(7S,8S,8'S)-4,4'-dibenzyloxy-3,3'-dimethoxy-7,9'-epoxylignane-4,4',9-triol | 1350444-52-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (7S,8S,8'S)-4,4'-dibenzyloxy-3,3'-dimethoxy-7,9'-epoxylignane-4,4',9-triol
• 英文别名: 4-[[(3S,4S,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
• CAS: 1350444-52-8
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: MHXCIKYXNYCMHY-STXHMFSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (7S,8S,8'S)-4,4'-dibenzyloxy-3,3'-dimethoxy-7,9'-epoxylignan-9-ol 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (7S,8S,8'S)-4,4'-dibenzyloxy-3,3'-dimethoxy-7,9'-epoxylignane-4,4',9-triol
  参考文献：
  名称：

  Stereoselective Syntheses of All Stereoisomers of Lariciresinol and Their Plant Growth Inhibitory Activities

  摘要：

  All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all cis stereoisomers, the 8-position configurations of which were achieved by employing stereoselective hydroboration. (-)-Lariciresinol and its 7S,8S,8'R stereoisomer inhibited the root growth of Italian ryegrass to 51-55% relative to the negative control, whereas other stereoisomers had less effect. These results demonstrate that the stereochemistry of lignans is one of the important factors influencing their inhibitory activity.

  DOI：

  10.1021/jf203222w

文献信息

• Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum
  作者：Zhi-Qiang Xia、Michael A Costa、John Proctor、Laurence B Davin、Norman G Lewis

  DOI：10.1016/s0031-9422(00)00242-9

  日期：2000.11

  Given the importance of the antitumor/antiviral lignans, podophyllotoxin and 5-methoxypodophyllotoxin, as biotechnological targets, their biosynthetic pathways were investigated in Podophyllum peltatum and Linum flavum. Entry into their pathways was established to occur via dirigent mediated coupling of E-coniferyl alcohol to afford (+)-pinoresinol; the encoding gene was cloned and the recombinant protein subsequently obtained. Radiolabeled substrate studies using partially purified enzyme preparations next revealed (+)-pinoresinol was enantiospecifically converted sequentially into (+)-lariciresinol and (-)-secoisolariciresinol via the action of an NADPH-dependent bifunctional pinoresinol/lariciresinol reductase. The resulting (-)-secoisolariciresinol was enantiospecifically dehydrogenated into (-)-matairesinol, as evidenced through the conversion of both radio- and stable isotopically labeled secoisolariciresinol into matairesinol, this being catalyzed by the NAD-dependent secoisolariciresinol dehydrogenase. (-)-Matairesinol was further hydroxylated to afford 7'-hydroxymatairesinol, this being efficiently metabolized into 5-methoxypodophyllotoxin. Thus much of the overall biosynthetic pathway to podophyllotoxin has been established, that is, from the dirigent mediated coupling of E-coniferyl alcohol to the subsequent conversions leading to 7'-hydroxymatairesinol. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Stereoselective Syntheses of All Stereoisomers of Lariciresinol and Their Plant Growth Inhibitory Activities
  作者：Hisashi Nishiwaki、Mitsuko Kumamoto、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf203222w

  日期：2011.12.28

  All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all cis stereoisomers, the 8-position configurations of which were achieved by employing stereoselective hydroboration. (-)-Lariciresinol and its 7S,8S,8'R stereoisomer inhibited the root growth of Italian ryegrass to 51-55% relative to the negative control, whereas other stereoisomers had less effect. These results demonstrate that the stereochemistry of lignans is one of the important factors influencing their inhibitory activity.