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

ISBN-13: 9783709194089 / Angielski / Miękka / 2012 / 176 str.

A. a. L. Gunatilaka; C. Tamm; P. Walser-Volken

Opis

Contents: A.A. Leslie Gunatilaka: Triterpenoid Quinonemethides and Related Compounds (Celastroloids). - P. Walser-Volken and Ch. Tamm: The Spirostaphylotrichins and Related Microbial Metabolites. 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

Triterpenoid Quinonemethides and Related Compounds (Celastroloids).- 1. Introduction.- 2. General Structural Features and Nomenclature.- 3. The Families of Celastroloids.- 3.1. Quinonemethide Triterpenoids.- 3.2. 14(15)-Enequinonemethide Triterpenoids.- 3.3. 9(1 l)-Enequinonemethide Triterpenoids.- 3.4. Phenolic and 6-Oxophenolic Triterpenoids.- 3.5. 7-Oxoquinonemethide Triterpenoids.- 3.6. Dimeric Celastroloids.- 3.7. Miscellaneous Celastroloids.- 4. Natural Occurrence.- 4.1. Taxonomic Considerations.- 4.2. Plant Sources of Celastroloids.- 4.3. Distribution of Natural Celastroloids.- 4.4. Celastroloids from Tissue Cultures.- 5. Derivatives of Celastroloids.- 6. The Chemistry of Celastroloids.- 6.1. Isolation Techniques.- 6.2. Structure Elucidation.- 6.2.1. Early Structural Studies of Celastrol and Pristimerin.- 6.2.2. Application of Spectroscopic Techniques.- 6.2.2.1. UV/VIS and ORD/CD Spectroscopy.- 6.2.2.2. Infrared Spectroscopy.- 6.2.2.3. NMR Spectroscopy.- 6.2.2.3.1. 1H-NMR Spectroscopy.- 6.2.2.3.2. 13C-NMR Spectroscopy.- 6.2.2.4. Mass Spectrometry.- 6.2.2.5. X-Ray Crystallography.- 6.3. Chemical Reactions.- 6.3.1. General Chemical Characterization.- 6.3.2. Degradation and Oxidation.- 6.3.3. Reduction and Derivatization.- 6.3.4. Addition Reactions.- 6.3.5. Rearrangements.- 6.3.6. Photochemistry.- 7. Partial Synthesis.- 8. Biosynthetic Aspects.- 9. Biological Activity.- 9.1. Antimicrobial Activity.- 9.2. Antitumor Activity.- 9.3. Other Biological Activities.- 10. Conclusions.- Addendum.- Acknowledgements.- References.- The Spirostaphylotrichins and Related Microbial Metabolites.- 1. Introduction.- 2. Isolation of Spirostaphylotrichin A (1), B (2), C and D (3/4), Q (5), R (6) and F (7) from Cultures of Staphylotrichum coccosporum.- 3. Biosynthetic Studies.- 3.1. Feeding Experiments with 14C-, 13C, and 2H-Labelled Precursors.- 3.1.1. Experiments with 14C-Labelled Precursors.- 3.1.2. Experiments with 13C- and 2H-Labelled Precursors.- 3.2. Investigation of Mutant Strains and Isolation of Further Spirostaphylotrichins.- 3.2.1. Mutagen Treatment and Selection of Mutants.- 3.2.2. The Mutant Strain P 84.- 3.2.3. The Mutant Strain P 649.- 4. Investigation of the Epimerization of Spirostaphylotrichins.- 5. Discussion of the Results Regarding the Biosynthesis of the Spirostaphylotrichins.- 6. Synthetic Approaches Towards the Spirostaphylotrichins.- 7. Related Fungal Metabolites: Triticones, Arthropsolides, and Other Compounds.- 7.1. Triticones.- 7.2. Arthropsolides and Related Compounds.- References.- Author Index.