Preface v
Abbreviations, Symbols and Definitions xv
Introduction xvii
The Beginning of the Chemical Study of xix
Bioluminescence
Luciferin xx
Photoprotein xxi
Chemical Studies on Bioluminescence in the Last xxii
One Hundred Years
Chemical Study of Bioluminescence in the Future xxiv
The Contents of this Book xxvi
The Fireflies and Luminous Insects 1 (29)
The Fireflies 3 (20)
Essential Factors in the Firefly 3 (2)
Luminescence Reaction
Firefly Luciferin and Oxyluciferin 5 (3)
Firefly Luciferase 8 (3)
Assays of Luciferase Activity, ATP and 11 (1)
Luciferin
General Characteristics of the 12 (3)
Bioluminescence of Fireflies
Mechanisms of the Bioluminescence 15 (2)
Light Emitters in the Firefly 17 (2)
Luminescence System
A Note on the Dioxetanone Pathway and 19 (4)
the 18O-incorporation Experiment
Phengodidae and Elateroidae 23 (2)
Phengodidae 24 (1)
Elateridae 24 (1)
Diptera 25 (5)
The Glow-worm Arachnocampa 25 (2)
The American Glow-worm Orfelia 27 (3)
Luminous Bacteria 30 (17)
Factors Required for Bioluminescence 31 (2)
Bacterial Luciferase 33 (2)
Long-chain Aldehyde 35 (2)
Mechanism of Luminescence Reaction 37 (2)
Assay of Luciferase Activity 39 (2)
Quantum Yield of Long-chain Aldehydes 41 (1)
In vivo Luminescence of Luminous Bacteria 41 (6)
The Ostracod Cypridina (Vargula) and Other 47 (43)
Luminous Crustaceans
The Ostracod Cypridina 49 (22)
Overview of Ostracoda 49 (2)
Cypridina hilgendorfii Muller 51 (2)
Research on Cypridina Luminescence 53 (2)
before 1955
Purification and Crystallization of 55 (3)
Cypridina Luciferin
Properties of Cypridina Luciferin 58 (4)
Oxyluciferin and Etioluciferin 62 (1)
Purification and Molecular Properties 62 (2)
of Cypridina Luciferase
Luciferin-luciferase Luminescence 64 (5)
Reaction
Quantum Yield 69 (2)
Euphausiids Euphausia pacifica and 71 (11)
Meganyctiphanes norvegica
Involvement of the Fluorescent Compound 71 (3)
F and Protein P
Fluorescent Compound F 74 (5)
Protein P 79 (1)
Luminescence Reaction 80 (2)
The Decapod Shrimp Oplophorus 82 (6)
gracilirostris
Oplophorus Luciferase 82 (1)
Coelenterazine-luciferase Reaction 83 (5)
Copepoda 88 (2)
The Jellyfish Aequorea and Other Luminous 90 (69)
Coelenterates
The Hydrozoan Medusa Aequorea aequorea 92 (41)
History of the Biochemical Study of 94 (1)
Aequorea Bioluminescence
Extraction and Purification of Aequorin 95 (5)
Properties of Aequorin 100 (11)
Discovery of the Coelenterazine Moiety 111 (2)
in Aequorin
Regeneration of Aequorin from 113 (3)
Apoaequorin
Recombinant Aequorin 116 (2)
Semisynthetic Aequorins 118 (11)
The In Vivo Luminescence of Aequorea 129 (4)
The Hydroid Obelia (Hydrozoan) 133 (4)
Natural Obelins 133 (1)
Recombinant Obelin 134 (3)
The Hydrozoan Medusa Phialidium gregarium 137 (1)
Other Bioluminescent Hydrozoans 138 (2)
The Scyphozoans Pelagia and Periphylla 140 (7)
Pelagia noctiluca 140 (1)
Periphylla periphylla 140 (7)
The Anthozoan Renilla (Sea Pansy) 147 (4)
Green Fluorescent Protein (GFP) 151 (3)
The Ctenophores 154 (5)
The Coelenterazines 159 (21)
Discovery of Coelenterazine 159 (1)
Occurrence of Coelenterazine 160 (5)
Properties of Coelenterazine and its 165 (3)
Derivatives
Chemi- and Bioluminescence Reactions of 168 (5)
Coelenterazine
Chemical Reactions of Coelenterazine 173 (3)
Synthesis of Coelenterazines 176 (1)
Coelenterazine Luciferases 176 (4)
Luminous Mollusca 180 (36)
The Limpet Latia 182 (10)
The Clam Pholas dactylus 192 (7)
Luminous Squids (Cephalopoda) 199 (17)
The Firefly Squid Watasenia scintillans 200 (4)
The Purpleback Flying Squid 204 (6)
