α-trans-zearalenone | 36455-71-7

• 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
• 英文名称: α-trans-zearalenone
• 英文别名: Z-7α-zearalenol；1H-2-Benzoxacyclotetradecin-1-one,3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7R,11E)-；(4S,8R,12Z)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one
• CAS: 36455-71-7
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: FPQFYIAXQDXNOR-DJAXHYAWSA-N

物化性质

• 沸点：
  599.0±50.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  玉米烯酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.25h， 生成 α-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

• Determination of the conformation of E and Z zearalenone and Their 7α- and 7β-Hydroxy Congeners
  作者：Mirjana Gelo、Zlata Raza、Vitomir Šunjić、Jia Guo、Günther Snatzke

  DOI：10.1016/s0957-4166(00)86149-2

  日期：1991.1

  The CD spectra of some resorcylic acid macrocyclic lactones (RAL) are reported. The spectra of the E,Z-isomeric ketones 1,6 are very similar in shape and magnitude. The Cotton effects of the 7-alpha-alcohols 2 and 7 are also of the same shape, but the DELTA-epsilon-values of 7 are only ca. 50% of those of the others. The E-7-beta-ol 3 gives a completely different CD, whereas in the Z-series 8 shows a similar CD curve as 6 and 7, but with again reduced magnitude. The CDs of the acetates 4 and 5 are very similar to those of the corresponding alcohols 2 and 3, resp. The effect of the 7-alpha- and 7-beta-hydroxy or acetoxy group on the absolute conformation of the "chain" from C(5) to C(10) is thus transmitted to the absolute value of the torsional angle of the inherently chiral chromophore C(11)-C(12)-C(12a)-C(1a)-C(= O)O in 2,3 and 4,5, resp. The CD spectra of the E,Z-isomers do not exhibit straightforward correlation with the configuration around the C = C double bond.
• <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.