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Recent Advances in Polyphenol Research, Volume 6

Recent Advances in Polyphenol Research, Volume 6





Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They are crucial constituents of a large and diverse range of biological functions and processes, and provide many benefits to both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions, are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents.

This sixth volume of the highly regarded Recent Advances in Polyphenol Research series is edited by Heidi Halbwirth, Karl Stich, Véronique Cheynier and Stéphane Quideau, and is a continuance of the series’ tradition of compiling a cornucopia of cutting-edge chapters, written by some of the leading experts in their respective fields of polyphenol sciences. Highlighted herein are some of the most recent and pertinent developments in polyphenol research, covering such major areas as:

  • Chemistry and physicochemistry
  • Biosynthesis, genetics & metabolic engineering
  • Roles in plants and ecosystems
  • Food, nutrition & health
  • Applied polyphenols

This book is a distillation of the most current information, and as such, will surely prove an invaluable source for chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists.  



1 The Lignans: A Family of Biologically Active Polyphenolic Secondary Metabolites
Anna K.F. Albertson and Jean-Philip Lumb

1.1 Introduction

1.2 Biosynthesis of lignans

1.3 Synthetic approaches to lignans and derivatives

1.3.1 Biomimetic and bio-inspired approaches

1.3.2 Dibenzylbutyrolactones

1.3.3 Arylnaphthalenes and Aryltetralins

1.3.4 2,5-Diaryltetrahydrofurans

1.3.5 2-Aryl-4-benzyltetrahydrofurans

1.3.6 Furofurans

1.3.7 Dibenzocyclooctadienes

1.4 Conclusion


2 Anthocyanin accumulation is controlled by layers of repression
Andrew C Allan, Kathy E. Schwinn and Richard V. Espley

2.1 Introduction

2.2 MYBs and bHLHs directly activate anthocyanin production

2.3 Exciting phenotypes in horticulture are often caused by variations in the expression of key MYBs

2.4 Is there a cost to the plant of over-accumulation of anthocyanins?

2.5 Controlling anthocyanin levels

2.5.1 Fine control of MYB activator expression

2.6 The MYB activator is degraded at night

2.7 MYB activator competes with MYB repressors

2.8 miRNA targeted degradation of MYB transcript

2.9 Turnover of anthocyanin vacuolar content by peroxidases

2.10 Summary


3 The subtleties of subcellular distribution: pointing the way to underexplored functions for flavonoid enzymes and end products
Brenda S.J. Winkel

3.1 Multi-enzyme complexes and metabolic networks

3.2 New insights from global surveys of protein interactions

3.3 The flavonoid metabolon

3.3.1 Earliest evidence

3.3.2 Protein interactions in Arabidopsis

3.3.3 Corroboration in other species

3.4 Subcellular distribution of flavonoid enzymes and evidence for alternative metabolons

3.4.1 Cytoplasmic and vacuolar localization

3.4.2 Plastid and mitochondrial localization

3.4.3 Nuclear localization Flavonoids Flavonoid enzymes

3.5 Post-translational modifications – an underexplored area of flavonoid metabolism

3.6 Why do we need to know?

3.7 Future prospects


4 Transcriptional and metabolite profiling analyses uncover novel genes essential for polyphenol accumulation
Wilfried Schwab, Ludwig Ring and Chuankui Song

