Chapter 1 : Polyphenol Extraction from Foods
1 Introduction
2 Solvent Extraction
Factors that Influence the Efficiency of Solvent Extraction
Sample Preparation
The Extraction Process
Solvent Extraction Using Different pH Values
Solvent Extraction of Anthocyanins
Solvent Extraction of Flavan-3-ols
Auxiliary Operations
Microwave-assisted Extraction
3 Solid-phase Extraction
Fractionation of Phenolic Compounds
Chapter 1 : Polyphenol Extraction from Foods
1 Introduction
2 Solvent Extraction
Factors that Influence the Efficiency of Solvent Extraction
Sample Preparation
The Extraction Process
Solvent Extraction Using Different pH Values
Solvent Extraction of Anthocyanins
Solvent Extraction of Flavan-3-ols
Auxiliary Operations
Microwave-assisted Extraction
3 Solid-phase Extraction
Fractionation of Phenolic Compounds
Solid-phase Extraction of Anthocyanidins
Solid-phase Extraction of Proanthocyanidins
4 Supercritical Fluid Extraction
5 Pressurized Liquid Extraction
References
Chapter 2 : Methods of Polyphenol Extraction from Biological Fluids and Tissues
1 Introduction
Primary Considerations
2 Polyphenol Extraction
Solvent Extraction
Comparing Solvents for Extraction of Quercetin Conjugates
Solid-phase Extraction
3 Hydrolysis
Acid Hydrolysis
Enzymic Hydrolysis
4 Particular Problems with Sulfate determination
5 Storage of Samples
6 Summary
References
Chapter 3 : Application of LC-MS for the Identification of Polyphenols
1 Introduction
2 Analysis of Anthocyanins and Derived Pigments
Methodology
Results
3 Analysis of Catechins and Proanthocyanidins
Methodology
Results
4 Analysis of Flavonols and Flavonol Metabolites
Methodology
Results
Acknowledgements
References
Chapter 4 : The Use of HPLC with Coulometric Detection in the Analysis of Flavonoids in Complex Matrices
1 Introduction
2 Basics of Electrochemistry
3 Principle of Coulometric Array Detection
4 Determination of Analysis Conditions
5 Sensitivity in Coulometric Detection
6 Analysis of Flavonoids Using HPLC with Coulometric Array Detection
7 Voltammetric Characteristics of Flavonoids
8 Conditions of Analysis for Each Class of Flavonoid
9 Specific Applications of Coulometric Array Detection in the Field of Flavonoid Bioavailability
10 Specific Applications of Coulometric Array Detection in the Field of Food Analysis
Use of Fingerprints
Estimation of the Overall Antioxidant Capacity
11 Conclusions
Acknowledgements
References
Chapter 5 : On-line Identification of Flavonoids by HPLC Coupled to Diode Array Detection
1 Introduction
2 Anthocyanins
RP-HPLC Elution Characteristics
Spectral Characteristics
3 Flavan-3-ols (Catechins, Proanthocyanidins, Condensed Tannins)
4 Flavones and Flavonols
Chromatographic Behaviour
UV-visible Spectroscopy
5 Flavanones, Dihydroflavonols and Isoflavonoids
Flavanones
Dihydroflavonols
Isoflavonoids
6 Chalcones and Aurones
Chalcones
Aurones
7 Dihydrochalcones
References
Chapter 6 : Application of LC-NMR in the Structure Elicidation of Polyphenols
1 Introduction
2 Principle of Operation of LC- NMR
Solvent Suppression
Operation in the On-flow Mode
Operation in the Stop-flow Mode
Sensitivity
Limitations
Hardware Set-up
3 Generalities on the 1H-NMR of Polyphenols
4 Strategies for the On-line Identification of Polyphenols
5 Stop-flow LC-1H-NMR of the Flavonoids and Xanthones from Gentiana ottonis
6 Stop-flow LC-1H-NMR with 2D Correlation Experiments for the Structure Elucidation of a Flavanone of Monotse englerii
7 On-flow LC-1H-NMR Characterisation of the Isoflavone and Isoflavanone Constituents of Erythrina vogelii
Preliminary LC-UV-DAD and High Resolution LC-APCI-Q TOF-MS-MS Analyses
Low-flow LC-NMR with Microfractionation
LC-UV-DAD with Post-column Derivatisation
Interpretation of the On-line Data
8 Other Applications of LC- NMR for the Study of Polyphenols
9 Conclusions
References
Chapter 7 : Polyphenols: Measurement and Calculation of Their Physical Chemistry Properties
1 Introduction
2 Free Radical Chemistry of Flavan-3-ols
Generation of Phenoxyl Radical by Pulsed Radiolysis and Flash Photolysis
Radiolytic Experiments on Simple Phenols
Radiolytic Experiments on Flavan-3-ols
Flash Photolysis Experiments on Selectively Protected Flavan-3-ols
4 Redox Properties of Flavan-3-ols
3 Acid-Base Properties of Flavan-3-ols
Determination of Redox Potential of Phenol by Pulse Radiolysis
Simple Phenols
Polyphenols
Determination of Redox Potential by Fast Cyclic Voltammetry on Selectively Protected Flavan-3-ols
5 Conclusion and Perspectives: A New Insight into Antioxidative Properties of Flavan-3-ols
References
Chapter 8 : Enzymatic Synthesis of Quercetin Glucosides and Glucuronides
