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

ISBN-13: 9783709191217 / Angielski / Miękka / 2012 / 212 str.

E. Casadevall; D. P. Chakraborty; C. Largeau

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 in 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

Lipids and Macromolecular Lipids of the Hydrocarbon-rich Microalga Botryococcus braunii. Chemical Structure and Biosynthesis. Geochemical and Biotechnological Importance.- I. Introduction.- II. Structure, Abundance and Biosynthesis of Lipids and Macromolecular Lipids in B. braunii.- 1. Hydrocarbons.- 1.1 Straight Chain Hydrocarbons (A Race).- 1.2 Botryococcenes (B Race).- 1.3 Lycopadiene (L Race).- 2. Classical Lipids.- 2.1 n-Fatty Acids.- 2.2 Triacylglycerols.- 2.3 Sterols.- 2.4 Carotenoids.- 3. Non-classical Lipids of the A Race.- 3.1 Botryals.- 3.2 n-Alkenylphenols.- 3.3 Epoxides.- 3.4 Ether Lipids.- 3.5 Methyl-branched Fatty Aldehydes and Fatty Acids.- 4. Macromolecular Lipids.- 4.1 B. braunii Rubber.- 4.2 Resistant Biopolymers from Outer Walls (PRB).- III. Geochemical Implications of B. braunii Composition.- 1. Role of PRB in Fossilization.- 2. Role of B. braunii Hydrocarbons as Biomarkers.- IV. B. braunii Biotechnology.- 1. Relationship Between Hydrocarbon Production and Physiological State.- 2. Influence of Various Culture Parameters on Hydrocarbon Production.- 2.1 Medium Composition.- 2.2 Light.- 2.3 B. braunii Strain.- 2.4 Associated Bacteria.- 3. Immobilized Cultures.- 4. Hydrocarbon Recovery.- V. Conclusion.- References.- Carbazole Alkaloids III.- I. Introduction.- A. Nomenclature.- B. Occurrence.- C. Detection of Carbazoles.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. Ultraviolet Absorption Spectra.- 2. IR Spectra.- 3. NMR Spectra.- (a) 1H-NMR Spectra.- (b) Application of the Nuclear Overhauser Effect.- (c) 13C-NMR Spectra.- 4. Mass Spectra.- 5. X-ray Crystallographic Methods.- B. Degradative Reactions.- C. Synthesis of Carbazoles.- 1. Synthesis of Tricyclic Alkaloids.- (a) From Arylamines.- (i) Electrophilic Aromatic Substitution.- (ii) Lewis-acid Catalysed Aliphatic Diazocoupling.- (b) From Diphenylamines.- (c) From Indoles.- (x) From Indole-2-Carboxylates.- (y) From 2-Alkylated Indoles.- (z) Cycloaddition Reactions.- (i) From 3-Vinylindoles.- (ii) From 2-Vinylindoles.- (iii) From Indole-2,3-quinodimethane and Analogues.- (iv) Benzannelation of Indoles.- (d) Biomimetic hydroxylation of 3-methylcarbazole.- 2. Synthesis of Tetracyclic Alkaloids.- (a) Alkaloids with a C18-Skeleton.- (i) Diphenylamine Route.- (ii) Introduction of a C5-unit with 3,3-Dimethylacrylic acid.- (b) Benzo-b-Carbazoles and Carbazoloquinones.- (c) Tetracyclic Alkaloids with a C23-Skeleton and Their Pentacyclic and Hexacyclic Cyclomers.- 3. Synthesis of Biscarbazoles.- (a) Synthesis of Alkaloids with a C26-Skeleton.- (i) Synthesis of Bismurrayafolinol Acetate.- (ii) Biomimetic Dimerisation.- (b) Formation of Alkaloids with C31- and C36-Skeletons.- (i) Nafion 117 Catalysed Dimerisation.- (ii) BF3-Etherate Catalysed Dimerisation.- 4. Transformations and Photochemical Reactions.- (a) Transformations.- (i) Thermal Transformation of Mahanimbine.- (ii) Racemisation and Inversion of Mahanimbine.- (b) Photochemical Reactions.- (i) Dimerisation of Vinylcarbazole.- (ii) Photo-Fries Rearrangement of N-Substituted Carbazoles.- (iii) Ring Expansion of Pyranocarbazoles.- (c) Formation of Bicyclodihydrooxepinocarbazole from Dihydrooxepinocarbazoles.- (d) Photochemical Synthesis of Benzocarbazoles.- III. Biogenesis of Carbazole Alkaloids.- IV. Biological and Therapeutic Properties of Carbazoles Alkaloids and Congeners.- V. Chemistry of Carbazole Alkaloids.- A. Alkaloids from Higher Plants.- (i) C13-Alkaloids.- 1. Murrayastine.- 2. Murrayaline.- 3. 0-Demethylmurrayanine.- 4. 3-Formylcarbazole.- 5. N-Methoxy-3-formylcarbazole.- 6. Carbazole.- (ii) C18-Alkaloids.- 1. Dihydroxygirinimbine.- 2. Pyrayafoline.- 3. Isomurrayafoline B.- 4. Atanisatin.- (iii) C23-Alkaloids.- 1. Murrayazolinol.- (iv) Carbazoloquinones.- 1. Pyrayaquinone A.- 2. Pyrayaquinone B.- 3. Pyrayaquinone C.- (v) Dimeric Carbazole Alkaloids.- (a) C26-Alkaloids.- 1. Bismurrayafolinol.- 2. Oxydimurrayafoline.- 3. Murrafoline F.- (b) C31-Alkaloids.- 1. Murrafoline B.- 2. Murrafoline D.- 3. Murrafoline E.- (c) C36-Alkaloids.- 1. Murrafoline C.- B. Alkaloids from Lower Plants.- (i) Carbazomycins.- 1. Carbazomycin C.- 2. Carbazomycin D.- 3. Carbazomycinal.- 4. 6-Methoxycarbazomycinal.- 5. Carbazomycin G.- 6. Carbazomycin H.- (ii) Kinamycins.- 1. Kinamycin C.- 2. Kinamycins A, B, and D.- 3. Prekinamycin.- 4. Ketoanhydrokinamycin.- 5. Kinamycin E.- 6. Deacetylkinamycin.- (iii) Tubingensins.- 1. Tubingensin A.- 2. Tubingensin B.- C. Alkaloids from Mammals.- References.- The Bryostatins.- 1. Introduction.- 2. Bryozoans and Bugula neritina Linnaeus.- 3. Isolation and Structure Elucidation of the Bryostatins.- 3.1. Bryostatins 1–3.- 3.2. Bryostatin 4.- 3.3. Bryostatins 5–7.- 3.4. Bryostatin 8.- 3.5. Bryostatin 9.- 3.6. Bryostatins 10 and 11.- 3.7. Bryostatins 12 and 13.- 3.8. Bryostatins A and B.- 4. Bioassay Guided Isolation.- 5. Chemical Transformations.- 6. Absolute Configuration.- 7. Spectral and Analytical Characterization.- 8. Antineoplastic and Cytostatic Activities.- 9. Inhibition of Tumor Promotion.- 10. General Biological Properties.- 10.1. Immunological.- 10.2. Hematopoietic.- 10.3. Microbiological.- 11. Mechanism of Action.- 12. Implications for Cancer Treatment.- 13. Conclusions.- Acknowledgement.- References.- Author Index.