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Группа авторов. Recent Advances in Polyphenol Research
Table of Contents
List of Tables
List of Illustrations
Guide
Pages
Recent Advances in Polyphenol Research
Recent Advances in Polyphenol Research
Contributors
Preface
Acknowledgements
1 Achieving Complexity at the Bottom Through the Flavylium Cation‐Based Multistate : A Comprehensive Kinetic and Thermodynamic Study
1.1 Introduction
1.2 Flavylium Cation as a Metamorphosis Generator
1.3 Extending the Multistate of Anthocyanins and Related Compounds to the Basic Region
1.3.1 Reverse pH Jumps from Pseudo‐equilibrium Followed by Stopped Flow UV‐visible Spectroscopy
1.3.2 Reverse pH Jumps from Equilibrium
1.4 The Kinetic Processes
1.4.1 Heavenly Blue Anthocyanin
1.4.2 2‐Hydroxyflavylium Derivatives and Flavanones
1.4.3 6,8 Rearrangements
1.4.3.1 Unveiling the 6,8 Rearrangement Through Host‐Guest Complexation
1.5 Conclusions and Perspectives
References
Endnotes
2 Proanthocyanidin Oligomers with Doubly Linked (A‐Type) Interflavan Connectivity : Structure and Synthesis
2.1 Introduction
2.2 Structure
2.3 Synthetic Studies
2.3.1 Hypothetical Biosynthetic Routes
2.3.2 Retrosynthesis
2.3.3 Oxidative Conversion from B‐type PAs (Route I)
2.3.4 Approaches via an Acyclic Precursor (Route II)
2.3.5 Annulation Approach (Route III)
2.3.6 Total Synthesis
2.3.6.1 Synthesis of Diinsininol Aglycon (45)
2.3.6.2 Synthesis of Procyanidin A2 (3)
2.3.6.3 Synthesis of (+)‐Cinnamtannin B1 (62)
2.3.6.4 Synthesis of Selligueain A (63)
2.3.6.5 Synthesis of Procyanidin A2 (3)
2.4 Conclusion
References
3 Answering the Call of the Wild: Polyphenols in Traditional Therapeutic Practice
3.1 Introduction
3.2 The Wildcrafting Tradition
3.3 How Wildcrafted Edible Plants Differ from Agricultural Commodities
3.4 Animal Mimickry/Zoopharmacognosy
3.5 Probing the Mechanisms Behind Polyphenol‐rich Traditional Medicines Bioactivity
3.5.1 Phlorotannins in Alaskan Seaweeds/Marine Algae
3.5.2 Isolating Phytoactive Principles from the Mediterranean Region
3.5.3 Drug Discovery in Cooperation with Traditional Healers in Botswana
3.5.4 Antidiabetic Mechanisms of Wild Tundra Berries
3.6 Commercialization Prospects for Wildcrafted Polyphenol‐rich Plants
3.7 Acknowledgements
References
4 Causes and Consequences of Condensed Tannin Variation in Populus: A Molecules to Ecosystems Perspective
4.1 Introduction
4.2 Condensed Tannin Biosynthesis
4.3 Allocational Tradeoffs Influence CT Production
4.4 Causes of Quantitative and Qualitative Variation in Populus CTs. 4.4.1 Genetic Variation in CT Quantity and Quality
4.4.2 Developmental Variation in CT Quantity and Quality. 4.4.2.1 Seasonal Variation
4.4.2.2 Ontogenetic Variation
4.4.3 Environmental Variation in CT Quantity and Quality. 4.4.3.1 Abiotic Environment
4.4.3.2 Biotic Environment
4.5 Roles of CT Variation in Populus‐Environment Interactions
4.5.1 Biological Activity of CTs. 4.5.1.1 Mode of Action
4.5.1.2 Trends in Observed CT Biological Activity
