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9 recordsLinked to original sources
PubMed1977

Synthesis of tenuazonic acid analogues.

The synthesis of two 1.5-diaryltetramic acids, aryl analogues of tenuazonic acid, is described. The reactivity of position 4 of these tetramic acids towards primary and secondary amines, and o-methylation led to the synthesis of 4-substituted-delta3-pyrroline-2-one. Further, reactivity of position 3 has been indicated by the formation of 3-arylidenepyrrolidine-2.4-diones and by diazo-coupling. The structures assigned to the new compounds are substantiated by IR and NMR data.

Antibiotics, Antineoplastic↗
PubMed1977

Tenuazonic acid production by Alternaria alternata and Alternaria tenuissima isolated from cotton.

Cultures of Alternaria alternata (three isolates) and Alternaria tenuissima (three isolates) obtained from cottonseeds and bolls were toxigenic when cultured on various laboratory media. A mycotoxin was isolated and identified as tenuazonic acid by using solvent partition, thin-layer chromatography, and instrument analyses. Toxicity was monitored with brine shrimp and chicken embryo bioassays. All cultures except A. alternata 938 produced tenuazonic acid when grown on cottonseed and on yeast extract-sucrose broth. The most toxin (266 mg/kg) was produced by A. tenuissima 843 on cottonseed.

Alternaria↗
PubMed2026

Integrated histone and proteome analyses reveal convergent and distinct hepatotoxic mechanisms of tenuazonic acid and deoxynivalenol.

Mycotoxins are widespread dietary contaminants whose health impacts are expected to intensify under climate change. Although their mechanisms of toxicity remain incompletely understood, epigenetic dysregulation has been increasingly implicated. Here, mass spectrometry-based multi-omics was used to profile histone post-translational modifications and proteome dynamics in HepG2 cells exposed to seven mycotoxin conditions. Time-resolved analyses identified tenuazonic acid as the dominant cellular disruptor, inducing alterations in H3K27 and H1 variants, and revealing a previously unrecognized oxidative modification of the H1.0 N-terminal methionine (H1.0N-term0AcM0Ox) that retains the protein's N-terminal acetylation. An Alternaria toxin mixture induced similar H1 responses, largely driven by tenuazonic acid, while deoxynivalenol produced convergent chromatin and proteomic alterations. Proteomic remodeling was characterized by increased protein translation, reduced mitochondrial complex IV expression, and impaired cholesterol biosynthesis, whereas sterigmatocystin activated DNA replication and repair pathways. Together, these findings demonstrate that mycotoxins disrupt chromatin organization, protein synthesis, and lipid metabolism, providing toxicological insight into hepatocellular dysfunction. These findings warrant further validation and mechanistic investigation in future hypothesis-driven studies of mycotoxin exposure.

Trichothecenes↗
PubMed1979

Toxins of molds from decaying tomato fruit.

Among 27 mold isolates from decaying tomatoes, culture filtrates or ethyl acetate extracts of 8 isolates grown in yeast extract-sucrose medium were markedly toxic (mortality, greater than 50%) to brine shrimp larvae. The toxicity of six of these isolates could be attributed to the presence of citrinin, tenuazonic acid, or T-2 toxin. Ethyl acetate extracts of five Alternaria isolates and one Fusarium isolate were mutagenic for Salmonella typhimurium strains. In ripe tomatoes inoculated with toxin-producing isolates and incubated at 25 degrees C, one Alternaria alternata isolate produced tenuazonic acid in seven of seven tomatoes at levels of up to 106 micrograms/g and alternariol methyl ether in one of the seven tomatoes at 0.8 microgram/g. Another A. alternata isolate produced tenuazonic acid or alternariol methyl ether at much lower levels in only three of seven tomatoes. Patulin and citrinin were produced by a Penicillium expansum isolate at levels of up to 8.4 and 0.76 microgram/g, respectively. In tomatoes incubated at 15 degrees C, a Fusarium sulphureum isolate produced T-2 toxin, HT-2 toxin, and neosolaniol at levels of up to 37.5, 37.8 and 5.6 micrograms/g, respectively. If these mycotoxins are thermostable, they may occur at detectable levels in tomato products whenever partially moldy tomatoes are used as raw material.

Animals↗
PubMed1975

Inhibition of epidermal DNA synthesis by cycloheximide and other inhibitors of protein synthesis.

Cycloheximide, pactamycin and tenuazonic acid inhibit protein synthesis in eukaryotic cells. It is the purpose of these studies to determine whether these agents would be effective in vivo inhibitors of epidermal DNA synthesis. Single I.P. administration of 1.5 mg/kg cycloheximide, 0, 1 or 3 hours prior to a 45 minute pulse of thymidine-3H inhibited epidermal DNA synthesis by 68%, 63% and 88%, respectively. This response was dose related at 3.75 hours after cycloheximide with no effect at 0.375 mg/kg and maximal inhibition at 1.5 mg/kg. Epidermal DNA synthesis was inhibited 18, 29 and 62% at doses of 1.5, 3.0 and 6.0 mg/kg pactamycin administered 3 hours before thymidine-3H. Similarly, at doses of 70 and 140 mg/kg tenuazonic acid, epidermal DNA synthesis was inhibited by 50% and 60%, respectively. These data suggest the possible use of protein synthesis inhibitors in epidermal disorders.

Animals↗
PubMed2026

Comprehensive study on pesticide residues and mycotoxins in freeze-dried strawberries and raspberries.

Freeze-dried fruit has gained popularity because it preserves the flavour and nutritional value of fresh fruit while providing extended shelf life. Despite this, there are concerns regarding its chemical safety. This study evaluated 58 freeze-dried fruit products from the Czech retail market, focusing on potential contamination. Pesticide residues and mycotoxins were determined using LC-MS/MS and GC-MS/MS. Overall, 111 pesticide residues (or their metabolites) and 3 mycotoxins were quantified. After applying processing factors, 12 pesticide residues exceeded EU maximum residue limits. Prohibited substances, including carbofuran, omethoate, and haloxyfop, were detected. Tenuazonic acid was found in 71% of samples, while alternariol and tentoxin were detected less frequently. More than half (54%) of strawberry samples contained 10 or more pesticide residues, indicating potential cumulative exposure concerns, particularly for children with lower body weight. These findings highlight the need for continued monitoring of freeze-dried fruits and further assessment of dietary exposure.

Pesticide Residues↗