Recent Advances in Polyphenol Research, Volume 1

Fouad Daayf, Vincenzo Lattanzio

• Publisher: Wiley-Blackwell
• Year: 2009
• Print ISBN:
  9781405158374
• Edition: 1
• eBook ISBN:
  9781444302417
• Topic: Biological Sciences
• Subtopic: Botany
• Index: Biological Sciences

Polyphenols are the second most abundant class of substances in nature, and include tannins and flavonoids, many of which have extremely important antioxidant properties which have now been shown to have a key role in the prevention of cancer in humans.

This important book covers polyphenol chemistry, biosynthesis and genetic manipulation, ecology and plant physiology, food and nutritional aspects and the effects of polyphenols on health. Included within the contents are cutting edge chapters on biotic and abiotic stress in plants, safety and toxicity in foods, functionality and nutraceutical benefits in nutrition, and aspects of pharmaceutical and cosmetic discovery and development.

Sponsored by Groupe Polyphenols, this landmark book has been edited by Professor Fouad Daayf and Professor Vincenzo Lattanzio, who have drawn together an impressive list of internationally respected contributing authors, each providing a comprehensive review of the current situation regarding each important subject covered.

Recent Advances in Polyphenol Research is an important publication which will be of great use to chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, food scientists and nutritionists. Libraries in all universities and research establishments where these subjects are studied and taught should have copies of this book on their shelves.

