(-)-medioresinol | 125638-34-8

• 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: (-)-medioresinol
• 英文别名: 4-[(3R,3aS,6R,6aS)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol
• CAS: 125638-34-8
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: VJOBNGRIBLNUKN-HANNOOJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-(7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5-tetramethoxy-7,9':7',9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol 在 sodium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 120.0h， 以0.9 mg的产率得到(-)-medioresinol
  参考文献：
  名称：

  Lignans and Neolignans from Sinocalamus affinis and Their Absolute Configurations

  摘要：

  Twenty-two new lignans and neolignans (1-22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and egthro aryl glycerol units in different neolignans and the CD data [particularly the Rh-2(OCOCF3)(4)-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 mu M, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 +/- 5.9% and 71.7 +/- 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 +/- 2.8% to 91.6 +/- 6.4%, 107.2 +/- 8.0%, and 97.6 +/- 8.5%, respectively.

  DOI：

  10.1021/np200117y

文献信息

• Pinoresinol‐lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
  作者：Julianne K. Hwang、Syed G.A. Moinuddin、Laurence B. Davin、Norman G. Lewis

  DOI：10.1002/chir.23218

  日期：2020.6

  Two western red cedar pinoresinol‐lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8‐ and 8′‐linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can

  研究了两个西部红柏松脂松香醇-larresresinol还原酶（PLR）的同系物，以确定它们的对映选择性，底物通用性和动力学性质。PLR位于产生的稀疏蛋白质，针叶树醇衍生的立体选择性偶联的下游，以使其进入8和8'连接的呋喃呋喃木脂体木脂松酚。我们的研究表明，每个PLR同源物都可以通过修饰的芳环取代基对映异构地代谢不同的呋喃呋喃木脂素，但是其中C4 / C4'上的酚基对于催化是必不可少的。这些结果与PLR活性部位中醌甲基化物中间体的形成是一致的。定点诱变和动力学测量提供了对影响对映选择性和动力学性质的因素的进一步了解。根据这些数据，
• Dirigent Proteins Guide Asymmetric Heterocoupling for the Synthesis of Complex Natural Product Analogues
  作者：Stacie S. Kim、Elizabeth S. Sattely

  DOI：10.1021/jacs.0c13164

  日期：2021.4.7

  Phenylpropanoids are a class of abundant building blocks found in plants and derived from phenylalanine and tyrosine. Phenylpropanoid polymerization leads to the second most abundant biopolymer lignin while stereo- and site-selective coupling generates an array of lignan natural products with potent biological activity, including the topoisomerase inhibitor and chemotherapeutic etoposide. A key step

  Phenylpropanoids 是一类在植物中发现的丰富的结构单元，来源于苯丙氨酸和酪氨酸。苯丙烷聚合产生第二丰富的生物聚合物木质素，而立体和位点选择性偶联产生一系列具有强生物活性的木脂素天然产物，包括拓扑异构酶抑制剂和化疗药物依托泊苷。依托泊苷生物合成的一个关键步骤涉及一种植物指示蛋白，该蛋白促进松柏醇（一种常见的苯丙素）选择性二聚化，形成 (+)-松脂醇，一种关键的 C 2对称通路中间体。尽管这种偶联反应具有优雅和快速组装依托泊苷支架的能力，但尚未利用定向蛋白来生成其他复杂的木脂素天然产物。在这里，我们证明了来自鬼臼属植物的致敏蛋白与漆酶结合可以引导异源天然和合成松柏醇类似物的偶联，用于松脂醇类似物的对映选择性合成。这种复杂性产生的途径非常直接和有效：三个新键和四个立体中心在一个步骤中由两种不同的非手性单体产生。我们预计我们的结果将使难以获得的非天然木脂素类似物和依托泊苷衍生物的生物
• Lignans and Neolignans from <i>Sinocalamus affinis</i> and Their Absolute Configurations
  作者：Liang Xiong、Chenggeng Zhu、Yanru Li、Ye Tian、Sheng Lin、Shaopeng Yuan、Jinfeng Hu、Qi Hou、Naihong Chen、Yongchun Yang、Jiangong Shi

  DOI：10.1021/np200117y

  日期：2011.5.27

  Twenty-two new lignans and neolignans (1-22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and egthro aryl glycerol units in different neolignans and the CD data [particularly the Rh-2(OCOCF3)(4)-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 mu M, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 +/- 5.9% and 71.7 +/- 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 +/- 2.8% to 91.6 +/- 6.4%, 107.2 +/- 8.0%, and 97.6 +/- 8.5%, respectively.