Bioactive Natural Products Detection Isolation and Structural Determination 2nd Edition by Steven Colegate, Russell Molyneux 1498774814 9781498774819

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ISBN 10: 1498774814

ISBN 13: 9781498774819

Author: Steven M. Colegate; Russell J. Molyneux

Following the successful format of the original, this new edition presents applications of the most recent techniques for the detection, isolation, and structural determination of bioactive natural products. It features new case studies and illustrations that demonstrate applications of techniques covered in the book. Complementing as much as replacing the first edition, most of the contributors are new. The text includes updates on chemical extraction, and NMR-based structure determination, and new contributions on liquid chromatography linked with mass and NMR spectroscopy, dereplication approaches, assessment of source material for natural products and novel bioassay development.

Bioactive Natural Products Detection Isolation and Structural Determination 2nd Table of contents:

Chapter 1 An Introduction and Overview

1.1 Introduction

1.2 The Multidisciplinary Approach

1.3 Why Isolate Biologically Active Natural Products?

1.4 Detection and Isolation

1.5 Structure Determination

1.6 Overview

1.6.1 Methods of Detection, Isolation, and Structural Determination

1.6.1.1 Detection and Isolation

1.6.1.2 Structure Determination

1.6.2 Specific Case Studies

1.7 Conclusions

Chapter 2 Detection and Isolation of Bioactive Natural Products

2.1 Introduction

2.2 Detection of Biologically Active Metabolites

2.3 Screening For Bioactive Metabolites

2.3.1 Primary Screening Assays

2.3.1.1 Brine Shrimp Lethality Test

2.3.1.2 Crown Gall Tumor Bioassay

2.3.1.3 Starfish or Sea Urchin Assay

2.3.1.4 Bioassays for Antibiotic Activity

2.3.1.5 Bioautography

2.3.1.6 Allelopathy

2.3.1.7 Insecticidal Activity

2.3.2 Specialized Screening Assays

2.3.2.1 Antiviral Activity

2.3.2.2 Cytotoxicity, Antitumor, and Antineoplastic Activity

2.3.2.3 Immunosuppressive Activity

2.3.2.4 Antimalarial Activity

2.3.2.5 Amoebicidal Activity

2.3.2.6 Antimycobacterial Activity

2.4 Isolation and Separation

2.4.1 Extraction

2.4.1.1 Dry Biological Material

2.4.1.2 Fresh Material

2.4.1.3 Liquid Culture Broth and Other Biological Fluids

2.4.1.4 Extraction of Water-Soluble Metabolites

2.4.1.5 Removal of Fatty Material

2.4.1.6 Supercritical Fluid and Accelerated Solvent Extraction

2.4.2 Chromatography

2.4.2.1 Liquid-Liquid Chromatography

2.4.2.1.1 Countercurrent Chromatography

2.4.2.1.2 Modern Countercurrent Chromatography

2.4.2.2 Planar Chromatography

2.4.2.2.1 Preparative Thin Layer Chromatography

2.4.2.2.2 Centrifugal Thin Layer Chromatography

2.4.2.2.3 Overpressure Layer Chromatography and Automated Multiple Development

2.4.2.2.4 Multidimensional Planar Chromatography

2.4.2.3 Column Chromatography

2.4.2.3.1 Gel Filtration

2.4.2.3.2 Preparative Column Chromatography

2.4.2.4 Preparative Pressure Liquid Chromatography

2.4.2.4.1 Low-Pressure Lc

2.4.2.4.2 Medium-Pressure Lc

2.4.2.4.3 High-Performance (Pressure) Lc

2.4.3 Separation of Similar Compounds

2.4.4 Separation of Different Classes of Compounds

2.4.5 Other Chromatographic Techniques

2.5 Modern Strategies

2.5.1 High Throughput Screening

2.5.2 Dereplication

2.5.2.1 Biological Screening

2.5.2.2 Chemical Screening

2.5.2.3 New Approach to Natural Products Discovery

2.6 Artifacts

2.6.1 Artifacts from Extraction

2.6.2 Artifacts from Separations

2.7 Concluding Remarks

References

Chapter 3 Nuclear Magnetic Resonance Spectroscopy: Strategies for Structural Determination

