5.Fecundity 40444440044.44440044000444040444440044404040444.0444…。04444044404 227 a)Egg production.. 227 b)Sperm production 228 C）Offspring rearing.. 228 6.Genetic quality 229 7.Photoprotection...... 229 E.Measurement of Carotenoids and Colour in Ecological Studies … 229 1.Carotenoid analysis and colour measurement 229 2.Sampling range 230 3.Temporal changes in colouration 230 F.Applied Value of Carotenoid Colouration 231 1.Maintaining colouration and health in captive animals 231 2.Conservation implications of carotenoid signals.............. 231 G.Conclusions 232 References 232 Chapter 12:Carotenoids in Aquaculture:Fish and Crustaceans Bjorn Bjerkeng A.Introduction .237 B.Market Issues 239 C.Importance of Pigmentation 240 1.Colouration-ecoloical and evolutionary aspects 240 2.Salmon muscle colour ......................................................... 241 3.Embryonic development and larval growth 242 D.Sources of Dietary Carotenoids 245 E.Car0 tenoid Utilizati0n......................... 247 1.Uptake from the gastrointestinal tract 247 2.Distribution in muscle and integument 248 3.Alternative administration 249 F.Conclusion 250 References 250
xiv 5. Fecundity ……………………………………………………………….. 227 a) Egg production ……………………………………………………… 227 b) Sperm production …………………………………………………… 228 c) Offspring rearing ……………………………………………………. 228 6. Genetic quality ………………………………………………………….. 229 7. Photoprotection …………………………………………………………. 229 E. Measurement of Carotenoids and Colour in Ecological Studies ……….. 229 1. Carotenoid analysis and colour measurement ………………………….. 229 2. Sampling range …………………………………………………………. 230 3. Temporal changes in colouration ……………………………………….. 230 F. Applied Value of Carotenoid Colouration ……………………………….. 231 1. Maintaining colouration and health in captive animals ………………… 231 2. Conservation implications of carotenoid signals ……………………….. 231 G. Conclusions …………………………………………………………………. 232 References ……………………………………………………………………… 232 Chapter 12: Carotenoids in Aquaculture: Fish and Crustaceans Bjørn Bjerkeng A. Introduction ………………………………………………………………… 237 B. Market Issues ………………………………………………………………. 239 C. Importance of Pigmentation ………………………………………………. 240 1. Colouration - ecological and evolutionary aspects ……………………... 240 2. Salmon muscle colour ………………………………………………….. 241 3. Embryonic development and larval growth ……………………………. 242 D. Sources of Dietary Carotenoids …………………………………………… 245 E. Carotenoid Utilization ……………………………………………………… 247 1. Uptake from the gastrointestinal tract …………………………………... 247 2. Distribution in muscle and integument …………………………………. 248 3. Alternative administration ………………………………………………. 249 F. Conclusion …………………………………………………………………... 250 References ……………………………………………………………………… 250
Chapter 13:Xanthophylls in Poultry Feeding Dietmar E.Breithaupt A.Introduction 255 B.Legal Situation in the European Union (EU) 257 C.Analysis 258 D.Application of Xanthophylls in Poultry Farming 261 E.Conclusion References 263 Chapter 14:Carotenoids in Photosynthesis Alison Telfer.Andrew Pascal and Andrew Gall A.Introduction 265 1.General comments …4小………4小4…小小小小………小4… 265 2.Photosvnthesis............... 265 3.Role of carotenoids 268 B.Photosynthetic Pigment-Protein Complexes 269 C.Reaction Centres:Structure and Function 270 1.Type 2 reaction centres 270 a)General features............................................................. 270 b)Location of carotenoids 272 2.Type I reaction centres. 273 D.Light Harvesting:Antenna Structure and Function 275 1.General aspects 275 2.Antenna complexes... 277 a）LH complexes 277 b)LHC-type complexes:Chlorophyll a/b proteins 281 c)Core-type complexes:chlorophyll a proteins 287 dChl00s0ms,,.4....,,., 289 e)The peridinin-chlorophyll-protein complex(PCP)in dinoflagellate algae ........... 291 f)Carotenes or xanthophylls?.... 291 E.Photoprotection 292 1.Over-excitation of photosystems and production of toxic oxygen species.292 2.The valve reaction:chlorophyll triplet quenching by carotenoids 293 3.Singlet oxygen quenching ......................... 。。。。 294 4.Non-photochemical quenching and the xanthophyll cycle 296 5.Cytochrome bofcomplex.. 297
