Naturally Occurring Organohalogen Compounds - a Comprehensive Update

by Gribble, Gordon W.

• ISBN13: 9783211993224
• ISBN10: 3211993223
• Edition: 1st
• Format: Hardcover
• Copyright: 2010-01-03
• Publisher: Springer Nature

Summary

Despite the long association of organohalogen compounds with human activities, nature is the producer of nearly 5,000 halogen-containing chemicals. Once dismissed as accidents of nature or isolation artifacts, organohalogen compounds represent an important and ever growing class of natural products, in many cases exhibiting exceptional biological activity. Since the last comprehensive review in 1996 (Vol. 68, this series), there have been discovered an additional 2,500 organochlorine, organobromine, and other organohalogen compounds. These natural organohalogens are biosynthesized by bacteria, fungi, lichen, plants, marine organisms of all types, insects, and higher animals including humans. These compounds are also formed abiogenically, as in volcanoes, forest fires, and other geothermal events.In some instances, natural organohalogens are precisely the same chemicals that man synthesizes for industrial use, and some of the quantities of these natural chemicals far exceed the quantities emitted by man.

Table of Contents

List of Contributors	p. xv
Introduction	p. 1
Origins	p. 3
Marine Environment	p. 3
Terrestrial Environment	p. 5
Extraterrestrial Enviroment	p. 8
Occurrence	p. 9
Simple Alkanes	p. 9
Chloromethane	p. 9
Dichloromethane	p. 12
Trichloromethane	p. 13
Tetrachloromethane (Carbon Tetrachloride)	p. 15
Bromomethane	p. 15
Other Simple Bromoalkanes	p. 17
Mixed Bromochloromethanes	p. 18
Iodomethanes	p. 19
Other Simple Iodoalkanes	p. 19
Mixed Iodomethanes	p. 20
Simple Alkenes	p. 20
Simple Alkynes	p. 22
Simple Organofluorines	p. 23
Other Simple Organochlorines	p. 24
Simple Functionalized Acyclic Organohalogens	p. 25
Simple functionalized Cyclic Organohalogens	p. 27
Cyclopentanes	p. 27
Cyclitols and Benzoquinones	p. 28
Terpenes	p. 32
Monoterpenes	p. 32
Sesquiterpenes	p. 38
Diterpenes	p. 60
Higher Terpenes	p. 86
Steroids	p. 92
Marine Nonterpenes: C15 Acetogenins	p. 96
Iridoids	p. 104
Lipids and Fatty Acids	p. 105
Fluorine-Containing Carboxylic Acids	p. 124
Prostaglandins	p. 127
Furanones	p. 130
Amino Acids and Peptides	p. 134
Alkaloids	p. 174
Heterocycles	p. 177
Pyrroles	p. 177
Indoles	p. 197
Carbazoles	p. 217
Indolocarbazoles	p. 217
Carbolines	p. 218
Quinolines and Other Nitrogen Heterocycles	p. 220
Benzofurans and Related Compounds	p. 226
Pyrones and Chromones	p. 227
Coumarins and Isocoumarins	p. 227
Flavones and Isoflavones	p. 231
Carbohydrates	p. 231
Polyacetylenes	p. 231
Terrestrial Polyacetylenes and Derived Thiophenes	p. 231
Marine Polyacetylenes	p. 232
Enediynes	p. 232
Macrolides and Polyethers	p. 234
Naphthoquinones, Higher Quinones, and Related Compounds	p. 249
Tetracyclines	p. 253
Aromatics	p. 254
Simple Phenols	p. i
Terrestrial	p. 256
Marine	p. 265
Complex Phenols	p. 270
Diphenylmethanes and Related Compounds	p. 270
Diphenyl Ethers	p. 273
Tyrosines	p. 281
Depsides	p. 314
Depsidones	p. 315
Xamhones	p. 317
Anthraquinones and Related Compounds	p. 319
Griseofulvin and Related Compounds	p. 322
Miscellaneous Fungal Metabolites and Other Complex Phenols	p. 322
Glycopeptides	p. 328
Orthosomycins	p. 333
Dioxins and Dibenzofurans	p. 337
Humic Acids	p. 345
Biohalogenation	p. 349
Introduction	p. 349
Chloroperoxidase	p. 349
Bromoperoxidase	p. 355
Halogenases, Other Haloperoxidases and Peroxidases	p. 356
Myeloperoxidase	p. 360
Abiotic Processes	p. 361
Biofluorination	p. 361
Biosynthesis	p. 362
Biodegradation	p. 367
Natural Function	p. 369
Significance	p. 375
Outlook	p. 377
References	p. 379
Author Index	p. 507
Subject Index	p. 577
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