Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum.
The isolation, structure determination, total synthesis and antifungal activity of erucalexin, a novel phytoalexin produced by the wild crucifer dog mustard are described. Erucalexin is a structurally unique plant alkaloid, representing the first example of a spiro[2H-indole-2,5'(4'H)-thiazol]-3-one, likely derived from a C-3-C-2 carbon migration in a 3-substituted indolyl nucleus.
Pedras
M Soledade C
MS
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan, CanadaS7N 5C9. s.pedras@usask.ca
Suchy
Mojmir
M
Ahiahonu
Pearson W K
PW
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001203:Ascomycota / Q000187:drug effects; D032701:Biomimetics; D019607:Brassicaceae / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000737:chemistry*; D012232:Rhizoctonia / Q000187:drug effects; D012717:Sesquiterpenes; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013729:Terpenes; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D000094162:Phytoalexins
D000935:Antifungal Agents; D007211:Indoles; D010936:Plant Extracts; D012717:Sesquiterpenes; D013141:Spiro Compounds; D013729:Terpenes; D013844:Thiazoles; C511235:erucalexin; D000094162:Phytoalexins