Isolation, identification, and characteristics of the phytotoxin produced by the fungus Alternaria cirsinoxia

Берестецкий, А. О.; Yuzikhin, O. S.; Katkova, A. S.; Добродумов, А. В.; Sivogrivov, D. E.; Kolombet, L. V.

doi:10.1134/s0003683810010138

Cited by 23 publications

(14 citation statements)

References 21 publications

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“…In previous studies, zinniol toxicity was evaluated by direct application of this compound on leaves of different plant species (including carrot) at relatively high concentrations ranging from 150 µM to 1 mM [24] , [26] , [48] . Application of 500 µM zinniol to Tagetes erecta cell suspensions was deleterious for the cultures [28] .…”

Section: Discussionmentioning

confidence: 99%

Partial Resistance of Carrot to Alternaria dauci Correlates with In Vitro Cultured Carrot Cell Resistance to Fungal Exudates

et al. 2014

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Although different mechanisms have been proposed in the recent years, plant pathogen partial resistance is still poorly understood. Components of the chemical warfare, including the production of plant defense compounds and plant resistance to pathogen-produced toxins, are likely to play a role. Toxins are indeed recognized as important determinants of pathogenicity in necrotrophic fungi. Partial resistance based on quantitative resistance loci and linked to a pathogen-produced toxin has never been fully described. We tested this hypothesis using the Alternaria dauci – carrot pathosystem. Alternaria dauci, causing carrot leaf blight, is a necrotrophic fungus known to produce zinniol, a compound described as a non-host selective toxin. Embryogenic cellular cultures from carrot genotypes varying in resistance against A. dauci were confronted with zinniol at different concentrations or to fungal exudates (raw, organic or aqueous extracts). The plant response was analyzed through the measurement of cytoplasmic esterase activity, as a marker of cell viability, and the differentiation of somatic embryos in cellular cultures. A differential response to toxicity was demonstrated between susceptible and partially resistant genotypes, with a good correlation noted between the resistance to the fungus at the whole plant level and resistance at the cellular level to fungal exudates from raw and organic extracts. No toxic reaction of embryogenic cultures was observed after treatment with the aqueous extract or zinniol used at physiological concentration. Moreover, we did not detect zinniol in toxic fungal extracts by UHPLC analysis. These results suggest that strong phytotoxic compounds are present in the organic extract and remain to be characterized. Our results clearly show that carrot tolerance to A. dauci toxins is one component of its partial resistance.

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Section: Discussionmentioning

confidence: 99%

Partial Resistance of Carrot to Alternaria dauci Correlates with In Vitro Cultured Carrot Cell Resistance to Fungal Exudates

et al. 2014

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“…After that, half of them were punctured in the center with a dissecting needle, and 10 μL of test-solution was applied to the central area of each disc. The details of leaf puncture bioassay are given in Berestetskiy et al, 2010 [ 56 ] and Poluektova et al, 2018 [ 35 ]. The diameter of the necrotic lesions was measured 120 h after treatment.…”

Section: Methodsmentioning

confidence: 99%

Effect of Adjuvants on Herbicidal Activity and Selectivity of Three Phytotoxins Produced by the Fungus, Stagonospora cirsii

Dubovik

Dalinova

Berestetskiy

2020

Plants

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The use of many fungal phytotoxins as natural herbicides is still limited because they cannot penetrate leaf cuticle without injury and a little is known on their selectivity. In order to assess the herbicidal potential of phytotoxic 10-membered lactones (stagonolide A, stagonolide K, and herbarumin I), the selection of adjuvants, the evaluation of selectivity of the toxins and the efficacy of their formulations were performed. Among four adjuvants tested, Hasten™ (0.1%, v/v) increased phytotoxic activity of all the toxins assayed on non-punctured leaf discs of Sonchus arvensis. When assayed on intact leaf fragments of 18 plants species, 10 species were low to moderately sensitive to stagonolide A, while just five and three species were sensitive to stagonolide K and herbarumin I, respectively. Both leaf damage or addition of Hasten™ (0.1%) to the formulations of the compounds considerably increased or altered the sensitivity of plants to the toxins. Stagonolide A was shown to be non-selective phytotoxin. The selectivity profile of stagonolide K and herbarumin I depended on the leaf wounding or the adjuvant addition. Stagonolide A and herbarumin I formulated in 0.5% Hasten™ showed considerable herbicidal effect on S. arvensis aerial shoots. This study supported the potential of the oil-based adjuvant Hasten™ to increase the herbicidal efficacy of natural phytotoxins.

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“…Leaf segments of couch-grass (Elytrigia repens) of 2 cm length and leaf discs of perennial sowthistle (Sonchus arvensis) of 1 cm in diameter were punctured with a sharp needle in the center and were treated with solutions of isolated compounds in 5% EtOH at a concentration of 2 mg/mL as described previously [31]. Typically, for this bioassay samples of isolated compounds (400 µg) were dissolved in EtOH (10 µL) ultrasonically, and then, water (190 µL) was added and the samples were vortexed.…”

Section: Phytotoxic Activitymentioning

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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Isolation, identification, and characteristics of the phytotoxin produced by the fungus Alternaria cirsinoxia

Cited by 23 publications

References 21 publications

Partial Resistance of Carrot to Alternaria dauci Correlates with In Vitro Cultured Carrot Cell Resistance to Fungal Exudates

Partial Resistance of Carrot to Alternaria dauci Correlates with In Vitro Cultured Carrot Cell Resistance to Fungal Exudates

Effect of Adjuvants on Herbicidal Activity and Selectivity of Three Phytotoxins Produced by the Fungus, Stagonospora cirsii

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

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