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

The cyanogenic glycosides, here defined as glycosidic derivatives of iX-hydroxynitriles, represent a rather limited class of natural products, which are widely distributed in the plant kingdom and, to a small ex­ tent, even in animals. A characteristic feature of these glycosides is their ability to release hydrocyanic acid on treatment with dilute acids or appropriate enzymes. The term "cyanogenic" is used to designate this property, regardless of whether pure substances, plants, or animals, are serving as the source. In the latter cases the term "cyanophoric" is occasionally employed synonymously. Cyanogenesis in plants was probably first discovered by SCHRADER in 1803 (Io3) working with bitter almonds. In 1830, ROBIQUET and BOUTRON-CHARLARD (IOO) succeeded in isolating the parent glycoside, namely amygdalin. Over the years, a total of 18 cyanogenic glycosides have been isolated and characterized more or less completely (Table I, p. 76). It will be noted that the majority of these compounds has been isolated in the era of classical organic chemistry and that progress in .discovering new compounds, not to mention new structural types, has been surprisingly slow. It is worth remembering here that the mechanism ·of cyanogenesis has been established only in the minority of known cyanogenic species. The cyanogenic glycosides have last been reviewed in 1958 by DILLE­ MANN (36). Since then, no complete reviews in this field have appeared. It is the purpose of the present article to survey the more recent ad­ vances and, hopefully, to stimulate continued interest in these interesting .compounds.

Structural and Biogenetic Relationships of Isoflavonoids.- I. Introduction.- II. Isoflavones.- III. Isoflavanones.- IV. Rotenoids.- V. Pterocarpans.- VI. Isoflavans.- VII. 3-Aryl-4-hydroxycoumarins.- VIII. Coumestans.- IX. Other Types of Isoflavonoids.- X. Biogenesis of Isoflavonoids.- References.- Recent Advances in the Chemistry of Cyanogenic Glycosides.- I. Introduction.- II. General Chemical Considerations.- III. Detection.- IV. Isolation.- V. Structure Elucidation.- VI. Synthesis.- VII. Distribution.- VIII. Biosynthesis.- IX. Metabolic Aspects.- References.- Naturstoffe mit Pyridinstruktur und ihre Biosynthese.- Einführung.- Peptide Alkaloids.- I. Introduction.- II. General Properties of Peptide Alkaloids.- III. General Methods and Techniques of Structural Determination.- IV. Structure and Properties of Peptide Alkaloids.- V. Ultraviolet Spectra of Peptide Alkaloids.- VI. NMR Spectra of Peptide Alkaloids.- VII. Mass Spectra of Aryloxy Macrocyclic Peptide Alkaloids.- VIII. Pharmacological Properties of Peptide Alkaloids.- IX. Tables.- References.- Insektensexuallockstoffe.- I. Einleitung.- II. Insektensexuallockstoffe.- III. Weitere Pheromone.- IV. Insektenhormone.- Arthropod Molting Hormones.- I. Introduction.- II. Hormonal Regulation of Growth of Insects and Crustaceans.- III. Occurrence in Animals.- IV. Occurrence in Plants.- V. Isolation and Assay.- VI. Structure Determination and Chemistry.- VII. Synthesis.- VIII. Biosynthesis and Catabolism.- IX. Tables.- References.- Total Synthesis of Prostaglandins.- I. Introduction.- II. Structure and Chemical Transformations of the Prostaglandins.- III. General Approaches to Prostaglandin Synthesis.- IV. Synthetic Routes to Structurally Simplified Prostaglandins.- V. Synthetic Routes to Prostaglandin Analogs.- VI.Miscellaneous Synthetic Approaches.- VII. Resolution of Racemic Prostaglandins.- References.- Chemistry of Cephalosporin Antibiotics.- I. Introduction.- II. Isolation and Structure of Cephalosporin Antibiotics.- III. Chemical Transformations of Cephalosporin C.- IV. Physicochemical Properties of Cephalosporanates.- V. Syntheses of Cephalosporins.- VI. Biosynthesis.- VII. Biological Activity of Cephalosporanates.- References.- Oligosaccharide der Frauenmilch.- I. Einleitung.- II. Isolierung und Analyse der Oligosaccharide.- III. Beschreibung der Zucker.- IV. Vergleich der freien Kohlenhydrate der Milch und des Urins mit den konjugierten Oligosacchariden der Glykosphingolipide.- V. Biosynthese und Blutgruppenmerkmale.- Glucagon: Chemistry and Action.- I. Introduction.- II. Assay.- III. Chemical Aspects.- IV. Site of Formation and Release.- V. Glucagon in Blood.- VI. Glucagon Action.- VII. Physiologic Role.- References.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.