Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean
Abstract
The estrogenic isoflavones of soybeans and their glycosides are products of the shikimate pathway, the target pathway of glyphosate. This study tested the hypothesis that nonphytotoxic levels of glyphosate and other herbicides known to affect phenolic compound biosynthesis might influence levels of these nutraceutical compounds in glyphosate-resistant soybeans. The effects of glyphosate and other herbicides were determined on estrogenic isoflavones and shikimate in glyphosate-resistant soybeans from identical experiments conducted on different cultivars in Mississippi and Missouri. Four commonly used herbicide treatments were compared to a hand-weeded control. The herbicide treatments were (1) glyphosate at 1260 g/ha at 3 weeks after planting (WAP), followed by glyphosate at 840 g/ha at 6 WAP; (2) sulfentrazone at 168 g/ha plus chlorimuron at 34 g/ha applied preemergence (PRE), followed by glyphosate at 1260 g/ha at 6 WAP; (3) sulfentrazone at 168 g/ha plus chlorimuron at 34 g/ha applied PRE, followed by glyphosate at 1260 g/ha at full bloom; and (4) sulfentrazone at 168 g/ha plus chlorimuron at 34 g/ha applied PRE, followed by acifluorfen at 280 g/ha plus bentazon at 560 g/ha plus clethodim at 140 g/ha at 6 WAP. Soybeans were harvested at maturity, and seeds were analyzed for daidzein, daidzin, genistein, genistin, glycitin, glycitein, shikimate, glyphosate, and the glyphosate degradation product, aminomethylphosphonic acid (AMPA). There were no remarkable effects of any treatment on the contents of any of the biosynthetic compounds in soybean seed from either test site, indicating that early and later season applications of glyphosate have no effects on phytoestrogen levels in glyphosate-resistant soybeans. Glyphosate and AMPA residues were higher in seeds from treatment 3 than from the other two treatments in which glyphosate was used earlier. Intermediate levels were found in treatments 1 and 2. Low levels of glyphosate and AMPA were found in treatment 4 and a hand-weeded control, apparently due to herbicide drift.
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The EPSPS enzyme drives the first step of aromatic amino acid biosynthesis in the plant shikimate pathway.
“This enzyme is known to drive the first step of aromatic amino acid biosynthesis in the plant shikimate pathway; in addition estrogenic isoflavones and their glycosides are also products of this pathway (Duke et al., 2003).”
From RETRACTED: Long term toxicity of a Roundup herbicide and a Roundup-tolerant genetically modified maize (2012) · cites this paper as Duke et al., 2003
Estrogenic isoflavones and their glycosides are products of the plant shikimate pathway.
“This enzyme is known to drive the first step of aromatic amino acid biosynthesis in the plant shikimate pathway; in addition estrogenic isoflavones and their glycosides are also products of this pathway (Duke et al., 2003).”
From RETRACTED: Long term toxicity of a Roundup herbicide and a Roundup-tolerant genetically modified maize (2012) · cites this paper as Duke et al., 2003
Estrogenic isoflavones and their glycosides are also products of the plant shikimate pathway.
“In addition, estrogenic isoflavones and their glycosides are also products of this pathway [68].”
