Secondary Plant Products

ISBN-13: 9783642673627 / Angielski / Miękka / 2011 / 674 str.

E. a. Bell; B. V. Charlwood

Opis

It is impossible in a single volume to deal comprehensively with all classes of secondary plant compounds. In the earlier series of this Encyclopedia emphasis was laid on the isoprenoids and plant phenols. While these compounds have not been neglected in the present volume we have attempted to achieve a more balanced presentation by drawing attention to the importance of nitrogenous secondary metabolites such as the alkaloids, amines and non-protein amino acids. Most of the compounds or groups of compounds included in Volume 8 are of restricted distribution within the plant kingdom and wherever possible we have provided information concerning their chemistry, biochemistry, taxonomic signifi cance and probable ecological roles. Secondary compounds cannot be defined in terms of restricted distribution, however, nor can they be defined without refer ence to the plants in which they occur, as it is possible that a given compound occurring in two species may have a primary role in one and not in the other. As our knowledge of biochemistry increases we shall no doubt find it necessary to revise our ideas concerning the roles of a great many of the compounds which are found in plants."

Spis treści

1 Historical Introduction.- References.- 2 The Possible Significance of Secondary Compounds in Plants.- 1 Introduction.- 2 Phylogenetic Significance.- 3 Ecological Significance.- References.- 3 Expression and Control of Secondary Metabolism.- 1 Introduction: Expression of Secondary Metabolism — a Feature of Cell Specialization.- 2 Regulation of Enzyme Amount in Secondary Metabolism.- 3 Regulation of Enzyme Activity.- 4 Compartmentation as Principle of Control in Secondary Metabolism.- 5 Integration of Secondary Metabolism in Programs of Differentiation and Development.- 5.1 The Influence of Nutrients.- 5.2 Action of Signals.- 5.3 Coordinated Enzyme Expression.- 5.4 Sequential Gene Expression in Secondary Metabolism.- 5.5 Secondary Metabolism and Cell Specialization.- 6 Some Speculations About the Evolution of the Control Mechanisms in Secondary Metabolism.- 7 Summary.- References.- 4 The Alkaloids.- 4.1 Alkaloids Derived from Ornithine, Lysine, and Nicotinic Acid.- 1 Alkaloids Derived from Ornithine.- 1.1 Introduction.- 1.2 The Tobacco Alkaloids.- 1.3 Tropane Alkaloids.- 1.4 Pyrrolizidine Alkaloids.- 1.5 Phenanthroindolizidine Alkaloids.- 2 Alkaloids Derived from Lysine.- 2.1 Unsymmetrical Incorporation of Lysine.- 2.2 Symmetrical Incorporation of Lysine.- 2.3 Lycopodium Alkaloids.- 2.4 Securinine.- 2.5 Mimosine.- 3 Alkaloids Derived from Nicotinic Acid.- 3.1 Introduction.- 3.2 The Tobacco Alkaloids.- 3.3 Dioscorine.- 3.4 Ricinine and Other Pyridones.- References.- 4.2 Alkaloids Derived from Phenylalanine and Tyrosine.- 1 Introduction.- 2 Alkaloids Derived from Phenylalanine.- 2.1 Ephedra Alkaloids.- 2.2 Cytochalasins.- 2.3 Gliotoxin.- 2.4 Tenellin.- 2.5 Taxus Alkaloids.- 2.6 The Lunaria Alkaloids.- 2.7 The Lythraceae Alkaloids.- 3 Alkaloids Derived from Tyrosine and/or DOPA.