160. Herbal Pharmacology

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160. Herbal Pharmacology

160. Herbal Pharmacology

 

 

CATEGORY: Medical & Medicine – 500 Courses

COURSE NUMBER: 160

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Syllabus

Preface xiii
Contributors xvii
1 The Chemistry and Biology of Epothilones—Lead Structures
for the Discovery of Improved Microtubule Inhibitors 1
Karl-Heinz Altmann
1.1. Introduction 1
1.2. Biological Effects of Epo B 4
1.2.1 In Vitro Activity 4
1.2.2 In Vivo Antitumor Activity 8
1.3. Epothilone Analogs and SAR Studies 9
1.3.1 Lactam-Based Analogs 9
1.3.2 Modifications in the C9–C11 Region 10
1.3.3 Modifications of the Epoxide Moiety 13
1.3.4 C-26-Modified Analogs 17
1.3.5 Side-Chain Modifications 18
1.3.6 Aza-Epothilones 22
1.4. Pharmacophore Modeling and Conformational Studies 25
1.5. Epothilone Analogs in Clinical Development 26
1.6. Conclusions 28
Acknowledgments 29
References 29

2 The Chemistry and Biology of Vancomycin and Other
Glycopeptide Antibiotic Derivatives 35
Roderich D. Su ̈ssmuth
2.1. Introduction 35
2.2. Classification of Glycopeptide Antibiotics 37
2.3. Mode of Action 39
2.4. Glycopeptide Resistance 40
2.5. Biosynthesis 43
2.6. Total Synthesis 45
2.7. Glycopeptides as Chiral Selectors in Chromatography and
Capillary Electrophoresis 47
2.8. Structural Modifications of Glycopeptide Antibiotics and
Structure Activity Relationship (SAR) Studies 49
2.8.1 Modifications of Glycopeptide Antibiotics 51
2.8.2 Rational Concepts for the Design of Novel Glycopeptides 58
2.8.3 Conclusions 64
Acknowledgment 65
References 65
3 Structure Modifications and Their Influences on Antitumor
and Other Related Activities of Taxol and Its Analogs 73
Wei-Shuo Fang, Qi-Cheng Fang, and Xiao-Tian Liang
3.1. Discovery and Research and Development of Taxol 73
3.2. Paclitaxel Analogs Active Against Normal Tumor Cells 74
3.2.1 C-13 Side Chain 74
3.2.2 A Ring and Its Substitutions 81
3.2.3 B Ring and Its Substitutions 87
3.2.4 C Ring and Its Substitutions 94
3.2.5 D Ring 101
3.2.6 Macrocyclic Analogs 103
3.2.7 Miscellaneous 104
3.3. Exploration on Mechanism of Paclitaxel Related to Tubulin
Binding and Quest for Its Pharmacophore 106
3.3.1 Biochemical Mechanism of Paclitaxel Related
to Tubulin Binding 106
3.3.2 Identification of Bioactive Conformations and Quest
for a Pharmacophore for Paclitaxel 108

3.4. Natural and Semisynthetic Taxoids Overcoming Multidrug
Resistance (MDR) 111

3.4.1 Structure-Modified Taxoids With Better Activity Toward
MDR Tumors 111
3.4.2 Nonpaclitaxel-Type Taxoids With MDR Reversal Activities 114
3.4.3 Factors Contributing to the Resistance to Paclitaxel 115
3.5 Design, Synthesis and Pharmacological Activity of Prodrugs
of Paclitaxel 117
3.5.1 Prodrugs Prepared to Improve Water Solubility 117
3.5.2 Prodrugs Designed for Enhancing Specificity 119
3.6 Other Biological Actions of Paclitaxel 121
3.7 New Antimicrotubule Molecules Mimicking Action of Paclitaxel 122
3.8 Conclusion 123
Acknowledgments 124
References 124
4 The Overview of Studies on Huperzine A: A Natural Drug
for the Treatment of Alzheimer’s Disease 143
Da-Yuan Zhu, Chang-Heng Tan, and Yi-Ming Li
4.1 Introduction 143
4.1.1 Powerful AChEI Originated From Traditional
Chinese Medicine 143
4.1.2 Alzheimer’s Disease 144
4.2. Profiles of HA 145
4.2.1 Discovery of HA 145
4.2.2 Physical Appearance of HA 145
4.3. Plant Resources 147
4.4. Pharmacology 148
4.4.1 Effects on Cholinesterase Activity 148
4.4.2 Effects on Learning and Memory 149
4.4.3 Effects on the Protection of Neuronal Cells 150
4.4.4 Toxicology 152
4.4.5 Effects on Miscellaneous Targets 152
4.5. Clinical Trials 152
4.6. Synthesis of HA and Its Analogs 154
4.6.1 Synthesis of Racemic HA 154
4.6.2 Synthesis of Optically Pure ()-HA 157
4.6.3 Studies on the Structure–Activity Relationship 161
4.7. Structural Biology 166
4.7.1 Interaction Between HA and AChE 166

