T-2 toxin | 239106-70-8

• 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: T-2 toxin
• 英文别名: T2 toxin；toxin T2；[(1S,2R,4S,7R,9R,10R,11S,12R)-11-acetyloxy-2-(acetyloxymethyl)-10-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-yl] 3-methylbutanoate
• CAS: 239106-70-8
• 化学式: C₂₄H₃₄O₉
• 分子量: 466.529
• InChiKey: BXFOFFBJRFZBQZ-FHAHJZMBSA-N

物化性质

• 沸点：
  544.9±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 颜色/状态：
  White needles from benzene & Skellysolve B; acetate deriv: amorphous solid from ether & pentane
• 熔点：
  151.5 °C
• 溶解度：
  In water, 95.9 mg/L at 25 °C (est)
• 蒸汽压力：
  3.06X10-11 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Stable in the solid form
• 旋光度：
  Specific optical rotation: (c = 2.58 in ethanol): +15 °C at 26 °C/D
• 分解：
  Hazardous decomposition products formed under fire conditions. - Carbon oxides

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

ADMET

代谢

给一头哺乳期母牛口服180毫克T-2毒素后，从其尿液中获得了两种主要代谢物。它们是3'-羟基-HT 2毒素和3'-羟基T 2毒素。

Two major metabolites were obtained from the urine of a lactating cow given 180 mg of T-2 toxin orally. They were 3'-hydroxy-HT 2 toxin & 3'-hydroxy T 2 toxin.

来源:Hazardous Substances Data Bank (HSDB)

代谢

人类肝脏酶在体外将T2-三线镰刀菌毒素去乙酰化成HT2-三线镰刀菌毒素。

Human liver enzymes deacetylate T2-trichothecene to HT2-trichothecene in vitro.

来源:Hazardous Substances Data Bank (HSDB)

代谢

口服给予小鼠和大鼠(3)H-T2-三线霉素(1 mg/kg体重)的放射性，在72小时内以粪便(55%)和尿液(15%)的形式回收。 ... 分析大鼠粪便中回收的放射性，发现剂量的2.7%以未改变的T2-三线霉素形式排出，7.5%以4-O-脱乙酰化T2-三线霉素(HT2-三线霉素)形式排出...其余的粪便排泄产物未鉴定。 在尿液中，鉴定出HT2-三线霉素，占总剂量的1.4%，以及8-羟基二乙酰氧基斯卡波醇(1.8%)；还分离出3种未鉴定的代谢物...。 环氧基团...似乎是它的毒理学活性的关键；肝脏通过环氧水解酶来解毒T2-三线霉素。 在体外，大鼠肝脏匀浆将T2-三线霉素代谢为HT2-三线霉素，T2-三线霉素四醇，4-脱乙酰新线醇...和新线醇... 从HT2-三线霉素中也获得了相同的代谢物，这表明T2-三线霉素优先在C-4位置水解，生成NT2-三线霉素。

The radioactivity of orally admin (3)H-T2-trichothecene (1 mg/kg body wt) to mice & rats was recovered in feces (55%) & urine (15%) within 72 hr. ... Analysis of the radioactivity recovered in feces of rats revealed that 2.7% of the dose was excreted as unchanged T2-trichothecene & 7.5% as 4-O-deacetylated T2-trichothecene (HT2-trichothecene)...the remaining fecal excretion products were not identified. In urine, HT2-trichothecene, representing 1.4% of the total dose & 8-hydroxydiacetoxyscirpenol (1.8%) were identified; 3 unidentified metabolites...were also isolated. The epoxide moeity...seems to be essential for its toxicological activity; the liver detoxifies T2-trichothecene, probably through epoxide hydrolase. In vitro, rat liver homogenate metabolizes T2-trichothecene to HT2-trichothecene, T2-trichothecene tetraol, 4-deacetylneosolaniol...& neosolaniol... The same metabolites were obtained from HT2-trichothecene, indicating that T2-trichothecene was preferentially hydrolyzed at the C-4 position to give NT2-trichothecene.

