Chemical mediators: the remarkable structure and host-selectivity of depsilairdin, a sesquiterpenic depsipeptide containing a new amino acid.
The chemical structure determination of depsilairdin, a highly selective phytotoxin produced by the plant pathogenic fungus Leptosphaeriamaculans/Phoma lingam, is described. The elucidation of the unusual chemical structure used a combination of NMR spectral data and X-ray crystallography. The absolute configuration was established using chemical degradation and synthesis of (3S,6R)-3,6-diisopropyl-2,5-morpholinedione and its (3R,6S) and (3R,6R) stereoisomers. Similar to the fungal pathogen, depsilairdin caused strong lesions only on brown mustard leaves but not on related species. [structure: see text]
Pedras
M Soledade C
MS
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada. s.pedras@usask.ca
Chumala
Paulos B
PB
Quail
J Wilson
JW
D047630:Depsipeptides / Q000737:chemistry* / Q000494:pharmacology; D009149:Mustard Plant / Q000187:drug effects; D009183:Mycotoxins / Q000737:chemistry* / Q000494:pharmacology; D010935:Plant Diseases / Q000209:etiology; D018515:Plant Leaves / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology
D047630:Depsipeptides; D009183:Mycotoxins; D012717:Sesquiterpenes; C507168:depsilairdin