3.1 Introduction

3.2 Basic Principles of Nmr Spectroscopy

3.2.1 The Conditions Necessary for Resonance

3.2.2 The Chemical Shift

3.2.3 Spin-Spin Coupling

3.2.4 The Nuclear Overhauser Effect

3.2.5 Pulsed Fourier Transform Nmr Spectroscopy

3.2.6 Pulse Sequences and Two Dimensional Nmr Experiments

3.2.7 The Nmr Spectrometer

3.3 Strategy For Solving Structures

3.4 Obtaining the Basic Information

3.4.1 The 1H Spectrum

3.4.2 The 13C Spectrum

3.4.2.1 The 1H Decoupled 13C Spectrum

3.4.2.2 Determining the Number of Directly Attached Hydrogen Atoms

3.4.2.2.1 Fully Coupled 13C Spectra

3.4.2.2.2 Single-Frequency Off-Resonance Decoupled Spectra

3.4.2.2.3 J-Modulated Spin Echo Procedures

3.4.2.2.4 Methods Involving Polarization Transfer: Dept, Inept

3.5 Establishing the 1H Coupling Networks

3.5.1 Spin-Spin Decoupling Experiments

3.5.2 Two Dimensional Homonuclear Correlation Experiments

3.5.3 One Dimensional Versions of the Cosy Experiment

3.6 Correlating Resonances Due To Directly Bonded 1H and 13C Nuclei

3.6.1 Two Dimensional Heteronuclear Chemical Shift Correlation Experiments

3.6.2 One Dimensional Heteronuclear Chemical Shift Correlation Experiments

3.7 Long-Range Heteronuclear Chemical Shift Correlation

3.7.1 Long-Range Heteronuclear Correlation Techniques

3.7.1.1 Two Dimensional Methods

3.7.1.2 One Dimensional Methods

3.7.2 Relayed Coherence Transfer Experiments

3.8 Establishing Molecular Structure Via 13C-13C Coupling

3.9 Establishing the Proximity of Nuclei Through Space

3.9.1 The Noe Difference Experiment

3.9.2 The Two Dimensional Noesy Experiment

3.9.3 The ge-1D Noesy Experiment

3.9.4 The Roesy Experiment

3.10 Three Dimensional Experiments

3.11 Concluding Remarks

References

Chapter 4 Quantitative Nmr of Bioactive Natural Products

4.1 Introduction

4.1.1 The New Kid on the Block?

4.1.1.1 A New Potential Role for Nmr

4.1.1.2 Definition of Qnmr Terms

4.1.2 The Biological Perspective of Quantitative Nmr

4.1.2.1 Biological Activity and Qnmr Correlation

4.1.2.2 Metabolomics and Biomarkers

4.1.3 The Benefits of Quantitative Nmr

4.1.3.1 The Dual Character of Qnmr

4.1.3.2 The No-Cost Extension Aspect of Qhnmr

4.1.4 General Quantitative Nmr Considerations

4.1.4.1 General Advantages of Qnmr

4.1.4.2 Nuclei Suitable for Qnmr

4.2 The Quantitative Nmr Experiment

4.2.1 General Considerations

4.2.2 Sample Preparation

4.2.3 Signal Proportionality

4.2.3.1 Radio Frequency Excitation and Nmr Observables

4.2.3.2 External Quantitative Analysis

4.2.3.3 Spectrometer Hardware Configuration for Removal of Sidebands, Artifacts, and Satellites

4.2.3.3.1 Sample Spinning

4.2.3.3.2 Removal of 13C Satellites

4.2.3.4 Other Considerations

4.2.4 Common Nmr Workflow

4.2.4.1 Optimization of Qhnmr Acquisition Parameters

4.2.4.1.1 Spectral Window Selection

4.2.4.1.2 Transmitter Offset Selection

4.2.4.1.3 Pulse Width Selection

4.2.4.1.4 Acquisition Time Selection

4.2.4.1.5 Relaxation Delay Selection

4.2.4.1.6 Setting the Number of Scans or Transients

4.2.4.1.7 Receiver Gain Setting

4.2.4.1.8 Steady-State (“Dummy”) Pulses

4.2.4.1.9 Carbon Decoupling

4.2.4.2 Postacquisition Processing

4.3 Quantitative Nmr Applications To Bioactive Natural Products

