Recent Advances in Polyphenol Research -- Contents -- Contributors -- Preface -- 1 Plant Phenolics: A Biochemical and Physiological Perspective -- 1.1 The general phenolic metabolism in plants -- 1.2 Effect of non-freezing low temperature stress on phenolic metabolism in crop plants -- 1.3 Plant phenolics as defence compounds -- 1.3.1 Phenolic-mediated induced resistance of apples against fungal pathogens -- 1.3.2 Contribution of vigna phenolics to plant protection against insects -- 1.4 Diversion of carbon skeletons from primary to phenolic-related secondary metabolism -- 1.4.1 Metabolic costs of adaptive responses to adverse environmental conditions -- 1.4.2 Transduction pathway between nutrient depletion and enhanced polyphenol content -- References -- 2 Polyphenols: From Plant Adaptation to Useful Chemical Resources -- 2.1 The emergence of phenolic metabolism and the adaptation of plants to a terrestrial environment -- 2.2 The shikimate pathway: a complex and subtle interface between primary metabolism and phenolic metabolism -- 2.2.1 Quinic acid, a specific component of higher plants -- 2.2.2 The postchorismate branch of the shikimate pathway leading to phenylalanine: one or two metabolic routes in plants? -- 2.2.2.1 Intracellular location of enzymes -- 2.2.2.2 Complex and new regulatory mechanisms in the shikimate pathway -- 2.3 Plant (poly)phenols: a diversified reservoir of useful chemicals -- 2.3.1 The health-promoting properties of polyphenols -- 2.3.2 A new time for lignocellulosics utilization through biotechnology -- 2.3.2.1 Biomass pretreatment and enzymatic conversion of polysaccharides -- 2.3.2.2 Lignins: degradation, bioconversion -- 2.3.2.3 The fermentation step towards the production of bioalcohols -- 2.3.2.4 Biorefinery pilot plants -- 2.3.2.5 Quality and availability of the upstream resource -- 2.3.2.6 Future prospects.

2.3.3 Chemical and catalytic valorization of polyphenols -- 2.4 Concluding remarks -- Acknowledgments -- References -- 3 Fifty Years of Polyphenol-Protein Complexes -- 3.1 Introduction -- 3.2 Precipitable complexes -- 3.3 Soluble complexes -- 3.4 Proline-rich proteins -- 3.5 Mechanisms of binding -- 3.6 Stoichiometry of binding -- 3.7 Protein conformation -- 3.8 Covalent tannin-protein complexes -- 3.9 Conclusions -- Acknowledgments -- References -- 4 Chemistry of Flavonoids in Color Development -- 4.1 Introduction -- 4.2 Synthetic studies on anthocyanins toward polyacylated pigments -- 4.2.1 Previously reported syntheses of anthocyanins -- 4.2.2 Synthesis of anthocyanin using biomimetic oxidation -- 4.2.3 Transformation of flavonol derivatives to anthocyanins via a flavenol glycoside -- 4.3 Synthesis of copigments for studying blue color development -- 4.3.1 Copigmentation in metalloanthocyanins -- 4.3.2 Synthesis of glycosylated flavones -- 4.3.3 Chiral recognition in metalloanthocyanin formation -- 4.3.4 Synthesis of acylquinic acid derivatives for studies on hydrangea coloration -- 4.4 Conclusion -- Abbreviations -- Acknowledgments -- References -- 5 Colouring up Plant Biotechnology -- 5.1 Introduction -- 5.2 Plant production of anthocyanins -- 5.2.1 Synthesis of anthocyanins -- 5.2.2 Transport of anthocyanins -- 5.2.3 Decoration of anthocyanins -- 5.2.4 Factors affecting the colour of anthocyanins -- 5.2.5 Copigmentation -- 5.2.6 Transcriptional regulation of anthocyanin biosynthesis -- 5.3 Engineering anthocyanin production in plants -- 5.3.1 An in vivo reporter of promoter activity -- 5.3.2 Biofortified crops -- 5.3.3 Visually traceable system for VIGS analysis of gene function -- 5.4 Conclusions -- Acknowledgements -- References -- 6 Anthocyanin Biosynthesis, Regulation, and Transport: New Insights from Model Species.

