Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: Structures, syntheses and antifungal activity

Phytochemistry

Volumn 64, Issue 5, 2003, Pages 949-956

  Pedras, M S C ^a   Chumala, P B ^a   Suchy, M ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

4 Methoxyindolyl 3 acetonitrile; Asalexin A; Brassicaceae; Crucifer; G Leptosphaeria maculans; Phoma lingam; Phytoalexin; Stinkweed; Thlaspi arvense; Wasalexin synthesis

Indexed keywords

ARVELEXIN; COPPER CHLORIDE; ISOVITEXIN; PHYTOALEXIN; UNCLASSIFIED DRUG; WASALEXIN A;

ANTIFUNGAL ACTIVITY; ARTICLE; CRUCIFERA; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FANWEED; FUNGUS; LEPTOSPHAERIA MACULANS; PLANT; PLANT DEFENSE; STRESS;

BRASSICACEAE; LEPTOSPHAERIA; LEPTOSPHAERIA MACULANS; PHOMA; PHOMA LINGAM; THLASPI; THLASPI ARVENSE;

EID: 0142026148     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(03)00441-2     Document Type: Article

References (20)

1. Bailey, J.A., Mansfield, J.W. (Eds.), 1982. Phytoalexins. Blackie and Son, Glasgow, UK, p.334.
2. Behringer, H., Weissauer, H., 1952. Über eine neue Synthese des β-Oxindolyl-(3)-alanins (α-Oxy-tryptophans); ein Betrag zum Anwendungsbereich der Sörensenschen Aminosäure-Synthese. Chemische Berichte 85, 743-751.
3. Briggs, L.H., Cambie, R.C., 1958. The extractives of Vitex lucens-I. Tetrahedron 3, 269-273.
4. Filler, R., Woods, S.M., White, W.L., 1989. Polyfluoroaralkyl amines. Further studies on the reactivity of 4,5,6,7-tetrafluoroindole. Canadian Journal of Chemistry 67, 1837-1841.
5. Gugel, R.K., Séguin-Swartz, -G., Petrie, A., 1990. Pathogenicity of three isolates of Leptosphaeria maculans on Brassica species and other crucifers. Canadian Journal of Plant Pathology 12, 75-82.
6. Horowitz, R.M., Gentili, B., 1964. Structure of vitexin and isovitexin. Chemistry and Industry 498-499.
7. Kawase, M., Kitamura, T., Kikugawa, Y., 1989. Electrophilic aromatic substitution with N-methoxy-N-acylnitrenium ions generated from N-chloro-N-methoxyamides: syntheses of nitrogen heterocyclic compounds bearing a N-methoxyamide group. Journal of Organic Chemistry 54, 3394-3403.
8. Kikugawa, Y., Kawase, M., 1984. Electrophilic aromatic substitution with a nitrenium ion generated from N-chloro-N-methoxyamides. Application to the synthesis of 1-methoxy-2-oxoindoles. Journal of the American Chemical Society 106, 5728-5729.
9. Nomoto, M., Tamura, S., 1970. Isolation and identification of indole derivatives in clubroots of Chinese cabbage. Agricultural and Biological Chemistry 34, 1590-1592.
10. Pedras, M.S.C., Nycholat, C.M., Montaut, S., Xu, Y., Khan, A.K., 2002. Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry 59, 611-625.
11. Pedras, M.S.C., Okanga, F.I., 1999. Strategies of cruciferous pathogenic fungi: detoxification of the phytoalexin cyclobrassinin by mimicry. Journal of the Agricultural and Food Chemistry 47, 1196-1202.
12. Pedras, M.S.C., Sorensen, J.L., 1998. Phytoalexin accumulation and production of antifungal compounds by the crucifer wasabi. Phytochemistry 49, 1959-1965.
13. Pedras, M.S.C., Sorensen, J.L., Okanga, F.I., Zaharia, I.L., 1999. Wasalexins A and B, new phytoalexins from wasabi: isolation, synthesis, and antifungal activity. Bioorganic & Medicinal Chemistry Letters 9, 3015-3020.
14. Pedras, M.S.C., Okanga, F.I., Zaharia, I.L., Khan, A.K., 2000. Phytoalexins from crucifers: synthesis, biosynthesis, and bio-transformation. Phytochemistry 53, 161-176.
15. Petrie, A., Séguin-Swartz, G., Gugel, R.K., 1995. Latent infection of Brassicaceae in the field by Leptosphaeria maculans (blackleg). Canadian Journal of Plant Pathology 17, 75-81.
16. Ramarathnam, N., Osawa, T., Namiki, M., Kawakishi, S., 1989. Chemical studies on novel rice hull antioxidants. 2. Identification of isovitexin, a C-glycosyl flavonoid. Journal of the Agricultural and Food Chemistry 37, 316-319.
17. Sakan, T., Kusuda, K., Miwa, T., 1964. The base-catalyzed condensation of o-nitroacetophenone. II. The ozonolysis of methyl ether of compound A, a condensation product, and the structure of compound B, another product. Bulletin of the Chemical Society of Japan 37, 1681-1684.
18. Somei, M., Yamada, F., Kurauchi, T., Nagahama, Y., Hasegawa, M., Teranishi, S., Sato, H., Kaneko, C., 2001. The chemistry of Indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N -methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry. Chemical and Pharmaceutical Bulletin 49, 87-96.
19. The Arabidopsis Genome Initiative, 2000. Nature (London) 408, 796-826.
20. Yamada, F., Hashizume, T., Somei, M., 1998. Chemistry of indoles. 83. Simple one step syntheses of indole-3-acetonitriles from indole-3-carboxaldehydes. Heterocycles 47, 509-516.