Recent Advances in Polyphenol Research

Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They express a large and diverse panel of biological activities including beneficial effects on both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions (also referred to as vegetable tannins), are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents. Sponsored by the scholarly society Groupe Polyphénols, this publication, which is the fifth volume in this highly regarded Recent Advances in Polyphenol Research series, is edited by Kumi Yoshida, Véronique Cheynier and Stéphane Quideau. They have once again, like their predecessors, put together an impressive collection of cutting-edge chapters written by expert scientists, internationally respected in their respective field of polyphenol sciences. This Volume 5 highlights some of the latest information and opinion on the following major research topics about polyphenols: Chemistry, physicochemistry & materials science Biosynthesis, genetic & metabolic engineering Plant & ecosystem, lignocellulosic biomass Food, nutrition & health Natural medicine & Kampo Tannins & their functions Chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists will all find this book an invaluable resource. Libraries in all universities and research institutions where these disciplines are studied and taught should have copies on their bookshelves.

Auteur

Kumi Yoshida and Veronique Cheynier are the authors of Recent Advances in Polyphenol Research, Volume 5, published by Wiley.

Contenu
Contributors xv

Preface xix

1 The Physical Chemistry of Polyphenols: Insights into the Activity of Polyphenols in Humans at the Molecular Level 1
Olivier Dangles, Claire Dufour, Claire Tonnelé and Patrick Trouillas

1.1 Introduction 1

1.2 Molecular complexation of polyphenols 4

1.3 Polyphenols as electron donors 11

1.4 Polyphenols as ligands for metal ions 21

1.5 Conclusions 27

References 28

2 Polyphenols in Bryophytes: Structures, Biological Activities, and Bio- and Total Syntheses 36
Yoshinori Asakawa

2.1 Introduction 36

2.1 Distribution of cyclic and acyclic bis-bibenzyls in Marchantiophyta (liverworts) 37

2.3 Biosynthesis of bis-bibenzyls 39

2.4 The structures of bis-bibenzyls and their total synthesis 50

2.5 Biological activity of bis-bibenzyls 58

2.6 Conclusions 60

Acknowledgments 61

References 61

3 Oxidation Mechanism of Polyphenols and Chemistry of Black Tea 67
Yosuke Matsuo and Takashi Tanaka

3.1 Introduction 67

3.2 Catechin oxidation and production of theaflavins 71

3.3 Theasinensins 73

3.4 Coupled oxidation mechanism 75

3.5 Bicyclo[3.2.1]octane intermediates 77

3.6 Structures of catechin oxidation products 78

3.7 Oligomeric oxidation products 82

3.8 Conclusions 84

Acknowledgments 85

References 85

4 A Proteomic-Based Quantitative Analysis of the Relationship Between Monolignol Biosynthetic Protein Abundance and Lignin Content Using Transgenic Populus trichocarpa 89
Jack P. Wang, Sermsawat Tunlaya-Anukit, Rui Shi, Ting-Feng Yeh, Ling Chuang, Fikret Isik, Chenmin Yang, Jie Liu, Quanzi Li, Philip L. Loziuk, Punith P. Naik, David C. Muddiman, Joel J. Ducoste, Cranos M. Williams, Ronald R. Sederoff and Vincent L. Chiang

4.1 Introduction 90

4.2 Results 94

4.3 Discussion 101

4.4 Materials and methods 102

References 104

5 Monolignol Biosynthesis and Regulation in Grasses 108
Peng Xu and Laigeng Li

5.1 Introduction 108

5.2 Unique cell walls in grasses 109

5.3 Lignin deposition in grasses 110

5.4 Monolignol biosynthesis in grasses 111

5.5 Regulation of monolignol biosynthesis in grasses 114

5.6 Remarks 119

Acknowledgments 119

References 120

6 Creation of Flower Color Mutants Using Ion Beams and a Comprehensive Analysis of Anthocyanin Composition and Genetic Background 127
Yoshihiro Hase

6.1 Introduction 127

6.2 Induction of flower color mutants by ion beams 129

6.3 Mutagenic effects and the molecular nature of the mutations 131

6.4 Comprehensive analyses of flower color, pigments, and associated genes in fragrant cyclamen 131

6.5 Mutagenesis and screening 133

6.6 Genetic background and the obtained mutants 136

6.7 Carnations with peculiar glittering colors 137

6.8 Conclusion 139

Acknowledgments 140

References 140

7 Flavonols Regulate Plant Growth and Development through Regulation of Auxin Transport and Cellular Redox Status 143
Sheena R. Gayomba, Justin M. Watkins and Gloria K. Muday

7.1 Introduction 143

7.2 The flavonoids and their biosynthetic pathway 144

7.3 Flavonoids affect root elongation and gravitropism through alteration of auxin transport 146

7.4 Mechanisms by which flavonols regulate IAA transport 149

7.5 Lateral root formation 151

7.6 Cotyledon, trichome, and root hair development 152

7.7 Inflorescence architecture 154

7.8 Fertility and pollen development 154

7.9 Flavonols modulate ROS signaling in guard cells to regulate stomatal aperture 155

7.10 Transcriptional machinery that controls synthesis of flavonoids 157 7....