nordeoxynivalenol B | 103776-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: nordeoxynivalenol B
• 英文别名: (2R,3R,3aR,8bR)-3a-(hydroxymethyl)-6,8b-dimethyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2,3,5-triol
• CAS: 103776-39-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: PAKXMQGHFZXKNF-ICGCDAGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  nordeoxynivalenol B 生成 Acetic acid (2R,3R,3aR,8bR)-2,5-diacetoxy-3a-acetoxymethyl-6,8b-dimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3-yl ester
  参考文献：
  名称：

  Alkaline degradation of the mycotoxin 4-deoxynivalenol

  摘要：

  DOI：

  10.1016/s0040-4039(86)80037-5
• 作为产物：
  描述：

  deoxynivalenol 在 sodium hydroxide 作用下， 反应 1.0h， 生成 (2R,2aS,3aR,7bS)-2,6-Dihydroxy-7c-hydroxymethyl-5,7b-dimethyl-2,2a,3a,4,7b,7c-hexahydro-1H-3-oxa-benzo[a]cyclopropa[gh]pentalen-7-one 、 nordeoxynivalenol B 、 nordeoxynivalenol C
  参考文献：
  名称：

  Alkaline degradation of the mycotoxin 4-deoxynivalenol

  摘要：

  DOI：

  10.1016/s0040-4039(86)80037-5

文献信息

• Thermal Degradation of the <i>Fusarium</i> Mycotoxin Deoxynivalenol
  作者：Michael Bretz、Marita Beyer、Benedikt Cramer、Anja Knecht、Hans-Ulrich Humpf

  DOI：10.1021/jf061008g

  日期：2006.8.1

  Deoxynivalenol (DON) is a toxic secondary metabolite produced by molds of the Fusarium genus, which are able to infect cereal crops in the field. Concerning its rate of occurrence and mean concentration, DON is one of the most important mycotoxins in cereal commodities. Its toxic effects range from causing diarrhea, vomiting, and gastro-intestinal inflammation to noncompetitive inhibition of the biosynthesis of proteins in eukaryotic cells. To study the stability of DON under food-processing conditions such as cooking or baking, we performed model heating experiments and screened the residue for degradation products. Heating of DON and 3-acetyldeoxynivalenol (3-AcDON), especially under alkaline conditions, gave a mixture of compounds, which were isolated and structurally elucidated by NMR and MS experiments. Three of these compounds were already known (norDON A, norDON B, and norDON C), while four were new and named 9-hydroxymethyl DON lactone, norDON D, norDON E, and norDON F. The significance of the DON degradation products was checked by analyzing commercially available food samples. norDON A, B, and C were detected in 29-66% of the samples in mean concentrations ranging from 3 to 15 mu g/kg. Furthermore, cell culture experiments using IHKE cells showed that the compounds that were detected in food samples are less cytotoxic in the formazan dye cytotoxicity assay compared to DON. Whereas DON revealed a median effective concentration (EC50) at 1.1 mu mol/L, all other compounds did not show any significant effect up to 100 mu mol/L. These findings indicate that the degradation of DON under thermal treatment might reduce the toxicity of DON contaminated food.
• Alkaline degradation of the mycotoxin 4-deoxynivalenol
  作者：J. Christopher Young、Barbara A. Blackwell、John W. ApSimon

  DOI：10.1016/s0040-4039(86)80037-5

  日期：1986.1