Juha-Pekka Salminen, current Communication Manager of Groupe Polyphénols (board member since 2018), is Full Professor of Natural Compound Chemistry at the University of Turku, Finland. His research group specializes in analytical chemistry, chemical ecology and bioactivity studies of large polyphenols, with a focus on ellagitannins and proanthocyanidins and their distribution and significance in the plant kingdom. Kristiina Wähälä, current Vice-President of the Groupe Polyphénols (2012–2014, 2018–2020) is Professor of Organic Chemistry at the University of Helsinki, Finland. Her research is focused on synthesis, analysis, and isotopical labelling of plant polyphenols and their metabolites in humans in connection with drug discovery and binding studies to target enzymes. The focus on her chemical synthesis is on environmentally benign methods, green chemistry and biomass utilization. Victor de Freitas, former President of the Groupe Polyphénols (2016–2021), is Full Professor at the Faculty of Sciences of the University of Porto, Portugal. His research on polyphenols include: structural characterization, chemical transformations in plants and foods during harvest and storage, influence on the sensory properties of foods (color, astringency and bitterness), and other biological properties. Stéphane Quideau, former President of the Groupe Polyphénols (2008–2012), is Full Professor of Organic and Bioorganic Chemistry at the University of Bordeaux, France, and Senior Member of the “Institut Universitaire de France.” His laboratory is involved in research on plant polyphenol chemistry and chemical biology, with particular interests in ellagitannin chemical reactivity and synthesis, and in polyphenol–protein interactions.

• ContributorsPrefaceAcknowledgements1 Lignins and Lignification: New Developments and Emerging ConceptsJohn Ralph, Hoon Kim, Fachuang Lu, Rebecca A. Smith, Steven D. Karlen, Nuoendagula, Koichi Yoshioka, Alexis Eugene, Sarah Liu, Canan Sener, Daisuke Ando, Mingjie Chen, Yanding Li, Leta L. Landucci, Sally A. Ralph, Vitaliy I. Timokhin, Wu Lan, Jorge Rencoret, José C. del Río1.1 Introduction1.2 The monolignol pathway and interacting pathways -- New lignins1.3 Lignin conjugates, 'clip-offs' -- new discoveries, and enhancing levels1.4 Features of lignification, and the possibility of new polymerization pathways1.5 The value of model studies and synthesis -- a reminder1.6 New or improved analytics1.7 Conclusions and Opportunities2 Synthesis of epigallocatechin gallate, nobiletin and their derivatives for chemical-biology studiesTomohiro Asakawa, Makoto Inai and Toshiyuki Kan2.1 Synthetic investigations of catechin derivatives2.2 Synthesis and application of fluorescent catechin probes2.3 Generation of catechin antibody2.4 PET imaging of biodistribution of catechin2.5 Practical synthesis of nobiletin2.6 Derivatization of desmethyl nobiletins2.7 PET imaging of biodistribution of nobiletin2.8 Synthesis and application of fluorescent nobiletin probe2.9 Conclusions3 Procyanidins in the Onset and Progression of Colorectal Cancer: Recent Advances and Open QuestionsWei Zhu, Gerardo G. Mackenzie and Patricia I. Oteiza3.1 Introduction3.2 Procyanidins:chemistry and metabolism3.3 Procyanidins and CRC: epidemiological evidence3.4 Procyanidins and CRC: rodent studies3.5 Procyanidins and CRC: mechanisms of actions3.6 Conclusions and open questions3.7 Acknowledgements4 The Potential of Low Molecular Weight (Poly)phenol Metabolites for Attenuating Neuroinflammation and Treatment of Neurodegenerative DiseasesDaniela Marques, Rafael Carecho, Diogo Carregosa and Cláudia Nunes dos Santos4.1 Introduction - Neurodegenerative disorders, dietary (poly)phenols and neuroinflammation4.2 (Poly)phenols