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

• Contributors xvPreface xix1 The Physical Chemistry of Polyphenols: Insights into the Activity of Polyphenols in Humans at the Molecular Level 1Olivier Dangles, Claire Dufour, Claire Tonnelé and Patrick Trouillas1.1 Introduction 11.2 Molecular complexation of polyphenols 41.3 Polyphenols as electron donors 111.4 Polyphenols as ligands for metal ions 211.5 Conclusions 27References 282 Polyphenols in Bryophytes: Structures, Biological Activities, and Bio- and Total Syntheses 36Yoshinori Asakawa2.1 Introduction 362.1 Distribution of cyclic and acyclic bis-bibenzyls in Marchantiophyta (liverworts) 372.3 Biosynthesis of bis-bibenzyls 392.4 The structures of bis-bibenzyls and their total synthesis 502.5 Biological activity of bis-bibenzyls 582.6 Conclusions 60Acknowledgments 61References 613 Oxidation Mechanism of Polyphenols and Chemistry of Black Tea 67Yosuke Matsuo and Takashi Tanaka3.1 Introduction 673.2 Catechin oxidation and production of theaflavins 713.3 Theasinensins 733.4 Coupled oxidation mechanism 753.5 Bicyclo[3.2.1]octane intermediates 773.6 Structures of catechin oxidation products 783.7 Oligomeric oxidation products 823.8 Conclusions 84Acknowledgments 85References 854 A Proteomic-Based Quantitative Analysis of the Relationship Between Monolignol Biosynthetic Protein Abundance and Lignin Content Using Transgenic Populus trichocarpa 89Jack 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. Chiang4.1 Introduction 904.2 Results 944.3 Discussion 1014.4 Materials and methods 102References 1045 Monolignol Biosynthesis and Regulation in Grasses 108Peng Xu and Laigeng Li5.1 Introduction 1085.2 Unique cell walls in grasses 1095.3 Lignin deposition in grasses 1105.4 Monolignol biosynthesis in grasses 1115.5 Regulation of monolignol biosynthesis in grasses 1145.6 Remarks 119Acknowledgments 119References 1206 Creation of Flower Color Mutants Using Ion Beams and a Comprehensive Analysis of Anthocyanin Composition and Genetic Background 127Yoshihiro Hase6.1 Introduction 1276.2 Induction of flower color mutants by ion beams 1296.3 Mutagenic effects and the molecular nature of the mutations 1316.4 Comprehensive analyses of flower color, pigments, and associated genes in fragrant cyclamen 1316.5 Mutagenesis and screening 1336.6 Genetic background and the obtained mutants 1366.7 Carnations with peculiar glittering colors 1376.8 Conclusion 139Acknowledgments 140References 1407 Flavonols Regulate Plant Growth and Development through Regulation of Auxin Transport and Cellular Redox Status 143Sheena R. Gayomba, Justin M. Watkins and Gloria K. Muday7.1 Introduction 1437.2 The flavonoids and their biosynthetic pathway 1447.3 Flavonoids affect root elongation and gravitropism through alteration of auxin transport 1467.4 Mechanisms by which flavonols regulate IAA transport 1497.5 Lateral root formation 1517.6 Cotyledon, trichome, and root hair development 1527.7 Inflorescence architecture 1547.8 Fertility and pollen development 1547.9 Flavonols modulate ROS signaling in guard cells to regulate stomatal aperture 1557.10 Transcriptional machinery that controls synthesis of flavonoids 1577.11 Hormonal controls of flavonoid synthesis 1607.12 Flavonoid synthesis is regulated by light 1617.13 Conclusions 162Acknowledgments 163References 1638 Structure of Polyacylated Anthocyanins and Their UV Protective Effect 171Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo8.1 Introduction 1718.2 Occurrence and structure of polyacylated anthocyanins in blue flowers 1738.3 Molecular associations of polyacylated anthocyanins in blue flower petals 1788.4 UV protection of polyacylated anthocyanins from solar radiation 1838.5 Conclusion 187References 1889 The Involvement of Anthocyanin-Rich Foods in Retinal Damage 193Kenjirou Ogawa and Hideaki Hara9.1 Introduction 1939.2 Anthocyanin-rich foods for eye health 1959.3 Experimental models to mimic eye diseases and the effect of anthocyanin-rich foods 1969.4 Conclusions 201References 20310 Prevention and Treatment of Diabetes Using Polyphenols via Activation of AMP-Activated Protein Kinase and Stimulation of Glucagon-like Peptide-1 Secretion 206Takanori Tsuda10.1 Introduction 20610.2 Activation of AMPK and metabolic