Mutagenicity of the mycotoxin botryodiplodin in the salmonella typhimurium/microsomal activation test

Moulé, Y.; Decloître, F.; Hamon, Gérard

doi:10.1002/em.2860030311

Cited by 16 publications

(7 citation statements)

References 16 publications

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“…In addition, (±)-botryodiplodin induced phytotoxic responses indistinguishable from those induced by (−)-botryodiplodin, when compared in duckweed (L. pausicostata) plantlet cultures and soybean leaf discs in culture (see below). Identical activity of (±)-botryodiplodin and (−)-botryodiplodin is consistent with extensive studies on the mechanism of action of (−)-botryodiplodin by Moule et al (1981a;1981b; [36][37][38], which indicated that the toxin acts by chemical reactions in cell nuclei that covalently cross-link proteins to DNA, and not by interacting with a chiral binding site on any enzyme or receptor that might require an optically active form. Although (+)-botryodiplodin has been prepared by chemical synthesis [39], its biological activity, or the lack thereof, has not been reported by these investigators or others.…”

Section: Synthesis Of (±)-Botryodiplodinsupporting

confidence: 86%

“…(±)-Botryodiplodin was selected for use in these studies, because it is readily synthesized chemically in larger amounts than were available by fermentation [32]. The mechanism of action of botryodiplodin has been extensively studied by Moule et al [36][37][38], who provided evidence for non-enzymatic (i.e., chemical) crosslinking of DNA to protein. There have been no reports of botryodiplodin binding specifically to a chiral binding site on any enzyme or receptor.…”

Section: Preparation Of (±)-Botryodiplodinmentioning

confidence: 99%

“…The biological activity level of (±)-botryodiplodin was confirmed using antibacterial activity, the type of activity used to guide the initial isolation of (−)-botryodiplodin by Sen Gupta et al (1966) [26], and the most easily measured of its numerous reported biological activities, including antifungal [56], phytotoxic [25,32], anti-cancer [37,57], mutagenic [36], and antifertility [58] activities. Antibacterial activity was compared on samples of (±)-botryodiplodin, prepared as described above, and (−)-botryodiplodin purified as described by Ramezani et al (2007) [32] from culture filtrates of M. phaseolina isolated from a soybean plant with charcoal rot disease in Mississippi.…”

Section: Assay Of Antibacterial Activity Of Botryodiplodinmentioning

confidence: 99%

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Phytotoxic Responses of Soybean (Glycine max L.) to Botryodiplodin, a Toxin Produced by the Charcoal Rot Disease Fungus, Macrophomina phaseolina

Abbas

Bellaloui

Butler

et al. 2020

Toxins

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Toxins have been proposed to facilitate fungal root infection by creating regions of readily-penetrated necrotic tissue when applied externally to intact roots. Isolates of the charcoal rot disease fungus, Macrophomina phaseolina, from soybean plants in Mississippi produced a phytotoxic toxin, (−)-botryodiplodin, but no detectable phaseolinone, a toxin previously proposed to play a role in the root infection mechanism. This study was undertaken to determine if (−)-botryodiplodin induces toxic responses of the types that could facilitate root infection. (±)-Botryodiplodin prepared by chemical synthesis caused phytotoxic effects identical to those observed with (−)-botryodiplodin preparations from M. phaseolina culture filtrates, consistent with fungus-induced phytotoxicity being due to (−)-botryodiplodin, not phaseolinone or other unknown impurities. Soybean leaf disc cultures of Saline cultivar were more susceptible to (±)-botryodiplodin phytotoxicity than were cultures of two charcoal rot-resistant genotypes, DS97-84-1 and DT97-4290. (±)-Botryodiplodin caused similar phytotoxicity in actively growing duckweed (Lemna pausicostata) plantlet cultures, but at much lower concentrations. In soybean seedlings growing in hydroponic culture, (±)-botryodiplodin added to culture medium inhibited lateral and tap root growth, and caused loss of root caps and normal root tip cellular structure. Thus, botryodiplodin applied externally to undisturbed soybean roots induced phytotoxic responses of types expected to facilitate fungal root infection.

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Section: Synthesis Of (±)-Botryodiplodinsupporting

confidence: 86%

Section: Preparation Of (±)-Botryodiplodinmentioning

confidence: 99%

Section: Assay Of Antibacterial Activity Of Botryodiplodinmentioning

confidence: 99%

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Phytotoxic Responses of Soybean (Glycine max L.) to Botryodiplodin, a Toxin Produced by the Charcoal Rot Disease Fungus, Macrophomina phaseolina

Abbas

Bellaloui

Butler

et al. 2020

Toxins

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“…botryodiplodin (BD) (6, 63, 96), a mutagenic mycotoxin (67). BD forms DPCs in eukaryotic cells (66,69) and blocks DNA synthesis in a manner consistent with a DNA-damaging agent (68).…”