1 Introduction
2 Production of Quercetin Glycosides
Preparation of Crude Onion Enzyme Extract
Preparation of Crude Leek Enzyme Extract
Enzymatic Synthesis of Quercetin Glycosides
Enzymatic Synthesis of Radio-labelled Quercetin Glycosides
HPLC Analysis for Flavonoids
3 Production of Quercetin Glucuronides
Production of Pig Liver Extract
Enzymatic Synthesis of Flavonoid Glucuronides
Enzymatic Synthesis of Radio-labelled Quercetin Glucuronides
Liquid Chromatography-Mass Spectrometry (LC-MS)
HPLC Analysis for Flavonoids
4 Concluding Remarks
Acknowledgements
References
Chapter 9 : Chemical Synthesis of Flavonoid Conjugates
1 Introduction
2 Strategies for the Preparation of Flavonoid Conjugates
The Total Synthesis of Basic Structures
The Hemisynthesis of Conjugates
3 Typical Experimental Procedures
2,4-Dihydroxyphenyl-4-hydroxybenzyl Ketone
2,4,6- Trihydroxyphenyl-4-hydroxybenzyl Ketone
Daidzein
oméga-Methoxyphoracetophenone
3,4-Dihydroxybenzoyl Chloride
3-Methylquercetin
Daidzein 7-Sulfate Potassium Salt
Quercetin 3-Sulfate
Quercetin 3' -Sulfate
Quercetin 7-bêta-D-Glucuronide (and Quercetin 4'-bêta-D-Glucuronide)
Daidzein 7-Glucuronide
Quercetin 3-0-b-D-Glucuronide
Isorhamnetin
Rhamnetin
4' -Methylcatechin and 3' -Methylcatechin
References
Chapter 10 : Quantitative Determination of Flavonols in Plant Foods and Biological Fluids
1 Introduction
2 Flavonols in Plant Foods
UV Detection of Total Flavonols after Acid Hydrolysis
UV Detection of Individual Flavonol Glycosides
3 Flavonols in Biological Fluids
Fluorescence Detection of Total Flavonols after Acid Hydrolysis
Electrochemical Detection of Conjugated Flavonols and of Total Flavonols after Enzymatic Hydrolysis
References
Chapter 11 : Analysis and Purification of Catechins and Their Transformation Products
1 Introduction
2 Catechin and Related Compound Isolation
Extraction
Separation Protocols
Physical Properties of Fresh Leaf Flavan-3-ols and Related Compounds
NMR Spectroscopy of Fresh Leaf Flavan-3-ols and Related Compounds
3 Flavan-3-ol Dimeric Oxidation Products
Extraction
Separation Protocols
Physical Properties of Black Tea Dimeric Flavonoid Oxidation Products
4 Flavan-3-ol Polymeric Oxidation Products
Roberts Fractionation
Theafulvin Fractionation
Black Tea Fractionation by Solvent Precipitation
5 Determination of Total Polyphenols in Tea Using the Folin-Ciocalteu Reagent
Reagents
Apparatus
Preparation of test sample
Procedure
Appendix A: HPLC Conditions for Flavan-3-ol Dimeric Oxidation Products
Appendix B: Structures of Flavan-3-ol Dimeric Oxidation Products
References
Chapter 12 : Analysis and Purification of Proanthocyanidin Oligomers
1 Introduction
2 Extraction and Purification of Proanthocyanidin Oligomers
Extraction
Purification
3 Characterization of Proanthocyanidin Oligomers
Thiolysis
Mass Spectrometry
NMR
4 Quantification of Proanthocyanidin Oligomers
Colorimetric Methods
Reversed-phase HPLC
Normal-phase HPLC
Detection
5 Conclusion
References
Chapter 13 : Analysis of Polymeric Proanthocyanidins and Complex Polyphenols
1 Introduction
2 Structure of Proanthocyanidin Polymers and Tannin-like Compounds
Proanthocyanidins
Tannin-like Compounds
3 Analysis and Characterization
Extraction from Plant Tissues
Sample Clean-up by Liquid-liquid or Solid-phase Extraction
Fractionation According to Molecular Weight
Quantitation and Characterization of Polymeric Tannins
4 Conclusion
References
Chapter 14 : The Analysis and Characterization of Chlorogenic Foods and Other Cinnamates
1 Introduction
2 The Cinnamate Conjugates
The Chlorogenic Acids
Other Cinnamate Conjugates
Cinnamate Transformation Products
3 Analysis and Characterization
Structure and Hydrophobicity
Extraction from Plant Tissues
Extraction from Animal Tissues
Sample Clean-up by Solvent Partition and Solid-phase Adsorption
Artefacts
Hydrolysis/Saponification
Availability of Authentic Standard Compounds
Chromatography
Spectroscopic and Other Physical Properties
Mass Spectroscopy
References
Chapter 15 : Analysis of Anthocyanins
1 Introduction
2 Chemistry
Structure
Stability
3 Methods of Analysis
Extraction
Isolation and Purification
Detection and Identification
Techniques of Hydrolysis
References
Chapter 16 : Analysis and Purification of Flavanones, Chalcones and Dihydrochalcones
1 Introduction
2 Extraction
3 Chemical Transformation
4 Chromatographic Analysis
5 Isolation and Purification
6 UV Spectroscopy
Flavanones
Chalcones
Dihydrochalcones
7 1H NMR Spectroscopy
Flavanones
Chalcones
Dihydrochalcones
8 HPLC-ESI (Electrospray lonization) Mass Spectrometry
References
Subject Index
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