metabolism and distribution4.3 (Poly)phenol metabolites and their brain permeability4.4 LMW (poly)phenols metabolites as effectors for attenuating neuroinflammation4.5 Concluding remarks5 Deciphering Complex Natural Mixtures through Metabolome Mining of Mass Spectrometry Data: the Plant Specialized Metabolome as a Case StudyJustin J.J. van der Hooft, Madeleine Ernst, Daniel Papenberg, Kyo Bin Kang, Iris F. Kappers, Marnix H. Medema, Pieter C. Dorrestein, and Simon Rogers5.1 Introduction5.2 Materials and methods5.3 Results and discussion5.4 Current limitations5.5 Conclusions5.6 Outlook5.7 Acknowledgements6 Application of MS-based Metabolomics to Investigate Biomarkers of Apple Consumption Resulting from Microbiota and Host Metabolism InteractionsFulvio Mattivi and Maria M. Ulaszewska6.1 Introduction6.2 Materials and methods6.3 Results and discussion6.4 Conclusions7 Non-extractable polyphenols should be systematically included in polyphenols analysisEnrique Báez-García, Sonia G. Sáyago-Ayerdi and Jara Pérez-Jiménez7.1 Introduction: the concept of non-extractable polyphenols7.2 Analysis of non-extractable polyphenols7.3 Why should non-extractable polyphenols be systematically included in polyphenol analysis?7.4 Relevance of the determination of non-extractable polyphenols in quality control7.5. Perspectives8 Template-mediated engineering of functional metal--phenolic complex coatingsSteve Spoljaric, J.J. Richardson, Yi Ju, Frank Caruso8.1 Introduction8.2 Template-mediated techniques to deposit MPNs8.3 MPN film properties8.4 MPN surface interactions and applications8.5 Upscaling considerations and challenges8.6 Method automation: possibilities and outlook8.7 Conclusions9 Highly Efficient Production of Dihydroflavonol 4-Reductases in Tobacco Cells and Refinement of the BuOH-HCl Enzymatic AssayLingping Zhu, Saku Mattila, Roosa Matomäki, Lorenzo Mollo, Sharmin Ahamed, Sara M. Abdou, Hany Bashandy and Teemu H. Teeri9.1 Introduction9.2 Results9.3 Materials and methods9.4 Discussion10 A long and winding road: the evolution of transcriptional regulation of polyphenol biosynthesisCathie Martin, Jie Li and Nick W. Albert10.1 Introduction10.2 The importance of R2R3Myb transcription factors (TFs) in the regulation of phenylpropanoid metabolism in plants10.3 The role of bHLH proteins in the regulation of phenylpropanoid metabolism10.4 The role of the WDR in the MBW complex in the regulation of polyphenol metabolism10.5 Additional factors regulating transcriptional control of the MBW complex10.6 Conclusions10.7 Acknowledgements11 Analysis of Proanthocyanidins in Food Ingredients by the 4-(Dimethylamino)cinnamaldehyde ReactionDaniel Esquivel-Alvarado, Emilia Alfaro-Viquez, Andrew Birmingham, Abigail Kramschuster, Christian G. Krueger, and Jess D. Reed11.1. Introduction11.2. Background on the 4-(dimethylamino)cinnalmaldehyde (DMAC) reaction with PACs11.3. Mechanism of the acid catalyzed DMAC reaction with PACs11.4 Absorption and emission spectra of the DMAC reaction products11.5 Standards for the DMAC reaction and accuracy of the method11.6 Interaction of PAC-DMAC reaction products with Extra-Intestinal Pathogenic Escherichia coli11.7 Conclusions12 Reactions of Ellagitannins Related to their Metabolism in Higher PlantsTakashi Tanaka12.1 Introduction12.2 Structural variety of ellagitannin acyl groups12.3 Reactions of the DHHDP group12.4 Decomposition of 1,4-DHHDP-α-D-glucose12.5 Amariin as a precursor of geraniin12.6 Triterpene HHDP esters in Castanopsis sieboldii12.7 Highly-oxidized ellagitannins in Carpinus japonica12.8 Similarity of catechin oxidation to oxidation of methyl gallate12.9 Production mechanism of DHHDP and HHDP12.10 Oxidative degradation of ellagitannins12.11 ConclusionsReferencesIndex

