Plant natural products: synthesis, biological functions and practical applications / Herwig O. Gutzeit and Jutta Ludwig-Muller

Incluye bibliografía: páginas 379-403 e índice: páginas 405-422

Preface.. 1 Biosynthesis and Chemical Properties of Natural Substances in Plants.. 1.1 Selected Classes of Secondary Metabolites.. 1.1.1 Occurrence and Compartmentation.. 1.1.2 Biosynthesis.. 1.1.2.1 Alkaloids.. 1.1.2.2 Phenol Derivatives, Especially Flavonoids.. 1.1.2.3 Betalains.. 1.1.2.4 Cyanogenic Glycosides, Glucosinolates, and other Indole Derivatives.. 1.1.2.5 Terpenes.. 1.1.3 Transcriptional Control.. 1.1.4 Transport of Secondary Metabolites.. 1.2 Evolution of Natural Compounds in Plants.. 1.2.1 Parallel Evolution of Similar Pathways.. 1.2.2 Gene Duplication.. 1.2.3 Gene Clusters.. 1.2.4 Natural Variation.. 1.2.5 Modulation of Different Molecules with Similar Functions.. 1.2.6 Evolution by Stress Factors.. 1.2.6.1 Abiotic Stress.. 1.2.6.2 Biotic Factors.. 1.3 Biotechnological Applications.. 1.3.1 Identification and Quantification of Natural Plant Products.. 1.3.2 Biological Activity.. 1.3.3 Biotechnological Production of Natural Compounds.. 2 Function of Natural Substances in Plants.. 2.1 Secondary Compounds in Primary Metabolism.. 2.2 Development.. 2.2.1 Vegetative Growth.. 2.2.1.1 Structural Polymers.. 2.2.1.2 Flavonoids and Auxin Transport.. 2.2.1.3 Glucosinolates and the Biosynthesis of IAA.. 2.2.1.4 Polar Growth.. 2.2.1.5 Cytoskeleton and Cell Cycle.. 2.2.1.6 Alkaloids and Growth.. 2.2.1.7 Senescence.. 2.2.2 Reproduction: Male Fertility.. 2.2.3 Flower Biology: Pollination.. 2.2.3.1 Nutrients.. 2.2.3.2 Aroma Volatiles.. 2.2.3.3 Color.. 2.2.4 Fruit and Seeds.. 2.2.4.1 Fruit Development.. 2.2.4.2 Seed Formation.. 2.2.4.3 Seed Dispersal.. 2.2.4.4 Seed Dormancy.. 2.3 Abiotic Stress.. 2.3.1 Antioxidative Properties in Plants.. 2.3.2 Light and UV Irradiation.. 2.3.3 High Temperatures.. 2.3.4 Cold, Salt, and Drought Stress.. 2.3.5 Nutrient Deficiency.. 2.3.6 Environmental Pollution.. 2.3.6.1 Heavy Metal Stress.. 2.3.6.2 Air Pollution.. 2.4 Symbioses.. 2.4.1 Rhizobia.. 2.4.2 Mycorrhiza