Table of contents

• Contributors
• Preface
• Chapter 1 Plant Phenolics – Secondary Metabolites with Diverse Functions
• 1.1 Secondary metabolism in the interactions between plants and their environment
• 1.2 Function and use of plant phenolics
• 1.2.1 UV sunscreens
• 1.2.2 Phenolics as signal compounds
• 1.2.3 Phenolics as pigments
• 1.2.4 Phenolics and plant growth
• 1.2.5 Phenolics and plant defense
• 1.2.5.1 Fungal pathogens
• 1.2.5.2 Phenolics and plant–insect interactions
• 1.2.6 Plant phenolics and health
• 1.3 Note
• 1.4 References
• Chapter 2 Lignification: are Lignins Biosynthesized via simple Combinatorial Chemistry or via Proteinaceous Control and Template Replication?
• 2.1 Introduction
• 2.2 The current theory
• 2.3 Is there a need for a new theory?
• 2.3.1 The challenge hypothesis (proteinaceous control and template replication)
• 2.3.2 Has the challenge hypothesis become a theory?
• 2.4 Are criticisms of the current theory valid?
• 2.4.1 Lignification as a biochemical anomaly
• 2.4.2 The • • -ether frequency anomaly
• 2.4.3 ‘Obligatory’ linkages?
• 2.5 Is there anything wrong with the dirigent hypothesis?
• 2.5.1 Monomer substitution
• 2.5.1.1 Has monomer substitution been disproven?
• 2.5.1.2 Malleability of lignification: what makes a good monolignol substitute?
• 2.5.2 ‘Well-defined primary structure’
• 2.5.2.1 Sequencing of lignin oligomers
• 2.5.2.2 Monomer-independent sequences
• 2.5.2.3 The ‘urgent need to sequence lignin primary structure’
• 2.5.3 Lignins’ racemic nature
• 2.5.3.1 The ‘number of isomers’ problem
• 2.5.4 Comments on template replication
• 2.5.5 Polymer branching
• 2.6 Why the new hypothesis is not in contention
• 2.7 Is lignification a biochemical anomaly?
• 2.7.1 Ferulate dehydrodimerization is combinatorial
• 2.7.2 Polysaccharide primary structure is NOT absolutely dictated
• 2.8 Summary comments on the dirigent/replication hypothesis
• 2.9 Conclusions
• 2.10 Notes
• 2.11 References
• Chapter 3 Flavonoid–Protein Binding Processes and their Potential Impact on Human Health
• 3.1 Introduction
• 3.2 Biologically relevant chemical properties of flavonoids
• 3.3 Binding processes prior to absorption
• 3.4 Binding processes involved in flavonoid bioavailability
• 3.4.1 Absorption and conjugation
• 3.4.2 Transport in plasma
• 3.4.3 Tissue distribution and cellular metabolism
• 3.5 Binding processes involved in the potential health effects of flavonoids
• 3.5.1 Inhibition of enzymes involved in ROS production
• 3.5.2 Modulation of the redox properties of flavonoids by binding to proteins
• 3.5.3 Inhibition of protein kinases
• 3.5.4 Inhibition of cytochrome P450 enzymes
• 3.5.5 Regulation of gene expression
• 3.6 Conclusion
• 3.7 References
• Chapter 4 Methods for Synthesizing the Cocoa-Derived Oligomeric Epi-Catechins – Observations on the Anticancer Activity of the Cocoa Polyphenols
• 4.1 Introduction
• 4.2 Synthesis of procyanidins
• 4.2.1 General chemical properties of cocoa procyanidins
• 4.2.2 Earlier synthetic work
• 4.2.3 The synthesis of benzyl-protected building blocks
• 4.2.4 Inter-flavan bond formation using benzyl-protected building blocks
• 4.2.5 Establishment of inter-flavan bond stereochemistry
• 4.2.6 Further developments
• 4.3 Anticancer activity
• 4.4 Acknowledgments
• 4.5 References
• Chapter 5 Gene Discovery and Metabolic Engineering in the Phenylpropanoid Pathway
• 5.1 Introduction
• 5.2 Biosynthesis and functions of isoflavones
• 5.3 Dietary sources of isoflavones
• 5.4 Metabolic engineering of isoflavones
• 5.4.1 Metabolic engineering by ectopic expression of IFS
• 5.4.2 Structural biology-assisted design and metabolic engineering with an artificial bifunctional IFS enzyme
• 5.5 Gene discovery in the proanthocyanidin biosynthetic pathway
• 5.5.1 Structural genes for PA biosynthesis
• 5.5.2 Regulatory genes for PA biosynthesis
• 5.6 Metabolic engineering of PAs in plants
• 5.7 Glycosyltransferases for modification of phenylpropanoid compounds – in-vitro biochemistry and in-vivo function
• 5.7.1 UGTs active with non-flavonoid phenolic compounds
