93. B Vitamins & Folate

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93. B Vitamins & Folate

 

 

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Syllabus

Chapter 1 Historical Context of Vitamin B 3

Hideyuki Hayashi
1.1 Evidence for the Presence of Unidentified
Factors Essential for Life 3
1.2 Establishment of the Concept of Vitamins 4
1.3 Resolution of Vitamin B 6
1.4 Discovery that Vitamins act as Coenzymes 6
1.5 Influence on the Research into other Vitamins 8
1.6 Microbial Nutritional Factors and Vitamins 9
1.7 Vitamin B6 10
1.8 Anaemia and Vitamins 12
1.9 Concluding Remarks 14
Summary Points 15
Key Facts about Beriberi in the Russo-Japanese War (1905) 15
List of Abbreviations 16
References 16
Chapter 2 B Vitamins and Disease 21

Jutta Dierkes and Ottar Nyga ̊rd
2.1 Introduction 21
2.2 The Role of Different Study Types 22
2.3 Treatment of Deficiency or Supplementation without
Reference to Vitamin Status 23
2.4 Mechanisms 24
2.5 Cardiovascular Disease 25
2.5.1 Folic acid, Vitamin B12 and Vitamin B6 25
2.5.2 Niacin in Cholesterol Reduction 26

Food and Nutritional Components in Focus No. 4
B Vitamins and Folate: Chemistry, Analysis, Function and Effects
Edited by Victor R. Preedy
r The Royal Society of Chemistry 2013
Published by the Royal Society of Chemistry, www.rsc.org

2.6 Cancer 27
2.7 Prevention of Age-related Cognitive
Decline or Dementia 28
2.8 Renal Disease 28
2.9 Concluding Remarks 30
Summary Points 30
List of Abbreviations 31
References 31

Chapter 3 Vitamins and Folate Fortification in the Context

of Cardiovascular Disease Prevention 35
Alexios S. Antonopoulos, Cheerag Shirodaria and
Charalambos Antoniades
3.1 Introduction 35
3.2 Homocysteinaemia as a Risk Factor for
Atherosclerosis 36
3.2.1 Mechanisms of Homocysteine-mediated
Vascular Disease 36
3.2.2 Epidemiological Evidence on Homocysteine as
a Cardiovascular Risk Factor 37
3.3 Cardiovascular Effects of Folic Acid, B6 and B12:
Any Need for Folate Fortification? 37
3.3.1 B Vitamins as Homocysteine Lowering Agents 37
3.3.2 Effects on Proinflammatory Mechanisms 39
3.3.3 Effects on Endothelial Function 39
3.3.4 Further Mechanistic Insights in Human
Vessels 40
3.3.5 Effects on Atheroma Progression 40
3.4 Folate and B Vitamins in Cardiovascular Disease:
Insights from Clinical Trials and Folate Fortification
Programme 42
3.4.1 Homocysteine Lowering and Cardiovascular
Disease Prevention 42
3.4.2 Criticism of Randomized Clinical Trials 43
3.4.3 Is Folate Fortification and B Vitamins
Administration Safe? 46
3.5 Concluding Remarks 47
Summary Points 47
Key Facts about B Vitamins as Therapeutic Agents in
Cardiovascular Disease 48
Definitions of Words and Terms 48
List of Abbreviations 49
References 50

Chapter 4 The Importance of Vitamins in Biochemistry and Disease as
Illustrated by Thiamine Diphosphate (ThDP) Dependent
Enzymes 55
Shinya Fushinobu and Ryuichiro Suzuki
4.1 Reactions of ThDP-dependent Enzymes 55
4.1.1 General Mechanism 55
4.1.2 Pyruvate-processing Enzymes 57
4.1.3 Transketolase and Phosphoketolase 59
4.2 Structures and Classification 61
4.2.1 Structures of TK and PK 61
4.2.2 Structures of Other ThDP-Dependent
Enzymes 62
4.2.3 Classification of ThDP-Dependent Enzyme
Families 62
Summary Points 63
Key Facts 64
Key Facts about the History of Structural and
Functional Studies on ThDP-dependent Enzymes 64
Key Facts about Metabolic Pathways Involving
ThDP-dependent Enzymes 64
Definitions of Words and Terms 65
List of Abbreviations 65
References 66

Chemistry and Biochemistry
Chapter 5 The Chemistry, Biochemistry and Metabolism

of Thiamin (Vitamin B1) 71
Lucien Bettendorff
5.1 Introduction 71
5.2 Chemical Properties of Thiamin 72
5.3 Thiamin Biosynthesis and Degradation 77
5.4 Riboswitches 77
5.5 Thiamin Transport 78
5.5.1 Thiamin Transporters in Mammalian Cells 78
5.5.2 Mitochondrial Transport of Thiamin
Diphosphate 79

5.6 Distribution of Thiamin Derivatives in Living
Organisms 79
5.6.1 Occurrence of ThDP 80
5.6.2 Occurrence of ThTP 80
5.6.3 Occurrence of Adenylated Thiamin
Derivatives 81

5.7 Metabolism of Thiamin Phosphates 81
5.7.1 Free and Bound ThDP Pools Coexist in the
Same Cell 81
5.7.2 Synthesis of Thiamin Diphosphate 83
5.7.3 Synthesis of ThTP 84
5.7.4 Synthesis of AThTP 84
5.7.5 Hydrolysis of ThMP 84
5.7.6 Hydrolysis of ThDP 85
5.7.7 Hydrolysis of ThTP 85
5.7.8 Thiamin-binding Proteins 86
5.8 Concluding Remarks 87
Summary Points 87
Key Facts about Thiamin-related Diseases in Humans 88
Definitions of Words and Terms 88
List of Abbreviations 89
References 89

