HT-2 toxin | 26934-87-2

• 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
• 英文名称: HT-2 toxin
• 英文别名: 15-acetoxy-3α,4β-dihydroxy-8α-[3-methylbutyryloxy]-12,13-epoxytrichothec-9-ene；HT2-toxin；ALX-630-113-M001；mycotoxin HT-2；HT-2；[(1S,2R,4S,7R,9R,10R,11S,12S)-2-(acetyloxymethyl)-10,11-dihydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-yl] 3-methylbutanoate
• CAS: 26934-87-2
• 化学式: C₂₂H₃₂O₈
• 分子量: 424.491
• InChiKey: PNKLMTPXERFKEN-MLXHEQMXSA-N

物化性质

• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 闪点：
  2 °C
• 溶解度：
  二氯甲烷：5 mg/ml； DMSO：可溶；乙醇：可溶
• 碰撞截面：
  203 Ų [M+NH4]+ [CCS Type: TW, Method: calibrated with polyalanine]

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  Xn,T+,F,T
• 安全说明：
  S16,S22,S26,S36/37,S36/37/39,S45
• 危险类别码：
  R20/21/22,R36,R36/37/38,R26/27/28,R11
• WGK Germany：
  2,3
• 海关编码：
  29329990
• 危险品运输编号：
  UN 3462 6.1/PG 1
• 包装等级：
  I
• 危险类别：
  6.1(a)

制备方法与用途

生物活性方面，HT-2毒素是T-2毒素的活性去乙酰化代谢物，能够抑制植物蛋白质合成及细胞增殖。

反应信息

• 作为反应物：
  描述：

  HT-2 toxin 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 1.0h， 生成 4α,15-Diacetoxy-3α-hydroxy-8α-<(3-methylbutyryl)oxy>-12,13-epoxytrichothec-9-ene
  参考文献：
  名称：

  Structure-activity studies of trichothecenes: cytotoxicity of analogs and reaction products derived from T-2 toxin and neosolaniol

  摘要：

  Forty-two analogues and reaction products derived from T-2 toxin or neosolaniol were assayed for their cytotoxicity to cultured mouse lymphoma cells. Structure-activity relationships confirmed the stereospecific nature of the cytotoxic action of T-2. Cytotoxicity was particularly susceptible to changes at C3, C4, C9, and C10 but was relatively unaffected by changes at C8, which appears to represent a region of steric tolerance in the interaction of T-2 with a cellular constituent. The most potent compounds were T-2, diacetoxyscirpenol, and a series of C8 ester analogues 11 and 31-35.

  DOI：

  10.1021/jm00123a008
• 作为产物：
  描述：

  T-2 toxin 在 水 作用下， 反应 6.0h， 生成 4,15-diacetoxy-10,12-cyclohexa-(10H)-3,9,12-trihydroxy-8-(3-methylbutyryloxy)trichothecene 、 HT-2 toxin
  参考文献：
  名称：

  Structural Elucidation of T-2 Toxin Thermal Degradation Products and Investigations toward Their Occurrence in Retail Food

  摘要：

  The stability of T-2 toxin under the conditions of baking or cooking was investigated using heating experiments with the model substances alpha-D-glucose, alpha-D-methyl-glucopyranosid, N-alpha-acetyl-L-lysine methyl ester, and N-alpha-acetyl-cysteine methyl ester. The reaction residue was screened for degradation products using gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography with evaporative light-scattering detection (HPLC-ELSD). Although T-2 toxin was degraded under all conditions, only heating of T-2 toxin with a-D-glucose produced a mixture of three degradation products, which were isolated and identified by MS and nuclear magnetic resonance (NMR) experiments. The reaction mechanism for the formation of the T-2 degradation products was elucidated by quantum chemical calculations. The relevance of these degradation products was investigated by baking experiments as well as the analysis of retail food samples. In cell-culture studies using immortalized human kidney epithelial (IHKE) cells, the T-2 degradation products were less cytotoxic (formazan dye cytotoxicity assay) compared to T-2 toxin.

  DOI：

  10.1021/jf803516s

文献信息

• UDP-Glucosyltransferases from Rice, Brachypodium, and Barley: Substrate Specificities and Synthesis of Type A and B Trichothecene-3-O-β-d-glucosides
  作者：Herbert Michlmayr、Elisabeth Varga、Alexandra Malachová、Philipp Fruhmann、Marta Piątkowska、Christian Hametner、Jana Šofrová、Günther Jaunecker、Georg Häubl、Marc Lemmens、Franz Berthiller、Gerhard Adam

  DOI：10.3390/toxins10030111

  日期：——

  abilities to glucosylate the most relevant type A and B trichothecenes. HvUGT13248, which prefers nivalenol over deoxynivalenol, is also able to conjugate C-4 acetylated trichothecenes (e.g., T-2 toxin) to some degree while OsUGT79 and Bradi5g03300 are completely inactive with C-4 acetylated derivatives. The type A trichothecenes HT-2 toxin and T-2 triol are the kinetically preferred substrates in the