4.3.1 Basic Considerations

4.3.2 Internal Standards

4.3.2.1 Some Precautions with Internal Standards

4.3.2.2 Use of Solvent Signals as Internal Standards

4.3.3 External Standards

4.3.3.1 Concentric Tubes

4.3.3.2 Separate Analyses of Analytes and Standards

4.3.3.3 Electronic Signals (The Eretic Method)

4.3.4 Quantitative Hnmr Analysis of Ursolic Acid Samples

4.3.5 Sample-Specific Considerations

4.3.5.1 Sample Purity

4.3.5.2 Proton Counts

4.3.5.3 Concentration

4.3.5.4 Proton Exchange

4.3.5.5 Paramagnetism

4.3.5.6 Nuclear Overhauser Enhancements

4.4 Conclusions

4.5 Summary and Outlook

References

Chapter 5 Development and Application of Lc-Nmr Techniques to the Identification of Bioactive Natural Products

5.1 Introduction

5.2 Direct Hyphenation of Lc-Nmr

5.2.1 Principle of Lc-Nmr

5.2.1.1 Nmr Flow Cell Design

5.2.1.2 Experimental Arrangement

5.2.1.3 Sensitivity

5.2.1.4 Dynamic Range and Solvent Suppression

5.2.1.5 Hplc Separation of Crude Plant Extracts

5.2.2 Modes of Operation of Lc-Nmr in Direct Hyphenation

5.2.2.1 On-Flow

5.2.2.2 Stop-Flow

5.2.2.3 Loop Storage

5.2.2.4 Time Slicing

5.2.3 “Hypernation”: Integration of Lc-Nmr in Multiple Hyphenation

5.2.4 Application to the Analysis of Crude Plant Extracts

5.2.4.1 Chemical Screening by On-Flow Lc-Nmr

5.2.4.1.1 Antifungal Isoflavones from E. vogelii

5.2.4.1.2 Tropane Alkaloids from E. vacciniifolium

5.2.4.2 Detailed Structural Investigation by Stop-Flow Lc-Nmr

5.2.4.2.1 Prenylated Flavanones from Monotes englerii

5.2.4.2.2 Oxidation Products of Hyperforin from Hypericum perforatum

5.2.4.3 Study of Unstable Compounds: Iridoids from Jamesbrittenia fodina

5.2.4.4 Study of Epimerization Reactions

5.2.4.5 Online Absolute Configuration Determination

5.2.5 Limitations of the Direct Hyphenation of Lc-Nmr

5.2.5.1 Restricted Observable Nmr

5.2.5.2 Chemical Shift Differences

5.2.5.3 Lack of Sensitivity

5.3 Indirect Hyphenation of Nmr: At-Line Versus Online Approaches

5.3.1 Spe-Nmr

5.3.2 Cap-Nmr

5.3.2.1 Rutin

5.3.2.2 Swertiamarin and Sweroside

5.3.3 De Novo Structural Determination: Antioxidant Flavonoids from E. scheuchzeri

5.4 Review of the Latest Applications of Direct and Indirect Hyphenation of Nmr

5.5 Conclusion

References

Chapter 6 Determination of the Absolute Configuration of Bioactive Natural Products Using Exciton Chirality Circular Dichroism

6.1 Introduction

6.2 Exciton Chirality Method

6.2.1 Basic Principle of the Exciton Chirality Method

6.2.2 Special Features of the Exciton Chirality Method

6.2.2.1 Chromophores Used for Exciton Coupling

6.2.2.2 Additivity of Cd Amplitudes

6.2.3 Applications of the Exciton Chirality Method

6.2.3.1 Exciton Coupling between Different Chromophores

6.2.3.2 Other Applications of the Exciton Chirality Method

6.2.3.2.1 Stereochemical Assignment of Carboxylic Acid Groups

6.2.3.2.2 Stereochemical Assignment of Sulfanyl Groups

6.2.3.3 Absolute Configurational Assignment of Compounds with a Single Stereogenic Center

6.2.3.4 Fluorescence-Detected Exciton-Coupled Circular Dichroism

6.3 Conclusions

References

Chapter 7 Separation of Enantiomeric Mixtures of Alkaloids and Their Biological Evaluation