change 20710.3 GLP-1 action and diabetes prevention/suppression 21210.4 Future issues and prospects 220References 22211 Beneficial Vascular Responses to Proanthocyanidins: Critical Assessment of Plant-Based Test Materials and Insight into the Signaling Pathways 226Herbert Kolodziej11.1 Introduction 22711.2 Appraisal of test materials 22811.3 Endothelial dysfunction 23311.4 In vitro test systems 23411.5 Vasorelaxant mechanisms 23511.6 Bioavailability and metabolic transformation: the missing link in the evidence to action in the body 24911.7 Conclusions 250References 25112 Polyphenols for Brain and Cognitive Health 259Katherine H. M. Cox and Andrew Scholey12.1 Introduction 25912.2 Studies of total polyphenols and cognition 26012.3 Pine bark 27212.4 Discussion and conclusions 283References 28313 Curcumin and Cancer Metastasis 289Ikuo Saiki13.1 Introduction 29013.2 Effects of curcumin on intra-hepatic metastasis of liver cancer 29313.3 Effects of curcumin on lymp node metastasis of lung cancer 29813.4 Effects of curcumin on tumor angiogenesis 30313.5 Conclusions 307References 30714 Phytochemical and Pharmacological Overview of Cistanche Species 313Hai-Ning Lv, Ke-Wu Zeng, Yue-Lin Song, Yong Jiang and Peng-Fei Tu14.1 Introduction 31314.2 Chemical constituents of Cistanche species 31414.3 Bioactivities of the extracts and pure compounds from Cistanche species 32214.4 Conclusions 334References 334Index 342

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

• Contributors xvPreface xix1 The Physical Chemistry of Polyphenols: Insights into the Activity of Polyphenols in Humans at the Molecular Level 1Olivier Dangles, Claire Dufour, Claire Tonnelé and Patrick Trouillas1.1 Introduction 11.2 Molecular complexation of polyphenols 41.3 Polyphenols as electron donors 111.4 Polyphenols as ligands for metal ions 211.5 Conclusions 27References 282 Polyphenols in Bryophytes: Structures, Biological Activities, and Bio- and Total Syntheses 36Yoshinori Asakawa2.1 Introduction 362.1 Distribution of cyclic and acyclic bis-bibenzyls in Marchantiophyta (liverworts) 372.3 Biosynthesis of bis-bibenzyls 392.4 The structures of bis-bibenzyls and their total synthesis 502.5 Biological activity of bis-bibenzyls 582.6 Conclusions 60Acknowledgments 61References 613 Oxidation Mechanism of Polyphenols and Chemistry of Black Tea 67Yosuke Matsuo and Takashi Tanaka3.1 Introduction 673.2 Catechin oxidation and production of theaflavins 713.3 Theasinensins 733.4 Coupled oxidation mechanism 753.5 Bicyclo[3.2.1]octane intermediates 773.6 Structures of catechin oxidation products 783.7 Oligomeric oxidation products 823.8 Conclusions 84Acknowledgments 85References 854 A Proteomic-Based Quantitative Analysis of the Relationship Between Monolignol Biosynthetic Protein Abundance and Lignin Content Using Transgenic Populus trichocarpa 89Jack 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. Chiang4.1 Introduction 904.2 Results 944.3 Discussion 1014.4 Materials and methods 102References 1045 Monolignol Biosynthesis and Regulation in Grasses 108Peng Xu and Laigeng Li5.1 Introduction 1085.2 Unique cell walls in grasses 1095.3 Lignin deposition in grasses 1105.4 Monolignol biosynthesis in grasses 1115.5 Regulation of monolignol biosynthesis in grasses 1145.6 Remarks 119Acknowledgments 119References 1206 Creation of Flower Color Mutants Using Ion Beams and a Comprehensive Analysis of Anthocyanin Composition and Genetic Background 127Yoshihiro Hase6.1 Introduction 1276.2 Induction of flower color mutants by ion beams 1296.3 Mutagenic effects and the molecular nature of the mutations 1316.4 Comprehensive analyses of flower color, pigments, and associated genes in fragrant cyclamen 1316.5 Mutagenesis and screening 1336.6 Genetic background and the obtained mutants 1366.7 Carnations with peculiar glittering colors 1376.8 Conclusion 139Acknowledgments 140References 1407 Flavonols Regulate Plant Growth and Development through Regulation of Auxin Transport and Cellular Redox Status 143Sheena R. Gayomba, Justin M. Watkins and Gloria K. Muday7.1 Introduction 1437.2 The flavonoids and their biosynthetic pathway 1447.3 Flavonoids affect root elongation and gravitropism through alteration of auxin transport 1467.4 Mechanisms by which flavonols