5α-hydroxy-isozaluzanin C | 142808-75-1

• 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: 5α-hydroxy-isozaluzanin C
• 英文别名: 5alpha-Hydroxyisozaluzanin C；(3aS,6aS,8R,9aS,9bS)-8,9a-dihydroxy-3,6,9-trimethylidene-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• CAS: 142808-75-1
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: HMESILYTXGPCSC-DKBOKBLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5α-hydroxy-isozaluzanin C 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 氯仿 、 水 为溶剂， 以28 %的产率得到1α,5α-dihydroxyisozaluzanin C
  参考文献：
  名称：

  植物毒性植物来源的 Eudesmanolides 和 Guaianolides 的生物勘探用于控制 Amaranthus viridis、Echinochloa crus-galli 和 Lolium perenne 杂草

  摘要：

  在生物测定中，针对农业中关注的三种杂草（Amaranthus viridis L.、Echinochloa crus-galli L. 和 Lolium perenne）评估了一系列 Eudesmanolides 和 guajanolides 的植物毒性，包括天然产物和通过植物分离倍半萜内酯半合成获得的新衍生物L.).Eudesmanolides 和 愈创木内酯 均对所有物种的根和芽生长具有活性，其中 eudesmanolides 普遍表现出改进的活性。用作阳性对照的除草剂获得的 IC50 值（分别在根和芽生长时，A. viridis：27.8 和 85.7 μM;E. crus-galli：167.5 和 288.2 μM;L. perenne： 99.1 和 571.4 μM）在大多数病例中得到改善。讨论了结构-活性关系，发现 A 环和 C-13 的羟基化以及羟基的位置、数量和方向以及

  DOI：

  10.1021/acs.jafc.3c06901
• 作为产物：
  描述：

  去氢木香内酯 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以60%的产率得到5α-hydroxy-isozaluzanin C
  参考文献：
  名称：

  Sesquiterpene Lactones with Potential Use as Natural Herbicide Models. 2. Guaianolides

  摘要：

  A structure-activity study to evaluate the effect of 17 guaianolide sesquiterpene lactones (in a range of 100-0.001 muM) on the growth and germination of several mono- and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. Specific conditions for the selective mono- or polyhydroxylation of guaianolides using the SeO2/tert-butyl hydroperoxide system are presented and discussed. The high regio- and stereoselectivities of the reaction are explained through the specific structural requirements of the bulky first adduct formed during the ene reaction. These compounds appear to have deeper effects on the growth of either monocots or dicots than the previously tested germacranolides. Otherwise, the lactone group seems to be necessary for the activity, though it does not necessarily need to be unsaturated. However, the presence of a second and easily accessible unsaturated carbonyl system greatly enhances the inhibitory activity. Lipophilicity and the stereochemistry of the possible anchoring sites are also crucial factors for the activity. Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead compounds.

  DOI：

  10.1021/jf0005364

文献信息

• Application of Hansch's Model to Guaianolide Ester Derivatives:  A Quantitative Structure−Activity Relationship Study
  作者：Francisco A. Macías、Raúl F. Velasco、Diego Castellano、Juan C. G. Galindo

  DOI：10.1021/jf048703d

  日期：2005.5.1

  Data show a strong influence of lipophilia, expressed as logP values. Specially, data from alkylic side chain ester derivatives adjust to the mathematical model based on Hansch's transport theory; hence, a quantitative structure-activity relationships (QSAR) correlation with a high degree of reliance is provided. Moreover, all active compounds fit the Lipinski's rule of five. Also, the presence of additional

  进行了一项定量结构活性研究，以评估亲脂性/水溶性对黄化胚芽鞘胚延长的影响，已使用34个具有不同数目的羟基和不同长度和结构的酯侧链的愈创木酚内酯：直链，支链，芳族和不饱和。已对化合物的浓度范围在10到1000 microM之间进行了测试。数据显示出亲脂性的强烈影响，表示为logP值。特别地，来自烷基侧链酯衍生物的数据会根据Hansch的运输理论调整为数学模型。因此，提供了高度依赖的定量构效关系（QSAR）相关性。此外，所有活性化合物均符合Lipinski的五个规则。还，基本骨架中其他羟基及其衍生物的存在不会影响作用方式，但会极大地影响活性，因为它们会改变通过膜和水相的传输。最后，第二个羟基通过增加范德华相互作用的差异来增强烷基侧链衍生物之间活性的差异。
• Dehydrozaluzanin C: a potent plant growth regulator with potential use as a natural herbicide template
  作者：Francisco A. Macı́as、Juan C.G. Galindo、José M.G. Molinillo、Diego Castellano

  DOI：10.1016/s0031-9422(00)00070-4

  日期：2000.5

  dehydrozaluzanin C (former DHZ) is a sesquiterpene lactone obtained from different weeds of the Compositae family. Its potential as a plant growth regulator has been evaluated by using a phytotoxic allelopathic bioassay, where the commercial herbicide Logran is used as internal reference. The evaluation is made based on their effects on germination and growth over several dicotyledon and monocotyledon species. The

  天然产物 dehydrozaluzanin C（原 DHZ）是从菊科不同杂草中获得的倍半萜内酯。它作为植物生长调节剂的潜力已通过使用植物毒性化感生物测定进行评估，其中商业除草剂 Logran 用作内部参考。评估基于它们对几种双子叶植物和单子叶植物物种的萌发和生长的影响。在 1000-0.001 microM 范围内测试了活性。在几乎所有情况下，DHZ 在 1000 microM 时比内部参考更活跃，其活性低于 100 microM 时的内部参考水平。这些结果证实 DHZ 是一种有效的植物生长调节剂，是开发新除草剂模型的良好候选者。
• Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents
  作者：Yuan-Zhen Xu、Xue-Yan Gu、Shou-Jiao Peng、Jian-Guo Fang、Ying-Mei Zhang、De-Jun Huang、Jian-Jun Chen、Kun Gao

  DOI：10.1016/j.ejmech.2015.03.001

  日期：2015.4

  Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive alpha-methylene-gamma-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 mu M. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design. (C) 2015 Published by Elsevier Masson SAS.
• Developing new herbicide models from allelochemicals
  作者：Francisco A Macías、Juan C G Galindo、José M G Molinillo、Diego Castellano、Raúl F Velasco、David Chinchilla

  DOI：10.1002/(sici)1096-9063(199906)55:6<662::aid-ps3>3.0.co;2-q

  日期：1999.6
• Sesquiterpene Lactones with Potential Use as Natural Herbicide Models. 2. Guaianolides
  作者：Francisco A. Macías、Juan C. G. Galindo、Diego Castellano、Raúl F. Velasco

  DOI：10.1021/jf0005364

  日期：2000.11.1

  A structure-activity study to evaluate the effect of 17 guaianolide sesquiterpene lactones (in a range of 100-0.001 muM) on the growth and germination of several mono- and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. Specific conditions for the selective mono- or polyhydroxylation of guaianolides using the SeO2/tert-butyl hydroperoxide system are presented and discussed. The high regio- and stereoselectivities of the reaction are explained through the specific structural requirements of the bulky first adduct formed during the ene reaction. These compounds appear to have deeper effects on the growth of either monocots or dicots than the previously tested germacranolides. Otherwise, the lactone group seems to be necessary for the activity, though it does not necessarily need to be unsaturated. However, the presence of a second and easily accessible unsaturated carbonyl system greatly enhances the inhibitory activity. Lipophilicity and the stereochemistry of the possible anchoring sites are also crucial factors for the activity. Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead compounds.