Guaianolides in apiaceae: Perspectives on pharmacology and biosynthesis

Phytochemistry Reviews

Volumn 8, Issue 3, 2009, Pages 581-599

  Drew, Damian Paul ^a   Krichau, Nadja ^a   Reichwald, Kirsten ^a   Simonsen, Henrik Toft ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

SERCA inhibition; Sesquiterpene lactones; Thapsigargin

Indexed keywords

ARCHANGELOLIDE; COSTUNOLIDE; EUDESMANOLIDE DERIVATIVE; FEGOLIDE; GRADOLIDE; GUAIANOLIDE DERIVATIVE; ISOPRENOID; MEVALONIC ACID; MONTANOLIDE; NORTRILOBOLIDE; PARTHENOLIDE; SARCOPLASMIC RETICULUM CALCIUM TRANSPORTING ADENOSINE TRIPHOSPHATASE; SESQUITERPENE LACTONE DERIVATIVE; THAPSIGARGICIN; THAPSIGARGIN; THAPSITRANSTAGIN; THAPSIVILLOSIN A; THAPSIVILLOSIN B; THAPSIVILLOSIN C; THAPSIVILLOSIN D; THAPSIVILLOSIN E; THAPSIVILLOSIN F; THAPSIVILLOSIN G; THAPSIVILLOSIN H; THAPSIVILLOSIN I; THAPSIVILLOSIN J; THAPSIVILLOSIN K; THAPSIVILLOSIN L; TRILOBOLIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

APIALES; APOPTOSIS; CONFERENCE PAPER; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; EPOXIDATION; NONHUMAN; PHYTOCHEMISTRY; PLASTID; PRIORITY JOURNAL;

APIACEAE; THAPSIA;

EID: 70350112403     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-009-9130-z     Document Type: Conference Paper

References (87)