7.1 Introduction

7.1.1 Enantiomers

7.1.2 Anabasine and Ammodendrine Enantiomers

7.1.3 Optical Rotation Measurements

7.2 Isolation of Anabasine and Ammodendrine Enantiomers

7.2.1 Synthesis and Separation of Anabasine and Ammodendrine-Based Diastereomers

7.2.2 Conversion of Diastereomers to Enantiomers

7.2.3 Enantiomeric Purity

7.2.3.1 Hplc Measurements

7.2.3.2 Optical Rotation Measurements

7.3 Bioactivity

7.3.1 Mouse Toxicity

7.3.2 Human Fetal Nicotinic Acetylcholine Receptor

7.4 Conclusions

7.5 Implications

References

Chapter 8 Dereplication and Discovery of Natural Products by Uv Spectroscopy

8.1 Introduction

8.1.1 The New Chemoinformatic Era of Natural Product Chemistry

8.1.2 The Chemotaxonomic Screening Approach

8.2 Potential and Limitations of Uv Spectroscopy

8.3 A Few Important Fungi and Their Metabolites

8.4 Characteristic Uv Spectra of Fungal Polyketides, Alkaloids, and Terpenoids

8.4.1 Alkaloids

8.4.2 Polyketides

8.4.3 Terpenoids

8.5 Databases and Algorithms

8.5.1 Structure of Hplc-Dad Data

8.5.2 Data Processing/Analysis

8.5.2.1 Noise Reduction

8.5.2.2 Baseline (Background) Correction

8.5.2.3 Chromatographic Alignment

8.5.2.4 Peak Detection

8.5.2.5 Deconvolution of Chromatographic Peaks

8.5.2.6 Peak Purity

8.5.2.7 Standard Library Search Methods

8.5.3 X-Hitting

8.5.3.1 Cross-Hitting

8.5.3.2 New-Hitting

8.6 Conclusions and Perspectives

References

Chapter 9 Liquid Chromatography-Mass Spectrometry in Natural Product Research

9.1 Introduction

9.2 Mass Spectrometry As An Integral Part of An Isolation-Characterization System

9.2.1 Interfaces between Lc and Ms

9.2.1.1 Electrospray Ionization

9.2.1.2 Atmospheric Pressure Chemical Ionization

9.2.1.3 Dual Ionization Mode Capability

9.2.1.4 Limiting Considerations

9.2.2 Common Mass Analyzers for Lc-Ms

9.2.2.1 Quadrupole Analyzer

9.2.2.2 Ion Trap Analyzer

9.2.2.3 Time-of-Flight Analyzer

9.2.2.4 Tandem-in-Space Analyzers

9.3 Applications of Lc-Ms In the Screening and Characterization of Natural Products

9.4 Roles of Lc-Ms In Quality Control of Herbal Products

9.4.1 Fingerprinting for Authentication of Plant Materials

9.4.2 Standardization of Herbal Medicines

9.4.2.1 Uv Detector for Quantification with Ms for Identification

9.4.2.2 Selected Ion Monitoring Mode in Ms

9.4.2.3 Multiple-Reaction Monitoring Mode in Tandem Ms/Ms

9.4.3 Lc-Ms for Detection of Toxic Components and Synthetic Adulterants

9.4.3.1 Detection of Aristolochic Acids I and Ii in Herbal Products

9.4.3.1.1 Solid-Phase Extraction

9.4.3.1.2 Tandem Mass Spectrometric Analysis

9.4.3.2 Sieving out Adulterants from Herbal Products

9.5 Roles of Lc-Ms In Metabolism and Pharmacokinetic Studies of Natural Products

9.6 Summary and Conclusions

References

Chapter 10 Application of High-Speed Countercurrent Chromatography to the Isolation of Bioactive Natural Products

