Isoflavones: Chemistry, Analysis, Function and Effects

711 Pages·2012·8.841 MB·English

by  Victor R Preedy, K Nara, Dongmin Liu, P Kachlicki, Rita C Alves, R Baber, F Bucar, B H Chen, J Park, R Bolanos, R Priefer, M A. G. Koffas, Kristina Wahala, Y Vodovotz, Murray Mitchell, B T Akingbemi, Francesco Squadrito, Yves Jacquot, K Ishii, Dorin Boldor, Wahajuddin, Zhong Li, A Zafra-Gomez, Lei Wan, Dra M Teresa Blay, Daniel Scherman, S Sehmisch, Sue K Park, Craige C Wrenn, J A Bomser, Joesph M Wu, Edwin L Lephart, R Huang, Paul B Tchouwou, Giulia Corona, Brian Stephens

Food and Nutritional Components in Focus
Edited by Victor R. Preedy
Isoflavones
Chemistry, Analysis, Function and Effects
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Isoflavones
Chemistry, Analysis, Function and Effects
Food and Nutritional Components in Focus
Series Editor:
Professor Victor R Preedy, School of Medicine, King’s College London, UK
Titles in the Series:
1: Vitamin A and Carotenoids: Chemistry, Analysis, Function and Effects
2: Caffeine: Chemistry, Analysis, Function and Effects
3: Dietary Sugars: Chemistry, Analysis, Function and Effects
4: B Vitamins and Folate: Chemistry, Analysis, Function and Effects
5: Isoflavones: Chemistry, Analysis, Function and Effects
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Isoflavones
Chemistry, Analysis, Function and Effects
Edited by
Victor R Preedy
School of Medicine, King’s College London, UK
FoodandNutritionalComponentsinFocusNo.5
ISBN: 978-1-84973-419-6
ISSN: 2045-1695
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Preface
In the past three decades there have been major advances in our under-
standing of the chemistry and function of nutritional components. This has
been enhanced by rapid developments in analytical techniques and instru-
mentation. Chemists, food scientists and nutritionists are, however, separated
by divergent skills, and professional disciplines. Hitherto this transdisci-
plinary divide has been difficult to bridge.
TheseriesFoodandNutritionalComponentsinFocusaimstocoverinasingle
volumethechemistry,analysis,functionandeffectsofsinglecomponentsinthe
diet or its food matrix. Its aim is to embrace scientific disciplines so that
information becomes more meaningful and applicable to health in general.
The series Food and Nutritional Components in Focus covers the latest
knowledge base and has a structured format.
Isoflavones has four major sections, namely:
Isoflavones in Context
Chemistry and Biochemistry
Analysis
Function and Effects
Thefirstsectioncoversphytoestrogensinhealthandplants,thenmaterialon
isoflavones in foods and the diet. The chemistry and biochemistry section
covers structures, bioconversion and biotransformation, the human estrogen
receptor,homonuclearNMRspectroscopy,genistein,daidzein,xenoestrogens,
methylated derivatives and non-natural isoflavonoids. The section on analysis
includesfoods,beverages,nuts,traditionalmedicines,herbs,pharmacologically
active isoflavones, plasma and urine. Methodology encompasses microwave-
extraction,HPLC,LC-MS/MSandLC-UV/PDAandmanyothertechniques.
Finally, the section on function and effects covers ingestion of isoflavones by
FoodandNutritionalComponentsinFocusNo.5
Isoflavones:Chemistry,Analysis,FunctionandEffects
EditedbyVictorRPreedy
rTheRoyalSocietyofChemistry2013
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
v
vi Preface
different populations, isoflavones in beverages, inherited metabolic diseases,
mucopolysaccharidoses, clinical trials,obesity,inflammation inadipose tissue,
menopausal vasomotor syndrome, estrogenic activity, testicular function,
thyroid function, gastric cancer, learning and memory, prenatal exposure, cell
proliferation,bone, NMDA and GABA receptors, and insulin secretion.
Individual isoflavones are also described, such as daidzein, genistein and gly-
citein,aswellastheirderivatives,suchasequolandtetrahydroxyisoflavone.As
isoflavonesoccurwithinacomplexplantmatrix,otherestrogenicandbioactive
compounds in isoflavones-rich foods, e.g. coumestrol, are described for com-
parative reference.
Each chapter transcends the intellectual divide with a novel cohort of fea-
