Recent advances in polyphenol research, Volume 5

Content: 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 Tonnele 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