葚孢菌素 | 1456-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 葚孢菌素
• 英文名称: sporidesmin A
• 英文别名: sporidesmin；(1R,2R,3S,11R,14R)-6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
• CAS: 1456-55-9
• 化学式: C₁₈H₂₀ClN₃O₆S₂
• 分子量: 473.958
• InChiKey: QTONANGUNATZOU-ICTVWZTPSA-N

物化性质

• 熔点：
  179° (dependent on rate of heating)
• 比旋光度：
  D20 -45° (c = 0.98 in methanol)
• 沸点：
  761.4±60.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  9

ADMET

毒理性

• 毒性总结

Sporidesmin及其还原（二硫醇）形式会与谷胱甘肽和其他硫醇进行循环还原/自动氧化反应，产生有毒的超氧自由基、过氧化氢和羟基自由基。它靶向肝脏，引起周围胆管炎和胆管阻塞，导致胆汁成分在血液中积聚。在牲畜中，这会导致叶红素积累，叶红素是由反刍动物瘤胃中微生物降解叶绿素产生的一种光动力代谢物。高血浆水平的叶红素会使动物对阳光变得敏感。（A3097, A3098）

Sporidesmin and its reduced (dithiol) form undergo cyclic reduction/autoxidation reactions with glutathione and other thiols, generating toxic superoxide radicals, hydrogen peroxide, and hydroxy radicals. It targets the liver, causing pericholangitis and the occlusion of bile ducts, which leads to the accumulation of bile constitutents in the bloodstream. In livestock, this results in a build up of phylloerythrin, a photodyamic metabolite produced by the microbial degradation of chlorophyll in the rumen. High plasma levels of phylloerythrin cause the animals to become sensitive to sunlight. (A3097, A3098)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

未列在IARC（国际癌症研究机构）的名单上。

Not listed by IARC.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

Sporidesmin是一种强烈的肝毒素，会导致胆管周围炎和胆管阻塞，进而导致胆汁成分在血液中积聚。这已知会导致家畜出现pithomycotoxicosis（面部湿疹，其特征是对光过敏）。Sporidesmin也可能对人类具有致癌性。

Sporidesmin is a potent hepatotoxin, causing liver damage from pericholangitis and the occlusion of bile ducts, which results in the accumulation of bile constitutents in the bloodstream. This is known to lead to pithomycotoxicosis (facial eczema, characterized by photosensitisation) in livestock. Sporidesmin may also be carcinogenic in humans. (A3095, A3096)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服、皮肤、吸入和parenteral（被污染的药物）。

Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

Sporidesmin导致腹泻和食欲不振。Pithomycotoxicosis的特征是皮肤的光敏反应。

Sporidesmin causes diarrhea and lack of appetite. Pithomycotoxicosis is characterized by photosensitisation of the skin. (A3095)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  6.1(b)
• 包装等级：
  III
• 危险类别：
  6.1(b)

反应信息

• 作为反应物：
  描述：

  葚孢菌素 在 双氧水 、 三苯基膦 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 生成 Dethiosporidesminsulfoxid
  参考文献：
  名称：

  Sporidesmins。第十一部分。三苯基膦与表聚硫代二氧杂哌嗪的反应

  摘要：

  脱氢gliotoxin和sporidesmin与三苯膦反应生成表硫代二氧杂哌嗪和三苯膦硫化物。该反应涉及二氧杂哌嗪环的不对称中心的差向异构化。用过酸处理时，亚砜中的表硫二氧杂哌嗪和这些化合物是外消旋的。提出的证据表明，杀孢子素E与三苯基膦的反应主要发生在与硫结合的硫原子上，并且该三硫化物的一种构象优先与另一种构象反应。

  DOI：

  10.1039/j39710001189
• 作为产物：
  描述：

  11b,12c-diacetoxy-10-chloro-8,9-dimethoxy-2ξ-(4-methoxy-phenyl)-4,7,14-trimethyl-(6at,11bt)-6a,7,11b,12-tetrahydro-4,12a-azaethano-[1,3,5]dithiazepino[5',4':1,5]pyrrolo[2,3-b]indole-5,13-dione 生成 葚孢菌素
  参考文献：
  名称：

  孢子菌素A的全合成。

  摘要：

  DOI：

  10.1021/ja00800a079

文献信息

• Sporidesmins. Part X. Synthesis of polysulphides by reaction of dihydrogen disulphide with disulphides and thiols
  作者：S. Safe、A. Taylor

  DOI：10.1039/j39700000432

  日期：——

  disulphide was slow. By contrast phenylmethanethiol reacted smoothly with the reagent to give di-, tri-, tetra-, and penta-sulphides, and this oxidation appears to be general. The epitrithiadioxopiperazines were light-sensitive and were converted photolytically into equimolecular mixtures of di-, and tetra-sulphides. By use of 35S-labelled polysulphides it was shown that the photolysed sulphur was that inserted

  sporidesmin E的结构表明，它是由sporidesmin通过类似于过氧化物酶的硫化酶生物合成的。因此，已经研究了二硫化二氢与杀孢子素，脱氢胶质毒素和其他二硫化物的反应。在所有情况下均获得多硫化物，但是二苄基二硫化物与二氢二硫化物的反应缓慢。相比之下，苯甲硫醇与试剂平稳反应，生成二硫化物，三硫化物，四硫化物和五硫化物，这种氧化似乎很普遍。Epitrithiadioxopiperazines对光敏感，可以光解为二硫化物和四硫化物的等分子混合物。通过使用35 S-标记的多硫化物，表明光解的硫是由二硫化二氢插入的硫。
• Lipoxygenase genes, promoters, transit peptides and proteins thereof
  申请人：——

