Flavonoids Chemistry Biochemistry And Applications 1st Edition by Øyvind Andersen, Kenneth Markham 0849320216 9780849320217

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ISBN 10: 0849320216 

ISBN 13: 9780849320217

Author: Øyvind M. Andersen, kenneth R. Markham 

Advances in the flavonoid field have been nothing short of spectacular over the last 20 years. While the medical field has noticed flavonoids for their potential antioxidant, anticancer and cardioprotectant characteristics, growers and processors in plant sciences have utilized flavonoid biosynthesis and the genetic manipulation of the flavonoid

Flavonoids Chemistry Biochemistry And Applications 1st Table of contents:

1. Separation and Quantification of Flavonoids

1.1 Introduction

1.2 Extraction

1.3 Preparative Separation

1.3.1 Preliminary Purification

1.3.2 Preparative Methods

1.3.2.1 High-Performance Liquid Chromatography

1.3.2.2 Medium-Pressure Liquid Chromatography

1.3.2.3 Centrifugal Partition Chromatography

1.4 Analytical Methods

1.4.1 Sample Preparation

1.4.2 Thin-Layer Chromatography

1.4.3 High-Performance Liquid Chromatography

1.4.4 High-Performance Liquid Chromatography-Ultraviolet Spectrophotometry

1.4.5 High-Performance Liquid Chromatography-Mass Spectrometry

1.4.6 High-Performance Liquid Chromatography-Nuclear Magnetic Resonance

1.4.7 Capillary Electrophoresis

1.5 Outlook

References

2. Spectroscopic Techniques Applied to Flavonoids

2.1 Introduction

2.2 NMR Spectroscopy

2.2.1 Introduction

2.2.2 NMR Solvents

2.2.3 NMR Experiments

2.2.3.1 COSY and TOCSY

2.2.3.2 1H−13C Heteronuclear NMR Experiments

2.2.3.3 Improved Versions of the HMBC Experiment

2.2.3.4 Nuclear Overhauser Enhancement Spectroscopy

2.2.3.5 Rotating Frame Overhauser Effect Spectroscopy

2.2.3.6 Two- and Three-Dimensional HSQC-TOCSY, HSQC-NOESY, HSQC-ROESY, HMQC-NOESY, HMQC-ROESY

2.2.4 Solid-State NMR

2.2.5 Liquid Chromatography-NMR

2.2.6 NMR Data on Flavonoid Classes

2.3 Mass Spectrometry

2.3.1 MS Instrumentation and Techniques

2.3.1.1 Electron Impact and Chemical Ionization

2.3.1.2 Fast Atom Bombardment

2.3.1.3 Matrix-Assisted Laser Desorption Ionization

2.3.1.4 Electrospray Ionization and Atmospheric Pressure Chemical Ionization

2.3.1.5 Tandem (MS–MS) and Multiple (MSn) Mass Spectrometry

2.3.1.6 Mass Analyzers

2.3.2 Coupled Techniques Involving Mass Spectrometry

2.3.2.1 Gas Chromatography Coupled to Mass Spectrometry

2.3.2.2 High-Performance Liquid Chromatography Coupled to Mass Spectrometry

2.3.2.3 Capillary Electrophoresis Coupled to Mass Spectrometry

2.3.3 Structural Information

2.3.4 Quantitative Considerations

2.4 Vibrational Spectroscopy (IR and Raman)

2.4.1 IR and Raman Spectroscopic Techniques in Studies of Flavonoid Structures

2.4.2 IR and Raman Spectroscopic Techniques in Studies of Complexes Involving Flavonoids

2.4.3 Two-Dimensional IR Analysis

2.4.4 Coupled Techniques Involving Vibrational Spectroscopy

2.4.5 Near-Infrared Spectroscopy

2.5 Ultraviolet-Visible Absorption Spectroscopy

2.5.1 Online UV Absorption Spectroscopy in Chromatography

2.5.2 UV–Vis Absorption Spectroscopy on Anthocyanins