来源:Hazardous Substances Data Bank (HSDB)

代谢

曲霉菌属产生的三环烯类是倍半萜类毒素。由于这些霉菌毒素非常稳定，因此对微生物转化产生了兴趣，这些转化能够去除被污染的谷物或谷物产品中的毒素。对23种属于毛霉科（子囊菌门，子囊菌亚门）的酵母菌种进行了测试，包括四种毛霉科物种和19种目前归类于芽枝霉属的无性物种，以检测它们将三环烯T-2毒素转化为较少毒性产物的能力。这些物种产生了三种生物转化类型：乙酰化形成3-乙酰T-2毒素，糖基化形成T-2毒素3-葡萄糖苷，以及去除异戊酰基团形成新构菌醇。一些物种产生了多种生物转化类型。三种芽枝霉属物种将T-2毒素转化为T-2毒素3-葡萄糖苷，这是一种在曲霉感染的谷物中被识别为隐蔽霉菌毒素的化合物。这是首次报告微生物全细胞方法生产三环烯糖苷，T-2毒素3-葡萄糖苷的大量可用性将促进毒性测试和开发检测农业和其他产品中这种化合物的方法。

Trichothecenes are sesquiterpenoid toxins produced by Fusarium species. Since these mycotoxins are very stable, there is interest in microbial transformations that can remove toxins from contaminated grain or cereal products. Twenty-three yeast species assigned to the Trichomonascus clade (Saccharomycotina, Ascomycota), including four Trichomonascus species and 19 anamorphic species presently classified in Blastobotrys, were tested for their ability to convert the trichothecene T-2 toxin to less-toxic products. These species gave three types of biotransformations: acetylation to 3-acetyl T-2 toxin, glycosylation to T-2 toxin 3-glucoside, and removal of the isovaleryl group to form neosolaniol. Some species gave more than one type of biotransformation. Three Blastobotrys species converted T-2 toxin into T-2 toxin 3-glucoside, a compound that has been identified as a masked mycotoxin in Fusarium-infected grain. This is the first report of a microbial whole-cell method for producing trichothecene glycosides, and the potential large-scale availability of T-2 toxin 3-glucoside will facilitate toxicity testing and development of methods for detection of this compound in agricultural and other products.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：没有关于来自串珠镰刀菌的毒素对人类致癌性的数据。T-2毒素在实验动物中的致癌性有有限证据。总体评估：来自串珠镰刀菌的毒素对人类的致癌性无法分类（第3组）。

Evaluation: No data were available on the carcinogenicity to humans of toxins derived from Fusarium sporotrichioides. There is limited evidence in experimental animals for the carcinogenicity of T-2 toxin. Overall evaluation: Toxins derived from Fusarium sporotrichiodes are not classifiable as to their carcinogenicity to humans (Group 3).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：T2-三线镰孢霉毒素

IARC Carcinogenic Agent:T2-Trichothecene

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第31卷：（1983年）某些食品添加剂、饲料添加剂和天然存在物质

IARC Monographs:Volume 31: (1983) Some Food Additives, Feed Additives and Naturally Occurring Substances

来源:International Agency for Research on Cancer (IARC)

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

吸收、分配和排泄

T2-三嗪烯能轻易通过猪和鼠的皮肤和肠道被吸收。

T2-Trichothecene is readily absorbed through skin & the gut in pigs & rats.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

T-2毒素会通过哺乳期牛和猪的乳汁传播。

T-2 toxin is transmitted in the milk in lactating cattle & pigs.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

估计每天口服1毫克/千克体重的T-2毒素，连续8天的鸡所产的蛋，相当于饮食中含有的1.6毫克/千克T-2毒素，含有0.9微克此物质。

Estimated that the eggs from chickens treated orally with 1 mg T-2 toxin/kg body weight daily for 8 consecutive days, which is equivalent to 1.6 mg/kg dietary T-2, contain 0.9 ug of this material.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

口服给予小鼠和大鼠(3)H-T2-三线霉素(1 mg/kg体重)后，72小时内通过粪便(55%)和尿液(15%)排出。它分布在肝脏、肾脏和其他器官中，没有特定的积累。