4.1 Introduction

4.2 Transcriptional and metabolite profiling analyses in strawberry fruit

4.2.1 Analysis of soluble phenolics

4.2.2 Transcript analysis

4.3 Characterization of Peroxidase

4.2.3 Expression analysis

4.2.4 Functional analysis

4.4 Competition of the lignin and flavonoid/anthocyanin pathways as demonstrated by the activity of peroxidase

4.5 Candidate genes putatively correlated with phenolics accumulation in strawberry fruit

4.5.1 Selection of candidates

4.5.2 Effects on metabolites

4.6 Acylphloroglucinol biosynthesis in strawberry fruit

4.6.1 Downregulation of CHS/VPS activity

4.4.2 Isotope labeling experiment

4.7 Glucosylation of acylphloroglucinols

4.7.1 Total in vitro synthesis of strawberry APG glucosides

4.7.2 Downregulation of UGT71K3 in strawberry fruit

4.7.3 Promiscuous activity as an anthocyanidin glucosyltransferase

4.8 Conclusion


5 Dietary (poly)phenols and vascular health
Christine Morand, Nicolas Barber-Chamoux, Laurent-Emmanuel Monfoulet and Dragan Milenkovic

5.1 Introduction

5.2 Vascular health: a prerequisite to prevent cardiometabolic diseases and cognitive decline

5.2.1 Vascular function and cardiometabolic diseases

5.2.2 Vascular function and cognitive decline

5.3 Diet and vascular health

5.4 (Poly)phenols: a major family of dietary plant bioactive compounds

5.5 Fate of (poly)phenols in the body and biological activities

5.6 Nutritional interest of flavonoids in protecting cardiovascular health

5.7 Limitation of knowledge and strategy for research

5.8 Findings from translational research on citrus flavanones and vascular health

5.9 Conclusion


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
Dirk Hölscher

6.1 Introduction

6.2 The plant genus Hypericum

6.3 Phenylphenalenones: plant secondary metabolites of the Haemodoraceae

6.4 Phenalenone-type phytoalexins

6.5 Laser microdissection and cryogenic NMR as a combined tool for cell type-specific metabolite profiling

6.6 Matrix-free UV-laser desorption/ionization (LDI) at the single-cell level: distribution of secondary metabolites of Hypericum species

6.7 LDI-MSI-based detection of phenalenone-type phytoalexins in a banana-nematode-interaction

6.8 LDI-FT-ICR-MSI reveals the occurrence of phenylphenalenones in red paracytic stomata



7 Metabolomics strategies for the dereplication of polyphenols and other metabolites in complex natural extracts
Jean-Luc Wolfender, Pierre-Marie Allard, Miwa Kubo and Emerson Ferreira Queiroz

7.1 Introduction

7.2 Metabolite profiling and metabolomics

7.2.1 Resolution and throughput improvement of metabolite profiling methods

7.3 Metabolite annotation and dereplication

7.4 Targeted isolation of original polyphenols

7.5 Conclusions


8 Polyphenols from plant roots: an expanding biological frontier
Ryosuke Munakata, Romain Larbat, Léonor Duriot, Alexandre Olry, Carole Gavira,  Benoit Mignard, Alain Hehn and Frédéric Bourgaud

8.1 Introduction

8.2 Polyphenols in the roots vs shoots: not more, not less, but often different

8.2.1 Examples of root specific polyphenols Flavonoids/Isoflavonoids Naphtoquinones Phenylphenalenone Caffeic acid dihydroxyphenethyl glucosides

8.2.2 Phenolics in roots: general evolutionary context, distribution and translocation

8.3 Allelochemical functions of root polyphenols

8.3.1 Plant microbe interactions Rhizobia Arbuscular mycorrhizal fungi Plant growth promoting Rhizobacteria Endophytes Soil.borne plant pathogens

8.3.2 Plant-nematode and plant-insect herbivore interactions

8.3.3 Plant allelopathy

8.4 Physiological functions of root polyphenols in plants

8.4.1 Inhibition of auxin transport

8.4.2 Nutrient uptake in the rhizosphere

8.4.3 Detoxifying agents (i.e., anti-oxidizing agent)

8.5 Biotechnologies to produce root polyphenols

8.5.1 Production of valuable polyphenols in plant cell/tissue culture

8.5.2 Production of valuable root polyphenols in organ culture systems Hairy roots cultivation systems Adventitious root cultures