2.5.3 UV–Vis Absorption Spectroscopy Involving Flavonoids in Complexes

2.6 Color Measurements Using Commission Internationale de l’Eclairage Specifications

2.6.1 Colorimetric Studies on Pure Anthocyanins

2.6.2 Anthocyanin-Based Colors of Plants and Products Derived Therefrom

2.7 Circular Dichroism Spectroscopy

2.7.1 Determination of Absolute Flavonoid Configuration

2.7.2 Circular Dichroism in Studies of Molecular Flavonoid Interaction

2.8 X-Ray Crystallography

2.8.1 X-Ray Studies on Flavonoid Structures

2.8.2 X-Ray Studies on Complexes Involving Flavonoids

References

3. Molecular Biology and Biotechnology of Flavonoid Biosynthesis

3.1 The Scope of the Review

3.2 Overview of Flavonoid Biosynthesis

3.3 Biosynthesis of Flavonoid Precursors

3.3.1 Acetyl-CoA Carboxylase

3.3.2 Phenylalanine Ammonia Lyase

3.3.3 Cinnamate 4-Hydroxylase

3.3.4 4-Coumarate:CoA Ligase

3.3.5 Modification of Hydroxycinnamic Acid-CoA Esters

3.4 Formation of Anthocyanins

3.4.1 Chalcone Synthase

3.4.2 Chalcone Isomerase

3.4.3 Flavanone 3β-Hydroxylase

3.4.4 Dihydroflavonol 4-Reductase

3.4.5 Anthocyanidin Synthase

3.4.6 Formation of Anthocyanidin 3-O-Glycoside

3.4.7 Formation of 3-Deoxyanthocyanin

3.4.8 Flavonoid 3′-Hydroxylase and Flavonoid 3′,5′-Hydroxylase

3.4.9 Anthocyanin Modification Enzymes

3.4.9.1 Anthocyanin Glycosyltransferases

3.4.9.2 Anthocyanin Methyltransferases

3.4.9.3 Anthocyanin Acyltransferases

3.5 Formation of Proanthocyanidins and Phlobaphenes

3.5.1 Leucoanthocyanidin Reductase

3.5.2 Anthocyanidin Reductase

3.5.3 Proanthocyanidin Polymerization

3.6 Formation of Flavones and Flavonols

3.7 Flavone and Flavonol Modification Enzymes

3.7.1 Flavone and Flavonol Glycosyltransferases

3.7.2 Flavone and Flavonol Methyltransferases

3.7.3 Flavone and Flavonol Sulfotransferases

3.8 Biosynthesis of 5-Deoxyflavonoids

3.9 Biosynthesis of Isoflavonoids and their Derivatives

3.9.1 2-Hydroxyisoflavanone Synthase

3.9.2 4′-O-Methylation

3.9.3 Isoflavone 2′- and 3′-Hydroxylase

3.9.4 Isoflavone Reductase

3.9.5 Vestitone Reductase

3.9.6 Pterocarpan 6a-Hydroxylase

3.9.7 SAM:6a-Hydroxymaackiain 3-O-Methyltransferase

3.9.8 Pterocarpan Prenyltransferases

3.9.9 Prenylpterocarpan Cyclases

3.9.10 Isoflavonoid Glucosyltransferases and Malonyltransferases

3.9.11 Flavonoid 6-Hydroxylase

3.10 Formation of Aurones

3.11 Other Activities of Flavonoid Biosynthesis

3.12 Vacuolar Importation of Flavonoids

3.13 Enzyme Complexes and Metabolic Channeling

3.14 Assigning Enzyme Function from DNA Sequence or Recombinant Proteins

3.15 Regulation of Flavonoid Gene Transcription

3.15.1 Environmental Regulation of Early Biosynthetic Steps

3.15.2 Regulation of Anthocyanin Biosynthesis

3.15.3 Regulation of Proanthocyanidin Biosynthesis

3.15.4 Regulation of the Production of Other Flavonoids

3.16 Genetic Modification of Flavonoid Biosynthesis

3.16.1 Preventing Flavonoid Production

3.16.2 Redirecting Substrate in the Flavonoid Pathway

3.16.3 Introducing Novel Flavonoid Compounds

3.16.3.1 Chalcones, Aurones, and Flavonols

3.16.3.2 Altering Dihydroflavonol 4-Reductase Activity

3.16.3.3 Isoflavonoids

3.16.3.4 Altering B-Ring Hydroxylation