4.7.2 Structure-Based HA Analog Design 167
4.8. ZT-1: New Generation of HA AChE 169
4.8.1 Pharmacology 170
4.8.2 Toxicology 170
4.8.3 Pharmacokinetics 171
4.8.4 Clinical Trials 172
Abbreviations 172
References 173
5 Qinghaosu (Artemisinin)—A Fantastic Antimalarial
Drug from a Traditional Chinese Medicine 183
Ying Li, Hao Huang, and Yu-Lin Wu
5.1. Introduction 183
5.2. Qinghaosu and Qinghao (Artemisia annua L. Composites) 184
5.2.1. Discovery and Structure Determination of Qinghaosu 184
5.2.2. The Phytochemistry of Qinghao and Other Natural
Products from Qinghao 188
5.3. Reaction of Qinghaosu 197
5.3.1. Reduction of Qinghaosu 198
5.3.2. Acidic Degradation of Qinghaosu 199
5.3.3. Miscellaneous Chemical Reaction 201
5.3.4. Biotransformation 201
5.4. Chemical Synthesis and Biosynthesis of Qinghaosu 202
5.4.1. Partial Synthesis and Total Synthesis of Qinghaosu 202
5.4.2. Biogenetic Synthesis of Qinghaosu 204
5.5. Derivatives and Antimalarial Activity 206
5.5.1 Modification on C-12 of Qinghaosu 207
5.5.2 Water-Soluble Qinghaosu Derivatives 212
5.5.3 Modification on C-11 or/and C-12 215
5.5.4 Modification on C-4 or/and C-12 215
5.5.5 Modification on C-3 or/and C-13 216
5.5.6 Modification on C-13 216
5.5.7 Modification on C-11 and C-12 217
5.5.8 Azaartemisinin 217
5.5.9 Carbaartemisinin 218
5.5.10 Steroidal Qinghaosu Derivatives 218
5.5.11 Dimers and Trimers 219
5.5.12 1,2,4-Trioxanes and 1,2,4,5-Tetraoxanes 221

