Note: Isoflavones -- Contents -- Isoflavones in Context -- Chapter 1 Phytoestrogens in Health: The Role of Isoflavones -- 1.1 Introduction -- 1.2 Absorption, Metabolism and Excretion of Isoflavones -- 1.3 Mechanisms of Action of Isoflavones -- 1.4 Clinical Effects of Isoflavones -- 1.4.1 Cardiovascular Health -- 1.4.2 The Brain -- 1.4.3 Bone Health -- 1.4.4 Breast Cancer -- 1.4.5 Prostate Cancer -- 1.4.6 Menopausal Symptoms -- 1.5 Areas in Dispute -- Summary Points -- Key Facts -- List of Abbreviations -- References -- Chapter 2 Phytoestrogens in Plants: With Special Reference to Isoflavones -- 2.1 Characterization of Phytoestrogens -- 2.2 Distribution of Phytoestrogens in the Plant Kingdom -- 2.2.1 Phytoestrogens other than Isoflavones -- 2.2.2 Isoflavones -- 2.3 Chemical Features of Plant Isoflavones -- 2.4 Biosynthesis of Isoflavones -- 2.5 Localisation of Isoflavones in Plants -- 2.6 Biological Function of Isoflavones in Plants -- 2.6.1 Interaction of Isoflavones with Micro-organisms of the Rhizosphere -- 2.6.2 Isoflavones as Phytoalexins and Phytoanticipins -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chapter 3 Isoflavones in Foods and Ingestion in the Diet -- 3.1 Introduction -- 3.2 An Overview of Structure and Analysis of Dietary Isoflavones -- 3.2.1 Structure -- 3.2.2 Analysis -- 3.3 Isoflavone Content in Selected Foods -- 3.4 Growth, Variety, Environmental and Post-harvest Storage Conditions Affecting Isoflavone Composition in Soybeans -- 3.5 Isoflavone Composition as Affected by Processing -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chemistry and Biochemistry -- Chapter 4 The Chemistry/Biochemistry of the Bioconversion of Isoflavones in Food Preparation -- 4.1 Introduction. , 4.2 Bioconversion of Isoflavones from Glycosides to Aglycones -- 4.3 Enzymatic Transformation of Isoflavone Isomers in Fermented Soymilk -- 4.4 β-Glycosidase Reaction during Bioconversion of Isoflavones -- Summary Points -- Key Facts -- Definitions of Word and Terms -- List of Abbreviations -- References -- Chapter 5 Chemistry and Synthesis of Daidzein and its Methylated Derivatives: Formononetin, Isoformononetin, and Dimethyldaidzein -- 5.1 Introduction -- 5.2 Synthesis of Daidzein (1) -- 5.2.1 Synthesis of Daidzein: BF3 · OEt2-catalyzed Friedel-Crafts Acylation and Ring Closure -- 5.2.2 Synthesis of Daidzein: RCM with Grubbs' Catalyst -- 5.2.3 Synthesis of Daidzein: I2-Mediated Cyclization -- 5.2.4 Synthesis of Daidzein: Oxidative Rearrangement with Thallium(III) Nitrate -- 5.3 Synthesis of Formononetin (2) -- 5.3.1 Carbonyls as One-carbon Electrophiles -- 5.3.2 Activated Aldehyde Surrogates as One-carbon Surrogates -- 5.4 Synthesis of Isoformononetin (3) -- 5.4.1 Selective Methylation of Daidzein (1) -- 5.4.2 Suzuki-mediated Synthesis -- 5.5 Synthesis of Dimethyldaidzein (4) -- 5.5.1 Synthesis of Dimethyldaidzein: Polymer-supported Iodobenzene Diacetate (PSIBD)-promoted Oxidative Rearrangement -- 5.5.2 Synthesis of Dimethyldaidzein: Organolead-mediated Arylation -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chapter 6 Non-natural Isoflavonoids -- 6.1 Introduction -- 6.2 Phenylpropanoid and Isoflavonoid Pathways -- 6.3 Isoflavanoids -- 6.4 Non-natural Isoflavonoids -- 6.4.1 Semi-synthesis of Non-natural Isoflavonoids -- 6.4.2 Chemical Synthesis of Non-natural Flavanones -- 6.4.3 ER Assay -- 6.4.4 Protein Engineering of Uridine Diphosphate Glycoslytransferase (UGT) -- 6.5 Structural and Functional Studies of IFS -- Summary Points -- Key Facts -- Definitions of Words and Terms. , List of Abbreviations -- References -- Chapter 7 The Structure of Isoflavones by 1D and 2D Homonuclear and Heteronuclear NMR Spectroscopy -- 7.1 Introduction -- 7.2 Structure Elucidation: Establishing Spectral Correlations -- 7.3 Chromatography-NMR -- 7.4 Conformation and NMR -- 7.5 Substituent Effects and Prediction of Structures -- 7.6 Isoflavone Metabolites -- 7.7 Solvent Effects -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- Acknowledgement -- References -- Chapter 8 Biotransformation and Transfer of Genistein: a Comparison with Xenoestrogens and a Focus on the Human Placenta -- 8.1 Biotransformation of Genistein Compounds in the Gastrointestinal Tract -- 8.1.1 Deglycosylation of Genistin in the Small Intestine -- 8.1.2 Glucuronidation and Sulfation of Genistein -- 8.1.3 Hydroxylation of Genistein in the Liver -- 8.1.4 Breakdown of Genistein and Luminal