Juha-Pekka Salminen, current Communication Manager of Groupe Polyphénols (board member since 2018), is Full Professor of Natural Compound Chemistry at the University of Turku, Finland. His research group specializes in analytical chemistry, chemical ecology and bioactivity studies of large polyphenols, with a focus on ellagitannins and proanthocyanidins and their distribution and significance in the plant kingdom. Kristiina Wähälä, current Vice-President of the Groupe Polyphénols (2012–2014, 2018–2020) is Professor of Organic Chemistry at the University of Helsinki, Finland. Her research is focused on synthesis, analysis, and isotopical labelling of plant polyphenols and their metabolites in humans in connection with drug discovery and binding studies to target enzymes. The focus on her chemical synthesis is on environmentally benign methods, green chemistry and biomass utilization. Victor de Freitas, former President of the Groupe Polyphénols (2016–2021), is Full Professor at the Faculty of Sciences of the University of Porto, Portugal. His research on polyphenols include: structural characterization, chemical transformations in plants and foods during harvest and storage, influence on the sensory properties of foods (color, astringency and bitterness), and other biological properties. Stéphane Quideau, former President of the Groupe Polyphénols (2008–2012), is Full Professor of Organic and Bioorganic Chemistry at the University of Bordeaux, France, and Senior Member of the “Institut Universitaire de France.” His laboratory is involved in research on plant polyphenol chemistry and chemical biology, with particular interests in ellagitannin chemical reactivity and synthesis, and in polyphenol–protein interactions.

• ContributorsPrefaceAcknowledgements1 Lignins and Lignification: New Developments and Emerging ConceptsJohn Ralph, Hoon Kim, Fachuang Lu, Rebecca A. Smith, Steven D. Karlen, Nuoendagula, Koichi Yoshioka, Alexis Eugene, Sarah Liu, Canan Sener, Daisuke Ando, Mingjie Chen, Yanding Li, Leta L. Landucci, Sally A. Ralph, Vitaliy I. Timokhin, Wu Lan, Jorge Rencoret, José C. del Río1.1 Introduction1.2 The monolignol pathway and interacting pathways -- New lignins1.3 Lignin conjugates, 'clip-offs' -- new discoveries, and enhancing levels1.4 Features of lignification, and the possibility of new polymerization pathways1.5 The value of model studies and synthesis -- a reminder1.6 New or improved analytics1.7 Conclusions and Opportunities2 Synthesis of epigallocatechin gallate, nobiletin and their derivatives for chemical-biology studiesTomohiro Asakawa, Makoto Inai and Toshiyuki Kan2.1 Synthetic investigations of catechin derivatives2.2 Synthesis and application of fluorescent catechin probes2.3 Generation of catechin antibody2.4 PET imaging of biodistribution of catechin2.5 Practical synthesis of nobiletin2.6 Derivatization of desmethyl nobiletins2.7 PET imaging of biodistribution of nobiletin2.8 Synthesis and application of fluorescent nobiletin probe2.9 Conclusions3 Procyanidins in the Onset and Progression of Colorectal Cancer: Recent Advances and Open QuestionsWei Zhu, Gerardo G. Mackenzie and Patricia I. Oteiza3.1 Introduction3.2 Procyanidins:chemistry and metabolism3.3 Procyanidins and CRC: epidemiological evidence3.4 Procyanidins and CRC: rodent studies3.5 Procyanidins and CRC: mechanisms of actions3.6 Conclusions and open questions3.7 Acknowledgements4 The Potential of Low Molecular Weight (Poly)phenol Metabolites for Attenuating Neuroinflammation and Treatment of Neurodegenerative DiseasesDaniela Marques, Rafael Carecho, Diogo Carregosa and Cláudia Nunes dos Santos4.1 Introduction - Neurodegenerative disorders, dietary (poly)phenols and neuroinflammation4.2 (Poly)phenols