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Cover image for The chemistry of fungi
Title:
The chemistry of fungi
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Publication Information:
Cambridge, UK : Royal Society of Chemistry, 2008
Physical Description:
xi, 221 p. : ill. ; 25 cm.
ISBN:
9780854041367
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30000010210684 QR84 H36 2008 Open Access Book Book
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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 Introductionp. 1
1.2 Structure of Fungip. 2
1.3 Classification of Fungip. 4
1.4 The Fungal Cell Wallp. 5
1.5 History of Fungal Metabolitesp. 6
1.5.1 Fungal Metabolites in the Nineteenth Centuryp. 7
1.5.2 Fungal Metabolites 1900-1940p. 8
1.5.3 Fungi in the Antibiotic Era, 1940-1960p. 10
1.5.4 Study of Fungal Plant Diseases 1940-1965p. 12
1.5.5 Impact of Spectroscopic Methods on Structure Elucidationp. 13
1.5.6 Fungal Metabolites 1965-2005p. 13
1.5.7 History of Biosynthetic Studies with Fungip. 15
Chapter 2 The Chemistry of Growing Fungi
2.1 The Culture Mediump. 18
2.2 Laboratory Fermentationp. 20
2.3 Isolation of Fungal Metabolitesp. 21
2.4 The Stages in a Fermentationp. 23
2.5 Utilization of the Constituents of the Mediump. 25
2.6 Fungi Growing in the Wildp. 28
2.7 Biosynthetic Experimentsp. 29
Chapter 3 Fungal Metabolites Derived from Amino Acids
3.1 Introductionp. 32
3.2 Penicillinsp. 33
3.3 Cephalosporinsp. 36
3.4 Biosynthesis of [beta]-Lactamsp. 37
3.5 Metabolites Containing a Diketopiperazine Ringp. 39
3.5.1 Mycelianamidep. 40
3.5.2 Gliotoxinp. 40
3.6 The Cyclopenin-Viridicatin Group of Metabolitesp. 42
3.7 Tryptophan-derived Metabolitesp. 42
3.8 Glutamic Acid Derivativesp. 44
3.9 Fungal Peptidesp. 45
Chapter 4 Polyketides from Fungi
4.1 Introductionp. 47
4.2 Polyketide Biosynthesisp. 48
4.3 Triketidesp. 50
4.4 Tetraketidesp. 51
4.4.1 6-Methylsalicylic Acidp. 51
4.4.2 Patulin and Penicillic Acidp. 52
4.4.3 Gladiolic Acid and its Relativesp. 55
4.4.4 Tetraketide Tropolonesp. 56
4.4.5 Mycophenolic Acidp. 57
4.5 Pentaketidesp. 58
4.5.1 Citrininp. 58
4.5.2 Terreinp. 60
4.6 Hepta- and Octaketidesp. 61
4.6.1 Griseofulvinp. 61
4.6.2 Cladosporin (Asperentin)p. 64
4.7 Polyketide Lactonesp. 65
4.8 Statinsp. 66
4.9 Cytochalasinsp. 68
4.10 Fatty Acids from Fungip. 68
4.11 Polyacetylenes from the Higher Fungip. 70
Chapter 5 Terpenoid Fungal Metabolites
5.1 Introductionp. 73
5.2 Biosynthesis of Fungal Terpenoidsp. 73
5.3 Monoterpenoidsp. 76
5.4 Sesquiterpenoidsp. 76
5.4.1 Cyclonerodiolp. 77
5.4.2 Helicobasidinp. 78
5.4.3 Trichothecenesp. 78
5.4.4 PR-Toxinp. 81
5.4.5 Botryanesp. 81
5.4.6 Culmorin and Helminthosporalp. 84
5.4.7 Sesquiterpenoids of the Basidiomycetesp. 85
5.5 Diterpenoid Fungal Metabolitesp. 93
