The macrocidins: novel cyclic tetramic acids with herbicidal activity produced by Phoma macrostoma.
Field isolates of Phoma macrostoma were obtained from diseased Canada thistle growing in several geographically diverse regions. Bleaching and chlorotic symptoms were present on the infected plants. The isolates grown in liquid culture were found to produce phytotoxic metabolites which also caused bleaching when applied foliarly to several broadleaf species. Bioassay-directed isolation led to the discovery of macrocidins A and B, the first representatives of a new family of cyclic tetramic acids. This new chemotype may offer significant potential as a template for herbicide design.
Graupner
Paul R
PR
Natural Products Discovery, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, USA. pgraupner@dow.com
Carr
Andy
A
Clancy
Erin
E
Gilbert
Jeffrey
J
Bailey
Karen L
KL
Derby
Jo-Anne
JA
Gerwick
B Clifford
BC
D002170:Canada; D031180:Cirsium / Q000187:drug effects; D006540:Herbicides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D003904:Mitosporic Fungi / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010572:Pest Control, Biological; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000097566:Cyclophanes
D006540:Herbicides; D009183:Mycotoxins; D011760:Pyrrolidinones; C482758:macrocidin A; D000097566:Cyclophanes; C482759:macrocidin B; C009435:tetramic acid