title: Isolation and characterization of a new less-toxic derivative of the Fusarium mycotoxin diacetoxyscirpenol after thermal treatment.
abstract: Trichothecenes are an important class of mycotoxins that act as potent protein synthesis inhibitors in eukaryotic organisms. The compound 4,15-diacetoxyscirpenol is highly toxic for plants and animals. Potatoes are especially prone to be contaminated with 4,15-diacetoxyscirpenol after infection with Fusarium sambucinum. In the current study, the reduction of 4,15-diacetoxyscirpenol during thermal treatment in aqueous solution was monitored. A new derivative was detected and named DAS-M1. After isolation, DAS-M1 was characterized with LC-HR-MS and LC-MS/MS and structurally elucidated with (1)H, (13)C, and 2D NMR. Potatoes were inoculated with F. sambucinum, and the infected potatoes were cooked at 100 or 121 °C, respectively. A reduction of 4,15-diacetoxyscirpenol from about 26% (1 h at 100 °C) to 100% (4 h at 121 °C) was detected by means of LC-MS/MS analysis. The effects of different pH values on the reduction of 4,15-diacetoxyscirpenol were investigated, showing higher conversion rates at more acidic pH values. In addition, the toxicity of 4,15-diacetoxyscirpenol and DAS-M1 was compared in vitro using a wheat germ transcription/translation assay and in vivo on Saccharomyces cerevisiae. The results show that the inhibitory effect of DAS-M1 on yeast growth is about 50 times lower and inhibition of protein synthesis is about 100 times lower than that of 4,15-diacetoxyscirpenol.
authors.affiliation: Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences Vienna, Konrad Lorenz Strasse 20, 3430 Tulln, Austria.
authors.forename: Mehrdad
authors.initials: M
authors.lastname: Shams
authors.forename: Rudolf
authors.initials: R
authors.lastname: Mitterbauer
authors.forename: Roberto
authors.initials: R
authors.lastname: Corradini
authors.forename: Gerlinde
authors.initials: G
authors.lastname: Wiesenberger
authors.forename: Chiara
authors.initials: C
authors.lastname: Dall'Asta
authors.forename: Rainer
authors.initials: R
authors.lastname: Schuhmacher
authors.forename: Rudolf
authors.initials: R
authors.lastname: Krska
authors.forename: Gerhard
authors.initials: G
authors.lastname: Adam
authors.forename: Franz
authors.initials: F
authors.lastname: Berthiller
mesh_terms: D003374:Coumarins / Q000378:metabolism*; D005506:Food Contamination / Q000032:analysis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000032:analysis* / Q000737:chemistry / Q000633:toxicity*; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D009183:Mycotoxins / Q000032:analysis; D035281:Plant Tubers / Q000737:chemistry / Q000382:microbiology; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D011198:Solanum tuberosum / Q000737:chemistry* / Q000382:microbiology
chemical_list: C506431:4,15-diacetoxyscirpenol; D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D009183:Mycotoxins; C559139:fusariumin