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

ISBN-13: 9783709187166 / Angielski / Miękka / 2012 / 328 str.

J. G. Buchanan; P. Crews; B. Epe

Spis treści

Pro-Inflammatory, Tumour-Promoting and Anti-Tumour Diterpenes of the Plant Families Euphorbiaceae and Thymelaeaceae.- I. Introduction.- II. Classification of Structural Types.- III. Botanical Considerations.- 1. The Family Euphorbiaceae.- 2. The Family Thymelaeaceae.- IV. Biosynthetic Relationships.- V. Isolation of Diterpenes.- VI. The Macrocyclic Diterpenes.- 1. Casbane Type.- 2. Jatrophane Type.- 3. Lathyrane Type.- 4. Jatropholane and Crotofolane Types.- 5. Rhamnofolane.- VII. Tigliane Diterpenes.- 1. Phorbol and Its Esters.- 2. Distribution of Phorbol Esters in Plants.- 3. Identification of Phorbol Esters.- 4. 4-Deoxyphorbol Esters.- 5. Other 4-Deoxyphorbol Derivatives.- 6. Identification of 4-Deoxyphorbol Esters.- 7. 12-Deoxyphorbol Esters.- 8. Identification of 12-Deoxyphorbol Esters.- 9. 12-Deoxy-16-Hydroxyphorbol Esters.- 10. Other 12-Deoxyphorbol Derivatives.- 11. 16-Hydroxyphorbol Esters.- VIII. Ingenane Derivatives.- 1. Ingenol.- 2. Distribution of Ingenol Esters in Plants.- 3. 5-Deoxyingenol.- 4. 16-Hydroxyingenol.- 5.. 13-Hydroxyingenol.- 6. 13,19-Dihydroxyingenol.- 7. 20-Deoxyingenol.- IX. Daphnane Derivatives.- 1. Daphnetoxin Type.- 2. 12-Hydroxydaphnetoxin Type.- 3. Resiniferonol Type.- 4. 1-Alkyldaphnane Type.- X. Closing Remarks.- Acknowledgements.- References.- Bitter Principles of Cneoraceae.- I. Introduction.- II. Nomenclature and Classification.- III. Constitution and Configuration of Cneorins A, B, C and D.- 1. Structural Studies by Ozonolysis.- 2.. Establishment of Relative and Absolute Configuration.- 3. Carbon Skeleton of Cneorins A —D: Numbering of C-Atoms.- 4. Configuration of Cneorin-CI.- 5. Configuration of Cneorin B, BI and BIII.- a). Elucidation of the Configuration at Carbon Atoms 7 and 9.- b). Elucidation of the Configuration at Carbon Atoms 5, 10, 13 and 17.- c). Hydrogenolysis of Cneorins BIII and CIII.- d). The Steric Series B and C with (17R)- and (17 S)-Configuration.- 6. Intramolecular Cyclisation to Cneorins BII and CII.- 7.. Constitution and Configuration of Cneorins A and D and Pyrolysis of Cneorin-D.- IV. The Series of Stereoisomeric ?8(30)-Olefms.- V. Stereoisomeric Alcohols with an 8-OH Group and (5 S, 10 R)-Configuration.- VI. Cneorins and Tricoccins with a C-7 Carbonyl Group.- 1. Cneorin-F and Tricoccin-S14.- 2. The Tricoccins R9, R12 and Their Epi-compounds.- VII. C-7 Hemiacetals and Methylacetals with (5S, 10R, 17R)-Configuration.- 1. Cneorin K and K1.- 2. Tricoccin R1 and R10.- VIII. C-9 Hemiacetals with (5S, 8S, 10R-Configuration.- IX. Cyclic Peroxides.- X. Bitter Principles with a ?-Lactol Ring (C-15 Hemiacetals).- 1. Precursors of Known Cneoroids.- 2. C-15 Cycloacetals.- 3. ?-Lactols with the Partial Structure of Ring A of Obacunone.- XI. Tetranortriterpenoids from Cneoraceae.- 1. 3,4-seco-Meliacans.- 2. 7,8-seco-Meliacans.- 3. 3,4-16,17-seco-Meliacans (Limonin Group).- 4. 3,4-7,8-16,17-seco-Meliacans.- XII. Protolimonoids.- 1. Tirucallan-(20 S)-Triterpenoids.- 2. Apotirucallan-(20 S)-Triterpenoids.- XIII. Comments on Biosynthesis of Cneorins and Tricoccins.- XIV. Tables of Natural Bitter Principles from Cneoraceae.- 1. Cneorins from Neochamaelea pulverulenta (Vent.) Erdtm. of Known Constitution and Configuration.- 2. Cneorins of Unknown Structure.- 3. Tricoccins from Cneorum tricoccon L. of Known Constitution and Configuration.- 4. Tricoccins of Unknown Structure.- References.- Chemical and Biological Aspects of Marine Monoterpenes.- I. Introduction.- II. Structural Variation.- III. The Role of Halogens in Biogenesis.- 1. Introduction.- 2. Acyclic Structures.- 3. Monocyclic Structures.- IV. Relationships Between Taxonomy and Occurrence of Structural Types.- 1. Introduction.- 2. The Plocamiaceae Family.- 3. The Rhizophyllidaceae Family.- 4. The Ceramiaceae Family.- 5. Degraded and Mixed Biogenetic Monoterpenes.- 6. Conclusion.- V. Metabolite Transfer and Biological Activity.- VI. Spectroscopic and Chemical Properties.- 1. Introduction.- 2. Halogen Content and Regiochemistry.- 3. Stereochemistry.- 4. Artifacts.- 5. Conclusions.- VII. Physical and Spectroscopic Tables.- 1. Table 13 A—H: Summary of Structures and Carbon-13 NMR Chemical Shifts.- 2. Table 14: Physical Properties.- Acknowledgement.- References.- The C-Nucleoside Antibiotics.- I. Introduction.- II. General Aspects of C-Nucleosides.- III. Showdomycin.- IV. The Formycins.- V. Pyrazofurin (Pyrazomycin).- VI. Oxazinomycin (Minimycin).- VII. The Ezomycins.- VIII.. Biosynthesis of C-Nucleoside Antibiotics.- References.- Author Index.