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Summary
Summary
Fungi occupy an important place in the natural world, as non-photosynthetic organisms, they obtain their nutrients from the degradation of organic material. They use many of their secondary metabolites to secure a place in a competitive natural environment and to protect themselves from predation. The diverse structures, biosyntheses and biological activities of fungal metabolites have attracted chemists for many years. Fungi are ubiquitous and their activities affect many aspects of our daily lives whether it be as sources of pharmaceuticals and food or as spoilage organisms and the causes of diseases in plants and man. The chemistry of the fungi involved in these activities has been the subject of considerable study particularly over the last fifty years. Although their ramifications can be large as in the spread of plant diseases, the quantities of the metabolites which could be isolated precluded much chemical work until the advent of spectroscopic methods. Whereas many natural products derived from plants were isolated prior to the 1960s on a scale which permitted extensive chemical degradation, this was rarely the case for fungal metabolites. This book is an introduction to the chemistry of fungal metabolites. The aim is to illustrate within the context of fungal metabolites, the historical progression from chemical to spectroscopic methods of structure elucidation, the development in biosynthetic studies from establishing sequences and mechanisms to chemical enzymology and genetics and the increasing understanding of the biological roles of natural products. The book begins with a historical introduction followed by a description of the general chemical features which contribute to the growth of fungi. There are many thousands of fungal metabolites whose structures are known and the book does not aim to list them all as there are databases to fulfill this role. The book's aim is to describe some of the more important metabolites classified according to their biosynthetic origin. Biosynthesis provides a unifying feature underlying the diverse structures of fungal metabolites and the chapters covering this area begin with a general outline of the relevant biosynthetic pathway before presenting a detailed description of particular metabolites. Investigations into these biosyntheses have utilized many subtle isotopic labelling experiments and compounds that are fungal pigments and those which are distinctive metabolites of the more conspicuous Basidiomycetes are treated separately. Many fungal metabolites are involved in the interactions of fungi with plants and others are toxic to man and some of these are described in further chapters. Fungi have the ability to transform chemicals in ways which can complement conventional reactions and the use of fungi as reagents forms the subject of the final chapter. This book will be particularly useful to anybody about to embark on a career in chemical microbiology by providing an overall perspective of fungal metabolites as well as an essential reference tool for more general chemists.
Author Notes
James R. Hanson, Department of Chemistry, University of Sussex, Brighton, UK
Table of Contents
Chapter 1 Fungi and the Development of Microbiological Chemistry | |
1.1 Introduction | p. 1 |
1.2 Structure of Fungi | p. 2 |
1.3 Classification of Fungi | p. 4 |
1.4 The Fungal Cell Wall | p. 5 |
1.5 History of Fungal Metabolites | p. 6 |
1.5.1 Fungal Metabolites in the Nineteenth Century | p. 7 |
1.5.2 Fungal Metabolites 1900-1940 | p. 8 |
1.5.3 Fungi in the Antibiotic Era, 1940-1960 | p. 10 |
1.5.4 Study of Fungal Plant Diseases 1940-1965 | p. 12 |
1.5.5 Impact of Spectroscopic Methods on Structure Elucidation | p. 13 |
1.5.6 Fungal Metabolites 1965-2005 | p. 13 |
1.5.7 History of Biosynthetic Studies with Fungi | p. 15 |
Chapter 2 The Chemistry of Growing Fungi | |
2.1 The Culture Medium | p. 18 |
2.2 Laboratory Fermentation | p. 20 |
2.3 Isolation of Fungal Metabolites | p. 21 |
2.4 The Stages in a Fermentation | p. 23 |
2.5 Utilization of the Constituents of the Medium | p. 25 |
2.6 Fungi Growing in the Wild | p. 28 |
2.7 Biosynthetic Experiments | p. 29 |
Chapter 3 Fungal Metabolites Derived from Amino Acids | |
3.1 Introduction | p. 32 |
3.2 Penicillins | p. 33 |
3.3 Cephalosporins | p. 36 |
3.4 Biosynthesis of [beta]-Lactams | p. 37 |
3.5 Metabolites Containing a Diketopiperazine Ring | p. 39 |
3.5.1 Mycelianamide | p. 40 |
