(3S,7R)-illudin M | 1146-04-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: (3S,7R)-illudin M
• 英文别名: (3'R)-3'r,6't-dihydroxy-2',2',4',6'c-tetramethyl-2',3'-dihydro-spiro[cyclopropane-1,5'-inden]-7'-one；(3'R)-3'r,6't-Dihydroxy-2',2',4',6'c-tetramethyl-2',3'-dihydro-spiro[cyclopropan-1,5'-inden]-7'-on；(1R,5S)-1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-one
• CAS: 1146-04-9；19903-66-3
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: QVMDIQLUNODCTG-GXTWGEPZSA-N

物化性质

• 熔点：
  120-122.5° (Matsumoto); mp 128-130° (McMorris)
• 沸点：
  452.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

生物活性

Illudin M 是一种细胞毒性真菌倍半萜，可以从 O. olearius 蘑菇培养基中分离得到。它能够使 DNA 烷基化，并具有抗肿瘤活性。

体外研究

在体外实验中，Illudin M 在浓度为 0.01-10 μM 的范围内（24-120 小时）表现出细胞毒性并诱导凋亡。具体结果显示如下：

细胞系	浓度	培养时间	结果
胰腺癌 PANC-1	0.01 μM, 1 μM, 10 μM	24 小时、48 小时、72 小时、96 小时、120 小时	在肿瘤细胞中诱导凋亡（PANC-1 中为 86%；HT-29 中为 48%），但在正常人类皮肤成纤维细胞 (HFs) 中诱导的凋亡更为显著（89%）

这些结果表明 Illudin M 对多种癌细胞表现出较高的选择性和有效性。

反应信息

• 作为反应物：
  描述：

  (3S,7R)-illudin M 、 盐酸 生成 (1R,3R)-6-(2-chloroethyl)-2,2,5,7-tetramethyl-1,3-dihydroindene-1,3,4-triol
  参考文献：
  名称：

  MCMORRIS, TREVOR C.;KELNER, MICHAEL J.;CHADHA, RAJ K.;SIEGEL, JAY S.;MOON+, TETRAHEDRON, 45,(1989) N7, C. 5433-5440

  摘要：

  DOI：
• 作为产物：
  描述：

  Dihydroilludin M 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3S,7R)-illudin M
  参考文献：
  名称：

  Cytotoxic Illudane Sesquiterpenes from the Fungus Granulobasidium vellereum (Ellis and Cragin) Jülich

  摘要：

  Eight illudane sesquiterpenes were obtained from the wood-decomposing fungus Granulobasidium vellereum (Ellis and Cragin) Julich; among them were the enantiomers of the known compounds illudin M (1) and dihydroilludin M (4) and the diastereomers of illudin M (2) and illudin S (3), as well as two previously undescribed illudanes (5, 6). The cytotoxicity of compounds 14 and 6 was evaluated against two tumor cell lines (Huh7 and MT4), which showed that compounds 13 had potent cytotoxic activity, whereas compounds 4 and 6 had no or only moderate effects at concentrations up to 400 mu M. Surprisingly, both compounds 2 and 3 were about 10 times more potent than 1. When the chemical reactivity of 1 and 2 was tested, compound 2 was shown to have a substantially higher reaction rate when reacted both with 2 M HCl and with cysteine, indicating that the difference in cytotoxicity is probably due to chemical reactivity and not to enzymatic affinity.

  DOI：

  10.1021/acs.jnatprod.5b00500

文献信息

• Total Synthesis of (.+-.)-Illudin M
  作者：Frederick R. Kinder、Kenneth W. Bair

  DOI：10.1021/jo00102a020

  日期：1994.11

  (+/-)-Illudin M (1) was synthesized in six steps starting from 1-acetyl-1-(diazoacetyl)cyclopropane (4) and 4-bromo-5,5-dimethyl-2-cyclopentenone (5). The key step of the synthesis featured a carbonyl ylide 1,3-dipolar cycloaddition reaction that was mediated by the formation of a rhodium(II) carbenoid from 4 and catalytic rhodium(II) diacetate.

  以1-乙酰基-1-(叠氮乙酸基)环丙烷(4)和4-溴-5,5-二甲基-2-环戊烯酮(5)为起始原料，经过六步反应合成了(+/-)-伊卢丁 M（1）。其中的关键步骤是通过4与催化量的铑(II)二乙酸盐生成的铑(II)卡宾介导，完成了一个羰基烯胺的1,3-二极环加成反应。
• Total synthesis of dl-illudin M
  作者：Takeshi Matsumoto、Haruhisa Shirahama、Akitami Ichihara、Hyonsobb Shin、Shohei Kagawa、Fujio Sakan、Sojiro Matsumoto、Shuji Nishida

  DOI：10.1021/ja01014a077

  日期：1968.6
• MCMORRIS, TREVOR C.;KELNER, MICHAEL J.;CHADHA, RAJ K.;SIEGEL, JAY S.;MOON+, TETRAHEDRON, 45,(1989) N7, C. 5433-5440
  作者：MCMORRIS, TREVOR C.、KELNER, MICHAEL J.、CHADHA, RAJ K.、SIEGEL, JAY S.、MOON+

  DOI：——

  日期：——
• Cytotoxic Illudane Sesquiterpenes from the Fungus <i>Granulobasidium vellereum</i> (Ellis and Cragin) Jülich
  作者：Christina Nord、Audrius Menkis、Anders Broberg

  DOI：10.1021/acs.jnatprod.5b00500

  日期：2015.11.25

  Eight illudane sesquiterpenes were obtained from the wood-decomposing fungus Granulobasidium vellereum (Ellis and Cragin) Julich; among them were the enantiomers of the known compounds illudin M (1) and dihydroilludin M (4) and the diastereomers of illudin M (2) and illudin S (3), as well as two previously undescribed illudanes (5, 6). The cytotoxicity of compounds 14 and 6 was evaluated against two tumor cell lines (Huh7 and MT4), which showed that compounds 13 had potent cytotoxic activity, whereas compounds 4 and 6 had no or only moderate effects at concentrations up to 400 mu M. Surprisingly, both compounds 2 and 3 were about 10 times more potent than 1. When the chemical reactivity of 1 and 2 was tested, compound 2 was shown to have a substantially higher reaction rate when reacted both with 2 M HCl and with cysteine, indicating that the difference in cytotoxicity is probably due to chemical reactivity and not to enzymatic affinity.