3.16.3.5 Altering Secondary Modifications

3.16.4 Modulating Pathway Regulation

3.17 Concluding Comments

3.18 Acknowledgments

References

4. Flavonoids in Foods

4.1 Introduction

4.2 Database Development

4.2.1 Database Development

4.2.2 Selection of Foods and Flavonoid Classes

4.2.3 Collation and Evaluation of Literature Sources

4.3 Database of Flavonoids in Foods

4.3.1 Fruits

4.3.2 Vegetables

4.3.3 Beverages

4.3.4 Miscellaneous Foods

4.4 Quality and Completeness of Flavonoid Content Data

4.4.1 Factors Affecting Flavonoid Content of Food

4.4.1.1 Analytical Variations

4.4.1.2 Environmental Factors

4.4.1.3 Species Characteristics

4.4.1.4 Processing and Storage

4.5 Estimated Dietary Flavonoid Intake

4.5.1 Estimation of Dietary Flavonoid Intake

4.5.2 Previous Estimations of Dietary Flavonoid Intake

4.5.3 Estimation of Scottish Dietary Flavonoid Intake Using the New Comprehensive Flavonoid Database

4.5.4 Comparison with Other Estimates of Dietary Flavonoid Intake

4.5.5 Future Requirements to Improve Database

4.6 Conclusions

4.7 Acknowledgments

References

Appendix 1

Botanical Names of Fruits

Botanical Names of Vegetables

Botanical Names of Herbs and Spices

Botanical Names of Legumes

Appendix 2: References Used for Database Compilation

5. Flavonoids in Wine

5.1 Introduction

5.2 Analytical Procedures

5.2.1 Extraction and Fractionation of Flavonoids from Grape and Wine

5.2.2 Analysis of Lower Molecular Weight Flavonoids

5.2.2.1 ]HPLC Coupled to Mass Spectrometry

5.2.2.2 Analysis of Flavonoid Constitutive Moieties

5.2.2.3 Nuclear Magnetic Resonance

5.2.3 Analysis of Higher Molecular Weight Flavonoids

5.2.3.1 Acid-Catalyzed Cleavage in the Presence of Nucleophilic Agents

5.2.3.2 Mass Spectrometry

5.3 Grape Flavonoids

5.3.1 Structure and Distribution in Grape

5.3.1.1 Anthocyanins

5.3.1.2 Flavanols

5.3.1.3 Flavonols, Flavones, and Dihydroflavonols

5.3.2 Impact ofVarietal and Environmental Factors on Grape Flavonoids

5.4 Extraction of Grape Flavonoids into the Wine

5.5 Reactions of Flavonoids in Musts and Wines

5.5.1 Reactivity ofFlavonoid Compounds

5.5.2 Enzymatic Reactions

5.5.2.1 Hydrolytic Enzymes

5.5.2.2 Enzymatic Oxidation and Subsequent Reactions

5.5.3 Chemical Reactions

5.5.3.1 Products of Direct Anthocyanin-Flavanol Addition

5.5.3.2 Products of Acetaldehyde-Mediated Reactions

5.5.3.3 Other Pyranoanthocyanins

5.5.3.4 Condensation Reactions with Other Aldehydes

5.5.4 Factors Controlling Flavonoid Reactions in Wine

5.6 Physicochemical and Organoleptic Properties of Grape and Wine Flavonoids

5.6.1 Impact of Flavonoid Reactions on Wine Color

5.6.2 Impact of Flavonoid Reactions on Wine Taste Properties

References

6. Dietary Flavonoids and Health — Broadening the Perspective

6.1 Introduction

6.2 The Diversity of Dietary PPT

6.3 The Intake of PPT

6.4 Absorption of PPT and the Nature of the Plasma Metabolites

6.4.1 Introduction

6.4.2 Flavanols, Flavanol Gallates, and Proanthocyanidins

6.4.3 Flavonol Glycosides

6.4.4 Flavones and Polymethylflavones

6.4.5 Isoflavones

6.4.6 Flavanones

6.4.7 Chalcones, Dihdyrochalcones, and Retrochalcones

6.4.8 Anthocyanins

6.4.9 Stilbenes

