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

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).