The synthesis and biological evaluation of labelled karrikinolides for the elucidation of the mode of action of the seed germination stimulant

Tetrahedron

Volumn 67, Issue 1, 2011, Pages 152-157

  Scaffidi, Adrian ^a   Flematti, Gavin R ^a   Nelson, David C ^a   Dixon, Kingsley W ^a,b   Smith, Steven M ^a   Ghisalberti, Emilio L ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b KINGS PARK AND BOTANIC GARDEN   (Australia)

Author keywords

Germination stimulant; Karrikinolide; Karrikins; Seed dormancy; Smoke

Indexed keywords

3A,4,5,7,7A 3 METHYL 2H FURO[2,3 C]PYRAN 2 ONE C5 13; 5 (9 AZIDONONOXY)METHYL 3 METHYL 2H FURO[2,3 C]PYRAN 2 ONE; 5 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]METHYL 3 METHYL 2H FURO[2,3 C]PYRAN 2 ONE; 5 [3 AZIDO 5 (AZIDOMETHYL)BENZYLOXY]METHYL 3 METHYL 2H FURO[2,3 C]PYRAN 2 ONE; 5 AZIDOMETHYL 3 METHYL 2H FURO[2,3 C]PYRAN 2 ONE; 7 3 METHYL 2H FURO[2,3 C]PYRAN 2 ONE H 3; BUTENOLIDE; KARRIKINOLIDE; N [1 [9 [(3 METHYL 2 OXO 2H FURO[2,3 C]PYRAN 5 YL)METHOXY]NONYL 1H 1,2,3 TRIAZOL 4 YL]METHYL] 5 (2 OXOHEXAHYDRO 1H THIENO[3,4 D]IMIDAZOL-4-YL)PENTANAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BRASSICA; BRASSICA TORUNEFORTII; CHEMICAL STRUCTURE; GERMINATION; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

EID: 78649781711     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.006     Document Type: Article

References (35)

1. K.W. Dixon, D.J. Merritt, G.R. Flematti, and E.L. Ghisalberti Acta Hortic. 813 2009 155
2. S. Roche, K.W. Dixon, and J.S. Pate Aust. J. Bot. 45 1997 783
3. N.A.C. Brown S. Afr. J. Bot. 70 2004 559
4. J.E. Keeley, and C.J. Fotheringham Ecology 79 1998 2320
5. M.A. Pérez-Fernández, and S. Rodríguez- Echeverría J. Chem. Ecol. 29 2003 237
6. S.M. Pierce, K. Esler, and R.M. Cowling Oecologia 102 1995 520
7. G.R. Flematti, E.L. Ghisalberti, K.W. Dixon, and R.D. Trengove Science 305 2004 977
8. J.C. Stevens, D.J. Merritt, G.R. Flematti, E.L. Ghisalberti, and K.W. Dixon Plant Soil 298 2007 113
9. G.R. Flematti, E.L. Ghisalberti, K.W. Dixon, and R.D. Trengove J. Agric. Food Chem. 57 2009 9475
10. D.C. Nelson, J.-A. Riseborough, G.R. Flematti, J. Stevens, E.L. Ghisalberti, K.W. Dixon, and S.M. Smith Plant Physiol. 149 2009 863
11. D.J. Merritt, M. Kristiansen, G.R. Flematti, S.R. Turner, E.L. Ghisalberti, R.D. Trengove, and K.W. Dixon Seed Science Research 16 2006 29
12. G.R. Flematti, E.L. Ghisalberti, K.W. Dixon, and R.D. Trengove Tetrahedron Lett. 46 2005 5719
13. K. Sun, Y. Chen, T. Wagerle, D. Linnstaedt, M. Currie, P. Chmura, Y. Song, and M. Xu Tetrahedron Lett. 49 2008 2922
14. R. Nagase, M. Katayama, H. Mura, N. Matsuo, and Y. Tanabe Tetrahedron Lett. 49 2008 4509
15. E.D. Goddard-Borger, E.L. Ghisalberti, and R.V. Stick Eur. J. Org. Chem. 2007 3925
16. G.R. Flematti, A. Scaffidi, E.D. Goddard-Borger, C.H. Heath, D.C. Nelson, L.E. Commander, R.V. Stick, K.W. Dixon, S.M. Smith, and E.L. Ghisalberti J. Agric. Food Chem. 58 2010 8612
17. R.J. Beynon, and J.M. Pratt Mol. Cell. Proteomics 4 2005 857
18. P. Bailon, and D.V. Weber Nature 335 1988 839
19. K. Kotzyba-Hibert, I. Kapfer, and M. Goeldner Angew. Chem., Int. Ed. 34 2003 1296
20. J.L. Guerquin-Kern, T.D. Wu, C. Quintana, and A. Croisy Biochim. Biophys. Acta 2005 228
21. A.S. Raghavana, and H.C. Hang Drug Discovery Today 14 2009 178
22. B. Zwanenburg, A.S. Mwakaboko, A. Reizelman, G. Anilkumar, and D. Sethumadhavan Pest Manage. Sci. 65 2009 478
23. J.A. Prescher, D.H. Dube, and C.R. Bertozzi Nature 430 2004 873
24. P.V. Chang, J.A. Prescher, M.J. Hangauer, and C.R. Bertozzi J. Am. Chem. Soc. 129 2007 8400
25. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
26. Q. Wang, T.R. Chan, R. Hilgraf, V.V. Fokin, K.B. Sharpless, and M.G. Finn J. Am. Chem. Soc. 125 2003 3192
27. F. Kaschani, S.H.L. Verhelst, P.F. Van Swieten, M. Verdoes, C.-S. Wong, Z. Wang, M. Kaiser, H.S. Overkleeft, M. Bogyo, and R.A.L. van der Hoorn The Plant J. 57 2009 373
28. J.M. Nyangulu, M.M. Galka, A. Jadhav, Y. Gai, C.M. Graham, K.M. Nelson, A.J. Cutler, D.C. Taylor, G.M. Banowetz, and S.R. Abrams J. Am. Chem. Soc. 127 2005 1662
29. N.M. Green, L. Konieczny, E.J. Toms, and R.C. Valentine Biochem. J. 125 1971 781
30. P.E. Nielson, and O. Buchardt Photochem. Photobiol. 35 1982 317
31. M. Hashimoto, and Y. Hatanaka Eur. J. Org. Chem. 2008 2513
32. R.E. Galardy, L.C. Craig, and M.P. Printz Nat. New Biol. 242 1973 127
33. T. Hosoya, T. Hiramatsu, T. Ikemoto, M. Nakanishi, H. Aoyama, A. Hosoya, T. Iwata, K. Maruyama, M. Endo, and M. Suzuki Org. Biomol. Chem. 2 2004 637
34. P.H. Amavam-Zollo, and P. Sinay Carbohydr. Res. 150 1986 199
35. T. Hosoya, T. Hiramatsu, T. Ikemoto, H. Aoyama, T. Ohmae, M. Endoc, and M. Suzuki Bioorg. Med. Chem. Lett. 15 2005 1289