Blepharismone: a Conjugation-Inducing Tryptophan Derivative in the Ciliate Blepharisma

Chapters in this book

1. Frontmatter I
2. Preface V
3. CONTENTS VII
4. OPENING SESSION
5. Adolf Butenandt's Work on the Metabolism of Tryptophan 1
6. Tryptophan, the Heart of the Toxic Peptides from Amanita Mushrooms 13
7. Forty Years of Trypto-Fun 21
8. Indoleamine Dioxygenase - a Possible Biological Function 33
9. QUALITATIVE AND QUANTITATIVE ANALYSIS OF TRYPTOPHAN AND ITS METABOLITES
10. Liquid Chromatography/Electrochemistry Determination of Biogenic Amines: Improved Performance Using Low Dead Volume Multiple Electrode Transducers 45
11. GLC and HPLC Analysis of Tryptophan, Kynurenine and Related Metabolites 55
12. Monitoring of Tryptophan Levels in Biological Fluids by HPLC: An Improved Method 63
13. Rapid Determination of Tryptophan and its Metabolitesalong the Kynurenine Pathway by HPLC 67
14. HPLC-Analysis of Xanthurenic Acid and its 8-Methyl-Ether 71
15. Free and Total Tryptophan Microdetermination by an Automated Fluorometric Method 77
16. Comparison of HPLC and GC-MS Methods for the Determination of Tryptophan and its Indole Metabolites in Biological Samples 83
17. Pineal Indoles: Their Determination by High Performance Liquid Chromatography and the Influence of Diurnal Variation and Tryptophan Administration on their Level in the Rat 91
18. Higher-Order Derivative Spectrophotometry for the Quantitative Determination of Tryptophan, Tyrosine and Phenylalanine in Two- and Three-Component Mixtures, Peptides and Proteins 95
19. The Application of a Spectrofluorometer-Optical- Multichannel Analyzer System to the Determination of Tryptophan 103
20. Picomole Determination of Tryptophan by Derivatization to 9-Hydroxymethyl-ß-Carboline 107
21. Determination of Tryptophan in Food after Alkaline Hydrolysis: An Evaluation 111
22. Colorimetric Determination of Tryptophan in Corn-Cob Mix (CCM) 115
23. Comparison of Tryptophan Assays for Food Proteins 119
24. WORKSHOP: ANALYSIS OF TRYPTOPHAN
25. Discussion at the Workshop on "Analysis of Tryptophan" 127
26. TRYPTOPHAN AND SEROTONIN: NEUROBIOLOGY
27. Tryptophan Transport to the Brain: Newer Findings and Older Ones Reconsidered 145
28. Tryptophan Availability and Serotonin Synthesis in Rat Brain: Effects of Experimental Diabetes 161
29. Anatomy and Function of Central Serotoninergic Neurons 173
30. Serotonin Receptor Binding Sites: Localization and Role in the Brain and Peripheral Tissues 189
31. Involvement of 5-HT₂ (S₂)- Receptor Sites in the Serotonin-Induced Activation of Cat Platelets 197
32. The Regulation of 5-Hydroxytryptamine Release from Superfused Synaptosomes by Tryptophan 201
33. Selective Increases in High Affinity Tryptophan Transport in Synaptosomes from Different Brain Areas Incubated in Sodium-Free Media 205
34. Formation and Function of Tetrahydro-ß-Carbolines with Special Reference to their Action on [3H] - Tryptamine Binding Sites 209
35. Regulations of Serotonergic Neurons Innervating the Basal Ganglia: In vivo Release Studies 217
36. Blood Platelets as Models for Neurons: Similarities of the 5-Hydroxytryptamine Systems 231
37. In vivo Metabolism of ¹⁴C-5-HT, ¹⁴C-5.6-DHT and ¹⁴C-5.7-DHT by MAO/COMT/Aldehyde Dehydrogenase in Rat Brain 241
38. Tryptophan Metabolism in the Pineal Gland 251
