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Soy Isoflavones: Database Development, Estrogenic Activity of Glycitein and Hypocholesterolemic Effect of Daidzein Tongtong Song Iowa State University

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Soy Isoflavones: Database Development, Estrogenic Activity of Glycitein and Hypocholesterolemic Effect of Daidzein Tongtong Song Iowa State University Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1998 Soy isoflavones: database development, estrogenic activity of glycitein and hypocholesterolemic effect of daidzein Tongtong Song Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Agriculture Commons, Food Science Commons, and the Human and Clinical Nutrition Commons Recommended Citation Song, Tongtong, "Soy isoflavones: database development, estrogenic activity of glycitein and hypocholesterolemic effect of daidzein " (1998). Retrospective Theses and Dissertations. 12528. https://lib.dr.iastate.edu/rtd/12528 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly fi-om the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter fece, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. 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UMI A Bell & Howell Information Company 300 North Zeeb Road, Ann Aibor MI 48106-1346 USA 3I3/76M700 800/521-0600 Soy isoflavones: Database development, estrogenic activity of giycitein and hypocholesterolemic effect of daidzein by Tongtong Song A dissertation submitted to the graduate faculty in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Major; Food Science and Technology Major Professor: Patricia A. Murphy Iowa State University Ames, Iowa 1998 Copyright © Tongtong Song, 1998. All rights reser\'ed. UMI Number: 9911644 Copyright 1998 by Song, Tongtong All rights reserved- UMI Microform 9911644 Copyright 1999, by UMI Company. Ail rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. UMI 300 North Zeeb Road Ann Arbor, MI 48103 II Graduate College Iowa State University This is to certify that the Doctoral dissertation of Tongtong Song has met the dissertation requirements of Iowa State University Signature was redacted for privacy. ^ ?^ommittee Member Signature was redacted for privacy. Committee Member Signature was redacted for privacy. Committee Member Signature was redacted for privacy. Committee Member Signature was redacted for privacy. Major Professi Signature was redacted for privacy. For the Major Program, Signature was redacted for privacy. 'e Gr duate College Ill TABLE OF CONTENTS ABSTRACT vi GENERAL INTRODUCTION 1 A. Introduction 1 B. Dissertation Organization 3 LITERATURE REVIEW 4 A. Plant Sources and Analytical Chemistry of Isoflavones 4 B. Sources of Isoflavone Standards: Isolation. Purification and ChemicalSynthesis 15 C. How Do Plants Make Isoflavones? 17 D. .Are Isoflavones Good Antioxidants? 19 E. Estrogenic or Antiestrogenic? 21 F. Isoflavone Metabolism and Bioavailability 31 G. Are Isoflavones Cancer Preventive? 35 H. Soy Protein is Hypocholesteroiemic, What About Soy Isoflavones? 41 I. Soy Isoflavones: Cure for Postmenopausal Osteoporosis? 44 J. Isoflavones and Alcohol Intake 46 K. References 47 iv ISOFLAVONE ANALYSIS: NEW INTERNAL STANDARD AND QUALITY CONTROL 66 Abstract 66 Introduction 67 Materials and methods 68 Results and discussions 72 Acknowledgements 77 References 78 ESTROGENIC ACTIVITY OF GLYCITEIN, A SOY ISOFLAVONE 89 Abstract 89 Introduction 90 Materials and methods 91 Results and discussions 95 Ac know ledgements 99 References 100 SOY ISOFLAVONES, SOYGERM, SOYGERM EXTRACT AND ISOFLAVONE-FREE SOY PROTEIN LOWER PLASMA CHOLESTEROL LEVELS IN HAMSTERS 105 Abstract 105 Introduction 106 Materials and methods 108 V Results Ill Discussions 112 Acknowledgements 116 References 117 GENERAL CONCLUSIONS 127 ACKiNOWLEDGEMENTS 130 Soy isoflavones are proposed to have certain health protective activities, including prevention of cancer, lowering blood cholesterol levels and reducing postmenopausal bone loss. To evaluate the health-enhancing properties of isoflavones, a stable and inexpensive source of these compounds is necessary. Chemical synthesis is a practical way to obtain pure isoflavones. The synthesis of daidzein was modified to a simple, fast and high yield method by cyclizing 2,4,4'-trihydroxydeoxybenzoin (THB) with boron trifluoride etherate and methanesulphonyl chloride. The yield was >86%, and the piunty of synthesized daidzein was >98%. The intermediate of daidzein synthesis, THB, with a similar structure to the isoflavones. proved to be an excellent internal standard in soy isoflavone analysis. The estrogenic activity of glycitein was investigated by using in vivo mice uterine enlargement assay and in vitro estrogen receptor (ER) binding assay. Glycitein demonstrated an estrogenic response in mice uterine enlargement assay 3 times greater than genistein, but 30,000 times less than diethylstillbestrol (DES). Glycitein bound to mice uterine cytosol estrogen receptor proteins with an affinity similar to daidzein but 20 times lower than genistein. This is the first report demonstrates that glycitein has estrogenic activity comparable to daidzein and genistein. Glycitein, although only accounts for 5 to 10% of the total isoflavones in soybeans, can not be neglected in evaluating isoflavones" health enhancing properties and in development of isoflavone database in foods. The dietary effects of soy protein, with or without isoflavones. daidzein and soygerm on plasma cholesterol levels were investigated in golden Syrian hamsters. Daidzein. soygerm or soygerm extract, when added to casein diet. lowered plasma total cholesterol by 15% to 28% (P<0.01) and LDL-cholesterol by 15 to 50% (P<0,01) in both male and female hamsters compared with the casein control group. Soy protein and isoflavone-depleted soy protein, when compared with the casein control, significantly lowered total cholesterol (P<0.01) and LDL-cholesterol (P<0.01) levels for both genders. These data suggest that the isoflavone daidzein. soygerm and soy protein with or without isoflavones. have the abilit\' to lower plasma cholesterol levels in hamsters. 1 GENERAL INTRODUCTION A. Introduction Soybeans contain significant amounts of isoflavones at 1-3 mg/g. Three types of isoflavones are found in soybeans: daidzein. genistein. and glycitein. These isoflavones predominantly occur as glucoside forms in soybeans. The isoflavones have been associated with different health-enhancing properties such as prevention of breast and prostate cancers; lowering blood cholesterol levels, thus, decreasing the risk of cardiovascular diseases; prevention of bone resorption and reduction of postmenopausal symptoms such as hot flash. The need to perform studies on isoflavone's possible health-enhancing properties requires an inexpensive, stable source of pure isoflavones. However, commercial isoflavones are very expensive and from limited sources. Isolation of isoflavones from soybeans is time consuming and provides very low yields. Chemical synthesis is a practical way to produce large quantity of pure isoflavones. To develop a simple, fast and high yield protocol to synthesize isoflavones is one important objective of my research. In order to fully and safely utilize the health-enhancing properties of soy isoflavones. a database of isoflavone content of soy products is needed. Development of a database of isoflavones in foods requires accurate and precise evaluation of different food systems. Usually a good internal standard is required to perform recovery studies and quality control. Selection of an appropriate internal standard and performance of quality control during the database development is another objective of my research. Numerous studies have been performed on the isoflavones. daidzein and genistein. They have weak estrogenic activity, which may be associated with their health-enhancing properties. In addition, genistein is a specific inhibitor of protein tyrosine kinase, a critical enzyme in cellular signal transduction and cellular proliferation. Genistein inhibits the activity of DNA topoisomerase II. an enzyme that is very important in DNA replication and cell proliferation. The antioxidant activity of daidzein and genistein may contribute to their observed anticancer activities
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