10.1 Introduction

10.2 High-Speed Countercurrent Chromatography

10.2.1 Principle

10.2.2 Apparatus

10.2.3 Methodology

10.3 Application of Hsccc To the Isolation of Bioactive Natural Products

10.3.1 Isocratic Elution

10.3.1.1 One-Step Hsccc Separation Using Isocratic Elution

10.3.1.1.1 Carotenoids and Squalene from Microalgae

10.3.1.1.2 Extraction of Active Components from Herbal Medicines

10.3.1.2 Two-Step Hsccc Separations Using Isocratic Elution

10.3.2 Stepwise or Gradient Elution

10.3.3 Multidimensional Ccc

10.3.4 pH Zone-Refining Ccc

10.3.5 Cross-Axis Ccc

10.3.6 Other Methods

10.3.6.1 Dual-Mode Ccc

10.3.6.2 Elution-Extrusion Ccc

10.3.6.3 Foam Ccc

10.3.6.4 Eluate Detection Systems

10.3.6.5 Small Coil-Volume Ccc

10.3.6.6 Large-Scale Ccc

10.4 Conclusions

References

Chapter 11 Biosensing Approach in Natural Product Research

11.1 Introduction

11.2 Biosensors

11.2.1 Catalytic Biosensors

11.2.2 Affinity Biosensors

11.3 Transduction Principles

11.3.1 Electrochemical Detection

11.3.2 Piezoelectric Detection (Mass-Sensitive Devices)

11.3.3 Optical Detection: Surface Plasmon Resonance-Based Sensing

11.4 Catalytic Biosensors For the Detection of Specific Functional Moieties

11.4.1 Cysteine Sulfoxides

11.4.2 Glucosinolates

11.4.3 Cyanogenic Glycosides

11.4.4 Polyphenols

11.5 Evaluation of Antioxidant Properties

11.5.1 Superoxide Dismutase-Based Biosensor

11.5.2 Laccase-Based Biosensor

11.5.3 Cytochrome c-Based Biosensor

11.5.4 Dna-Based Biosensor

11.6 Affinity Sensors

11.6.1 Immunosensors

11.6.1.1 Optical Sensing for Glycyrrhizin and Paclitaxel

11.6.1.1.1 Surface Plasmon Resonance

11.6.1.1.2 Fluorometric

11.6.1.2 Piezoelectric Sensing for Cocaine

11.6.2 Synthetic Receptors: Molecular Imprinted Polymers for Caffeine Detection

11.6.3 Dna-Based Sensors

11.6.4 Optical Sensing for Antiendotoxins

11.7 Biosensor Based On the Modulation of the Biological Activity of the Receptor

11.7.1 Tissue Biosensors

11.7.2 Microphysiometer to Monitor the Cell Response to Compounds

11.7.3 Enzyme Biosensors

11.8 Future Perspectives

References

Chapter 12 Anticancer Drug Discovery and Development from Natural Products

12.1 Introduction

12.1.1 The Role of Traditional Medicine in Drug Discovery

12.1.2 The Role of Marine Organisms in Drug Discovery

12.1.3 The Role of Microorganisms in Drug Discovery

12.1.4 Microbial Symbionts

12.1.5 The Ongoing Role of Natural Products

12.2 Anticancer Agents From Plant Sources

12.2.1 Plant-Derived Drugs in Clinical Use

12.2.2 Plant-Derived Agents in Clinical Development

12.2.3 Plant-Derived Agents in Preclinical Development

12.3 Anticancer Agents From Marine Sources

12.3.1 Clinically Studied Marine-Derived Anticancer Agents

12.3.1.1 Marine-Derived Agents Now Withdrawn from Clinical Trials

12.3.1.2 Marine-Derived Agents Currently in Clinical Trials

12.3.2 Marine-Derived Agents in Preclinical Development

12.3.2.1 Tubulin Interactive Agents

12.3.2.2 Vacuolar-Atpase Inhibitors

12.3.2.3 Dna Polymerase a Inhibitors

