Cover
Contributors
Preface
Acknowledgements
1 The Lignans: A Family of Biologically Active Polyphenolic Secondary Metabolites
1. 1.1 Introduction
2. 1.2 Biosynthesis of Lignans
3. 1.3 Synthetic Approaches to Lignans and Derivatives
4. 1.4 Conclusion
5. References
2 Anthocyanin Accumulation is Controlled by Layers of Repression
1. 2.1 Introduction
2. 2.2 MYBs and bHLHs Directly Activate Anthocyanin Production
3. 2.3 Exciting Phenotypes in Horticulture are often Caused by Variations in the Expression of Key MYBs
4. 2.4 Is There a Cost to the Plant of Overaccumulation of Anthocyanins?
5. 2.5 Controlling Anthocyanin Levels
6. 2.6 The MYB Activator is Degraded at Night
7. 2.7 MYB Activator Competes with MYB Repressors
8. 2.8 miRNA‐Targeted Degradation of MYB Transcript
9. 2.9 Turnover of Anthocyanin Vacuolar Content by Peroxidases
10. 2.10 Summary
11. References
3 The Subtleties of Subcellular Distribution: Pointing the Way to Underexplored Functions for Flavonoid Enzymes and EndProducts
1. 3.1 Multienzyme Complexes and Metabolic Networks
2. 3.2 New Insights from Global Surveys of Protein Interactions
3. 3.3 The Flavonoid Metabolon
4. 3.4 Subcellular Distribution of Flavonoid Enzymes and Evidence for Alternative Metabolons
5. 3.5 Posttranslational Modifications – An Underexplored Area of Flavonoid Metabolism
6. 3.6 Why Do We Need to Know?
7. 3.7 Future Prospects
8. References
4 Transcriptional and Metabolite Profiling Analyses Uncover Novel Genes Essential for Polyphenol Accumulation
1. 4.1 Introduction
2. 4.2 Transcriptional and Metabolite Profiling Analyses in Strawberry Fruit
3. 4.3 Characterization of Peroxidase 27
4. 4.4 Competition of the Lignin and Flavonoid/Anthocyanin Pathways as Demonstrated by the Activity of Peroxidase 27
5. 4.5 Candidate Genes Putatively Correlated with Phenolics Accumulation in Strawberry Fruit
6. 4.6 Acylphloroglucinol Biosynthesis in Strawberry Fruit
7. 4.7 Glucosylation of Acylphloroglucinols
8. 4.8 Conclusion
9. References
5 Dietary (Poly)Phenols and Vascular Health
1. 5.1 Introduction
2. 5.2 Vascular Health: A Prerequisite to Prevent Cardiometabolic Diseases and Cognitive Decline
3. 5.3 Diet and Vascular Health
4. 5.4 (Poly)Phenols: A Major Family of Dietary Plant Bioactive Compounds
5. 5.5 Fate of (Poly)Phenols in the Body and Biological Activities
6. 5.6 Nutritional Effects of Flavonoids in Protecting Cardiovascular Health
7. 5.7 Limitation of Knowledge and Strategy for Research
8. 5.8 Findings from Translational Research on Citrus Flavanones and Vascular Health
9. 5.9 Conclusion
10. References
6 Cellular‐Specific Detection of Polyphenolic Compounds by NMR‐and MS‐Based Techniques: Application to the Representative Polycyclic Aromatics of Members of the Hypericaceae, the Musaceae and the Haemodoraceae
1. 6.1 Introduction
2. 6.2 The Plant Genus Hypericum
3. 6.3 Phenylphenalenones: Plant Secondary Metabolites of the Haemodoraceae
4. 6.4 Phenalenone‐Type Phytoalexins
5. 6.5 Laser Microdissection and Cryogenic NMR as a Combined Tool for Cell Type‐Specific Metabolite Profiling