Section: Lge 2 Cross-links Dna With Proteinsmentioning

confidence: 99%

Levuglandins and Isolevuglandins: Stealthy Toxins of Oxidative Injury

Salomon

2005

Antioxidants & Redox Signaling

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Inspired by a reaction discovered through basic research on the chemistry of the bicyclic peroxide nucleus of the prostaglandin endoperoxide PGH2, we postulated that levulinaldehyde derivatives with prostaglandin side chains, levuglandins (LGs), and structurally isomeric analogues, isolevuglandins (iso[n]LGs), would be generated by nonenzymatic rearrangements of prostanoid and isoprostanoid endoperoxides. Two decades of subsequent studies culminated in our discoveries of the LG and isoLG pathways, branches of the cyclooxygenase and isoprostane pathways, respectively. In cells, PGH2 rearranges nonenzymatically to LGs even in the presence of enzymes that use PGH2 as a substrate. IsoLGs, also known as isoketals or neuroketals, are generated in vivo through free radical-induced autoxidation of polyunsaturated phospholipid esters. Hydrolysis occurs after rapid adduction of isoLG phospholipids to proteins. The proclivity of these reactive species to avidly bind covalently with and cross-link proteins and nucleic acids complicated the hunt for LGs and isoLGs in vivo. The extraordinary reactivity of these "stealthy toxins" underlies much, if not all, of the biological consequences of LG and isoLG generation. They interfere with protein function and are among the most potent neurotoxic products of lipid oxidation known. Because they can accumulate over the lifetimes of proteins, iso[n]LG-protein adducts represent a convenient dosimeter of oxidative stress.

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“…Penicillium stipitatum Thom] [ 29 ], M. phaseolina [ 21 ] and others [ 30 ]. This mycotoxin has received attention due to its potent antibiotic [ 31 ], anticancer [ 32 ] mutagenic, cytotoxic [ 33 ] and phytotoxic activities [ 34 ], as well as the ability to induce protein-DNA crosslinking in mammalian cells [ 35 , 36 ]. Among (−)-botryodiplodin producing fungi, P. roqueforti is a common contaminant of processed food [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Pigment Produced by Glycine-Stimulated Macrophomina Phaseolina Is a (−)-Botryodiplodin Reaction Product and the Basis for an In-Culture Assay for (−)-Botryodiplodin Production

et al. 2022

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An isolate of Macrophomina phaseolina from muskmelons (Cucumis melo) was reported by Dunlap and Bruton to produce red pigment(s) in melons and in culture in the presence of added glycine, alanine, leucine, or asparagine in the medium, but not with some other amino acids and nitrogen-containing compounds. We explored the generality and mechanism of this pigment production response using pathogenic M. phaseolina isolates from soybean plants expressing symptoms of charcoal rot disease. A survey of 42 M. phaseolina isolates growing on Czapek-Dox agar medium supplemented with glycine confirmed pigment production by 71% of isolates at the optimal glycine concentration (10 g/L). Studies in this laboratory have demonstrated that some pathogenic isolates of M. phaseolina produce the mycotoxin (−)-botryodiplodin, which has been reported to react with amino acids, proteins, and other amines to produce red pigments. Time course studies showed a significant positive correlation between pigment and (−)-botryodiplodin production by selected M. phaseolina isolates with maximum production at seven to eight days. Pigments produced in agar culture medium supplemented with glycine, beta-alanine, or other amines exhibited similar UV-vis adsorption spectra as did pigments produced by (±)-botryodiplodin reacting in the same agar medium. In a separate study of 39 M. phaseolina isolates, red pigment production (OD520) on 10 g/L glycine-supplemented Czapek-Dox agar medium correlated significantly with (−)-botryodiplodin production (LC/MS analysis of culture filtrates) in parallel cultures on un-supplemented medium. These results support pigment production on glycine-supplemented agar medium as a simple and inexpensive in-culture method for detecting (−)-botryodiplodin production by M. phaseolina isolates.

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Mutagenicity of the mycotoxin botryodiplodin in the salmonella typhimurium/microsomal activation test

Abstract: Botryodiplodin, a mycotoxin synthesized by some strains of Penicillium roqueforti was tested for lethal and mutagenic effects on Salmonella typhimurium (TA98). Botryodiplodin was active in the histidine reversion system without metabolic activation.

Cited by 16 publications

References 16 publications

Phytotoxic Responses of Soybean (Glycine max L.) to Botryodiplodin, a Toxin Produced by the Charcoal Rot Disease Fungus, Macrophomina phaseolina

Phytotoxic Responses of Soybean (Glycine max L.) to Botryodiplodin, a Toxin Produced by the Charcoal Rot Disease Fungus, Macrophomina phaseolina

Levuglandins and Isolevuglandins: Stealthy Toxins of Oxidative Injury

Pigment Produced by Glycine-Stimulated Macrophomina Phaseolina Is a (−)-Botryodiplodin Reaction Product and the Basis for an In-Culture Assay for (−)-Botryodiplodin Production

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