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

ISBN-13: 9783709173435 / Angielski / Miękka / 2012 / 365 str.

A. Andersen; S. B. Christensen; D. Deepak

Opis

For centuries preparations containing resin from the root of Thapsia garganica L. (Fig. 1) have been used in Arabian and European medicine for treatment of pulmonary diseases, catarrh and as counterirritants for relief of rheumatic pains (1). The properties of the resin were described already by Theophrastos (372-287 B. C. ), Dioscorides (approximately A. D. 50), and Plinius (A. D. 24-79) (2). Radix Thapsiae and Resina Thapsiae have been included in several pharmacopoeias, the latest in the French pharmacopoeia from 1937. The two major active principles were about Fig. I. Thapsia garganica References, pp.163-167 Sesquiterpenoids from Thapsia Species 131 Thapsigargin (1), Rl: Oct, R2= But Thapsigargicin (2), Rl= Hex, R2 = But Thapsitranstagin (3), Rl: iVai, R2= 2-MeBut Thapsivillosin A (4), Rl= Ang, R2= Sen Thapsivillosin B ( 5), Rl: Ang, R2= 2-MeBut Thapsivillosin C ( 6), Rl= Oct, R2= 2-MeBut Thapsivillosin D ( 7), Rl: 6-MeOct, R2= Sen Thapsivillosin E ( 8), Rl: 6-MeOct, R2= 2-MeBut Thapsivillosin G ( 9), Rl= 6-MeHcp, R2= 2-MeBut Thapsivillosin H ( 10), Rl or R2= Ang or Sen Thapsivillosin I ( 11), Rl= Ang, R2= But Thapsivillosin J ( 12), Rl: iVai, R2= But Thapsivillosin K ( 13), Rl: Sen, R2= 2-MeBut Chart 1. Hexaoxygenated thapsigargins found in Thapsia two decades ago found to be the sesquiterpene lactones thapsigargin (1) and thapsigargicin (2) (3).

Spis treści

The Explosion of Structural Information on Insect Neuropeptides.- 1. Introduction.- 2. General Methods Used for Isolation, Identification and Characterization of Insect Neuropeptides.- 2.1. Biological Assays.- 2.1.1. Adipokinetic Bioassay.- 2.1.2. Myotropic Bioassay.- 2.2. Liquid Chromatography.- 2.3. Edman Degradation Sequencing, Mass Spectrometry and Peptide Synthesis.- 2.4. Immunological Techniques (RIA, ELISA, Immunocytochemistry).- 2.5. Molecular Biological Techniques.- 3. The Insect Neuropeptides.- 3.1. Peptides Involved in Homeostasis and Metabolism.- 3.1.1. Adipokinetic and Hypertrehalosaemic Peptides.- 3.1.2. Diuretic and Antidiuretic Peptides.- 3.2. Peptides Regulating Reproduction, Growth and Development.- 3.2.1. Pheromone Biosynthesis Activating Neuropeptides.- 3.2.2. Allatotropins and Allatostatins.- 3.2.2.1. Allatotropins.- 3.2.2.2. Allatostatins.- 3.2.3. Prothoracicotropic Hormone, Bombyxin and Other Insulin-Related Neuropeptides.- 3.2.3.1. Prothoracicotropic Hormone.- 3.2.3.2. Bombyxin.- 3.2.3.3. Locusta Insulin-Related Peptide.- 3.2.4. Eclosion Hormones.- 3.2.5. Peptides Affecting Gonad Activity.- 3.2.5.1. Ovary Maturating Peptide and Neuroparsin of Locusta migratoria.- 3.2.5.2. Oostatic Hormones of Diptera.- 3.2.6. Diapause Hormones.- 3.3. Peptides Modifying Spontaneous Muscle Contractions:Mytropic Peptides.- 3.3.1. Proctolin and Cardiostimulatory Peptides.- 3.3.2. Myokinins.- 3.3.3. Sulfakinins.- 3.3.4. Pyrokinins/Myotropins.- 3.3.5. Tachykinins.- 3.3.6. Periviscerokinin.- 3.3.7. Accessory Glands- and Midgut Myotropins and Others.- 3.3.8. Myoinhibitory Peptides and Other FMRF amide Related Peptides (FaRPs).- 3.4. Chromatotropic Factors in Insects.- 4. Conclusions.- Acknowledgments.- References.- Sesquiterpenoids from Thapsia Species and Medicinal Chemistry of the Thapsigargins.- 1. Introduction.- 2. Taxonomy of Thapsia.- 2.1. Thapsia garganica and Thapsia transtagana.- 2.2. Thapsia maxima.- 2.3. Thapsia villosa.- 2.4. Thapsia gymnesica.- 3. Elucidation of the Structure of Thapsigargin.- 4. Proazulenic Slovanolides.- 5. Non-lactonic Sesquiterpenoids from Thapsia.- 6. Pharmacological Activity of the Thapsigargins.- 7. Molecular Pharmacology.- 8. Chemistry of Thapsigargin.- 8.1. Changes at C(8).- 8.2. Changes at C(3).- 8.3. Changes of the Vicinal Diol.- 8.4. Changes of Lactone Carbonyl Group.- 8.5. Changes at O(10).- 9. Structure Activity Relationships.- 10. Metabolic Catabolism of Thapsigargin.- References.- Pregnane Glycosides.- 1. Introduction.- 2. Isolation and Identification.- 2.1. Thin Layer and Column Chromatography.- 2.2. Sephadex LH-20 Chromatography.- 2.3. Flash Chromatography.- 2.4. Low Pressure Liquid Chromatography (LPLC).- 2.5. High Performance Liquid Chromatography (HPLC).- 3. Structure Elucidation.- 3.1. One-Dimensional NMR Spectroscopy.- 3.2. Two-Dimensional NMR Spectroscopy.- 3.3. Mass Spectrometry.- 3.4. I.R. Spectroscopy.- 3.5. U.V. Spectroscopy.- 3.6. Optical Rotatory Dispersion.- 3.7. Hydrolysis of Pregnane Glycosides.- 4. Pregnane Aglycons.- 5. Sugars of Pregnane Glycosides.- 5.1. General and Monosaccharides.- 5.2. Disaccharides from Pregnane Glycosides.- 5.3. Trisaccharides from Pregnane Glycosides.- 6. Biosynthesis of Pregnane Glycosides.- 7. Biological Activity.- Acknowledgement.- References.- Author Index.