List of Contributors ........................................... xv
1 Introduction ................................................. 1
2 Origins ...................................................... 3
2.1 Marine Environment ...................................... 3
2.2 Terrestrial Environment ................................. 5
2.3 Extraterrestrial Environment ............................ 8
3 Occurrence ................................................... 9
3.1 Simple Alkanes .......................................... 9
3.1.1 Chloromethane .................................... 9
3.1.2 Dichloromethane ................................. 12
3.1.3 Trichloromethane ................................ 13
3.1.4 Tetrachloromethane (Carbon Tetrachloride) ....... 15
3.1.5 Bromomethane .................................... 15
3.1.6 Other Simple Bromoalkanes ....................... 17
3.1.7 Mixed Bromochloromethanes ....................... 18
3.1.8 Iodometfianes ................................... 19
3.1.9 Other Simple Iodoalkanes ........................ 19
3.1.10 Mixed Iodomethanes .............................. 20
3.1.11 Simple Alkenes .................................. 20
3.1.12 Simple Alkynes .................................. 22
3.1.13 Simple Organofluorines .......................... 23
3.1.14 Other Simple Organochlorines .................... 24
3.2 Simple Functionalized Acyclic Organohalogens ........... 25
3.3 Simple Functionalized Cyclic Organohalogens ............ 27
3.3.1 Cyclopentanes ................................... 27
3.3.2 Cyclitols and Benzoquinones ..................... 28
3.4 Terpenes ............................................... 32
3.4.1 Monoterpenes .................................... 32
3.4.2 Sesquiterpenes .................................. 38
3.4.3 Diterpenes ...................................... 60
3.4.4 Higher Terpenes ................................. 86
3.5 Steroids ............................................... 92
3.6 Marine Nonterpenes: C15 Acetogenins .................... 96
3.7 Iridoids .............................................. 104
3.8 Lipids and Fatty Acids ................................ 105
3.9 Fluorine-Containing Carboxylic Acids .................. 124
3.10 Prostaglandins ........................................ 127
3.11 Furanones ............................................. 130
3.12 Amino Acids and Peptides .............................. 134
3.13 Alkaloids ............................................. 174
3.14 Heterocycles .......................................... 177
3.14.1 Pyrroles ....................................... 177
3.14.2 Indoles ........................................ 197
3.14.3 Carbazoles ..................................... 217
3.14.4 Indolocarbazoles ............................... 217
3.14.5 Carbolines ..................................... 218
3.14.6 Quinolines and Other Nitrogen Heterocycles ..... 220
3.14.7 Benzofurans and Related Compounds .............. 226
3.14.8 Pyrones and Chromones .......................... 227
3.14.9 Coumarins and Isocoumarins ..................... 227
3.14.10 Flavones and Isoflavones ...................... 231
3.14.11 Carbohydrates ................................. 231
3.15 Polyacetylenes ........................................ 231
3.15.1 Terrestrial Polyacetylenes and Derived
Thiophenes ..................................... 231
3.15.2 Marine Polyacetylenes .......................... 232
3.16 Enediynes ............................................. 232
3.17 Macrolides and Polyethers ............................. 234
3.18 Naphthoquinones, Higher Quinones, and Related
Compounds ............................................. 249
3.19 Tetracyclines ......................................... 253
3.20 Aromatics ............................................. 254
3.21 Simple Phenols ........................................ 256
3.21.1 Terrestrial .................................... 256
3.21.2 Marine ......................................... 265
3.22 Complex Phenols ....................................... 270
3.22.1 Diphenylmethanes and Related Compounds ......... 270
3.22.2 Diphenyl Ethers ................................ 273
3.22.3 Tyrosines ...................................... 281
3.22.4 Depsides ....................................... 314
3.22.5 Depsidones ..................................... 315
3.22.6 Xanthones ...................................... 317
3.22.7 Anthraquinones and Related Compounds ........... 319
3.22.8 Griseofulvin and Related Compounds ............. 322
3.22.9 Miscellaneous Fungal Metabolites and Other
Complex Phenols ................................ 322
3.23 Glycopeptides ......................................... 328
3.24 Orthosomycins ......................................... 333
3.25 Dioxins and Dibenzofurans ............................. 337
3.26 Humic Acids ........................................... 345
4 Biohalogenation ............................................ 349
4.1 Introduction .......................................... 349
4.2 Chloroperoxidase ...................................... 349
4.3 Bromoperoxidase ....................................... 355
4.4 Halogenases, Other Haloperoxidases and Peroxidases .... 356
4.5 Myeloperoxidase ....................................... 360
4.6 Abiotic Processes ..................................... 361
4.7 Biofluorination ....................................... 361
4.8 Biosynthesis .......................................... 362
5 Biodegradation ............................................. 367
6 Natural Function ........................................... 369
7 Significance ............................................... 375
8 Outlook .................................................... 377
References .................................................... 379
Author Index .................................................. 507
Subject Index ................................................. 577
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