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Table of Contents


	Abbreviations, Symbols and Definitions	xiii
	Introduction	xvii
1	The Fireflies and Luminous Insects	1
1.1	The Fireflies	2
1.1.1	An overview of the firefly luminescence reaction	2
1.1.2	Firefly luciferin and oxyluciferin	5
1.1.3	Firefly luciferase	7
1.1.4	Assays of luciferase activity, ATP and luciferin	10
1.1.5	General characteristics of the bioluminescence of fireflies	11
1.1.6	Mechanism of firefly bioluminescence	15
1.1.7	Identification of light emitter	17
1.1.8	Anoteon the dioxetanone pathway and the ¹⁸O-incorporation experiment	20
1.2	Phengodidae and Elateroidae	24
1.2.1	Phengodidae	25
1.2.2	Elateridae	25
1.3	Diptera	26
1.3.1	The glow-worm Amchnocampa	26
1.3.2	The American glow-worm Orfelia	29
2	Luminous Bacteria	31
2.1	Factors Required for Bioluminescence	32
2.2	Bacterial Luciferase	33
2.3	Long-chain Aldehyde	35
2.4	Mechanism of Luminescence Reaction	38
2.5	Assay of Luciferase Activity	39
2.6	Quantum Yield of Long-chain Aldehydes	41
2.7	In vivo Luminescence of Luminous Bacteria	42
3	The Ostracod Cypridina (Vargula) and Other Luminous Crustaceans	49
3.1	The Ostracod Cypridina	51
3.1.1	Overview of Ostracoda	51
3.1.2	Cypridina hilgmdorfii Muller	52
3.1.3	Research on Cypridina luminescence before 1955	55
3.1.4	Purification and crystallization of Cypridina luciferin	56
3.1.5	Properties of Cypridina luciferin	60
3.1.6	Oxyluciferin and etioluciferin	63
3.1.7	Purification and molecular properties of Cypridina luciferase	64
3.1.8	Luciferin-luciferase luminescence reaction	65
3.1.9	Quantum yield	71
3.2	Euphausiids Euphausia pacifica and Meganyctiphanes Norvegica	73
3.2.1	Involvement of the fluorescent compound F and protein P	74
3.2.2	Fluorescent compound F	75
3.2.3	Protein P	80
3.2.4	Luminescence reaction	81
3.3	The Decapod Shrimp Oplophorusgracilirostris	83
3.3.1	Oplophorus luciferase	83
3.3.2	Coelenterazine-luciferase reaction	85
3.4	Copepoda	89
4	The Jellyfish Aequorea and Other Luminous Coelenterates	91
4.1	The Hydrozoan Medusa Aequorea aequorea	92
4.1.1	History of the biochemica I study of Aequorea bioluminescence	95
4.1.2	Extraction and purification of aequorin	96
4.1.3	Properties of aequorin	101
4.1.4	Discovery of the coelenterazine moiety in aequorin	112
4.1.5	Regeneration of aequorin from apoaequorin	114
4.1.6	Recombinant aequorin	117
4.1.7	Semisynthetic aequorins	119
4.1.8	The in vivo luminescence of Aequorea	130
4.2	The Hydroid Obelia (Hydrozoan)	131
4.2.1	Natural obelins	132
4.2.2	Recombinant obelin	133
4.3	The Hydrozoan Medusa Pbialidium gregmiunt	136
4.4	Other Bioluminescent Hydrozoans	138
4.5	The Scyphozoans Pelagia, and Periphylla	139
4.5.1	Pelagia noctiluca	139
4.5.2	Periphylla periphylla	139
4.6	The Anthozoan Renilla (Sea Pansy)	146
4.7	The Ctenophores	149
4.8	The green fluorescent protein (GFP)	154
4.8.1	Properties of Aequorea GFP	156
4.8.2	Chromophore of Aequorea GFP	158
4.8.3	Various natural GFPs	159
4.8.4	Various improved forms of GFP	162
5	The Coelenterazines	167
5.1	Discovery of Coelenterazine	167
5.2	Occurrence of Coelenterazine	168
5.3	Properties of Coelenterazine and its Derivatives	173
5.4	Chemi- and Bioluminescence Reactions of Coelenterazine	175
5.5	Various Chemical Reactions of Coelenterazine	182
5.6	Synthesis of CoeJenterazines	185
5.7	Coelenterazine Luciferases	185
6	Luminous Mollusca	139
6.1	The Limpet Latia	190
6.2	The Clam Photos dactylus	201
6.3	Luminous Squids (Cephalopoda)	208
6.3.1	The firefly squid Watasenia scintillans	209
