Bioluminescence: Chemical Principles And Methods

Contents......Page 6
Preface......Page 4
Abbreviations, Symbols and Definitions......Page 13
Introduction......Page 15
The Beginning of the Chemical Study of Bioluminescence......Page 17
Luciferin......Page 18
Photoprotein......Page 19
Chemical Studies on Bioluminescence in the Last One Hundred Years......Page 20
Chemical Study of Bioluminescence in the Future......Page 22
The Contents of this Book......Page 24
1 The Fireflies and Luminous Insects......Page 26
1.1.1 Essential Factors in the Firefly Luminescence Reaction......Page 28
1.1.2 Firefly Luciferin and Oxyluciferin......Page 30
1.1.3 Firefly Luciferase......Page 33
1.1.4 Assays of Luciferase Activity, ATP and Luciferin......Page 36
1.1.5 General Characteristics of the Bioluminescence of Fireflies......Page 37
1.1.6 Mechanisms of the Bioluminescence......Page 40
1.1.7 Light Emitters in the Firefly Luminescence System......Page 42
1.1.8 A Note on the Dioxetanone Pathway and the 18O-incorporation Experiment......Page 44
1.2 Phengodidae and Elateroidae......Page 48
1.2.2 Elateridae......Page 49
1.3.1 The Glow-worm Arachnocampa......Page 50
1.3.2 The American Glow-worm Orfelia......Page 52
2 Luminous Bacteria......Page 55
2.1 Factors Required for Bioluminescence......Page 56
2.2 Bacterial Luciferase......Page 58
2.3 Long-chain Aldehyde......Page 60
2.4 Mechanism of Luminescence Reaction......Page 62
2.5 Assay of Luciferase Activity......Page 64
2.7 In vivo Luminescence of Luminous Bacteria......Page 66
3 The Ostracod Cypridina (Vargula) and Other Luminous Crustaceans......Page 72
3.1.1 Overview of Ostracoda......Page 74
3.1.2 Cypridina hilgendorfii Muller......Page 76
3.1.3 Research on Cypridina Luminescence before 1955......Page 78
3.1.4 Purification and Crystallization of Cypridina Luciferin......Page 80
3.1.5 Properties of Cypridina Luciferin......Page 83
3.1.7 Purification and Molecular Properties of Cypridina Luciferase......Page 87
3.1.8 Luciferin-luciferase Luminescence Reaction......Page 89
3.1.9 Quantum Yield......Page 94
3.2.1 Involvement of the Fluorescent Compound F and Protein P......Page 96
3.2.2 Fluorescent Compound F......Page 99
3.2.3 Protein P......Page 104
3.2.4 Luminescence Reaction......Page 105
3.3.1 Oplophorus Luciferase......Page 107
3.3.2 Coelenterazine-luciferase Reaction......Page 108
3.4 Copepoda......Page 113
4 The Jellyfish Aequorea and Other Luminous Coelenterafes......Page 115
4.1 The Hydrozoan Medusa Aequorea aequorea......Page 117
4.1.1 History of the Biochemical Study of Aequorea Bioluminescence......Page 119
4.1.2 Extraction and Purification of Aequorin......Page 120
4.1.3 Properties of Aequorin......Page 125
4.1.4 Discovery of the Coelenterazine Moiety in Aequorin......Page 136
4.1.5 Regeneration of Aequorin from Apoaequorin......Page 138
4.1.6 Recombinant Aequorin......Page 141
4.1.7 Semisynthetic Aequorins......Page 143
4.1.8 The In Vivo Luminescence of Aequorea......Page 154
4.2.1 Natural Obelins......Page 158
4.2.2 Recombinant Obelin......Page 159
4.3 The Hydrozoan Medusa Phialidium gregarium......Page 162
4.4 Other Bioluminescent Hydrozoans......Page 163
4.5.2 Periphylla periphylla......Page 165
4.6 The Anthozoan Renilla (Sea Pansy)......Page 172
4.7 Green Fluorescent Protein (GFP)......Page 176
4.8 The Ctenophores......Page 179
5.1 Discovery of Coelenterazine......Page 184
5.2 Occurrence of Coelenterazine......Page 185
5.3 Properties of Coelenterazine and its Derivatives......Page 190
5.4 Chemi- and Bioluminescence Reactions of Coelenterazine......Page 193
5.5 Chemical Reactions of Coelenterazine......Page 198
5.7 Coelenterazine Luciferases......Page 201
6 Luminous Mollusca......Page 205
6.1 The Limpet Latia......Page 207
