5-epi-ilimaquinone | 96806-31-4

• 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: 5-epi-ilimaquinone
• 英文别名: epi-ilimaquinone；3-[[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 96806-31-4
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: JJWITJNSXCXULM-UPOGBMBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-epi-ilimaquinone 在 sodium dithionite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以66%的产率得到5-epi-ilimaquinol
  参考文献：
  名称：

  Exerting DNA Damaging Effects of the Ilimaquinones through the Active Hydroquinone Species

  摘要：

  拥有醌基团的海绵源倍半萜醌物质ilimaquinone（1）被假设通过氧化还原循环过程表达其细胞毒性，产生可导致DNA损伤的活性产物。为了确定1的DNA损伤效应并检查氧化还原转化是否参与其功能，测试并比较了1、相应的氢醌（2）和氢醌三乙酸酯（3）以及它们的5-表异构体（4-6）的DNA损伤性质。直接与质粒DNA孵育时，氢醌是唯一能够切割DNA的活性物种。然而，在细胞基础试验中，醌和氢醌三乙酸酯的活性与相应的氢醌相同，并且所有物质以类似的方式损伤细胞DNA。当细胞预先暴露于NAD（P）H：醌氧还原酶1（NQO1）抑制剂二香豆素时，1和4的原位还原得到了支持，其细胞毒性降低。结果确认了ilimaquinones 1和4的DNA损伤活性，并表明需要经历原位转化为活性氢醌，从而作为细胞毒性机制的一部分发挥DNA损伤性质。

  DOI：

  10.3390/scipharm89020026

文献信息

• A Ring-Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators
  作者：Laurent Evanno、David Lachkar、Assia Lamali、Asmaa Boufridi、Blandine Séon-Méniel、Florent Tintillier、Denis Saulnier、Stéphanie Denis、Grégory Genta-Jouve、Jean-Christophe Jullian、Karine Leblanc、Mehdi A. Beniddir、Sylvain Petek、Cécile Debitus、Erwan Poupon

  DOI：10.1002/ejoc.201800047

  日期：2018.6.7

  focussed biological activities of this library were also investigated; quorum sensing activity of Vibrio harveyi was envisaged and some of the new compounds were shown to be good quorum sensing inhibitor candidates, whereas others were activators. Toxicities were also evaluated and some products showed micromolar activities against human umbilical vein endothelium, human hepatocellular carcinoma and human

  我们在此报告了一种应用于海洋天然物质 ilimaquinone 和 5-epi-ilimaquinone 的环扭曲策略。合成了一个化学多样化的分子库，包括倍半萜部分的重排和醌环的原始重组。化学信息学分析评估了结构多样性的兴起和化学空间的探索。还研究了该文库的一些重点生物活性；设想了哈维弧菌的群体感应活性，并且一些新化合物被证明是良好的群体感应抑制剂候选物，而其他化合物则是激活剂。还评估了毒性，一些产品显示出对人脐静脉内皮、人肝细胞癌和人肺癌 (A549) 细胞的微摩尔活性。
• Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis
  作者：Asmaa Boufridi、David Lachkar、Dirk Erpenbeck、Mehdi A. Beniddir、Laurent Evanno、Sylvain Petek、Cécile Debitus、Erwan Poupon

  DOI：10.1071/ch16455

  日期：——

  Dactylospongia metachromia and Dactylospongia elegans collected from French Polynesia were studied with a particular focus on the variation of the diastereomeric ratio between ilimaquinone (4) and 5-epi-ilimaquinone (5). More than 100 samples, covering an area of 4100 km2, were studied to try to clarify this intriguing issue. Nuclear magnetic resonance appeared as the non-destructive, straightforward technique of choice for a relative quantitative study. A random distribution, unique at that point in nature, is observed and leads to biosynthetic considerations. Biological evaluation of both compounds was also performed and showed moderate discrepancies in cytotoxicity and apoptosis induction.

  研究人员对从法属波利尼西亚采集到的 Dactylospongia metachromia 和 Dactylospongia elegans 进行了研究，重点研究了ilimaquinone（4）和 5-epi-ilimaquinone （5）之间非对映异构体比例的变化。研究了 100 多个样本，覆盖面积达 4100 平方公里，试图弄清这个有趣的问题。核磁共振似乎是进行相对定量研究的非破坏性、直接的首选技术。研究人员观察到了自然界中独一无二的随机分布，并由此引发了生物合成方面的思考。此外，还对这两种化合物进行了生物学评估，结果显示它们在细胞毒性和诱导细胞凋亡方面存在一定差异。
• Exerting DNA Damaging Effects of the Ilimaquinones through the Active Hydroquinone Species
  作者：Apisada Jiso、Laphatrada Yurasakpong、Sirorat Janta、Kulathida Chaithirayanon、Anuchit Plubrukarn

  DOI：10.3390/scipharm89020026

  日期：——

  Possessing the quinone moiety, ilimaquinone (1), a sponge–derived sesquiterpene quinone, has been hypothesised to express its cytotoxicity through a redox cycling process, yielding active product(s) that can cause DNA damage. To determine the DNA damaging effects of 1 and examine whether a redox transformation may participate in its functions, the DNA damaging properties of 1, the corresponding hydroquinone (2) and hydroquinone triacetates (3) and their 5-epimeric counterparts (4–6) were tested and compared. When incubated directly with plasmid DNA, the hydroquinones were the only active species capable of cleaving the DNA. In cell-based assays, however, the quinones and hydroquinone triacetates were active in the same range as that of the corresponding hydroquinones, and all damaged the cellular DNA in a similar manner. The in situ reduction of 1 and 4 were supported by the decreases in the cytotoxicity when cells were pre-exposed to dicoumarol, an NAD(P)H:quinone oxidoreductase 1 (NQO1) inhibitor. The results confirmed the DNA damaging activities of the ilimaquinones 1 and 4, and indicated the necessity to undergo an in-situ transformation into the active hydroquinones, thereby exerting the DNA damaging properties as parts of the cytotoxic mechanisms.

  拥有醌基团的海绵源倍半萜醌物质ilimaquinone（1）被假设通过氧化还原循环过程表达其细胞毒性，产生可导致DNA损伤的活性产物。为了确定1的DNA损伤效应并检查氧化还原转化是否参与其功能，测试并比较了1、相应的氢醌（2）和氢醌三乙酸酯（3）以及它们的5-表异构体（4-6）的DNA损伤性质。直接与质粒DNA孵育时，氢醌是唯一能够切割DNA的活性物种。然而，在细胞基础试验中，醌和氢醌三乙酸酯的活性与相应的氢醌相同，并且所有物质以类似的方式损伤细胞DNA。当细胞预先暴露于NAD（P）H：醌氧还原酶1（NQO1）抑制剂二香豆素时，1和4的原位还原得到了支持，其细胞毒性降低。结果确认了ilimaquinones 1和4的DNA损伤活性，并表明需要经历原位转化为活性氢醌，从而作为细胞毒性机制的一部分发挥DNA损伤性质。