12.3.2.4 Reductive Dna-Cleaving Agents

12.3.2.5 Potential Cyclin-Dependent Kinase (Cdk) Inhibitors

12.3.2.6 Actin-Active Agents

12.3.2.7 Telomerase Inhibitors

12.4 Anticancer Agents From Microbial Sources

12.4.1 Microbial-Derived Drugs in Clinical Use

12.4.2 Microbial-Derived Agents in Clinical Development

12.4.3 Microbial-Derived Agents in Preclinical Development

12.5 Targeted Delivery of Natural Products

12.6 Conclusions

12.7 Personal Insight and Future Directions

References

Chapter 13 Sourcing Natural Products from Endophytic Microbes

13.1 Introduction

13.2 The Need For and Pursuit of Microbial Products

13.2.1 New Medicines

13.2.2 Potential Agricultural and Industrial Needs

13.3 Endophytic Microbes

13.4 rationale for plant selection

13.5 Endophytes and Biodiversity

13.6 Endophytes and Natural Products

13.6.1 Isolation, Preservation, and Storage of Endophytic Cultures for Product Isolation

13.6.2 Some Examples of Bioactive Natural Products from Endophytes

13.6.2.1 Endophytic Fungal Products as Antibiotics

13.6.2.2 Endophytic Bacterial Products as Antibiotics

13.6.2.2.1 Endophytic Pseudomonas Species

13.6.2.2.2 Endophytic Streptomyces Species

13.6.2.3 Volatile Antibiotics from Endophytes

13.6.2.4 Antiviral Compounds from Endophytes

13.6.2.5 Endophytic Fungal Products as Anticancer Agents

13.6.2.6 Endophytic Fungal Products as Antioxidants

13.6.2.7 Endophytic Fungal Products as Immunosuppressive Compounds

13.6.3 Surprising Results from Molecular Biological Studies of P. microspora

13.7 Concluding Statements

Acknowledgments

References

Chapter 14 Isolation of Bioactive Natural Products from Myxobacteria

14.1 Introduction

14.2 Screening Method

14.3 Cystothiazoles

14.3.1 Production and Isolation

14.3.2 Production of Derivatives

14.3.2.1 Large-Scale Fermentation

14.3.2.2 Biotransformation

14.3.2.3 Chemical Synthesis

14.3.3 Biological Activity

14.3.3.1 Anti-Phytophthora Activity

14.3.3.2 Antimicrobial Spectrum

14.3.3.3 Cytotoxicity

14.4 Myxalamide Derivatives

14.4.1 Isolation and Structures

14.4.2 Biological Activity

14.5 Haliangicins

14.5.1 Production and Isolation

14.5.2 Biological Activity

14.6 Summary

References

Chapter 15 Naturally Occurring Glycosidase Inhibitors

15.1 Introduction

15.1.1 The Definition of Naturally Occurring Glycosidase Inhibitors

15.1.2 The Roles of Naturally Occurring Glycosidase Inhibitors

15.1.3 Distribution of Glycosidase Inhibitors

15.1.4 The Therapeutic Value of Alkaloidal Glycosidase Inhibitors

15.1.5 Importance of Alkaloidal Glycosidase Inhibitors in Herbal Medicines and Foods

15.2 Extraction and Processing of Alkaloidal Glycosidase Inhibitors

15.3 Analysis

15.3.1 Gas Chromatography-Mass Spectroscopy

15.3.2 High Performance Liquid Chromatography

15.3.3 Thin Layer Chromatography

15.3.4 High-Voltage Paper Electrophoresis

15.3.5 Glycosidase Inhibition Assay

15.3.6 Nmr

15.4 Personal Insight

References

Chapter 16 Bioassay-Directed Isolation and Identification of Antiaflatoxigenic Constituents of Walnuts

