15-acetylnivalenol | 68165-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 15-acetylnivalenol
• 英文别名: [(1S,2R,3S,7R,9R,10R,11S,12S)-3,10,11-trihydroxy-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate
• CAS: 68165-52-6
• 化学式: C₁₇H₂₂O₈
• 分子量: 354.357
• InChiKey: FBXXVJXDIZNZLY-CAYGJDLQSA-N

物化性质

• 沸点：
  575.3±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  雪腐镰刀菌烯醇 、 乙酸酐 在 吡啶 作用下， 以4 mg的产率得到15-acetylnivalenol
  参考文献：
  名称：

  Preparation of Monoclonal Antibodies Specifically Reacting with the Trichothecene Mycotoxins Nivalenol and 15-Acetylnivalenol via the Introduction of a Linker Molecule into Its C-15 Position

  摘要：

  新戊烯醇（NIV）是一种单端孢霉烯霉菌毒素，其毒性高于脱氧雪腐镰刀菌烯醇。谷物感染镰刀菌（疮痂病或镰刀菌头疫病的致病菌）后，谷物中会积累这种毒素。免疫测定是一种快速简便的分析方法，是监测谷物中 NIV 的必要手段。然而，此前还没有制备出针对 NIV 的特异性抗体。为了建立免疫测定法，我们制备了 NIV，引入了连接体，并生成了针对 NIV 的抗体。NIV 是通过合成吸附剂和硅胶的层析过程从压榨大麦中获得的九州镰刀菌培养物中制备的。NIV 与戊二酸酐反应，在单半戊二酰-NIV 转变为二半戊二酰-NIV 之前停止反应。15-O-Hemiglutaryl-NIV 通过制备型高效液相色谱分离，并采用活性酯法与匙孔帽贝血青素（KLH）结合。用 NIV-KLH 结合物免疫小鼠，制备了两种不同的单克隆抗体。50%的抑制浓度值分别为 36 和 37 纳克/毫升。在直接竞争性酶联免疫吸附试验中，这些抗体也表现出很高的反应活性，能与 NIV 和 15-乙酰基-NIV 发生特异性反应，但不能与脱氧雪腐镰刀菌烯醇和 4-乙酰基-NIV 发生特异性反应。

  DOI：

  10.3390/toxins14110747

文献信息

• 4-<i>O</i>-Acetylation and 3-<i>O</i>-Acetylation of Trichothecenes by Trichothecene 15-<i>O</i>-Acetyltransferase Encoded by<i>Fusarium Tri3</i>
  作者：Takeshi TOKAI、Naoko TAKAHASHI-ANDO、Masumi IZAWA、Takashi KAMAKURA、Minoru YOSHIDA、Makoto FUJIMURA、Makoto KIMURA

  DOI：10.1271/bbb.80501

  日期：2008.9.23

  In the biosynthesis of Fusarium trichothecenes, the C-3 hydroxyl group of isotrichodermol must be acetylated by TRI101 for subsequent pathway genes to function. Despite the importance of this 3-O-acetylation step in biosynthesis, Tri101 is both physically and evolutionarily unrelated to other Tri genes in the trichothecene gene cluster. To gain insight into the evolutionary history of the cluster, we purified recombinant TRI3 (rTRI3), one of the two cluster gene-encoded trichothecene O-acetyltransferases, and examined to determine whether this 15-O-acetyltransferase can add an acetyl to the C-3 hydroxyl group of isotrichodermol. When a high concentration of rTRI3 was used in the assay (final concentration, 50 μm), we observed 3-O-acetylation activity against isotrichodermol that was more than 105 times less efficient than the known 15-O-acetylation activity against 15-deacetylcalonectrin. The rTRI3 protein also exhibited 4-O-acetylation activity when nivalenol was used as a substrate; in addition to 15-acetylnivalenol, di-acetylated derivatives, 4,15-diacetylnivalenol, and, to a lesser extent, 3,15-diacetylnivalenol, were also detected at high enzyme concentrations. The significance of the trace trichothecene 3-O-acetyltransferase activity detected in rTRI3 is discussed in relation to the evolution of the trichothecene gene cluster.