8.5.3 Production of polyphenols by aeroponic/hydroponic cultivation systems

8.5.4 Metabolic engineering for the production of root polyphenols Bacteria used as a platform of production Production in yeast

8.6 Conclusion


9 Biosynthesis of polyphenols in recombinant microorganisms: A path to sustainability
Kanika Sharma, Jian Zha, Sonam Chouhan, Sanjay Guleria and Mattheos A.G. Koffas

9.1 Introduction

9.2 Flavonoids

9.2.1 Biosynthesis of flavonoids and their derivatives

9.2.2 Metabolic engineering of flavonoids and their derivatives

9.3 Stilbenes

9.3.1 Biosynthesis of resveratrol and its derivatives

9.3.2 Metabolic engineering of resveratrol and its derivatives

9.4 Coumarins

9.4.1 Biosynthesis of coumarins

9.4.2 Metabolic engineering of coumarins

9.5 Summary and conclusions


10 Revisiting wine polyphenols chemistry in relation to their sensorial characteristics
Victor de Freitas

10.1 Introduction

10.2 Astringency of polyphenols

10.2.1 Astringency perception mechanisms

10.2.2 Physiological response of astringency

10.3 Bitter taste of polyphenols

10.4 Red Wine Colour

10.5 Conclusion


11 Advances in biobased thermosetting polymers
Hélène Fulcrand, Laurent Rouméas, Guillaume Billerach, Chahinez Aouf and Eric Dubreucq

11.1 Introduction

11.2 Industrial sources of polyphenols

11.3 Principles of thermoset production

11.4 Relationships between structure and reactivity of polyphenols

11.4.1 Lignins Phenolation Methylolation (hydroxymethylation) Demethylation

11.4.2 Tannins

11.5 Thermosets from industrial lignins and tannins

11.5.1 Uses in phenol-aldehyde materials The partial substitution of phenol in PF-based resins Fortification of synthetic resins Full phenol substitution in PF-based resins Tannins self-condensation and tannins-lignins condensation

11.5.2 Uses in Polyurethanes Reaction of polyphenol hydroxy groups with isocyanate Isocyanate-free polyurethane

11.5.3 Uses in Polyesters

11.5.4 Uses in Epoxy resins As epoxy prepolymers As hardeners

11.6 Depolymerization of lignins and tannins to produce phenolic building blocks and their glycidylether derivatives

11.6.1 Lignin depolymerization

11.6.2 Condensed tannin depolymerization Quantitative production of flavan-type monomers by depolymerization Production of epoxy thermosets with furan depolymerization products

11.7 Development of dimethyloxirane monophenols and bisphenols as thermosetting building blocks

11.7.1 Conversion of di-functional monophenols into dimethyloxirane monophenols Glycidylation of difunctional monophenols Functionalization through epoxidation

11.7.2 Hemisynthesis of dimethyloxirane bisphenols and trimethyloxirane trisphenols Coupling monophenols through phenolic hydroxy groups

11.8 Conclusion

12 Understanding the misunderstood: Products and mechanisms of the degradation of curcumin
Claus Schneider

12.1 Introduction

12.2 Degradation of curcumin – A historical and personal perspective

12.3 The degradation is an autoxidation

12.4 Novel products of the degradation/autoxidation of curcumin

12.5 Transformation of curcumin to bicyclopentadione

12.6 A proposed mechanism for the autoxidation of curcumin

12.7 Microbial degradation of curcumin

12.8 Concluding remarks


13 How to model a metabolon: theoretical strategies
Julien Diharce and Serge Antonczak

13.1 Introduction

13.2 Localization

13.3 Existing strutures

13.4 3D structures of enzymes – Homology Modeling

13.5 Ways of access to active sites – Randomly Accelerated Molecular Dynamics

13.6 Protein-Protein association – Protein-Protein Docking

13.7 Substrate channeling and molecular dynamics

13.8 Metabolon

13.9 Conclusion