FORTSCHRITTE PROGRESS IN THE CHEMISTRY OF ORGANIC NATURAL PRODUCTS HBRAUSOEOEBBN VON BDITED BY REDIGE PAR

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1 FORTSCHRITTE DER CHEMIE ORGANISCHER NATURSTOFFE PROGRESS IN THE CHEMISTRY OF ORGANIC NATURAL PRODUCTS PROGRES DANS LA CHIMIE DES SUBSTANCES ORGANIQUES NATURELLES HBRAUSOEOEBBN VON BDITED BY REDIGE PAR L. ZECHMEISTER CALIFORNIA INSTITUTE OF TECHNOLOGY, PASADENA SECHZEHNTER BAND SIXTEENTH VOLUME SEIZIEME VOLUME VERFASSER AUTHORS AUTEURS J. BONNER. K. FREUDENBERG. H. KUHN. E. E. V AN T AMELEN z. VALENT A. K. WEINGES. K. WIESNER MIT 27 ABBILDUNGEN WITH 27 FIGURES AVEC 27 ILLUSTRATIONS WI EN S P R I N G E R. V E R LAG 1958

2 ISBN-13: e-isbn-13: DOl: 1O.l007! ALLE RECHTE, INSBESONDERE DAS DER OBERSETZUNG IN FREMDE SPRACHEN, VORBEHALTEN SOFTCOVER REPRINT OF THE HARDCOVER 1ST EDITION 1958

3 Inhaltsverzeichnis. Contents. - Table des matieres. Catechine, andere Hydroxy-flavane und Hydroxy-flavene. Von KARL FREUDENBERG und KLAUS WEINGES, Chemisches Institut der Universitli.t Heidelberg I I. Altere Arbeiten I 2. Die bekannten Hydroxy-flavane Eigenschaften, Herstellung der Hydroxy-flavane..., 5 4. Kondensation durch Sli.uren Hydroxy-flavene Leucoanthocyanidin-hydrate, Acetate der Pseudoanthocyanidine und der Pseudoanthocyanidin-hydride Oxydations- und Reduktionsiibergli.nge in der CeCaCe-Reihe Cyanomaclurin Catechin-3-gallat und Catechin-3-glucosid..., Stereochemie der Catechine II. Biogenese der CeCaCe-Gruppe Literaturverzeichnis Recent Progress in the Chemistry of the Aconite-Garrya Alkaloids. By KAREL WIESNER and ZDENEK VALENTA, Department of Chemistry, The University of New Brunswick, Fredericton, N. B., Canada I. Introduction II. Garrya Alkaloids The Structure of Veatchine and Garryine Environment of the Nitrogen Structure of the Skeleton... 3 I Structure of the Oxoveatchine Dicarboxylic Acids Structure Assignment to Veatchine and Garryine The Stereochemistry of the Garrya Skeleton and its Influence on the Properties of Garrya Alkaloids The Structure of Cuauchichicine and Garryfoline Configuration of the Secondary Hydroxyl Group in Veatchine and Garryfoline..., 42

4 IV Inhaltsverzeichnis. - Contents. - Table des matieres. III. The Structure of Atisine Original Degradation Work on Atisine Similarity of Atisine with the Garrya Alkaloids and the Deduction of the Atisine Structure Some Confirmatory Evidence IV. Biogenesis of Veatchine and Atisine and Consideration of the Stereochemistry of Atisine V. The Structure of Ajaconine VI. The Structure of Napelline VII. The Chemistry of Hetisine VIII. Lycoctonine and Delpheline I. The Chemistry of Lycoctonine Oxidation Studies Skeletal Changes The,Chemistry of Delpheline Environment of the Nitrogen Transformations in the Demethylene Series The Carbon Skeleton of Delpheline Biogenesis of Lycoctonine and Delpheline IX. The Chemistry of Delphinine References Structural Chemistry of Actinomycetes Antibiotics. By E. E. VAN TAMELEN, Department of Chemistry, The University of Wisconsin, Madison, Wisconsin Introduction I. Actidione (Cycloheximide) Actinomycins Actithiazic Acid Amicetin Aureomycin (Chlorotetracycline) Aureothricin and Thiolutin Azaserine Chloromycetin (Chloramphenicol) Cycloserine (Oxamycin) Elaiomycin II. Erythromycin Etamycin (Viridogrisein) Magnamycin (Carbomycin)... IIO 14. Methymycin... II3 15. Mycomycin Netropsin... ' Nocardamine Novobiocin Puromycin (Achromycin) Sarkomycin Streptomycin Terramycin

5 Inhaltsverzeichnis. - Contents. - Table des matieres. v 23. Tetracycline Valinomycin References Protein Synthesis in Plants. By JAMES BONNER, California Institute of Technology, Pasadena. California I. Introduction II. Isolation of Microsomes III. Structure of the Microsomes..., IV. Role of the Microsomes in Protein Synthesis V. Biology of the Microsomes 1. Nuclear Microsomes Origin of Microsomes Transfer of Microsomal RNA..., Synthesis of the Microsomal Components Kinetics of Microsomal Labeling VI. Protein Synthesis as a Catenary Sequence Amino Acid Activation Transfer to Soluble RNA The Microsome as Acceptor of Amino Acid Alternative Pathways of Peptide Synthesis VII. Protein Synthesis in Mitochondria and Chloroplasts VIII. Protein Synthesis in Varied Plant Organs Developing Fruits and Seeds Leaves IX. Conclusion References The Electron Gas Theory of the Color of Natural and Artificial Dyes: Problems and Principles. By HANS KUHN, Physikalisch Chemisches Institut der Universitat Marburg a. d. Lahn..., 169 I. Some Experimental Facts Concerning Color and Structure Polyacetylenes, Polyenes, Symmetrical Cyanine Dyes, and Some Similar Compounds Aza Derivatives of Symmetrical Cyanine Type Compounds Acridine Type Bridge Formation in Symmetrical Cyanine Type Compounds... "..., Some Other Types of Resonance Systems Causing Absorption of Visible Light II. Some General Principles and Postulates...,... ',' I. Light Quanta and the Einstein-Bohr Frequency Relation... ' Wave Particle Duality of the Electron and the de Broglie Relationship Standing Electron Waves. The Pauli Principle The Chemical Bond; (J and :n Electron States

6 VI Inhaltsverzeichnis. - Contents. - Table des matieres. III. Quantum Mechanical Determination of the Position of the Absorption Bands of Simple Dyes A Simple Model of Symmetrical Cyanine Dyes A Simple Treatment of the Aza Derivatives of Symmetrical Cyanine Type Compounds References Namenverzeichnis. Index of Names. Index des Auteurs Sachverzeichnis. Index of Subjects. Index des Matieres