  公开号：US20040103453A1

  公开（公告）日：2004-05-27

  This invention describes novel lipoxygenase genes and promoters, transit peptides and proteins derived therefrom. More specifically, this invention describes novel promoters that confer chemically inducible but not wound- or pathogen-inducible expression to an associated nucleotide sequence. The invention further describes peptides capable of targeting and associated protein to plastids and proteins having lipoxygenase activity which can be used to inhibit fungal mycotoxins. The invention also describes recombinant sequences containing such promoter sequences, and/or sequences encoding transit peptides and proteins according to the invention. The said recombinant DNA sequences may be used to create transgenic plants, but especially transgenic plants expressing a nucleotide sequence of interest in response to chemicals but not in response to wounding or pathogens.

  本发明描述了新型的脂氧合酶基因和启动子、转运肽和由此衍生的蛋白质。更具体地，本发明描述了赋予化学诱导但不是伤口或病原体诱导表达与相关核苷酸序列相关的新型启动子。该发明还描述了能够将相关蛋白质定向到质体的肽和具有脂氧合酶活性的蛋白质，可用于抑制真菌毒素。该发明还描述了包含此类启动子序列和/或根据本发明编码转运肽和蛋白质的序列的重组序列。这些重组DNA序列可用于创建转基因植物，尤其是在对化学物质做出反应但不对伤口或病原体做出反应的转基因植物表达感兴趣的核苷酸序列。
• Curable Composition
  申请人：Kato Hidetoshi

  公开号：US20080119620A1

  公开（公告）日：2008-05-22

  The curable composition of this invention is a curable composition comprising 1 to 20 parts by weight of an organic peroxide and 0.0005 to 10 parts by weight of a redox reaction initiator containing at least one metal selected from copper, iron, lead, potassium, manganese, indium, nickel and cobalt per 100 parts by weight of a polysulfide polymer with a viscosity of 0.5 to 50 Pa·s at 25° C. The curable composition of this invention has good curing properties. The cured material obtained by curing the curable composition of this invention is not swollen or does not decline in strength even if it is immersed in hot water for a long period of time, showing good water resistance. The curable composition of this invention can be suitably used as a sealant of double glazings, aircraft, civil engineering and architecture.

  本发明的可固化组合物是一种可固化组合物，其包括有机过氧化物1至20重量份和氧化还原反应引发剂0.0005至10重量份，其中每100重量份聚硫化物粘度为0.5至50 Pa·s，所述氧化还原反应引发剂包含至少一种金属，所述金属包括铜、铁、铅、钾、锰、铟、镍和钴。本发明的可固化组合物具有良好的固化性能。使用本发明的可固化组合物固化得到的固化材料即使长时间浸泡在热水中也不会膨胀或强度下降，具有良好的耐水性。本发明的可固化组合物可适用于双层玻璃、飞机、土木工程和建筑的密封剂。
• Immunoregulation
  申请人：THE AUSTRALIAN NATIONAL UNIVERSITY

  公开号：EP0163475A2

  公开（公告）日：1985-12-04

  Donor tissue is treated prior to implantation in a recipient with a compound from the class known as epipolythiodioxopiperazines in order to prevent graft rejection.

  在将捐献组织植入受体之前，先用一种被称为环戊氧哌嗪的化合物对其进行处理，以防止移植排斥反应。
• Sequence-determined DNA fragments and corresponding polypeptides encoded thereby
  申请人：Ceres Incorporated

  公开号：EP1033405A2

  公开（公告）日：2000-09-06

  The present invention provides DNA molecules that constitute fragments of the genome of a plant, and polypeptides encoded thereby. The DNA molecules are useful for specifying a gene product in cells, either as a promoter or as a protein coding sequence or as an UTR or as a 3' termination sequence, and are also useful in controlling the behavior of a gene in the chromosome, in controlling the expression of a gene or as tools for genetic mapping, recognizing or isolating identical or related DNA fragments, or identification of a particular individual organism, or for clustering of a group of organisms with a common trait. 0Arabidopsis DNA is used in the present experiment, but the procedure is a general one.

  本发明提供了构成植物基因组片段的 DNA 分子及其编码的多肽。这些 DNA 分子可作为启动子或蛋白质编码序列或 UTR 或 3'终止序列，用于指定细胞中的基因产物，也可用于控制染色体中基因的行为，控制基因的表达，或作为基因绘图、识别或分离相同或相关 DNA 片段、或识别特定生物个体、或对具有共同性状的生物群体进行聚类的工具。 本实验中使用的是拟南芥 DNA，但这是一个通用程序。