6.4.10 Hydroxybenzoic Acids, Hydroxycinnamic Acids, and Associated Conjugates

6.4.11 Oleuropein, Tyrosol, and Hydroxytyrosol

6.4.12 Hydrolyzable Tannins

6.4.13 Lignins and Lignans

6.4.14 Derived Polyphenols

6.4.15 Person-to-Person Variation

6.5 PPT Metabolites in Tissues

6.5.1 Pseudo-Pharmacokinetic and Redox Properties

6.5.2 Binding to Plasma Proteins

6.5.3 Effects on the Vascular System

6.5.4 Transformation of PPT Metabolites after Absorption

6.6 PPT Prior to Absorption

6.6.1 Interaction with Tissues and Nutrients Prior to Absorption

6.6.2 Modulation of the Gut Microflora — Prebiotic Effects

6.6.3 Modulation of the Postprandial Surge in Plasma Glucose — Glycemic Index

6.7 Safety Assessment of Dietary PPT

6.8 Conclusions and Future Research Requirements

References

7. Isoflavonoids and Human Health

7.1 Introduction

7.2 Isoflavonoids: Dietary Sources and Intakes, Metabolism, and Bioavailability

7.2.1 Dietary Sources and Intakes

7.2.2 Metabolism and Bioavailability

7.3 Isoflavonoids and Cancer Prevention

7.3.1 Hormone-Dependent Cancer Prevention by Isoflavonoids

7.3.2 Estrogens and Risk of Breast Cancer

7.3.3 Estrogen Receptor Mediated Events

7.3.4 Animal Models

7.3.5 Mechanisms of Anticancer Action of Isoflavonoids

7.3.6 Clinical Studies

7.4 Protection by Isoflavonoids against Cardiovascular Disease

7.4.1 Cholesterol-Lowering and Isoflavonoids

7.4.2 Antioxidant Action

7.4.3 Arterial Function

7.4.4 Cellular Effects

7.5 Protection by Isoflavonoids against Osteoporosis, Cognitive Decline, and Menopausal Symptoms?

7.5.1 Osteoporosis

7.5.2 Menopausal Symptoms and Cognitive Decline

7.6 Isoflavonoids: Potential Risks

7.7 Isoflavonoids and Human Health: Conclusions

References

8. Flavonoid Functions in Plants

8.1 Introduction

8.2 Anthocyanins and 3-Deoxyanthocyanins

8.2.1 Defense

8.2.2 Protection from Solar Ultraviolet

8.2.3 Photoprotection

8.2.4 Antioxidant Activity

8.2.5 Anthocyanins as a Generalized Stress Response

8.3 Colorless Flavonoids

8.3.1 Stress Protection

8.3.1.1 Ultraviolet Radiation

8.3.1.2 Temperature Stress

8.3.1.3 Heavy Metal Tolerance

8.3.1.4 Oxidative Stress

8.3.2 Reproduction and Early Plant Development

8.3.2.1 Chemical Signals as Attractants for Pollination and Seed Dispersal

8.3.2.2 Flavonoids in Pollen, and Their Role in Plant Sexual Reproduction

8.3.2.3 Seeds and Seedling Development

8.3.3 Signaling — A Role as Chemical Messengers

8.3.3.1 Defense Against Pathogenic Microbes

8.3.3.2 Roles in Agrobacterium Infection

8.3.3.3 Legume Nodulation

8.3.3.4 Mycorrhizal Fungi

8.3.3.5 Parasitic Plants

8.3.3.6 Regulation of Auxin

8.3.4 Protection from Insect and Mammalian Herbivory

8.4 Conclusions

References

9. Flavonoid-Protein Interactions

9.1 General Considerations

9.1.1 The Biological Significance of Flavonoid-Protein Interactions in Man

9.1.2 Molecular Interactions Responsible for Flavonoid–Protein Complexation

9.1.3 Specificity of Flavonoid-Protein Interactions

9.2 Examples of Flavonoid-Protein Interactions in Man

9.2.1 Interactions Prior to Intestinal Absorption

9.2.1.1 Interactions with Salivary Proteins and Astringency

9.2.1.2 Interactions in the Gastrointestinal Tract

