4-Formylaminooxyvinylglycine, an herbicidal germination-arrest factor from Pseudomonas rhizosphere bacteria.
A new oxyvinylglycine has been identified as a naturally occurring herbicide that irreversibly arrests germination of the seeds of grassy weeds, such as annual bluegrass (Poa annua), without significantly affecting the growth of established grass seedlings and mature plants or germination of the seeds of broadleaf plant species (dicots). Previously, Pseudomonas fluorescens WH6 and over 20 other rhizosphere bacteria were isolated and selected for their ability to arrest germination of P. annua seeds. The germination-arrest factor (GAF, 1) responsible for this developmentally specific herbicidal action has now been isolated from the culture filtrate of P. fluorescens WH6. Purification of this highly polar, low molecular weight natural product allowed its structure to be assigned as 4-formylaminooxy-l-vinylglycine on the basis of NMR spectroscopic and mass spectrometric data, in combination with D/L-amino acid oxidase reactions to establish the absolute configuration. Assay results for P. annua inhibition by related compounds known to regulate plant growth are presented, and a cellular target for 1 is proposed. Furthermore, using bioassays, TLC, and capillary NMR spectroscopy, it has been shown that GAF (1) is secreted by all other herbicidally active rhizosphere bacteria in our collection.
McPhail
Kerry L
KL
College of Pharmacy, 203 Pharmacy Building, Oregon State University, Corvallis, Oregon 97331, United States. kerry.mcphail@oregonstate.edu
Armstrong
Donald J
DJ
Azevedo
Mark D
MD
Banowetz
Gary M
GM
Mills
Dallice I
DI
D018525:Germination / Q000187:drug effects*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006540:Herbicides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D057685:Plant Weeds / Q000187:drug effects; D031785:Poa / Q000187:drug effects*; D011549:Pseudomonas / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry
C554266:4-formylaminooxyvinylglycine; D006540:Herbicides; D005998:Glycine