Recent Advances in Polyphenol Research

Cover
Title Page
Copyright Page
Dedications
Contents
Contributors
Preface
Acknowledgments
Chapter 1 Lignins and Lignification: New Developments and Emerging Concepts
1.1 Introduction
1.2 The Monolignol Pathway and Interacting Pathways – New Lignins
1.2.1 Truncated Monolignol Biosynthesis
1.2.2 Phenolics from Beyond the Monolignol Biosynthetic Pathway
1.2.3 Lignin Design, and the Concept of an Ideal Lignin
1.3 Lignin Conjugates, “Clip-Offs’ – New Discoveries, and Enhancing Levels
1.3.1 Clip-Offs and Their Elevation
1.3.2 Exploring Monolignol Conjugates in Compositionally Extreme Lignins
1.4 Features of Lignification and the Possibility of New Polymerization Pathways
1.4.1 Features of Lignification
1.5 The Case for Model Studies and Synthesis
1.5.1 The Value of Proper Low-Molecular-Mass Model Compounds
1.5.2 Synthetic Lignin Polymers, Dehydrogenation Polymers (DHPs)
1.6 New or Improved Analytics
1.7 Conclusions and Opportunities
Acknowledgments
References
Chapter 2 Synthesis of Epigallocatechin Gallate, Nobiletin, and Their Derivatives for Chemical-Biological Studies
2.1 Synthetic Investigations of Catechin Derivatives
2.2 Synthesis and Application of Fluorescent Catechin Probes
2.3 Generation of Catechin Antibody
2.4 PET Imaging of Biodistribution of Catechin
2.5 Practical Synthesis of Nobiletin
2.6 Derivatization of Desmethyl Nobiletins
2.7 PET Imaging of Biodistribution of Nobiletin
2.8 Synthesis and Application of Fluorescent Nobiletin Probe
2.9 Conclusions
References
Chapter 3 Procyanidins in the Onset and Progression of Colorectal Cancer: Recent Advances and Open Questions
3.1 Introduction
3.2 Procyanidins: Chemistry and Metabolism
3.3 Procyanidins and CRC: Epidemiological Evidence
3.4 Procyanidins and CRC: Rodent Studies
3.5 Procyanidins and CRC: Mechanisms of Action
3.5.1 Interactions with Membranes
3.5.2 Inflammation and the NF-B Pathway
3.5.3 EGFR and IGF1R Pathways
3.6 Conclusions and Open Questions
Acknowledgments
Conflict of Interest Disclosure
References
Chapter 4 The Potential of Low Molecular Weight (Poly)phenol Metabolites for Attenuating Neuroinflammation and Treatment of Neurodegenerative Diseases
4.1 Introduction: Neurodegenerative Disorders, Dietary (Poly)phenols and Neuroinflammation
4.2 (Poly)phenols: Metabolism and Distribution
4.3 (Poly)phenol Metabolites and Their Brain Permeability
4.4 LMW (Poly)phenol Metabolites as Effectors for Attenuating Neuroinflammation
4.5 Concluding Remarks
Acknowledgments
References
Chapter 5 Deciphering Complex Natural Mixtures through Metabolome Mining of Mass Spectrometry Data: The Plant Specialized Metabolome as a Case Study
5.1 Introduction
5.2 Materials and Methods
5.2.1 Case Studies
5.2.2 Metabolome Mining Tools
5.2.3 Metabolome Annotation Tools
5.3 Results and Discussion
5.3.1 Rhamnaceae Case Study
5.3.2 Euphorbia Case Study
5.3.3 Pepper Case Study
5.3.4 Other Plant Metabolomics Studies
5.4 Current Limitations
5.5 Conclusions
5.6 Outlook
5.6.1 Extended Natural Product Candidate Structure Space
5.6.2 Improved Mass Spectral Similarity Scoring
5.6.3 Combined Genome and Metabolome Analyses
5.6.4 Linking Complementary Analytical Tools
5.6.5 Future Perspective: Chemically Informed Repository-Scale Analyses
Acknowledgments
References
Chapter 6 Application of MS-Based Metabolomics to Investigate Biomarkers of Apple Consumption Resulting from Microbiota and Host Metabolism Interactions
6.1 Introduction
6.2 Materials and Methods
6.2.1 Acute Intake Study
6.2.2 Long-Term Intake Study
6.2.3 Metabolomic Analysis
6.2.4 Data Processing and Statistical Analysis
6.2.5 Metabolomic Data Sharing
6.3 Results and Discussion
6.3.1 Lessons from the Acute Study
6.3.2 Lessons from the Prolonged Exposure Study
6.4 Conclusion
Acknowledgments
Funding
References
Chapter 7 Non-Extractable Polyphenols Should be Systematically Included in Polyphenol Analysis
