Title Page ; Copyright Page; Contents; Contributors; Preface; Chapter 1 The Physical Chemistry of Polyphenols: Insights into the Activity of Polyphenols in Humans at the Molecular Level; 1.1 Introduction; 1.2 Molecular complexation of polyphenols; 1.2.1 Polyphenol-protein binding; 1.2.1.1 Interactions in the digestive tract; 1.2.1.2 Interactions beyond intestinal absorption; 1.2.2 Interactions with membranes; 1.3 Polyphenols as electron donors; 1.3.1 The physicochemical bases of polyphenol-to-ROS electron transfer ; 1.3.1.1 Thermodynamics descriptors.

1.3.1.2 Kinetics of hydrogen atom transfer; 1.3.1.3 Kinetics and mechanisms; 1.3.2 ROS scavenging by polyphenols in the gastrointestinal tract; 1.4 Polyphenols as ligands for metal ions; 1.4.1 Interactions of polyphenols with iron and copper ions; 1.4.2 A preliminary theoretical study of iron-polyphenol binding; 1.4.2.1 Charge states, spin states, and geometries; 1.4.2.2 Oxidation of the bideprotonated catechol; 1.5 Conclusions; References; Chapter 2 Polyphenols in Bryophytes: Structures, Biological Activities, and Bio- and Total Syntheses ; 2.1 Introduction.

2.2 Distribution of cyclic and acyclic bis-bibenzyls in Marchantiophyta (liverworts); 2.3 Biosynthesis of bis-bibenzyls ; 2.4 The structures of bis-bibenzyls and their total synthesis ; 2.5 Biological activity of bis-bibenzyls ; 2.6 Conclusions; Acknowledgments; References; Chapter 3 Oxidation Mechanism of Polyphenols and Chemistry of Black Tea; 3.1 Introduction; 3.2 Catechin oxidation and production of theaflavins; 3.3 Theasinensins; 3.4 Coupled oxidation mechanism; 3.5 Bicyclo[3.2.1]octane intermediates; 3.6 Structures of catechin oxidation products; 3.7 Oligomeric oxidation products.

3.8 Conclusions; Acknowledgments; References; Chapter 4 A Proteomic-Based Quantitative Analysis of the Relationship Between Monolignol Biosynthetic Protein Abundance and Lignin Content Using Transgenic Populus trichocarpa ; 4.1 Introduction; 4.2 Results; 4.2.1 Production of transgenic trees downregulated for genes in monolignol biosynthesis; 4.2.2 Absolute quantification of protein abundance; 4.2.3 Variation in protein abundance in wild-type and transgenic plants ; 4.2.4 Variation in lignin content; 4.2.5 Relationship of lignin content and protein abundance; 4.3 Discussion.

4.4 Materials and methods; 4.4.1 Production of transgenic trees; 4.4.2 Proteomic analysis; 4.4.3 Lignin quantification; 4.4.4 Statistical analysis; References; Chapter 5 Monolignol Biosynthesis and Regulation in Grasses; 5.1 Introduction; 5.2 Unique cell walls in grasses; 5.3 Lignin deposition in grasses; 5.4 Monolignol biosynthesis in grasses; 5.4.1 Proposed pathway for monolignol biosynthesis; 5.4.2 Monolignol biosynthetic genes in grasses; 5.4.3 Functional genomics of monolignol biosynthesis in grass species; 5.5 Regulation of monolignol biosynthesis in grasses.

5.5.1 Lignin regulation in secondary cell wall biosynthesis.