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

ISBN-13: 9783709173428 / Angielski / Miękka / 2012 / 333 str.

E. Fattorusso; R. J. Highet; D. L. Klayman

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

Naturally Occurring Plant Coumarins.- I. Scope of the Review.- II. Progress in the Past Six Years.- III. Introduction to Tables.- Table 1. 7-Oxygenated Coumarins.- 1.1 6-Substituted-7-Oxygenated Coumarins.- 1.2 8-Substituted-7-Oxygenated Coumarins.- 1.3 5,6-Disubstituted-7-Oxygenated Coumarins.- 1.4 6,8-Disubstituted-7-Oxygenated Coumarins.- Table 2. 5,7-Dioxygenated Coumarins.- Table 3. 6,7-Dioxygenated Coumarins.- Table 4. 7,8-Dioxygenated Coumarins.- Table 5. 5,6,7-Trioxygenated Coumarins.- Table 6. 5,7,8-Trioxygenated Coumarins.- Table 7. 6,7,8-Trioxygenated Coumarins.- Table 8. 5,6,7,8-Tetraoxygenated Coumarins.- Table 9. 3-Substituted Coumarins.- 9.1 3-Aryl-Substituted Coumarins.- Table 10. 4-Substituted Coumarins.- 10.1 4-Aryl-Substituted Coumarins.- Table 11. Miscellaneous Coumarins.- 11.1 3-Aryl-Oxygenated Coumarins.- 11.2 Coumestans.- Table 12. Biscoumarins.- Table 13. Triscoumarins.- Amendments/Additions to Entries in Reference (171) and/or Reference [172]..- Table 1. Coumarin and 7-Oxygenated Coumarins.- 1.1 6-Substituted-7-Oxygenated Coumarins.- 1.2 8-Substituted-7-Oxygenated Coumarins.- Table 2. 5,7-Dioxygenated Coumarins.- Table 3. 6,7-Dioxygenated Coumarins.- Table 4. 7,8-Dioxygenated Coumarins.- Table 5. 5,6,7-Trioxygenated Coumarins.- Table 6. 5,7,8-Trioxygenated Coumarins.- Table 7. 6,7,8-Trioxygenated Coumarins.- Table 8. 5,6,7,8-Tetraoxygenated Coumarins.- Table 9. 3-Substituted Coumarins.- 9.1 3-Aryl-Substituted Coumarins.- Table 10. 4-Substituted Coumarins.- 10.1 4-Aryl-Substituted Coumarins.- Table 11. Miscellaneous Coumarins.- 11.1 3-Aryl-Oxygenated Coumarins.- 11.2 Coumestans.- Table 12. Biscoumarins.- Formula Index.- Trivial Name Index.- References.- Artemisinin: An Endoperoxidic Antimalarial from Artemisia annua L..- 1. Introduction.- 1.1. Historical.- 1.2. History of the Qinghao Plant.- 1.3. Modern History of Artemisia annua L. in Chinese Medicine.- 2. Artemisia annua L. and its Constituents.- 2.1. Taxonomy.- 2.2. Geographic Distribution.- 2.3. Cultivation.- 2.4. Cell Culture.- 2.5. Isolation of Artemisinin from A. annua.- 2.6. Other Constituents of A. annua.- 3. Artemisinin Structure Determination.- 4. Artemisinin Syntheses.- 4.1. From ( - )-Isopulegol.- 4.2. From (R)-(+)-Hydroxymenthol.- 4.3. From 3(R)-Methyl-6-phenylsulfmyl-cyclohexanone.- 4.4. From ( + )-Isolimonene.- 4.5. From Artemisinic Acid.- 4.6. From Arteannunin B.- 5. Physical Measurements and Analyses.- 5.1. NMR.- 5.1.1. 1H.- 5.1.2. 13C.- 5.2. Circular Dichroism.- 5.3. Infrared.- 5.4. Mass Spectroscopy.- 5.5. X-Ray Crystallography.- 5.6. Quantitative TLC.- 5.7. Titrimetric.- 5.8. HPLC.- 5.8.1. Electrochemical Detection.- 5.8.2. UV Detection Methods.- 5.8.3. Capillary Gas Chromatography.- 5.8.4. Diverse Analytical Methods.- 5.8.5. Radiolabelling.- 5.8.6. Radioimmuno Assay.- 6. Reactions of Artemisinin and its Derivatives.- 6.1. Thermolysis.