9,9'-二-O-(E)-阿魏酰开环异落叶松脂素 | 56973-66-1

• 物质功能分类: 天然产物 - 木脂素
• 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
• 中文名称: 9,9'-二-O-(E)-阿魏酰开环异落叶松脂素
• 英文名称: (-)-(2R,3R)-1,4-O-diferuloylsecoisolariciresinol
• 英文别名: (-)-9,9'-di-[O-(E)-feruloyl]secoisolariciresinol；9,9'-O-di-(E)-feruloyl-(-)-secoisolariciresinol；9,9'-O-diferuloyl-(-)-secoisolariciresinol；1,4-O-diferuloylsecoisolariciresinol；9,9'-Di-O-(E)-feruloylsecoisolariciresinol；[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxybutyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 56973-66-1
• 化学式: C₄₀H₄₂O₁₂
• 分子量: 714.766
• InChiKey: MOFDLYLEJWQRHD-KYHQCPCQSA-N

物化性质

• 熔点：
  181 °C
• 沸点：
  914.1±65.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  52
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  12

安全信息

• 储存条件：
  储存温度应保持在2-8℃，需干燥并密封保存。

制备方法与用途

1,4-二阿魏酰仲油酸蓖麻油醇（化合物7）是从金丝桃中分离得到的天然产物。这种化合物可用于癌症研究。

反应信息

• 作为反应物：
  描述：

  9,9'-二-O-(E)-阿魏酰开环异落叶松脂素 生成 [(2R,3R)-2,3-bis[(4-acetyloxy-3-methoxyphenyl)methyl]-4-[(E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoyl]oxybutyl] (E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  KARIKOME, HIROYUKI;MIMAKI, YOSHIHIRO;SASHIDA, YUTAKA, PHYTOCHEMISTRY, 30,(1991) N, C. 315-319

  摘要：

  DOI：
• 作为产物：
  描述：

  Dimethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 lithium 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 104.0h， 生成 9,9'-二-O-(E)-阿魏酰开环异落叶松脂素
  参考文献：
  名称：

  Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives

  摘要：

  One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the 1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 mu M except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.014

文献信息

• Chemical Evaluation of Betula Species in Japan. I. Constituents of Betula ermanii.
  作者：Hiroyuki FUCHINO、Tetsuya SATOH、Nobutoshi TANAKA

  DOI：10.1248/cpb.43.1937

  日期：——

  The constituents of Betula ermanii CHAM. in Japan were identified as follws. Fresh leaves : 20(S), 24(R)-epoxydammmaran-3β, 11α, 25-triol (1), 3-O-β-D-glucopyranoside of 1 (2), 2'-acetate of 2 (3), 11, 2'-diacetate of 2 (4), dammar-24-en-3β-, 11α-20(S)-triol (5), 3-O-β-D-2-O-acetylglucopyranoside of 5 (6). Outer bark : betulin (7), betulin 3-caffeate (8), oleanolic acid (9). Inner bark : (+)-lyoniresinol 3α-O-α-L-rhamnopyranoside (10), (-)-lyoniresinol 3α-O-β-D-xylopyranoside (11), 9, 9'di-O-feruloyl-(-)-secoisolariciresinol (12), acerogenin E (13), 3, 4, 5-trimethoxyphenol β-D-apiofuranosyl(1→6)-β-D-glucopyranoside (14), 4-(4-hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (15), (+)-catechine 7-O-β-D-xylopyranoside (16), lupeol (17), monogynol A (18). Root outer bark : lupeol caffeate (19), betulin 3-caffeate (8), oleanolic acid caffeate (20), dammarendiol II 3-caffeate (21). Compounds 2, 3, 4, 6, 19 and 21 are new.

  日本桦木（Betula ermanii CHAM.）的成分鉴定如下。鲜叶：20(S)，24(R)-epoxydammmaran-3β，11α，25-triol (1)，3-O-β-D-吡喃葡萄糖苷 1 (2)，2 的 2'-acetate (3)，11，2'-diacetate of 2 (4)，dammar-24-en-3β-，11α-20(S)-triol (5)，3-O-β-D-2-O-acetylglucopyranoside of 5 (6)。外树皮：白桦脂素（7）、白桦脂素 3-咖啡酸酯（8）、齐墩果酸（9）。内树皮 ：(+)-lyoniresinol 3α-O-α-L-rhamnopyranoside (10)，(-)-lyoniresinol 3α-O-β-D-xylopyranoside (11)，9, 9'di-O-feruloyl-(-)-secoisolariciresinol (12)，acerogenin E (13)，3, 4、5-trimethoxyphenolβ-D-apiofuranosyl(1→6)-β-D-glucopyranoside(14)、4-(4-羟基苯基)-2-丁醇 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside(15)、(+)-儿茶素 7-O-β-D-xylopyranoside(16)、羽扇豆醇 (17)、单炔醇 A (18)。根外树皮：羽扇豆醇咖啡酸酯（19）、白桦林 3-咖啡酸酯（8）、齐墩果酸咖啡酸酯（20）、达玛姻二醇 II 3-咖啡酸酯（21）。化合物 2、3、4、6、19 和 21 是新化合物。
• Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives
  作者：Eunyoung Lee、V.S. Jamal Ahamed、Mahto Sanjeev Kumar、Seog Woo Rhee、Surk-Sik Moon、In Seok Hong

  DOI：10.1016/j.bmcl.2011.09.014

  日期：2011.11

  One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the 1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 mu M except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. (C) 2011 Elsevier Ltd. All rights reserved.
• KARIKOME, HIROYUKI;MIMAKI, YOSHIHIRO;SASHIDA, YUTAKA, PHYTOCHEMISTRY, 30,(1991) N, C. 315-319
  作者：KARIKOME, HIROYUKI、MIMAKI, YOSHIHIRO、SASHIDA, YUTAKA

  DOI：——

  日期：——