T-2 mycotoxin | 21259-20-1

• 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: T-2 mycotoxin
• 英文别名: [(1S,2R,4S,7R,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: 21259-20-1
• 化学式: C₂₄H₃₄O₉
• 分子量: 466.5
• InChiKey: BXFOFFBJRFZBQZ-PPFYZKLNSA-N

物化性质

• 熔点：
  151.5℃
• 比旋光度：
  D26 +15° (c = 2.58 in ethanol)
• 沸点：
  489.35°C (rough estimate)
• 密度：
  1.1942 (rough estimate)
• 闪点：
  2 °C
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL； DMSO:PBS(pH7.2)(1:1)：0.5mg/ml；乙醇：20mg/mL
• 颜色/状态：
  White needles from benzene & Skellysolve B; acetate deriv: amorphous solid from ether & pentane
• 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。 环氧化合物基团...似乎是其毒理学活性的关键；肝脏通过环氧化物水解酶来解毒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-脱乙酰新萎蒿醇...和新萎蒿醇... 从HT2-三线霉素也得到了相同的代谢物，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

T2-三环脱氧烯容易通过猪和鼠的皮肤和肠道吸收。

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

估计那些每天口服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/千克的T-2毒素，含有0.9微克的这种物质。

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。在小鼠口服给药后30分钟和豚鼠肌肉注射后，血浆中的放射性标记物达到最大水平……。在通过饲料给予(3)H-T-2毒素的雏鸡中，血液、血浆、腹脂肪、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，而在肌肉、皮肤、胆汁和胆囊中则在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)

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,S28,S36,S36/37,S36/37/39,S45
• 危险类别码：
  R20/21/22,R38,R36,R26/27/28,R11
• WGK Germany：
  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

概述

T-2毒素是由镰刀菌产生的A类单端孢霉烯族真菌毒素中毒性最强的一种，对人畜危害较大。它广泛分布于全球各地的玉米和小麦田间作物以及库存谷物中，并在1973年被联合国粮农组织（FAO）和世界卫生组织（WHO）列为天然存在的危险食品污染毒物之一。

性质

T-2毒素是一种四环倍半萜烯化合物，化学名为4β-15-二乙酰氧基-3α-羟基-8α-(3-甲基丁酰氧)-12,13-环氧单端孢霉-9-烯，分子式为C₂₄H₃₄O₉。该毒素性质稳定，在食物生产和加工过程中不易被高压灭菌灭活。需在200～210℃下灭菌30～40分钟或浸泡于NaClO-NaOH溶液中至少4小时才能灭活。一些真菌和酶可以改变并去除T-2毒素的毒性，而环氧环和双键被认为是主要的毒性基团。

生物活性

T-2毒素（T-2 Mycotoxin）是由各种镰刀菌种产生的真菌毒素，在小鼠和大鼠中的半数致死量分别为5.2 mg/kg BWa和1.5 mg/kg BWa。在动物体内，T-2毒素可以转化为多种代谢产物，如HT-2毒素和T-2-triol，这些均为水解产物。

该毒素作为抑制肽基转移酶（60s核糖体亚基）结合及蛋白质合成的抑制剂，在DNA和RNA的合成、磷脂代谢方面干扰，并增加肝脏中脂质过氧化物的水平。此外，它还能在免疫系统、胃肠道组织以及胎儿组织中诱导细胞凋亡。