Studies in Natural Products Chemistry, Volume 44

547 Pages·2015·39.688 MB·English

by  Atta-ur-Rahman

Studies in Natural
Products Chemistry
Volume 44
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Studies in Natural
Products Chemistry
Volume 44
Edited by
Atta-ur-Rahman, FRS
International Center for Chemical and Biological Sciences
H.E.J. Research Institute of Chemistry
University of Karachi
Karachi, Pakistan
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ISBN: 978-0-444-63460-3
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Contents
Contributors xi
Preface xv
1. Terpenoids and Sterols from Mushrooms 1
Yasunori Yaoita, Masao Kikuchi and Koichi Machida
Introduction 1
Sesquiterpenoids 2
Lactarane-Type Sesquiterpenoids 2
Marasmane-Type Sesquiterpenoids 5
Nardosinane-Type and Aristolane-Type Sesquiterpenoids 7
Protoilludane-Type Sesquiterpenoids 7
Russulane-Type Norsesquiterpenoids 8
Triterpenoids 11
Lanostane-Type Triterpenoids 11
Cucurbitane-Type Triterpenoids 14
Sterols 14
Sterols Bearing 5a,6a-Epoxy Group 15
Sterols Bearing 5a,9a-Epidioxy and 5b,9b-Dihydroxy Groups 17
Sterols Bearing Enone, Diene, and Ketone Moieties 19
Sterols Bearing 3b,5a,6b,7a-Tetrahydroxy, 3b,5a,6a,9a-Tetrahydroxy,
and 3b,5a,6b,9a-Tetrahydroxy Groups 20
23-Methylergostane-Type Sterols 21
Sterols Bearing 1,2,3,4,5,10,19-Heptanor Structure 22
Meroterpenoids 23
Conclusions 27
References 29
2. From Bench to Bedside: Natural Products
and Analogs for the Treatment of Neglected
Tropical Diseases (NTDs) 33
Simone Kobe de Oliveira, Louise Domeneghini Chiaradia-Delatorre,
Alessandra Mascarello, Beatriz Veleirinho, Fernanda Ramlov, Shirley
Kuhnen, Rosendo Augusto Yunes and Marcelo Maraschin
Introduction 33
Neglected Tropical Diseases 50
Tuberculosis 50
v
vi Contents
Leishmaniasis 53
Malaria 55
Chagas Disease (American Trypanosomiasis) 61
Human African Trypanosomiasis (Sleeping Sickness) 64
Dengue 68
Lymphatic Filariasis (Elephantiasis) 71
Helminthiasis 74
Leprosy (Hansen Disease) 76
Trachoma 77
Buruli Ulcer 78
Schistosomiasis 79
Conclusions 82
References 83
3. Febrifugine and Its Analogs: Studies for Their Antimalarial
and Other Therapeutic Properties 93
Sanjoy Singh Ningthoujam, Anupam Das Talukdar,
Deepa Nath, Norazah Basar, Kumar Singh Potsangbam
and Manabendra Dutta Choudhury
Introduction 93
Discovery 94
Structure Elucidation 95
Chemical and Physical Properties of Febrifugine 96
Synthesis of Febrifugine 98
Pharmacology of Febrifugine 100
Antimalarial Activity of Febrifugine 100
Anticoccidial Activity 103
Toxicity 103
Febrifugine Analogs 104
Halofuginone 105
Antimalarial Properties 105
Coccidiosis 106
Autoimmune Diseases 107
Other Diseases 107
Polypharmacy 108
Concluding Remarks 109
Acknowledgments 109
References 110
4. Macrocyclic N-Methylated Cyclic Peptides
and Depsipeptides 113
Rani Maharani, Brad E. Sleebs and Andrew B. Hughes
Introduction 113
Aureobasidins 114
Introduction 114
Isolation 114
Contents vii
Classification of Abs 117
Structural Determination 121
Biological Activity 127
Synthesis 130
Cyclosporins 138
Introduction 138
Isolation 139
Classification of Cs 140
Structural Determination 147
Biological Activity 150
Synthesis 155
Dolastatin 168
Introduction 168
Isolation 168
Classification of Cyclic Peptides 169
Structure Determination 176
Biological Activity 179
Synthesis 180
Didemnins 188
Introduction 188
Isolation 189
Classification of Didemnins 193
Structural Determination 196
Biological Activity 202
Synthesis 207
Miscellaneous Cyclopeptides and Cyclodepsipeptide 217
Introduction 217
Omphalotins 218
Petriellin 222
Clavariopsins 226
Somamides 230
Salinamides 234
Conclusion 239
References 241
5. Anticancer Drugs and Potential Anticancer
Leads Inspired by Natural Products 251
Prasat Kittakoop
Introduction 251
Tubulin/Microtubule-Targeted Anticancer Agents 253
Heat Shock Protein 90 Inhibitors as Anticancer Agents 258
Inhibitors of Hedgehog Signaling Pathway as Anticancer Agents 266
Histone Deacetylase Inhibitors as Anticancer Agents 271
Inhibitors of Tyrosine Kinases as Anticancer Agents 278
Inhibitors of Cyclin-Dependent Kinases as Anticancer Agents 286
Acknowledgments 295
References 297
viii Contents
6. Synthetic Aspects of Brassinosteroids 309
Vladimir A. Khripach, Vladimir N. Zhabinskii and Yuri V. Ermolovich
Introduction 309
Methodology 310
Natural BS 316
Isotopically Labeled BS 320
BS Analogs 326
Inhibitors of BS Biosynthesis 341
Conjugates 342
Acknowledgment 346
References 347
7. The Chemistry and Bioactivity of Macrolides
from Marine Microorganisms 353
Qing-Ai Liu, Juan-Juan Zheng, Yu-Cheng Gu,
Chang-Yun Wang and Chang-Lun Shao
Introduction 353
Isolation, Identification, and Biological Activities 355
10-Membered Macrolides 355
12-Membered Macrolides 358
13–16-Membered Macrolides 360
20–30-Membered Macrolides 364
More than 30-Membered Macrolides 367
Other Marine Macrolides 369
Chemical Synthesis 371
Modiolide A 371
Xestodectalactones A–C 371
Sporiolides A and B 379
Aspergillides 381
Lyngbouilloside 384
RALs 386
Cyanolide A 388
Macrosphelide H 390
Halichoblelide 390
Arenicolide A 392
Conclusion 395
References 396
8. Protein Kinase Inhibitors from Microorganisms 403
P. Radhika, M. Murali Krishna Kumar and K. Purna Nagasree
Introduction 403
Microbial Alkaloids as Protein Kinase Inhibitors 405
Bisindolocarbazole Alkaloids 405
Contents ix
Miscellaneous Alkaloidal Kinase Inhibitors 411
Benzoquinones 416
Polyphenols and Other Related Compounds 425
Peptides 431
Miscellaneous 432
Concluding Remarks 437
References 438
9. Possible Anti-Parkinson’s Disease
Therapeutics from Nature: A Review 447
Abhijit Dey and Jitendra Nath De
Introduction 450
Anti-PD Activity of Plant-Derived Natural Compounds 464
Anti-PD Activity of Crude/Semipurified Plant
Extracts/Fractions 496
Anti-PD Herbal Formulations 504
Discussion 504
Concluding Remarks 505
References 508
Index 521