Carotenoids: Volume 5: Nutrition and Health

464 Pages·2009·5.895 MB·English

by  George Britton, Synnøve Liaaen-Jensen, Hanspeter Pfander (auth.), Dr. George Britton, Prof. Dr. Hanspeter Pfander, Professor Dr. Dr. h.c. Synnøve Liaaen-Jensen (eds.)

Carotenoids
Volume 5: Nutrition and Health
Edited by G. Britton
S. Liaaen-Jensen
H. Pfander
Birkhäuser Verlag
Basel · Boston · Berlin
Editors:
Dr. George Britton Professor Dr. Dr. h.c. Synnøve Liaaen-Jensen
53 Forest Road Organic Chemistry Laboratories
Meols Department of Chemistry
Wirral Norwegian University of Science and
Merseyside Technology (NTNU)
CH47 6AT 7491 Trondheim
UK Norway
Prof. Dr. Hanspeter Pfander
CaroteNature GmbH
Chief Operating Officer
Muristrasse 8e
3006 Bern
Switzerland
Library of Congress Control Number: 2008932322
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ISBN 978-3-7643-7500-3 Birkhäuser Verlag, Basel – Boston – Berlin
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v
Dedication
NORMAN I. KRINSKY
29th June 1928 – 28th November 2008
For a period of more than 50 years from his Ph.D work on ‘Studies of Carotenoids and
Vitamin A Complexes with Proteins in Plasma and Tissues’, through his post-doctoral work
on vision, in the Harvard laboratory of Nobel laureate George Wald, to his long and
productive career at Tufts University, Boston, the name ‘Norman Krinsky’ has been
synonymous with ‘Carotenoids in Human Health and Nutrition’. A true giant in the field,
Norman pioneered so much of current thinking and understanding of the nutritional value and
health benefits of carotenoids, and this work is continued by the talented and dedicated group
of colleagues that he assembled at Tufts. It is no coincidence that so many chapters in this
Volume come from his associates, past and present, with him as a co-author on two of them.
A great teacher and communicator, Norman leaves us other legacies. The Gordon Research
Conferences on Carotenoids, initiated by him in 1992, continue to go from strength to
strength. He was co-chair of the 8th International Symposium on Carotenoids in Boston in
1987, and co-editor of the proceedings, published as Carotenoids: Chemistry and Biology
(editors N. I. Krinsky, M. M. Mathews-Roth and R. F. Taylor, 1990), and his more recent
book Carotenoids in Health and Disease (editors N. I. Krinsky, S. T. Mayne and H. Sies,
2004) is a most valuable collection of research reports on the subject.
Norman Krinsky’s contribution to carotenoid science is immense but he is also
remembered for his humanity and humour, his warmth, wit and wisdom. Always interested in
other people and their work, he was ever ready to guide and advise and has been a great
inspiration to so many. His perceptive comments and questions at conferences, always
constructive, never destructive, are legendary.
The editors all have our own memories of Norman, who was a good friend of all of us. He
will be very much missed; we will not see his like again.
That the field of Carotenoids in Human Nutrition and Health is as active and exciting as it
is today is due in no small part to our friend Norman Krinsky. It is most fitting and a great
honour for us to dedicate this volume to him and his memory.
vii
Contents
List of Contributors ............................................................................................................ xxiii
Preface ................................................................................................................................. xxvii
Editors’ Notes on the Use of this Book .............................................................................. xxix
In memoriam ....................................................................................................................... xxxi
Editors’ Acknowledgements .............................................................................................. xxxii
Abbreviations ..................................................................................................................... xxxiii

Chapter 1: Editors’ Introduction: A Healthy Debate
George Britton, Synnøve Liaaen-Jensen and Hanspeter Pfander

A. Introduction ......................................................................................................................... 1(cid:2)
B. Volume 5 ............................................................................................................................... 2(cid:2)
1. Strategy ............................................................................................................................... 2(cid:2)
2. Relation to other volumes .................................................................................................. 2(cid:2)
3. Content of Volume 5 ........................................................................................................... 3(cid:2)
a) Nutrition ..................................................................................................................... 3(cid:2)
b) Carotenoids in health and disease ............................................................................. 4(cid:2)
C. Conclusions .......................................................................................................................... 6
References ................................................................................................................................. 6

Chapter 2: Analysis of Carotenoids in Nutritional Studies(cid:2)
Frederick Khachik

