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

606 Pages·2012·16.47 MB·English
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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 Titles in the Series: 1: Vitamin A and Carotenoids: Chemistry, Analysis, Function and Effects How to obtain future titles on publication: A standing order plan is available for this series. A standing order will bring delivery of each new volume immediately on publication. For further information please contact: Book Sales Department, Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge, CB4 0WF, UK Telephone: +44 (0)1223 420066, Fax: +44 (0)1223 420247 Email: 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 All rights reserved Apart from fair dealing for the purposes of research for non-commercial purposes or for private study, criticism or review, as permitted under the Copyright, Designs and Patents Act 1988 and the Copyright and Related Rights Regulations 2003, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry or the copyright owner, or in the case of reproduction in accordance with the terms of licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at the address printed on this page. The RSC is not responsible for individual opinions expressed in this work. Published by The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 0WF, UK Registered Charity Number 207890 For further information see our web site at www.rsc.org Printed in the United Kingdom by Henry Ling Limited, at the Dorset Press, Dorchester, DT1 1HD 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 PDuobwlinslhoeadd eodn o2n1 1A7u Ogucstto b2e0r1 2 0o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP007 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 VPDuioebwwlins Olhoenadldi enoden o2n1 1A7u Ogucstot b2e0r1 20 o1n2 http://pubs.rsc.org | doi:10.1039/9781849735506-FP007

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