1. Ahmed S (1998) Isolation and Structural elucidation of chemical constituents from Fumaria indica, Ferula oopoda and Withania somnifera. Ph.D. Thesis, University of Karachi
2. SP Andrews M Ball F Wierschem E Cleator S Oliver K Hogenauer O Simic A Antonello U Hunger MD Smith SV Ley 2007 Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition Chem Eur J 13 20 5688 5712 10.1002/chem.200700302 10.1002/chem.200700302 (Pubitemid 47117393)
3. G Appendino MG Valle R Caniato EM Cappelletti 1986 Sesquiterpene Lactones from Laserpitium garganicum Phytochem 25 7 1747 1749 10.1016/S0031-9422(00) 81252-2 10.1016/S0031-9422(00)81252-2
4. R Azarken FM Guerra FJ Moreno-Dorado ZD Jorge GM Massanet 2008 Substituent effects in the transannular cyclizations of germacranes. Synthesis of 6-epi-costunolide and five natural steiractinolides Tetrahedron 64 10896 10905 10.1016/j.tet.2008.09.017 10.1016/j.tet.2008.09.017
5. Barton Sir D, Nakanishi K, Meth-Cohn O (1999) Comprehensive natural products chemistry. Elsevier Science Ltd, London
6. AC Beekman WV Woerdenbag N Pras AWT Konings HV Wikström TJ Schmidt 1997 Structure-cytotoxicity relationship of some helenanolide-type sesquiterpene lactones J Nat Prod 60 252 257 10.1021/np960517h 9090867 10.1021/np960517h (Pubitemid 27146459)
7. MR Berenbaum 2001 Chemical mediation of coevolution: phylogenetic evidence for apiaceae and associates Ann Mo Bot Gard 88 45 59 10.2307/2666131 10.2307/2666131
8. Berg JM, Tymoczkom JL, Stryer L (2007) Biochemistry. W.H. Freeman and company, New York
9. CM Bertea A Voster FWA Verstappen M Maffei J Beekwilder HJ Bouwmeester 2006 Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library Arch Biochem Biophys 448 1-2 3 12 10.1016/j.abb.2006.02.026 16579958 10.1016/j.abb.2006.02.026
10. JA Bick BM Lange 2003 Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: unidirectional transport of intermediates across the chloroplast envelope membrane Arch Biochem Biophys 415 2 146 154 10.1016/S0003-9861(03)00233-9 12831836 10.1016/S0003-9861(03)00233-9 (Pubitemid 36794126)
11. J Bohlmann G Meyer-Gauen R Croteau 1998 Plant terpenoid synthases: molecular biology and phylogenetic analysis Proc Natl Acad Sci USA 95 8 4126 4133 10.1073/pnas.95.8.4126 9539701 10.1073/pnas.95.8.4126 (Pubitemid 28207876)
12. SS Chandran A Nan DM Rosen H Ghandehari SR Denmeade 2007 A prostate-specific antigen activated N-(2-hydroxypropyl) methacrylamide copolymer prodrug as dual-targeted therapy for prostate cancer Mol Cancer Ther 6 11 2928 2937 10.1158/1535-7163.MCT-07-0392 18025277 10.1158/1535-7163.MCT-07-0392 (Pubitemid 350206771)
13. MCY Chang JD Keasling 2006 Production of isoprenoid pharmaceuticals by engineered microbes Nat Chem Biol 2 12 674 681 10.1038/nchembio836 17108985 10.1038/nchembio836 (Pubitemid 44764209)
14. JH Choi J Ha JH Park JY Lee YS Lee HJ Park JW Choi Y Masuda K Nakaya KT Lee 2002 Costunolide triggers apoptosis in human leukemia U937 cells by depleting intracellular thiols Jpn J Cancer Res 93 1327 1333 12495472
15. Christensen SB, Norup E, Rasmussen U (1984a) Chemistry and structure-activity relationship of the histamine secretagogue thapsigargin and related compounds. In: Krogsgaard-Larsen P, Christensen SB, Kofod H (eds) Natural products and drug development. Munksgaard, Copenhagen
16. SB Christensen E Norup U Rasmussen JO Madsen 1984 Structure of histamine releasing guaianolides from Thapsia species Phytochem 23 8 1659 1663 10.1016/S0031-9422(00)83463-9 10.1016/S0031-9422(00)83463-9
17. SB Christensen A Andersen UW Smitt 1997 Sesquiterpenoids from Thapsia species and medicinal chemistry of the thapsigargins Fortschr Chem Org Naturst 71 129 167 9250023
18. SB Christensen A Andersen H Kromann M Treiman B Tombal S Denmeade JT Isaacs 1999 Thapsigargin analogues for targeting programmed death of androgen-independent prostate cancer cells Bioorg Med Chem 7 7 1273 1280 10.1016/S0968-0896(99)00074-7 10465403 10.1016/S0968-0896(99)00074-7 (Pubitemid 29292369)