- 3.1 Simple Phenylethylamines.- 3.2 Simple Isoquinoline Alkaloids.- 3.3 Benzylisoquinolines and Related Alkaloids Derived from Two Moles of Tyrosine.- 3.4 Isoquinoline Alkaloids from Norbelladine (Amaryllidaceae Alkaloids).- 3.5 Colchicine.- 3.6 Emetine and Related Ipecacuanha Alkaloids.- 3.7 Betalains.- 3.8 Alkaloids Derived from Noradrenaline.- 3.9 Complex Alkaloids Formed from Tyrosine and a Different Precursor.- References.- 4.3 Alkaloids Derived from Tryptophan and Anthranilic Acid.- 1 Indole Alkaloids.- 1.1 Introduction.- 1.2 Structural Types of Indole Alkaloids.- 1.3 Biochemistry of Indole Alkaloids.- 2 Alkaloids Derived from Anthranilic Acid.- 2.1 Introduction.- 2.2 Protoalkaloids.- 2.3 Quinoline Alkaloids.- 2.4 Quinazolines.- 2.5 Acridine Alkaloids.- 2.6 Miscellaneous.- References.- 4.4 Alkaloids Derived from Histidine and Other Precursors.- 1 Alkaloids Derived from Histidine.- 1.1 Dolicotheline.- 1.2 Pilocarpine.- 2 Alkaloids Derived from Other Precursors.- 2.1 Alkaloids Derived by Linear Combination of Acetate.- 2.2 Alkaloids Derived from Isoleucine.- References.- 4.5 Isoprenoid Alkaloids.- 1 General Introduction.- 2 Terpenoid Alkaloids.- 2.1 Introduction.- 2.2 Monoterpenoid Alkaloids.- 2.3 Sesquiterpenoid Alkaloids.- 2.4 Diterpenoid Alkaloids.- 2.5 Triterpenoid Alkaloids.- 3 Steroidal Alkaloids.- 3.1 Introduction.- 3.2 Solanum Alkaloids.- 3.3 Veratrum Alkaloids.- 3.4 Alkaloids of the Apocynaceae.- 3.5 Alkaloids of the Buxaceae.- References.- 5 The Isoprenoids.- 5.1 The Terpenoids.- 1 Introduction.- 2 Distribution of the Terpenoids.- 2.1 General.- 2.2 Hemiterpenes.- 2.3 Monoterpenes.- 2.4 Sesquiterpenes.- 2.5 Diterpenes.- 2.6 Sesterterpenes.- 2.7 Nonsteroidal Triterpenes.- 3 Structural Diversity of Biosynthesis of C5 to C30 Compounds.- 3.1 Hemiterpenes (C5 Compounds).- 3.2 Monoterpenes (CIO Compounds).- 3.3 Sesquiterpenes (CI5 Compounds).- 3.4 Diterpenes (C20 Compounds).- 3.5 Sesterterpenes (C25 Compounds).- 3.6 Nonsteroidal Triterpenes (C30 Compounds).- 4 Terpene Biosynthesis in Cell-Free Extracts and Tissue Culture.- 4.1 Cell-Free Extracts.- 4.2 Tissue Cultures.- References.- 5.2 Steroids.- 1 Introduction.- 2 Sterols.- 2.1 Structure.- 2.2 Classification.- 2.3 Distribution.- 2.4 Biosynthesis.- 2.5 Seed Germination and Plant Growth.- 2.6 Physiological Function.- 3 Steryl Esters.- 3.1 Occurrence and Distribution.- 3.2 Biosynthesis.- 3.3 Physiological Function.- 4 Steryl Glycosides and Acylsteryl Glycosides.- 4.1 Occurrence and Distribution.- 4.2 Biosynthesis.- 4.3 Physiological Function.- 5 Ecdysteroids.- 5.1 Terminology, Chemistry, Isolation, and Distribution.- 5.2 Biosynthesis.- 5.3 Function.- 6 Progestagens.- 7 Corticosteroids.- 7.1 Occurrence.- 7.2 Physiological Function.- 8 Estrogens and Androgens.- 8.1 Occurrence.- 8.2 Biosynthesis.- 8.3 Physiological Function.- 9 Cardenolides.- 9.1 Chemistry and Distribution.- 9.2 Biosynthesis.- 9.3 Physiological Function.- 10 Sapogenins.- References.- 5.3 Carotenoids.- 1 Introduction.- 2 Biosynthesis.- 2.1 General Pathway.- 2.2 Stereochemistry.- 3 Higher Plants.- 3.1 Leaves.- 3.2 Anthers and Pollen.- 3.3 Flowers.- 3.4 Seeds.- 3.5 Fruit.- 3.6 Roots.