The radioactivity of orally admin (3)H-T2-trichothecene (1 mg/kg body wt) to mice & rats was recovered in feces (55%) & urine (15%) within 72 hr. It was distributed in the liver, kidneys & other organs, without specific accumulation.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(3)H-T-2毒素口服给予小鼠和大鼠后，迅速分布到组织中，并通过粪便和尿液排出。口服给药后，小鼠血浆中放射性标记物含量在30分钟内达到最大值……，而豚鼠在肌肉注射后……也达到最大值。在通过饲料给予(3)H-T-2毒素的雏鸡中，血液、血浆、腹脂、心脏、肾脏、肌胃、肝脏和剩余胴体中的最大水平在4小时内达到，而肌肉、皮肤、胆汁和胆囊中的最大水平在12小时内达到……。T-2毒素在猪组织中的分布与鸡相似……。

(3)H-T-2 Toxin given orally to mice and rats was distributed rapidly to tissues and eliminated in feces and urine. Maximal levels of radiolabel were found after 30 min in plasma of mice after oral administration ... and of guinea pigs after intramuscular injection ... . In chicks administered (3)H-T-2 toxin in the diet, maximal levels were reached by 4 hr in blood, plasma, abdominal fat, heart, kidneys, gizzard, liver and the remainder of the carcass and by 12 hr in muscle, skin, bile and gall bladder ... . The distribution of T-2 toxin in tissues of swine was similar to that in chickens ... .

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  己二酸酐 、 T-2 toxin 在 吡啶 作用下， 反应 4.0h， 生成 T-2 hemiadipate
  参考文献：
  名称：

  单克隆抗体的生产以及间接竞争性酶联免疫吸附试验的发展，用于筛选牛奶中的T-2毒素。

  摘要：

  为了快速监测牛奶中的T-2毒素，产生了针对T-2毒素单克隆抗体（mAb）的高度特异性，并开发了一种灵敏的间接竞争性酶联免疫吸附测定（ic-ELISA）。首先将T-2毒素转化为T-2-己二酸酐（T-2HA），然后合成匙孔血蓝蛋白（KLH）和病毒样颗粒（VLP）并与T-2HA偶联，作为包被和免疫原抗原，分别。接种雌性Balb / c小鼠并融合细胞后，产生了高亲和力的mAb。优化后，开发的ic-ELISA的50％抑制浓度（IC50）估计为0.137 ng mL-1。基于该mAb，使用稀释方法开发了优化的ic-ELISA方案以制备牛奶样品。牛奶中T-2毒素的检出限为0.827 ng mL-1，加标样品（2.5、5和10 ng mL-1）中T-2毒素的平均回收率在85.0％至98.9％之间，CV在6.1％至8.6％之间。ic-ELISA通过HPLC-MS / MS方法验证，所有结果表明，它是检测牛奶中T-2毒素的合适筛选方法。

  DOI：

  10.1016/j.toxicon.2018.10.307
• 作为产物：
  描述：

  4β,15-diacetoxy-3α-(2-tetrahydropyranyloxy)scirpene 在 selenium(IV) oxide 、 4-甲基苯磺酸吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 25.0h， 生成 T-2 toxin
  参考文献：
  名称：

  Synthesis of HT-2 toxin, neosolaniol, T-2 toxin, 3'-hydroxy T-2 toxin, and sporotrichiol from anguidine by routes involving hydroxyl inversion/esterification

  摘要：

  DOI：

  10.1021/jo00391a063

文献信息

• MYCOTOXIN ADSORBANT BASED ON A BETAINE DERIVATIVE FOR BALANCED ANIMAL FEED
  申请人：NUTEK, S.A. DE C.V.

