secoisolariciresinol-4',4''-diacetate | 1206712-52-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: secoisolariciresinol-4',4''-diacetate
• 英文别名: [4-[(2R,3R)-3-[(4-acetyloxy-3-methoxyphenyl)methyl]-4-hydroxy-2-(hydroxymethyl)butyl]-2-methoxyphenyl] acetate
• CAS: 1206712-52-8
• 化学式: C₂₄H₃₀O₈
• 分子量: 446.497
• InChiKey: PSOKFLHWZQAZQK-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  开环异落叶松树脂酚 、 乙酰氯 反应 12.0h， 以63%的产率得到secoisolariciresinol-4',4''-diacetate
  参考文献：
  名称：

  DNA-protector and cytotoxic activity of secoisolariciresinol diglucoside derivatives

  摘要：

  研究了苯丙烷木脂素的化学结构与DNA保护剂和细胞毒活性之间的关系。从亚麻种子中分离的木脂素开环异落叶松树脂醇二葡萄糖苷 (SDG) 合成类似物。结果表明，SDG 衍生物开环异落叶松树脂醇和开环异落叶松树脂醇-4',4"-二乙酸酯（非糖苷）在体外表现出比起始木脂素更高的细胞毒活性。苷元酚羟基乙酰化后，细胞毒性略有升高，而 DNA 保护剂活性则大幅降低。不含碳水化合物的衍生物的DNA保护活性略高于起始SDG的活性。这是通过丁二醇羟基与自由基的结合来解释的。有人提出，细胞毒性衍生物的活性是通过诱导肿瘤细胞凋亡来介导的。

  DOI：

  10.1007/s10600-010-9720-4

文献信息

• Antiestrogenic and antiproliferative potency of secoisolariciresinol diglucoside derivatives on MCF-7 breast cancer cells
  作者：Alexander M. Scherbakov、Olga V. Stasevich、Diana I. Salnikova、Olga E. Andreeva、Ekaterina I. Mikhaevich

  DOI：10.1080/14786419.2020.1826479

  日期：2021.12.17

  Secoisolariciresinol diglucoside (SDG) is isolated fromLinum usitatissimumseeds. The antiproliferative effects of SDG(1)and its derivatives secoisolariciresinol(2)and secoisolariciresinol-4 ', 4 ''-diacetate (3)have been evaluated on MCF-7 breast cancer cells and normal breast epithelial line MCF-10A. Lignan1has not shown cytotoxic effects on MCF-7 cells, while derivatives2and3have inhibited cell growth with IC(50)values of 25 and 11 mu M, respectively. Estrogen receptor alpha is a key growth driver in MCF-7 cells. Compound1did not affect the activity of ER alpha, while derivatives2and3showed significant antiestrogenic effects. Compounds2and3caused apoptosis in the MCF-7 line, determined by the cleavage of PARP. SDG derivative3enhanced the effect of doxorubicin. SDG derivatives can be considered as promising agents that exhibit a combined antiestrogen and proapoptotic effect in hormone-dependent breast cancer cells.