metabolism and distribution4.3 (Poly)phenol metabolites and their brain permeability4.4 LMW (poly)phenols metabolites as effectors for attenuating neuroinflammation4.5 Concluding remarks5 Deciphering Complex Natural Mixtures through Metabolome Mining of Mass Spectrometry Data: the Plant Specialized Metabolome as a Case StudyJustin J.J. van der Hooft, Madeleine Ernst, Daniel Papenberg, Kyo Bin Kang, Iris F. Kappers, Marnix H. Medema, Pieter C. Dorrestein, and Simon Rogers5.1 Introduction5.2 Materials and methods5.3 Results and discussion5.4 Current limitations5.5 Conclusions5.6 Outlook5.7 Acknowledgements6 Application of MS-based Metabolomics to Investigate Biomarkers of Apple Consumption Resulting from Microbiota and Host Metabolism InteractionsFulvio Mattivi and Maria M. Ulaszewska6.1 Introduction6.2 Materials and methods6.3 Results and discussion6.4 Conclusions7 Non-extractable polyphenols should be systematically included in polyphenols analysisEnrique Báez-García, Sonia G. Sáyago-Ayerdi and Jara Pérez-Jiménez7.1 Introduction: the concept of non-extractable polyphenols7.2 Analysis of non-extractable polyphenols7.3 Why should non-extractable polyphenols be systematically included in polyphenol analysis?7.4 Relevance of the determination of non-extractable polyphenols in quality control7.5. Perspectives8 Template-mediated engineering of functional metal--phenolic complex coatingsSteve Spoljaric, J.J. Richardson, Yi Ju, Frank Caruso8.1 Introduction8.2 Template-mediated techniques to deposit MPNs8.3 MPN film properties8.4 MPN surface interactions and applications8.5 Upscaling considerations and challenges8.6 Method automation: possibilities and outlook8.7 Conclusions9 Highly Efficient Production of Dihydroflavonol 4-Reductases in Tobacco Cells and Refinement of the BuOH-HCl Enzymatic AssayLingping Zhu, Saku Mattila, Roosa Matomäki, Lorenzo Mollo, Sharmin Ahamed, Sara M. Abdou, Hany Bashandy and Teemu H. Teeri9.1 Introduction9.2 Results9.3 Materials and methods9.4 Discussion10 A long and winding road: the evolution of transcriptional regulation of polyphenol biosynthesisCathie Martin, Jie Li and Nick W. Albert10.1 Introduction10.2 The importance of R2R3Myb transcription factors (TFs) in the regulation of phenylpropanoid metabolism in plants10.3 The role of bHLH proteins in the regulation of phenylpropanoid metabolism10.4 The role of the WDR in the MBW complex in the regulation of polyphenol metabolism10.5 Additional factors regulating transcriptional control of the MBW complex10.6 Conclusions10.7 Acknowledgements11 Analysis of Proanthocyanidins in Food Ingredients by the 4-(Dimethylamino)cinnamaldehyde ReactionDaniel Esquivel-Alvarado, Emilia Alfaro-Viquez, Andrew Birmingham, Abigail Kramschuster, Christian G. Krueger, and Jess D. Reed11.1. Introduction11.2. Background on the 4-(dimethylamino)cinnalmaldehyde (DMAC) reaction with PACs11.3. Mechanism of the acid catalyzed DMAC reaction with PACs11.4 Absorption and emission spectra of the DMAC reaction products11.5 Standards for the DMAC reaction and accuracy of the method11.6 Interaction of PAC-DMAC reaction products with Extra-Intestinal Pathogenic Escherichia coli11.7 Conclusions12 Reactions of Ellagitannins Related to their Metabolism in Higher PlantsTakashi Tanaka12.1 Introduction12.2 Structural variety of ellagitannin acyl groups12.3 Reactions of the DHHDP group12.4 Decomposition of 1,4-DHHDP-α-D-glucose12.5 Amariin as a precursor of geraniin12.6 Triterpene HHDP esters in Castanopsis sieboldii12.7 Highly-oxidized ellagitannins in Carpinus japonica12.8 Similarity of catechin oxidation to oxidation of methyl gallate12.9 Production mechanism of DHHDP and HHDP12.10 Oxidative degradation of ellagitannins12.11 ConclusionsReferencesIndex

