3-乙酰脱氧瓜萎镰菌醇 | 50722-38-8

• 物质功能分类: 分析化学 - 标准品 - 食品和化妆品标准品
• 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
• 中文名称: 3-乙酰脱氧瓜萎镰菌醇
• 中文别名: 3-乙酰基脱氧雪腐镰刀菌烯醇
• 英文名称: 3-O-acetyl-4-deoxynivalenol
• 英文别名: 3-acetyl-4-deoxynivalenol；3-acetoxydeoxynivalenol；3-acetyl-deoxynivalenol；3-acetyldeoxynivalenol；deoxynivalenol；3-acetyl-DON；[(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate
• CAS: 50722-38-8
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: ADFIQZBYNGPCGY-HTJQZXIKSA-N

物化性质

• 熔点：
  185.75°C
• 沸点：
  394.5°C (rough estimate)
• 密度：
  1.2179 (rough estimate)
• 闪点：
  2 °C
• 溶解度：
  DMF：30mg/mL； DMSO：25mg/mL；乙醇：30mg/mL； PBS（pH 7.2）：10 mg/mL
• LogP：
  -0.448 (est)
• 碰撞截面：
  196 Ų [M+H3C2O2]- [CCS Type: TW, Method: calibrated with polyalanine]

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 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：
  106
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  Xn,F,T
• 安全说明：
  S16,S26,S36/37,S45
• 危险类别码：
  R23/24/25,R20/21/22,R36,R11
• WGK Germany：
  2,3
• 海关编码：
  29329990
• 危险品运输编号：
  UN 2811 6.1/PG 2
• RTECS号：
  YD0150000
• 包装等级：
  I
• 危险类别：
  6.1(a)
• 危险标志：
  GHS06
• 危险性描述：
  H300,H311,H331
• 危险性防范说明：
  P261,P264,P280,P301 + P310,P311

制备方法与用途

生物活性

3-乙酰去雪腐镰刀菌烯醇（3-Acetyldeoxynivalenol）是一种单端孢霉烯霉菌毒素，脱氧雪腐镰刀菌烯醇 (DON) 的乙酰化衍生物。它能够穿透血脑屏障 (BBB)，具有较强的毒性。

类别

有毒物品

毒性分级

剧毒

急性毒性

• 口服 - 小鼠 LD50: 34 毫克/公斤
• 腹腔 - 小鼠 LD50：47 毫克/公斤

刺激数据

• 皮肤 - 豚鼠 0.004 毫克 轻度刺激

可燃性危险特性

可燃；加热分解时释放刺激烟雾

储运特性

应存放在通风、低温和干燥的仓库中，并与食品原料分开存放。

灭火剂

干粉、泡沫、砂土、二氧化碳，以及雾状水

反应信息

• 作为反应物：
  描述：

  3-乙酰脱氧瓜萎镰菌醇 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以94%的产率得到脱氧雪腐镰刀菌烯醇
  参考文献：
  名称：

  脱氧雪腐镰刀菌烯醇、其乙酰化衍生物和 T2-毒素的硫酸化

  摘要：

  介绍了单端孢霉烯真菌毒素的几种硫酸盐的合成。脱氧雪腐镰刀菌烯醇 (DON) 及其乙酰化衍生物由 3-乙酰脱氧雪腐镰刀菌烯醇 (3ADON) 合成，并用作硫酸化的底物，以获得一系列五种不同的基于 DON 的硫酸盐以及 T2-toxin-3-sulfate。怀疑这些物质是在植物和人类的 II 期代谢过程中形成的。硫酸化使用硫酰基咪唑鎓盐进行，该盐在使用前合成。所有受保护的中间体和最终产品均通过 NMR 进行表征，并将作为参考材料用于真菌毒素毒理学和生物分析领域的进一步研究。

  DOI：

  10.1016/j.tet.2014.05.064

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。
• Thermal Degradation of the <i>Fusarium</i> Mycotoxin Deoxynivalenol
  作者：Michael Bretz、Marita Beyer、Benedikt Cramer、Anja Knecht、Hans-Ulrich Humpf

  DOI：10.1021/jf061008g

  日期：2006.8.1

  Deoxynivalenol (DON) is a toxic secondary metabolite produced by molds of the Fusarium genus, which are able to infect cereal crops in the field. Concerning its rate of occurrence and mean concentration, DON is one of the most important mycotoxins in cereal commodities. Its toxic effects range from causing diarrhea, vomiting, and gastro-intestinal inflammation to noncompetitive inhibition of the biosynthesis of proteins in eukaryotic cells. To study the stability of DON under food-processing conditions such as cooking or baking, we performed model heating experiments and screened the residue for degradation products. Heating of DON and 3-acetyldeoxynivalenol (3-AcDON), especially under alkaline conditions, gave a mixture of compounds, which were isolated and structurally elucidated by NMR and MS experiments. Three of these compounds were already known (norDON A, norDON B, and norDON C), while four were new and named 9-hydroxymethyl DON lactone, norDON D, norDON E, and norDON F. The significance of the DON degradation products was checked by analyzing commercially available food samples. norDON A, B, and C were detected in 29-66% of the samples in mean concentrations ranging from 3 to 15 mu g/kg. Furthermore, cell culture experiments using IHKE cells showed that the compounds that were detected in food samples are less cytotoxic in the formazan dye cytotoxicity assay compared to DON. Whereas DON revealed a median effective concentration (EC50) at 1.1 mu mol/L, all other compounds did not show any significant effect up to 100 mu mol/L. These findings indicate that the degradation of DON under thermal treatment might reduce the toxicity of DON contaminated food.