xv Chapter 13: Xanthophylls in Poultry Feeding Dietmar E. Breithaupt A. Introduction ………………………………………………………………… 255 B. Legal Situation in the European Union (EU) …………………………….. 257 C. Analysis ……………………………………………………………………... 258 D. Application of Xanthophylls in Poultry Farming ………………………... 261 E. Conclusion ………………………………………………………………….. 263 References ……………………………………………………………………... 263 Chapter 14: Carotenoids in Photosynthesis Alison Telfer, Andrew Pascal and Andrew Gall A. Introduction ………………………………………………………………... 265 1. General comments ………………………………………………………. 265 2. Photosynthesis …………………………………………………………... 265 3. Role of carotenoids ……………………………………………………... 268 B. Photosynthetic Pigment-Protein Complexes …………………………….. 269 C. Reaction Centres: Structure and Function ………………………………. 270 1. Type 2 reaction centres …………………………………………………. 270 a) General features …………………………………………………….. 270 b) Location of carotenoids …………………………………………….. 272 2. Type 1 reaction centres …………………………………………………. 273 D. Light Harvesting: Antenna Structure and Function ……………………. 275 1. General aspects …………………………………………………………. 275 2. Antenna complexes ……………………………………………………... 277 a) LH complexes ………………………………………………………. 277 b) LHC-type complexes: Chlorophyll a/b proteins ……………………. 281 c) Core-type complexes: chlorophyll a proteins ………………………. 287 d) Chlorosomes ………………………………………………………... 289 e) The peridinin-chlorophyll-protein complex (PCP) in dinoflagellate algae ………………………………………………………………… 291 f) Carotenes or xanthophylls? …………………………………………. 291 E. Photoprotection ……………………………………………………………. 292 1. Over-excitation of photosystems and production of toxic oxygen species . 292 2. The valve reaction: chlorophyll triplet quenching by carotenoids ……… 293 3. Singlet oxygen quenching ………………………………………………. 294 4. Non-photochemical quenching and the xanthophyll cycle ……………... 296 5. Cytochrome b6f complex ……………………………………………….. 297
F.Electron Donation:Carotenoid Oxidation in G.Assembly and Reconstitution of Complexes... 299 1.Bacteria 299 2.Higher plants 303 H.Carotenoid Bandshift:a Monitor of the Membrane Potential 304 I.Evolutionary Considerations 304 References 305 Chapter 15:Functions of Carotenoid Metabolites and Breakdown Products George Britton A.Introduction 309 B.CzoCompounds:Retinoids 310 1.Vitamin A........... 310 2.Retinol 311 3.Retinoic acid 311 4.Retinal and photoreceptors 312 a)Visual pigment 312 b)）Rhodopsin… 313 c)Colour vision 317 d)Bacteriorhodopsin 317 e)Chlamydomonas 319 C.Cio-Cis Norisoprenoids 319 1.Formation and diversity 319 2.Perfume/flavour/aroma compounds 320 3.Abscisic acid… 321 4.Trisporic acid 322 5.Grasshopper ketone 322 D.Polymers:Sporopollenin 322 E.Other Carotenoid Breakdown Products and Human Health 323 References 323 Chapter 16:Cleavage of B-Carotene to Retinal Adrian Wyss and Johannes von Lintig A.Introduction 325 B.Pioneering Work. 327
xvi F. Electron Donation: Carotenoid Oxidation in PSII ………………………. 298 G. Assembly and Reconstitution of Complexes ……………………………… 299 1. Bacteria …………………………………………………………………. 299 2. Higher plants ……………………………………………………………. 303 H. Carotenoid Bandshift: a Monitor of the Membrane Potential ………….. 304 I. Evolutionary Considerations ………………………………………………. 304 References ……………………………………………………………………… 305 Chapter 15: Functions of Carotenoid Metabolites and Breakdown Products George Britton A. Introduction ………………………………………………………………… 309 B. C20 Compounds: Retinoids ………………………………………………… 310 1. Vitamin A ………………………………………………………………. 310 2. Retinol …………………………………………………………………... 311 3. Retinoic acid ……………………………………………………………. 311 4. Retinal and photoreceptors ……………………………………………… 312 a) Visual pigments …………………………………………………….. 312 b) Rhodopsin …………………………………………………………... 313 c) Colour vision ………………………………………………………... 317 d) Bacteriorhodopsin …………………………………………………... 317 e) Chlamydomonas ……………………………………………………. 319 C. C10 – C15 Norisoprenoids …………………………………………………... 319 1. Formation and diversity ………………………………………………… 319 2. Perfume/flavour/aroma compounds …………………………………….. 320 3. Abscisic acid ……………………………………………………………. 321 4. Trisporic acid …………………………………………………………… 322 5. Grasshopper ketone …………………………………………………….. 322 D. Polymers: Sporopollenin …………………………………………………... 322 E. Other Carotenoid Breakdown Products and Human Health …………… 323 References ……………………………………………………………………… 323 Chapter 16: Cleavage of -Carotene to Retinal Adrian Wyss and Johannes von Lintig A. Introduction ………………………………………………………………… 325 B. Pioneering Work …………………………………………………………… 327