5.6. Pharmacology and Chemical Biology of Qinghaosu
and Its Derivatives 221
5.6.1 Bioactivities of Qinghaosu Derivatives and Analogs 221
5.6.2 Early Biologically Morphologic Observation of the
Antimalarial Action of Qinghaosu 224
5.6.3 The Free Radical Reaction of Qinghaosu and Its
Derivatives With Fe(II) 225
5.6.4 Antimalarial Activity and the Free Radical Reaction
of Qinghaosu and Its Derivatives 230
5.6.5 Interaction of Biomolecules with Carbon-Centered
Free Radical 235
5.6.6 Another Point of View and Summary 238
5.7 Conclusion 239
References 239
6 Progress of Studies on the Natural Cembranoids
from the Soft Coral Species of Sarcophyton Genus 257
Yulin Li, Lizeng Peng, and Tao Zhang
6.1. Introduction 257
6.2. Cembrane-Type Constituents from the Sarcophyton Genus 258
6.2.1 Sarcophytols from the Sarcophyton Genus 258
6.2.2 The Other Cembrane-Type Constituents
from the Sarcophyton Genus 260
6.3. Physiological Action of Sarcophytol A and Sarcophytol B 265
6.4. Total Synthesis of the Natural Cembranoids 266
6.4.1 Total Synthesis of Sarcophytols 267
6.4.2 Total Synthesis of Cembrene A and C 271
6.4.3 Total Synthesis of Several Natural Epoxy Cembrenoids 277
6.4.4 Total Synthesis of Cembranolides 287
6.5. Studies on Novel Macrocyclization Methods of
Cembrane-Type Diterpenoids 291
6.5.1 A Stille Cyclization Approach to ()-Isocembrene 291
Acknowledgments 296
References 296
7 Medicinal Chemistry of Ginkgolides from Ginkgo biloba 301
Kristian Strømgaard
7.1. Introduction 301
7.1.1 Ginkgo biloba Extract 301
7.1.2 Isolation and Structure Elucidation of Ginkgolides 304
7.1.3 Biosynthesis of Ginkgolides 306
7.1.4 Chemistry of Ginkgolides 307
7.2. Ginkgolides and the PAF Receptor 308
7.3. Ginkgolides and Glycine Receptors 312
7.4. Various Effects of Ginkgolides 314
7.5. Conclusions and Outlook 315
Acknowledgment 315
References 315
8 Recent Progress in Calophyllum Coumarins as
Potent Anti-HIV Agents 325
Lin Wang, Tao Ma, and Gang Liu
8.1. Introduction 325
8.2. Anti-HIV-1 Activity of Calophyllum Coumarins 329
8.2.1 Anti-HIV-1 Activity of Calanolides 329
8.2.2 Anti-HIV-1 Activity of Inophyllums 331
8.2.3 Anti-HIV-1 Activity of Cordatolides 333
8.3. Pharmacology of Calanolides 333
8.3.1 Pharmacology of (þ)-Calanolide A 333
8.3.2 Clinical Trial of (þ)-Calanolide A 334
8.4. Preparation of Calophyllum Coumarins 334
8.4.1 Total Synthesis of Racemic Calophyllum Coumarins 334
8.4.2 Preparation of Optically Active Calophyllum Coumarins 340
8.5. Structure Modification of Calanolides 349
8.6. Conclusion 350
References 351
9 Recent Progress and Prospects on Plant-Derived
Anti-HIV Agents and Analogs 357
Donglei Yu and Kuo-Hsiung Lee
9.1. Introduction 357
9.2. Khellactone Coumarin Analogs as Anti-HIV Agents 358
9.2.1 Suksdorfin as a New Anti-HIV Agent 358
9.2.2 Pyrano-30

,40 Stereoselectivity and Modification 359
9.2.3 Coumarin Skeleton Modification 362
9.2.4 SAR Conclusions 373
9.2.5 Mechanism of Action 374

9.3. Biphenyl Derivatives as Anti-HIV Agents 374
9.3.1 SAR Analysis of Naturally Occurring
Dibenzocyclooctadiene Lignans 374
9.3.2 Structural Modifications 376
9.3.3 SAR Conclusions 378
9.3.4 Mechanism of Action of Biphenyl Derivatives 378
9.4. Triterpene Betulinic Acid Derivatives as Anti-HIV Agents 379
9.4.1 Betulinic Acid Derivatives as Entry Inhibitors 379
9.4.2 Betulinic Acid Derivatives as Maturation Inhibitors 386
9.4.3 Bifunctional Betulinic Acid Derivatives with Dual
Mechanisms of Action 389
9.5. Conclusions 391
Acknowledgments 391
References 391
10 Recent Progress on the Chemical Synthesis of Annonaceous
Acetogenins and Their Structurally Modified Mimics 399
Tai-Shan Hu, Yu-Lin Wu, and Zhu-Jun Yao
10.1. Introduction 399
10.2. Total Synthesis of Mono-THF Acetogenins 401
10.3. Total Synthesis of Bis-THF Acetogenins 413
10.4. Total Synthesis of THP-Containing Acetogenins 422
10.5. Design and Synthesis of Mimics of Acetogenins 428
10.6. Summary 437
References 437
Index 443

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