Chapter 6 Chemistry and Biochemistry of Riboflavin and

Related Compounds 93
Mariana C. Monteiro and Daniel Perrone
6.1 Chemistry of Riboflavin 93
6.1.1 Structure and General Properties 93
6.1.2 Modes of Degradation and Stability in Foods 95
6.2 Biochemistry of Riboflavin 97
6.2.1 Digestion, Bioavailability, Absorption and
Transport 97
6.2.2 Metabolism, Storage and Excretion 100
6.2.3 Biological Functions 101
6.2.4 Requirements and Intakes 101
Summary Points 103
Key Facts about Digestion and Absorption 103
Definitions of Words and Terms 104
List of Abbreviations 105
References 105
Chapter 7 The Chemistry and Biochemistry of Niacin (B3) 108

Asdrubal Aguilera-Me ́ndez, Cynthia Ferna ́ndez-Lainez,
Isabel Ibarra-Gonza ́lez and Cristina Fernandez-Mejia
7.1 Introduction 108
7.2 Niacin Chemistry 109
7.3 Niacin Daily Requirement, Food Sources and Niacin
Deficiency 110
7.4 Factors and Diseases Affecting Niacin Requirement 110
7.5 Metabolism 111
7.5.1 Niacin de novo Synthesis from Tryptophan 111
7.5.2 NAD Biosynthesis 113
7.5.3 NADP Biosynthesis 114
7.5.4 NAD Recycling 114
7.6 NAD/NAPD Chemical and Structural Proprieties 115
7.7 NAD/NADP Metabolic Actions 115
7.7.1 Energy Metabolism and Oxidation Processes 115
7.7.2 Protective Action of NADP 118
7.7.3 Non-redox Adenosine Diphosphate
(ADP)-Ribose Transfer Reactions 119
7.8 Concluding Remarks 121
Summary Points 122
Key Facts about Niacin History 122
Definitions of Words and Terms 123
List of Abbreviations 123
Acknowledgments 124
References 124
Chapter 8 The Chemistry of Pantothenic Acid (Vitamin B5) 127

Katsumi Shibata and Tsutomu Fukuwatari
8.1 Introduction 127
8.2 Chemical Structure of Pantothenic Acid and its
Related Compounds 127
8.3 Stereoisomers of Pantothenic Acid 128
8.4 Characteristic Properties of D-(þ)-Pantothenic Acid 129
8.5 Stability of D-(þ)-Pantothenic Acid 130
8.6 Analogues of Pantothenic Acid 130
8.6.1 Panthenol 130
8.6.2 Pantetheine 131
8.6.3 Pantethine 131
8.6.4 Coenzyme A (CoA) 132
8.6.5 Iso-coenzyme A (Iso-CoA) 132
Summary Points 132
Key Facts 133
Definitions of Words and Terms 133
List of Abbreviations 133
References 134
Chapter 9 The Chemistry and Biochemistry of Vitamin B6: Synthesis of
Novel Analogues of Vitamin B6 135
Dajana Gasˇo Sokacˇ, Spomenka Kovacˇ, Valentina Busˇic ́,
Colin R. Martin and Jasna Vorkapic ́ Furacˇ
9.1 Introduction 135

9.2 Discovery of Vitamin B6 136
9.3 Function of Vitamin B6 138
9.4 Diversity of Vitamin B6 Derivatives 140
Summary Points 142
Key facts about Antidotes and Oxidative Stress 142
Definitions of Words and Terms 143
List of Abbreviations 143
References 143
Chapter 10 Biochemistry of Biotin 146
Janos Zempleni, Wei Kay Eng, Mahendra P. Singh and
Scott Baier
10.1 Introduction 146
10.1.1 History 146
10.1.2 Biosynthesis 147
10.2 Catabolism of Biotin 147
10.3 Biochemistry of Biotin 148
10.3.1 Biotin-dependent Carboxylases 148
10.3.2 Biotinylation of Histones 150
10.3.3 HLCS 151
10.3.4 Biotinidase 152
10.3.5 Cell Signalling 152
10.4 Biotin–Drug Interactions 153
Summary Points 153
Key Facts about Histones 154
Definitions of Words and Terms 154
List of Abbreviations 154
Acknowledgments 154
References 155
Chapter 11 The Chemistry of Folate 158

Abalo Chango
11.1 Introduction 158
11.2 Chemistry 158
11.2.1 Extraction and Isolation 159
11.2.2 Structure 160
11.2.3 Physicochemical Properties 160
11.3 Analysis 160
11.4 Concluding Remarks 162
Summary Points 162
Key Facts 162
List of Abbreviations 162
Acknowledgements 162
References 163

Chapter 12 The Chemistry of Cobalamins 164

Alexios S. Antonopoulos and Charalambos Antoniades
12.1 Introduction 164
12.2 Chemical Structure of Cobalamins 164
12.3 Natural Forms of Cobalamins 166
12.4 Biochemistry of Cobalamins 166
12.4.1 Methionine Synthase 167
12.4.2 Methylmalonyl-CoA Mutase 167
12.5 Concluding Remarks 168
Summary Points 168
Key Facts about the Chemistry of Cobalamins 168
Definitions of Words and Terms 169
List of Abbreviations 169
References 170