6. 6.6 Matrix‐free UV Laser Desorption/Ionization (LDI) at the Single‐Cell Level: Distribution of Secondary Metabolites of Hypericum Species
7. 6.7 LDI‐MSI‐Based Detection of Phenalenone‐Type Phytoalexins in a Banana–Nematode Interaction
8. 6.8 LDI‐FT‐ICR‐MSI Reveals the Occurrence of Phenylphenalenones in Red Paracytic Stomata
9. 6.9 Conclusion
10. 6.10 Acknowledgements
11. References
7 Metabolomics Strategies for the Dereplication of Polyphenols and Other Metabolites in Complex Natural Extracts
1. 7.1 Introduction
2. 7.2 Metabolite Profiling and Metabolomics
3. 7.3 Metabolite Annotation and Dereplication
4. 7.4 Targeted Isolation of Original Polyphenols
5. 7.5 Conclusion
6. References
8 Polyphenols from Plant Roots: An Expanding Biological Frontier
1. 8.1 Introduction
2. 8.2 Polyphenols in Roots versus Shoots: Not More, Not Less, But Often Different
3. 8.3 Allelochemical Functions of Root Polyphenols
4. 8.4 Physiological Functions of Root Polyphenols in Plants
5. 8.5 Biotechnologies to Produce Root Polyphenols
6. 8.6 Conclusion
7. References
9 Biosynthesis of Polyphenols in Recombinant Micro‐organisms: A Path to Sustainability
1. 9.1 Introduction
2. 9.2 Flavonoids
3. 9.3 Stilbenes
4. 9.4 Coumarins
5. 9.5 Conclusion
6. References
10 Revisiting Wine Polyphenols Chemistry in Relation to Their Sensory Characteristics
1. 10.1 Introduction
2. 10.2 Astringency of Polyphenols
3. 10.3 Bitter Taste of Polyphenols
4. 10.4 Red Wine Colour
5. 10.5 Conclusion
6. References
11 Advances in Bio‐based Thermosetting Polymers
1. 11.1 Introduction
2. 11.2 Industrial Sources of Polyphenols
3. 11.3 Principles of Thermoset Production
4. 11.4 Relationships between Structure and Reactivity of Polyphenols
5. 11.5 Thermosets from Industrial Lignins and Tannins
6. 11.6 Depolymerization of Lignins and Tannins to Produce Phenolic Building Blocks and their Glycidylether Derivatives
7. 11.7 Development of Dimethyloxirane Monophenols and Bisphenols as Thermosetting Building Blocks
8. 11.8 Conclusion
9. References
12 Understanding the Misunderstood: Products and Mechanisms of the Degradation of Curcumin
1. 12.1 Introduction
2. 12.2 Degradation of Curcumin – A Historical and Personal Perspective
3. 12.3 The Degradation is an Autoxidation
4. 12.4 Novel Products of the Degradation/Autoxidation of Curcumin
5. 12.5 Transformation of Curcumin to Bicyclopentadione
6. 12.6 A Proposed Mechanism for the Autoxidation of Curcumin
7. 12.7 Microbial Degradation of Curcumin
8. 12.8 Conclusion
9. References
13 How to Model a Metabolon: Theoretical Strategies
1. 13.1 Introduction
2. 13.2 Localization
3. 13.3 Existing Structures
4. 13.4 Three‐Dimensional Structures of Enzymes: Homology Modelling
5. 13.5 Modes of Access to Active Sites: Randomly Accelerated Molecular Dynamics
6. 13.6 Protein–Protein Association: Protein–Protein Docking
7. 13.7 Substrate Channelling and Molecular Dynamics
8. 13.8 Metabolon
9. 13.9 Conclusion
10. References
Index
End User License Agreement

