Probing the Phytopathogenic Blackleg Fungus with a Phytoalexin Homolog

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 416-417

  Pedras, M Soledade C ^a   Okanga, Francis I ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001645281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971702i     Document Type: Article

References (28)

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2. (b) Brooks, C. J.; Watson, D. G. Nat. Prod. Rep. 1991, 367-389.
3. (a) Daniel, M., Purkayastha, R. P., Eds. Handbook of Phytoalexin Metabolism and Action; Marcel Dekker: Inc.: New York, 1995; p 650.
4. (b) Van Etten, H. D.; Mathews, D. E.; Mathews, P. S. Annu. Rev. Phytopathol. 1989, 27, 143-164.
5. First isolation of brassinin (1): Takasugi, M.; Katsui, N.; Shirata, A.; J. Chem. Soc., Chem. Commun. 1986, 1077-1078. Metabolism of brassinin: Pedras, M. S. C.; Taylor, J. L. J. Org. Chem. 1991, 56, 2619-2621.
6. First isolation of brassinin (1): Takasugi, M.; Katsui, N.; Shirata, A.; J. Chem. Soc., Chem. Commun. 1986, 1077-1078. Metabolism of brassinin: Pedras, M. S. C.; Taylor, J. L. J. Org. Chem. 1991, 56, 2619-2621.
7. (a) Pedras, M. S. C.; Borgmann, I.; Taylor, J. L. Phytochem. (Life Sci. Adv.) 1992, 11, 1-7.
8. (b) Pedras, M. S. C.; Taylor, J. L. J. Nat. Prod. 1993, 56, 731-738.
9. For a review on the blackleg fungus see, for example: Pedras, M. S. C.; Séguin-Swartz, G. Can. J. Plant Pathol. 1992, 14, 67-75.
10. Pedras, M. S. C.; Khan, A. K.; Smith, K. C.; Stettner, S. L. Can. J. Chem. 1997, 75, 825-828.
11. First isolation of brassicanal A (2): Monde, K.; Katsui, N.; Shirata, A. Chemistry Lett. 1990, 209-210. Metabolism of brassicanal A: Pedras, M. S. C.; Khan, A. Q. J. Agric. Food Chem. 1996, 44, 3403-3407.
12. First isolation of brassicanal A (2): Monde, K.; Katsui, N.; Shirata, A. Chemistry Lett. 1990, 209-210. Metabolism of brassicanal A: Pedras, M. S. C.; Khan, A. Q. J. Agric. Food Chem. 1996, 44, 3403-3407.
13. First isolation of brassilexin (3): Devys, M.; Barbier, M.; Loiselet, I.; Rouxel, T.; Sarniguet, A.; Kollmann, A.; Bousquet, J. Tetrahedron Lett. 1988, 29, 6447-6448. Metabolism of brassilexin: Pedras, M. S. C.; Khan, A. Q.; Taylor, J. L. In Phytochemicals for Pest Control; Hedin, P. A., Hollingworth, R. M., Masler, E. P., Miyamoto, J., Thompson, D. G., Eds.; ACS Symposium Series 658; American Chemical Society: Washington, DC, 1997; pp 155-166.
14. First isolation of brassilexin (3): Devys, M.; Barbier, M.; Loiselet, I.; Rouxel, T.; Sarniguet, A.; Kollmann, A.; Bousquet, J. Tetrahedron Lett. 1988, 29, 6447-6448. Metabolism of brassilexin: Pedras, M. S. C.; Khan, A. Q.; Taylor, J. L. In Phytochemicals for Pest Control; Hedin, P. A., Hollingworth, R. M., Masler, E. P., Miyamoto, J., Thompson, D. G., Eds.; ACS Symposium Series 658; American Chemical Society: Washington, DC, 1997; pp 155-166.
15. First isolation of cyclobrassinin (4) see ref 3. Metabolism of cyclobrassinin: Pedras, M. S. C.; Okanga, F. I. Chem. Commun., in press.
16. For a recent review on cruciferous phytoalexins see ref 8.
17. -4 M).
18. Cultures were incubated with 5 up to 3 weeks; 6, 7, and 9-11 were detected in cultures after 24 h of incubation, whereas 8 and 12 were detected after 5 days of incubation.
19. 2O/Py).
20. 3 Nevertheless, considering the sharpness of its NMR resonances, it appeared that only one isomer was present and an E stereochemistry would allow intramolecular hydrogen bonding.
21. Spectroscopic data are in complete agreement with the proposed structures. See the Supporting Information.
22. Prepared as reported in ref 4.
23. Compound 11 was isolated in 40% yield together with 5 (20%) and polar unidentified products.
24. (a) Szabo-Pusztay, K; Szabo, L, Synthesis 1979, 276-277.
25. (b) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p 317.
26. Segall, Y.; Casida, J. E. J. Agric. Food Chem. 1983, 31, 242-246.
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28. Kametani, T.; Kanaya, N.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1981, 959-963.