39. Some Physiological Responses and Effects of the Pineal Indoleamine Melatonin 259
40. Pharmacologic Regulation of Serum N-Acetylserotonin 267
41. N-Acetyltryptophan: Biochemical and Pharmacological Studies 271
42. Serotonin, a Major Metabolite of Tryptophan in the Rabbit Retina 275
43. Effect of 5-Hydroxyanthranilic Acid on Arachidonate Metabolites Function in Platelet Aggregation System 285
44. WORKSHOP: CLINICAL AND BEHAVIOURAL EFFECTS OF TRYPTOPHAN
45. Introduction to Workshop 291
46. Tryptophan and Human Sleep: An Analysis of 43 Studies 297
47. L-Tryptophan in Chronic Insomnia 305
48. Tryptophan (500 mg) Decreases Subjectively Perceived Sleep Latency and Increases Sleep Depth in Man 311
49. Further Evidence of the Hypnotic Properties of Tryptophan 315
50. The Therapeutic Action of Tryptophan in Depression, Mania, and Aggression 321
51. The Effects of Dietary Tryptophan on Chronic Maxillofacial Pain Tolerance 325
52. PATHOLOGY, CLINICAL ASPECTS
53. Modulation of Serotonin Receptors by L-Valine in Hepatic Encephalopathy 333
54. Effect of a B-Vitamin on Tryptophan Metabolism in South African Bantu with Pellagra 339
55. Studies on the Urinary Excretion of Xanthurenic Acid in Diabetics 347
56. Urinary Excretion of Xanthurenic Acid and Zinc in Diabetes 355
57. Studies of the Clinical Importance and Molecular Defect of Hereditary Vitamin B₆ Dependent Xanthurenic Aciduria 359
58. Tryptophan - Nicotinic Acid Pathway in Cardiovascular Diseases 365
59. The Dependence of Stress Induced Increases in Functional 5HT Activity on Increased Tryptophan Availability: Evidence that in vivo Electrochemistry Monitors 5-Hydroxyindole Release 383
60. Increased Availability of Tryptophan to the Brain in Stress is not Mediated via Changes in Competing Amino Acids 387
61. Free and Bound Plasma Tryptophan Levels in Psychiatric Disorders 391
62. Cerebrospinal Fluid 5HIAA and Tryptophan in Depression and Suicide 397
63. The Influence of L5-Hydroxytryptophan (L5-HTP) on Clinical and Biochemical Parameters in Depressive Patients 401
64. Plasma Tryptophan Levels and 5-Hydroxytryptamine Synthesis in the Brain and the Spinal Cord in "Arthritic" Rats 405
65. Effects of Antirheumatic Drugs and Tricyclic Antidepressants on Total and Free Serum Tryptophan Levels in Arthritic Rats 409
66. Tryptophan, Serotonin and 5-Hydroxyindoleacetic Acid Levels in Human CSF in Relation to Pain 413
67. Dynamics of Plasma Tryptophan Following Antimigraine Drugs 417
68. Comparison of Morphine and Meptazinol Effects on Rat Tryptophan Disposition and Metabolism 425
69. Decreased Concentrations of Tryptophan and Serotonin in the Brain of Developing Hyperphenylalaninemic Rats - A Contribution to the Understanding of the Metabolic Effects in Phenylketonuria 429
70. Cofactor Dependency of Serotonin and Catecholamine Biosynthesis in Patients with Atypical Phenylketonuria and Endogenous Depression 437
71. Tryptophan, 5-Hydroxytryptophan and Dopa Metabolism in the Rat with Experimental Phenylketonuria 443
72. The Role of Tryptophan Oxidation in Ocular Tissue Damage 449
73. Tryptophan and Kynurenine in Senile Cataract 469
74. Urinary 5-Hydroxyindoleacetic Acid and Serum Phénobarbital of Children Suffering from Epilepsy 473
75. Anticonvulsant Drugs Produce Different Effects on Plasma Tryptophan Concentrations in Epileptic Patients 479