  公开号：EP3476477A1

  公开（公告）日：2019-05-01

  The present invention provides a mycotoxin adsorbent based on a highly specific betaine derivative for trichothecenes A and B, and especially for vomitoxin (or deoxynivalenol) and T-2 toxin; as well as a process for preparing said mycotoxin adsorbent. The mycotoxin adsorbent of the invention is obtained by modifying the surface of an aluminosilicate by means of an organic amphoteric compound with a carboxyl group that provides it with high polarity properties. The mycotoxin adsorbent is useful for preparing balanced feed from animals that avoid the toxic effects of mycotoxins.

  本发明提供了一种基于高特异性甜菜碱衍生物的霉菌毒素吸附剂，可吸附单端孢霉烯 A 和 B，特别是呕吐毒素（或脱氧雪腐镰刀菌醇）和 T-2 毒素；还提供了一种制备上述霉菌毒素吸附剂的工艺。本发明的霉菌毒素吸附剂是通过一种带有羧基的有机两性化合物对硅酸铝表面进行改性而得到的，这种改性使其具有高极性。这种霉菌毒素吸附剂可用于配制均衡的动物饲料，以避免霉菌毒素的毒性影响。
• Adsorbent of micotoxins based on a betaine derivative for balanced animal foods
  申请人：Nutek, S.A. DE C.V.

  公开号：US10806164B2

  公开（公告）日：2020-10-20

  The present invention provides a mycotoxin adsorbent based on a highly specific betaine derivative for trichothecenes A and B, and especially for vomitoxin (or deoxynivalenol) and T-2 toxin; as well as a process for preparing said mycotoxin adsorbent. The mycotoxin adsorbent of the invention is obtained by modifying the surface of an aluminosilicate by means of an organic amphoteric compound with a carboxyl group that provides it with high polarity properties. The mycotoxin adsorbent is useful for preparing balanced feed from animals that avoid the toxic effects of mycotoxins.

  本发明提供了一种基于高特异性甜菜碱衍生物的霉菌毒素吸附剂，可吸附单端孢霉烯 A 和 B，特别是呕吐毒素（或脱氧雪腐镰刀菌醇）和 T-2 毒素；还提供了一种制备上述霉菌毒素吸附剂的工艺。本发明的霉菌毒素吸附剂是通过一种带有羧基的有机两性化合物对硅酸铝表面进行改性而得到的，这种改性使其具有高极性。这种霉菌毒素吸附剂可用于配制均衡的动物饲料，以避免霉菌毒素的毒性影响。
• Trichothecene-transforming alcohol dehydrogenase, method for transforming trichothecenes and trichothecene-transforming additive
  申请人：Erber Aktiengesellschaft

  公开号：US11001812B2

  公开（公告）日：2021-05-11

  An alcohol dehydrogenase of sequence ID numbers 2, 3 or 4 containing metal ions and a quinone cofactor, or in addition, a functional variant exhibiting a sequence identity of at least 80%, preferably at least 86%, especially preferred at least 89% and at least one redox cofactor for the transformation of at least one trichothecene exhibiting a hydroxyl group on the C-3 atom, as well as a method for the enzymatic transformation of trichothecenes and a trichothecene-transforming additive.

  一种序列 ID 号为 2、3 或 4 的醇脱氢酶，含有金属离子和醌辅助因子，或此外还含有一种功能变体，其序列同一性至少为 80%，优选至少为 86%，特别优选至少为 89%，并含有至少一种氧化还原辅助因子，用于转化至少一种 C-3 原子上带有羟基的单端孢霉烯，以及一种单端孢霉烯酶促转化方法和一种单端孢霉烯转化添加剂。
• ANDERSON, D. W.;BLACK, R. M.;LEIGH, D. A.;STODDART, J. F., TETRAHEDRON LETT., 28,(1987) N 23, 2653-2656
  作者：ANDERSON, D. W.、BLACK, R. M.、LEIGH, D. A.、STODDART, J. F.

  DOI：——

  日期：——
• IMPROVED POLYPEPTIDES CAPABLE OF CONVERTING SUBSTRATE 3-KETO- DEOXYNIVALENOL INTO 3-EPI- DEOXYNIVALENOL
  申请人：Erber Aktiengesellschaft

  公开号：EP4022047A1

  公开（公告）日：2022-07-06