List of Tables

Chapter 1
1. Table 1.1 Synthetic oxidative couplings of coniferyl alcohol.
Chapter 3
1. Table 3.1 Flavonoid enzymes reported to exhibit nuclear localization.
Chapter 8
1. Table 8.1 Biological targets affected by root polyphenols and plant physiolog...
Chapter 9
1. Table 9.1 Biosynthesis of certain polyphenols in recombinant micro‐organisms.
Chapter 10
1. Table 10.1 Maximum half effective concentration (EC₅₀, μM) for activation of ...
Chapter 11
1. Table 11.1 Characteristics of industrial lignins.

List of Illustrations

Chapter 1
1. Figure 1.1 Selected biologically active lignan natural products.
2. Figure 1.2 Structural classes of lignans.
3. Scheme 1.1 Biosynthesis of (+)‐pinoresinol.
4. Scheme 1.2 (a) Main coupling pathways for oxidative coupling of coniferyl alc...
5. Figure 1.3 Crystal structure of dirigent protein from Pisum sativum.
6. Scheme 1.3 Biosynthetic pathway for conversion of pinoresinol to podophylloto...
7. Scheme 1.4 Synthesis of dibenzylbutanes 31–32.
8. Scheme 1.5 Synthesis of 2,5‐diaryltetrahydrofurans 33–34 and aryldihydronapht...
9. Scheme 1.6 Synthesis of (+)‐yangambin (45), (+)‐sesamin (46) and (+)‐eudesmin...
10. Scheme 1.7 Reaction pathways in the divergent synthesis of 2,5‐diaryltetrahyd...
11. Scheme 1.8 Synthesis of (+)‐galbelgin (55).
12. Scheme 1.9 Synthesis of (−)‐cyclogalgravin (58), (−)‐pycnanthulignene B (60),...
13. Scheme 1.10 Synthesis of (±)‐tanegool (66) and (±)‐pinoresinol (5).
14. Scheme 1.11 General methods for the synthesis of dibenzylbutyrolactones.
15. Scheme 1.12 Synthesis of (±)‐yatein (27).
16. Scheme 1.13 Synthesis of (±)‐5′‐methoxyyatein (77).
17. Scheme 1.14 Synthesis of (−)‐7′‐(S)‐hydroxyarctigenin (85).
18. Scheme 1.15 Synthesis of (−)‐bursehernin (92).
19. Scheme 1.16 Synthesis of (−)‐hinokinin (98).
20. Scheme 1.17 Synthesis of (−)‐podophyllotoxin (1).
21. Scheme 1.18 Synthesis of chimensin (110) and taiwanin C (111).
22. Scheme 1.19 Synthesis of justicidin B (115).
23. Scheme 1.20 Synthesis of (+)‐podophyllotoxin (1).
24. Scheme 1.21 Synthesis of (−)‐sacidumlignan B (129) and sacidumlignan A (130)....
25. Scheme 1.22 Synthesis of (±)‐cyclogalgravin (58) and aryltetralins 136–142.
26. Scheme 1.23 Synthesis of aryldihydronaphthalenes 56, 60 and aryltetralins 138
27. Scheme 1.24 Initial Garratt–Braverman studies for synthesis of arylnaphthalen...
28. Scheme 1.25 Synthesis of taiwanin C (111) and justicidin E (172).
29. Scheme 1.26 Synthesis of arylnaphthalenes 115, 175–177.
30. Scheme 1.27 Synthesis of justicidin E (172), taiwanin C (111), and daurinol (
31. Scheme 1.28 Synthesis of arylnaphthalene lignans 111, 115, 184–185.
32. Scheme 1.29 Synthesis of justicidin E (173), helioxanthin (188) and retrojust...
33. Scheme 1.30 Synthesis of justicidin E (172), taiwanin C (111) and retrojustic...
34. Scheme 1.31 Synthesis of (+)‐galbulin (136).
35. Scheme 1.32 Synthesis of diphyllin (208), justicidin A (209) and taiwanin E (
36. Scheme 1.33 General methods for the synthesis of 2,5‐diaryltetrahydrofurans. ...
37. Scheme 1.34 Synthesis of (+)‐veraguensin (221).
38. Scheme 1.35 Synthesis of (+)‐galbelgin (55).
39. Scheme 1.36 Synthesis of (+)‐beilschmin A (238).