19. AV Christiansen H Paalum SM Andersen A Pujadas UW Smitt 1997 Quantitative determination of thapsigargins in roots and fruits from Thapsia gymnesica Planta Med 63 565 567 10.1055/s-2006-957769 17252379 10.1055/s-2006-957769 (Pubitemid 28035461)
20. JW De Kraker MCR Franssen A de Groot WA Konig HJ Bouwmeester 1998 (+)-Germacrene A biosynthesis-The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory Plant Physiol 117 4 1381 1392 10.1104/pp.117.4.1381 9701594 10.1104/pp.117.4.1381
21. JW De Kraker MCR Franssen MCF Dalm A de Groot HJ Bouwmeester 2001 Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene A hydroxylase and NADP(+)-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis Plant Physiol 125 4 1930 1940 10.1104/pp.125.4.1930 11299372 10.1104/pp.125.4.1930 (Pubitemid 32375775)
22. JW De Kraker MCR Franssen M Joerink A de Groot HJ Bouwmeester 2002 Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome P450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory Plant Physiol 129 1 257 268 10.1104/pp.010957 12011356 10.1104/pp.010957 (Pubitemid 34535933)
23. SR Denmeade JT Isaacs 2005 The SERCA pump as a therapeutic target: making a "smart bomb" for prostate cancer Cancer Biol Ther 4 1 14 22 15662118
24. SR Denmeade XS Lin JT Isaacs 1996 Role of programmed (apoptotic) cell death during the progression and therapy for prostate cancer Prostate 28 4 251 265 10.1002/(SICI)1097-0045(199604)28:4<251::AID-PROS6>3.0.CO;2-G 8602401 10.1002/(SICI)1097-0045(199604)28:4<251::AID-PROS6>3.0.CO;2-G (Pubitemid 26119117)
25. PM Dewick 1995 The Biosynthesis of C-5-C-20 Terpenoid Compounds Nat Prod Rep 12 507 534 10.1039/np9951200507 7478287 10.1039/np9951200507
26. M Djermanovic M Stefanovic V Djermanovic M Milovanovic 1995 Structure elucidation of the sesquiterpene lactones from plant species Laserpitium latifolium L J Herbs Spices Med Plants 3 2 3 10 10.1300/J044v03n02-02 10.1300/J044v03n02-02
27. G Falsone H Haddad D Wendisch 1986 Sesquiterpene lactone triesters with unusual structures from Thapsia garganica L (Umbelliferae) Arch Pharm (Weinheim) 319 4 372 379 10.1002/ardp.19863190414 10.1002/ardp.19863190414 (Pubitemid 16166317)
28. BM Fraga 2006 Natural sesquiterpenoids Nat Prod Rep 23 943 972 10.1039/b507870a 17119641 10.1039/b507870a (Pubitemid 44808995)
29. GenSpera (2009) Technology information, GenSpera, Inc, San Antonio, Texas, USA. http://www.genspera.com. Cited 23 Feb 2009
30. EL Ghisalberti 1994 The Daucane (Carotane) class of sesquiterpenes Phytochem 37 3 597 623 10.1016/S0031-9422(00)90327-3 10.1016/S0031-9422(00) 90327-3 (Pubitemid 2156068)
31. D Hampel A Mosandl M Wust 2005 Biosynthesis of mono- and sesquiterpenes in carrot roots and leaves (Daucus carota L.): metabolic cross talk of cytosolic mevalonate and plastidial methylerythritol phosphate pathways Phytochem 66 3 305 311 10.1016/j.phytochem.2004.12.010 10.1016/j.phytochem.2004.12.010 (Pubitemid 40169990)
32. A Hemmerlin JF Hoeffler O Meyer D Tritsch IA Kagan C Grosdemange-Billiard M Rohmer TJ Bach 2003 Cross-talk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in tobacco bright yellow-2 cells J Biol Chem 278 29 26666 26676 10.1074/jbc.M302526200 12736259 10.1074/jbc.M302526200 (Pubitemid 36876812)
33. M Holub M Budesinsky 1986 Review article number 20. Sesquiterpene lactones of the umbelliferae Phytochem 25 9 2015 2026 10.1016/0031-9422(86) 80060-7 10.1016/0031-9422(86)80060-7
34. M Holub Z Samek 1973 On Terpenes. 222. Structure of archangelolide, a sesquiterpenic lactone from Laserpitium archangelica wulf Collect Czech Chem Commun 38 3 731 738
35. M Holub R Degroote V Herout F Sorm 1968 Plant Substances. 28. Oxygen-containing components of light petroleum extract of Laser trilobum (L) Borkh root structure of laserine Collect Czech Chem Commun 33 9 2911
36. M Holub V Herout Z Samek O Motl 1972 Terpenes. 214. Structure of 2 sesquiterpenic lactones, isomontanolide and acetylisomontanolide from Laserpitium siler L Collect Czech Chem Commun 37 4 1186
