3.3.2 Isoflavone concentrations in soymilks from other South East Asian countries ……………………………………………….…..86 3.4 Quantification of isoflavones in tofu………………………………………………...89 v 3.4.1 Isoflavone contents in commercially available tofu samples from Singapore ……………………………………………..89 3.4.2 Isoflavone concentrations in tofu samples from other South East Asian countries…………………………………………………………………....92 3.5 Discussion on the results of isoflavone analysis……………………………………..94 Chapter 4 Effect of extraction methods and UHT treatment conditions on the level of isoflavones during soymilk manufacture.………………………………………………..98 4.1 Isoflavone levels in soymilk prepared by hot-grind versus cold-grind method……...99 4.2 Isoflavone levels in soymilk subjected to direct versus indirect UHT treatment…..108 4.3 Okara and isoflavone losses………………………………………………………...109 4.4 General discussion……………………………………………………………….....112 Chapter 5 Effect of different coagulants on the isoflavone levels and physical properties of firm tofu………………………………………………………………………….…..114 5.1 Effect of different coagulants on the isoflavone levels in tofu.………………….…115 5.2 Effect of different coagulants on the physical properties of tofu…………..…….…120 5.2.1 Evaluation of yield, moisture and color of tofu…………………………..121 5.2.2 Evaluation of the textural properties of tofu……………………………...123 5.3 Evaluation of the expelled tofu wheys……………………...………………………126 5.3.1 Tofu wheys and its pH effect……………………………………………..126 5.3.2 Isoflavones in tofu wheys……………………...…………………………129 vi Chapter 6 Concentration and profile of isoflavones in soy based supplements, health products and infant formulas: evaluation of its level of intake…………………..….….132 6.1 Isoflavones in soy supplements…………………………………………………….133 6.2 Isoflavones in soy based health products………………………………………..….137 6.3 Isoflavones in soy based infant formulas…………………………..……………….143 6.4 Evaluation of product labels, contents, intake and need for standardization of isoflavone levels…………………………………………………………………….…..146 PART III CONCLUSIONS AND FUTURE RESEARCH………………………....148 Chapter 7 Conclusions and future research…………………………….……………....149 7.1 Conclusions………………………………………………………………….……...149 7.2 Suggestions for future research…………………………………………………..…151 REFERENCES……………………………………………………………...………….153 APPENDICES..........................................................................................................…...181 vii SUMMARY Isoflavones are phytoestrogens, belonging to a group of phenolic compounds found in soybeans and soy foods. The parent isoflavones in soybeans are genistein, daidzein and glycitein, while their respective glucosides are genistin, daidzin and glycitin. Others include their corresponding acetyl and malonyl glucosides. These compounds have been associated with the decreased incidence of different types of cancers, cardiovascular
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