9.2.2 Interactions Involved in Flavonoid Bioavailability

9.2.2.1 Intestinal Absorption

9.2.2.2 Conjugation Enzymes

9.2.2.3 Plasma Proteins

9.2.3 Interactions Potentially Involved in Cellular Health Effects

9.2.3.1 ATP-Binding Proteins

9.2.3.2 Ligand–Receptor Interactions

9.2.3.3 Redox Enzymes

9.2.3.4 Modulation of Antioxidant Properties and Oxidation Pathways by Binding to Proteins

9.3 Conclusion and Perspectives

References

10. The Anthocyanins

10.1 Introduction

10.1.1 Anthocyanin Structures

10.1.2 Nutritional Supplements — Health Aspects

10.1.3 Food Colorants

10.1.4 Molecular Biology, Biosynthesis, and Functions

10.1.5 Analytical Methods and Instrumentation

10.2 Anthocyanin Chemistry

10.2.1 General Aspects and Nomenclature

10.2.2 Anthocyanidins

10.2.3 Anthocyanins Not Based on the Common Anthocyanidins

10.2.4 Glycosides

10.2.4.1 Monosaccharides

10.2.4.2 Disaccharides

10.2.4.3 Trisaccharides

10.2.4.4 Glycosidic Linkages

10.2.5 Anthocyanins with Acylation

10.2.5.1 Acylation with Phenolic Acids

10.2.5.2 Acylation with Aliphatic Acids

10.2.6 Dimeric Flavonoids Including an Anthocyanin Unit

10.2.7 Metalloanthocyanins

10.2.8 Anthocyanin Colors and Stability

10.3 Anthocyanin Production

10.3.1 Cell Cultures

10.3.2 Synthesis

10.4 Anthocyanin Localization in Plant Cells

10.5 Chemotaxonomic Patterns

10.5.1 Alliaceae

10.5.2 Convolvulaceae

10.5.3 Cruciferae

10.5.4 Gentianaceae

10.5.5 Geraniaceae

10.5.6 Labiatae

10.5.7 Leguminosae

10.5.8 Liliaceae

10.5.9 Nymphaeaceae

10.5.10 Orchidaceae

10.5.11 Ranunculaceae

10.5.12 Solanaceae

References

Appendix

11. Flavans and Proanthocyanidins

11.1 Introduction

11.2 Nomenclature

11.3 Structures and Distribution

11.3.1 Flavans, Flavan-3-ols, Flavan-4-ols, and Flavan-3,4-diols

11.3.1.1 Flavans

11.3.1.2 Flavan-3-ols

11.3.1.3 Flavan-4-ols

11.3.1.4 Flavan-3,4-diols

11.3.2 Proanthocyanidins

11.3.2.1 B-Type Proanthocyanidins

11.3.2.2 A-Type Proanthocyanidins

11.3.3 Nonproanthocyanidins with Flavan or Flavan-3-ol Constituent Units

11.3.4 Complex Tannins

11.3.5 Miscellaneous

11.3.6 NMR and Conformational Analysis of Proanthocyanidins

11.3.7 HPLC-MS Analysis of Proanthocyanidins

References

12. Flavones and Flavonols

12.1 Introduction

12.2 Organization of the Tables

12.3 Flavones

12.4 Flavonols

12.5 Flavones with Other Substituents

12.5.1 C-Methylflavones and C2/C3-Substituted Flavones

12.5.2 Methylenedioxyflavones

12.5.3 C-Prenylflavones

12.5.4 O-Prenylflavones

12.5.5 Pyranoflavones

12.5.6 Furanoflavones

12.5.7 Furano- and Pyrano-Substitution

12.5.8 C-Prenyl- and Pyrano-Substitution

12.5.9 C-Linked Aromatic- and Ketopyrano-Substitution

12.5.10 Tephrosia Flavones

12.5.11 Artocarpus Flavones

12.5.12 Flavone-Coumarin Hybrids

12.6 Flavonols with Other Substituents

12.6.1 C-Methylflavonols

12.6.2 Methylenedioxyflavonols

12.6.3 C-Prenylflavonols

12.6.4 O-Prenylflavonols

12.6.5 Pyranoflavonols

12.6.6 Furanoflavonols

12.6.7 C-Prenyl- and Pyrano-Substitution

12.6.8 Flavonols with Aromatic Substituents

12.6.9 Various Cycloflavonols

12.6.10 Hybrid Structures

12.6.11 Furanoflavonols of Vellozia