Analysis

Chapter 13 Assay of B Vitamins and other Water-soluble Vitamins

in Honey 173
Marco Ciulu, Nadia Spano, Severyn Salis, Maria I. Pilo,
Ignazio Floris, Luca Pireddu and Gavino Sanna
13.1 Honey 173
13.2 Vitamins in Honey 174
13.2.1 B Group Vitamins in Honey 177
13.2.2 Vitamin C: Ascorbic Acid 180
13.3 Assay of Water-soluble Vitamins in Honey 180
13.3.1 Assay of B Group Vitamins in Honey 180
13.3.2 Assay of Vitamin C in Honey 182
13.4 Validation 183
13.4.1 LoD and LoQ 184
13.4.2 Linearity 184
13.4.3 Precision 186
13.4.4 Trueness 186
13.5 Concluding Remarks 187
Summary Points 187
Key Facts 187
Key Facts about Honey 187
Key Facts about the Vitamins in Honey 188
Key Facts about Assaying Water-soluble
Vitamins in Honey 188
Key Facts about Assaying B Group Vitamins in Honey 188
Key Facts about Assaying Vitamin C in Honey 188
Key Facts about Validation Protocols 188

Definitions of Words and Terms 188
List of Abbreviations 189
References 191

Chapter 14 Analytical Trends in the Simultaneous Determination
of Vitamins B1, B6 and B12 in Food Products
and Dietary Supplements 195
Anna Lebiedzin ́ska and Marcin L. Marszałł
14.1 Introduction 195
14.2 Analysis of B Vitamins in Food Products and
Dietary Supplements 197
14.3 Simultaneous Analysis of Vitamins B in Food
Supplements and Food Products by HPLC 199
14.4 Simultaneous Analysis of Vitamins B6 and B12 in
Seafood Products 200
Summary Points 205
Key Facts about Electrochemical Detection 205
Definitions of Words and Terms 206
List of Abbreviations 206
References 207

Chapter 15 Spectrofluorimetric Analysis of Vitamin B1 in
Pharmaceutical Preparations, Bio-fluid and
Food Samples 210
Sang Hak Lee, Mohammad Kamruzzaman and
Al-Mahmnur Alam
15.1 Introduction 210
15.2 Fluorescence Determination of Vitamin B1 using
Various Catalysts 211
15.3 Extraction-based Determination 215
15.4 Nanomaterial-based Determination of Vitamin B1 217
15.5 Flow Injection and Other Techniques 217
15.6 Concluding Remarks 219
Summary Points 219
Key Facts 220
Key Facts about Spectrofluorimetry 220
Key Facts about Nanomaterials 220
Key Facts about Oxidation 220
Definitions of Words and Terms 220
List of Abbreviations 222
References 222

Chapter 16 Measurement of Thiamine Levels in Human Tissue 227

Natalie M. Zahr, Mary E. Lough, Young-Chul Jung
and Edith V. Sullivan
16.1 Introduction 227
16.2 Thiamine Measurements in Human Urine 228
16.3 Thiamine Measurements in Human Blood 230
16.3.1 Erythrocyte Transketolase Activation
and the TDP Effect 230
16.3.2 High Performance Liquid Chromatography
Methods 233
16.4 Thiamine Measurements in Other Human Tissue 234
16.4.1 Thiamine Measurements in Human Heart,
Liver, and Other Organs 234
16.4.2 Thiamine Measurements in Human
Cerebrospinal Fluid 239
16.4.3 Thiamine Measurements in Human Brain 240
16.5 Concluding Remarks 241
Summary Points 241
Key Facts 241
Key Facts about High Performance Liquid
Chromatography (HPLC) 241
Key Facts about Thiamine Diphosphate (TDP) 242
Key Facts about Wernicke–Korsakoff Syndrome
(WKS) 242
Definition of Words and Terms 243
List of Abbreviations 244
References 244
Chapter 17 The Assay of Thiamine in Food 252

Henryk Zielin ́ski and Juana Frias
17.1 Food as a Source of Thiamine 252
17.2 The Recommended Dietary Allowance for Thiamine 253
17.3 Overview of Analytical Methods 254
17.4 Analysis of Thiamine in Food 255
17.4.1 Extraction Procedures 255
17.4.2 Microbiological Methods for Thiamine
Analysis 256
17.4.3 Chemical Methods of Thiamine Analysis 257
17.4.4 Electrochemical Methods 264
17.4.5 Animal Assays (Biological Methods) 264
Summary Points 265
Key Facts 265

Definitions of Words and Terms 266
List of Abbreviations 266
References 267
Chapter 18 Assays of Riboflavin in Food using Solid-phase Extraction 271
Marcela A. Segundo, Marcelo V. Oso ́rio, Hugo M. Oliveira,
Luı ́sa Barreiros and Luı ́s M. Magalha ̃es
18.1 Introduction 271
18.2 Batch Solid-phase Extraction Methods 273
18.3 Automatic Flow Based Solid-phase Extraction
Methods 274
18.3.1 Off-line Method 275
18.3.2 On-line Methods 276
18.4 Concluding Remarks 281
Summary Points 281
Key Facts 281
Key Facts about Solid-phase Extraction 281
Key Facts about Flow Injection Analysis 282
Definitions of Words and Terms 282
List of Abbreviations 283
References 283
Chapter 19 Isotope Dilution Mass Spectrometry for Niacin in Food 285

Robert J. Goldschmidt and Wayne R. Wolf
19.1 Introduction 285
19.2 Methodological Considerations 287
19.2.1 Equilibration Requirement in IDMS 287
19.2.2 Sample Preparation and Analysis 287
19.3 IDMS Calculations 289
19.4 Isotopic Effect in Fragmentation of Nicotinic Acid 290
19.5 Illustrative Results for Food Samples 290
19.6 Concluding Remarks 295
Summary Points 296
Key Facts about Isotope Dilution Mass Spectrometry 296
Definitions of Words and Terms 297
List of Abbreviations 299
References 300
Chapter 20 Analysis of Pantothenic Acid (Vitamin B5) 302

Tsutomu Fukuwatari and Katsumi Shibata
20.1 Introduction 302
20.2 Extraction for Measurement 303
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20.3 Analytical Methods 304
20.3.1 Microbiological Assay 304

