Naturally Occurring Organohalogen Compounds - A Comprehensive Update (Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products Book 91)

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. Springer 3211993223 1 DOI: 10.1007/978-3-211-99323-1 8 Brief CV – Gordon W. Gribble 7 Acknowledgements 7 Contents 7 List of Contributors 7 Chapter 1: Introduction 13 Chapter 2: Origins 14 Marine Environment 14 Terrestrial Environment 16 Extraterrestrial Environment 19 Chapter 3: Occurrence 20 Simple Alkanes 20 Chloromethane 20 Marine 20 Terrestrial Biogenic 21 Terrestrial Abiotic 22 Biomass Combustion 22 Volcanic Emissions 23 Biogenesis 23 Dichloromethane 23 Trichloromethane 24 Marine 24 Terrestrial Biogenic 25 Biomass Combustion 26 Volcanic Emissions 26 Tetrachloromethane (Carbon Tetrachloride) 26 Bromomethane 26 Marine 27 Terrestrial Biogenic 28 Terrestrial Abiotic 28 Biomass Combustion 28 Volcanic Emissions 28 Other Simple Bromoalkanes 28 Marine 28 Volcanic Emissions 29 Mixed Bromochloromethanes 29 Iodomethanes 30 Marine 30 Terrestrial 30 Other Simple Iodoalkanes 30 Marine 30 Volcanic Emissions 31 Mixed Iodomethanes 31 Simple Alkenes 31 Marine 31 Terrestrial Biogenic 32 Terrestrial Abiotic 32 Volcanic Emissions 32 Simple Alkynes 33 Terrestrial Abiotic 33 Volcanic Emissions 34 Simple Organofluorines 34 Other Simple Organochlorines 35 Simple Functionalized Acyclic Organohalogens 36 Simple Functionalized Cyclic Organohalogens 38 Cyclopentanes 38 Cyclitols and Benzoquinones 39 Terpenes 43 Monoterpenes 43 Acyclic Monoterpenes 43 Alicyclic Monoterpenes 46 Sesquiterpenes 49 Terrestrial Sesquiterpene Lactones 49 Indanone Sesquiterpenes 55 Other Terrestrial Sesquiterpenes 55 Marine Sesquiterpenes 57 Monocyclic and Other Simple Sesquiterpenes 58 Chamigrene and Related Types 62 Eudesmane and Other Types 65 Cuparene, Laurene, and Other Aromatic Types 68 Diterpenes 71 Terrestrial Diterpenes 71 Marine Diterpenes 73 Diterpenes of Aplysia 73 Diterpenes of Laurencia 74 Sphaerococcus and Other Red Algae Diterpenes 78 Sponge Diterpenes 79 Gorgonian Diterpenes 81 Higher Terpenes 97 Steroids 103 Marine Nonterpenes: C15 Acetogenins 107 Iridoids 115 Lipids and Fatty Acids 116 Fluorine-Containing Carboxylic Acids 135 Prostaglandins 138 Furanones 141 Amino Acids and Peptides 145 Alkaloids 185 Heterocycles 188 Pyrroles 188 Indoles 208 Carbazoles 228 Indolocarbazoles 228 Carbolines 229 Quinolines and Other Nitrogen Heterocycles 231 Benzofurans and Related Compounds 237 Pyrones and Chromones 238 Coumarins and Isocoumarins 238 Flavones and Isoflavones 242 Carbohydrates 242 Polyacetylenes 242 Terrestrial Polyacetylenes and Derived Thiophenes 242 Marine Polyacetylenes 243 Enediynes 243 Macrolides and Polyethers 245 Naphthoquinones, Higher Quinones, and Related Compounds 260 Tetracyclines 264 Aromatics 265 Simple Phenols 267 Terrestrial 267 Marine 276 Complex Phenols 281 Diphenylmethanes and Related Compounds 281 Diphenyl Ethers 284 Tyrosines 292 Simple Tyrosines, Thyroxine, and Related Compounds 292 Transformed Tyrosines, Tyramines, Phenethylamines and Related Compounds 293 Transformed Multiple Tyrosines 311 Bastadins 323 Depsides 325 Depsidones 326 Xanthones 328 Anthraquinones and Related Compounds 330 Griseofulvin and Related Compounds 333 Miscellaneous Fungal Metabolites and Other Complex Phenols 333 Glycopeptides 339 Orthosomycins 344 Dioxins and Dibenzofurans 348 Humic Acids 356 Chapter 4: Biohalogenation 360 Introduction 360 Chloroperoxidase 360 Bromoperoxidase 366 Halogenases, Other Haloperoxidases and Peroxidases 367 Myeloperoxidase 371 Abiotic Processes 372 Biofluorination 372 Biosynthesis 373 Chapter 5: Biodegradation 377 Chapter 6: Natural Function 379 Chapter 7: Significance 385 Chapter 8: Outlook 387 Chapter : References 389 : Author Index 516 : Subject Index 586 ISBN-13:,9783211993224 ISBN-13: 9783211993224 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 Origins: Marine environment. Terrestrial environment. Extraterrestrial environment. Occurrence: Simple alkanes. Simple functionalized acyclic organohalogens. Simple functionalized cyclic organohalogens. Terpenes. Steroids. Marine nonterpenes: C15 acetogenins. Iridoids. Lipids and fatty acids. Fluorine-contaning carboxylic acids. Prostaglandins. Furanones. Amino acids and peptides. Alkaloids. Heterocycles. Polyacetylenes. Enediynes. Macrolides and polyethers. Naphthaoquinones, higher quinones, and related compounds. Tetracyclines. Aromatics. Simple phenols. Complex phenols. Glycopeptides. Orthosomycins. Dioxins and dibenzofurans. Humic acids. Biohalogentation: Introduction. Chloroperoxidase. Bromoperoxidase. Halogenases, other haloperoxidases and peroxidases. Myeloperoxidase. Abiotic processes. Biofluorination. Biosynthesis. Biodegredation. Natural Function. Significance. Outlook. Front Matter....Pages i-xv Introduction....Pages 1-1 Origins....Pages 3-8 Occurrence....Pages 9-348 Biohalogenation....Pages 349-365 Biodegradation....Pages 367-368 Natural Function....Pages 369-374 Significance....Pages 375-376 Outlook....Pages 377-378 Back Matter....Pages 379-613 Since the last comprehensive review on organohalogen compounds in 1996, an additional 2500 organochlorine, organobromine and other organohalogen compounds have been discovered. This book discusses all those latest discoveries in the field