Structure of phaseolinone, a novel phytotoxin from

Dhar, Tarun K.; Siddiqui, K. A. I.; Ali, Esahak

doi:10.1016/0040-4039(82)80157-3

Cited by 20 publications

(18 citation statements)

References 3 publications

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“…The resistance mechanism to phaseolinone toxicity at cellular level merits further investigation. Because phaseolinone contains an epoxide group in its structure (Dhar et al, 1982), its phytotoxic activity may be similar to known biological activity of other epoxide-containing compounds which involves cell growth inhibition by nonspecific alkylation of nucleophiles such as protein, DNA and RNA (Jerina and Daly, 1974). If detoxification of epoxide-containing compounds is the basis of host resistance, the enzyme epoxide hydratase may play an important role in the detoxification process (Walton and Earle, 1983).…”

Section: Discussionmentioning

confidence: 99%

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Differential Responses of Guayule (Parthenium argentatum Gray) Genotypes to Culture Filtrate and Toxin from Macrophomina phaseolina (Tassi) Goidanich

Kuti

Schading²,

Latigo

et al. 1997

Journal of Phytopathology

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The potential for using cell-free culture filtrate (CFCF) and toxin (phaseolinone) from Macrophomina phaseolina for rapid and efTective screening procedures for charcoal rot resistance in guayule (Parthenium argentatum) germplasm was assessed. The CFCF and partially purified phaseolinone were incorporated into modified Murashige and Skoog solid medium at the rates of 0-100% (v/v) and 0-1000^g ml"', respectively. The medium pH was adjusted to 5.8 before solidifying with 0.8% agar. Fourweek-old seedlings of 10 guayule genotypes were planted in the medium, incubated and rated for phytotoxic symptoms and tissue damage over a 15-day period. In a greenhouse study, seedling growth, phytotoxicity and damage severity were compared in 12-week-o!d guayule seedlings root-inoculated with M. phaseolina microsderotia. There were significant differences (P = 0.05) in genotypic responses to the fungus, the filtrate and the toxin inoculations. Time until phytotoxic symptoms developed was inversely related to the concentrations of CFCF and the toxin. Phytotoxic symptoms were produced 6 days after exposure to 50% CFCF and 48 h after exposure to 1000/jg ml"' of partially purified phaseolinone. A comparison of photomicrographs of the control and toxintreated root tissues revealed no damage to the control roots and extensive damage to epidermal layers of the treated roots, which was evident 48 h after exposure to lOO^g ml"' level of phaseolinone. Significant correlations were found between tolerance to the fungus and insensitivity to the culture filtrate (r = 0.89, P = 0.05) and the toxin (r = 0.95, P = 0.001) suggesting the possibility of screening for resistance to M. phaseolina using CFCF or phaseolinone. The genotypic reactions to the CFCF were also correlated with reactions to the toxin {r = 0.90, P = 0.05). Guayule breeding lines 'UCIOT and 'P3-r exhibited the greatest tolerance to the pathogen and insensitivity to the CFCF or the toxin whereas 'Cal6', 'Cal7', 'N576', 'N9-5', M1605' and 'N6-5' were very susceptible to the pathogen and sensitive to the CFCF or the toxin. Zusammenfassung Unterscbiedliche Reaktionen von Guayole-Genotypen {Par-themum argentatum Gray) gegenuber dem Kulturflltrat and dem Toxin von Macrophomina pkaseolina (Tassi) GoidanichUntersucht wurde die mogliche Anwendung von zellfreiem Kulturfiltrat (CFCF) und dem Toxin (Phaseolinon) von Macrophomina phaseolina in einem schnellen und zuverlassigen Verfahren bei der Resistenzprtlfung in Guayule {Parthenium argentatum). Das CFCF und das teilgereinigte Phaseolinon wurden dem modifizierten Murashige und Skoog-Agarmedium in den Konzentrationen 0 bis 100% (v/v) bzw. 0 bis 1000 /ig/ml beigemischt. Der pH-Wert des Mediums wurde bei 5,8 eingestellt und anschlieBend mit 0,8% Agar versehen. Vier Wochen alte Samlinge von 10 Guayule-Genotypen wurden in diesen Medien gepflanzt, inkubiert und bonitiert auf phytotoxische Symptome und Gewebezerstorung uber einem Zeitraum von 15 Tagen. Das Samlingswachstum, die Phytotoxizitat sowie die Befallsintensitat wurden in Gewachshausversuc...