20.3.2 Radioimmunoassay (RIA) and Enzyme-
linked Immunosorbent Assay (ELISA) 307

20.3.3 High-performance Liquid Chromatography
(HPLC) 307
20.3.4 Mass Spectrometry (MS) 310
20.3.5 Optical Biosensor-based Immunoassay 311
20.4 Concluding Remarks 312
Summary Points 312
Key Facts about AOAC International 312
Definitions of Words and Terms 313
List of Abbreviations 314
References 314

Chapter 21 High-performance Liquid Chromatography Mass
Spectrometry Analysis of Pantothenic Acid (Vitamin B5) in
Multivitamin Dietary Supplements 317
Pei Chen
21.1 Introduction 317
21.1.1 Pantothenic Acid Supplementation: Aims
and Problems 318
21.1.2 Chemical Properties of Pantothenic
Acid 318
21.1.3 History of Analysis of Pantothenic
Acid 318

21.2 Review of Analysis of Pantothenic Acid Using
High-performance Liquid Chromatography 319
21.2.1 Introduction to High-performance Liquid
Chromatography 319
21.2.2 Earlier HPLC Method for Pantothenic Acid
Analysis 319
21.2.3 Common Detection Techniques for HPLC 320
21.3 Analysis of Pantothenic Acid Using Liquid
Chromatography Mass Spectrometry 320
21.3.1 LC-MS Interfaces 320
21.3.2 Ion Suppression 320
21.3.3 Mass Analysers 321
21.3.4 Stable Isotope Dilution Mass Spectrometry 322
21.3.5 Mobile Phases for LC-MS 322
21.4 Analysis of Pantothenic Acid Using LC/MS in
Multivitamin Dietary Supplements 322
21.4.1 Reference Standard 322
21.4.2 Sample Preparation 322

21.4.3 Chromatography 323
21.4.4 LC-MS Analysis 325
Summary Points 326
Key Facts 327
Key Facts about the National Institute of Standards
and Technology 327
Key Facts about Standard Reference Material
(SRM) 3280 327
Definitions of Words and Terms 327
List of Abbreviations 331
References 332

Chapter 22 Enzymatic HPLC Assay for all Six

Vitamin B6 Forms 335
Toshiharu Yagi
22.1 Current Status and Challenges of Vitamin B6
Analysis 335
22.2 Enzymatic Reactions for Conversion of
Vitamin B6 Forms and PNG into 4-PLA 337
22.3 Materials and Methods 338
22.3.1 Materials 338
22.3.2 Enzyme Activity Determination 338
22.3.3 HPLC System 339
22.3.4 Enzymatic Conversion into 4-PLA and
Calculation 339
22.3.5 Sample Preparation 342
22.4 Chromatograms from Analyses of Standard
4-PLA and Pistachio Nuts, and Contents of
Vitamin B6 Forms and PNG in the Sample
and Human Urine 342
22.4.1 Chromatographic Analyses of Standard
4-PLA, Vitamin B6 Forms and PNG 342
22.4.2 Analysis of all Vitamin B6 Forms and PNG
in Pistachio Nuts 342
22.4.3 Analysis of Vitamin B6 Forms and PNG in
Human Urine 348
22.5 Concluding Remarks 349
Summary Points 349
Key Facts 349
Key Facts about Vitamin B6 349
Key Facts about Enzymes 350
Definitions of Words and Terms 350
List of Abbreviations 351
References 351

Chapter 23 Analysis of Biotin (Vitamin B7) and Folic Acid (Vitamin B9):
A Focus on Immunosensor Development with Liposomal
Amplification 353
Ja-an Annie Ho, Yu-Hsuan Lai, Li-Chen Wu,
Shen-Huan Liang, Song-Ling Wong and Jr-Jiun Liou
23.1 Introduction 353
23.2 Current Available Analytical Methods for Biotin and
Folate 355
23.2.1 Analytical Methods for Biotin 355
23.2.2 Analytical Methods for Folic Acid 357
23.3 Application of Liposome in the Development of New
Immunosensing Systems for Biotin and Folic Acid 358
23.3.1 Immunosensors for Biotin 358
23.3.2 Immunosensors for Folic Acid 364
23.4 Concluding Remarks 367
Summary Points 369
Key Facts about Immunosensors 369
Definitions of Words and Terms 370
List of Abbreviations 371
References 372
Chapter 24 Biotin Analysis in Dairy Products 377

David C. Woollard and Harvey E. Indyk
24.1 Introduction 377
24.2 Microbiological Methods 379
24.3 Biological Methods 380
24.4 Chromatographic and Physicochemical Methods 381
24.5 Ligand-binding Methods 385
24.5.1 Labelled Techniques 385
24.5.2 Non-Labelled Techniques 387
24.6 Biotin Forms and Concentration in Milk and
Dairy Products 389
Summary Points 391
Key Facts 391
Definitions of Words and Terms 392
List of Abbreviations 392
References 393
Chapter 25 Quantitation of Folates by Stable Isotope Dilution Assays 396

Michael Rychlik
25.1 Folates 396
25.2 Current Methods for the Analysis of Folates 398

25.2.1 Microbiological Assays 398
25.2.2 Binding Assays 399
25.2.3 Chromatography 399
25.3 Stable Isotope Dilution Assays 399
25.4 Benefits and Limitations of Folate SIDAs 401
25.4.1 Benefits 401
25.4.2 Limitations 401
25.5 Application of SIDAs to Folate Analysis 403
25.5.1 Stable Isotopologues of Folates 403
25.5.2 SIDAs in Food Folate Analysis 405
25.5.3 Tracer Folates and SIDAs in Folate
Analysis of Clinical Samples 405
25.6 Method Comparisons 407
25.6.1 Folates in Blood Plasma 408
25.6.2 Comparisons of Folates Analyses
in Foods 410
25.7 Perspectives 412
Summary Points 412
Key Facts 413
Definitions of Words and Terms 413
List of Abbreviations 414
Acknowledgment 414
References 414