Symplectoteuthis oualaniensis (Tobi-ika)
The Luminous Flying Squid 210 (6)
Symplectoteuthis luminosa (Suji-ika)
Annelida 216 (32)
The Tubeworm Chaetopterus variopedatus 216 (9)
Biochemistry of the Luminescence of 218 (3)
Chaetopterus variopedatus
Properties of the Chaetopterus 221 (4)
Photoprotein and its Luminescence
Reaction
The Bermuda Fireworm Odontosyllis 225 (9)
Luminous Earthworms (Oligochaeta) 234 (8)
Polynoid Scaleworm Harmothoe lunulata 242 (4)
The Polychaete Tomopteris 246 (2)
Dinoflagellates and Other Protozoa 248 (18)
Radiolarians 248 (1)
Dinoflagellates 249 (17)
Cultivation and Harvesting of 251 (1)
Dinoflagellates
Scintillons 251 (1)
The Luciferase of Gonyaulax polyedra 252 (4)
Extraction and Purification of 256 (2)
Dinoflagellate Luciferin
Properties of Dinoflagellate Luciferin 258 (2)
Chemical Structures of Dinoflagellate 260 (3)
Luciferin and its Oxidation Products
Chemical Mechanism of Dinoflagellate 263 (1)
Bioluminescence
Luciferin Binding Protein of 264 (2)
Dinoflagellates
Luminous Fungi 266 (35)
An Overview on Fungal Bioluminescence 266 (2)
Early Studies on the Biochemistry of 268 (3)
Luminous Fungi
Role of Superoxide in Fungal Luminescence 271 (4)
Studies on Panellus stipticus 275 (19)
Panal 277 (2)
Activation Products of Panal 279 (3)
PS-A and PS-B 282 (1)
Activation of PS-A and PS-B 283 (6)
Mechanism of the in vivo 289 (2)
Bioluminescence of P. stipticus
Synthetic Studies of Panellus Luciferin 291 (3)
Studies on Mycena citricolor 294 (4)
Luciferin Obtained by Kuwabara and 294 (1)
Wassink
Studies on the Mycena citricolor 294 (4)
Luminescence by the Author
Summary on the Chemistry of Fungal 298 (3)
Luminescence
Other Luminous Organisms 301 (32)
Ophiuroidea: Brittle Stars 301 (6)
The Brittle Star Ophiopsila californica 302 (5)
The Brittle Star Amphiura filiformis 307 (1)
Millipede Luminodesmus sequoiae 307 (7)
(Diplopoda)
Centipede Orphaneus brevilabiatus 314 (1)
(Chilopoda)
Hemicordata 315 (4)
The Acorn Worm Balanoglossus biminiensis 315 (3)
The Luciferin of Ptychodera flava 318 (1)
Tunicates (Phylum Chordata) 319 (3)
The Luminous Fishes 322 (11)
Coastal and Shallow-water Fishes that 323 (4)
Utilize Cypridina Luciferin
Oceanic Deep-sea Luminous Fishes 327 (3)
Future Research on Fish Bioluminescence 330 (3)
Appendix 333 (46)
Taxonomic Classification of Selected 333 (7)
Luminous Organisms
Lists of Luciferins, Luciferases and 340 (9)
Photoproteins Isolated
Miscellaneous Technical Information 349 (26)
Basic Principle of the Isolation of 349 (1)
Bioluminescent Substances
Reversible Inhibition of Bioluminescence 350 (3)
Extraction of Luciferin-luciferase 353 (1)
Systems
Solubilization of Proteins 353 (2)
Purification 355 (1)
Storage of Samples 356 (4)
Measurement of Luminescence 360 (1)
Calibration of Luminometer and the 361 (2)
Measurement of Quantum Yield
Measurements of Coelenterazine, its 363 (1)
Derivatives, and other Important
Substances in Bioluminescence
Assay of Coelenterazine 363 (1)
Assay of the Coelenterazine Luciferase 364 (1)
Activity
Assay of the Stabilized Forms of 365 (1)
Coelenterazine
Assay of Dehydrocoelenterazine 366 (1)
Assay of Cypridina Luciferin 366 (1)
Assay of Cypridina Luciferase 367 (1)
Assay of Ca2+ -sensitive Photoproteins 368 (1)
Measuring Bioluminescence in the Field 369 (1)
18O-Labeling of the Reaction Product CO2 370 (4)
Glass Blowing 374 (1)
Advice to Students Who are Interested in 375 (4)
Studying the Chemistry of Bioluminescence
References 379 (76)
Index 455
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