A. Introduction ......................................................................................................................... 7
B.(cid:2)Isolation and Characterization ........................................................................................... 8(cid:2)
1.(cid:2)Strategy ............................................................................................................................... 8(cid:2)
2.(cid:2)Extraction ........................................................................................................................... 9(cid:2)
3. Saponification ................................................................................................................... 10(cid:2)
4. Fractionation of carotenoids by thin-layer and column chromatography ........................ 11(cid:2)
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C. Identification and Structure Elucidation ........................................................................ 12(cid:2)
D.(cid:2)HPLC of Carotenoids: General Aspects .......................................................................... 12(cid:2)
1. Special features of carotenoids and HPLC ....................................................................... 13(cid:2)
2. Strategy ............................................................................................................................. 14(cid:2)
3. Choice of system: Normal phase or reversed phase? ....................................................... 14(cid:2)
4. Normal phase .................................................................................................................... 14(cid:2)
a)(cid:2)Silica columns .......................................................................................................... 14(cid:2)
b) Silica-based bonded nitrile (CN) columns ............................................................... 16(cid:2)
5. Reversed phase ................................................................................................................. 17(cid:2)
a) C columns .............................................................................................................. 17(cid:2)
18
b) C columns .............................................................................................................. 19(cid:2)
30
6. Temperature ..................................................................................................................... 20(cid:2)
7. Test chromatograms – standard mixture .......................................................................... 20(cid:2)
8. Avoiding injection artefacts and peak distortion .............................................................. 21(cid:2)
E.(cid:2)Examples of Separations ................................................................................................... 23(cid:2)
1.(cid:2)Separation of carotenes .................................................................................................... 23(cid:2)
2. Separation of xanthophylls ............................................................................................... 25(cid:2)
3. E/Z Isomers ...................................................................................................................... 25(cid:2)
a) Carotenes ................................................................................................................. 26(cid:2)
b) Xanthophylls ............................................................................................................. 26(cid:2)
4. Acyl esters ........................................................................................................................ 26(cid:2)
5. Optical isomers/enantiomers ............................................................................................ 28(cid:2)
F. Quantitative Analysis of Carotenoids by HPLC ............................................................. 28(cid:2)
1. Selection of an internal standard ...................................................................................... 28(cid:2)
a) Requirements of an internal standard ...................................................................... 28(cid:2)
b) Examples of internal standards ................................................................................ 29(cid:2)
c) Internal standard for carotenol esters...................................................................... 30(cid:2)
2. Use of an internal standard ............................................................................................... 30(cid:2)
3. Preparation of the internal standard calibration curves .................................................... 31(cid:2)
G. HPLC of Carotenoids in Food ......................................................................................... 31(cid:2)
1. Green vegetables and fruits .............................................................................................. 31(cid:2)
2. Yellow/red fruits and vegetables containing mainly carotenes ........................................ 33(cid:2)
3. Yellow/orange fruits and vegetables containing mainly xanthophylls and xanthophyll
esters ..................................................................................................................................... 36(cid:2)
H.(cid:2)Analysis of Carotenoids in Human Serum, Milk, Major Organs, and Tissues ........... 39(cid:2)
1. Human serum and milk .................................................................................................... 39(cid:2)
2. Major organs .................................................................................................................... 41(cid:2)
I.(cid:2)Conclusions .......................................................................................................................... 43(cid:2)
References ............................................................................................................................... 43
ix
Chapter 3: Carotenoids in Food(cid:2)
George Britton and Frederick Khachik