  在镰刀菌毒素的生物合成中，isotrichodermol 的 C-3 羟基必须通过 TRI101 乙酰化，以便后续通路基因发挥功能。尽管这一 3-O-乙酰化步骤在生物合成中至关重要，但 Tri101 在物理和进化上都与萎蔫酸基因簇中的其他 Tri 基因无关。为了深入了解该基因簇的进化历史，我们纯化了其中一种编码萎蔫酸 O-乙酰基转移酶的基因簇 TRI3（rTRI3），并检测了这种 15-O-乙酰基转移酶是否能将乙酰基添加到 isotrichodermol 的 C-3 羟基上。当在检测中使用高浓度的 rTRI3 时（最终浓度为 50 μM），我们观察到对 isotrichodermol 的 3-O-乙酰化活性，其效率比对 15-去乙酰甲虫素已知的 15-O-乙酰化活性低 105 倍以上。当以雪腐镰刀菌烯醇作为底物时，rTRI3 蛋白还表现出 4-O-乙酰化活性；除了 15-乙酰雪腐镰刀菌烯醇外，在高酶浓度下还检测到二乙酰化衍生物 4,15-二乙酰雪腐镰刀菌烯醇，以及较少程度的 3,15-二乙酰雪腐镰刀菌烯醇。本文讨论了在 rTRI3 中检测到的微量萎蔫酸 3-O-乙酰基转移酶活性与萎蔫酸基因簇进化之间的关系。
• Preparation of Monoclonal Antibodies Specifically Reacting with the Trichothecene Mycotoxins Nivalenol and 15-Acetylnivalenol via the Introduction of a Linker Molecule into Its C-15 Position
  作者：Kyoko Noda、Yuki Hirakawa、Tomomi Nishino、Ritsuto Sekizuka、Marin Kishimoto、Tomohiro Furukawa、Sakiko Sawane、Ayu Matsunaga、Naoki Kobayashi、Kazutoshi Sugita、Kenji Oonaka、Hiroko Kawakami、Yuji Otsuka、Tetsuya Yamamoto、Toshihiro Yamamoto、Taku Yoshiya、Maiko Watanabe、Machiko Saka、Keiko Momma、Masayo Kushiro、Shiro Miyake

  DOI：10.3390/toxins14110747

  日期：——

  Nivalenol (NIV) is a trichothecene mycotoxin that is more toxic than deoxynivalenol. It accumulates in grains due to infection with Fusarium species, which are the causative agents of scab or Fusarium head blight. An immunoassay, which is a rapid and easy analytical method, is necessary for monitoring NIV in grains. However, a specific antibody against NIV has not been prepared previously. To establish an immunoassay, we prepared NIV, introduced a linker, and generated antibodies against it. NIV was prepared from a culture of Fusarium kyushuense obtained from pressed barley through chromatographic procedures with synthetic adsorbents and silica gel. NIV was reacted with glutaric anhydride, and the reaction was stopped before mono-hemiglutaryl-NIV was changed to di-hemiglutaryl-NIV. 15-O-Hemiglutaryl-NIV was isolated via preparative HPLC and bound to keyhole limpet hemocyanin (KLH) using the active ester method. Two different monoclonal antibodies were prepared by immunizing mice with the NIV-KLH conjugate. The 50% inhibitory concentration values were 36 and 37 ng/mL. These antibodies also showed high reactivity in a direct competitive enzyme-linked immunosorbent assay and specifically reacted with NIV and 15-acetyl-NIV but not with deoxynivalenol and 4-acetyl-NIV.

  新戊烯醇（NIV）是一种单端孢霉烯霉菌毒素，其毒性高于脱氧雪腐镰刀菌烯醇。谷物感染镰刀菌（疮痂病或镰刀菌头疫病的致病菌）后，谷物中会积累这种毒素。免疫测定是一种快速简便的分析方法，是监测谷物中 NIV 的必要手段。然而，此前还没有制备出针对 NIV 的特异性抗体。为了建立免疫测定法，我们制备了 NIV，引入了连接体，并生成了针对 NIV 的抗体。NIV 是通过合成吸附剂和硅胶的层析过程从压榨大麦中获得的九州镰刀菌培养物中制备的。NIV 与戊二酸酐反应，在单半戊二酰-NIV 转变为二半戊二酰-NIV 之前停止反应。15-O-Hemiglutaryl-NIV 通过制备型高效液相色谱分离，并采用活性酯法与匙孔帽贝血青素（KLH）结合。用 NIV-KLH 结合物免疫小鼠，制备了两种不同的单克隆抗体。50%的抑制浓度值分别为 36 和 37 纳克/毫升。在直接竞争性酶联免疫吸附试验中，这些抗体也表现出很高的反应活性，能与 NIV 和 15-乙酰基-NIV 发生特异性反应，但不能与脱氧雪腐镰刀菌烯醇和 4-乙酰基-NIV 发生特异性反应。