37. M Holub Z Samek S Vasickova M Masojidkova 1978 Terpenes. 251. 11-hydroxy-1-beta-H, 5-beta-H, 6-alpha-, 7-alpha-H-guaian-6, 12-olides-relative and absolute-configuration of sesquiterpenic lactones montanolide, isomontanolide, acetylisomontanolide and related substances Collect Czech Chem Commun 43 9 2444 2470
38. M Holub O Motl Z Samek 1978 Terpenes. 252. Structure and relative and absolute-configurations of sesquiterpenic lactones gradolide and polhovolide from Laserpitium Siler L Collect Czech Chem Commun 43 9 2471 2477
39. M Holub J Toman V Herout 1987 The phylogenetic-relationships of the asteraceae and apiaceae based on phytochemical characters Biochem Syst Ecol 15 3 321 326 10.1016/0305-1978(87)90006-8 10.1016/0305-1978(87)90006-8
40. M Iranshahi ST Hosseini AR Shahverdi K Molazade SS Khan VU Ahmad 2008 Diversolides A-G, guaianolides from the roots of Ferula diversivittata Phytochem 69 2753 2757 10.1016/j.phytochem.2008.08.009 Observe that retraction of claims on diversolides A, C-G are in the process of being printed
41. CM Jakobsen SR Denmeade JT Isaacs A Gady CE Olsen SB Christensen 2001 Design, synthesis, and pharmacological evaluation of thapsigargin analogues for targeting apoptosis to prostatic cancer cells J Med Chem 44 26 4696 4703 10.1021/jm010985a 11741487 10.1021/jm010985a (Pubitemid 33144479)
42. MH Kabilov AI Saidkhodzhaev VM Malikov S Melibaev 1994 Sesquiterpene lactones of Ferula koso-poljanskyi Chem Nat Compd 30 4 523 10.1007/BF00630416 10.1007/BF00630416
43. SH Lee MY Lee HM Kang DC Han KH Son DC Yang ND Sung CW Lee HM Kim BM Kwon 2003 Anti-tumor activity of the farnesyl-protein transferase inhibitors arteminolides, isolated from artemisa Bioorg Med Chem 11 4545 4549 10.1016/j.bmc.2003.08.008 14527550 10.1016/j.bmc.2003.08.008 (Pubitemid 37194258)
44. YS Li JJ Chen H Zhou SD Luo HY Wang DY Zhu 2003 Two new guaianolides and a new daucene derivative from Sinodielsia yunnanensis Planta Med 69 10 962 964 10.1055/s-2003-45111 14648405 10.1055/s-2003-45111 (Pubitemid 38005458)
45. HZ Liu KG Jensen LM Tran M Chen L Zhai CE Olsen H Sohoel SR Denmeade JT Isaacs SB Christensen 2006 Cytotoxic phenylpropanoids and an additional thapsigargin analogue isolated from Thapsia garganica Phytochem 67 24 2651 2658 10.1016/j.phytochem.2006.10.005 10.1016/j.phytochem.2006.10.005 (Pubitemid 44778824)
46. S Milosavljevic V Bulatovic M Stefanovic 1999 Sesquiterpene lactones from the Yugoslavian wild growing plant families asteraceae and apiaceae J Serb Chem Soc 64 7-8 397 442
47. B Muckensturm F Diyani J-P Reduron 1995 Grilactone and other terpenoids from Anthriscus nitida Biochem Syst Ecol 23 7/8 875 876 10.1016/0305-1978(95) 00058-5 10.1016/0305-1978(95)00058-5 (Pubitemid 3023142)
48. B Muckensturm F Diyani DL Nouën S Fkih-Tetouani J-P Reduron 1997 Ammolactone, a guaianolide from a medicinal plant, Ammodaucus leucotrichus Phytochem 44 5 907 910 10.1016/S0031-9422(96)00621-8 10.1016/S0031-9422(96) 00621-8 (Pubitemid 27093170)
49. J Nawrot Z Smitalova M Holub 1983 Terpenes. 273. Deterrent activity of sesquiterpene lactones from the umbelliferae against storage pests Biochem Syst Ecol 11 3 243 245 10.1016/0305-1978(83)90061-3 10.1016/0305-1978(83)90061-3
50. E Norup UW Smitt SB Christensen 1986 The potencies of Thapsigargin and analogs as activators of rat peritoneal mast-cells Planta Med 52 4 251 255 10.1055/s-2007-969144 17345299 10.1055/s-2007-969144
51. MR Nurmukhamedova SZ Kasymov S Melibaev 1982 Grilactone from Ferula-Penninervis Him Prir Soedin 2 261
52. MR Nurmukhamedova SZ Kasymov GP Sidyakin 1983 Ferolid-A new lactone from Ferula-Penninervis Him Prir Soedin 4 533
53. MR Nurmukhamedova S Kasymov ND Abdullaev GP Sidyakin 1985 Structure of fegolide Him Prir Soedin 3 335 337
54. K Okada H Kasahara S Yamaguchi H Kawaide Y Kamiya H Nojiri H Yamane 2008 Genetic evidence for the role of isopentenyl diphosphate isomerases in the mevalonate pathway and plant development in arabidopsis Plant Cell Physiol 49 4 604 616 10.1093/pcp/pcn032 18303110 10.1093/pcp/pcn032