40. Scheme 1.37 Synthesis of (−)‐virgatusin (243) and (+)‐urinaligran (244).
41. Scheme 1.38 Synthesis of (+)‐virgatusin (243).
42. Scheme 1.39 Synthesis of (+)‐sylvone (256).
43. Scheme 1.40 Synthesis of (+)‐magnolone (265).
44. Scheme 1.41 Synthesis of 2‐aryl‐4‐benzyltetrahydrofurans 273–276.
45. Scheme 1.42 Synthesis of (−)‐magnofargesin (287).
46. Scheme 1.43 Synthesis of (+)‐yangambin (45).
47. Scheme 1.44 Synthesis of (−)‐wodeshial (301).
48. Scheme 1.45 Synthesis of furofurans 309–314.
49. Scheme 1.46 Synthesis of furofurans 46, 322–325.
50. Scheme 1.47 Synthesis of (−)‐wuweizisu (335).
51. Scheme 1.48 Synthesis of (+)‐isoschizandrin (344).
52. Scheme 1.49 Synthesis of dibenzocyclooctadiene lignans 353–360.
53. Scheme 1.50 Synthesis of (−)‐steganone (369).
54. Scheme 1.51 Synthesis of (−)‐isoschizandrin (344).
55. Scheme 1.52 Synthesis of (±)‐deoxyschizandrin (390).
Chapter 2
1. Figure 2.1 MYB transcription factors are regulated at the level of expression...
Chapter 3
1. Figure 3.1 Early model of organization of phenylpropanoid metabolism at the e...
2. Figure 3.2 Model of the soybean isoflavonoid metabolon. Tandem cytochrome P45...
3. Figure 3.3 Flavonoid enzyme interactions. Summary of interactions observed to...
4. Figure 3.4 Molecular mass variants of CHI. Two forms are observed for the nat...
Chapter 4
1. Figure 4.1 Analysis of phenolic compounds in strawberry fruits and calculatio...
2. Figure 4.2 Hierarchical clustering analysis of the metabolite levels. Rows ar...
3. Figure 4.3 The anthocyanin and lignin pathways compete for common substrates....
4. Figure 4.4 Metabolite profiling analysis, structural formula of acylphloroglu...
5. Figure 4.5 Reduced levels of APGs in both transient and stable CHS‐silenced f...
6. Figure 4.6 Downregulation of UGT71K3. (a) Fruit phenotypes and (b) effect of
7. Figure 4.7 APG biosynthesis pathway in strawberry. CHS, chalcone synthase; Co...
Chapter 5
1. Figure 5.1 Pivotal role of vascular function in human health.
2. Figure 5.2 Diversity of dietary (poly)phenols.
3. Figure 5.3 Fate of dietary (poly)phenols in the body: native forms are not th...
4. Figure 5.4 Biological properties of (poly)phenols of interest for human healt...
5. Figure 5.5 Clinical evidence of the role of flavanones in the beneficial effe...
6. Figure 5.6 Nutrigenomic effects induced by the consumption of orange juice an...
7. Figure 5.7 Impact of a dietary supplementation of naringin in a murine model ...
8. Figure 5.8 Exposure to plasma metabolites of naringenin reduced the adhesion ...
Chapter 6
1. Figure 6.1 Chemical structures of secondary metabolites of the genus Hypericu...
2. Figure 6.2 Structural formula of haemocorin and the six (theoretical) basic s...
3. Figure 6.3 General structures of the phenylphenalenone‐type compounds.
4. Figure 6.4 pH‐caused transformations of anthocyanidins and phenylphenalenone‐...
5. Figure 6.5 Different PKS pathways, closely related to the biosynthesis of phe...
6. Figure 6.6 Comparison of a sequence of the biosynthesis of stilbenes, chalcon...
7. Figure 6.7 Proposed hypothetical sequence of the biosynthesis of the phenylph...
8. Figure 6.8 Microscopic images (magnification 400×) of a single SC of D. pilla...
