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Über dieses Buch

Twenty years after the idea of this Carotenoids book series was first discussed, we are finally reaching the end of the project. Carotenoids Volumes 4 and 5 now move us into the great field of biology, and cover the functions of carotenoids and the actions of carotenoids in nutrition and health. In the classic 1971 Isler book Carotenoids, carotenoid functions were covered in just one chapter. Now, thanks to technical developments and multidisciplinary approaches that make it possible to study functional processes in great detail, this subject is the most rapidly expanding area of carotenoid research, and occupies two full volumes. These can be used as stand-alone books, but they are really planned to be used together and to complete the coverage of the carotenoid field begun in earlier volumes, as the final part of a coordinated series. The general philosophy and strategy of the series, to have expert authors review, analyse and present information and give guidance on practical strategies and procedures is maintained in Volumes 4 and 5, though the subject matter does not lend itself to the kind of detailed Worked Examples that were featured in earlier volumes. It has also been the aim that these publications should be useful for both experienced carotenoid researchers and newcomers to the field.

Inhaltsverzeichnis

Frontmatter

Chapter 1. Special Molecules, Special Properties

Abstract
This is a book about functions of carotenoids. The reader may therefore be surprised to find that the first half of the book is chemistry. This should not be a surprise, however. The target for researchers now is not simply to discover and describe functions and actions, but to understand their mechanisms. This requires understanding of the underlying fundamental principles and appreciation of the application of the advanced techniques now used to elucidate details of structure and of processes that may occur on a very short timescale.
George Britton, Synnøve Liaaen-Jensen, Hanspeter Pfander

Chapter 2. Structure and Chirality

Abstract
Naturally occurring carotenoids display considerable structural diversity, including different carbon skeletons, various types of oxygen functions and variable degree of unsaturation (double-bond equivalents) due to cyclization, double, triple or allenic bonds. In the Carotenoids Handbook the structures and properties of the known naturally occurring carotenoids (published up to 2003) are presented in two groups, (i) those considered to be proved unequivocally (Main List, some 500 compounds) and (ii) those requiring additional supporting evidence or proof of natural occurrence (Supplementary List, some 225 compounds).
Synnøve Liaaen-Jensen

Chapter 3. E/Z Isomers and Isomerization

Abstract
The natural occurrence of several carotenoid cis isomers and their biological significance were not anticipated in 1962, when the classical monograph on cis-trans isomeric carotenoids [1] was published. More recent research has demonstrated that various cis isomers occur naturally in bacteria plants, algae and invertebrate animals, and are present in human blood and tissues. The participation of cis isomers in the biosynthethic route to coloured carotenoids is well established (Volume 3, Chapter 2). Important biological functions of (15Z)-carotenoids in photosynthesis have been revealed [2]. In relation to health aspects of carotenoids, the bioavailability of cis isomers may be higher than that of the all-trans isomer [3], and accumulated evidence suggests that cis/trans isomerization may occur in biological tissues, particularly of lycopene (31) in human serum [4] (Volume 5, Chapter 7).
Synnøve Liaaen-Jensen, Bjart Frode Lutnœes

Chapter 4. Three-dimensional Structures of Carotenoids by X-ray Crystallography

Abstract
The number of crystal structures of carotenoid molecules and carotenoid derivatives deposited in the Cambridge Crystallographic Data Centre [1] is still relatively small, but has increased compared with the previous survey [2]. The list is summarized in Table 1.
Madeleine Helliwell

Chapter 5. Aggregation and Interface Behaviour of Carotenoids

Abstract
Molecular aggregates attract considerable attention, as they bridge the gap between the physics of single molecules and structurally ordered crystals. Molecular self-assembly in biological systems is highly specific and fundamentally important for correct functioning in living organisms.
Sonja Köhn, Henrike Kolbe, Michael Korger, Christian Köpsel, Bernhard Mayer, Helmut Auweter, Erik Lüddecke, Hans Bettermann, Hans-Dieter Martin