2.4.3 Endophytic Fungi.. 2.4.4 Lichens.. 2.5 Defense.. 2.5.1 Pathogens.. 2.5.1.1 Preformed Defense Response.. 2.5.1.2 Induced-Defense Response.. 2.5.1.3 Systemic Acquired Resistance.. 2.5.2 Antimicrobial Potential in Plant Protection (Biofumigation.. 2.5.3 Invertebrate Herbivores.. 2.5.3.1 Insects.. 2.5.3.2 Phytopathogenic Fungi Alter the Chemical Defense of Plants Against Insects.. 2.5.3.3 Biological Plant Protection Against Insects with Secondary Metabolites.. 2.5.3.4 Nematodes.. 2.5.3.5 Snails/Slugs.. 2.5.4 Parasitic Plants.. 2.6 Allelopathy.. 3 Biological Effects on Microorganisms and Animals.. 3.1 Coevolution.. 3.1.1 Adaptation Mechanisms of Microbes and Herbivores.. 3.1.1.1 Fungi.. 3.1.1.2 Insects.. 3.1.1.3 Vertebrates.. 3.1.2 Attraction of Insects.. 3.2 Effects on Vertebrates: An Overview.. 3.2.1 Structural and Functional Diversity of Natural Substances: Challenges and Promises.. 3.2.2 Molecular Interactions with Cellular Components.. 3.2.2.1 Protein Targets.. 3.2.2.2 Interaction with Nucleic Acids.. 3.2.2.3 Interaction with Lipids.. 3.2.2.4 Interaction with Carbohydrates.. 3.2.2.5 Metal Chelators.. 3.2.3 Visualization of Natural Substances in Living Cells.. 4 Metabolism and Toxicity of Natural Substances in Mammals.. 4.1 Metabolism of Natural Substances in Mammals.. 4.1.1 Principles of Pharmacokinetics.. 4.1.1.1 Absorption, Distribution, Metabolism, and Excretion.. 4.1.2 Case Studies of Selected Natural Compounds.. 4.1.2.1 Quercetin.. 4.1.2.2 Catechins and Proanthocyanidins.. 4.1.2.3 Resveratrol.. 4.1.2.4 Morphine.. 4.1.2.5 Nicotine.. 4.1.3 Metabolic Bioactivation.. 4.1.4 Effects on Enzymes Controlling Biotransformation and Bioavailability.. 4.1.4.1 Medical Importance.. 4.1.5 Genetic Polymorphisms.. 4.1.5.1 Genetic Polymorphisms of Key Metabolic Enzymes.. 4.1.5.2 Caffeine.. 4.1.5.3 Nicotine.. 4.1.5.4 Codeine and Morphine.. 4.1.5.5 Pharmacogenomics and Personalized Medicine.. 4.2 Toxicity

4.2.1 Basic Toxicology.. 4.2.1.1 Cytotoxicity.. 4.2.2 Toxicity of Selected Natural Substances.. 4.2.2.1 Animal Poisons.. 4.2.2.2 Poisons in Plants, Fungi, and Bacteria.. 4.2.2.3 Taxus Alkaloids.. 4.2.2.4 Phallotoxins and Amatoxins.. 4.2.2.5 Ricin.. 4.2.2.6 Bacterial Toxins.. 4.2.3 Strategies and Difficulties in Toxicological Evaluations.. 4.2.3.1 Mutagenicity and Cancerogenicity.. 4.2.3.2 Reprotoxicity and Developmental Toxicity.. 4.2.3.3 Experimental Variables and Limitations of Test Systems.. 5 Examples of Physiological Effects of Natural Substances Present in Food and in Medicinal Plants.. 5.1 Are Antioxidants Good for Health?.. 5.1.1 Generation and Homeostatic Control of Reactive Oxygen and Nitrogen Species.. 5.1.2 Function of ROS/RNS as Signaling Molecules for Cellular Functions.. 5.1.3 Oxidative Stress in Human Diseases and in Aging.. 5.1.4 Natural Substances Affecting Redox Homeostasis.. 5.1.4.1 Reduction of ROS in a Redox Reaction.. 5.1.4.2 Formation of Chelates with Metals.. 5.1.4.3 Inhibition of Enzymes Involved in Stress Defense.. 5.1.4.4 Initiation of an Adaptive Response.. 5.1.5 Hormesis and the Benefits of Temporary Mild Oxidative Stress.. 5.2 Endocrine Effects of Natural Substances.. 5.2.1 Are Endocrine Disruptors a Threat to Animal and Human Health?.. 5.2.2 How Do Phytoestrogens Interfere with the Endocrine System?.. 5.2.2.1 The Estradiol Receptor is a Target of Natural Substances.. 5.2.2.2 Natural Compounds Affecting Steroid Biosynthesis.. 5.2.2.3 Other Activities of Phytoestrogens.. 5.2.3 Evaluation of Risks and Benefits of Phytoestrogens to Treat Common Diseases.. 5.2.3.1 Phytoestrogens and Reproductive Functions.. 5.2.3.2 Do Phytoestrogens Protect Against Breast Cancer?.. 5.2.3.3 Hormone Replacement Therapy.. 5.2.3.4 Other Physiological Effects of Phytoestrogens.. 5.2.3.5 Phytoestrogens Illustrate the Experimental Challenge of a Mechanistic Analysis.. 5.2.4 Transgeneration Effects