5.5.1 Virescenosidesp. 94
5.5.2 Rosanesp. 94
5.5.3 Gibberellins and Kaurenolidesp. 97
5.5.4 Aphidicolinp. 101
5.5.5 Pleuromutilinp. 102
5.5.6 Fusicoccins and Cotyleninsp. 102
5.6 Sesterterpenoidsp. 104
5.7 Fungal Triterpenoids and Steroidsp. 105
5.7.1 Ergosterolp. 106
5.7.2 Fusidane Steroidal Antibioticsp. 107
5.7.3 Viridin, Wortmannin and their Relativesp. 111
5.7.4 Triterpenoids of the Basidiomycetesp. 113
5.8 Meroterpenoidsp. 116
Chapter 6 Fungal Metabolites Derived from the Citric Acid Cycle
6.1 Introductionp. 120
6.2 Citric Acid and Related Acidsp. 120
6.3 Fungal Tetronic Acidsp. 122
6.4 Canadensolide and Avenaciolidep. 123
6.5 Nonadridesp. 124
6.6 Squalestatinsp. 126
Chapter 7 Pigments and Odours of Fungi
7.1 Introductionp. 127
7.2 Polyketide Fungal Pigmentsp. 128
7.2.1 Fumigatinp. 128
7.2.2 Auroglaucin and Flavoglaucinp. 129
7.2.3 Hydroxyanthraquinone Pigmentsp. 129
7.2.4 Xanthone and Naphthopyrone Pigmentsp. 130
7.2.5 Extended and Dimeric Quinonesp. 131
7.3 Fungal Pigments Derived from the Shikimate Pathwayp. 132
7.3.1 Terphenylsp. 132
7.3.2 Pulvinic Acidsp. 133
7.4 Some Pigments Containing Nitrogenp. 135
7.5 Terpenoid Pigmentsp. 138
7.5.1 Fungal Carotenoidsp. 138
7.6 Lichen Substancesp. 140
7.7 Odours of Fungip. 142
7.7.1 Organoleptic Components of Mushroomsp. 142
7.7.2 Volatile Fungal Metabolites Containing Sulfurp. 144
Chapter 8 The Chemistry of Some Fungal Diseases of Plants
8.1 Introductionp. 147
8.2 General Chemistry of Plant-Fungal Interactionsp. 148
8.3 Chemistry of some Leaf-spot Diseasesp. 149
8.3.1 Botrytis cinereap. 149
8.3.2 Alternaria Leaf-spot Diseasesp. 151
8.3.3 Cercospora Leaf-spot Diseasesp. 153
8.3.4 Diseases Caused by Colletotrichum Speciesp. 154
8.4 Fungal Diseases of the Gramineaep. 155
8.5 Root-infecting Fungip. 157
8.6 Some Fungal Diseases of Treesp. 159
8.6.1 Dutch Elm Diseasep. 159
8.6.2 Eutypa Diebackp. 160
8.6.3 Armillaria melleap. 161
8.6.4 Phytophthora cinnamomip. 162
8.6.5 Silver-leaf Diseasep. 162
8.6.6 Nectria galligena Cankerp. 162
8.6.7 Canker Diseases of Cypressp. 163
8.7 Trichoderma Species as Anti-fungal Agentsp. 163
8.8 Fungal Diseases of Plants and Global Warmingp. 164
Chapter 9 Mycotoxins
9.1 Introductionp. 165
9.2 Ergotismp. 165
9.3 Trichothecenes as Mycotoxinsp. 166
9.4 Other Fusarium Toxinsp. 168
9.5 Aflatoxinsp. 169
9.6 Mycotoxins of Penicillium Speciesp. 171
9.7 Poisonous Mushroomsp. 173
Chapter 10 Fungi as Reagents
10.1 Introductionp. 177
10.2 Xenobiotic Transformationsp. 177
10.2.1 Microbial Hydrolysisp. 178
10.2.2 Microbial Redox Reactionsp. 179
10.2.3 Microbiological Hydroxylationp. 180
10.3 Biosynthetically-patterned Biotransformationsp. 183
Epiloguep. 188
Further Reading and Bibliographyp. 190
Glossaryp. 204
Subject Indexp. 209
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