Juha-Pekka Salminen, current Communication Manager of Groupe Polyphénols (board member since 2018), is Full Professor of Natural Compound Chemistry at the University of Turku, Finland. His research group specializes in analytical chemistry, chemical ecology and bioactivity studies of large polyphenols, with a focus on ellagitannins and proanthocyanidins and their distribution and significance in the plant kingdom. Kristiina Wähälä, current Vice-President of the Groupe Polyphénols (2012–2014, 2018–2020) is Professor of Organic Chemistry at the University of Helsinki, Finland. Her research is focused on synthesis, analysis, and isotopical labelling of plant polyphenols and their metabolites in humans in connection with drug discovery and binding studies to target enzymes. The focus on her chemical synthesis is on environmentally benign methods, green chemistry and biomass utilization. Victor de Freitas, former President of the Groupe Polyphénols (2016–2021), is Full Professor at the Faculty of Sciences of the University of Porto, Portugal. His research on polyphenols include: structural characterization, chemical transformations in plants and foods during harvest and storage, influence on the sensory properties of foods (color, astringency and bitterness), and other biological properties. Stéphane Quideau, former President of the Groupe Polyphénols (2008–2012), is Full Professor of Organic and Bioorganic Chemistry at the University of Bordeaux, France, and Senior Member of the “Institut Universitaire de France.” His laboratory is involved in research on plant polyphenol chemistry and chemical biology, with particular interests in ellagitannin chemical reactivity and synthesis, and in polyphenol–protein interactions.

• ContributorsPrefaceAcknowledgements1 Lignins and Lignification: New Developments and Emerging ConceptsJohn Ralph, Hoon Kim, Fachuang Lu, Rebecca A. Smith, Steven D. Karlen, Nuoendagula, Koichi Yoshioka, Alexis Eugene, Sarah Liu, Canan Sener, Daisuke Ando, Mingjie Chen, Yanding Li, Leta L. Landucci, Sally A. Ralph, Vitaliy I. Timokhin, Wu Lan, Jorge Rencoret, José C. del Río1.1 Introduction1.2 The monolignol pathway and interacting pathways -- New lignins1.3 Lignin conjugates, 'clip-offs' -- new discoveries, and enhancing levels1.4 Features of lignification, and the possibility of new polymerization pathways1.5 The value of model studies and synthesis -- a reminder1.6 New or improved analytics1.7 Conclusions and Opportunities2 Synthesis of epigallocatechin gallate, nobiletin and their derivatives for chemical-biology studiesTomohiro Asakawa, Makoto Inai and Toshiyuki Kan2.1 Synthetic investigations of catechin derivatives2.2 Synthesis and application of fluorescent catechin probes2.3 Generation of catechin antibody2.4 PET imaging of biodistribution of catechin2.5 Practical synthesis of nobiletin2.6 Derivatization of desmethyl nobiletins2.7 PET imaging of biodistribution of nobiletin2.8 Synthesis and application of fluorescent nobiletin probe2.9 Conclusions3 Procyanidins in the Onset and Progression of Colorectal Cancer: Recent Advances and Open QuestionsWei Zhu, Gerardo G. Mackenzie and Patricia I. Oteiza3.1 Introduction3.2 Procyanidins:chemistry and metabolism3.3 Procyanidins and CRC: epidemiological evidence3.4 Procyanidins and CRC: rodent studies3.5 Procyanidins and CRC: mechanisms of actions3.6 Conclusions and open questions3.7 Acknowledgements4 The Potential of Low Molecular Weight (Poly)phenol Metabolites for Attenuating Neuroinflammation and Treatment of Neurodegenerative DiseasesDaniela Marques, Rafael Carecho, Diogo Carregosa and Cláudia Nunes dos Santos4.1 Introduction - Neurodegenerative disorders, dietary (poly)phenols and neuroinflammation4.2 (Poly)phenols