Chapter 26 Analysis of Cobalamins (Vitamin B12) in Human Samples:
An Overview of Methodology 419
Dorte L. Lildballe and Ebba Nexo
26.1 Introduction 419
26.2 Cobalamins in Humans 420
26.2.1 Cobalamins in Human Serum 420
26.3 Analysis of Cobalamins in Human Serum 421
26.3.1 Sample Preparation 422
26.3.2 Calibrators 424
26.3.3 Analytical Principles 425
26.3.4 Choice of Method 430
26.4 Concluding Remarks 432
Summary Points 432
Key Facts 433
Key Facts about Assay Validation 433
Key Facts about Cobalamin Analysis in Human
Samples 434
Definitions of Words and Terms 434
List of Abbreviations 436
References 436

Chapter 27 Assay by Biosensor and Chemiluminescence for Vitamin B12 439

M.S. Thakur and L. Sagaya Selva Kumar
27.1 Introduction to Biosensors 439
27.2 Biosensor-based Assay for Vitamin B12 440
27.3 Chemiluminescence 442
27.3.1 Enzyme-based Enhanced CL 443
27.3.2 Chemiluminescence of Luminol 443
27.3.3 Chemiluminescence of the Dioxetane,
CDP-Star 443
27.3.4 Chemiluminescence of Acridans 444
27.3.5 Electrochemiluminescence 445
27.4 Chemiluminescence Analysis of Vitamin B12 445
27.4.1 Acridium Ester Based Chemiluminescence 445
27.4.2 Luminol Based Chemiluminescence 445
27.4.3 Chemiluminescence Work at CFTRI 447
27.5 Concluding Remarks 452
Summary Points 452
Key Facts 453
Definition of Words and Terms 454
List of Abbreviations 454
References 455

Chapter 28 The Diagnostic Value of Measuring Holotranscobalamin
(Active Vitamin B12) in Human Serum: A Clinical
Biochemistry Viewpoint 458
Fabrizia Bamonti and Cristina Novembrino
28.1 Introduction 458
28.2 HoloTC Analytical Performance 461
28.2.1 Pre-analytical Phase 461
28.2.2 Analytic Phase 462
28.2.3 Post-analytical Phase: Clinical Studies 464
28.3 Clinical Significance and Utility 469
28.3.1 Vitamin B12 Status of Elderly People 469
28.3.2 Vitamin B12 Status of Vegetarians and Vegans 470
28.3.3 Vitamin B12 Status in Different Countries
and Ethnic Groups 471
28.3.4 HoloTC in Subjects with Renal Failure 471
28.3.5 Vitamin B12 Status in Pregnancy 471
28.4 Discussion 471
28.4.1 Asymptomatic Subjects’ HoloTC
Concentrations 472
28.4.2 Asymptomatic Subjects’ ‘Hcy Panel’ 474
28.5 Concluding Remarks 474
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Summary Points 474
Key Facts about Cobalamin Deficiency 475
Definitions of Key Terms 475
List of Abbreviations 476
References 476

Function and Effects

Chapter 29 B Vitamins (Folate, B6 and B12) in Relation to Stroke and its
Cognitive Decline 481
Concepcio ́n Sa ́nchez-Moreno and Antonio Jime ́nez-Escrig
29.1 Introduction 481
29.2 B Vitamins: Folate, B12, B6 484
29.3 Homocysteine 494
29.4 Concluding Remarks 495
Summary Points 495
Key Facts 496
Key Features of B Vitamins: Folate, Vitamin B6 and
Vitamin B12 496
Key Features of Stroke 496
Definitions of Words and Terms 497
List of Abbreviations 498
References 498
Chapter 30 Epilepsy and B Vitamins 504

Terje Apeland, Roald E. Strandjord and
Mohammad Azam Mansoor
30.1 Introduction 504
30.2 Infrequent B Vitamin Disorders may Induce Epilepsy 504
30.2.1 Vitamin B6 505
30.2.2 Folate 506
30.2.3 Thiamine 507
30.2.4 Vitamin B12 508
30.3 Antiepileptic Drugs and B Vitamins 508
30.3.1 AEDs and Folate 509
30.3.2 AEDs and Vitamin B6 513
30.3.3 AEDs and Vitamin B12 514
30.3.4 AEDs and Vitamin B2 515
30.3.5 AEDs and Vitamin B7 (Biotin) 515
30.3.6 AEDs and Vitamin B1 516
30.4 AEDs and Vitamin Supplementation 516
30.4.1 Folic Acid Supplements 517
30.4.2 Supplements with Vitamins B1, B2, B6, B7
and B12 517

Summary Points 518
Key Facts 518
Key Features about Epilepsy 518
Key Facts about Epilepsy Treatment 519
Key Facts about the C677T Polymorphism of
MTHFR 519
Definitions of Words and Terms 520
List of Abbreviations 520
References 521

