(8R)-3,3'-dimethoxy-4,4',9,9'-tetrahydroxy-5',8-lignan 3'-O-β-d-glucopyranoside

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (8R)-3,3'-dimethoxy-4,4',9,9'-tetrahydroxy-5',8-lignan 3'-O-β-d-glucopyranoside
• 化学式: C₂₅H₃₄O₁₁
• 分子量: 510.538
• InChiKey: FAEJRJHGZYVUEC-ZNPUKKALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  189.53
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (8R)-3,3'-dimethoxy-4,4',9,9'-tetrahydroxy-5',8-lignan 3'-O-β-d-glucopyranoside 在 三氟乙酸 作用下， 反应 2.0h， 生成 可得然胶
  参考文献：
  名称：

  Three new glycosides from the whole plant of Clematis lasiandra Maxim and their cytotoxicity

  摘要：

  Phytochemical investigation on the whole plant of Clematis lasiandra Maxim led to the isolation of two new phenolic glycosides (1 and 2), one new lignanoid glycoside (3), together with three known lignanoid glycosides (4-6). The structures of the new compounds were elucidated as 4-O-beta-D-galactopyranosylethyl-E-caffeate (1), 4-O-beta-D-galactopyranosyl-3-hydroxyl-phenylethene (2) and (8R)-3,3'-dimethoxy-4,4',9,9'-tetrahydroxy-5',8-lignan 3'-O-beta-D-glucopyranoside (3), on the basis of extensive spectral analysis and chemical evidence. The characteristic of the polymerized C-5'-C-8 type lignanoid aglycone in glycoside 3 was found from genus Clematis for the first time. Compounds 1-6 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, the new glycosides 1 and 2 showed significant cytotoxicity against those three tumor cell lines with IC50 in the range from 9.73 to 22.31 mu M, while lignanoid glycosides 3-6 showed weak cytotoxicity to those test cell lines with IC50 value more than 52.71 mu M. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.09.004

文献信息

• Three new glycosides from the whole plant of Clematis lasiandra Maxim and their cytotoxicity
  作者：Xiang-Rong Tian、Jun-Tao Feng、Zhi-Qing Ma、Na Xie、Jing Zhang、Xing Zhang、Hai-Feng Tang

  DOI：10.1016/j.phytol.2014.09.004

  日期：2014.12

  Phytochemical investigation on the whole plant of Clematis lasiandra Maxim led to the isolation of two new phenolic glycosides (1 and 2), one new lignanoid glycoside (3), together with three known lignanoid glycosides (4-6). The structures of the new compounds were elucidated as 4-O-beta-D-galactopyranosylethyl-E-caffeate (1), 4-O-beta-D-galactopyranosyl-3-hydroxyl-phenylethene (2) and (8R)-3,3'-dimethoxy-4,4',9,9'-tetrahydroxy-5',8-lignan 3'-O-beta-D-glucopyranoside (3), on the basis of extensive spectral analysis and chemical evidence. The characteristic of the polymerized C-5'-C-8 type lignanoid aglycone in glycoside 3 was found from genus Clematis for the first time. Compounds 1-6 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, the new glycosides 1 and 2 showed significant cytotoxicity against those three tumor cell lines with IC50 in the range from 9.73 to 22.31 mu M, while lignanoid glycosides 3-6 showed weak cytotoxicity to those test cell lines with IC50 value more than 52.71 mu M. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.