6.2 The Clam Pholas dactylus......Page 217
6.3 Luminous Squids (Cephalopoda)......Page 224
6.3.1 The Firefly Squid Watasenia scintillans......Page 225
6.3.2 The Purpleback Flying Squid Symplectoteuthis oualaniensis (Tobi-ika)......Page 229
6.3.3 The Luminous Flying Squid Symplectoteuthis luminosa (Suji-ika)......Page 235
7.1 The Tube worm Chaetopterus variopedatus......Page 241
7.1.1 Biochemistry of the Luminescence of Chaetopterus variopedatus......Page 243
7.1.2 Properties of the Chaetopterus Photoprotein and its Luminescence Reaction......Page 246
7.2 The Bermuda Fireworm Odontosyllis......Page 250
7.3 Luminous Earthworms (Oligochaeta)......Page 259
7.4 Polynoid Scaleworm Harmothoe lunulata......Page 267
7.5 The Polychaete Tomopteris......Page 271
8.1 Radiolarians......Page 273
8.2 Dinoflagellates......Page 274
8.2.2 Scintillons......Page 276
8.2.3 The Luciferase of Gonyaulax polyedra......Page 277
8.2.4 Extraction and Purification of Dinoflagellate Luciferin......Page 281
8.2.5 Properties of Dinoflagellate Luciferin......Page 283
8.2.6 Chemical Structures of Dinoflagellate Luciferin and its Oxidation Products......Page 285
8.2.7 Chemical Mechanism of Dinoflagellate Bioluminescence......Page 288
8.2.8 Luciferin Binding Protein of Dinoflagellates......Page 289
9.1 An Overview on Fungal Bioluminescence......Page 291
9.2 Early Studies on the Biochemistry of Luminous Fungi......Page 293
9.3 Role of Superoxide in Fungal Luminescence......Page 296
9.4 Studies on Panellus stipticus......Page 300
9.4.1 Panal......Page 302
9.4.2 Activation Products of Panal......Page 304
9.4.3 PS-A and PS-B......Page 307
9.4.4 Activation of PS-A and PS-B......Page 308
9.4.5 Mechanism of the in vivo Bioluminescence of P. stipticus......Page 314
9.4.6 Synthetic Studies of Panellus Luciferin......Page 316
9.5.2 Studies on the Mycena citricolor Luminescence by the Author......Page 319
9.6 Summary on the Chemistry of Fungal Luminescence......Page 323
10.1 Ophiuroidea: Brittle Stars......Page 326
10.1.1 The Brittle Star Ophiopsila californica......Page 327
10.2 Millipede Luminodesmus sequoiae (Diplopoda)......Page 332
10.3 Centipede Orphaneus brevilabiatus (Chilopoda)......Page 339
10.4.1 The Acorn Worm Balanoglossus biminiensis......Page 340
10.4.2 The Luciferin of Ptycbodera flava......Page 343
10.5 Tunicates (Phylum Chordata)......Page 344
10.6 The Luminous Fishes......Page 347
10.6.1 Coastal and Shallow-water Fishes that Utilize Cypridina Luciferin......Page 348
10.6.2 Oceanic Deep-sea Luminous Fishes......Page 352
10.6.3 Future Research on Fish Bioluminescence......Page 355
A Taxonomic Classification of Selected Luminous Organisms......Page 357
B Lists of Luciferins, Luciferases and Photoproteins Isolated......Page 364
C1 Basic Principle of the Isolation of Bioluminescent Substances......Page 373
C1.1 Reversible Inhibition of Bioluminescence......Page 374
C1.3 Solubilization of Proteins......Page 377
C1.4 Purification......Page 379
C2 Storage of Samples......Page 380
C3 Measurement of Luminescence......Page 384
C4 Calibration of Luminometer and the Measurement of Quantum Yield......Page 385
C5.1 Assay of Coelenterazine......Page 387
C5.2 Assay of the Coelenterazine Luciferase Activity......Page 388
C5.3 Assay of the Stabilized Forms of Coelenterazine......Page 389
C5.5 Assay of Cypridina Luciferin......Page 390
C5.6 Assay of Cypridina Luciferase......Page 391
C5.7 Assay of Ca2+ -sensitive Photoproteins......Page 392
C5.8 Measuring Bioluminescence in the Field......Page 393
C6 18O-Labeling of the Reaction Product C02......Page 394
C7 Glass Blowing......Page 398
D Advice to Students Who are Interested in Studying the Chemistry of Bioluminescence......Page 399
References......Page 403
Index......Page 479