Chapter 31 B Vitamins and Folate in Multiple Micronutrient

Intervention: Function and Effects 524
Faruk Ahmed
31.1 Introduction 524
31.2 Functions of B Vitamins 525
31.3 Effect of Supplementation 526
31.3.1 Haemoglobin Concentration 526
31.3.2 Micronutrient Status 527
31.3.3 Growth in Children 528
31.3.4 Morbidity in Children 528
31.3.5 Birth Outcomes 529
31.3.6 Cognitive Function 531
31.3.7 Cardiovascular Disease 532
31.4 Concluding Remarks 532
Summary Points 533
Key Facts 533
Key Facts about Multiple Micronutrient
Intervention 533
Key Facts about Anaemia (Low Haemoglobin
in Blood) 534
Key Facts about Homocysteine 534
Definition of Words and Terms 534
List of Abbreviations 535
References 535
Chapter 32 Wernicke’s Encephalopathy caused by Thiamine (Vitamin B1)
Deficiency 538
Alan S. Hazell
32.1 Introduction 538
32.2 Neuroanatomical Damage in Wernicke’s
Encephalopathy and Thiamine Deficiency 539
32.3 Thiamine-dependent Enzymes 539
32.4 Pathophysiology of Thiamine Deficiency 540
32.5 Glucose Utilization in Thiamine Deficiency 541
32.6 Excitotoxicity and Thiamine Deficiency 542

32.7 Oxidative Stress and Thiamine Deficiency 544
32.8 Inflammation in Thiamine Deficiency and
Wernicke’s Encephalopathy 544
32.9 Blood–Brain Barrier in Thiamine Deficiency 545
32.10 Neurodegenerative Disease and Thiamine Deficiency 545
32.11 Relative Contributions of Thiamine Deficiency and
Alcohol to Wernicke’s Encephalopathy 546
32.12 Concluding Remarks 547
Summary Points 547
Key Facts about Wernicke’s Encephalopathy 548
Definitions of Words and Terms 548
List of Abbreviations 549
Acknowledgements 549
References 550
Chapter 33 Disturbances in Acetyl-CoA Metabolism: A Key Factor
in Preclinical and Overt Thiamine Deficiency
Encephalopathy 553
Andrzej Szutowicz, Agnieszka Jankowska-Kulawy and
Hanna Bielarczyk
33.1 Introduction 553
33.2 Sources of Neuronal Susceptibility to Thiamine
Diphosphate Deficiency 555
33.3 Brain Thiamine Diphosphate Levels and
Encephalopathy 557
33.4 Transmitter Systems in Thiamine Deficiency
Encephalopathy 557
33.4.1 Glutamate 558
33.4.2 Acetylcholine 559
33.5 Acetyl-CoA Metabolism a Primary Target for TDP
Deficiency 560
33.5.1 Sources of Acetyl-CoA in the Brain 560
33.5.2 Acetyl-CoA Compartmentalization in Brain
Cells 562
33.5.3 Redistribution of Acetyl-CoA in Brain
Subcellular Compartments in Pathological
Conditions 563
33.6 Alcoholism and Subclinical Thiamine Deficiency 564
33.7 Screening for Minimal or Asymptomatic Thiamine
Deficiency 565
Summary Points 566
Key Facts 566
Definitions of Words and Terms 567
List of Abbreviations 568

Acknowledgements 569
References 569

Chapter 34 Thiamine Deficiency and Neuronal Calcium

Homeostasis 572
Zunji Ke and Jia Luo
34.1 Introduction 572
34.2 Thiamine Deficiency Disrupts Homeostasis
of Intracellular Ca21 574
34.3 Consequences of TD-induced Disruption
of Ca21 Homeostasis 575
Summary Points 576
Key Facts about Glutamate Receptors 576
Definitions of Words and Terms 577
List of Abbreviations 577
References 578

Chapter 35 Role of Thiamine in Obesity-related Diabetes:

Modification of the Gene Expression 580
Yuka Kohda, Takao Tanaka and
Hitoshi Matsumura
35.1 Introduction 580
35.2 Does Thiamine Intervention Decrease the Extent of
Weight Gain? 581
35.3 Thiamine Intervention Decreases not only Body
Weight but also Visceral Fat Mass and Adipocyte Size 581
35.4 Thiamine Decreases Hepatic Triglyceride
Accumulation and Modulates PDH Activity 584
35.5 Thiamine Differentially Modifies Transcript Expression
Levels of Genes Involved in Carbohydrate Metabolism,
Lipid Metabolism, Vascular Physiology and
Carcinogenesis in the Liver 585
35.6 Concluding Remarks 587
Summary Points 587
Key Facts 588
Key Features of Otsuka Long–Evans Tokushima
Fatty Rats 588
Key Features of Thiamine Intervention in OLETF Rats 588
Key Features of Obesity Worldwide 588
Key Features of Microarray Analysis 589
Definitions of Words and Terms 589
List of Abbreviations 590
References 590

Chapter 36 Riboflavin Uptake 592

Magdalena Zielin ́ska-Dawidziak
36.1 Introduction 592
36.2 Recognized Mechanisms of Riboflavin Transport 594
36.2.1 Passive Diffusion 594
36.2.2 Carrier-mediated Transport 594
36.2.3 Receptor-mediated Endocytosis 594
36.3 Absorption and Transport of Riboflavin 595
36.3.1 Small Intestine 595
36.3.2 Large Intestine 598
36.3.3 Blood 602
36.3.4 Liver cells 602
36.3.5 Brain 603
36.3.6 Placenta 604
36.3.7 Kidneys 604
36.3.8 Ocular System 605
36.4 Concluding Remarks 605
Summary Points 606
Key Facts about Enterocytes 606
Definition of Words and Terms 606
List of Abbreviations 607
References 607
Chapter 37 Riboflavin and b-oxidation Flavoenzymes 611