- 3.7 Formation and Metabolism.- 3.8 Contribution to Flower Colour.- 3.9 Taxonomic Significance of Fruit Carotenoids.- 4 Mosses, Liverworts and Spore-Bearing Vascular Plants.- 5 Algae.- 5.1 Distribution.- 5.2 Localization.- 5.3 Carotenoids and Algal Taxonomy and Evolution.- 6 Function.- 6.1 Introduction.- 6.2 Photosynthesis.- 6.3 Photoprotection.- 6.4 The Xanthophyll Cycle..- 6.5 Phototropism.- References.- 5.4 Polyisoprenoids.- 5.4.1 Polyprenols and Terpenoid Quinones and Chromanols.- 1 Introduction.- 2 Polyprenols.- 2.1 Nature and Distribution.- 2.2 Seasonal Variation and Intracellular Distribution.- 2.3 Biosynthesis.- 2.4 Function.- 3 Terpenoid Quinones and Chromanols.- 3.1 Nature and Distribution.- 3.2 Intracellular Distribution.- 3.3 Biosynthesis.- 3.4 Formation in Relation to Plant Development.- 3.5 Function.- References.- 5.4.2 Polyisoprene.- 1 Introduction.- 2 Occurrence.- 2.1 Rubber, Gutta, and Chicle.- 2.2 Mode of Occurrence of Polyisoprene in Plants.- 2.3 The Laticiferous System in Hevea brasiliensis.- 2.4 The Composition of Latex.- 2.5 The Polyisoprene Particle in Plants.- 3 Chemical and Physical Properties of Polyisoprene.- 3.1 Purification.- 3.2 Molecular Structure.- 3.3 Physical Properties.- 3.4 The Gel-Phase in Natural Rubber.- 3.5 Molecular Weight.- 3.6 Chemical Properties.- 4 Biosynthesis of Rubber.- 5 Role of Polyisoprene in Plants.- 6 The Artificial Stimulation of the Flow of Latex from Hevea brasiliensis.- 7 Breeding of Hevea brasiliensis.- 8 Propagation and Tissue Culture of Hevea brasiliensis.- References.- 6 Plant Phenolics.- 1 Introduction.- 2 Phenolic Aglycones.- 2.1 Simple Phenols and Phenolic Acids.- 2.2 Phenylpropanoids.- 2.3 Flavonoids.- 2.4 Xanthones and Stilbenes.- 2.5 Quinones.- 2.6 Miscellaneous Phenols.- 3 Phenolic Conjugates.- 3.1 Functional Significance of Conjugation.- 3.2 Glycosidic Variation.- 3.3 Bound Forms of Hydroxycinnamic Acids.- 3.4 Lipid-Soluble Derivatives.- 3.5 Sulphates.- 3.6 Polymers.- 4 Biosynthesis and Metabolism of Phenolics.- 4.1 Carbon Pathway.- 4.2 Enzymology.- 4.3 Physiology of Biosynthesis.- 4.4 Turnover and Metabolism.- 5 Phenolic Production in Tissue and Cell Culture.- 5.1 Introduction.- 5.2 Qualitative Aspects.- 5.3 Metabolic Aspects.- 6 Functions of Phenolics in Plants.- 6.1 Physiological Intractions.- 6.2 Ecological Significance.- References.- 7 Non-Protein Amino Acids in Plants.- 1 Introduction.- 2 Chemistry and Occurrence.- 2.1 Neutral Aliphatic Amino Acids.- 2.2 Sulphur and Selenium-Containing Amino Acids.- 2.3 Imino Acids.- 2.4 Acidic Amino Acids and Amides.- 2.5 Basic Amino Acids and Related Compounds.- 2.6 Heterocyclic Amino Acids.- 2.7 Aromatic Amino Acids.- 2.8 Miscellaneous Amino Acids.- 3 Accumulation of Non-Protein Amino Acids.- 4 Biosynthesis of Non-Protein Amino Acids.- 5 The Distribution of Non-Protein Amino Acids.- 6 Ecological Significance of Non-Protein Amino Acids.- References.- 8 Plant Amines.- 1 Introduction.- 2 Aliphatic Monoamines.- 3 Di- and Polyamines.- 3.1 Growth Effects.- 3.2 Effect of Mineral Nutrition on Amine Metabolism.- 3.3 Biosynthesis of the Di- and Polyamines.- 3.4 Polyamine Conjugates.- 4 Amine Oxidases.- 5 Histamine.