regulate IAA transport 1497.5 Lateral root formation 1517.6 Cotyledon, trichome, and root hair development 1527.7 Inflorescence architecture 1547.8 Fertility and pollen development 1547.9 Flavonols modulate ROS signaling in guard cells to regulate stomatal aperture 1557.10 Transcriptional machinery that controls synthesis of flavonoids 1577.11 Hormonal controls of flavonoid synthesis 1607.12 Flavonoid synthesis is regulated by light 1617.13 Conclusions 162Acknowledgments 163References 1638 Structure of Polyacylated Anthocyanins and Their UV Protective Effect 171Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo8.1 Introduction 1718.2 Occurrence and structure of polyacylated anthocyanins in blue flowers 1738.3 Molecular associations of polyacylated anthocyanins in blue flower petals 1788.4 UV protection of polyacylated anthocyanins from solar radiation 1838.5 Conclusion 187References 1889 The Involvement of Anthocyanin-Rich Foods in Retinal Damage 193Kenjirou Ogawa and Hideaki Hara9.1 Introduction 1939.2 Anthocyanin-rich foods for eye health 1959.3 Experimental models to mimic eye diseases and the effect of anthocyanin-rich foods 1969.4 Conclusions 201References 20310 Prevention and Treatment of Diabetes Using Polyphenols via Activation of AMP-Activated Protein Kinase and Stimulation of Glucagon-like Peptide-1 Secretion 206Takanori Tsuda10.1 Introduction 20610.2 Activation of AMPK and metabolic change 20710.3 GLP-1 action and diabetes prevention/suppression 21210.4 Future issues and prospects 220References 22211 Beneficial Vascular Responses to Proanthocyanidins: Critical Assessment of Plant-Based Test Materials and Insight into the Signaling Pathways 226Herbert Kolodziej11.1 Introduction 22711.2 Appraisal of test materials 22811.3 Endothelial dysfunction 23311.4 In vitro test systems 23411.5 Vasorelaxant mechanisms 23511.6 Bioavailability and metabolic transformation: the missing link in the evidence to action in the body 24911.7 Conclusions 250References 25112 Polyphenols for Brain and Cognitive Health 259Katherine H. M. Cox and Andrew Scholey12.1 Introduction 25912.2 Studies of total polyphenols and cognition 26012.3 Pine bark 27212.4 Discussion and conclusions 283References 28313 Curcumin and Cancer Metastasis 289Ikuo Saiki13.1 Introduction 29013.2 Effects of curcumin on intra-hepatic metastasis of liver cancer 29313.3 Effects of curcumin on lymp node metastasis of lung cancer 29813.4 Effects of curcumin on tumor angiogenesis 30313.5 Conclusions 307References 30714 Phytochemical and Pharmacological Overview of Cistanche Species 313Hai-Ning Lv, Ke-Wu Zeng, Yue-Lin Song, Yong Jiang and Peng-Fei Tu14.1 Introduction 31314.2 Chemical constituents of Cistanche species 31414.3 Bioactivities of the extracts and pure compounds from Cistanche species 32214.4 Conclusions 334References 334Index 342

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

• Contributors xvPreface xix1 The Physical Chemistry of Polyphenols: Insights into the Activity of Polyphenols in Humans at the Molecular Level 1Olivier Dangles, Claire Dufour, Claire Tonnelé and Patrick Trouillas1.1 Introduction 11.2 Molecular complexation of polyphenols 41.3 Polyphenols as electron donors 111.4 Polyphenols as ligands for metal ions 211.5 Conclusions 27References 282 Polyphenols in Bryophytes: Structures, Biological Activities, and Bio- and Total Syntheses 36Yoshinori Asakawa2.1 Introduction 362.1 Distribution of cyclic and acyclic bis-bibenzyls in Marchantiophyta (liverworts) 372.3 Biosynthesis of bis-bibenzyls 392.4 The structures of bis-bibenzyls and their total synthesis 502.5 Biological activity of bis-bibenzyls 582.6 Conclusions 60Acknowledgments 61References 613 Oxidation Mechanism of Polyphenols and Chemistry of Black Tea 67Yosuke Matsuo and Takashi Tanaka3.1 Introduction 673.2 Catechin oxidation and production of theaflavins 713.3 Theasinensins 733.4 Coupled oxidation mechanism 753.5 Bicyclo[3.2.1]octane intermediates 773.6 Structures of catechin oxidation products 783.7 Oligomeric oxidation products 823.8 Conclusions 84Acknowledgments 85References 854 A Proteomic-Based Quantitative Analysis of the Relationship Between Monolignol Biosynthetic Protein Abundance and Lignin Content Using Transgenic Populus trichocarpa 