Ba ́rbara J. Henriques, Joa ̃o V. Rodrigues and
Cla ́udio M. Gomes
37.1 Riboflavin Metabolism and Chemistry 611
37.1.1 Riboflavin Metabolism 612
37.1.2 Flavin Chemistry and Flavoproteins 613
37.2 Mitochondrial b-oxidation Flavoenzymes 613
37.2.1 Overview of Mitochondrial b-oxidation 614
37.2.2 The Flavoprotein Enzymatic Machinery 615
37.3 Riboflavin Effects in Defective b-oxidation
Flavoenzymes 621
37.3.1 Proteomics Responses to Riboflavin
Supplementation 622
37.3.2 Molecular Basis for Effects of ETF
Flavinylation 623
37.4 Concluding Remarks 626
Summary Points 626
Key Facts 627
Key Facts about Flavoproteins 627
Key Facts about Inborn Errors of Fatty Acid
Oxidation 628

Definitions of Words and Terms 628
List of Abbreviations 629
Acknowledgements 630
References 630
Chapter 38 Function and Effects of Niacin (Niacinamide, Vitamin B3) 633

Ahmed A. Megan, Said O. Muhidin, Mahir A. Hamad
and Mohamed H Ahmed
38.1 Food Sources of Niacin 633
38.2 Absorption, Excretion and Clinical Features of
Niacin Deficiency 634
38.3 Niacin Overdose 634
38.4 Cellular Function and Effects of Niacin 634
38.4.1 Niacin and Cellular Lipid Metabolism 636
38.4.2 Non-oxidative and Reduction Reactions
involving Niacin (NAD Substrate) 636
38.4.3 DNA Repair 637
38.4.4 Apoptosis and Necrosis 637
38.5 Metabolic Effects of Niacin 638
38.5.1 Niacin and Lipid Metabolism and
Atherosclerosis 638
38.5.2 Effect of Niacin on Atherosclerosis,
Inflammation and Vascular Reactivity 641

38.5.3 Niacin and Dyslipidaemia and Hyper-
phosphatemia with Chronic Kidney Disease 643

38.5.4 Effect of Niacin on Insulin Sensitivity and
Glucose Metabolism 645
38.5.5 Niacin and Cardiovascular Disease 646
Summary Points 648
Key Facts 649
List of Abbreviations 649
References 651
Chapter 39 Pharmacological Use of Niacin for Lipoprotein Disorders 660
John R. Guyton, Wanda C. Lakey, Kristen B. Campbell and
Nicole G. Greyshock
39.1 Introduction 660
39.2 Mechanisms of Action 661
39.2.1 Role of the Niacin Receptor (GPR109A) in
Inhibiting Non-esterified Fatty Acid Release
from Adipocytes 661
39.2.2 Effects on Apolipoprotein B-containing
Lipoproteins 662

39.2.3 Niacin-Related Mechanisms to Increase
HDL and Reverse Cholesterol Transport 662
39.2.4 Niacin-Induced Cutaneous Flushing 663
39.2.5 Niacin-Induced Reduction in Inflammation
and Oxidative Stress 663
39.3 Lipoprotein Effects of Niacin 663
39.4 Adverse Effects and Drug Administration 664
39.4.1 Flushing 664
39.4.2 Hepatotoxicity 664
39.4.3 Myopathy 665
39.4.4 Insulin Resistance and Hyperglycemia 665
39.5 Randomized Trials with Cardiovascular and Clinical
Endpoints 665
39.5.1 Coronary Drug Project, the Only Large
Monotherapy Trial 665
39.5.2 Smaller Randomized Trials with Anatomic
Endpoints 667
39.5.3 The AIM-HIGH Study 667
Summary Points 668
Key Facts 669
Key Facts about Mechanisms in Niacin
Pharmacology 669
Key Facts about Niacin’s Effects on Lipoproteins 669
Key Facts about Niacin and Atherosclerosis
Prevention 669
Definitions of Words and Terms 670
List of Abbreviations 671
References 671
Chapter 40 Pellagra: Psychiatric Manifestations 675
Ravi Prakash, Priyanka Rastogi and Suprakash Choudhary
40.1 Introduction 675
40.2 Common Early Psychiatric Features 676
40.3 Cognitive Deficits in Pellagra 676
40.4 Psychotic Spectrum Features in Pellagra 677
40.5 Case Vignette: A Unique case of Pellagra Delusional
Parasitosis 678
40.6 Neurophysiological Mechanisms of
Pellagra–Psychiatric Features 680
Summary Points 681
Key Facts 681
Key Facts about Pellagra 681
Key Facts about Neuropathophysiological
Understanding of Pellagra 682

Definitions of Words and Terms 682
List of Abbreviations 683
References 683
Chapter 41 Pantetheine and Pantetheinase: From Energy Metabolism
to Immunity 685
Takeaki Nitto
41.1 The Synthesis and Metabolism of Coenzyme A 685
41.2 Enzymatic Features of Pantetheinase 686
41.3 Pantetheinase Gene Family 687
41.3.1 Pantetheinase/Vanin-1/VNN1 687
41.3.2 GPI-80/VNN2 688
41.3.3 Vanin-3/VNN3 689
41.4 Role of Pantetheinase in vivo: Regulation of
Inflammation rather than CoA Metabolism? 690
41.4.1 Vanin-1 Deficient Mice 690
41.4.2 Cysteamine: A Key Player in Inflammation
and Host Defence 691

41.5 Panetetheinase Family Genes and Proteins as
Indicators of Human Diseases 692
41.6 Studies on Pantetheinase in Future 692
Summary Points 693
Key Facts 693
Key Facts about Neutrophils 693
Key Facts about Cysteamine 694
Definitions of Words and Terms 694
List of Abbreviations 695
References 695

Chapter 42 Function and Effects of Pyridoxine (Vitamin B6):