4.5.2 Relationships of Populus CTs to Organism Performance: CTs as Agents of Defense
4.5.3 Relationships of Populus CTs to Community Structure
4.5.4 Relationships of Populus CTs to Ecosystem Function
4.6 Importance of CTs in Populus‐dominated Ecosystems of the Anthropocene. 4.6.1 Condensed Tannins and Populus Ecology
4.6.2 Condensed Tannins and Populus Evolution
4.7 Conclusions and Challenges
4.8 Acknowledgements
References
5 Matrix‐Assisted Laser Desorption/Ionization Time‐of‐Flight Mass Spectrometry (MALDI‐TOF MS) of Proanthocyanidins to Determine Authenticity of Functional Foods and Dietary Supplements
5.1 Introduction
5.2 Introduction to Matrix‐Assisted Laser Desorption/Ionization Time‐of‐Flight Mass Spectrometry (MALDI‐TOF MS)
5.3 Mass Spectrometry of Proanthocyanidins
5.4 Deconvolution of Isotope Patterns of A‐ to B‐type Interflavan Bonds in Proanthocyanidins
5.4.1 Isotope Distributions
5.4.2 Precision and Accuracy Validation for Binary Mixtures of Procyanidin A2 and B2
5.4.3 Deconvolution of Cranberry PAC Ratios of A‐ to B‐type Bonds within Each Degree of Polymerization
5.4.4 Deconvolution Application for PAC Structure in Studies of Bioactivity
5.4.5 MALDI‐TOF MS for Mixtures of Isolated Cranberry and Apple Proanthocyanidins
5.5 Multivariate Analysis of MALDI‐TOF MS Spectra Data
5.6 Conclusion
References
6 Challenges in Analyzing Bioactive Proanthocyanidins
6.1 Introduction
6.2 Structural Diversity of Proanthocyanidins
6.3 Noted Challenges in Proanthocyanidin Analysis
6.4 Fate of Proanthocyanidins in the Digestive Tract and During Plant Fermentation
6.5 Definition and Possible Origins of Nonextractable Proanthocyanidins (NEPAs)
6.6 Universal Problems of Proanthocyanidin Analysis. 6.6.1 The Need for Reference Materials
6.6.2 Extraction and Purification of Proanthocyanidins for Use as In‐house Standards
6.6.3 Gram Scale Isolation and Purification of Proanthocyanidins
6.6.4 Separation of Proanthocyanidin Mixtures and Preparation of ‘DESIGNER’ Extract Resources
6.7 Proanthocyanidin Characterization by Depolymerization
6.8 Mass Spectrometry. 6.8.1 Matrix‐Assisted Laser Desorption Ionization – Time of Flight Mass Spectrometry (MALDI TOF MS)
6.8.2 LC‐MS/MS
6.9 Nuclear Magnetic Resonance Spectroscopy
6.9.1 Use of Variable Temperature 1H NMR Spectroscopy
6.9.2 Use of Solution‐State 13C NMR Spectroscopy
6.9.3 Use of Solid‐State 13C NMR Spectroscopy
6.9.4 Use of 1H–13C HSQC NMR Spectroscopy
6.9.5 Use of 31P NMR Spectroscopy
6.10 Colorimetry
6.11 Infrared Spectroscopy
6.12 Conclusions
6.13 Acknowledgments
References
7 Lignin Monomers Derived from the Flavonoid and Hydroxystilbene Biosynthetic Pathways
7.1 Lignin Monomers Derived from the Monolignol Biosynthetic Pathway. 7.1.1 ‘Canonical’ Monolignols
7.1.2 Other ‘Nonconventional’ Lignin Monomers
7.2 Flavonoid and Hydroxystilbene Biosynthetic Pathways
7.3 Radical Coupling of Flavonoids and Hydroxystilbenes with Monolignols – Flavonolignans and Stilbenolignans
7.3.1 Flavonolignans
7.3.2 Stilbenolignans
