Vitamin A and Carotenoids: Chemistry, Analysis, Function and Effects

606 Pages·2012·16.47 MB·English

by  J Lin, Victor R Preedy, Ronda Greaves, M Petkovich, T Miyazawa, Beatrice Albertini, V Baskaran, T Bohn, L Jia, Ewa Czeczuga-Semeniuk, C Tode, M K Kim, H A Tajmir-Riahi, Alessandra. Gentili, J. S Khillan, N A Patel, Gerald Woollard, Anita Oberholster, Ange

Vitamin A and Carotenoids
Chemistry, Analysis, Function and Effects
PDuobwlinshloeadd oedn o21n A17u gOucstto 2b0e1r 22 0o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP001
Food and Nutritional Components in Focus
Series Editors:
Professor Victor R Preedy, School of Medicine, King’s College London, UK
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Vitamin A and Carotenoids
Chemistry, Analysis, Function
and Effects
Edited by
Victor R Preedy
School of Medicine, King’s College London, UK
Email:
Food and Nutritional Components in Focus No. 1
ISBN: 978-1-84973-368-7
ISSN: 2045-1695
A catalogue record for this book is available from the British Library
# The Royal Society of Chemistry 2012
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VPDuioebwlin sOhloneadldi noeedn o21n A17u gOucstto 2b0e1r 22 0o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP001
Preface
PROFESSOR VICTOR R PREEDY BSC PHD DSC FIBIOL
FRSPH FRCPATH
In the past three decades there have been major advances in our understanding
of the chemistry and function of nutritional components. This has been
enhanced by rapid developments in analytical techniques and instrumentation.
Chemists, food scientists and nutritionists are, however, separated by divergent
skills, and professional disciplines. Hitherto this transdisciplinary divide has
been difficult to bridge.
The series Food and Nutritional Components in Focus aims to cover in a
single volume the chemistry, analysis, function and effects of components in
the 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 imparts holistic
information and covers the latest knowledge with a structured format.
Vitamin A and Carotenoids has four major sections, namely:
Vitamin A and Carotenoids in Context
Chemistry and Biochemistry
Analysis
Function and Effects
The first section covers vitamin A terminology, vitamin A in context of other
vitamins, b-carotene and supplementation. The Chemistry and Biochemistry
section covers basic features, nomenclature, metabolites, structural analysis,
complexes with DNA and RNA, encapsulation, thermal degradation and
bioavailability. The section on Analysis includes blood, nutritional status,
plants and fruit, milk, dairy products and many specific foods. There are
various assay techniques such as HPLC, capillary and thin-layer chromato-
Food and Nutritional Components in Focus No. 1
Vitamin A and Carotenoids: Chemistry, Analysis, Function and Effects
Edited by Victor R Preedy
# The Royal Society of Chemistry 2012
Published by the Royal Society of Chemistry, www.rsc.org
v
PDuobwlinslhoeadd eodn o2n1 1A7u Ogucstto b2e0r1 2 0o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP005
vi Preface
graphy, NMR, mass spectrometry and other methods. Finally, the section on
Function and Effects includes the distribution of Vitamin A and their
metabolites in human tissue, deficiencies, receptors, developmental growth,
signalling, 9-cis-retinoic acid, cancer risk, the immune system, brain and lung.
Each Chapter transcends the intellectual divide with a novel cohort of
features namely by containing:
N Summary Points
N Key Facts (areas of focus explained for the lay person)
N Definitions of Words and Terms
It is designed for chemists, biochemists, 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
VPDuioebwwlins Olhoenadldi enoden o2n1 1A7u Ogucstot b2e0r1 20 o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP005
Contents
Vitamin A and Carotenoids in Context
Chapter 1 Retinol, Retinoic Acid, Carotenes and Carotenoids: Vitamin A
Structure and Terminology 3
Gerald Wollard
1.1 Introductory Remarks 3
1.2 Structure and Function of Carotenoids 4
1.2.1 Central Carotenoid Chain 4
1.2.2 The End Ring Systems 5
1.3 Biosynthesis 6
1.3.1 Biosynthetic Pathway 6
1.3.2 Key Observations for Carotenoid Biosynthesis 7
1.4 Trivial Names of Carotenoids 8
1.4.1 Origins of Trivial Names 8
1.4.2 Major Nutritional Carotenoids 9
1.4.3 Provitamin A Carotenoids 9
1.4.4 Ambiguities in Trivial Names 9
1.5 IUPAC Definitions 9
1.5.1 Systematic Names 9
1.5.2 Semi-systematic Names 11
1.6 Stereochemistry of Carotenoids 14
1.6.1 Stereoisomers 14