9. Figure 6.9 Detection of hypericin (m/z 503) and pseudo‐hypericin (m/z 519) in...
10. Figure 6.10 LDI‐MSI detection of hypericin (m/z 503) and pseudo‐hypericin (m/
11. Figure 6.11 Negative ion mode LDI‐MSI of the lesions of Ykm5. (a) Optical ima...
12. Figure 6.12 Positive ion mode LDI‐MSI of R. similis after motility bioassay w...
13. Figure 6.13 Negative ion mode LDI‐FT‐ICR‐MSI of red pseudo‐stem material of M...
14. Figure 6.14 Structures of phenylphenalenone‐type phytoanticipins (6–9). (6) A...
Chapter 7
1. Figure 7.1 Metabolite profiling obtained for a Ginkgo biloba standardized ext...
2. Figure 7.2 UHPLC‐HRMS analysis of a Ginkgo biloba extract. (a) Total ion curr...
3. Figure 7.3 Dereplication workflow based on molecular formula determination an...
4. Figure 7.4 Example of application of a retention time prediction tool for der...
5. Figure 7.5 Ion mobility infusion analysis of the crude extract of Ginkgo bilo...
6. Figure 7.6 Differences in fragmentation patterns between two types of MS‐MS i...
7. Figure 7.7 Molecular networking of the MeOH extract of the leaves of Ginkgo b...
8. Figure 7.8 Molecular network of a cluster of prenylated stilbene derivatives ...
9. Figure 7.9 Metabolite profiling of the hydroethanolic extract of the roots of...
10. Figure 7.10 Structures of the unusual polyphenols identified in the hydroalco...
Chapter 8
1. Figure 8.1 Relative concentration of secondary metabolites in roots versus le...
2. Figure 8.2 Structure of polyphenol families frequently found in roots. (a) Fl...
3. Figure 8.3 Root polyphenol distribution through microscopy and MALDI imaging....
4. Figure 8.4 Schematic overview of the rhizospheric interactions mediated by po...
5. Figure 8.5 Examples of root cultures for the production of natural compounds....
6. Figure 8.6 Production of root natural compounds (here tropane alkaloids) (h, ...
7. Figure 8.7 Root systems obtained with soilless grown plants. (a) Overview of ...
Chapter 9
1. Figure 9.1 Detailed biosynthetic steps for flavonoids. 3GT, uridine, flavanon...
2. Figure 9.2 Central metabolic pathways connecting malonyl‐CoA with the plant f...
3. Figure 9.3 Engineered biosynthetic pathways for the methylated resveratrol an...
4. Figure 9.4 Types of coumarins found in higher plants.
5. Figure 9.5 Biosynthesis pathway of simple coumarins (umbelliferone, esculetin...
Chapter 10
1. Figure 10.1 Structures of Vitis vinifera anthocyanins.
2. Figure 10.2 Structures of flavanol monomers and a general structure of conden...
3. Figure 10.3 Schema of the interaction between condensed tannins and proteins....
4. Figure 10.4 Interaction between protein and polyphenols acting as a cross‐lin...
5. Figure 10.5 Network of the equilibrium forms of anthocyanins in an acidic to ...
6. Figure 10.6 Anthocyanin‐derived pigments found in wines.
7. Figure 10.7 Schemes of formation of bluish pyranoanthocyanin compounds in win...
Chapter 11
1. Figure 11.1 Typical constitutive units in lignins and condensed tannins. Typi...
2. Figure 11.2 Thermoset synthesis: typical functional groups of the two compone...
3. Figure 11.3 Lignin modifications to improve its reactivity.
