Progress in the chemistry of organic natural products. Volume 114

This book describes current understandings and recent progress in four areas: in the first one, the cytochalasans, a group of fungal derived natural products characterized by a perhydro-isoindolone core fused with a macrocyclic ring are shown to exhibit high structural diversity and a broad spectrum of bioactivities. The second one is dedicated to a description of bioactive compounds from the medicinal plants of Myanmar, the third one is dedicated to new structure elucidation techniques in the field of sesquiterpenes. The last one discusses the endogenous natural products that are produced by human cells including endogenous amines, steroids, and fatty acid derived natural products. The co-metabolism and natural product production of the human microbiome is also described including tryptophan, bile acids, choline, and cysteine. Contents 6 Progress in the Chemistry of Cytochalasans 7 1 Introduction 8 2 The Structural Diversity of Cytochalasans and Their Origins 9 2.1 The Cytochalasin Group 12 2.2 The Pyrichalasin Group 35 2.3 The Chaetoglobosin Group 42 2.4 The Aspochalasin Group 60 2.5 The Alachalasin Group 77 2.6 Trichalasin 77 2.7 Future Prospects 78 3 Biological Activities of Cytochalasans 79 3.1 Cytotoxicity and Potential Anticancer Activities 80 3.2 Antimicrobial Activities 83 3.3 Antiparasitic Activities 84 3.4 Anti-inflammatory Effects 85 3.5 Antiviral Activities 85 3.6 Phytotoxic Effects and Ecological Role 86 3.7 Future Prospects 87 4 Biosynthesis of Cytochalasans 88 4.1 Cytochalasan Gene Clusters 89 4.2 Investigations into the Biosynthesis of Cytochalasans 92 4.3 Future Prospects 103 5 Chemical Syntheses of Cytochalasans 104 5.1 Synthesis of Periconiasin G 107 5.2 Syntheses of Cytochalasin B and L-696,474 107 5.3 Total Syntheses of Periconiasins A–E 111 5.4 Total Synthesis of Aspochalasins D and B and (+)-Aspergillin PZ 114 5.5 Total Synthesis of Asperchalasine A and Related Derivatives 117 5.6 Future Prospects 121 6 Conclusions 123 References 124 Bioactive Compounds from Medicinal Plants in Myanmar 141 1 Introduction 142 2 Phytochemicals and Pharmacological Activities of Medicinal Plants from Myanmar 143 2.1 Acacia concinna Wall. 143 2.2 Orthosiphon stamineus Benth. 149 2.3 Panax zingiberensis C.Y. Wu & Feng (Myanmar wild ginseng) 151 2.4 Caesalpinia crista L. 154 2.5 Elephantopus scaber L. 158 2.6 Phyllanthus niruri L. 161 2.7 Streptocaulon tomentosum Wight & Arn. 164 2.8 Curcuma comosa Roxb. 168 2.9 Vitis repens Wight & Arn. 172 2.10 Boesenbergia pandurata (Roxb.) Schltr. (Boesenbergia rotunda (L.) Mansf.) 174 2.11 Kayea assamica King & Prain 180 2.12 Cordia fragrantissima Kurz. 184 2.13 Thanakha plants: Hesperethusa crenulata L. and Limonia acidissima L. 186 2.14 Soymida febrifuga (Roxb.) A. Juss. 191 2.15 Vitex negundo L. 195 2.16 Diospyros burmanica Kurz. 198 2.17 Cinnamomum inunctum Kurz. 198 2.18 Kaempferia pulchra Ridl. 200 2.19 Picrasma javanica Blume 204 2.20 Curcuma amada Roxb. 207 2.21 Vitex trifolia L. 210 2.22 Mansonia gagei Drumm. 212 2.23 Premna integrifolia L. (syn.: P. serratifolia L.) 214 2.24 Picrorhiza kurroa Royle ex Benth. 219 2.25 Jatropha multifida L. 222 2.26 Swertia chirata Buch.-Ham. ex Wall. 225 3 Synthesis Aspects 227 4 Conclusions 231 References 232 New Techniques of Structure Elucidation for Sesquiterpenes 258 1 Introduction 259 2 Techniques Based on NMR Spectroscopy 259 2.1 Calculation of Chemical Shifts 260 2.2 Calculation of Coupling Constants 267 2.3 Residual Dipolar Couplings 273 2.4 Advanced Mosher’s Methods 275 2.5 Use of Cryoprobes for NMR Measurements 279 3 Techniques Based on Chiroptical Properties 281 3.1 Vibrational Circular Dichroism 281 3.2 Electronic Circular Dichroism 285 4 Techniques Based on X-Ray Diffraction 296 4.1 Calculation of the Flack Parameter 297 4.2 Calculation of the Flack and Hooft Parameters 303 5 Conclusions 308 References 309 Human Endogenous Natural Products 317 1 Introduction 318 2 Endogenous Natural Products 318 2.1 Endogenous Amines 318 2.2 Steroid Natural Products 321 2.3 Fatty Acid-Derived Natural Products 324 3 Host–Microbe Co-metabolism 326 3.1 Presence and Function of the Human Microbiota 326 3.2 Co-Metabolism of Tryptophan and Other Aromatic Amino Acids 328 3.3 Co-Metabolism of Bile Acids 328 3.4 Co-Metabolism of Choline 331 3.5 Co-Metabolism of Cysteine and Other Sulfur-Containing Compounds 332 4 Human Natural Products and Disease 332 4.1 Steroidogenic Inherited Diseases 332 4.2 Trimethylamine Oxide and Atherosclerosis 333 5 Techniques for the Identification of Metabolites 333 5.1 Mass Spectrometry 335 5.2 Nuclear Magnetic Resonance Spectroscopy 336 6 Conclusions 337 References 338