Recent Advances in Polyphenol Research

Contributors xv Preface xix 1 Plant Phenolics: A Biochemical and Physiological Perspective 1 Vincenzo Lattanzio, Angela Cardinali and Vito Linsalata 1.1 The general phenolic metabolism in plants 1 1.2 Effect of non-freezing low temperature stress on phenolic metabolism in crop plants 6 1.3 Plant phenolics as defence compounds 11 1.4 Diversion of carbon skeletons from primary to phenolic-related secondary metabolism 19 References 26 2 Polyphenols: From Plant Adaptation to Useful Chemical Resources 41 Alain-Michel Boudet 2.1 The emergence of phenolic metabolism and the adaptation of plants to a terrestrial environment 41 2.2 The shikimate pathway: a complex and subtle interface between primary metabolism and phenolic metabolism 47 2.3 Plant (poly)phenols: a diversified reservoir of useful chemicals 56 2.4 Concluding remarks 63 Acknowledgments 64 References 64 3 Fifty Years of Polyphenol-Protein Complexes 71 Ann E. Hagerman 3.1 Introduction 71 3.2 Precipitable complexes 74 3.3 Soluble complexes 76 3.4 Proline-rich proteins 78 3.5 Mechanisms of binding 79 3.6 Stoichiometry of binding 80 3.7 Protein conformation 82 3.8 Covalent tannin-protein complexes 83 3.9 Conclusions 90 Acknowledgments 91 References 91 4 Chemistry of Flavonoids in Color Development 99 Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo 4.1 Introduction 99 4.2 Synthetic studies on anthocyanins toward polyacylated pigments 103 4.3 Synthesis of copigments for studying blue color development 109 4.4 Conclusion 122 Abbreviations 123 Acknowledgments 124 References 124 5 Colouring up Plant Biotechnology 131 Cathie Martin, Yang Zhang, Laurence Tomlinson, Kalyani Kallam, Jie Luo, Jonathan D.G. Jones, Antonio Granell, Diego Orzaez and Eugenio Butelli 5.1 Introduction 131 5.2 Plant production of anthocyanins 132 5.3 Engineering anthocyanin production in plants 137 5.4 Conclusions 139 Acknowledgements 139 References 139 6 Anthocyanin Biosynthesis, Regulation, and Transport: New Insights from Model Species 143 Lucille Pourcel, Andrés Bohórquez-Restrepo, Niloufer G. Irani and Erich Grotewold 6.1 Anthocyanins and related pigments in model plant species 143 6.2 Transcriptional regulation of anthocyanin biosynthetic genes 147 6.3 Anthocyanin transport and subvacuolar localization 151 6.4 Concluding remarks 154 References 154 7 Shedding Light on the Black Boxes of the Proanthocyanidin Pathway with Grapevine 161 Yung-Fen Huang, Véronique Cheynier and Nancy Terrier 7.1 Tools available on grape to study PA biosynthesis 161 7.2 Biosynthesis 167 7.3 Regulation of the pathway 176 References 182 8 Phenolic Compounds in Plant Defense and Pathogen Counter-defense Mechanisms 191 Fouad Daayf, Abdelbasset El Hadrami, Ahmed F. El-Bebany, Maria A. Henriquez, Zhen Yao, Holly Derksen, Isma¨il El-Hadrami and Lorne R. Adam 8.1 Introduction 191 8.2 Plant defenses and pathogen counter-defenses 192 8.3 Phenolic-related plant responses to pathogens 194 8.4 Pathogens counter-defense against plants' phenolic-related defenses 200 8.5 Concluding remarks 202 Acknowledgments 203 References 203 9 Absorption and Metabolism of Dietary Chlorogenic Acids and Procyanidins 209 Gary Williamson and Angelique Stalmach 9.1 Introduction 209 9.2 Procyanidins 210 9.3 Chlorogenic acids and hydroxycinnamates 214 References 218 10 Extra-Virgin Olive Oil--Healthful Properties of Its Phenolic Constituents 223 Francesco Visioli and Elena Bernardini 10.1 Introduction 223 10.2 Epidemiological studies 225 10.3 In vitro studies on olive oil's phenolics 225 10.4 In vivo studies 228 10.5 Olive oil and cancer 231 10.6 Potential mechanisms of action of olive phenols--to be elucidated 232 10.7 Focus on hydroxytyrosol 233 10.8 Olive mill waste water as a source of olive phenols 236 10.9 Conclusions 240 Acknowledgments 244 References 244 11 Analysis and Characterisation of Flavonoid Phase II Metabolites 249 Celestino Santos-Buelga, Susana González-Manzano, Montserrat Dueñas and Ana M. González-Param´as 11.1 Introduction 249 11.2 Flavonoid metabolism 251 11.3 Preparation of metabolites 253 11.4 Characterisation of flavonoid metabolites 258 11.5 Extraction and preparation 263 11.6 Analysis of metabolites in biological samples 268 Acknowledgments 277 References 277 12 High-speed Countercurrent Chromatography in the Separation of Polyphenols 287 Andrew Marston 12.1 Foreword 287 12.2 High-speed countercurrent chromatography 288 12.3 Separations of polyphenols 291 12.4 Extensions of the basic countercurrent chromatography method 302 References 307 13 Strategies for the Controlled Synthesis of Oligomeric Polyphenols 311 Scott A. Snyder 13.1 Introduction 311 13.2 Serial oligomer families 313 13.3 Oligomer families with diverse bond connections 319 13.4 Conclusion 345 Acknowledgments 345 References 346 Index 353 A color plate section is located between pages 12 and 13. 2