4. Figure 11.4 Comparative reactivity of lignins and condensed tannins.
5. Figure 11.5 Alkoxylation of polyphenol polymers to improve their solubility i...
6. Figure 11.6 Glycidylation products of gallotannins from Tara pod extract.
7. Figure 11.7 Schematic depolymerization of condensed tannins showing the main ...
8. Figure 11.8 Examples of conversion pathways of furylated (epi)catechin into p...
9. Figure 11.9 Biobased epoxy resin made from a grape seed tannin extract.
10. Figure 11.10 Examples of phenolic structures obtained by lignin depolymerisat...
11. Figure 11.11 Synthesis of di‐methyloxirane derivatives from vanillin derivati...
12. Figure 11.12 Synthesis of di‐methyloxirane derivative from dihydroeugenol.
13. Figure 11.13 Conversion pathways of eugenol, isoeugenol and 4‐vinyl guaiacol ...
14. Figure 11.14 Epoxidation of the allylated derivatives of gallic acid and vani...
15. Figure 11.15 Examples of bis‐ or trisphenols obtained by the coupling of lign...
16. Figure 11.16 Coupling reactions of ethyl‐dihydroferulate ester and vanillin. ...
17. Figure 11.17 Laccase oxidative coupling of vanillin and sinapyl alcohol.
18. Figure 11.18 Cross‐metathesis‐assisted coupling of glycidylated 4‐vinyl guaia...
19. Figure 11.19 Synthesis of epoxidized bis‐ and trisphenols from eugenol.
Chapter 12
1. Figure 12.1 Products of the photo‐induced degradation of curcumin.
2. Figure 12.2 Proposed formation of cleavage products in the photo‐induced and ...
3. Figure 12.3 Structure of (2Z,5E)‐2‐hydroxy‐6‐(4‐...
4. Figure 12.4 Structures of the main bicyclopentadione degradation product and ...
5. Figure 12.5 Structures of arachidonic acid, the cyclo‐oxygenase products PGG₂
6. Figure 12.6 The ‘sequential proton‐loss electron transfer’ mechanism leads to...
7. Figure 12.7 Products of the dimerization of curcumin and the reaction with li...
8. Figure 12.8 RP‐HPLC analysis with radiodetection of an autoxidation reaction ...
9. Figure 12.9 Degradation products of curcumin. The numbers correspond to the p...
10. Figure 12.10 The labelling strategy used to determine the origin of the oxyge...
11. Figure 12.11 Proposed mechanism for the exchange of oxygen in the transformat...
12. Figure 12.12 Demethoxy‐ and bisdemethoxy‐curcumin and their major oxidation p...
13. Figure 12.13 Proposed mechanism for the autoxidation of curcumin. Source: Gor...
14. Figure 12.14 Structures of a curcumin cyclopentadione endoperoxide (a suggest...
15. Figure 12.15 Suggested intramolecular [2 + 2] cycloaddition of a synthetic cu...
16. Figure 12.16 Products of the microbial degradation of curcumin, and structure...
17. Figure 12.17 Proposed mechanism for cleavage of curcumin via dioxetane interm...
Chapter 13
1. Figure 13.1 Partial scheme from the biosynthetic pathway of flavonoids. Enzym...
2. Figure 13.2 Homology modelling refers to protocols where a 3D structure of an...
3. Figure 13.3 Ingress and egress route characterization towards or from an enzy...
4. Figure 13.4 Protein–protein complex reconstruction. (a) On a grid surrounding...
5. Figure 13.5 Substrate channelling event observed in a DFR‐LAR complex. (a) Pa...
6. Figure 13.6 First model of a three‐enzyme metabolon involved in flavonoid bio...