3.5.2 Gliotoxin | p. 40 |
3.6 The Cyclopenin-Viridicatin Group of Metabolites | p. 42 |
3.7 Tryptophan-derived Metabolites | p. 42 |
3.8 Glutamic Acid Derivatives | p. 44 |
3.9 Fungal Peptides | p. 45 |
Chapter 4 Polyketides from Fungi | |
4.1 Introduction | p. 47 |
4.2 Polyketide Biosynthesis | p. 48 |
4.3 Triketides | p. 50 |
4.4 Tetraketides | p. 51 |
4.4.1 6-Methylsalicylic Acid | p. 51 |
4.4.2 Patulin and Penicillic Acid | p. 52 |
4.4.3 Gladiolic Acid and its Relatives | p. 55 |
4.4.4 Tetraketide Tropolones | p. 56 |
4.4.5 Mycophenolic Acid | p. 57 |
4.5 Pentaketides | p. 58 |
4.5.1 Citrinin | p. 58 |
4.5.2 Terrein | p. 60 |
4.6 Hepta- and Octaketides | p. 61 |
4.6.1 Griseofulvin | p. 61 |
4.6.2 Cladosporin (Asperentin) | p. 64 |
4.7 Polyketide Lactones | p. 65 |
4.8 Statins | p. 66 |
4.9 Cytochalasins | p. 68 |
4.10 Fatty Acids from Fungi | p. 68 |
4.11 Polyacetylenes from the Higher Fungi | p. 70 |
Chapter 5 Terpenoid Fungal Metabolites | |
5.1 Introduction | p. 73 |
5.2 Biosynthesis of Fungal Terpenoids | p. 73 |
5.3 Monoterpenoids | p. 76 |
5.4 Sesquiterpenoids | p. 76 |
5.4.1 Cyclonerodiol | p. 77 |
5.4.2 Helicobasidin | p. 78 |
5.4.3 Trichothecenes | p. 78 |
5.4.4 PR-Toxin | p. 81 |
5.4.5 Botryanes | p. 81 |
5.4.6 Culmorin and Helminthosporal | p. 84 |
5.4.7 Sesquiterpenoids of the Basidiomycetes | p. 85 |
5.5 Diterpenoid Fungal Metabolites | p. 93 |
5.5.1 Virescenosides | p. 94 |
5.5.2 Rosanes | p. 94 |
5.5.3 Gibberellins and Kaurenolides | p. 97 |
5.5.4 Aphidicolin | p. 101 |
5.5.5 Pleuromutilin | p. 102 |
5.5.6 Fusicoccins and Cotylenins | p. 102 |
5.6 Sesterterpenoids | p. 104 |
5.7 Fungal Triterpenoids and Steroids | p. 105 |
5.7.1 Ergosterol | p. 106 |
5.7.2 Fusidane Steroidal Antibiotics | p. 107 |
5.7.3 Viridin, Wortmannin and their Relatives | p. 111 |
5.7.4 Triterpenoids of the Basidiomycetes | p. 113 |
5.8 Meroterpenoids | p. 116 |
Chapter 6 Fungal Metabolites Derived from the Citric Acid Cycle | |
6.1 Introduction | p. 120 |
6.2 Citric Acid and Related Acids | p. 120 |
6.3 Fungal Tetronic Acids | p. 122 |
6.4 Canadensolide and Avenaciolide | p. 123 |
6.5 Nonadrides | p. 124 |
6.6 Squalestatins | p. 126 |
Chapter 7 Pigments and Odours of Fungi | |
7.1 Introduction | p. 127 |
7.2 Polyketide Fungal Pigments | p. 128 |
7.2.1 Fumigatin | p. 128 |
7.2.2 Auroglaucin and Flavoglaucin | p. 129 |
7.2.3 Hydroxyanthraquinone Pigments | p. 129 |
7.2.4 Xanthone and Naphthopyrone Pigments | p. 130 |
7.2.5 Extended and Dimeric Quinones | p. 131 |
7.3 Fungal Pigments Derived from the Shikimate Pathway | p. 132 |
7.3.1 Terphenyls | p. 132 |
7.3.2 Pulvinic Acids | p. 133 |
7.4 Some Pigments Containing Nitrogen | p. 135 |
7.5 Terpenoid Pigments | p. 138 |
7.5.1 Fungal Carotenoids | p. 138 |
7.6 Lichen Substances | p. 140 |
7.7 Odours of Fungi | p. 142 |
7.7.1 Organoleptic Components of Mushrooms | p. 142 |
7.7.2 Volatile Fungal Metabolites Containing Sulfur | p. 144 |
Chapter 8 The Chemistry of Some Fungal Diseases of Plants | |
8.1 Introduction | p. 147 |
8.2 General Chemistry of Plant-Fungal Interactions | p. 148 |
8.3 Chemistry of some Leaf-spot Diseases | p. 149 |
8.3.1 Botrytis cinerea | p. 149 |
8.3.2 Alternaria Leaf-spot Diseases | p. 151 |
8.3.3 Cercospora Leaf-spot Diseases | p. 153 |
8.3.4 Diseases Caused by Colletotrichum Species | p. 154 |
8.4 Fungal Diseases of the Gramineae | p. 155 |
8.5 Root-infecting Fungi | p. 157 |
8.6 Some Fungal Diseases of Trees | p. 159 |
8.6.1 Dutch Elm Disease | p. 159 |
8.6.2 Eutypa Dieback | p. 160 |
8.6.3 Armillaria mellea | p. 161 |
8.6.4 Phytophthora cinnamomi | p. 162 |
8.6.5 Silver-leaf Disease | p. 162 |
8.6.6 Nectria galligena Canker | p. 162 |
8.6.7 Canker Diseases of Cypress | p. 163 |
8.7 Trichoderma Species as Anti-fungal Agents | p. 163 |
8.8 Fungal Diseases of Plants and Global Warming | p. 164 |
Chapter 9 Mycotoxins | |
9.1 Introduction | p. 165 |
9.2 Ergotism | p. 165 |
9.3 Trichothecenes as Mycotoxins | p. 166 |
9.4 Other Fusarium Toxins | p. 168 |
9.5 Aflatoxins | p. 169 |
9.6 Mycotoxins of Penicillium Species | p. 171 |
9.7 Poisonous Mushrooms | p. 173 |
Chapter 10 Fungi as Reagents | |
10.1 Introduction | p. 177 |
10.2 Xenobiotic Transformations | p. 177 |
10.2.1 Microbial Hydrolysis | p. 178 |
10.2.2 Microbial Redox Reactions | p. 179 |
10.2.3 Microbiological Hydroxylation | p. 180 |
10.3 Biosynthetically-patterned Biotransformations | p. 183 |
Epilogue | p. 188 |
Further Reading and Bibliography | p. 190 |
Glossary | p. 204 |
Subject Index | p. 209 |