(-)-heraclenol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (-)-heraclenol
• 英文别名: 9-[(2S)-2,3-dihydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: FOINLJRVEBYARJ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-heraclenol 、 乙酸酐 在 吡啶 作用下， 反应 48.0h， 以24.9 mg的产率得到(+)-heraclenol acetate
  参考文献：
  名称：

  来自Magydaris pastinacea的香豆素作为与肿瘤相关的碳酸酐酶IX和XII的抑制剂：分离，生物学研究和计算机评估。

  摘要：

  在对高等植物中人碳酸酐酶（hCA）抑制剂的体外筛选中，Magydaris pastinacea种子的石油醚和乙酸乙酯提取物选择性抑制hCA IX和hCA XII亚型。对提取物的植物化学研究导致分离出十个线性呋喃香豆素（1-10），四个简单的香豆素（12-15）和新的角二氢呋喃香豆素（11）。基于1 D和2 D NMR，MS和ECD数据分析，阐明了分离出的化合物的结构。所有分离的化合物均对普遍存在的胞质亚型hCA I和II无活性（Ki> 10,000 nM），而对与肿瘤相关的亚型hCA IX和XII具有显着活性。伞形肾上腺素是最有效的香豆素抑制hCA XII亚型，Ki为5.7 nM。

  DOI：

  10.1080/14756366.2020.1713114
• 作为产物：
  描述：

  Claucoumarin C 在 盐酸 作用下， 以 水 为溶剂， 反应 8.0h， 生成 (-)-heraclenol
  参考文献：
  名称：

  Bioactive furanocoumarins from stems of Clausena lansium

  摘要：

  Clausena lansium Skeels, a member of the Rutaceae, is a shrub or small tree with grapelike fruits. Several parts of this plant have been used in folk medicine. A bioactive constituent investigation of the stems of C lansium herein resulted in isolation of four furanocoumarins, claucoumarins A-D, and 13 known analogs. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, MS, and NMR experiments, and their absolute configurations were determined by CD experiments. Using an in vitro system, several of these compounds showed selective neuroprotective effects at a concentration of 10 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.08.002

文献信息

• Chemical profile of the roots of Clausena lansium and their inhibitory effects of the over-activation in BV-2 microglial cells
  作者：Yingjie Wang、Gang Chen、Di Zhou、Libin Xu、Qingqi Meng、Bin Lin、Jinle Hao、Fuxin Sun、Yue Hou、Ning Li

  DOI：10.1016/j.phytochem.2024.114008

  日期：2024.4
• Coumarins from<i>Magydaris pastinacea</i>as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation
  作者：Benedetta Fois、Simona Distinto、Rita Meleddu、Serenella Deplano、Elias Maccioni、Costantino Floris、Antonella Rosa、Mariella Nieddu、Pierluigi Caboni、Claudia Sissi、Andrea Angeli、Claudiu T. Supuran、Filippo Cottiglia

  DOI：10.1080/14756366.2020.1713114

  日期：2020.1.1

  In an in vitro screening for human carbonic anhydrase (hCA) inhibiting agents from higher plants, the petroleum ether and ethyl acetate extracts of Magydaris pastinacea seeds selectively inhibited hCA IX and hCA XII isoforms. The phytochemical investigation of the extracts led to the isolation of ten linear furocoumarins (1-10), four simple coumarins (12-15) and a new angular dihydrofurocoumarin (11)

  在对高等植物中人碳酸酐酶（hCA）抑制剂的体外筛选中，Magydaris pastinacea种子的石油醚和乙酸乙酯提取物选择性抑制hCA IX和hCA XII亚型。对提取物的植物化学研究导致分离出十个线性呋喃香豆素（1-10），四个简单的香豆素（12-15）和新的角二氢呋喃香豆素（11）。基于1 D和2 D NMR，MS和ECD数据分析，阐明了分离出的化合物的结构。所有分离的化合物均对普遍存在的胞质亚型hCA I和II无活性（Ki> 10,000 nM），而对与肿瘤相关的亚型hCA IX和XII具有显着活性。伞形肾上腺素是最有效的香豆素抑制hCA XII亚型，Ki为5.7 nM。
• Bioactive furanocoumarins from stems of Clausena lansium
  作者：Hang Liu、Fei Li、Chuang-Jun Li、Jing-Zhi Yang、Li Li、Nai-Hong Chen、Dong-Ming Zhang

  DOI：10.1016/j.phytochem.2014.08.002

  日期：2014.11

  Clausena lansium Skeels, a member of the Rutaceae, is a shrub or small tree with grapelike fruits. Several parts of this plant have been used in folk medicine. A bioactive constituent investigation of the stems of C lansium herein resulted in isolation of four furanocoumarins, claucoumarins A-D, and 13 known analogs. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, MS, and NMR experiments, and their absolute configurations were determined by CD experiments. Using an in vitro system, several of these compounds showed selective neuroprotective effects at a concentration of 10 mu M. (C) 2014 Elsevier Ltd. All rights reserved.