Phenolic compound biochemistry / by Wilfred Vermerris and Ralph Nicholson

Includes bibliographical references and index

Table Of Contents: PREFACE CHAPTER 1 Families of Phenolic Compounds and Means of Classification 1. Definitions 2. Classification 3. Classes of phenolic compounds 3.1 Simple phenolics 3.2 Phenolic acids and aldehydes 3.3 Acetophenones and phenylacetic acids 3.4 Cinnamic acids 3.5 Coumarins 3.6 Flavonoids 3.6.1 Chalcones 3.6.2 Aurones 3.6.3 Flavonoids 3.6.3.1 Flavanones 3.6.3.2 Flavanonols 3.6.3.3 Leucoanthocyanidins 3.6.3.4 Flavones 3.6.3.5 Anthocyanidins and deoxyanthocyandins 3.6.3.6 Anthocyanins 3.7 Biflavonyls 3.8 Benzophenones, xanthones and stilbenes 3.9 Benzoquinones, anthraquinones and naphthaquinones 3.10 Betacyanins 3.11 Lignans 3.12 Lignin 3.13 Tannins 3.13.1 Condensed tannins 3.13.2 Gallotannins 3.13.3 Ellagitannins 3.13.4 Complex tannins 3.14 Phlobaphenes 4. References CHAPTER 2 Chemical Properties of Phenolic Compounds 1.1 The benzene ring 1.2 Planar versus non-planar bonds 1.3 The acidic nature of the phenolic hydroxyl group 1.3.1 The effects of substituents on acidity 1.3.2 Use of acidity in separations 1.4 Hydrogen bonding and the phenolic hydroxyl group 1.4.1 Intra- and inter-molecular hydrogen bonds 1.4.2 Stability of the hydrogen bond ring 1.5 Metal complexes 1.6 Esterification 1.7 Ethers and glycosides 1.8 Oxidation of the phenolic hydroxyl group 1.8.1 Auto-oxidation of phenolic compounds 1.8.2 Enzymatic oxidation of the phenolic hydroxyl group 1.8.2.1 E.C. 1.10.3 1.8.2.2 E.C. 1.14.18.1 1.8.2.3 E.C. 1.11.1. 1.9 Reactive oxygen species and antioxidants 2. References CHAPTER 3 Biosynthesis of Phenolic Compounds 1. Introduction 2. Protein isolation and purification 3. Gene cloning strategies 3.1 Insertional mutagenesis 3.2 Map-based cloning 3.3 The candidate-gene approach 3.4 QTL mapping 4. Isolation and characterization of recombinant proteins 5. Carbohydrate catabolism 5.1 Glycolysis 5.2 The pentose phosphate pathway 6. The shikimate pathway 7. The general phenylpropanoid pathway 8. Biosynthesis of phenolic acids 8.1 Salicylic acid 8.2 Gallic acid 9. Biosynthesis of flavonoids and condensed tannins 9.1 Structural genes and enzymes 9.2 Regulatory genes 10. Monolignol biosynthesis 11. Lignan biosynthesis 12. Lignin biosynthesis 12.1 Genetic control of lignification 12.2 Monolignol transport and polymerization 12.3 Modification of lignin for agro-industrial applications 12.3.1 Pulp and paper industry 12.3.2 Forage and silage quality 12.3.3 Ethanol production from ligno-cellulosic biomass 13. Hydroxycinnamic acid biosynthesis 14. Biosynthesis of sinapoyl esters 15. Coumarin biosynthesis 16. Stilbene biosynthesis 17. Biosynthesis of gallotarmins and ellagitannins 18. References CHAPTER 4 Isolation and Identification of Phenolic Compounds 1. Introduction 2. Isolation of phenolic compounds 2.1 Total phenolic content: the Folin-Ciocalteu reagent 2.2 Determining the content of condensed tannins 2.2.1 The butanol-HCl assay 2.2.2 The vanillin assay 2.2.3 Precipitation of condensed tannins with formaldehyde 2.3 Determining the content of gallotannins 2.3.1 The potassium iodate assay 2.3.2 The rhodanine assay 2.4 Determining the content of ellagitannins 2.4.1 Nitrous acid oxidation 2.4.2 The NaNO2/HCl assay 2.5 Determining lignin content 2.5.1 Klason lignin 2.5.2 Acid detergent lignin 2.5.3 Thioglycolic acid lignin 2.5.4 Acetylbromide lignin 3. Identification and characterization of phenolic compounds 3.1 Thin layer chromatography 3.2 Liquid chromatography: HPLC and LC-MS 3.3 Gas chromatography 3.4 Methods for the identification of lignin subunit composition 3.4.1 The nitrobenzene oxidation 3.4.2 Thioacidolysis 3.4.3 Derivatiation Followed by Reductive Cleavage 3.4.4 Analytical pyrolysis 3.4.5 Nuclear magnetic resonance 3.4.6 Fourier-transform infrared spectroscopy and near infrared reflectance spectroscopy 4. Visualization of phenolic compounds in planta using histochemical stains 4.1 An overview of histochemical staining protocols 4.2 Visualizing plant-pathogen interactions involving phenolics with histochemical stains 5. References CHAPTER 5 Analysis of Phenolic Compounds with Mass Spectrometry 1. The principles of mass spectrometry 1.1 Ionization 1.2 Mass Analysis 1.3 Detectors 1.4 Sample introduction 2. New developments in mass spectrometry 2.1 Fast atom bombardment 2.2 Plasma desorption ionization 2.3 Electrospray ionization 2.4 Matrix-assisted laser desorption ionization 3. Quantitation 4. References CHAPTER 6 The Role of Phenols in Plant Defense 1. Preformed antimicrobial and insecticidal metabolites 1.1 Chlorogenic acid 1.2 Phloridzin and phloretin 1.3 Cyanogenic glycosides 1.4 Tuliposides 1.5 Protocatechuic acid 1.6 Lignin 1.7 C-glycosyl flavones 2. Compounds formed in response to pathogen attack 2.1 3-Deoxyanthocyanidins 2.2 Pisatin 2.3 Stilbenes 2.4 Salicylic acid 2.5 Lignin 3. References CHAPTER 7 Phenolic Compounds and their Effects on Human Health 1. Introduction 2. Antioxidant properties 3. Disease prevention 4. Activity against toxins 5. References Appendix Index