  单端孢菌素毒素是多种植物病原性镰刀菌属物种已证实或怀疑的毒力因子。植物可以通过糖基化作用在不同程度上解毒，这是一种由 UDP-葡萄糖基转移酶 (UGT) 催化的反应。由于许多单端孢菌烯-葡萄糖结合物的分析标准品不可用，因此有关此类化合物的信息有限。在此，先前鉴定的脱氧雪腐镰刀菌烯醇缀合 UGT HvUGT13248（大麦）、OsUGT79（大米）和 Bradi5g03300（短柄草）在大肠杆菌中表达，经过亲和纯化，并表征了它们对最相关的 A 型和 B 型单端孢霉烯族化合物进行糖基化的能力。 HvUGT13248 更喜欢雪腐镰刀菌烯醇而不是脱氧雪腐镰刀菌烯醇，它也能够在一定程度上缀合 C-4 乙酰化单端孢霉烯族化合物（例如 T-2 毒素），而 OsUGT79 和 Bradi5g03300 对 C-4 乙酰化衍生物完全没有活性。对于 HvUGT13248 和 Bradi5g03300，A 型单端孢霉烯族毒素
• HT-2 Toxin 4-Glucuronide as New T-2 Toxin Metabolite: Enzymatic Synthesis, Analysis, and Species Specific Formation of T-2 and HT-2 Toxin Glucuronides by Rat, Mouse, Pig, and Human Liver Microsomes
  作者：Tanja Welsch、Hans-Ulrich Humpf

  DOI：10.1021/jf302571y

  日期：2012.10.10

  spectroscopy (NMR) and mass spectrometry revealed that besides T-2 toxin glucuronide and HT-2 toxin 3-glucuronide also the newly identified isomer HT-2 toxin 4-glucuronide was formed. Glucuronidation of T-2 and HT-2 toxin in liver microsomes of rat, mouse, pig, and human was compared and metabolites were analyzed directly by liquid chromatography coupled with tandem mass spectrometry (LC–MS/MS). A distinct

  霉菌毒素T-2毒素的葡萄糖苷酸及其I期代谢产物HT-2毒素是体内和体外重要的II期代谢产物情况。由于标准物质对于直接定量这些葡糖醛酸苷是必不可少的，因此优化了利用肝脏微粒体酶促合成T-2和HT-2毒素葡糖醛酸苷的方法。通过核磁共振波谱（NMR）和质谱的结构阐明，除了T-2毒素葡糖苷酸和HT-2毒素3-葡糖苷酸外，还形成了新鉴定的异构体HT-2毒素4-葡糖醛酸。比较了大鼠，小鼠，猪和人肝微粒体中T-2和HT-2毒素的葡萄糖醛酸苷化，并通过液相色谱-串联质谱（LC-MS / MS）直接分析了代谢产物。观察到独特的，物种特异性的T-2和HT-2毒素的葡萄糖醛酸化模式，并且存在有趣的个体差异。直到最近，在通过β-葡糖醛酸糖苷酶酶促切割葡糖醛酸化物后，通过定量糖苷配基，经常间接地分析了葡糖醛酸化物。因此，使用来自植物的β-葡糖醛酸糖苷酶可水解T-2和HT-2毒素葡糖醛酸糖的水解效率。比较了螺旋血球，牛肝和大肠杆菌。
• CD additivity in trichothecene benzoates: application as a microanalytical method for trichothecene characterization
  作者：Eugene M. Oltz、Koji Nakanishi、Boris Yagen、David G. Corley、George E. Rottinghaus、Michael S. Tempesta

  DOI：10.1016/s0040-4020(01)90546-0

  日期：——

  The additivity relation in values of split CD curves previously established with pyranose p-bromobenzoates was shown to be valid for p-bromobenzoates of the cage-like trichothecene system (which also possesses a primary hydroxyl group). This suggests that additivity is generally valid even for congested multichromophoric molecules. The relation has been integrated Into a new micro method for trichothecene

  已显示先前用吡喃糖对溴苯甲酸酯建立的拆分CD曲线值的可加性关系对于笼形三茂金属体系（也具有伯羟基）的对溴苯甲酸酯是有效的。这表明，加性一般甚至对于拥挤的多发色分子也是有效的。该关系已被整合到一种新的用于表征单端孢烯的微方法中，该方法已被用于亚微克水平的（MC-72083）中的一种新的单端孢烯。
• Novel 3,4- and 8,15-polyether analogues of macrocyclic trichothecenes
  作者：Derek W. Anderson、Robin M. Black、David A. Leigh、J.Fraser Stoddart

  DOI：10.1016/s0040-4039(00)96174-4

  日期：1987.1
• The catalytic activity of cytochrome P450 3A22 is critical for the metabolism of T-2 toxin in porcine reservoirs
  作者：Xiaohu Ge、Junping Wang、Jing Liu、Jun Jiang、Huina Lin、Jun Wu、Man Ouyang、Xianqing Tang、Ming Zheng、Ming Liao、Yiqun Deng

  DOI：10.1016/j.catcom.2010.08.003

  日期：2010.11

  Contamination of food by T 2 toxin a trichothecene mycotoxin poses a serious threat to human health We report the identification of cytochrome P450 3A22 (CYP3A22) responsible for 3' hydroxylation of T-2 and HT-2 in pigs The present study shows that T-2 toxin significantly induces CYP3A22 expression in primary piglet hepatocytes Moreover recombinant pig CYP3A22 converted T-2 toxin into TC-1 (3'-OH T-2 toxin) and HT 2 toxin into TC-3 (3'-OH HT-2 toxin) in vitro These results suggest that pig CYP3A22 primarily eliminates T-2 and HT-2 toxins by 3'-hydroxylation of isovaleryl groups Therefore CYP3A22 is critical for xenobiotic metabolism and endogenous biochemical biotransformation of trichothecene mycotoxin in porcine reservoirs (C) 2010 Elsevier B V All rights reserved