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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).
List of contents
The Explosion of Structural Information on Insect Neuropeptides.- 1. Introduction.- 2. General Methods Used for Isolation, Identification and Characterization of Insect Neuropeptides.- 3. The Insect Neuropeptides.- 4. Conclusions.- Acknowledgments.- References.- Sesquiterpenoids from Thapsia Species and Medicinal Chemistry of the Thapsigargins.- 1. Introduction.- 2. Taxonomy of Thapsia.- 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.- 9. Structure Activity Relationships.- 10. Metabolic Catabolism of Thapsigargin.- References.- Pregnane Glycosides.- 1. Introduction.- 2. Isolation and Identification.- 3. Structure Elucidation.- 4. Pregnane Aglycons.- 5. Sugars of Pregnane Glycosides.- 6. Biosynthesis of Pregnane Glycosides.- 7. Biological Activity.- Acknowledgement.- References.- Author Index.