An Epidemiological Review of Evidence 699
Junko Ishihara and Hiroyasu Iso
42.1 Overall Characteristics and Function 699
42.2 Current Recommended Intake and Chronic Diseases 701
42.3 Epidemiologic Evidence of Vitamin B6 and Vascular
Disease 702
42.3.1 Findings on Dietary Intake in Prospective
Observational Studies 702
42.3.2 Findings on Blood Level in Prospective
Observational Studies 703
42.3.3 Findings from Clinical Trials 703
42.3.4 Current Knowledge of the Effect on
Vascular Disease 704
42.4 Epidemiologic Evidence of Vitamin B6 and Cancer 704
42.4.1 Findings on Dietary Intake in Observational
Studies 704
42.4.2 Findings for Blood Level in Observational
Studies 706
42.4.3 Findings from Clinical Trials 706
42.4.4 Current Knowledge of Effect on Cancer 707
Summary Points 707
Key Facts: Levels of Evidence Reliability 707
Definitions of Words and Terms 708
List of Abbreviations 709
References 709
Chapter 43 Function and Effects of Biotin 716
Jean-Jacques Houri, Philippe Mougenot, Franc ̧ ois Guyon
and Bernard Do
43.1 Biotin and Biochemical Pathways 716
43.2 Biotin and Regulation of Gene Expression 718
43.3 Sources of Biotin and Human Biotin Requirements 720
43.4 Bioavailability 721
43.5 Pharmacological Effects of Biotin 721
43.6 Physiopathological Aspects of Biotin Deficiency 722
43.6.1 Causes of Biotin Deficiency 722
43.6.2 Biotin Deficiency Assessment 724
43.7 Consequences of Biotin Deficiency 725
Summary Points 727
Key Facts about Prosthetic Groups 727
Definitions of Words and Terms 727
List of Abbreviations 728
References 728
Chapter 44 The Importance of Folate in Health 734
Abalo Chango, David Watkins and Latifa Abdennebi-Najar
44.1 Introduction 734
44.2 Folate Absorption, Transport and Metabolism 736
44.2.1 Absorption 736
44.2.2 Folate Transport 737
44.2.3 Distribution, Storage and Excretion 738
44.2.4 Metabolism 738
44.3 Biochemical Function, Consequences of Folate
Deficiency and Health Alteration 740
44.3.1 Biochemical Function 740
44.3.2 Folate Deficiency and Health Alteration 742
44.4 Common Genetic Variation in Folate Metabolism 745

44.5 Synthetic Folic Acid Use for Health:
Supplementation, Fortification and Adverse
Effect 746
44.6 Folate Nutrigenetics, Nutrigenomics and Epigenetics
For Future Investigations 747
44.7 Concluding Remarks 747
Summary Points 748
Key Facts: Folate discovery and neural tube defects 748
Definitions of Words and Terms 748
List of Abbreviations 749
Acknowledgments 750
References 750

Chapter 45 Homocysteine and Vascular Disease: A Review of the
Published Results of 11 Trials involving 52 260
Individuals 754
Robert Clarke and Jane Armitage
45.1 Introduction 754
45.2 Observational Studies of Homocysteine and
Cardiovascular Disease 755
45.3 Homocysteine, Folate and Cancer 756
45.4 Trials of B Vitamins for Prevention of
Cardiovascular Disease 757
45.4.1 Homocysteine-lowering Trials for
Prevention of Cardiovascular Disease 757
45.4.2 Methodological Considerations 758
45.5 Effects of B Vitamins on Cardiovascular Disease,
Cancer and Mortality 758
45.5.1 Characteristics of the Participating Trials 758
45.5.2 Effects on CHD and Stroke Outcomes 759
45.5.3 Effects on Cancer and All-cause Mortality
Outcomes 760
45.6 Analysis of the Role of B Vitamins for Prevention of
Cardiovascular Disease 762
Summary Points 764
Key Facts 765
List of Abbreviations 765
References 765
Chapter 46 Vitamin B12 and Folate in Dementia 769

Rachna Agarwal
46.1 Introduction 769
46.2 Vitamin B12, Folate and Homocysteine 771
46.2.1 Biochemistry 771

46.2.2 One-carbon Metabolism and Brain
Functions 771
46.2.3 Interrelationship between vitamin
B12, Folate and Homocysteine 772
46.3 Status of B Vitamins in Dementia 772
46.4 Old Age and Decline in Vitamin B Status 773
46.5 Vitamin B and Cognitive Decline Mechanism 775
46.6 Role of Laboratory Indicators in Detecting Vitamin
B Status 777
46.7 Treatment-related Issues 777
46.7.1 Vitamin B12 Supplementation 778
46.7.2 Folate Supplementation 779
46.8 Concluding Remarks 779
Summary Points 780
Key Facts 780
Definition of Words and Terms 781
List of Abbreviations 781
References 782
Chapter 47 Cobalamin and Nutritional Implications in Kidney Disease 786

Katsushi Koyama
47.1 Intake and Absorption of Vitamin B12 786
47.2 Intracellular Metabolism of Vitamin B12 787
47.2.1 Cyanocobalamin Trafficking Chaperone and
CKD 787
47.2.2 Abnormal Cyanide Metabolism in CKD and
Oxidative Stress 787
47.3 Does CKD Induce Vitamin B12 Deficiency? 790
47.4 Vitamin B12-related Biomarkers and CKD 793
47.4.1 Homocysteine—the Best Known Biomarker
Associated with Vitamin B12 793
47.4.2 Manifestation of Hyperhomocysteinemia 793
47.5 Association with Vitamin B6 796
47.6 Concluding Remarks 798
Summary Points 798
Key Facts 799
Key Facts about Chronic Kidney Disease 799
Key Facts about Homocysteine 799
Key Facts about Asymmetric Dimethylarginine 800
Definitions of Words and Terms 800
List of Abbreviations 801
References 802
Subject Index 805

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