xvi C.Cloning the Genes Coding for the Cleavage Enzymes … 328 D.Identification of an Excentric Cleavage Enzyme..... 330 E.A Novel Family of Sequence-related and Structure-related Non-haem Iron Oxygenases 331 F.Biochemical Properties of B-Carotene 15,15'-Oxygenase 1(BCO1)........ 333 G.Mechanisms of Cleavage 334 1.Central versus excentric cleavage. 34 2.Dioxygenase or monooxygenase? 335 H.Regulation.............. 335 I.The Role of Carotenoid Cleavage Enzymes during Development 337 J.Carotenoid Cleavage Enzymes in Different Tissues 338 K Outlook 338 References 339 Chapter 17:Enzymic Pathways for Formation of Carotenoid Cleavage Products Peter Fleischmann and Holger Zorn B.Structural Diversity of Carotenoid-derived Flavour Compounds .. ..342 C.General Model for Carotenoid-related Flavour Formation and Release. 346 D.Cleavage of the C(11,12)Double Bond:(9Z)-Epoxycarotenoid Dioxygenases (NCED) 350 E.Cleavage of the C(9,10)or C(,10)Double Bond:Carotenoid Cleavage Dioxygenases(CCD) 353 F.Cleavage of c(7,8)and C(5,6)Double Bonds .............. 356 G.Cleavage of Apocarotenals 358 H.Unspecific Enzyme-based Cleavage .................... 362 1.Co-oxidation 362 2.Plant and Fungal Peroxidases 363 References....... 364 Index 367
xvii C. Cloning the Genes Coding for the Cleavage Enzymes ………………….. 328 D. Identification of an Excentric Cleavage Enzyme ………………………… 330 E. A Novel Family of Sequence-related and Structure-related Non-haem Iron Oxygenases …………………………………………………………… 331 F. Biochemical Properties of -Carotene 15,15'-Oxygenase 1 (BCO1) …….. 333 G. Mechanisms of Cleavage …………………………………………………... 334 1. Central versus excentric cleavage ………………………………………. 334 2. Dioxygenase or monooxygenase? ………………………………………. 335 H. Regulation …………………………………………………………………... 335 I. The Role of Carotenoid Cleavage Enzymes during Development ……….. 337 J. Carotenoid Cleavage Enzymes in Different Tissues ……………………… 338 Outlook ……………………………………………………………………... References ……………………………………………………………………… Chapter 17: Enzymic Pathways for Formation of Carotenoid Cleavage Products Peter Fleischmann and Holger Zorn A. Introduction ………………………………………………………………… 341 B. Structural Diversity of Carotenoid-derived Flavour Compounds ………. 342 C. General Model for Carotenoid-related Flavour Formation and Release ... 346 D. Cleavage of the C(11,12) Double Bond: (9Z)-Epoxycarotenoid Dioxygenases (NCED) …………………………………………………….. 350 E. Cleavage of the C(9,10) or C(9’,10’) Double Bond: Carotenoid Cleavage Dioxygenases (CCD) ………………………………………………………. 353 F. Cleavage of C(7,8) and C(5,6) Double Bonds ……………………………... 356 G. Cleavage of Apocarotenals ………………………………………………… 358 H. Unspecific Enzyme-based Cleavage ………………………………………. 362 1. Co-oxidation …………………………………………………………….. 362 2. Plant and Fungal Peroxidases …………………………………………... 363 References ……………………………………………………………………… 364 Index ……………………………………………………………………………. 367
xi品 List of Contributors 2 1542 uweter@basf.com) Hans bettermann Institute for Physical Chemistry University of Dusseldorf Universitatstrasse l 40225 Dusseldorf Germany (betterma@uni-duesseldorf de Bjom Bjerkeng Nofima Akvaforsk-Fiskeriforskning AS and Conservation School of Biosci nces Unversity Cornwall Campus Penryn TR109EZ UK (j.d.blount@ex.ac.uk) Dietmar E.Breithaupt GMCoKG 73728 Esslingen
xviii List of Contributors Helmut Auweter BASF AG ZKM/D – J542S 67056 Luwigshafen Germany (helmut.auweter@basf.com) Hans Bettermann Institute for Physical Chemistry University of Düsseldorf Universitätstrasse 1 40225 Düsseldorf Germany (betterma@uni-duesseldorf.de) Bjørn Bjerkeng Nofima Akvaforsk-Fiskeriforskning AS 6600 Sunndalsøra Norway (bjorn.bjerkeng@nofima.no) Jonathan D. Blount Centre for Ecology and Conservation School of Biosciences Unversity of Exeter Cornwall Campus Penryn TR10 9EZ UK (j.d.blount@ex.ac.uk) Dietmar E. Breithaupt Rich. Hengstenberg GMBH & Co KG Mettingerstr. 109 73728 Esslingen Germany (dietmar.breithaupt@hengstenberg.de)