Chemistry of Fungi

by Hanson, James R.

• ISBN13: 9780854041367
• ISBN10: 0854041362
• Edition: 1st
• Format: Hardcover
• Copyright: 2008-10-01
• Publisher: Royal Society of Chemistry

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 structural diversity of fungal metabolites, the unifying role of biosynthetic studies in rationalising these and the growing ecological understanding of the role of fungal metabolites has attracted the interest of chemists for many years. In addition, a number of aspects of modern biotechnology are now associated with fungi and their metabolites and the production of pharmaceuticals creating a whole new sphere of interest in this area.

Author Biography

James R. Hanson, Department of Chemistry, University of Sussex, Brighton, UK

Table of Contents

Fungi and the Development of Microbiological Chemistry
Introduction	p. 1
Structure of Fungi	p. 2
Classification of Fungi	p. 4
The Fungal Cell Wall	p. 5
History of Fungal Metabolites	p. 6
Fungal Metabolites in the Nineteenth Century	p. 7
Fungal Metabolites 1900-1940	p. 8
Fungi in the Antibiotic Era, 1940-1960	p. 10
Study of Fungal Plant Diseases 1940-1965	p. 12
Impact of Spectroscopic Methods on Structure Elucidation	p. 13
Fungal Metabolites 1965-2005	p. 13
History of Biosynthetic Studies with Fungi	p. 15
The Chemistry of Growing Fungi
The Culture Medium	p. 18
Laboratory Fermentation	p. 20
Isolation of Fungal Metabolites	p. 21
The Stages in a Fermentation	p. 23
Utilization of the Constituents of the Medium	p. 25
Fungi Growing in the Wild	p. 28
Biosynthetic Experiments	p. 29
Fungal Metabolites Derived from Amino Acids
Introduction	p. 32
Penicillins	p. 33
Cephalosporins	p. 36
Biosynthesis of [beta]-Lactams	p. 37
Metabolites Containing a Diketopiperazine Ring	p. 39
Mycelianamide	p. 40
Gliotoxin	p. 40
The Cyclopenin-Viridicatin Group of Metabolites	p. 42
Tryptophan-derived Metabolites	p. 42
Glutamic Acid Derivatives	p. 44
Fungal Peptides	p. 45
Polyketides from Fungi
Introduction	p. 47
Polyketide Biosynthesis	p. 48
Triketides	p. 50
Tetraketides	p. 51
6-Methylsalicylic Acid	p. 51
Patulin and Penicillic Acid	p. 52
Gladiolic Acid and its Relatives	p. 55
Tetraketide Tropolones	p. 56
Mycophenolic Acid	p. 57
Pentaketides	p. 58
Citrinin	p. 58
Terrein	p. 60
Hepta- and Octaketides	p. 61
Griseofulvin	p. 61
Cladosporin (Asperentin)	p. 64
Polyketide Lactones	p. 65
Statins	p. 66
Cytochalasins	p. 68
Fatty Acids from Fungi	p. 68
Polyacetylenes from the Higher Fungi	p. 70
Terpenoid Fungal Metabolites
Introduction	p. 73
Biosynthesis of Fungal Terpenoids	p. 73
Monoterpenoids	p. 76
Sesquiterpenoids	p. 76
Cyclonerodiol	p. 77
Helicobasidin	p. 78
Trichothecenes	p. 78
PR-Toxin	p. 81
Botryanes	p. 81
Culmorin and Helminthosporal	p. 84
Sesquiterpenoids of the Basidiomycetes	p. 85
Diterpenoid Fungal Metabolites	p. 93
Virescenosides	p. 94
Rosanes	p. 94
Gibberellins and Kaurenolides	p. 97
Aphidicolin	p. 101
Pleuromutilin	p. 102
Fusicoccins and Cotylenins	p. 102
Sesterterpenoids	p. 104
Fungal Triterpenoids and Steroids	p. 105
Ergosterol	p. 106
Fusidane Steroidal Antibiotics	p. 107
Viridin, Wortmannin and their Relatives	p. 111
Triterpenoids of the Basidiomycetes	p. 113
Meroterpenoids	p. 116
Fungal Metabolites Derived from the Citric Acid Cycle
Introduction	p. 120
Citric Acid and Related Acids	p. 120
Fungal Tetronic Acids	p. 122
Canadensolide and Avenaciolide	p. 123
Nonadrides	p. 124
Squalestatins	p. 126
Pigments and Odours of Fungi
Introduction	p. 127
Polyketide Fungal Pigments	p. 128
Fumigatin	p. 128
Auroglaucin and Flavoglaucin	p. 129
Hydroxyanthraquinone Pigments	p. 129
Xanthone and Naphthopyrone Pigments	p. 130
Extended and Dimeric Quinones	p. 131
Fungal Pigments Derived from the Shikimate Pathway	p. 132
Terphenyls	p. 132
Pulvinic Acids	p. 133
Some Pigments Containing Nitrogen	p. 135
Terpenoid Pigments	p. 138
Fungal Carotenoids	p. 138
Lichen Substances	p. 140
Odours of Fungi	p. 142
Organoleptic Components of Mushrooms	p. 142
Volatile Fungal Metabolites Containing Sulfur	p. 144
The Chemistry of Some Fungal Diseases of Plants
Introduction	p. 147
General Chemistry of Plant-Fungal Interactions	p. 148
Chemistry of some Leaf-spot Diseases	p. 149
Botrytis cinerea	p. 149
Alternaria Leaf-spot Diseases	p. 151
Cercospora Leaf-spot Diseases	p. 153
Diseases Caused by Colletotrichum Species	p. 154
Fungal Diseases of the Gramineae	p. 155
Root-infecting Fungi	p. 157
Some Fungal Diseases of Trees	p. 159
Dutch Elm Disease	p. 159
Eutypa Dieback	p. 160
Armillaria mellea	p. 161
Phytophthora cinnamomi	p. 162
Silver-leaf Disease	p. 162
Nectria galligena Canker	p. 162
Canker Diseases of Cypress	p. 163
Trichoderma Species as Anti-fungal Agents	p. 163
Fungal Diseases of Plants and Global Warming	p. 164
Mycotoxins
Introduction	p. 165
Ergotism	p. 165
Trichothecenes as Mycotoxins	p. 166
Other Fusarium Toxins	p. 168
Aflatoxins	p. 169
Mycotoxins of Penicillium Species	p. 171
Poisonous Mushrooms	p. 173
Fungi as Reagents
Introduction	p. 177
Xenobiotic Transformations	p. 177
Microbial Hydrolysis	p. 178
Microbial Redox Reactions	p. 179
Microbiological Hydroxylation	p. 180
Biosynthetically-patterned Biotransformations	p. 183
Epilogue	p. 188
Further Reading and Bibliography	p. 190
Glossary	p. 204
Subject Index	p. 209
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