Contributors

Anna K.F. Albertson
Department of Chemistry, McGill University, Montreal, Québec, Canada

Andrew C. Allan
Plant & Food Research, University of Auckland, Auckland, New Zealand

Pierre‐Marie Allard
Bioactive Natural Products Unit, School of Pharmaceutical Sciences, University of Geneva, Geneva, Switzerland

Serge Antonczak
Institute of Chemistry of Nice, University of Nice‐Sophia Antipolis, Nice, France

Chahinez Aouf
SPO SPIRAL, INRA Montpellier SupAgro, UMR 1083, Montpellier, France

Nicolas Barber‐Chamoux
Department of Cardiology, INSERM, UMR 766, Clermont‐Ferrand University Hospital, Clermont‐Ferrand, France

Guillaume Billerach
SPO SPIRAL, INRA Montpellier SupAgro, UMR 1083, Montpellier, France

Frédéric Bourgaud
Plant Advanced Technologies, Vandoeuvre, France

Sonam Chouhan
Natural Product Laboratory, Division of Biochemistry, Faculty of Basic Sciences, Sher‐e‐Kashmir University of Agricultural Sciences and Technology of Jammu, Jammu, India

Victor de Freitas
Faculty of Science, University of Porto, Porto, Portugal

Julien Diharce
Institute of Organic and Analytical Chemistry, University of Orléans, Orléans, France

Eric Dubreucq
SPO SPIRAL, INRA Montpellier SupAgro, UMR 1083, Montpellier, France

Léonor Duriot
Plant Advanced Technologies, Vandoeuvre, France

Richard V. Espley
Plant & Food Research, University of Auckland, Auckland, New Zealand

Hélène Fulcrand
SPO SPIRAL, INRA Montpellier SupAgro, UMR 1083, Montpellier, France

Carole Gavira
Plant Advanced Technologies, Vandoeuvre, France

Sanjay Guleria
Natural Product Laboratory, Division of Biochemistry, Faculty of Basic Sciences, Sher‐e‐Kashmir University of Agricultural Sciences and Technology of Jammu, Jammu, India

Alain Hehn
Agronomy and Environment Laboratory, INRA, University of Lorraine, Vandoeuvre, France

Dirk Hölscher
Max Planck Institute for Chemical Ecology, Jena; University of Kassel, Witzenhausen, Germany

Mattheos A.G. Koffas
Department of Chemical and Biological Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, USA

Miwa Kubo
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan

Romain Larbat
Agronomy and Environment Laboratory, INRA, University of Lorraine, Vandoeuvre, France

Jean‐Philip Lumb
Department of Chemistry, McGill University, Montreal, Québec, Canada

Benoit Mignard
Plant Advanced Technologies, Vandoeuvre, France

Dragan Milenkovic
Human Nutrition Unit, INRA, UMR 1019, University of Clermont Auvergne, Clermont‐Ferrand, France

Laurent‐Emmanuel Monfoulet
Human Nutrition Unit, INRA, UMR 1019, University of Clermont Auvergne, Clermont‐Ferrand, France

Christine Morand
Human Nutrition Unit, INRA, UMR 1019, University of Clermont Auvergne, Clermont‐Ferrand, France

Ryosuke Munakata
Agronomy and Environment Laboratory, INRA, University of Lorraine, Vandoeuvre, France

Alexandre Olry
Agronomy and Environment Laboratory, INRA, University of Lorraine, Vandoeuvre, France

Emerson Ferreira Queiroz
Bioactive Natural Products Unit, School of Pharmaceutical Sciences, University of Geneva, Geneva, Switzerland

Ludwig Ring
Biotechnology of Natural Products, Technical University Munich, Freising, Germany

Laurent Rouméas
SPO SPIRAL, INRA Montpellier SupAgro, UMR 1083, Montpellier, France

Claus Schneider
Department of Pharmacology, Vanderbilt University, Nashville, USA

Wilfried Schwab
Biotechnology of Natural Products, Technical University Munich, Freising, Germany

Kathy E. Schwinn
Plant & Food Research, Palmerston North, New Zealand

Kanika Sharma
Natural Product Laboratory, Division of Biochemistry, Faculty of Basic Sciences, Sher‐e‐Kashmir University of Agricultural Sciences and Technology of Jammu, Jammu, India

Chuankui Song
Biotechnology of Natural Products, Technical University Munich, Freising, Germany

Brenda S.J. Winkel
Department of Biological Sciences, Virginia Tech, Blacksburg, USA

Jean‐Luc Wolfender
Bioactive Natural Products Unit, School of Pharmaceutical Sciences, University of Geneva, Geneva, Switzerland

Jian Zha
Department of Chemical and Biological Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, USA