55. DP Piet R Schrijvers MCR Franssen A de Groot 1995 Biotransformation of Germacrane epoxides by Cichorium intybus Tetrahedron 51 22 6303 6314 10.1016/0040-4020(95)00272-A 10.1016/0040-4020(95)00272-A
56. M Pinar M Rico B Rodriguez 1982 Desangeloylshairidin, a sesquiterpene lactone from Guillonea scabra Phytochem 21 1802 1804
57. M Pinar B Rodriguez M Rico A Perales J Fayos 1983 Guillonein, An epoxyguaianolide from Guillonea scabra, X-Ray structure determination Phytochem 22 987 990 10.1016/0031-9422(83)85037-7 10.1016/0031-9422(83)85037-7
58. U Rasmussen SB Christensen F Sandberg 1978 Thapsigargine and thapsigargicine, two new histamine liberators from Thapsia garganica L Acta Pharm Suec 15 2 133 140 79299
59. U Rasmussen SB Christensen F Sandberg 1981 Phytochemistry of the genus Thapsia Planta Med 43 336 341 10.1055/s-2007-971521 17402057 10.1055/s-2007-971521
60. DK Ro EM Paradise M Ouellet KJ Fisher KL Newman JM Ndungu KA Ho RA Eachus TS Ham J Kirby MCY Chang ST Withers Y Shiba R Sarpong JD Keasling 2006 Production of the antimalarial drug precursor artemisinic acid in engineered yeast Nature 440 7086 940 943 10.1038/nature04640 16612385 10.1038/nature04640
61. F Rohdich S Hecht K Gartner P Adam C Krieger S Amslinger D Arigoni A Bacher W Eisenreich 2002 Studies on the nonmevalonate terpene biosynthetic pathway: metabolic role of IspH (LytB) protein Proc Natl Acad Sci USA 99 3 1158 1163 10.1073/pnas.032658999 11818558 10.1073/pnas.032658999 (Pubitemid 34136463)
62. M Rohmer M Knani P Simonin B Sutter H Sahm 1993 Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate Biochem J 295 517 524 8240251
63. D Rontein S Onillon G Herbette A Lesot D Werck-Reichhart C Sallaud A Tissier 2008 CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5), 11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane J Biol Chem 283 10 6067 6075 10.1074/jbc.M708950200 18167342 10.1074/jbc.M708950200
64. JJ Rubal FM Guerra FJ Moreno-Dorado ZD Jorge GM Massanet H Sohoel UW Smitt K Frydenvang SB Christensen C Nielsen M Erikson 2006 Sesquiterpenes from Thapsia nitida var. meridionalis and Thapsia nitida var. nitida J Nat Prod 69 11 1566 1571 10.1021/np0603065 17125222 10.1021/np0603065 (Pubitemid 46031806)
65. JJ Rubal FM Guerra FJ Moreno-Dorado M Akssira F Mellouki AJ Pujadas ZD Jorge GM Massanet 2007 Sulfur-containing sesquiterpenes from Thapsia villosa Tetrahedron 60 159 164 10.1016/j.tet.2003.10.079 10.1016/j.tet.2003.10.079
66. JJ Rubal FJ Moreno-Dorado FM Guerra ZD Jorge A Saouf M Akssira F Mellouki R Romero-Garrido GM Massanet 2007 A pyran-2-one and four meroterpenoids from Thapsia transtagana and their implication in the biosynthesis of transtaganolides Phytochem 68 2480 2486 10.1016/j.phytochem.2007.06.023 10.1016/j.phytochem.2007.06.023 (Pubitemid 47429721)
67. P Rüngeler V Castro G Mora N Gören W Vichnewski HL Pahl I Merfort TJ Schmidt 1999 Inhibition of transcription factor NF-κB by sesquiterpene lactones: a proposed molecular mechanism of action Bioorg Med Chem 7 2343 2352 10.1016/S0968-0896(99)00195-9 10632044 10.1016/S0968-0896(99)00195- 9 (Pubitemid 30122736)
68. Rychlewska U, Hodgson DJ, Holub M, Budesinsky M, Smitalova Z (1985) On Terpenes 288 The Structure of 2-Oxo-8-alpha-angeloyloxy-11-alpha-acetoxy-5-beta- H,6-alpha-H,7-alpha-H-guai-1(10),3-dien-6,12-olide, a sesquiterpene lactone from Laserpitium prutenicum L. Revision of the stereostructures of native 2-oxoguai-1(10),3-dien-6,12-olides from the species of the Umbelliferae family. Collect Czech Chem Commun 50(11):2607-2624
69. GV Sagitdinova AI Saidkhodzhaev VM Malikov MG Pimenov S Melibeav 1990 Sesquiterpene lactones of Ferula clematidifolia and Ligularia alpigena Him Prir Soedin 4 553 555
70. Schall A, Reiser O (2008) Synthesis of biologically active guaianolides with a trans-annulated lactone moiety. Eur J Org Chem 2353-2364. doi: 10.1002/ejoc.200700880