Chapter 6. Carotenoid-Protein Interactions

Abstract
Chapter 5 shows that the aggregation of carotenoid molecules can have a profound effect on their properties and hence their functioning in biological systems. Another important influence is the interaction between carotenoids and other molecules. The way that interactions of carotenoids with lipid bilayers influence the structure and properties of membranes and membrane-asociated processes is discussed in Chapter 10, and the aggregation of carotenoid molecules within the bilayers in Chapter 5. Of particular importance, though, are interactions between carotenoids and proteins. These allow the hydrophobic carotenoids to be transported, to exist, and to function in an aqueous environment. In some cases they may modify strongly the light-absorption properties and hence the colour and photochemistry of the carotenoids.
George Britton, John R. Helliwell

Chapter 7. Carotenoid Radicals and Radical Ions

Abstract
Various types of carotenoid-derived ions, radicals and radical ions are referred to in this Chapter and elsewhere in this Volume. The different species are defined below and their relationship to the parent carotenoid is illustrated by the example of β-carotene (3, C40H56).
Ali El-Agamey, David J McGarvey

Chapter 8. Structure and Properties of Carotenoid Cations

Abstract
Naturally occurring carotenoids are familiar as yellow, orange or red pigments with λmax below 600 nm in organic solvents. Carotenoids with short polyene chains, such as the triene phytoene (44) and the pentaene phytofluene (42), absorb light only in the UV region and are colourless. Compounds that absorb light in the near infrared (NIR) region above ca. 900 nm are also colourless, unless they also absorb light in the 600–900 nm region, in which case they appear blue. True carotenoproteins (Chapter 6) are purple-blue and absorb light above 600 nm.
Synnove Liaane-Jensen, Bjart Frode Lutnees

Chapter 9. Excited Electronic States, Photochemistry and Photophysics of Carotenoids

Abstract
The most striking characteristic of carotenoids is their palette of colours. Absorption of light in the visible region of the electromagnetic spectrum by molecules such as β-carotene (3) and lycopene (31) not only readily accounts for their colours but also signals the ability of these long-chain polyenes to serve as antenna pigments in diverse photosynthetic systems [14].
Harry A. Frank, Ronald L. Christensen

Chapter 10. Functions of Intact Carotenoids

Abstract
The traditional view that carotenoids are a class of plant pigments does not do justice to their versatility. This versatility will become clear from the overview of the biological roles of carotenoids, in animals and microorganisms as well as in plants, that is given in this Chapter. It has become customary and convenient to differentiate biological effects of carotenoids into functions, actions and associations [1]. ‘Functions’ have been defined as effects or properties that are essential for the normal well-being of the organism. Biological responses that follow the administration of carotenoids in the diet or as supplements are considered as ‘actions’. When an effect is seen but a causal relationship to the carotenoid has not been demonstrated, this is described as an ‘association’. The line between these is often not clear, however.
George Britton

Chapter 11. Signal Functions of Carotenoid Colouration

Abstract
The importance of carotenoids for natural colouration, in relation to other classes of pigments and structural colours, has been outlined in Chapter 10. But colour only has significance if it is perceived, identified and interpreted by other organisms (animals). In other words, colour is a means of communication, a signal. Now, in this Chapter, this new direction for carotenoid research, behavioural ecology, is highlighted. Various hypotheses that have been proposed to explain the signal functions of colour, and particularly of carotenoids, in plants and animals are discussed and the empirical evidence to support these hypotheses is presented.
Jonathan D. Blount, Kevin J. McGraw

Chapter 12. Carotenoids in Aquaculture: Fish and Crustaceans

Abstract
This Chapter deals with selected topics on the use of carotenoids for colouration in aquaculture and incudes examples from ecological studies which support our understanding of functions and actions of carotenoids and colouration in fishes and crustaceans. Animal colours may be physical or structural in origin [1], e.g. Tyndall blues and iridescent diffraction colours, or they may be due to pigments, including carotenoids (Chapter 10).
Bjorn Bjerkeng