• 5.7.2 Glycosylation of flavonoid compounds
• 5.7.3 Problems for the functional annotation of UGTs
• 5.8 Concerted strategies for metabolic engineering
• 5.9 References
• 5.10 Abbreviation list of the pathway genes
• Chapter 6 Recent Advances in the Molecular Biology and Metabolic Engineering of Flavonoid Biosynthesis in Ornamental Plants
• 6.1 Introduction
• 6.2 Metabolic engineering of flavonoid production in flowers
• 6.2.1 Engineering yellow flower colors
• 6.2.2 Engineering blue flower colors
• 6.3 Anthocyanic vacuolar inclusions
• 6.4 Regulation of anthocyanin biosynthesis
• 6.5 Concluding comments
• 6.6 References
• Chapter 7 Recent Advances in the Field of Anthocyanins – Main Focus on Structures
• 7.1 Introduction
• 7.2 Anthocyanidins
• 7.3 Anthocyanidin equilibrium forms
• 7.4 New anthocyanin glycosides
• 7.5 New anthocyanin acylglycosides
• 7.6 Flavonoid complexes including at least one anthocyanidin subunit
• 7.7 Metalloanthocyanins
• 7.8 Biosynthesis and molecular biology
• 7.9 Anthocyanin localization in plant cells
• 7.10 Acknowledgments
• 7.11 Notes
• 7.12 References
• Chapter 8 Salicylic Acid and Induced Plant Defenses
• 8.1 Induced resistance and phenolics
• 8.2 The biosynthesis of SA
• 8.3 The network of signaling and the action of SA
• 8.4 Conclusions
• 8.5 Acknowledgment
• 8.6 References
• Chapter 9 Phenols and the Onset and Expression of Plant Disease Resistance
• 9.1 Introduction
• 9.2 Biosynthetic origins of defense-associated phenolic compounds
• 9.3 Phenolic compounds as preformed defenses
• 9.3.1 Resistance of onion bulbs
• 9.3.2 Fusarium wilt of carnation
• 9.3.3 Mango fruit and Alternaria
• 9.3.4 Regulation of preformed antifungal compounds by phenols in avocado
• 9.3.5 Chlorogenic acid and the infection of stone fruit by Monilinia
• 9.4 Active defense
• 9.5 Localized defenses
• 9.5.1 Phenolic phytoalexins
• 9.5.2 Phenolic structural defenses
• 9.5.3 Plant phenols and induced disease resistance
• 9.6 Responses of the induced plant
• 9.6.1 Induced resistance in green bean and C. lindemunthianum
• 9.6.2 Acibenzolar-S-methyl mediated induced resistance
• 9.6.3 Plant growth-promoting rhizobacteria and induced resistance
• 9.6.4 Silicon as a modulator of defense and phenolic compounds
• 9.7 Chemical induction of phenolic compounds and resistance
• 9.7.1 Structural phenolic compounds and induced resistance
• 9.7.2 Antioxidant activity of phenolic compounds and plant defense
• 9.8 Phenols and defense: a multitude of roles
• 9.9 Acknowledgment
• 9.10 References
• Chapter 10 Bioactivity, Absorption, and Metabolism of Anthocyanins
• 10.1 Introduction
• 10.1.1 Structural characteristics
• 10.2 Bioactivity
• 10.2.1 Antioxidant activity
• 10.2.2 Anti-inflammatory effects
• 10.2.3 Anti-atherogenic effects
• 10.2.4 Anticarcinogenic effects
• 10.2.5 Antibacterial and antiviral activity
• 10.2.6 Neuroprotective effects
• 10.2.7 Prevention of obesity
• 10.2.8 Gastric protective effects
• 10.2.9 Improvement of vision
• 10.3 Absorption of anthocyanins
• 10.3.1 Variability of absorption
• 10.3.1.1 Variations in dosage
• 10.3.1.2 Chemical structure of the anthocyanins
• 10.3.1.3 Food matrix
• 10.3.1.4 Analytical methodology
• 10.3.2 Elimination
• 10.3.3 The concentration of anthocyanins in human blood and urine is very low
• 10.3.4 Suggested mechanisms of anthocyanin absorption
• 10.3.5 Structural transformations of anthocyanins
• 10.4 Metabolism of anthocyanins
• 10.4.1 Human studies
• 10.4.2 Animal studies
• 10.4.2.1 Rat studies
• 10.4.2.2 Pig studies
• 10.4.3 Potential mechanisms of anthocyanin metabolism
• 10.5 Conclusions
• 10.6 References
• Chapter 11 Bioavailability, Metabolism, and Bioactivity of Food Ellagic Acid and Related Polyphenols
• 11.1 Introduction
• 11.2 Ellagitannins and ellagic acid as examples of bioactive polyphenols
• 11.3 Evaluation of antioxidant activity in vitro
• 11.4 Biological activity associated with ellagitannin-rich food intake; clinical studies
• 11.5 Questions arising after the demonstration of the large antioxidant activity in vitro and the biological activity associated with the intake of ellagitannin-rich food
