1α,5α-dihydroxyisozaluzanin C | 142808-76-2

• 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: 1α,5α-dihydroxyisozaluzanin C
• 英文别名: (3aS,6aR,8R,9aS,9bS)-6a,8,9a-trihydroxy-3,6,9-trimethylidene-3a,4,5,7,8,9b-hexahydroazuleno[4,5-b]furan-2-one
• CAS: 142808-76-2
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: IICSMQDQXPQQJS-OEMOEHNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1α,5α-dihydroxyisozaluzanin C 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(3S,3aS,6aR,8R,9aS,9bS)-6a,8,9a-Trihydroxy-3-methyl-6,9-dimethylene-decahydro-azuleno[4,5-b]furan-2-one
  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
• 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 12.17h， 生成 1α,5α-dihydroxyisozaluzanin 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

• Potential allelopathic activity of several sesquiterpene lactone models
  作者：Francisco A. Macías、Juan Carlos G. Galindo、Guillermo M. Massanet

  DOI：10.1016/0031-9422(92)80343-d

  日期：1992.6

  and synthetic sesquiterpene lactones with eudesmanolide, melampolide, cis,cis -germacranolide, and guaianolide skeletons have been prepared and tested as allelochemicals. The effect of a series of aqueous solutions at 10 −4 -10 −9 M ofthis collection is evaluated. The specific structural requirements related to their activity is discussed. The natural sesquiterpene lactones soulangianolide A, melampomagnolide

  摘要 已制备并测试了 12 种天然和合成倍半萜内酯的集合，这些内酯具有 eudesmanolide、melampolide、cis、cis-germacranolide 和 guaianolide 骨架。评估了该集合的10 -4 -10 -9 M 处的一系列水溶液的效果。讨论了与其活动相关的具体结构要求。已使用SeO 2 和叔丁基过氧化氢从木香内酯、小白菊内酯和脱氢木香内酯合成天然倍半萜内酯soulangianolide A、melampomagnolide A和B、zaluzanin C和isozaluzanin C。合成化合物的结构通过核磁共振光谱确定。
• Fungicidal activity of natural and synthetic sesquiterpene lactone analogs
  作者：D.E. Wedge、J.C.G. Galindo、F.A. Macı́as

  DOI：10.1016/s0031-9422(00)00008-x

  日期：2000.4

  Fungicidal activity of 36 natural and synthetic sesquiterpene lactones with guaianolide, trans, trans-germacranolide, cis, cis-germacranolide, melampolide, and eudesmanolide carbon skeletons was evaluated against the phytopathogenic fungi Colletotrichum acutatum, C. fragariae, C. gloeosporioides, Fusarium oxysporum, Botrytis cinerea, and Phomopsis sp. Dose-response data for the active compounds dehydrozaluzanin

  评估了 36 种天然和合成倍半萜内酯与愈创木酚内酯、反式、反式-germacranolide、顺式、顺式-germacranolide、melampolide 和eudesmanolide 碳骨架对植物病原真菌Colletotrichum acutatum、C. fragariae、C. gloeosporium, gloeosporioides 的杀真菌活性Botrytis cinerea 和 Phomopsis sp。提供了活性化合物 dehydrozaluzanin C、dehydrocostuslactone、5alpha-hydroxydehydrocostuslacone、costunolide 和 zaluzanin C 的剂量反应数据。一种新的 96 孔微生物测定程序用于快速轻松地评估抗真菌活性，用于将这些化合物与商业杀菌剂标准进行比较。还提出了一些构效结论。
• Bioprospection of Phytotoxic Plant-Derived Eudesmanolides and Guaianolides for the Control of <i>Amaranthus viridis</i>, <i>Echinochloa crus-galli</i>, and <i>Lolium perenne</i> Weeds
  作者：Jesús G. Zorrilla、David M. Cárdenas、Carlos Rial、José M.G. Molinillo、Rosa M. Varela、Marco Masi、Francisco A. Macías

  DOI：10.1021/acs.jafc.3c06901

  日期：2024.1.24

  phytotoxicities of a selection of eudesmanolides and guaianolides, including natural products and new derivatives obtained by semisynthesis from plant-isolated sesquiterpene lactones, were evaluated in bioassays against three weeds of concern in agriculture (Amaranthus viridis L., Echinochloa crus-galli L., and Lolium perenne L.). Both eudesmanolides and guaianolides were active against the root and

  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
• 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