Recent Advances in Polyphenol Research, Volume 5

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

7.11 Hormonal controls of flavonoid synthesis 160

7.12 Flavonoid synthesis is regulated by light 161

7.13 Conclusions 162

Acknowledgments 163

References 163

8 Structure of Polyacylated Anthocyanins and Their UV Protective Effect 171
Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo

8.1 Introduction 171

8.2 Occurrence and structure of polyacylated anthocyanins in blue flowers 173

8.3 Molecular associations of polyacylated anthocyanins in blue flower petals 178

8.4 UV protection of polyacylated anthocyanins from solar radiation 183

8.5 Conclusion 187

References 188

9 The Involvement of Anthocyanin-Rich Foods in Retinal Damage 193
Kenjirou Ogawa and Hideaki Hara

9.1 Introduction 193

9.2 Anthocyanin-rich foods for eye health 195

9.3 Experimental models to mimic eye diseases and the effect of anthocyanin-rich foods 196

9.4 Conclusions 201

References 203

10 Prevention and Treatment of Diabetes Using Polyphenols via Activation of AMP-Activated Protein Kinase and Stimulation of Glucagon-like Peptide-1 Secretion 206
Takanori Tsuda

10.1 Introduction 206

10.2 Activation of AMPK and metabolic change 207

10.3 GLP-1 action and diabetes prevention/suppression 212

10.4 Future issues and prospects 220

References 222

11 Beneficial Vascular Responses to Proanthocyanidins: Critical Assessment of Plant-Based Test Materials and Insight into the Signaling Pathways 226
Herbert Kolodziej

11.1 Introduction 227

11.2 Appraisal of test materials 228

11.3 Endothelial dysfunction 233

11.4 In vitro test systems 234

11.5 Vasorelaxant mechanisms 235

11.6 Bioavailability and metabolic transformation: the missing link in the evidence to action in the body 249

11.7 Conclusions 250

References 251

12 Polyphenols for Brain and Cognitive Health 259
Katherine H. M. Cox and Andrew Scholey

12.1 Introduction 259

12.2 Studies of total polyphenols and cognition 260

12.3 Pine bark 272

12.4 Discussion and conclusions 283

References 283

13 Curcumin and Cancer Metastasis 289
Ikuo Saiki

13.1 Introduction 290

13.2 Effects of curcumin on intra-hepatic metastasis of liver cancer 293

13.3 Effects of curcumin on lymp node metastasis of lung cancer 298

13.4 Effects of curcumin on tumor angiogenesis 303

13.5 Conclusions 307

References 307

14 Phytochemical and Pharmacological Overview of Cistanche Species 313
Hai-Ning Lv, Ke-Wu Zeng, Yue-Lin Song, Yong Jiang and Peng-Fei Tu

14.1 Introduction 313

14.2 Chemical constituents of Cistanche species 314

14.3 Bioactivities of the extracts and pure compounds from Cistanche species 322

14.4 Conclusions 334

References 334

Index 342