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Peer-reviewedCC BYJournal of Agricultural and Food Chemistry

Catalytic Promiscuity Underpins Metabolic Resistance to Auxinic Herbicides in Echinochloa phyllopogon

  • Pattarasuda Chayapakdee1,2
  • Kowit Hengphasatporn3,4
  • Takuya Yamaguchi5,6
  • Danrui Su7,8
  • Niña Gracel Dimaano9,10
  • Yasuteru Shigeta3,4
  • Yukari Sunohara11,4
  • Hiroshi Matsumoto11,4
  • Satoshi Iwakami12,7,8
12 affiliations
  1. 1Center of Excellence in Microbial Diversity and Sustainable Utilization, Agrobiodiversity in Highland and Sustainable Utilization Research Group, and Department of Biology, Faculty of Science
  2. 2Chiang Mai University
  3. 3Center for Computational Sciences
  4. 4University of Tsukuba
  5. 5Biotechnology Research Center and Department of Biotechnology
  6. 6Toyama Prefectural University
  7. 7Tokyo University of Agriculture and Technology
  8. 8United Graduate School of Agricultural Science
  9. 9Institute of Weed Science, Entomology and Plant Pathology, College of Agriculture and Food Science
  10. 10University of the Philippines Los Baños
  11. 11Graduate School of Life and Environmental Sciences
  12. 12Institute of Agriculture
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Abstract

Auxinic herbicides are critically important tools for weed control in modern agriculture. Although resistant weed populations have been increasing in recent years, the underlying mechanisms remain largely unknown. In a multiple-herbicide resistant line of the paddy weed Echinochloa phyllopogon , overexpression of catalytically promiscuous CYP81A P450 enzymes has been shown to confer resistance to diverse herbicides. Here, we investigated the role of these P450s in quinclorac resistance in E. phyllopogon . Arabidopsis thaliana plants expressing CYP81A12 and CYP81A21 genes, previously demonstrated to metabolize other herbicides, showed low but detectable levels of quinclorac resistance. A similar activity was also observed for CYP81A24, another promiscuous enzyme present in E. phyllopogon . Moreover, Escherichia coli strains expressing these genes produced putative hydroxylated metabolites of quinclorac. In silico analyses revealed that quinclorac binds stably near the catalytic heme center of CYP81A12, CYP81A21, and CYP81A24, but not CYP81A18, the importance of spatial alignment between the substrate recognition site and the heme center in determining metabolic activity and resistance potential. Consistent with the phenotype of resistant E. phyllopogon , A. thaliana expressing CYP81A12 and CYP81A21 produced significantly less ethylene following quinclorac treatment, linking P450-mediated metabolism to the suppression of quinclorac-induced phytotoxic responses. Finally, we demonstrated that CYP81A enzymes also confer resistance to other auxinic herbicides, florpyrauxifen-benzyl and 2,4-D. These findings provide new insights into the molecular basis of auxinic herbicide resistance and underscore the role of CYP81A P450s in metabolic detoxification and the prevention of herbicide-induced phytotoxic responses.

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Cite

BibTeXRIS
BibTeX
@article{chayapakdee2026catalytic,
  title = {{Catalytic Promiscuity Underpins Metabolic Resistance to Auxinic Herbicides in Echinochloa phyllopogon}},
  author = {Pattarasuda Chayapakdee and Kowit Hengphasatporn and Takuya Yamaguchi and Danrui Su and Niña Gracel Dimaano and Yasuteru Shigeta and Yukari Sunohara and Hiroshi Matsumoto and Satoshi Iwakami},
  journal = {Journal of Agricultural and Food Chemistry},
  year = {2026},
  month = jun,
  doi = {10.1021/acs.jafc.6c02002},
  url = {https://doi.org/10.1021/acs.jafc.6c02002},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Catalytic Promiscuity Underpins Metabolic Resistance to Auxinic Herbicides in Echinochloa phyllopogon
AU  - Pattarasuda Chayapakdee
AU  - Kowit Hengphasatporn
AU  - Takuya Yamaguchi
AU  - Danrui Su
AU  - Niña Gracel Dimaano
AU  - Yasuteru Shigeta
AU  - Yukari Sunohara
AU  - Hiroshi Matsumoto
AU  - Satoshi Iwakami
PY  - 2026
DA  - 2026/06/16
JO  - Journal of Agricultural and Food Chemistry
DO  - 10.1021/acs.jafc.6c02002
UR  - https://doi.org/10.1021/acs.jafc.6c02002
AB  - Auxinic herbicides are critically important tools for weed control in modern agriculture. Although resistant weed populations have been increasing in recent years, the underlying mechanisms remain largely unknown. In a multiple-herbicide resistant line of the paddy weed Echinochloa phyllopogon , overexpression of catalytically promiscuous CYP81A P450 enzymes has been shown to confer resistance to diverse herbicides. Here, we investigated the role of these P450s in quinclorac resistance in E. phyllopogon . Arabidopsis thaliana plants expressing CYP81A12 and CYP81A21 genes, previously demonstrated to metabolize other herbicides, showed low but detectable levels of quinclorac resistance. A similar activity was also observed for CYP81A24, another promiscuous enzyme present in E. phyllopogon . Moreover, Escherichia coli strains expressing these genes produced putative hydroxylated metabolites of quinclorac. In silico analyses revealed that quinclorac binds stably near the catalytic heme center of CYP81A12, CYP81A21, and CYP81A24, but not CYP81A18, the importance of spatial alignment between the substrate recognition site and the heme center in determining metabolic activity and resistance potential. Consistent with the phenotype of resistant E. phyllopogon , A. thaliana expressing CYP81A12 and CYP81A21 produced significantly less ethylene following quinclorac treatment, linking P450-mediated metabolism to the suppression of quinclorac-induced phytotoxic responses. Finally, we demonstrated that CYP81A enzymes also confer resistance to other auxinic herbicides, florpyrauxifen-benzyl and 2,4-D. These findings provide new insights into the molecular basis of auxinic herbicide resistance and underscore the role of CYP81A P450s in metabolic detoxification and the prevention of herbicide-induced phytotoxic responses.
SN  - 0021-8561
SN  - 1520-5118
ER  -