From Plant to Patient: Thapsigargin, a Tool for Understanding …
103
40. Tutin TG, Heywood VH, Burges NA, Moore DM, Valentine DH, Walter SM, Webb DA (1968)
Flora Europea. Cambridge University Press, Cambridge, UK
41. Smitt UW (1995) A chemotaxonomic investigation of Thapsia villosa L., Apiaceae (Umbelliferae). Bot J Linn Soc 119:367
42. Weitzel C, Rønsted N, Spalik K, Simonsen HT (2014) Resurrecting deadly carrots: towards a
revision of Thapsia (Apiaceae) based on phylogenic analysis of nrITS sequences and chemical
profiles. Bot J Linn Soc 174:620
43. De Pascual TJ, Moran JR, Fernandez A, Grande M (1986) Non-acetalic thapsane sesquiterpenoids from Thapsia villosa var. minor. Phytochemistry 25:1171
44. Smitt UW, Cornett C, Norup E, Christensen SB (1990) Hydroindene sesquiterpenes from
Thapsia villosa. Phytochemistry 29:873
45. Lemmich E, Jensen B, Rasmussen U (1984) (8R,14S)-8-Angeloyloxythapsan-14-ol, a
sesquiterpene with a novel carbon skeleton, from Thapsia villosa. Phytochemistry 23:809
46. De Pascual Teresa J, Moran JR, Fernandez A, Grande M (1986) Hemiacetalic thapsane
derivatives from Thapsia villosa var. minor. Phytochemistry 2:703
47. Saouf A, Guerra FM, Rubal JJ, Moreno-Dorado FJ, Akssira M, Mellouki F, Lopez M, Pujadas
AJ, Jorge ZD, Massanet GM (2005) Transtaganolides A–D: Novel metabolites from Thapsia
transtagana. Org Lett 7:881
48. Appendino G, Prosperini S, Valdivia C, Ballero M, Colombano G, Billington RA, Genazzani AA, Sterner O (2005) SERCA-inhibiting activity of C-19 terpenolides from Thapsia
garganica and their possible biogenesis. J Nat Prod 68:1213
49. Navarrete C, Sancho R, Caballero FJ, Pollastro F, Fiebich BL, Sterner O, Appendino G,
Munoz E (2006) Basiliolides, a class of tetracyclic C-19 dilactones from Thapsia garganica,
release Ca 2+ from the endoplasmic reticulum and regulate the activity of the transcription
factors nuclear factor of activated T cells, nuclear factor-κB, and activator protein 1 in T
lymphocytes. J Pharmacol Exp Ther 319:422
50. Jo D-G, Jun J-I, Chang J-W, Hong Y-M, Song S, Cho D-H, Shim SM, Lee H-J, Cho C, Kim
DH, Jung Y-K (2004) Calcium binding of ARC mediates regulation of caspase 8 and cell
death. Mol Cell Biol 24:9763
51. Larsen PK, Sandberg F (1970) Constituents of umbelliferous plants. XV. Coumarins from
Thapsia garganica L. The structure of a new coumarin. Acta Chem Scand 24:1113
52. Larsson R, Sterner O, Johansson M (2009) Biomimetic synthesis toward the transtaganolides/basiliolides. Org Lett 11:657
53. Larsson R, Scheeren HW, Aben RWM, Johansson M, Sterner O (2013) Total synthesis of
transtaganolide E and F: insight in the biosynthesis of the transtaganolides. Eur J Org Chem
2013:6955
54. Avato P, Cornett C, Andersen A, Smitt UW, Christensen SB (1993) Localization of the acyl
groups in proazulene guaianolides from Thapsia transtagana and Thapsia garganica. J Nat
Prod 56:411
55. Avato P (1991) Essential oil of Thapsia garganica. Planta Med 57:585
56. Smitt UW, Cornett C, Andersen A, Christensen SB (1990) New proazulene guaianolides from
Thapsia villosa. J Nat Prod 53:1479
57. Smitt UW, Moldt P, Christensen SB (1986) Structure of a pro-1,4-dimethylazulene guaianolide
from Thapsia garganica L. Acta Chem Scand B 40:711
58. Smith MB, March J (2001) The Prins reaction. In: Smith MB, March J (eds) March’s advanced
organic chemistry, 5th edn. Wiley, New York, p 124
59. Smith MB, March J (2001) Pyrolysis of carboxylic acids and esters of carboxylic acids. In:
Smith MB, March J(eds) March’s advanced organic chemistry, 5th edn. Wiley, New York, p
1329
60. Mukaiyama T, Echigo Y (1978) A new method for the preparation of ketones by decarbonylation of α-hydroxycarboxylic acid with 2-chlorobenzoxazolium salt. Chem Lett
1978:49
61. March J (1985) Decarbonylation of acids and esters. In: March J (ed) Advanced organic