7.4 Lignin Monomers Derived from the Flavonoid and Hydroxystilbene Biosynthetic Pathways
7.4.1 Lignin Monomers from the Flavonoid Biosynthetic Pathway – Tricin (and Naringenin and Apigenin in Rice Mutants)
7.4.2 Lignin Monomers from the Hydroxystilbene Biosynthetic Pathway – Resveratrol, Isorhapontigenin, and Piceatannol, and Their O‐glucosides Piceid, Isorhapontin, and Astringin
7.5 Conclusions and Future Prospects
7.6 Acknowledgments
References
8 Complex Regulation of Proanthocyanidin Biosynthesis in Plants by R2R3 MYB Activators and Repressors
8.1 Introduction to PAs and Flavan‐3‐ols
8.2 Regulation of PA and Flavonoid Biosynthesis by MYB Transcription Factors
8.3 The Importance of Repressor MYBs in PA and Flavonoid Metabolism
8.4 The Complex Interaction of PA MYB Activators, MYB Repressors, and bHLH Transcription Factors
8.5 Developmental and Plant Hormone‐Mediated Regulation of the PA Pathway via MYBs
8.6 Stress Activation of PA Synthesis by MYBs in Poplar and Other Woody Plants
8.7 Summary and Conclusions
8.8 Acknowledgments
References
9 Conservation and Divergence Between Bryophytes and Angiosperms in the Biosynthesis and Regulation of Flavonoid Production
9.1 Introduction. 9.1.1 The Bryophytes
9.1.2 Evolution of the Phenylpropanoid Pathway
9.2 Flavonoid Biosynthesis in Basal Plants
9.3 Origins of the Phenylpropanoid Biosynthetic Pathway and Conservation Across the Embryophytes. 9.3.1 Phenylalanine Ammonia Lyase
9.3.2 Cinnamate 4‐hydroxylase
9.3.3 4‐Coumarate‐CoA Ligase (4CL)
9.3.4 Chalcone Synthase
9.3.5 Chalcone Isomerase and Chalcone Isomerase‐like
9.3.6 Hydroxylation Activities
9.4 Notable Phenylpropanoids of Bryophytes
9.4.1 Hydroxycinnamic Acid Derivatives: Rosmarinic Acid and Lignans
9.4.2 Hydroxycinnamic Acid Derivatives: Coumarins
9.4.3 Bis ‐bibenzyls
9.4.4 Flavones and Flavonols
9.4.5 Aurones and Auronidins
9.4.6 3‐Deoxyanthocyanins
9.4.7 Sphagnorubins
9.5 Regulation of Flavonoid Production
9.5.1 Activation of Flavonoid Biosynthesis in Response to UVB Light Exposure
9.5.2 The Role of MYB Transcription Factors in Regulating Flavonoid Biosynthesis in Land Plants
9.6 Concluding Remarks
9.7 Acknowledgements
References
10 Matching Proanthocyanidin Use with Appropriate Analytical Method
10.1 Introduction
10.2 General Proanthocyanidin Structure and Analysis
10.3 Red Wine Mouthfeel
10.4 Biological Activity
10.5 Summary
References
11 Imaging Polyphenolic Compounds in Plant Tissues
11.1 Introduction
11.2 The Chemical Nature and Intrinsic Fluorescence Properties of Polyphenols
11.3 Microscopy‐based Methods for Imaging Plant Phenolic Compounds. 11.3.1 Multispectral Fluorescence Detection
11.3.2 Fluorescence Lifetime Microscopy (FLIM)
11.3.3 Raman Microscopy
11.4 Polyphenols and Microscopy Imaging. 11.4.1 Anthocyanins
11.4.2 Lignin
11.4.3 (Poly)phenolic Compounds in Cell Walls, Cuticles, and Suberin
11.5 Future Challenges and Opportunities in Imaging Plant Metabolites
11.6 Acknowledgments
References
Index
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