TY  - BOOK
AU  - Vermerris Wilfred
AU  - Nicholson,Ralph L
TI  - Phenolic compound biochemistry
SN  - 1402051638
AV  - QD341.P5 V47 2006
PY  - 2006///]
CY  - Dordrecht, The Netherlands
PB  - Springer
KW  - Phenols
KW  - Synthesis
KW  - Identification
KW  - Botanical chemistry
KW  - Mass spectrometry
N1  - 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
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