1.6.2 Geometric Isomers 14
1.7 Structure of Retinol 15
1.7.1 Prototypical Vitamin A Compounds 15
1.7.2 Chemical Nature of Retinol 15
1.7.3 Retinol Systematic Name 16
1.7.4 Retinol Semi-systematic Name 16
Food and Nutritional Components in Focus No. 1
Vitamin A and Carotenoids: Chemistry, Analysis, Function and Effects
Edited by Victor R Preedy
# The Royal Society of Chemistry 2012
Published by the Royal Society of Chemistry, www.rsc.org
vii
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viii Contents
1.7.5 Retinol Trivial Names 16
1.7.6 Retinol cis–trans Isomerism 16
1.7.7 Retinol from Symmetrical Cleavage of
Carotenoids 17
1.8 Retinoids: Derivatives of Retinol 17
1.8.1 Retinal 18
1.8.2 Retinoic Acid 18
1.8.3 Retinoid Geometric Isomers 19
Key Facts 20
List of Abbreviations 21
References 21
Chapter 2 Vitamin A in the Context of Other Vitamins and Minerals 23
Jennifer H. Lin and Kuang-Yu Liu
2.1 Sources of Vitamin A and Other Vitamins and
Minerals 23
2.2 Intakes of Vitamin A as well as Other Vitamins and
Minerals Around the World 24
2.2.1 In the Malnourished Countries 24
2.2.2 In the USA and Europe 26
2.3 Interaction of Vitamin A with Other Vitamins and
Minerals 27
2.3.1 Vitamin A and Zinc 27
2.3.2 Vitamin A and Iron 28
2.3.3 Vitamin A and Vitamin D 29
2.4 Chronic Disease Prevention with Supplementation of
Vitamin A Alone or in Combination with Other
Vitamins and Minerals 29
2.4.1 Cancer Prevention 31
2.4.2 Prevention of Vascular Events 32
2.4.3 Prevention of Other Diseases 32
2.5 Conclusion 33
Summary Points 33
Key Facts 33
Definition of Words and Terms 34
List of Abbreviations 35
References 35
Chapter 3 The Importance of b-Carotene in the Context of Vitamin A 39
Hans K. Biesalski and Donatus Nohr
3.1 Introduction 39
3.2 b-Carotene as Antioxidant and/or Pro-oxidant 41
3.2.1 Antioxidant/Pro-oxidant Activities 41
3.2.2 Radical Scavenging Properties 41
3.2.3 Singlet Oxygen Quenching 41
VPDuioebwwlins Olhoenadldi enoden o2n1 1A7u Ogucstot b2e0r1 20 o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP007
Contents ix
3.3 Necessity of Vitamin A 42
3.3.1 How Much b-Carotene is Needed to Ensure
Sufficient Vitamin A Supply? 44
3.3.2 For Embryonic Development and Pregnant
Women 44
3.4 b-Carotene as Provitamin A 44
3.4.1 Natural Sources of b-Carotene 44
3.4.2 Bioavailability of b-Carotene 45
3.4.3 The Role of b-Carotene as Provitamin A for
Vegetarians 46
3.4.4 Supply of the Population with Preformed
Vitamin A 47
3.4.5 Basic Need for b-Carotene to Ensure a
Sufficient Intake to Meet the Vitamin A
Requirement? 48
Summary Points 50
Key Facts 50
Definition of Words and Terms 51
List of Abbreviations 51
References 52
Chapter 4 Vitamin A in the Context of Supplementation 55
Frank T. Wieringa, Marjoleine A. Dijkhuizen and
Jacques Berger
4.1 The Rational for Vitamin A Supplementation 55
4.2 Vitamin A Supplementation for Children between 6
and 59 Months of Age 56
4.3 Vitamin A Supplementation for Whom? And does it
Work? 58
4.3.1 Vitamin A Supplementation of Newborns 58
4.3.2 Vitamin A Supplementation for Women
Directly after Delivery 58
4.3.3 Vitamin A Supplementation of Pregnant
Women 59
4.3.4 Vitamin A Supplementation and HIV Infection 60
4.3.5 Vitamin A Supplementation and Measles
Infection 60
4.4 Time for Reflection 61
4.5 Vitamin A and the Immune System 62
Summary Points 64
Key Facts 64
List of Abbreviations 66
References 66
VPDuioebwwlins Olhoenadldi enoden o2n1 1A7u Ogucstot b2e0r1 20 o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP007
x Contents
Chemistry and Biochemistry
Chapter 5 The Chemistry of Vitamin A 73
Alessandra Gentili
5.1 Introduction 73
5.2 Physicochemical Properties 76
5.2.1 Appearance and Solubility 76
5.2.2 Chemical Stability 76
5.3 Spectral Properties 77
5.4 Mass Spectrometry 82
Summary Points 82
Key Facts 84
List of Abbreviations 86
References 86
Chapter 6 Nomenclature of Vitamin A and Related Metabolites 90
Niketa A. Patel
6.1 Introduction 90
6.2 Nomenclature 91
Summary Points 93
Key Facts 93
Definition of Words and Terms 93
List of Abbreviations 94
Acknowledgements 94
References 94
Analysis
Chapter 7 Structural Analysis of Vitamin A Complexes with DNA
and RNA 97
H. A. Tajmir-Riahi and P. Bourassa
7.1 Introduction 97
7.2 Analytical Methods 98
7.2.1 FTIR Spectroscopy 98
7.2.2 CD Spectroscopy 98
7.2.3 Fluorescence Spectroscopy 99
7.2.4 Molecular Modelling 100
7.3 Structural Characterization 100
7.3.1 FTIR Spectra of Retinoid–DNA and Retinoid–
RNA Complexes 100
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