Chapter 13. Xanthophylls in Poultry Feeding

Abstract
Since most consumers associate an intense colour of food with healthy animals and high food quality, xanthophylls are widely used as feed additives to generate products that meet consumers’ demands. An important large-scale application is in poultry farming, where xanthophylls are added to feed to give the golden colour of egg yolk that is so much appreciated. Now, with numerous new applications in human food, in the pharmaceutical industry, and in cosmetic products, there is an increasing demand for xanthophylls on the international market (Volume 5, Chapter 4).
Diemar R. Breithaupt

Chapter 14. Carotenoids in Photosynthesis

Abstract
Carotenoids are the secret ingredient in photosynthesis; masked by the green of chlorophyll, they are only revealed in their true glory during senescence, when chlorophyll is degraded to display the glowing colours of autumn. Yet the presence of these orange and yellow pigments is absolutely essential for oxygenic photosynthesis. This Chapter will explain the importance of carotenoids to oxygenic organisms and also their roles in anoxygenic photosynthetic bacteria, where their presence is often more obvious but in other ways may be less crucial.
Alison Telfer, Andrew Pascal, Andrew Gall

Chapter 15. Functions of Carotenoid Metabolites and Breakdown Products

Abstract
It is not only intact carotenoids but also fragments of carotenoid molecules that have important natural functions and actions. The electron-rich polyene chain of the carotenoids is very susceptible to oxidative breakdown, which may be enzymic or non-enzymic. Central cleavage gives C20 compounds, retinoids, as described in Chapter 16. Cleavage at other positions gives smaller fragments, notably C10, C13 and C15 compounds that retain the carotenoid end group. The formation of these is described in Chapter 17 and in Volume 3, Chapter 4. Oxidative breakdown can also take place during storage, processing and curing of plant material, and the products contribute to the desired aroma/flavour properties of, for example, tea, wine and tobacco. The importance of vitamin A (C20) in animals is well known. Vitamin A deficiency is still a major concern in many parts of the world. It can lead to blindness and serious ill-health or death, especially in young children. Volatile smaller carotenoid fragments (‘norisoprenoids’) are widespread scent/flavour compounds in plants.
George Britton

Chapter 16. Cleavage of β-Carotene to Retinal

Abstract
Elucidating the physiological roles played by vitamins has always been a major goal of nutritionists and biochemists. In humans, vitamin A deficiency disorder (VADD) in milder forms leads to night blindness, whilst more severe progression can lead to corneal malformations, e.g. xerophthalmia (See Volume 5, Chapters 8 and 9). This deficiency also affects the immune system, leads to infertility and causes malformations during embryogenesis. The molecular basis for these diverse effects lies in the dual role of vitamin A (retinol, 1) derivatives. In all visual systems, retinal (2), or a closely related compound such as 3-hydroxyretinal (3), is the chromophore of the visual pigments (e.g. rhodopsin) [1,2]. In vertebrates, the derivative retinoic acid (RA, 4) is a major signalling molecule that controls a wide range of processes. Retinoic acid is the ligand of the nuclear retinoic acid receptors (RARs) and retinoid X receptors (RXRs) [36] (see Chapter 15).
Adrian Wyss, Johannes von Lintig

Chapter 17. Enzymic Pathways for Formation of Carotenoid Cleavage Products

Abstract
Degraded carotenoids (apocarotenoids, norisoprenoids) have been a subject of intensive research for several decades. From the perspective of human physiology and nutrition, the retinoids, acting as vitamins, signalling molecules, and visual pigments, attracted the greatest attention (Chapters 15 and 16). Plant scientists, however, detected a wealth of different apocarotenoids, presumably derived by the excentric cleavage of carotenoids in various species, the plant hormone abscisic acid (1, Scheme 6) being the best-investigated example. With the onset of fruit ripening, flower opening or senescence of green tissues, carotenoids are degraded oxidatively to smaller, volatile compounds. The natural biological functions of the reaction products are outlined in Chapter 15. As many of these apocarotenoids act as potent flavour compounds, food chemists and flavourists worldwide have investigated meticulously their structural and sensory properties. Many aspects of carotenoid metabolites and breakdown products as aroma compounds are presented in a comprehensive book [1].
Peter Fleischmann, Holger Zorn

Backmatter

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