A. Introduction ....................................................................................................................... 45(cid:2)
B. Distribution of Carotenoids in Vegetables and Fruits ................................................... 47(cid:2)
1. Green vegetables and fruits .............................................................................................. 47(cid:2)
2. Yellow, orange and red fruits and vegetables .................................................................. 49(cid:2)
a) Fruits ........................................................................................................................ 49(cid:2)
b) Roots ......................................................................................................................... 52(cid:2)
c) Seeds ......................................................................................................................... 52(cid:2)
d) Flowers ..................................................................................................................... 53(cid:2)
e) Oils ........................................................................................................................... 53(cid:2)
3. Animal-derived food products ......................................................................................... 53(cid:2)
a) Eggs .......................................................................................................................... 54(cid:2)
b) Dairy produce .......................................................................................................... 54(cid:2)
c) Seafood ..................................................................................................................... 54(cid:2)
4. Good sources .................................................................................................................... 55(cid:2)
5. Additives, colourants ........................................................................................................ 57(cid:2)
C. Effects of Environmental Conditions and Cultivation Practice .................................... 57(cid:2)
D.(cid:2)Effects of Storage, Processing and Cooking .................................................................... 58(cid:2)
1. Stability and loss or retention of carotenoids ................................................................... 58(cid:2)
2. Storage, cooking and processing ...................................................................................... 59(cid:2)
a) Transport and storage .............................................................................................. 59(cid:2)
b) Cooking and processing ........................................................................................... 60(cid:2)
3. Causes and mechanisms ................................................................................................... 61(cid:2)
a) Oxidation .................................................................................................................. 61(cid:2)
b) Geometrical isomerization ....................................................................................... 62(cid:2)
c)(cid:2)Other changes ........................................................................................................... 63(cid:2)
E.(cid:2)Conclusions and Recommendations ................................................................................. 63(cid:2)
1. Analytical data .................................................................................................................. 63(cid:2)
a)(cid:2)HPLC ........................................................................................................................ 63(cid:2)
b) Visual assessment ..................................................................................................... 64(cid:2)
c) Instrumental .............................................................................................................. 65(cid:2)
2. Some general conclusions ................................................................................................ 65(cid:2)
References ............................................................................................................................... 65
x
Chapter 4: Supplements(cid:2)
Alan Mortensen

A. Introduction ....................................................................................................................... 67(cid:2)
1. Market .............................................................................................................................. 67(cid:2)
2. Legal ................................................................................................................................. 70(cid:2)
B. Carotenoids in Supplements ............................................................................................. 71(cid:2)
1. Which carotenoids? .......................................................................................................... 71(cid:2)
2. Formulations ..................................................................................................................... 73(cid:2)
a) Oil suspensions and oleoresins ................................................................................ 74(cid:2)
b) Water-miscible formulations .................................................................................... 74(cid:2)
3. Analysis ............................................................................................................................ 75(cid:2)
C. Health Issues ...................................................................................................................... 76(cid:2)
1. Selling points .................................................................................................................... 76(cid:2)
2. Bioavailability .................................................................................................................. 77(cid:2)
3. Recommendations ............................................................................................................ 79(cid:2)
References ............................................................................................................................... 80

Chapter 5: Microbial and Microalgal Carotenoids as Colourants and
Supplements
Laurent Dufossé

A. Introduction ....................................................................................................................... 83(cid:2)
B. Carotenoid Production by Microorganisms and Microalgae ........................................ 84(cid:2)
1. β-Carotene ........................................................................................................................ 85(cid:2)
a) Dunaliella species ..................................................................................................... 85(cid:2)
b) Blakeslea trispora ..................................................................................................... 86(cid:2)
c) Phycomyces blakesleeanus ....................................................................................... 87(cid:2)
d) Mucor circinelloides ................................................................................................. 88(cid:2)
2. Lycopene .......................................................................................................................... 88(cid:2)
a) Blakeslea trispora ..................................................................................................... 88(cid:2)
b) Fusarium sporotrichioides ........................................................................................ 89(cid:2)
3. Astaxanthin ....................................................................................................................... 89(cid:2)
a) Haematococcus pluvialis .......................................................................................... 89(cid:2)
b) Xanthophyllomyces dendrorhous (formerly Phaffia rhodozyma) ............................ 90(cid:2)
c) Agrobacterium aurantiacum and other bacteria ...................................................... 91(cid:2)
4. Zeaxanthin ........................................................................................................................ 91(cid:2)
5. Canthaxanthin ................................................................................................................... 92(cid:2)
6. Torulene and torularhodin ................................................................................................ 93(cid:2)
xi
C. Prospects for Carotenoid Production by Genetically Modified Microorganisms ....... 93(cid:2)
1. Escherichia coli and other hosts ....................................................................................... 93(cid:2)
2. Directed evolution and combinatorial biosynthesis ......................................................... 94(cid:2)
D. Concluding Comments ...................................................................................................... 95(cid:2)
References ............................................................................................................................... 96

Chapter 6: Genetic Manipulation of Carotenoid Content and Composition
in Crop Plants(cid:2)
Paul D. Fraser and Peter M. Bramley