6.1 Anthocyanins and related pigments in model plant species -- 6.1.1 General characteristics of anthocyanins -- 6.1.2 Anthocyanin biosynthetic enzymes -- 6.1.3 Anthocyanins in Arabidopsis -- 6.2 Transcriptional regulation of anthocyanin biosynthetic genes -- 6.2.1 Maize -- 6.2.2 Arabidopsis -- 6.2.3 Petunia -- 6.2.4 Snapdragon -- 6.3 Anthocyanin transport and subvacuolar localization -- 6.4 Concluding remarks -- References -- 7 Shedding Light on the Black Boxes of the Proanthocyanidin Pathway with Grapevine -- 7.1 Tools available on grape to study PA biosynthesis -- 7.1.1 Grape PAs -- 7.1.1.1 Grape PA structure -- 7.1.1.2 Grape PA variations according to genotype, tissue and development -- 7.1.2 Grape genetic and genomic tools -- 7.2 Biosynthesis -- 7.2.1 Enzymes of the pathway -- 7.2.2 Transport and storage of PAs -- 7.2.3 PA polymerisation -- 7.2.3.1 Nature of the extension units -- 7.2.3.2 Enzymatic or chemical polymerisation -- 7.2.3.3 Subcellular localisation of polymerisation -- 7.3 Regulation of the pathway -- References -- 8 Phenolic Compounds in Plant Defense and Pathogen Counter-defense Mechanisms -- 8.1 Introduction -- 8.2 Plant defenses and pathogen counter-defenses -- 8.3 Phenolic-related plant responses to pathogens -- 8.3.1 Cotton-Verticillium dahliae -- 8.3.2 Cucumber-Sphaerotheca fuliginea -- 8.3.3 Chickpea-Fusarium oxysporum f. sp. ciceris -- 8.3.4 Potato-Verticillium dahliae -- 8.3.5 Potato-Phytophthora infestans -- 8.3.6 Sunflower-Verticillium dahliae -- 8.3.7 Date palm-Fusarium oxysporum f. sp. albedinis -- 8.3.8 Canola-Leptosphaeria maculans -- 8.3.9 Saskatoons-Entomosporium mespili -- 8.4 Pathogens counter-defense against plants' phenolic-related defenses -- 8.4.1 Phytophthora infestans -- 8.4.2 Verticillium dahliae -- 8.5 Concluding remarks -- Acknowledgments -- References.

9 Absorption and Metabolism of Dietary Chlorogenic Acids and Procyanidins -- 9.1 Introduction -- 9.2 Procyanidins -- 9.2.1 Gut lumen stability of procyanidins -- 9.2.2 Absorption of intact procyanidins from the small intestine -- 9.2.3 Mechanism of absorption across small intestine -- 9.2.4 Absorption from the colon after microbial metabolism -- 9.3 Chlorogenic acids and hydroxycinnamates -- 9.3.1 Transport of chlorogenic acids -- 9.3.2 Chlorogenic acid absorption in humans -- 9.3.3 Chlorogenic acid metabolism -- References -- 10 Extra-Virgin Olive Oil-Healthful Properties of Its Phenolic Constituents -- 10.1 Introduction -- 10.2 Epidemiological studies -- 10.3 In vitro studies on olive oil's phenolics -- 10.4 In vivo studies -- 10.5 Olive oil and cancer -- 10.6 Potential mechanisms of action of olive phenols-to be elucidated -- 10.7 Focus on hydroxytyrosol -- 10.8 Olive mill waste water as a source of olive phenols -- 10.9 Conclusions -- Acknowledgments -- References -- 11 Analysis and Characterisation of Flavonoid Phase II Metabolites -- 11.1 Introduction -- 11.2 Flavonoid metabolism -- 11.3 Preparation of metabolites -- 11.3.1 Isolation from plant sources -- 11.3.2 Enzymatic synthesis of metabolites -- 11.3.3 Chemical synthesis -- 11.3.4 Purification of metabolites -- 11.4 Characterisation of flavonoid metabolites -- 11.4.1 UV spectra -- 11.4.2 Nuclear magnetic resonance -- 11.4.3 Mass spectrometry -- 11.5 Extraction and preparation -- 11.5.1 Sample preparation and storage -- 11.5.2 Hydrolysis -- 11.5.3 Solvent extraction -- 11.5.4 Solid phase extraction -- 11.6 Analysis of metabolites in biological samples -- 11.6.1 Quantification of total polyphenol metabolites -- 11.6.2 Analysis of individual metabolites -- 11.6.3 High performance liquid chromatography -- 11.6.4 Detection systems.

11.6.5 Trends in the chromatographic analysis of flavonoid metabolites -- Acknowledgments -- References -- 12 High-speed Countercurrent Chromatography in the Separation of Polyphenols -- 12.1 Foreword -- 12.2 High-speed countercurrent chromatography -- 12.3 Separations of polyphenols -- 12.3.1 Preparative applications -- 12.3.1.1 Stilbene glycosides -- 12.3.1.2 Flavonolignans -- 12.3.1.3 Flavonoids -- 12.3.1.4 Anthocyanins -- 12.3.1.5 Proanthocyanidins and tannins -- 12.3.2 Analytical applications -- 12.4 Extensions of the basic countercurrent chromatography method -- 12.4.1 Reversed-phase operation -- 12.4.2 Multiple dual-mode operation -- 12.4.3 Elution-extrusion -- 12.4.4 Gradient elution -- 12.4.5 HSCCC/MS -- 12.4.6 Complexation HSCCC -- 12.4.7 High-performance CCC -- References -- 13 Strategies for the Controlled Synthesis of Oligomeric Polyphenols -- 13.1 Introduction -- 13.2 Serial oligomer families -- 13.2.1 Overview -- 13.2.2 Catechin-derived oligomers -- 13.2.3 Ellagitannin-derived oligomers -- 13.3 Oligomer families with diverse bond connections -- 13.3.1 Overview -- 13.3.2 The resveratrol family of oligomeric natural products -- 13.3.2.1 Introduction -- 13.3.2.2 Biomimetic approaches -- 13.3.2.3 Stepwise synthesis approaches -- 13.3.3 Rosmarinic-acid-derived oligomers -- 13.4 Conclusion -- Acknowledgments -- References -- Index -- A color plate section is located between pages 12 and 13.