71. SV Serkerov 1980 Stereochemistry of Guaianolides of Ferula oopoda Him Prir Soedin 5 629 633
72. SV Serkerov U Rikhlevska AN Aleskerova NF Mirbabaev 1991 New guanolide-Opofersin from Ferula Oopoda roots Him Prir Soedin 3 318 319
73. B Siedle AJ García-Piñeres R Murillo J Schulte-Mönting V Castro P Rüngeler CA Klaas FB Da Costa W Kisiel I Merfort 2004 Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-κB J Med Chem 47 6042 6054 10.1021/jm049937r 15537359 10.1021/jm049937r (Pubitemid 39507346)
74. Z Smitalova M Budesinsky D Saman S Vasickova M Holub 1984 On Terpenes. 279. Components of the extract from the underground parts of Laserpitium siler L of Slovenian origin, mainly sesquiterpenic lactones Collect Czech Chem Commun 49 4 852 870
75. Z Smitalova M Budesinsky D Saman M Holub 1986 On Terpenes. 291. Minor sesquiterpenic lactones of Laser trilobum (L) Borkh species Collect Czech Chem Commun 51 6 1323 1339
76. UW Smitt C Cornett A Andersen SB Christensen P Avato 1990 New proazulene guaianolides from Thapsia villosa J Nat Prod 53 6 1479 1484 10.1021/np50072a012 1708405 10.1021/np50072a012
77. UW Smitt AK Jager A Adsersen L Gudiksen 1995 Comparative studies in phytochemistry and fruit anatomy of Thapsia garganica and T. transtagana, Apiaceae (Umbelliferae) Bot J Linn Soc 117 4 281 292 10.1006/bojl.1995.0019 10.1006/bojl.1995.0019
78. H Søhoel AM Jensen JV Moller P Nissen SR Denmeade JT Isaacs CE Olsen SB Christensen 2006 Natural products as starting materials for development of second-generation SERCA inhibitors targeted towards prostate cancer cells Bioorg Med Chem 14 8 2810 2815 10.1016/j.bmc.2005.12.001 16412648 10.1016/j.bmc.2005.12.001 (Pubitemid 43343668)
79. Q Song ML Gomezbarrios EL Hopper MA Hjortso NH Fischer 1995 Biosynthetic-studies of lactucin derivatives in hairy root cultures of Lactuca floridana Phytochem 40 6 1659 1665 10.1016/0031-9422(95)00478-P 10.1016/0031-9422(95)00478-P (Pubitemid 3009256)
80. CL Steele J Crock J Bohlmann R Croteau 1998 Sesquiterpene synthases from grand fir (Abies grandis)-Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization and bacterial expression of delta-selinene synthase and gamma-humulene synthase J Biol Chem 273 4 2078 2089 10.1074/jbc.273.4.2078 9442047 10.1074/jbc.273.4.2078 (Pubitemid 28069256)
81. K Suzuki M Okasaka Y Kashiwada Y Takaishi G Honda M Ito Y Takeda OK Kodzhimatov O Ashurmetov M Sekiya Y Ikeshiro 2007 Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity J Nat Prod 70 12 1915 1918 10.1021/np0703996 18052129 10.1021/np0703996
82. KH Teoh DR Polichuk DW Reed G Nowak PS Covello 2006 Artemisia annua L (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin FEBS Lett 580 5 1411 1416 10.1016/j.febslet.2006.01.065 16458889 10.1016/j.febslet.2006.01.065 (Pubitemid 43222008)
83. C Toyoshima H Nomura 2002 Structural changes in the calcium pump accompanying the dissociation of calcium Nature 418 6898 605 611 10.1038/nature00944 12167852 10.1038/nature00944 (Pubitemid 34886857)
84. NH Wang M Taniguchi D Tsuji M Doi H Ohishi K Yoza K Baba 2003 Four guaianolides from Sinodielsia yunnanensis Chem Pharm Bull (Tokyo) 51 1 68 70 10.1248/cpb.51.68 10.1248/cpb.51.68 (Pubitemid 41702019)
85. M Wictome M Holub JM East AG Lee 1994 The importance of the hydroxyl moieties for inhibition of Ca2+-ATPases by trilobolide and 2, 5-di(tert-butyl)-1, 4-benzohydroquinone Biochem Biophys Res Commun 199 2 916 921 10.1006/bbrc.1994.1316 8135840 10.1006/bbrc.1994.1316
86. ST Withers JD Keasling 2007 Biosynthesis and engineering of isoprenoid small molecules Appl Microbiol Biotechnol 73 5 980 990 10.1007/s00253-006-0593-1 17115212 10.1007/s00253-006-0593-1 (Pubitemid 44974305)
87. S Zhang YK Won CN Ong HM Shen 2005 Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms Curr Med Chem Anticancer Agents 5 3 239 249 10.2174/1568011053765976 15992352 10.2174/1568011053765976 (Pubitemid 40645593)