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Section: Discussionmentioning

confidence: 99%

“…Phaseolinone (Fig. 1) is a non-specific diepoxy exotoxin produced by M. phaseolina in culture and has been shown to inhibit seed germination and cause (Dhar et al, 1982).…”

Section: Introductionmentioning

confidence: 99%

Differential Responses of Guayule (Parthenium argentatum Gray) Genotypes to Culture Filtrate and Toxin from Macrophomina phaseolina (Tassi) Goidanich

Kuti

Schading²,

Latigo

et al. 1997

Journal of Phytopathology

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“…The first studies on the phytotoxins produced by M. phaseolina reported the purification and the properties of the exotoxin produced by the pathogen isolated in India [ 11 ]. Subsequently, the main phytotoxin structure, an eremophilane sesquiterpenoid named phaseolinone, was determined [ 12 ]. Recently, from strain 2013-1 of M. phaseolina , obtained from infected soybean roots growing in Pergamino, Argentina, two new phytotoxic penta- and tetra-substituted cyclopentenones, named phaseocyclopentenones A and B, together with guignardone A, were isolated.…”

Section: Introductionmentioning

confidence: 99%

Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite

Castaldi

Masi²,

Sautua

et al. 2021

Biomolecules

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Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was to identify the natural compounds responsible for their antifungal activity. Only the culture filtrates of P. fluorescens 9 showed strong antifungal activity against M. phaseolina. Its organic extract contained phenazine and mesaconic acid (1 and 2), whose antifungal activity was tested against M. phaseolina, as well as Cercospora nicotianae and Colletotrichum truncatum, other pathogens of soybean; however, only compound 1 exhibited activity. The antifungal activity of compound 1 was compared to phenazine-1-carboxylic acid (PCA, 3), 2-hydroxyphenazine (2-OH P, 4), and various semisynthetic phenazine nitro derivatives in order to perform a structure–activity relationship (SAR) study. PCA and phenazine exhibited the same percentage of growth inhibition in M. phaseolina and C. truncatum, whereas PCA (3) showed lower activity against C. nicotianae than phenazine. 2-Hydroxyphenazine (4) showed no antifungal activity against M. phaseolina. The results of the SAR study showed that electron attractor (COOH and NO2) or repulsor (OH) groups significantly affect the antifungal growth, as well as their α- or β-location on the phenazine ring. Both PCA and phenazine could be proposed as biopesticides to control the soybean pathogens M. phaseolina, C. nicotianae, and C. truncatum, and these results should prompt an investigation of their large-scale production and their suitable formulation for greenhouse and field applications.

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“…Charcoal rot is caused by the fungus Macrophomina phaseolina (Tassi) Goid which infects plant roots from the soil by a toxin-mediated mechanism. Macrophomina phaseolina secretes two toxins (Figure 2), phaseolinone [15] [16] and (-)-botryodiplodin [17]. Although the mechanisms of charcoal rot infection via toxins are not well understood, infection of crop through the roots is [67].…”

Section: Introductionmentioning

confidence: 99%

Soybean Seed Phenolics, Sugars, and Minerals Are Altered by Charcoal Rot Infection in MG III Soybean Cultivars

Bellaloui¹,

Mengistu²,

Zobiole³

et al. 2014

FNS

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Soybean seed is a major source of phytochemical compounds that impact human health nutrition and livestock meal. Charcoal rot is a disease caused by the fungus Macrophomina phaseolina (Tassi) Goid, and thought to infect the plants through roots by a toxin-mediated mechanism, resulting in yield loss and poor seed quality, especially under drought conditions. Limited information is available on the effect of charcoal rot on seed phytochemical compounds and mineral nutrition in soybean. Therefore, the objective of this research was to investigate the effect of charcoal rot infection on seed phenol, seed coat lignin, isoflavones, and minerals using susceptible (S) (DK 3964) and moderately resistant (MR) (AG 3905) maturity group (MG)III soybean cultivars to charcoal rot. A two-year field experiment was conducted, and infested soil with charcoal rot (infested soil conditions, INF) or control (non-infested soil conditions, NINF) was used. The results showed that the moderately resistant genotype had higher concentrations of seed phenolics, total isoflavones, and seed coat lignin under infested and non-infested conditions and under irrigated or non-irrigated conditions compared with the susceptible genotype. The same general trend was found for seed K, Ca, P, Mn, Zn, B, and Cu concentrations in the moderately resistant genotype compared with the susceptible genotype. Our research demonstrated that these seed phytochemical constituents may explain the differences between susceptible and moderately resistant cultivars and may play an important role in the resistance to charcoal rot.

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Structure of phaseolinone, a novel phytotoxin from

Cited by 20 publications

References 3 publications

Differential Responses of Guayule (Parthenium argentatum Gray) Genotypes to Culture Filtrate and Toxin from Macrophomina phaseolina (Tassi) Goidanich

Differential Responses of Guayule (Parthenium argentatum Gray) Genotypes to Culture Filtrate and Toxin from Macrophomina phaseolina (Tassi) Goidanich

Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite

Soybean Seed Phenolics, Sugars, and Minerals Are Altered by Charcoal Rot Infection in MG III Soybean Cultivars

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