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

ISBN-13: 9783709189085 / Angielski / Miękka / 2012 / 224 str.

H. Achenbach; P. Bhattacharyya; D. P. Chakraborty

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 Perylenequinones.- 1. Introduction.- 2. Natural Perylenequinones in General.- 2.1. Perylene and Its Derivatives.- 2.2. Types of Perylenequinones Obtainable from Natural Sources. Occurrence.- 2.3. General Properties and Reactions of Natural Perylenequinones.- 2.4. Spectroscopic Properties.- 2.5. Chemical Reactions.- 2.6. Synthesis.- 3. Individual Natural Perylenequinones.- 3.1. 4,9-Dihydroxyperylene-3,10-quinone.- 3.2. Aspergillin.- 3.3. Elsinochromes.- 3.3.1. Occurrence and Formation.- 3.3.2. Isolation and Purification.- 3.3.3. Structure of Elsinochromes.- 3.4. Cercosporin.- 3.5. Phleichromes.- 3.6. Cladochromes.- 3.7. Pigments from Mutants of Cercospora kikuchii.- 3.8. Hypocrellin.- 3.9. The Aphins.- 3.9.1. The Protoaphins.- 3.9.2. The Xanthoaphins and the Chrysoaphins.- 3.9.3. The Erythroaphins ; Rhodoaphin.- 4. Stereochemistry.- 5. Tautomerism.- 6. Biosynthesis.- 7. Biological Activity.- 8. Partially Reduced Perylenequinones.- 8.1. Altertoxin I and Dihydroalterperylenol.- 8.2. Alterperylenol, Alteichin, and Altertoxin II.- 8.3. Stemphyltoxins I-IV.- 8.4. Stemphyperylenol and Altertoxin III.- Addendum.- References.- The Pigments of the Flexirubin-Type. A Novel Class of Natural Products.- I. Introduction.- II. Structure Elucidation of Flexirubin.- III. Isolation and Separation of Flexirubin-Type Pigments.- IV. General Comments on Structure Elucidation of Flexirubin-Type Pigments.- V. Spectroscopic Properties of Flexirubin-Type Pigments.- 1. Mass Spectra.- 2. Proton-NMR-Spectra.- 3. 13C-NMR-Spectra.- 4. Electronic Spectra.- VI. Synthetic Approaches to Flexirubin-Type Pigments.- VII. Biosynthesis of Flexirubin-Type Pigments.- VIII. Closing Remarks.- References.- Structure, Stability and Color Variation of Natural Anthocyanins.- 1. Introduction.- 2. Structure Determination.- 2.1 Mass Spectra of Anthocyanins.- 2.2 1-NMR Spectra.- 2.3 Structure Determination of Heavenly Blue Anthocyanin.- 2.4 Other Anthocyanins Acylated with Two or More Aromatic Acids.- 2.5 Anthocyanins Acylated with Aliphatic Dicarboxylic Acids.- 3. Stabilization Effect of Inorganic Salts.- 4. Self-Association.- 5. Co-Pigmentation.- 6. Intramolecular Sandwich Type Stacking.- 7. Metalloanthocyanins.- 7.1 Commelinin.- 7.2 Protocyanin.- References.- Carbazole Alkaloids.- I. Introduction.- A. Occurrence.- B. Detection of Carbazoles by Chromatographic Methods.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. 13C NMR Spectra.- B. Synthesis of Carbazoles.- 1. Palladium Promoted Cyclisation of Diphenylamine.- 2. Acid Catalysed Cyclisation of ?-Ketosulphoxide.- 3. In situ Vinyl Indole Synthesis of Carbazoles.- 4. Preparation by Application of the Nenitzescu Synthesis.- 5. Thermal Cyclisation.- 6. Free Radical Cyclisation of Diphenylamine to Carbazole.- 7. Intramolecular Diels-Aider Cycloaddition of Vinylketenimines.- 8. Diels-Alder Reaction of Indole-2,3-quinodimethane.- 9. Synthesis of Carbazoles via 2-Vinylindoles.- 10. Synthesis of Pyranocarbazole Alkaloids of the C18-Carbon Skeleton Group.- III. Biogenesis of Carbazole Alkaloids.- IV. Biological Properties of Carbazole Alkaloids and Related Compounds.- V. Chemistry of Carbazole Alkaloids.- A. Members of the C13-Skeleton Group.- 1. Mukonal.- 2. 2-Methoxy-3-methylcarbazole.- 3. Mukoline and Mukolidine.- 4. 2-Hydroxy-3-methylcarbazole.- 5. Glycozolinol.- 6. Glycozolidol.- 7. Glycozolidal.- 8. Lansine.- 9. Koenoline.- 10. Murrayafoline-A.- B. Members of the C18-Skeleton Group.- 1. Mukonicine.- 2. Heptazolicine.- 3. Clausenapin.- 4. Clausenatin.- 5. Mupamine.- 6. Murrayafoline-B.- 7. Ekeberginine.- C. Members of the C23-Skeleton Group.- 1. Exozoline.- 2. Mahanimbinol.- 3. Mahanimboline.- 4. Isomurrayazoline.- 5. (+) Murrayazoline.- D. Dimeric Carbazoles.- 1. Bismurrayafoline-A.- 2. Bismurrayafoline-B.- 3. (±) Murrafoline.- E. Carbazolequinones.- 1. Murrayaquinone-A.- 2. Murrayaquinone-B.- 3. Murrayaquinone-C and Murrayaquinone-D.- F. Carbazoles from Other Sources.- 1. Hyellazole.- 2. 6-Chlorohyellazole.- 3. Carbazomycin B.- 4. Carbazomycin A.- References.- Author Index.