From Republished study: long-term toxicity of a Roundup herbicide and a Roundup-tolerantgenetically modified maize (2014) · cites this paper as [68]
Cites
Principles and Procedures of Statistics: A Biometrical Approach
Steel, R. G. D., & Torrie, J. H. (1980) · Andalas University Repository (Andalas University) · Cited by 15,510 · see citing works
Herbicides: Chemistry, Degradation, and Mode of Action
Kearney, P. C., & Kaufman, D. D. (1976) · Cited by 597 · see citing works
Dietary estrogens—A probable cause of infertility and liver disease in captive cheetahs
Setchell, K. D. R., Gosselin, S. J., Welsh, M. B., Johnston, J. O., Balistreri, W. F., Kramer, L., Dresser, B. L., & Tarr, M. J. (1987) · Gastroenterology · doi:10.1016/0016-5085(87)91006-7 · Cited by 353 · see citing works
The Composition of Glyphosate-Tolerant Soybean Seeds Is Equivalent to that of Conventional Soybeans
Padgette, S. R., Taylor, N. B., Nida, D. L., Bailey, M. R., MacDonald, J., Holden, L. R., & Fuchs, R. L. (1996) · Journal of Nutrition · doi:10.1093/jn/126.3.702 · Cited by 278 · see citing works
Zhou, Y., & Lee, A. S. (1998) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/90.5.381 · Cited by 144 · see citing works
Pline, W. A., Wilcut, J. W., Duke, S. O., et al. (2001) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0110699 · Cited by 142 · see citing works
Self-citationGlyphosate induction of elevated levels of hydroxybenzoic acids in higher plants
Lydon, J., & Duke, S. O. (1988) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00082a036 · Cited by 119 · see citing works
Self-citationReddy, K. N., Hoagland, R. E., & Zablotowicz, R. M. (2000) · Journal of New Seeds · doi:10.1300/j153v02n03_03 · Cited by 110 · see citing works
Self-citationCompositional Analysis of Glyphosate-Tolerant Soybeans Treated with Glyphosate
Taylor, N. B., Fuchs, R. L., MacDonald, J., Shariff, A. R., & Padgette, S. R. (1999) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf990056g · Cited by 108 · see citing works
Hoagland, R. E. (1980) · Weed Science · doi:10.1017/s0043174500055545 · Cited by 101 · see citing works
Pline, W. A., Wu, J., & Hatzios, K. K. (1999) · Pesticide Biochemistry and Physiology · doi:10.1006/pest.1999.2437 · Cited by 87 · see citing works
Accumulation of Shikimic Acid: A Technique for Screening Glyphosate Efficacy
Harring, T., Streibig, J. C., & Husted, S. (1998) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf9802124 · Cited by 84 · see citing works
Potter, S. M. (1996) · Current Opinion in Lipidology · doi:10.1097/00041433-199608000-00013 · Cited by 79 · see citing works
Plant metabolism of herbicides with CP bonds: Glyphosate
Komoßa, D., Gennity, I., & Sandermann, H. (1992) · Pesticide Biochemistry and Physiology · doi:10.1016/0048-3575(92)90022-r · Cited by 72 · see citing works
Lappé, M., Bailey, E., Childress, C., et al. (1998) · Journal of Medicinal Food · doi:10.1089/jmf.1998.1.241 · Cited by 71 · see citing works
Kneer, R., Poulev, A., OLESINSKI, A. A., et al. (1999) · Journal of Experimental Botany · doi:10.1093/jxb/50.339.1553 · Cited by 70 · see citing works
Glyphosate‐resistant soybean as a weed management tool: Opportunities and challenges
Reddy, K. N. (2001) · Weed Biology and Management · doi:10.1046/j.1445-6664.2001.00032.x · Cited by 66 · see citing works
Self-citationHolliday, M. J. (1982) · Phytopathology · doi:10.1094/phyto-72-1470 · Cited by 56 · see citing works
Acifluorfen increases the leaf content of phytoalexins and stress metabolites in several crops
Kőmíves, T., & Casida, J. E. (1983) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00118a018 · Cited by 55 · see citing works
Cessna, A. J., Darwent, A. L., Townley-Smith, L., et al. (2002) · Canadian Journal of Plant Science · doi:10.4141/p01-094 · Cited by 41 · see citing works
