TY - JOUR
T1 - Observation and identification of 2-C-methyl-d-erythritol-2,4-cyclopyrophosphate in horseweed and ryegrass treated with glyphosate
AU - Ge, Xia
AU - D'Avignon, D. André
AU - Ackerman, Joseph J.H.
AU - Sammons, R. Douglas
N1 - Funding Information:
The authors gratefully acknowledge support of this work by Monsanto Company and the assistance of Dr. Jeff Kao of the Washington University NMR Facility.
PY - 2012/11
Y1 - 2012/11
N2 - Glyphosate is the world's most important and widely used herbicide with a global market forecast to exceed a million metric tons before end of the current decade. While using 31P NMR in vivo to determine the fate of glyphosate in horseweed (Conyza canadensis (L.) Cronquist), we observed the glyphosate-induced appearance of an unexpected phosphorous containing compound that, in some cases, presented at millimolar concentrations [X. Ge, D.A. d'Avignon, J.J.H. Ackerman, R.D. Sammons, Rapid vacuolar sequestration: the horseweed glyphosate resistance mechanism, Pest Manag. Sci. 66 (2010) 345-348.]. Additional studies showed appearance of the same compound could be induced in ryegrass (Lolium multiflorum Lam) and other plant species by glyphosate exposure. We have isolated and identified the phosphorous containing compound as 2-C-methyl-d-erythritol-2,4-cyclopyrophosphate (MEcPP), one of the intermediates of the methylerythritol 4-phosphate (MEP) pathway, which is critical in plants for the production of isoprenoids. Herein, we describe conditions under which MEcPP can be produced in plants as well as the isolation and characterization of this metabolite.
AB - Glyphosate is the world's most important and widely used herbicide with a global market forecast to exceed a million metric tons before end of the current decade. While using 31P NMR in vivo to determine the fate of glyphosate in horseweed (Conyza canadensis (L.) Cronquist), we observed the glyphosate-induced appearance of an unexpected phosphorous containing compound that, in some cases, presented at millimolar concentrations [X. Ge, D.A. d'Avignon, J.J.H. Ackerman, R.D. Sammons, Rapid vacuolar sequestration: the horseweed glyphosate resistance mechanism, Pest Manag. Sci. 66 (2010) 345-348.]. Additional studies showed appearance of the same compound could be induced in ryegrass (Lolium multiflorum Lam) and other plant species by glyphosate exposure. We have isolated and identified the phosphorous containing compound as 2-C-methyl-d-erythritol-2,4-cyclopyrophosphate (MEcPP), one of the intermediates of the methylerythritol 4-phosphate (MEP) pathway, which is critical in plants for the production of isoprenoids. Herein, we describe conditions under which MEcPP can be produced in plants as well as the isolation and characterization of this metabolite.
KW - Conyza canadensis
KW - Glyphosate
KW - In vivo P NMR
KW - Lolium spp
KW - MEP pathway
KW - Metabolic flux
UR - http://www.scopus.com/inward/record.url?scp=84870298779&partnerID=8YFLogxK
U2 - 10.1016/j.pestbp.2012.07.009
DO - 10.1016/j.pestbp.2012.07.009
M3 - Article
AN - SCOPUS:84870298779
SN - 0048-3575
VL - 104
SP - 187
EP - 191
JO - Pesticide Biochemistry and Physiology
JF - Pesticide Biochemistry and Physiology
IS - 3
ER -