chemistry, 3rd edn. Wiley, New York, p 341
103
40. Tutin TG, Heywood VH, Burges NA, Moore DM, Valentine DH, Walter SM, Webb DA (1968)
Flora Europea. Cambridge University Press, Cambridge, UK
41. Smitt UW (1995) A chemotaxonomic investigation of Thapsia villosa L., Apiaceae (Umbelliferae). Bot J Linn Soc 119:367
42. Weitzel C, Rønsted N, Spalik K, Simonsen HT (2014) Resurrecting deadly carrots: towards a
revision of Thapsia (Apiaceae) based on phylogenic analysis of nrITS sequences and chemical
profiles. Bot J Linn Soc 174:620
43. De Pascual TJ, Moran JR, Fernandez A, Grande M (1986) Non-acetalic thapsane sesquiterpenoids from Thapsia villosa var. minor. Phytochemistry 25:1171
44. Smitt UW, Cornett C, Norup E, Christensen SB (1990) Hydroindene sesquiterpenes from
Thapsia villosa. Phytochemistry 29:873
45. Lemmich E, Jensen B, Rasmussen U (1984) (8R,14S)-8-Angeloyloxythapsan-14-ol, a
sesquiterpene with a novel carbon skeleton, from Thapsia villosa. Phytochemistry 23:809
46. De Pascual Teresa J, Moran JR, Fernandez A, Grande M (1986) Hemiacetalic thapsane
derivatives from Thapsia villosa var. minor. Phytochemistry 2:703
47. Saouf A, Guerra FM, Rubal JJ, Moreno-Dorado FJ, Akssira M, Mellouki F, Lopez M, Pujadas
AJ, Jorge ZD, Massanet GM (2005) Transtaganolides A–D: Novel metabolites from Thapsia
transtagana. Org Lett 7:881
48. Appendino G, Prosperini S, Valdivia C, Ballero M, Colombano G, Billington RA, Genazzani AA, Sterner O (2005) SERCA-inhibiting activity of C-19 terpenolides from Thapsia
garganica and their possible biogenesis. J Nat Prod 68:1213
49. Navarrete C, Sancho R, Caballero FJ, Pollastro F, Fiebich BL, Sterner O, Appendino G,
Munoz E (2006) Basiliolides, a class of tetracyclic C-19 dilactones from Thapsia garganica,
release Ca 2+ from the endoplasmic reticulum and regulate the activity of the transcription
factors nuclear factor of activated T cells, nuclear factor-κB, and activator protein 1 in T
lymphocytes. J Pharmacol Exp Ther 319:422
50. Jo D-G, Jun J-I, Chang J-W, Hong Y-M, Song S, Cho D-H, Shim SM, Lee H-J, Cho C, Kim
DH, Jung Y-K (2004) Calcium binding of ARC mediates regulation of caspase 8 and cell
death. Mol Cell Biol 24:9763
51. Larsen PK, Sandberg F (1970) Constituents of umbelliferous plants. XV. Coumarins from
Thapsia garganica L. The structure of a new coumarin. Acta Chem Scand 24:1113
52. Larsson R, Sterner O, Johansson M (2009) Biomimetic synthesis toward the transtaganolides/basiliolides. Org Lett 11:657
53. Larsson R, Scheeren HW, Aben RWM, Johansson M, Sterner O (2013) Total synthesis of
transtaganolide E and F: insight in the biosynthesis of the transtaganolides. Eur J Org Chem
2013:6955
54. Avato P, Cornett C, Andersen A, Smitt UW, Christensen SB (1993) Localization of the acyl
groups in proazulene guaianolides from Thapsia transtagana and Thapsia garganica. J Nat
Prod 56:411
55. Avato P (1991) Essential oil of Thapsia garganica. Planta Med 57:585
56. Smitt UW, Cornett C, Andersen A, Christensen SB (1990) New proazulene guaianolides from
Thapsia villosa. J Nat Prod 53:1479
57. Smitt UW, Moldt P, Christensen SB (1986) Structure of a pro-1,4-dimethylazulene guaianolide
from Thapsia garganica L. Acta Chem Scand B 40:711
58. Smith MB, March J (2001) The Prins reaction. In: Smith MB, March J (eds) March’s advanced
organic chemistry, 5th edn. Wiley, New York, p 124
59. Smith MB, March J (2001) Pyrolysis of carboxylic acids and esters of carboxylic acids. In:
Smith MB, March J(eds) March’s advanced organic chemistry, 5th edn. Wiley, New York, p
1329
60. Mukaiyama T, Echigo Y (1978) A new method for the preparation of ketones by decarbonylation of α-hydroxycarboxylic acid with 2-chlorobenzoxazolium salt. Chem Lett
1978:49
61. March J (1985) Decarbonylation of acids and esters. In: March J (ed) Advanced organic
chemistry, 3rd edn. Wiley, New York, p 341