Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products 85

ISBN-13: 9783211837832 / Angielski / Twarda / 2002 / 262 str.

W. Herz; H. Falk; G. W. Kirby

Opis

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Spis treści

Natural Products Derived from Naphthalenoid Precursors by Oxidative Dimerization.- 1. Introduction.- 2. Isolation and Structure Elucidation.- 2.1. Spirobisnaphthalenes with Two Oxygen Bridges.- 2.2. Spirobisnaphthalenes with Three Oxygen Bridges (Preussomerins).- 2.3. Spirobisnaphthalenes with Two Oxygen Bridges and One C-C Bridge (Spiroxins).- 2.4. Determination of Relative and Absolute Stereochemistry.- 3. Biological Activity.- 4. Biosynthesis.- 5. Synthesis.- 5.1. Biomimetic Type Approach.- 5.2. Spiroketalization Approach.- Acknowledgements.- References.- Prokaryotic Glycoproteins.- 1. Introduction.- 2. S-Layer Glycoproteins.- 2.1. Uniqueness of S-Layer Glycoproteins.- 2.2. From Chemical Composition to Structural Concept.- 2.3. Biosynthesis.- 2.4. Molecular Biological Insights.- 2.5. Perspectives.- 3. Non-S-Layer Glycoproteins.- 3.1. Intracellular Glycoproteins.- 3.2. Membrane-Associated Glycoproteins.- 3.3. Surface-Associated Glycoproteins.- 3.4. Extracellular Glycoproteins.- 3.5. “Cellular” Glycoproteins.- 3.6. Synthetic Glycopeptides and Glycoproteins.- 4. Conclusions.- Acknowledgements.- References.- Carbazole Alkaloids IV.- I. Introduction.- A. Nomenclature.- B.Occurrence.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. Ultraviolet Absorption Spectra.- 2. IR Spectra.- 3. NMR Spectra.- 4. Mass Spectra.- 5. X-ray Crystallography.- B. Chemical Methods.- C. Synthesis.- 1. Synthesis from Monocyclic Systems.- 2. Synthesis from Bicyclic Systems.- 3. Synthesis from Tricyclic Systems.- 4. Synthesis of Carbazoles by Electrocyclisation.- 5. Synthesis by Photolytic Methods.- III. Biogenesis of Carbazole Alkaloids.- IV. Biological and Therapeutic Properties of Carbazoles and Carbazole Alkaloids.- V. Chemistry of Carbazole Alkaloids.- A. Alkaloids from Higher Plants.- i) C13-Alkaloids.- 1. 9-Carboethoxy-3-methylcarbazole.- 2. Clausenol.- 3. Clausenine.- 4. 9-Formyl-3-methylcarbazole.- 5. Murrayaline B.- 6. 2-Methyl-7-hydroxycarbazole or 2-Hydroxy-7-methylcarbazole.- 7. N-Methoxy-3-hydroxymethylcarbazole.- 8. 3-Formyl-7-hydroxycarbazole.- 9. 0-Methylmukonal.- 10. 3-Formyl-6-methoxycarbazole.- 11. 7-Methoxymukonal.- 12. Clausenal.- 13. 6-Methoxymurrayanine.- 14. 7-Methoxy-O-methylmukonal.- 15. Murrayaline C.- 16. Carbazole-3-carboxylic Acid.- 17.3-Carbomethoxycarbazole.- 18. Clauszoline C.- 19. 3-Carbomethoxy-6-methoxycarbazole.- 20. Clauszoline I.- 21. Clauszoline J.- 22. Clauszoline K.- 23. Clauszoline L.- 24. Clauszoline M.- ii) C18-Alkaloids.- 1. Clauszoline B.- 2. Clauszoline D.- 3. Euchrestine A.- 4. Eustofoline D.- 5. Furostifoline.- 6. Glycomaurine.- 7. Glycomaurol.- 8. 7-Methoxyheptaphylline.- 9. 7-Methoxymurrayacine.- 10. Murrayamine A.- 11. Pyrayafoline B.- 12. Pyrayafoline C.- 13. Mukoenine A.- 14. Mukoenine C.- 15. Murrayaquinone E.- 16. Clauszoline H.- iii) C23-Alkaloids.- 1. Clauszoline A.- 2. Clauszoline F.- 3. Euchrestine B.- 4. Euchrestine C.- 5. Euchrestine D.- 6. Euchrestine E.- 7. Eustifoline B.- 8. Eustifoline C.- 9. Isomahanine.- 10. (+)-Mahanine.- 11. Murrayaline D.- 12. Murrayamine B.- 13..Murrayamine C.- 14. Murrayanol.- 15. Pyrayafoline D.- 16. Murrayaquinone C.- 17. Murrayaquinone D.- 18. Pyrayafoline E.- 19. Mukoenine B.- iv) Dimeric Carbazole Alkaloids from Higher Plants.- a) C26-Alkaloids.- 1. Indole Dimer.- 2. Bis-2-hydroxy-3-methylcarbazole.- 3. Bismurrayaquinone A.- 4. Chrestifoline A.- 5. Cherestifoline D.- 6. Murrastifoline A.- 7. Murrastifoline B.- 8. Murrastifoline F.- b) C31-Alkaloids.- 1. Chrestifoline B.- 2. Murrafoline G.- 3. Murrastifoline D.- 4. Murrastifoline E.- c) C36-Alkaloids.- 1.Chrestifoline C.- 2. Murrafoline H.- 3. Murrastifoline C.- 4. Bis-7-hydroxygirinimbine A.- 5. Bis-7-hydroxygirinimbine B.- 6. Murranimbine.- d) C46-Alkaloids.- 1. Bismahanine.- 2. Bismurrayafoline C.- 3. Bismurrayafoline D.- B. Alkaloids from Lower Plants.- i) Alkaloids from Microbial Sources.- a) Alkaloids Built on a Carbazole Skeleton.- 1. Aflavazole.- 2. Carazostatin.- 3. Carquinostatin A.- b) Indolocarbazoles.- i) Alkaloids Built on an Indolocarbazole Skeleton (Two Nitrogens).- 1. Antitumor Compound AT 2433 Al.- 2. Antitumor Compound AT 2433 A2.- 3. Antitumor Compound AT 2433 B1.- 4. Antitumor Compound AT 2433 B2.- 5. Arcyriaflavin B.- 6. Arcyriaflavin C.- 7. Protein Kinase C Inhibitor K-252a.- 8. Protein Kinase C Inhibitor K-252b.- 9. Protein Kinase C Inhibitor K-252c.- 10. Protein Kinase C Inhibitor K-252d.- 11. Rebeccamycin.- 12. Staurosporine.- 13. Tan 1030 A.- 14. Tan 999.- 15. UCN-01.- ii) Alkaloids from Marine Sources.- 1. 1-Methylcarbazole.- 2. 1-Acetylcarbazole.- 3. Aldose Reductase Inhibitors.- References.- Author Index.