16.1 Introduction

16.2 Bioassay For Antiaflatoxigenic Activity

16.2.1 Fungal Cultures and Inoculation of Media

16.2.1.1 Preparation of Fungal Cultures

16.2.1.2 Preparation of Media

16.2.2 Analysis for Aflatoxins

16.2.2.1 Extraction of Fungal Cultures and Growth Media

16.2.2.2 Hplc Analysis for Aflatoxin B1

16.3 Identification of Aflatoxin Resistance Factors In Tree Nuts

16.3.1 Comparison of Tree Nut Species and Varieties

16.3.2 Tissue Localization of Resistance Factors

16.4 Isolation and Structure Determination

16.4.1 Sequential Extraction and Bioassay of Fractions

16.4.2 Identification of Antiaflatoxigenic Constituents

16.4.3 Analysis of Gallic and Ellagic Acid Content in Walnuts

16.4.3.1 Hplc Analysis of Gallic and Ellagic Acids

16.4.3.2 Contents of Gallic and Ellagic Acid in Walnut Cultivars

16.5 Hydrolyzable Tannin Structure-Activity Considerations

16.6 Mechanism of Antiaflatoxigenic Activity

16.7 Conclusions

References

Chapter 17 Bioactive Peptides in Hen Eggs

17.1 Introduction

17.2 Albumen Peptides

17.2.1 Antimicrobial Activity

17.2.1.1 Lysozyme

17.2.1.2 Ovalbumin

17.2.1.3 Ovotransferrin

17.2.1.4 Avidin

17.2.1.5 Ovomucin

17.2.1.6 Cystatin

17.2.2 Antiadhesive Properties

17.2.3 Immunomodulating Activity

17.2.3.1 Ovalbumin and Ovomucin

17.2.3.2 Lysozyme

17.2.3.3 Ovotransferrin

17.2.3.4 Cystatin

17.2.4 Hypocholesterolemic Activity

17.2.5 Anticancer Activity

17.2.5.1 Lysozyme and Ovomucin

17.2.5.2 Avidin

17.2.5.3 Cystatin

17.2.6 Antihypertensive Activity

17.2.7 Antioxidant Activity

17.2.8 Protease Inhibition

17.2.8.1 Ovomacroglobulin

17.2.8.2 Cystatin

17.2.8.3 Ovomucoid and Ovoinhibitor

17.2.9 Biospecific Ligand Activity

17.3 Egg Yolk Peptides

17.3.1 Antimicrobial Activity

17.3.2 Antiadhesive Properties

17.3.3 Immunomodulating Activity

17.3.4 Antihypertensive Activity

17.3.5 Antioxidant Activity

17.3.6 Nutrient Bioavailability

17.4 Eggshell and Membrane Peptides

References

Chapter 18 Biological Fingerprinting Analysis: Strategy for Screening Bioactive Compounds in Traditional Chinese Medicines

