1,4,8-trihydroxy-3-naphthalenecarboxylic acid 1-O-β-D-glucopyranoside ethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,4,8-trihydroxy-3-naphthalenecarboxylic acid 1-O-β-D-glucopyranoside ethyl ester
• 英文别名: 1,4,8-trihydroxy-3-naphthalenecarboxylic acid-1-O-β-D-glucopyranoside ethyl ester
• 化学式: C₁₉H₂₂O₁₀
• 分子量: 410.378
• InChiKey: XQAZFDNLTGAOLS-PITHAFQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.39
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  166.14
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,4,8-trihydroxy-3-naphthalenecarboxylic acid 1-O-β-D-glucopyranoside ethyl ester 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 可得然胶
  参考文献：
  名称：

  Studies on Cytotoxic Activity against HepG-2 Cells of Naphthoquinones from Green Walnut Husks of Juglans mandshurica Maxim

  摘要：

  从胡桃楸（Juglans mandshurica Maxim）的青核桃壳中分离出27种萘醌及其衍生物，包括4种新的萘基葡萄糖苷和23种已知化合物。通过大量光谱分析，阐明了4种新的萘基葡萄糖苷的结构。通过MTT（3-(4,5-二甲基-2-噻唑基)-2,5-二苯基溴化四唑）检测法，评估了所有这些化合物对人类肝癌细胞系HepG-2生长的细胞毒性活性。结果表明，大多数萘醌的无糖苷形式在体外表现出比萘基葡萄糖苷更好的细胞毒性，IC50值在7.33-88.23μM之间。同时，讨论了这些化合物的初步结构活性关系。

  DOI：

  10.3390/molecules200915572

文献信息

• Studies on Cytotoxic Activity against HepG-2 Cells of Naphthoquinones from Green Walnut Husks of Juglans mandshurica Maxim
  作者：Yuanyuan Zhou、Bingyou Yang、Yanqiu Jiang、Zhaoxi Liu、Yuxin Liu、Xiaoli Wang、Haixue Kuang

  DOI：10.3390/molecules200915572

  日期：——

  Twenty-seven naphthoquinones and their derivatives, including four new naphthalenyl glucosides and twenty-three known compounds, were isolated from green walnut husks, which came from Juglans mandshurica Maxim. The structures of four new naphthalenyl glucosides were elucidated based on extensive spectroscopic analyses. All of these compounds were evaluated for their cytotoxic activities against the growth of human cancer cells lines HepG-2 by MTT [3-(4,5-dimethylthiazo l-2-yl)-2,5 diphenyl tetrazolium bromide] assay. The results were shown that most naphthoquinones in an aglycone form exhibited better cytotoxicity in vitro than naphthalenyl glucosides with IC50 values in the range of 7.33–88.23 μM. Meanwhile, preliminary structure-activity relationships for these compounds were discussed.

  从胡桃楸（Juglans mandshurica Maxim）的青核桃壳中分离出27种萘醌及其衍生物，包括4种新的萘基葡萄糖苷和23种已知化合物。通过大量光谱分析，阐明了4种新的萘基葡萄糖苷的结构。通过MTT（3-(4,5-二甲基-2-噻唑基)-2,5-二苯基溴化四唑）检测法，评估了所有这些化合物对人类肝癌细胞系HepG-2生长的细胞毒性活性。结果表明，大多数萘醌的无糖苷形式在体外表现出比萘基葡萄糖苷更好的细胞毒性，IC50值在7.33-88.23μM之间。同时，讨论了这些化合物的初步结构活性关系。