Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences Vienna, Konrad Lorenz Strasse 20, 3430 Tulln, Austria.
J Agric Food Chem. 2011 Sep 14;59(17):9709-14. doi: 10.1021/jf2022176. Epub 2011 Aug 9.
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.
单端孢霉烯族化合物是一类重要的真菌毒素，它们在真核生物中作为有效的蛋白质合成抑制剂。化合物 4,15-二乙酰基脱氧雪腐镰刀菌烯醇对植物和动物具有高毒性。受茄病镰刀菌感染的马铃薯特别容易受到 4,15-二乙酰基脱氧雪腐镰刀菌烯醇的污染。在当前的研究中，监测了水溶液中热处理过程中 4,15-二乙酰基脱氧雪腐镰刀菌烯醇的减少情况。检测到并命名了一种新的衍生物，称为 DAS-M1。通过 LC-HR-MS 和 LC-MS/MS 对 DAS-M1 进行了分离和表征，并通过 1H、13C 和 2D NMR 对其结构进行了阐明。将茄病镰刀菌接种到马铃薯上，然后分别在 100 或 121°C 下对感染的马铃薯进行烹饪。通过 LC-MS/MS 分析检测到 4,15-二乙酰基脱氧雪腐镰刀菌烯醇从约 26%（100°C 时 1 小时）减少到 100%（121°C 时 4 小时）。研究了不同 pH 值对 4,15-二乙酰基脱氧雪腐镰刀菌烯醇还原的影响，结果表明在更酸性的 pH 值下转化率更高。此外，还在体外使用小麦胚转录/翻译测定法和体内在酿酒酵母上比较了 4,15-二乙酰基脱氧雪腐镰刀菌烯醇和 DAS-M1 的毒性。结果表明，DAS-M1 对酵母生长的抑制作用比 4,15-二乙酰基脱氧雪腐镰刀菌烯醇低约 50 倍，对蛋白质合成的抑制作用低约 100 倍。