- 6.2. Chemical.- 6.2.1. Reactions with Alkali.- 6.2.2. Reactions with Ammonia and Amines.- 6.2.3. Reactions with Acid.- 6.2.3.1. Arteether.- 6.2.3.2. Dihydroartemisinin.- 6.2.3.3. Acid-Catalyzed Additions to Anhydrodihydroartemisinin.- 6.2.3.3.1. Triphenylphosphine Hydrobromide.- 6.2.3.3.2. p-Toluenesulfonic Acid.- 6.2.3.4. Acid-Catalyzed Rearrangements of Artemisinin Derivatives.- 6.2.3.4.1. Lewis Acids.- 6.2.3.4.2. Silica Gel-Catalyzed Rearrangements.- 6.2.4. Reaction of Artemisinin with Reducing Agents.- 6.2.4.1.Lithium Aluminum Hydride.- 6.2.4.2. Sodium Borohydride.- 6.2.4.3. A Mixture of Sodium Borohydride and Boron Trifluoride.- 6.2.4.4. Hydrogenation.- 6.2.5. Bromination.- 6.2.6. Fluorinated Artemisinin Derivatives.- 6.2.7. Epoxidation of Anhydrodihydroartemisinin.- 6.2.8. Osmium Tetroxide Oxidation.- 7. Dihydroartemisinin Derivatives.- 7.1. Derivatives with Enhanced Oil Solubility.- 7.1.1. Ethers.- 7.1.2. Esters.- 7.1.3. Carbonates.- 7.2. Derivatives with Enhanced Water Solubility.- 7.2.1. Sodium Artesunate.- 7.2.2. Sodium Artelinate and Related Derivatives.- 7.3. Artemisinin Derivatives.- 7.3.1. (+)-Deoxoartemisinin.- 7.3.2. (+)-Homodeoxoartemisinin.- 7.3.3. (+)-10-Alkyldeoxoartemisinin.- 7.3.4. (+)-10?-Allyldeoxoartemisinin.- 7.3.5. C-3 and C-9 Substituted 10-Deoxoartemisinins.- 7.3.6. C-14 Modified Deoxoartemisinins.- 8. Simplified Artemisinin Derivatives.- 8.1. 9-Desmethylartemisinin.- 8.2. 6,9-Bisnorartemisinin.- 8.3. (+)-8a,9-Secoartemisinin.- 8.4. (+)-4,5-Secoartemisinin.- 8.5. (+)-Hexahydroisochroman-3-one.- 8.6. 4,5-Desethanoartemisinin.- 8.7. 9-Alkyl-9-desmethylartemisinin.- 8.8. C-3 and C-9 Modified Artemisinin Derivatives.- 8.9. Carba-Analogs of Artemisinin.- 9. Quantitative Structure-Activity Analyses.- 10. Tricyclic 1,2,4-Trioxane Analogs.- 11. Metabolism.- 11.1. Microbial Metabolites of Artemisinin and its Derivatives.- 11.2. Mammalian Metabolites.- 12. Test Data of Artemisinin Derivatives.- 12.1. In Vitro.- 12.2. In Vivo.- 13. Toxicity.- 14. Pharmacology and Pharmacokinetics.- 15. Clinical Evaluation of Artemisinin and Derivatives.- 15.1. Dihydroartemisinin.- 16. Mechanisms of Action.- 17. Other Peroxides.- 17.1. Naturally Occurring Peroxides.- 17.2. Synthetic Peroxides.- 18. Conclusion.- References.- Marine Glycolipids.- 1. Introduction.- 2. Isolation Procedures.- 3. Determination of the Structure of Glycolipids.- 3.1. Determination of the Structure of the Sugar Portion.- 3.2. Determination of the Structure of the Lipid Portion.- 4. Glycoglycerolipids.- 5. Glycosphingolipids.- 5.1. Neutral Glycosphingolipids.- 5.2. Phosphorus-Containing Glycosphingolipids.- 5.3. Gangliosides.- 6. Other Glycolipids.- 7. Biological Activities.- 7.1. Immunological Activity.- 7.2. Pharmacological Activity.- References.- Author Index.

O autorze

Diese bekannte Reihe behandelt in Beiträgen bedeutender Autoren den jeweils letzten Stand des Wissens über die verschiedenen Klassen der in der Natur auftretenden Verbindungen. Es werden behandelt: Vorkommen, Reindarstellung, Struktur, chemische Eigenschaften, Synthese, Biogenese und Funktion.