α-zearalenol-14-β-D-glucuronide | 1032558-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-zearalenol-14-β-D-glucuronide
• 英文别名: α-zearalenol 4-O-β-D-glucuronide；(2S,3S,4S,5R,6S)-6-[[(4S,8R,12E)-8,18-dihydroxy-4-methyl-2-oxo-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1032558-21-6
• 化学式: C₂₄H₃₂O₁₁
• 分子量: 496.511
• InChiKey: ZVJWVFZDQLKJMD-AXSGHRSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  玉米烯酮 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 β-zearalenol-14-β-D-glucuronide 、 α-zearalenol-14-β-D-glucuronide
  参考文献：
  名称：

  同时制备α/β-玉米赤霉烯醇糖苷和葡糖醛酸苷

  摘要：

  报道了一种改进和可重现的方法，用于制备霉菌毒素玉米赤霉烯酮（ZEN）的两种代谢产物霉菌毒素α-和β-玉米赤霉烯醇（α，β-ZEL）的四种不同糖苷。这些缀合或掩盖的霉菌毒素是在植物（葡萄糖苷）或动物和人（葡萄糖苷酸）的II期新陈代谢过程中形成的。将改良的区域选择性Königs-Knorr葡萄糖醛酸苷化应用于ZEN，随后还原真菌毒素的酮基，导致ZEL的α-和β-构型，还导致葡萄糖醛酸甲酯的部分还原，以获得相应的葡糖苷。糖部分脱保护后，使用制备型HPLC一次分离出α-和β-玉米烯醇-14-β，D-葡糖醛酸苷以及相应的葡糖苷。

  DOI：

  10.1016/j.carres.2013.03.002

文献信息

• Preparative Enzymatic Synthesis of Glucuronides of Zearalenone and Five of Its Metabolites
  作者：David E. Stevenson、Richard P. Hansen、Jared I. Loader、Dwayne J. Jensen、Janine M. Cooney、Alistair L. Wilkins、Christopher O. Miles

  DOI：10.1021/jf800379z

  日期：2008.6.1

  The resorcylic acid lactones zearalenone (1), alpha-zearalenol (2), beta-zearalenol (3), alpha-zearalanol (zeranol) (4), beta-zearalanol (taleranol) (5), and zearalanone (6) were converted to their glucuronides on a preparative scale in good yields. Reactions were conducted with bovine uridine 5'-diphosphoglucuronyl transferase (UDPGT) as catalyst and uridine 5'-diphosphoglucuronic acid (UDPGA) as cofactor. The glucuronides were isolated by column chromatography and characterized by NMR spectroscopy and mass spectrometry. Although the principal products were 4-O-glucuronides (i.e., linkage through a phenolic hydroxyl), significant quantities of the 6'-O-glucuronides (i.e., linkage through the aliphatic hydroxyl) of alcohols 2, 4, and 5 were also isolated. In the case of 3, the 2-O-glucuronide was isolated as the minor product. Overall isolated yields of glucuronides, performed on a 20-50 mg scale, were typically ca. 80%. based on, the resorcylic acid lactone starting material. LC-UV-MS(2) analysis of purified specimens revealed MS(2) fragmentations useful for defining the point of attachment of the glucuronide moiety to the zearalenone nucleus.