Ecotoxicological characterisation of a mycoherbicide mixture isolated from the fungus <i>Ascochyta caulina</i>

Fumagalli, P; Andolfi, Anna; Avolio, Fabiana; Boari, Angela; Cimmino, Alessio; Finizio, Antonio

doi:10.1002/ps.3447

Cited by 14 publications

(11 citation statements)

References 23 publications

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“…Many fungi are known to produce very toxic compounds such as mycotoxins constraining the use of some effective but toxigenic mycoherbicidal agents (e.g., based on Fusarium spp.). Moreover, despite a number of registered mycoherbicides and a long list of potential ones [7], the toxicological risks of their application have been evaluated on limited number of fungal species such as Stagonospora convolvuli, Ascochyta caulina, Myrothetium verrucarium [8][9][10]. Recently, among phytotoxic compounds isolated from S. cirsii, a potential bioherbicide for Sonchus arvensis biocontrol, the most potent stagonolide A was considered as a mycotoxin due to a broad spectrum of biological activity [11,12].…”

Section: Introductionmentioning

confidence: 99%

Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

et al. 2020

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The fungus, Alternaria sonchi is considered to be a potential agent for the biocontrol of perennial sowthistle (Sonchus arvensis). A new chlorinated xanthone, methyl 8-hydroxy-3-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (1) and a new benzophenone derivative, 5-chloromoniliphenone (2), were isolated together with eleven structurally related compounds (3–13) from the solid culture of the fungus, which is used for the production of bioherbicidal inoculum of A. sonchi. Their structures were determined by spectroscopic (mostly by NMR and MS) methods. Alternethanoxins A and B, which were reported in A. sonchi earlier, were re-identified as moniliphenone and pinselin, respectively. The isolated compounds were tested for phytotoxic, antimicrobial, insecticidal, cytotoxic and esterase-inhibition activities. They did not demonstrate high phytotoxicity (lesions up to 2.5 mm in diameter/length at a concentration of 2 mg/mL) when tested on leaf disks/segments of perennial sowthistle (Sonchus arvensis) and couch grass (Elytrigia repens). They did not possess acute toxicity to Paramecium caudatum, and showed moderate to low cytotoxicity (IC50 > 25 µg/mL) for U937 and K562 tumor cell lines. However, chloromonilicin and methyl 3,8-dihydroxy-6-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (4) were shown to have antimicrobial properties with MIC 0.5–5 µg/disc. Compound 4 and chloromonilinic acid B were found to have contact insecticidal activity to wheat aphid (Schizaphis graminum) at 1 mg/mL. Compounds 2 and methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate displayed selective carboxylesterase inhibition activity at concentration of 100 µg/mL. Therefore, the waste solid substrate for production of A. sonchi spores can be re-utilized for the isolation of a number of valuable natural products.

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Section: Introductionmentioning

confidence: 99%

Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

et al. 2020

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“…1, Table S1 ESI †), was isolated from the mixture of toxins obtained by a basic eluate of cation exchange chromatography carried out on the fungal culture ltrates. 39 A new phytotoxic enol tautomer of 4-pyridylpyruvic acid, named ascosonchine (4, Fig. Furthermore, the simultaneous application of toxins or fungal spores, together with low doses of synthetic herbicides (metribuzin and rimsulfuron at 1/5 of the labeled rate), gave better results than single-agent treatments.…”

Section: Introductionmentioning

confidence: 99%

Fungal phytotoxins with potential herbicidal activity: chemical and biological characterization

Cimmino¹,

Masi²,

Evidente³

et al. 2015

Nat. Prod. Rep.

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155

149

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Covering: 2007 to 2015 Fungal phytotoxins are secondary metabolites playing an important role in the induction of disease symptoms interfering with host plant physiological processes. Although fungal pathogens represent a heavy constraint for agrarian production and for forest and environmental heritage, they can also represent an ecofriendly alternative to manage weeds. Indeed, the phytotoxins produced by weed pathogenic fungi are an efficient tool to design natural, safe bioherbicides. Their use could avoid that of synthetic pesticides causing resistance in the host plants and the long term impact of residues in agricultural products with a risk to human and animal health. The isolation and structural and biological characterization of phytotoxins produced by pathogenic fungi for weeds, including parasitic plants, are described. Structure activity relationships and mode of action studies for some phytotoxins are also reported to elucidate the herbicide potential of these promising fungal metabolites.

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“…The results obtained in both acute and chronic toxicity tests with Eisenia foetida indicated a very low toxicity of ACTs for terrestrial organisms. In general, the comparison of the ecotoxicological profile of ATCs with other herbicides has shown a lower ecotoxicity for the tested mixture [24].…”

Section: Ecotoxicological Characterization Of a Mycoherbicide A Caulmentioning

confidence: 87%

Fungal Phytotoxins with Potential Herbicidal Activity to Control Chenopodium album

Cimmino

Masi

Evidente

2015

Natural Product Communications

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This review deals with the isolation and chemical and biological characterization of phytotoxins produced by Ascochyta caulina and Phoma chenopodiicola proposed as mycoherbicides for the biological control of Chenopodium album, a worldwide spread weed which causes serious problems to some agrarian crops, including sugar beet and maize. Studies on the structure activity relationships and on the modes of actions of toxins isolated are also described, as well as the optimization of analytical methods focused on selection of the best fungal toxin producers. The attempts to scale up production of these phytotoxins aimed to obtain sufficient amounts for their application in greenhouse and field trials are also reported.

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Ecotoxicological characterisation of a mycoherbicide mixture isolated from the fungus Ascochyta caulina

Cited by 14 publications

References 23 publications

Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

Fungal phytotoxins with potential herbicidal activity: chemical and biological characterization

Fungal Phytotoxins with Potential Herbicidal Activity to Control Chenopodium album

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