12.7 Flavone and Flavonol Esters

12.8 Chlorinated Flavonoids

12.9 Flavonoids of Helminthostachys

12.10 Comments on Distribution and Accumulation

References

Appendix

13. Flavone and Flavonol O-Glycosides

13.1 Introduction

13.2 Separation, Purification, and Identification

13.3 New Flavone and Flavonol O-Glycosides

13.3.1 Monosaccharides

13.3.2 Disaccharides

13.3.3 Trisaccharides

13.3.4 Tetrasaccharides

13.3.5 Sulfate Conjugates

13.3.6 Acylated Derivatives

13.3.7 New Flavone Glycosides — Further Considerations

13.3.8 New Flavonol Glycosides — Further Considerations

13.3.9 Glycosides of Prenylated Flavones and Flavonols, and of Pyrano and Methylenedioxyflavonols

13.4 Distribution Patterns

References

Appendix A

Appendix B

14. C-Glycosylflavonoids

14.1 Natural Sources and Some Taxonomic Implications

14.1.1 Plant Species Rich in C-Glycosylflavonoids

14.1.2 C-Glycosylflavonoids and Taxonomic Aspects

14.1.2.1 Ferns

14.1.2.2 Angiospermae Monocotyledonae

14.1.2.3 Angiospermae Dicotyledonae

14.2 Naturally Occurring C-Glycosylflavonoids

14.2.1 Mono-C-Glycosylflavonoids

14.2.2 Di- and Tri-C-Glycosylflavonoids

14.2.3 O-Glycosyl-C-Glycosylflavonoids

14.2.4 O-Acyl-C-Glycosylflavonoids

14.3 Separation and Identification of C-Glycosylflavonoids

14.3.1 Capillary Zone Electrophoresis Separation

14.3.1.1 Qualitative Aspects

14.3.1.2 Quantitative Aspects

14.3.2 High-Speed Countercurrent Chromatography Separation

14.3.3 New Polymers for Column Chromatography

14.3.4 Mass Spectrometry and Structural Identification

14.3.4.1 Fast Atom Bombardment and Tandem Mass Spectrometry

14.3.4.2 Liquid Chromatography–Mass Spectrometry: Thermospray and Atmospheric Pressure Ionization

14.3.4.3 LC–API-MSMS.

14.3.5 NMR Spectroscopy and Fine Structure Elucidation

14.3.5.1 Improved NMR Techniques

14.3.5.2 NMR and Rotational Isomers

14.4 Synthesis of C-Glycosylflavonoids

14.4.1 O–C Glycoside Rearrangement

14.4.2 Fries-Type Rearrangement

14.4.3 Via C-b-D-Glucopyranosyl 2,6-Dimethoxybenzene

14.5 C-Glycosylflavonoids and Vacuolar Storage

14.6 Biological Properties of C-Glycosylflavonoids.

14.6.1 Antioxidant Activity of C-Glycosylflavonoids

14.6.2 C-Glycosylflavonoids and Plant–Insect Relationships

14.6.2.1 Zea mays and Helicoverpa zea

14.6.2.2 Oryza sativa and Nilaparvata lugens

14.6.3 C-Glycosylflavonoids and Antimolluscidal Activity

14.6.4 C-Glycosylflavonoids and Plant–Microorganism Relationships

14.6.4.1 Arbuscular Mycorrhiza: Cucumis melo and Glomus caledonium

14.6.4.2 Disease: Cucumis sativus and Podosphaera xanthii

14.6.5 Antibacterial Role of C-Glycosylflavonoids

14.6.6 C-Glycosylflavonoids and General Animal Physiology

14.6.6.1 Antinociceptive Activity

14.6.6.2 Antispasmodic Activity

14.6.6.3 Sedative Activity

14.6.6.4 Antihepatotoxic Activity

14.6.6.5 Antiinflammatory Activity

14.6.6.6 Antidiabetic Activity

14.6.6.7 Antihypertensive Activity

14.7 Manufacture and Cultivation Process and C-Glycosylflavonoids

References

15. Flavanones and Dihydroflavonols

16. Chalcones, Dihydrochalcones, and Aurones

17. Bi-, Tri-, Tetra-, Penta-, and Hexaflavonoids

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