A. Introduction ....................................................................................................................... 99(cid:2)
B. Strategies for Enhancing Carotenoids in Crop Plants ................................................. 101(cid:2)
1. General considerations ................................................................................................... 101(cid:2)
2. Experimental strategies .................................................................................................. 101(cid:2)
3. Optimizing conditions .................................................................................................... 104(cid:2)
a) Choice of crop ........................................................................................................ 105(cid:2)
b) Choice of biosynthetic step(s) to target .................................................................. 105(cid:2)
c) Choice of promoter and gene/cDNA ...................................................................... 106(cid:2)
d) Targeting of the transgenic protein........................................................................ 107(cid:2)
C. Examples of the Application of Metabolic Engineering to Carotenoid Formation in
Crop Plants ........................................................................................................................... 107(cid:2)
1. Tomato ........................................................................................................................... 107(cid:2)
2. Potato .............................................................................................................................. 110(cid:2)
3. Carrot .............................................................................................................................. 110(cid:2)
4. Rice ................................................................................................................................. 111(cid:2)
5. Canola (rape seed) .......................................................................................................... 111(cid:2)
D. Conclusions and Perspectives ......................................................................................... 111(cid:2)
References ............................................................................................................................. 112

Chapter 7: Absorption, Transport, Distribution in Tissues and
Bioavailability(cid:2)
Kirstie Canene-Adams and John W. Erdman Jr

A. Introduction ..................................................................................................................... 115(cid:2)
B. Absorption, Transport, and Storage in Tissues ............................................................ 116(cid:2)
1. Overview ........................................................................................................................ 116(cid:2)
2. Solubilization and incorporation into micelles ............................................................... 117(cid:2)
3. Intestinal absorption ....................................................................................................... 119(cid:2)
xii
4. Transport in blood .......................................................................................................... 121(cid:2)
a) Incorporation into chylomicrons............................................................................ 121(cid:2)
b) Other lipoproteins .................................................................................................. 121(cid:2)
5. Accumulation and distribution in tissues ....................................................................... 122(cid:2)
a) General features ..................................................................................................... 122(cid:2)
b) Blood ...................................................................................................................... 123(cid:2)
c) Liver........................................................................................................................ 124(cid:2)
d) Adipose tissue ......................................................................................................... 125(cid:2)
e) Eyes ........................................................................................................................ 125(cid:2)
f) Breast milk and colostrum ...................................................................................... 126(cid:2)
g) Breast ..................................................................................................................... 128(cid:2)
h) Male reproductive tissues ...................................................................................... 128(cid:2)
i) Skin .......................................................................................................................... 130(cid:2)
j) Adrenals .................................................................................................................. 130(cid:2)
C. Bioavailability .................................................................................................................. 131(cid:2)
1. Introduction .................................................................................................................... 131(cid:2)
2. Effect of food matrix ...................................................................................................... 132(cid:2)
a) Carotenoids in fruits and vegetables ...................................................................... 132(cid:2)
b) Location of carotenoids.......................................................................................... 132(cid:2)
3. Effect of food processing ............................................................................................... 133(cid:2)
4. Structure and isomeric form of the carotenoid ............................................................... 134(cid:2)
a) β-Carotene ............................................................................................................. 134(cid:2)
b) Lycopene ................................................................................................................ 135(cid:2)
5. Effects of other dietary factors ....................................................................................... 135(cid:2)
a) Dietary fat .............................................................................................................. 136(cid:2)
b) Inhibitors in the diet ............................................................................................... 136(cid:2)
c) Interactions between carotenoids ........................................................................... 138(cid:2)
6. Human factors ................................................................................................................ 139(cid:2)
a) ‘Non-responders’ ................................................................................................... 139(cid:2)
b) Age.......................................................................................................................... 139(cid:2)
c) Parasitic infections ................................................................................................. 140(cid:2)
D. Methods for Evaluating Carotenoid Bioavailability .................................................... 140(cid:2)
1. Oral-faecal balance ......................................................................................................... 141(cid:2)
2. Blood response ............................................................................................................... 141(cid:2)
3. Triacylglycerol-rich fraction response ........................................................................... 142(cid:2)
4. Digestion methods in vitro ............................................................................................. 142(cid:2)
5. Stable isotopes ................................................................................................................ 143(cid:2)
6. Raman spectroscopy ....................................................................................................... 143(cid:2)
E. The Future ........................................................................................................................ 144(cid:2)
References ............................................................................................................................. 144