7.1 Introduction: The Concept of Non-Extractable Polyphenols
7.2 Analysis of Non-Extractable Polyphenols
7.2.1 Preparation of Solutions of Non-Extractable Polyphenols
7.2.2 Analysis of the Profile of NEPP
7.2.3 Determination of the Content of Non-Extractable Polyphenols. Which Standard?
7.2.4 Analysis of Dietary Fiber: Connection with Non-Extractable Polyphenols
7.3 Why Should Non-Extractable Polyphenols be Systematically Included in Polyphenol Analysis?
7.3.1 Intake of NEPP in Different Populations
7.3.2 Metabolism of NEPP
7.3.3 Beneficial Effects Attributed to NEPP
7.4 Relevance of the Determination of Non-Extractable Polyphenols in Quality Control
7.4.1 Comprehensive Characterization of Vegetal Materials
7.4.2 Identification of New Botanical Sources with Potential Applications
7.4.3 Comparison Between Varieties
7.4.4 Evaluation of Processing Effects
7.5 Perspectives
References
Chapter 8 Template-Mediated Engineering of Functional Metal–Phenolic Complex Coatings
8.1 Introduction
8.2 Template-Mediated Techniques to Deposit MPNs
8.3 MPN Film Properties
8.4 MPN Surface Interactions and Applications
8.5 Upscaling Considerations and Challenges
8.5.1 Reagent Considerations
8.5.2 Engineering Controls
8.5.3 Washing and Solvents
8.5.4 Human Resources and Training
8.5.5 Environmental Health and Safety Considerations
8.6 Method Automation: Possibilities and Outlook
8.6.1 Automated Assembly Techniques
8.7 Conclusions
References
Chapter 9 Highly Efficient Production of Dihydroflavonol 4-Reductases in Tobacco Cells and Refinement of the BuOH-HCl Enzymatic Assay
9.1 Introduction
9.2 Results
9.2.1 Transient Expression from Hypertranslatable Vectors
9.2.2 BuOH-HCl Assay Revisited
9.2.3 Substrate Profiles of Different DFRs
9.3 Materials and Methods
9.3.1 Plant Material and Chemicals
9.3.2 Isolation of DFR Encoding Sequences and Plasmid Construction
9.3.3 Protein Extraction and Purification
9.3.4 BuOH-HCl Assay
9.3.5 HPLC
9.4 Discussion
Acknowledgements
References
Chapter 10 A Long and Winding Road: The Evolution of Transcriptional Regulation of Polyphenol Biosynthesis
10.1 Introduction
10.2 The Importance of R2R3Myb Transcription Factors (TFs) in the Regulation of Phenylpropanoid Metabolism in Plants
10.2.1 R2R3Myb TFs Regulate Specialized Branches of Polyphenol Metabolism
10.2.2 R2R3Myb Transcriptional Repressors Controlling Phenylpropanoid Metabolism
10.2.3 Stand-Alone R2R3Myb Transcriptional Activators
10.2.4 R2R3Myb TFs Working in MBW Complexes to Regulate Phenylpropanoid Metabolism
10.3 The Role of bHLH Proteins in the Regulation of Phenylpropanoid Metabolism
10.3.1 Roles of bHLH-1 and bHLH-2 Clades in RegulatingAnthocyanin Biosynthesis
10.3.2 Roles of bHLH-1 and bHLH-2 Clades in the Regulation of Proanthocyanidin Biosynthesis
10.4 The Role of the WDR in the MBW Complex in the Regulation of Polyphenol Metabolism
10.5 Additional Factors Regulating Transcriptional Controlof the MBW Complex
10.6 Conclusions
Acknowledgments
References
Chapter 11 Analysis of Proanthocyanidins in Food Ingredients by the 4-(Dimethylamino)cinnamaldehyde Reaction
11.1 Introduction
11.2 Background on the 4-(Dimethylamino)cinnalmaldehyde (DMAC) Reaction with PACs
11.3 Mechanism of the Acid-Catalyzed DMAC Reaction with PACs
11.4 Absorption and Emission Spectra of the DMAC Reaction Products
11.5 Standards for the DMAC Reaction and Accuracy of the Method
11.6 Interaction of PAC-DMAC Reaction Products with Extra-Intestinal Pathogenic Escherichia coli
11.7 Conclusion
References
Chapter 12 Reactions of Ellagitannins Related to Their Metabolism in Higher Plants
12.1 Introduction
12.2 Structural Variety of Ellagitannin Acyl Groups
12.3 Reactions of the DHHDP Group
12.4 Decomposition of 1,4-DHHDP--d-glucose
12.5 Amariin as a Precursor of Geraniin
12.6 Triterpenoid HHDP Esters in Castanopsis sieboldii
12.7 Highly Oxidized Ellagitannins in Carpinus japonica
12.8 Similarity of Catechin Oxidation to Oxidation of Methyl Gallate
12.9 Production Mechanism of DHHDP and HHDP
12.10 Oxidative Degradation of Ellagitannins
12.10.1 Degradation of Pedunculagins in the Leaves of Common Camellia Species
12.10.2 Degradation of Vescalagin in the Leaves of Japanese Blue Oak
12.10.3 Degradation of Vescalagin with Wood-Decaying Fungi
12.11 Conclusions
References
Index
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