• 11.5.1 Bioavailability and metabolism of ellagitannins and ellagic acid and distribution of the metabolites in different tissues
• 11.5.2 Evaluation of the biological activity of ellagitannin metabolites produced in vivo
• 11.6 Conclusion
• 11.7 Acknowledgments
• 11.8 References
• Chapter 12 Multiplicity of Phenolic Oxidation Products in Apple Juices and Ciders, from Synthetic Medium to Commercial Products
• 12.1 Introduction
• 12.2 Preparation and characterization of the caffeoylquinic acid o-quinone solution
• 12.3 Incubation of caffeoylquinic acid o-quinone in model solutions
• 12.3.1 Incubation of caffeoylquinic acid o-quinone with caffeoylquinic acid
• 12.3.2 Incubation of caffeoylquinic acid o-quinone with ( ••) -epicatechin
• 12.4 LC-MS analysis of oxidation products in commercial apple beverages
• 12.5 Conclusions
• 12.6 Acknowledgments
• 12.7 References
• Chapter 13 Phytoestrogens in Drug Discovery for Controlling Steroid Biosynthesis
• 13.1 Introduction
• 13.2 Aromatase
• 13.2.1 Natural phytoestrogens as aromatase inhibitors
• 13.2.1.1 Anti-aromatase activity of phytoestrogens in human placental microsome-based assays
• 13.2.1.2 Anti-aromatase activity of phytoestrogens in cell-based assays
• 13.2.1.3 Anti-aromatase activity of phytoestrogens in recombinant-enzyme assays
• 13.2.1.4 The anti-aromatase activity of various phytoestrogens
• 13.2.2 The structure–activity relationship of phytoestrogens
• 13.2.3 Phytoestrogens as lead compounds for aromatase inhibition
• 13.3 17B-Hydroxysteroid dehydrogenases and their inhibition by phytoestrogens
• 13.3.1 17B-HSD type 1
• 13.3.1.1 Binding of phytoestrogens to 17 • -HSD1
• 13.3.2 17B-HSD types 2 and 4
• 13.3.3 Fungal 17B -HSDcl
• 13.3.3.1 Binding of phytoestrogens to 17 B -HSDcl
• 13.3.4 17B -HSD type 3
• 13.3.5 17B -HSD type 5
• 13.3.6 Phytoestrogens as lead compounds for 17B -HSD inhibitors
• 13.4 Conclusions
• 13.5 Acknowledgments
• 13.6 References
• Chapter 14 Recent Advances in the Chemical Synthesis and Biological Activity of Phenolic Metabolites
• 14.1 Introduction
• 14.2 The different sites of generation of phenolic metabolites
• 14.2.1 The saliva
• 14.2.2 The stomach
• 14.2.3 The small intestine
• 14.2.4 The colon
• 14.2.5 The liver
• 14.2.6 Metabolism at the target tissues or cells
• 14.3 Nature of the metabolites of phenolic compounds
• 14.3.1 Flavone and flavonol metabolites
• 14.3.2 Flavanonone and flavanonol metabolites
• 14.3.3 Flavan 3-ol metabolites
• 14.3.4 Ellagic tannin metabolites
• 14.3.5 Lignan metabolites
• 14.3.6 Isoflavone metabolites
• 14.3.7 Hydroxycinnamic acid metabolites
• 14.3.8 Curcumin metabolites
• 14.3.9 Resveratrol metabolites
• 14.4 The chemical synthesis of phenolic conjugates
• 14.4.1 The preparation of O-glucuronides
• 14.4.2 The preparation of O-sulfates
• 14.5 The biological properties of phenolic conjugates
• 14.5.1 Antioxidant properties
• 14.5.1.1 Flavonol conjugates
• 14.5.1.2 Flavone conjugates
• 14.5.1.3 Flavanone conjugates
• 14.5.1.4 Flavan 3-ol conjugates
• 14.5.1.5 Isoflavone conjugates
• 14.5.1.6 The case of the 7-O-conjugates
• 14.5.2 Pro-oxidant properties
• 14.5.3 Interaction with signaling cascades
• 14.5.4 Enzyme inhibition
• 14.5.4.1 Aldose reductase
• 14.5.4.2 B -glucuronidase
• 14.5.4.3 Xanthine oxidase
• 14.5.4.4 Glycerol 3-phosphate dehydrogenase
• 14.5.4.5 Cyclooxygenase-2
• 14.5.5 Effect on vascular function and angiogenesis
• 14.5.6 Non-covalent binding to proteins
• 14.5.7 Activity of microbial and tissular metabolites
• 14.6 The cellular transport of phenolic conjugates
• 14.6.1 Cellular efflux
• 14.6.2 Cellular uptake
• 14.7 Conclusions
• 14.8 References
• Chapter 15 Polyphenols and Gene Expression
• 15.1 Introduction
• 15.2 The effects of polyphenols on the expression of genes underlying detoxification mechanisms
• 15.3 Polyphenols and the expression of genes underlying cancer-relevant processes
• 15.4 The impact of polyphenols on the expression of genes underlying atherosclerosis-relevant processes
• 15.5 References
• Index