Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

- 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