The Alkaloids: Chemistry and Biology (Volume 61) (The Alkaloids, Volume 61)

In this volume of The Alkaloids: Chemistry and Biology the recent progress on two classes of alkaloids, the Lycopodium alkaloids and the dibromotyrosine alkaloids, is presented. TheAlkaloidsVolume61Chem1388_f.jpg 1 1.pdf 2 Contents 2 2.pdf 3 Contributors 3 3.pdf 4 Preface 4 4.pdf 5 THE LYCOPODIUM ALKALOIDS 5 Introduction 5 Structures of Representative Alkaloids 6 Huperzines 6 Lycoposerramines 12 Serratezomines 12 Complanadine A 17 Lyconadin A 18 Senepodines 20 Lyconesidines 23 Himeradine A 25 Sieboldine A 27 Cermizines 29 Lucidines 32 Miscellaneous 33 Biosynthesis and Biogenesis 34 Biosynthesis of Lycopodium Alkaloids 34 Biogenesis of Lycoposerramines 35 Biogenesis of Macleanine 35 Biogenesis of Serratezomines 35 Biogenesis of Lyconadin A 39 Biogenesis of Senepodines 39 Biogenesis of Himeradine A 40 Biogenesis of Sieboldine A 40 Biogenesis of Cermizines 41 Total Synthesis 42 Magellanine (98) 42 Lycopodine (92) 43 Huperzine B (2) 44 Paniculatine (146) 45 Luciduline (160) 45 Na-Acetyl-Nb-methylphlegmarine (174) 46 Spirolucidine (193) 47 (+-)-13-Deoxyserratine (203) 47 Pharmacology of Huperzine A (1) 48 Total Synthesis of Huperzine A (1) 52 SAR Studies of Huperzine A (1) 53 Analogues of Huperzine A and Inhibitory Activities of AChE 53 Molecular Modeling and X-ray Studies 56 Conclusions 56 References 58 5.pdf 62 THE MARINE BROMOTYROSINE DERIVATIVES 62 Introduction 62 Isolation and Structure Elucidation 64 Simple Bromotyrosine Derivatives 64 Spirocyclohexadienylisoxazoline Bromotyrosine Derivatives 70 Bis-Spirocyclohexadienylisoxazolines 70 Mono-spirocyclohexadienylisoxazolines 75 Simple Mono-spirocyclohexadienylisoxazolines 75 Bromotyrosine Mono-spirocyclohexadienylisoxazoline 76 Histamine Mono-spirocyclohexadienylisoxazolines 77 Linear Side Chain Mono-spirocyclohexadienylisoxazolines 80 Spirooxepinisoxazoline (Oxepin) Bromotyrosine Derivatives 80 Oximes 82 Oxime-histamines 82 Oxime-Disulfides 83 Oxime-Bromotyramines 87 Other Oxime Structures 89 Bastadins 90 Bastadins 90 Hemibastadins 93 Other Structural Classes 95 Spectroscopic Data 101 Biosynthesis of Bromotyrosine Derivatives 102 Biogenesis of Isospiroxazoline 102 Biogenesis of the Psammaplysins 219 Biosynthesis of Psammaplin type of compounds 220 Synthesis 221 Synthesis of small bromotyrosine derivatives 221 Synthesis of spirocyclohexadienylisoxazoline 224 Synthesis of bastadins 224 Bioactivity 236 Antimicrobial activity 237 Antivancer activity 237 Antifouling 242 Enzyme activity 248 Antiviral activity 253 Calcium channel regulator 254 Other activities 254 Conclusions 256 References 256 6.pdf 266 CUMULATIVE INDEX OF TITLES 266 7.pdf 273 INDEX 273 Content: Contents Page v Contributors Page vii Preface Page ix The Lycopodium Alkaloids Original Research Article Pages 1-57 Jun’ichi Kobayashi, Hiroshi Morita The Marine Bromotyrosine Derivatives Original Research Article Pages 59-262 Jiangnan Peng, Jing Li, Mark T. Hamann Cumulative Index of Titles Pages 263-269 Index Pages 271-282 Alkaloids are a major group of natural products derived from a variety of organisms, which are widely used as medicinal and biological agents. This work covers the field of chemotaxonomy, structure elucidation, synthesis, biosynthesis, and biology of various classes of alkaloids from higher and lower plants, marine organisms, and others. Provides coverage of the field of the chemotaxonomy, structure elucidation, synthesis, biosynthesis, and biology of various classes of alkaloids from higher and lower plants, marine organisms, and various terrestrial animals. Each volume provides a detailed coverage of particular classes or sources of alkaloids Part of a monographic series on alkaloids providing coverage of the expanding field of the chemotaxonomy, structure elucidation, synthesis, biosynthesis and biology of all classes of alkaloids, this volume deals with plant biotechnology and how to get alkaloids from mushrooms.