6.3.2	The purpleback flying squid Symplectoteuthis oualaniensis (Tobi-ika)	214
6.3.3	The luminous flying squid Symplectoteuthis luminosa (Suji-ika)	219
7	Annelida	225
7.1	The Tubeworm Chaetopterus variopedatus	225
7.1.1	Biochemistry of the Luminescence of Chaetoptertts variopedatus	226
7.1.2	Properties of the Chaetopterus photoprotein and its luminescence reaction	230
7.2	The Bermuda Fireworm Odontosytlis	233
7.3	Luminous Earthworms (Oligochaeta)	243
7.4	Polynoid Scaleworm Harmothoe lunulata	251
7.5	The Polychaete Tomopteris	255
8	Dinoffagellates and Other Protozoa	257
8.1	Radiolarians	257
8.2	Dinoflagellates	258
8.2.1	Cultivation and harvesting of dinoflagellates	259
8.2.2	Scintillons	260
8.2.3	The ludferase of Gonyaulaxpolyedm	261
8.2.4	Extraction and purification of dinoflagellate luciferin	264
8.2.5	Properties of dinoflagellate luciferin	266
8.2.6	Chemical structures of dinoflagellate luciferin and its oxidation products	269
8.2.7	Chemical mechanism of dinoflagellate bioluminescence	272
8.2.8	Luciferin binding protein of dinoflagellates	273
9	Luminous Fungi	275
9.1	An Overview on Fungal Bioluminescence	275
9.2	Early Studies on the Biochemistry of Luminous Fungi	277
9.3	Role of Superoxide in Fungal Luminescence	279
9.4	Studies on Pcmellusstipticus	284
9.4.1	Panal	285
9.4.2	Activation products of panal	287
9.4.3	PS-AandPS-B	290
9.4.4	Activation of PS-A and PS-B	292
9.4.5	Mechanism of the in vivo bioluminescence of P. stipticus	297
9.4.6	Synthetic studies of Panellus luciferin	300
9.5	Studies on Mycenn citricolor	301
9.5.1	Luciferin obtained Kuwabara and Wassink	301
9.5.2	Studies on the Mycena citricolor luminescence by the author	303
9.6	Summary on the Chemistry of Fungal Luminescence	307
10	Other Luminous Organisms	309
10.1	Ophiuroidea: Brittle Stars	309
10.1.1	The brittle star Ophiopsila californica	310
10.1.2	The brittle star Amphiura filiformis	314
10.2	Millipede Luminodesmus sequoiae (Diplopoda)	315
10.3	Centipede Orphaneus brevilabiatus (Chilopoda)	321
10.4	Hemicordata	322
10.4.1	The acorn worm Balanoglossus biminiensis	323
10.4.2	The luciferin of Ptychodera flava	325
10.5	Tunicates (Phylum Chordata)	327
10.6	The Luminous Fishes	329
10.6.1	Coastal and shallow-water fishes that utilize Cypridina luciferin	330
10.6.2	Oceanic deep-sea luminous fishes	334
10.6.3	Future research on fish bioluminescence	337
	Appendix	339
A	Taxonomic Classification of Selected Luminous Organisms	339
B	Lists of Luciferins, Luciferases and Photoproteins Isolated	345
C	Miscellaneous Technical Information	353
C1	Basic Principle of the Isolation of Bioluminescent Substances	353
C1.1	Reversible inhibition of bioluminescence	354
C1.2	Extraction of luciferin-luciferase systems	357
C1.3	Solubilization of proteins	357
C1.4	Purification	359
C2	Storage of Samples	360
C3	Measurement of Luminescence	363
C4	Calibration of Luminometer and the Measurement of Quantum Yield	365
C5	Detection and Assay of Coelenterazine, its Derivatives, and Other Important Substances in Bioluminescence	367
C5.1	Assay of coelenterazine	367
C5.2	Assay of the coelenterazine luciferase Activity	368
C5.3	Assay of the stabilized forms of coelenterazine	369
C5.4	Assay of dehydrocoelenterazine	370
C5.5	Assay of Cypridina luciferin	370
C5.6	Assay of Cypridina, luciferase	371
C5.7	Assay of Ca²⁺-sensitive Photoproteins	372
C5.8	Measuring bioluminescence in the field	373
C6	¹⁸O-Labeling of the Reaction Product CO₂	374
C7	Glassblowing	378
D	Advice to Students Who are Interested in Studying the Chemistry of Bioluminescence	379
	References	383
	Index	457