Preface

Polyphenols are secondary metabolites that are widely distributed in the plant kingdom and characterized by a large diversity of chemical structures. As supported by the international academic society Groupe Polyphénols, which organizes the biennial International Conference on Polyphenols (ICP), the term polyphenol should be exclusively used for plant secondary metabolites derived from the phenylpropanoid and/or polyketide pathway(s), featuring more than one phenolic ring and being devoid of any nitrogen‐based functional group (www.groupepolyphenols.com/the‐society/why‐bother‐with‐polyphenols). Several thousand structures have been isolated and characterized from plants so far, ranging from quite simple phenolic molecules to highly polymerized compounds with molecular weights of more than 30 000 Da. As a result of the huge diversity of structures, polyphenols possess diverse physicochemical properties. Over the years, scientists from all over the world have been fascinated by these molecules, trying to shed light on their chemistry, properties and physiological relevance in plants, humans and ecosystems. In addition, there is increasing interest in the valorization of polyphenols obtained as natural by‐products from, for example, the lignocellulose industry or agroindustrial waste streams for use as bioactive substances in dietary supplements and functional food, additives in food and cosmetic products to mediate antioxidant activity, natural coloration or flavours, and as raw materials for emerging products such as multifunctional polymer coatings or antibacterial packaging.

The book series Recent Advances in Polyphenol Research started in 2008 upon the occasion of the 24th ICP in Salamanca, Spain. The content of the first volume was mostly based on review articles written by plenary lecturers of the previous ICP, which had taken place in Winnipeg, Canada. Since then, this flagship publication of the Groupe Polyphénols has been released every two years to provide the reader with authoritative updates on various topics of polyphenol research written by ICP plenary lecturers and invited expert contributors.

This sixth volume of the series presents chapters representing a distillation of the topics covered during the 28th ICP, which was organized and hosted by the Technische Universität Wien in July 2016 in Vienna, Austria. This beautiful setting is represented on the cover by a photo of the dome of the stunning Art Nouveau church by Otto Wagner in Vienna. Participants were given a chance to visit this church in person during one of the social events organized during the conference.

Five main topics of the polyphenol sciences were selected for the scientific programme of this memorable ICP 2016 edition.

Chemistry and Physicochemistry, covering structures, reactivity, organic synthesis, molecular modelling, fundamental aspects, chemical analysis, spectroscopy, molecular associations, and interactions of polyphenols.
Biosynthesis, Genetics and Metabolic Engineering, covering molecular biology, genetics, enzymology, gene expression and regulation, trafficking, biotechnology, horticultural science, and molecular breeding related to polyphenols.
Roles in Plants and Ecosystems, covering plant growth and development, biotic and abiotic stress, resistance, ecophysiology, sustainable development, valorization, plant environmental system, forest chemistry, and lignin and lignan.
Food, Nutrition and Health, covering food ingredients, nutrient components, functional food, mode of action, bio‐availability and metabolism, food processing, influence on food and beverage properties, cosmetics, antioxidant activity of polyphenols.
Applied Polyphenolics, covering new findings on sources of isolated and standardized polyphenolic fractions and novel epigenetic polyphenol mechanisms, as well as industrial implementations of newly gleaned knowledge on polyphenols.

The 13 chapters of this volume highlight advances in our understanding of (i) polyphenol biosynthesis with a focus on (sub)cellular distribution and organization of the pathways, novel genes and transcription factors, (ii) bioactive and dietary compounds with a focus on health and taste, (iii) innovative sources of polyphenol compounds and their characterization and (iv) emerging products such as thermosetting polymers.

The conference was attended by 272 scientists from 40 countries, with 209 paper contributions, comprising 55 oral communications and 154 poster presentations.

The sixth volume of Recent Advances in Polyphenol Research contains chapters from 13 invited conference speakers and expert contributors. The support and assistance of the Groupe Polyphénols, the BachBERRY group, several Austrian academic associations and foundations, notably the Technische Universität Wien, the City of Vienna and the Vienna Convention Bureau, and several private sponsors are gratefully acknowledged, as the great success of the 28th International Conference on Polyphenols would not have been possible without their contributions. As a final note, the editors would also like to deeply thank all of the plenary, communication and poster presenters for the quality of their contributions, from basic science to more applied fields, and all of the attendees.

Heidi Halbwirth
Karl Stich
Véronique Cheynier
Stéphane Quideau