7α,β-trans-zearalenol | 194795-92-1

• 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: 7α,β-trans-zearalenol
• 英文别名: α-trans-zearalenone；zearalenol；zearalenone；(3S,11E)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one；(4S,12E)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one
• CAS: 194795-92-1
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: FPQFYIAXQDXNOR-FLBVUZLHSA-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

• 作为反应物：
  描述：

  乙酸乙烯酯 、 7α,β-trans-zearalenol 在 Pseudomonas fluorescens 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 6'-Acetyl-beta-zearalenol
  参考文献：
  名称：

  间苯二酸大环内酯衍生的仲醇绝对构象与荧光假单胞菌脂肪酶在有机溶剂中的立体选择性反乙酰化的相关性

  摘要：

  非对映体对的Transacetylation秒。衍生自间苯二酸的大环内酯的醇；7α，β-反式-zearalenols（1，2，全名，（3S，7R和3S，7S）反式- 3,4,5,6,9,10八氢7,14,16三羟基-3-甲基-1H-2- benzoxacyclotetradecine -1-酮），7α，β-顺-zearalenols（5，6），和7α，β-zearanols（9，10，全名。，（3S，7R和3S，7S）乙酸乙烯酯催化3,4,5,6,9,10,11,12-十氢-714,16-三羟基-3-甲基-1H-2-苯并氧杂环十四烷-1-酮）假单胞菌 研究了正庚烷和乙腈中的荧光假单胞菌脂肪酶。它具有很高的立体选择性。非对映体过量的7β-O-乙酸酯通常接近100％。ķ中号，V最大和特异性恒转矩压最大值/ K中号不显著为7β-不同的立体异构体2，6和10。但是，它们在从正庚烷到乙腈的过程中会发

  DOI：

  10.1016/s0040-4020(01)85687-8

文献信息

• Enzymatic kinetic separation of stereoisomeric macrocyclic lactone derivatives, 7α,β-O-acyl trans-zearalenols and 7α,β-O-acyl zearanols
  作者：Mirjana Gelo、Vitomir Šunjić

  DOI：10.1016/s0040-4020(01)88241-7

  日期：1992.1

  determined by HPLC) approaches 100% for 1,2, 80% for 3,4, and varies between 10% and 90% for 5,6 and 7,8, respectively. Faster and less stereoselective hydrolysis is observed for 7α,β-O-chloroacetyl derivatives 3,4 and 7,8 as compared with acetyl derivatives 1,2 and 5,6. The effect of ionic strength and of organic cosolvent on the rate and selectivity is studied. Explanation of stereoselectivity of this enzymatic

  间苯二酸大环内酯，7α，β-O-玉米赤霉烯醇（1,2和3,4全名：反-3,4,5,6,9,10-八氢-14,16-二羟基-7）的非对映异构体混合物-酰氧基-3-甲基1H-2-苯并氧杂环十四烷-1-酮（3S，7S或3S，7R）和7α，β-酰基硬脂醇（5,6和7,8，全名：3,4,5脂肪酶水解1,6,9,10,11,12-十氢-14,16-二羟基-7-酰氧基-3-甲基-1H-2-苯并氧杂环十四烷-1-酮（3S，7S或3S，7R） 。动力学分离得到具有完全的位点选择性和几乎完全的非对映选择性的7β-醇。在所检查的脂肪酶中，来自假单胞菌属，荧光假单胞菌和圆柱形念珠菌的那些。表现出最广泛的底物特异性。在所有情况下，7β醇都是主要产物，非对映体过量（以HPLC测定的百分数，以％计）接近1,2％为100％，3,4为80％，而5,6和7为10％至90％不等。，8。与乙酰基衍生物1,2和5,6相比，观察到7α，β-O-氯乙酰基衍生物3
• <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.
• LACTONE HYDROLASE AND METHOD OF DEGRADING ALPHA-ZEARALENOL USING THE SAME
  申请人：TIANJIN INSTITUTE OF INDUSTRIAL BIOTECHNOLOGY, CHINESE ACADEMY OF SCIENCES

  公开号：US20170191046A1

  公开（公告）日：2017-07-06

  A lactone hydrolase having improved activity towards α-zearalenol is disclosed. The lactone hydrolase has a modified amino acid sequence of SEQ ID NO: 5, wherein the modification is a substitution of valine at position 167 with histidine. A method of degrading α-zearalenol using such lactone hydrolase is also disclosed.
• Correlation of the absolute conformation of sec alcohols derived from macrocyclic lactones of resorcylic acid and their stereoselective transacetylation in organic solvents by Pseudomonas fluorescens lipase
  作者：Mirjana Gelo-Pujić、Snježana Antolić、Biserka Kojić-Prodić、Vitomir Šunjić

  DOI：10.1016/s0040-4020(01)85687-8

  日期：1994.1

  Transacetylation of diastereomeric pairs of sec. alcohols, derived from macrocyclic lactones of resorcylic acid; 7α,β-trans-zearalenols (1,2, full names., (3S,7R and 3S,7S) trans- 3,4,5,6,9,10-octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecine-1-ones), 7α,β-cis-zearalenols (5,6),and 7α,β-zearanols (9,10,full names., (3S,7R and 3S,7S) 3,4,5,6,9,10,11,12-decahydro-714,16-trihydroxy-3

  非对映体对的Transacetylation秒。衍生自间苯二酸的大环内酯的醇；7α，β-反式-zearalenols（1，2，全名，（3S，7R和3S，7S）反式- 3,4,5,6,9,10八氢7,14,16三羟基-3-甲基-1H-2- benzoxacyclotetradecine -1-酮），7α，β-顺-zearalenols（5，6），和7α，β-zearanols（9，10，全名。，（3S，7R和3S，7S）乙酸乙烯酯催化3,4,5,6,9,10,11,12-十氢-714,16-三羟基-3-甲基-1H-2-苯并氧杂环十四烷-1-酮）假单胞菌 研究了正庚烷和乙腈中的荧光假单胞菌脂肪酶。它具有很高的立体选择性。非对映体过量的7β-O-乙酸酯通常接近100％。ķ中号，V最大和特异性恒转矩压最大值/ K中号不显著为7β-不同的立体异构体2，6和10。但是，它们在从正庚烷到乙腈的过程中会发