76. The Role of Metabolism in 3-Methylindole-Induced Acute Lung Injury 483
77. Beta-Carboline Levels in Blood of Smokers and Non-Smokers 491
78. The Relationship between Tryptophan, Tryptophan Metabolites and Bladder Cancer 503
79. Role of Indoleamine 2,3-Dioxygenase in the Defence Mechanism against Tumor Growth 513
80. The Relationship between Plasma Kynurenine and Indoleamine 2,3-Dioxygenase Activity in the Extrahepatic Tissues 517
81. L-Tryptophan Metabolism along the Kynurenine Pathway in Human Malignant Melanoma 521
82. NUTRITIONAL ASPECTS
83. Content and Stability of Tryptophan in Foods 527
84. Increased Aromatic Amine (Kynurenine) in Dried Fish Meat under Sunlight 535
85. Tryptophan Requirement of Farm Animals 537
86. Pattern of Radioactivity from Endogenous 3H-Tryptophan Excreted in the Urine of Fasted or Rats Fed Diets Containing Different Levels of Casein 545
87. Protein/Carbohydrate Selection in Rats Following Administration of Tryptophan, Glucose or a Mixture of Amino Acids 549
88. Influence of Tryptophan on Gastric Mucosal Protein Synthesis 553
89. Tryptophan and Intestinal Secretion 563
90. Tryptophan Metabolism in Undernourished Developing Rat Brain 567
91. Effect of Tryptophan on Protein Utilization and Energy Intake of Pigs 571
92. A High Carbohydrate, Protein-Free Meal, either at Breakfast or in the Evening Does not Alter Plasma Tryptophan to Large Neutral Amino Acid Ratios in Healthy Men 579
93. Effects of Large Neutral Amino Acids on Tryptophan Transport into the Brain during Development 583
94. Contribution of Exegenous N¹⁵ -Tryptophan to Plasma and Red Blood Cell Tryptophan and Kynurenine in Healthy Humans 587
95. Carbohydrate Meal Increases Brain 5-Hydroxytryptamine Synthesis in the Adult Rat only after Prolonged Fasting 591
96. Exogenous Tryptophan: A Study of its Effects on the Levels of Aromatic Amine(s) in Cerebral and Hepatic Tissues in Mice 595
97. Influence of Excess Leucine Intake on the Conversion of Tryptophan to NAD in Rats Fed Low Protein Diet 599
98. The Pellagragenic Action of a Dietary Excess of Leucine: Effects of a High-Leucine Diet on Tryptophan Metabolism 603
99. Effect of Cadmium on some Key Enzymes of Tryptophan - NAD Pathway in Rats in vivo 607
100. The Influence of Increased Availability of Tryptophan on the Formation of Tryptamine and Serotonin during Early Ontogenesis 613
101. TRYPTOPHAN METABOLISM IN MAMMALS
102. Tryptophan Metabolism and its Control in Mammalian Liver 625
103. Tryptophan Metabolism by the Isolated, Perfused Liver and Kidney of Rat (Quantification of the Metabolism by the Compartmental Analysis) 633
104. Effects of Oestrogens on the Metabolism of Tryptophan Implications for the Interpretation of the Tryptophan Load Test for Vitamin B₆ Nutritional Status 637
105. The Functions and Regulation of Tryptophan Pyrrolase 641
106. Kynurenine Aminotransferase Activity in Human and other Mammalian Tissues 651
107. Intracellular Localization and Characterization of 3-Hydroxykynureninase in Human Liver 657
108. Time-Course of 5-HTP Metabolism in Rabbits: Relevance of Transaminating Pathway 661
109. Tryptophan Aminotransferase Activity in Rat Liver 665
110. The Oxygenation of Tryptophan and Indoles with Superoxide Ion and Dioxygen in the Presence of Copper and Ruthenium Catalysts 669
