Validation of serine/threonine protein phosphatase as the herbicide target site of endothall

Bajsa, Joanna; Pan, Zhiqiang; Dayan, Franck E.; Owens, Daniel K.; Duke, Stephen O.

doi:10.1016/j.pestbp.2011.10.007

Cited by 38 publications

(47 citation statements)

References 35 publications

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“…1). Similar results were found with endothall, a commercial herbicide that is a close chemical analogue of cantharidin, which also inhibits serine/threonine protein phosphatases (Bajsa et al, 2012). The natural phytotoxin coronatine, an analog of the hormone methyl jasmonic acid (MeJA), influenced 35 % of the genes regulated by MeJA in tomato (Uppalapati et al, 2005).…”

Section: Transcriptomicssupporting

confidence: 71%

Omics Methods for Probing the Mode of Action of Natural and Synthetic Phytotoxins

2013

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For a little over a decade, omics methods (transcriptomics, proteomics, metabolomics, and physionomics) have been used to discover and probe the mode of action of both synthetic and natural phytotoxins. For mode of action discovery, the strategy for each of these approaches is to generate an omics profile for phytotoxins with known molecular targets and to compare this library of responses to the responses of compounds with unknown modes of action. Using more than one omics approach enhances the probability of success. Generally, compounds with the same mode of action generate similar responses with a particular omics method. Stress and detoxification responses to phytotoxins can be much clearer than effects directly related to the target site. Clues to new modes of action must be validated with in vitro enzyme effects or genetic approaches. Thus far, the only new phytotoxin target site discovered with omics approaches (metabolomics and physionomics) is that of cinmethylin and structurally related 5-benzyloxymethyl-1,2-isoxazolines. These omics approaches pointed to tyrosine amino-transferase as the target, which was verified by enzyme assays and genetic methods. In addition to being a useful tool of mode of action discovery, omics methods provide detailed information on genetic and biochemical impacts of phytotoxins. Such information can be useful in understanding the full impact of natural phytotoxins in both agricultural and natural ecosystems.

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Section: Transcriptomicssupporting

confidence: 71%

Omics Methods for Probing the Mode of Action of Natural and Synthetic Phytotoxins

2013

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“…Previous studies by our group demonstrated that both in vivo and in vitro, there are significant inhibitory effects from CTD, NCTD and their analogues on PSPs of Plutella xylostella, suggesting that their modes of action may be related to impeding insect PSPs activity [24]. More recently, strong evidence indicates that the commercial herbicide mode of action of endothall, an analogue of NCTD, was intimately related to the inhibition of PSPs [25].…”

Section: Introductionmentioning

confidence: 94%

Synthesis and Biological Evaluation of Norcantharidin Derivatives Possessing an Aromatic Amine Moiety as Antifungal Agents

et al. 2015

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Based on the structure of naturally produced cantharidin, different arylamine groups were linked to the norcantharidin scaffold to provide thirty six compounds. Their structures were confirmed by melting point, 1 H-NMR, 13 C-NMR and HRMS-ESI studies. These synthetic compounds were tested as fungistatic agents against eight phytopathogenic fungi using the mycelium growth rate method. Of these thirty six derivatives, seven displayed stronger antifungal activity than did norcantharidin, seven showed higher activity than did cantharidin and three exhibited more significant activity than that of thiabendazole. In particular, 3-(3 1 -chloro-phenyl)carbamoyl norcantharidate II-8 showed the most significant fungicidal activity against Sclerotinia fructigena and S. sclerotiorum, with IC 50 values of 0.88 and 0.97 µg/mL, respectively. The preliminary structure-activity relationship data of these compounds revealed that: (1) the benzene ring is critical for the improvement of the spectrum of antifungal activity (3-phenylcarbamoyl norcantharidate II-1 vs norcantharidin and cantharidin); (2) among the three sites, including the C-2 1 , C-3 1 and C-4 1 positions of the phenyl ring, the presence of a halogen atom at the C-3 1 position of the benzene ring caused the most significant increase in antifungal activity; (3) compounds with strongly electron-drawing or electron-donating groups substitutions were found to have a poor antifungal activity; and (4) compared with fluorine, bromine and iodine, chlorine substituted at the C-3 1 position of the benzene ring most greatly promoted fungistatic activity. Thus, compound II-8 has emerged as new lead structure for the development of new fungicides.

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“…Endothall is a commercial herbicide that is structurally similar to cantharidin and also inhibits plant Ser/Thr protein phosphatases. This herbicide is primarily used for aquatic weed control (Netherland et al, 2000;Bajsa et al, 2011a).…”

Section: Ser/thr Protein Phosphatasesmentioning

confidence: 99%

Natural Compounds as Next-Generation Herbicides

2014

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Validation of serine/threonine protein phosphatase as the herbicide target site of endothall

Cited by 38 publications

References 35 publications

Omics Methods for Probing the Mode of Action of Natural and Synthetic Phytotoxins

Omics Methods for Probing the Mode of Action of Natural and Synthetic Phytotoxins

Synthesis and Biological Evaluation of Norcantharidin Derivatives Possessing an Aromatic Amine Moiety as Antifungal Agents

Natural Compounds as Next-Generation Herbicides

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