ArticlePlant physiology2008
A pathogenic fungi diphenyl ether phytotoxin targets plant enoyl (acyl carrier protein) reductase.
Article in Plant physiology, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 48 citations in OpenAlex.
- The natural herbicide rhein targets photosystem I.Scientific reports · 2024Article
- Proving the Mode of Action of Phytotoxic Phytochemicals.Plants (Basel, Switzerland) · 2020Review
- Isolation, identification and characterization of Streptomyces metabolites as a potential bioherbicide.PloS one · 2019Article
- Sensitivities of seven algal species to triclosan, fluoxetine and their mixtures.Scientific reports · 2018Article
- Proteomic Analysis Reveals the Positive Roles of the Plant-Growth-Promoting Rhizobacterium NSY50 in the Response of Cucumber Roots to FusariumFrontiers in plant science · 2016Article
- Deficient plastidic fatty acid synthesis triggers cell death by modulating mitochondrial reactive oxygen species.Cell research · 2015Article
- Using modern tools to probe the structure-function relationship of fatty acid synthases.Chembiochem : a European journal of chemical biology · 2015Review
- Triclosan Computational Conformational Chemistry Analysis for Antimicrobial Properties in Polymers.Journal of nature and science · 2015Article
- Sarmentine, a natural herbicide from Piper species with multiple herbicide mechanisms of action.Frontiers in plant science · 2015Article
- Sunflower (Helianthus annuus) fatty acid synthase complex: enoyl-[acyl carrier protein]-reductase genes.Planta · 2015Article
- Natural compounds as next-generation herbicides.Plant physiology · 2014Review
- Computational conformational antimicrobial analysis developing mechanomolecular theory for polymer biomaterials in materials science and engineering.International journal of computational materials science and engineering · 2014Article
- Investigation of the Fusarium virguliforme fvtox1 mutants revealed that the FvTox1 toxin is involved in foliar sudden death syndrome development in soybean.Current genetics · 2013Article
- Modes of action of microbially-produced phytotoxins.Toxins · 2011Review
- Gliotoxin in Aspergillus fumigatus: an example that mycotoxins are potential virulence factors.Mycotoxin research · 2009Article
- Triclosan antimicrobial polymers.AIMS molecular scienceArticle
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cyperin is a natural diphenyl ether phytotoxin produced by several fungal plant pathogens. At high concentrations, this metabolite inhibits protoporphyrinogen oxidase, a key enzyme in porphyrin synthesis. However, unlike its herbicide structural analogs, the mode of action of cyperin is not light dependent, causing loss of membrane integrity in the dark. We report that this natural diphenyl ether inhibits Arabidopsis (Arabidopsis thaliana) enoyl (acyl carrier protein) reductase (ENR). This enzyme is also sensitive to triclosan, a synthetic antimicrobial diphenyl ether. Whereas cyperin was much less potent than triclosan on this target site, their ability to cause light-independent disruption of membrane integrity and inhibition of ENR is similar at their respective phytotoxic concentrations. The sequence of ENR is highly conserved within higher plants and a homology model of Arabidopsis ENR was derived from the crystal structure of the protein from Brassica napus. Cyperin mimicked the binding of triclosan in the binding pocket of ENR. Both molecules were stabilized by the pi-pi stacking interaction between one of their phenyl rings and the nicotinamide ring of the NAD(+). Furthermore, the side chain of tyrosine is involved in hydrogen bonding with a phenolic hydroxy group of cyperin. Therefore, cyperin may contribute to the virulence of the pathogens by inhibiting ENR and destabilizing the membrane integrity of the cells surrounding the point of infection.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.