- 6 Tryptamines.- 7 Phenethylamines.- References.- 9 Cyanogenic Glycosides.- 1 Introduction.- 2 Structure and General Chemical Properties.- 2.1 Structure.- 2.2 Properties of Cyanogenic Glycosides.- 3 Detection, Isolation, and Characterization.- 3.1 Detection of Cyanogenic Glycosides.- 3.2 Isolation.- 3.3 Characterization.- 4 Distribution.- 4.1 Occurrence of Cyanogenesis.- 4.2 Natural Distribution.- 4.3 Literature on Cyanogens in Plants.- 5 Metabolism of Cyanogenic Glycosides.- 5.1 Biosynthesis.- 5.2 Catabolism in Plants.- 6 Physiological Role of Cyanogenic Glycosides.- References.- 10 Glucosinolates.- 1 Introduction.- 2 General Structure and Nomenclature.- 3 Glucosinolate Side Chains.- 4 Occurrence.- 5 Myrosinase and Glucosinolate Hydrolytic Products.- 6 Glucosinolates and Myrosinase in Plant Cell Cultures.- 7 Quantitative Analysis.- 8 Biosynthesis.- 8.1 Glucosinolates from Amino Acids.- 8.2 Intermediates Between Amino Acids and Glucosinolates.- 8.3 Glucosinolate Interconversions.- 9 Elimination of Glucosinolates Through Plant Breeding.- References.- 11 Betalains.- 1 Introduction.- 2 Naturally Occurring Betalains in the Centrospermae.- 2.1 Betacyanins.- 2.2 Betaxanthins.- 2.3 Betalamic Acid.- 3 Detection and Isolation of Betalains.- 4 Biogenesis of Betalains.- 4.1 Extra-Diol Cleavage of L-DOPA to Betalamic Acid.- 4.2 Incorporation of Labeled Precursors.- 4.3 Control of Betalain Biogenesis.- 5 Synthesis of Betalains.- 6 Function of Betalains.- 7 Phylogenetic Significance of Betalains with Respect to the Centrospermae…..- 7.1 Sieve-Element Plastids.- 7.2 C4 Photosynthesis in the Centrospermae.- 7.3 DNA-RNA Hybridization Data.- 7.4 Summary.- 8 Betalains in Mushrooms.- References.- 12 Plant Lipids of Taxonomic Significance.- 1 Introduction.- 2 Fatty Acids.- 2.1 Commonly Occurring Fatty Acids.- 2.2 Fatty Acids of Unusual Structure.- 2.3 The Use of Fatty Acids for Taxonomic Purposes.- 3 Waxes.- 3.1 Hydrocarbons.- 3.2 Secondary Alcohols and Ketones.- 3.3 Wax Esters.- 3.4 Fatty Acids and Fatty Alcohols.- 3.5 The Use of Waxes as a Taxonomic Tool.- 4 Cutin.- 4.1 The Nature and Origin of Cutin Monomers.- 4.2 The Use of Cutin Monomers for Taxonomic Purposes.- 5 Suberin.- 6 Polyketides.- 7 Acetylenic Compounds.- 7.1 The Nature and Metabolism of Acetylenes.- 7.2 The Use of Acetylenes for Taxonomic Purposes.- 8 Cyanolipids.- References.- 13 Plant Carbohydrates.- 1 Introduction.- 2 Arabinans, Galactans and Arabinogalactans.- 3 Plant Gum Exudates Based on Arabinogalactan Structures.- 3.1 Acacia Gums in Relation to Species of Origin.- 3.2 Gums, Mainly of Arabinogalactan Type, from Other Genera, Families, and Orders.- 4 Plant Polysaccharide Gums of the D-Galacturono-L-Rhamnan Type.- 4.1 Apiogalacturonans.- 5 Gum Exudates of D-Xylan Type.- 6 Polysaccharide Components of Bark and Seeds.- 6.1 Xyloglucans from Cotyledon Cell Walls and from Endosperm.- 6.2 Galactomannans.- 6.3 Glucomannans.- 6.4 Acidic Polysaccharides.- 7 Carbohydrates of Marine Algae.- 7.1 Polysaccharides of Phaeophyta.- 7.2 Polysaccharides of Rhodophyta.- 7.3 Polysaccharides of Chlorophyta.- 8 Conclusion.- References.- Author Index.- Species Index.