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231225s2021 xx |||||o 00| ||eng c |
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|a 10.1111/nph.17708
|2 doi
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|a pubmed24n1100.xml
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|a (NLM)34480751
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|a DE-627
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|c DE-627
|e rakwb
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|a eng
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|a Concepcion, Jeanaflor Crystal T
|e verfasserin
|4 aut
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|a Resistance to a nonselective 4-hydroxyphenylpyruvate dioxygenase-inhibiting herbicide via novel reduction-dehydration-glutathione conjugation in Amaranthus tuberculatus
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|c 2021
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
|b c
|2 rdamedia
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|a ƒa Online-Ressource
|b cr
|2 rdacarrier
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|a Date Completed 06.01.2022
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|a Date Revised 31.07.2022
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a © 2021 The Authors. New Phytologist © 2021 New Phytologist Foundation.
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|a Metabolic resistance to 4-hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicides is a threat in controlling waterhemp (Amaranthus tuberculatus) in the USA. We investigated resistance mechanisms to syncarpic acid-3 (SA3), a nonselective, noncommercial HPPD-inhibiting herbicide metabolically robust to Phase I oxidation, in multiple-herbicide-resistant (MHR) waterhemp populations (SIR and NEB) and HPPD inhibitor-sensitive populations (ACR and SEN). Dose-response experiments with SA3 provided ED50 -based resistant : sensitive ratios of at least 18-fold. Metabolism experiments quantifying parent SA3 remaining in excised leaves during a time course indicated MHR populations displayed faster rates of SA3 metabolism compared to HPPD inhibitor-sensitive populations. SA3 metabolites were identified via LC-MS-based untargeted metabolomics in whole plants. A Phase I metabolite, likely generated by cytochrome P450-mediated alkyl hydroxylation, was detected but was not associated with resistance. A Phase I metabolite consistent with ketone reduction followed by water elimination was detected, creating a putative α,β-unsaturated carbonyl resembling a Michael acceptor site. A Phase II glutathione-SA3 conjugate was associated with resistance. Our results revealed a novel reduction-dehydration-GSH conjugation detoxification mechanism. SA3 metabolism in MHR waterhemp is thus atypical compared to commercial HPPD-inhibiting herbicides. This previously uncharacterized detoxification mechanism presents a unique opportunity for future biorational design by blocking known sites of herbicide metabolism in weeds
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a 4-HPPD inhibitor
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|a cytochrome P450
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|a detoxification
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|a glutathione conjugation
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|a syncarpic acid
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|a triketones
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|a untargeted metabolomics
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|a waterhemp
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|a Herbicides
|2 NLM
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|a Dioxygenases
|2 NLM
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| 650 |
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|a EC 1.13.11.-
|2 NLM
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|a 4-Hydroxyphenylpyruvate Dioxygenase
|2 NLM
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| 650 |
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|a EC 1.13.11.27
|2 NLM
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| 650 |
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|a Glutathione
|2 NLM
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| 650 |
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|a GAN16C9B8O
|2 NLM
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| 700 |
1 |
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|a Kaundun, Shiv S
|e verfasserin
|4 aut
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| 700 |
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|a Morris, James A
|e verfasserin
|4 aut
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| 700 |
1 |
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|a Hutchings, Sarah-Jane
|e verfasserin
|4 aut
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| 700 |
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|a Strom, Seth A
|e verfasserin
|4 aut
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| 700 |
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|a Lygin, Anatoli V
|e verfasserin
|4 aut
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| 700 |
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|a Riechers, Dean E
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t The New phytologist
|d 1979
|g 232(2021), 5 vom: 04. Dez., Seite 2089-2105
|w (DE-627)NLM09818248X
|x 1469-8137
|7 nnns
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| 773 |
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|g volume:232
|g year:2021
|g number:5
|g day:04
|g month:12
|g pages:2089-2105
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|u http://dx.doi.org/10.1111/nph.17708
|3 Volltext
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|d 232
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|h 2089-2105
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