18.1 Introduction

18.2 Biological Fingerprinting Analysis of Traditional Chinese Medicines

18.2.1 Biological Target-Interaction Chromatography

18.2.1.1 Targeting Hsa and Human Serum

18.2.1.2 Targeting Dna

18.2.1.3 Targeting Tublin and Microtubules

18.2.2 Biological Fingerprinting Analysis by Affinity Chromatography with Immobilized Target Molecules

18.2.2.1 Immobilized Liposome and Biomembrane Chromatography

18.2.2.2 Immobilized Plasma Proteins Chromatography

18.2.2.3 Immobilized Dna Chromatography

18.2.3 2D-Hplc: Coupling Affinity Chromatography to Reverse-Phase Hplc

18.2.4 Biological Fingerprinting Analysis Based on In Vitro Metabolism

18.3 Pharmacological Screening With Animal Models

18.3.1 Pharmacological Screening in Biofluids

18.3.2 Pharmacological Screening with Organ and Tissue Models

18.4 Screening Methods With Cellular Models

18.5 Screening Based on the Activity of Receptors and Enzymes

18.6 Application of Mass Spectrometry

18.7 Conclusions and Perspectives

Acknowledgments

References

Chapter 19 Antimalarial Compounds from Traditionally Used Medicinal Plants

19.1 Introduction

19.2 Development of Bioassays For Antimalarial Activity

19.2.1 The Life Cycle of Malaria Infection

19.2.2 Bioassays for the Erythrocytic Stage of Plasmodium

19.2.2.1 Incorporation of Radiolabeled Precursors

19.2.2.2 Colorimetric, Fluorometric, and Flow Cytometry-Based Assays

19.2.2.3 Interlaboratory Variation

19.2.2.4 In Vivo Methods

19.2.3 Bioassays for the Hepatic Stage of Plasmodium

19.2.4 Bioassays for Parasite Targets

19.2.4.1 Inhibition of Heme Polymerization

19.2.4.2 Apicoplast-Based Targets

19.2.4.3 Other Biochemical-Based Targets and Amelioration of Resistance

19.3 Selection of Plants

19.4 Extraction and Isolation

19.4.1 Extraction

19.4.2 Screening for Activity

19.4.3 Isolation of Active Components

19.4.4 Structure Determination

19.5 Examples of Active Compounds

19.5.1 Terpenoids

19.5.1.1 Sesquiterpenoids

19.5.1.2 Diterpenoids

19.5.1.3 Triterpenoids

19.5.1.3.1 Pentacyclic Triterpenes

19.5.1.3.2 Quassinoids

19.5.1.3.3 Limonoids

19.5.2 Phenolics

19.5.2.1 Simple

19.5.2.2 Lignans

19.5.2.3 Aurones

19.5.2.4 Flavonoids

19.5.2.5 Xanthones

19.5.2.6 Quinones

19.5.3 Alkaloids

19.5.3.1 Quinolines

19.5.3.2 Steroidal Alkaloids

19.5.3.3 Bisbenzylisoquinolines

19.5.3.4 Naphthylisoquinolines

19.5.3.5 Resistance-Modulating Alkaloids

19.5.3.6 Indoloquinolines

19.5.3.7 Indolomonoterpenoid Alkaloids

19.5.3.8 Other Alkaloids

19.5.4 Plants and Natural Products Active at the Hepatic Cycle of Infection

19.5.5 Other Sources of Natural Antimalarial Compounds

19.6 Conclusion

References

Chapter 20 Germination Stimulant in Smoke: Isolation and Identification

20.1 Introduction

20.2 Isolation

20.2.1 Germination Bioassay

20.2.2 Types of Smoke That Stimulate Germination

20.2.3 Extraction of the Bioactive Agent

20.3 Separation

20.3.1 Column Chromatography

20.3.2 Preparative Hplc Methods

20.3.3 Hplc-Ms Analysis

20.3.4 Possible Identification: Tropolones

20.3.5 Restart: Increase Initial Concentrations

20.4 Identification

20.4.1 Nmr Spectroscopy

20.4.2 Synthesis

20.4.3 Confirmation of Activity

20.5 Concluding Remarks

References

Chapter 21 Plant-Associated Toxins: Bioactivity-Guided Isolation, Elisa, and Lc-Ms Detection

21.1 Introduction

21.2 The In Vivo Bioactivity-Guided Isolation of Toxic Cucurbitacin Steroidal Glucosides From Stemodia Kingii

21.2.1 Clinical and Pathological Descriptions of the Intoxication of Sheep

21.2.2 Development and Validation of a Mouse Bioassay

21.2.3 Isolation of the Toxins

21.2.3.1 Extraction

21.2.3.2 Chromatography

21.2.3.2.1 Column Chromatography

21.2.3.2.2 Radial Chromatography

21.2.4 Structural Elucidation

21.2.4.1 Physicochemical Analysis

21.2.4.2 High Pressure Liquid Chromatography-Mass Spectrometry

21.2.4.3 Nmr Spectroscopy

21.2.5 Conclusions and Future Research

21.3 The In Vitro Detection of Hepatocytotoxic Fungal Metabolites Potentially Related To Acute Bovine Liver Disease

21.3.1 Description of the Intoxication

21.3.2 Detection of Hepatocytotoxins

21.3.2.1 In Vitro Culture of Drechslera biseptata and Rat Liver Hepatocytes

21.3.2.2 In Vitro Assessment of Extracts

21.3.3 Hplc-Ms of Hepatocytotoxic Extracts

21.3.4 Conclusions and Future Research

21.4 Elisa Detection of Low-Molecular-Weight Bioactive Natural Products

21.4.1 Phomopsins

21.4.1.1 Source and Biological Activity of the Phomopsins

21.4.1.2 Development of a Phomopsin Elisa

21.4.1.2.1 Antibody Production

21.4.1.2.2 Incorporation of Phomopsin Antibodies into an Elisa

21.4.1.3 Application of the Phomopsin Elisa

21.4.2 Corynetoxins

21.4.2.1 Source of Corynetoxins

21.4.2.2 Development of the Corynetoxin Elisa

21.4.2.3 Application of Elisa

21.5 Hplc-Ms Detection and Tentative Identification of Toxic Pyrrolizidine Alkaloids

21.5.1 Toxic Pyrrolizidine Alkaloids

21.5.2 Detection in Plant Extracts

21.5.2.1 Echium plantagineum and Echium vulgare

21.5.2.2 Senecio ovatus and Senecio jacobaea

21.5.3 Detection and Quantitation in Honey

21.6 Personal Insight and Future Directions

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