پیشرفت‌های اخیر در پژوهش‌های پلی‌فنول، جلد ۱ ۲۰۰۹
Recent Advances in Polyphenol Research, Volume 1 2009

1. Contributors

2. Preface

3. 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

16. 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

46. 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

62. 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

74. 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

92. 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

101. 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

114. 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

121. 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

146. 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

177. 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

188. 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

198. 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

220. 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

266. 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

272. Index