Wasalexins A and B, new phytoalexins from wasabi: Isolation, synthesis, and antifungal activity

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 20, 1999, Pages 3015-3020

  Pedras, M Soledade C ^a   Sorensen, John L ^a   Okanga, Francis I ^a   Zaharia, Irina L ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PHYTOALEXIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRUCIFERA; FUNGICIDAL ACTIVITY; FUNGUS; ISOLATION PROCEDURE; NONHUMAN; PLANT LEAF; SYNTHESIS;

ANTIFUNGAL AGENTS; BRASSICACEAE; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; SULFIDES;

BRASSICACEAE; EUTREMA WASABI; FUNGI; JAPONICA; LEPTOSPHAERIA BICOLOR; LEPTOSPHAERIA MACULANS; PHOMA; PLENODOMUS WASABIAE;

EID: 0033581599     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00523-5     Document Type: Article

References (26)

1. Brooks, C. J.; Watson, D. G. Nat. Prod. Rep. 1985, 427, and references therein.
2. (a) Dixon, R. A. Biol. Rev. 1986, 61, 239;
3. (b) Dixon, R. A.; Harrison, M. J.; Lamb, C. J. Annual Rev. Plant Phytopathol. 1994, 32, 479;
4. (c) Kúc, J. Annual Rev. Phytopathol. 1995, 33, 275;
5. (d) Smith, C. J. New Phytol. 1996, 132, 1.
6. For a recent review on brassica phytoalexins: 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, 1997; pp 155-166.
7. (a) Pedras, M. S. C.; Taylor, J. L.; Morales, V. M. Phytochemistry 1995, 37, 1215;
8. (b) Taylor, J. L.; Pedras, M. S. C.; Morales, V. M. Trends in Microbiology 1995, 3, 202.
9. Pedras, M. S. C.; Sorensen, J. L., Phytochemistry 1998, 49, 1959.
10. 3CN, at a flow rate 1.0 mL/min over 35 min.
11. Conn, K. L.; Browne, L. M.; Tewari, J. P.; Ayer, W. A. J. Plant Biochem. Biotech. 1994, 3, 125.
12. -1.
13. Monde, K., Sasaki, K., Shirata, A. and Takasugi, M., Phytochemistry 1991, 30, 3921.
14. In the standard HMBC experiment a coupling over four bonds is usually not observed (Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093).
15. Although long range couplings over four, or even five bonds can be detected by HMBC, either special modifications to the routine pulse sequence, (Furihata, K.; Seto, H. Tetrahedron Lett. 1995, 36, 2817)
16. or newer pulsed field gradients (Wagner, R.; Berger, S. Magn. Reson. Chem. 1998, 36, S44) are required.
17. Gribble, G. W.; Heald, P. W. Synthesis 1975, 650.
18. Murahashi, S.; Oda, T.; Sugahara, T.; Masui, Y. J. Org. Chem. 1990, 55, 1744.
19. -1.
20. Wenkert, E.; Bhattacharyya, N. K.; Reid, T. L.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 797.
21. Behringer, H.; Wessauer, H. Chem. Ber. 1952, 85, 743.
22. -1.
23. Kawasaki, T.; Kodama, A.; Noshida, T.; Shimizu, K.; Somei, M. Heterocycles 1991, 32, 221.
24. 3; however, 10b could not be obtained as a single compound due to isomerization to 10a (<10%) during purification.
25. 2).
26. 7 spores / mL in 500 μL solutions of compound to be tested (3% Tween 80 and 2% DMSO in minimal medium) were incubated still under constant fluorescent light, at 24 ± 1° C. The percentage of spore germination was determined by counting about 300 spores (in randomly selected fields) for each replicate.