Studies in Natural Products Chemistry

Contributors
Preface
Chapter 1: Glycosphingolipid Ligands for Invariant Natural Killer T cells as Immunostimulants
Abstract

Introduction

Synthesis of KRN7000

X-Ray Crystallographic Analysis

Stereostructure of the Sphingosine Part of KRN7000

SAR Studies on KRN7000

Th1-Type Analogs of KRN7000

Th2-Type Analogs of KRN7000

Summary of SAR Study

Evaluation of the Binding Affinity by SPR Spectroscopy

Molecular Dynamics Simulation Study

Research Intended to Discover the Natural Microbial and Endogenous Ligands of NKT Cells

Concluding Remarks

Acknowledgments

Chapter 2: Synthesis of Imidazole Alkaloids Originated in Marine Sponges
Abstract

Introduction

Syntheses of Naamidines A–I

Syntheses of Preclathridine A and Clathridine A

Syntheses of Naamines

Syntheses of Isonaamines and Isonaamidines

Synthesis of Pyronaamidine

Discovered, but not yet Synthesized Imidazole Alkaloids

Chapter 3: Cerebrosides from Marine Organisms
Abstract

Introduction

Isolation and Purification

Structural Elucidation

Chemical Structures

Conclusions

Acknowledgments

Chapter 4: Isolation and Analysis of Lignin–Carbohydrate Complexes Preparations with Traditional and Advanced Methods: A Review
Abstract

Introduction

Isolation of LCC Preparations from Wood and Pulps

LCC Analysis

Quantification of LCC Linkages

General Discussion

Implementation of Enzymes in LCC Studies

Conclusions

Chapter 5: Isolation, Characterization, and Biological Activities of Polysaccharides from Medicinal Plants and Mushrooms
Abstract

Introduction

Molecular Basis of Cancer Formation and Development

Isolation and Purification of Polysaccharides

Polysaccharide Structure–Function Relationship and Mechanism of Action

Rational and Targeted Design and Screening Programs for Chemotherapeutics

Polysaccharides from Plants and Mushrooms with Immunomodulatory and Anticancer Activities

Concluding Remarks and Direction for Future Research

Chapter 6: Natural Compounds (Small Molecules) as Potential and Real Drugs of Alzheimer's Disease: A Critical Review
Abstract

Introduction

Pathophysiology of AD

Perspectives of Small Molecules Effect Study

Conclusion

Acknowledgments

Chapter 7: Natural Antiviral Compounds
Abstract

Introduction

Virus

Concluding Remarks

Chapter 8: Chemopreventive Properties of Fruit Phenolic Compounds and Their Possible Mode of Actions
Abstract

Introduction

Cancer

Fruit Phenolic Compounds

Chemoprevention

Chemopreventive Properties of Fruit Phenolic Compounds

Conclusion

Acknowledgments

Chapter 9: Plant Secondary Metabolites: Structure–Activity Relationships in Human Health Prevention and Treatment of Common Diseases
Abstract

Introduction

Nutraceuticals

Plant Chemical Defenses

Natural Products in Medicine

Phenolic Compounds

α,β-Unsaturated δ-Lactones

Terpenoids

Nitrogen Compounds

Sulfur Compounds

Concluding Remarks

Acknowledgments

Chapter 10: Assignment of Regio- and Stereochemistry of Natural Products Using Mass Spectrometry Chlorogenic Acids and Derivatives as a Case Study
Abstract

Introduction

Chlorogenic Acids

MS and Identification of CGAs

LC–MS and LC–MSn Identification of CGAs in Green Coffee Beans

Identification of Monoacyl Quinic Acids

Identification of Di- and Triacyl Quinic Acids

Mechanistic Considerations

Assignment of Side Chain Regiochemistry Feruloyl Versus Isoferuloylquinic Acids

Cinnamoyl Shikimic Acids

Quinic Acid Lactones

Quinic Acid Esters

Epimers of Quinic Acid—Distinction of Diastereoisomeric Compounds

Distinguishing Multiple Isomers in Direct Infusion Experiments

Energy-Resolved Mass Spectra

General Experimental Considerations in Tandem MS

Outlook and Conclusion

Chapter 11: Tetrapyrrole Compounds of Cyanobacteria
Abstract

Introduction

Synthesis of Macrocyclic and Linear Tetrapyrrole Compounds

Corrinoid Compounds in Edible Cyanobacteria

Physiological Functions of Corrinoid Compounds in Cyanobacteria

Phycobilins in Edible Cyanobacteria

Concluding Remarks

Chapter 12: Recent Progress in the Synthesis of 2,6-Disubstituted Hydroxypiperidine Alkaloids
Abstract

Introduction

Metal-Catalyzed Formation of the Piperidine Ring

Piperidine Ring Formation via Intramolecular Nucleophilic Attack

Piperidine Ring Formation by Intramolecular Nucleophilic Displacement

Piperidine Ring Formation from Furan Derivatives

Piperidine Ring Formation via Amidomercuration

Other Methods for Formation of the Piperidine Ring

Concluding Remarks

Acknowledgment

Chapter 13: Structure, Biological Properties, and Total Synthesis of Polyhydroxylated Pyrrolizidines of the Hyacinthacines Family
Introduction

Natural Occurrence, Isolation, and Structure Determination of Hyacinthacines

Biological Activities of Hyacinthacines

Total Syntheses of Hyacinthacines

Conclusion

Chapter 14: The Synthesis of Seven-Membered Rings in Natural Products
Abstract

Introduction

Synthetic Methodology Directed to Seven-Membered Rings

One-Carbon Ring Expansion Methodologies

Natural Product Syntheses with Seven-Membered Ring Incorporation

Conclusion and Perspectives

Acknowledgments

Index