Auxin-like effects of the natural coumarin scopoletin on Arabidopsis cell structure and morphology

Elisa Graña; Aitana Costas-Gil; Sabela Longueira; María Celeiro; Marta Teijeira; Manuel J Reigosa; Adela M Sánchez-Moreiras

doi:10.1016/j.jplph.2017.07.007

Auxin-like effects of the natural coumarin scopoletin on Arabidopsis cell structure and morphology

J Plant Physiol. 2017 Nov:218:45-55. doi: 10.1016/j.jplph.2017.07.007. Epub 2017 Jul 13.

Authors

Elisa Graña¹, Aitana Costas-Gil², Sabela Longueira³, María Celeiro⁴, Marta Teijeira⁵, Manuel J Reigosa⁶, Adela M Sánchez-Moreiras⁷

Affiliations

¹ Department of Plant Biology and Soil Science, Faculty of Biology, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain. Electronic address: eli-grana@uvigo.es.
² Department of Plant Biology and Soil Science, Faculty of Biology, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain. Electronic address: aitanacostasgil@gmail.com.
³ Department of Plant Biology and Soil Science, Faculty of Biology, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain. Electronic address: sabela.92@hotmail.com.
⁴ Department of Organic Chemistry, Faculty of Chemistry, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain. Electronic address: maria_gc8@hotmail.es.
⁵ Department of Organic Chemistry, Faculty of Chemistry, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain; Instituto de Investigación Sanitaria Galicia Sur (IISGS), Universidade de Vigo, 36310 Vigo, Spain. Electronic address: qomaca@uvigo.es.
⁶ Department of Plant Biology and Soil Science, Faculty of Biology, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain. Electronic address: mreigosa@uvigo.es.
⁷ Department of Plant Biology and Soil Science, Faculty of Biology, University of Vigo, Campus Lagoas-Marcosende s/n, 36310 Vigo, Spain. Electronic address: adela@uvigo.es.

PMID: 28772153
DOI: 10.1016/j.jplph.2017.07.007

Abstract

The mode of action and phytotoxic potential of scopoletin, a natural compound belonging to the group of coumarins, has been evaluated in detail. Analysis conducted by light and electron transmission microscopy showed strong cell and tissue abnormalities on treated roots, such as cell wall malformations, multi-nucleated cells, abnormal nuclei and tissue disorganization. Scopoletin compromised root development by inducing wrong microtubule assembling, mitochondrial membrane depolarization and ultimate cell death, in a way similar to auxin herbicides. The structural similarities of the natural compound scopoletin and the auxin herbicide 2,4-D, as well as the ability of scopoletin to fit into the auxin-binding site TIR1, were analyzed, suggesting that the phytotoxic activity of scopoletin matches with that exhibited by auxinic herbicides.

Keywords: Auxinic bioherbicide; Coumarin; Mode of action; Phytotoxicity; Secondary metabolite; TIR1.

MeSH terms

2,4-Dichlorophenoxyacetic Acid / chemistry
Arabidopsis / drug effects*
Arabidopsis / metabolism
Arabidopsis Proteins / genetics
Arabidopsis Proteins / metabolism
F-Box Proteins / genetics
F-Box Proteins / metabolism
Herbicides / chemistry
Indoleacetic Acids / metabolism
Indoleacetic Acids / toxicity*
Microscopy, Electron, Transmission
Plant Cells / drug effects
Plant Cells / metabolism*
Plant Growth Regulators / metabolism
Plant Growth Regulators / toxicity*
Receptors, Cell Surface / genetics
Receptors, Cell Surface / metabolism
Scopoletin / metabolism
Scopoletin / toxicity*

Substances

Arabidopsis Proteins
F-Box Proteins
Herbicides
Indoleacetic Acids
Plant Growth Regulators
Receptors, Cell Surface
TIR1 protein, Arabidopsis
2,4-Dichlorophenoxyacetic Acid
Scopoletin