玉米烯酮-(全碳-13) | 911392-43-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 中文名称: 玉米烯酮-(全碳-13)
• 英文名称: trans-zearalenone
• 英文别名: ¹³C₁₈-zearalenone；Zearalenone-13C18；(4S,12E)-16,18-dihydroxy-4-(113C)methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
• CAS: 911392-43-3
• 化学式: C₁₈H₂₂O₅
• 分子量: 336.172
• InChiKey: MBMQEIFVQACCCH-NMEASMPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  玉米烯酮-(全碳-13) 以 乙酸乙酯 为溶剂， 反应 8.0h， 生成 trans-zearalenone
  参考文献：
  名称：

  In Vitro Phase I Metabolism of cis-Zearalenone

  摘要：

  The present study investigates the in vitro phase I metabolism of cis-zearalenone (cis-ZEN) in rat liver microsomes and human liver microsomes. cis-ZEN is an often ignored isomer of the trans-configured Fusarium mycotoxin zearalenone (transZEN). Upon the influence of (UV-) light, trans-ZEN isomeriXes to cis-ZEN. Therefore, cis-ZEN is also present in food and feed. The aim of our.study was to evaluate the in vitro phase I metabolism of cis-ZEN in comparison to that of trans-ZEN. As a result, an extensive thetabolizatiOn cis-ZEN is observed for rat and human liver inicrosoines as analyzed by,IIPLC-MS/MS and high- HO resolution MS. Kinetic Investigations based on the substrate depletion approach showed no significant difference in rate cis-zearalenone constants and half-live for,cis and trans-ZEN in rat microsomes. In contrast, cis-ZEN Wa, depleted about 1.4-fold faster than transZEN in human microgornes. The metabolite pattern of cis-ZEN revealecLa total of 10 phase I'metabolites. Its reduction products, a- and 13-cis-zearalenol (beta and fl-cis-ZEL), were found as metabolites in both species, with a-cis-ZEI, being a major metabolite in rat liver microsomes. Both compounds were identified' by co-chromatography with synthesized authentic standards. A further major metabolite in rat microsomes was Monohydroxylated cis-ZEN. In human rnicrOsornes, monohydroxylated cis-ZEN is the single dominant peak of the metabolite profile. Our study discloses three metabolic pathways for cis-ZEN: reduction of the keto-group, monohydroxylation, and a combination of both. Because these routes have been reported for trans-ZEN, we conclude that the phase I metabolism of cis-ZEN is essentially similar to that of its trans isomer. As trans-ZEN is prone to metabolic activation, leading to the formation of more estrogenic metabolites, the novel metabolitWof cisZEN reported in this study, in particular a-cis-ZEL, might also show higheri estrogenicity.

  DOI：

  10.1021/tx500312g

文献信息

• <i>In Vitro</i> Phase I Metabolism of <i>cis</i>-Zearalenone
  作者：Sarah S. Drzymala、Antje J. Herrmann、Ronald Maul、Dietmar Pfeifer、Leif-Alexander Garbe、Matthias Koch

  DOI：10.1021/tx500312g

  日期：2014.11.17

  The present study investigates the in vitro phase I metabolism of cis-zearalenone (cis-ZEN) in rat liver microsomes and human liver microsomes. cis-ZEN is an often ignored isomer of the trans-configured Fusarium mycotoxin zearalenone (transZEN). Upon the influence of (UV-) light, trans-ZEN isomeriXes to cis-ZEN. Therefore, cis-ZEN is also present in food and feed. The aim of our.study was to evaluate the in vitro phase I metabolism of cis-ZEN in comparison to that of trans-ZEN. As a result, an extensive thetabolizatiOn cis-ZEN is observed for rat and human liver inicrosoines as analyzed by,IIPLC-MS/MS and high- HO resolution MS. Kinetic Investigations based on the substrate depletion approach showed no significant difference in rate cis-zearalenone constants and half-live for,cis and trans-ZEN in rat microsomes. In contrast, cis-ZEN Wa, depleted about 1.4-fold faster than transZEN in human microgornes. The metabolite pattern of cis-ZEN revealecLa total of 10 phase I'metabolites. Its reduction products, a- and 13-cis-zearalenol (beta and fl-cis-ZEL), were found as metabolites in both species, with a-cis-ZEI, being a major metabolite in rat liver microsomes. Both compounds were identified' by co-chromatography with synthesized authentic standards. A further major metabolite in rat microsomes was Monohydroxylated cis-ZEN. In human rnicrOsornes, monohydroxylated cis-ZEN is the single dominant peak of the metabolite profile. Our study discloses three metabolic pathways for cis-ZEN: reduction of the keto-group, monohydroxylation, and a combination of both. Because these routes have been reported for trans-ZEN, we conclude that the phase I metabolism of cis-ZEN is essentially similar to that of its trans isomer. As trans-ZEN is prone to metabolic activation, leading to the formation of more estrogenic metabolites, the novel metabolitWof cisZEN reported in this study, in particular a-cis-ZEL, might also show higheri estrogenicity.