5.2.5 Natural Substances Interfering with Nonsteroidal Signaling.. 5.3 Interference with Neural Functions.. 5.3.1 Basic Features of the Nervous System and Synaptic Transmission.. 5.3.2 Bioactivity of Cannabinoids.. 5.3.2.1 Effects of Phytocannabinoids on Neural Functions.. 5.3.2.2 Medical Applications of Phytoestrogens.. 5.3.3 Discovery and Bioactivity of Opioids.. 5.3.4 Analgesic Properties of Opioids and Cannabinoids.. 5.3.4.1 Analgesic Effects of Opioids.. 5.3.4.2 Analgesic Activity of Cannabinoids.. 5.3.5 The Hallucinogenic Drugs Psilocin, Psilocybin, and Mescaline.. 5.3.6 Natural Substances Affecting Cholinergic Signaling.. 5.3.6.1 The Cholinergic Synapse.. 5.3.6.2 Cholinergic Signaling is a Target for Natural Substances.. 5.3.6.3 Inhibitors of AChE.. 5.3.6.4 Medical Applications of AChE Inhibitors.. 5.3.7 Sympathomimetic Substances.. 6 Nature's Drugstore for a Healthy Life.. 6.1 Biologically Active Food and Food Components.. 6.1.1 The Quantity of Food Intake Affects Life Expectancy.. 6.1.2 Resveratrol: Longevity and Health with Grapes?.. 6.1.3 Food with Health-Promoting Bioactive Substances.. 6.1.3.1 Grapes (Resveratrol.. 6.1.3.2 Broccoli (Sulforaphane.. 6.1.3.3 Hops (Xanthohumol.. 6.1.3.4 Green Tea (Epigallocatechin.. -Gallate.. 6.1.3.5 Garlic (Allicin.. 6.1.3.6 Other Polyphenol-Rich Foods.. 6.1.3.7 Is There a General Mechanistic Principle for Health-Promoting Substances in Food?.. 6.1.4 Functional Food: Does it Hold the Promise?.. 6.2 Natural Compounds in Pharmacological Research.. 6.2.1 Mining for Bioactive Compounds in Marine and Terrestrial Organisms.. 6.2.2 Medicinal Chemistry Inspired by Natural Products.. 6.2.2.1 Lessons from Natural Substances About Relevant Targets.. 6.2.2.2 Natural Chemical Scaffolds and their Pharmacological Optimization.. 6.2.2.3 Systematic Computational Analysis of Natural Scaffolds and Peptide Motifs.. 6.3 The Problem of Complexity: Analysis and Consequences

6.3.1 Many Targets: A Problem?.. 6.3.2 From Pharmacology to Polypharmacology.. 6.3.3 Reverse Pharmacology Inspired by Traditional Medicine.. Further Reading.. Index

In contrast to existing books which either focus exclusively on the pharmacological properties of plant natural products or cover the secondary metabolism of plants as one section in general plant science book, this is the first to cover all aspects in one volume. It has all the features of a modern textbook, including color figures, questions and answers and a complimentary website. In addition, the introductory chapters provide sufficient background knowledge in the chemistry and biochemistry of plant natural products and their biotechnological applications to allow its use as a true stand-alone text for student courses. eng