Cessna, A. J., Darwent, A. L., Kirkland, K. J., et al. (1994) · Canadian Journal of Plant Science · doi:10.4141/cjps94-117 · Cited by 38 · see citing works
Isoflavone content of soya-based laboratory animal diets
MURPHY, P., Farmakalidis, E., & Johnson, L. D. (1982) · Food and Chemical Toxicology · doi:10.1016/s0278-6915(82)80299-8 · Cited by 36 · see citing works
Alferness, P. L., WIEBE, L. A., Collaborators:, et al. (2001) · Journal of AOAC International · doi:10.1093/jaoac/84.3.823 · Cited by 31 · see citing works
Genetic Engineering Crops for Improved Weed Management Traits
Duke, S. O., Scheffler, B. E., Dayan, F. E., et al. (2002) · ACS symposium series · doi:10.1021/bk-2002-0829.ch006 · Cited by 28 · see citing works
Self-citationResidues of glyphosate and its metabolite AMPA in canola seed following preharvest applications
Cessna, A. J., Darwent, A. L., Townley-Smith, L., et al. (2000) · Canadian Journal of Plant Science · doi:10.4141/p99-062 · Cited by 27 · see citing works
Suttle, J. C., & Schreiner, D. R. (1982) · Canadian Journal of Botany · doi:10.1139/b82-097 · Cited by 23 · see citing works
Boer, S. H. D. (1982) · Phytopathology · doi:10.1094/phyto-72-1474 · Cited by 23 · see citing works
Hoagland, R. E., & Duke, S. O. (1981) · Weed Science · doi:10.1017/s0043174500039953 · Cited by 18 · see citing works
Self-citationHoagland, R. E., & Duke, S. O. (1983) · Weed Science · doi:10.1017/s0043174500070855 · Cited by 18 · see citing works
Self-citationTransgenic crops: a view from the US Extension Service
Baldwin, F. L. (2000) · Pest Management Science · doi:10.1002/1526-4998(200007)56:7 · Cited by 12 · see citing works
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RetractedSéralini, G.-E., Clair, E., Mesnage, R., Gress, S., Defarge, N., Malatesta, M., Hennequin, D., & de Vendômois, J. S. (2014) · Environmental Sciences Europe · doi:10.1186/s12302-014-0014-5 · Cited by 299 · see citing works
Unintended compositional changes in genetically modified (GM) crops: 20 years of research
Herman, R. A., & Price, W. D. (2013) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf400135r · Cited by 156 · see citing works
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Cuhra, M., Bøhn, T., & Cuhra, P. (2016) · Frontiers in Environmental Science · doi:10.3389/fenvs.2016.00028 · Cited by 106 · see citing works
Cuhra, M. (2015) · Environmental Sciences Europe · doi:10.1186/s12302-015-0052-7 · Cited by 77 · see citing works
- Authors
- Duke, S. O., Rimando, A. M., Pace, P. F., Reddy, K. N., & Smeda, R. J.
- Affiliations
- Agricultural Research Service (US)
- Corresponding author
- Duke, Stephen O.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-12-05
- Volume
- 51
- Issue
- 1
- Pages
- 340-344
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2110460506
- Cited by
- 195
- References
- 30
- Citations by year
- 2026: 5 · 2025: 4 · 2024: 2 · 2023: 2 · 2022: 6 · 2021: 10 · 2020: 8 · 2019: 8 · 2018: 2 · 2017: 12 · 2016: 11 · 2015: 19 · 2014: 19 · 2013: 10 · 2012: 12
- FWCI
- 4.22
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Agricultural and Food Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Weed Control and Herbicide Applications
- Health Sciences › Medicine › Pathology and Forensic Medicine › Phytoestrogen effects and research
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Genetically Modified Organisms Research
- Keywords
- glyphosate-resistant soybean, glyphosate, aminomethylphosphonic acid, isoflavones, phytoestrogens, shikimate pathway, herbicide residues, sulfentrazone, chlorimuron, acifluorfen, clethodim, daidzein, genistein, seed nutrient content, herbicide application timing, hand weeding
- MeSH terms
- Glyphosate, Drug Resistance, Glycine, Herbicides, Isoflavones, Isoxazoles, Seeds, Shikimic Acid, Glycine max, Tetrazoles, Genistein, Organophosphonates
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