Phenalenone-type phytoalexins from Musa acuminata. Synthesis of 4-phenyl-phenalenones

作者: Javier G. Luis , Winston Q. Fletcher , Fernando Echeverri , Teresa A. Grillo

DOI: 10.1016/S0040-4020(01)85707-0

关键词: Carbon-13 NMRStereochemistryHeteronuclear moleculePhytoalexinPhenolsMusa acuminataProton NMRChemical synthesisFusarium oxysporumChemistry

摘要: Abstract Two new 4-phenyl-phenalenone-type phytoalexins ( 2 , 3 ) have been isolated from rhizomes of Musa acuminata infected with the fungus Fusarium oxysporum . The structures were elucidated on basis spectroscopic evidence, chemical correlation and synthesis commercial phenalen-1-one. shift for all hydrogen carbon atoms in substances unambiguously established by mono- bidimensional, homo- heteronuclear NMR experiments 1 H NMR, 13 C COSY, HMQC HMBC). In preliminary “in vitro” assays, shown inhibitory activity growth germinative tube f. sp. cubense race 4

参考文章(6)
Peter Albersheim, A. G. Darvill, Michael McNeil, B. S. Valent, M. G. Hahn, Gary Lyon, J. K. Sharp, A. E. Desjardins, M. W. Spellman, L. M. Ross, B. K. Robertson, Per Aman, L.- E. Franzen, Structure and function of complex carbohydrates active in regulating plant-microbe interactions Pure and Applied Chemistry. ,vol. 53, pp. 79- 88 ,(1981) , 10.1351/PAC198153010079
Javier G. Luis, Fernando Echeverri, Winston Quinones, Ivan Brito, Matias Lopez, Fernando Torres, Gloria Cardona, Zahira Aguiar, Carlos Pelaez, Mauricio Rojas, Irenolone and emenolone: two new types of phytoalexin from Musa paradisiaca Journal of Organic Chemistry. ,vol. 58, pp. 4306- 4308 ,(1993) , 10.1021/JO00068A027
Lee A. Hadwiger, Ali Jafri, Sharon von Broembsen, Robert Eddy, Mode of Pisatin Induction Plant Physiology. ,vol. 53, pp. 52- 63 ,(1974) , 10.1104/PP.53.1.52
R Cooke, R Thomas, Colouring Matters of Australian Plants. XVIII. Constituents of Anigozanthos rufus Australian Journal of Chemistry. ,vol. 28, pp. 1053- 1057 ,(1975) , 10.1071/CH9751053
W. Clark Still, Stannylation/destannylation. New syntheses of carbonyl compounds via organotin intermediates Journal of the American Chemical Society. ,vol. 99, pp. 4836- 4838 ,(1977) , 10.1021/JA00456A057
P Wharton, D Bohlen, Communications- Hydrazine Reduction of α, β-Epoxy Ketones to Allylic Alcohols Journal of Organic Chemistry. ,vol. 26, pp. 3615- 3616 ,(1961) , 10.1021/JO01067A117