111. Serotonin- and Melatonin-Dependent Light Emission Induced by Xanthine Oxidase 673
112. The in vivo Effect of Sodium Fluoride on the Key Enzymes of Tryptophan Metabolism 677
113. Roles of Active Oxygen and Superoxide Dismutase in Anthranilatnide Hydroxylation and its Derived Phenoxazinone-Like Pigment Formation by Rat Liver Microsomal Monooxygenase System 681
114. Protective Effect of Tryptophan upon the Influence of N-Methylformamide on the Development, the NAD Synthesis, and the Activity of the Adenosine Diphosphate Ribosyl Transferase of Rat Embryos 685
115. Induction of Tyrosine Aminotransferase by Tryptophan in Rat Liver 689
116. TRYPTOPHAN METABOLISM IN INSECTS
117. Tryptophan Metabolism in Drosophila 697
118. Roles of Active Oxygen and Catalase in the Formation of Phenoxazinone Pigments Catalysed by Manganese Ion 711
119. Ommochrome-Potassium Urate Complex as Pigment of Red Faeces of Locusta migratoria (Insecta, Orthoptera, Acrididae) 715
120. Changes in Fluorescence and Size of the Cytoplasmic Granules in the Malpighian Tubules of Drosophila melanogaster Linked with Tryptophan Metabolism 719
121. Hormonal Control of Pigmentation in Manduca sexta 723
122. Tryptophan Metabolism and Morphological Color Change in Insects 733
123. The Structure of Papiliochrome II, the Yellow Wing Pigment of the Papilionid Butterflies 743
124. Some Chemical Properties of Papiliochrome R 747
125. TRYPTOPHAN METABOLISM IN PLANTS AND MICROORGANISMS
126. Metabolism of Tryptophan in Pseudomonas aureofaciens 753
127. Does Tryptophan Side Chain Oxidase from Pseudomonas ATCC 29574 Contain a Quinoprotein? 761
128. Tryptophan Side Chain Oxidase (TSO) - Structure and Reaction Mechanism 765
129. Characterization of three Tryptophan Aminotransferases from Candida maltosa 769
130. Anthranilate Hydroxylase and the Short-Cut-Pathway for the Biosynthesis of Nicotinamide Nucleotides in Aspergillus niger 773
131. Biosynthesis of Tryptophan Derived Alkaloids in Higher Plants: Enzymati Formation of the Sarpagine-Ajmaline Group 777
132. Acridone Alkaloid Biosynthesis in Tissue Cultures of Ruta graveolens 785
133. Isolation and Biological Activities of Diterpene Anthraniloyl and 3-Hydroxyanthraniloyl Peptide Esters from Euphorbia mi Iii 789
134. New Biological Significance of Indole-Containing Compounds as Initiators or Tumor Promoters in Chemical Carcinogenesis 793
135. Biosynthesis of Serotonin and Auxin in Seeds of Juglans regia 803
136. Blepharismone: a Conjugation-Inducing Tryptophan Derivative in the Ciliate Blepharisma 807
137. Biological Activity of Blepharismone Derivatives - An Approach Towards Biogenesis of the Hormone 815
138. TRYPTOPHAN IN PROTEINS AND PEPTIDES
139. Advances in the Chemical Modification of Tryptophan in Peptides and Proteins 829
140. Peptide Bond Cleavage at Tryptophan with Cyanogen Bromide - Mechanism of the Reaction 839
141. Tryptophan, a Pitfall for the Peptide Chemist 845
142. Photochemical arid Radiochemical Reactions of Tryptophan: Modification of a Single-Strand Binding Protein from Bacteriophage T4 853
143. X-Ray Structure Analyses of Tryptophan Derivatives as Models for Stereochemical Aspects of the Toxic Peptides from Amanita Mushrooms 861
144. AUTHOR INDEX 865
145. SUBJECT INDEX 869
146. ABBREVATIONS 889
147. Backmatter 891