1  Cover

      2  Series Page

      3  Title Page

      4  Copyright Page

      5  Contributors

      6  Preface

      7  Acknowledgements

      8  1 Achieving Complexity at the Bottom Through the Flavylium Cation‐Based Multistate 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 1.4 The Kinetic Processes 1.5 Conclusions and Perspectives References

      9  2 Proanthocyanidin Oligomers with Doubly Linked (A‐Type) Interflavan Connectivity 2.1 Introduction 2.2 Structure 2.3 Synthetic Studies 2.4 Conclusion References

      10  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 3.6 Commercialization Prospects for Wildcrafted Polyphenol‐rich Plants 3.7 Acknowledgements References

      11  4 Causes and Consequences of Condensed Tannin Variation in Populus 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 4.5 Roles of CT Variation in Populus‐Environment Interactions 4.6 Importance of CTs in Populus‐dominated Ecosystems of the Anthropocene 4.7 Conclusions and Challenges 4.8 Acknowledgements References

      12  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 5.5 Multivariate Analysis of MALDI‐TOF MS Spectra Data 5.6 Conclusion References

      13  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 6.7 Proanthocyanidin Characterization by Depolymerization 6.8 Mass Spectrometry 6.9 Nuclear Magnetic Resonance Spectroscopy 6.10 Colorimetry 6.11 Infrared Spectroscopy 6.12 Conclusions 6.13 Acknowledgments References

      14  7 Lignin Monomers Derived from the Flavonoid and Hydroxystilbene Biosynthetic Pathways 7.1 Lignin