89Jack 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. Chiang4.1 Introduction 904.2 Results 944.3 Discussion 1014.4 Materials and methods 102References 1045 Monolignol Biosynthesis and Regulation in Grasses 108Peng Xu and Laigeng Li5.1 Introduction 1085.2 Unique cell walls in grasses 1095.3 Lignin deposition in grasses 1105.4 Monolignol biosynthesis in grasses 1115.5 Regulation of monolignol biosynthesis in grasses 1145.6 Remarks 119Acknowledgments 119References 1206 Creation of Flower Color Mutants Using Ion Beams and a Comprehensive Analysis of Anthocyanin Composition and Genetic Background 127Yoshihiro Hase6.1 Introduction 1276.2 Induction of flower color mutants by ion beams 1296.3 Mutagenic effects and the molecular nature of the mutations 1316.4 Comprehensive analyses of flower color, pigments, and associated genes in fragrant cyclamen 1316.5 Mutagenesis and screening 1336.6 Genetic background and the obtained mutants 1366.7 Carnations with peculiar glittering colors 1376.8 Conclusion 139Acknowledgments 140References 1407 Flavonols Regulate Plant Growth and Development through Regulation of Auxin Transport and Cellular Redox Status 143Sheena R. Gayomba, Justin M. Watkins and Gloria K. Muday7.1 Introduction 1437.2 The flavonoids and their biosynthetic pathway 1447.3 Flavonoids affect root elongation and gravitropism through alteration of auxin transport 1467.4 Mechanisms by which flavonols regulate IAA transport 1497.5 Lateral root formation 1517.6 Cotyledon, trichome, and root hair development 1527.7 Inflorescence architecture 1547.8 Fertility and pollen development 1547.9 Flavonols modulate ROS signaling in guard cells to regulate stomatal aperture 1557.10 Transcriptional machinery that controls synthesis of flavonoids 1577.11 Hormonal controls of flavonoid synthesis 1607.12 Flavonoid synthesis is regulated by light 1617.13 Conclusions 162Acknowledgments 163References 1638 Structure of Polyacylated Anthocyanins and Their UV Protective Effect 171Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo8.1 Introduction 1718.2 Occurrence and structure of polyacylated anthocyanins in blue flowers 1738.3 Molecular associations of polyacylated anthocyanins in blue flower petals 1788.4 UV protection of polyacylated anthocyanins from solar radiation 1838.5 Conclusion 187References 1889 The Involvement of Anthocyanin-Rich Foods in Retinal Damage 193Kenjirou Ogawa and Hideaki Hara9.1 Introduction 1939.2 Anthocyanin-rich foods for eye health 1959.3 Experimental models to mimic eye diseases and the effect of anthocyanin-rich foods 1969.4 Conclusions 201References 20310 Prevention and Treatment of Diabetes Using Polyphenols via Activation of AMP-Activated Protein Kinase and Stimulation of Glucagon-like Peptide-1 Secretion 206Takanori Tsuda10.1 Introduction 20610.2 Activation of AMPK and metabolic change 20710.3 GLP-1 action and diabetes prevention/suppression 21210.4 Future issues and prospects 220References 22211 Beneficial Vascular Responses to Proanthocyanidins: Critical Assessment of Plant-Based Test Materials and Insight into the Signaling Pathways 226Herbert Kolodziej11.1 Introduction 22711.2 Appraisal of test materials 22811.3 Endothelial dysfunction 23311.4 In vitro test systems 23411.5 Vasorelaxant mechanisms 23511.6 Bioavailability and metabolic transformation: the missing link in the evidence to action in the body 24911.7 Conclusions 250References 25112 Polyphenols for Brain and Cognitive Health 259Katherine H. M. Cox and Andrew Scholey12.1 Introduction 25912.2 Studies of total polyphenols and cognition 26012.3 Pine bark 27212.4 Discussion and conclusions 283References 28313 Curcumin and Cancer Metastasis 289Ikuo Saiki13.1 Introduction 29013.2 Effects of curcumin on intra-hepatic metastasis of liver cancer 29313.3 Effects of curcumin on lymp node metastasis of lung cancer 29813.4 Effects of curcumin on tumor angiogenesis 30313.5 Conclusions 307References 30714 Phytochemical and Pharmacological Overview of Cistanche Species 313Hai-Ning Lv, Ke-Wu Zeng, Yue-Lin Song, Yong Jiang and Peng-Fei Tu14.1 Introduction 31314.2 Chemical constituents of Cistanche species 31414.3 Bioactivities of the extracts and pure compounds from Cistanche species 32214.4 Conclusions 334References 334Index 342