tures namely by containing:
(cid:2) Abstract
(cid:2) Summary Points
(cid:2) Key Facts (areas of focus explained for the lay person)
(cid:2) Definitions of Words and Terms
It is designed for chemists, food scientist and nutritionists, as well as
healthcare workers and research scientists. Contributions are from leading
national and international experts, including contributions from world-
renowned institutions.
Professor Victor R Preedy
King’s College London
Contents
Isoflavones in Context
Chapter 1 Phytoestrogens in Health: The Role of Isoflavones 3
Rodney J. Baber
1.1 Introduction 3
1.2 Absorption,MetabolismandExcretionofIsoflavones 4
1.3 Mechanisms of Action of Isoflavones 5
1.4 Clinical Effects of Isoflavones 6
1.4.1 Cardiovascular Health 6
1.4.2 The Brain 6
1.4.3 Bone Health 7
1.4.4 Breast Cancer 7
1.4.5 Prostate Cancer 8
1.4.6 Menopausal Symptoms 8
1.5 Areas in Dispute 8
Summary Points 9
Key Facts 9
List of Abbreviations 10
References 10
Chapter 2 Phytoestrogens in Plants: With Special Reference
to Isoflavones 14
Franz Bucar
2.1 Characterization of Phytoestrogens 14
2.2 Distribution of Phytoestrogens in the Plant Kingdom 15
2.2.1 Phytoestrogens other than Isoflavones 15
2.2.2 Isoflavones 15
FoodandNutritionalComponentsinFocusNo.5
Isoflavones:Chemistry,Analysis,FunctionandEffects
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vii
viii Contents
2.3 Chemical Features of Plant Isoflavones 17
2.4 Biosynthesis of Isoflavones 18
2.5 Localisation of Isoflavones in Plants 19
2.6 Biological Function of Isoflavones in Plants 22
2.6.1 Interaction of Isoflavones with
Micro-organisms of the Rhizosphere 22
2.6.2 IsoflavonesasPhytoalexinsandPhytoanticipins 22
Summary Points 23
Key Facts 24
Definitions of Words and Terms 24
List of Abbreviations 25
References 26
Chapter 3 Isoflavones in Foods and Ingestion in the Diet 28
Baskaran Stephen Inbaraj and Bing Huei Chen
3.1 Introduction 28
3.2 An Overview of Structure and Analysis of Dietary
Isoflavones 29
3.2.1 Structure 29
3.2.2 Analysis 29
3.3 Isoflavone Content in Selected Foods 31
3.4 Growth, Variety, Environmental and Post-harvest
Storage Conditions AffectingIsoflavone Composition
in Soybeans 31
3.5 Isoflavone Composition as Affected by Processing 36
Summary Points 41
Key Facts 41
Definitions of Words and Terms 41
List of Abbreviations 42
References 43
Chemistry and Biochemistry
Chapter 4 The Chemistry/Biochemistry of the Bioconversion of
Isoflavones in Food Preparation 49
Kashif Ghafoor, Fahad Y. Al-Juhaimi and Jiyong Park
4.1 Introduction 49
4.2 Bioconversion of Isoflavones from Glycosides to
Aglycones 53
4.3 Enzymatic Transformation of Isoflavone Isomers
in Fermented Soymilk 54
4.4 b-Glycosidase Reaction during Bioconversion of
Isoflavones 56
Contents ix
Summary Points 57
Key Facts 57
Definitions of Word and Terms 57
List of Abbreviations 58
References 59
Chapter 5 Chemistry and Synthesis of Daidzein and its Methylated
Derivatives: Formononetin, Isoformononetin, and
Dimethyldaidzein 61
VincentM.Carroll,JeffreyD.St.Denis,KyleF.Biegasiewicz
and Ronny Priefer
5.1 Introduction 61
5.2 Synthesis of Daidzein (1) 63
5.2.1 Synthesis of Daidzein: BF (cid:3)OEt -catalyzed
3 2
Friedel–Crafts Acylation and Ring Closure 63
5.2.2 Synthesis of Daidzein: RCM with Grubbs’
Catalyst 64
5.2.3 SynthesisofDaidzein:I -MediatedCyclization 64
2
5.2.4 Synthesis of Daidzein: Oxidative
Rearrangement with Thallium(III) Nitrate 67
5.3 Synthesis of Formononetin (2) 67
5.3.1 Carbonyls as One-carbon Electrophiles 69
5.3.2 Activated Aldehyde Surrogates as One-carbon
Surrogates 70
5.4 Synthesis of Isoformononetin (3) 73
5.4.1 Selective Methylation of Daidzein (1) 73
5.4.2 Suzuki-mediated Synthesis 74
5.5 Synthesis of Dimethyldaidzein (4) 74
5.5.1 Synthesis of Dimethyldaidzein:
Polymer-supported Iodobenzene Diacetate
(PSIBD)-promoted Oxidative Rearrangement 76
5.5.2 Synthesis of Dimethyldaidzein:
Organolead-mediated Arylation 76
Summary Points 78
Key Facts 79
Definitions of Words and Terms 79
List of Abbreviations 79
References 80
Chapter 6 Non-natural Isoflavonoids 83
Namita Bhan and Mattheos Koffas
6.1 Introduction 83
6.2 Phenylpropanoid and Isoflavonoid Pathways 83
6.3 Isoflavanoids 85