metabolism and distribution4.3 (Poly)phenol metabolites and their brain permeability4.4 LMW (poly)phenols metabolites as effectors for attenuating neuroinflammation4.5 Concluding remarks5 Deciphering Complex Natural Mixtures through Metabolome Mining of Mass Spectrometry Data: the Plant Specialized Metabolome as a Case StudyJustin J.J. van der Hooft, Madeleine Ernst, Daniel Papenberg, Kyo Bin Kang, Iris F. Kappers, Marnix H. Medema, Pieter C. Dorrestein, and Simon Rogers5.1 Introduction5.2 Materials and methods5.3 Results and discussion5.4 Current limitations5.5 Conclusions5.6 Outlook5.7 Acknowledgements6 Application of MS-based Metabolomics to Investigate Biomarkers of Apple Consumption Resulting from Microbiota and Host Metabolism InteractionsFulvio Mattivi and Maria M. Ulaszewska6.1 Introduction6.2 Materials and methods6.3 Results and discussion6.4 Conclusions7 Non-extractable polyphenols should be systematically included in polyphenols analysisEnrique Báez-García, Sonia G. Sáyago-Ayerdi and Jara Pérez-Jiménez7.1 Introduction: the concept of non-extractable polyphenols7.2 Analysis of non-extractable polyphenols7.3 Why should non-extractable polyphenols be systematically included in polyphenol analysis?7.4 Relevance of the determination of non-extractable polyphenols in quality control7.5. Perspectives8 Template-mediated engineering of functional metal--phenolic complex coatingsSteve Spoljaric, J.J. Richardson, Yi Ju, Frank Caruso8.1 Introduction8.2 Template-mediated techniques to deposit MPNs8.3 MPN film properties8.4 MPN surface interactions and applications8.5 Upscaling considerations and challenges8.6 Method automation: possibilities and outlook8.7 Conclusions9 Highly Efficient Production of Dihydroflavonol 4-Reductases in Tobacco Cells and Refinement of the BuOH-HCl Enzymatic AssayLingping Zhu, Saku Mattila, Roosa Matomäki, Lorenzo Mollo, Sharmin Ahamed, Sara M. Abdou, Hany Bashandy and Teemu H. Teeri9.1 Introduction9.2 Results9.3 Materials and methods9.4 Discussion10 A long and winding road: the evolution of transcriptional regulation of polyphenol biosynthesisCathie Martin, Jie Li and Nick W. Albert10.1 Introduction10.2 The importance of R2R3Myb transcription factors (TFs) in the regulation of phenylpropanoid metabolism in plants10.3 The role of bHLH proteins in the regulation of phenylpropanoid metabolism10.4 The role of the WDR in the MBW complex in the regulation of polyphenol metabolism10.5 Additional factors regulating transcriptional control of the MBW complex10.6 Conclusions10.7 Acknowledgements11 Analysis of Proanthocyanidins in Food Ingredients by the 4-(Dimethylamino)cinnamaldehyde ReactionDaniel Esquivel-Alvarado, Emilia Alfaro-Viquez, Andrew Birmingham, Abigail Kramschuster, Christian G. Krueger, and Jess D. Reed11.1. Introduction11.2. Background on the 4-(dimethylamino)cinnalmaldehyde (DMAC) reaction with PACs11.3. Mechanism of the acid catalyzed DMAC reaction with PACs11.4 Absorption and emission spectra of the DMAC reaction products11.5 Standards for the DMAC reaction and accuracy of the method11.6 Interaction of PAC-DMAC reaction products with Extra-Intestinal Pathogenic Escherichia coli11.7 Conclusions12 Reactions of Ellagitannins Related to their Metabolism in Higher PlantsTakashi Tanaka12.1 Introduction12.2 Structural variety of ellagitannin acyl groups12.3 Reactions of the DHHDP group12.4 Decomposition of 1,4-DHHDP-α-D-glucose12.5 Amariin as a precursor of geraniin12.6 Triterpene HHDP esters in Castanopsis sieboldii12.7 Highly-oxidized ellagitannins in Carpinus japonica12.8 Similarity of catechin oxidation to oxidation of methyl gallate12.9 Production mechanism of DHHDP and HHDP12.10 Oxidative degradation of ellagitannins12.11 ConclusionsReferencesIndex