Metabolism of the host-selective toxins destruxin B and homodestruxin B: Probing a plant disease resistance trait

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1655-1658

  Pedras, M Soledade C ^a   Zaharia, Irina L ^a   Gai, Yuanzhu ^a   Smith, Kevin C ^a   Ward, Dale E ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000617874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991042z     Document Type: Article

References (25)

1. For recent reviews, see, inter alia: (a) Staskawicz, B. J.; et al. Science 1995, 268, 661.
2. (b) Cornelissen, B. J. C.; Melchers, L. S. Plant Physiol. 1993, 101, 709.
3. (c) Lamb, C. J.; et al. In Biotechnology in Agriculture; You, C. B., Chen, Z., Ding, Y., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands; 1993; p 45.
4. Johal, G. S.; Briggs, S. P. Science 1992, 258, 985.
5. For recent reviews, see: (a) Walton, J. D. Plant Cell 1996, 8, 1723.
6. (b) Walton, J. D.; Panaccione, D. G. Annu. Rev. Phytopathol. 1993, 31, 275 and references therein.
7. Yoneyama, K.; Anzai, H. In Biotechnology in Plant Disease Control; Wiley-Lyss, 1993; p 115.
8. (a) Pedras, M. S. C. Recent Res. Devel. Agric. Food Chem., 1998, 2, 513.
9. (b) Pedras, M. S. C.; Biesenthal, C. J. Can. J. Micro. 1998, 44, 547.
10. (c) Ward, D. E.; Vázquez, A.; Pedras, M. S. C. J. Org. Chem. 1999, 64, 1657.
11. Saharan, G. S. In Breeding Oilseed Brassicas; Labana, K. S., Banga, S. S., Banga, S. K., Eds.; Springer-Verlag: Berlin, 1993; p 181. Canola refers to varieties of rapeseed containing very low amounts of erucic acid and glucosinolates.
12. 6 dpm/mg.
13. All new compounds gave satisfactory spectroscopic data.
14. Ward, D. E.; Lazny, R.; Pedras, M. S. C. Tetrahedron Lett. 1997, 38, 339.
15. 9
16. Liquid scintillation counting was performed on a Beckman LS-6500 connected to a Wyse WY-370 data system, and results are quench corrected and reported in dpm.
17. 2O.
18. 14C counting window was 15-100 keV with an update time of 6 s.
19. The EtOAc residue was fractionated by multiple column chromatography (C-18 reversed phase silica gel, J. T. Baker, 40 μm) eluting with acetonitrile-water, gradient elution 30:70 to 100:0. The fractions were combined after HPLC analysis and further fractionated by PTLC on silica gel, 250 μm, developed in acetone-hexane (65:35) to yield chromatographically homogeneous material (TLC and HPLC).
20. -1) 3385, 3297, 2961, 1730, 1672, 1631, 1514, 1441, 1230, 1182.
21. All the destruxins reported so far were isolated from diverse fungal species; for recent reports see, for example: (a) Krasnoff, S. B.; Gibson, D. M. J. Nat. Prod. 1996, 59, 485.
22. (b) Cai, P.; Smith, D.; Katz, B.; Pearce, C.; Venables, D.; Houck, D. J. Nat. Prod. 1998, 61, 290.
23. Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933.
24. Stevens, C. M.; Tarbell, D. S. J. Org. Chem. 1954, 19, 1996.
25. Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346.