Structure elucidation and in vitro cytotoxicity of ochratoxin α amide, a new degradation product of ochratoxin A

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• 作者：Andrea Bittner ; Benedikt Cramer ; Henning Harrer ; Hans-Ulrich Humpf
• 关键词：Ochratoxin A ; Degradation ; Detoxification ; Roasting ; Extrusion ; Ochratoxin α amide ; Thermal stability ; Light ; Coffee
• 刊名：Mycotoxin Research
• 出版年：2015
• 出版时间：May 2015
• 年：2015
• 卷：31
• 期：2
• 页码：83-90
• 全文大小：609 KB
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• 作者单位：Andrea Bittner (1)
  Benedikt Cramer (1)
  Henning Harrer (1)
  Hans-Ulrich Humpf (1)
  
  1. Institute of Food Chemistry, Westf?lische Wilhelms-Universit?t Münster, Corrensstrasse 45, 48149, Münster, Germany
  
• 刊物主题：Microbiology; Medical Microbiology; Chemistry/Food Science, general; Medicine/Public Health, general;
• 出版者：Springer Berlin Heidelberg
• ISSN：1867-1632

文摘

The mycotoxin ochratoxin A is a secondary metabolite occurring in a wide range of commodities. During the exposure of ochratoxin A to white and blue light, a cleavage between the carbon atom C-14 and the nitrogen atom was described. As a reaction product, the new compound ochratoxin α amide has been proposed based on mass spectrometry (MS) experiments. In the following study, we observed that this compound is also formed at high temperatures such as used for example during coffee roasting and therefore represents a further thermal ochratoxin A degradation product. To confirm the structure of ochratoxin α amide, the compound was prepared in large scale and complete structure elucidation via nuclear magnetic resonance (NMR) and MS was performed. Additionally, first studies on the toxicity of ochratoxin α amide were performed using immortalized human kidney epithelial (IHKE) cells, a cell line known to be sensitive against ochratoxin A with an IC₅₀ value of 0.5?μM. Using this system, ochratoxin α amide revealed no cytotoxicity up to concentrations of 50?μM. Thus, these results propose that the thermal degradation of ochratoxin A to ochratoxin α amide might be a detoxification process. Finally, we present a sample preparation and a HPLC-tandem mass spectrometry (HPLC-MS/MS) method for the analysis of ochratoxin α amide in extrudates and checked its formation during the extrusion of artificially contaminated wheat grits at 150 and 180?°C, whereas no ochratoxin α amide was detectable under these conditions.