Excretion -- 8.1.5 Transfer of Genistein in Placenta -- 8.2 A Comparison with Other Xenoestrogens -- 8.2.1 Chemical Structure of BPA and NP -- 8.2.2 Biotransformation of Xenoestrogens -- 8.2.3 Placenta Transfer -- 8.3 Conclusion -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chapter 9 The Biological Effects of Genistein and its Intracellular Metabolite, 5,7,3',4'-Tetrahydroxyisoflavone -- 9.1 Genistein and its Biological Activities -- 9.1.1 Oestrogenic Activity -- 9.1.2 Anticancer Effects -- 9.1.3 Antioxidant Action -- 9.1.4 Anti-inflammatory Activity -- 9.2 Intracellular Formation of the Genistein Metabolite 5,7,3',4'-Tetrahydroxyisoflavone (THIF) -- 9.3 THIF and Cancer -- 9.4 THIF and Endothelial Function -- 9.5 Summary -- Summary Points -- Key Facts -- List of Abbreviations -- References -- Chapter 10 Genistein Chemistry and Biochemistry -- 10.1 Introduction. , 10.2 Chemical Structure and Interaction with Estrogen Receptors -- 10.3 Metabolism -- 10.4 Conclusion -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chapter 11 Isoflavones and Human Estrogen Receptor: When Plants Synthesize Mammalian Hormone Mimetics -- 11.1 Introduction -- 11.2 From Plant Biosynthesis to Mammalian Biosynthesis -- 11.2.1 Biosynthesis of Isoflavonoids in Leguminous Cells -- 11.2.2 Biosynthesis of Isoflavonoids in ERs -- 11.3 Interaction of Isoflavonoids with ERs -- 11.4 Mammalian Metabolism and Bioavailability -- 11.5 Biochemical and Physiological Functions of Isoflavonoids -- 11.5.1 Estrogenic-related Effects -- 11.5.2 Non-estrogenic-related Effects -- 11.6 Conclusion -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Analysis -- Chapter 12 Continuous Microwave-assisted Isoflavone Extraction -- 12.1 Introduction -- 12.2 Microwave Extraction System Designs -- 12.3 Microwave-assisted Extraction Process -- 12.4 Oil Separation and Isoflavone Purification -- 12.5 Significant Results and Discussion -- 12.5.1 Isoflavones (and Oil) Yields -- 12.5.2 Influence of Time and Temperature on the Oil and Isoflavones Extraction Yield - Reaction Kinetics -- 12.6 Conclusion -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- Acknowledgements -- References -- Chapter 13 Isoflavones: High-performance Liquid Chromatographic Analysis of Glucuronic Acid- and Sulfuric Acid-conjugated Metabolites of Daidzein and Genistein in Human Plasma and Urine -- 13.1 Introduction -- 13.2 Conventional Methods -- 13.2.1 Selective Enzymatic Hydrolysis -- 13.2.2 Fractionation by Ion-exchange Chromatography -- 13.2.3 Direct Assay -- 13.3 A Simple Direct Assay of Conjugated Metabolites Using HPLC-UV. , 13.3.1 Reference Compounds -- 13.3.2 SPE -- 13.3.3 Chromatographic Conditions -- 13.3.4 Application -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chapter 14 High-throughput Quantification of Pharmacologically Active Isoflavones using LC-UV/PDA and LC-MS/MS -- 14.1 Introduction -- 14.2 High-throughput HPLC-UV/MS Analytical/Bioanalytical Methods -- 14.2.1 High-throughput HPLC Methods using UV Detection -- 14.2.2 High-throughput HPLC Methods using MS -- 14.3 Conclusions -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- References -- Chapter 15 Methods for Isoflavones: A Focus on Beverage Analysis -- 15.1 Introduction -- 15.2 Methods of Extraction -- 15.2.1 Direct Extraction -- 15.2.2 Hydrolysis -- 15.2.3 Internal Standards -- 15.3 Chromatographic Methods -- 15.4 Conclusion -- Summary Points -- Key Facts -- Definitions of Words and Terms -- List of Abbreviations -- Acknowledgements -- References -- Chapter 16 The Determination of Isoflavones in Supplemented Foods: An Overview -- 16.1 Introduction -- 16.2 Isoflavone Isolation -- 16.3 Techniques for the Analysis of Isoflavones in Supplemented Food -- 16.3.1 Liquid Chromatography (LC) -- 16.3.2 Gas Ghromatography (GC) -- 16.3.3 Capillary Electrophoresis (CE) -- 16.3.4 Mass Spectrometry (MS) -- 16.3.5 Immunoanalysis -- 16.4 Conclusions -- Summary Points -- Key Facts -- Definition of Words and Terms -- List of Abbreviations -- References -- Chapter 17 Isoflavones: LC-MS/MS Profiling of Isoflavone Glycosides and Other Conjugates -- 17.1 Introduction -- 17.2 Chromatographic Separation of Flavonoids -- 17.3 Mass Spectrometry (MS) as a Tool for Identification of Isoflavone Glycoconjugates -- 17.4 Sources of Structural Variability of Flavonoid Compounds. , 17.5 Differentiation of Isoflavone and Flavone Glycoconjugates with Instrumental Methods.